5-(3-Methyl-5-phen­oxy-1-phenyl­pyrazol-4-yl)-1,3,4-thia­diazol-2-amine

Sun, Y.-R.; Liu, G.; Liu, C.-J.; Wang, J.-D.

doi:10.1107/S1600536807034009

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5-(3-Methyl-5-phenoxy-1-phenylpyrazol-4-yl)-1,3,4-thiadiazol-2-amine

Y.-R. Sun, G. Liu, C.-J. Liu and J.-D. Wang

There are two molecules in the asymmetric unit of the title compound, C₁₈H₁₅N₅OS. The two molecules differ by less than 3° in the dihedral angles between corresponding planar units. Hydrogen bonding between the two molecules creates a one-dimensional chain along the c direction.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807034009/om2139sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807034009/om2139Isup2.hkl Contains datablock I

CCDC reference: 657775

checkCIF report

Key indicators

Single-crystal X-ray study
T = 153 K
Mean (C-C) = 0.002 Å
R factor = 0.036
wR factor = 0.101
Data-to-parameter ratio = 17.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.66 mm
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C32    -   C33     ..       6.01 su
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?
PLAT322_ALERT_2_C Check Hybridisation of  S2     in Main Residue .          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Compounds including 1,3,4-thiadiazole ring are known to possess several biological properties, such as antibacterial, antitubercular, antineoplastic activities (Thomasco et al., 2003; Foroumadi et al., 2002; Supuran & Scozzafava, 2000). Pyrazoles also have widespread biological activity, such as antisepsis, antileukosis, antitumor (Akbas et al., 2005; Daidone et al., 2004; Park et al., 2005). In an attempt to achieve new compounds with possible biological activities, we designed and synthesized 2-amino-5-(1-phenyl-3-methyl-5-phenoxylpyrazole-4-yl)-1,3,4-thiadiazole(1). The asymmetric unit has two molecules, and structures of the two molecules are nearly identical.

Related literature top

For related literature, see: Akbas et al. (2005); Daidone et al. (2004); Foroumadi et al. (2002); Park et al. (2005); Supuran & Scozzafava (2000); Thomasco et al. (2003).

Experimental top

To the mixture of 1-phenyl-3-methyl-5-phenoxylpyrazole-4-formylic acid(4 mmol) and aminothiourea(4 mmol), phosphorus oxychloride(10 mL) was slowly added with stirring in ice bath. The reaction mixture was slowly heated to reflux 2 h at about 358 K, then cooled, and cold water (30 mL) added. The solution was slowly heated to reflux 6 h at about 393 K, then filtered. To neutralize the filtrate, 25% KOH was added to reach pH = 8–9. The product was isolated by filtration, washed with water, and dried at room temperature for a yield 65.2% (0.912 g), m.p. 497–498 K. Block-like single-crystal of the title compound were grown from a solution of ethanol by slow evaporation.

Structure description top

For related literature, see: Akbas et al. (2005); Daidone et al. (2004); Foroumadi et al. (2002); Park et al. (2005); Supuran & Scozzafava (2000); Thomasco et al. (2003).

Computing details top

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

Figures top

Fig. 1. A view of the moleculer structure of the two molecules of the aymmetric unit, showing the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level, and H atoms are shown as small spheres of arbitrary radii.

5-(3-Methyl-5-phenoxy-1-phenylpyrazol-4-yl)-1,3,4-thiadiazol-2-amine top

Crystal data top

C₁₈H₁₅N₅OS	D_x = 1.363 Mg m⁻³
M_r = 349.41	Melting point: 498 K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 20.2987 (5) Å	Cell parameters from 26663 reflections
b = 9.6934 (3) Å	θ = 3.0–27.5°
c = 19.0726 (6) Å	µ = 0.21 mm⁻¹
β = 114.846 (1)°	T = 153 K
V = 3405.43 (17) Å³	Block, colorless
Z = 8	0.66 × 0.43 × 0.31 mm
F(000) = 1456

Data collection top

Rigaku R-AXIS SPIDER diffractometer	7772 independent reflections
Radiation source: fine-focus sealed tube	6769 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ω scans	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: empirical (using intensity measurements) (ABSCOR; Higashi, 1995)	h = −24→26
T_min = 0.876, T_max = 0.939	k = −12→12
32693 measured reflections	l = −24→23

