N′-[1-(2-Hy­droxy­phen­yl)ethyl­idene]thio­phene-2-carbohydrazide

Jiang, J.-H.

doi:10.1107/S1600536810050002

organic compounds

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Volume 67| Part 1| January 2011| Page o32

https://doi.org/10.1107/S1600536810050002

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N′-[1-(2-Hydroxyphenyl)ethylidene]thiophene-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 19 November 2010; accepted 30 November 2010; online 4 December 2010)

The title compound, C₁₃H₁₂N₂O₂S, was prepared by the reaction of 1-(2-hydroxyphenyl)ethanone and thiophene-2-carbohydrazide. The dihedral angle between the benzene and thiophene rings is 10.07 (17)°. An intramolecular O—H⋯N hydrogen bond may influence the molecular conformation. In the crystal, molecules are linked by N—H⋯O hydrogen bonds into chains along [010].

Related literature

For applications of Schiff base compounds, see: Casas et al. (2000 ); Habermehl et al. (2006 ). For related structures, see: Li & Jian (2010 ); Li & Meng (2010 ).

Experimental

Crystal data

C₁₃H₁₂N₂O₂S
M_r = 260.31
Orthorhombic, P b c a
a = 13.454 (3) Å
b = 7.6303 (15) Å
c = 24.305 (5) Å
V = 2495.1 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 293 K
0.25 × 0.20 × 0.19 mm

Data collection

Bruker SMART CCD diffractometer
16044 measured reflections
2189 independent reflections
1047 reflections with I > 2σ(I)
R_int = 0.156

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.126
S = 0.89
2189 reflections
172 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.94 (4)	2.11 (4)	3.023 (4)	164 (3)
O2—H2O⋯N2	0.81 (4)	1.80 (4)	2.536 (4)	150 (4)
Symmetry code: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

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/S1600536810050002/lh5171sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810050002/lh5171Isup2.hkl

checkCIF report

Comment top

Schiff-base have received considerable attention as they can be utilized as effective ligands in coordination chemistry. (Casas et al., 2000). They are important intermediates which have been reported to be chiral coordination compounds with many interesting properties (Habermehl et al., 2006). As part of our search for new schiff-base compounds we synthesized the title compound (I), and its crystal structure is determined herein.

The molecular structure of the title compound is shown in Fig. 1. In the molecule, the dihedral angle between the benzene ring and the thiophene ring is 10.07 (17)°. In the crystal structure, molecules are linked by the N—H···O hydrogen bonds to form one-dimensional chains along [010]. Bond lengths and angles agree with those common to related structures (Li & Jian, 2010a,b).

Related literature top

For applications of Schiff base compounds, see: Casas et al. (2000); Habermehl et al. (2006). For related structures, see: Li & Jian (2010); Li & Meng (2010).

Experimental top

A mixture of 1-(2-hydroxyphenyl)ethanone (0.01 mol) and thiophene-2-carbohydrazide (0.01 mol) was stirred in refluxing ethanol (20 mL) for 2 h to afford the title compound (0.092 mol, yield 92%). Single crystals suitable for X-ray measurements were obtained by recrystallization of the title compound from ethanol at room temperature.

Structure description top

For applications of Schiff base compounds, see: Casas et al. (2000); Habermehl et al. (2006). 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 molecular structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme.

N'-[1-(2-Hydroxyphenyl)ethylidene]thiophene-2-carbohydrazide top

Crystal data top

C₁₃H₁₂N₂O₂S	F(000) = 1088
M_r = 260.31	D_x = 1.386 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2839 reflections
a = 13.454 (3) Å	θ = 3.0–27.5°
b = 7.6303 (15) Å	µ = 0.25 mm⁻¹
c = 24.305 (5) Å	T = 293 K
V = 2495.1 (9) Å³	Block, colorless
Z = 8	0.25 × 0.20 × 0.19 mm

