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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2009 Nov 7;65(Pt 12):o3032–o3033. doi: 10.1107/S1600536809046017

6-Butyl-5-(4-methoxy­phen­oxy)-3-phenyl-3H-1,2,3-triazolo[4,5-d]pyrimidin-7(6H)-one

Xiao-Hua Zeng a, Shou-Heng Deng b,*, Ping Chen b, Hong-Mei Wang a, Zuan Ma a
PMCID: PMC2971827  PMID: 21578768

Abstract

The asymmetric unit of the title compound, C21H21N5O3, consists of two geometrically similar mol­ecules. The fused rings of the triazolo[4,5-d]pyrimidine system are nearly coplanar, making dihedral angels of 1.48 (18) and 1.34 (16)°, and the phenyl rings are twisted by 12.3 (1) and 8.7 (1)° with respect to the triazolopyrimidine plane. The ethyl groups of the n-butyl side chains are disordered over two sites in each of the independent mol­ecules, the ratios of occupancies being 0.60:0.40 and 0.61:0.39.

Related literature

For the biological activity of 8-aza­guanine derivatives, see: Roblin et al. (1945); Ding et al. (2004); Mitchell et al. (1950); Levine et al. (1963); Montgomery et al. (1962)); Yamamoto et al. (1967); Bariana (1971); Holland et al. (1975). For related structures, see: Wang et al. (2006); Zeng et al. (2006, 2009); Zhao, Hu et al. (2005); Zhao, Wang & Ding (2005); Zhao, Xie et al. (2005).graphic file with name e-65-o3032-scheme1.jpg

Experimental

Crystal data

  • C21H21N5O3

  • M r = 391.43

  • Triclinic, Inline graphic

  • a = 11.5167 (13) Å

  • b = 12.4026 (13) Å

  • c = 14.9353 (16) Å

  • α = 78.795 (2)°

  • β = 76.207 (2)°

  • γ = 76.360 (2)°

  • V = 1991.7 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 298 K

  • 0.15 × 0.12 × 0.10 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T min = 0.987, T max = 0.991

  • 11898 measured reflections

  • 6940 independent reflections

  • 5252 reflections with I > 2σ(I)

  • R int = 0.061

Refinement

  • R[F 2 > 2σ(F 2)] = 0.079

  • wR(F 2) = 0.212

  • S = 1.07

  • 6940 reflections

  • 567 parameters

  • 12 restraints

  • H-atom parameters constrained

  • Δρmax = 0.44 e Å−3

  • Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL97 (Sheldrick, 2008).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809046017/ya2108sup1.cif

e-65-o3032-sup1.cif (35.9KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809046017/ya2108Isup2.hkl

e-65-o3032-Isup2.hkl (339.6KB, hkl)

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

Acknowledgments

We gratefully acknowledge financial support of this work by the National Basic Research Program of China (2003CB114400), the National Natural Science Foundation of China (20372023, 20102001), the Educational Commission of Hubei Province (grant Nos. B200624004, B20092412), the Shiyan Municipal Science and Technology Bureau (grant No. 20061835) and Yunyang Medical College (grant Nos. 2007QDJ15, 2007ZQB19, 2007ZQB20).

supplementary crystallographic information

Comment

The derivatives of heterocycles containing 8-azaguanine system, which are well known bioisosteres of guanine, are of great importance because of their remarkable biological properties, such as antimicrobial or antifungal activities (Roblin et al., 1945; Ding et al., 2004), encephaloma cell inhibitor (Mitchell et al., 1950; Levine et al., 1963), antileukemia (Montgomery et al., 1962), hypersusceptibility inhibitor and acesodyne activities (Yamamoto et al., 1967; Bariana, 1971; Holland et al., 1975).

In recent years, Zhao's group succeeded in synthesizing the derivatives of 8-azaguanine via aza-Wittig reaction of beta-ethoxycarbonyl iminophosphorane with aromatic isocyanates (Zhao, Xie et al., 2005). As a continuation of the quest for new biologically active derivatives of 8-azaguanine, the title compound was obtained from beta-ethoxycarbonyl iminophosphorane and aliphatic isocyanate and structurally characterized.

The asymmetric unit of the crystal of the title compound, C21H21N5O3, consists of two geometrically similar molecules (Fig. 1), the bond lengths and angles in triazolopyrimidinone moiety are in good agreement with those observed for a closely related structures (Zhao, Hu et al., 2005; Zhao, Wang & Ding, 2005). The fused rings of the triazolo[4,5-d]pyrimidine ring system are as usual coplanar (e.g. see structures by Wang et al., 2006 and Zeng et al., 2009), and the phenyl rings are twisted with respect to the triazolopyrimidine plane by 12.3 (1)° and 8.7 (1)° in each of the two independent molecules.

Experimental

To the solution of carbodiimide, prepared according to Zeng et al. (2006) in a mixed solvent (CH2Cl2/CH3CN, 1:4 v/v, 15 ml), was added 4-chlorophenol (3 mmol) and K2CO3 (6 mmol). After the reaction mixture was stirred for 12 h, the solvent was removed under reduced pressure and the residue was recrystallized from EtOH to give the title compound in 93% yield (m.p. 426 K). Elemental analysis: calculated for C21H21N5O3: C, 64.44; H, 5.41; N, 17.89%. Found: C, 63.62; H, 5.68; N, 17.51%. Crystals suitable for X-ray diffraction study were obtained by recrystallization from hexane and dichloromethane (1:3 v/v) at room temperature.

