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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o140.
Published online 2007 December 6. doi:  10.1107/S1600536807063295
PMCID: PMC2915209

13b,13c-Di-2-pyridyl-5,7,12,13b,13c,14-hexa­hydro-6H,13H-5a,6a,12a,13a-tetra­azabenz[5,6]azuleno[2,1,8-ija]benz[f]azulene-6,13-dione methanol hemisolvate

Abstract

The title compound, C30H24N6O2·0.5CH3OH, a glycoluril derivative with two pyridine substituents on the convex face of the glycoluril system, is an important inter­mediate for the synthesis of more complex glycoluril derivatives. The compound crystallizes with two independent mol­ecules in the asymmetric unit, one of which exhibits disorder of one benzene ring over two orientations with refined site occupancy factors 0.65 (4):0.35 (4). The crystal structure contains several short C—H(...)O contacts, and the methanol mol­ecule forms an O—H(...)O hydrogen bond to one of the glycoluril mol­ecules.

Related literature

For synthetic details, see: Wang et al. (2006 [triangle]). For general related literature, see: Adrian & Wilcox (1989 [triangle]); Behrend et al. (1905 [triangle]); Freeman et al. (1981 [triangle]); Rowan et al. (1999 [triangle]); Rebek (2005 [triangle]); Sanderson et al. (1989 [triangle]); Wu et al. (2002 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o140-scheme1.jpg

Experimental

Crystal data

  • C30H24N6O2·0.5CH4O
  • M r = 516.57
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o140-efi1.jpg
  • a = 15.0063 (10) Å
  • b = 20.5919 (13) Å
  • c = 18.0864 (12) Å
  • β = 113.405 (1)°
  • V = 5129.0 (6) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 292 (2) K
  • 0.30 × 0.30 × 0.20 mm

Data collection

  • Bruker SMART 4K CCD diffractometer
  • Absorption correction: none
  • 68334 measured reflections
  • 8988 independent reflections
  • 7325 reflections with I > 2σ(I)
  • R int = 0.037

Refinement

  • R[F 2 > 2σ(F 2)] = 0.074
  • wR(F 2) = 0.208
  • S = 1.08
  • 8988 reflections
  • 734 parameters
  • H-atom parameters constrained
  • Δρmax = 0.68 e Å−3
  • Δρmin = −0.56 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2001 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807063295/bi2258sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063295/bi2258Isup2.hkl

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

Acknowledgments

The authors are grateful to Central China Normal University.

supplementary crystallographic information

Comment

In 1905, Behrend synthesized an insoluble polymeric material now known as Behrend's polymer using an acid-induced condensation reaction of glycoluril and formaldehyde (Behrend et al., 1905). The molecular structure was characterized and named as cucurbituril by Mock and co-workers in 1981 (Freeman et al., 1981). Glycoluril and its derivatives have been widely used as building blocks for supramolecular chemistry, for example in the formation of molecular clefts, armatures, bowls, tweezers and clips (Adrian & Wilcox, 1989; Freeman et al., 1981; Rebek, 2005; Sanderson et al., 1989; Rowan et al., 1999; Wu et al., 2002). As a part of our ongoing investigation into glycoluril derivatives, we report the crystal structure of the title compound.

The clip-shaped molecular structure is shown in Fig. 1. It has six fused rings and two pyridine rings. The crystal structure contains several short C—H···O contacts, and the methanol molecule forms an O—H···O hydrogen bond to one of the glycoluril molecules.

Experimental

The compound was synthesized according to a literature procedure (Wang et al., 2006) in 31% isolated yield. Crystals suitable for X-ray analysis were obtained by slow evaporation of a chloroform and methanol solution (20:1 v/v) at 293 K.

Refinement

One phenyl ring of one molecule is disordered. It was modelled in two orientations, constrained to be regular hexagons, with refined site occupancy factors 0.35 (4):0.65 (4). H atoms bound to C were positioned geometrically and constrained to ride on their parent atoms, with d(C—H) = 0.93–0.97 Å and with Uiso(H) = 1.2 or 1.5Ueq(C). The H atom of the methanol molecule was placed along the O5···O2 vector with d(O5—H5) = 0.82 Å and refined as riding on O5 with Uiso(H) = 1.5Ueq(O).

Figures

Fig. 1.
The structure of the non-disordered molecule in the asymmetric unit, with displacement ellipsoids drawn at the 50% proability level for non-H atoms.

Crystal data

C30H24N6O2·0.5CH4OF000 = 2168
Mr = 516.57Dx = 1.338 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9377 reflections
a = 15.0063 (10) Åθ = 2.3–24.5º
b = 20.5919 (13) ŵ = 0.09 mm1
c = 18.0864 (12) ÅT = 292 (2) K
β = 113.405 (1)ºBlock, colourless
V = 5129.0 (6) Å30.30 × 0.30 × 0.20 mm
Z = 8

