5-(2-Bromo-phen-yl)-1,3,4-thia-diazol-2-amine.

In the title compound, C(8)H(6)BrN(3)S, the thia-diazole ring is oriented at a dihedral angle of 48.35 (3)° with respect to the bromo-phenyl ring. In the crystal structure, inter-molecular N-H⋯N hydrogen bonds link the mol-ecules.

Related literature

For related literature, see: Nakagawa et al. (1996 ▶); Omar et al. (1986 ▶); Wang et al. (1999 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C8H6BrN3S

M = 256.13

Monoclinic,

a = 14.869 (3) Å

b = 8.0250 (16) Å

c = 7.9480 (16) Å

β = 97.43 (3)°

V = 940.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 4.54 mm−1

T = 298 (2) K

0.30 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.343, T max = 0.659

1832 measured reflections

1694 independent reflections

972 reflections with I > 2σ(I)

R int = 0.034

3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.153

S = 0.97

1694 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.57 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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/S1600536808027827/hk2522sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808027827/hk2522Isup2.hkl

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

C8H6BrN3S	F(000) = 504
Mr = 256.13	Dx = 1.809 Mg m−3
Monoclinic, P21/c	Melting point = 486–487 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 14.869 (3) Å	Cell parameters from 25 reflections
b = 8.0250 (16) Å	θ = 10–14°
c = 7.9480 (16) Å	µ = 4.55 mm−1
β = 97.43 (3)°	T = 298 K
V = 940.4 (3) Å3	Block, colorless
Z = 4	0.30 × 0.10 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	972 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.034
graphite	θmax = 25.2°, θmin = 1.4°
ω/2θ scans	h = −17→17
Absorption correction: ψ scan (North et al., 1968)	k = 0→9
Tmin = 0.343, Tmax = 0.659	l = 0→9
1832 measured reflections	3 standard reflections every 120 min
1694 independent reflections	intensity decay: none

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153	H-atom parameters constrained
S = 0.97	w = 1/[σ2(Fo2) + (0.0838P)2] where P = (Fo2 + 2Fc2)/3
1694 reflections	(Δ/σ)max < 0.001
118 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.57 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
Br	0.88329 (5)	1.09232 (10)	1.09121 (14)	0.0845 (5)
S	0.65602 (11)	1.1146 (2)	1.0932 (2)	0.0458 (5)
N1	0.6259 (3)	0.9573 (7)	0.8134 (6)	0.0424 (13)
N2	0.5587 (3)	1.0773 (6)	0.8048 (6)	0.0430 (13)
N3	0.5081 (3)	1.2909 (6)	0.9666 (6)	0.0480 (14)
H3A	0.4635	1.3143	0.8901	0.058*
H3B	0.5158	1.3467	1.0597	0.058*
C1	0.7308 (5)	0.6693 (8)	0.9656 (9)	0.0512 (18)
H1	0.6722	0.6431	0.9176	0.061*
C2	0.7921 (5)	0.5423 (8)	1.0064 (10)	0.0591 (19)
H2	0.7750	0.4319	0.9866	0.071*
C3	0.8787 (5)	0.5816 (10)	1.0769 (10)	0.068 (2)
H3	0.9204	0.4968	1.1067	0.081*
C4	0.9041 (4)	0.7438 (10)	1.1036 (9)	0.059 (2)
H4	0.9630	0.7698	1.1506	0.071*
C5	0.8416 (4)	0.8692 (8)	1.0602 (9)	0.0493 (17)
C6	0.7542 (4)	0.8348 (7)	0.9941 (8)	0.0378 (14)
C7	0.6811 (4)	0.9618 (8)	0.9507 (7)	0.0363 (14)
C8	0.5647 (4)	1.1688 (7)	0.9412 (7)	0.0332 (14)

