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Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): o874–o875.
Published online 2008 April 18. doi:  10.1107/S1600536808006740
PMCID: PMC2961315

Bis[4-(dimethyl­amino)phen­yl]diazene oxide

Abstract

The asymmetric unit of the title compound, C16H20N4O, contains six independent approximately planar mol­ecules and is best described as a commensurate modulation of a P21/c parent. Two sets of disordered mol­ecules share almost the same locations (related by an in-plane translation), ensuring that the c-glide plane condition is not attained. C—H(...)O inter­actions provide structural cohesion. The site occupancy factors of the disordered molecules are ca 0.72/0.28 and 0.67/0.33.

Related literature

For general background, see: Kay et al. (2004 [triangle]); Gainsford et al. (2007 [triangle], 2008 [triangle]). For related structures, see: Greci et al. (2003 [triangle]); Domański et al. (2001 [triangle]); Ejsmont et al. (2002 [triangle]); Browning et al. (1974 [triangle]). For related literature, see: Allen (2002 [triangle]); Desiraju & Steiner (1999 [triangle]); Flack (1983 [triangle]); Flack & Bernardinelli (2000 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o874-scheme1.jpg

Experimental

Crystal data

  • C16H20N4O
  • M r = 284.36
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o874-efi1.jpg
  • a = 12.0080 (6) Å
  • b = 22.0379 (11) Å
  • c = 17.3408 (8) Å
  • β = 109.450 (3)°
  • V = 4327.0 (4) Å3
  • Z = 12
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 99 (2) K
  • 0.66 × 0.25 × 0.17 mm

Data collection

  • Bruker–Nonius APEX2 CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2006 [triangle]; Blessing, 1995 [triangle]) T min = 0.800, T max = 1.000 (expected range = 0.789–0.986)
  • 106040 measured reflections
  • 13444 independent reflections
  • 8097 reflections with I > 2σ(I)
  • R int = 0.062

Refinement

  • R[F 2 > 2σ(F 2)] = 0.109
  • wR(F 2) = 0.374
  • S = 1.03
  • 13444 reflections
  • 1113 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.79 e Å−3
  • Δρmin = −0.69 e Å−3

Data collection: APEX2 (Bruker, 2006 [triangle]); cell refinement: SAINT (Bruker, 2006 [triangle]); data reduction: SAINT and SADABS (Bruker, 2006 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]), PLATON (Spek, 2003 [triangle]) and Mercury (Macrae et al., 2006 [triangle]); software used to prepare material for publication: SHELXL97, PLATON and Mercury.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808006740/sj2473sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808006740/sj2473Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank Professor Ward T. Robinson and Dr J. Wikaira of the University of Canterbury, New Zealand, for their assistance with the data collection.

supplementary crystallographic information

Comment

During the preparation of the chromophore 2-{3-cyano-4-[(4-dimethylamino-phenylimino)-methyl]-5,5-dimethyl-5H -furan-2-ylidene}-malonitrile we isolated the title compound as a byproduct. There are at least 27 reported structures containing a 4-azoxybenzene moiety (Cambridge Structural Database, Version 5.29 with November 2007 updates; Allen, 2002). Of these, four are closely related or have been extensively analysed: 1-(4-Aminophenyl)-2-phenyldiazene 2-oxide (α & β) which crystallized as different polymorphs (QIKFEV, Domański et al.(2001); QIKFEV01, Ejsmont et al. (2002)), the p-dimethylaminoazoxybenzene (MAZXBZ, Browning et al. (1974)) and the 3-chloro adduct which was also isolated as a side product (EMUQOS, Greci et al., 2003).

The asymmetric unit contains six copies of the title chiro compound which are shown in Figures 1–6. The structure can be described as a commensurate modulation of a P21/c parent with 1/3 the b axis (Figure 7). Figures 5 & 6 depict the disordered molecules 5 & 6, with the minor components (given numbers 8 & 7 respectively) related by a translation along the molecule by 1–1.5Å (i.e. close to a bond length): hence in Figure 6, atoms N61 & C73 coincide and were refined on one site (see experimental). The convention we used for atom labelling is C(N,O)xn where x is the molecule number and n is the atom number (see Tables 1 & 2). Because of the approximations involved in refining the two disordered molecules (5,8 & 6,7) (reflected in larger su values), we use only average dimensions for molecules 1–4 in the discussion below. It is however noted that all the structures (1–6) are nearly superimposable with weighted r.m.s. fits ranging from 0.016Å to 0.071Å (Spek, 2003).

Overall the molecules are close to being planar with average interplanar angles between the two phenyl rings of 3.4 (3)°. From the previous studies of the trans-4-aminoazoxybenzenes (QIKFEV, QIKFEV01) it is clear that the molecules found here are similar to the QIKFEV α isomer with the average Caryl—NO length longer than the Caryl—N (1.474 versus 1.456 Å). The dimethylamino nitrogen atoms (Nx1 & Nx4) are close to planar with their bound atoms (Cx1,Cx2,Cx3 & Cx12,Cx15,Cx16): average out of plane deviations are 0.019 (8) and 0.035 (9)Å respectively similar to EMUQOS values. The (average) dimensions of the two phenyl rings do not support any quinonoid deformation. The character of the substituent to the phenyl rings (quoted by Domanski et al. (2001)) being electron-releasing is observed with the ipso angles at Cx3, Cx12 & Cx9 being 118.0 (4), 117.6 (4) & 117.6 (5)° respectively compared with that at Cx6 (120.4 (1)°). In the studies noted, there is some ambivalence about the intramolecular contact between Ox1 and Hx10(on Cx10) as to whether it is attractive or not. The average Hx5···Ox1 and Cx5–Hx5···Ox1 dimensions (2.36 Å) and angle (100°) compare with the Hx10···Ox1 values of 2.16Å and 118°, confirming the latter are attractive weak interactions (Desiraju & Steiner (1999)).

The Cx14—Hx14···O(n)1 intermolecular interactions, involving the proton on the opposite side of the Cx9—Cx14 ring to the intramolecular interaction, links non-parallel molecules into dimers (Table 2), as has been observed before in MAZXBZ with H···O 2.44Å and C—H···O 172°. The resulting "herringbone" structure has molecules in approximate layers parallel to the (1,2,-1) and (-1,2,1) planes.

Experimental

To a solution of 4,5,5-trimethyl-3-cyano-2(5H)-furanylidenepropane dinitrile (1.0 g, 5.02 mmol) in 20 ml of absolute ethanol was added the N,N-dimethylamino-4-nitrosoaniline (829 mg, 5.52 mmol) and the reaction mixture was refluxed for 1 h. in the presence of piperidine acetate as catalyst. This reaction mixture was then cooled and filtered. The crude material was chromatographed (silica gel, dichloromethane) to afford 4,4'-bis(dimethylamino)azoxybenzene (71 mg, 5%), (I), as a brownish red solid. This was the third major product eluted from the column. m.p. 250–252°C; 1H NMR (300 MHz, DMSO) δ 3.02 (12 H, s, 4 x CH3), 6.77 (4 H, d, J 12.0 Hz, ArH), 8.03(2 H, d, J 9.0 Hz, ArH), 8.16 (2 H, d, J 9.0 Hz, ArH),; 13C NMR (75 MHz, DMSO) δ 39.2, 111.2, 111.4, 122.9, 127.6. M+ m/z for C16H21N4O 285.1715, Found 285.1704.

Refinement

In the absence of significant anomalous scattering, the values of the Flack (1983) parameter were indeterminate (Flack & Bernardinelli, 2000). Accordingly, the Friedel-equivalent reflections were merged prior to the final refinements. A total of 16 reflections were omitted from the refinement; all but 3 were measured at low theta with unbalanced backgrounds resulting in (outlier) negative intensities.

Preliminary analysis (structural solution) indicated that the space group might be P21/c (at the 94% level (Spek, 2003)) but this was ruled out by the definite breaking of the c glide absence condition. The central N=N+(O–) is often disordered in these structures; the final difference Fourier maps indicate that this may be partially the case for molecules 3 & 4. Refinement was only successful in the reported space group. The disordered fragments based on O71 and O81 (corresponding to molecules O61 & O51 respectively, see Figures 5 & 7) were each given one common Uiso value and a complementary occupancy to the adjacent one-bond shifted molecule: so molecules 6/7 had occupancies of 0.674 (7)/0.326 (7) with Uiso 0.0392 (16) Å2 (molecule 7) and 5/8 occupancies of 0.724 (6)/0.276 (6) with Uiso 0.0332 (15) Å2 (molecule 8). H atoms on the minor disordered molecules (O71 & O81) were not located or included.

Atoms that were unstable to refinement as anisotropic atoms, or gave highly prolate parameters, were refined with isotropic thermal parameters.

All H atoms bound to carbon were constrained to their expected geometries (C—H 0.98, 0.99 Å). All methyl and tertiary H atoms were refined with Uiso 1.5 & 1.2 times respectively that of the Ueq of their parent atom.