Refinement

All H atoms were placed in the geometrically calculated positions and treated as riding atoms, with C—H = 0.93–0.97 Å, and Uiso(H) = 1.2Ueq(C) [1.5Ueq(C) for methyl H atoms]. The terminal ethyl groups of the n-butyl substituent are disordered in both molecules; the occupancy refinement yielded ratio 0.60 : 0.40 and 0.61 : 0.39 for each of the two molecules. The bond lengths and the 1,3-distances in these groups were restrained during the refinement to be within the ranges of 1,54 ± 0.01 Å and 2.45 ± 0.01 Å respectively.

Figures

Fig. 1.

Fig. 1.

The asymmetric unit of the title compound with atomic numbering scheme and displacement ellipsoids drawn at the 30% probability level; only major components of disordered butyl groups are shown. H-Atoms are omitted.

Crystal data

C21H21N5O3 Z = 4
Mr = 391.43 F(000) = 824
Triclinic, P1 Dx = 1.305 Mg m3
Hall symbol: -P 1 Mo Kα radiation, λ = 0.71073 Å
a = 11.5167 (13) Å Cell parameters from 4234 reflections
b = 12.4026 (13) Å θ = 2.3–25.4°
c = 14.9353 (16) Å µ = 0.09 mm1
α = 78.795 (2)° T = 298 K
β = 76.207 (2)° Block, colorless
γ = 76.360 (2)° 0.15 × 0.12 × 0.10 mm
V = 1991.7 (4) Å3

Data collection

Bruker SMART CCD area-detector diffractometer 6940 independent reflections
Radiation source: fine-focus sealed tube 5252 reflections with I > 2σ(I)
graphite Rint = 0.061
φ and ω scans θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) h = −13→13
Tmin = 0.987, Tmax = 0.991 k = −13→14
11898 measured reflections l = −17→17

Refinement

Refinement on F2 Primary atom site location: structure-invariant direct methods
Least-squares matrix: full Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.079 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.212 H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0878P)2 + 0.7377P] where P = (Fo2 + 2Fc2)/3
6940 reflections (Δ/σ)max < 0.001
567 parameters Δρmax = 0.44 e Å3
12 restraints Δρmin = −0.22 e Å3

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)

