N'-[(E)-2-Chloro-benzyl-idene]thio-phene-2-carbohydrazide.

There are two independent mol-ecules in the asymmetric unit of the title compound, C12H9ClN2OS, a Schiff base derived from hydrazide, in which the dihedral angles between the thio-phene and benzene rings are 3.6 (3) and 7.3 (3)°. In the crystal, the two independent mol-ecules are arranged about an approximate non-crystallographic inversion center and are connected by two N-H⋯O hydrogen bonds. Weak C-H⋯Cl contacts are also present. Conversely, there are neither significant aromatic stacking inter-actions nor contacts involving S atoms.

Related literature

For applications of Schiff bases, see: Cimerman et al. (1997 ▶); Ren et al. (2002 ▶). For related structures, see: Warad et al. (2009 ▶); Jiang (2010 ▶, 2011 ▶); Li & Jian (2010 ▶); Li & Meng (2010 ▶).

Experimental

Crystal data

C12H9ClN2OS

M = 264.72

Orthorhombic,

a = 24.9465 (15) Å

b = 4.3709 (3) Å

c = 21.8091 (13) Å

V = 2378.0 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.48 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Agilent Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.870, T max = 0.954

9965 measured reflections

3845 independent reflections

3341 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.113

S = 1.08

3845 reflections

316 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.32 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813020850/bh2481sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813020850/bh2481Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813020850/bh2481Isup3.cml

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

C12H9ClN2OS	F(000) = 1088
Mr = 264.72	Dx = 1.479 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3090 reflections
a = 24.9465 (15) Å	θ = 2.9–29.2°
b = 4.3709 (3) Å	µ = 0.48 mm−1
c = 21.8091 (13) Å	T = 293 K
V = 2378.0 (2) Å3	Parallelpiped, colourless
Z = 8	0.30 × 0.20 × 0.10 mm

