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Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): o2195.
Published online 2008 October 25. doi:  10.1107/S1600536808034442
PMCID: PMC2959611

Non-merohedrally twinned hexa­methyl­enetetra­mine–4-nitro­phenol–water (1/2/1), triclinic modification

Abstract

The asymmetric unit of the title cocrystal, C6H12N4·2C6H5NO3·H2O, contains four formula units, which are linked by O—H(...)O and O—H(...)N hydrogen bonds into chains in the crystal. The crystal studied was a non-merohedral twin, with a minor twin component of 19%.

Related literature

For the background to this study and the C2 modification, see: Ng et al. (2001 [triangle]). The P1 modification is a non-merohedral twin; for the treatment of twinned diffraction data, see: Spek (2003 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o2195-scheme1.jpg

Experimental

Crystal data

  • C6H12N4·2C6H5NO3·H2O
  • M r = 436.43
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2195-efi1.jpg
  • a = 6.9325 (1) Å
  • b = 11.6867 (2) Å
  • c = 25.0826 (5) Å
  • α = 96.728 (1)°
  • β = 92.449 (1)°
  • γ = 89.971 (1)°
  • V = 2016.29 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 100 (2) K
  • 0.29 × 0.18 × 0.03 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: none
  • 32727 measured reflections
  • 9162 independent reflections
  • 7405 reflections with I > 2σ(I)
  • R int = 0.045

Refinement

  • R[F 2 > 2σ(F 2)] = 0.079
  • wR(F 2) = 0.232
  • S = 1.06
  • 9162 reflections
  • 1118 parameters
  • 27 restraints
  • H-atom parameters constrained
  • Δρmax = 0.54 e Å−3
  • Δρmin = −0.59 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808034442/lh2700sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034442/lh2700Isup2.hkl

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

Acknowledgments

I thank the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

The literature reports that the reaction of colorless hexamethylenetetramine and faint-yellow 4-nitrophenol in water/acetone yields deep yellow crystals. Two triclinic modifcations have been reported along with their unit cell cell constants [cell dimensions are 5.899 (1), 7.056 (1), 25.185 (11) Å, 87.53 (3), 96.71 (3), 90.0 (2)° for one polymorph and 11.781 (5), 7.046 (1), 25.174 (9) Å, 87.53 (2), 96.69 (3), 89.98 (2)° for the other polymorph]. In our studies, we found that the first polymorph is, in fact, a monoclinic C2 compound [49.989 (4), 5.9014 (5), 7.0556 (6) Å, β = 92.432 (2) °] (Ng et al., 2001). However, although we were able to confirm the triclinic unit-cell dimensions of the second polymorph, we were not able to determine its crystal structure from the room-temperature measurements.

In the present study, we identified the title compound in space group P1 (Fig. 1), which also exists as plates, similar to the C2 compound (whose unit-cell volume at low temperature is not significantly different from that at room temperature). The triclinic polymorph has a significantly smaller volume [2016.29 (6) Å3] than the monoclinic polymorph [2079.6 (3) Å3], and is consequently denser (density 1.438 kg M-3) than the monoclinic polymorph (density 1.394 kg M-3). There does not appear to be a crystallographic relationship between the two modifications other than for one long axis. The triclinic polymorph is a nonmerohedral twin, the twin component being 18.9%.

Experimental

The compound was obtained as deep yellow plates from the reaction of hexamethylenetetramine and 4-nitrophenol in acetone-water (Ng et al., 2001).

Refinement

The carbon- and oxygen-bound H-atoms were placed in calculated positions (C–H 0.95, O–H 0.84 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5U(C,O). An sp2-type of hybridization was assumed for the hydroxy groups, i.e., the phenolic H-atom is coplanar with the phenylene ring. Hydrogen atoms were placed on the phenolic oxygen atoms rather than on the ammonium nitrogen atoms as the compound displays hydroxyl absorption bands, as noted in the previous study (Ng et al., 2001).

The water H-atoms were placed in chemically sensible positions on the basis of hydrogen bonding but were not refined; their temperature factors were similarly tied. The anisotropic temperature factors of the water O-atoms were restrained to be nearly isotropic. Of the eight H-atoms, four of them are about 2 Å from another H-atom; nevertheless, these four form unambigously short hydrogen bonds with acceptor atoms.

From the reflections used in the initial indexing of the unit cell, the CELL_NOW routine of the APEX2 package (Bruker, 2007) had suggested the presence of a twin component, the routine giving the twin law as (-1 0 0, 0 - 1 0, -0.313 0 1). The routine also suggested that the minor twin component was rotated from the principal component by 179.8° about the reciprocal axis along (0 0 1). The structure initially refined to an R index of 9.1% when twinning was not considered.

The TwinRotMat routine in PLATON (Spek, 2003) gave the twin law as (1 0 0, 0 - 1 0, -1/3 0 - 1); 3001 reflections are overlapped. [The routine gave a second twin law (-1 0 0, 0 - 1 0, 0.309 0.503 1) with 1837 overlapping reflections.] The inclusion of the twin law in the refinement gave lowered the R index from 7.9%; the twin component refined to 18.9%. An examination of the standard deviations in bond distances showed that these were somewhat decreased. Both twin laws do not lead to a metrically larger monoclinic unit cell. For example, the first gave the cell as 6.933, 11.685, 25.086 Å, 96.73, 92.82, 90.04 °.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of the noncentrosymmetric, triclinic unit-cell contents of C6H12N4.2C6H5NO3.H2O. The probability level is 70%; H-atoms are shown as spheres of arbrary radius.

Crystal data

C6H12N4·2C6H5NO3·H2OZ = 4
Mr = 436.43F(000) = 920
Triclinic, P1Dx = 1.438 Mg m3
Hall symbol: P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.9325 (1) ÅCell parameters from 8939 reflections
b = 11.6867 (2) Åθ = 2.5–28.4°
c = 25.0826 (5) ŵ = 0.11 mm1
α = 96.728 (1)°T = 100 K
β = 92.449 (1)°Plate, yellow
γ = 89.971 (1)°0.29 × 0.18 × 0.03 mm
V = 2016.29 (6) Å3

Data collection

Bruker SMART APEX diffractometer7405 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.045
graphiteθmax = 27.5°, θmin = 0.8°
ω scansh = −8→8
32727 measured reflectionsk = −15→15
9162 independent reflectionsl = −32→32

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.079Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.232H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.1474P)2 + 2.0674P] where P = (Fo2 + 2Fc2)/3
9162 reflections(Δ/σ)max = 0.001
1118 parametersΔρmax = 0.54 e Å3
27 restraintsΔρmin = −0.59 e Å3

