Crystal structure of (E)-N-phenyl-N'-[1-(thio-phen-2-yl)ethyl-idene]formo-hydrazide.

In the title compound, C13H12N2OS, the planes of the thio-phene and phenyl rings are nearly perpendicular to each other, making a dihedral angle of 86.42 (12)°. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming a helical chain along the b-axis direction.

Related literature

For the biological activity of thio­phene derivatives, see: Bondock et al. (2010 ▶); Bellina et al. (2007 ▶); Konstanti­nova et al. (2009 ▶); Al-Said et al. (2011 ▶). For the crystal structure of a similar compound, viz. (E)-N′-[1-(thio­phen-2-yl)ethyl­idene]benzohydrazide, see: Shan et al. (2011 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C13H12N2OS

M = 244.32

Orthorhombic,

a = 5.4960 (7) Å

b = 11.0177 (13) Å

c = 20.249 (2) Å

V = 1226.1 (2) Å3

Z = 4

Cu Kα radiation

μ = 2.22 mm−1

T = 296 K

0.25 × 0.22 × 0.20 mm

Data collection

Bruker X8 Proteum diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T min = 0.604, T max = 0.662

6298 measured reflections

2010 independent reflections

1904 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.102

S = 1.10

2010 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack (1983 ▶), 805 Friedel pairs

Absolute structure parameter: 0.02 (2)

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814016511/is5369sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814016511/is5369Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814016511/is5369Isup3.cml

Click here for additional data file.

ORTEP . DOI: 10.1107/S1600536814016511/is5369fig1.tif

ORTEP view of the mol­ecule with the atom-labeling scheme. The displacement ellipsoids are drawn at the 50% probability level.

Click here for additional data file.

a . DOI: 10.1107/S1600536814016511/is5369fig2.tif

A mol­ecular packing view of the title compound down the a-axis.

CCDC reference: 1014287

Additional supporting information: crystallographic information; 3D view; checkCIF report

C13H12N2OS	F(000) = 512
Mr = 244.32	Dx = 1.324 Mg m−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6298 reflections
a = 5.4960 (7) Å	θ = 4.4–64.6°
b = 11.0177 (13) Å	µ = 2.22 mm−1
c = 20.249 (2) Å	T = 296 K
V = 1226.1 (2) Å3	Block, pale yellow
Z = 4	0.25 × 0.22 × 0.20 mm

Bruker X8 Proteum diffractometer	2010 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode	1904 reflections with I > 2σ(I)
Helios multilayer optics monochromator	Rint = 0.042
Detector resolution: 10.7 pixels mm-1	θmax = 64.6°, θmin = 4.4°
φ and ω scans	h = −2→6
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −12→12
Tmin = 0.604, Tmax = 0.662	l = −23→22
6298 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.038	w = 1/[σ2(Fo2) + (0.0605P)2 + 0.0861P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.102	(Δ/σ)max = 0.001
S = 1.10	Δρmax = 0.21 e Å−3
2010 reflections	Δρmin = −0.20 e Å−3
165 parameters	Extinction correction: SHELXL, FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
0 restraints	Extinction coefficient: 0.0158 (16)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 805 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.02 (2)

