A monoclinic polymorph of N-eth­oxy­carbonyl-N′-(3-phenyl-1H-1,2,4-triazol-5-yl)thio­urea

Dolzhenko, A.V.; Tan, G.K.; Dolzhenko, A.V.; Koh, L.L.; Chui, W.K.

doi:10.1107/S1600536810026164

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 8| August 2010| Pages o1990-o1991

https://doi.org/10.1107/S1600536810026164

Open

access

A monoclinic polymorph of N-ethoxycarbonyl-N′-(3-phenyl-1H-1,2,4-triazol-5-yl)thiourea

Anton V. Dolzhenko,^a ^*‡ Geok Kheng Tan,^b Anna V. Dolzhenko,^c Lip Lin Koh ^b and Wai Keung Chui ^a

^aDepartment of Pharmacy, Faculty of Science, National University of Singapore, 18 Science Drive 4, Singapore 117543, Singapore, ^bDepartment of Chemistry, Faculty of Science, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore, and ^cPerm State Pharmaceutical Academy, 2 Polevaya Street, Perm 614990, Russian Federation
^*Correspondence e-mail: dolzhenkoav@gmail.com

(Received 28 June 2010; accepted 2 July 2010; online 10 July 2010)

The title compound, C₁₂H₁₃N₅O₂S {systematic name: ethyl N-[N-(3-phenyl-1H-1,2,4-triazol-5-yl)carbamothioyl]carbamate}, is a monoclinic polymorph (space group P2₁/c) which crystallizes with three similar independent molecules in the asymmetric unit. The triazole ring makes dihedral angles of 6.6 (2), 8.4 (2) and 10.6 (2)° with the phenyl ring in the three independent molecules. The structure was previously reported [Dolzhenko et al. (2010a ). Acta Cryst., E46, o425] as a triclinic polymorph crystallizing in space group P $[\overline{1}]$ . Molecules in both polymorphs possess two S(6) rings generated by intramolecular N—H⋯S and N—H⋯O hydrogen bonds, resulting in similar molecular geometries. However, the two polymorphs differ in the crystal packing. In contrast to the dimers of the triclinic polymorph, molecules of the monoclinic polymorph are connected by intermolecular N—H⋯S and N—H⋯N hydrogen bonds, forming pseudosymmetric trimers arranged in sheets parallel to (302).

Related literature

For the synthesis, tautomerism and crystal structure studies of related 1,2,4-triazoles, see: Dolzhenko et al. (2007 , 2009a ,b ,c ). For the crystal structure of the triclinic polymorph, see: Dolzhenko et al. (2010a). For the crystal structure of N-carbethoxy-N′-(3-aryl-1H-1,2,4-triazol-5-yl)thiourea, see: Dolzhenko et al. (2010b ). For the graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₂H₁₃N₅O₂S
M_r = 291.33
Monoclinic, P 2₁ /c
a = 13.4743 (6) Å
b = 20.4817 (9) Å
c = 15.0266 (7) Å
β = 104.040 (1)°
V = 4023.1 (3) Å³
Z = 12
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 223 K
0.56 × 0.24 × 0.12 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ) T_min = 0.872, T_max = 0.971
28189 measured reflections
9216 independent reflections
5772 reflections with I > 2σ(I)
R_int = 0.055

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.164
S = 1.03
9216 reflections
598 parameters
86 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.85 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯S1	0.90 (1)	2.44 (3)	2.978 (2)	119 (2)
N8—H8N⋯S2	0.90 (1)	2.42 (3)	2.975 (2)	121 (2)
N13—H13N⋯S3	0.90 (1)	2.44 (3)	2.997 (2)	120 (2)
N8—H8N⋯S3	0.90 (1)	2.44 (2)	3.253 (2)	150 (2)
N3—H3N⋯S2ⁱ	0.90 (2)	2.43 (2)	3.238 (2)	151 (2)
N13—H13N⋯S1ⁱⁱ	0.90 (2)	2.49 (3)	3.306 (3)	151 (2)
N4—H4N⋯O2	0.89 (1)	1.94 (2)	2.661 (3)	137 (2)
N9—H9N⋯O4	0.90 (1)	1.91 (2)	2.648 (3)	138 (2)
N14—H14N⋯O6	0.89 (1)	1.90 (2)	2.619 (3)	136 (2)
N10—H10N⋯N2ⁱⁱ	0.89 (2)	2.51 (2)	3.390 (3)	170 (2)
N15—H15N⋯N7	0.89 (2)	2.31 (2)	3.197 (3)	180 (3)
Symmetry codes: (i) x, y, z-1; (ii) x, y, z+1.

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: SHELXS97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810026164/ci5124sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810026164/ci5124Isup2.hkl

checkCIF report

Comment top

In our studies on the triazole tautomerism in solution and crystals (Dolzhenko et al., 2009a,b,c), we reported recently the crystal structure of N-carbethoxy-N'-(3-phenyl-1H-1,2,4-triazol-5-yl)thiourea, which crystallized in the triclinic P1 space group (Dolzhenko et al., 2010a). Herein, we present a new monoclinic polymorph of N-carbethoxy-N'-(3-phenyl-1H-1,2,4-triazol-5-yl)thiourea, which crystallized in the P2₁/c space group with three similar crystallographically independent molecules in the asymmetric unit (Fig. 1). The molecules in both polymorphs exist in the same tautomeric form and possess similar molecular geometry.

In both polymorph, the N—H···S hydrogen bonds between the endocyclic NH group of the triazole ring and the thioureido sulfur atom (Fig. 2 and Table 1) are arranged in a S6 graph-set motif (Bernstein et al., 1995) stabilizing the tautomer structure. The general configurations of the carbethoxythiourea group in the title molecule replicate that of previously reported for triclinic polymorph (Dolzhenko et al., 2010a) and a similar structure (Dolzhenko et al., 2010b). The strong intramolecular hydrogen bonding between carbonyl oxygen atom and thiourea NH group arranged in S(6) graph-set motif which is common for carbethoxythioureas (Dolzhenko et al., 2010a,b). In the three independent molecules, the triazole ring make dihedral angles of 6.6 (2)°, 8.4 (2)° and 10.6 (2)° with the corresponding phenyl rings [cf. 6.59 (10)° for the triclinic polymorph (Dolzhenko et al., 2010a)].

