(E)-N'-(2-Thienyl-methyl-idene)-p-toluene-sulfono-hydrazide.

The S-N(H)-N=C linkage in the title mol-ecule, C(12)H(12)N(2)O(2)S(2), is non-planar [torsion angle = 15.5 (1)°] as the amino N atom is pyramidally coordinated. The amino group acts as a hydrogen-bond donor to an O atom of an adjacent mol-ecule, generating chains running parallel to the c axis.

Related literature

For the structure of the (E)-N′-benzyl­idene-p-toluene­sulf­ono­hydrazide homolog, see: Mehrabi et al. (2008 ▶).

Experimental

Crystal data

C12H12N2O2S2

M = 280.36

Monoclinic,

a = 14.3758 (10) Å

b = 9.8613 (7) Å

c = 9.6172 (7) Å

β = 104.981 (1)°

V = 1317.03 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.40 mm−1

T = 100 K

0.40 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.857, T max = 0.925

8238 measured reflections

3022 independent reflections

2728 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.085

S = 1.04

3022 reflections

168 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810032708/pk2261sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810032708/pk2261Isup2.hkl

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

C12H12N2O2S2	F(000) = 584
Mr = 280.36	Dx = 1.414 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4750 reflections
a = 14.3758 (10) Å	θ = 2.5–28.3°
b = 9.8613 (7) Å	µ = 0.40 mm−1
c = 9.6172 (7) Å	T = 100 K
β = 104.981 (1)°	Prism, yellow
V = 1317.03 (16) Å3	0.40 × 0.20 × 0.20 mm
Z = 4

Bruker SMART APEX diffractometer	3022 independent reflections
Radiation source: fine-focus sealed tube	2728 reflections with I > 2σ(I)
graphite	Rint = 0.020
ω scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→18
Tmin = 0.857, Tmax = 0.925	k = −12→12
8238 measured reflections	l = −8→12

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0458P)2 + 0.7746P] where P = (Fo2 + 2Fc2)/3
3022 reflections	(Δ/σ)max = 0.001
168 parameters	Δρmax = 0.42 e Å−3
1 restraint	Δρmin = −0.36 e Å−3

	x	y	z	Uiso*/Ueq
S1	0.16267 (2)	0.25347 (3)	0.52894 (3)	0.01262 (10)
S2	0.51633 (3)	0.43030 (4)	0.75091 (4)	0.02186 (11)
O1	0.18378 (8)	0.21042 (11)	0.67638 (11)	0.0176 (2)
O2	0.08674 (7)	0.18970 (10)	0.42362 (11)	0.0174 (2)
N1	0.26105 (9)	0.22234 (13)	0.47478 (13)	0.0148 (2)
H1	0.2522 (14)	0.235 (2)	0.3840 (11)	0.024 (5)*
N2	0.34437 (9)	0.28097 (12)	0.56466 (13)	0.0156 (2)
C1	0.14605 (10)	0.42992 (14)	0.52115 (15)	0.0136 (3)
C2	0.08653 (10)	0.48722 (15)	0.39742 (15)	0.0159 (3)
H2	0.0530	0.4313	0.3203	0.019*
C3	0.07698 (10)	0.62763 (15)	0.38847 (15)	0.0170 (3)
H3	0.0360	0.6673	0.3048	0.020*
C4	0.12658 (10)	0.71101 (15)	0.50031 (16)	0.0172 (3)
C5	0.18520 (11)	0.65074 (15)	0.62312 (16)	0.0206 (3)
H5	0.2189	0.7065	0.7003	0.025*
C6	0.19530 (11)	0.51082 (15)	0.63480 (15)	0.0191 (3)
H6	0.2353	0.4710	0.7192	0.023*
C7	0.11737 (12)	0.86307 (15)	0.48857 (17)	0.0216 (3)
H7A	0.1290	0.9025	0.5851	0.032*
H7B	0.0524	0.8870	0.4322	0.032*
H7C	0.1647	0.8987	0.4408	0.032*
C8	0.41651 (11)	0.28677 (14)	0.51016 (16)	0.0169 (3)
H8	0.4109	0.2523	0.4161	0.020*
C9	0.50662 (10)	0.34545 (15)	0.59069 (16)	0.0173 (3)
C10	0.59275 (11)	0.34852 (15)	0.55085 (17)	0.0208 (3)
H10	0.6019	0.3079	0.4658	0.025*
C11	0.66556 (11)	0.41995 (16)	0.65279 (19)	0.0235 (3)
H11	0.7291	0.4324	0.6431	0.028*
C12	0.63483 (11)	0.46843 (16)	0.76529 (18)	0.0238 (3)
H12	0.6745	0.5179	0.8432	0.029*

