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Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): o413.
Published online 2008 January 9. doi:  10.1107/S1600536807068353
PMCID: PMC2960310
Copyright © International Union of Crystallography 2008
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,ab* and Yan-Ping Lia
aKey Laboratory of Oil and Gas Fine Chemicals, Ministry of Education, School of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046, People’s Republic of China
bSchool of Sciences, Xi’an Jiaotong University, Xian 710049, People’s Republic of China
Correspondence e-mail: pxylcj/at/126.com
Received November 14, 2007; Accepted December 24, 2007.
This is an open-access article distributed under the terms described at http://journals.iucr.org/services/termsofuse.html.
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 [triangle]); Akbas et al. (2005 [triangle]); Daidone et al. (2004 [triangle]); Park et al. (2005 [triangle]); Thomasco et al. (2003 [triangle]); Foroumadi et al. (2002 [triangle]); Supuran & Scozzafava (2000 [triangle]).
An external file that holds a picture, illustration, etc. Object name is e-64-0o413-scheme1.jpg Object name is e-64-0o413-scheme1.jpg
Crystal data
  • C23H22N6O2S2
  • M r = 478.58
  • Triclinic, An external file that holds a picture, illustration, etc. Object name is e-64-0o413-efi1.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).
​
Table 1
Table 1
Hydrogen-bond geometry (Å, °)
Supplementary Material
Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807068353/rk2066sup1.cif
Click here to view.(25K, cif)
Structure factors: contains datablocks I. DOI: 10.1107/S1600536807068353/rk2066Isup2.hkl
Click here to view.(253K, hkl)
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
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.
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 (more ...)
Crystal data
C23H22N6O2S2Z = 2
Mr = 478.58F000 = 500
Triclinic, P1Dx = 1.391 Mg m−3
Hall symbol: -P 1Melting point = 461–463 K
a = 8.4489 (3) ÅMo Kα radiation λ = 0.71073 Å
b = 9.9099 (4) ÅCell parameters from 7971 reflections
c = 14.3492 (5) Åθ = 3.1–27.5º
α = 86.089 (1)ºµ = 0.27 mm−1
β = 74.048 (1)ºT = 153 (2) K
γ = 81.591 (1)ºBlock, yellow
V = 1142.25 (7) Å30.32 × 0.15 × 0.13 mm
Data collection
Rigaku R-AXIS Spider diffractometer5171 independent reflections
Radiation source: fine-focus sealed tube3376 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.024
T = 153(2) Kθmax = 27.5º