The monoclinic and triclinic polymorphs are significantly different in crystal packing. In contrast to the dimers of triclinic polymorph (Dolzhenko et al., 2010a), molecules of monoclinic polymorph are connected with intermolecular hydrogen bonding of the C═S···H—N—N···H—N pattern forming pseudosymmetric trimer structures arranged in sheets parallel to the (302) plane.

Related literature top

For the synthesis, tautomerism and crystal structure studies of related 1,2,4-triazoles, see: Dolzhenko et al. (2007, 2009a,b,c). For the crystal structure of the triclinic polymorph, see: Dolzhenko et al. (2010a). For the crystal structure of N-carbethoxy-N'-(3-aryl-1H-1,2,4-triazol-5-yl)thiourea, see: Dolzhenko et al. (2010b). For the graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995).

Experimental top

The title compound was synthesized by nucleophilic addition of 3(5)-amino-5(3)-phenyl-1H-1,2,4-triazole (Dolzhenko et al., 2007), to ethoxycarbonyl isothiocyanate in DMF solution at room temperature (Fig.3). Single crystals suitable for crystallographic analysis were grown by recrystallization from toluene.

Structure description top

For the synthesis, tautomerism and crystal structure studies of related 1,2,4-triazoles, see: Dolzhenko et al. (2007, 2009a,b,c). For the crystal structure of the triclinic polymorph, see: Dolzhenko et al. (2010a). For the crystal structure of N-carbethoxy-N'-(3-aryl-1H-1,2,4-triazol-5-yl)thiourea, see: Dolzhenko et al. (2010b). For the graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995).

Computing details top

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

Figures top

	Fig. 1. Crystal packing of the title compound, viewed along the c axis.
	Fig. 2. Synthesis of N-carbethoxy-N'-(3-phenyl-1H-1,2,4-triazol-5-yl)thiourea

ethyl N-[N-(3-phenyl-1H-1,2,4-triazol-5- yl)carbamothioyl]carbamate top

Crystal data top

C₁₂H₁₃N₅O₂S	F(000) = 1824
M_r = 291.33	D_x = 1.443 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 454 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.4743 (6) Å	Cell parameters from 3587 reflections
b = 20.4817 (9) Å	θ = 2.4–21.7°
c = 15.0266 (7) Å	µ = 0.25 mm⁻¹
β = 104.040 (1)°	T = 223 K
V = 4023.1 (3) Å³	Rod, colourless
Z = 12	0.56 × 0.24 × 0.12 mm

Data collection top

Bruker SMART APEX CCD diffractometer	9216 independent reflections
Radiation source: fine-focus sealed tube	5772 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
φ and ω scans	θ_max = 27.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −17→17
T_min = 0.872, T_max = 0.971	k = −25→26
28189 measured reflections	l = −11→19

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0784P)² + 0.4202P] where P = (F_o² + 2F_c²)/3
9216 reflections	(Δ/σ)_max = 0.001
598 parameters	Δρ_max = 0.85 e Å⁻³
86 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

C₁₂H₁₃N₅O₂S	V = 4023.1 (3) Å³
M_r = 291.33	Z = 12
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.4743 (6) Å	µ = 0.25 mm⁻¹
b = 20.4817 (9) Å	T = 223 K
c = 15.0266 (7) Å	0.56 × 0.24 × 0.12 mm
β = 104.040 (1)°