Data collection

Bruker SMART 4K CCD diffractometer7325 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.037
Monochromator: graphiteθmax = 25.0º
T = 292(2) Kθmin = 1.5º
[var phi] and ω scansh = −17→17
Absorption correction: nonek = −24→24
68334 measured reflectionsl = −21→21
8988 independent 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)] = 0.074H-atom parameters constrained
wR(F2) = 0.208  w = 1/[σ2(Fo2) + (0.0999P)2 + 4.5477P] where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
8988 reflectionsΔρmax = 0.68 e Å3
734 parametersΔρmin = −0.56 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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)
O10.35883 (16)0.31312 (11)0.35693 (14)0.0567 (6)
O20.07810 (17)0.35765 (11)0.48148 (13)0.0545 (6)
O30.39873 (17)0.60364 (10)−0.02765 (13)0.0543 (6)
O40.19640 (17)0.56407 (12)0.16797 (17)0.0685 (7)
N10.20302 (17)0.35391 (11)0.29519 (14)0.0407 (5)
N20.09710 (19)0.37701 (11)0.36331 (14)0.0445 (6)
N30.22538 (17)0.25952 (11)0.35859 (14)0.0392 (5)
N40.09295 (18)0.27518 (11)0.40090 (14)0.0425 (6)
N50.0373 (2)0.35266 (15)0.14809 (18)0.0683 (8)
N60.0988 (2)0.20264 (13)0.21698 (16)0.0559 (7)
N70.41144 (16)0.52050 (10)0.06155 (13)0.0367 (5)
N80.30693 (16)0.50807 (11)0.13356 (14)0.0386 (5)
N90.42379 (18)0.62206 (11)0.10440 (14)0.0428 (6)
N100.35400 (18)0.60006 (12)0.20074 (15)0.0469 (6)
N110.45044 (18)0.43855 (11)0.24979 (14)0.0436 (6)
N120.6039 (2)0.60347 (15)0.22005 (18)0.0622 (8)
C10.1993 (2)0.47681 (13)0.39507 (18)0.0459 (7)
C20.2288 (3)0.51885 (16)0.4606 (2)0.0591 (9)
H2A0.18780.52730.48680.071*
C30.3195 (3)0.54821 (18)0.4871 (2)0.0719 (11)
H3A0.33860.57670.53050.086*
C40.3810 (3)0.53545 (19)0.4495 (3)0.0751 (11)
H4A0.44140.55550.46680.090*
C50.3524 (3)0.49261 (17)0.3858 (2)0.0619 (9)
H5A0.39470.48330.36110.074*
C60.2621 (2)0.46312 (14)0.35764 (18)0.0467 (7)
C70.2320 (2)0.41998 (14)0.28440 (18)0.0456 (7)
H7A0.17810.44050.24110.055*
H7B0.28560.41720.26740.055*
C80.0980 (2)0.44777 (14)0.36560 (19)0.0490 (7)
H8A0.06700.46220.40060.059*
H8B0.06010.46410.31190.059*
C90.2722 (2)0.30936 (14)0.34003 (16)0.0402 (6)
C100.0892 (2)0.33885 (14)0.42135 (17)0.0416 (6)
C110.1102 (2)0.34124 (13)0.29936 (16)0.0388 (6)
C120.0234 (2)0.35063 (13)0.21877 (18)0.0439 (7)
C13−0.0634 (2)0.35483 (15)0.2217 (2)0.0498 (7)
H13A−0.07010.35380.27060.060*
C14−0.1411 (3)0.3606 (2)0.1518 (3)0.0805 (12)
H14A−0.20220.36320.15330.097*
C15−0.1345 (3)0.36297 (19)0.0794 (3)0.0781 (13)
H15A−0.19000.36700.03210.094*
C16−0.0452 (3)0.35929 (18)0.0773 (2)0.0694 (11)
H16A−0.03920.36120.02810.083*
C170.1225 (2)0.26936 (13)0.33361 (16)0.0382 (6)
C180.0639 (2)0.21802 (13)0.27268 (17)0.0431 (7)
C19−0.0185 (2)0.19128 (17)0.2750 (2)0.0594 (9)
H19A−0.04090.20330.31410.071*
C20−0.0675 (3)0.1451 (2)0.2162 (3)0.0824 (13)
H20A−0.12340.12530.21560.099*
C21−0.0318 (3)0.12943 (19)0.1588 (3)0.0781 (13)
H21A−0.06310.09870.11930.094*
C220.0484 (3)0.15912 (17)0.1608 (2)0.0681 (10)
H22A0.07050.14900.12090.082*
C230.1178 (2)0.22462 (15)0.46324 (19)0.0509 (8)
H23A0.10130.18270.43680.061*
H23B0.07770.23080.49350.061*
C240.2763 (2)0.20382 (14)0.40696 (18)0.0458 (7)
H24A0.33690.19750.40060.055*
H24B0.23700.16520.38700.055*
C250.2223 (2)0.22286 (14)0.52156 (18)0.0484 (7)
C260.2459 (3)0.22988 (16)0.6038 (2)0.0607 (9)
H26A0.19680.23730.62190.073*
C270.3410 (3)0.22604 (18)0.6590 (2)0.0715 (11)
H27A0.35550.23040.71370.086*
C280.4138 (3)0.21574 (18)0.6329 (2)0.0690 (11)
H28A0.47790.21330.67000.083*
C290.3925 (3)0.20886 (16)0.5515 (2)0.0583 (9)
H29A0.44260.20220.53440.070*
C300.2977 (2)0.21183 (13)0.49543 (18)0.0457 (7)
C310.2024 (2)0.46144 (13)0.00128 (17)0.0417 (7)
C320.1017 (2)0.46010 (15)−0.0412 (2)0.0533 (8)
H32A0.06160.4563−0.01330.064*
C330.0610 (3)0.46441 (16)−0.1245 (2)0.0631 (10)
H33A−0.00600.4626−0.15220.076*
C340.1189 (3)0.47125 (17)−0.1659 (2)0.0621 (9)
H34A0.09140.4740−0.22180.075*
C350.2192 (3)0.47408 (14)−0.12473 (18)0.0519 (8)
H35A0.25820.4795−0.15340.062*
C360.2618 (2)0.46896 (13)−0.04157 (17)0.0419 (7)
C370.3715 (2)0.46951 (13)0.00118 (17)0.0406 (6)