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

xyzUiso*/Ueq
O10.0000 (8)1.0000 (4)0.25000 (18)0.0288 (11)
H1O0.02380.93380.23490.043*
O2−0.0311 (8)1.1938 (5)0.4909 (2)0.0323 (12)
O30.0203 (9)1.0152 (5)0.4999 (2)0.0368 (13)
O40.1866 (8)0.5010 (4)0.24997 (18)0.0284 (11)
H4O0.15810.43500.23470.043*
O50.2458 (9)0.5146 (5)0.5001 (2)0.0384 (13)
O60.2985 (8)0.6929 (5)0.4906 (2)0.0366 (13)
O70.7337 (8)0.5701 (4)0.53257 (18)0.0290 (11)
H7O0.71090.51130.54760.044*
O80.7134 (9)0.4609 (5)0.2824 (2)0.0362 (12)
O90.7653 (8)0.6442 (5)0.2920 (2)0.0334 (12)
O100.5468 (8)1.0711 (4)0.53237 (18)0.0276 (10)
H10O0.57461.01220.54740.041*
O110.4365 (8)1.1433 (5)0.2920 (2)0.0340 (12)
O120.4867 (9)0.9602 (5)0.2824 (2)0.0380 (13)
O13−0.4576 (7)0.8156 (4)−0.01168 (18)0.0230 (10)
H13O−0.43520.78110.01550.034*
O14−0.3262 (8)0.6738 (5)−0.25474 (18)0.0296 (11)
O15−0.2837 (8)0.5090 (4)−0.2236 (2)0.0300 (11)
O160.5311 (7)0.3152 (4)−0.01184 (17)0.0203 (9)
H16O0.55240.28070.01540.031*
O170.7228 (8)0.0100 (4)−0.2232 (2)0.0300 (11)
O180.6630 (8)0.1727 (5)−0.25473 (18)0.0286 (11)
O191.1932 (7)0.5177 (4)0.79411 (17)0.0216 (9)
H19O1.16720.47060.76680.032*
O201.0140 (8)0.3173 (4)1.0065 (2)0.0314 (11)
O211.0754 (7)0.4958 (4)1.03766 (18)0.0275 (11)
O220.2051 (7)1.0164 (4)0.79460 (17)0.0211 (9)
H22O0.18470.96840.76730.032*
O230.0583 (8)0.9965 (4)1.03681 (18)0.0280 (11)
O240.0167 (8)0.8168 (5)1.0063 (2)0.0319 (11)
O1W0.0925 (7)0.7915 (4)0.2163 (2)0.0270 (11)
H1W1−0.00250.77660.19490.040*
H1W20.19510.77320.20090.040*
O2W0.0751 (7)0.2933 (4)0.21581 (19)0.0262 (10)
H2W10.17410.26180.20280.039*
H2W2−0.02220.27150.19600.039*
O3W0.6416 (7)0.3774 (4)0.5660 (2)0.0265 (10)
H3W10.73850.37780.58720.040*
H3W20.54110.36810.58260.040*
O4W0.6586 (7)0.8806 (4)0.56655 (19)0.0262 (10)
H4W10.55820.85350.57760.039*
H4W20.75360.86790.58690.039*
N1−0.2389 (8)0.6989 (5)0.1583 (2)0.0203 (11)
N2−0.4161 (7)0.6974 (4)0.07192 (19)0.0137 (9)
N3−0.4233 (7)0.5292 (4)0.1213 (2)0.0174 (10)
N4−0.5907 (8)0.7054 (4)0.1549 (2)0.0177 (10)
N50.3858 (8)0.2002 (4)0.1548 (2)0.0186 (10)
N60.5578 (8)0.1966 (4)0.07150 (19)0.0158 (10)
N70.7398 (7)0.2066 (4)0.1580 (2)0.0168 (10)
N80.5663 (8)0.0292 (4)0.1221 (2)0.0176 (10)
N90.9764 (9)0.3147 (5)0.6242 (2)0.0215 (11)
N101.1517 (7)0.3569 (4)0.71079 (19)0.0145 (9)
N111.3260 (8)0.3234 (4)0.6276 (2)0.0186 (11)
N121.1612 (8)0.1638 (4)0.6617 (2)0.0177 (10)
N130.3488 (8)0.8184 (4)0.6275 (2)0.0182 (10)
N140.1774 (7)0.8557 (4)0.7111 (2)0.0153 (10)
N150.1693 (8)0.6638 (4)0.6604 (2)0.0186 (10)
N16−0.0046 (7)0.8238 (4)0.6246 (2)0.0161 (10)
N17−0.0069 (8)1.0923 (5)0.4722 (2)0.0245 (12)
N180.2681 (8)0.5919 (5)0.4719 (2)0.0250 (12)
N190.7411 (8)0.5523 (6)0.3108 (2)0.0266 (12)
N200.4658 (8)1.0512 (5)0.3104 (2)0.0242 (12)
N21−0.3186 (7)0.6122 (5)−0.2173 (2)0.0174 (10)
N220.6797 (7)0.1124 (5)−0.2169 (2)0.0175 (10)
N231.0573 (7)0.4161 (5)0.9999 (2)0.0183 (10)
N240.0513 (7)0.9164 (5)0.9994 (2)0.0172 (10)
C1−0.2423 (10)0.7362 (5)0.1042 (3)0.0207 (12)
H1A−0.23540.82140.10760.031*
H1B−0.12710.70560.08550.031*
C2−0.2474 (9)0.5718 (5)0.1523 (2)0.0174 (12)
H2A−0.13230.54030.13380.021*
H2B−0.24600.54480.18830.021*
C3−0.4100 (10)0.7455 (5)0.1854 (2)0.0212 (13)
H3A−0.40460.83070.18920.025*
H3B−0.41050.72090.22190.025*
C4−0.4255 (10)0.5694 (5)0.0684 (2)0.0182 (12)
H4A−0.54500.54180.04790.022*
H4B−0.31420.53610.04860.022*
C5−0.5887 (8)0.7429 (5)0.1016 (2)0.0155 (11)
H5A−0.58720.82810.10500.019*
H5B−0.70790.71570.08080.019*
C6−0.5935 (11)0.5792 (6)0.1499 (3)0.0252 (14)
H6A−0.71340.55050.12990.030*
H6B−0.59380.55360.18610.030*
C70.3855 (9)0.2376 (5)0.1010 (2)0.0178 (12)
H7A0.38180.32280.10430.021*
H7B0.26770.20790.08030.021*
C80.5609 (9)0.2481 (5)0.1850 (2)0.0188 (12)
H8A0.56350.22520.22180.023*
H8B0.55680.33330.18790.023*
C90.3924 (10)0.0751 (5)0.1503 (3)0.0204 (12)
H9A0.27470.04290.13030.024*
H9B0.39410.05000.18670.024*
C100.7320 (8)0.2417 (5)0.1038 (2)0.0165 (11)
H10A0.84880.21350.08510.020*
H10B0.73250.32690.10640.020*
C110.5590 (9)0.0687 (5)0.0686 (2)0.0165 (11)
H11A0.44140.03730.04830.020*
H11B0.67240.03840.04890.020*
C120.7385 (9)0.0797 (5)0.1529 (3)0.0197 (12)
H12A0.74250.05440.18930.024*
H12B0.85590.05050.13480.024*
C130.9783 (9)0.3790 (5)0.6782 (2)0.0201 (12)
H13A0.97050.46240.67490.024*
H13B0.86290.35730.69670.024*
C141.1467 (10)0.3480 (5)0.5971 (2)0.0207 (12)
H14A1.14090.43130.59330.025*
H14B1.14760.30520.56060.025*
C150.9837 (9)0.1904 (5)0.6306 (2)0.0195 (12)
H15A0.86900.16880.64940.023*
H15B0.98150.14460.59470.023*
C161.1610 (9)0.2318 (5)0.7147 (2)0.0167 (11)
H16A1.27970.21480.73570.020*
H16B1.04890.20870.73420.020*
C171.3241 (9)0.3878 (5)0.6812 (2)0.0160 (11)
H17A1.32230.47140.67790.019*
H17B1.44340.37110.70190.019*
C181.3299 (11)0.1996 (5)0.6329 (3)0.0256 (15)
H18A1.45040.18120.65270.031*
H18B1.32980.15560.59660.031*
C190.3499 (10)0.8824 (5)0.6815 (2)0.0205 (12)
H19A0.35350.96600.67840.025*
H19B0.46800.86280.70210.025*
C200.3416 (10)0.6948 (5)0.6319 (3)0.0221 (13)
H20A0.45970.67220.65160.026*
H20B0.33850.65160.59550.026*
C210.1729 (9)0.8512 (5)0.5974 (2)0.0177 (11)
H21A0.16960.80940.56060.021*
H21B0.17700.93480.59420.021*
C220.1745 (9)0.7298 (5)0.7137 (2)0.0178 (12)
H22A0.29090.70800.73450.021*
H22B0.05980.70970.73300.021*
C230.0025 (8)0.8851 (5)0.6791 (2)0.0161 (11)
H23A−0.11410.86560.69760.019*
H23B0.00140.96920.67680.019*
C24−0.0049 (10)0.6986 (5)0.6296 (3)0.0213 (13)
H24A−0.00980.65490.59330.026*