ω scansθmin = 3.1º
Absorption correction: empirical (using intensity measurements)(ABSCOR; Higashi, 1995)h = −10→10
Tmin = 0.919, Tmax = 0.966k = −12→12
11326 measured reflectionsl = −18→18
Refinement
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-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 reflectionsΔρmax = 0.36 e Å−3
317 parametersΔρmin = −0.54 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Special details
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 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.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
xyzUiso*/UeqOcc. (<1)
S10.56160 (7)0.15893 (6)0.37164 (4)0.04016 (19)
S20.56697 (9)0.18955 (7)0.58112 (5)0.0511 (2)
O10.72651 (18)0.43251 (15)0.78717 (10)0.0330 (3)
O20.7995 (2)0.57769 (18)0.48360 (11)0.0438 (4)
N10.8356 (2)0.63699 (19)0.78887 (13)0.0328 (4)
N20.8911 (2)0.74382 (19)0.72761 (13)0.0360 (4)
N30.6887 (2)0.4151 (2)0.59251 (13)0.0346 (4)
H3A0.66520.39160.65460.042*
N40.6649 (2)0.3756 (2)0.44130 (13)0.0357 (4)
H4A0.70850.45220.42610.043*
N50.6442 (3)0.3835 (2)0.28420 (14)0.0439 (5)
N60.6035 (3)0.3101 (2)0.21699 (14)0.0480 (5)
C10.9603 (3)0.6775 (3)0.91597 (18)0.0408 (5)
H1A1.05400.70370.86810.049*
C20.9530 (3)0.6782 (3)1.01344 (19)0.0467 (6)
H2B1.04200.70611.03260.056*
C30.8177 (3)0.6388 (3)1.08327 (18)0.0452 (6)
H3B0.81460.63891.15000.054*
C40.6870 (3)0.5994 (3)1.05608 (17)0.0418 (6)
H4B0.59460.57141.10410.050*
C50.6905 (3)0.6005 (2)0.95854 (16)0.0364 (5)
H5B0.59960.57610.93950.044*
C60.8294 (3)0.6380 (2)0.88941 (16)0.0336 (5)
C70.9194 (3)0.8149 (3)0.55833 (18)0.0433 (6)
H7A0.96350.89080.57860.065*
H7B0.82060.85020.53660.065*
H7C1.00400.76830.50500.065*
C80.8741 (3)0.7167 (2)0.64179 (16)0.0354 (5)
C90.8061 (3)0.5921 (2)0.64604 (15)0.0325 (5)
C100.7862 (3)0.5469 (2)0.74127 (16)0.0320 (5)
C110.8364 (3)0.3093 (2)0.77255 (14)0.0283 (4)
C120.7675 (3)0.1955 (3)0.81626 (19)0.0417 (6)
H12A0.65670.20360.85630.050*
C130.8630 (3)0.0697 (3)0.8006 (2)0.0516 (7)
H13A0.8178−0.01000.83020.062*
C141.0242 (3)0.0589 (3)0.7422 (2)0.0530 (7)
H14A1.0888−0.02820.73080.064*
C151.0906 (3)0.1736 (3)0.70074 (19)0.0473 (6)
H15A1.20160.16570.66090.057*
C160.9973 (3)0.3014 (3)0.71634 (16)0.0370 (5)
H16A1.04380.38140.68870.044*
C170.7669 (3)0.5307 (2)0.56726 (16)0.0329 (5)
C180.6421 (3)0.3310 (2)0.53439 (16)0.0335 (5)
C190.6281 (3)0.3158 (2)0.36680 (16)0.0351 (5)
C200.5602 (3)0.1932 (3)0.25151 (17)0.0428 (6)
C210.5096 (4)0.0933 (3)0.1944 (2)0.0555 (7)
H21A0.41530.05220.23830.067*