Data collection top

Bruker SMART CCD diffractometer	1047 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.156
Graphite monochromator	θ_max = 25.0°, θ_min = 3.0°
φ and ω scans	h = −16→14
16044 measured reflections	k = −9→9
2189 independent reflections	l = −28→28

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 0.89	w = 1/[σ²(F_o²) + (0.0573P)²] where P = (F_o² + 2F_c²)/3
2189 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₃H₁₂N₂O₂S	V = 2495.1 (9) Å³
M_r = 260.31	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 13.454 (3) Å	µ = 0.25 mm⁻¹
b = 7.6303 (15) Å	T = 293 K
c = 24.305 (5) Å	0.25 × 0.20 × 0.19 mm

Data collection top

Bruker SMART CCD diffractometer	1047 reflections with I > 2σ(I)
16044 measured reflections	R_int = 0.156
2189 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 0.89	Δρ_max = 0.23 e Å⁻³
2189 reflections	Δρ_min = −0.29 e Å⁻³
172 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	0.44225 (8)	0.02138 (15)	0.75337 (5)	0.0783 (4)
O1	0.37088 (16)	0.2689 (3)	0.84114 (10)	0.0546 (7)
O2	0.31584 (19)	0.3541 (4)	0.98652 (13)	0.0591 (8)
N1	0.2282 (2)	0.1203 (4)	0.85835 (12)	0.0498 (8)
N2	0.2212 (2)	0.2088 (4)	0.90867 (12)	0.0491 (8)
C1	0.3999 (3)	−0.1057 (5)	0.70050 (16)	0.0698 (12)
H1	0.4408	−0.1542	0.6737	0.084*
C2	0.3020 (3)	−0.1273 (4)	0.70204 (15)	0.0562 (10)
H2A	0.2668	−0.1921	0.6761	0.067*
C3	0.2570 (3)	−0.0416 (4)	0.74723 (16)	0.0502 (9)
H3A	0.1891	−0.0430	0.7543	0.060*
C4	0.3251 (2)	0.0437 (4)	0.77919 (15)	0.0457 (9)
C5	0.3114 (3)	0.1538 (5)	0.82858 (14)	0.0462 (9)
C6	0.1375 (2)	0.2103 (4)	0.93416 (15)	0.0453 (9)
C7	0.0439 (2)	0.1341 (5)	0.91119 (16)	0.0632 (11)
H7A	0.0469	0.1355	0.8717	0.095*
H7B	−0.0119	0.2024	0.9233	0.095*
H7C	0.0366	0.0156	0.9238	0.095*
C8	0.1386 (2)	0.2934 (4)	0.98860 (14)	0.0421 (9)
