N'-(4-Bromo-benzyl-idene)thio-phene-2-carbohydrazide.

In the title compound, C(12)H(9)BrN(2)OS, the dihedral angle between the aromatic rings is 10.0 (2)°. In the crystal structure, inversion dimers linked by pairs of N-H⋯O hydrogen bonds occur, generating R(2) (2)(8) loops. Weak aromatic π-π stacking [centroid-centroid separations = 3.825 (3) and 3.866 (3) Å] also occurs.

Related literature

For background to Schiff bases, see: Cimerman et al. (1997 ▶). For a related structure, see: Girgis (2006 ▶).

Experimental

Crystal data

C12H9BrN2OS

M = 309.18

Monoclinic,

a = 6.0700 (12) Å

b = 16.983 (3) Å

c = 11.643 (2) Å

β = 94.85 (3)°

V = 1195.9 (4) Å3

Z = 4

Mo Kα radiation

μ = 3.60 mm−1

T = 293 K

0.23 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer

8238 measured reflections

2079 independent reflections

1614 reflections with I > 2σ(I)

R int = 0.086

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.163

S = 1.03

2079 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.75 e Å−3

Δρmin = −0.84 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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/S1600536810010603/hb5368sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010603/hb5368Isup2.hkl

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

C12H9BrN2OS	F(000) = 616
Mr = 309.18	Dx = 1.717 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1614 reflections
a = 6.0700 (12) Å	θ = 3.5–25.3°
b = 16.983 (3) Å	µ = 3.60 mm−1
c = 11.643 (2) Å	T = 293 K
β = 94.85 (3)°	Block, colorless
V = 1195.9 (4) Å3	0.23 × 0.20 × 0.18 mm
Z = 4

Bruker SMART CCD diffractometer	1614 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.086
graphite	θmax = 25.3°, θmin = 3.5°
ω scans	h = −6→7
8238 measured reflections	k = −19→19
2079 independent reflections	l = −13→13

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
2079 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.75 e Å−3
0 restraints	Δρmin = −0.84 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.15443 (9)	0.87907 (3)	0.25958 (4)	0.0509 (3)
S1	−0.8655 (2)	0.61910 (7)	0.37457 (11)	0.0437 (4)
C6	−0.5332 (9)	0.6311 (2)	0.0959 (4)	0.0382 (11)
H6A	−0.5211	0.6061	0.0256	0.046*
N2	−0.6908 (7)	0.61169 (19)	0.1589 (3)	0.0390 (9)
C10	−0.0606 (8)	0.8041 (3)	0.2068 (4)	0.0396 (11)
N1	−0.8383 (6)	0.5559 (2)	0.1135 (3)	0.0390 (9)
H1A	−0.8193	0.5353	0.0475	0.047*
O1	−1.1473 (6)	0.4869 (2)	0.1217 (3)	0.0526 (9)
C5	−1.0117 (8)	0.5329 (2)	0.1702 (4)	0.0401 (11)
C1	−1.0383 (9)	0.6136 (3)	0.4824 (5)	0.0466 (13)
H1B	−1.0099	0.6383	0.5534	0.056*
C3	−1.2229 (8)	0.5388 (3)	0.3431 (4)	0.0431 (11)
H3A	−1.3366	0.5075	0.3099	0.052*
C11	−0.2387 (9)	0.7887 (3)	0.2738 (4)	0.0456 (12)
H11A	−0.2529	0.8163	0.3418	0.055*
C7	−0.3756 (7)	0.6916 (2)	0.1350 (4)	0.0363 (10)
C12	−0.3902 (8)	0.7326 (3)	0.2374 (4)	0.0449 (12)
H12A	−0.5061	0.7217	0.2822	0.054*
C4	−1.0404 (8)	0.5594 (2)	0.2876 (4)	0.0381 (10)
C9	−0.0451 (8)	0.7655 (2)	0.1054 (4)	0.0430 (11)
H9A	0.0705	0.7767	0.0604	0.052*
C8	−0.2019 (9)	0.7093 (3)	0.0693 (4)	0.0445 (12)
H8A	−0.1903	0.6832	−0.0001	0.053*
C2	−1.2204 (8)	0.5698 (2)	0.4544 (4)	0.0433 (11)
H2B	−1.3312	0.5612	0.5034	0.052*

