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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2011 Sep 30;67(Pt 10):o2727. doi: 10.1107/S1600536811035197

rac-3-{4-[(4-Nitro­benzyl­idene)amino]-3-phenyl-5-sulfanyl­idene-4,5-dihydro-1H-1,2,4-triazol-1-yl}-1,3-diphenyl­propan-1-one

Wei Wang a,b,*, Yan Gao b, Chao Xu b, Wen-peng Wu b, Qing-lei Liu a
PMCID: PMC3201282  PMID: 22058798

Abstract

In the title mol­ecule, C30H23N5O3S, the 1,2,4-triazole ring is approximately planar (r.m.s. deviation = 0.006 Å), and forms dihedral angles of 66.0 (2), 65.1 (2), 30.1 (2) and 28.1 (2)° with the four phenyl rings. The phenyl ring of the benzyl group directly attached to the triazole ring is almost perpendicular to the nitro­phenyl ring, making a dihedral angle of 84.9 (2)°.

Related literature

For the crystal structures of related 1,2,4-triazole-5(4H)-thione derivatives, see: Al-Tamimi et al. (2010 ▶); Fun et al. (2009 ▶); Gao et al. (2011 ▶); Tan et al. (2010 ▶); Wang et al. (2011 ▶); Zhao et al. (2010 ▶).graphic file with name e-67-o2727-scheme1.jpg

Experimental

Crystal data

  • C30H23N5O3S

  • M r = 533.59

  • Monoclinic, Inline graphic

  • a = 13.3303 (13) Å

  • b = 21.832 (2) Å

  • c = 9.2773 (9) Å

  • β = 98.213 (3)°

  • V = 2672.2 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.16 mm−1

  • T = 113 K

  • 0.20 × 0.18 × 0.12 mm

Data collection

  • Rigaku Saturn CCD area-detector diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.968, T max = 0.981

  • 27241 measured reflections

  • 6372 independent reflections

  • 5124 reflections with I > 2σ(I)

  • R int = 0.040

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049

  • wR(F 2) = 0.131

  • S = 1.10

  • 6372 reflections

  • 352 parameters

  • H-atom parameters constrained

  • Δρmax = 0.33 e Å−3

  • Δρmin = −0.25 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811035197/zs2140sup1.cif

e-67-o2727-sup1.cif (24.9KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035197/zs2140Isup2.hkl

e-67-o2727-Isup2.hkl (311.9KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536811035197/zs2140Isup3.cml

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

Acknowledgments

We gratefully acknowledge support of this study by the Key Laboratory Project of Liaoning Province (No. 2008S127) and the Doctoral Starting Foundation of Liaoning Province (No. 20071103).

supplementary crystallographic information

Comment

In a continuation of the structural study by our group of Mannich base derivatives synthesized by the reaction of amino heterocycles and aromatic aldehydes (Wang et al., 2011), we present here the crystal structure of the title compound, C30H23N5O3S.

In this compound the bond lengths and angles are comparable with those reported in the related 1,2,4-triazole-5(4H)-thione derivatives (Al-Tamimi et al., 2010; Fun et al., 2009; Tan et al., 2010; Wang et al., 2011). The 1,2,4-triazole ring is planar with an r.m.s 0.0055 (2) Å and a maximium deviation of 0.0083 (2) Å for atom N3. The C1 and C2 atoms of the 1,2,4-triazole ring show distorted Csp2 hybridization states with bond angles of 102.69 (13)° (N1—C1—N3); 131.16 (12)° (N3—C1—S1); 110.38 (13)° (N2—C2—N3) and 126.98 (14)° (N3—C2—C25), which are similar to those in the other reported triazole derivatives (Zhao et al., 2010; Gao et al., 2011). The 1,2,4-triazole ring forms dihedral angles of 114.0 (2), 114.9 (2), 151.9 (2)° and 149.9 (2)° with the phenyl rings C6—C11, C12—C17 and C25—C30 and the nitrophenyl ring C19—C24. The phenyl ring of the benzyl group attached to atom N1 of the triazole ring (C12—C17) is almost perpendicular to the nitrophenyl ring, with a dihedral angle of 95.1 (2)°.