H37A0.39230.42780.02720.049*
H37B0.39890.4742−0.03890.049*
C380.2450 (2)0.45412 (14)0.09123 (17)0.0436 (7)
H38A0.19250.45000.10940.052*
H38B0.28260.41430.10530.052*
C390.4092 (2)0.58470 (13)0.03871 (17)0.0387 (6)
C400.2763 (2)0.55784 (14)0.16627 (18)0.0446 (7)
C410.40525 (19)0.51493 (13)0.13935 (16)0.0356 (6)
C420.47331 (19)0.46232 (12)0.19148 (16)0.0352 (6)
C430.5554 (2)0.44407 (15)0.18015 (18)0.0480 (7)
H43A0.56800.46070.13750.058*
C440.6183 (2)0.40048 (17)0.2335 (2)0.0569 (8)
H44A0.67470.38770.22780.068*
C450.5969 (2)0.37631 (15)0.29470 (19)0.0534 (8)
H45A0.63860.34730.33180.064*
C460.5128 (2)0.39569 (15)0.30031 (18)0.0506 (8)
H46A0.49780.37830.34140.061*
C470.43119 (19)0.58581 (12)0.17507 (16)0.0368 (6)
C480.5309 (2)0.59353 (13)0.24317 (18)0.0432 (7)
C490.5433 (3)0.58788 (17)0.3217 (2)0.0641 (10)
H49A0.49070.58010.33540.077*
C500.6374 (4)0.5941 (2)0.3814 (2)0.0857 (14)
H50A0.64850.59090.43570.103*
C510.7112 (3)0.6047 (2)0.3587 (3)0.0900 (15)
H51A0.77420.60930.39720.108*
C520.6927 (3)0.6086 (2)0.2786 (3)0.0837 (13)
H52A0.74480.61530.26400.100*
C530.3372 (3)0.66679 (18)0.2196 (3)0.0716 (11)
H53A0.30090.66350.25350.086*
H53B0.40050.68390.25360.086*
C540.4285 (3)0.69218 (14)0.1041 (2)0.0551 (8)
H54A0.43630.70710.05610.066*
H54B0.48360.70730.15090.066*
C550.2959 (10)0.7108 (7)0.1688 (15)0.044 (4)0.35 (4)
C560.2138 (12)0.7415 (6)0.170 (2)0.080 (6)0.35 (4)
H56A0.19450.73410.21170.096*0.35 (4)
C570.1606 (8)0.7833 (6)0.107 (3)0.093 (8)0.35 (4)
H57A0.10560.80380.10780.111*0.35 (4)
C580.1894 (11)0.7943 (7)0.0442 (19)0.081 (9)0.35 (4)
H58A0.15380.82230.00250.098*0.35 (4)
C590.2715 (16)0.7636 (8)0.0434 (12)0.063 (6)0.35 (4)
H59A0.29080.77100.00120.075*0.35 (4)
C600.3248 (12)0.7219 (9)0.1057 (11)0.049 (5)0.35 (4)
C55'0.2892 (6)0.7118 (4)0.1367 (10)0.055 (3)0.65 (4)
C56'0.2005 (6)0.7420 (4)0.1204 (15)0.087 (5)0.65 (4)
H56B0.16680.73390.15280.104*0.65 (4)
C57'0.1622 (5)0.7843 (4)0.0555 (15)0.102 (7)0.65 (4)
H57B0.10290.80450.04450.122*0.65 (4)
C58'0.2126 (11)0.7965 (4)0.0070 (11)0.104 (5)0.65 (4)
H58B0.18700.8248−0.03650.125*0.65 (4)
C59'0.3013 (11)0.7663 (5)0.0233 (8)0.084 (3)0.65 (4)
H59B0.33500.7745−0.00920.100*0.65 (4)
C60'0.3396 (6)0.7240 (5)0.0882 (7)0.052 (2)0.65 (4)
O5−0.0697 (6)0.4504 (5)0.4616 (6)0.258 (4)
H5−0.02620.42410.46820.387*
C61−0.1370 (6)0.4555 (6)0.3734 (6)0.212 (5)
H61A−0.20310.45170.36790.318*
H61B−0.12270.42130.34380.318*
H61C−0.12790.49680.35270.318*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0433 (13)0.0615 (14)0.0635 (14)−0.0031 (10)0.0194 (11)0.0080 (11)
O20.0630 (14)0.0619 (14)0.0436 (12)0.0062 (11)0.0264 (11)−0.0034 (10)
O30.0763 (15)0.0461 (12)0.0429 (12)0.0023 (10)0.0260 (11)0.0108 (10)
O40.0515 (14)0.0611 (15)0.105 (2)−0.0080 (11)0.0435 (14)−0.0164 (14)
N10.0454 (13)0.0360 (12)0.0385 (13)−0.0021 (10)0.0144 (11)0.0030 (10)
N20.0605 (16)0.0339 (12)0.0416 (13)0.0004 (11)0.0230 (12)−0.0023 (10)
N30.0423 (13)0.0357 (12)0.0378 (12)0.0014 (10)0.0140 (10)0.0041 (10)
N40.0514 (14)0.0398 (13)0.0399 (13)0.0016 (11)0.0218 (11)0.0047 (10)
N50.087 (2)0.0580 (18)0.0514 (17)0.0009 (15)0.0179 (16)0.0024 (14)
N60.0739 (19)0.0483 (15)0.0435 (15)0.0020 (13)0.0210 (14)−0.0044 (12)
N70.0405 (12)0.0330 (11)0.0322 (12)0.0002 (9)0.0097 (10)0.0026 (9)
N80.0357 (12)0.0348 (12)0.0433 (13)−0.0040 (9)0.0135 (10)−0.0010 (10)
N90.0537 (14)0.0300 (12)0.0423 (13)−0.0022 (10)0.0164 (11)0.0037 (10)
N100.0496 (14)0.0411 (13)0.0553 (15)−0.0076 (11)0.0264 (12)−0.0116 (11)
N110.0489 (14)0.0401 (13)0.0392 (13)−0.0025 (11)0.0146 (11)0.0071 (11)
N120.0423 (15)0.0643 (18)0.0726 (19)−0.0092 (13)0.0149 (14)−0.0130 (15)
C10.0575 (18)0.0294 (14)0.0404 (16)0.0046 (12)0.0085 (14)0.0043 (12)
C20.073 (2)0.0465 (18)0.0454 (18)0.0114 (16)0.0101 (16)−0.0056 (14)
C30.075 (3)0.057 (2)0.058 (2)−0.0013 (19)−0.001 (2)−0.0200 (17)
C40.065 (2)0.063 (2)0.083 (3)−0.0108 (19)0.013 (2)−0.018 (2)
C50.059 (2)0.0515 (19)0.072 (2)−0.0100 (16)0.0225 (18)−0.0065 (17)
C60.0570 (18)0.0340 (15)0.0443 (16)−0.0008 (13)0.0152 (14)0.0050 (12)
C70.0538 (17)0.0419 (15)0.0413 (16)−0.0046 (13)0.0191 (14)0.0066 (13)
