1-(4-Methyl­benzo­yl)-3-[5-(4-pyrid­yl)-1,3,4-thia­diazol-2-yl]urea

Zhan, X.-H.; Wang, Z.-Y.; Tan, X.-H.; Tan, Z.-W.; Song, X.-J.

doi:10.1107/S1600536808035149

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2255

doi:10.1107/S1600536808035149

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1-(4-Methylbenzoyl)-3-[5-(4-pyridyl)-1,3,4-thiadiazol-2-yl]urea

Xiu-Huan Zhan,^a,^b Zi-Yun Wang,^a Xiao-Hong Tan,^c Zhi-Wei Tan ^c and Xin-Jian Song ^a,^b ^*

^aDepartment of Chemistry, Zhoukou Normal University, Zhoukou 466000, People's Republic of China, ^bKey Laboratory of Biological Resources Protection and Utilization of Hubei Province, Hubei University for Nationalities, Enshi, Hubei 445000, People's Republic of China, and ^cSchool of Chemical and Environmental Engineering, Hubei University for Nationalities, Enshi, Hubei 445000, People's Republic of China
^*Correspondence e-mail: whxjsong@yahoo.com.cn

(Received 14 October 2008; accepted 28 October 2008; online 8 November 2008)

In the title compound, C₁₆H₁₃N₅O₂S, the five non-H atoms of the urea linkage adopt a planar configuration owing to the presence of an intramolecular N—H⋯O hydrogen bond. The maximum deviation from planarity is 0.022 (2) Å. The thiadiazole and pyridine heterocyclic rings are close to being coplanar, with a dihedral angle of 6.7 (2)° between their mean planes. Intermolecular N—H⋯O hydrogen bonds link two neighbouring molecules into centrosymmetric R₂²(8) dimers. Four C atoms and the attached H atoms of the benzene ring are disordered over two positions of equal occupancy.

Related literature

For general background, see: Chen et al. (2005 ); Foroumadi et al. (2002 ); Song et al. (2007 ); Song et al. (2008 ). For related structures, see: Song & Tan et al. (2005 ). For the synthesis, see: Song & Feng et al. (2005 ).

Experimental

Crystal data

C₁₆H₁₃N₅O₂S
M_r = 339.37
Triclinic, $[P \overline 1]$
a = 5.0563 (5) Å
b = 11.8561 (11) Å
c = 13.2506 (12) Å
α = 88.892 (2)°
β = 80.849 (2)°
γ = 77.989 (2)°
V = 766.99 (13) Å³
Z = 2
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 297 (2) K
0.20 × 0.10 × 0.04 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
6171 measured reflections
2978 independent reflections
2120 reflections with I > 2σ(I)
R_int = 0.096

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.195
S = 1.06
2978 reflections
214 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.86	1.90	2.583 (3)	135
N1—H1⋯O2ⁱ	0.86	2.10	2.935 (3)	165
Symmetry code: (i) -x+2, -y+2, -z.

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: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808035149/fj2164sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808035149/fj2164Isup2.hkl

checkCIF report

Comment top

1,3,4-Thiadiazole derivatives have been reported to possess broad spectrum bioactivities (Foroumadi et al., 2002; Song et al., 2007). Urea derivatives, especially aroylurea derivatives, have attracted many chemist's interest owing to their diverse biological effects, such as insecticidal, fungicidal, herbicidal and plant-growth regulating activities (Chen et al., 2005; Song et al., 2008). Furthermore, pyridine derivatives have become one of research hotspots in modern agrochemistry and medicinal chemistry. In our continuing search for new plant-growth regulators, we would like to investigate aroyl ureas incorporating both 1,3,4-thiadiazole and pyridine rings, including the title compound.