Experimental

The title compound was synthesized in the reaction of 4-nitrobenzaldehyde (2.0 mmol) and 3-(4-amino-3-phenyl-5-thioxo-4,5- dihydro-1H-1,2,4-triazol-1-yl)-1,3-diphenylpropan-1-one (2.0 mmol), by refluxing in ethanol. The reaction progress was monitored via TLC. The resulting precipitate was filtered off, washed with cold ethanol, dried and purified to give the target product as a colorless solid in 66% yield. Crystals suitable for single-crystal X-ray analysis were grown by slow evaporation of a solution in chloroform–ethanol (1:1).

Refinement

Hydrogen atoms were positioned geometrically and refined as riding (C—H = 0.95-1.00 Å) and allowed to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.

Fig. 1.

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A view of a molecule of the title compound showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 60% probability level.

Crystal data

C30H23N5O3S F(000) = 1112
Mr = 533.59 Dx = 1.326 Mg m−3
Monoclinic, P21/c Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc Cell parameters from 8592 reflections
a = 13.3303 (13) Å θ = 1.5–27.9°
b = 21.832 (2) Å µ = 0.16 mm−1
c = 9.2773 (9) Å T = 113 K
β = 98.213 (3)° Prism, colorless
V = 2672.2 (4) Å3 0.20 × 0.18 × 0.12 mm
Z = 4
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Data collection