C80.0604 (19)0.0369 (15)0.0481 (17)0.0089 (13)0.0196 (15)−0.0010 (13)
C90.0455 (17)0.0406 (15)0.0349 (15)−0.0006 (12)0.0163 (13)−0.0001 (12)
C100.0410 (15)0.0448 (16)0.0371 (15)0.0021 (12)0.0135 (12)−0.0022 (13)
C110.0452 (15)0.0348 (14)0.0353 (14)−0.0004 (12)0.0147 (12)−0.0011 (11)
C120.0532 (18)0.0300 (14)0.0423 (16)0.0023 (12)0.0125 (14)0.0001 (12)
C130.0404 (17)0.0543 (18)0.0531 (18)0.0045 (13)0.0171 (15)−0.0012 (14)
C140.050 (2)0.066 (2)0.111 (4)0.0054 (18)0.018 (2)−0.006 (2)
C150.069 (3)0.055 (2)0.071 (3)0.0021 (18)−0.013 (2)−0.0084 (19)
C160.097 (3)0.057 (2)0.0376 (18)0.001 (2)0.0095 (19)−0.0014 (15)
C170.0431 (15)0.0342 (14)0.0366 (14)−0.0007 (11)0.0153 (12)0.0014 (11)
C180.0454 (16)0.0349 (14)0.0417 (16)0.0003 (12)0.0095 (13)0.0045 (12)
C190.0473 (18)0.059 (2)0.068 (2)−0.0096 (15)0.0185 (16)0.0004 (17)
C200.052 (2)0.065 (2)0.104 (3)−0.0199 (18)0.004 (2)0.013 (2)
C210.088 (3)0.049 (2)0.061 (2)−0.003 (2)−0.009 (2)−0.0051 (18)
C220.097 (3)0.0494 (19)0.0464 (19)0.006 (2)0.0160 (19)−0.0099 (16)
C230.065 (2)0.0446 (17)0.0488 (18)0.0008 (14)0.0285 (16)0.0108 (14)
C240.0520 (17)0.0369 (15)0.0465 (17)0.0068 (13)0.0175 (14)0.0041 (13)
C250.068 (2)0.0330 (14)0.0429 (17)0.0021 (14)0.0203 (15)0.0084 (12)
C260.094 (3)0.0449 (18)0.0457 (19)0.0077 (17)0.0307 (19)0.0088 (14)
C270.109 (3)0.053 (2)0.0367 (18)0.009 (2)0.013 (2)0.0074 (15)
C280.079 (3)0.054 (2)0.049 (2)0.0058 (18)−0.0007 (19)0.0093 (16)
C290.060 (2)0.0464 (18)0.057 (2)0.0100 (15)0.0111 (17)0.0105 (15)
C300.0580 (19)0.0316 (14)0.0410 (16)0.0053 (13)0.0128 (14)0.0059 (12)
C310.0425 (15)0.0289 (13)0.0448 (16)−0.0042 (11)0.0081 (13)−0.0024 (12)
C320.0455 (17)0.0415 (16)0.063 (2)−0.0067 (13)0.0107 (15)−0.0044 (14)
C330.0502 (19)0.0500 (19)0.062 (2)0.0000 (15)−0.0062 (17)−0.0052 (16)
C340.066 (2)0.056 (2)0.0421 (18)0.0001 (17)−0.0025 (17)−0.0024 (15)
C350.065 (2)0.0390 (16)0.0425 (17)−0.0024 (14)0.0113 (15)−0.0031 (13)
C360.0479 (16)0.0279 (13)0.0406 (16)−0.0001 (11)0.0078 (13)−0.0012 (11)
C370.0467 (16)0.0342 (14)0.0390 (15)0.0028 (12)0.0148 (13)0.0000 (11)
C380.0432 (16)0.0380 (15)0.0468 (16)−0.0082 (12)0.0151 (13)0.0014 (12)
C390.0383 (15)0.0376 (14)0.0392 (16)0.0033 (11)0.0142 (12)0.0079 (12)
C400.0399 (16)0.0428 (16)0.0517 (17)−0.0038 (12)0.0187 (14)−0.0024 (13)
C410.0358 (14)0.0333 (13)0.0345 (14)−0.0035 (11)0.0105 (11)0.0018 (11)
C420.0379 (14)0.0303 (13)0.0330 (14)−0.0017 (11)0.0094 (11)0.0006 (11)
C430.0475 (17)0.0503 (17)0.0453 (17)0.0058 (14)0.0176 (14)0.0098 (14)
C440.0470 (18)0.060 (2)0.056 (2)0.0154 (15)0.0132 (15)0.0068 (16)
C450.0540 (19)0.0443 (17)0.0456 (18)0.0077 (14)0.0026 (15)0.0093 (14)
C460.061 (2)0.0446 (17)0.0381 (16)−0.0054 (14)0.0115 (14)0.0094 (13)
C470.0370 (14)0.0319 (13)0.0378 (14)−0.0006 (11)0.0109 (12)0.0016 (11)
C480.0457 (16)0.0310 (14)0.0438 (16)−0.0021 (12)0.0080 (13)0.0001 (12)
C490.076 (2)0.056 (2)0.0451 (19)−0.0144 (17)0.0075 (17)0.0062 (15)
C500.101 (4)0.063 (2)0.053 (2)−0.009 (2)−0.012 (2)0.0104 (18)
C510.064 (3)0.064 (3)0.093 (4)−0.005 (2)−0.020 (3)−0.010 (2)
C520.041 (2)0.085 (3)0.104 (4)−0.0090 (19)0.007 (2)−0.024 (3)
C530.067 (2)0.053 (2)0.112 (3)−0.0120 (18)0.053 (2)−0.030 (2)
C540.073 (2)0.0297 (15)0.0549 (19)−0.0029 (15)0.0171 (17)0.0048 (13)
C550.037 (6)0.033 (5)0.048 (10)−0.002 (4)0.002 (6)−0.020 (6)
C560.055 (7)0.049 (7)0.122 (17)0.000 (5)0.022 (10)−0.022 (9)
C570.050 (7)0.059 (8)0.15 (2)0.022 (6)0.024 (10)0.017 (11)
C580.051 (8)0.044 (8)0.104 (19)0.012 (6)−0.017 (10)0.014 (9)
C590.062 (10)0.029 (6)0.057 (9)0.008 (6)−0.019 (6)0.005 (5)
C600.052 (9)0.031 (7)0.051 (9)0.015 (7)0.007 (7)−0.006 (6)
C55'0.049 (4)0.040 (4)0.059 (8)0.003 (3)0.003 (4)−0.021 (4)
C56'0.048 (4)0.056 (4)0.142 (13)0.003 (3)0.023 (5)−0.028 (6)
C57'0.054 (5)0.060 (6)0.153 (17)0.011 (4)0.002 (7)−0.004 (6)
C58'0.087 (7)0.054 (4)0.118 (9)0.003 (4)−0.017 (7)0.013 (5)
C59'0.093 (7)0.043 (4)0.080 (6)−0.007 (5)−0.002 (5)0.002 (4)
C60'0.058 (4)0.029 (3)0.052 (5)−0.007 (3)0.003 (3)−0.007 (3)
O50.199 (7)0.350 (11)0.249 (9)0.050 (7)0.115 (7)−0.061 (8)
C610.123 (6)0.364 (16)0.150 (7)0.087 (8)0.056 (6)0.070 (9)