x y z Uiso*/Ueq Occ. (<1)
C1 0.3813 (3) 1.1282 (3) −0.0630 (2) 0.0704 (8)
C2 0.4159 (3) 1.2053 (3) −0.1390 (3) 0.0929 (11)
H2 0.4473 1.2648 −0.1315 0.112*
C3 0.4038 (4) 1.1937 (4) −0.2255 (3) 0.1134 (15)
H3 0.4286 1.2451 −0.2767 0.136*
C4 0.3560 (4) 1.1082 (4) −0.2378 (3) 0.1053 (13)
H4 0.3469 1.1021 −0.2968 0.126*
C5 0.3215 (3) 1.0312 (3) −0.1625 (3) 0.0918 (10)
H5 0.2897 0.9721 −0.1703 0.110*
C6 0.3341 (3) 1.0418 (3) −0.0745 (2) 0.0789 (9)
H6 0.3103 0.9900 −0.0233 0.095*
C7 0.3573 (3) 1.0900 (2) 0.1139 (2) 0.0642 (7)
C8 0.4017 (3) 1.1368 (3) 0.1700 (3) 0.0748 (8)
C9 0.3731 (3) 1.1058 (3) 0.2691 (3) 0.0856 (10)
C10 0.2607 (3) 0.9846 (3) 0.2292 (2) 0.0708 (8)
C11 0.1502 (3) 0.8491 (3) 0.2166 (2) 0.0695 (8)
C12 0.0289 (3) 0.8462 (3) 0.2362 (2) 0.0759 (9)
H12 −0.0257 0.8930 0.2758 0.091*
C13 −0.0129 (3) 0.7744 (3) 0.1976 (2) 0.0775 (9)
H13 −0.0955 0.7721 0.2110 0.093*
C14 0.0688 (3) 0.7057 (3) 0.1388 (2) 0.0732 (8)
C15 0.1902 (3) 0.7121 (3) 0.1176 (2) 0.0810 (9)
H15 0.2447 0.6676 0.0761 0.097*
C16 0.2326 (3) 0.7834 (3) 0.1569 (2) 0.0767 (9)
H16 0.3149 0.7867 0.1432 0.092*
C17 −0.0777 (4) 0.6012 (4) 0.1313 (3) 0.1118 (14)
H17A −0.0869 0.5741 0.1969 0.168*
H17B −0.0848 0.5438 0.0993 0.168*
H17C −0.1401 0.6663 0.1212 0.168*
C18 0.2467 (5) 0.9939 (4) 0.3997 (3) 0.1173 (14)
H18A 0.2351 1.0582 0.4312 0.141*
H18B 0.1682 0.9732 0.4084 0.141*
C19 0.3312 (5) 0.9008 (5) 0.4395 (3) 0.1241 (15)
H19A 0.4072 0.9247 0.4342 0.149* 0.60
H19B 0.3485 0.8401 0.4030 0.149* 0.60
H19C 0.4133 0.9143 0.4292 0.149* 0.40
H19D 0.3321 0.8293 0.4218 0.149* 0.40
C20 0.2846 (11) 0.8550 (9) 0.5437 (5) 0.121 (4) 0.60
H20A 0.2018 0.8435 0.5531 0.145* 0.60
H20B 0.3363 0.7840 0.5619 0.145* 0.60
C21 0.2888 (10) 0.9402 (8) 0.5999 (5) 0.132 (3) 0.60
H21A 0.3635 0.9671 0.5768 0.198* 0.60
H21B 0.2846 0.9068 0.6639 0.198* 0.60
H21C 0.2209 1.0016 0.5952 0.198* 0.60
C22 −0.1449 (3) 0.6338 (2) 0.43768 (18) 0.0621 (7)
C23 −0.1744 (3) 0.5483 (3) 0.4068 (2) 0.0720 (8)
H23 −0.1134 0.4941 0.3790 0.086*
C24 −0.2963 (3) 0.5440 (3) 0.4179 (2) 0.0820 (9)
H24 −0.3169 0.4866 0.3967 0.098*
C25 −0.3869 (3) 0.6231 (4) 0.4594 (2) 0.0891 (10)
H25 −0.4685 0.6199 0.4663 0.107*
C26 −0.3555 (4) 0.7063 (4) 0.4904 (3) 0.1013 (12)
H26 −0.4164 0.7599 0.5191 0.122*
C27 −0.2362 (4) 0.7126 (3) 0.4800 (3) 0.0895 (10)
H27 −0.2165 0.7701 0.5016 0.107*
C28 0.0845 (3) 0.5873 (2) 0.37838 (19) 0.0593 (7)
C29 0.1745 (3) 0.6332 (3) 0.3916 (2) 0.0678 (8)
C30 0.2988 (3) 0.5944 (3) 0.3509 (3) 0.0815 (10)
C31 0.2108 (3) 0.4696 (3) 0.2899 (2) 0.0733 (8)
C32 0.1543 (3) 0.3377 (3) 0.2199 (2) 0.0700 (8)
