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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2008 Jan 9;64(Pt 2):o413. doi: 10.1107/S1600536807068353

N-[(3-Methyl-5-phen­oxy-1-phenyl­pyrazol-4-yl)carbon­yl]-N′-(5-propyl-1,3,4-thia­diazol-2-yl)thio­urea

Yan-Rong Sun a, Gang Liu a, Chen-Jiang Liu a,b,*, Yan-Ping Li a
PMCID: PMC2960310  PMID: 21201441

Abstract

In the crystal structure of the title compound, C23H22N6O2S2, there are two intra­molecular N—H⋯O hydrogen bonds. The propyl chain is disordered over two sites, with occupancy factors of 0.639 (5) and 0.361 (5).

Related literature

For pharmacological and biological properties, see: Ranise et al. (2003 ▶); Akbas et al. (2005 ▶); Daidone et al. (2004 ▶); Park et al. (2005 ▶); Thomasco et al. (2003 ▶); Foroumadi et al. (2002 ▶); Supuran & Scozzafava (2000 ▶).graphic file with name e-64-0o413-scheme1.jpg

Experimental

Crystal data

  • C23H22N6O2S2

  • M r = 478.58

  • Triclinic, Inline graphic

  • a = 8.4489 (3) Å

  • b = 9.9099 (4) Å

  • c = 14.3492 (5) Å

  • α = 86.089 (1)°

  • β = 74.048 (1)°

  • γ = 81.591 (1)°

  • V = 1142.25 (7) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.27 mm−1

  • T = 153 (2) K

  • 0.32 × 0.15 × 0.13 mm

Data collection

  • Rigaku R-AXIS SPIDER diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.919, T max = 0.966

  • 11326 measured reflections

  • 5171 independent reflections

  • 3376 reflections with I > 2σ(I)

  • R int = 0.024

Refinement

  • R[F 2 > 2σ(F 2)] = 0.042

  • wR(F 2) = 0.165

  • S = 1.05

  • 5171 reflections

  • 317 parameters

  • H-atom parameters constrained

  • Δρmax = 0.36 e Å−3

  • Δρmin = −0.54 e Å−3

Data collection: RAPID-AUTO (Rigaku 2004 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807068353/rk2066sup1.cif

e-64-0o413-sup1.cif (24.5KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807068353/rk2066Isup2.hkl

e-64-0o413-Isup2.hkl (253.2KB, hkl)

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N3—H3A⋯O1 0.88 2.18 2.917 (2) 141
N4—H4A⋯O2 0.88 1.89 2.623 (2) 139
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Acknowledgments

The authors gratefully acknowledge support from the National Natural Science Foundation of China (grant No. 20662009), the Program for Century Excellent Talents in Universities (grant No. NCET-04-0987) and the Specialized Research Fund for the Doctoral Program of Higher Education (grant No. 20050755003).

supplementary crystallographic information

Comment

In previous papers, aroylthioureas were reported to be endowed with various and interesting pharmacological properties (Ranize et al., 2003). Compounds including pyrazole ring are known to possess several biological properties, such as antisepsis, antileukosis, antitumor (Akbas et al., 2005; Daidone et al., 2004; Park et al., 2005). The 1,3,4-thiadiazoles also have widespread biological activity, such as antibacterial, antitubercular, antineoplastic activities (Thomasco et al., 2003; Foroumadi et al., 2002; Supuran & Scozzafava, 2000). Due to identical molecular including many heterocyclic nucleus can attain to effective superimposetion of biological activity, we designed and synthesized N-(2-propyl-1,3,4-thiodiazol-5-yl)-N'-(1-phenyl-3-methyl-5- phenoxylpyrazol-4-yl)-carbonylthiourea.

The molecule of the title complex (Fig. 1) has two intramolecular hydrogen bonds, which were formed between N3—H3A and O1 and between N4—H4A and O2, which lead to the formation of two six–membered closed loop. Creation of these (pseudo) rings is crucial for the molecular conformations, because it prevents free rotation within the central carbonylthiourea moiety and locks its atoms in a nearly planar arrangement.