Geometric parameters (Å, °)

O1—C91.213 (3)C25—C301.408 (4)
O2—C101.227 (3)C26—C271.381 (6)
O3—C391.211 (3)C26—H26A0.930
O4—C401.219 (4)C27—C281.368 (6)
N1—C91.382 (4)C27—H27A0.930
N1—C111.449 (4)C28—C291.383 (5)
N1—C71.465 (4)C28—H28A0.930
N2—C101.353 (4)C29—C301.382 (5)
N2—C111.449 (4)C29—H29A0.930
N2—C81.458 (4)C31—C321.397 (4)
N3—C91.360 (4)C31—C361.402 (4)
N3—C171.440 (4)C31—C381.501 (4)
N3—C241.461 (4)C32—C331.384 (5)
N4—C101.369 (4)C32—H32A0.930
N4—C171.456 (4)C33—C341.361 (6)
N4—C231.470 (4)C33—H33A0.930
N5—C121.375 (4)C34—C351.390 (5)
N5—C161.390 (5)C34—H34A0.930
N6—C221.340 (4)C35—C361.385 (4)
N6—C181.345 (4)C35—H35A0.930
N7—C391.381 (3)C36—C371.515 (4)
N7—C411.451 (3)C37—H37A0.970
N7—C371.461 (3)C37—H37B0.970
N8—C401.352 (4)C38—H38A0.970
N8—C411.444 (3)C38—H38B0.970
N8—C381.456 (3)C41—C421.530 (4)
N9—C391.358 (4)C41—C471.581 (4)
N9—C541.446 (4)C42—C431.378 (4)
N9—C471.446 (3)C43—C441.380 (4)
N10—C401.388 (4)C43—H43A0.930
N10—C471.439 (4)C44—C451.363 (5)
N10—C531.462 (4)C44—H44A0.930
N11—C421.326 (3)C45—C461.365 (5)
N11—C461.346 (4)C45—H45A0.930
N12—C481.335 (4)C46—H46A0.930
N12—C521.337 (5)C47—C481.522 (4)
C1—C61.390 (5)C48—C491.362 (5)
C1—C21.391 (4)C49—C501.402 (6)
C1—C81.519 (5)C49—H49A0.930
C2—C31.389 (5)C50—C511.343 (7)
C2—H2A0.9300C50—H50A0.930
C3—C41.372 (6)C51—C521.365 (7)
C3—H3A0.930C51—H51A0.930
C4—C51.377 (5)C52—H52A0.930
C4—H4A0.930C53—C551.264 (19)
C5—C61.384 (5)C53—C55'1.664 (15)
C5—H5A0.930C53—H53A0.970
C6—C71.507 (4)C53—H53B0.970
C7—H7A0.970C54—C60'1.409 (10)
C7—H7B0.970C54—C601.683 (17)
C8—H8A0.970C54—H54A0.970
C8—H8B0.970C54—H54B0.970
C11—C121.533 (4)C55—C561.390
C11—C171.587 (4)C55—C601.390
C12—C131.327 (4)C56—C571.390
C13—C141.341 (5)C56—H56A0.930
C13—H13A0.930C57—C581.390
C14—C151.353 (7)C57—H57A0.930
C14—H14A0.930C58—C591.390
C15—C161.358 (6)C58—H58A0.930
C15—H15A0.930C59—C601.390
C16—H16A0.930C59—H59A0.930
C17—C181.528 (4)C55'—C56'1.390
C18—C191.369 (4)C55'—C60'1.390
C19—C201.398 (6)C56'—C57'1.390
C19—H19A0.930C56'—H56B0.930
C20—C211.382 (7)C57'—C58'1.390
C20—H20A0.930C57'—H57B0.930
C21—C221.338 (6)C58'—C59'1.390
C21—H21A0.930C58'—H58B0.930
C22—H22A0.930C59'—C60'1.390
C23—C251.503 (5)C59'—H59B0.930
C23—H23A0.970O5—C611.515 (10)
C23—H23B0.970O5—H50.820
C24—C301.511 (4)C61—H61A0.960
C24—H24A0.970C61—H61B0.960
C24—H24B0.970C61—H61C0.960
C25—C261.393 (4)
C9—N1—C11111.4 (2)C36—C31—C38121.3 (3)
C9—N1—C7120.1 (2)C33—C32—C31120.7 (3)
C11—N1—C7121.1 (2)C33—C32—H32A119.7
C10—N2—C11113.9 (2)C31—C32—H32A119.7
C10—N2—C8124.1 (2)C34—C33—C32120.2 (3)
C11—N2—C8121.9 (2)C34—C33—H33A119.9
C9—N3—C17114.3 (2)C32—C33—H33A119.9
C9—N3—C24122.8 (2)C33—C34—C35120.1 (3)
C17—N3—C24122.6 (2)C33—C34—H34A120.0
C10—N4—C17111.3 (2)C35—C34—H34A120.0
C10—N4—C23119.7 (2)C36—C35—C34120.9 (3)
C17—N4—C23121.0 (2)C36—C35—H35A119.6
C12—N5—C16116.9 (3)C34—C35—H35A119.6
C22—N6—C18117.0 (3)C35—C36—C31119.2 (3)
C39—N7—C41111.2 (2)C35—C36—C37119.5 (3)
C39—N7—C37120.7 (2)C31—C36—C37121.2 (2)
C41—N7—C37120.2 (2)N7—C37—C36115.3 (2)
C40—N8—C41114.1 (2)N7—C37—H37A108.5
C40—N8—C38123.5 (2)C36—C37—H37A108.5
C41—N8—C38122.2 (2)N7—C37—H37B108.5
C39—N9—C54123.6 (2)C36—C37—H37B108.5
C39—N9—C47114.2 (2)H37A—C37—H37B107.5
C54—N9—C47122.2 (2)N8—C38—C31113.7 (2)
C40—N10—C47111.6 (2)N8—C38—H38A108.8
C40—N10—C53120.1 (3)C31—C38—H38A108.8
C47—N10—C53120.2 (2)N8—C38—H38B108.8
C42—N11—C46116.9 (3)C31—C38—H38B108.8
C48—N12—C52116.6 (4)H38A—C38—H38B107.7
C6—C1—C2119.6 (3)O3—C39—N9126.6 (3)
C6—C1—C8121.8 (3)O3—C39—N7125.6 (3)