The crystal structure (Fig.1) revealed that the urea linkage unit O1—C8—N1—C9—N2—H2 adopts the stable conformation due to the the formation of a strong intramolecular N—H···O hydrogen bond to give a planar six-membered ring, as reported (Song and Tan et al., 2005), which is essentially coplanar with a maximum deviation from planarity of 0.022 (2)Å for atom O1. The thiadiazole and pyridine heterocyclic fragments also lie essentially in the same plane, the maximum deviation from that plane being 0.059 (3)Å for atom C15. The dihedral angle between the two mean planes is 6.7 (2)°. All bond lengths and angles are as expected. In the crystal structure, the molecules are linked by complementary N—H···O hydrogen bonds into centrosymmetric R₂²(8) dimers (Fig. 2 and Table 1).

Related literature top

For general background, see: Chen et al. (2005); Foroumadi et al. (2002); Song et al. (2007); Song et al. (2008). For related structures, see: Song & Tan et al. (2005). For the synthesis, see: Song & Feng et al. (2005).

Experimental top

The title compound was prepared according to the procedure of Song and Feng et al. (2005). Suitable crystals were obtained by vapor diffusion of methanol in DMF at room temperature (m.p. >573 K). Elemental analysis: analysis calculated for C₁₆H₁₃N₅O₂S: C 56.63, H 3.86, N 20.64%; found: C 56.55, H 3.76, N 20.81%.

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: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented by circles of arbitrary size. Both disorder components are shown.
	Fig. 2. A partial packing diagram for (I) [symmetry code: (a) 2 - x, 2 - y, -z]. Hydrogen bonds are indicated by dashed lines.

1-(4-Methylbenzoyl)-3-[5-(4-pyridyl)-1,3,4-thiadiazol-2-yl]urea top

Crystal data top

C₁₆H₁₃N₅O₂S	Z = 2
M_r = 339.37	F(000) = 352
Triclinic, P1	D_x = 1.469 Mg m⁻³
Hall symbol: -P 1	Melting point > 573 K
a = 5.0563 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.8561 (11) Å	Cell parameters from 1721 reflections
c = 13.2506 (12) Å	θ = 2.3–24.7°
α = 88.892 (2)°	µ = 0.23 mm⁻¹
β = 80.849 (2)°	T = 297 K
γ = 77.989 (2)°	Block, colorless
V = 766.99 (13) Å³	0.20 × 0.10 × 0.04 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2120 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.096
Graphite monochromator	θ_max = 26.0°, θ_min = 1.8°
ϕ and ω scans	h = −6→6
6171 measured reflections	k = −14→14
2978 independent reflections	l = −16→16