Refinement top

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0577P)² + 0.8824P] where P = (F_o² + 2F_c²)/3
7772 reflections	(Δ/σ)_max = 0.001
453 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₁₈H₁₅N₅OS	V = 3405.43 (17) Å³
M_r = 349.41	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 20.2987 (5) Å	µ = 0.21 mm⁻¹
b = 9.6934 (3) Å	T = 153 K
c = 19.0726 (6) Å	0.66 × 0.43 × 0.31 mm
β = 114.846 (1)°

Data collection top

Rigaku R-AXIS SPIDER diffractometer	7772 independent reflections
Absorption correction: empirical (using intensity measurements) (ABSCOR; Higashi, 1995)	6769 reflections with I > 2σ(I)
T_min = 0.876, T_max = 0.939	R_int = 0.020
32693 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.05	Δρ_max = 0.24 e Å⁻³
7772 reflections	Δρ_min = −0.41 e Å⁻³
453 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
S1	0.430303 (16)	0.79622 (3)	0.268570 (16)	0.02420 (8)
S2	0.053694 (17)	0.72302 (4)	0.263009 (18)	0.03485 (10)
O1	0.52710 (4)	0.88205 (9)	0.18168 (5)	0.02343 (18)
O2	−0.04172 (5)	0.82952 (9)	0.34655 (5)	0.02735 (19)
N1	0.33984 (6)	0.79945 (13)	0.34137 (6)	0.0323 (3)
H1A	0.2967	0.7916	0.3416	0.039*
H1B	0.3779	0.8193	0.3844	0.039*
N2	0.29285 (6)	0.75129 (12)	0.20940 (6)	0.0250 (2)
N3	0.31332 (5)	0.73761 (11)	0.14935 (6)	0.0236 (2)
N4	0.43532 (5)	0.68631 (11)	0.01202 (6)	0.0234 (2)
N5	0.49192 (5)	0.76583 (11)	0.06123 (6)	0.0225 (2)
N6	0.14095 (6)	0.71887 (15)	0.18704 (7)	0.0384 (3)
H6A	0.1835	0.7101	0.1857	0.046*
H6B	0.1017	0.7308	0.1439	0.046*
N7	0.19232 (6)	0.69641 (13)	0.32166 (6)	0.0295 (2)
N8	0.17298 (6)	0.68692 (12)	0.38289 (6)	0.0285 (2)
N9	0.05654 (5)	0.67127 (12)	0.52749 (6)	0.0269 (2)
N10	−0.00125 (5)	0.74338 (12)	0.47454 (6)	0.0249 (2)
C1	0.58095 (6)	0.93578 (13)	0.06074 (7)	0.0267 (3)
H1C	0.5691	0.9941	0.0938	0.032*
C2	0.63228 (7)	0.97676 (15)	0.03447 (8)	0.0316 (3)
H2B	0.6565	1.0627	0.0506	0.038*
C3	0.64825 (8)	0.89297 (16)	−0.01502 (9)	0.0380 (3)
H3B	0.6829	0.9219	−0.0333	0.046*
C4	0.61364 (9)	0.76660 (17)	−0.03796 (10)	0.0414 (3)
H4B	0.6242	0.7099	−0.0726	0.050*
C5	0.56374 (8)	0.72254 (15)	−0.01070 (8)	0.0334 (3)
H5A	0.5412	0.6348	−0.0251	0.040*
C6	0.54718 (6)	0.80857 (13)	0.03806 (7)	0.0235 (2)
C7	0.32015 (7)	0.59679 (14)	0.00612 (7)	0.0283 (3)
H7B	0.3224	0.5393	−0.0351	0.042*
H7C	0.2798	0.6622	−0.0161	0.042*
H7D	0.3126	0.5380	0.0439	0.042*
C8	0.38972 (6)	0.67421 (12)	0.04516 (6)	0.0218 (2)
C9	0.41636 (6)	0.74462 (12)	0.11713 (6)	0.0212 (2)
C10	0.48134 (6)	0.80017 (12)	0.12464 (6)	0.0209 (2)
C11	0.59244 (6)	0.82460 (12)	0.23525 (6)	0.0206 (2)
C12	0.60255 (7)	0.68515 (13)	0.25028 (8)	0.0289 (3)
H12A	0.5653	0.6208	0.2227	0.035*
C13	0.66881 (8)	0.64136 (15)	0.30706 (8)	0.0342 (3)