C2—C1—C8118.7 (3)N9—C39—N7107.7 (2)
C3—C2—C1120.1 (4)O4—C40—N8126.8 (3)
C3—C2—H2A119.9O4—C40—N10125.6 (3)
C1—C2—H2A119.9N8—C40—N10107.5 (2)
C4—C3—C2120.4 (3)N8—C41—N7113.2 (2)
C4—C3—H3A119.8N8—C41—C42112.8 (2)
C2—C3—H3A119.8N7—C41—C42111.7 (2)
C3—C4—C5119.3 (4)N8—C41—C47101.5 (2)
C3—C4—H4A120.3N7—C41—C47102.9 (2)
C5—C4—H4A120.3C42—C41—C47114.0 (2)
C4—C5—C6121.6 (4)N11—C42—C43123.1 (3)
C4—C5—H5A119.2N11—C42—C41115.5 (2)
C6—C5—H5A119.2C43—C42—C41121.2 (2)
C5—C6—C1119.1 (3)C42—C43—C44118.5 (3)
C5—C6—C7119.3 (3)C42—C43—H43A120.8
C1—C6—C7121.5 (3)C44—C43—H43A120.8
N1—C7—C6115.6 (2)C45—C44—C43119.3 (3)
N1—C7—H7A108.4C45—C44—H44A120.4
C6—C7—H7A108.4C43—C44—H44A120.4
N1—C7—H7B108.4C44—C45—C46118.5 (3)
C6—C7—H7B108.4C44—C45—H45A120.8
H7A—C7—H7B107.5C46—C45—H45A120.8
N2—C8—C1113.6 (2)N11—C46—C45123.7 (3)
N2—C8—H8A108.8N11—C46—H46A118.1
C1—C8—H8A108.8C45—C46—H46A118.1
N2—C8—H8B108.8N10—C47—N9113.0 (2)
C1—C8—H8B108.8N10—C47—C48112.1 (2)
H8A—C8—H8B107.7N9—C47—C48111.5 (2)
O1—C9—N3126.4 (3)N10—C47—C41102.8 (2)
O1—C9—N1125.9 (3)N9—C47—C41101.3 (2)
N3—C9—N1107.7 (2)C48—C47—C41115.5 (2)
O2—C10—N2126.1 (3)N12—C48—C49123.4 (3)
O2—C10—N4125.2 (3)N12—C48—C47115.3 (3)
N2—C10—N4108.7 (2)C49—C48—C47121.2 (3)
N1—C11—N2112.8 (2)C48—C49—C50118.3 (4)
N1—C11—C12113.5 (2)C48—C49—H49A120.8
N2—C11—C12111.2 (2)C50—C49—H49A120.8
N1—C11—C17102.9 (2)C51—C50—C49118.7 (4)
N2—C11—C17101.2 (2)C51—C50—H50A120.7
C12—C11—C17114.3 (2)C49—C50—H50A120.7
C13—C12—N5123.2 (3)C50—C51—C52119.3 (4)
C13—C12—C11116.5 (3)C50—C51—H51A120.4
N5—C12—C11120.2 (3)C52—C51—H51A120.4
C12—C13—C14117.9 (4)N12—C52—C51123.7 (4)
C12—C13—H13A121.0N12—C52—H52A118.1
C14—C13—H13A121.0C51—C52—H52A118.1
C13—C14—C15123.0 (4)C55—C53—N10125.7 (10)
C13—C14—H14A118.5N10—C53—C55'111.5 (5)
C15—C14—H14A118.5C55—C53—H53A105.9
C14—C15—C16118.5 (4)N10—C53—H53A105.9
C14—C15—H15A120.7C55'—C53—H53A117.2
C16—C15—H15A120.7C55—C53—H53B105.9
C15—C16—N5120.4 (4)N10—C53—H53B105.9
C15—C16—H16A119.8C55'—C53—H53B109.4
N5—C16—H16A119.8H53A—C53—H53B106.2
N3—C17—N4113.2 (2)C60'—C54—N9114.9 (5)
N3—C17—C18111.5 (2)N9—C54—C60108.4 (8)
N4—C17—C18112.4 (2)C60'—C54—H54A96.4
N3—C17—C11101.4 (2)N9—C54—H54A110.0
N4—C17—C11102.9 (2)C60—C54—H54A110.0
C18—C17—C11114.8 (2)C60'—C54—H54B116.0
N6—C18—C19123.6 (3)N9—C54—H54B110.0
N6—C18—C17114.8 (3)C60—C54—H54B110.0
C19—C18—C17121.6 (3)H54A—C54—H54B108.4
C18—C19—C20117.2 (4)C53—C55—C56119.9 (10)
C18—C19—H19A121.4C53—C55—C60119.5 (10)
C20—C19—H19A121.4C56—C55—C60120.0
C21—C20—C19119.2 (4)C57—C56—C55120.0
C21—C20—H20A120.4C57—C56—H56A120.0
C19—C20—H20A120.4C55—C56—H56A120.0
C22—C21—C20119.0 (4)C56—C57—C58120.0
C22—C21—H21A120.5C56—C57—H57A120.0
C20—C21—H21A120.5C58—C57—H57A120.0
C21—C22—N6123.9 (4)C59—C58—C57120.0
C21—C22—H22A118.1C59—C58—H58A120.0
N6—C22—H22A118.1C57—C58—H58A120.0
N4—C23—C25115.6 (2)C60—C59—C58120.0
N4—C23—H23A108.4C60—C59—H59A120.0
C25—C23—H23A108.4C58—C59—H59A120.0
N4—C23—H23B108.4C59—C60—C55120.0
C25—C23—H23B108.4C59—C60—C54116.6 (8)
H23A—C23—H23B107.5C55—C60—C54123.1 (7)
N3—C24—C30112.9 (2)C56'—C55'—C60'120.0
N3—C24—H24A109.0C56'—C55'—C53118.4 (5)
C30—C24—H24A109.0C60'—C55'—C53121.3 (5)
N3—C24—H24B109.0C57'—C56'—C55'120.0
C30—C24—H24B109.0C57'—C56'—H56B120.0
H24A—C24—H24B107.8C55'—C56'—H56B120.0
C26—C25—C30118.5 (3)C56'—C57'—C58'120.0
C26—C25—C23120.0 (3)C56'—C57'—H57B120.0
C30—C25—C23121.5 (3)C58'—C57'—H57B120.0
C27—C26—C25121.2 (4)C59'—C58'—C57'120.0
C27—C26—H26A119.4C59'—C58'—H58B120.0
C25—C26—H26A119.4C57'—C58'—H58B120.0