Figures

Fig. 1.
Molecular structure of molecule 1 of the asymmetic unit (Farrugia, 1997); displacement ellipsoids are shown at the 50% probability level.
Fig. 2.
Molecular structure of molecule 2 of the asymmetic unit (Farrugia, 1997); displacement ellipsoids are shown at the 50% probability level.
Fig. 3.
Molecular structure of molecule 3 of the asymmetic unit (Farrugia, 1997); displacement ellipsoids are shown at the 50% probability level.
Fig. 4.
Molecular structure of molecule 4 of the asymmetic unit (Farrugia, 1997); displacement ellipsoids are shown at the 50% probability level.
Fig. 5.
PLATON (Spek, 2003) view of the disordered molecular unit based on molecule 5 (see text). Occupancies of the O51/O81 based units are 0.724 (6)/0.276 (6).
Fig. 6.
PLATON (Spek, 2003) view of the disordered molecular unit based on molecule 6 (see text). Occupancies of the O61/O71 based units are 0.674 (7)/0.326 (7).
Fig. 7.
Packing diagram (Mercury; Macrae et al., 2006) of the unit cell showing the 1/3 relationship down the b axis. One terminal methylamino (Nx4) of each unique molecule is labelled. Minor disorder molecules breaking c glide symmetry are shown as "+" signs. ...

Crystal data

C16H20N4OF000 = 1824
Mr = 284.36Dx = 1.310 Mg m3
Monoclinic, P21Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 8860 reflections
a = 12.0080 (6) Åθ = 2.5–29.5º
b = 22.0379 (11) ŵ = 0.09 mm1
c = 17.3408 (8) ÅT = 99 (2) K
β = 109.450 (3)ºNeedles, orange
V = 4327.0 (4) Å30.66 × 0.25 × 0.17 mm
Z = 12