C33 0.0893 (3) 0.2762 (3) 0.2924 (2) 0.0785 (9)
H33 0.0932 0.2781 0.3536 0.094*
C34 0.0188 (3) 0.2120 (3) 0.2740 (2) 0.0786 (9)
H34 −0.0263 0.1710 0.3232 0.094*
C35 0.0135 (3) 0.2071 (3) 0.1841 (2) 0.0701 (8)
C36 0.0764 (3) 0.2719 (3) 0.1126 (2) 0.0783 (9)
H36 0.0713 0.2714 0.0515 0.094*
C37 0.1466 (3) 0.3373 (3) 0.1306 (2) 0.0781 (9)
H37 0.1887 0.3812 0.0818 0.094*
C38 −0.0400 (5) 0.1100 (4) 0.0814 (3) 0.1248 (17)
H38A −0.0841 0.1719 0.0454 0.187*
H38B −0.0717 0.0439 0.0850 0.187*
H38C 0.0448 0.0972 0.0521 0.187*
C39 0.4370 (5) 0.4412 (4) 0.2681 (5) 0.1387 (19)
H39A 0.4898 0.4463 0.3083 0.166*
H39B 0.4363 0.3626 0.2704 0.166*
C40 0.4816 (4) 0.4881 (4) 0.1756 (5) 0.1389 (19)
H40A 0.4737 0.5671 0.1781 0.167* 0.61
H40B 0.4220 0.4841 0.1407 0.167* 0.61
H40C 0.4748 0.5685 0.1698 0.167* 0.39
H40D 0.4417 0.4716 0.1310 0.167* 0.39
C41 0.6105 (11) 0.4531 (16) 0.1097 (10) 0.266 (13) 0.61
H41A 0.6056 0.4016 0.0701 0.319* 0.61
H41B 0.6361 0.5188 0.0703 0.319* 0.61
C42 0.6979 (10) 0.3988 (19) 0.1703 (12) 0.284 (11) 0.61
H42A 0.7216 0.4550 0.1942 0.427* 0.61
H42B 0.7687 0.3562 0.1350 0.427* 0.61
H42C 0.6605 0.3497 0.2212 0.427* 0.61
C20' 0.2534 (19) 0.9186 (14) 0.5406 (7) 0.208 (14) 0.40
H20C 0.2578 0.9900 0.5557 0.250* 0.40
H20D 0.1686 0.9167 0.5446 0.250* 0.40
C21' 0.3110 (14) 0.8215 (16) 0.6063 (8) 0.170 (7) 0.40
H21D 0.3036 0.7518 0.5914 0.255* 0.40
H21E 0.2700 0.8287 0.6694 0.255* 0.40
H21F 0.3957 0.8229 0.5992 0.255* 0.40
C41' 0.6174 (7) 0.4221 (14) 0.1683 (10) 0.131 (6) 0.39
H41C 0.6526 0.4362 0.2167 0.157* 0.39
H41D 0.6214 0.3421 0.1743 0.157* 0.39
C42' 0.6838 (12) 0.4652 (15) 0.0738 (11) 0.174 (8) 0.39
H42D 0.6476 0.4508 0.0268 0.261* 0.39
H42E 0.7680 0.4279 0.0651 0.261* 0.39
H42F 0.6785 0.5445 0.0689 0.261* 0.39
N1 0.3984 (2) 1.1397 (2) 0.0256 (2) 0.0718 (7)
N2 0.4667 (3) 1.2151 (2) 0.0314 (3) 0.0924 (9)
N3 0.4686 (3) 1.2126 (2) 0.1183 (3) 0.0922 (9)
N4 0.2861 (2) 1.0120 (2) 0.13914 (17) 0.0651 (6)
N5 0.2979 (3) 1.0252 (2) 0.29391 (19) 0.0853 (8)
N6 −0.0203 (2) 0.64224 (19) 0.42687 (15) 0.0627 (6)
N7 0.0072 (3) 0.7202 (2) 0.46881 (18) 0.0786 (8)
N8 0.1237 (3) 0.7147 (2) 0.44767 (18) 0.0818 (8)
N9 0.0976 (2) 0.50531 (19) 0.32598 (16) 0.0607 (6)
N10 0.3093 (2) 0.5042 (2) 0.3012 (2) 0.0888 (9)
O1 0.4041 (3) 1.1411 (2) 0.3284 (2) 0.1146 (9)
O2 0.1887 (2) 0.9109 (2) 0.26967 (15) 0.0907 (7)
O3 0.3883 (2) 0.6278 (2) 0.3538 (2) 0.1099 (9)
O4 0.2423 (2) 0.3919 (2) 0.23281 (19) 0.0926 (7)
O5 0.0382 (2) 0.6299 (2) 0.09702 (18) 0.0975 (8)
O6 −0.0535 (2) 0.1350 (2) 0.17288 (18) 0.0985 (8)

Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
C1 0.0525 (16) 0.0621 (19) 0.080 (2) −0.0022 (14) −0.0041 (14) 0.0059 (16)
C2 0.083 (2) 0.082 (2) 0.095 (3) −0.0164 (19) −0.0054 (19) 0.016 (2)
C3 0.103 (3) 0.118 (4) 0.089 (3) −0.017 (3) −0.004 (2) 0.031 (3)
C4 0.088 (3) 0.134 (4) 0.071 (2) −0.006 (3) −0.0051 (19) 0.006 (2)
C5 0.086 (2) 0.104 (3) 0.075 (2) −0.012 (2) −0.0074 (18) −0.008 (2)
C6 0.069 (2) 0.080 (2) 0.072 (2) −0.0116 (17) −0.0004 (15) 0.0038 (17)
C7 0.0537 (16) 0.0508 (16) 0.079 (2) −0.0017 (13) −0.0093 (14) −0.0045 (15)
C8 0.0682 (19) 0.0572 (18) 0.096 (2) −0.0068 (15) −0.0154 (17) −0.0129 (17)
C9 0.092 (2) 0.073 (2) 0.098 (3) −0.0042 (19) −0.031 (2) −0.026 (2)
C10 0.0747 (19) 0.0667 (19) 0.070 (2) −0.0118 (16) −0.0160 (15) −0.0097 (16)
C11 0.085 (2) 0.0651 (18) 0.0525 (16) −0.0167 (17) −0.0152 (15) 0.0094 (14)
C12 0.072 (2) 0.071 (2) 0.0683 (19) −0.0076 (16) −0.0023 (15) 0.0062 (16)
C13 0.0637 (19) 0.084 (2) 0.075 (2) −0.0144 (17) −0.0173 (16) 0.0143 (18)
C14 0.072 (2) 0.074 (2) 0.0682 (19) −0.0107 (17) −0.0227 (16) 0.0077 (16)
C15 0.074 (2) 0.084 (2) 0.078 (2) −0.0077 (18) −0.0110 (16) −0.0093 (18)
C16 0.0640 (19) 0.080 (2) 0.082 (2) −0.0157 (17) −0.0182 (16) 0.0023 (18)
C17 0.113 (3) 0.139 (4) 0.100 (3) −0.057 (3) −0.036 (2) 0.002 (3)
C18 0.135 (4) 0.123 (4) 0.108 (3) −0.033 (3) −0.042 (3) −0.021 (3)
C19 0.124 (4) 0.139 (4) 0.119 (4) −0.041 (3) −0.033 (3) −0.011 (3)
C20 0.171 (8) 0.147 (10) 0.065 (5) −0.097 (7) −0.039 (5) 0.034 (5)
C21 0.197 (9) 0.137 (8) 0.071 (5) −0.052 (7) −0.016 (5) −0.029 (5)
C22 0.082 (2) 0.0595 (17) 0.0467 (14) −0.0145 (15) −0.0234 (13) 0.0009 (13)
C23 0.081 (2) 0.075 (2) 0.0632 (18) −0.0214 (17) −0.0150 (15) −0.0092 (15)
C24 0.089 (2) 0.094 (2) 0.073 (2) −0.032 (2) −0.0205 (18) −0.0121 (18)
C25 0.075 (2) 0.116 (3) 0.075 (2) −0.011 (2) −0.0279 (18) −0.006 (2)
C26 0.088 (3) 0.105 (3) 0.112 (3) 0.010 (2) −0.038 (2) −0.033 (2)
C27 0.104 (3) 0.079 (2) 0.096 (3) −0.007 (2) −0.040 (2) −0.027 (2)
C28 0.0784 (19) 0.0533 (16) 0.0523 (15) −0.0204 (15) −0.0306 (14) 0.0081 (13)
C29 0.090 (2) 0.0656 (18) 0.0599 (17) −0.0326 (17) −0.0351 (16) 0.0073 (15)
C30 0.086 (2) 0.078 (2) 0.097 (2) −0.0317 (19) −0.049 (2) 0.0062 (18)
C31 0.068 (2) 0.0630 (19) 0.097 (2) −0.0120 (15) −0.0364 (17) −0.0077 (17)
C32 0.0551 (17) 0.0622 (18) 0.093 (2) −0.0032 (14) −0.0152 (15) −0.0213 (17)
C33 0.087 (2) 0.078 (2) 0.071 (2) −0.0079 (18) −0.0181 (17) −0.0196 (17)
C34 0.086 (2) 0.081 (2) 0.069 (2) −0.0279 (18) −0.0039 (16) −0.0120 (17)
C35 0.0668 (18) 0.0706 (19) 0.073 (2) −0.0176 (15) −0.0114 (15) −0.0085 (16)
C36 0.089 (2) 0.083 (2) 0.0656 (19) −0.0233 (19) −0.0201 (16) −0.0038 (17)
C37 0.076 (2) 0.074 (2) 0.080 (2) −0.0204 (17) −0.0094 (16) −0.0014 (17)
C38 0.166 (5) 0.150 (4) 0.093 (3) −0.082 (4) −0.041 (3) −0.017 (3)
C39 0.111 (4) 0.105 (4) 0.219 (7) −0.035 (3) −0.059 (4) −0.020 (4)
C40 0.109 (4) 0.106 (4) 0.202 (6) −0.027 (3) −0.032 (4) −0.015 (4)
C41 0.162 (15) 0.182 (13) 0.32 (3) 0.038 (11) 0.090 (15) 0.014 (17)
C42 0.108 (9) 0.44 (3) 0.254 (19) 0.042 (14) −0.034 (11) −0.048 (19)
C20' 0.41 (4) 0.164 (19) 0.071 (10) −0.15 (2) −0.052 (14) 0.041 (11)
C21' 0.121 (11) 0.22 (2) 0.132 (13) −0.017 (12) 0.003 (9) 0.008 (13)
C41' 0.044 (6) 0.194 (18) 0.154 (13) −0.035 (8) −0.026 (7) −0.002 (11)
C42' 0.100 (11) 0.192 (16) 0.205 (18) −0.034 (11) 0.076 (12) −0.095 (15)
N1 0.0600 (15) 0.0578 (15) 0.0877 (19) −0.0113 (12) −0.0045 (13) −0.0002 (13)
N2 0.082 (2) 0.0746 (19) 0.115 (3) −0.0258 (16) −0.0075 (17) −0.0036 (18)
N3 0.085 (2) 0.0727 (19) 0.121 (3) −0.0197 (16) −0.0201 (18) −0.0163 (18)
N4 0.0657 (15) 0.0622 (15) 0.0607 (15) −0.0086 (12) −0.0096 (11) −0.0021 (11)
N5 0.102 (2) 0.0855 (19) 0.0711 (18) −0.0220 (17) −0.0203 (15) −0.0098 (15)
N6 0.0871 (18) 0.0588 (14) 0.0496 (13) −0.0233 (13) −0.0235 (12) −0.0023 (11)
N7 0.111 (2) 0.0760 (17) 0.0627 (15) −0.0389 (16) −0.0237 (15) −0.0095 (13)
N8 0.117 (2) 0.0825 (19) 0.0650 (16) −0.0486 (18) −0.0337 (15) −0.0017 (14)
N9 0.0634 (15) 0.0572 (14) 0.0666 (14) −0.0112 (11) −0.0280 (11) −0.0040 (11)
N10 0.0599 (16) 0.0815 (19) 0.134 (3) −0.0122 (14) −0.0391 (16) −0.0159 (18)
O1 0.144 (3) 0.103 (2) 0.114 (2) −0.0306 (18) −0.0407 (18) −0.0324 (17)
O2 0.1180 (19) 0.0982 (17) 0.0616 (13) −0.0480 (16) −0.0136 (12) 0.0013 (12)
O3 0.0943 (18) 0.114 (2) 0.147 (2) −0.0462 (16) −0.0537 (17) −0.0124 (18)
O4 0.0615 (13) 0.0880 (16) 0.138 (2) −0.0121 (12) −0.0179 (13) −0.0449 (16)
O5 0.0979 (18) 0.1090 (19) 0.0956 (17) −0.0366 (15) −0.0251 (14) −0.0123 (15)
O6 0.1103 (19) 0.1090 (19) 0.0899 (17) −0.0546 (16) −0.0113 (14) −0.0179 (14)

