N′-[1-(2-Hydroxy­phen­yl)ethyl­idene]benzene­sulfonohydrazide

Tai, X.-S.; Xu, J.; Feng, Y.-M.; Liang, Z.-P.

doi:10.1107/S1600536808010970

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o904

doi:10.1107/S1600536808010970

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N′-[1-(2-Hydroxyphenyl)ethylidene]benzenesulfonohydrazide

Xi-Shi Tai,^a ^* Jun Xu,^b Yi-Min Feng ^a and Zu-Pei Liang ^a

^aDepartment of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China, and ^bWeifang Institute of Supervision and Inspection of product Quality, Weifang 261061, People's Republic of China
^*Correspondence e-mail: taixishi@lzu.edu.cn

(Received 19 April 2008; accepted 19 April 2008; online 26 April 2008)

In the title compound, C₁₄H₁₄N₂O₃S, the conformation is stabilized by an intramoleclar O—H⋯N hydrogen bond and the dihedral angle between the aromatic ring planes is 79.55 (18)°. In the crystal structure, intermolecular N—H⋯O hydrogen bonds lead to [100] chains of molecules.

Related literature

For related literature, see: Tai et al. (2003 ).

Experimental

Crystal data

C₁₄H₁₄N₂O₃S
M_r = 290.33
Monoclinic, P 2₁ /n
a = 5.2435 (9) Å
b = 13.2515 (18) Å
c = 20.375 (2) Å
β = 90.531 (2)°
V = 1415.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 298 (2) K
0.50 × 0.40 × 0.37 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.891, T_max = 0.918
7165 measured reflections
2484 independent reflections
1755 reflections with I > 2σ(I)
R_int = 0.062

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.131
S = 1.04
2484 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N2	0.82	1.85	2.561 (3)	145
N1—H1⋯O2ⁱ	0.90	2.20	3.093 (3)	174
Symmetry code: (i) x+1, y, z.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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/S1600536808010970/hb2723sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808010970/hb2723Isup2.hkl

checkCIF report

Comment top

As part of our ongoing studies of the coordination chemistry of aroylhydrazones as potential ligands (Tai et al., 2003), we now report the synthesis and structure of the title compound, (I), (Fig. 1).

The molecular conformation is stabilised by an intramoleclar O-H···N hydrogen bond (Table 1) and the dihedral angle between the aromatic ring planes is 79.55 (18)°. In the crystal, an intermolecular N-H···O hydrogen bond lead to [100] chains of molecules.

Related literature top

For related literature, see: Tai et al. (2003).

Experimental top

3 mmol of 2'-hydroxyacetophenone (3 mmol) was added to a solution of benzenesulfonyl hydrazide (3 mmol) in 10 ml of 95% ethanol. The mixture was continuously stirred for 3 h at refluxing temperature, evaporating some ethanol, then, upon cooling, the solid product was collected by filtration and dried in vacuo (yield 68%). Colourless blocks of (I) were obtained by evaporation from a methanol solution after 3 days.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 (I) showing 40% displacement ellipsoids (arbitrary spheres for the H atoms). The hydrogen bond is indicated by a double-dashed line.

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

Crystal data top

C₁₄H₁₄N₂O₃S	F(000) = 608
M_r = 290.33	D_x = 1.362 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2187 reflections
a = 5.2435 (9) Å	θ = 2.5–26.2°
b = 13.2515 (18) Å	µ = 0.24 mm⁻¹
c = 20.375 (2) Å	T = 298 K
β = 90.531 (2)°	Block, colourless
V = 1415.7 (3) Å³	0.50 × 0.40 × 0.37 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	2484 independent reflections
Radiation source: fine-focus sealed tube	1755 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.062
ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −6→6
T_min = 0.891, T_max = 0.918	k = −15→15
7165 measured reflections	l = −20→24

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.047	H-atom parameters constrained
wR(F²) = 0.131	w = 1/[σ²(F_o²) + (0.0428P)² + 0.8643P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
2484 reflections	Δρ_max = 0.26 e Å⁻³
182 parameters	Δρ_min = −0.26 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.018 (2)