	U11	U22	U33	U12	U13	U23
Br1	0.0496 (5)	0.0514 (4)	0.0511 (5)	−0.01021 (19)	0.0003 (3)	0.00256 (19)
S1	0.0465 (8)	0.0495 (8)	0.0352 (8)	−0.0095 (5)	0.0039 (6)	−0.0090 (5)
C6	0.049 (3)	0.036 (2)	0.029 (3)	0.002 (2)	0.002 (2)	0.0009 (17)
N2	0.046 (3)	0.0360 (19)	0.034 (2)	−0.0016 (16)	−0.0017 (18)	−0.0028 (15)
C10	0.042 (3)	0.038 (2)	0.039 (3)	0.0005 (19)	0.002 (2)	0.0079 (18)
N1	0.041 (2)	0.040 (2)	0.036 (2)	−0.0064 (17)	0.0026 (17)	−0.0082 (15)
O1	0.060 (3)	0.055 (2)	0.042 (2)	−0.0194 (17)	0.0048 (17)	−0.0114 (15)
C5	0.047 (3)	0.034 (2)	0.039 (3)	−0.006 (2)	−0.001 (2)	−0.0020 (18)
C1	0.050 (3)	0.055 (3)	0.035 (3)	0.003 (2)	0.007 (2)	−0.009 (2)
C3	0.044 (3)	0.046 (3)	0.039 (3)	−0.010 (2)	0.006 (2)	−0.005 (2)
C11	0.051 (3)	0.049 (3)	0.037 (3)	−0.008 (2)	0.009 (2)	−0.008 (2)
C7	0.036 (3)	0.038 (2)	0.035 (3)	0.0043 (19)	0.0031 (19)	0.0085 (18)
C12	0.037 (3)	0.051 (3)	0.048 (3)	−0.007 (2)	0.012 (2)	−0.004 (2)
C4	0.048 (3)	0.033 (2)	0.033 (3)	0.0037 (19)	−0.002 (2)	−0.0031 (16)
C9	0.042 (3)	0.040 (2)	0.048 (3)	0.002 (2)	0.012 (2)	0.005 (2)
C8	0.058 (3)	0.041 (2)	0.036 (3)	0.000 (2)	0.010 (2)	−0.0029 (19)
C2	0.040 (3)	0.049 (3)	0.043 (3)	−0.001 (2)	0.013 (2)	−0.004 (2)

Br1—C10	1.889 (5)	C1—H1B	0.9300
S1—C1	1.705 (5)	C3—C4	1.374 (7)
S1—C4	1.732 (5)	C3—C2	1.397 (6)
C6—N2	1.296 (6)	C3—H3A	0.9300
C6—C7	1.450 (7)	C11—C12	1.366 (7)
C6—H6A	0.9300	C11—H11A	0.9300
N2—N1	1.378 (5)	C7—C8	1.387 (6)
C10—C9	1.360 (6)	C7—C12	1.391 (6)
C10—C11	1.410 (7)	C12—H12A	0.9300
N1—C5	1.347 (6)	C9—C8	1.387 (7)
N1—H1A	0.8600	C9—H9A	0.9300
O1—C5	1.236 (5)	C8—H8A	0.9300
C5—C4	1.464 (6)	C2—H2B	0.9300
C1—C2	1.349 (7)
C1—S1—C4	90.8 (2)	C12—C11—H11A	120.5
N2—C6—C7	120.1 (4)	C10—C11—H11A	120.5
N2—C6—H6A	120.0	C8—C7—C12	118.0 (4)
C7—C6—H6A	120.0	C8—C7—C6	119.6 (4)
C6—N2—N1	116.4 (4)	C12—C7—C6	122.4 (4)
C9—C10—C11	120.2 (5)	C11—C12—C7	121.8 (4)
C9—C10—Br1	120.7 (4)	C11—C12—H12A	119.1
C11—C10—Br1	119.1 (4)	C7—C12—H12A	119.1
C5—N1—N2	121.4 (4)	C3—C4—C5	121.7 (4)
C5—N1—H1A	119.3	C3—C4—S1	110.6 (3)
N2—N1—H1A	119.3	C5—C4—S1	127.7 (4)
O1—C5—N1	118.5 (4)	C10—C9—C8	119.9 (4)
O1—C5—C4	119.6 (4)	C10—C9—H9A	120.1
N1—C5—C4	121.9 (4)	C8—C9—H9A	120.1
C2—C1—S1	113.3 (4)	C7—C8—C9	121.1 (4)
C2—C1—H1B	123.4	C7—C8—H8A	119.4
S1—C1—H1B	123.4	C9—C8—H8A	119.4
C4—C3—C2	113.2 (4)	C1—C2—C3	112.1 (4)
C4—C3—H3A	123.4	C1—C2—H2B	124.0
C2—C3—H3A	123.4	C3—C2—H2B	124.0
C12—C11—C10	119.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.86	2.00	2.828 (5)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.86	2.00	2.828 (5)	161

Symmetry code: (i) .