H21B0.46750.14550.14280.067*
C220.6339 (5)−0.0172 (4)0.1491 (3)0.0465 (11)0.639 (5)
H22A0.5827−0.07670.11630.056*0.639 (5)
H22B0.6754−0.07300.19950.056*0.639 (5)
C230.7787 (7)0.0383 (5)0.0753 (3)0.0568 (13)0.639 (5)
H23A0.8616−0.03780.04650.085*0.639 (5)
H23B0.82930.09720.10770.085*0.639 (5)
H23C0.73810.09120.02430.085*0.639 (5)
C22'0.6510 (12)0.0828 (9)0.0931 (5)0.053 (2)0.361 (5)
H22C0.65630.17300.05910.064*0.361 (5)
H22D0.76110.04900.10380.064*0.361 (5)
C23'0.6019 (12)−0.0149 (10)0.0362 (6)0.064 (3)0.361 (5)
H23D0.6845−0.0268−0.02670.096*0.361 (5)
H23E0.49310.02050.02600.096*0.361 (5)
H23F0.5954−0.10290.07150.096*0.361 (5)
Atomic displacement parameters (Å2)
U11U22U33U12U13U23
S10.0411 (3)0.0325 (3)0.0431 (3)−0.0066 (2)−0.0042 (3)−0.0007 (2)
S20.0611 (4)0.0503 (4)0.0486 (4)−0.0317 (3)−0.0178 (3)0.0171 (3)
O10.0335 (8)0.0240 (8)0.0338 (8)−0.0074 (6)0.0049 (6)0.0028 (6)
O20.0581 (11)0.0374 (10)0.0327 (8)−0.0179 (8)−0.0026 (8)0.0059 (7)
N10.0345 (9)0.0273 (10)0.0335 (9)−0.0100 (8)−0.0016 (8)0.0017 (8)
N20.0399 (10)0.0260 (10)0.0380 (10)−0.0109 (8)−0.0015 (8)0.0055 (8)
N30.0350 (10)0.0361 (11)0.0306 (9)−0.0125 (8)−0.0027 (8)0.0046 (8)
N40.0368 (10)0.0328 (11)0.0341 (9)−0.0113 (8)−0.0009 (8)0.0025 (8)
N50.0511 (12)0.0401 (12)0.0344 (10)−0.0093 (10)0.0008 (9)−0.0035 (9)
N60.0606 (14)0.0455 (14)0.0335 (10)−0.0092 (11)−0.0020 (10)−0.0095 (9)
C10.0337 (12)0.0384 (14)0.0479 (13)−0.0099 (10)−0.0050 (11)0.0007 (11)
C20.0472 (14)0.0464 (16)0.0520 (15)−0.0117 (12)−0.0202 (12)−0.0003 (12)
C30.0545 (15)0.0401 (15)0.0429 (13)−0.0073 (12)−0.0157 (12)−0.0015 (11)
C40.0441 (13)0.0412 (14)0.0363 (12)−0.0096 (11)−0.0024 (11)−0.0015 (10)
C50.0322 (11)0.0381 (13)0.0357 (11)−0.0091 (10)−0.0016 (9)−0.0014 (10)
C60.0359 (11)0.0248 (11)0.0356 (11)−0.0041 (9)−0.0029 (9)0.0021 (9)
C70.0466 (13)0.0353 (14)0.0425 (13)−0.0110 (11)−0.0026 (11)0.0099 (10)
C80.0352 (11)0.0273 (12)0.0376 (11)−0.0055 (9)0.0004 (10)0.0014 (9)
C90.0313 (11)0.0259 (11)0.0332 (11)−0.0043 (9)0.0029 (9)0.0013 (9)
C100.0296 (10)0.0242 (11)0.0367 (11)−0.0054 (8)0.0007 (9)0.0005 (9)
C110.0316 (10)0.0262 (11)0.0272 (9)−0.0060 (8)−0.0065 (8)−0.0029 (8)
C120.0357 (12)0.0302 (13)0.0578 (15)−0.0106 (10)−0.0077 (11)0.0013 (11)
C130.0462 (14)0.0266 (13)0.084 (2)−0.0097 (11)−0.0190 (14)0.0010 (13)
C140.0469 (15)0.0330 (14)0.080 (2)0.0041 (12)−0.0211 (14)−0.0101 (13)
C150.0344 (12)0.0494 (16)0.0518 (14)0.0023 (11)−0.0049 (11)−0.0035 (12)
C160.0361 (12)0.0368 (13)0.0359 (11)−0.0075 (10)−0.0057 (10)0.0041 (10)