Agilent Xcalibur Eos diffractometer	3845 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3341 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 16.0534 pixels mm-1	θmax = 25.0°, θmin = 3.2°
ω scans	h = −29→29
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −5→4
Tmin = 0.870, Tmax = 0.954	l = −25→21
9965 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0575P)2 + 0.3988P] where P = (Fo2 + 2Fc2)/3
3845 reflections	(Δ/σ)max < 0.001
316 parameters	Δρmax = 0.32 e Å−3
1 restraint	Δρmin = −0.32 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
S1	0.30063 (4)	0.4329 (3)	0.72298 (6)	0.0619 (3)
O1	0.17505 (11)	−0.0648 (6)	0.67301 (13)	0.0509 (7)
N1	0.17938 (14)	0.2450 (8)	0.7547 (2)	0.0414 (9)
H1A	0.1555 (17)	0.166 (10)	0.770 (2)	0.046 (13)*
N2	0.20518 (12)	0.4548 (7)	0.78995 (15)	0.0363 (7)
Cl1	0.11381 (5)	0.7410 (3)	0.94945 (7)	0.0663 (4)
C1	0.34789 (17)	0.3764 (12)	0.6679 (2)	0.0598 (12)
H1	0.3823	0.4576	0.6701	0.072*
C2	0.33115 (19)	0.2071 (12)	0.6219 (3)	0.0684 (16)
H2B	0.3532	0.1601	0.5889	0.082*
C3	0.27627 (15)	0.0975 (10)	0.6257 (2)	0.0502 (11)
H3	0.2582	−0.0210	0.5969	0.060*
C4	0.25557 (16)	0.2105 (8)	0.6832 (2)	0.0412 (11)
C5	0.20111 (14)	0.1229 (9)	0.70353 (18)	0.0372 (9)
C6	0.17984 (14)	0.5461 (8)	0.83769 (19)	0.0376 (9)
H6A	0.1454	0.4745	0.8454	0.045*
C7	0.20468 (14)	0.7612 (8)	0.8799 (2)	0.0357 (10)
C8	0.17872 (15)	0.8624 (8)	0.93273 (19)	0.0427 (9)
C9	0.20295 (19)	1.0600 (10)	0.9746 (2)	0.0527 (11)
H9A	0.1849	1.1230	1.0098	0.063*
C10	0.25406 (18)	1.1590 (11)	0.9628 (3)	0.0580 (13)
H10A	0.2707	1.2914	0.9902	0.070*
C11	0.28077 (17)	1.0671 (9)	0.9117 (2)	0.0551 (11)
H11A	0.3156	1.1352	0.9048	0.066*
C12	0.25639 (14)	0.8721 (9)	0.8698 (2)	0.0451 (10)
H12A	0.2748	0.8147	0.8345	0.054*
S2	0.45222 (4)	−0.0291 (3)	0.74612 (7)	0.0598 (3)
O2	0.57997 (11)	−0.5028 (7)	0.79635 (13)	0.0506 (7)
N3	0.57520 (13)	−0.1945 (7)	0.71524 (18)	0.0367 (8)
H3A	0.6055 (17)	−0.260 (9)	0.705 (2)	0.050 (13)*
N4	0.54883 (11)	0.0161 (7)	0.67961 (15)	0.0365 (7)
Cl2	0.63843 (4)	0.3111 (3)	0.52014 (6)	0.0597 (3)
C13	0.40651 (17)	−0.0776 (12)	0.8022 (3)	0.0656 (14)
H13	0.3718	−0.0001	0.8000	0.079*
C14	0.4247 (2)	−0.2383 (13)	0.8504 (3)	0.0694 (17)
H14A	0.4040	−0.2836	0.8846	0.083*
C15	0.47921 (17)	−0.3327 (11)	0.8438 (2)	0.0565 (12)
H15	0.4986	−0.4426	0.8728	0.068*
C16	0.49924 (15)	−0.2344 (8)	0.7868 (2)	0.0384 (10)
C17	0.55391 (15)	−0.3165 (9)	0.7665 (2)	0.0401 (10)
C18	0.57349 (13)	0.1124 (8)	0.63301 (19)	0.0356 (8)
H18A	0.6082	0.0442	0.6253	0.043*
C19	0.54850 (14)	0.3293 (8)	0.5909 (2)	0.0352 (9)
C20	0.57460 (14)	0.4371 (8)	0.53871 (18)	0.0390 (9)
C21	0.54954 (18)	0.6404 (9)	0.4982 (2)	0.0497 (10)
H21A	0.5678	0.7094	0.4636	0.060*
C22	0.49814 (19)	0.7381 (9)	0.5093 (3)	0.0558 (14)
H22A	0.4811	0.8710	0.4823	0.067*
C23	0.47194 (17)	0.6338 (10)	0.5620 (2)	0.0523 (11)
H23A	0.4373	0.7006	0.5705	0.063*
C24	0.49638 (16)	0.4368 (9)	0.6010 (2)	0.0441 (10)
H24A	0.4779	0.3706	0.6355	0.053*