Rigaku Saturn CCD area-detector diffractometer 6372 independent reflections
Radiation source: rotating anode 5124 reflections with I > 2σ(I)
multilayer Rint = 0.040
Detector resolution: 14.63 pixels mm-1 θmax = 27.9°, θmin = 1.5°
φ and ω scans h = −15→17
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) k = −27→28
Tmin = 0.968, Tmax = 0.981 l = −12→12
27241 measured reflections
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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)] = 0.049 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131 H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.0667P)2 + 0.1147P] where P = (Fo2 + 2Fc2)/3
6372 reflections (Δ/σ)max < 0.001
352 parameters Δρmax = 0.33 e Å−3
0 restraints Δρmin = −0.25 e Å−3
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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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
S1 0.40778 (3) 0.258871 (19) 0.46718 (5) 0.03324 (14)
O1 0.33880 (9) 0.08657 (5) 0.76721 (14) 0.0346 (3)
O2 −0.05157 (12) 0.41949 (7) −0.22517 (19) 0.0649 (5)
O3 −0.07948 (10) 0.33342 (7) −0.34027 (17) 0.0545 (4)
N1 0.41855 (9) 0.13669 (6) 0.49993 (14) 0.0250 (3)
N2 0.37677 (10) 0.08227 (6) 0.44644 (15) 0.0273 (3)
N3 0.30586 (9) 0.16063 (6) 0.32011 (14) 0.0265 (3)
N4 0.23159 (10) 0.18795 (7) 0.22006 (15) 0.0305 (3)
N5 −0.03993 (11) 0.36460 (8) −0.23724 (19) 0.0440 (4)
C1 0.37777 (12) 0.18629 (7) 0.42770 (17) 0.0258 (3)
C2 0.30761 (12) 0.09772 (7) 0.33837 (18) 0.0268 (4)
C3 0.49357 (11) 0.13916 (7) 0.63312 (17) 0.0244 (3)
H3 0.4677 0.1679 0.7033 0.029*
C4 0.50513 (11) 0.07593 (7) 0.70349 (17) 0.0252 (3)
H4A 0.5231 0.0462 0.6307 0.030*
H4B 0.5621 0.0772 0.7846 0.030*
C5 0.41174 (12) 0.05325 (7) 0.76135 (17) 0.0255 (3)
C6 0.41222 (11) −0.01130 (7) 0.81389 (16) 0.0246 (3)
C7 0.50162 (12) −0.04455 (7) 0.84342 (17) 0.0264 (3)
H7 0.5640 −0.0265 0.8279 0.032*
C8 0.50025 (13) −0.10395 (7) 0.89538 (18) 0.0306 (4)
H8 0.5617 −0.1265 0.9151 0.037*
C9 0.40986 (13) −0.13060 (8) 0.91858 (19) 0.0332 (4)
H9 0.4091 −0.1715 0.9534 0.040*
C10 0.32011 (14) −0.09748 (8) 0.89083 (19) 0.0342 (4)
H10 0.2580 −0.1155 0.9079 0.041*
C11 0.32128 (12) −0.03833 (8) 0.83847 (18) 0.0305 (4)
H11 0.2598 −0.0159 0.8190 0.037*
