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

Li, Y.-F.; Jiang, J.-H.; Jian, F.-F.

doi:10.1107/S1600536810021483

organic compounds

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Volume 66| Part 7| July 2010| Page o1719

doi:10.1107/S1600536810021483

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

Yu-Feng Li,^a Jin-He Jiang ^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 2 June 2010; accepted 5 June 2010; online 18 June 2010)

In the title compound, C₁₂H₁₀N₂O₂S, the dihedral angle between the benzene and thiophene rings is 23.34 (16)°. In the crystal structure, molecules are linked by N—H⋯O and O—H⋯O hydrogen bonds, forming (100) sheets.

Related literature

For background to the pharmacological properties of Schiff bases, see: Ren et al. (2002 ). For a related structure, see: Li et al. (2009 ).

Experimental

Crystal data

C₁₂H₁₀N₂O₂S
M_r = 246.28
Monoclinic, P 2₁ /c
a = 9.5622 (19) Å
b = 12.404 (3) Å
c = 9.991 (2) Å
β = 104.40 (3)°
V = 1147.8 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 293 K
0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer
10889 measured reflections
2629 independent reflections
1501 reflections with I > 2σ(I)
R_int = 0.057

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.181
S = 1.07
2629 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.38 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	2.09	2.887 (3)	154
O2—H2C⋯O1ⁱⁱ	0.82	2.10	2.913 (3)	174
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+3, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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: 10.1107/S1600536810021483/hb5483sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810021483/hb5483Isup2.hkl

checkCIF report

Comment top

Schiff bases derivatives have attracted much attention due to their pharmacological activity (Ren et al., 2002). As part of an investigation of the properties of Schiff bases functioning as ligands, we synthesized the title compound (I), and describe its structure here. The title compound contains two independent molecules in the unit. The dihedral angle between the aromatic rings is [23.33 (16)°]. In the crystal lattice, the N—H···O and O—H···O intramolecular hydrogen bonds which form the molecule structures.

Bond lengths and angles are comparable to those in a related compound (Li et al., 2009).

Related literature top

For background to the pharmacological properties of Schiff bases, see: Ren et al. (2002). For a related structure, see: Li et al. (2009).

Experimental top

A mixture of 4-methylbenzaldehyde (0.1 mol), and thiophene-2-carbohydrazide (0.1 mol) was stirred in refluxing ethanol (20 ml) for 4 h to afford the title compound (0.092 mol, yield 92%). Colourless blocks of (I) were obtained by recrystallization from ethanol at room temperature.

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-Hydroxybenzylidene)thiophene-2-carbohydrazide top

Crystal data top

C₁₂H₁₀N₂O₂S	F(000) = 512
M_r = 246.28	D_x = 1.425 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1501 reflections
a = 9.5622 (19) Å	θ = 3.1–27.5°
b = 12.404 (3) Å	µ = 0.27 mm⁻¹
c = 9.991 (2) Å	T = 293 K
β = 104.40 (3)°	Block, colorless
V = 1147.8 (4) Å³	0.22 × 0.20 × 0.18 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	1501 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.057
Graphite monochromator	θ_max = 27.5°, θ_min = 3.1°
phi and ω scans	h = −12→12
10889 measured reflections	k = −16→16
2629 independent reflections	l = −11→12

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.181	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
2629 reflections	(Δ/σ)_max < 0.001
154 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₁₂H₁₀N₂O₂S	V = 1147.8 (4) Å³
M_r = 246.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.5622 (19) Å	µ = 0.27 mm⁻¹
b = 12.404 (3) Å	T = 293 K
c = 9.991 (2) Å	0.22 × 0.20 × 0.18 mm
β = 104.40 (3)°