H13A	0.6770	0.5457	0.3182	0.041*
C14	0.72283 (7)	0.73517 (15)	0.34745 (8)	0.0324 (3)
H14A	0.7677	0.7042	0.3864	0.039*
C15	0.71116 (7)	0.87414 (15)	0.33085 (8)	0.0334 (3)
H15A	0.7482	0.9389	0.3583	0.040*
C16	0.64566 (7)	0.91945 (13)	0.27442 (7)	0.0288 (3)
H16A	0.6376	1.0150	0.2629	0.035*
C17	0.38236 (6)	0.75766 (12)	0.17010 (6)	0.0208 (2)
C18	0.34753 (7)	0.78104 (12)	0.27530 (7)	0.0236 (2)
C19	−0.08683 (7)	0.92639 (14)	0.46842 (8)	0.0306 (3)
H19A	−0.0778	0.9722	0.4293	0.037*
C20	−0.13382 (7)	0.98335 (16)	0.49647 (8)	0.0371 (3)
H20A	−0.1574	1.0683	0.4760	0.044*
C21	−0.14653 (8)	0.9176 (2)	0.55371 (9)	0.0460 (4)
H21A	−0.1782	0.9578	0.5731	0.055*
C22	−0.11300 (8)	0.7928 (2)	0.58291 (9)	0.0484 (4)
H22A	−0.1219	0.7475	0.6223	0.058*
C23	−0.06649 (7)	0.73330 (17)	0.55515 (8)	0.0360 (3)
H23A	−0.0440	0.6471	0.5747	0.043*
C24	−0.05322 (6)	0.80151 (14)	0.49835 (7)	0.0261 (3)
C25	0.16923 (7)	0.56799 (15)	0.53478 (8)	0.0318 (3)
H25A	0.1701	0.5290	0.5826	0.048*
H25B	0.2101	0.6317	0.5473	0.048*
H25C	0.1731	0.4934	0.5020	0.048*
C26	0.09973 (6)	0.64382 (13)	0.49282 (7)	0.0248 (2)
C27	0.07052 (6)	0.69711 (13)	0.41642 (7)	0.0238 (2)
C28	0.00615 (6)	0.75820 (13)	0.40755 (7)	0.0238 (2)
C29	−0.10629 (6)	0.76360 (14)	0.29741 (7)	0.0249 (2)
C30	−0.11821 (7)	0.62435 (15)	0.29970 (9)	0.0356 (3)
H30A	−0.0826	0.5666	0.3365	0.043*
C31	−0.18401 (9)	0.57004 (19)	0.24642 (10)	0.0491 (4)
H31A	−0.1932	0.4741	0.2471	0.059*
C32	−0.23534 (8)	0.6529 (2)	0.19326 (9)	0.0497 (4)
H32A	−0.2797	0.6145	0.1571	0.060*
C33	−0.22249 (8)	0.7914 (2)	0.19243 (9)	0.0504 (5)
H33A	−0.2583	0.8489	0.1557	0.061*
C34	−0.15764 (8)	0.84882 (17)	0.24470 (8)	0.0378 (3)
H34A	−0.1489	0.9450	0.2441	0.045*
C35	0.10357 (6)	0.69930 (13)	0.36219 (7)	0.0242 (2)
C36	0.13585 (7)	0.71394 (14)	0.25529 (7)	0.0280 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02217 (15)	0.03248 (17)	0.01766 (15)	−0.00192 (11)	0.00807 (12)	−0.00262 (11)
S2	0.02132 (15)	0.0625 (2)	0.01953 (16)	0.00335 (14)	0.00740 (13)	0.00420 (14)
O1	0.0210 (4)	0.0248 (4)	0.0194 (4)	0.0012 (3)	0.0036 (3)	−0.0025 (3)
O2	0.0248 (4)	0.0307 (5)	0.0223 (4)	0.0007 (3)	0.0059 (4)	0.0038 (3)
N1	0.0266 (5)	0.0531 (7)	0.0187 (5)	0.0006 (5)	0.0112 (4)	−0.0021 (5)
N2	0.0228 (5)	0.0347 (6)	0.0186 (5)	0.0040 (4)	0.0098 (4)	0.0025 (4)
N3	0.0222 (5)	0.0309 (5)	0.0181 (5)	0.0034 (4)	0.0090 (4)	0.0021 (4)
N4	0.0203 (5)	0.0300 (5)	0.0181 (5)	−0.0027 (4)	0.0064 (4)	−0.0027 (4)
N5	0.0190 (5)	0.0291 (5)	0.0184 (5)	−0.0018 (4)	0.0070 (4)	−0.0017 (4)
N6	0.0264 (6)	0.0677 (9)	0.0219 (6)	0.0031 (5)	0.0110 (5)	0.0056 (5)
N7	0.0234 (5)	0.0446 (7)	0.0214 (5)	0.0003 (4)	0.0102 (4)	0.0019 (4)
N8	0.0228 (5)	0.0421 (6)	0.0203 (5)	−0.0014 (4)	0.0088 (4)	0.0003 (4)