Data collection top

Bruker SMART APEX CCD diffractometer	9216 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	5772 reflections with I > 2σ(I)
T_min = 0.872, T_max = 0.971	R_int = 0.055
28189 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	86 restraints
wR(F²) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.85 e Å⁻³
9216 reflections	Δρ_min = −0.52 e Å⁻³
598 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	Occ. (<1)
S1	0.20531 (6)	0.64994 (3)	−0.06103 (6)	0.0441 (2)
S2	0.17227 (7)	0.48747 (3)	0.97238 (6)	0.0513 (2)
S3	0.31718 (9)	0.53635 (4)	0.83353 (7)	0.0713 (3)
O1	0.23376 (15)	0.88193 (8)	−0.06109 (14)	0.0410 (5)
O2	0.17439 (15)	0.85011 (9)	0.06024 (14)	0.0404 (5)
O3	0.04408 (16)	0.38003 (9)	1.20243 (14)	0.0455 (5)
O4	0.06816 (16)	0.30621 (9)	1.09867 (14)	0.0445 (5)
O6	0.4656 (2)	0.50555 (10)	0.59819 (18)	0.0682 (7)
N1	0.07377 (17)	0.68052 (10)	0.18244 (15)	0.0328 (5)
N2	0.07758 (18)	0.57196 (10)	0.15331 (16)	0.0369 (5)
N3	0.11842 (18)	0.60701 (10)	0.09369 (16)	0.0347 (5)
H3N	0.1465 (19)	0.5860 (12)	0.0535 (15)	0.042*
N4	0.15156 (17)	0.72134 (10)	0.06799 (16)	0.0327 (5)
H4N	0.144 (2)	0.7611 (7)	0.0893 (18)	0.039*
N5	0.21787 (18)	0.77628 (10)	−0.03862 (16)	0.0354 (5)
H5N	0.244 (2)	0.7715 (14)	−0.0874 (13)	0.043*
N6	0.21916 (17)	0.28401 (10)	0.88026 (16)	0.0339 (5)
N7	0.28571 (17)	0.35600 (10)	0.79634 (16)	0.0372 (5)
N8	0.24310 (17)	0.38767 (10)	0.85782 (16)	0.0353 (5)
H8N	0.243 (2)	0.4314 (5)	0.860 (2)	0.042*
N9	0.15402 (17)	0.35768 (10)	0.97396 (16)	0.0340 (5)
H9N	0.1309 (19)	0.3232 (9)	0.9998 (18)	0.041*
N10	0.09302 (18)	0.41605 (10)	1.08206 (16)	0.0361 (5)
H10N	0.087 (2)	0.4548 (8)	1.1074 (18)	0.043*
N11	0.40967 (17)	0.69867 (10)	0.67246 (16)	0.0361 (5)
N12	0.34161 (18)	0.74325 (10)	0.78232 (18)	0.0418 (6)
N13	0.34239 (19)	0.67680 (10)	0.78753 (17)	0.0391 (6)
H13N	0.318 (2)	0.6556 (13)	0.8300 (15)	0.047*
N14	0.39497 (18)	0.58664 (10)	0.70279 (16)	0.0349 (5)
H14N	0.421 (2)	0.5794 (14)	0.6543 (13)	0.042*
N15	0.37852 (18)	0.47458 (10)	0.70418 (17)	0.0373 (6)
H15N	0.353 (2)	0.4418 (10)	0.7300 (18)	0.045*
C1	−0.0235 (2)	0.65393 (13)	0.3321 (2)	0.0389 (7)
H1	−0.0021	0.6967	0.3239	0.047*
C2	−0.0761 (2)	0.64147 (14)	0.3989 (2)	0.0455 (7)
H2	−0.0906	0.6756	0.4355	0.055*
C3	−0.1069 (2)	0.57897 (14)	0.4112 (2)	0.0483 (8)
H3	−0.1420	0.5705	0.4569	0.058*
C4	−0.0870 (2)	0.52842 (14)	0.3573 (2)	0.0462 (8)
H4	−0.1090	0.4858	0.3659	0.055*
C5	−0.0343 (2)	0.54099 (13)	0.2905 (2)	0.0409 (7)
H5	−0.0203	0.5067	0.2538	0.049*
C6	−0.0022 (2)	0.60396 (12)	0.27731 (19)	0.0328 (6)
C7	0.0510 (2)	0.61851 (12)	0.20477 (19)	0.0316 (6)
C8	0.11565 (19)	0.67033 (12)	0.11294 (18)	0.0303 (6)
C9	0.1901 (2)	0.71755 (12)	−0.00656 (19)	0.0317 (6)
C10	0.2060 (2)	0.83789 (12)	−0.0065 (2)	0.0336 (6)
C11	0.2122 (2)	0.94956 (12)	−0.0410 (2)	0.0422 (7)
H11A	0.2514	0.9618	0.0205	0.051*
H11B	0.1392	0.9551	−0.0441	0.051*
C12	0.2431 (2)	0.99114 (13)	−0.1123 (2)	0.0506 (8)
H12A	0.3157	0.9858	−0.1076	0.061*
H12B	0.2286	1.0366	−0.1024	0.061*
H12C	0.2049	0.9778	−0.1729	0.061*
C13	0.2936 (2)	0.17599 (13)	0.7891 (2)	0.0432 (7)
H13	0.2675	0.1673	0.8404	0.052*
C14	0.3236 (3)	0.12477 (14)	0.7417 (2)	0.0517 (8)
H14	0.3181	0.0817	0.7614	0.062*
C15	0.3612 (2)	0.13640 (14)	0.6660 (2)	0.0491 (8)
H15	0.3809	0.1015	0.6334	0.059*
C16	0.3697 (3)	0.20008 (15)	0.6385 (2)	0.0531 (8)
H16	0.3960	0.2086	0.5872	0.064*
C17	0.3401 (2)	0.25111 (14)	0.6854 (2)	0.0460 (7)
H17	0.3459	0.2942	0.6656	0.055*
C18	0.3016 (2)	0.23983 (12)	0.7617 (2)	0.0348 (6)
C19	0.2690 (2)	0.29402 (12)	0.81255 (19)	0.0333 (6)
C20	0.2040 (2)	0.34429 (12)	0.90587 (19)	0.0317 (6)
C21	0.1390 (2)	0.41679 (12)	1.00938 (19)	0.0329 (6)
C22	0.0671 (2)	0.36185 (13)	1.1259 (2)	0.0366 (6)
C23	0.0197 (3)	0.32624 (14)	1.2587 (2)	0.0491 (8)
H23A	0.0681	0.2902	1.2611	0.059*
H23B	−0.0495	0.3099	1.2323	0.059*
C24	0.0270 (3)	0.35195 (17)	1.3519 (3)	0.0707 (11)
H24A	0.0939	0.3714	1.3754	0.085*
H24B	0.0174	0.3166	1.3919	0.085*
H24C	−0.0255	0.3847	1.3496	0.085*
C25	0.4554 (2)	0.82809 (14)	0.6144 (2)	0.0499 (8)
H25	0.4852	0.7915	0.5933	0.060*
C26	0.4684 (3)	0.88965 (16)	0.5801 (3)	0.0598 (9)
H26	0.5072	0.8948	0.5364	0.072*
C27	0.4241 (3)	0.94289 (15)	0.6103 (3)	0.0633 (10)
H27	0.4321	0.9846	0.5869	0.076*
C28	0.3683 (3)	0.93515 (15)	0.6747 (3)	0.0591 (10)
H28	0.3381	0.9718	0.6951	0.071*
C29	0.3559 (2)	0.87429 (13)	0.7100 (2)	0.0485 (8)
H29	0.3181	0.8697	0.7546	0.058*
C30	0.3992 (2)	0.82008 (13)	0.6793 (2)	0.0403 (7)
C31	0.3835 (2)	0.75410 (12)	0.7126 (2)	0.0357 (6)
C32	0.3826 (2)	0.65233 (12)	0.72182 (19)	0.0327 (6)
C33	0.3652 (2)	0.53406 (12)	0.7427 (2)	0.0353 (6)
C34	0.4265 (3)	0.46419 (14)	0.6349 (2)	0.0472 (8)
O5	0.4364 (4)	0.4001 (3)	0.6227 (3)	0.0402 (13)	0.634 (7)
C35	0.4867 (5)	0.3865 (3)	0.5460 (5)	0.0637 (17)	0.634 (7)
H35A	0.4571	0.4146	0.4935	0.076*	0.634 (7)
H35B	0.5600	0.3959	0.5660	0.076*	0.634 (7)
C36	0.4716 (6)	0.3202 (3)	0.5201 (5)	0.0745 (18)	0.634 (7)
H36A	0.5042	0.3111	0.4705	0.089*	0.634 (7)
H36B	0.3989	0.3112	0.4998	0.089*	0.634 (7)
H36C	0.5015	0.2926	0.5722	0.089*	0.634 (7)
O5A	0.3960 (7)	0.4021 (5)	0.5995 (6)	0.041 (2)	0.366 (7)