Data collection

Bruker–Nonius APEX2 CCD area-detector diffractometer13444 independent reflections
Radiation source: fine-focus sealed tube8097 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.062
Detector resolution: 8.192 pixels mm-1θmax = 30.6º
T = 99(2) Kθmin = 1.8º
[var phi] and ω scansh = −17→17
Absorption correction: multi-scan(SADABS; Bruker, 2006; Blessing, 1995)k = −31→31
Tmin = 0.800, Tmax = 1.0l = −24→24
106040 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.109H-atom parameters constrained
wR(F2) = 0.374  w = 1/[σ2(Fo2) + (0.167P)2 + 10.2925P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.050
13444 reflectionsΔρmax = 0.79 e Å3
1113 parametersΔρmin = −0.69 e Å3
1 restraintExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
O110.2603 (4)0.1917 (2)0.2315 (3)0.0314 (11)
N110.4478 (5)0.1429 (3)0.6120 (4)0.0285 (12)
N120.2049 (5)0.1611 (3)0.2714 (4)0.0296 (12)
N130.1027 (5)0.1379 (2)0.2445 (3)0.0238 (10)
N14−0.2037 (5)0.1412 (3)−0.0806 (3)0.0299 (12)*
C110.4004 (7)0.1082 (4)0.6655 (5)0.0342 (15)
H11A0.32480.12570.66410.051*
H11B0.45620.10960.72160.051*
H11C0.38860.06600.64690.051*
C120.5543 (6)0.1753 (4)0.6473 (5)0.0371 (16)
H12A0.62040.15160.64200.056*
H12B0.56660.18260.70540.056*
H12C0.54970.21420.61910.056*
C130.3877 (5)0.1446 (3)0.5288 (4)0.0273 (13)
C140.4370 (6)0.1769 (3)0.4765 (4)0.0272 (13)
H140.51160.19640.49850.033*
C150.3754 (6)0.1797 (3)0.3941 (4)0.0306 (14)
H150.40980.20060.35960.037*
C160.2679 (6)0.1539 (3)0.3598 (4)0.0243 (12)
C170.2170 (6)0.1222 (3)0.4099 (4)0.0266 (13)
H170.14150.10400.38660.032*
C180.2767 (6)0.1174 (3)0.4934 (4)0.0271 (13)
H180.24210.09540.52680.032*
C190.0346 (6)0.1450 (3)0.1614 (4)0.0243 (12)*
C1100.0650 (6)0.1720 (3)0.0964 (4)0.0256 (12)*
H1100.14120.18920.10730.031*
C111−0.0159 (6)0.1735 (3)0.0168 (4)0.0266 (12)*
H1110.00310.1946−0.02500.032*
C112−0.1269 (5)0.1432 (3)−0.0017 (3)0.0219 (11)*
C113−0.1568 (6)0.1185 (3)0.0639 (4)0.0278 (13)
H113−0.23390.10250.05390.033*
C114−0.0770 (6)0.1169 (3)0.1416 (4)0.0282 (13)
H114−0.09730.09640.18320.034*
C115−0.3180 (6)0.1151 (3)−0.1004 (4)0.0325 (14)*
H15A−0.31360.0783−0.06780.049*
H15B−0.34770.1048−0.15870.049*
H15C−0.37160.1443−0.08840.049*
C116−0.1732 (7)0.1686 (4)−0.1472 (4)0.0343 (15)
H16A−0.19490.2116−0.15160.052*
H16B−0.21600.1479−0.19850.052*
H16C−0.08800.1647−0.13630.052*
O210.7507 (4)0.3591 (3)0.7787 (3)0.0356 (12)
N210.5621 (5)0.3088 (3)0.3987 (4)0.0354 (13)
N220.8010 (5)0.3283 (3)0.7351 (4)0.0339 (13)*
N230.9052 (5)0.3045 (3)0.7629 (4)0.0314 (13)
N241.2173 (5)0.3106 (3)1.0890 (4)0.0342 (13)
C210.6101 (7)0.2753 (4)0.3452 (5)0.0402 (17)
H21A0.55560.27790.28890.060*
H21B0.62060.23270.36230.060*
H21C0.68660.29260.34820.060*
C220.4564 (7)0.3421 (4)0.3643 (6)0.0438 (19)
H22A0.39420.32450.38220.066*
H22B0.43240.34040.30450.066*
H22C0.46950.38440.38230.066*
C230.6200 (6)0.3111 (3)0.4801 (5)0.0299 (14)
C240.5710 (7)0.3433 (3)0.5320 (5)0.0340 (15)
H240.49660.36280.50950.041*
C250.6305 (6)0.3464 (4)0.6145 (4)0.0349 (15)*
H250.59470.36620.64890.042*
C260.7402 (7)0.3217 (3)0.6480 (4)0.0286 (13)
C270.7936 (7)0.2906 (3)0.5994 (5)0.0324 (14)
H270.86920.27260.62340.039*
C280.7353 (6)0.2863 (3)0.5159 (5)0.0327 (15)
H280.77260.26670.48230.039*
C290.9751 (6)0.3115 (3)0.8476 (4)0.0300 (13)
C2100.9447 (6)0.3369 (3)0.9122 (5)0.0343 (16)
H2100.86740.35260.90160.041*
C2111.0259 (6)0.3395 (3)0.9919 (5)0.0321 (14)
H2111.00660.36091.03330.039*
C2121.1371 (6)0.3100 (3)1.0105 (4)0.0278 (13)*
C2141.0861 (7)0.2834 (3)0.8665 (5)0.0321 (14)
H2141.10600.26290.82460.039*
C2131.1669 (6)0.2850 (3)0.9447 (4)0.0301 (14)
H2131.24390.26900.95460.036*
C2151.3306 (7)0.2831 (4)1.1090 (5)0.0378 (16)*
H25A1.32290.24341.08220.057*
H25B1.36440.27791.16840.057*
H25C1.38250.30911.09010.057*
C2161.1852 (8)0.3344 (4)1.1571 (5)0.0416 (18)
H26A1.20020.37821.16190.062*
H26B1.23270.31431.20780.062*
H26C1.10130.32681.14740.062*
O310.2305 (5)0.2080 (3)0.7569 (4)0.0414 (13)
N310.0438 (7)0.2581 (4)0.3779 (6)0.052 (2)
N320.2833 (6)0.2369 (3)0.7173 (4)0.0394 (14)*
N330.3846 (8)0.2583 (3)0.7408 (6)0.056 (2)
N340.6924 (5)0.2553 (3)1.0709 (4)0.0403 (15)
C310.0907 (9)0.2913 (5)0.3239 (6)0.052 (2)
H31A0.09540.33450.33800.078*
H31B0.03880.28590.26720.078*
H31C0.16980.27610.32970.078*
C32−0.0663 (8)0.2233 (5)0.3395 (7)0.054 (2)
H32A−0.12690.23670.36210.081*
H32B−0.05080.17990.35060.081*
H32C−0.09420.23010.28030.081*
C330.1018 (7)0.2551 (4)0.4614 (5)0.0385 (17)
C340.0536 (7)0.2251 (4)0.5129 (6)0.0424 (19)
H34−0.02230.20720.49010.051*
C350.1127 (7)0.2199 (4)0.5985 (6)0.0414 (18)
H350.07810.19950.63320.050*
C360.2245 (8)0.2465 (4)0.6288 (6)0.046 (2)
C370.2731 (8)0.2789 (4)0.5789 (6)0.044 (2)
H370.34810.29770.60170.053*
C380.2120 (7)0.2837 (4)0.4962 (6)0.0413 (19)
H380.24470.30650.46250.050*
C390.4524 (8)0.2500 (4)0.8300 (6)0.0413 (18)
C3100.4268 (7)0.2212 (3)0.8940 (6)0.0406 (19)
H3100.35420.20010.88330.049*
C3110.5055 (7)0.2233 (3)0.9720 (5)0.0372 (17)
H3110.48400.20531.01480.045*
C3120.6153 (7)0.2506 (3)0.9911 (6)0.044 (2)
C3130.6446 (7)0.2772 (3)0.9275 (6)0.0403 (19)
H3130.71910.29630.93820.048*
C3140.5644 (8)0.2757 (4)0.8484 (6)0.045 (2)
H3140.58660.29270.80540.054*
C3150.8103 (7)0.2825 (4)1.0885 (6)0.049 (2)
H35A0.84830.26531.05140.074*
H35B0.85850.27371.14520.074*
H35C0.80240.32651.08060.074*
C3160.6622 (8)0.2286 (5)1.1377 (6)0.050 (2)
H36A0.59730.25151.14610.074*
H36B0.73120.22981.18770.074*
H36C0.63780.18641.12440.074*
O410.7975 (5)0.3742 (3)0.2746 (4)0.0451 (14)
N410.9841 (6)0.4259 (4)0.6541 (4)0.0423 (15)
N420.7443 (7)0.4037 (3)0.3130 (5)0.0460 (18)
N430.6439 (7)0.4265 (3)0.2899 (5)0.0485 (18)
N440.3356 (6)0.4182 (3)−0.0370 (5)0.0414 (16)
C410.9366 (7)0.4595 (4)0.7077 (5)0.0397 (17)
H41A0.93900.50300.69680.060*
H41B0.98390.45120.76480.060*
H41C0.85470.44700.69800.060*
C421.0936 (7)0.3916 (4)0.6925 (6)0.0438 (19)
H42A1.11460.39350.75210.066*
H42B1.15740.40930.67630.066*
H42C1.08180.34920.67460.066*
C430.9267 (6)0.4240 (3)0.5705 (5)0.0342 (15)
C440.9742 (7)0.3915 (4)0.5200 (6)0.0431 (19)
H441.04740.37120.54360.052*
C450.9170 (8)0.3880 (4)0.4349 (6)0.047 (2)
H450.95350.36910.40020.056*
C460.8027 (7)0.4138 (4)0.4032 (5)0.0397 (17)
C470.7565 (7)0.4461 (4)0.4530 (6)0.0426 (18)
H470.68260.46590.42970.051*