	U11	U22	U33	U12	U13	U23
S1	0.0423 (5)	0.0769 (8)	0.0665 (8)	−0.0039 (6)	0.0064 (5)	−0.0024 (7)
O1	0.0488 (15)	0.0610 (17)	0.0427 (17)	−0.0089 (14)	0.0008 (13)	−0.0127 (15)
N1	0.0348 (18)	0.0425 (19)	0.047 (3)	−0.0051 (15)	0.0052 (18)	−0.0039 (16)
N2	0.0339 (15)	0.0370 (17)	0.0382 (19)	−0.0004 (13)	0.0010 (14)	−0.0001 (15)
Cl1	0.0465 (6)	0.0949 (9)	0.0576 (9)	−0.0116 (6)	0.0170 (6)	−0.0179 (7)
C1	0.039 (2)	0.073 (3)	0.067 (4)	0.004 (2)	0.014 (2)	0.008 (3)
C2	0.056 (3)	0.080 (4)	0.070 (5)	0.017 (3)	0.026 (3)	0.006 (3)
C3	0.038 (2)	0.058 (2)	0.055 (3)	0.0039 (18)	0.014 (2)	0.003 (2)
C4	0.038 (2)	0.043 (2)	0.043 (3)	0.0051 (16)	0.0018 (19)	0.0027 (19)
C5	0.0393 (19)	0.042 (2)	0.031 (2)	0.0044 (17)	0.0010 (16)	0.0014 (19)
C6	0.0319 (17)	0.039 (2)	0.042 (2)	−0.0008 (16)	0.0034 (16)	0.0036 (18)
C7	0.035 (2)	0.0319 (19)	0.040 (3)	0.0033 (14)	0.0008 (17)	0.0033 (17)
C8	0.0385 (19)	0.042 (2)	0.048 (3)	0.0041 (17)	0.0052 (17)	0.001 (2)
C9	0.064 (3)	0.052 (3)	0.042 (3)	0.003 (2)	−0.001 (2)	−0.011 (2)
C10	0.061 (3)	0.053 (3)	0.059 (4)	−0.007 (2)	−0.010 (3)	−0.015 (3)
C11	0.041 (2)	0.058 (3)	0.067 (3)	−0.010 (2)	−0.008 (2)	0.006 (3)
C12	0.040 (2)	0.049 (2)	0.046 (3)	−0.0008 (18)	0.0025 (18)	−0.003 (2)
S2	0.0419 (5)	0.0785 (8)	0.0590 (7)	0.0063 (5)	0.0047 (5)	0.0152 (7)
O2	0.0478 (15)	0.0633 (17)	0.0407 (17)	0.0165 (13)	0.0013 (14)	0.0141 (15)
N3	0.0345 (17)	0.0403 (17)	0.035 (2)	0.0015 (14)	0.0038 (16)	0.0036 (16)
N4	0.0341 (15)	0.0363 (16)	0.039 (2)	0.0009 (13)	0.0017 (14)	0.0008 (15)
Cl2	0.0472 (6)	0.0745 (7)	0.0574 (9)	−0.0028 (5)	0.0165 (6)	0.0058 (7)
C13	0.040 (2)	0.081 (3)	0.076 (4)	0.006 (2)	0.009 (2)	0.019 (3)
C14	0.067 (3)	0.088 (4)	0.053 (4)	0.006 (3)	0.026 (3)	0.024 (3)
C15	0.042 (2)	0.072 (3)	0.056 (3)	0.008 (2)	0.015 (2)	0.006 (3)
C16	0.041 (2)	0.039 (2)	0.035 (3)	−0.0035 (16)	0.0003 (19)	0.0010 (17)
C17	0.0366 (19)	0.040 (2)	0.044 (3)	−0.0036 (17)	−0.0027 (17)	−0.0040 (19)
C18	0.0311 (16)	0.0359 (19)	0.040 (2)	−0.0023 (15)	0.0006 (16)	−0.0043 (18)
C19	0.037 (2)	0.0332 (19)	0.035 (3)	−0.0094 (16)	−0.0012 (17)	−0.0077 (17)
C20	0.0425 (19)	0.038 (2)	0.037 (2)	−0.0054 (16)	0.0015 (16)	−0.0065 (18)
C21	0.070 (3)	0.044 (2)	0.036 (2)	−0.010 (2)	−0.002 (2)	0.005 (2)
C22	0.066 (3)	0.044 (2)	0.058 (4)	0.005 (2)	−0.020 (3)	0.003 (2)
C23	0.044 (2)	0.050 (2)	0.062 (3)	0.004 (2)	−0.005 (2)	−0.003 (2)
C24	0.041 (2)	0.041 (2)	0.050 (3)	−0.0003 (17)	0.0006 (17)	−0.003 (2)