Crystal data top

C₁₄H₁₄N₂O₃S	V = 1415.7 (3) Å³
M_r = 290.33	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.2435 (9) Å	µ = 0.24 mm⁻¹
b = 13.2515 (18) Å	T = 298 K
c = 20.375 (2) Å	0.50 × 0.40 × 0.37 mm
β = 90.531 (2)°

Data collection top

Bruker SMART CCD diffractometer	2484 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1755 reflections with I > 2σ(I)
T_min = 0.891, T_max = 0.918	R_int = 0.062
7165 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.131	H-atom parameters constrained
S = 1.04	Δρ_max = 0.26 e Å⁻³
2484 reflections	Δρ_min = −0.26 e Å⁻³
182 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
N1	0.3921 (4)	0.13317 (15)	0.94596 (10)	0.0397 (6)
H1	0.5569	0.1345	0.9587	0.048*
N2	0.3516 (4)	0.21056 (16)	0.90070 (10)	0.0378 (5)
O1	0.2888 (4)	0.06000 (14)	1.05125 (9)	0.0589 (6)
O2	−0.0427 (4)	0.15363 (16)	0.98874 (10)	0.0560 (6)
O3	0.0643 (4)	0.35673 (15)	0.86405 (10)	0.0590 (6)
H3	0.1123	0.3112	0.8884	0.089*
S1	0.21361 (14)	0.14329 (5)	1.01133 (3)	0.0403 (3)
C1	0.2935 (5)	0.2560 (2)	1.05229 (13)	0.0414 (7)
C2	0.1465 (7)	0.3404 (2)	1.04223 (18)	0.0659 (10)
H2	0.0090	0.3388	1.0131	0.079*
C3	0.2063 (10)	0.4282 (3)	1.0763 (2)	0.0931 (14)
H3A	0.1108	0.4864	1.0694	0.112*
C4	0.4057 (10)	0.4288 (4)	1.1200 (3)	0.1013 (16)
H4	0.4428	0.4871	1.1436	0.122*
C5	0.5504 (8)	0.3446 (4)	1.1293 (2)	0.0922 (14)
H5	0.6876	0.3463	1.1586	0.111*
C6	0.4952 (6)	0.2567 (3)	1.09574 (17)	0.0651 (9)
H6	0.5928	0.1990	1.1024	0.078*
C7	0.6988 (6)	0.1407 (2)	0.83455 (14)	0.0472 (7)
H7A	0.8593	0.1693	0.8479	0.071*
H7B	0.7018	0.1265	0.7884	0.071*
H7C	0.6699	0.0793	0.8584	0.071*
C8	0.4892 (5)	0.21397 (19)	0.84856 (12)	0.0357 (6)
C9	0.4232 (5)	0.29502 (19)	0.80152 (12)	0.0381 (6)
C10	0.2176 (5)	0.3608 (2)	0.81077 (13)	0.0421 (7)
C11	0.1611 (6)	0.4351 (2)	0.76493 (15)	0.0553 (8)