C480.8136 (6)0.4505 (3)0.5349 (5)0.0354 (15)
H480.77760.47140.56830.043*
C490.5769 (8)0.4172 (4)0.2026 (6)0.0436 (19)
C4100.6031 (6)0.3912 (4)0.1390 (6)0.0401 (18)
H4100.67950.37430.14950.048*
C4110.5249 (7)0.3885 (3)0.0613 (6)0.0409 (19)
H4110.54460.36670.02040.049*
C4120.4141 (6)0.4183 (3)0.0416 (5)0.0343 (15)
C4130.3850 (7)0.4432 (3)0.1062 (5)0.0381 (18)
H4130.30800.45920.09610.046*
C4140.4664 (7)0.4451 (4)0.1855 (5)0.0393 (16)
H4140.44690.46530.22770.047*
C4150.2199 (7)0.4465 (4)−0.0554 (5)0.0433 (17)*
H45A0.16460.4280−0.10470.065*
H45B0.22640.4900−0.06440.065*
H45C0.19100.4404−0.00930.065*
C4160.3707 (8)0.3947 (4)−0.1030 (5)0.0470 (19)*
H46A0.42550.4232−0.11500.071*
H46B0.30080.3896−0.15180.071*
H46C0.40980.3554−0.08720.071*
O510.3067 (6)0.5245 (4)0.2846 (4)0.0333 (15)0.724 (6)
N510.4915 (6)0.4732 (4)0.6635 (5)0.0276 (15)0.724 (6)
N520.2534 (6)0.4933 (3)0.3272 (5)0.0223 (15)*0.724 (6)
N530.1494 (6)0.4704 (4)0.2959 (5)0.0251 (15)0.724 (6)
N54−0.1486 (6)0.4743 (3)−0.0247 (4)0.0203 (13)*0.724 (6)
C510.4444 (9)0.4402 (5)0.7159 (6)0.035 (2)0.724 (6)
H51A0.38090.46370.72530.052*0.724 (6)
H51B0.50680.43260.76820.052*0.724 (6)
H51C0.41280.40130.69030.052*0.724 (6)
C520.5992 (8)0.5067 (6)0.6998 (6)0.041 (3)0.724 (6)
H52A0.58300.55030.69180.061*0.724 (6)
H52B0.65710.49490.67380.061*0.724 (6)
H52C0.63100.49780.75840.061*0.724 (6)
C530.4320 (7)0.4775 (4)0.5818 (5)0.0188 (16)*0.724 (6)
C540.4811 (8)0.5084 (4)0.5292 (6)0.0262 (17)0.724 (6)
H540.55770.52550.55140.031*0.724 (6)
C550.4221 (8)0.5141 (4)0.4483 (6)0.0231 (18)*0.724 (6)
H550.45520.53780.41550.028*0.724 (6)
C560.3148 (8)0.4861 (4)0.4128 (5)0.0243 (16)0.724 (6)
C570.2605 (8)0.4549 (4)0.4613 (6)0.0255 (19)*0.724 (6)
H570.18410.43780.43750.031*0.724 (6)
C580.3211 (7)0.4493 (4)0.5454 (5)0.0259 (17)0.724 (6)
H580.28720.42620.57830.031*0.724 (6)
C590.0828 (7)0.4753 (4)0.2134 (5)0.0202 (17)*0.724 (6)
C5100.1170 (8)0.5044 (4)0.1516 (5)0.0262 (17)0.724 (6)
H5100.19070.52480.16430.031*0.724 (6)
C5110.0366 (8)0.5019 (4)0.0698 (5)0.0203 (17)*0.724 (6)
H5110.06040.51800.02690.024*0.724 (6)
C512−0.0766 (7)0.4765 (4)0.0504 (5)0.0196 (14)0.724 (6)
C513−0.1071 (8)0.4492 (4)0.1152 (5)0.0224 (18)*0.724 (6)
H513−0.18170.43010.10390.027*0.724 (6)
C514−0.0298 (8)0.4505 (4)0.1936 (5)0.0259 (17)0.724 (6)
H514−0.05380.43380.23610.031*0.724 (6)
C515−0.2662 (8)0.4479 (4)−0.0488 (6)0.0318 (19)0.724 (6)
H55A−0.26550.4125−0.01440.048*0.724 (6)
H55B−0.29010.4353−0.10620.048*0.724 (6)
H55C−0.32220.4781−0.04200.048*0.724 (6)
C516−0.1176 (8)0.5007 (5)−0.0933 (6)0.032 (2)0.724 (6)
H56A−0.12630.5449−0.09320.047*0.724 (6)
H56B−0.17030.4842−0.14510.047*0.724 (6)
H56C−0.03570.4904−0.08710.047*0.724 (6)
O610.7398 (8)0.0396 (4)0.2128 (7)0.046 (2)0.674 (7)
N610.9297 (8)0.0927 (4)0.5843 (5)0.061 (3)*0.674 (7)
N620.6883 (7)0.0680 (4)0.2551 (5)0.0270 (17)*0.674 (7)
N630.5853 (10)0.0893 (5)0.2278 (8)0.037 (2)*0.674 (7)
N640.2734 (8)0.0849 (5)−0.0971 (6)0.0320 (19)*0.674 (7)
C610.8824 (10)0.1239 (6)0.6478 (8)0.041 (3)0.674 (7)
H61A0.83190.15830.62200.061*0.674 (7)
H61B0.94900.13850.69410.061*0.674 (7)
H61C0.83640.09460.66740.061*0.674 (7)
C621.0398 (11)0.0546 (7)0.6284 (10)0.050 (3)0.674 (7)
H62A1.02360.02850.66910.075*0.674 (7)
H62B1.10600.08160.65560.075*0.674 (7)
H62C1.06010.02940.58840.075*0.674 (7)
C630.8699 (9)0.0878 (5)0.5080 (6)0.030 (2)*0.674 (7)
C640.9224 (10)0.0607 (5)0.4530 (8)0.033 (2)*0.674 (7)
H641.00190.04710.47370.040*0.674 (7)
C650.8603 (9)0.0541 (5)0.3712 (7)0.032 (2)*0.674 (7)
H650.89480.03330.33670.039*0.674 (7)
C660.7487 (11)0.0775 (6)0.3393 (8)0.036 (2)*0.674 (7)
C670.6967 (11)0.1085 (5)0.3937 (9)0.040 (3)0.674 (7)
H670.61860.12400.37250.048*0.674 (7)
C680.7587 (10)0.1151 (5)0.4735 (8)0.031 (2)*0.674 (7)
H680.72690.13860.50710.037*0.674 (7)
C690.5198 (8)0.0830 (5)0.1439 (7)0.028 (2)0.674 (7)
C6100.5435 (9)0.0536 (4)0.0783 (7)0.0233 (18)*0.674 (7)
H6100.61430.03100.08850.028*0.674 (7)
C6110.4656 (9)0.0575 (4)0.0008 (7)0.028 (2)0.674 (7)
H6110.49040.0421−0.04200.033*0.674 (7)
C6120.3493 (8)0.0829 (4)−0.0215 (6)0.0202 (16)*0.674 (7)
C6130.3270 (9)0.1098 (5)0.0460 (6)0.0243 (18)*0.674 (7)
H6130.25390.13010.03660.029*0.674 (7)
C6140.4052 (10)0.1081 (5)0.1241 (7)0.0257 (19)*0.674 (7)
H6140.38160.12450.16690.031*0.674 (7)
C6150.1567 (8)0.1132 (5)−0.1147 (7)0.030 (2)0.674 (7)
H65A0.12190.1001−0.07370.045*0.674 (7)
H65B0.10530.1008−0.16920.045*0.674 (7)
H65C0.16530.1574−0.11280.045*0.674 (7)
C6160.3071 (12)0.0613 (6)−0.1642 (9)0.044 (3)0.674 (7)
H66A0.37040.0864−0.17130.066*0.674 (7)
H66B0.23870.0621−0.21450.066*0.674 (7)
H66C0.33510.0195−0.15210.066*0.674 (7)
O710.7848 (15)0.0407 (8)0.2568 (11)0.0392 (16)*0.326 (7)
N710.9709 (17)0.0889 (9)0.6398 (12)0.0392 (16)*0.326 (7)
N720.7342 (18)0.0704 (9)0.3016 (14)0.0392 (16)*0.326 (7)
N730.6248 (18)0.0929 (10)0.2716 (13)0.0392 (16)*0.326 (7)
N740.3176 (19)0.0895 (10)−0.0585 (15)0.0392 (16)*0.326 (7)
C710.928 (2)0.1216 (11)0.6991 (15)0.0392 (16)*0.326 (7)
C721.085 (2)0.0566 (11)0.6823 (15)0.0392 (16)*0.326 (7)
C730.9297 (8)0.0927 (4)0.5843 (5)0.0392 (16)*0.326 (7)
C740.955 (2)0.0575 (11)0.4994 (15)0.0392 (16)*0.326 (7)
C750.897 (2)0.0515 (11)0.4145 (18)0.0392 (16)*0.326 (7)
C760.784 (2)0.0811 (11)0.3878 (15)0.0392 (16)*0.326 (7)
C770.744 (2)0.1132 (12)0.439 (2)0.0392 (16)*0.326 (7)
C780.803 (2)0.1176 (11)0.5202 (15)0.0392 (16)*0.326 (7)
C790.566 (2)0.0846 (12)0.1887 (19)0.0392 (16)*0.326 (7)
C7100.579 (2)0.0576 (12)0.1158 (17)0.0392 (16)*0.326 (7)
C7110.517 (2)0.0525 (12)0.0420 (19)0.0392 (16)*0.326 (7)
C7120.399 (2)0.0862 (11)0.0239 (14)0.0392 (16)*0.326 (7)
C7130.369 (2)0.1109 (11)0.0872 (18)0.0392 (16)*0.326 (7)
C7140.451 (2)0.1110 (11)0.1669 (15)0.0392 (16)*0.326 (7)
C7150.205 (2)0.1199 (11)−0.0706 (15)0.0392 (16)*0.326 (7)
C7160.355 (2)0.0676 (12)−0.1252 (16)0.0392 (16)*0.326 (7)
O810.2568 (15)0.5270 (8)0.2269 (11)0.0332 (15)*0.276 (6)
N810.450 (2)0.4766 (11)0.6105 (17)0.0332 (15)*0.276 (6)
N820.1979 (18)0.4941 (10)0.2666 (13)0.0332 (15)*0.276 (6)
N830.102 (2)0.4712 (11)0.2388 (16)0.0332 (15)*0.276 (6)
N84−0.2127 (18)0.4776 (10)−0.0865 (12)0.0332 (15)*0.276 (6)
C810.396 (2)0.4413 (12)0.6636 (16)0.0332 (15)*0.276 (6)
C820.548 (2)0.5087 (11)0.6387 (15)0.0332 (15)*0.276 (6)
C830.378 (2)0.4779 (12)0.5188 (15)0.0332 (15)*0.276 (6)