	U11	U22	U33	U12	U13	U23
S1	0.01349 (18)	0.01241 (17)	0.01124 (17)	−0.00057 (12)	0.00189 (13)	0.00002 (11)
S2	0.0198 (2)	0.0240 (2)	0.0209 (2)	−0.00308 (14)	0.00374 (15)	−0.00061 (14)
O1	0.0225 (5)	0.0173 (5)	0.0128 (5)	−0.0004 (4)	0.0045 (4)	0.0019 (4)
O2	0.0160 (5)	0.0164 (5)	0.0175 (5)	−0.0029 (4)	0.0002 (4)	−0.0010 (4)
N1	0.0137 (6)	0.0176 (6)	0.0120 (6)	0.0007 (4)	0.0014 (4)	−0.0019 (4)
N2	0.0142 (6)	0.0142 (5)	0.0163 (6)	−0.0001 (4)	0.0000 (5)	0.0006 (4)
C1	0.0136 (6)	0.0128 (6)	0.0149 (6)	0.0002 (5)	0.0048 (5)	0.0003 (5)
C2	0.0133 (6)	0.0180 (7)	0.0152 (6)	−0.0005 (5)	0.0018 (5)	−0.0011 (5)
C3	0.0136 (6)	0.0192 (7)	0.0168 (7)	0.0024 (5)	0.0017 (5)	0.0031 (5)
C4	0.0161 (7)	0.0159 (7)	0.0210 (7)	0.0011 (5)	0.0073 (6)	0.0017 (5)
C5	0.0249 (7)	0.0170 (7)	0.0177 (7)	−0.0016 (6)	0.0013 (6)	−0.0032 (6)
C6	0.0226 (7)	0.0179 (7)	0.0138 (7)	0.0015 (6)	−0.0005 (5)	0.0002 (5)
C7	0.0246 (8)	0.0143 (7)	0.0256 (8)	0.0008 (6)	0.0062 (6)	0.0017 (6)
C8	0.0184 (7)	0.0140 (6)	0.0176 (7)	0.0017 (5)	0.0032 (5)	0.0006 (5)
C9	0.0169 (7)	0.0145 (6)	0.0199 (7)	0.0012 (5)	0.0038 (5)	0.0026 (5)
C10	0.0203 (7)	0.0163 (7)	0.0248 (8)	−0.0010 (6)	0.0040 (6)	0.0040 (6)
C11	0.0164 (7)	0.0190 (7)	0.0340 (9)	−0.0011 (6)	0.0048 (6)	0.0077 (6)
C12	0.0189 (7)	0.0192 (7)	0.0293 (8)	−0.0042 (6)	−0.0006 (6)	0.0035 (6)