Geometric parameters (Å, °)

C1—C6 1.366 (4) C25—H25 0.9300
C1—C2 1.379 (5) C26—C27 1.364 (5)
C1—N1 1.422 (4) C26—H26 0.9300
C2—C3 1.370 (6) C27—H27 0.9300
C2—H2 0.9300 C28—N6 1.354 (4)
C3—C4 1.365 (6) C28—N9 1.360 (4)
C3—H3 0.9300 C28—C29 1.363 (4)
C4—C5 1.373 (5) C29—N8 1.373 (4)
C4—H4 0.9300 C29—C30 1.422 (5)
C5—C6 1.390 (5) C30—O3 1.211 (4)
C5—H5 0.9300 C30—N10 1.426 (4)
C6—H6 0.9300 C31—N9 1.293 (4)
C7—C8 1.354 (4) C31—O4 1.339 (4)
C7—N4 1.355 (4) C31—N10 1.359 (4)
C7—N1 1.366 (4) C32—C37 1.359 (5)
C8—N3 1.360 (4) C32—C33 1.371 (5)
C8—C9 1.432 (5) C32—O4 1.407 (4)
C9—O1 1.217 (4) C33—C34 1.365 (4)
C9—N5 1.413 (5) C33—H33 0.9300
C10—N4 1.301 (4) C34—C35 1.373 (4)
C10—O2 1.339 (4) C34—H34 0.9300
C10—N5 1.363 (4) C35—O6 1.367 (4)
C11—C12 1.365 (4) C35—C36 1.371 (4)
C11—C16 1.368 (5) C36—C37 1.372 (4)
C11—O2 1.406 (4) C36—H36 0.9300
C12—C13 1.376 (5) C37—H37 0.9300
C12—H12 0.9300 C38—O6 1.424 (5)
C13—C14 1.379 (5) C38—H38A 0.9600
C13—H13 0.9300 C38—H38B 0.9600
C14—O5 1.374 (4) C38—H38C 0.9600
C14—C15 1.376 (4) C39—C40 1.414 (8)
C15—C16 1.382 (5) C39—N10 1.510 (6)
C15—H15 0.9300 C39—H39A 0.9700
C16—H16 0.9300 C39—H39B 0.9700
C17—O5 1.413 (4) C40—C41' 1.574 (9)
C17—H17A 0.9600 C40—C41 1.590 (9)
C17—H17B 0.9600 C40—H40A 0.9700
C17—H17C 0.9600 C40—H40B 0.9700
C18—C19 1.454 (6) C40—H40C 0.9700
C18—N5 1.556 (5) C40—H40D 0.9700
C18—H18A 0.9700 C41—C42 1.471 (10)
C18—H18B 0.9700 C41—H41A 0.9700
C19—C20 1.560 (7) C41—H41B 0.9700
C19—C20' 1.587 (10) C42—H42A 0.9600
C19—H19A 0.9700 C42—H42B 0.9600
C19—H19B 0.9700 C42—H42C 0.9600
C19—H19C 0.9700 C20'—C21' 1.525 (10)
C19—H19D 0.9700 C20'—H20C 0.9700
C20—C21 1.486 (8) C20'—H20D 0.9700
C20—H20A 0.9700 C21'—H21D 0.9600
C20—H20B 0.9700 C21'—H21E 0.9600
C21—H21A 0.9600 C21'—H21F 0.9600
C21—H21B 0.9600 C41'—C42' 1.499 (10)
C21—H21C 0.9600 C41'—H41C 0.9700
C22—C23 1.373 (4) C41'—H41D 0.9700
C22—C27 1.377 (5) C42'—H42D 0.9600
C22—N6 1.432 (4) C42'—H42E 0.9600
C23—C24 1.387 (5) C42'—H42F 0.9600
C23—H23 0.9300 N1—N2 1.384 (4)
C24—C25 1.372 (5) N2—N3 1.298 (4)
C24—H24 0.9300 N6—N7 1.379 (3)
C25—C26 1.361 (5) N7—N8 1.292 (4)
C6—C1—C2 119.8 (4) N8—C29—C30 129.9 (3)
C6—C1—N1 121.5 (3) O3—C30—C29 129.1 (4)
C2—C1—N1 118.8 (3) O3—C30—N10 120.7 (4)
C3—C2—C1 119.6 (4) C29—C30—N10 110.2 (3)
C3—C2—H2 120.2 N9—C31—O4 120.8 (3)
C1—C2—H2 120.2 N9—C31—N10 127.0 (3)
C4—C3—C2 121.2 (4) O4—C31—N10 112.2 (3)
C4—C3—H3 119.4 C37—C32—C33 120.5 (3)
C2—C3—H3 119.4 C37—C32—O4 117.0 (3)
C3—C4—C5 119.4 (4) C33—C32—O4 122.0 (3)
C3—C4—H4 120.3 C34—C33—C32 119.3 (3)
C5—C4—H4 120.3 C34—C33—H33 120.3
C4—C5—C6 119.9 (4) C32—C33—H33 120.3
C4—C5—H5 120.1 C33—C34—C35 121.0 (3)
C6—C5—H5 120.1 C33—C34—H34 119.5
C1—C6—C5 120.1 (3) C35—C34—H34 119.5
C1—C6—H6 119.9 O6—C35—C36 124.8 (3)
C5—C6—H6 119.9 O6—C35—C34 116.4 (3)
C8—C7—N4 127.8 (3) C36—C35—C34 118.8 (3)
C8—C7—N1 105.1 (3) C35—C36—C37 120.5 (3)
N4—C7—N1 127.0 (3) C35—C36—H36 119.7
C7—C8—N3 110.2 (3) C37—C36—H36 119.7
C7—C8—C9 120.2 (3) C32—C37—C36 119.8 (3)
N3—C8—C9 129.5 (3) C32—C37—H37 120.1
O1—C9—N5 120.9 (4) C36—C37—H37 120.1
O1—C9—C8 128.0 (4) O6—C38—H38A 109.5
N5—C9—C8 111.0 (3) O6—C38—H38B 109.5
N4—C10—O2 121.5 (3) H38A—C38—H38B 109.5
N4—C10—N5 127.2 (3) O6—C38—H38C 109.5
O2—C10—N5 111.3 (3) H38A—C38—H38C 109.5
C12—C11—C16 121.4 (3) H38B—C38—H38C 109.5
C12—C11—O2 116.8 (3) C40—C39—N10 109.1 (4)
