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

In the title compound, C(12)H(9)ClN(2)OS, the dihedral angle between the aromatic rings is 9.78 (11)°. 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 = 3.7210 (15) and 3.8706 (15) Å] also occurs.

Related literature

For the isostructural bromo-compound and background information, see the preceding paper: Jiang (2010 ▶).

Experimental

Crystal data

C12H9ClN2OS

M = 264.72

Monoclinic,

a = 6.0040 (12) Å

b = 16.831 (3) Å

c = 11.557 (2) Å

β = 94.38 (3)°

V = 1164.5 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.49 mm−1

T = 293 K

0.21 × 0.19 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.491, T max = 0.728

11069 measured reflections

2660 independent reflections

1778 reflections with I > 2σ(I)

R int = 0.115

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.141

S = 0.94

2660 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.33 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/S1600536810010615/hb5369sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010615/hb5369Isup2.hkl

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

C12H9ClN2OS	F(000) = 544
Mr = 264.72	Dx = 1.510 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1778 reflections
a = 6.0040 (12) Å	θ = 3–27.5°
b = 16.831 (3) Å	µ = 0.49 mm−1
c = 11.557 (2) Å	T = 293 K
β = 94.38 (3)°	Block, colorless
V = 1164.5 (4) Å3	0.21 × 0.19 × 0.18 mm
Z = 4

Bruker SMART CCD diffractometer	2660 independent reflections
Radiation source: fine-focus sealed tube	1778 reflections with I > 2σ(I)
graphite	Rint = 0.115
ω scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −7→7
Tmin = 0.491, Tmax = 0.728	k = −21→21
11069 measured reflections	l = −14→14

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) = 0.141	H-atom parameters constrained
S = 0.94	w = 1/[σ2(Fo2) + (0.061P)2] where P = (Fo2 + 2Fc2)/3
2660 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −0.33 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
S1	0.13248 (10)	0.11796 (4)	0.87758 (5)	0.0454 (2)
Cl11	1.14308 (10)	0.37422 (4)	0.75642 (6)	0.0564 (2)
C6	0.4682 (4)	0.12975 (13)	0.5974 (2)	0.0415 (5)
H6A	0.4793	0.1052	0.5260	0.050*
N1	0.3130 (3)	0.10929 (11)	0.66045 (16)	0.0405 (5)
O1	−0.1503 (3)	−0.01594 (11)	0.62318 (14)	0.0543 (5)
N2	0.1660 (3)	0.05312 (11)	0.61567 (15)	0.0435 (5)
H2A	0.1869	0.0321	0.5495	0.052*
C4	−0.0422 (3)	0.05737 (13)	0.79080 (18)	0.0371 (5)
C10	0.9430 (3)	0.30429 (13)	0.7075 (2)	0.0419 (5)
C5	−0.0117 (3)	0.02976 (13)	0.67292 (19)	0.0409 (5)
C12	0.6114 (4)	0.23305 (15)	0.7390 (2)	0.0462 (6)
H12A	0.4937	0.2222	0.7844	0.055*
C3	−0.2281 (4)	0.03656 (14)	0.8471 (2)	0.0448 (5)
H3A	−0.3420	0.0043	0.8145	0.054*
C1	−0.0417 (4)	0.11356 (14)	0.9866 (2)	0.0474 (6)
H1A	−0.0129	0.1389	1.0577	0.057*
C7	0.6284 (3)	0.19098 (13)	0.63533 (18)	0.0385 (5)
C8	0.8067 (4)	0.20886 (14)	0.5689 (2)	0.0452 (6)
H8A	0.8200	0.1823	0.4992	0.054*
C11	0.7646 (4)	0.28965 (15)	0.7745 (2)	0.0499 (6)
H11A	0.7498	0.3180	0.8426	0.060*
C9	0.9633 (4)	0.26525 (15)	0.6049 (2)	0.0465 (6)
H9A	1.0814	0.2767	0.5601	0.056*
C2	−0.2269 (4)	0.06935 (15)	0.9593 (2)	0.0482 (6)
H2B	−0.3401	0.0616	1.0088	0.058*

