N'-[(E)-(4-Bromo-2-thienyl)methyl-ene]isonicotinohydrazide.

In title compound, C(11)H(8)BrN(3)OS, the dihedral angle between the two aromatic rings is 27.61 (14)° and the Br atom is disordered over two sites with an occupancy ratio of 0.804 (2):0.196 (2). In the crystal, the mol-ecules are linked by N-H⋯O, C-H⋯O and C-H⋯N inter-actions, resulting in chains.

Related literature

For related structures, see: Jing et al. (2007 ▶); Shafiq et al. (2009 ▶); Wang et al. (2007 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C11H8BrN3OS

M = 310.17

Orthorhombic,

a = 14.3507 (6) Å

b = 48.732 (2) Å

c = 7.2115 (3) Å

V = 5043.3 (4) Å3

Z = 16

Mo Kα radiation

μ = 3.41 mm−1

T = 296 K

0.26 × 0.14 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.567, T max = 0.666

12209 measured reflections

2837 independent reflections

1954 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.113

S = 1.04

2837 reflections

158 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.48 e Å−3

Absolute structure: Flack (1983 ▶), 1205 Friedal Pairs

Flack parameter: −0.002 (13)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680903709X/hb5101sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680903709X/hb5101Isup2.hkl

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

C11H8BrN3OS	F(000) = 2464
Mr = 310.17	Dx = 1.634 Mg m−3
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 2837 reflections
a = 14.3507 (6) Å	θ = 3.0–27.9°
b = 48.732 (2) Å	µ = 3.41 mm−1
c = 7.2115 (3) Å	T = 296 K
V = 5043.3 (4) Å3	Cut needle, light yellow
Z = 16	0.26 × 0.14 × 0.12 mm

Bruker Kappa APEXII CCD diffractometer	2837 independent reflections
Radiation source: fine-focus sealed tube	1954 reflections with I > 2σ(I)
graphite	Rint = 0.035
Detector resolution: 7.50 pixels mm-1	θmax = 27.9°, θmin = 3.0°
ω scans	h = −18→18
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −64→63
Tmin = 0.567, Tmax = 0.666	l = −9→9
12209 measured 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)] = 0.044	H-atom parameters constrained
wR(F2) = 0.113	w = 1/[σ2(Fo2) + (0.0415P)2 + 9.3783P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2837 reflections	Δρmax = 0.56 e Å−3
158 parameters	Δρmin = −0.48 e Å−3
2 restraints	Absolute structure: Flack (1983), 1205 Friedal Pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.002 (13)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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)
Br1A	0.42406 (6)	0.25903 (2)	−0.16312 (17)	0.0946 (5)	0.804 (2)
Br1B	0.4270 (3)	0.26462 (9)	−0.0262 (10)	0.0946 (5)	0.196 (2)
S1	0.44553 (8)	0.17467 (2)	0.0252 (2)	0.0549 (4)
O1	0.27773 (19)	0.09307 (6)	0.2899 (5)	0.0505 (10)
N1	−0.0545 (3)	0.06098 (14)	0.3270 (10)	0.099 (3)
N2	0.1935 (2)	0.12740 (7)	0.1634 (5)	0.0406 (11)
N3	0.2717 (2)	0.14261 (7)	0.1259 (5)	0.0424 (11)
C1	0.1129 (3)	0.08803 (8)	0.2787 (6)	0.0418 (14)
C2	0.0333 (3)	0.10184 (10)	0.3343 (7)	0.0527 (16)
C3	−0.0467 (3)	0.08712 (15)	0.3572 (10)	0.080 (3)
C4	0.0234 (5)	0.04764 (13)	0.2750 (10)	0.092 (3)
C5	0.1084 (4)	0.06041 (10)	0.2517 (8)	0.0620 (19)
C6	0.2039 (3)	0.10290 (8)	0.2448 (6)	0.0382 (14)
C7	0.2561 (3)	0.16678 (9)	0.0670 (7)	0.0460 (16)
C8	0.3315 (3)	0.18499 (9)	0.0213 (7)	0.0470 (14)
C9	0.3246 (3)	0.21142 (11)	−0.0287 (9)	0.068 (2)
C10	0.4113 (3)	0.22347 (9)	−0.0687 (9)	0.0643 (19)
C11	0.4832 (3)	0.20625 (11)	−0.0432 (9)	0.0653 (18)
H2	0.13903	0.13346	0.13520	0.0485*
H2A	0.03442	0.12066	0.35548	0.0632*
H3	−0.09935	0.09650	0.39733	0.0962*
H4	0.01970	0.02885	0.25376	0.1106*
H5	0.16110	0.05044	0.21847	0.0746*
H7	0.19500	0.17278	0.05327	0.0554*
H9	0.26831	0.22080	−0.03612	0.0813*
H11	0.54538	0.21094	−0.06045	0.0783*