C35A	0.4221 (8)	0.3748 (5)	0.5141 (6)	0.076 (3)	0.366 (7)
H35C	0.3752	0.3392	0.4884	0.091*	0.366 (7)
H35D	0.4166	0.4089	0.4675	0.091*	0.366 (7)
C36A	0.5241 (7)	0.3513 (7)	0.5415 (9)	0.088 (3)	0.366 (7)
H36D	0.5445	0.3340	0.4886	0.106*	0.366 (7)
H36E	0.5281	0.3171	0.5869	0.106*	0.366 (7)
H36F	0.5694	0.3868	0.5679	0.106*	0.366 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0679 (5)	0.0275 (3)	0.0481 (5)	0.0027 (3)	0.0359 (4)	−0.0004 (3)
S2	0.0890 (6)	0.0220 (3)	0.0586 (5)	−0.0087 (3)	0.0485 (5)	−0.0055 (3)
S3	0.1328 (9)	0.0264 (4)	0.0852 (7)	−0.0089 (4)	0.0859 (7)	−0.0078 (4)
O1	0.0559 (12)	0.0216 (9)	0.0544 (13)	−0.0001 (8)	0.0309 (10)	0.0031 (9)
O2	0.0540 (12)	0.0286 (9)	0.0454 (12)	−0.0025 (8)	0.0254 (10)	−0.0023 (9)
O3	0.0715 (14)	0.0304 (10)	0.0441 (12)	−0.0072 (9)	0.0322 (11)	0.0013 (9)
O4	0.0625 (13)	0.0262 (10)	0.0512 (13)	−0.0044 (9)	0.0263 (11)	0.0021 (9)
O6	0.121 (2)	0.0318 (11)	0.0786 (17)	0.0009 (12)	0.0760 (16)	0.0008 (12)
N1	0.0418 (13)	0.0264 (11)	0.0341 (13)	0.0006 (9)	0.0166 (10)	−0.0002 (10)
N2	0.0496 (14)	0.0283 (11)	0.0377 (13)	−0.0019 (10)	0.0198 (11)	0.0033 (10)
N3	0.0477 (14)	0.0252 (11)	0.0378 (13)	0.0000 (10)	0.0229 (11)	−0.0001 (10)
N4	0.0452 (13)	0.0216 (10)	0.0368 (13)	0.0009 (9)	0.0207 (11)	0.0000 (10)
N5	0.0494 (14)	0.0254 (11)	0.0393 (14)	0.0012 (10)	0.0261 (11)	0.0027 (10)
N6	0.0449 (13)	0.0208 (10)	0.0377 (13)	0.0008 (9)	0.0135 (11)	−0.0021 (10)
N7	0.0485 (14)	0.0272 (11)	0.0408 (14)	−0.0003 (10)	0.0204 (11)	−0.0054 (11)
N8	0.0501 (14)	0.0213 (10)	0.0411 (14)	−0.0016 (10)	0.0235 (11)	−0.0023 (10)
N9	0.0490 (14)	0.0192 (10)	0.0383 (13)	−0.0029 (9)	0.0198 (11)	0.0004 (10)
N10	0.0510 (14)	0.0240 (11)	0.0402 (14)	0.0000 (10)	0.0242 (11)	−0.0002 (10)
N11	0.0446 (14)	0.0246 (11)	0.0413 (14)	−0.0028 (9)	0.0146 (11)	0.0024 (10)
N12	0.0541 (15)	0.0229 (11)	0.0496 (16)	−0.0003 (10)	0.0148 (13)	−0.0021 (11)
N13	0.0577 (16)	0.0243 (11)	0.0412 (15)	−0.0009 (10)	0.0235 (12)	−0.0014 (11)
N14	0.0503 (14)	0.0232 (10)	0.0381 (14)	−0.0002 (10)	0.0244 (11)	−0.0007 (10)
N15	0.0537 (15)	0.0208 (11)	0.0461 (15)	−0.0024 (10)	0.0287 (12)	−0.0028 (10)
C1	0.0518 (18)	0.0317 (14)	0.0360 (16)	−0.0018 (12)	0.0163 (13)	0.0029 (13)
C2	0.066 (2)	0.0379 (16)	0.0387 (17)	0.0036 (14)	0.0235 (15)	0.0006 (14)
C3	0.071 (2)	0.0423 (17)	0.0416 (17)	0.0021 (15)	0.0328 (16)	0.0105 (15)
C4	0.063 (2)	0.0311 (14)	0.0522 (19)	−0.0042 (13)	0.0298 (16)	0.0100 (14)
C5	0.0547 (18)	0.0312 (14)	0.0425 (17)	−0.0002 (12)	0.0232 (14)	0.0013 (13)
C6	0.0382 (15)	0.0285 (13)	0.0336 (15)	−0.0001 (11)	0.0127 (12)	0.0050 (12)
C7	0.0368 (15)	0.0268 (13)	0.0335 (15)	0.0009 (11)	0.0129 (12)	0.0015 (12)
C8	0.0344 (14)	0.0258 (12)	0.0327 (15)	0.0015 (10)	0.0118 (12)	0.0001 (12)
C9	0.0354 (14)	0.0254 (12)	0.0378 (15)	−0.0005 (10)	0.0155 (12)	0.0045 (12)
C10	0.0333 (15)	0.0265 (13)	0.0437 (17)	−0.0017 (10)	0.0146 (13)	0.0004 (12)
C11	0.0544 (18)	0.0239 (13)	0.0523 (19)	0.0022 (12)	0.0210 (15)	0.0014 (13)
C12	0.062 (2)	0.0268 (14)	0.071 (2)	0.0003 (13)	0.0310 (18)	0.0062 (15)
C13	0.0514 (18)	0.0285 (14)	0.0544 (19)	0.0027 (12)	0.0219 (15)	−0.0029 (14)
C14	0.068 (2)	0.0262 (14)	0.066 (2)	0.0040 (14)	0.0261 (18)	−0.0050 (15)
C15	0.056 (2)	0.0363 (16)	0.056 (2)	0.0050 (14)	0.0173 (16)	−0.0157 (15)
C16	0.069 (2)	0.0500 (19)	0.048 (2)	−0.0010 (16)	0.0298 (17)	−0.0092 (16)
C17	0.065 (2)	0.0281 (14)	0.0504 (19)	−0.0030 (13)	0.0243 (16)	−0.0037 (14)
C18	0.0348 (15)	0.0277 (13)	0.0422 (17)	−0.0012 (11)	0.0099 (12)	−0.0042 (12)
C19	0.0367 (15)	0.0278 (13)	0.0353 (16)	−0.0022 (11)	0.0085 (12)	−0.0011 (12)
C20	0.0347 (15)	0.0257 (12)	0.0340 (15)	−0.0011 (10)	0.0068 (12)	−0.0009 (12)
C21	0.0406 (15)	0.0252 (12)	0.0350 (15)	0.0001 (11)	0.0133 (12)	−0.0004 (12)
C22	0.0437 (16)	0.0321 (15)	0.0377 (16)	−0.0013 (12)	0.0169 (13)	0.0031 (13)
C23	0.066 (2)	0.0380 (16)	0.0505 (19)	−0.0121 (14)	0.0289 (17)	0.0066 (15)
C24	0.116 (3)	0.052 (2)	0.062 (2)	−0.011 (2)	0.059 (2)	0.0019 (19)
C25	0.0508 (19)	0.0303 (15)	0.069 (2)	−0.0012 (13)	0.0158 (17)	0.0057 (15)
C26	0.062 (2)	0.0415 (18)	0.076 (3)	−0.0066 (15)	0.0177 (19)	0.0157 (18)
C27	0.070 (2)	0.0277 (16)	0.084 (3)	−0.0066 (15)	0.004 (2)	0.0120 (18)
C28	0.073 (2)	0.0249 (15)	0.073 (3)	0.0055 (15)	0.005 (2)	−0.0047 (16)
C29	0.057 (2)	0.0295 (15)	0.056 (2)	0.0001 (13)	0.0076 (16)	−0.0052 (14)
C30	0.0403 (16)	0.0268 (13)	0.0480 (18)	−0.0036 (12)	−0.0004 (14)	0.0009 (13)
C31	0.0388 (16)	0.0237 (13)	0.0425 (17)	−0.0014 (11)	0.0055 (13)	−0.0012 (12)
C32	0.0366 (15)	0.0248 (12)	0.0374 (15)	−0.0012 (11)	0.0101 (12)	−0.0020 (12)
C33	0.0439 (16)	0.0266 (13)	0.0418 (16)	−0.0023 (11)	0.0227 (13)	−0.0036 (12)
C34	0.069 (2)	0.0275 (14)	0.054 (2)	0.0017 (14)	0.0334 (17)	−0.0047 (14)
O5	0.047 (3)	0.0255 (19)	0.053 (3)	0.002 (2)	0.021 (2)	−0.010 (2)
C35	0.067 (4)	0.050 (3)	0.092 (4)	−0.011 (3)	0.056 (3)	−0.030 (3)
C36	0.089 (4)	0.064 (3)	0.086 (4)	−0.012 (3)	0.051 (3)	−0.016 (3)
O5A	0.060 (6)	0.032 (3)	0.026 (3)	0.022 (4)	0.001 (4)	−0.001 (3)
C35A	0.077 (5)	0.058 (4)	0.096 (5)	−0.006 (4)	0.028 (4)	0.024 (4)
C36A	0.083 (5)	0.080 (6)	0.107 (5)	−0.016 (5)	0.034 (5)	0.001 (5)