Data collection top

Bruker SMART CCD diffractometer	1501 reflections with I > 2σ(I)
10889 measured reflections	R_int = 0.057
2629 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.181	H-atom parameters constrained
S = 1.07	Δρ_max = 0.27 e Å⁻³
2629 reflections	Δρ_min = −0.38 e Å⁻³
154 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	0.89443 (10)	0.07271 (7)	0.19012 (8)	0.0713 (3)
N2	1.2232 (2)	0.37439 (19)	0.1118 (2)	0.0452 (6)
O1	1.1172 (2)	0.24125 (17)	0.27388 (17)	0.0548 (6)
N1	1.1217 (2)	0.29541 (19)	0.0602 (2)	0.0482 (6)
H1A	1.0911	0.2863	−0.0275	0.058*
C12	1.4377 (3)	0.5507 (2)	0.1730 (3)	0.0464 (6)
H12A	1.4518	0.4976	0.2407	0.056*
C4	0.9590 (3)	0.1566 (2)	0.0840 (2)	0.0435 (6)
C5	1.0717 (3)	0.2334 (2)	0.1475 (2)	0.0406 (6)
C7	1.3299 (3)	0.5378 (2)	0.0519 (2)	0.0430 (6)
C6	1.2339 (3)	0.4464 (2)	0.0230 (3)	0.0483 (7)
H6A	1.1759	0.4392	−0.0663	0.058*
C11	1.5235 (3)	0.6408 (2)	0.1941 (3)	0.0506 (7)
H11A	1.5936	0.6491	0.2767	0.061*
O2	1.5867 (3)	0.81085 (19)	0.1088 (2)	0.0816 (8)
H2C	1.6718	0.7957	0.1418	0.122*
C10	1.5063 (3)	0.7198 (2)	0.0930 (3)	0.0518 (7)
C8	1.3140 (3)	0.6189 (2)	−0.0471 (3)	0.0510 (7)
H8A	1.2427	0.6120	−0.1291	0.061*
C9	1.3999 (3)	0.7083 (2)	−0.0273 (3)	0.0569 (8)
H9A	1.3866	0.7613	−0.0951	0.068*
C3	0.8883 (4)	0.1398 (3)	−0.0502 (3)	0.0647 (9)
H3A	0.9077	0.1779	−0.1237	0.078*
C2	0.7834 (4)	0.0591 (3)	−0.0662 (3)	0.0756 (11)
H2B	0.7253	0.0377	−0.1512	0.091*
C1	0.7759 (4)	0.0163 (3)	0.0548 (3)	0.0765 (11)
H1B	0.7124	−0.0386	0.0632	0.092*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0791 (6)	0.0780 (6)	0.0592 (5)	−0.0243 (5)	0.0220 (4)	0.0166 (4)
N2	0.0506 (13)	0.0473 (14)	0.0398 (10)	−0.0127 (10)	0.0151 (10)	−0.0051 (9)
O1	0.0635 (13)	0.0682 (14)	0.0331 (9)	−0.0089 (10)	0.0129 (8)	0.0017 (8)
N1	0.0592 (15)	0.0545 (14)	0.0323 (10)	−0.0207 (11)	0.0138 (9)	−0.0059 (9)
C12	0.0476 (16)	0.0448 (15)	0.0466 (13)	−0.0047 (12)	0.0113 (12)	0.0066 (11)
C4	0.0461 (15)	0.0454 (15)	0.0416 (13)	−0.0069 (12)	0.0155 (11)	0.0010 (10)
C5	0.0446 (15)	0.0421 (14)	0.0374 (12)	−0.0003 (11)	0.0145 (10)	0.0003 (10)
C7	0.0485 (15)	0.0430 (15)	0.0398 (12)	−0.0050 (12)	0.0151 (11)	−0.0050 (10)
C6	0.0552 (17)	0.0510 (16)	0.0393 (13)	−0.0130 (13)	0.0129 (12)	−0.0049 (11)
C11	0.0465 (16)	0.0493 (17)	0.0514 (14)	−0.0048 (13)	0.0035 (12)	0.0062 (12)
O2	0.0694 (16)	0.0573 (15)	0.0975 (17)	−0.0248 (12)	−0.0184 (13)	0.0290 (12)
C10	0.0473 (16)	0.0409 (16)	0.0640 (17)	−0.0058 (13)	0.0078 (13)	0.0081 (12)
C8	0.0577 (18)	0.0497 (17)	0.0423 (13)	−0.0090 (14)	0.0064 (12)	0.0018 (11)
C9	0.063 (2)	0.0483 (18)	0.0543 (15)	−0.0072 (14)	0.0048 (14)	0.0120 (12)
C3	0.075 (2)	0.074 (2)	0.0457 (15)	−0.0327 (18)	0.0160 (15)	−0.0009 (14)
C2	0.079 (2)	0.085 (3)	0.0599 (18)	−0.041 (2)	0.0132 (17)	−0.0104 (16)
C1	0.073 (2)	0.071 (2)	0.088 (2)	−0.0361 (19)	0.0245 (19)	0.0017 (18)