	U11	U22	U33	U12	U13	U23
Br1A	0.0709 (4)	0.0603 (5)	0.1526 (14)	−0.0081 (3)	0.0142 (7)	0.0410 (7)
Br1B	0.0709 (4)	0.0603 (5)	0.1526 (14)	−0.0081 (3)	0.0142 (7)	0.0410 (7)
S1	0.0358 (5)	0.0516 (7)	0.0773 (9)	0.0035 (5)	−0.0020 (6)	0.0081 (6)
O1	0.0291 (14)	0.0495 (17)	0.073 (2)	0.0004 (12)	−0.0118 (16)	0.0034 (17)
N1	0.056 (3)	0.111 (5)	0.130 (5)	−0.041 (3)	−0.031 (3)	0.053 (4)
N2	0.0250 (16)	0.0437 (19)	0.053 (2)	−0.0055 (14)	−0.0080 (15)	0.0056 (16)
N3	0.0281 (16)	0.049 (2)	0.050 (2)	−0.0061 (15)	−0.0043 (15)	0.0029 (16)
C1	0.0315 (19)	0.048 (2)	0.046 (3)	−0.0076 (17)	−0.0167 (19)	0.007 (2)
C2	0.037 (2)	0.062 (3)	0.059 (3)	0.0025 (19)	−0.002 (2)	0.022 (2)
C3	0.039 (3)	0.108 (5)	0.094 (5)	−0.011 (3)	−0.012 (3)	0.042 (4)
C4	0.091 (5)	0.068 (4)	0.118 (6)	−0.032 (3)	−0.041 (4)	0.030 (4)
C5	0.062 (3)	0.046 (3)	0.078 (4)	−0.007 (2)	−0.026 (3)	0.012 (3)
C6	0.0276 (19)	0.043 (2)	0.044 (3)	−0.0029 (16)	−0.0040 (17)	−0.0027 (19)
C7	0.029 (2)	0.056 (3)	0.053 (3)	−0.0051 (18)	−0.0089 (19)	0.011 (2)
C8	0.034 (2)	0.049 (2)	0.058 (3)	0.0006 (17)	−0.008 (2)	0.006 (2)
C9	0.039 (2)	0.057 (3)	0.107 (5)	0.002 (2)	−0.008 (3)	0.026 (3)
C10	0.045 (3)	0.046 (3)	0.102 (4)	−0.007 (2)	−0.001 (3)	0.017 (3)
C11	0.035 (2)	0.063 (3)	0.098 (4)	−0.003 (2)	0.000 (3)	0.015 (3)