Geometric parameters (Å, º) top

S1—C9	1.647 (3)	C5—C6	1.390 (4)
S2—C21	1.651 (3)	C5—H5	0.94
S3—C33	1.647 (3)	C6—C7	1.473 (4)
O1—C10	1.332 (3)	C11—C12	1.503 (4)
O1—C11	1.462 (3)	C11—H11A	0.98
O2—C10	1.208 (3)	C11—H11B	0.98
O3—C22	1.316 (3)	C12—H12A	0.97
O3—C23	1.474 (3)	C12—H12B	0.97
O4—C22	1.212 (3)	C12—H12C	0.97
O6—C34	1.200 (3)	C13—C14	1.382 (4)
N1—C8	1.318 (3)	C13—C18	1.383 (4)
N1—C7	1.367 (3)	C13—H13	0.94
N2—C7	1.330 (3)	C14—C15	1.374 (4)
N2—N3	1.364 (3)	C14—H14	0.94
N3—C8	1.331 (3)	C15—C16	1.381 (4)
N3—H3N	0.897 (10)	C15—H15	0.94
N4—C9	1.346 (3)	C16—C17	1.373 (4)
N4—C8	1.393 (3)	C16—H16	0.94
N4—H4N	0.889 (10)	C17—C18	1.387 (4)
N5—C10	1.374 (3)	C17—H17	0.94
N5—C9	1.381 (3)	C18—C19	1.473 (4)
N5—H5N	0.890 (10)	C23—C24	1.476 (5)
N6—C20	1.324 (3)	C23—H23A	0.98
N6—C19	1.364 (3)	C23—H23B	0.98
N7—C19	1.322 (3)	C24—H24A	0.97
N7—N8	1.364 (3)	C24—H24B	0.97
N8—C20	1.331 (3)	C24—H24C	0.97
N8—H8N	0.897 (10)	C25—C30	1.382 (4)
N9—C21	1.357 (3)	C25—C26	1.389 (4)
N9—C20	1.382 (3)	C25—H25	0.94
N9—H9N	0.896 (10)	C26—C27	1.372 (5)
N10—C22	1.378 (3)	C26—H26	0.94
N10—C21	1.380 (3)	C27—C28	1.371 (5)
N10—H10N	0.892 (10)	C27—H27	0.94
N11—C32	1.310 (3)	C28—C29	1.381 (4)
N11—C31	1.371 (3)	C28—H28	0.94
N12—C31	1.324 (4)	C29—C30	1.384 (4)
N12—N13	1.363 (3)	C29—H29	0.94
N13—C32	1.334 (3)	C30—C31	1.474 (4)
N13—H13N	0.896 (10)	C34—O5	1.337 (6)
N14—C33	1.341 (3)	C34—O5A	1.401 (12)
N14—C32	1.394 (3)	O5—C35	1.499 (6)
N14—H14N	0.891 (10)	C35—C36	1.414 (6)
N15—C34	1.369 (4)	C35—H35A	0.98
N15—C33	1.379 (3)	C35—H35B	0.98
N15—H15N	0.883 (10)	C36—H36A	0.97
C1—C2	1.384 (4)	C36—H36B	0.97
C1—C6	1.387 (4)	C36—H36C	0.97
C1—H1	0.94	O5A—C35A	1.517 (7)
C2—C3	1.372 (4)	C35A—C36A	1.420 (7)
C2—H2	0.94	C35A—H35C	0.98
C3—C4	1.380 (4)	C35A—H35D	0.98
C3—H3	0.94	C36A—H36D	0.97
C4—C5	1.388 (4)	C36A—H36E	0.97
C4—H4	0.94	C36A—H36F	0.97