Geometric parameters (Å, º) top

S1—C1	1.685 (4)	C6—H6A	0.9300
S1—C4	1.707 (2)	C11—C10	1.387 (4)
N2—C6	1.281 (3)	C11—H11A	0.9300
N2—N1	1.385 (3)	O2—C10	1.354 (3)
O1—C5	1.233 (3)	O2—H2C	0.8200
N1—C5	1.337 (3)	C10—C9	1.375 (4)
N1—H1A	0.8600	C8—C9	1.364 (4)
C12—C11	1.371 (4)	C8—H8A	0.9300
C12—C7	1.390 (4)	C9—H9A	0.9300
C12—H12A	0.9300	C3—C2	1.398 (4)
C4—C3	1.360 (4)	C3—H3A	0.9300
C4—C5	1.461 (4)	C2—C1	1.339 (4)
C7—C8	1.392 (4)	C2—H2B	0.9300
C7—C6	1.443 (4)	C1—H1B	0.9300

C1—S1—C4	91.70 (14)	C12—C11—H11A	119.8
C6—N2—N1	113.9 (2)	C10—C11—H11A	119.8
C5—N1—N2	119.68 (19)	C10—O2—H2C	109.5
C5—N1—H1A	120.2	O2—C10—C9	117.6 (3)
N2—N1—H1A	120.2	O2—C10—C11	122.9 (3)
C11—C12—C7	120.9 (2)	C9—C10—C11	119.5 (3)
C11—C12—H12A	119.6	C9—C8—C7	121.9 (3)
C7—C12—H12A	119.6	C9—C8—H8A	119.1
C3—C4—C5	131.4 (2)	C7—C8—H8A	119.1
C3—C4—S1	110.6 (2)	C8—C9—C10	119.9 (3)
C5—C4—S1	118.01 (18)	C8—C9—H9A	120.0
O1—C5—N1	122.0 (2)	C10—C9—H9A	120.0
O1—C5—C4	122.1 (2)	C4—C3—C2	112.9 (3)
N1—C5—C4	115.9 (2)	C4—C3—H3A	123.5
C12—C7—C8	117.5 (3)	C2—C3—H3A	123.5
C12—C7—C6	124.2 (2)	C1—C2—C3	112.3 (3)
C8—C7—C6	118.3 (2)	C1—C2—H2B	123.9
N2—C6—C7	124.5 (2)	C3—C2—H2B	123.9
N2—C6—H6A	117.8	C2—C1—S1	112.6 (3)
C7—C6—H6A	117.8	C2—C1—H1B	123.7
C12—C11—C10	120.3 (3)	S1—C1—H1B	123.7

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.86	2.09	2.887 (3)	154
O2—H2C···O1ⁱⁱ	0.82	2.10	2.913 (3)	174

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+3, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₀N₂O₂S
M_r	246.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	9.5622 (19), 12.404 (3), 9.991 (2)
β (°)	104.40 (3)
V (Å³)	1147.8 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.22 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10889, 2629, 1501
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.181, 1.07
No. of reflections	2629
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.38

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	2.09	2.887 (3)	154
O2—H2C···O1ⁱⁱ	0.82	2.10	2.913 (3)	174

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+3, y+1/2, −z+1/2.

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Li, Y.-F., Liu, H.-X. & Jian, F.-F. (2009). Acta Cryst. E65, o2959. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ren, S. J., Wang, R. B. & Komatsu, K. (2002). J. Med. Chem. 45, 410–419. Web of Science CrossRef PubMed CAS 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 66| Part 7| July 2010| Page o1719

doi:10.1107/S1600536810021483

Open

access