C9	0.0523 (3)	0.3054 (4)	1.02020 (16)	0.0541 (10)
H9A	−0.0066	0.2609	1.0059	0.065*
C10	0.0510 (3)	0.3801 (5)	1.07136 (16)	0.0626 (11)
H10A	−0.0080	0.3859	1.0912	0.075*
C11	0.1374 (3)	0.4465 (5)	1.09333 (16)	0.0603 (11)
H11A	0.1368	0.4981	1.1280	0.072*
C12	0.2244 (3)	0.4366 (5)	1.06408 (16)	0.0571 (10)
H12A	0.2827	0.4812	1.0791	0.069*
C13	0.2261 (3)	0.3603 (4)	1.01196 (15)	0.0456 (9)
H1N	0.186 (3)	0.023 (5)	0.8545 (16)	0.082 (13)*
H2O	0.305 (3)	0.315 (6)	0.9561 (19)	0.094 (19)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0552 (6)	0.0905 (8)	0.0893 (9)	−0.0020 (6)	0.0197 (6)	−0.0246 (7)
O1	0.0464 (15)	0.0593 (15)	0.0581 (17)	−0.0070 (12)	−0.0021 (12)	−0.0067 (13)
O2	0.0448 (16)	0.0713 (19)	0.061 (2)	−0.0090 (13)	0.0029 (15)	−0.0080 (16)
N1	0.0521 (19)	0.0515 (19)	0.046 (2)	−0.0051 (16)	0.0061 (15)	−0.0075 (17)
N2	0.0530 (19)	0.0485 (18)	0.046 (2)	−0.0035 (14)	0.0054 (15)	−0.0057 (16)
C1	0.085 (3)	0.063 (3)	0.061 (3)	0.003 (2)	0.019 (2)	−0.013 (2)
C2	0.074 (3)	0.044 (2)	0.051 (3)	0.006 (2)	0.004 (2)	−0.0002 (19)
C3	0.053 (2)	0.045 (2)	0.053 (2)	0.0025 (17)	0.008 (2)	0.004 (2)
C4	0.045 (2)	0.046 (2)	0.046 (2)	0.0064 (16)	0.0065 (17)	0.0029 (18)
C5	0.044 (2)	0.049 (2)	0.046 (2)	0.0054 (18)	−0.0015 (18)	0.0014 (19)
C6	0.042 (2)	0.045 (2)	0.050 (2)	−0.0035 (16)	−0.0012 (18)	0.0007 (18)
C7	0.054 (2)	0.068 (3)	0.068 (3)	−0.001 (2)	−0.003 (2)	−0.019 (2)
C8	0.043 (2)	0.044 (2)	0.038 (2)	−0.0019 (15)	0.0009 (17)	0.0021 (17)
C9	0.048 (2)	0.059 (3)	0.055 (3)	−0.0081 (18)	0.007 (2)	0.000 (2)
C10	0.062 (3)	0.075 (3)	0.051 (3)	0.000 (2)	0.015 (2)	0.005 (2)
C11	0.076 (3)	0.065 (3)	0.040 (2)	0.003 (2)	0.008 (2)	0.000 (2)
C12	0.062 (3)	0.056 (2)	0.053 (3)	−0.0039 (19)	−0.004 (2)	0.000 (2)
C13	0.047 (2)	0.041 (2)	0.049 (2)	0.0011 (17)	0.0033 (18)	0.0015 (19)