S1—C1	1.701 (5)	S2—C13	1.686 (5)
S1—C4	1.720 (5)	S2—C16	1.723 (4)
O1—C5	1.240 (4)	O2—C17	1.229 (5)
N1—C5	1.350 (5)	N3—C17	1.347 (6)
N1—N2	1.359 (5)	N3—N4	1.373 (4)
N1—H1A	0.77 (4)	N3—H3A	0.84 (4)
N2—C6	1.282 (5)	N4—C18	1.260 (5)
Cl1—C8	1.743 (4)	Cl2—C20	1.733 (4)
C1—C2	1.314 (8)	C13—C14	1.342 (7)
C1—H1	0.9300	C13—H13	0.9300
C2—C3	1.453 (6)	C14—C15	1.427 (6)
C2—H2B	0.9300	C14—H14A	0.9300
C3—C4	1.445 (7)	C15—C16	1.407 (7)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.479 (5)	C16—C17	1.478 (5)
C6—C7	1.454 (6)	C18—C19	1.459 (6)
C6—H6A	0.9300	C18—H18A	0.9300
C7—C8	1.393 (6)	C19—C20	1.394 (6)
C7—C12	1.396 (5)	C19—C24	1.400 (5)
C8—C9	1.395 (6)	C20—C21	1.401 (6)
C9—C10	1.371 (6)	C21—C22	1.373 (6)
C9—H9A	0.9300	C21—H21A	0.9300
C10—C11	1.358 (7)	C22—C23	1.399 (7)
C10—H10A	0.9300	C22—H22A	0.9300
C11—C12	1.390 (6)	C23—C24	1.354 (6)
C11—H11A	0.9300	C23—H23A	0.9300
C12—H12A	0.9300	C24—H24A	0.9300
C1—S1—C4	90.9 (3)	C13—S2—C16	91.2 (2)
C5—N1—N2	123.0 (4)	C17—N3—N4	123.1 (3)
C5—N1—H1A	120 (4)	C17—N3—H3A	117 (3)
N2—N1—H1A	115 (4)	N4—N3—H3A	120 (3)
C6—N2—N1	115.9 (3)	C18—N4—N3	116.5 (3)
C2—C1—S1	113.6 (4)	C14—C13—S2	113.8 (4)
C2—C1—H1	123.2	C14—C13—H13	123.1
S1—C1—H1	123.2	S2—C13—H13	123.1
C1—C2—C3	116.2 (5)	C13—C14—C15	113.3 (5)
C1—C2—H2B	121.9	C13—C14—H14A	123.3
C3—C2—H2B	121.9	C15—C14—H14A	123.3
C4—C3—C2	105.8 (4)	C16—C15—C14	109.8 (4)
C4—C3—H3	127.1	C16—C15—H15	125.1
C2—C3—H3	127.1	C14—C15—H15	125.1
C3—C4—C5	120.0 (4)	C15—C16—C17	121.2 (4)
C3—C4—S1	113.4 (3)	C15—C16—S2	111.8 (3)
C5—C4—S1	126.6 (4)	C17—C16—S2	126.9 (4)
O1—C5—N1	119.6 (3)	O2—C17—N3	119.6 (4)
O1—C5—C4	119.5 (4)	O2—C17—C16	119.4 (4)
N1—C5—C4	120.9 (4)	N3—C17—C16	121.1 (4)
N2—C6—C7	120.4 (3)	N4—C18—C19	121.0 (3)
N2—C6—H6A	119.8	N4—C18—H18A	119.5
C7—C6—H6A	119.8	C19—C18—H18A	119.5
C8—C7—C12	116.7 (4)	C20—C19—C24	116.6 (4)
C8—C7—C6	122.0 (3)	C20—C19—C18	122.3 (3)
C12—C7—C6	121.2 (4)	C24—C19—C18	121.1 (4)
C7—C8—C9	122.5 (4)	C19—C20—C21	121.5 (4)
C7—C8—Cl1	120.5 (3)	C19—C20—Cl2	120.8 (3)
C9—C8—Cl1	117.0 (3)	C21—C20—Cl2	117.6 (3)
C10—C9—C8	118.3 (4)	C22—C21—C20	120.1 (4)
C10—C9—H9A	120.8	C22—C21—H21A	119.9