C16—C11—O2 121.2 (3) C40—C39—H39A 109.9
C11—C12—C13 120.2 (3) N10—C39—H39A 109.9
C11—C12—H12 119.9 C40—C39—H39B 109.9
C13—C12—H12 119.9 N10—C39—H39B 109.9
C12—C13—C14 119.3 (3) H39A—C39—H39B 108.3
C12—C13—H13 120.3 C39—C40—C41' 97.0 (6)
C14—C13—H13 120.3 C39—C40—C41 129.1 (7)
O5—C14—C15 115.7 (3) C41'—C40—C41 33.0 (6)
O5—C14—C13 124.6 (3) C39—C40—H40A 105.0
C15—C14—C13 119.7 (3) C41'—C40—H40A 112.3
C14—C15—C16 121.0 (3) C41—C40—H40A 105.0
C14—C15—H15 119.5 C39—C40—H40B 105.0
C16—C15—H15 119.5 C41'—C40—H40B 128.6
C11—C16—C15 118.3 (3) C41—C40—H40B 105.0
C11—C16—H16 120.9 H40A—C40—H40B 105.9
C15—C16—H16 120.9 C39—C40—H40C 111.7
O5—C17—H17A 109.5 C41'—C40—H40C 112.5
O5—C17—H17B 109.5 C41—C40—H40C 101.3
H17A—C17—H17B 109.5 H40A—C40—H40C 7.0
O5—C17—H17C 109.5 H40B—C40—H40C 101.4
H17A—C17—H17C 109.5 C39—C40—H40D 112.6
H17B—C17—H17C 109.5 C41'—C40—H40D 112.7
C19—C18—N5 109.9 (4) C41—C40—H40D 89.7
C19—C18—H18A 109.7 H40A—C40—H40D 115.4
N5—C18—H18A 109.7 H40B—C40—H40D 16.0
C19—C18—H18B 109.7 H40C—C40—H40D 109.8
N5—C18—H18B 109.7 C42—C41—C40 107.2 (9)
H18A—C18—H18B 108.2 C42—C41—H41A 110.3
C18—C19—C20 114.6 (6) C40—C41—H41A 110.3
C18—C19—C20' 89.4 (7) C42—C41—H41B 110.3
C20—C19—C20' 28.8 (6) C40—C41—H41B 110.3
C18—C19—H19A 108.6 H41A—C41—H41B 108.5
C20—C19—H19A 108.6 C21'—C20'—C19 105.0 (9)
C20'—C19—H19A 106.6 C21'—C20'—H20C 110.7
C18—C19—H19B 108.6 C19—C20'—H20C 110.7
C20—C19—H19B 108.6 C21'—C20'—H20D 110.7
C20'—C19—H19B 133.2 C19—C20'—H20D 110.7
H19A—C19—H19B 107.6 H20C—C20'—H20D 108.8
C18—C19—H19C 113.7 C20'—C21'—H21D 109.5
C20—C19—H19C 111.4 C20'—C21'—H21E 109.5
C20'—C19—H19C 113.5 H21D—C21'—H21E 109.5
H19A—C19—H19C 9.2 C20'—C21'—H21F 109.5
H19B—C19—H19C 98.5 H21D—C21'—H21F 109.5
C18—C19—H19D 113.7 H21E—C21'—H21F 109.5
C20—C19—H19D 90.2 C42'—C41'—C40 105.5 (8)
C20'—C19—H19D 114.1 C42'—C41'—H41C 110.6
H19A—C19—H19D 120.1 C40—C41'—H41C 110.6
H19B—C19—H19D 19.2 C42'—C41'—H41D 110.6
H19C—C19—H19D 111.0 C40—C41'—H41D 110.6
C21—C20—C19 107.0 (6) H41C—C41'—H41D 108.8
C21—C20—H20A 110.3 C41'—C42'—H42D 109.5
C19—C20—H20A 110.3 C41'—C42'—H42E 109.5
C21—C20—H20B 110.3 H42D—C42'—H42E 109.5
C19—C20—H20B 110.3 C41'—C42'—H42F 109.5
H20A—C20—H20B 108.6 H42D—C42'—H42F 109.5
C23—C22—C27 119.8 (3) H42E—C42'—H42F 109.5
C23—C22—N6 120.9 (3) C7—N1—N2 108.1 (3)
C27—C22—N6 119.3 (3) C7—N1—C1 132.5 (3)
C22—C23—C24 119.0 (3) N2—N1—C1 119.4 (3)
C22—C23—H23 120.5 N3—N2—N1 108.7 (3)
C24—C23—H23 120.5 N2—N3—C8 107.8 (3)
C25—C24—C23 121.0 (3) C10—N4—C7 111.3 (3)
C25—C24—H24 119.5 C10—N5—C9 122.4 (3)
C23—C24—H24 119.5 C10—N5—C18 120.5 (3)
C26—C25—C24 118.9 (3) C9—N5—C18 116.7 (3)
C26—C25—H25 120.5 C28—N6—N7 108.7 (2)
C24—C25—H25 120.5 C28—N6—C22 131.7 (2)
C25—C26—C27 121.2 (4) N7—N6—C22 119.5 (3)
C25—C26—H26 119.4 N8—N7—N6 108.7 (3)
C27—C26—H26 119.4 N7—N8—C29 108.0 (2)
C26—C27—C22 120.1 (3) C31—N9—C28 111.8 (2)
C26—C27—H27 119.9 C31—N10—C30 122.8 (3)
C22—C27—H27 119.9 C31—N10—C39 120.7 (3)
N6—C28—N9 127.6 (2) C30—N10—C39 116.3 (3)
N6—C28—C29 105.3 (3) C10—O2—C11 121.3 (2)
N9—C28—C29 127.0 (3) C31—O4—C32 120.4 (2)
C28—C29—N8 109.2 (3) C14—O5—C17 118.2 (3)
C28—C29—C30 121.0 (3) C35—O6—C38 117.6 (3)
C6—C1—C2—C3 −0.7 (5) N4—C7—N1—N2 179.2 (3)
N1—C1—C2—C3 178.0 (3) C8—C7—N1—C1 −178.7 (3)
C1—C2—C3—C4 1.1 (6) N4—C7—N1—C1 0.4 (5)
C2—C3—C4—C5 −1.2 (6) C6—C1—N1—C7 −13.3 (5)
C3—C4—C5—C6 0.8 (6) C2—C1—N1—C7 168.0 (3)