N9	0.0213 (5)	0.0372 (6)	0.0192 (5)	0.0019 (4)	0.0058 (4)	0.0016 (4)
N10	0.0194 (5)	0.0349 (6)	0.0189 (5)	0.0014 (4)	0.0065 (4)	0.0007 (4)
C1	0.0248 (6)	0.0296 (6)	0.0249 (6)	0.0019 (5)	0.0094 (5)	0.0029 (5)
C2	0.0276 (6)	0.0338 (7)	0.0319 (7)	−0.0019 (5)	0.0111 (5)	0.0075 (5)
C3	0.0332 (7)	0.0480 (9)	0.0409 (8)	−0.0021 (6)	0.0235 (6)	0.0069 (6)
C4	0.0443 (8)	0.0474 (9)	0.0465 (9)	−0.0021 (7)	0.0328 (8)	−0.0055 (7)
C5	0.0348 (7)	0.0354 (7)	0.0379 (7)	−0.0032 (5)	0.0230 (6)	−0.0048 (6)
C6	0.0190 (5)	0.0310 (6)	0.0209 (6)	0.0022 (4)	0.0088 (5)	0.0045 (5)
C7	0.0250 (6)	0.0360 (7)	0.0230 (6)	−0.0064 (5)	0.0094 (5)	−0.0040 (5)
C8	0.0215 (5)	0.0261 (6)	0.0166 (5)	0.0001 (4)	0.0066 (4)	0.0007 (4)
C9	0.0213 (5)	0.0251 (6)	0.0165 (5)	0.0014 (4)	0.0071 (4)	0.0016 (4)
C10	0.0205 (5)	0.0236 (5)	0.0167 (5)	0.0020 (4)	0.0059 (4)	0.0006 (4)
C11	0.0196 (5)	0.0254 (6)	0.0165 (5)	0.0011 (4)	0.0073 (4)	−0.0005 (4)
C12	0.0289 (6)	0.0244 (6)	0.0284 (6)	−0.0028 (5)	0.0070 (5)	0.0001 (5)
C13	0.0364 (7)	0.0276 (6)	0.0333 (7)	0.0070 (5)	0.0096 (6)	0.0044 (5)
C14	0.0245 (6)	0.0436 (8)	0.0243 (6)	0.0088 (5)	0.0055 (5)	0.0011 (5)
C15	0.0241 (6)	0.0394 (8)	0.0292 (7)	−0.0045 (5)	0.0038 (5)	−0.0072 (6)
C16	0.0283 (6)	0.0247 (6)	0.0285 (6)	−0.0015 (5)	0.0070 (5)	−0.0028 (5)
C17	0.0220 (5)	0.0232 (5)	0.0161 (5)	0.0021 (4)	0.0070 (4)	0.0017 (4)
C18	0.0246 (6)	0.0260 (6)	0.0214 (6)	0.0039 (4)	0.0110 (5)	0.0031 (4)
C19	0.0246 (6)	0.0352 (7)	0.0295 (7)	−0.0037 (5)	0.0089 (5)	−0.0052 (5)
C20	0.0254 (6)	0.0434 (8)	0.0360 (8)	0.0026 (6)	0.0066 (6)	−0.0123 (6)
C21	0.0279 (7)	0.0770 (12)	0.0327 (8)	0.0111 (7)	0.0124 (6)	−0.0084 (7)
C22	0.0328 (7)	0.0861 (13)	0.0318 (8)	0.0097 (8)	0.0191 (7)	0.0092 (8)
C23	0.0266 (6)	0.0548 (9)	0.0276 (7)	0.0049 (6)	0.0123 (6)	0.0064 (6)
C24	0.0180 (5)	0.0374 (7)	0.0216 (6)	−0.0028 (5)	0.0070 (5)	−0.0061 (5)
C25	0.0244 (6)	0.0430 (8)	0.0245 (6)	0.0050 (5)	0.0068 (5)	0.0028 (5)
C26	0.0212 (5)	0.0312 (6)	0.0196 (5)	−0.0021 (5)	0.0063 (5)	−0.0018 (5)
C27	0.0213 (5)	0.0296 (6)	0.0189 (6)	−0.0020 (4)	0.0070 (5)	−0.0017 (4)
C28	0.0211 (5)	0.0293 (6)	0.0189 (6)	−0.0021 (4)	0.0063 (5)	−0.0004 (4)
C29	0.0214 (5)	0.0349 (7)	0.0181 (5)	0.0048 (5)	0.0081 (5)	−0.0011 (5)
C30	0.0286 (6)	0.0337 (7)	0.0373 (7)	0.0028 (5)	0.0069 (6)	−0.0039 (6)
C31	0.0389 (8)	0.0492 (10)	0.0530 (10)	−0.0079 (7)	0.0133 (8)	−0.0193 (8)
C32	0.0275 (7)	0.0824 (13)	0.0322 (8)	−0.0039 (8)	0.0056 (6)	−0.0215 (8)
C33	0.0302 (7)	0.0860 (14)	0.0261 (7)	0.0194 (8)	0.0031 (6)	0.0071 (8)
C34	0.0354 (7)	0.0438 (8)	0.0304 (7)	0.0124 (6)	0.0102 (6)	0.0085 (6)
C35	0.0228 (5)	0.0294 (6)	0.0184 (5)	−0.0013 (4)	0.0066 (5)	−0.0016 (4)
C36	0.0244 (6)	0.0373 (7)	0.0230 (6)	0.0000 (5)	0.0106 (5)	0.0010 (5)