C8—C9—H9A	120.8	C20—C21—H21A	119.9
C11—C10—C9	121.2 (4)	C21—C22—C23	118.7 (4)
C11—C10—H10A	119.4	C21—C22—H22A	120.6
C9—C10—H10A	119.4	C23—C22—H22A	120.6
C10—C11—C12	120.4 (4)	C24—C23—C22	120.8 (4)
C10—C11—H11A	119.8	C24—C23—H23A	119.6
C12—C11—H11A	119.8	C22—C23—H23A	119.6
C11—C12—C7	120.9 (4)	C23—C24—C19	122.3 (4)
C11—C12—H12A	119.6	C23—C24—H24A	118.9
C7—C12—H12A	119.6	C19—C24—H24A	118.9
C5—N1—N2—C6	−178.9 (4)	C17—N3—N4—C18	179.7 (4)
C4—S1—C1—C2	1.1 (4)	C16—S2—C13—C14	0.5 (5)
S1—C1—C2—C3	−0.2 (6)	S2—C13—C14—C15	0.3 (7)
C1—C2—C3—C4	−1.1 (6)	C13—C14—C15—C16	−1.1 (7)
C2—C3—C4—C5	−176.0 (4)	C14—C15—C16—C17	−176.5 (4)
C2—C3—C4—S1	1.9 (5)	C14—C15—C16—S2	1.5 (5)
C1—S1—C4—C3	−1.8 (3)	C13—S2—C16—C15	−1.2 (4)
C1—S1—C4—C5	176.0 (4)	C13—S2—C16—C17	176.7 (4)
N2—N1—C5—O1	−179.1 (3)	N4—N3—C17—O2	−179.6 (3)
N2—N1—C5—C4	0.7 (6)	N4—N3—C17—C16	1.6 (6)
C3—C4—C5—O1	5.1 (6)	C15—C16—C17—O2	8.7 (6)
S1—C4—C5—O1	−172.5 (3)	S2—C16—C17—O2	−168.9 (3)
C3—C4—C5—N1	−174.7 (4)	C15—C16—C17—N3	−172.5 (4)
S1—C4—C5—N1	7.6 (6)	S2—C16—C17—N3	9.9 (6)
N1—N2—C6—C7	177.5 (3)	N3—N4—C18—C19	178.0 (3)
N2—C6—C7—C8	−179.1 (3)	N4—C18—C19—C20	−179.3 (3)
N2—C6—C7—C12	−0.2 (6)	N4—C18—C19—C24	−0.1 (5)
C12—C7—C8—C9	−1.3 (6)	C24—C19—C20—C21	−0.6 (5)
C6—C7—C8—C9	177.6 (4)	C18—C19—C20—C21	178.7 (3)
C12—C7—C8—Cl1	179.4 (3)	C24—C19—C20—Cl2	−177.9 (3)
C6—C7—C8—Cl1	−1.7 (5)	C18—C19—C20—Cl2	1.3 (5)
C7—C8—C9—C10	0.5 (6)	C19—C20—C21—C22	0.0 (6)
Cl1—C8—C9—C10	179.9 (4)	Cl2—C20—C21—C22	177.4 (3)
C8—C9—C10—C11	−0.2 (7)	C20—C21—C22—C23	0.8 (6)
C9—C10—C11—C12	0.7 (7)	C21—C22—C23—C24	−1.0 (7)
C10—C11—C12—C7	−1.5 (6)	C22—C23—C24—C19	0.3 (6)
C8—C7—C12—C11	1.7 (6)	C20—C19—C24—C23	0.5 (6)
C6—C7—C12—C11	−177.2 (4)	C18—C19—C24—C23	−178.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1i	0.84 (4)	2.02 (5)	2.856 (4)	175 (4)
N1—H1A···O2ii	0.77 (4)	2.09 (4)	2.845 (5)	166 (5)
C10—H10A···Cl2iii	0.93	2.93	3.758 (5)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O1i	0.84 (4)	2.02 (5)	2.856 (4)	175 (4)
N1—H1A⋯O2ii	0.77 (4)	2.09 (4)	2.845 (5)	166 (5)
C10—H10A⋯Cl2iii	0.93	2.93	3.758 (5)	149

Symmetry codes: (i) ; (ii) ; (iii) .