H24B−0.12200.67890.64800.026*
C25−0.0037 (10)1.0192 (6)0.3040 (2)0.0218 (12)
C26−0.0437 (8)1.1300 (5)0.3267 (3)0.0179 (12)
H26−0.06981.18890.30430.022*
C27−0.0455 (9)1.1545 (5)0.3820 (3)0.0192 (12)
H27−0.06931.23070.39790.023*
C28−0.0120 (9)1.0666 (5)0.4139 (2)0.0182 (12)
C290.0255 (9)0.9538 (5)0.3917 (2)0.0181 (12)
H290.05070.89480.41410.022*
C300.0249 (9)0.9302 (5)0.3361 (3)0.0206 (12)
H300.04400.85360.31990.025*
C310.2107 (10)0.5189 (6)0.3035 (2)0.0211 (12)
C320.1907 (9)0.4298 (6)0.3359 (3)0.0217 (12)
H320.16460.35330.32000.026*
C330.2095 (9)0.4548 (5)0.3915 (2)0.0179 (12)
H330.19260.39590.41390.021*
C340.2530 (8)0.5658 (6)0.4136 (2)0.0180 (11)
C350.2770 (8)0.6543 (5)0.3821 (2)0.0161 (11)
H350.30620.73030.39820.019*
C360.2579 (8)0.6301 (5)0.3268 (2)0.0167 (11)
H360.27690.68940.30470.020*
C370.7389 (9)0.5622 (6)0.4788 (2)0.0193 (12)
C380.7091 (9)0.4570 (6)0.4465 (2)0.0212 (12)
H380.68840.38840.46240.025*
C390.7101 (8)0.4539 (5)0.3911 (2)0.0164 (11)
H390.68660.38360.36860.020*
C400.7463 (9)0.5554 (5)0.3688 (2)0.0173 (11)
C410.7790 (9)0.6587 (6)0.4008 (3)0.0203 (12)
H410.80270.72700.38490.024*
C420.7772 (8)0.6619 (5)0.4559 (3)0.0180 (12)
H420.80200.73220.47820.022*
C430.5223 (10)1.0629 (6)0.4788 (2)0.0209 (12)
C440.4768 (8)1.1615 (5)0.4559 (2)0.0171 (11)
H440.45841.23180.47820.021*
C450.4578 (8)1.1589 (5)0.4006 (2)0.0168 (11)
H450.42951.22710.38460.020*
C460.4812 (9)1.0541 (6)0.3689 (2)0.0201 (12)
C470.5250 (8)0.9543 (5)0.3906 (2)0.0179 (11)
H470.54190.88430.36790.022*
C480.5443 (9)0.9572 (6)0.4463 (2)0.0214 (12)
H480.57190.88870.46220.026*
C49−0.4198 (8)0.7649 (5)−0.0601 (2)0.0140 (11)
C50−0.4591 (8)0.8252 (5)−0.1044 (2)0.0165 (11)
H50−0.51270.9003−0.09890.020*
C51−0.4212 (9)0.7776 (5)−0.1559 (2)0.0173 (11)
H51−0.44450.8198−0.18560.021*
C52−0.3481 (8)0.6664 (5)−0.1630 (2)0.0155 (11)
C53−0.3059 (8)0.6042 (5)−0.1202 (2)0.0149 (11)
H53−0.25580.5283−0.12630.018*
C54−0.3381 (8)0.6545 (5)−0.0682 (2)0.0155 (11)
H54−0.30490.6143−0.03830.019*
C550.5742 (8)0.2650 (5)−0.0603 (2)0.0143 (11)
C560.6575 (9)0.1544 (5)−0.0677 (2)0.0161 (11)
H560.68850.1141−0.03770.019*
C570.6938 (8)0.1048 (5)−0.1198 (2)0.0157 (11)
H570.74690.0296−0.12570.019*
C580.6512 (9)0.1666 (5)−0.1629 (2)0.0170 (11)
C590.5750 (8)0.2779 (5)−0.1556 (2)0.0157 (11)
H590.55040.3197−0.18550.019*
C600.5364 (8)0.3255 (5)−0.1046 (2)0.0147 (11)
H600.48320.4007−0.09920.018*
C611.1547 (8)0.4908 (5)0.8427 (2)0.0136 (10)
C621.0706 (8)0.3851 (5)0.8509 (2)0.0152 (11)
H621.03490.33040.82110.018*
C631.0400 (9)0.3610 (5)0.9029 (2)0.0167 (11)
H630.98940.28830.90900.020*
C641.0840 (9)0.4442 (5)0.9457 (2)0.0172 (11)
C651.1611 (9)0.5519 (5)0.9384 (2)0.0177 (11)
H651.18810.60840.96820.021*
C661.1967 (8)0.5737 (5)0.8870 (2)0.0149 (11)
H661.25040.64590.88140.018*
C670.1603 (8)0.9904 (5)0.8427 (2)0.0152 (11)
C680.1968 (8)1.0732 (5)0.8871 (2)0.0143 (11)
H680.25071.14550.88170.017*
C690.1565 (8)1.0522 (5)0.9382 (2)0.0165 (11)
H690.17911.10940.96800.020*
C700.0813 (9)0.9442 (5)0.9452 (2)0.0169 (11)
C710.0430 (8)0.8595 (5)0.9024 (2)0.0144 (11)
H71−0.00670.78650.90830.017*
C720.0790 (9)0.8836 (5)0.8507 (2)0.0160 (11)
H720.04860.82800.82080.019*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.038 (3)0.032 (3)0.015 (2)0.007 (2)−0.0044 (19)−0.0010 (18)
O20.034 (3)0.038 (3)0.021 (2)0.000 (2)−0.0021 (19)−0.014 (2)
O30.052 (3)0.044 (3)0.016 (2)0.005 (3)0.002 (2)0.009 (2)
O40.044 (3)0.030 (3)0.011 (2)−0.005 (2)0.0047 (19)0.0012 (17)
O50.044 (3)0.052 (4)0.020 (2)−0.008 (3)0.000 (2)0.012 (2)
O60.043 (3)0.039 (3)0.023 (3)0.000 (2)0.001 (2)−0.015 (2)
O70.037 (3)0.034 (3)0.017 (2)−0.008 (2)−0.0012 (19)0.0047 (19)
O80.043 (3)0.047 (3)0.018 (2)−0.006 (3)0.003 (2)−0.001 (2)
O90.038 (3)0.043 (3)0.022 (2)−0.001 (2)0.001 (2)0.020 (2)
O100.039 (3)0.030 (2)0.015 (2)0.006 (2)0.0028 (19)0.0038 (18)
O110.035 (3)0.046 (3)0.026 (3)−0.001 (2)0.002 (2)0.021 (2)
O120.042 (3)0.049 (3)0.020 (2)0.006 (3)0.000 (2)−0.005 (2)
O130.035 (3)0.018 (2)0.015 (2)0.0063 (18)−0.0012 (18)0.0024 (17)
O140.037 (3)0.041 (3)0.012 (2)0.007 (2)0.0015 (19)0.0080 (19)
O150.038 (3)0.028 (3)0.021 (2)0.011 (2)0.000 (2)−0.0076 (19)
O160.031 (3)0.016 (2)0.015 (2)0.0058 (17)−0.0016 (17)0.0031 (16)
O170.039 (3)0.027 (3)0.022 (2)0.010 (2)−0.001 (2)−0.0046 (19)
O180.034 (3)0.040 (3)0.013 (2)0.006 (2)0.0028 (18)0.0068 (19)
O190.033 (3)0.017 (2)0.0142 (19)−0.0049 (18)0.0021 (18)0.0011 (16)
O200.041 (3)0.029 (3)0.026 (2)−0.010 (2)0.005 (2)0.012 (2)
O210.032 (3)0.034 (3)0.015 (2)−0.007 (2)0.0038 (19)−0.0055 (19)
O220.029 (2)0.019 (2)0.015 (2)−0.0065 (18)0.0019 (17)0.0026 (16)
O230.034 (3)0.034 (3)0.015 (2)−0.005 (2)0.0035 (19)−0.0032 (19)
O240.041 (3)0.031 (3)0.025 (2)−0.013 (2)0.002 (2)0.011 (2)
O1W0.018 (2)0.034 (3)0.026 (2)0.0048 (18)0.0031 (18)−0.0127 (19)
O2W0.016 (2)0.033 (3)0.026 (2)−0.0023 (18)0.0024 (17)−0.0124 (19)
O3W0.018 (2)0.039 (3)0.027 (2)−0.0014 (18)0.0039 (18)0.019 (2)
O4W0.014 (2)0.042 (3)0.027 (2)0.0012 (18)0.0032 (17)0.022 (2)
N10.026 (3)0.017 (3)0.017 (2)0.000 (2)−0.001 (2)0.000 (2)
N20.019 (2)0.010 (2)0.012 (2)0.0003 (17)0.0041 (18)0.0011 (17)
N30.021 (3)0.013 (2)0.019 (2)−0.0008 (19)0.0010 (19)0.0029 (18)
N40.019 (3)0.015 (2)0.019 (2)0.0030 (19)0.0045 (19)0.0017 (19)
N50.022 (3)0.019 (3)0.014 (2)−0.002 (2)0.0038 (19)−0.0009 (19)
N60.023 (3)0.012 (2)0.013 (2)0.0032 (18)0.0036 (19)0.0006 (17)
N70.013 (2)0.017 (2)0.020 (2)−0.0024 (18)−0.0020 (19)0.0025 (19)