	U11	U22	U33	U12	U13	U23
S1	0.0461 (4)	0.0519 (4)	0.0386 (4)	−0.0061 (3)	0.0064 (3)	−0.0075 (2)
Cl11	0.0523 (4)	0.0568 (5)	0.0598 (4)	−0.0115 (3)	0.0023 (3)	0.0021 (3)
C6	0.0449 (12)	0.0451 (14)	0.0355 (11)	0.0036 (10)	0.0087 (10)	−0.0003 (9)
N1	0.0414 (10)	0.0429 (11)	0.0375 (10)	−0.0030 (8)	0.0046 (8)	−0.0026 (8)
O1	0.0608 (10)	0.0597 (11)	0.0433 (9)	−0.0207 (9)	0.0103 (8)	−0.0127 (8)
N2	0.0453 (10)	0.0479 (12)	0.0381 (10)	−0.0055 (9)	0.0082 (8)	−0.0093 (9)
C4	0.0402 (10)	0.0361 (12)	0.0349 (11)	0.0006 (9)	0.0020 (9)	−0.0009 (9)
C10	0.0396 (11)	0.0387 (13)	0.0470 (13)	−0.0025 (9)	0.0017 (10)	0.0067 (10)
C5	0.0434 (11)	0.0403 (13)	0.0387 (12)	−0.0006 (10)	0.0022 (9)	−0.0013 (10)
C12	0.0448 (12)	0.0498 (15)	0.0458 (13)	−0.0024 (11)	0.0156 (10)	−0.0004 (11)
C3	0.0450 (12)	0.0451 (14)	0.0447 (13)	−0.0039 (10)	0.0056 (10)	−0.0021 (10)
C1	0.0563 (14)	0.0494 (15)	0.0373 (13)	−0.0001 (11)	0.0079 (11)	−0.0047 (10)
C7	0.0388 (11)	0.0399 (13)	0.0370 (11)	0.0033 (9)	0.0046 (9)	0.0054 (9)
C8	0.0467 (12)	0.0491 (14)	0.0413 (13)	0.0022 (11)	0.0127 (10)	0.0000 (10)
C11	0.0550 (13)	0.0530 (15)	0.0426 (13)	−0.0033 (12)	0.0102 (11)	−0.0072 (11)
C9	0.0430 (12)	0.0514 (15)	0.0465 (13)	−0.0026 (11)	0.0132 (10)	0.0059 (11)
C2	0.0498 (13)	0.0535 (15)	0.0426 (13)	0.0012 (11)	0.0129 (10)	−0.0008 (11)

S1—C1	1.699 (3)	C12—C11	1.365 (3)
S1—C4	1.728 (2)	C12—C7	1.402 (3)
Cl11—C10	1.745 (2)	C12—H12A	0.9300
C6—N1	1.273 (3)	C3—C2	1.408 (3)
C6—C7	1.454 (3)	C3—H3A	0.9300
C6—H6A	0.9300	C1—C2	1.355 (3)
N1—N2	1.368 (2)	C1—H1A	0.9300
O1—C5	1.242 (3)	C7—C8	1.397 (3)
N2—C5	1.356 (3)	C8—C9	1.378 (3)
N2—H2A	0.8600	C8—H8A	0.9300
C4—C3	1.379 (3)	C11—H11A	0.9300
C4—C5	1.464 (3)	C9—H9A	0.9300
C10—C9	1.369 (3)	C2—H2B	0.9300
C10—C11	1.392 (3)
C1—S1—C4	91.38 (11)	C4—C3—H3A	123.6
N1—C6—C7	121.0 (2)	C2—C3—H3A	123.6
N1—C6—H6A	119.5	C2—C1—S1	113.05 (18)
C7—C6—H6A	119.5	C2—C1—H1A	123.5
C6—N1—N2	116.72 (19)	S1—C1—H1A	123.5
C5—N2—N1	121.65 (18)	C8—C7—C12	118.0 (2)
C5—N2—H2A	119.2	C8—C7—C6	120.3 (2)
N1—N2—H2A	119.2	C12—C7—C6	121.7 (2)
C3—C4—C5	121.4 (2)	C9—C8—C7	121.1 (2)
C3—C4—S1	110.67 (16)	C9—C8—H8A	119.5
C5—C4—S1	127.88 (17)	C7—C8—H8A	119.5
C9—C10—C11	121.4 (2)	C12—C11—C10	119.1 (2)
C9—C10—Cl11	120.03 (18)	C12—C11—H11A	120.5
C11—C10—Cl11	118.62 (18)	C10—C11—H11A	120.5
O1—C5—N2	118.6 (2)	C10—C9—C8	119.3 (2)
O1—C5—C4	120.0 (2)	C10—C9—H9A	120.4
N2—C5—C4	121.4 (2)	C8—C9—H9A	120.4
C11—C12—C7	121.2 (2)	C1—C2—C3	112.1 (2)
C11—C12—H12A	119.4	C1—C2—H2B	124.0
C7—C12—H12A	119.4	C3—C2—H2B	124.0
C4—C3—C2	112.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1i	0.86	2.01	2.825 (2)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1i	0.86	2.01	2.825 (2)	158

Symmetry code: (i) .