	U11	U22	U33	U12	U13	U23
Br	0.0417 (5)	0.0576 (5)	0.1483 (10)	−0.0105 (4)	−0.0096 (5)	−0.0066 (6)
S	0.0396 (9)	0.0538 (10)	0.0394 (9)	0.0102 (8)	−0.0131 (7)	−0.0097 (8)
N1	0.042 (3)	0.046 (3)	0.037 (3)	0.000 (3)	−0.001 (3)	−0.003 (3)
N2	0.045 (3)	0.043 (3)	0.037 (3)	0.008 (3)	−0.008 (2)	−0.005 (3)
N3	0.049 (3)	0.056 (4)	0.036 (3)	0.015 (3)	−0.008 (2)	−0.007 (3)
C1	0.046 (4)	0.049 (4)	0.057 (5)	−0.003 (3)	0.005 (3)	0.001 (4)
C2	0.057 (4)	0.035 (4)	0.086 (5)	0.004 (3)	0.013 (4)	0.004 (4)
C3	0.050 (4)	0.068 (6)	0.083 (6)	0.021 (4)	0.005 (4)	0.012 (5)
C4	0.037 (4)	0.064 (5)	0.073 (5)	0.009 (4)	−0.003 (4)	0.009 (4)
C5	0.031 (3)	0.049 (4)	0.065 (4)	−0.004 (3)	−0.004 (3)	0.006 (3)
C6	0.038 (3)	0.040 (3)	0.036 (3)	−0.002 (3)	0.006 (3)	−0.004 (3)
C7	0.029 (3)	0.042 (3)	0.037 (3)	−0.006 (3)	0.001 (3)	0.001 (3)
C8	0.029 (3)	0.035 (3)	0.034 (4)	0.000 (3)	−0.003 (3)	0.004 (3)

Br—C5	1.901 (7)	C3—H3	0.9300
N1—N2	1.383 (7)	C4—C5	1.383 (9)
N3—H3A	0.8600	C4—H4	0.9300
N3—H3B	0.8600	C5—C6	1.365 (8)
C1—C2	1.377 (9)	C6—C7	1.498 (8)
C1—C6	1.384 (8)	C7—N1	1.278 (7)
C1—H1	0.9300	C7—S	1.742 (6)
C2—C3	1.373 (10)	C8—N2	1.302 (7)
C2—H2	0.9300	C8—N3	1.325 (7)
C3—C4	1.365 (11)	C8—S	1.752 (6)
C2—C1—C6	121.8 (7)	C5—C6—C1	117.6 (6)
C2—C1—H1	119.1	C5—C6—C7	125.3 (6)
C6—C1—H1	119.1	C1—C6—C7	117.1 (6)
C3—C2—C1	118.9 (7)	N1—C7—C6	123.0 (6)
C3—C2—H2	120.5	N1—C7—S	114.0 (5)
C1—C2—H2	120.5	C6—C7—S	122.6 (4)
C4—C3—C2	120.6 (7)	N2—C8—N3	124.6 (5)
C4—C3—H3	119.7	N2—C8—S	113.4 (4)
C2—C3—H3	119.7	N3—C8—S	122.0 (5)
C3—C4—C5	119.4 (6)	C7—N1—N2	113.7 (5)
C3—C4—H4	120.3	C8—N2—N1	112.4 (5)
C5—C4—H4	120.3	C8—N3—H3A	120.0
C6—C5—C4	121.6 (6)	C8—N3—H3B	120.0
C6—C5—Br	121.2 (5)	H3A—N3—H3B	120.0
C4—C5—Br	117.1 (5)	C7—S—C8	86.4 (3)
C6—C1—C2—C3	−0.2 (11)	C1—C6—C7—N1	−44.3 (9)
C1—C2—C3—C4	−1.0 (12)	C5—C6—C7—S	−51.2 (8)
C2—C3—C4—C5	0.5 (12)	C1—C6—C7—S	128.4 (6)
C3—C4—C5—C6	1.3 (11)	C6—C7—N1—N2	174.6 (5)
C3—C4—C5—Br	−177.2 (6)	S—C7—N1—N2	1.3 (7)
C4—C5—C6—C1	−2.5 (11)	N3—C8—N2—N1	−179.0 (6)
Br—C5—C6—C1	176.0 (5)	S—C8—N2—N1	0.6 (6)
C4—C5—C6—C7	177.2 (6)	C7—N1—N2—C8	−1.2 (7)
Br—C5—C6—C7	−4.4 (9)	N1—C7—S—C8	−0.8 (5)
C2—C1—C6—C5	1.9 (11)	C6—C7—S—C8	−174.1 (5)
C2—C1—C6—C7	−177.8 (6)	N2—C8—S—C7	0.1 (5)
C5—C6—C7—N1	136.1 (7)	N3—C8—S—C7	179.6 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N1i	0.86	2.27	3.092 (7)	160.
N3—H3A···N2i	0.86	2.61	3.221 (7)	129.
N3—H3B···N2ii	0.86	2.06	2.896 (7)	163.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯N1i	0.86	2.27	3.092 (7)	160
N3—H3A⋯N2i	0.86	2.61	3.221 (7)	129
N3—H3B⋯N2ii	0.86	2.06	2.896 (7)	163

Symmetry codes: (i) ; (ii) .