C840.443 (3)0.5115 (13)0.478 (2)0.0332 (15)*0.276 (6)
C850.368 (2)0.5129 (11)0.3862 (15)0.0332 (15)*0.276 (6)
C860.270 (2)0.4881 (12)0.3595 (19)0.0332 (15)*0.276 (6)
C870.214 (2)0.4570 (12)0.4066 (15)0.0332 (15)*0.276 (6)
C880.275 (2)0.4508 (13)0.492 (2)0.0332 (15)*0.276 (6)
C890.028 (2)0.4783 (12)0.1540 (15)0.0332 (15)*0.276 (6)
C8100.065 (3)0.5061 (13)0.0922 (19)0.0332 (15)*0.276 (6)
C811−0.025 (2)0.5085 (11)0.0060 (15)0.0332 (15)*0.276 (6)
C813−0.167 (2)0.4549 (11)0.0545 (15)0.0332 (15)*0.276 (6)
C814−0.075 (3)0.4494 (13)0.139 (2)0.0332 (15)*0.276 (6)
C815−0.326 (2)0.4524 (11)−0.1049 (15)0.0332 (15)*0.276 (6)
C816−0.184 (2)0.5034 (11)−0.1507 (15)0.0332 (15)*0.276 (6)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O110.027 (2)0.039 (3)0.035 (2)−0.010 (2)0.0199 (19)0.003 (2)
N110.020 (2)0.033 (3)0.034 (3)0.001 (2)0.011 (2)−0.002 (2)
N120.033 (3)0.022 (2)0.046 (3)0.001 (2)0.028 (2)0.003 (2)
N130.023 (2)0.022 (2)0.031 (2)0.0015 (19)0.0146 (19)0.0025 (19)
C110.030 (3)0.041 (4)0.035 (3)0.000 (3)0.015 (3)0.006 (3)
C120.025 (3)0.042 (4)0.040 (3)−0.006 (3)0.006 (3)−0.002 (3)
C130.020 (3)0.027 (3)0.038 (3)0.005 (2)0.014 (2)0.007 (3)
C140.023 (3)0.026 (3)0.037 (3)0.003 (2)0.015 (2)0.000 (2)
C150.031 (3)0.029 (3)0.036 (3)0.006 (3)0.016 (3)0.009 (3)
C160.025 (3)0.016 (3)0.036 (3)0.002 (2)0.016 (2)−0.002 (2)
C170.023 (3)0.028 (3)0.031 (3)0.000 (2)0.012 (2)0.003 (2)
C180.022 (3)0.026 (3)0.035 (3)0.001 (2)0.012 (2)−0.001 (2)
C1130.026 (3)0.029 (3)0.036 (3)−0.010 (2)0.020 (3)−0.008 (3)
C1140.034 (3)0.021 (3)0.035 (3)0.003 (2)0.018 (3)0.003 (2)
C1160.038 (4)0.038 (4)0.031 (3)0.000 (3)0.018 (3)0.002 (3)
O210.028 (2)0.041 (3)0.049 (3)0.004 (2)0.026 (2)−0.006 (2)
N210.029 (3)0.037 (3)0.048 (3)0.008 (2)0.023 (2)0.007 (3)
N230.034 (3)0.019 (2)0.057 (4)0.005 (2)0.036 (3)0.001 (2)
N240.031 (3)0.039 (3)0.039 (3)0.005 (2)0.020 (2)−0.006 (2)
C210.040 (4)0.037 (4)0.054 (4)0.006 (3)0.030 (3)0.002 (3)
C220.033 (4)0.047 (5)0.058 (5)0.010 (3)0.024 (3)0.004 (4)
C230.027 (3)0.021 (3)0.053 (4)−0.004 (2)0.029 (3)−0.003 (2)
C240.033 (3)0.033 (3)0.047 (4)−0.001 (3)0.028 (3)0.003 (3)
C260.042 (3)0.017 (3)0.037 (3)−0.007 (2)0.025 (3)−0.002 (2)
C270.032 (3)0.027 (3)0.046 (4)0.003 (3)0.023 (3)0.002 (3)
C280.033 (3)0.023 (3)0.051 (4)0.003 (2)0.026 (3)0.004 (3)
C290.034 (3)0.024 (3)0.039 (3)−0.001 (3)0.021 (3)0.007 (3)
C2100.029 (3)0.024 (3)0.056 (4)−0.007 (2)0.022 (3)−0.003 (3)
C2110.027 (3)0.029 (3)0.048 (4)0.004 (3)0.023 (3)0.005 (3)
C2140.037 (3)0.024 (3)0.041 (3)−0.002 (2)0.022 (3)−0.001 (3)
C2130.033 (3)0.025 (3)0.044 (3)0.011 (2)0.028 (3)0.009 (3)
C2160.044 (4)0.043 (5)0.047 (4)0.005 (4)0.027 (3)−0.010 (3)
O310.040 (3)0.040 (3)0.056 (3)−0.008 (2)0.032 (3)0.007 (2)
N310.045 (4)0.048 (4)0.072 (5)−0.003 (3)0.032 (4)0.014 (4)
N330.059 (5)0.032 (4)0.106 (7)−0.018 (3)0.064 (5)−0.016 (4)
N340.024 (3)0.042 (3)0.060 (4)−0.006 (2)0.021 (3)0.006 (3)
C310.056 (5)0.042 (5)0.077 (6)0.010 (4)0.046 (5)0.015 (4)
C320.041 (4)0.051 (5)0.078 (6)−0.003 (4)0.033 (4)0.001 (5)
C330.037 (4)0.030 (4)0.057 (5)0.004 (3)0.027 (3)−0.008 (3)
C340.033 (4)0.036 (4)0.066 (5)0.004 (3)0.028 (4)0.011 (4)
C350.041 (4)0.031 (4)0.062 (5)0.007 (3)0.032 (4)0.003 (3)
C360.044 (4)0.040 (4)0.059 (5)0.013 (4)0.025 (4)−0.003 (4)
C370.038 (4)0.030 (4)0.066 (5)0.005 (3)0.021 (4)−0.012 (3)
C380.035 (4)0.029 (4)0.074 (5)0.004 (3)0.036 (4)0.004 (3)
C390.047 (4)0.025 (3)0.059 (5)0.009 (3)0.026 (4)−0.009 (3)
C3100.030 (3)0.025 (3)0.077 (5)−0.010 (2)0.032 (3)−0.024 (3)
C3110.032 (3)0.026 (3)0.068 (5)0.002 (2)0.037 (3)0.000 (3)
C3120.042 (4)0.022 (3)0.084 (6)−0.004 (3)0.041 (4)−0.009 (3)
C3130.038 (4)0.019 (3)0.075 (6)0.002 (3)0.034 (4)−0.004 (3)
C3140.053 (5)0.027 (4)0.072 (6)−0.006 (3)0.044 (4)−0.007 (3)
C3150.032 (3)0.045 (4)0.078 (6)−0.015 (3)0.029 (4)−0.012 (4)
C3160.039 (4)0.059 (6)0.060 (5)−0.009 (4)0.029 (4)−0.002 (4)
O410.039 (3)0.043 (3)0.069 (4)0.006 (3)0.039 (3)−0.004 (3)
N410.035 (3)0.048 (4)0.051 (4)0.005 (3)0.022 (3)−0.005 (3)
N420.054 (4)0.027 (3)0.081 (5)0.001 (3)0.054 (4)0.000 (3)
N430.056 (4)0.027 (3)0.081 (5)0.009 (3)0.047 (4)0.003 (3)
N440.035 (3)0.035 (3)0.063 (4)0.000 (2)0.029 (3)−0.015 (3)
C410.040 (4)0.037 (4)0.049 (4)0.006 (3)0.024 (3)0.003 (3)
C420.031 (3)0.046 (5)0.061 (5)0.009 (3)0.025 (3)0.001 (4)
C430.032 (3)0.028 (3)0.052 (4)−0.005 (2)0.026 (3)0.002 (3)
C440.040 (4)0.041 (4)0.062 (5)0.000 (3)0.036 (4)−0.005 (4)
C450.051 (4)0.038 (4)0.070 (6)−0.003 (3)0.044 (4)0.009 (4)
C460.045 (4)0.032 (4)0.052 (4)−0.008 (3)0.029 (3)0.002 (3)
C470.040 (4)0.032 (4)0.064 (5)−0.001 (3)0.028 (4)0.011 (3)
C480.031 (3)0.028 (3)0.058 (4)−0.001 (3)0.028 (3)−0.003 (3)
C490.047 (4)0.023 (3)0.066 (5)−0.009 (3)0.026 (4)0.005 (3)
C4100.025 (3)0.027 (4)0.075 (5)0.005 (3)0.026 (3)0.014 (3)
C4110.038 (4)0.022 (3)0.081 (6)−0.007 (3)0.044 (4)−0.007 (3)
C4120.033 (3)0.022 (3)0.061 (4)0.003 (3)0.034 (3)0.003 (3)
C4130.040 (4)0.019 (3)0.071 (5)−0.006 (3)0.039 (4)−0.003 (3)
C4140.048 (4)0.031 (4)0.050 (4)0.003 (3)0.031 (3)0.008 (3)
O510.035 (3)0.035 (4)0.040 (4)−0.009 (3)0.025 (3)0.000 (3)
N510.023 (3)0.030 (4)0.030 (4)−0.001 (3)0.008 (3)0.003 (3)
N530.019 (3)0.027 (4)0.037 (4)0.005 (3)0.019 (3)0.000 (3)
C510.033 (5)0.037 (5)0.040 (5)0.003 (4)0.021 (4)0.009 (4)
C520.023 (4)0.057 (7)0.039 (5)0.004 (4)0.005 (4)0.004 (5)
C540.025 (4)0.018 (4)0.036 (5)0.002 (3)0.011 (3)0.000 (3)
C560.027 (4)0.020 (4)0.029 (4)0.007 (3)0.012 (3)0.001 (3)
C580.022 (4)0.020 (4)0.035 (4)0.000 (3)0.009 (3)−0.001 (3)
C5100.032 (4)0.019 (4)0.032 (4)0.003 (3)0.017 (3)−0.005 (3)
C5120.026 (4)0.013 (3)0.025 (3)0.005 (3)0.016 (3)−0.001 (3)
C5140.031 (4)0.020 (4)0.032 (4)0.004 (3)0.018 (3)0.001 (3)
C5150.026 (4)0.023 (4)0.055 (5)−0.001 (3)0.024 (4)−0.001 (4)
C5160.034 (4)0.033 (4)0.038 (4)0.006 (3)0.026 (4)0.012 (3)
O610.038 (4)0.039 (5)0.074 (6)0.013 (4)0.038 (4)−0.001 (4)
C610.031 (5)0.033 (6)0.065 (8)−0.008 (4)0.025 (5)−0.011 (5)
C620.031 (6)0.043 (7)0.080 (10)0.000 (5)0.024 (6)0.002 (7)
C670.034 (5)0.025 (5)0.059 (7)−0.014 (4)0.012 (5)0.001 (5)
C690.020 (4)0.021 (4)0.044 (6)−0.002 (3)0.013 (4)0.012 (4)
C6110.026 (4)0.015 (4)0.054 (6)0.011 (3)0.029 (5)0.016 (4)
C6150.022 (4)0.032 (5)0.043 (5)0.006 (3)0.021 (4)0.004 (4)
C6160.044 (6)0.047 (7)0.055 (7)0.000 (6)0.037 (6)−0.005 (6)