C10—O1—C11	114.5 (2)	C16—C17—C18	120.7 (3)
C22—O3—C23	115.0 (2)	C16—C17—H17	119.6
C8—N1—C7	102.2 (2)	C18—C17—H17	119.6
C7—N2—N3	102.3 (2)	C13—C18—C17	118.4 (3)
C8—N3—N2	109.5 (2)	C13—C18—C19	120.2 (3)
C8—N3—H3N	130.7 (18)	C17—C18—C19	121.4 (2)
N2—N3—H3N	119.6 (18)	N7—C19—N6	114.7 (2)
C9—N4—C8	127.6 (2)	N7—C19—C18	122.9 (2)
C9—N4—H4N	116.9 (19)	N6—C19—C18	122.4 (2)
C8—N4—H4N	115.4 (19)	N6—C20—N8	110.8 (2)
C10—N5—C9	127.8 (2)	N6—C20—N9	122.5 (2)
C10—N5—H5N	119.5 (19)	N8—C20—N9	126.7 (2)
C9—N5—H5N	112.6 (19)	N9—C21—N10	116.0 (2)
C20—N6—C19	102.4 (2)	N9—C21—S2	124.9 (2)
C19—N7—N8	102.3 (2)	N10—C21—S2	119.12 (19)
C20—N8—N7	109.7 (2)	O4—C22—O3	125.9 (3)
C20—N8—H8N	130 (2)	O4—C22—N10	124.8 (3)
N7—N8—H8N	121 (2)	O3—C22—N10	109.3 (2)
C21—N9—C20	127.8 (2)	O3—C23—C24	107.8 (2)
C21—N9—H9N	115.6 (18)	O3—C23—H23A	110.2
C20—N9—H9N	116.5 (18)	C24—C23—H23A	110.2
C22—N10—C21	127.0 (2)	O3—C23—H23B	110.2
C22—N10—H10N	116.9 (19)	C24—C23—H23B	110.2
C21—N10—H10N	115.7 (19)	H23A—C23—H23B	108.5
C32—N11—C31	102.4 (2)	C23—C24—H24A	109.5
C31—N12—N13	102.4 (2)	C23—C24—H24B	109.5
C32—N13—N12	109.4 (2)	H24A—C24—H24B	109.5
C32—N13—H13N	128.9 (19)	C23—C24—H24C	109.5
N12—N13—H13N	121.8 (19)	H24A—C24—H24C	109.5
C33—N14—C32	128.3 (2)	H24B—C24—H24C	109.5
C33—N14—H14N	116.7 (19)	C30—C25—C26	120.7 (3)
C32—N14—H14N	114.7 (19)	C30—C25—H25	119.7
C34—N15—C33	126.2 (2)	C26—C25—H25	119.7
C34—N15—H15N	121.2 (19)	C27—C26—C25	119.6 (4)
C33—N15—H15N	112.7 (19)	C27—C26—H26	120.2
C2—C1—C6	120.7 (3)	C25—C26—H26	120.2
C2—C1—H1	119.7	C28—C27—C26	119.9 (3)
C6—C1—H1	119.7	C28—C27—H27	120.0
C3—C2—C1	119.7 (3)	C26—C27—H27	120.0
C3—C2—H2	120.2	C27—C28—C29	120.9 (3)
C1—C2—H2	120.2	C27—C28—H28	119.5
C2—C3—C4	120.8 (3)	C29—C28—H28	119.5
C2—C3—H3	119.6	C28—C29—C30	119.7 (3)
C4—C3—H3	119.6	C28—C29—H29	120.1
C3—C4—C5	119.5 (3)	C30—C29—H29	120.1
C3—C4—H4	120.3	C25—C30—C29	119.1 (3)
C5—C4—H4	120.3	C25—C30—C31	119.8 (3)
C4—C5—C6	120.5 (3)	C29—C30—C31	121.0 (3)
C4—C5—H5	119.8	N12—C31—N11	114.4 (2)
C6—C5—H5	119.8	N12—C31—C30	123.1 (3)
C1—C6—C5	118.9 (3)	N11—C31—C30	122.5 (3)
C1—C6—C7	119.9 (2)	N11—C32—N13	111.5 (2)
C5—C6—C7	121.2 (2)	N11—C32—N14	121.3 (2)
N2—C7—N1	114.5 (2)	N13—C32—N14	127.2 (2)
N2—C7—C6	122.2 (2)	N14—C33—N15	116.0 (2)
N1—C7—C6	123.2 (2)	N14—C33—S3	124.6 (2)
N1—C8—N3	111.5 (2)	N15—C33—S3	119.4 (2)
N1—C8—N4	122.1 (2)	O6—C34—O5	124.1 (3)
N3—C8—N4	126.4 (2)	O6—C34—N15	125.5 (3)
N4—C9—N5	115.6 (2)	O5—C34—N15	109.7 (3)
N4—C9—S1	125.57 (19)	O6—C34—O5A	125.9 (5)
N5—C9—S1	118.8 (2)	N15—C34—O5A	106.3 (4)
O2—C10—O1	125.4 (2)	C34—O5—C35	111.5 (5)
O2—C10—N5	125.2 (2)	C36—C35—O5	109.2 (5)
O1—C10—N5	109.4 (2)	C36—C35—H35A	109.8
O1—C11—C12	106.7 (2)	O5—C35—H35A	109.8
O1—C11—H11A	110.4	C36—C35—H35B	109.8
C12—C11—H11A	110.4	O5—C35—H35B	109.8
O1—C11—H11B	110.4	H35A—C35—H35B	108.3
C12—C11—H11B	110.4	C35—C36—H36A	109.5
H11A—C11—H11B	108.6	C35—C36—H36B	109.5
C11—C12—H12A	109.5	H36A—C36—H36B	109.5
C11—C12—H12B	109.5	C35—C36—H36C	109.5
H12A—C12—H12B	109.5	H36A—C36—H36C	109.5
C11—C12—H12C	109.5	H36B—C36—H36C	109.5
H12A—C12—H12C	109.5	C34—O5A—C35A	123.3 (9)
H12B—C12—H12C	109.5	C36A—C35A—O5A	106.6 (6)
C14—C13—C18	120.7 (3)	C36A—C35A—H35C	110.4
C14—C13—H13	119.6	O5A—C35A—H35C	110.4
C18—C13—H13	119.6	C36A—C35A—H35D	110.4
C15—C14—C13	120.5 (3)	O5A—C35A—H35D	110.4
C15—C14—H14	119.7	H35C—C35A—H35D	108.6
C13—C14—H14	119.7	C35A—C36A—H36D	109.5
C14—C15—C16	119.0 (3)	C35A—C36A—H36E	109.5
C14—C15—H15	120.5	H36D—C36A—H36E	109.5
C16—C15—H15	120.5	C35A—C36A—H36F	109.5
C17—C16—C15	120.7 (3)	H36D—C36A—H36F	109.5
C17—C16—H16	119.7	H36E—C36A—H36F	109.5
C15—C16—H16	119.7

