4-[(2-Bromo-benzyl-idene)amino]-3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione.

In the title compound, C(14)H(10)BrN(5)S, the dihedral angle between the triazole ring and the pyridine and bromo-benzene rings are 26.42 (13) and 6.28 (13)°, respectively. The molecule exists as a thione in the solid state. In the crystal, mol-ecules are linked by N-H⋯N hydrogen bonds, generating [010] C(8) chains.

Related literature

For related structures, see: Zou et al. (2008 ▶); Kashaev et al. (2010 ▶); Liu & Liu (2011 ▶); Liu, Pan, Weng, Tan et al. (2012 ▶); Liu, Tan, Weng & Liu (2012 ▶); Tan et al. (2012 ▶).

Experimental

Crystal data

C14H10BrN5S

M = 360.24

Monoclinic,

a = 10.406 (3) Å

b = 17.299 (5) Å

c = 15.858 (4) Å

β = 103.719 (5)°

V = 2773.3 (13) Å3

Z = 8

Mo Kα radiation

μ = 3.12 mm−1

T = 113 K

0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.575, T max = 0.706

14119 measured reflections

3293 independent reflections

2565 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.087

S = 1.08

3293 reflections

194 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.54 e Å−3

Δρmin = −0.42 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812024439/hb6820sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812024439/hb6820Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812024439/hb6820Isup3.cml

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

C14H10BrN5S	F(000) = 1440
Mr = 360.24	Dx = 1.726 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.406 (3) Å	Cell parameters from 5149 reflections
b = 17.299 (5) Å	θ = 2.3–27.9°
c = 15.858 (4) Å	µ = 3.12 mm−1
β = 103.719 (5)°	T = 113 K
V = 2773.3 (13) Å3	Prism, colorless
Z = 8	0.20 × 0.18 × 0.12 mm

Rigaku Saturn CCD diffractometer	3293 independent reflections
Radiation source: rotating anode	2565 reflections with I > 2σ(I)
Multilayer monochromator	Rint = 0.036
Detector resolution: 14.63 pixels mm-1	θmax = 27.9°, θmin = 2.3°
ω and φ scans	h = −13→13
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −22→22
Tmin = 0.575, Tmax = 0.706	l = −20→20
14119 measured reflections

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0476P)2 + 0.9724P] where P = (Fo2 + 2Fc2)/3
3293 reflections	(Δ/σ)max = 0.003
194 parameters	Δρmax = 0.54 e Å−3
1 restraint	Δρmin = −0.42 e Å−3

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
Br1	0.42237 (3)	1.115195 (15)	1.078191 (18)	0.02495 (10)
S1	0.04950 (6)	1.18904 (3)	0.90838 (4)	0.01831 (15)
N1	−0.2275 (2)	0.76260 (12)	0.76957 (13)	0.0170 (4)
N2	−0.1987 (2)	1.05219 (11)	0.75708 (13)	0.0135 (4)
N3	−0.1441 (2)	1.12183 (11)	0.78721 (13)	0.0135 (4)
N4	−0.02113 (18)	1.03665 (11)	0.86394 (12)	0.0110 (4)
N5	0.0722 (2)	0.99264 (12)	0.92068 (13)	0.0165 (4)
C1	−0.1154 (3)	0.86370 (13)	0.86163 (16)	0.0157 (5)
H1	−0.0638	0.8787	0.9170	0.019*
C2	−0.1571 (3)	0.78812 (14)	0.84586 (17)	0.0185 (5)
H2	−0.1341	0.7521	0.8923	0.022*
C3	−0.2600 (2)	0.81462 (13)	0.70517 (17)	0.0178 (5)
H3A	−0.3098	0.7975	0.6502	0.021*
C4	−0.2249 (2)	0.89158 (13)	0.71470 (16)	0.0149 (5)
H4	−0.2511	0.9263	0.6673	0.018*
C5	−0.1507 (2)	0.91779 (13)	0.79426 (16)	0.0123 (5)
C6	−0.1234 (2)	1.00094 (13)	0.80478 (15)	0.0111 (4)
C7	−0.0371 (2)	1.11627 (13)	0.85297 (15)	0.0125 (5)
C8	0.1806 (2)	1.02341 (14)	0.96104 (16)	0.0177 (5)
H8	0.1978	1.0765	0.9533	0.021*
C9	0.2775 (2)	0.97532 (14)	1.01938 (15)	0.0158 (5)
C10	0.2607 (3)	0.89478 (14)	1.02189 (18)	0.0203 (5)
H10	0.1857	0.8714	0.9846	0.024*
C11	0.3519 (3)	0.84900 (15)	1.07796 (18)	0.0234 (6)
H11	0.3396	0.7946	1.0786	0.028*
C12	0.4613 (3)	0.88260 (16)	1.13319 (19)	0.0257 (6)
H12	0.5230	0.8511	1.1721	0.031*
C13	0.4808 (3)	0.96139 (16)	1.13185 (17)	0.0234 (6)
H13	0.5559	0.9843	1.1694	0.028*
C14	0.3892 (2)	1.00692 (14)	1.07490 (16)	0.0175 (5)
H3	−0.175 (3)	1.1661 (12)	0.761 (2)	0.049 (10)*