N80.022 (3)0.014 (2)0.016 (2)0.0020 (19)−0.0041 (19)0.0047 (18)
N90.030 (3)0.017 (3)0.018 (2)−0.002 (2)−0.001 (2)0.002 (2)
N100.016 (2)0.013 (2)0.015 (2)−0.0003 (17)0.0038 (18)0.0019 (17)
N110.020 (3)0.018 (3)0.019 (2)−0.0025 (19)0.006 (2)0.003 (2)
N120.023 (3)0.011 (2)0.020 (2)−0.0057 (19)0.003 (2)0.0027 (18)
N130.020 (3)0.018 (3)0.017 (2)0.001 (2)0.004 (2)0.0050 (19)
N140.019 (3)0.012 (2)0.015 (2)−0.0016 (18)0.0015 (18)0.0027 (17)
N150.024 (3)0.013 (2)0.019 (2)−0.0067 (19)−0.001 (2)0.0016 (19)
N160.011 (2)0.019 (2)0.017 (2)−0.0007 (18)−0.0027 (18)0.0006 (19)
N170.019 (3)0.034 (3)0.018 (3)−0.005 (2)0.004 (2)−0.005 (2)
N180.016 (3)0.037 (3)0.019 (3)0.004 (2)−0.002 (2)−0.005 (2)
N190.022 (3)0.042 (4)0.018 (3)0.007 (2)0.002 (2)0.009 (2)
N200.019 (3)0.038 (3)0.017 (3)−0.003 (2)−0.002 (2)0.011 (2)
N210.014 (2)0.026 (3)0.011 (2)0.0003 (19)0.0010 (18)0.0012 (19)
N220.014 (2)0.026 (3)0.013 (2)0.0007 (19)0.0017 (18)0.0009 (19)
N230.014 (2)0.024 (3)0.018 (2)−0.0007 (19)0.0029 (19)0.006 (2)
N240.014 (2)0.023 (3)0.015 (2)−0.0040 (19)−0.0002 (18)0.0025 (19)
C10.024 (3)0.017 (3)0.022 (3)−0.002 (2)0.003 (2)0.006 (2)
C20.021 (3)0.014 (3)0.017 (3)0.002 (2)0.003 (2)0.003 (2)
C30.029 (3)0.016 (3)0.018 (3)0.006 (2)0.004 (2)−0.001 (2)
C40.031 (3)0.010 (3)0.012 (3)0.005 (2)0.002 (2)−0.002 (2)
C50.016 (3)0.012 (3)0.019 (3)0.004 (2)0.005 (2)0.003 (2)
C60.031 (4)0.019 (3)0.028 (3)−0.005 (3)0.015 (3)0.005 (2)
C70.023 (3)0.016 (3)0.015 (3)0.006 (2)0.000 (2)0.003 (2)
C80.020 (3)0.019 (3)0.017 (3)−0.005 (2)0.001 (2)0.000 (2)
C90.022 (3)0.018 (3)0.021 (3)−0.010 (2)0.003 (2)0.002 (2)
C100.015 (3)0.013 (3)0.022 (3)−0.006 (2)0.005 (2)0.001 (2)
C110.026 (3)0.012 (3)0.012 (2)0.004 (2)0.001 (2)−0.001 (2)
C120.023 (3)0.015 (3)0.021 (3)−0.003 (2)−0.006 (2)0.003 (2)
C130.023 (3)0.018 (3)0.019 (3)0.002 (2)0.002 (2)0.000 (2)
C140.030 (3)0.019 (3)0.014 (3)−0.005 (2)0.003 (2)0.007 (2)
C150.025 (3)0.015 (3)0.019 (3)−0.004 (2)0.004 (2)0.002 (2)
C160.023 (3)0.013 (3)0.015 (3)−0.002 (2)0.000 (2)0.006 (2)
C170.019 (3)0.012 (3)0.016 (3)−0.003 (2)0.001 (2)0.000 (2)
C180.032 (4)0.015 (3)0.031 (3)0.007 (2)0.014 (3)0.002 (3)
C190.026 (3)0.016 (3)0.020 (3)−0.007 (2)0.001 (2)0.002 (2)
C200.027 (3)0.017 (3)0.022 (3)0.007 (2)0.006 (3)0.003 (2)
C210.019 (3)0.021 (3)0.014 (3)0.005 (2)0.004 (2)0.006 (2)
C220.026 (3)0.012 (3)0.016 (3)−0.004 (2)−0.002 (2)0.005 (2)
C230.013 (3)0.017 (3)0.018 (3)0.005 (2)0.004 (2)0.003 (2)
C240.024 (3)0.015 (3)0.024 (3)−0.002 (2)−0.005 (2)−0.001 (2)
C250.023 (3)0.027 (3)0.016 (3)0.007 (2)0.000 (2)0.006 (2)
C260.012 (3)0.018 (3)0.024 (3)0.002 (2)0.001 (2)0.007 (2)
C270.017 (3)0.016 (3)0.023 (3)−0.001 (2)−0.002 (2)0.000 (2)
C280.016 (3)0.025 (3)0.013 (3)−0.002 (2)0.001 (2)0.001 (2)
C290.016 (3)0.020 (3)0.018 (3)0.004 (2)0.000 (2)0.001 (2)
C300.019 (3)0.018 (3)0.024 (3)0.006 (2)0.000 (2)0.000 (2)
C310.025 (3)0.023 (3)0.015 (3)−0.003 (2)−0.004 (2)0.003 (2)
C320.021 (3)0.024 (3)0.021 (3)−0.005 (2)0.001 (2)0.003 (2)
C330.015 (3)0.017 (3)0.022 (3)0.003 (2)0.002 (2)0.006 (2)
C340.011 (3)0.027 (3)0.015 (3)0.001 (2)0.001 (2)0.000 (2)
C350.010 (3)0.013 (3)0.025 (3)−0.0014 (19)0.000 (2)−0.003 (2)
C360.011 (3)0.020 (3)0.020 (3)0.003 (2)0.003 (2)0.005 (2)
C370.016 (3)0.026 (3)0.016 (3)−0.008 (2)−0.002 (2)−0.001 (2)
C380.022 (3)0.021 (3)0.021 (3)−0.007 (2)−0.003 (2)0.008 (2)
C390.009 (3)0.019 (3)0.020 (3)−0.005 (2)−0.001 (2)0.001 (2)
C400.014 (3)0.024 (3)0.014 (3)0.002 (2)−0.002 (2)0.005 (2)
C410.016 (3)0.019 (3)0.026 (3)−0.001 (2)−0.003 (2)0.007 (2)
C420.012 (3)0.016 (3)0.026 (3)−0.003 (2)−0.001 (2)0.000 (2)
C430.024 (3)0.025 (3)0.013 (3)0.002 (2)−0.003 (2)0.002 (2)
C440.013 (3)0.018 (3)0.021 (3)−0.003 (2)0.003 (2)0.003 (2)
C450.015 (3)0.014 (3)0.022 (3)−0.002 (2)0.003 (2)0.008 (2)
C460.020 (3)0.027 (3)0.014 (3)−0.001 (2)0.001 (2)0.004 (2)
C470.012 (3)0.021 (3)0.020 (3)−0.003 (2)−0.001 (2)0.001 (2)
C480.024 (3)0.021 (3)0.019 (3)0.001 (2)0.003 (2)0.002 (2)
C490.014 (3)0.014 (3)0.015 (2)−0.003 (2)−0.003 (2)0.004 (2)
C500.014 (3)0.013 (3)0.024 (3)0.002 (2)−0.001 (2)0.007 (2)
C510.015 (3)0.021 (3)0.016 (3)−0.003 (2)0.000 (2)0.008 (2)
C520.013 (3)0.018 (3)0.016 (3)−0.003 (2)0.000 (2)0.001 (2)
C530.016 (3)0.012 (3)0.016 (3)−0.002 (2)−0.001 (2)0.000 (2)
C540.014 (3)0.016 (3)0.018 (3)0.001 (2)−0.001 (2)0.006 (2)
C550.015 (3)0.012 (3)0.016 (3)−0.001 (2)−0.002 (2)0.005 (2)
C560.015 (3)0.013 (3)0.021 (3)0.002 (2)−0.001 (2)0.004 (2)
C570.017 (3)0.012 (3)0.018 (3)0.001 (2)0.001 (2)0.000 (2)
C580.015 (3)0.020 (3)0.017 (3)−0.001 (2)0.001 (2)0.004 (2)
C590.012 (3)0.020 (3)0.016 (3)−0.002 (2)−0.002 (2)0.008 (2)
C600.010 (3)0.013 (3)0.022 (3)0.0011 (19)−0.003 (2)0.006 (2)
C610.011 (2)0.014 (3)0.016 (3)−0.001 (2)−0.002 (2)0.003 (2)
C620.017 (3)0.011 (3)0.017 (3)0.000 (2)−0.001 (2)−0.001 (2)
C630.020 (3)0.012 (3)0.019 (3)−0.004 (2)0.002 (2)0.003 (2)
C640.017 (3)0.020 (3)0.015 (3)0.005 (2)0.002 (2)0.003 (2)
C650.015 (3)0.015 (3)0.022 (3)0.002 (2)−0.003 (2)−0.002 (2)
C660.010 (3)0.010 (2)0.023 (3)−0.0008 (19)−0.003 (2)−0.001 (2)
C670.013 (3)0.014 (3)0.017 (3)−0.001 (2)−0.006 (2)0.002 (2)
C680.009 (3)0.011 (2)0.021 (3)−0.0021 (19)−0.004 (2)−0.001 (2)
C690.012 (3)0.015 (3)0.021 (3)0.002 (2)−0.004 (2)−0.003 (2)
C700.019 (3)0.019 (3)0.013 (3)0.003 (2)0.001 (2)0.002 (2)
C710.016 (3)0.009 (2)0.018 (3)−0.003 (2)0.000 (2)0.002 (2)
C720.019 (3)0.013 (3)0.016 (3)−0.001 (2)0.001 (2)0.002 (2)