S1—O2	1.4288 (10)	C4—C7	1.507 (2)
S1—O1	1.4355 (10)	C5—C6	1.389 (2)
S1—N1	1.6572 (13)	C5—H5	0.9500
S1—C1	1.7553 (14)	C6—H6	0.9500
S2—C12	1.7148 (16)	C7—H7A	0.9800
S2—C9	1.7270 (15)	C7—H7B	0.9800
N1—N2	1.4074 (16)	C7—H7C	0.9800
N1—H1	0.859 (9)	C8—C9	1.447 (2)
N2—C8	1.279 (2)	C8—H8	0.9500
C1—C6	1.3901 (19)	C9—C10	1.388 (2)
C1—C2	1.3932 (19)	C10—C11	1.422 (2)
C2—C3	1.392 (2)	C10—H10	0.9500
C2—H2	0.9500	C11—C12	1.357 (2)
C3—C4	1.395 (2)	C11—H11	0.9500
C3—H3	0.9500	C12—H12	0.9500
C4—C5	1.394 (2)
O2—S1—O1	119.85 (6)	C4—C5—H5	119.3
O2—S1—N1	104.68 (6)	C1—C6—C5	119.03 (13)
O1—S1—N1	106.02 (6)	C1—C6—H6	120.5
O2—S1—C1	109.60 (6)	C5—C6—H6	120.5
O1—S1—C1	109.08 (7)	C4—C7—H7A	109.5
N1—S1—C1	106.74 (6)	C4—C7—H7B	109.5
C12—S2—C9	91.59 (8)	H7A—C7—H7B	109.5
N2—N1—S1	113.01 (9)	C4—C7—H7C	109.5
N2—N1—H1	116.3 (13)	H7A—C7—H7C	109.5
S1—N1—H1	112.1 (13)	H7B—C7—H7C	109.5
C8—N2—N1	114.73 (12)	N2—C8—C9	120.48 (14)
C6—C1—C2	120.95 (13)	N2—C8—H8	119.8
C6—C1—S1	119.95 (11)	C9—C8—H8	119.8
C2—C1—S1	119.03 (11)	C10—C9—C8	126.88 (14)
C1—C2—C3	119.03 (13)	C10—C9—S2	111.33 (11)
C1—C2—H2	120.5	C8—C9—S2	121.73 (11)
C3—C2—H2	120.5	C9—C10—C11	111.76 (14)
C4—C3—C2	121.08 (13)	C9—C10—H10	124.1
C4—C3—H3	119.5	C11—C10—H10	124.1
C2—C3—H3	119.5	C12—C11—C10	113.01 (14)
C3—C4—C5	118.60 (13)	C12—C11—H11	123.5
C3—C4—C7	120.76 (13)	C10—C11—H11	123.5
C5—C4—C7	120.65 (14)	C11—C12—S2	112.32 (12)
C6—C5—C4	121.31 (14)	C11—C12—H12	123.8
C6—C5—H5	119.3	S2—C12—H12	123.8
O2—S1—N1—N2	178.54 (9)	C3—C4—C5—C6	0.5 (2)
O1—S1—N1—N2	−53.83 (11)	C7—C4—C5—C6	−179.24 (15)
C1—S1—N1—N2	62.38 (11)	C2—C1—C6—C5	−0.6 (2)
S1—N1—N2—C8	−164.50 (11)	S1—C1—C6—C5	176.50 (12)
O2—S1—C1—C6	163.60 (12)	C4—C5—C6—C1	0.2 (2)
O1—S1—C1—C6	30.58 (14)	N1—N2—C8—C9	179.61 (12)
N1—S1—C1—C6	−83.57 (13)	N2—C8—C9—C10	174.24 (14)
O2—S1—C1—C2	−19.24 (14)	N2—C8—C9—S2	−9.0 (2)
O1—S1—C1—C2	−152.26 (11)	C12—S2—C9—C10	−0.45 (12)
N1—S1—C1—C2	93.59 (12)	C12—S2—C9—C8	−177.63 (13)
C6—C1—C2—C3	0.2 (2)	C8—C9—C10—C11	177.28 (14)
S1—C1—C2—C3	−176.95 (11)	S2—C9—C10—C11	0.27 (16)
C1—C2—C3—C4	0.6 (2)	C9—C10—C11—C12	0.12 (19)
C2—C3—C4—C5	−1.0 (2)	C10—C11—C12—S2	−0.46 (18)
C2—C3—C4—C7	178.80 (14)	C9—S2—C12—C11	0.52 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86 (1)	2.06 (1)	2.874 (2)	159 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86 (1)	2.06 (1)	2.874 (2)	159 (2)

Symmetry code: (i) .