	U11	U22	U33	U12	U13	U23
Br1	0.01786 (15)	0.02020 (14)	0.03306 (18)	−0.00296 (10)	−0.00141 (11)	−0.00368 (11)
S1	0.0216 (3)	0.0097 (3)	0.0195 (3)	−0.0023 (2)	−0.0033 (3)	−0.0012 (2)
N1	0.0181 (11)	0.0111 (9)	0.0198 (12)	−0.0002 (8)	0.0006 (9)	−0.0007 (8)
N2	0.0148 (10)	0.0094 (9)	0.0149 (10)	−0.0007 (7)	0.0005 (8)	−0.0008 (8)
N3	0.0163 (10)	0.0082 (9)	0.0140 (11)	0.0002 (8)	−0.0005 (9)	0.0015 (8)
N4	0.0113 (9)	0.0078 (9)	0.0124 (10)	0.0010 (7)	−0.0001 (8)	0.0001 (8)
N5	0.0159 (10)	0.0134 (10)	0.0185 (11)	0.0026 (8)	0.0007 (9)	0.0012 (8)
C1	0.0190 (12)	0.0125 (10)	0.0135 (12)	−0.0014 (9)	−0.0003 (10)	0.0000 (9)
C2	0.0223 (13)	0.0137 (11)	0.0173 (13)	0.0006 (10)	0.0001 (11)	0.0031 (10)
C3	0.0193 (12)	0.0131 (11)	0.0187 (13)	−0.0028 (9)	0.0001 (10)	−0.0030 (10)
C4	0.0161 (12)	0.0144 (11)	0.0129 (12)	0.0004 (9)	0.0007 (10)	0.0025 (9)
C5	0.0095 (11)	0.0098 (10)	0.0168 (13)	0.0002 (8)	0.0017 (10)	−0.0006 (9)
C6	0.0108 (11)	0.0115 (10)	0.0106 (11)	−0.0002 (8)	0.0016 (9)	−0.0008 (9)
C7	0.0140 (11)	0.0098 (10)	0.0139 (12)	0.0003 (9)	0.0038 (10)	0.0015 (9)
C8	0.0162 (12)	0.0149 (11)	0.0206 (13)	0.0005 (9)	0.0017 (11)	−0.0011 (10)
C9	0.0143 (11)	0.0170 (11)	0.0159 (13)	0.0004 (9)	0.0032 (10)	0.0005 (10)
C10	0.0167 (12)	0.0197 (13)	0.0237 (15)	−0.0002 (10)	0.0032 (11)	−0.0007 (10)
C11	0.0266 (14)	0.0180 (13)	0.0257 (15)	0.0048 (11)	0.0064 (12)	0.0062 (11)
C12	0.0244 (14)	0.0285 (14)	0.0222 (15)	0.0100 (12)	0.0013 (12)	0.0065 (12)
C13	0.0157 (13)	0.0313 (15)	0.0207 (14)	0.0040 (11)	−0.0005 (11)	0.0001 (12)
C14	0.0169 (12)	0.0175 (12)	0.0183 (13)	0.0019 (10)	0.0043 (11)	−0.0003 (10)