Geometric parameters (Å, °)

O1—C251.347 (7)C9—H9A0.9900
O1—H1O0.8400C9—H9B0.9900
O2—N171.238 (8)C10—H10A0.9900
O3—N171.212 (8)C10—H10B0.9900
O4—C311.338 (7)C11—H11A0.9900
O4—H4O0.8400C11—H11B0.9900
O5—N181.225 (8)C12—H12A0.9900
O6—N181.233 (8)C12—H12B0.9900
O7—C371.343 (7)C13—H13A0.9900
O7—H7O0.8400C13—H13B0.9900
O8—N191.223 (8)C14—H14A0.9900
O9—N191.236 (8)C14—H14B0.9900
O10—C431.340 (7)C15—H15A0.9900
O10—H10O0.8400C15—H15B0.9900
O11—N201.233 (8)C16—H16A0.9900
O12—N201.216 (8)C16—H16B0.9900
O13—C491.325 (7)C17—H17A0.9900
O13—H13O0.8400C17—H17B0.9900
O14—N211.248 (7)C18—H18A0.9900
O15—N211.223 (7)C18—H18B0.9900
O16—C551.332 (7)C19—H19A0.9900
O16—H16O0.8400C19—H19B0.9900
O17—N221.227 (7)C20—H20A0.9900
O18—N221.247 (7)C20—H20B0.9900
O19—C611.332 (7)C21—H21A0.9900
O19—H19O0.8400C21—H21B0.9900
O20—N231.226 (7)C22—H22A0.9900
O21—N231.251 (7)C22—H22B0.9900
O22—C671.327 (7)C23—H23A0.9900
O22—H22O0.8400C23—H23B0.9900
O23—N241.244 (7)C24—H24A0.9900
O24—N241.222 (7)C24—H24B0.9900
O1W—H1W10.8369C25—C261.385 (9)
O1W—H1W20.8393C25—C301.397 (9)
O2W—H2W10.8385C26—C271.384 (9)
O2W—H2W20.8420C26—H260.9500
O3W—H3W10.8380C27—C281.388 (9)
O3W—H3W20.8396C27—H270.9500
O4W—H4W10.8366C28—C291.398 (8)
O4W—H4W20.8399C29—C301.390 (8)
N1—C31.465 (8)C29—H290.9500
N1—C11.472 (8)C30—H300.9500
N1—C21.475 (7)C31—C361.394 (9)
N2—C11.465 (8)C31—C321.404 (8)
N2—C41.489 (7)C32—C331.390 (8)
N2—C51.500 (7)C32—H320.9500
N3—C41.457 (7)C33—C341.379 (9)
N3—C21.473 (8)C33—H330.9500
N3—C61.490 (8)C34—C351.388 (8)
N4—C51.456 (7)C35—C361.382 (8)
N4—C61.465 (8)C35—H350.9500
N4—C31.486 (9)C36—H360.9500
N5—C91.455 (8)C37—C421.388 (8)
N5—C71.466 (7)C37—C381.401 (9)
N5—C81.477 (8)C38—C391.385 (8)
N6—C71.482 (7)C38—H380.9500
N6—C101.486 (8)C39—C401.396 (8)
N6—C111.488 (7)C39—H390.9500
N7—C101.465 (8)C40—C411.382 (9)
N7—C121.474 (8)C41—C421.380 (9)
N7—C81.491 (8)C41—H410.9500
N8—C111.468 (7)C42—H420.9500
N8—C121.478 (8)C43—C441.377 (8)
N8—C91.492 (8)C43—C481.410 (9)
N9—C141.463 (8)C44—C451.384 (8)
N9—C131.469 (8)C44—H440.9500
N9—C151.481 (8)C45—C461.393 (9)
N10—C131.465 (8)C45—H450.9500
N10—C161.479 (7)C46—C471.371 (9)
N10—C171.500 (7)C47—C481.396 (8)
N11—C171.461 (7)C47—H470.9500
N11—C181.468 (8)C48—H480.9500
N11—C141.477 (9)C49—C501.401 (8)
N12—C161.467 (8)C49—C541.405 (8)
N12—C151.480 (8)C50—C511.380 (8)
N12—C181.486 (8)C50—H500.9500
N13—C201.463 (8)C51—C521.390 (8)
N13—C191.468 (8)C51—H510.9500
N13—C211.481 (8)C52—C531.386 (8)
N14—C221.481 (7)C53—C541.395 (8)
N14—C191.487 (8)C53—H530.9500
N14—C231.489 (8)C54—H540.9500
N15—C221.464 (8)C55—C601.401 (7)
N15—C201.483 (8)C55—C561.411 (8)
N15—C241.487 (8)C56—C571.400 (8)
N16—C231.465 (8)C56—H560.9500
N16—C241.483 (8)C57—C581.389 (8)
N16—C211.486 (7)C57—H570.9500
N17—C281.455 (7)C58—C591.398 (8)
N18—C341.457 (7)C59—C601.372 (8)
N19—C401.451 (7)C59—H590.9500
N20—C461.463 (7)C60—H600.9500
N21—C521.455 (7)C61—C621.407 (8)
N22—C581.449 (8)C61—C661.407 (8)
N23—C641.454 (7)C62—C631.391 (8)
N24—C701.458 (7)C62—H620.9500
C1—H1A0.9900C63—C641.386 (8)
C1—H1B0.9900C63—H630.9500
C2—H2A0.9900C64—C651.403 (9)
C2—H2B0.9900C65—C661.375 (9)
C3—H3A0.9900C65—H650.9500
C3—H3B0.9900C66—H660.9500
C4—H4A0.9900C67—C681.402 (8)
C4—H4B0.9900C67—C721.409 (8)
C5—H5A0.9900C68—C691.374 (8)
C5—H5B0.9900C68—H680.9500
C6—H6A0.9900C69—C701.399 (8)
C6—H6B0.9900C69—H690.9500
C7—H7A0.9900C70—C711.390 (8)
C7—H7B0.9900C71—C721.390 (8)
C8—H8A0.9900C71—H710.9500
C8—H8B0.9900C72—H720.9500
C25—O1—H1O120.0N11—C18—N12111.6 (5)
C31—O4—H4O120.0N11—C18—H18A109.3
C37—O7—H7O120.0N12—C18—H18A109.3
C43—O10—H10O120.0N11—C18—H18B109.3
C49—O13—H13O120.0N12—C18—H18B109.3
C55—O16—H16O120.0H18A—C18—H18B108.0
C61—O19—H19O120.0N13—C19—N14112.0 (5)
C67—O22—H22O120.0N13—C19—H19A109.2
H1W1—O1W—H1W2110.0N14—C19—H19A109.2
H2W1—O2W—H2W2109.3N13—C19—H19B109.2
H3W1—O3W—H3W2109.7N14—C19—H19B109.2
H4W1—O4W—H4W2109.8H19A—C19—H19B107.9
C3—N1—C1108.2 (5)N13—C20—N15111.5 (5)
C3—N1—C2109.4 (5)N13—C20—H20A109.3
C1—N1—C2108.1 (5)N15—C20—H20A109.3
C1—N2—C4108.1 (5)N13—C20—H20B109.3
C1—N2—C5108.1 (5)N15—C20—H20B109.3