C170.0287 (10)0.0288 (11)0.0342 (11)−0.0025 (9)0.0028 (9)−0.0005 (9)
C180.0266 (10)0.0362 (13)0.0346 (11)−0.0069 (9)−0.0024 (9)0.0031 (9)
C190.0318 (11)0.0286 (12)0.0372 (11)−0.0041 (9)0.0035 (9)−0.0013 (9)
C200.0478 (14)0.0350 (14)0.0384 (12)−0.0033 (11)0.0005 (11)−0.0074 (10)
C210.0705 (19)0.0468 (17)0.0462 (15)−0.0094 (14)−0.0078 (14)−0.0112 (13)
C220.051 (2)0.038 (2)0.054 (2)−0.0081 (18)−0.019 (2)−0.0067 (19)
C230.063 (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)
Geometric parameters (Å, °)
S1—C191.719 (2)C7—H7C0.9800
S1—C201.737 (2)C8—C91.427 (3)
S2—C181.648 (2)C9—C101.381 (3)
O1—C101.362 (3)C9—C171.455 (3)
O1—C111.411 (3)C11—C161.371 (3)
O2—C171.230 (3)C11—C121.378 (3)
N1—C101.337 (3)C12—C131.378 (4)
N1—N21.380 (2)C12—H12A0.9500
N1—C61.430 (3)C13—C141.382 (4)
N2—C81.328 (3)C13—H13A0.9500
N3—C171.383 (3)C14—C151.368 (4)
N3—C181.384 (3)C14—H14A0.9500
N3—H3A0.8800C15—C161.387 (3)
N4—C181.349 (3)C15—H15A0.9500
N4—C191.384 (3)C16—H16A0.9500
N4—H4A0.8800C20—C211.503 (4)
N5—C191.305 (3)C21—C221.453 (5)
N5—N61.389 (3)C21—C22'1.607 (8)
N6—C201.292 (3)C21—H21A0.9900
C1—C61.379 (3)C21—H21B0.9900
C1—C21.383 (3)C22—C231.525 (6)
C1—H1A0.9500C22—H22A0.9900
C2—C31.382 (4)C22—H22B0.9900
C2—H2B0.9500C23—H23A0.9800
C3—C41.381 (3)C23—H23B0.9800
C3—H3B0.9500C23—H23C0.9800
C4—C51.391 (3)C22'—C23'1.479 (10)
C4—H4B0.9500C22'—H22C0.9900
C5—C61.392 (3)C22'—H22D0.9900
C5—H5B0.9500C23'—H23D0.9800
C7—C81.492 (3)C23'—H23E0.9800
C7—H7A0.9800C23'—H23F0.9800
C7—H7B0.9800
C19—S1—C2085.87 (11)C15—C14—C13120.0 (2)
C10—O1—C11116.95 (16)C15—C14—H14A120.0
C10—N1—N2110.63 (17)C13—C14—H14A120.0
C10—N1—C6129.28 (19)C14—C15—C16120.6 (2)
N2—N1—C6120.00 (17)C14—C15—H15A119.7
C8—N2—N1105.57 (18)C16—C15—H15A119.7
C17—N3—C18129.42 (18)C11—C16—C15118.4 (2)
C17—N3—H3A115.3C11—C16—H16A120.8
C18—N3—H3A115.3C15—C16—H16A120.8
C18—N4—C19128.0 (2)O2—C17—N3121.6 (2)
C18—N4—H4A116.0O2—C17—C9122.9 (2)
C19—N4—H4A116.0N3—C17—C9115.49 (19)
C19—N5—N6111.0 (2)N4—C18—N3114.41 (19)
C20—N6—N5112.6 (2)N4—C18—S2125.85 (18)
C6—C1—C2118.9 (2)N3—C18—S2119.73 (16)
C6—C1—H1A120.5N5—C19—N4117.9 (2)
C2—C1—H1A120.5N5—C19—S1115.74 (18)
C3—C2—C1120.8 (2)N4—C19—S1126.40 (17)
C3—C2—H2B119.6N6—C20—C21123.7 (2)
C1—C2—H2B119.6N6—C20—S1114.75 (18)
C4—C3—C2120.0 (2)C21—C20—S1121.5 (2)
C4—C3—H3B120.0C22—C21—C20118.1 (3)
C2—C3—H3B120.0C22—C21—C22'47.1 (4)
C3—C4—C5120.1 (2)C20—C21—C22'104.9 (3)
C3—C4—H4B119.9C22—C21—H21A107.8
C5—C4—H4B119.9C20—C21—H21A107.8
C4—C5—C6118.9 (2)C22'—C21—H21A146.2
C4—C5—H5B120.6C22—C21—H21B107.8