Geometric parameters (Å, º) top

S1—C4	1.705 (3)	C6—C8	1.467 (5)
S1—C1	1.708 (4)	C6—C7	1.495 (4)
O1—C5	1.227 (4)	C7—H7A	0.9600
O2—C13	1.357 (4)	C7—H7B	0.9600
O2—H2O	0.81 (4)	C7—H7C	0.9600
N1—C5	1.356 (4)	C8—C9	1.395 (4)
N1—N2	1.400 (4)	C8—C13	1.402 (4)
N1—H1N	0.94 (4)	C9—C10	1.368 (5)
N2—C6	1.285 (4)	C9—H9A	0.9300
C1—C2	1.327 (5)	C10—C11	1.377 (5)
C1—H1	0.9300	C10—H10A	0.9300
C2—C3	1.415 (5)	C11—C12	1.371 (5)
C2—H2A	0.9300	C11—H11A	0.9300
C3—C4	1.366 (5)	C12—C13	1.395 (5)
C3—H3A	0.9300	C12—H12A	0.9300
C4—C5	1.477 (5)

C4—S1—C1	91.4 (2)	C6—C7—H7A	109.5
C13—O2—H2O	105 (3)	C6—C7—H7B	109.5
C5—N1—N2	115.5 (3)	H7A—C7—H7B	109.5
C5—N1—H1N	126 (2)	C6—C7—H7C	109.5
N2—N1—H1N	115 (2)	H7A—C7—H7C	109.5
C6—N2—N1	119.0 (3)	H7B—C7—H7C	109.5
C2—C1—S1	112.4 (3)	C9—C8—C13	116.8 (3)
C2—C1—H1	123.8	C9—C8—C6	121.1 (3)
S1—C1—H1	123.8	C13—C8—C6	122.1 (3)
C1—C2—C3	112.9 (4)	C10—C9—C8	122.6 (4)
C1—C2—H2A	123.6	C10—C9—H9A	118.7
C3—C2—H2A	123.6	C8—C9—H9A	118.7
C4—C3—C2	112.0 (3)	C9—C10—C11	119.7 (4)
C4—C3—H3A	124.0	C9—C10—H10A	120.2
C2—C3—H3A	124.0	C11—C10—H10A	120.2
C3—C4—C5	130.5 (3)	C12—C11—C10	120.0 (4)
C3—C4—S1	111.3 (3)	C12—C11—H11A	120.0
C5—C4—S1	118.1 (3)	C10—C11—H11A	120.0
O1—C5—N1	122.7 (3)	C11—C12—C13	120.5 (4)
O1—C5—C4	121.9 (3)	C11—C12—H12A	119.8
N1—C5—C4	115.4 (3)	C13—C12—H12A	119.8
N2—C6—C8	115.4 (3)	O2—C13—C12	116.3 (3)
N2—C6—C7	123.7 (3)	O2—C13—C8	123.3 (3)
C8—C6—C7	120.9 (3)	C12—C13—C8	120.4 (3)

C5—N1—N2—C6	167.0 (3)	N2—C6—C8—C9	179.2 (3)
C4—S1—C1—C2	0.9 (3)	C7—C6—C8—C9	−0.7 (5)
S1—C1—C2—C3	−0.5 (4)	N2—C6—C8—C13	−2.3 (5)
C1—C2—C3—C4	−0.3 (5)	C7—C6—C8—C13	177.7 (3)
C2—C3—C4—C5	177.6 (3)	C13—C8—C9—C10	0.7 (5)
C2—C3—C4—S1	1.0 (4)	C6—C8—C9—C10	179.2 (3)
C1—S1—C4—C3	−1.1 (3)	C8—C9—C10—C11	−0.1 (6)
C1—S1—C4—C5	−178.1 (3)	C9—C10—C11—C12	−0.4 (6)
N2—N1—C5—O1	−8.5 (5)	C10—C11—C12—C13	0.3 (6)
N2—N1—C5—C4	172.4 (3)	C11—C12—C13—O2	−179.1 (3)
C3—C4—C5—O1	−153.3 (4)	C11—C12—C13—C8	0.4 (5)
S1—C4—C5—O1	23.1 (4)	C9—C8—C13—O2	178.5 (3)
C3—C4—C5—N1	25.8 (5)	C6—C8—C13—O2	0.1 (5)
S1—C4—C5—N1	−157.8 (3)	C9—C8—C13—C12	−0.8 (5)
N1—N2—C6—C8	175.2 (3)	C6—C8—C13—C12	−179.3 (3)
N1—N2—C6—C7	−4.8 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.94 (4)	2.11 (4)	3.023 (4)	164 (3)
O2—H2O···N2	0.81 (4)	1.80 (4)	2.536 (4)	150 (4)

Symmetry code: (i) −x+1/2, y−1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₂N₂O₂S
M_r	260.31
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	13.454 (3), 7.6303 (15), 24.305 (5)
V (Å³)	2495.1 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.25 × 0.20 × 0.19

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	16044, 2189, 1047
R_int	0.156
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.126, 0.89
No. of reflections	2189
No. of parameters	172
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.29

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—H1N···O1ⁱ	0.94 (4)	2.11 (4)	3.023 (4)	164 (3)
O2—H2O···N2	0.81 (4)	1.80 (4)	2.536 (4)	150 (4)

Symmetry code: (i) −x+1/2, y−1/2, z.

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Casas, J. S., Garcia-T, M. S. & Sordo, J. (2000). Coord. Chem. Rev. 209, 197–261. Web of Science CrossRef CAS Google Scholar
Habermehl, N. C., Angus, P. M. & Kilah, N. L. (2006). Inorg. Chem. 45, 1445–1462. Web of Science CSD CrossRef PubMed CAS 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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https://doi.org/10.1107/S1600536810050002

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