Geometric parameters (Å, °)

O11—N121.297 (7)C44—H440.9500
N11—C131.381 (8)C45—C461.418 (12)
N11—C121.414 (9)C45—H450.9500
N11—C111.456 (9)C46—C471.371 (11)
N12—N131.266 (8)C47—C481.359 (12)
N12—C161.475 (9)C47—H470.9500
N13—C191.409 (8)C48—H480.9500
N14—C1121.373 (8)C49—C4101.368 (12)
N14—C1151.422 (9)C49—C4141.402 (12)
N14—C1161.453 (9)C410—C4111.362 (13)
C11—H11A0.9800C410—H4100.9500
C11—H11B0.9800C411—C4121.420 (10)
C11—H11C0.9800C411—H4110.9500
C12—H12A0.9800C412—C4131.392 (10)
C12—H12B0.9800C413—C4141.398 (12)
C12—H12C0.9800C413—H4130.9500
C13—C181.402 (9)C414—H4140.9500
C13—C141.428 (9)C415—H45A0.9800
C14—C151.376 (10)C415—H45B0.9800
C14—H140.9500C415—H45C0.9800
C15—C161.354 (9)C416—H46A0.9800
C15—H150.9500C416—H46B0.9800
C16—C171.403 (9)C416—H46C0.9800
C17—C181.390 (9)O51—N521.321 (10)
C17—H170.9500N51—C531.361 (10)
C18—H180.9500N51—C511.422 (12)
C19—C1141.411 (9)N51—C521.439 (13)
C19—C1101.424 (9)N52—N531.287 (10)
C110—C1111.399 (8)N52—C561.429 (11)
C110—H1100.9500N53—C591.392 (10)
C111—C1121.429 (9)N54—C5121.303 (10)
C111—H1110.9500N54—C5151.454 (11)
C112—C1131.411 (9)N54—C5161.478 (10)
C113—C1141.369 (10)C51—H51A0.9800
C113—H1130.9500C51—H51B0.9800
C114—H1140.9500C51—H51C0.9800
C115—H15A0.9800C52—H52A0.9800
C115—H15B0.9800C52—H52B0.9800
C115—H15C0.9800C52—H52C0.9800
C116—H16A0.9800C53—C541.414 (12)
C116—H16B0.9800C53—C581.415 (11)
C116—H16C0.9800C54—C551.350 (12)
O21—N221.303 (8)C54—H540.9500
N21—C231.351 (10)C55—C561.375 (12)
N21—C221.414 (10)C55—H550.9500
N21—C211.447 (10)C56—C571.403 (13)
N22—N231.294 (9)C57—C581.402 (12)
N22—C261.450 (9)C57—H570.9500
N23—C291.436 (10)C58—H580.9500
N24—C2121.381 (9)C59—C5141.392 (12)
N24—C2151.423 (10)C59—C5101.421 (12)
N24—C2161.456 (9)C510—C5111.427 (12)
C21—H21A0.9800C510—H5100.9500
C21—H21B0.9800C511—C5121.403 (12)
C21—H21C0.9800C511—H5110.9500
C22—H22A0.9800C512—C5131.425 (11)
C22—H22B0.9800C513—C5141.367 (12)
C22—H22C0.9800C513—H5130.9500
C23—C241.419 (9)C514—H5140.9500
C23—C281.424 (10)C515—H55A0.9800
C24—C251.371 (10)C515—H55B0.9800
C24—H240.9500C515—H55C0.9800
C25—C261.364 (10)C516—H56A0.9800
C25—H250.9500C516—H56B0.9800
C26—C271.396 (9)C516—H56C0.9800
C27—C281.385 (10)O61—N621.270 (12)
C27—H270.9500N61—C631.282 (13)
C28—H280.9500N61—C621.538 (16)
C29—C2101.404 (10)N61—C611.558 (15)
C29—C2141.406 (10)N62—N631.259 (14)
C210—C2111.402 (11)N62—C661.413 (14)
C210—H2100.9500N63—C691.413 (14)
C211—C2121.423 (9)N64—C6121.325 (12)
C211—H2110.9500N64—C6161.449 (15)
C212—C2131.415 (9)N64—C6151.469 (13)
C214—C2131.381 (10)C61—H61A0.9800
C214—H2140.9500C61—H61B0.9800
C213—H2130.9500C61—H61C0.9800
C215—H25A0.9800C62—H62A0.9800
C215—H25B0.9800C62—H62B0.9800
C215—H25C0.9800C62—H62C0.9800
C216—H26A0.9800C63—C681.404 (15)
C216—H26B0.9800C63—C641.436 (16)
C216—H26C0.9800C64—C651.374 (14)
O31—N321.252 (8)C64—H640.9500
N31—C331.384 (12)C65—C661.369 (16)
N31—C311.444 (11)C65—H650.9500
N31—C321.482 (12)C66—C671.462 (18)
N32—N331.241 (10)C67—C681.344 (16)
N32—C361.476 (11)C67—H670.9500
N33—C391.501 (13)C68—H680.9500
N34—C3121.390 (12)C69—C6141.416 (14)
N34—C3161.448 (11)C69—C6101.417 (15)
N34—C3151.472 (9)C610—C6111.360 (15)
C31—H31A0.9800C610—H6100.9500
C31—H31B0.9800C611—C6121.432 (12)
C31—H31C0.9800C611—H6110.9500
C32—H32A0.9800C612—C6131.415 (13)
C32—H32B0.9800C613—C6141.367 (13)
C32—H32C0.9800C613—H6130.9500
C33—C341.383 (11)C614—H6140.9500
C33—C381.407 (11)C615—H65A0.9800
C34—C351.421 (13)C615—H65B0.9800
C34—H340.9500C615—H65C0.9800
C35—C361.397 (12)C616—H66A0.9800
C35—H350.9500C616—H66B0.9800
C36—C371.390 (13)C616—H66C0.9800
C37—C381.381 (12)O71—N721.31 (3)
C37—H370.9500N71—C711.48 (3)
C38—H380.9500N71—C721.51 (3)
C39—C3141.394 (12)N72—N731.34 (3)
C39—C3101.398 (12)N72—C761.43 (3)
C310—C3111.369 (12)N73—C791.38 (3)
C310—H3100.9500N74—C7121.44 (3)
C311—C3121.385 (10)N74—C7161.46 (3)
C311—H3110.9500N74—C7151.46 (3)
C312—C3131.393 (12)C74—C751.41 (3)
C313—C3141.389 (13)C75—C761.44 (3)
C313—H3130.9500C76—C771.34 (4)
C314—H3140.9500C77—C781.36 (4)
C315—H35A0.9800C79—C7141.43 (3)
C315—H35B0.9800C79—C7101.45 (4)
C315—H35C0.9800C710—C7111.25 (3)
C316—H36A0.9800C711—C7121.53 (3)
C316—H36B0.9800C712—C7131.38 (3)
C316—H36C0.9800C713—C7141.40 (3)
O41—N421.248 (8)O81—N821.35 (3)
N41—C431.384 (10)N81—C821.32 (3)
N41—C411.446 (10)N81—C811.51 (3)
N41—C421.469 (10)N81—C831.54 (4)
N42—N431.242 (10)N82—N831.20 (3)
N42—C461.502 (12)N82—C861.56 (4)
N43—C491.474 (12)N83—C891.45 (3)
N44—C4121.375 (10)N84—C8161.39 (3)
N44—C4161.442 (11)N84—C8151.40 (3)
N44—C4151.457 (10)C83—C881.31 (4)
C41—H41A0.9800C83—C841.42 (4)
C41—H41B0.9800C84—C851.55 (4)
C41—H41C0.9800C85—C861.24 (4)
C42—H42A0.9800C86—C871.40 (4)
C42—H42B0.9800C87—C881.42 (4)
C42—H42C0.9800C89—C8141.33 (4)
C43—C441.392 (10)C89—C8101.43 (4)
C43—C481.416 (10)C810—C8111.53 (4)
C44—C451.406 (13)C813—C8141.52 (4)
C13—N11—C12121.4 (6)C48—C47—H47119.1
C13—N11—C11120.0 (6)C46—C47—H47119.1
C12—N11—C11118.5 (6)C47—C48—C43120.2 (7)
N13—N12—O11128.2 (6)C47—C48—H48119.9
N13—N12—C16116.1 (5)C43—C48—H48119.9
O11—N12—C16115.7 (5)C410—C49—C414118.0 (8)
N12—N13—C19119.6 (5)C410—C49—N43133.9 (8)
C112—N14—C115121.8 (6)C414—C49—N43108.1 (7)
C112—N14—C116121.0 (6)C411—C410—C49123.2 (7)
C115—N14—C116117.0 (6)C411—C410—H410118.4
N11—C13—C18122.4 (6)C49—C410—H410118.4
N11—C13—C14119.5 (6)C410—C411—C412120.0 (7)
C18—C13—C14118.0 (6)C410—C411—H411120.0
C15—C14—C13119.3 (6)C412—C411—H411120.0
C15—C14—H14120.4N44—C412—C413121.7 (7)
C13—C14—H14120.4N44—C412—C411121.1 (7)
C16—C15—C14122.8 (7)C413—C412—C411117.0 (8)
C16—C15—H15118.6C412—C413—C414121.5 (7)
C14—C15—H15118.6C412—C413—H413119.2
C15—C16—C17119.1 (6)C414—C413—H413119.2
C15—C16—N12119.7 (6)C413—C414—C49119.8 (8)
C17—C16—N12121.2 (6)C413—C414—H414120.1
C18—C17—C16120.2 (6)C49—C414—H414120.1
C18—C17—H17119.9C53—N51—C51121.2 (8)
C16—C17—H17119.9C53—N51—C52120.2 (8)
C17—C18—C13120.6 (6)C51—N51—C52118.3 (8)
C17—C18—H18119.7N53—N52—O51123.4 (8)
C13—C18—H18119.7N53—N52—C56119.2 (8)
N13—C19—C114112.4 (6)O51—N52—C56117.4 (7)
N13—C19—C110129.9 (6)N52—N53—C59123.2 (7)
C114—C19—C110117.6 (6)C512—N54—C515124.0 (7)
C111—C110—C19121.0 (6)C512—N54—C516122.0 (7)
C111—C110—H110119.5C515—N54—C516114.0 (7)
C19—C110—H110119.5N51—C53—C54121.2 (8)
C110—C111—C112119.9 (6)N51—C53—C58121.6 (8)
C110—C111—H111120.0C54—C53—C58117.1 (8)
C112—C111—H111120.0C55—C54—C53121.9 (8)