C12 0.59542 (11) 0.16257 (7) 0.60266 (17) 0.0244 (3)
C13 0.64074 (12) 0.14022 (8) 0.48742 (18) 0.0305 (4)
H13 0.6057 0.1114 0.4219 0.037*
C14 0.73711 (13) 0.15985 (8) 0.4674 (2) 0.0363 (4)
H14 0.7679 0.1442 0.3888 0.044*
C15 0.78809 (13) 0.20224 (8) 0.5621 (2) 0.0358 (4)
H15 0.8536 0.2160 0.5482 0.043*
C16 0.74310 (13) 0.22440 (8) 0.67691 (19) 0.0335 (4)
H16 0.7783 0.2532 0.7424 0.040*
C17 0.64733 (12) 0.20516 (7) 0.69740 (18) 0.0291 (4)
H17 0.6169 0.2210 0.7761 0.035*
C18 0.23453 (13) 0.24544 (9) 0.1994 (2) 0.0375 (4)
H18 0.2862 0.2696 0.2532 0.045*
C19 0.15729 (12) 0.27428 (9) 0.0914 (2) 0.0363 (4)
C20 0.09104 (13) 0.24006 (8) −0.0091 (2) 0.0359 (4)
H20 0.0912 0.1966 −0.0037 0.043*
C21 0.02564 (13) 0.26954 (9) −0.1159 (2) 0.0368 (4)
H21 −0.0185 0.2469 −0.1858 0.044*
C22 0.02605 (12) 0.33251 (8) −0.1185 (2) 0.0356 (4)
C23 0.08666 (13) 0.36786 (9) −0.0181 (2) 0.0427 (5)
H23 0.0828 0.4113 −0.0206 0.051*
C24 0.15371 (13) 0.33767 (9) 0.0872 (2) 0.0422 (5)
H24 0.1974 0.3608 0.1568 0.051*
C25 0.24185 (12) 0.05265 (8) 0.25380 (19) 0.0321 (4)
C26 0.22312 (14) −0.00168 (8) 0.3235 (2) 0.0435 (5)
H26 0.2505 −0.0077 0.4227 0.052*
C27 0.16458 (16) −0.04698 (9) 0.2484 (3) 0.0564 (6)
H27 0.1526 −0.0843 0.2959 0.068*
C28 0.12366 (15) −0.03807 (10) 0.1051 (3) 0.0564 (6)
H28 0.0829 −0.0691 0.0544 0.068*
C29 0.14132 (14) 0.01515 (10) 0.0354 (2) 0.0497 (6)
H29 0.1124 0.0210 −0.0633 0.060*
C30 0.20157 (13) 0.06087 (9) 0.1082 (2) 0.0394 (5)
H30 0.2151 0.0974 0.0589 0.047*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
S1 0.0366 (3) 0.0258 (2) 0.0356 (3) 0.00011 (17) −0.00091 (18) 0.00255 (18)
O1 0.0319 (6) 0.0328 (6) 0.0388 (7) 0.0046 (5) 0.0042 (5) 0.0019 (5)
O2 0.0617 (10) 0.0478 (9) 0.0783 (12) 0.0076 (8) −0.0139 (8) 0.0202 (8)
O3 0.0449 (8) 0.0643 (10) 0.0487 (9) 0.0034 (7) −0.0129 (7) 0.0094 (7)
N1 0.0259 (7) 0.0233 (7) 0.0240 (7) 0.0000 (5) −0.0030 (5) −0.0019 (5)
N2 0.0260 (7) 0.0266 (7) 0.0273 (7) −0.0003 (5) −0.0034 (5) −0.0049 (6)
N3 0.0228 (7) 0.0326 (8) 0.0226 (7) 0.0029 (5) −0.0017 (5) 0.0005 (6)
N4 0.0257 (7) 0.0405 (8) 0.0237 (7) 0.0052 (6) −0.0020 (5) 0.0046 (6)
N5 0.0315 (8) 0.0484 (10) 0.0501 (11) 0.0016 (7) −0.0006 (7) 0.0160 (8)
C1 0.0236 (8) 0.0310 (9) 0.0221 (8) 0.0022 (6) 0.0015 (6) 0.0023 (6)
