N′-Benzyl­idene­thio­phene-2-carbohydrazide

Jiang, J.-H.

doi:10.1107/S1600536810050154

organic compounds

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https://doi.org/10.1107/S1600536810050154

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N′-Benzylidenethiophene-2-carbohydrazide

Jin-He Jiang ^a ^*

^aMicroscale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: weifangjjh@126.com

(Received 23 November 2010; accepted 1 December 2010; online 8 December 2010)

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 R₂²(8) loops.

Related literature

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

Experimental

Crystal data

C₁₂H₁₀N₂OS
M_r = 230.28
Monoclinic, C 2/c
a = 22.509 (5) Å
b = 5.3202 (11) Å
c = 20.855 (4) Å
β = 114.43 (3)°
V = 2273.8 (8) Å³
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[F² > 2σ(F²)] = 0.092
wR(F²) = 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

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) -x, -y+2, -z+1.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810050154/hb5756sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810050154/hb5756Isup2.hkl

checkCIF report

Related literature top

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

Experimental top

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.

Structure description top

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

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The moleculkar structure of the title compound showing 50% probability displacement ellipsoids.

N'-Benzylidenethiophene-2-carbohydrazide top

Crystal data top

C₁₂H₁₀N₂OS	F(000) = 960
M_r = 230.28	D_x = 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 top

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

Refinement top

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(F_o²) + (0.2P)²] where P = (F_o² + 2F_c²)/3
2115 reflections	(Δ/σ)_max < 0.001
145 parameters	Δρ_max = 0.89 e Å⁻³
3 restraints	Δρ_min = −0.58 e Å⁻³

Crystal data top

C₁₂H₁₀N₂OS	V = 2273.8 (8) Å³
M_r = 230.28	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 22.509 (5) Å	µ = 0.26 mm⁻¹
b = 5.3202 (11) Å	T = 293 K
c = 20.855 (4) Å	0.22 × 0.20 × 0.18 mm
β = 114.43 (3)°

Data collection top

Bruker SMART CCD diffractometer	1193 reflections with I > 2σ(I)
8661 measured reflections	R_int = 0.073
2115 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.092	3 restraints
wR(F²) = 0.328	H-atom parameters constrained
S = 1.11	Δρ_max = 0.89 e Å⁻³
2115 reflections	Δρ_min = −0.58 e Å⁻³
145 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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, º) top

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, º) top

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) −x, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₀N₂OS
M_r	230.28
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	22.509 (5), 5.3202 (11), 20.855 (4)
β (°)	114.43 (3)
V (Å³)	2273.8 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.22 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8661, 2115, 1193
R_int	0.073
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.092, 0.328, 1.11
No. of reflections	2115
No. of parameters	145
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.89, −0.58

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x, −y+2, −z+1.

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Li, Y.-F. & Jian, F.-F. (2010). Acta Cryst. E66, o1399. Web of Science CSD CrossRef IUCr Journals Google Scholar
Li, Y.-F. & Meng, F.-Y. (2010). Acta Cryst. E66, o2685. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 1| January 2011| Page o50

https://doi.org/10.1107/S1600536810050154

Open

access