C6—C5—H5B120.6C20—C21—H21B107.8
C1—C6—C5121.3 (2)C22'—C21—H21B69.9
C1—C6—N1119.4 (2)H21A—C21—H21B107.1
C5—C6—N1119.32 (19)C21—C22—C23110.9 (4)
C8—C7—H7A109.5C21—C22—H22A109.5
C8—C7—H7B109.5C23—C22—H22A109.5
H7A—C7—H7B109.5C21—C22—H22B109.5
C8—C7—H7C109.5C23—C22—H22B109.5
H7A—C7—H7C109.5H22A—C22—H22B108.0
H7B—C7—H7C109.5C22—C23—H23A109.5
N2—C8—C9111.13 (19)C22—C23—H23B109.5
N2—C8—C7119.6 (2)H23A—C23—H23B109.5
C9—C8—C7129.2 (2)C22—C23—H23C109.5
C10—C9—C8103.68 (19)H23A—C23—H23C109.5
C10—C9—C17129.3 (2)H23B—C23—H23C109.5
C8—C9—C17127.0 (2)C23'—C22'—C21105.3 (6)
N1—C10—O1121.07 (19)C23'—C22'—H22C110.7
N1—C10—C9108.98 (19)C21—C22'—H22C110.7
O1—C10—C9130.0 (2)C23'—C22'—H22D110.7
C16—C11—C12122.1 (2)C21—C22'—H22D110.7
C16—C11—O1123.2 (2)H22C—C22'—H22D108.8
C12—C11—O1114.70 (18)C22'—C23'—H23D109.5
C11—C12—C13118.6 (2)C22'—C23'—H23E109.5
C11—C12—H12A120.7H23D—C23'—H23E109.5
C13—C12—H12A120.7C22'—C23'—H23F109.5
C12—C13—C14120.3 (2)H23D—C23'—H23F109.5
C12—C13—H13A119.8H23E—C23'—H23F109.5
C14—C13—H13A119.8
C10—N1—N2—C80.1 (2)C11—C12—C13—C14−0.1 (4)
C6—N1—N2—C8−176.87 (19)C12—C13—C14—C151.1 (4)
C19—N5—N6—C20−0.2 (3)C13—C14—C15—C16−0.4 (4)
C6—C1—C2—C30.6 (4)C12—C11—C16—C152.3 (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—C61.9 (4)C18—N3—C17—O23.3 (4)
C2—C1—C6—C50.6 (4)C18—N3—C17—C9−177.0 (2)
C2—C1—C6—N1179.9 (2)C10—C9—C17—O2−175.8 (2)
C4—C5—C6—C1−1.9 (4)C8—C9—C17—O25.0 (4)
C4—C5—C6—N1178.8 (2)C10—C9—C17—N34.6 (3)
C10—N1—C6—C1140.6 (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—S21.5 (3)
N2—N1—C6—C5136.3 (2)C17—N3—C18—N4−5.9 (3)
N1—N2—C8—C90.4 (2)C17—N3—C18—S2173.78 (18)
N1—N2—C8—C7178.47 (19)N6—N5—C19—N4179.78 (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—N5173.0 (2)
N2—C8—C9—C17178.7 (2)C18—N4—C19—S1−6.8 (3)
C7—C8—C9—C170.9 (4)C20—S1—C19—N50.63 (19)
N2—N1—C10—O1179.90 (18)C20—S1—C19—N4−179.6 (2)
C6—N1—C10—O1−3.5 (3)N5—N6—C20—C21179.9 (2)
N2—N1—C10—C9−0.6 (2)N5—N6—C20—S10.7 (3)
C6—N1—C10—C9176.1 (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—C979.5 (3)N6—C20—C21—C2297.3 (4)
C8—C9—C10—N10.7 (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—O10.8 (4)C20—C21—C22—C23−61.3 (4)
C10—O1—C11—C160.9 (3)C22'—C21—C22—C2323.1 (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—C13175.9 (2)
Hydrogen-bond geometry (Å, °)
D—H···AD—HH···AD···AD—H···A
N3—H3A···O10.882.182.917 (2)141
N4—H4A···O20.881.892.623 (2)139
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2066).
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