N14—C112—C113121.6 (6)C55—C54—H54119.0
N14—C112—C111120.3 (6)C53—C54—H54119.0
C113—C112—C111118.0 (5)C54—C55—C56120.8 (9)
C114—C113—C112121.3 (6)C54—C55—H55119.6
C114—C113—H113119.4C56—C55—H55119.6
C112—C113—H113119.4C55—C56—C57120.3 (8)
C113—C114—C19121.7 (6)C55—C56—N52119.9 (8)
C113—C114—H114119.1C57—C56—N52119.6 (8)
C19—C114—H114119.1C58—C57—C56118.9 (8)
C23—N21—C22119.9 (6)C58—C57—H57120.6
C23—N21—C21120.8 (6)C56—C57—H57120.6
C22—N21—C21119.2 (7)C57—C58—C53120.7 (8)
N23—N22—O21124.9 (6)C57—C58—H58119.6
N23—N22—C26115.8 (6)C53—C58—H58119.6
O21—N22—C26119.2 (6)N53—C59—C514113.7 (8)
N22—N23—C29120.0 (6)N53—C59—C510126.8 (8)
C212—N24—C215122.1 (6)C514—C59—C510119.5 (8)
C212—N24—C216121.1 (6)C59—C510—C511117.5 (8)
C215—N24—C216116.5 (6)C59—C510—H510121.3
N21—C23—C24120.2 (6)C511—C510—H510121.3
N21—C23—C28121.9 (6)C512—C511—C510122.3 (8)
C24—C23—C28117.6 (7)C512—C511—H511118.8
C25—C24—C23120.3 (7)C510—C511—H511118.8
C25—C24—H24119.9N54—C512—C511121.4 (7)
C23—C24—H24119.9N54—C512—C513121.0 (8)
C26—C25—C24121.2 (7)C511—C512—C513117.5 (8)
C26—C25—H25119.4C514—C513—C512120.5 (8)
C24—C25—H25119.4C514—C513—H513119.7
C25—C26—C27120.8 (7)C512—C513—H513119.7
C25—C26—N22118.9 (6)C513—C514—C59122.4 (8)
C27—C26—N22120.4 (7)C513—C514—H514118.8
C28—C27—C26119.3 (7)C59—C514—H514118.8
C28—C27—H27120.3C63—N61—C62124.1 (10)
C26—C27—H27120.3C63—N61—C61123.8 (10)
C27—C28—C23120.6 (7)C62—N61—C61110.2 (10)
C27—C28—H28119.7N63—N62—O61124.9 (10)
C23—C28—H28119.7N63—N62—C66115.8 (10)
C210—C29—C214117.9 (7)O61—N62—C66119.3 (10)
C210—C29—N23129.7 (6)N62—N63—C69119.4 (10)
C214—C29—N23112.1 (6)C612—N64—C616119.9 (10)
C211—C210—C29121.5 (7)C612—N64—C615120.9 (9)
C211—C210—H210119.3C616—N64—C615119.2 (10)
C29—C210—H210119.3N61—C63—C68122.0 (10)
C210—C211—C212119.8 (7)N61—C63—C64120.1 (10)
C210—C211—H211120.1C68—C63—C64117.4 (10)
C212—C211—H211120.1C65—C64—C63121.5 (10)
N24—C212—C213121.2 (6)C65—C64—H64119.2
N24—C212—C211120.9 (6)C63—C64—H64119.2
C213—C212—C211117.7 (6)C66—C65—C64119.9 (11)
C213—C214—C29121.2 (7)C66—C65—H65120.0
C213—C214—H214119.4C64—C65—H65120.0
C29—C214—H214119.4C65—C66—N62117.2 (11)
C214—C213—C212121.3 (6)C65—C66—C67119.1 (11)
C214—C213—H213119.4N62—C66—C67123.6 (11)
C212—C213—H213119.4C68—C67—C66120.4 (12)
C33—N31—C31122.3 (8)C68—C67—H67119.8
C33—N31—C32120.5 (7)C66—C67—H67119.8
C31—N31—C32117.0 (9)C67—C68—C63121.0 (12)
N33—N32—O31129.3 (8)C67—C68—H68119.5
N33—N32—C36111.3 (8)C63—C68—H68119.5
O31—N32—C36119.3 (7)N63—C69—C614112.0 (10)
N32—N33—C39115.3 (7)N63—C69—C610132.9 (10)
C312—N34—C316120.3 (6)C614—C69—C610115.0 (10)
C312—N34—C315120.8 (7)C611—C610—C69120.5 (9)
C316—N34—C315118.6 (7)C611—C610—H610119.7
C34—C33—N31121.7 (8)C69—C610—H610119.7
C34—C33—C38118.2 (8)C610—C611—C612125.4 (9)
N31—C33—C38120.1 (8)C610—C611—H611117.3
C33—C34—C35122.9 (8)C612—C611—H611117.3
C33—C34—H34118.6N64—C612—C613123.2 (9)
C35—C34—H34118.6N64—C612—C611124.6 (9)
C36—C35—C34116.2 (8)C613—C612—C611112.1 (9)
C36—C35—H35121.9C614—C613—C612123.4 (9)
C34—C35—H35121.9C614—C613—H613118.3
C37—C36—C35122.1 (9)C612—C613—H613118.3
C37—C36—N32124.5 (8)C613—C614—C69122.8 (10)
C35—C36—N32113.4 (8)C613—C614—H614118.6
C38—C37—C36119.8 (8)C69—C614—H614118.6
C38—C37—H37120.1C71—N71—C72111.3 (18)
C36—C37—H37120.1O71—N72—N73123 (2)
C37—C38—C33120.7 (8)O71—N72—C76126 (2)
C37—C38—H38119.7N73—N72—C76111 (2)
C33—C38—H38119.7N72—N73—C79117 (2)
C314—C39—C310116.9 (8)C712—N74—C716119 (2)
C314—C39—N33109.7 (8)C712—N74—C715117 (2)
C310—C39—N33133.4 (8)C716—N74—C715124 (2)
C311—C310—C39120.5 (7)C74—C75—C76112 (2)
C311—C310—H310119.8C77—C76—N72131 (2)
C39—C310—H310119.8C77—C76—C75122 (2)
C310—C311—C312122.6 (8)N72—C76—C75106 (2)
C310—C311—H311118.7C76—C77—C78123 (3)
C312—C311—H311118.7N73—C79—C714109 (2)
C311—C312—N34122.4 (8)N73—C79—C710143 (2)
C311—C312—C313117.7 (9)C714—C79—C710108 (3)
N34—C312—C313119.8 (7)C711—C710—C79136 (3)
C314—C313—C312119.7 (8)C710—C711—C712111 (2)
C314—C313—H313120.1C713—C712—N74120 (2)
C312—C313—H313120.1C713—C712—C711120 (2)
C313—C314—C39122.3 (8)N74—C712—C711120 (2)
C313—C314—H314118.8C712—C713—C714120 (2)
C39—C314—H314118.8C713—C714—C79124 (2)
C43—N41—C41121.6 (7)C82—N81—C81124 (2)
C43—N41—C42121.2 (7)C82—N81—C83120 (2)
C41—N41—C42117.2 (7)C81—N81—C83116 (2)
N43—N42—O41130.8 (9)N83—N82—O81128 (2)
N43—N42—C46110.0 (7)N83—N82—C86121 (2)
O41—N42—C46119.2 (7)O81—N82—C86111.4 (18)
N42—N43—C49114.4 (7)N82—N83—C89123 (2)
C412—N44—C416120.2 (6)C816—N84—C815117 (2)
C412—N44—C415120.3 (6)C88—C83—C84132 (3)
C416—N44—C415119.3 (7)C88—C83—N81120 (2)
N41—C43—C44120.6 (7)C84—C83—N81108 (2)
N41—C43—C48121.0 (7)C83—C84—C85107 (2)
C44—C43—C48118.1 (8)C86—C85—C84122 (3)
C43—C44—C45122.0 (8)C85—C86—C87125 (3)
C43—C44—H44119.0C85—C86—N82119 (2)
C45—C44—H44119.0C87—C86—N82116 (2)
C44—C45—C46117.1 (7)C86—C87—C88119 (2)
C44—C45—H45121.4C83—C88—C87115 (3)
C46—C45—H45121.4C814—C89—C810124 (3)
C47—C46—C45120.4 (8)C814—C89—N83111 (2)
C47—C46—N42125.9 (8)C810—C89—N83124 (2)
C45—C46—N42113.6 (7)C89—C810—C811117 (2)
C48—C47—C46121.7 (8)C89—C814—C813119 (2)
O11—N12—N13—C19−1.1 (10)C415—N44—C412—C4132.4 (11)
C16—N12—N13—C19177.3 (5)C416—N44—C412—C411−8.4 (11)
C12—N11—C13—C18−174.1 (7)C415—N44—C412—C411177.0 (7)
C11—N11—C13—C184.6 (10)C410—C411—C412—N44177.5 (7)
C12—N11—C13—C143.5 (10)C410—C411—C412—C413−7.6 (10)
C11—N11—C13—C14−177.8 (6)N44—C412—C413—C414−177.8 (7)
N11—C13—C14—C15−178.4 (6)C411—C412—C413—C4147.3 (10)
C18—C13—C14—C15−0.8 (10)C412—C413—C414—C49−5.3 (11)
C13—C14—C15—C161.3 (11)C410—C49—C414—C4133.2 (11)
C14—C15—C16—C17−0.9 (10)N43—C49—C414—C413179.8 (7)
C14—C15—C16—N12177.2 (6)O51—N52—N53—C591.0 (13)
N13—N12—C16—C15−177.2 (6)C56—N52—N53—C59179.6 (8)
O11—N12—C16—C151.5 (9)C51—N51—C53—C54−177.5 (9)
N13—N12—C16—C170.9 (9)C52—N51—C53—C548.0 (13)
O11—N12—C16—C17179.5 (6)C51—N51—C53—C58−0.2 (14)
C15—C16—C17—C18−0.2 (10)C52—N51—C53—C58−174.6 (9)
N12—C16—C17—C18−178.2 (6)N51—C53—C54—C55−178.6 (9)
C16—C17—C18—C130.7 (10)C58—C53—C54—C554.0 (13)
N11—C13—C18—C17177.4 (6)C53—C54—C55—C56−4.8 (14)
C14—C13—C18—C17−0.2 (10)C54—C55—C56—C574.9 (14)
N12—N13—C19—C114−179.4 (6)C54—C55—C56—N52179.5 (8)
N12—N13—C19—C1105.2 (11)N53—N52—C56—C55−175.2 (8)
N13—C19—C110—C111178.7 (7)O51—N52—C56—C553.5 (12)
C114—C19—C110—C1113.6 (10)N53—N52—C56—C57−0.6 (12)
C19—C110—C111—C112−5.4 (10)O51—N52—C56—C57178.1 (8)