C2 0.0232 (8) 0.0315 (9) 0.0251 (8) 0.0021 (6) 0.0010 (6) −0.0042 (7)
C3 0.0258 (8) 0.0240 (8) 0.0217 (8) −0.0005 (6) −0.0020 (6) −0.0011 (6)
C4 0.0259 (8) 0.0253 (8) 0.0230 (8) −0.0001 (6) −0.0017 (6) 0.0005 (6)
C5 0.0275 (8) 0.0259 (8) 0.0213 (8) 0.0014 (6) −0.0027 (6) −0.0023 (6)
C6 0.0281 (8) 0.0258 (8) 0.0191 (8) −0.0018 (6) 0.0009 (6) −0.0032 (6)
C7 0.0287 (8) 0.0267 (8) 0.0232 (8) −0.0023 (6) 0.0018 (6) −0.0020 (6)
C8 0.0348 (9) 0.0290 (8) 0.0274 (9) 0.0017 (7) 0.0026 (7) −0.0002 (7)
C9 0.0447 (10) 0.0267 (8) 0.0278 (9) −0.0052 (7) 0.0041 (7) 0.0005 (7)
C10 0.0352 (9) 0.0357 (9) 0.0321 (10) −0.0100 (7) 0.0055 (7) −0.0012 (8)
C11 0.0273 (8) 0.0347 (9) 0.0288 (9) −0.0013 (7) 0.0019 (7) −0.0030 (7)
C12 0.0269 (8) 0.0221 (8) 0.0225 (8) 0.0005 (6) −0.0026 (6) 0.0025 (6)
C13 0.0334 (9) 0.0311 (9) 0.0255 (9) −0.0055 (7) −0.0004 (7) −0.0050 (7)
C14 0.0378 (10) 0.0422 (10) 0.0298 (9) −0.0041 (8) 0.0085 (7) −0.0060 (8)
C15 0.0314 (9) 0.0401 (10) 0.0359 (10) −0.0073 (8) 0.0049 (7) 0.0011 (8)
C16 0.0332 (9) 0.0298 (9) 0.0360 (10) −0.0072 (7) −0.0003 (7) −0.0045 (7)
C17 0.0316 (9) 0.0283 (8) 0.0268 (8) −0.0016 (7) 0.0015 (7) −0.0048 (7)
C18 0.0290 (9) 0.0465 (11) 0.0358 (10) 0.0001 (8) 0.0003 (7) 0.0075 (8)
C19 0.0250 (9) 0.0456 (11) 0.0376 (10) 0.0017 (7) 0.0023 (7) 0.0116 (8)
C20 0.0309 (9) 0.0395 (10) 0.0368 (10) 0.0007 (7) 0.0029 (7) 0.0073 (8)
C21 0.0254 (9) 0.0463 (11) 0.0384 (10) 0.0004 (8) 0.0034 (7) 0.0045 (8)
C22 0.0217 (8) 0.0459 (11) 0.0384 (10) 0.0008 (7) 0.0014 (7) 0.0124 (8)
C23 0.0324 (10) 0.0420 (11) 0.0523 (12) −0.0025 (8) 0.0010 (8) 0.0139 (9)
C24 0.0327 (10) 0.0443 (11) 0.0464 (12) −0.0056 (8) −0.0054 (8) 0.0087 (9)
C25 0.0236 (8) 0.0375 (10) 0.0331 (9) 0.0050 (7) −0.0031 (7) −0.0122 (8)
C26 0.0400 (11) 0.0356 (10) 0.0498 (12) 0.0003 (8) −0.0109 (9) −0.0092 (9)
C27 0.0500 (13) 0.0375 (11) 0.0750 (16) −0.0032 (9) −0.0141 (11) −0.0136 (11)
C28 0.0390 (11) 0.0530 (13) 0.0705 (16) 0.0023 (10) −0.0148 (10) −0.0310 (12)
C29 0.0320 (10) 0.0686 (15) 0.0441 (12) 0.0096 (10) −0.0092 (8) −0.0259 (11)
C30 0.0292 (9) 0.0521 (11) 0.0348 (10) 0.0064 (8) −0.0034 (7) −0.0142 (9)
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Geometric parameters (Å, °)

