1-(4-Methyl-benzo-yl)-3-[5-(4-pyrid-yl)-1,3,4-thia-diazol-2-yl]urea.

In the title compound, C(16)H(13)N(5)O(2)S, the five non-H atoms of the urea linkage adopt a planar configuration owing to the presence of an intra-molecular N-H⋯O hydrogen bond. The maximum deviation from planarity is 0.022 (2) Å. The thia-diazole and pyridine heterocyclic rings are close to being coplanar, with a dihedral angle of 6.7 (2)° between their mean planes. Inter-molecular N-H⋯O hydrogen bonds link two neighbouring mol-ecules into centrosymmetric R(2) (2)(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 = 339.37

Triclinic,

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[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.195

S = 1.06

2978 reflections

214 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.32 e Å−3

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.

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

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

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

C16H13N5O2S1	Z = 2
Mr = 339.37	F000 = 352
Triclinic, P1	Dx = 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 = 2.3–24.7º
α = 88.892 (2)º	µ = 0.23 mm−1
β = 80.849 (2)º	T = 297 (2) K
γ = 77.989 (2)º	Block, colorless
V = 766.99 (13) Å3	0.20 × 0.10 × 0.04 mm

Bruker SMART CCD area-detector diffractometer	2120 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.096
Monochromator: graphite	θmax = 26.0º
T = 297(2) K	θmin = 1.8º
φ and ω scans	h = −6→6
Absorption correction: none	k = −14→14
6171 measured reflections	l = −16→16
2978 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.062	H-atom parameters constrained
wR(F2) = 0.195	w = 1/[σ2(Fo2) + (0.1026P)2] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2978 reflections	Δρmax = 0.24 e Å−3
214 parameters	Δρmin = −0.32 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq	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*

	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)

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)

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

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) .