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 on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.05502 (12)	0.12455 (6)	0.72104 (3)	0.0539 (2)
O1	0.0434 (4)	−0.24121 (15)	0.55887 (8)	0.0526 (6)
N1	0.0078 (3)	0.00557 (16)	0.59394 (8)	0.0348 (5)
N2	0.0086 (3)	−0.04249 (15)	0.52882 (8)	0.0344 (5)
C1	−0.0682 (6)	0.1399 (3)	0.79702 (12)	0.0623 (10)
C2	−0.2635 (6)	0.0712 (3)	0.80591 (13)	0.0648 (10)
C3	−0.3227 (5)	0.0016 (2)	0.74907 (11)	0.0513 (8)
C4	−0.1639 (4)	0.02325 (18)	0.69777 (10)	0.0358 (6)
C5	−0.1724 (4)	−0.02503 (18)	0.63061 (10)	0.0331 (6)
C6	−0.3905 (4)	−0.0972 (2)	0.61062 (13)	0.0509 (8)
C7	0.0373 (4)	−0.16179 (19)	0.51733 (10)	0.0410 (7)
C8	0.0373 (4)	0.04484 (17)	0.47710 (9)	0.0325 (6)
C9	0.2273 (4)	0.0366 (2)	0.43330 (11)	0.0397 (6)
C10	0.2429 (4)	0.1192 (2)	0.38203 (12)	0.0479 (7)
C11	0.0710 (5)	0.2091 (2)	0.37516 (11)	0.0469 (7)
C12	−0.1151 (5)	0.2185 (2)	0.41975 (12)	0.0463 (8)
C13	−0.1322 (4)	0.1365 (2)	0.47156 (11)	0.0413 (6)
H1	−0.00560	0.19130	0.82930	0.0750*
H2	−0.35200	0.06880	0.84500	0.0780*
H3	−0.45300	−0.05220	0.74680	0.0620*
H6A	−0.39060	−0.10770	0.56360	0.0760*
H6B	−0.53550	−0.05510	0.62380	0.0760*
H6C	−0.38540	−0.17530	0.63170	0.0760*
H7	0.05420	−0.18570	0.47350	0.0490*
H9	0.34410	−0.02390	0.43800	0.0480*
H10	0.37060	0.11400	0.35200	0.0570*
H11	0.08130	0.26340	0.34010	0.0560*
H12	−0.23010	0.27990	0.41530	0.0560*
H13	−0.25720	0.14340	0.50230	0.0500*

	U11	U22	U33	U12	U13	U23
S1	0.0546 (4)	0.0703 (5)	0.0368 (3)	−0.0147 (3)	−0.0029 (3)	−0.0071 (3)
O1	0.0729 (11)	0.0375 (9)	0.0474 (9)	0.0049 (8)	0.0049 (8)	0.0096 (7)
N1	0.0402 (10)	0.0379 (9)	0.0263 (8)	−0.0024 (8)	−0.0012 (7)	−0.0037 (6)
N2	0.0452 (10)	0.0313 (8)	0.0266 (8)	0.0006 (8)	−0.0005 (7)	−0.0022 (7)
C1	0.085 (2)	0.0689 (17)	0.0330 (12)	0.0037 (16)	−0.0059 (13)	−0.0095 (11)
C2	0.0757 (18)	0.0819 (19)	0.0368 (13)	0.0055 (16)	0.0152 (13)	0.0000 (13)
C3	0.0524 (14)	0.0590 (15)	0.0426 (13)	−0.0041 (12)	0.0127 (11)	−0.0022 (11)
C4	0.0373 (10)	0.0370 (11)	0.0332 (10)	0.0038 (9)	0.0009 (8)	0.0026 (8)
C5	0.0317 (10)	0.0314 (10)	0.0362 (11)	0.0037 (8)	−0.0030 (8)	0.0008 (8)
C6	0.0372 (12)	0.0564 (15)	0.0592 (14)	−0.0111 (10)	0.0008 (11)	−0.0119 (12)
C7	0.0511 (12)	0.0353 (11)	0.0366 (11)	0.0020 (9)	0.0024 (10)	−0.0018 (9)
C8	0.0388 (10)	0.0296 (10)	0.0291 (9)	−0.0017 (8)	−0.0051 (8)	−0.0012 (8)
C9	0.0355 (10)	0.0392 (11)	0.0444 (12)	0.0049 (9)	0.0011 (9)	0.0016 (10)
C10	0.0456 (12)	0.0511 (13)	0.0469 (13)	−0.0056 (11)	0.0089 (10)	0.0094 (11)
C11	0.0604 (14)	0.0365 (11)	0.0439 (12)	−0.0080 (11)	−0.0054 (11)	0.0088 (9)
C12	0.0536 (14)	0.0350 (12)	0.0503 (13)	0.0084 (11)	−0.0087 (11)	0.0024 (10)
C13	0.0429 (11)	0.0416 (11)	0.0395 (11)	0.0083 (10)	0.0012 (10)	−0.0035 (10)