Br1A—C10	1.871 (5)	C2—C3	1.364 (7)
Br1B—C10	2.041 (6)	C4—C5	1.380 (9)
S1—C8	1.712 (4)	C7—C8	1.438 (6)
S1—C11	1.704 (5)	C8—C9	1.341 (7)
O1—C6	1.207 (5)	C9—C10	1.406 (6)
N1—C3	1.297 (10)	C10—C11	1.343 (6)
N1—C4	1.347 (9)	C2—H2A	0.9300
N2—N3	1.372 (4)	C3—H3	0.9300
N2—C6	1.339 (5)	C4—H4	0.9300
N3—C7	1.272 (6)	C5—H5	0.9300
N2—H2	0.8600	C7—H7	0.9300
C1—C2	1.385 (6)	C9—H9	0.9300
C1—C5	1.362 (6)	C11—H11	0.9300
C1—C6	1.513 (6)
C8—S1—C11	91.9 (2)	Br1A—C10—C11	123.6 (4)
C3—N1—C4	116.7 (5)	Br1B—C10—C9	118.5 (4)
N3—N2—C6	118.5 (3)	C9—C10—C11	113.0 (4)
N2—N3—C7	115.0 (3)	Br1B—C10—C11	120.6 (4)
C6—N2—H2	121.00	Br1A—C10—C9	123.3 (4)
N3—N2—H2	121.00	S1—C11—C10	111.1 (3)
C2—C1—C6	121.7 (4)	C1—C2—H2A	121.00
C5—C1—C6	119.4 (4)	C3—C2—H2A	121.00
C2—C1—C5	118.9 (4)	N1—C3—H3	118.00
C1—C2—C3	118.3 (5)	C2—C3—H3	118.00
N1—C3—C2	124.7 (5)	N1—C4—H4	118.00
N1—C4—C5	123.4 (6)	C5—C4—H4	118.00
C1—C5—C4	118.1 (5)	C1—C5—H5	121.00
N2—C6—C1	113.7 (3)	C4—C5—H5	121.00
O1—C6—C1	121.6 (4)	N3—C7—H7	120.00
O1—C6—N2	124.7 (4)	C8—C7—H7	119.00
N3—C7—C8	121.0 (4)	C8—C9—H9	123.00
C7—C8—C9	126.8 (4)	C10—C9—H9	123.00
S1—C8—C7	122.3 (3)	S1—C11—H11	124.00
S1—C8—C9	110.9 (3)	C10—C11—H11	124.00
C8—C9—C10	113.0 (4)
C11—S1—C8—C7	179.5 (5)	C2—C1—C6—N2	−38.5 (6)
C11—S1—C8—C9	−0.5 (5)	C5—C1—C6—O1	−39.9 (7)
C8—S1—C11—C10	−0.5 (5)	C5—C1—C6—N2	140.6 (5)
C4—N1—C3—C2	2.2 (11)	C1—C2—C3—N1	−1.5 (10)
C3—N1—C4—C5	−0.6 (11)	N1—C4—C5—C1	−1.6 (10)
C6—N2—N3—C7	−172.8 (4)	N3—C7—C8—S1	5.3 (7)
N3—N2—C6—O1	0.6 (6)	N3—C7—C8—C9	−174.7 (5)
N3—N2—C6—C1	−179.9 (3)	S1—C8—C9—C10	1.4 (7)
N2—N3—C7—C8	−179.7 (4)	C7—C8—C9—C10	−178.6 (5)
C5—C1—C2—C3	−0.9 (8)	C8—C9—C10—Br1A	174.2 (4)
C6—C1—C2—C3	178.3 (5)	C8—C9—C10—C11	−1.9 (8)
C2—C1—C5—C4	2.2 (8)	Br1A—C10—C11—S1	−174.6 (3)
C6—C1—C5—C4	−176.9 (5)	C9—C10—C11—S1	1.4 (7)
C2—C1—C6—O1	141.0 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.86	2.08	2.920 (4)	165
C7—H7···O1i	0.93	2.52	3.318 (5)	144
C11—H11···N1ii	0.93	2.60	3.277 (7)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.86	2.08	2.920 (4)	165
C7—H7⋯O1i	0.93	2.52	3.318 (5)	144
C11—H11⋯N1ii	0.93	2.60	3.277 (7)	130

Symmetry codes: (i) ; (ii) .