Experimental

A mixture of 1-phenyl-3-methyl-5-phenoxylpyrazole-4-isothiocyanate (1 mmol) and 5-propyl-2-amino-1,3,4-thiodiazole (1 mmol) in absolute acetonitrile was refluxed for 10 h at about 354–364 K, then the product was decanted from the hot solution in a funnel, and dried at room temperature for a yield 25.1% (0.12 g), m.p. 461–463 K. Block-like single-crystal of compound (I) was grown from solution of ethanol by slow evaporation.

Refinement

All H atoms were found in difference electron maps and were subsequently refined in the riding-model approximation with C—H = 0.95–0.99 Å, and with Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(C); N—H = 0.88 Å, and with Uiso(H) = 1.2Ueq(N).

It is disordered in the propyl moiety of molecule. The propyl chain was splited into two chains and the restraints applied to the two chains and the two chains can share the same C21 atom. The ratio of occupancy factors is 0.639 (5)/0.361.

Figures

Fig. 1.

Fig. 1.

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The molecule structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. The H atoms are shown as spheres of arbitrary radus. The intramolecular H bond are marked as dashed lines. Only major fragment of propyl chain are drawn.

Crystal data

C23H22N6O2S2 Z = 2
Mr = 478.58 F000 = 500
Triclinic, P1 Dx = 1.391 Mg m−3
Hall symbol: -P 1 Melting point = 461–463 K
a = 8.4489 (3) Å Mo Kα radiation λ = 0.71073 Å
b = 9.9099 (4) Å Cell parameters from 7971 reflections
c = 14.3492 (5) Å θ = 3.1–27.5º
α = 86.089 (1)º µ = 0.27 mm−1
β = 74.048 (1)º T = 153 (2) K
γ = 81.591 (1)º Block, yellow
V = 1142.25 (7) Å3 0.32 × 0.15 × 0.13 mm
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Data collection

Rigaku R-AXIS Spider diffractometer 5171 independent reflections
Radiation source: fine-focus sealed tube 3376 reflections with I > 2σ(I)
Monochromator: graphite Rint = 0.024
T = 153(2) K θmax = 27.5º
ω scans θmin = 3.1º
Absorption correction: empirical (using intensity measurements)(ABSCOR; Higashi, 1995) h = −10→10
Tmin = 0.919, Tmax = 0.966 k = −12→12
11326 measured reflections l = −18→18
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Refinement