C115—N14—C112—C1131.1 (10)C55—C56—C57—C58−4.2 (13)
C116—N14—C112—C113178.0 (7)N52—C56—C57—C58−178.9 (8)
C115—N14—C112—C111−175.7 (6)C56—C57—C58—C533.6 (14)
C116—N14—C112—C1111.3 (10)N51—C53—C58—C57179.2 (9)
C110—C111—C112—N14−175.9 (6)C54—C53—C58—C57−3.4 (13)
C110—C111—C112—C1137.2 (10)N52—N53—C59—C514−176.3 (8)
N14—C112—C113—C114175.6 (7)N52—N53—C59—C5101.1 (14)
C111—C112—C113—C114−7.6 (10)N53—C59—C510—C511177.3 (9)
C112—C113—C114—C196.1 (11)C514—C59—C510—C511−5.5 (13)
N13—C19—C114—C113−179.9 (6)C59—C510—C511—C5125.4 (13)
C110—C19—C114—C113−3.9 (10)C515—N54—C512—C511179.2 (8)
O21—N22—N23—C29−0.5 (10)C516—N54—C512—C511−2.6 (12)
C26—N22—N23—C29176.7 (6)C515—N54—C512—C5133.6 (13)
C22—N21—C23—C244.5 (10)C516—N54—C512—C513−178.2 (8)
C21—N21—C23—C24−178.9 (7)C510—C511—C512—N54−179.6 (8)
C22—N21—C23—C28−170.0 (7)C510—C511—C512—C513−3.9 (12)
C21—N21—C23—C286.6 (11)N54—C512—C513—C514178.4 (8)
N21—C23—C24—C25−179.0 (7)C511—C512—C513—C5142.7 (13)
C28—C23—C24—C25−4.3 (10)C512—C513—C514—C59−3.1 (14)
C23—C24—C25—C263.5 (11)N53—C59—C514—C513−177.9 (8)
C24—C25—C26—C27−2.1 (11)C510—C59—C514—C5134.6 (14)
C24—C25—C26—N22177.7 (7)O61—N62—N63—C69−1.0 (17)
N23—N22—C26—C25−179.2 (6)C66—N62—N63—C69178.5 (10)
O21—N22—C26—C25−1.8 (10)C62—N61—C63—C68168.2 (11)
N23—N22—C26—C270.6 (9)C61—N61—C63—C685.5 (17)
O21—N22—C26—C27178.0 (6)C62—N61—C63—C64−20.2 (17)
C25—C26—C27—C281.6 (10)C61—N61—C63—C64177.1 (10)
N22—C26—C27—C28−178.2 (6)N61—C63—C64—C65179.1 (11)
C26—C27—C28—C23−2.6 (11)C68—C63—C64—C65−8.9 (17)
N21—C23—C28—C27178.5 (7)C63—C64—C65—C664.8 (17)
C24—C23—C28—C273.9 (10)C64—C65—C66—N62−178.5 (10)
N22—N23—C29—C2106.6 (11)C64—C65—C66—C67−1.0 (17)
N22—N23—C29—C214−179.2 (6)N63—N62—C66—C65179.1 (11)
C214—C29—C210—C2115.9 (10)O61—N62—C66—C65−1.3 (16)
N23—C29—C210—C211179.8 (7)N63—N62—C66—C671.7 (16)
C29—C210—C211—C212−7.1 (11)O61—N62—C66—C67−178.7 (10)
C215—N24—C212—C213−3.8 (11)C65—C66—C67—C681.6 (17)
C216—N24—C212—C213−177.9 (7)N62—C66—C67—C68178.9 (11)
C215—N24—C212—C211−178.0 (7)C66—C67—C68—C63−6.0 (17)
C216—N24—C212—C2117.9 (11)N61—C63—C68—C67−178.8 (11)
C210—C211—C212—N24−178.3 (7)C64—C63—C68—C679.4 (17)
C210—C211—C212—C2137.3 (10)N62—N63—C69—C614178.5 (10)
C210—C29—C214—C213−5.2 (10)N62—N63—C69—C6103.2 (18)
N23—C29—C214—C213179.8 (6)N63—C69—C610—C611−176.3 (11)
C29—C214—C213—C2125.9 (11)C614—C69—C610—C6118.5 (14)
N24—C212—C213—C214178.8 (7)C69—C610—C611—C612−8.9 (15)
C211—C212—C213—C214−6.8 (11)C616—N64—C612—C613174.2 (10)
O31—N32—N33—C39−2.0 (13)C615—N64—C612—C613−3.2 (15)
C36—N32—N33—C39−179.2 (6)C616—N64—C612—C611−1.2 (16)
C31—N31—C33—C34177.4 (8)C615—N64—C612—C611−178.5 (9)
C32—N31—C33—C34−6.9 (13)C610—C611—C612—N64−178.1 (10)
C31—N31—C33—C38−1.7 (13)C610—C611—C612—C6136.0 (14)
C32—N31—C33—C38174.0 (8)N64—C612—C613—C614−179.7 (10)
N31—C33—C34—C35178.2 (8)C611—C612—C613—C614−3.8 (14)
C38—C33—C34—C35−2.6 (12)C612—C613—C614—C694.7 (16)
C33—C34—C35—C36−0.6 (12)N63—C69—C614—C613177.1 (10)
C34—C35—C36—C373.1 (12)C610—C69—C614—C613−6.7 (14)
C34—C35—C36—N32−177.2 (7)O71—N72—N73—C79−1(3)
N33—N32—C36—C37−4.0 (12)C76—N72—N73—C79−179 (2)
O31—N32—C36—C37178.5 (8)O71—N72—C76—C77176 (2)
N33—N32—C36—C35176.4 (7)N73—N72—C76—C77−6(4)
O31—N32—C36—C35−1.1 (11)O71—N72—C76—C75−2(3)
C35—C36—C37—C38−2.3 (12)N73—N72—C76—C75175.9 (19)
N32—C36—C37—C38178.1 (7)C74—C75—C76—C773(3)
C36—C37—C38—C33−1.2 (12)C74—C75—C76—N72−179 (2)
C34—C33—C38—C373.6 (12)N72—C76—C77—C78179 (2)
N31—C33—C38—C37−177.3 (8)C75—C76—C77—C78−4(4)
N32—N33—C39—C314179.7 (7)N72—N73—C79—C714180 (2)
N32—N33—C39—C3101.9 (13)N72—N73—C79—C7101(5)
C314—C39—C310—C3115.4 (11)N73—C79—C710—C711179 (3)
N33—C39—C310—C311−177.0 (8)C714—C79—C710—C7111(4)
C39—C310—C311—C312−3.4 (11)C79—C710—C711—C7124(4)
C310—C311—C312—N34176.6 (7)C716—N74—C712—C713175 (2)
C310—C311—C312—C3130.6 (11)C715—N74—C712—C7130(3)
C316—N34—C312—C3113.1 (12)C716—N74—C712—C711−8(3)
C315—N34—C312—C311177.6 (7)C715—N74—C712—C711177 (2)
C316—N34—C312—C313179.1 (8)C710—C711—C712—C713−7(3)
C315—N34—C312—C313−6.4 (11)C710—C711—C712—N74176 (2)
C311—C312—C313—C3140.0 (11)N74—C712—C713—C714−176 (2)
N34—C312—C313—C314−176.1 (7)C711—C712—C713—C7147(4)
C312—C313—C314—C392.3 (12)C712—C713—C714—C79−2(4)
C310—C39—C314—C313−4.9 (12)N73—C79—C714—C713179 (2)
N33—C39—C314—C313176.9 (7)C710—C79—C714—C713−2(3)
O41—N42—N43—C49−0.1 (12)O81—N82—N83—C89−3(4)
C46—N42—N43—C49−177.8 (6)C86—N82—N83—C89176 (2)
C41—N41—C43—C44179.8 (7)C82—N81—C83—C88−173 (3)
C42—N41—C43—C44−2.8 (12)C81—N81—C83—C882(3)
C41—N41—C43—C48−5.8 (12)C82—N81—C83—C846(3)
C42—N41—C43—C48171.7 (7)C81—N81—C83—C84−178 (2)
N41—C43—C44—C45179.0 (7)C88—C83—C84—C850(4)
C48—C43—C44—C454.4 (11)N81—C83—C84—C85−179.3 (19)
C43—C44—C45—C46−6.2 (12)C83—C84—C85—C860(4)
C44—C45—C46—C476.5 (12)C84—C85—C86—C871(4)
C44—C45—C46—N42−175.4 (7)C84—C85—C86—N82177 (2)
N43—N42—C46—C47−3.4 (11)N83—N82—C86—C85−179 (3)
O41—N42—C46—C47178.6 (7)O81—N82—C86—C850(3)
N43—N42—C46—C45178.7 (7)N83—N82—C86—C87−2(3)
O41—N42—C46—C450.7 (10)O81—N82—C86—C87177 (2)
C45—C46—C47—C48−5.3 (12)C85—C86—C87—C88−2(4)
N42—C46—C47—C48176.9 (7)N82—C86—C87—C88−179 (2)
C46—C47—C48—C433.3 (12)C84—C83—C88—C87−2(4)
N41—C43—C48—C47−177.3 (7)N81—C83—C88—C87178 (2)
C44—C43—C48—C47−2.8 (11)C86—C87—C88—C833(4)
N42—N43—C49—C410−4.1 (13)N82—N83—C89—C814−179 (3)
N42—N43—C49—C414−180.0 (7)N82—N83—C89—C8108(4)
C414—C49—C410—C411−3.6 (12)C814—C89—C810—C8117(4)
N43—C49—C410—C411−179.2 (8)N83—C89—C810—C811179 (2)
C49—C410—C411—C4126.0 (11)C810—C89—C814—C813−11 (4)
C416—N44—C412—C413176.9 (7)N83—C89—C814—C813176 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C15—H15···O110.952.352.708 (8)101
C25—H25···O210.952.412.745 (8)101
C35—H35···O310.952.322.651 (12)100
C45—H45···O410.952.362.687 (12)100
C55—H55···O510.952.382.722 (12)100
C65—H65···O610.952.332.663 (16)100
C110—H110···O110.952.152.742 (8)119
C114—H114···O61i0.952.513.328 (12)144
C210—H210···O210.952.132.727 (10)120
C214—H214···O31ii0.952.503.402 (10)158
C310—H310···O310.952.212.750 (12)115
C410—H410···O410.952.172.732 (11)117
C414—H414···O510.952.573.448 (12)153
C510—H510···O510.952.092.684 (11)120
C514—H514···O41i0.952.483.323 (11)148
C610—H610···O610.952.202.726 (16)115
C614—H614···O110.952.583.471 (12)156

Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2473).

References

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