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.195	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.1026P)²] where P = (F_o² + 2F_c²)/3
2978 reflections	(Δ/σ)_max < 0.001
214 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₆H₁₃N₅O₂S	γ = 77.989 (2)°
M_r = 339.37	V = 766.99 (13) Å³
Triclinic, P1	Z = 2
a = 5.0563 (5) Å	Mo Kα radiation
b = 11.8561 (11) Å	µ = 0.23 mm⁻¹
c = 13.2506 (12) Å	T = 297 K
α = 88.892 (2)°	0.20 × 0.10 × 0.04 mm
β = 80.849 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2120 reflections with I > 2σ(I)
6171 measured reflections	R_int = 0.096
2978 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	0 restraints
wR(F²) = 0.195	H-atom parameters constrained
S = 1.06	Δρ_max = 0.24 e Å⁻³
2978 reflections	Δρ_min = −0.32 e Å⁻³
214 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	0.59211 (17)	0.73166 (7)	−0.09171 (5)	0.0562 (3)
N1	0.8010 (5)	0.96100 (19)	0.13767 (16)	0.0449 (6)
H1	0.9109	1.0058	0.1159	0.054*
N2	0.5583 (5)	0.82578 (19)	0.09796 (16)	0.0459 (6)
H2	0.4995	0.8259	0.1625	0.055*
N3	0.2887 (6)	0.6962 (2)	0.07332 (18)	0.0565 (7)
N4	0.2335 (5)	0.6273 (2)	0.00007 (19)	0.0537 (7)
N5	0.3212 (7)	0.4482 (3)	−0.3539 (2)	0.0800 (9)
O1	0.5680 (6)	0.8977 (2)	0.27987 (16)	0.0916 (9)
O2	0.8225 (5)	0.90478 (17)	−0.02610 (13)	0.0574 (6)
C1	1.0069 (10)	1.2823 (3)	0.5070 (3)	0.0936 (14)
H1A	0.9255	1.2708	0.5759	0.140*
H1B	0.9400	1.3601	0.4874	0.140*
H1C	1.2024	1.2684	0.5025	0.140*
C2	0.9326 (7)	1.1995 (3)	0.4361 (2)	0.0567 (8)
C5	0.8036 (6)	1.0456 (2)	0.3046 (2)	0.0460 (7)
C3A	0.9463 (13)	1.2164 (5)	0.3343 (4)	0.0512 (14)*	0.50
H3A	0.9870	1.2852	0.3082	0.061*	0.50
C4A	0.9036 (12)	1.1382 (5)	0.2677 (4)	0.0432 (13)*	0.50
H4A	0.9429	1.1484	0.1976	0.052*	0.50
C6A	0.7810 (12)	1.0218 (5)	0.4113 (4)	0.0501 (14)*	0.50
H6A	0.7357	0.9534	0.4365	0.060*	0.50
C7A	0.8276 (13)	1.1023 (6)	0.4758 (5)	0.0533 (15)*	0.50
H7A	0.7903	1.0933	0.5462	0.064*	0.50
C3B	1.1141 (12)	1.1626 (5)	0.3379 (4)	0.0473 (13)*	0.50
H3B	1.2799	1.1857	0.3197	0.057*	0.50
C4B	1.0226 (12)	1.0914 (5)	0.2743 (4)	0.0405 (12)*	0.50
H4B	1.1179	1.0753	0.2084	0.049*	0.50
C6B	0.6374 (12)	1.0858 (5)	0.3994 (4)	0.0464 (13)*	0.50
H6B	0.4711	1.0634	0.4188	0.056*	0.50
C7B	0.7220 (13)	1.1576 (5)	0.4624 (4)	0.0468 (14)*	0.50
H7B	0.6200	1.1760	0.5270	0.056*	0.50
C8	0.7154 (7)	0.9624 (3)	0.2418 (2)	0.0518 (8)
C9	0.7317 (6)	0.8962 (2)	0.0638 (2)	0.0430 (7)
C10	0.4699 (6)	0.7538 (2)	0.03602 (19)	0.0422 (6)
C11	0.3759 (6)	0.6354 (2)	−0.0884 (2)	0.0454 (7)
C12	0.3576 (6)	0.5700 (2)	−0.1797 (2)	0.0503 (7)
C13	0.5012 (9)	0.5865 (4)	−0.2729 (3)	0.1010 (16)
H13	0.6168	0.6387	−0.2796	0.121*
C14	0.4754 (10)	0.5258 (4)	−0.3576 (3)	0.1101 (18)
H14	0.5720	0.5405	−0.4206	0.132*
C15	0.1854 (7)	0.4317 (3)	−0.2624 (3)	0.0663 (9)
H15	0.0759	0.3771	−0.2572	0.080*
C16	0.1956 (7)	0.4896 (3)	−0.1754 (2)	0.0581 (8)
H16	0.0937	0.4747	−0.1136	0.070*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0657 (6)	0.0700 (6)	0.0411 (5)	−0.0402 (4)	0.0034 (3)	−0.0127 (3)
N1	0.0545 (15)	0.0513 (13)	0.0352 (12)	−0.0283 (11)	−0.0024 (10)	−0.0022 (9)
N2	0.0566 (15)	0.0543 (14)	0.0333 (12)	−0.0283 (12)	−0.0042 (10)	−0.0003 (10)
N3	0.0751 (18)	0.0661 (16)	0.0403 (13)	−0.0439 (14)	−0.0060 (12)	0.0019 (11)
N4	0.0653 (17)	0.0581 (15)	0.0480 (14)	−0.0341 (13)	−0.0116 (12)	0.0018 (11)
N5	0.093 (2)	0.082 (2)	0.073 (2)	−0.0397 (18)	−0.0040 (17)	−0.0306 (16)
O1	0.145 (2)	0.119 (2)	0.0372 (12)	−0.0999 (19)	0.0036 (13)	−0.0042 (12)
O2	0.0811 (15)	0.0682 (13)	0.0326 (10)	−0.0449 (12)	0.0014 (9)	−0.0052 (9)
C1	0.156 (4)	0.078 (3)	0.062 (2)	−0.043 (3)	−0.035 (2)	−0.0158 (19)
C2	0.074 (2)	0.0541 (18)	0.0452 (17)	−0.0130 (16)	−0.0175 (15)	−0.0104 (13)
C5	0.0518 (17)	0.0528 (16)	0.0355 (14)	−0.0176 (13)	−0.0036 (12)	−0.0009 (12)
C8	0.066 (2)	0.0588 (18)	0.0353 (15)	−0.0287 (15)	−0.0031 (13)	−0.0002 (12)
C9	0.0544 (17)	0.0432 (15)	0.0353 (14)	−0.0201 (13)	−0.0055 (12)	−0.0010 (11)
C10	0.0485 (16)	0.0447 (15)	0.0374 (14)	−0.0173 (12)	−0.0088 (12)	0.0017 (11)
C11	0.0501 (17)	0.0461 (15)	0.0440 (16)	−0.0178 (13)	−0.0082 (13)	−0.0026 (12)
C12	0.0527 (18)	0.0505 (16)	0.0534 (18)	−0.0203 (14)	−0.0114 (14)	−0.0095 (13)
C13	0.125 (4)	0.136 (4)	0.063 (2)	−0.099 (3)	0.022 (2)	−0.037 (2)
C14	0.137 (4)	0.154 (4)	0.059 (2)	−0.099 (4)	0.023 (2)	−0.043 (2)
C15	0.079 (2)	0.0558 (19)	0.075 (2)	−0.0306 (18)	−0.0219 (19)	−0.0083 (16)
C16	0.073 (2)	0.0506 (17)	0.0576 (19)	−0.0263 (16)	−0.0127 (16)	−0.0013 (13)