C7—N2—N3—C8	0.9 (3)	C19—N6—C20—N9	179.4 (2)
C19—N7—N8—C20	−0.2 (3)	N7—N8—C20—N6	0.6 (3)
C31—N12—N13—C32	−0.6 (3)	N7—N8—C20—N9	−179.5 (2)
C6—C1—C2—C3	0.3 (5)	C21—N9—C20—N6	176.1 (3)
C1—C2—C3—C4	−0.6 (5)	C21—N9—C20—N8	−3.8 (5)
C2—C3—C4—C5	0.6 (5)	C20—N9—C21—N10	−175.3 (3)
C3—C4—C5—C6	−0.3 (5)	C20—N9—C21—S2	4.2 (4)
C2—C1—C6—C5	0.0 (4)	C22—N10—C21—N9	4.6 (4)
C2—C1—C6—C7	178.1 (3)	C22—N10—C21—S2	−175.0 (2)
C4—C5—C6—C1	0.0 (4)	C23—O3—C22—O4	1.2 (4)
C4—C5—C6—C7	−178.1 (3)	C23—O3—C22—N10	−177.1 (2)
N3—N2—C7—N1	−0.9 (3)	C21—N10—C22—O4	−10.9 (5)
N3—N2—C7—C6	176.8 (2)	C21—N10—C22—O3	167.5 (3)
C8—N1—C7—N2	0.6 (3)	C22—O3—C23—C24	163.0 (3)
C8—N1—C7—C6	−177.2 (2)	C30—C25—C26—C27	−0.6 (5)
C1—C6—C7—N2	176.7 (3)	C25—C26—C27—C28	0.6 (5)
C5—C6—C7—N2	−5.2 (4)	C26—C27—C28—C29	0.1 (5)
C1—C6—C7—N1	−5.7 (4)	C27—C28—C29—C30	−0.8 (5)
C5—C6—C7—N1	172.4 (3)	C26—C25—C30—C29	0.0 (5)
C7—N1—C8—N3	0.1 (3)	C26—C25—C30—C31	177.9 (3)
C7—N1—C8—N4	−179.7 (2)	C28—C29—C30—C25	0.7 (5)
N2—N3—C8—N1	−0.7 (3)	C28—C29—C30—C31	−177.2 (3)
N2—N3—C8—N4	179.1 (2)	N13—N12—C31—N11	0.7 (3)
C9—N4—C8—N1	−175.8 (3)	N13—N12—C31—C30	179.7 (2)
C9—N4—C8—N3	4.4 (4)	C32—N11—C31—N12	−0.6 (3)
C8—N4—C9—N5	178.4 (2)	C32—N11—C31—C30	−179.6 (2)
C8—N4—C9—S1	−1.1 (4)	C25—C30—C31—N12	171.4 (3)
C10—N5—C9—N4	−3.7 (4)	C29—C30—C31—N12	−10.6 (4)
C10—N5—C9—S1	175.9 (2)	C25—C30—C31—N11	−9.6 (4)
C11—O1—C10—O2	−6.9 (4)	C29—C30—C31—N11	168.3 (3)
C11—O1—C10—N5	172.5 (2)	C31—N11—C32—N13	0.1 (3)
C9—N5—C10—O2	5.1 (5)	C31—N11—C32—N14	179.1 (2)
C9—N5—C10—O1	−174.3 (2)	N12—N13—C32—N11	0.3 (3)
C10—O1—C11—C12	−176.9 (2)	N12—N13—C32—N14	−178.6 (3)
C18—C13—C14—C15	−0.5 (5)	C33—N14—C32—N11	−175.2 (3)
C13—C14—C15—C16	0.7 (5)	C33—N14—C32—N13	3.6 (5)
C14—C15—C16—C17	−0.6 (5)	C32—N14—C33—N15	173.9 (3)
C15—C16—C17—C18	0.4 (5)	C32—N14—C33—S3	−7.3 (4)
C14—C13—C18—C17	0.3 (4)	C34—N15—C33—N14	5.8 (4)
C14—C13—C18—C19	179.8 (3)	C34—N15—C33—S3	−173.0 (3)
C16—C17—C18—C13	−0.2 (5)	C33—N15—C34—O6	1.1 (6)
C16—C17—C18—C19	−179.7 (3)	C33—N15—C34—O5	172.4 (3)
N8—N7—C19—N6	−0.2 (3)	C33—N15—C34—O5A	−162.6 (4)
N8—N7—C19—C18	179.8 (2)	O6—C34—O5—C35	−9.8 (7)
C20—N6—C19—N7	0.6 (3)	N15—C34—O5—C35	178.8 (4)
C20—N6—C19—C18	−179.4 (2)	O5A—C34—O5—C35	93.0 (14)
C13—C18—C19—N7	172.0 (3)	C34—O5—C35—C36	−164.9 (7)
C17—C18—C19—N7	−8.6 (4)	O6—C34—O5A—C35A	8.9 (10)
C13—C18—C19—N6	−8.0 (4)	O5—C34—O5A—C35A	−85.4 (14)
C17—C18—C19—N6	171.4 (3)	N15—C34—O5A—C35A	172.6 (6)
C19—N6—C20—N8	−0.7 (3)	C34—O5A—C35A—C36A	80.4 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···S1	0.90 (1)	2.44 (3)	2.978 (2)	119 (2)
N8—H8N···S2	0.90 (1)	2.42 (3)	2.975 (2)	121 (2)
N13—H13N···S3	0.90 (1)	2.44 (3)	2.997 (2)	120 (2)
N8—H8N···S3	0.90 (1)	2.44 (2)	3.253 (2)	150 (2)
N3—H3N···S2ⁱ	0.90 (2)	2.43 (2)	3.238 (2)	151 (2)
N13—H13N···S1ⁱⁱ	0.90 (2)	2.49 (3)	3.306 (3)	151 (2)
N4—H4N···O2	0.89 (1)	1.94 (2)	2.661 (3)	137 (2)
N9—H9N···O4	0.90 (1)	1.91 (2)	2.648 (3)	138 (2)
N14—H14N···O6	0.89 (1)	1.90 (2)	2.619 (3)	136 (2)
N10—H10N···N2ⁱⁱ	0.89 (2)	2.51 (2)	3.390 (3)	170 (2)
N15—H15N···N7	0.89 (2)	2.31 (2)	3.197 (3)	180 (3)