Refinement on F2 Secondary atom site location: difference Fourier map
Least-squares matrix: full Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042 H-atom parameters constrained
wR(F2) = 0.165   w = 1/[σ2(Fo2) + (0.1061P)2] where P = (Fo2 + 2Fc2)/3
S = 1.05 (Δ/σ)max = 0.001
5171 reflections Δρmax = 0.36 e Å−3
317 parameters Δρmin = −0.54 e Å−3
Primary atom site location: structure-invariant direct methods Extinction correction: none
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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 > 2σ(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 Occ. (<1)
S1 0.56160 (7) 0.15893 (6) 0.37164 (4) 0.04016 (19)
S2 0.56697 (9) 0.18955 (7) 0.58112 (5) 0.0511 (2)
O1 0.72651 (18) 0.43251 (15) 0.78717 (10) 0.0330 (3)
O2 0.7995 (2) 0.57769 (18) 0.48360 (11) 0.0438 (4)
N1 0.8356 (2) 0.63699 (19) 0.78887 (13) 0.0328 (4)
N2 0.8911 (2) 0.74382 (19) 0.72761 (13) 0.0360 (4)
N3 0.6887 (2) 0.4151 (2) 0.59251 (13) 0.0346 (4)
H3A 0.6652 0.3916 0.6546 0.042*
N4 0.6649 (2) 0.3756 (2) 0.44130 (13) 0.0357 (4)
H4A 0.7085 0.4522 0.4261 0.043*
N5 0.6442 (3) 0.3835 (2) 0.28420 (14) 0.0439 (5)
N6 0.6035 (3) 0.3101 (2) 0.21699 (14) 0.0480 (5)
C1 0.9603 (3) 0.6775 (3) 0.91597 (18) 0.0408 (5)
H1A 1.0540 0.7037 0.8681 0.049*
C2 0.9530 (3) 0.6782 (3) 1.01344 (19) 0.0467 (6)
H2B 1.0420 0.7061 1.0326 0.056*
C3 0.8177 (3) 0.6388 (3) 1.08327 (18) 0.0452 (6)
H3B 0.8146 0.6389 1.1500 0.054*
C4 0.6870 (3) 0.5994 (3) 1.05608 (17) 0.0418 (6)
H4B 0.5946 0.5714 1.1041 0.050*
C5 0.6905 (3) 0.6005 (2) 0.95854 (16) 0.0364 (5)
H5B 0.5996 0.5761 0.9395 0.044*
C6 0.8294 (3) 0.6380 (2) 0.88941 (16) 0.0336 (5)
C7 0.9194 (3) 0.8149 (3) 0.55833 (18) 0.0433 (6)
H7A 0.9635 0.8908 0.5786 0.065*
H7B 0.8206 0.8502 0.5366 0.065*
H7C 1.0040 0.7683 0.5050 0.065*
C8 0.8741 (3) 0.7167 (2) 0.64179 (16) 0.0354 (5)
C9 0.8061 (3) 0.5921 (2) 0.64604 (15) 0.0325 (5)
C10 0.7862 (3) 0.5469 (2) 0.74127 (16) 0.0320 (5)
C11 0.8364 (3) 0.3093 (2) 0.77255 (14) 0.0283 (4)
C12 0.7675 (3) 0.1955 (3) 0.81626 (19) 0.0417 (6)