Geometric parameters (Å, º) top

S1—C10	1.712 (3)	C5—C6B	1.425 (6)
S1—C11	1.733 (3)	C5—C6A	1.427 (6)
N1—C8	1.378 (3)	C5—C8	1.483 (4)
N1—C9	1.386 (3)	C3A—C4A	1.363 (8)
N1—H1	0.8600	C3A—H3A	0.9300
N2—C9	1.354 (3)	C4A—H4A	0.9300
N2—C10	1.380 (3)	C6A—C7A	1.374 (8)
N2—H2	0.8600	C6A—H6A	0.9300
N3—C10	1.285 (3)	C7A—H7A	0.9300
N3—N4	1.379 (3)	C3B—C4B	1.397 (8)
N4—C11	1.287 (3)	C3B—H3B	0.9300
N5—C14	1.320 (5)	C4B—H4B	0.9300
N5—C15	1.327 (4)	C6B—C7B	1.378 (8)
O1—C8	1.225 (4)	C6B—H6B	0.9300
O2—C9	1.217 (3)	C7B—H7B	0.9300
C1—C2	1.512 (4)	C11—C12	1.475 (4)
C1—H1A	0.9600	C12—C13	1.362 (4)
C1—H1B	0.9600	C12—C16	1.375 (4)
C1—H1C	0.9600	C13—C14	1.382 (5)
C2—C7B	1.264 (6)	C13—H13	0.9300
C2—C3A	1.353 (6)	C14—H14	0.9300
C2—C7A	1.424 (7)	C15—C16	1.367 (5)
C2—C3B	1.483 (6)	C15—H15	0.9300
C5—C4B	1.335 (6)	C16—H16	0.9300
C5—C4A	1.353 (6)