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₃N₅O₂S
M_r	291.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	223
a, b, c (Å)	13.4743 (6), 20.4817 (9), 15.0266 (7)
β (°)	104.040 (1)
V (Å³)	4023.1 (3)
Z	12
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.56 × 0.24 × 0.12

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.872, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	28189, 9216, 5772
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.164, 1.03
No. of reflections	9216
No. of parameters	598
No. of restraints	86
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.85, −0.52

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···S1	0.90 (1)	2.44 (3)	2.978 (2)	119 (2)
N8—H8N···S2	0.90 (1)	2.42 (3)	2.975 (2)	121 (2)
N13—H13N···S3	0.90 (1)	2.44 (3)	2.997 (2)	120 (2)
N8—H8N···S3	0.90 (1)	2.44 (2)	3.253 (2)	150 (2)
N3—H3N···S2ⁱ	0.90 (2)	2.43 (2)	3.238 (2)	151 (2)
N13—H13N···S1ⁱⁱ	0.90 (2)	2.49 (3)	3.306 (3)	151 (2)
N4—H4N···O2	0.89 (1)	1.94 (2)	2.661 (3)	137 (2)
N9—H9N···O4	0.90 (1)	1.91 (2)	2.648 (3)	138 (2)
N14—H14N···O6	0.89 (1)	1.90 (2)	2.619 (3)	136 (2)
N10—H10N···N2ⁱⁱ	0.89 (2)	2.51 (2)	3.390 (3)	170 (2)
N15—H15N···N7	0.89 (2)	2.31 (2)	3.197 (3)	180 (3)

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

Footnotes

‡Thomson Reuters ResearcherID: B-1130-2008.

Acknowledgements

This work was supported by the National Medical Research Council, Singapore (grant No. NMRC/NIG/0019/2008).

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2001). SMART and SAINT. Bruker AXS GmbH, Karlsruhe, Germany. Google Scholar
Dolzhenko, A. V., Dolzhenko, A. V. & Chui, W. K. (2007). Tetrahedron, 63, 12888–12895. Web of Science CrossRef CAS Google Scholar
Dolzhenko, A. V., Pastorin, G., Dolzhenko, A. V. & Chui, W. K. (2009a). Tetrahedron Lett. 50, 2124–2128. Web of Science CrossRef CAS Google Scholar
Dolzhenko, A. V., Tan, G. K., Koh, L. L., Dolzhenko, A. V. & Chui, W. K. (2009b). Acta Cryst. E65, o126. Web of Science CSD CrossRef IUCr Journals Google Scholar
Dolzhenko, A. V., Tan, G. K., Koh, L. L., Dolzhenko, A. V. & Chui, W. K. (2009c). Acta Cryst. E65, o125. Web of Science CSD CrossRef IUCr Journals Google Scholar
Dolzhenko, A. V., Tan, G. K., Koh, L. L., Dolzhenko, A. V. & Chui, W. K. (2010a). Acta Cryst. E66, o425. Web of Science CSD CrossRef IUCr Journals Google Scholar
Dolzhenko, A. V., Tan, G. K., Koh, L. L., Dolzhenko, A. V. & Chui, W. K. (2010b). Acta Cryst. E66, o549–o550. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2001). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 8| August 2010| Pages o1990-o1991

https://doi.org/10.1107/S1600536810026164

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

A monoclinic polymorph of N-eth­­oxy­carbonyl-N′-(3-phenyl-1H-1,2,4-triazol-5-yl)thio­urea

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

A monoclinic polymorph of N-ethoxycarbonyl-N′-(3-phenyl-1H-1,2,4-triazol-5-yl)thiourea