C2—C1—C6—C5 0.3 (5) C6—C1—N1—N2 168.0 (3)
N1—C1—C6—C5 −178.3 (3) C2—C1—N1—N2 −10.6 (4)
C4—C5—C6—C1 −0.4 (5) C7—N1—N2—N3 0.2 (3)
N4—C7—C8—N3 −179.4 (3) C1—N1—N2—N3 179.1 (3)
N1—C7—C8—N3 −0.3 (3) N1—N2—N3—C8 −0.4 (4)
N4—C7—C8—C9 −0.8 (5) C7—C8—N3—N2 0.4 (4)
N1—C7—C8—C9 178.3 (3) C9—C8—N3—N2 −178.0 (3)
C7—C8—C9—O1 −178.8 (3) O2—C10—N4—C7 178.2 (3)
N3—C8—C9—O1 −0.5 (6) N5—C10—N4—C7 −0.2 (4)
C7—C8—C9—N5 0.2 (4) C8—C7—N4—C10 0.8 (4)
N3—C8—C9—N5 178.5 (3) N1—C7—N4—C10 −178.1 (3)
C16—C11—C12—C13 1.6 (5) N4—C10—N5—C9 −0.4 (5)
O2—C11—C12—C13 −170.2 (3) O2—C10—N5—C9 −178.9 (3)
C11—C12—C13—C14 −0.2 (4) N4—C10—N5—C18 172.7 (3)
C12—C13—C14—O5 179.2 (3) O2—C10—N5—C18 −5.9 (5)
C12—C13—C14—C15 −1.7 (5) O1—C9—N5—C10 179.4 (3)
O5—C14—C15—C16 −178.5 (3) C8—C9—N5—C10 0.3 (5)
C13—C14—C15—C16 2.3 (5) O1—C9—N5—C18 6.1 (5)
C12—C11—C16—C15 −1.0 (5) C8—C9—N5—C18 −173.0 (3)
O2—C11—C16—C15 170.4 (3) C19—C18—N5—C10 96.9 (4)
C14—C15—C16—C11 −1.0 (5) C19—C18—N5—C9 −89.7 (4)
N5—C18—C19—C20 −175.0 (4) N9—C28—N6—N7 −178.9 (2)
N5—C18—C19—C20' 170.7 (10) C29—C28—N6—N7 −0.1 (3)
C18—C19—C20—C21 −72.3 (10) N9—C28—N6—C22 −0.8 (4)
C20'—C19—C20—C21 −41 (2) C29—C28—N6—C22 178.0 (2)
C27—C22—C23—C24 0.9 (4) C23—C22—N6—C28 10.2 (4)
N6—C22—C23—C24 −179.4 (3) C27—C22—N6—C28 −170.0 (3)
C22—C23—C24—C25 −0.4 (5) C23—C22—N6—N7 −171.8 (2)
C23—C24—C25—C26 −0.3 (5) C27—C22—N6—N7 7.9 (4)
C24—C25—C26—C27 0.5 (6) C28—N6—N7—N8 0.1 (3)
C25—C26—C27—C22 −0.1 (6) C22—N6—N7—N8 −178.3 (2)
C23—C22—C27—C26 −0.7 (5) N6—N7—N8—C29 0.0 (3)
N6—C22—C27—C26 179.6 (3) C28—C29—N8—N7 −0.1 (3)
N6—C28—C29—N8 0.1 (3) C30—C29—N8—N7 −179.2 (3)
N9—C28—C29—N8 178.9 (2) O4—C31—N9—C28 −177.3 (3)
N6—C28—C29—C30 179.3 (3) N10—C31—N9—C28 1.1 (4)
N9—C28—C29—C30 −1.9 (4) N6—C28—N9—C31 −179.1 (3)
C28—C29—C30—O3 177.9 (3) C29—C28—N9—C31 2.4 (4)
N8—C29—C30—O3 −3.1 (6) N9—C31—N10—C30 −5.1 (5)
C28—C29—C30—N10 −1.8 (4) O4—C31—N10—C30 173.4 (3)
N8—C29—C30—N10 177.2 (3) N9—C31—N10—C39 169.6 (4)
C37—C32—C33—C34 1.7 (5) O4—C31—N10—C39 −11.9 (5)
O4—C32—C33—C34 −170.3 (3) O3—C30—N10—C31 −174.8 (3)
C32—C33—C34—C35 0.9 (5) C29—C30—N10—C31 5.0 (4)
C33—C34—C35—O6 176.0 (3) O3—C30—N10—C39 10.3 (5)
C33—C34—C35—C36 −2.8 (5) C29—C30—N10—C39 −169.9 (4)
O6—C35—C36—C37 −176.5 (3) C40—C39—N10—C31 91.3 (5)
C34—C35—C36—C37 2.3 (5) C40—C39—N10—C30 −93.7 (5)
C33—C32—C37—C36 −2.2 (5) N4—C10—O2—C11 8.4 (5)
O4—C32—C37—C36 170.1 (3) N5—C10—O2—C11 −173.0 (3)
C35—C36—C37—C32 0.2 (5) C12—C11—O2—C10 −132.0 (3)
N10—C39—C40—C41' 170.7 (7) C16—C11—O2—C10 56.2 (4)
N10—C39—C40—C41 179.6 (11) N9—C31—O4—C32 −7.8 (5)
C39—C40—C41—C42 −25 (2) N10—C31—O4—C32 173.6 (3)
C41'—C40—C41—C42 −9.0 (16) C37—C32—O4—C31 128.2 (3)
C18—C19—C20'—C21' 174.3 (17) C33—C32—O4—C31 −59.6 (4)
C20—C19—C20'—C21' 22.1 (13) C15—C14—O5—C17 166.1 (3)
C39—C40—C41'—C42' −177.3 (11) C13—C14—O5—C17 −14.8 (5)
C41—C40—C41'—C42' 15.4 (17) C36—C35—O6—C38 11.9 (5)
C8—C7—N1—N2 0.1 (3) C34—C35—O6—C38 −166.9 (4)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: YA2108).

References

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809046017/ya2108sup1.cif

e-65-o3032-sup1.cif (35.9KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809046017/ya2108Isup2.hkl

e-65-o3032-Isup2.hkl (339.6KB, hkl)

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


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