H11	0.0230	0.4779	0.7716	0.066*
C12	0.3072 (7)	0.4462 (3)	0.70987 (16)	0.0619 (9)
H12	0.2675	0.4960	0.6793	0.074*
C13	0.5109 (7)	0.3840 (3)	0.70007 (15)	0.0631 (9)
H13	0.6118	0.3920	0.6631	0.076*
C14	0.5665 (6)	0.3096 (2)	0.74492 (14)	0.0524 (8)
H14	0.7047	0.2673	0.7373	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0424 (14)	0.0379 (12)	0.0388 (12)	0.0084 (10)	0.0018 (10)	0.0056 (10)
N2	0.0423 (13)	0.0336 (12)	0.0374 (12)	0.0046 (10)	−0.0001 (10)	0.0029 (10)
O1	0.0933 (17)	0.0375 (11)	0.0461 (12)	0.0088 (11)	0.0154 (11)	0.0074 (9)
O2	0.0413 (13)	0.0634 (14)	0.0636 (13)	−0.0068 (10)	0.0049 (10)	−0.0136 (11)
O3	0.0633 (15)	0.0536 (13)	0.0605 (13)	0.0217 (11)	0.0148 (11)	0.0146 (10)
S1	0.0473 (5)	0.0335 (4)	0.0402 (4)	0.0002 (3)	0.0065 (3)	−0.0006 (3)
C1	0.0423 (17)	0.0383 (15)	0.0436 (16)	−0.0023 (12)	0.0051 (13)	−0.0047 (12)
C2	0.081 (3)	0.0445 (19)	0.073 (2)	0.0108 (17)	−0.0073 (19)	−0.0115 (16)
C3	0.123 (4)	0.046 (2)	0.111 (3)	0.009 (2)	0.011 (3)	−0.022 (2)
C4	0.102 (4)	0.084 (3)	0.118 (4)	−0.034 (3)	0.012 (3)	−0.050 (3)
C5	0.069 (3)	0.114 (4)	0.094 (3)	−0.019 (3)	−0.012 (2)	−0.045 (3)
C6	0.048 (2)	0.074 (2)	0.073 (2)	0.0026 (17)	−0.0069 (18)	−0.0137 (18)
C7	0.0505 (19)	0.0457 (16)	0.0457 (16)	0.0071 (14)	0.0069 (14)	−0.0027 (13)
C8	0.0362 (15)	0.0342 (14)	0.0366 (14)	−0.0051 (12)	−0.0013 (12)	−0.0055 (11)
C9	0.0418 (17)	0.0361 (14)	0.0363 (14)	−0.0049 (12)	−0.0048 (12)	−0.0004 (11)
C10	0.0421 (17)	0.0400 (15)	0.0442 (16)	−0.0037 (13)	−0.0021 (13)	0.0025 (13)
C11	0.056 (2)	0.0466 (18)	0.063 (2)	0.0022 (15)	−0.0082 (16)	0.0154 (15)
C12	0.071 (2)	0.059 (2)	0.055 (2)	−0.0072 (18)	−0.0139 (18)	0.0214 (16)
C13	0.076 (3)	0.069 (2)	0.0450 (18)	−0.0073 (19)	0.0049 (17)	0.0140 (16)
C14	0.056 (2)	0.0562 (19)	0.0448 (17)	0.0011 (15)	0.0025 (15)	0.0065 (14)

