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

In the title compound, C(13)H(12)N(2)OS, the dihedral angle between the aromatic rings is 14.84 (17)°. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds generate R(2) (2)(8) loops.

Related literature

For a related structure, see: Li & Jian (2010 ▶).

Experimental

Crystal data

C13H12N2OS

M = 244.31

Monoclinic,

a = 14.920 (3) Å

b = 5.3976 (11) Å

c = 15.636 (3) Å

β = 105.87 (3)°

V = 1211.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 293 K

0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer

10416 measured reflections

2697 independent reflections

1759 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.080

wR(F 2) = 0.275

S = 1.08

2697 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.73 e Å−3

Δρmin = −0.47 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/S1600536810017976/hb5447sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017976/hb5447Isup2.hkl

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

C13H12N2OS	F(000) = 512
Mr = 244.31	Dx = 1.340 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1759 reflections
a = 14.920 (3) Å	θ = 27.5–3.4°
b = 5.3976 (11) Å	µ = 0.25 mm−1
c = 15.636 (3) Å	T = 293 K
β = 105.87 (3)°	Block, colorless
V = 1211.2 (4) Å3	0.22 × 0.20 × 0.18 mm
Z = 4

Bruker SMART CCD diffractometer	1759 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.051
graphite	θmax = 27.5°, θmin = 3.4°
phi and ω scans	h = −19→19
10416 measured reflections	k = −6→6
2697 independent reflections	l = −20→20

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)] = 0.080	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.275	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.1685P)2 + 0.1567P] where P = (Fo2 + 2Fc2)/3
2697 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.73 e Å−3
0 restraints	Δρmin = −0.47 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	0.20737 (7)	0.6743 (2)	0.48624 (6)	0.0649 (4)
N1	0.17714 (18)	0.2992 (5)	0.59639 (17)	0.0481 (7)
N2	0.09655 (17)	0.2160 (6)	0.53950 (16)	0.0507 (7)
H2A	0.0658	0.1007	0.5569	0.061*
O1	−0.00815 (15)	0.2169 (5)	0.40660 (15)	0.0576 (7)
C9	0.0635 (2)	0.3089 (6)	0.4567 (2)	0.0461 (7)
C8	0.2059 (2)	0.1867 (6)	0.6707 (2)	0.0506 (8)
H8A	0.1713	0.0564	0.6841	0.061*
C5	0.2924 (2)	0.2600 (6)	0.7348 (2)	0.0476 (7)
C10	0.11121 (19)	0.5146 (6)	0.42646 (19)	0.0460 (7)
C2	0.4649 (2)	0.3822 (8)	0.8565 (2)	0.0573 (9)
C12	0.1361 (2)	0.8109 (7)	0.3262 (2)	0.0607 (10)
H12A	0.1276	0.9021	0.2741	0.073*
C7	0.4251 (2)	0.5308 (8)	0.7826 (2)	0.0636 (10)
H7A	0.4562	0.6732	0.7732	0.076*
C11	0.0757 (2)	0.6016 (6)	0.3332 (2)	0.0506 (8)
H11A	0.0261	0.5375	0.2889	0.061*
C3	0.4150 (3)	0.1770 (7)	0.8695 (2)	0.0665 (10)
H3A	0.4388	0.0766	0.9188	0.080*
C6	0.3420 (3)	0.4727 (8)	0.7240 (2)	0.0598 (9)
H6A	0.3176	0.5765	0.6758	0.072*
C4	0.3296 (3)	0.1174 (8)	0.8101 (2)	0.0631 (10)
H4A	0.2969	−0.0203	0.8211	0.076*
C13	0.2054 (2)	0.8631 (7)	0.4008 (2)	0.0582 (9)
H13A	0.2477	0.9916	0.4041	0.070*
C1	0.5603 (3)	0.4412 (11)	0.9168 (2)	0.0842 (14)
H1B	0.5764	0.3217	0.9640	0.126*
H1C	0.5598	0.6038	0.9415	0.126*
H1D	0.6054	0.4355	0.8833	0.126*