C4—N2—C5106.9 (4)H20A—C20—H20B108.0
C4—N3—C2109.4 (5)N13—C21—N16111.3 (5)
C4—N3—C6108.1 (5)N13—C21—H21A109.4
C2—N3—C6108.1 (5)N16—C21—H21A109.4
C5—N4—C6109.2 (5)N13—C21—H21B109.4
C5—N4—C3108.7 (5)N16—C21—H21B109.4
C6—N4—C3107.8 (5)H21A—C21—H21B108.0
C9—N5—C7109.4 (5)N15—C22—N14112.2 (4)
C9—N5—C8109.2 (5)N15—C22—H22A109.2
C7—N5—C8107.7 (5)N14—C22—H22A109.2
C7—N6—C10107.9 (4)N15—C22—H22B109.2
C7—N6—C11107.1 (5)N14—C22—H22B109.2
C10—N6—C11108.1 (5)H22A—C22—H22B107.9
C10—N7—C12107.9 (5)N16—C23—N14112.2 (4)
C10—N7—C8108.1 (5)N16—C23—H23A109.2
C12—N7—C8107.9 (5)N14—C23—H23A109.2
C11—N8—C12108.9 (5)N16—C23—H23B109.2
C11—N8—C9107.6 (5)N14—C23—H23B109.2
C12—N8—C9107.7 (5)H23A—C23—H23B107.9
C14—N9—C13108.5 (5)N16—C24—N15111.8 (5)
C14—N9—C15110.1 (5)N16—C24—H24A109.3
C13—N9—C15107.7 (5)N15—C24—H24A109.3
C13—N10—C16108.0 (5)N16—C24—H24B109.3
C13—N10—C17107.9 (5)N15—C24—H24B109.3
C16—N10—C17107.3 (4)H24A—C24—H24B107.9
C17—N11—C18109.0 (5)O1—C25—C26117.6 (6)
C17—N11—C14109.0 (5)O1—C25—C30121.6 (6)
C18—N11—C14108.2 (5)C26—C25—C30120.8 (6)
C16—N12—C15108.7 (5)C27—C26—C25119.7 (6)
C16—N12—C18108.6 (5)C27—C26—H26120.1
C15—N12—C18108.0 (5)C25—C26—H26120.1
C20—N13—C19109.3 (5)C26—C27—C28119.3 (6)
C20—N13—C21109.0 (5)C26—C27—H27120.3
C19—N13—C21108.0 (5)C28—C27—H27120.3
C22—N14—C19107.7 (5)C27—C28—C29121.8 (5)
C22—N14—C23107.8 (5)C27—C28—N17119.7 (6)
C19—N14—C23108.0 (5)C29—C28—N17118.5 (5)
C22—N15—C20108.6 (5)C30—C29—C28118.3 (5)
C22—N15—C24108.4 (5)C30—C29—H29120.9
C20—N15—C24107.8 (5)C28—C29—H29120.9
C23—N16—C24107.6 (5)C29—C30—C25120.0 (6)
C23—N16—C21109.0 (5)C29—C30—H30120.0
C24—N16—C21108.1 (5)C25—C30—H30120.0
O3—N17—O2123.1 (6)O4—C31—C36117.8 (5)
O3—N17—C28119.5 (6)O4—C31—C32122.1 (6)
O2—N17—C28117.3 (6)C36—C31—C32120.2 (6)
O5—N18—O6122.8 (6)C33—C32—C31119.3 (6)
O5—N18—C34119.5 (6)C33—C32—H32120.3
O6—N18—C34117.7 (6)C31—C32—H32120.3
O8—N19—O9122.4 (6)C34—C33—C32119.4 (5)
O8—N19—C40119.9 (6)C34—C33—H33120.3
O9—N19—C40117.7 (6)C32—C33—H33120.3
O12—N20—O11123.3 (6)C33—C34—C35121.9 (5)
O12—N20—C46119.3 (6)C33—C34—N18119.1 (5)
O11—N20—C46117.4 (6)C35—C34—N18119.0 (6)
O15—N21—O14123.4 (5)C36—C35—C34119.0 (5)
O15—N21—C52118.2 (5)C36—C35—H35120.5
O14—N21—C52118.3 (5)C34—C35—H35120.5
O17—N22—O18123.1 (5)C35—C36—C31120.2 (5)
O17—N22—C58118.4 (5)C35—C36—H36119.9
O18—N22—C58118.4 (5)C31—C36—H36119.9
O20—N23—O21123.0 (5)O7—C37—C42117.8 (6)
O20—N23—C64119.3 (5)O7—C37—C38121.6 (6)
O21—N23—C64117.7 (5)C42—C37—C38120.5 (6)
O24—N24—O23122.8 (5)C39—C38—C37119.5 (6)
O24—N24—C70119.2 (5)C39—C38—H38120.3
O23—N24—C70118.0 (5)C37—C38—H38120.3
N2—C1—N1112.6 (5)C38—C39—C40119.0 (5)
N2—C1—H1A109.1C38—C39—H39120.5
N1—C1—H1A109.1C40—C39—H39120.5
N2—C1—H1B109.1C41—C40—C39121.5 (5)
N1—C1—H1B109.1C41—C40—N19119.7 (6)
H1A—C1—H1B107.8C39—C40—N19118.8 (5)
N3—C2—N1110.9 (5)C42—C41—C40119.5 (6)
N3—C2—H2A109.5C42—C41—H41120.3
N1—C2—H2A109.5C40—C41—H41120.3
N3—C2—H2B109.5C41—C42—C37120.0 (6)
N1—C2—H2B109.5C41—C42—H42120.0
H2A—C2—H2B108.0C37—C42—H42120.0
N1—C3—N4111.4 (5)O10—C43—C44118.1 (6)
N1—C3—H3A109.3O10—C43—C48121.5 (6)
N4—C3—H3A109.3C44—C43—C48120.4 (6)
N1—C3—H3B109.3C43—C44—C45120.5 (6)
N4—C3—H3B109.3C43—C44—H44119.8
H3A—C3—H3B108.0C45—C44—H44119.8
N3—C4—N2112.1 (4)C44—C45—C46118.5 (5)
N3—C4—H4A109.2C44—C45—H45120.7
N2—C4—H4A109.2C46—C45—H45120.7
N3—C4—H4B109.2C47—C46—C45122.4 (5)
N2—C4—H4B109.2C47—C46—N20118.7 (6)
H4A—C4—H4B107.9C45—C46—N20118.8 (6)
N4—C5—N2111.6 (5)C46—C47—C48119.0 (6)
N4—C5—H5A109.3C46—C47—H47120.5
N2—C5—H5A109.3C48—C47—H47120.5
N4—C5—H5B109.3C47—C48—C43119.2 (6)
N2—C5—H5B109.3C47—C48—H48120.4
H5A—C5—H5B108.0C43—C48—H48120.4
N4—C6—N3111.6 (5)O13—C49—C50118.3 (5)
N4—C6—H6A109.3O13—C49—C54122.3 (5)
N3—C6—H6A109.3C50—C49—C54119.4 (5)
N4—C6—H6B109.3C51—C50—C49121.2 (5)
N3—C6—H6B109.3C51—C50—H50119.4
H6A—C6—H6B108.0C49—C50—H50119.4
N5—C7—N6112.1 (5)C50—C51—C52118.3 (5)
N5—C7—H7A109.2C50—C51—H51120.8
N6—C7—H7A109.2C52—C51—H51120.8
N5—C7—H7B109.2C53—C52—C51122.2 (5)
N6—C7—H7B109.2C53—C52—N21118.7 (5)
H7A—C7—H7B107.9C51—C52—N21119.1 (5)