Geometric parameters (Å, º) top

S1—C18	1.7442 (12)	C8—C9	1.4207 (16)
S1—C17	1.7545 (12)	C9—C10	1.3755 (16)
S2—C36	1.7370 (13)	C9—C17	1.4488 (15)
S2—C35	1.7454 (12)	C11—C16	1.3757 (17)
O1—C10	1.3517 (14)	C11—C12	1.3791 (17)
O1—C11	1.4050 (14)	C12—C13	1.3922 (18)
O2—C28	1.3512 (15)	C12—H12A	0.9500
O2—C29	1.4043 (15)	C13—C14	1.383 (2)
N1—C18	1.3452 (15)	C13—H13A	0.9500
N1—H1A	0.8800	C14—C15	1.381 (2)
N1—H1B	0.8800	C14—H14A	0.9500
N2—C18	1.3124 (16)	C15—C16	1.3844 (18)
N2—N3	1.3791 (13)	C15—H15A	0.9500
N3—C17	1.3007 (15)	C16—H16A	0.9500
N4—C8	1.3272 (15)	C19—C20	1.3892 (18)
N4—N5	1.3743 (14)	C19—C24	1.3891 (19)
N5—C10	1.3556 (15)	C19—H19A	0.9500
N5—C6	1.4288 (15)	C20—C21	1.379 (2)
N6—C36	1.3493 (17)	C20—H20A	0.9500
N6—H6A	0.8800	C21—C22	1.385 (3)
N6—H6B	0.8800	C21—H21A	0.9500
N7—C36	1.3136 (17)	C22—C23	1.387 (2)
N7—N8	1.3826 (14)	C22—H22A	0.9500
N8—C35	1.2991 (16)	C23—C24	1.3888 (19)
N9—C26	1.3279 (16)	C23—H23A	0.9500
N9—N10	1.3744 (14)	C25—C26	1.4908 (17)
N10—C28	1.3555 (15)	C25—H25A	0.9800
N10—C24	1.4279 (15)	C25—H25B	0.9800
C1—C6	1.3887 (18)	C25—H25C	0.9800
C1—C2	1.3904 (17)	C26—C27	1.4198 (17)
C1—H1C	0.9500	C27—C28	1.3787 (17)
C2—C3	1.383 (2)	C27—C35	1.4503 (16)
C2—H2B	0.9500	C29—C30	1.375 (2)
C3—C4	1.388 (2)	C29—C34	1.3781 (18)
C3—H3B	0.9500	C30—C31	1.398 (2)
C4—C5	1.3859 (19)	C30—H30A	0.9500
C4—H4B	0.9500	C31—C32	1.368 (3)
C5—C6	1.3915 (18)	C31—H31A	0.9500
C5—H5A	0.9500	C32—C33	1.369 (3)
C7—C8	1.4927 (16)	C32—H32A	0.9500
C7—H7B	0.9800	C33—C34	1.391 (2)
C7—H7C	0.9800	C33—H33A	0.9500
C7—H7D	0.9800	C34—H34A	0.9500