C28—C27—C26119.8 (3)C58'—C59'—C60'120.0
C28—C27—H27A120.1C58'—C59'—H59B120.0
C26—C27—H27A120.1C60'—C59'—H59B120.0
C27—C28—C29120.3 (4)C59'—C60'—C55'120.0
C27—C28—H28A119.8C59'—C60'—C54120.3 (6)
C29—C28—H28A119.8C55'—C60'—C54119.7 (6)
C30—C29—C28120.7 (4)C61—O5—H5111.1
C30—C29—H29A119.6O5—C61—H61A109.5
C28—C29—H29A119.6O5—C61—H61B109.5
C29—C30—C25119.4 (3)H61A—C61—H61B109.5
C29—C30—C24119.8 (3)O5—C61—H61C109.5
C25—C30—C24120.8 (3)H61A—C61—H61C109.5
C32—C31—C36118.9 (3)H61B—C61—H61C109.5
C32—C31—C38119.8 (3)
C6—C1—C2—C31.7 (5)C31—C36—C37—N7−59.5 (3)
C8—C1—C2—C3−177.5 (3)C40—N8—C38—C3197.9 (3)
C1—C2—C3—C4−0.7 (5)C41—N8—C38—C31−77.9 (3)
C2—C3—C4—C5−0.8 (6)C32—C31—C38—N8−122.8 (3)
C3—C4—C5—C61.4 (6)C36—C31—C38—N857.9 (4)
C4—C5—C6—C1−0.5 (5)C54—N9—C39—O30.4 (5)
C4—C5—C6—C7176.1 (3)C47—N9—C39—O3178.4 (3)
C2—C1—C6—C5−1.0 (4)C54—N9—C39—N7178.5 (3)
C8—C1—C6—C5178.1 (3)C47—N9—C39—N7−3.5 (3)
C2—C1—C6—C7−177.5 (3)C41—N7—C39—O3−168.4 (3)
C8—C1—C6—C71.6 (4)C37—N7—C39—O3−19.4 (4)
C9—N1—C7—C6−72.6 (3)C41—N7—C39—N913.5 (3)
C11—N1—C7—C674.7 (3)C37—N7—C39—N9162.5 (2)
C5—C6—C7—N1124.6 (3)C41—N8—C40—O4178.8 (3)
C1—C6—C7—N1−59.0 (4)C38—N8—C40—O42.7 (5)
C10—N2—C8—C198.7 (3)C41—N8—C40—N10−3.5 (3)
C11—N2—C8—C1−77.8 (3)C38—N8—C40—N10−179.5 (2)
C6—C1—C8—N256.8 (4)C47—N10—C40—O4−168.9 (3)
C2—C1—C8—N2−124.1 (3)C53—N10—C40—O4−20.3 (5)
C17—N3—C9—O1177.6 (3)C47—N10—C40—N813.3 (3)
C24—N3—C9—O13.6 (4)C53—N10—C40—N8161.9 (3)
C17—N3—C9—N1−5.0 (3)C40—N8—C41—N7−115.9 (3)
C24—N3—C9—N1−179.0 (2)C38—N8—C41—N760.2 (3)
C11—N1—C9—O1−169.0 (3)C40—N8—C41—C42116.0 (3)
C7—N1—C9—O1−18.8 (4)C38—N8—C41—C42−67.9 (3)
C11—N1—C9—N313.6 (3)C40—N8—C41—C47−6.4 (3)
C7—N1—C9—N3163.8 (2)C38—N8—C41—C47169.7 (2)
C11—N2—C10—O2179.8 (3)C39—N7—C41—N891.7 (3)
C8—N2—C10—O23.1 (5)C37—N7—C41—N8−57.5 (3)
C11—N2—C10—N4−2.0 (3)C39—N7—C41—C42−139.6 (2)
C8—N2—C10—N4−178.7 (3)C37—N7—C41—C4271.2 (3)
C17—N4—C10—O2−170.7 (3)C39—N7—C41—C47−16.9 (3)
C23—N4—C10—O2−21.6 (4)C37—N7—C41—C47−166.1 (2)
C17—N4—C10—N211.0 (3)C46—N11—C42—C431.4 (4)
C23—N4—C10—N2160.1 (3)C46—N11—C42—C41−175.3 (2)
C9—N1—C11—N292.4 (3)N8—C41—C42—N11−29.2 (3)
C7—N1—C11—N2−57.4 (3)N7—C41—C42—N11−158.1 (2)
C9—N1—C11—C12−139.9 (2)C47—C41—C42—N1185.8 (3)
C7—N1—C11—C1270.3 (3)N8—C41—C42—C43154.1 (3)
C9—N1—C11—C17−15.8 (3)N7—C41—C42—C4325.2 (3)
C7—N1—C11—C17−165.6 (2)C47—C41—C42—C43−90.9 (3)
C10—N2—C11—N1−116.0 (3)N11—C42—C43—C44−2.1 (5)
C8—N2—C11—N160.8 (3)C41—C42—C43—C44174.4 (3)
C10—N2—C11—C12115.1 (3)C42—C43—C44—C450.9 (5)
C8—N2—C11—C12−68.1 (3)C43—C44—C45—C460.8 (5)
C10—N2—C11—C17−6.7 (3)C42—N11—C46—C450.4 (4)
C8—N2—C11—C17170.0 (3)C44—C45—C46—N11−1.5 (5)
C16—N5—C12—C13−0.2 (5)C40—N10—C47—N991.8 (3)
C16—N5—C12—C11178.1 (3)C53—N10—C47—N9−56.8 (4)
N1—C11—C12—C13−164.8 (3)C40—N10—C47—C48−141.1 (2)
N2—C11—C12—C13−36.2 (3)C53—N10—C47—C4870.2 (4)
C17—C11—C12—C1377.6 (3)C40—N10—C47—C41−16.5 (3)
N1—C11—C12—N516.9 (4)C53—N10—C47—C41−165.1 (3)
N2—C11—C12—N5145.4 (3)C39—N9—C47—N10−115.9 (3)
C17—C11—C12—N5−100.7 (3)C54—N9—C47—N1062.2 (3)
N5—C12—C13—C140.7 (5)C39—N9—C47—C48116.7 (3)
C11—C12—C13—C14−177.6 (3)C54—N9—C47—C48−65.2 (3)
C12—C13—C14—C15−0.6 (6)C39—N9—C47—C41−6.6 (3)
C13—C14—C15—C16−0.1 (6)C54—N9—C47—C41171.4 (3)
C14—C15—C16—N50.6 (6)N8—C41—C47—N1013.1 (2)
C12—N5—C16—C15−0.5 (5)N7—C41—C47—N10130.5 (2)
C9—N3—C17—N4−114.1 (3)C42—C41—C47—N10−108.4 (2)
C24—N3—C17—N460.0 (3)N8—C41—C47—N9−103.9 (2)
C9—N3—C17—C18118.1 (3)N7—C41—C47—N913.5 (2)
C24—N3—C17—C18−67.9 (3)C42—C41—C47—N9134.6 (2)
C9—N3—C17—C11−4.6 (3)N8—C41—C47—C48135.5 (2)
