N′-(4-Methyl­benzyl­idene)thio­phene-2-carbohydrazide

Li, Y.-F.; Jian, F.-F.

doi:10.1107/S1600536810017976

organic compounds

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Volume 66| Part 6| June 2010| Page o1398

https://doi.org/10.1107/S1600536810017976

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N′-(4-Methylbenzylidene)thiophene-2-carbohydrazide

Yu-Feng Li ^a and Fang-Fang Jian ^b ^*

^aMicroscale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China, and ^bMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: liyufeng8111@163.com

(Received 13 May 2010; accepted 15 May 2010; online 22 May 2010)

In the title compound, C₁₃H₁₂N₂OS, 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 R₂²(8) loops.

Related literature

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

Experimental

Crystal data

C₁₃H₁₂N₂OS
M_r = 244.31
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.080
wR(F²) = 0.275
S = 1.08
2697 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.73 e Å⁻³
Δρ_min = −0.47 e Å⁻³

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) -x, -y, -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/S1600536810017976/hb5447sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810017976/hb5447Isup2.hkl

checkCIF report

Related literature top

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

Experimental top

A mixture of thiophene-2-carbohydrazide (0.10 mol) and 4-methylbenzaldehyde (0.10 mol) was stirred in refluxing ethanol (10 ml) for 4 h to afford the title compound (0.079 mol, yield 79%). Colourless blocks of (I) were obtained by recrystallization from ethanol at room temperature.

Structure description top

For a related structure, see: Li & Jian (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 structure of (I) showing 30% probability displacement ellipsoids.

N'-(4-Methylbenzylidene)thiophene-2-carbohydrazide top

Crystal data top

C₁₃H₁₂N₂OS	F(000) = 512
M_r = 244.31	D_x = 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

Data collection top

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

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)] = 0.080	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.275	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.1685P)² + 0.1567P] where P = (F_o² + 2F_c²)/3
2697 reflections	(Δ/σ)_max < 0.001
154 parameters	Δρ_max = 0.73 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₁₃H₁₂N₂OS	V = 1211.2 (4) Å³
M_r = 244.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.920 (3) Å	µ = 0.25 mm⁻¹
b = 5.3976 (11) Å	T = 293 K
c = 15.636 (3) Å	0.22 × 0.20 × 0.18 mm
β = 105.87 (3)°

Data collection top

Bruker SMART CCD diffractometer	1759 reflections with I > 2σ(I)
10416 measured reflections	R_int = 0.051
2697 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.080	0 restraints
wR(F²) = 0.275	H-atom parameters constrained
S = 1.08	Δρ_max = 0.73 e Å⁻³
2697 reflections	Δρ_min = −0.47 e Å⁻³
154 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₂N₂OS
M_r	244.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	14.920 (3), 5.3976 (11), 15.636 (3)
β (°)	105.87 (3)
V (Å³)	1211.2 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
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	10416, 2697, 1759
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.080, 0.275, 1.08
No. of reflections	2697
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.73, −0.47

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
N2—H2A···O1ⁱ	0.86	2.07	2.919 (4)	170

Symmetry code: (i) −x, −y, −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, o1397. 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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 6| June 2010| Page o1398

https://doi.org/10.1107/S1600536810017976

Open

access