C18—S1—C17	86.71 (5)	C14—C15—H15A	119.9
C36—S2—C35	86.84 (6)	C16—C15—H15A	119.9
C10—O1—C11	118.17 (9)	C11—C16—C15	119.26 (12)
C28—O2—C29	118.28 (10)	C11—C16—H16A	120.4
C18—N1—H1A	120.0	C15—C16—H16A	120.4
C18—N1—H1B	120.0	N3—C17—C9	122.87 (10)
H1A—N1—H1B	120.0	N3—C17—S1	113.56 (8)
C18—N2—N3	112.82 (10)	C9—C17—S1	123.54 (9)
C17—N3—N2	113.26 (10)	N2—C18—N1	122.82 (11)
C8—N4—N5	105.94 (9)	N2—C18—S1	113.65 (9)
C10—N5—N4	110.28 (9)	N1—C18—S1	123.52 (10)
C10—N5—C6	130.08 (10)	C20—C19—C24	119.10 (13)
N4—N5—C6	119.42 (9)	C20—C19—H19A	120.4
C36—N6—H6A	120.0	C24—C19—H19A	120.4
C36—N6—H6B	120.0	C21—C20—C19	120.55 (14)
H6A—N6—H6B	120.0	C21—C20—H20A	119.7
C36—N7—N8	112.34 (10)	C19—C20—H20A	119.7
C35—N8—N7	113.19 (10)	C20—C21—C22	119.89 (13)
C26—N9—N10	105.92 (10)	C20—C21—H21A	120.1
C28—N10—N9	110.37 (10)	C22—C21—H21A	120.1
C28—N10—C24	130.33 (11)	C21—C22—C23	120.51 (15)
N9—N10—C24	118.92 (10)	C21—C22—H22A	119.7
C6—C1—C2	119.22 (12)	C23—C22—H22A	119.7
C6—C1—H1C	120.4	C22—C23—C24	119.09 (15)
C2—C1—H1C	120.4	C22—C23—H23A	120.5
C3—C2—C1	120.27 (13)	C24—C23—H23A	120.5
C3—C2—H2B	119.9	C23—C24—C19	120.84 (12)
C1—C2—H2B	119.9	C23—C24—N10	118.13 (12)
C2—C3—C4	120.04 (12)	C19—C24—N10	120.95 (11)
C2—C3—H3B	120.0	C26—C25—H25A	109.5
C4—C3—H3B	120.0	C26—C25—H25B	109.5
C5—C4—C3	120.43 (14)	H25A—C25—H25B	109.5
C5—C4—H4B	119.8	C26—C25—H25C	109.5
C3—C4—H4B	119.8	H25A—C25—H25C	109.5
C4—C5—C6	119.08 (13)	H25B—C25—H25C	109.5
C4—C5—H5A	120.5	N9—C26—C27	111.09 (11)
C6—C5—H5A	120.5	N9—C26—C25	120.35 (11)
C1—C6—C5	120.93 (11)	C27—C26—C25	128.55 (11)
C1—C6—N5	120.67 (11)	C28—C27—C26	104.34 (10)
C5—C6—N5	118.33 (11)	C28—C27—C35	127.21 (11)
C8—C7—H7B	109.5	C26—C27—C35	128.21 (11)
C8—C7—H7C	109.5	O2—C28—N10	122.78 (11)
H7B—C7—H7C	109.5	O2—C28—C27	128.84 (11)
C8—C7—H7D	109.5	N10—C28—C27	108.27 (11)
H7B—C7—H7D	109.5	C30—C29—C34	121.48 (13)
H7C—C7—H7D	109.5	C30—C29—O2	123.56 (11)
N4—C8—C9	111.05 (10)	C34—C29—O2	114.95 (12)
N4—C8—C7	120.65 (10)	C29—C30—C31	118.28 (14)
C9—C8—C7	128.29 (10)	C29—C30—H30A	120.9
C10—C9—C8	104.34 (10)	C31—C30—H30A	120.9
C10—C9—C17	127.61 (11)	C32—C31—C30	121.03 (17)
C8—C9—C17	128.04 (11)	C32—C31—H31A	119.5
O1—C10—N5	123.32 (10)	C30—C31—H31A	119.5
O1—C10—C9	128.20 (10)	C31—C32—C33	119.66 (15)
N5—C10—C9	108.38 (10)	C31—C32—H32A	120.2
C16—C11—C12	121.86 (11)	C33—C32—H32A	120.2
C16—C11—O1	114.58 (10)	C32—C33—C34	120.81 (15)
C12—C11—O1	123.52 (11)	C32—C33—H33A	119.6
C11—C12—C13	118.12 (12)	C34—C33—H33A	119.6
C11—C12—H12A	120.9	C29—C34—C33	118.74 (15)
C13—C12—H12A	120.9	C29—C34—H34A	120.6
C14—C13—C12	120.90 (13)	C33—C34—H34A	120.6
C14—C13—H13A	119.6	N8—C35—C27	123.33 (11)
C12—C13—H13A	119.6	N8—C35—S2	113.75 (9)
C15—C14—C13	119.61 (12)	C27—C35—S2	122.91 (9)
C15—C14—H14A	120.2	N7—C36—N6	123.00 (12)
C13—C14—H14A	120.2	N7—C36—S2	113.89 (9)
C14—C15—C16	120.25 (12)	N6—C36—S2	123.06 (10)