C24—N3—C17—C11169.5 (2)N7—C41—C47—C48−107.2 (3)
C10—N4—C17—N394.1 (3)C42—C41—C47—C4813.9 (3)
C23—N4—C17—N3−54.6 (3)C52—N12—C48—C49−0.8 (5)
C10—N4—C17—C18−138.5 (2)C52—N12—C48—C47−178.2 (3)
C23—N4—C17—C1872.8 (3)N10—C47—C48—N12−157.8 (2)
C10—N4—C17—C11−14.5 (3)N9—C47—C48—N12−29.9 (3)
C23—N4—C17—C11−163.2 (2)C41—C47—C48—N1285.0 (3)
N1—C11—C17—N311.7 (2)N10—C47—C48—C4924.7 (4)
N2—C11—C17—N3−105.1 (2)N9—C47—C48—C49152.6 (3)
C12—C11—C17—N3135.2 (2)C41—C47—C48—C49−92.5 (3)
N1—C11—C17—N4129.0 (2)N12—C48—C49—C501.3 (5)
N2—C11—C17—N412.1 (3)C47—C48—C49—C50178.6 (3)
C12—C11—C17—N4−107.5 (3)C48—C49—C50—C51−0.6 (6)
N1—C11—C17—C18−108.7 (3)C49—C50—C51—C52−0.5 (6)
N2—C11—C17—C18134.5 (2)C48—N12—C52—C51−0.4 (6)
C12—C11—C17—C1814.9 (3)C50—C51—C52—N121.0 (7)
C22—N6—C18—C190.7 (5)C40—N10—C53—C55−68.9 (10)
C22—N6—C18—C17−178.2 (3)C47—N10—C53—C5577.0 (10)
N3—C17—C18—N6−40.7 (3)C40—N10—C53—C55'−73.7 (5)
N4—C17—C18—N6−169.0 (2)C47—N10—C53—C55'72.2 (5)
C11—C17—C18—N673.9 (3)C39—N9—C54—C60'93.1 (7)
N3—C17—C18—C19140.3 (3)C47—N9—C54—C60'−84.8 (7)
N4—C17—C18—C1912.0 (4)C39—N9—C54—C60105.9 (7)
C11—C17—C18—C19−105.1 (3)C47—N9—C54—C60−71.9 (7)
N6—C18—C19—C200.6 (5)N10—C53—C55—C56122.1 (8)
C17—C18—C19—C20179.4 (3)C55'—C53—C55—C56140 (4)
C18—C19—C20—C21−0.7 (5)N10—C53—C55—C60−49.0 (14)
C19—C20—C21—C22−0.4 (6)C55'—C53—C55—C60−31 (4)
C20—C21—C22—N61.8 (6)C53—C55—C56—C57−171.1 (15)
C18—N6—C22—C21−1.9 (5)C60—C55—C56—C570.0
C10—N4—C23—C25−72.3 (4)C55—C56—C57—C580.0
C17—N4—C23—C2573.8 (4)C56—C57—C58—C590.0
C9—N3—C24—C3094.1 (3)C57—C58—C59—C600.0
C17—N3—C24—C30−79.5 (3)C58—C59—C60—C550.0
N4—C23—C25—C26121.6 (3)C58—C59—C60—C54−174.7 (14)
N4—C23—C25—C30−60.8 (4)C53—C55—C60—C59171.1 (15)
C30—C25—C26—C27−0.1 (5)C56—C55—C60—C590.0
C23—C25—C26—C27177.6 (3)C53—C55—C60—C54−14.6 (18)
C25—C26—C27—C280.6 (5)C56—C55—C60—C54174.3 (15)
C26—C27—C28—C29−0.3 (5)C60'—C54—C60—C59−2(4)
C27—C28—C29—C30−0.4 (5)N9—C54—C60—C59−123.3 (8)
C28—C29—C30—C250.9 (5)C60'—C54—C60—C55−177 (5)
C28—C29—C30—C24−179.7 (3)N9—C54—C60—C5562.2 (11)
C26—C25—C30—C29−0.6 (4)C55—C53—C55'—C56'−42 (4)
C23—C25—C30—C29−178.2 (3)N10—C53—C55'—C56'122.1 (5)
C26—C25—C30—C24180.0 (3)C55—C53—C55'—C60'132 (4)
C23—C25—C30—C242.3 (4)N10—C53—C55'—C60'−63.4 (6)
N3—C24—C30—C29−121.8 (3)C60'—C55'—C56'—C57'0.0
N3—C24—C30—C2557.6 (4)C53—C55'—C56'—C57'174.6 (7)
C36—C31—C32—C331.7 (4)C55'—C56'—C57'—C58'0.0
C38—C31—C32—C33−177.7 (3)C56'—C57'—C58'—C59'0.0
C31—C32—C33—C34−1.2 (5)C57'—C58'—C59'—C60'0.0
C32—C33—C34—C35−0.1 (5)C58'—C59'—C60'—C55'0.0
C33—C34—C35—C361.1 (5)C58'—C59'—C60'—C54178.6 (8)
C34—C35—C36—C31−0.6 (4)C56'—C55'—C60'—C59'0.0
C34—C35—C36—C37177.6 (3)C53—C55'—C60'—C59'−174.4 (7)
C32—C31—C36—C35−0.7 (4)C56'—C55'—C60'—C54−178.6 (8)
C38—C31—C36—C35178.6 (3)C53—C55'—C60'—C546.9 (8)
C32—C31—C36—C37−178.9 (3)N9—C54—C60'—C59'−121.8 (5)
C38—C31—C36—C370.4 (4)C60—C54—C60'—C59'174 (5)
C39—N7—C37—C36−70.8 (3)N9—C54—C60'—C55'56.8 (7)
C41—N7—C37—C3675.5 (3)C60—C54—C60'—C55'−7(4)
C35—C36—C37—N7122.4 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O5—H5···O20.822.022.840 (8)178
C2—H2A···O5i0.932.353.279 (9)174
C22—H22A···O2ii0.932.573.462 (4)160
C43—H43A···O3iii0.932.603.249 (5)128
C46—H46A···O10.932.593.340 (4)138
C51—H51A···O2iv0.932.523.419 (4)164

Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, −y+1/2, z−1/2; (iii) −x+1, −y+1, −z; (iv) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BI2258).

References

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