S1—C1 1.6622 (16) C12—C17 1.394 (2)
O1—C5 1.2218 (18) C13—C14 1.392 (2)
O2—N5 1.215 (2) C13—H13 0.9500
O3—N5 1.229 (2) C14—C15 1.386 (2)
N1—C1 1.3466 (19) C14—H14 0.9500
N1—N2 1.3745 (17) C15—C16 1.382 (2)
N1—C3 1.4754 (18) C15—H15 0.9500
N2—C2 1.3058 (19) C16—C17 1.383 (2)
N3—C2 1.383 (2) C16—H16 0.9500
N3—N4 1.3911 (17) C17—H17 0.9500
N3—C1 1.3984 (19) C18—C19 1.471 (2)
N4—C18 1.271 (2) C18—H18 0.9500
N5—C22 1.483 (2) C19—C24 1.385 (3)
C2—C25 1.468 (2) C19—C20 1.405 (2)
C3—C12 1.515 (2) C20—C21 1.382 (2)
C3—C4 1.525 (2) C20—H20 0.9500
C3—H3 1.0000 C21—C22 1.375 (2)
C4—C5 1.508 (2) C21—H21 0.9500
C4—H4A 0.9900 C22—C23 1.379 (3)
C4—H4B 0.9900 C23—C24 1.392 (2)
C5—C6 1.491 (2) C23—H23 0.9500
C6—C7 1.389 (2) C24—H24 0.9500
C6—C11 1.396 (2) C25—C26 1.390 (3)
C7—C8 1.385 (2) C25—C30 1.392 (2)
C7—H7 0.9500 C26—C27 1.384 (3)
C8—C9 1.382 (2) C26—H26 0.9500
C8—H8 0.9500 C27—C28 1.377 (3)
C9—C10 1.390 (2) C27—H27 0.9500
C9—H9 0.9500 C28—C29 1.367 (3)
C10—C11 1.381 (2) C28—H28 0.9500
C10—H10 0.9500 C29—C30 1.394 (3)
C11—H11 0.9500 C29—H29 0.9500
C12—C13 1.389 (2) C30—H30 0.9500
C1—N1—N2 113.68 (12) C12—C13—H13 119.8
C1—N1—C3 124.37 (13) C14—C13—H13 119.8
N2—N1—C3 121.68 (12) C15—C14—C13 119.95 (16)
C2—N2—N1 105.02 (12) C15—C14—H14 120.0
C2—N3—N4 120.35 (12) C13—C14—H14 120.0
C2—N3—C1 108.21 (12) C16—C15—C14 119.68 (16)
N4—N3—C1 130.87 (13) C16—C15—H15 120.2
C18—N4—N3 119.33 (14) C14—C15—H15 120.2
O2—N5—O3 124.84 (16) C15—C16—C17 120.68 (15)
O2—N5—C22 117.86 (17) C15—C16—H16 119.7
O3—N5—C22 117.30 (15) C17—C16—H16 119.7
N1—C1—N3 102.69 (13) C16—C17—C12 120.07 (16)
N1—C1—S1 126.13 (12) C16—C17—H17 120.0
N3—C1—S1 131.16 (12) C12—C17—H17 120.0
N2—C2—N3 110.38 (13) N4—C18—C19 119.45 (16)
N2—C2—C25 122.63 (15) N4—C18—H18 120.3
N3—C2—C25 126.98 (14) C19—C18—H18 120.3
N1—C3—C12 111.99 (12) C24—C19—C20 119.79 (16)
N1—C3—C4 109.89 (12) C24—C19—C18 117.69 (16)
C12—C3—C4 110.29 (12) C20—C19—C18 122.47 (17)
N1—C3—H3 108.2 C21—C20—C19 120.06 (17)
C12—C3—H3 108.2 C21—C20—H20 120.0
C4—C3—H3 108.2 C19—C20—H20 120.0
C5—C4—C3 114.30 (13) C22—C21—C20 118.34 (17)
C5—C4—H4A 108.7 C22—C21—H21 120.8
C3—C4—H4A 108.7 C20—C21—H21 120.8
C5—C4—H4B 108.7 C21—C22—C23 123.43 (16)
C3—C4—H4B 108.7 C21—C22—N5 118.82 (16)
H4A—C4—H4B 107.6 C23—C22—N5 117.74 (16)
O1—C5—C6 120.97 (15) C22—C23—C24 117.70 (18)
O1—C5—C4 121.53 (14) C22—C23—H23 121.2
C6—C5—C4 117.49 (13) C24—C23—H23 121.2
C7—C6—C11 119.18 (15) C19—C24—C23 120.59 (17)
C7—C6—C5 121.46 (14) C19—C24—H24 119.7
C11—C6—C5 119.33 (14) C23—C24—H24 119.7
C8—C7—C6 120.30 (15) C26—C25—C30 119.43 (16)
C8—C7—H7 119.8 C26—C25—C2 117.15 (16)
C6—C7—H7 119.8 C30—C25—C2 123.37 (17)
C9—C8—C7 120.23 (16) C27—C26—C25 120.1 (2)
C9—C8—H8 119.9 C27—C26—H26 120.0
C7—C8—H8 119.9 C25—C26—H26 120.0
C8—C9—C10 119.91 (16) C28—C27—C26 120.1 (2)
C8—C9—H9 120.0 C28—C27—H27 119.9
C10—C9—H9 120.0 C26—C27—H27 119.9
C11—C10—C9 119.93 (16) C29—C28—C27 120.39 (19)
C11—C10—H10 120.0 C29—C28—H28 119.8
C9—C10—H10 120.0 C27—C28—H28 119.8
C10—C11—C6 120.44 (16) C28—C29—C30 120.36 (19)
C10—C11—H11 119.8 C28—C29—H29 119.8