Geometric parameters (Å, º) top

N1—N2	1.394 (3)	C5—H5	0.9300
N1—S1	1.641 (2)	C6—H6	0.9300
N1—H1	0.9000	C7—C8	1.496 (4)
N2—C8	1.291 (3)	C7—H7A	0.9600
O1—S1	1.4246 (19)	C7—H7B	0.9600
O2—S1	1.423 (2)	C7—H7C	0.9600
O3—C10	1.358 (3)	C8—C9	1.478 (4)
O3—H3	0.8200	C9—C14	1.395 (4)
S1—C1	1.760 (3)	C9—C10	1.401 (4)
C1—C2	1.372 (4)	C10—C11	1.387 (4)
C1—C6	1.373 (4)	C11—C12	1.372 (4)
C2—C3	1.390 (5)	C11—H11	0.9300
C2—H2	0.9300	C12—C13	1.366 (5)
C3—C4	1.367 (6)	C12—H12	0.9300
C3—H3A	0.9300	C13—C14	1.374 (4)
C4—C5	1.361 (6)	C13—H13	0.9300
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.380 (5)

N2—N1—S1	113.09 (16)	C5—C6—H6	120.6
N2—N1—H1	108.5	C8—C7—H7A	109.5
S1—N1—H1	108.5	C8—C7—H7B	109.5
C8—N2—N1	119.2 (2)	H7A—C7—H7B	109.5
C10—O3—H3	109.5	C8—C7—H7C	109.5
O2—S1—O1	120.99 (14)	H7A—C7—H7C	109.5
O2—S1—N1	106.82 (12)	H7B—C7—H7C	109.5
O1—S1—N1	104.08 (11)	N2—C8—C9	115.5 (2)
O2—S1—C1	106.95 (13)	N2—C8—C7	123.5 (2)
O1—S1—C1	108.88 (13)	C9—C8—C7	121.0 (2)
N1—S1—C1	108.63 (12)	C14—C9—C10	116.5 (2)
C2—C1—C6	121.3 (3)	C14—C9—C8	120.8 (2)
C2—C1—S1	119.3 (2)	C10—C9—C8	122.7 (2)
C6—C1—S1	119.3 (2)	O3—C10—C11	116.3 (3)
C1—C2—C3	118.9 (4)	O3—C10—C9	123.0 (2)
C1—C2—H2	120.5	C11—C10—C9	120.7 (3)
C3—C2—H2	120.5	C12—C11—C10	120.6 (3)
C4—C3—C2	119.9 (4)	C12—C11—H11	119.7
C4—C3—H3A	120.1	C10—C11—H11	119.7
C2—C3—H3A	120.1	C13—C12—C11	119.9 (3)
C5—C4—C3	120.5 (4)	C13—C12—H12	120.1
C5—C4—H4	119.7	C11—C12—H12	120.1
C3—C4—H4	119.7	C12—C13—C14	119.8 (3)
C4—C5—C6	120.6 (4)	C12—C13—H13	120.1
C4—C5—H5	119.7	C14—C13—H13	120.1
C6—C5—H5	119.7	C13—C14—C9	122.4 (3)
C1—C6—C5	118.8 (4)	C13—C14—H14	118.8
C1—C6—H6	120.6	C9—C14—H14	118.8

S1—N1—N2—C8	176.68 (19)	N1—N2—C8—C9	176.6 (2)
N2—N1—S1—O2	52.5 (2)	N1—N2—C8—C7	−2.1 (4)
N2—N1—S1—O1	−178.43 (18)	N2—C8—C9—C14	176.8 (2)
N2—N1—S1—C1	−62.5 (2)	C7—C8—C9—C14	−4.5 (4)
O2—S1—C1—C2	−17.1 (3)	N2—C8—C9—C10	−3.1 (4)
O1—S1—C1—C2	−149.4 (3)	C7—C8—C9—C10	175.6 (3)
N1—S1—C1—C2	97.9 (3)	C14—C9—C10—O3	−178.9 (3)
O2—S1—C1—C6	160.2 (2)	C8—C9—C10—O3	1.0 (4)
O1—S1—C1—C6	27.9 (3)	C14—C9—C10—C11	0.8 (4)
N1—S1—C1—C6	−84.8 (3)	C8—C9—C10—C11	−179.3 (3)
C6—C1—C2—C3	0.8 (5)	O3—C10—C11—C12	179.1 (3)
S1—C1—C2—C3	178.0 (3)	C9—C10—C11—C12	−0.6 (5)
C1—C2—C3—C4	−1.3 (6)	C10—C11—C12—C13	−0.3 (5)
C2—C3—C4—C5	1.6 (7)	C11—C12—C13—C14	1.0 (5)
C3—C4—C5—C6	−1.3 (7)	C12—C13—C14—C9	−0.7 (5)
C2—C1—C6—C5	−0.5 (5)	C10—C9—C14—C13	−0.2 (4)
S1—C1—C6—C5	−177.7 (3)	C8—C9—C14—C13	180.0 (3)
C4—C5—C6—C1	0.7 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N2	0.82	1.85	2.561 (3)	145
N1—H1···O2ⁱ	0.90	2.20	3.093 (3)	174

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₄N₂O₃S
M_r	290.33
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	5.2435 (9), 13.2515 (18), 20.375 (2)
β (°)	90.531 (2)
V (Å³)	1415.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.50 × 0.40 × 0.37

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.891, 0.918
No. of measured, independent and observed [I > 2σ(I)] reflections	7165, 2484, 1755
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.131, 1.04
No. of reflections	2484
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.26

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), 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
O3—H3···N2	0.82	1.85	2.561 (3)	145
N1—H1···O2ⁱ	0.90	2.20	3.093 (3)	174

Symmetry code: (i) x+1, y, z.

Acknowledgements

The authors thank the National Natural Science Foundation of China (20671073), the Natural Science Foundation of Shandong (Y2007B60), and the Science and Technology Foundation of Weifang University for research grants.

References

Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tai, X.-S., Yin, X.-H., Tan, M.-Y. & Li, Y.-Z. (2003). Acta Cryst. E59, o681–o682. Web of Science CSD CrossRef IUCr Journals Google Scholar