H12A 0.6567 0.2036 0.8563 0.050*
C13 0.8630 (3) 0.0697 (3) 0.8006 (2) 0.0516 (7)
H13A 0.8178 −0.0100 0.8302 0.062*
C14 1.0242 (3) 0.0589 (3) 0.7422 (2) 0.0530 (7)
H14A 1.0888 −0.0282 0.7308 0.064*
C15 1.0906 (3) 0.1736 (3) 0.70074 (19) 0.0473 (6)
H15A 1.2016 0.1657 0.6609 0.057*
C16 0.9973 (3) 0.3014 (3) 0.71634 (16) 0.0370 (5)
H16A 1.0438 0.3814 0.6887 0.044*
C17 0.7669 (3) 0.5307 (2) 0.56726 (16) 0.0329 (5)
C18 0.6421 (3) 0.3310 (2) 0.53439 (16) 0.0335 (5)
C19 0.6281 (3) 0.3158 (2) 0.36680 (16) 0.0351 (5)
C20 0.5602 (3) 0.1932 (3) 0.25151 (17) 0.0428 (6)
C21 0.5096 (4) 0.0933 (3) 0.1944 (2) 0.0555 (7)
H21A 0.4153 0.0522 0.2383 0.067*
H21B 0.4675 0.1455 0.1428 0.067*
C22 0.6339 (5) −0.0172 (4) 0.1491 (3) 0.0465 (11) 0.639 (5)
H22A 0.5827 −0.0767 0.1163 0.056* 0.639 (5)
H22B 0.6754 −0.0730 0.1995 0.056* 0.639 (5)
C23 0.7787 (7) 0.0383 (5) 0.0753 (3) 0.0568 (13) 0.639 (5)
H23A 0.8616 −0.0378 0.0465 0.085* 0.639 (5)
H23B 0.8293 0.0972 0.1077 0.085* 0.639 (5)
H23C 0.7381 0.0912 0.0243 0.085* 0.639 (5)
C22' 0.6510 (12) 0.0828 (9) 0.0931 (5) 0.053 (2) 0.361 (5)
H22C 0.6563 0.1730 0.0591 0.064* 0.361 (5)
H22D 0.7611 0.0490 0.1038 0.064* 0.361 (5)
C23' 0.6019 (12) −0.0149 (10) 0.0362 (6) 0.064 (3) 0.361 (5)
H23D 0.6845 −0.0268 −0.0267 0.096* 0.361 (5)
H23E 0.4931 0.0205 0.0260 0.096* 0.361 (5)
H23F 0.5954 −0.1029 0.0715 0.096* 0.361 (5)
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
S1 0.0411 (3) 0.0325 (3) 0.0431 (3) −0.0066 (2) −0.0042 (3) −0.0007 (2)
S2 0.0611 (4) 0.0503 (4) 0.0486 (4) −0.0317 (3) −0.0178 (3) 0.0171 (3)
O1 0.0335 (8) 0.0240 (8) 0.0338 (8) −0.0074 (6) 0.0049 (6) 0.0028 (6)
O2 0.0581 (11) 0.0374 (10) 0.0327 (8) −0.0179 (8) −0.0026 (8) 0.0059 (7)
N1 0.0345 (9) 0.0273 (10) 0.0335 (9) −0.0100 (8) −0.0016 (8) 0.0017 (8)
N2 0.0399 (10) 0.0260 (10) 0.0380 (10) −0.0109 (8) −0.0015 (8) 0.0055 (8)
N3 0.0350 (10) 0.0361 (11) 0.0306 (9) −0.0125 (8) −0.0027 (8) 0.0046 (8)
N4 0.0368 (10) 0.0328 (11) 0.0341 (9) −0.0113 (8) −0.0009 (8) 0.0025 (8)
N5 0.0511 (12) 0.0401 (12) 0.0344 (10) −0.0093 (10) 0.0008 (9) −0.0035 (9)