Br1—C14	1.903 (3)	C3—H3A	0.9500
S1—C7	1.671 (2)	C4—C5	1.390 (3)
N1—C2	1.332 (3)	C4—H4	0.9500
N1—C3	1.343 (3)	C5—C6	1.468 (3)
N2—C6	1.300 (3)	C8—C9	1.457 (3)
N2—N3	1.369 (3)	C8—H8	0.9500
N3—C7	1.336 (3)	C9—C14	1.393 (3)
N3—H3	0.896 (10)	C9—C10	1.406 (3)
N4—N5	1.385 (3)	C10—C11	1.385 (4)
N4—C6	1.386 (3)	C10—H10	0.9500
N4—C7	1.393 (3)	C11—C12	1.389 (4)
N5—C8	1.274 (3)	C11—H11	0.9500
C1—C2	1.382 (3)	C12—C13	1.379 (4)
C1—C5	1.402 (3)	C12—H12	0.9500
C1—H1	0.9500	C13—C14	1.391 (3)
C2—H2	0.9500	C13—H13	0.9500
C3—C4	1.380 (3)
C2—N1—C3	117.0 (2)	N4—C6—C5	127.6 (2)
C6—N2—N3	104.72 (19)	N3—C7—N4	102.8 (2)
C7—N3—N2	114.15 (19)	N3—C7—S1	127.00 (17)
C7—N3—H3	125 (2)	N4—C7—S1	130.19 (19)
N2—N3—H3	121 (2)	N5—C8—C9	118.5 (2)
N5—N4—C6	120.17 (18)	N5—C8—H8	120.7
N5—N4—C7	132.0 (2)	C9—C8—H8	120.7
C6—N4—C7	107.83 (19)	C14—C9—C10	117.5 (2)
C8—N5—N4	119.8 (2)	C14—C9—C8	121.7 (2)
C2—C1—C5	118.6 (2)	C10—C9—C8	120.8 (2)
C2—C1—H1	120.7	C11—C10—C9	120.9 (3)
C5—C1—H1	120.7	C11—C10—H10	119.5
N1—C2—C1	124.0 (2)	C9—C10—H10	119.5
N1—C2—H2	118.0	C10—C11—C12	120.0 (3)
C1—C2—H2	118.0	C10—C11—H11	120.0
N1—C3—C4	123.4 (2)	C12—C11—H11	120.0
N1—C3—H3A	118.3	C13—C12—C11	120.4 (3)
C4—C3—H3A	118.3	C13—C12—H12	119.8
C3—C4—C5	119.4 (2)	C11—C12—H12	119.8
C3—C4—H4	120.3	C12—C13—C14	119.3 (3)
C5—C4—H4	120.3	C12—C13—H13	120.4
C4—C5—C1	117.6 (2)	C14—C13—H13	120.4
C4—C5—C6	118.3 (2)	C13—C14—C9	121.9 (2)
C1—C5—C6	124.0 (2)	C13—C14—Br1	116.6 (2)
N2—C6—N4	110.48 (19)	C9—C14—Br1	121.48 (19)
N2—C6—C5	121.9 (2)
C6—N2—N3—C7	−0.5 (3)	N2—N3—C7—N4	1.4 (3)
C6—N4—N5—C8	164.5 (2)	N2—N3—C7—S1	−176.78 (17)
C7—N4—N5—C8	−16.5 (3)	N5—N4—C7—N3	179.1 (2)
C3—N1—C2—C1	−0.7 (4)	C6—N4—C7—N3	−1.7 (2)
C5—C1—C2—N1	1.2 (4)	N5—N4—C7—S1	−2.8 (4)
C2—N1—C3—C4	−0.3 (4)	C6—N4—C7—S1	176.36 (18)
N1—C3—C4—C5	0.7 (4)	N4—N5—C8—C9	−179.17 (19)
C3—C4—C5—C1	−0.1 (3)	N5—C8—C9—C14	−170.6 (2)
C3—C4—C5—C6	−175.3 (2)	N5—C8—C9—C10	9.0 (4)
C2—C1—C5—C4	−0.8 (3)	C14—C9—C10—C11	0.3 (4)
C2—C1—C5—C6	174.1 (2)	C8—C9—C10—C11	−179.3 (2)
N3—N2—C6—N4	−0.7 (2)	C9—C10—C11—C12	0.5 (4)
N3—N2—C6—C5	178.5 (2)	C10—C11—C12—C13	−0.8 (4)
N5—N4—C6—N2	−179.16 (18)	C11—C12—C13—C14	0.4 (4)
C7—N4—C6—N2	1.6 (3)	C12—C13—C14—C9	0.4 (4)
N5—N4—C6—C5	1.7 (3)	C12—C13—C14—Br1	179.2 (2)
C7—N4—C6—C5	−177.5 (2)	C10—C9—C14—C13	−0.8 (4)
C4—C5—C6—N2	23.8 (3)	C8—C9—C14—C13	178.8 (2)
C1—C5—C6—N2	−151.0 (2)	C10—C9—C14—Br1	−179.52 (18)
C4—C5—C6—N4	−157.1 (2)	C8—C9—C14—Br1	0.1 (3)
C1—C5—C6—N4	28.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N1i	0.90 (1)	1.95 (1)	2.821 (3)	163 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯N1i	0.90 (1)	1.95 (1)	2.821 (3)	163 (3)

Symmetry code: (i) .