N5—C8—N7111.4 (5)C52—C53—C54119.1 (5)
N5—C8—H8A109.3C52—C53—H53120.4
N7—C8—H8A109.3C54—C53—H53120.4
N5—C8—H8B109.3C53—C54—C49119.7 (5)
N7—C8—H8B109.3C53—C54—H54120.1
H8A—C8—H8B108.0C49—C54—H54120.1
N5—C9—N8111.5 (5)O16—C55—C60118.2 (5)
N5—C9—H9A109.3O16—C55—C56121.9 (5)
N8—C9—H9A109.3C60—C55—C56119.9 (5)
N5—C9—H9B109.3C57—C56—C55119.2 (5)
N8—C9—H9B109.3C57—C56—H56120.4
H9A—C9—H9B108.0C55—C56—H56120.4
N7—C10—N6112.5 (4)C58—C57—C56119.2 (5)
N7—C10—H10A109.1C58—C57—H57120.4
N6—C10—H10A109.1C56—C57—H57120.4
N7—C10—H10B109.1C57—C58—C59121.9 (5)
N6—C10—H10B109.1C57—C58—N22118.9 (5)
H10A—C10—H10B107.8C59—C58—N22119.1 (5)
N8—C11—N6112.1 (4)C60—C59—C58118.7 (5)
N8—C11—H11A109.2C60—C59—H59120.7
N6—C11—H11A109.2C58—C59—H59120.7
N8—C11—H11B109.2C59—C60—C55121.1 (5)
N6—C11—H11B109.2C59—C60—H60119.5
H11A—C11—H11B107.9C55—C60—H60119.5
N7—C12—N8112.6 (5)O19—C61—C62122.7 (5)
N7—C12—H12A109.1O19—C61—C66117.8 (5)
N8—C12—H12A109.1C62—C61—C66119.6 (5)
N7—C12—H12B109.1C63—C62—C61119.7 (5)
N8—C12—H12B109.1C63—C62—H62120.1
H12A—C12—H12B107.8C61—C62—H62120.1
N10—C13—N9112.7 (5)C64—C63—C62119.3 (5)
N10—C13—H13A109.1C64—C63—H63120.4
N9—C13—H13A109.1C62—C63—H63120.4
N10—C13—H13B109.1C63—C64—C65122.0 (5)
N9—C13—H13B109.1C63—C64—N23118.5 (5)
H13A—C13—H13B107.8C65—C64—N23119.4 (5)
N9—C14—N11111.0 (5)C66—C65—C64118.4 (5)
N9—C14—H14A109.4C66—C65—H65120.8
N11—C14—H14A109.4C64—C65—H65120.8
N9—C14—H14B109.4C65—C66—C61121.0 (5)
N11—C14—H14B109.4C65—C66—H66119.5
H14A—C14—H14B108.0C61—C66—H66119.5
N12—C15—N9110.4 (5)O22—C67—C68118.0 (5)
N12—C15—H15A109.6O22—C67—C72122.9 (5)
N9—C15—H15A109.6C68—C67—C72119.1 (5)
N12—C15—H15B109.6C69—C68—C67121.5 (5)
N9—C15—H15B109.6C69—C68—H68119.3
H15A—C15—H15B108.1C67—C68—H68119.3
N12—C16—N10112.1 (4)C68—C69—C70118.2 (5)
N12—C16—H16A109.2C68—C69—H69120.9
N10—C16—H16A109.2C70—C69—H69120.9
N12—C16—H16B109.2C71—C70—C69122.3 (5)
N10—C16—H16B109.2C71—C70—N24118.3 (5)
H16A—C16—H16B107.9C69—C70—N24119.3 (5)
N11—C17—N10111.4 (5)C70—C71—C72118.7 (5)
N11—C17—H17A109.3C70—C71—H71120.6
N10—C17—H17A109.3C72—C71—H71120.6
N11—C17—H17B109.3C71—C72—C67120.2 (5)
N10—C17—H17B109.3C71—C72—H72119.9
H17A—C17—H17B108.0C67—C72—H72119.9
C4—N2—C1—N1−57.6 (6)O2—N17—C28—C29176.5 (6)
C5—N2—C1—N157.7 (6)C27—C28—C29—C30−1.3 (9)
C3—N1—C1—N2−59.0 (6)N17—C28—C29—C30−178.5 (5)
C2—N1—C1—N259.4 (7)C28—C29—C30—C252.9 (9)
C4—N3—C2—N158.9 (6)O1—C25—C30—C29178.2 (6)
C6—N3—C2—N1−58.5 (6)C26—C25—C30—C29−4.1 (10)
C3—N1—C2—N358.8 (6)O4—C31—C32—C33−177.3 (6)
C1—N1—C2—N3−58.8 (6)C36—C31—C32—C333.0 (10)
C1—N1—C3—N458.8 (6)C31—C32—C33—C34−1.9 (9)
C2—N1—C3—N4−58.7 (6)C32—C33—C34—C350.6 (9)
C5—N4—C3—N1−59.5 (6)C32—C33—C34—N18178.6 (5)
C6—N4—C3—N158.8 (6)O5—N18—C34—C331.4 (8)
C2—N3—C4—N2−57.9 (6)O6—N18—C34—C33−176.8 (6)
C6—N3—C4—N259.6 (6)O5—N18—C34—C35179.5 (6)
C1—N2—C4—N356.6 (6)O6—N18—C34—C351.2 (8)
C5—N2—C4—N3−59.5 (6)C33—C34—C35—C36−0.4 (9)
C6—N4—C5—N2−59.1 (6)N18—C34—C35—C36−178.4 (5)
C3—N4—C5—N258.3 (6)C34—C35—C36—C311.5 (8)
C1—N2—C5—N4−57.4 (6)O4—C31—C36—C35177.5 (5)
C4—N2—C5—N458.7 (6)C32—C31—C36—C35−2.8 (9)
C5—N4—C6—N358.5 (7)O7—C37—C38—C39178.1 (6)
C3—N4—C6—N3−59.5 (7)C42—C37—C38—C39−2.6 (9)
C4—N3—C6—N4−58.4 (7)C37—C38—C39—C401.8 (9)
C2—N3—C6—N459.9 (7)C38—C39—C40—C41−0.6 (9)
C9—N5—C7—N6−58.5 (6)C38—C39—C40—N19−178.1 (5)
C8—N5—C7—N660.1 (6)O8—N19—C40—C41179.5 (6)
C10—N6—C7—N5−58.5 (6)O9—N19—C40—C41−0.6 (8)
C11—N6—C7—N557.8 (6)O8—N19—C40—C39−3.0 (9)
C9—N5—C8—N758.8 (6)O9—N19—C40—C39176.9 (6)
C7—N5—C8—N7−60.0 (6)C39—C40—C41—C420.3 (9)
C10—N7—C8—N559.0 (6)N19—C40—C41—C42177.8 (5)
C12—N7—C8—N5−57.4 (6)C40—C41—C42—C37−1.2 (9)
C7—N5—C9—N858.3 (6)O7—C37—C42—C41−178.3 (6)
C8—N5—C9—N8−59.3 (6)C38—C37—C42—C412.4 (9)
C11—N8—C9—N5−58.7 (6)O10—C43—C44—C45177.3 (6)
C12—N8—C9—N558.6 (6)C48—C43—C44—C45−1.9 (9)
C12—N7—C10—N658.7 (6)C43—C44—C45—C461.5 (9)
C8—N7—C10—N6−57.8 (6)C44—C45—C46—C47−1.0 (9)
C7—N6—C10—N757.4 (6)C44—C45—C46—N20−178.6 (5)
C11—N6—C10—N7−58.2 (6)O12—N20—C46—C472.1 (9)
C12—N8—C11—N6−56.9 (6)O11—N20—C46—C47−176.2 (6)
C9—N8—C11—N659.6 (6)O12—N20—C46—C45179.8 (6)
C7—N6—C11—N8−59.2 (6)O11—N20—C46—C451.4 (8)
