N′-Benzyl­idene­thio­phene-2-carbohydrazide

Abstract

In the title compound, C₁₂H₁₀N₂OS, the dihedral angle between the phenyl and thio­phene rings is 10.2 (3)°. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R ₂ ²(8) loops.

Related literature

For related structures, see: Li & Jian (2010 ▶); Li & Meng (2010 ▶).

Experimental

Crystal data

• C₁₂H₁₀N₂OS

• M _r = 230.28

• Monoclinic,

• a = 22.509 (5) Å

• b = 5.3202 (11) Å

• c = 20.855 (4) Å

• β = 114.43 (3)°

• V = 2273.8 (8) ų

• Z = 8

• Mo Kα radiation

• μ = 0.26 mm⁻¹

• T = 293 K

• 0.22 × 0.20 × 0.18 mm

Data collection

• Bruker SMART CCD diffractometer

• 8661 measured reflections

• 2115 independent reflections

• 1193 reflections with I > 2σ(I)

• R _int = 0.073

Refinement

• R[F ² > 2σ(F ²)] = 0.092

• wR(F ²) = 0.328

• S = 1.11

• 2115 reflections

• 145 parameters

• 3 restraints

• H-atom parameters constrained

• Δρ_max = 0.89 e Å⁻³

• Δρ_min = −0.58 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.

Supplementary Material

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.86	2.04	2.902 (6)	176

Symmetry code: (i) .

supplementary crystallographic information

Experimental

A mixture of benzaldehyde (0.01 mol) and thiophene-2-carbohydrazide (0.01 mol) was stirred in refluxing ethanol (10 mL) for 2 h to afford the title compound (0.087 mol, yield 87%). Colourless blocks of the title compound were obtained by recrystallization from ethanol at room temperature.

Refinement

H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H distances=0.97 Å, and with U_iso=1.2–1.5U_eq.

Figures

Fig. 1.

The moleculkar structure of the title compound showing 50% probability displacement ellipsoids.

Crystal data

C12H10N2OS	F(000) = 960
Mr = 230.28	Dx = 1.345 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2115 reflections
a = 22.509 (5) Å	θ = 3.5–25.5°
b = 5.3202 (11) Å	µ = 0.26 mm−1
c = 20.855 (4) Å	T = 293 K
β = 114.43 (3)°	Block, colorless
V = 2273.8 (8) Å3	0.22 × 0.20 × 0.18 mm
Z = 8

Data collection

Bruker SMART CCD diffractometer	1193 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.073
graphite	θmax = 25.5°, θmin = 3.5°
phi and ω scans	h = −26→26
8661 measured reflections	k = −5→6
2115 independent reflections	l = −25→25