C6—C11—H11 119.8 C30—C29—H29 119.8
C13—C12—C17 119.23 (15) C25—C30—C29 119.60 (19)
C13—C12—C3 121.66 (13) C25—C30—H30 120.2
C17—C12—C3 119.01 (14) C29—C30—H30 120.2
C12—C13—C14 120.38 (15)
C1—N1—N2—C2 −0.32 (18) N1—C3—C12—C17 136.38 (14)
C3—N1—N2—C2 173.93 (14) C4—C3—C12—C17 −100.89 (16)
C2—N3—N4—C18 −176.27 (16) C17—C12—C13—C14 0.4 (2)
C1—N3—N4—C18 13.5 (3) C3—C12—C13—C14 −176.07 (15)
N2—N1—C1—N3 −0.65 (17) C12—C13—C14—C15 −0.4 (3)
C3—N1—C1—N3 −174.72 (13) C13—C14—C15—C16 0.5 (3)
N2—N1—C1—S1 177.81 (12) C14—C15—C16—C17 −0.6 (3)
C3—N1—C1—S1 3.7 (2) C15—C16—C17—C12 0.6 (2)
C2—N3—C1—N1 1.33 (17) C13—C12—C17—C16 −0.5 (2)
N4—N3—C1—N1 172.49 (15) C3—C12—C17—C16 176.08 (14)
C2—N3—C1—S1 −177.02 (14) N3—N4—C18—C19 178.74 (15)
N4—N3—C1—S1 −5.9 (3) N4—C18—C19—C24 170.56 (18)
N1—N2—C2—N3 1.19 (18) N4—C18—C19—C20 −11.9 (3)
N1—N2—C2—C25 −177.76 (15) C24—C19—C20—C21 2.9 (3)
N4—N3—C2—N2 −173.91 (13) C18—C19—C20—C21 −174.62 (17)
C1—N3—C2—N2 −1.65 (19) C19—C20—C21—C22 −1.3 (3)
N4—N3—C2—C25 5.0 (2) C20—C21—C22—C23 −1.6 (3)
C1—N3—C2—C25 177.24 (16) C20—C21—C22—N5 176.85 (16)
C1—N1—C3—C12 −69.61 (19) O2—N5—C22—C21 168.08 (18)
N2—N1—C3—C12 116.77 (15) O3—N5—C22—C21 −11.4 (3)
C1—N1—C3—C4 167.44 (14) O2—N5—C22—C23 −13.4 (3)
N2—N1—C3—C4 −6.2 (2) O3—N5—C22—C23 167.13 (17)
N1—C3—C4—C5 −65.96 (17) C21—C22—C23—C24 2.8 (3)
C12—C3—C4—C5 170.10 (12) N5—C22—C23—C24 −175.60 (17)
C3—C4—C5—O1 −8.9 (2) C20—C19—C24—C23 −1.6 (3)
C3—C4—C5—C6 172.12 (13) C18—C19—C24—C23 176.04 (18)
O1—C5—C6—C7 −163.09 (15) C22—C23—C24—C19 −1.2 (3)
C4—C5—C6—C7 15.9 (2) N2—C2—C25—C26 26.7 (2)
O1—C5—C6—C11 14.8 (2) N3—C2—C25—C26 −152.10 (18)
C4—C5—C6—C11 −166.23 (14) N2—C2—C25—C30 −150.80 (17)
C11—C6—C7—C8 0.6 (2) N3—C2—C25—C30 30.4 (3)
C5—C6—C7—C8 178.48 (15) C30—C25—C26—C27 −0.2 (3)
C6—C7—C8—C9 −0.1 (2) C2—C25—C26—C27 −177.80 (17)
C7—C8—C9—C10 −0.5 (3) C25—C26—C27—C28 −0.8 (3)
C8—C9—C10—C11 0.8 (3) C26—C27—C28—C29 0.7 (3)
C9—C10—C11—C6 −0.4 (3) C27—C28—C29—C30 0.4 (3)
C7—C6—C11—C10 −0.3 (2) C26—C25—C30—C29 1.4 (3)
C5—C6—C11—C10 −178.26 (15) C2—C25—C30—C29 178.79 (16)
N1—C3—C12—C13 −47.16 (19) C28—C29—C30—C25 −1.5 (3)
C4—C3—C12—C13 75.57 (18)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2140).

References

  1. Al-Tamimi, A.-M. S., Bari, A., Al-Omar, M. A., Alrashood, K. A. & El-Emam, A. A. (2010). Acta Cryst. E66, o1756. [DOI] [PMC free article] [PubMed]
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  4. Rigaku/MSC (2005). CrystalClear Molecular Structure Corporation, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
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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 datablock(s) global, I. DOI: 10.1107/S1600536811035197/zs2140sup1.cif

e-67-o2727-sup1.cif (24.9KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035197/zs2140Isup2.hkl

e-67-o2727-Isup2.hkl (311.9KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536811035197/zs2140Isup3.cml

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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