C18—N2—N3—C17	−0.36 (15)	N3—N2—C18—S1	0.46 (14)
C8—N4—N5—C10	0.95 (13)	C17—S1—C18—N2	−0.33 (10)
C8—N4—N5—C6	−174.12 (10)	C17—S1—C18—N1	−179.62 (12)
C36—N7—N8—C35	−0.94 (17)	C24—C19—C20—C21	0.5 (2)
C26—N9—N10—C28	0.83 (14)	C19—C20—C21—C22	−0.9 (2)
C26—N9—N10—C24	−172.83 (11)	C20—C21—C22—C23	0.2 (3)
C6—C1—C2—C3	1.42 (19)	C21—C22—C23—C24	0.8 (2)
C1—C2—C3—C4	−0.8 (2)	C22—C23—C24—C19	−1.1 (2)
C2—C3—C4—C5	−0.9 (2)	C22—C23—C24—N10	175.63 (13)
C3—C4—C5—C6	2.0 (2)	C20—C19—C24—C23	0.46 (19)
C2—C1—C6—C5	−0.36 (19)	C20—C19—C24—N10	−176.23 (11)
C2—C1—C6—N5	−177.25 (11)	C28—N10—C24—C23	156.26 (13)
C4—C5—C6—C1	−1.3 (2)	N9—N10—C24—C23	−31.54 (17)
C4—C5—C6—N5	175.65 (13)	C28—N10—C24—C19	−27.0 (2)
C10—N5—C6—C1	−27.86 (19)	N9—N10—C24—C19	145.24 (12)
N4—N5—C6—C1	146.09 (11)	N10—N9—C26—C27	−0.30 (14)
C10—N5—C6—C5	155.17 (13)	N10—N9—C26—C25	178.83 (11)
N4—N5—C6—C5	−30.88 (17)	N9—C26—C27—C28	−0.31 (14)
N5—N4—C8—C9	−0.65 (13)	C25—C26—C27—C28	−179.36 (13)
N5—N4—C8—C7	178.21 (11)	N9—C26—C27—C35	174.30 (12)
N4—C8—C9—C10	0.12 (14)	C25—C26—C27—C35	−4.7 (2)
C7—C8—C9—C10	−178.63 (12)	C29—O2—C28—N10	−80.86 (15)
N4—C8—C9—C17	179.00 (11)	C29—O2—C28—C27	103.48 (15)
C7—C8—C9—C17	0.3 (2)	N9—N10—C28—O2	−177.49 (11)
C11—O1—C10—N5	−77.24 (14)	C24—N10—C28—O2	−4.8 (2)
C11—O1—C10—C9	106.74 (14)	N9—N10—C28—C27	−1.05 (14)
N4—N5—C10—O1	−177.60 (10)	C24—N10—C28—C27	171.67 (12)
C6—N5—C10—O1	−3.22 (19)	C26—C27—C28—O2	176.96 (12)
N4—N5—C10—C9	−0.90 (13)	C35—C27—C28—O2	2.3 (2)
C6—N5—C10—C9	173.49 (11)	C26—C27—C28—N10	0.81 (14)
C8—C9—C10—O1	176.97 (11)	C35—C27—C28—N10	−173.88 (12)
C17—C9—C10—O1	−1.9 (2)	C28—O2—C29—C30	−11.62 (17)
C8—C9—C10—N5	0.47 (13)	C28—O2—C29—C34	169.42 (11)
C17—C9—C10—N5	−178.42 (11)	C34—C29—C30—C31	0.5 (2)
C10—O1—C11—C16	159.41 (10)	O2—C29—C30—C31	−178.34 (13)
C10—O1—C11—C12	−22.92 (16)	C29—C30—C31—C32	0.0 (2)
C16—C11—C12—C13	0.19 (19)	C30—C31—C32—C33	−0.5 (2)
O1—C11—C12—C13	−177.32 (11)	C31—C32—C33—C34	0.4 (2)
C11—C12—C13—C14	0.3 (2)	C30—C29—C34—C33	−0.6 (2)
C12—C13—C14—C15	−0.5 (2)	O2—C29—C34—C33	178.33 (12)