Refinement

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)] = 0.092	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.328	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.2P)2] where P = (Fo2 + 2Fc2)/3
2115 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.89 e Å−3
3 restraints	Δρmin = −0.58 e Å−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.01403 (9)	0.3874 (4)	0.33888 (9)	0.0815 (8)
O1	0.06062 (18)	0.7464 (8)	0.51757 (18)	0.0651 (12)
N2	−0.06627 (19)	0.7700 (9)	0.3491 (2)	0.0503 (11)
N1	−0.02647 (19)	0.8312 (9)	0.4162 (2)	0.0550 (12)
H1A	−0.0355	0.9609	0.4352	0.066*
C7	−0.1623 (2)	0.8729 (10)	0.2456 (3)	0.0506 (13)
C3	0.1091 (2)	0.3226 (8)	0.4694 (2)	0.0362 (10)
H3A	0.1359	0.3392	0.5171	0.043*
C4	0.0476 (2)	0.4805 (10)	0.4224 (3)	0.0501 (13)
C6	−0.1143 (2)	0.9153 (11)	0.3186 (3)	0.0538 (13)
H6A	−0.1195	1.0535	0.3431	0.065*
C5	0.0276 (2)	0.6919 (11)	0.4546 (3)	0.0531 (14)
C8	−0.2152 (3)	1.0319 (13)	0.2163 (3)	0.0648 (16)
H8A	−0.2186	1.1702	0.2418	0.078*
C12	−0.1576 (3)	0.6708 (12)	0.2063 (3)	0.0634 (16)
H12A	−0.1227	0.5599	0.2254	0.076*
C10	−0.2577 (3)	0.7903 (14)	0.1120 (3)	0.0783 (19)
H10A	−0.2905	0.7606	0.0674	0.094*
C11	−0.2045 (3)	0.6333 (14)	0.1390 (3)	0.0744 (18)
H11A	−0.2001	0.5019	0.1118	0.089*
C2	0.1133 (3)	0.1422 (13)	0.4185 (4)	0.0732 (17)
H2B	0.1459	0.0208	0.4316	0.088*
C9	−0.2620 (3)	0.9899 (15)	0.1510 (3)	0.081 (2)
H9A	−0.2976	1.0982	0.1325	0.097*
C1	0.0680 (3)	0.1595 (12)	0.3516 (3)	0.0683 (17)
H1B	0.0670	0.0530	0.3158	0.082*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
S1	0.0945 (14)	0.0842 (15)	0.0706 (12)	0.0052 (9)	0.0389 (10)	−0.0072 (9)
O1	0.073 (2)	0.066 (3)	0.049 (2)	−0.002 (2)	0.0184 (18)	−0.0075 (18)
N2	0.047 (2)	0.056 (3)	0.047 (2)	−0.001 (2)	0.0179 (18)	0.000 (2)
N1	0.058 (3)	0.056 (3)	0.050 (2)	0.002 (2)	0.020 (2)	−0.003 (2)
C7	0.051 (3)	0.049 (3)	0.055 (3)	−0.003 (2)	0.026 (2)	0.001 (2)
C3	0.040 (2)	0.032 (2)	0.037 (2)	−0.0048 (18)	0.0171 (18)	−0.0054 (18)
C4	0.055 (3)	0.049 (3)	0.050 (3)	−0.005 (2)	0.026 (2)	0.005 (2)
C6	0.053 (3)	0.051 (3)	0.062 (3)	−0.003 (2)	0.029 (2)	−0.005 (3)
C5	0.055 (3)	0.054 (3)	0.055 (3)	−0.009 (2)	0.026 (2)	−0.001 (2)
C8	0.063 (3)	0.058 (4)	0.066 (4)	0.013 (3)	0.019 (3)	−0.004 (3)
C12	0.058 (3)	0.062 (4)	0.066 (3)	0.011 (3)	0.022 (3)	−0.005 (3)
C10	0.077 (4)	0.081 (5)	0.062 (4)	0.000 (4)	0.014 (3)	0.000 (3)
C11	0.076 (4)	0.070 (4)	0.069 (4)	0.003 (3)	0.022 (3)	−0.011 (3)
C2	0.064 (4)	0.067 (4)	0.091 (4)	0.008 (3)	0.034 (3)	0.013 (3)
C9	0.075 (4)	0.086 (5)	0.068 (4)	0.026 (4)	0.017 (3)	0.013 (4)
C1	0.074 (4)	0.069 (4)	0.073 (4)	0.005 (3)	0.042 (3)	−0.011 (3)

Geometric parameters (Å, °)

S1—C1	1.658 (6)	C6—H6A	0.9300
S1—C4	1.662 (5)	C8—C9	1.352 (8)
O1—C5	1.246 (6)	C8—H8A	0.9300
N2—C6	1.265 (7)	C12—C11	1.378 (8)
N2—N1	1.354 (5)	C12—H12A	0.9300
N1—C5	1.366 (7)	C10—C9	1.366 (10)
N1—H1A	0.8600	C10—C11	1.376 (9)
C7—C8	1.380 (7)	C10—H10A	0.9300
C7—C12	1.382 (8)	C11—H11A	0.9300
C7—C6	1.475 (7)	C2—C1	1.348 (8)
C3—C2	1.463 (8)	C2—H2B	0.9300
C3—C4	1.569 (7)	C9—H9A	0.9300
C3—H3A	0.9300	C1—H1B	0.9300
C4—C5	1.472 (8)
C1—S1—C4	93.7 (3)	C9—C8—H8A	119.5
C6—N2—N1	115.8 (5)	C7—C8—H8A	119.5
N2—N1—C5	121.6 (5)	C11—C12—C7	120.2 (5)
N2—N1—H1A	119.2	C11—C12—H12A	119.9
C5—N1—H1A	119.2	C7—C12—H12A	119.9
C8—C7—C12	118.5 (5)	C9—C10—C11	119.5 (6)
C8—C7—C6	119.6 (5)	C9—C10—H10A	120.2
C12—C7—C6	121.9 (5)	C11—C10—H10A	120.2
C2—C3—C4	101.8 (4)	C10—C11—C12	120.0 (6)
C2—C3—H3A	129.1	C10—C11—H11A	120.0
C4—C3—H3A	129.1	C12—C11—H11A	120.0
C5—C4—C3	118.8 (4)	C1—C2—C3	117.2 (5)
C5—C4—S1	127.9 (4)	C1—C2—H2B	121.4
C3—C4—S1	113.3 (4)	C3—C2—H2B	121.4
N2—C6—C7	122.2 (5)	C8—C9—C10	120.7 (6)
N2—C6—H6A	118.9	C8—C9—H9A	119.7
C7—C6—H6A	118.9	C10—C9—H9A	119.7
O1—C5—N1	119.3 (5)	C2—C1—S1	114.0 (5)
O1—C5—C4	119.8 (5)	C2—C1—H1B	123.0
N1—C5—C4	120.8 (5)	S1—C1—H1B	123.0
C9—C8—C7	121.1 (6)

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.86	2.04	2.902 (6)	176

Symmetry codes: (i) −x, −y+2, −z+1.