N6 0.0606 (14) 0.0455 (14) 0.0335 (10) −0.0092 (11) −0.0020 (10) −0.0095 (9)
C1 0.0337 (12) 0.0384 (14) 0.0479 (13) −0.0099 (10) −0.0050 (11) 0.0007 (11)
C2 0.0472 (14) 0.0464 (16) 0.0520 (15) −0.0117 (12) −0.0202 (12) −0.0003 (12)
C3 0.0545 (15) 0.0401 (15) 0.0429 (13) −0.0073 (12) −0.0157 (12) −0.0015 (11)
C4 0.0441 (13) 0.0412 (14) 0.0363 (12) −0.0096 (11) −0.0024 (11) −0.0015 (10)
C5 0.0322 (11) 0.0381 (13) 0.0357 (11) −0.0091 (10) −0.0016 (9) −0.0014 (10)
C6 0.0359 (11) 0.0248 (11) 0.0356 (11) −0.0041 (9) −0.0029 (9) 0.0021 (9)
C7 0.0466 (13) 0.0353 (14) 0.0425 (13) −0.0110 (11) −0.0026 (11) 0.0099 (10)
C8 0.0352 (11) 0.0273 (12) 0.0376 (11) −0.0055 (9) 0.0004 (10) 0.0014 (9)
C9 0.0313 (11) 0.0259 (11) 0.0332 (11) −0.0043 (9) 0.0029 (9) 0.0013 (9)
C10 0.0296 (10) 0.0242 (11) 0.0367 (11) −0.0054 (8) 0.0007 (9) 0.0005 (9)
C11 0.0316 (10) 0.0262 (11) 0.0272 (9) −0.0060 (8) −0.0065 (8) −0.0029 (8)
C12 0.0357 (12) 0.0302 (13) 0.0578 (15) −0.0106 (10) −0.0077 (11) 0.0013 (11)
C13 0.0462 (14) 0.0266 (13) 0.084 (2) −0.0097 (11) −0.0190 (14) 0.0010 (13)
C14 0.0469 (15) 0.0330 (14) 0.080 (2) 0.0041 (12) −0.0211 (14) −0.0101 (13)
C15 0.0344 (12) 0.0494 (16) 0.0518 (14) 0.0023 (11) −0.0049 (11) −0.0035 (12)
C16 0.0361 (12) 0.0368 (13) 0.0359 (11) −0.0075 (10) −0.0057 (10) 0.0041 (10)
C17 0.0287 (10) 0.0288 (11) 0.0342 (11) −0.0025 (9) 0.0028 (9) −0.0005 (9)
C18 0.0266 (10) 0.0362 (13) 0.0346 (11) −0.0069 (9) −0.0024 (9) 0.0031 (9)
C19 0.0318 (11) 0.0286 (12) 0.0372 (11) −0.0041 (9) 0.0035 (9) −0.0013 (9)
C20 0.0478 (14) 0.0350 (14) 0.0384 (12) −0.0033 (11) 0.0005 (11) −0.0074 (10)
C21 0.0705 (19) 0.0468 (17) 0.0462 (15) −0.0094 (14) −0.0078 (14) −0.0112 (13)
C22 0.051 (2) 0.038 (2) 0.054 (2) −0.0081 (18) −0.019 (2) −0.0067 (19)
C23 0.063 (3) 0.052 (3) 0.046 (2) −0.013 (2) 0.006 (2) −0.015 (2)
C22' 0.064 (6) 0.050 (5) 0.042 (4) −0.015 (4) −0.004 (4) −0.013 (4)
C23' 0.093 (6) 0.064 (6) 0.042 (4) −0.034 (5) −0.017 (4) −0.006 (4)
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Geometric parameters (Å, °)