C13—C14—C15—C16	0.3 (2)	C32—C33—C34—C29	0.2 (2)
C12—C11—C16—C15	−0.36 (19)	N7—N8—C35—C27	−178.05 (11)
O1—C11—C16—C15	177.35 (11)	N7—N8—C35—S2	0.50 (15)
C14—C15—C16—C11	0.1 (2)	C28—C27—C35—N8	153.50 (13)
N2—N3—C17—C9	178.14 (11)	C26—C27—C35—N8	−19.9 (2)
N2—N3—C17—S1	0.10 (13)	C28—C27—C35—S2	−24.92 (18)
C10—C9—C17—N3	159.30 (12)	C26—C27—C35—S2	161.64 (11)
C8—C9—C17—N3	−19.3 (2)	C36—S2—C35—N8	0.03 (11)
C10—C9—C17—S1	−22.85 (18)	C36—S2—C35—C27	178.59 (11)
C8—C9—C17—S1	158.51 (10)	N8—N7—C36—N6	−176.50 (13)
C18—S1—C17—N3	0.12 (10)	N8—N7—C36—S2	0.97 (15)
C18—S1—C17—C9	−177.90 (11)	C35—S2—C36—N7	−0.58 (11)
N3—N2—C18—N1	179.75 (11)	C35—S2—C36—N6	176.89 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N7	0.88	2.19	3.0266 (16)	158
N1—H1B···N4ⁱ	0.88	2.21	3.0113 (15)	150
N6—H6A···N2	0.88	2.11	2.9467 (15)	159
N6—H6B···N9ⁱⁱ	0.88	2.23	2.9915 (16)	145

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₅N₅OS
M_r	349.41
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	153
a, b, c (Å)	20.2987 (5), 9.6934 (3), 19.0726 (6)
β (°)	114.846 (1)
V (Å³)	3405.43 (17)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.66 × 0.43 × 0.31

Data collection
Diffractometer	Rigaku R-AXIS SPIDER
Absorption correction	Empirical (using intensity measurements) (ABSCOR; Higashi, 1995)
T_min, T_max	0.876, 0.939
No. of measured, independent and observed [I > 2σ(I)] reflections	32693, 7772, 6769
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.101, 1.05
No. of reflections	7772
No. of parameters	453
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.41

Computer programs: RAPID-AUTO (Rigaku, 2004), RAPID-AUTO, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3(Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N7	0.88	2.19	3.0266 (16)	157.8
N1—H1B···N4ⁱ	0.88	2.21	3.0113 (15)	150.4
N6—H6A···N2	0.88	2.11	2.9467 (15)	159.1
N6—H6B···N9ⁱⁱ	0.88	2.23	2.9915 (16)	145.0

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, −y+3/2, z−1/2.

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