C10—S1—C11	86.09 (12)	C6A—C7A—H7A	119.7
C8—N1—C9	127.9 (2)	C2—C7A—H7A	119.7
C8—N1—H1	116.1	C4B—C3B—C2	116.5 (5)
C9—N1—H1	116.1	C4B—C3B—H3B	121.8
C9—N2—C10	124.4 (2)	C2—C3B—H3B	121.8
C9—N2—H2	117.8	C5—C4B—C3B	122.4 (5)
C10—N2—H2	117.8	C5—C4B—H4B	118.8
C10—N3—N4	111.7 (2)	C3B—C4B—H4B	118.8
C11—N4—N3	112.8 (2)	C7B—C6B—C5	120.3 (5)
C14—N5—C15	115.8 (3)	C7B—C6B—H6B	119.9
C2—C1—H1A	109.5	C5—C6B—H6B	119.9
C2—C1—H1B	109.5	C2—C7B—C6B	122.7 (5)
H1A—C1—H1B	109.5	C2—C7B—H7B	118.7
C2—C1—H1C	109.5	C6B—C7B—H7B	118.7
H1A—C1—H1C	109.5	O1—C8—N1	120.4 (3)
H1B—C1—H1C	109.5	O1—C8—C5	121.8 (3)
C7B—C2—C3A	105.2 (4)	N1—C8—C5	117.7 (2)
C3A—C2—C7A	116.6 (4)	O2—C9—N2	123.3 (3)
C7B—C2—C3B	119.8 (4)	O2—C9—N1	120.5 (2)
C7A—C2—C3B	107.3 (4)	N2—C9—N1	116.2 (2)
C7B—C2—C1	120.0 (4)	N3—C10—N2	120.5 (2)
C3A—C2—C1	122.8 (4)	N3—C10—S1	115.5 (2)
C7A—C2—C1	120.5 (4)	N2—C10—S1	124.0 (2)
C3B—C2—C1	120.1 (4)	N4—C11—C12	123.7 (3)
C4B—C5—C6B	117.5 (4)	N4—C11—S1	114.0 (2)
C4A—C5—C6B	104.1 (4)	C12—C11—S1	122.3 (2)
C4B—C5—C6A	110.0 (4)	C13—C12—C16	116.6 (3)
C4A—C5—C6A	119.8 (4)	C13—C12—C11	121.4 (3)
C4B—C5—C8	123.5 (3)	C16—C12—C11	122.0 (3)
C4A—C5—C8	124.9 (3)	C12—C13—C14	120.2 (3)
C6B—C5—C8	118.9 (3)	C12—C13—H13	119.9
C6A—C5—C8	115.3 (3)	C14—C13—H13	119.9
C2—C3A—C4A	123.7 (5)	N5—C14—C13	123.5 (4)
C2—C3A—H3A	118.1	N5—C14—H14	118.2
C4A—C3A—H3A	118.1	C13—C14—H14	118.2
C5—C4A—C3A	119.4 (5)	N5—C15—C16	124.3 (3)
C5—C4A—H4A	120.3	N5—C15—H15	117.8
C3A—C4A—H4A	120.3	C16—C15—H15	117.8
C7A—C6A—C5	118.5 (5)	C15—C16—C12	119.6 (3)
C7A—C6A—H6A	120.8	C15—C16—H16	120.2
C5—C6A—H6A	120.8	C12—C16—H16	120.2
C6A—C7A—C2	120.7 (5)