S1—C19 1.719 (2) C7—H7C 0.9800
S1—C20 1.737 (2) C8—C9 1.427 (3)
S2—C18 1.648 (2) C9—C10 1.381 (3)
O1—C10 1.362 (3) C9—C17 1.455 (3)
O1—C11 1.411 (3) C11—C16 1.371 (3)
O2—C17 1.230 (3) C11—C12 1.378 (3)
N1—C10 1.337 (3) C12—C13 1.378 (4)
N1—N2 1.380 (2) C12—H12A 0.9500
N1—C6 1.430 (3) C13—C14 1.382 (4)
N2—C8 1.328 (3) C13—H13A 0.9500
N3—C17 1.383 (3) C14—C15 1.368 (4)
N3—C18 1.384 (3) C14—H14A 0.9500
N3—H3A 0.8800 C15—C16 1.387 (3)
N4—C18 1.349 (3) C15—H15A 0.9500
N4—C19 1.384 (3) C16—H16A 0.9500
N4—H4A 0.8800 C20—C21 1.503 (4)
N5—C19 1.305 (3) C21—C22 1.453 (5)
N5—N6 1.389 (3) C21—C22' 1.607 (8)
N6—C20 1.292 (3) C21—H21A 0.9900
C1—C6 1.379 (3) C21—H21B 0.9900
C1—C2 1.383 (3) C22—C23 1.525 (6)
C1—H1A 0.9500 C22—H22A 0.9900
C2—C3 1.382 (4) C22—H22B 0.9900
C2—H2B 0.9500 C23—H23A 0.9800
C3—C4 1.381 (3) C23—H23B 0.9800
C3—H3B 0.9500 C23—H23C 0.9800
C4—C5 1.391 (3) C22'—C23' 1.479 (10)
C4—H4B 0.9500 C22'—H22C 0.9900
C5—C6 1.392 (3) C22'—H22D 0.9900
C5—H5B 0.9500 C23'—H23D 0.9800
C7—C8 1.492 (3) C23'—H23E 0.9800
C7—H7A 0.9800 C23'—H23F 0.9800
C7—H7B 0.9800
C19—S1—C20 85.87 (11) C15—C14—C13 120.0 (2)
C10—O1—C11 116.95 (16) C15—C14—H14A 120.0
C10—N1—N2 110.63 (17) C13—C14—H14A 120.0
C10—N1—C6 129.28 (19) C14—C15—C16 120.6 (2)
N2—N1—C6 120.00 (17) C14—C15—H15A 119.7
C8—N2—N1 105.57 (18) C16—C15—H15A 119.7
C17—N3—C18 129.42 (18) C11—C16—C15 118.4 (2)
C17—N3—H3A 115.3 C11—C16—H16A 120.8
C18—N3—H3A 115.3 C15—C16—H16A 120.8
C18—N4—C19 128.0 (2) O2—C17—N3 121.6 (2)
C18—N4—H4A 116.0 O2—C17—C9 122.9 (2)
C19—N4—H4A 116.0 N3—C17—C9 115.49 (19)
C19—N5—N6 111.0 (2) N4—C18—N3 114.41 (19)
C20—N6—N5 112.6 (2) N4—C18—S2 125.85 (18)
C6—C1—C2 118.9 (2) N3—C18—S2 119.73 (16)
C6—C1—H1A 120.5 N5—C19—N4 117.9 (2)
C2—C1—H1A 120.5 N5—C19—S1 115.74 (18)
C3—C2—C1 120.8 (2) N4—C19—S1 126.40 (17)
C3—C2—H2B 119.6 N6—C20—C21 123.7 (2)
C1—C2—H2B 119.6 N6—C20—S1 114.75 (18)
C4—C3—C2 120.0 (2) C21—C20—S1 121.5 (2)
C4—C3—H3B 120.0 C22—C21—C20 118.1 (3)
C2—C3—H3B 120.0 C22—C21—C22' 47.1 (4)
C3—C4—C5 120.1 (2) C20—C21—C22' 104.9 (3)
C3—C4—H4B 119.9 C22—C21—H21A 107.8
C5—C4—H4B 119.9 C20—C21—H21A 107.8
C4—C5—C6 118.9 (2) C22'—C21—H21A 146.2
C4—C5—H5B 120.6 C22—C21—H21B 107.8
C6—C5—H5B 120.6 C20—C21—H21B 107.8
C1—C6—C5 121.3 (2) C22'—C21—H21B 69.9
C1—C6—N1 119.4 (2) H21A—C21—H21B 107.1
C5—C6—N1 119.32 (19) C21—C22—C23 110.9 (4)
C8—C7—H7A 109.5 C21—C22—H22A 109.5
C8—C7—H7B 109.5 C23—C22—H22A 109.5
H7A—C7—H7B 109.5 C21—C22—H22B 109.5
C8—C7—H7C 109.5 C23—C22—H22B 109.5
H7A—C7—H7C 109.5 H22A—C22—H22B 108.0
H7B—C7—H7C 109.5 C22—C23—H23A 109.5
N2—C8—C9 111.13 (19) C22—C23—H23B 109.5
N2—C8—C7 119.6 (2) H23A—C23—H23B 109.5
C9—C8—C7 129.2 (2) C22—C23—H23C 109.5
C10—C9—C8 103.68 (19) H23A—C23—H23C 109.5
C10—C9—C17 129.3 (2) H23B—C23—H23C 109.5