C10—N6—C11—N856.9 (6)C45—C46—C47—C480.9 (9)
C10—N7—C12—N8−58.3 (6)N20—C46—C47—C48178.5 (5)
C8—N7—C12—N858.3 (6)C46—C47—C48—C43−1.3 (9)
C11—N8—C12—N757.8 (6)O10—C43—C48—C47−177.4 (6)
C9—N8—C12—N7−58.7 (6)C44—C43—C48—C471.8 (10)
C16—N10—C13—N9−58.2 (6)O13—C49—C50—C51179.3 (5)
C17—N10—C13—N957.5 (6)C54—C49—C50—C510.8 (9)
C14—N9—C13—N10−59.1 (6)C49—C50—C51—C521.9 (9)
C15—N9—C13—N1060.0 (7)C50—C51—C52—C53−2.4 (9)
C13—N9—C14—N1159.0 (6)C50—C51—C52—N21176.2 (5)
C15—N9—C14—N11−58.6 (6)O15—N21—C52—C5310.0 (8)
C17—N11—C14—N9−59.7 (6)O14—N21—C52—C53−168.5 (5)
C18—N11—C14—N958.7 (6)O15—N21—C52—C51−168.6 (6)
C16—N12—C15—N959.6 (6)O14—N21—C52—C5112.8 (8)
C18—N12—C15—N9−58.0 (6)C51—C52—C53—C540.1 (9)
C14—N9—C15—N1258.4 (6)N21—C52—C53—C54−178.5 (5)
C13—N9—C15—N12−59.7 (6)C52—C53—C54—C492.6 (9)
C15—N12—C16—N10−58.5 (6)O13—C49—C54—C53178.4 (5)
C18—N12—C16—N1058.7 (6)C50—C49—C54—C53−3.1 (9)
C13—N10—C16—N1257.1 (6)O16—C55—C56—C57178.0 (5)
C17—N10—C16—N12−59.0 (6)C60—C55—C56—C57−2.6 (9)
C18—N11—C17—N10−59.4 (6)C55—C56—C57—C581.5 (9)
C14—N11—C17—N1058.5 (6)C56—C57—C58—C590.7 (9)
C13—N10—C17—N11−57.1 (6)C56—C57—C58—N22−176.8 (5)
C16—N10—C17—N1159.1 (6)O17—N22—C58—C576.9 (8)
C17—N11—C18—N1258.4 (7)O18—N22—C58—C57−171.7 (5)
C14—N11—C18—N12−60.0 (7)O17—N22—C58—C59−170.8 (6)
C16—N12—C18—N11−57.7 (7)O18—N22—C58—C5910.7 (8)
C15—N12—C18—N1160.0 (7)C57—C58—C59—C60−1.9 (9)
C20—N13—C19—N14−58.3 (7)N22—C58—C59—C60175.7 (5)
C21—N13—C19—N1460.0 (6)C58—C59—C60—C550.7 (9)
C22—N14—C19—N1357.6 (6)O16—C55—C60—C59−179.1 (5)
C23—N14—C19—N13−58.5 (6)C56—C55—C60—C591.5 (9)
C19—N13—C20—N1558.0 (7)O19—C61—C62—C63177.9 (5)
C21—N13—C20—N15−59.7 (6)C66—C61—C62—C63−3.7 (8)
C22—N15—C20—N13−58.1 (6)C61—C62—C63—C643.2 (9)
C24—N15—C20—N1359.2 (6)C62—C63—C64—C65−0.8 (9)
C20—N13—C21—N1659.1 (6)C62—C63—C64—N23−177.9 (5)
C19—N13—C21—N16−59.5 (6)O20—N23—C64—C636.7 (9)
C23—N16—C21—N1358.6 (6)O21—N23—C64—C63−171.7 (5)
C24—N16—C21—N13−58.1 (6)O20—N23—C64—C65−170.5 (6)
C20—N15—C22—N1458.8 (6)O21—N23—C64—C6511.1 (8)
C24—N15—C22—N14−58.2 (6)C63—C64—C65—C66−1.2 (9)
C19—N14—C22—N15−58.3 (6)N23—C64—C65—C66175.9 (5)
C23—N14—C22—N1558.0 (6)C64—C65—C66—C610.8 (9)
C24—N16—C23—N1459.5 (6)O19—C61—C66—C65−179.9 (5)
C21—N16—C23—N14−57.5 (6)C62—C61—C66—C651.6 (8)
C22—N14—C23—N16−58.9 (6)O22—C67—C68—C69−179.2 (5)
C19—N14—C23—N1657.1 (6)C72—C67—C68—C690.5 (9)
C23—N16—C24—N15−59.0 (6)C67—C68—C69—C701.4 (9)
C21—N16—C24—N1558.6 (6)C68—C69—C70—C71−1.3 (9)
C22—N15—C24—N1658.6 (6)C68—C69—C70—N24175.3 (5)
C20—N15—C24—N16−58.8 (6)O24—N24—C70—C718.9 (9)
O1—C25—C26—C27−178.8 (6)O23—N24—C70—C71−169.7 (5)
C30—C25—C26—C273.4 (10)O24—N24—C70—C69−167.9 (6)
C25—C26—C27—C28−1.7 (9)O23—N24—C70—C6913.5 (8)
C26—C27—C28—C290.7 (9)C69—C70—C71—C72−0.7 (9)
C26—C27—C28—N17177.9 (5)N24—C70—C71—C72−177.3 (5)
O3—N17—C28—C27179.2 (6)C70—C71—C72—C672.6 (9)
O2—N17—C28—C27−0.8 (8)O22—C67—C72—C71177.1 (6)
O3—N17—C28—C29−3.5 (9)C68—C67—C72—C71−2.6 (9)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1O···O1W0.841.752.574 (7)169
O4—H4O···O2W0.841.762.585 (7)168
O7—H7O···O3W0.841.762.584 (7)168
O10—H10O···O4W0.841.762.584 (7)168
O13—H13O···N20.841.812.649 (6)173
O16—H16O···N60.841.812.641 (6)170
O19—H19O···N100.841.822.648 (7)170
O22—H22O···N140.841.812.645 (7)171
O1W—H1W1···N10.842.012.814 (8)161
O1W—H1W2···N4i0.842.022.851 (7)169
O2W—H2W1···N50.842.022.837 (7)166
O2W—H2W2···N7ii0.841.982.811 (7)172
O3W—H3W1···N90.842.042.830 (8)158
O3W—H3W2···N11ii0.842.012.845 (7)170
O4W—H4W1···N130.842.032.832 (7)161
O4W—H4W2···N16i0.841.992.819 (7)171

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: LH2700).

References

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  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Ng, S. W., Hu, S.-Z., Hanna, J. V., Raj, S. S. S., Fun, H.-K., Razak, I. A., Wojciechowski, G. & Brzezinski, B. (2001). J. Mol. Struct.595, 189–194.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.
  • Westrip, S. P. (2008). publCIF In preparation.

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