C10—N3—N4—C11	0.4 (4)	C9—N1—C8—O1	3.1 (5)
C7B—C2—C3A—C4A	−43.7 (7)	C9—N1—C8—C5	−175.8 (3)
C7A—C2—C3A—C4A	−9.7 (8)	C4B—C5—C8—O1	158.9 (4)
C3B—C2—C3A—C4A	75.1 (7)	C4A—C5—C8—O1	−162.1 (4)
C1—C2—C3A—C4A	174.0 (5)	C6B—C5—C8—O1	−25.6 (5)
C4B—C5—C4A—C3A	−89.2 (8)	C6A—C5—C8—O1	18.8 (5)
C6B—C5—C4A—C3A	30.4 (7)	C4B—C5—C8—N1	−22.2 (5)
C6A—C5—C4A—C3A	−9.0 (8)	C4A—C5—C8—N1	16.8 (6)
C8—C5—C4A—C3A	172.0 (4)	C6B—C5—C8—N1	153.3 (3)
C2—C3A—C4A—C5	10.0 (9)	C6A—C5—C8—N1	−162.3 (3)
C4B—C5—C6A—C7A	42.4 (7)	C10—N2—C9—O2	1.7 (5)
C4A—C5—C6A—C7A	8.5 (7)	C10—N2—C9—N1	−179.0 (2)
C6B—C5—C6A—C7A	−66.8 (6)	C8—N1—C9—O2	179.4 (3)
C8—C5—C6A—C7A	−172.3 (5)	C8—N1—C9—N2	0.1 (5)
C5—C6A—C7A—C2	−8.6 (9)	N4—N3—C10—N2	−178.3 (2)
C7B—C2—C7A—C6A	86.0 (9)	N4—N3—C10—S1	0.4 (3)
C3A—C2—C7A—C6A	9.0 (8)	C9—N2—C10—N3	−174.6 (3)
C3B—C2—C7A—C6A	−32.1 (7)	C9—N2—C10—S1	6.8 (4)
C1—C2—C7A—C6A	−174.6 (5)	C11—S1—C10—N3	−0.7 (2)
C7B—C2—C3B—C4B	6.7 (7)	C11—S1—C10—N2	177.9 (3)
C3A—C2—C3B—C4B	−70.3 (7)	N3—N4—C11—C12	179.5 (3)
C7A—C2—C3B—C4B	40.9 (6)	N3—N4—C11—S1	−1.0 (3)
C1—C2—C3B—C4B	−176.4 (4)	C10—S1—C11—N4	1.0 (2)
C4A—C5—C4B—C3B	81.4 (8)	C10—S1—C11—C12	−179.5 (3)
C6B—C5—C4B—C3B	9.6 (8)	N4—C11—C12—C13	176.2 (3)
C6A—C5—C4B—C3B	−33.0 (7)	S1—C11—C12—C13	−3.3 (5)
C8—C5—C4B—C3B	−174.9 (4)	N4—C11—C12—C16	−3.7 (5)
C2—C3B—C4B—C5	−8.8 (8)	S1—C11—C12—C16	176.7 (2)
C4B—C5—C6B—C7B	−8.2 (7)	C16—C12—C13—C14	1.4 (7)
C4A—C5—C6B—C7B	−39.6 (6)	C11—C12—C13—C14	−178.6 (4)
C6A—C5—C6B—C7B	80.4 (7)	C15—N5—C14—C13	0.8 (8)
C8—C5—C6B—C7B	176.0 (5)	C12—C13—C14—N5	−1.8 (9)
C3A—C2—C7B—C6B	33.5 (7)	C14—N5—C15—C16	0.5 (6)
C7A—C2—C7B—C6B	−82.0 (8)	N5—C15—C16—C12	−0.8 (6)
C3B—C2—C7B—C6B	−6.0 (8)	C13—C12—C16—C15	−0.2 (5)
C1—C2—C7B—C6B	177.1 (5)	C11—C12—C16—C15	179.7 (3)
C5—C6B—C7B—C2	6.8 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	1.90	2.583 (3)	135
N1—H1···O2ⁱ	0.86	2.10	2.935 (3)	165

Symmetry code: (i) −x+2, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃N₅O₂S
M_r	339.37
Crystal system, space group	Triclinic, P1
Temperature (K)	297
a, b, c (Å)	5.0563 (5), 11.8561 (11), 13.2506 (12)
α, β, γ (°)	88.892 (2), 80.849 (2), 77.989 (2)
V (Å³)	766.99 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.20 × 0.10 × 0.04

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6171, 2978, 2120
R_int	0.096
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.195, 1.06
No. of reflections	2978
No. of parameters	214
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.32

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	1.90	2.583 (3)	135
N1—H1···O2ⁱ	0.86	2.10	2.935 (3)	165

Symmetry code: (i) −x+2, −y+2, −z.

Acknowledgements

The authors acknowledge financial support from the Scientific Research Fund for Distinguished Young and Middle-aged Talent of Hubei Provincial Department of Education (grant No. Q200729001) and the Natural Science Foundation of Hubei Province, China (grant No. 2007ABA001).

References

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