C8—C9—C17 127.0 (2) C23'—C22'—C21 105.3 (6)
N1—C10—O1 121.07 (19) C23'—C22'—H22C 110.7
N1—C10—C9 108.98 (19) C21—C22'—H22C 110.7
O1—C10—C9 130.0 (2) C23'—C22'—H22D 110.7
C16—C11—C12 122.1 (2) C21—C22'—H22D 110.7
C16—C11—O1 123.2 (2) H22C—C22'—H22D 108.8
C12—C11—O1 114.70 (18) C22'—C23'—H23D 109.5
C11—C12—C13 118.6 (2) C22'—C23'—H23E 109.5
C11—C12—H12A 120.7 H23D—C23'—H23E 109.5
C13—C12—H12A 120.7 C22'—C23'—H23F 109.5
C12—C13—C14 120.3 (2) H23D—C23'—H23F 109.5
C12—C13—H13A 119.8 H23E—C23'—H23F 109.5
C14—C13—H13A 119.8
C10—N1—N2—C8 0.1 (2) C11—C12—C13—C14 −0.1 (4)
C6—N1—N2—C8 −176.87 (19) C12—C13—C14—C15 1.1 (4)
C19—N5—N6—C20 −0.2 (3) C13—C14—C15—C16 −0.4 (4)
C6—C1—C2—C3 0.6 (4) C12—C11—C16—C15 2.3 (3)
C1—C2—C3—C4 −0.6 (4) O1—C11—C16—C15 −175.1 (2)
C2—C3—C4—C5 −0.6 (4) C14—C15—C16—C11 −1.3 (4)
C3—C4—C5—C6 1.9 (4) C18—N3—C17—O2 3.3 (4)
C2—C1—C6—C5 0.6 (4) C18—N3—C17—C9 −177.0 (2)
C2—C1—C6—N1 179.9 (2) C10—C9—C17—O2 −175.8 (2)
C4—C5—C6—C1 −1.9 (4) C8—C9—C17—O2 5.0 (4)
C4—C5—C6—N1 178.8 (2) C10—C9—C17—N3 4.6 (3)
C10—N1—C6—C1 140.6 (2) C8—C9—C17—N3 −174.7 (2)
N2—N1—C6—C1 −43.1 (3) C19—N4—C18—N3 −178.9 (2)
C10—N1—C6—C5 −40.1 (3) C19—N4—C18—S2 1.5 (3)
N2—N1—C6—C5 136.3 (2) C17—N3—C18—N4 −5.9 (3)
N1—N2—C8—C9 0.4 (2) C17—N3—C18—S2 173.78 (18)
N1—N2—C8—C7 178.47 (19) N6—N5—C19—N4 179.78 (19)
N2—C8—C9—C10 −0.7 (2) N6—N5—C19—S1 −0.4 (3)
C7—C8—C9—C10 −178.6 (2) C18—N4—C19—N5 173.0 (2)
N2—C8—C9—C17 178.7 (2) C18—N4—C19—S1 −6.8 (3)
C7—C8—C9—C17 0.9 (4) C20—S1—C19—N5 0.63 (19)
N2—N1—C10—O1 179.90 (18) C20—S1—C19—N4 −179.6 (2)
C6—N1—C10—O1 −3.5 (3) N5—N6—C20—C21 179.9 (2)
N2—N1—C10—C9 −0.6 (2) N5—N6—C20—S1 0.7 (3)
C6—N1—C10—C9 176.1 (2) C19—S1—C20—N6 −0.7 (2)
C11—O1—C10—N1 −101.1 (2) C19—S1—C20—C21 −179.9 (2)
C11—O1—C10—C9 79.5 (3) N6—C20—C21—C22 97.3 (4)
C8—C9—C10—N1 0.7 (2) S1—C20—C21—C22 −83.6 (3)
C17—C9—C10—N1 −178.7 (2) N6—C20—C21—C22' 48.3 (5)
C8—C9—C10—O1 −179.8 (2) S1—C20—C21—C22' −132.6 (4)
C17—C9—C10—O1 0.8 (4) C20—C21—C22—C23 −61.3 (4)
C10—O1—C11—C16 0.9 (3) C22'—C21—C22—C23 23.1 (5)
C10—O1—C11—C12 −176.69 (18) C22—C21—C22'—C23' 65.6 (6)
C16—C11—C12—C13 −1.7 (4) C20—C21—C22'—C23' −179.7 (6)
O1—C11—C12—C13 175.9 (2)
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Hydrogen-bond geometry (Å, °)

D—H···A D—H H···A D···A D—H···A
N3—H3A···O1 0.88 2.18 2.917 (2) 141
N4—H4A···O2 0.88 1.89 2.623 (2) 139
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2066).

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/S1600536807068353/rk2066sup1.cif

e-64-0o413-sup1.cif (24.5KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807068353/rk2066Isup2.hkl

e-64-0o413-Isup2.hkl (253.2KB, hkl)

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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