	U11	U22	U33	U12	U13	U23
S1	0.0703 (7)	0.0624 (8)	0.0608 (6)	−0.0180 (4)	0.0157 (5)	−0.0037 (4)
N1	0.0482 (14)	0.0436 (16)	0.0523 (14)	−0.0058 (11)	0.0134 (11)	−0.0062 (12)
N2	0.0476 (14)	0.0518 (18)	0.0515 (15)	−0.0119 (12)	0.0119 (11)	−0.0025 (12)
O1	0.0464 (12)	0.0575 (16)	0.0636 (14)	−0.0100 (10)	0.0059 (10)	−0.0006 (12)
C9	0.0418 (15)	0.0428 (19)	0.0553 (18)	−0.0020 (12)	0.0160 (13)	−0.0049 (13)
C8	0.0563 (18)	0.049 (2)	0.0486 (17)	−0.0078 (14)	0.0182 (13)	−0.0002 (14)
C5	0.0579 (18)	0.0424 (19)	0.0443 (15)	−0.0017 (14)	0.0170 (13)	−0.0032 (13)
C10	0.0402 (15)	0.0450 (19)	0.0521 (16)	0.0006 (12)	0.0114 (12)	−0.0028 (13)
C2	0.0542 (18)	0.071 (3)	0.0485 (17)	0.0056 (16)	0.0169 (14)	−0.0091 (16)
C12	0.0487 (18)	0.067 (3)	0.067 (2)	0.0068 (15)	0.0157 (15)	0.0172 (18)
C7	0.063 (2)	0.070 (3)	0.0566 (19)	−0.0181 (18)	0.0147 (15)	−0.0001 (18)
C11	0.0444 (16)	0.048 (2)	0.0649 (19)	0.0041 (13)	0.0249 (14)	0.0159 (15)
C3	0.077 (2)	0.063 (3)	0.052 (2)	0.0041 (19)	0.0038 (16)	0.0088 (17)
C6	0.069 (2)	0.055 (2)	0.0504 (17)	−0.0126 (17)	0.0085 (15)	0.0067 (16)
C4	0.078 (2)	0.053 (2)	0.057 (2)	−0.0079 (18)	0.0159 (17)	0.0089 (16)
C13	0.062 (2)	0.046 (2)	0.065 (2)	−0.0056 (15)	0.0150 (16)	0.0037 (16)
C1	0.058 (2)	0.131 (5)	0.059 (2)	0.001 (2)	0.0076 (17)	−0.013 (3)

S1—C13	1.673 (3)	C2—C1	1.511 (5)
S1—C10	1.715 (3)	C12—C13	1.360 (5)
N1—C8	1.277 (4)	C12—C11	1.468 (5)
N1—N2	1.362 (3)	C12—H12A	0.9300
N2—C9	1.350 (4)	C7—C6	1.362 (5)
N2—H2A	0.8600	C7—H7A	0.9300
O1—C9	1.242 (4)	C11—H11A	0.9300
C9—C10	1.465 (4)	C3—C4	1.394 (5)
C8—C5	1.455 (4)	C3—H3A	0.9300
C8—H8A	0.9300	C6—H6A	0.9300
C5—C4	1.389 (5)	C4—H4A	0.9300
C5—C6	1.400 (5)	C13—H13A	0.9300
C10—C11	1.486 (4)	C1—H1B	0.9600
C2—C3	1.380 (5)	C1—H1C	0.9600
C2—C7	1.399 (5)	C1—H1D	0.9600
C13—S1—C10	92.39 (16)	C6—C7—H7A	119.1
C8—N1—N2	117.1 (3)	C2—C7—H7A	119.1
C9—N2—N1	122.0 (3)	C12—C11—C10	104.7 (3)
C9—N2—H2A	119.0	C12—C11—H11A	127.6
N1—N2—H2A	119.0	C10—C11—H11A	127.6
O1—C9—N2	118.8 (3)	C2—C3—C4	121.3 (3)
O1—C9—C10	120.7 (3)	C2—C3—H3A	119.4
N2—C9—C10	120.5 (3)	C4—C3—H3A	119.4
N1—C8—C5	120.8 (3)	C7—C6—C5	121.5 (3)
N1—C8—H8A	119.6	C7—C6—H6A	119.3
C5—C8—H8A	119.6	C5—C6—H6A	119.3
C4—C5—C6	117.0 (3)	C5—C4—C3	121.2 (4)
C4—C5—C8	120.4 (3)	C5—C4—H4A	119.4
C6—C5—C8	122.6 (3)	C3—C4—H4A	119.4
C9—C10—C11	118.8 (3)	C12—C13—S1	113.7 (3)
C9—C10—S1	127.8 (2)	C12—C13—H13A	123.1
C11—C10—S1	113.4 (2)	S1—C13—H13A	123.1
C3—C2—C7	117.2 (3)	C2—C1—H1B	109.5
C3—C2—C1	122.1 (4)	C2—C1—H1C	109.5
C7—C2—C1	120.6 (4)	H1B—C1—H1C	109.5
C13—C12—C11	115.7 (3)	C2—C1—H1D	109.5
C13—C12—H12A	122.1	H1B—C1—H1D	109.5
C11—C12—H12A	122.1	H1C—C1—H1D	109.5
C6—C7—C2	121.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1i	0.86	2.07	2.919 (4)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1i	0.86	2.07	2.919 (4)	170

Symmetry code: (i) .