S1—C1	1.690 (3)	C10—C11	1.376 (3)
S1—C4	1.707 (2)	C11—C12	1.368 (4)
O1—C7	1.214 (3)	C12—C13	1.388 (3)
N1—N2	1.421 (2)	C1—H1	0.9300
N1—C5	1.283 (3)	C2—H2	0.9300
N2—C7	1.344 (3)	C3—H3	0.9300
N2—C8	1.431 (2)	C6—H6A	0.9600
C1—C2	1.326 (5)	C6—H6B	0.9600
C2—C3	1.421 (4)	C6—H6C	0.9600
C3—C4	1.378 (3)	C7—H7	0.9300
C4—C5	1.461 (3)	C9—H9	0.9300
C5—C6	1.494 (3)	C10—H10	0.9300
C8—C9	1.373 (3)	C11—H11	0.9300
C8—C13	1.379 (3)	C12—H12	0.9300
C9—C10	1.383 (3)	C13—H13	0.9300
C1—S1—C4	91.96 (13)	C2—C1—H1	123.00
N2—N1—C5	116.20 (17)	C1—C2—H2	124.00
N1—N2—C7	121.70 (16)	C3—C2—H2	124.00
N1—N2—C8	115.40 (15)	C2—C3—H3	124.00
C7—N2—C8	121.19 (16)	C4—C3—H3	124.00
S1—C1—C2	113.0 (2)	C5—C6—H6A	109.00
C1—C2—C3	112.6 (2)	C5—C6—H6B	109.00
C2—C3—C4	111.9 (2)	C5—C6—H6C	109.00
S1—C4—C3	110.58 (16)	H6A—C6—H6B	109.00
S1—C4—C5	121.16 (16)	H6A—C6—H6C	109.00
C3—C4—C5	128.2 (2)	H6B—C6—H6C	109.00
N1—C5—C4	114.73 (19)	O1—C7—H7	117.00
N1—C5—C6	127.04 (19)	N2—C7—H7	117.00
C4—C5—C6	118.13 (19)	C8—C9—H9	120.00
O1—C7—N2	126.02 (19)	C10—C9—H9	120.00
N2—C8—C9	120.81 (18)	C9—C10—H10	120.00
N2—C8—C13	118.53 (18)	C11—C10—H10	120.00
C9—C8—C13	120.65 (19)	C10—C11—H11	120.00
C8—C9—C10	119.2 (2)	C12—C11—H11	120.00
C9—C10—C11	120.5 (2)	C11—C12—H12	120.00
C10—C11—C12	120.1 (2)	C13—C12—H12	120.00
C11—C12—C13	120.0 (2)	C8—C13—H13	120.00
C8—C13—C12	119.5 (2)	C12—C13—H13	120.00
S1—C1—H1	124.00
C4—S1—C1—C2	0.9 (3)	C2—C3—C4—C5	−176.1 (2)
C1—S1—C4—C3	−1.3 (2)	C2—C3—C4—S1	1.4 (3)
C1—S1—C4—C5	176.4 (2)	S1—C4—C5—N1	6.3 (3)
C5—N1—N2—C7	−67.0 (2)	C3—C4—C5—N1	−176.4 (2)
C5—N1—N2—C8	127.7 (2)	C3—C4—C5—C6	7.0 (3)
N2—N1—C5—C4	178.38 (16)	S1—C4—C5—C6	−170.31 (16)
N2—N1—C5—C6	−5.3 (3)	N2—C8—C9—C10	176.94 (19)
C7—N2—C8—C13	135.3 (2)	C13—C8—C9—C10	−2.1 (3)
N1—N2—C7—O1	6.9 (3)	N2—C8—C13—C12	−176.7 (2)
C8—N2—C7—O1	171.3 (2)	C9—C8—C13—C12	2.3 (3)
N1—N2—C8—C9	121.6 (2)	C8—C9—C10—C11	0.4 (3)
C7—N2—C8—C9	−43.7 (3)	C9—C10—C11—C12	1.0 (4)
N1—N2—C8—C13	−59.4 (2)	C10—C11—C12—C13	−0.7 (4)
S1—C1—C2—C3	−0.3 (4)	C11—C12—C13—C8	−0.9 (3)
C1—C2—C3—C4	−0.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1i	0.93	2.39	3.202 (3)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O1i	0.93	2.39	3.202 (3)	145

Symmetry code: (i) .