N′-(2-Hydr­oxy-5-nitro­benzyl­idene)benzene­sulfonohydrazide

Yusnita, J.; Ali, H.M.; Puvaneswary, S.; Robinson, W.T.; Ng, S.W.

doi:10.1107/S1600536808022691

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1583

doi:10.1107/S1600536808022691

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N′-(2-Hydroxy-5-nitrobenzylidene)benzenesulfonohydrazide

Juahir Yusnita,^a Hapipah M. Ali,^a Subramaniam Puvaneswary,^a Ward T. Robinson ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 10 July 2008; accepted 19 July 2008; online 23 July 2008)

The molecule of the title compound, C₁₃H₁₁N₃O₅S, shows a phenyl group and an almost planar intramolecularly hydrogen-bonded N′-(2-hydroxy-5-phenylebenzylidene)hydrazino group disposed about the S atom. Adjacent molecules are linked by N—H⋯O_nitro hydrogen bonds, producing a linear chain that runs along the b axis of the unit cell.

Related literature

For 2′-[1-(2-hydroxyphenyl)ethylidene]benzenesulfonohydrazide, see: Tai et al. (2008 ).

Experimental

Crystal data

C₁₃H₁₁N₃O₅S
M_r = 321.31
Monoclinic, P 2₁ /c
a = 7.8188 (1) Å
b = 14.5904 (2) Å
c = 11.9083 (1) Å
β = 98.159 (1)°
V = 1344.74 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 100 (2) K
0.47 × 0.40 × 0.33 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.883, T_max = 0.916
16761 measured reflections
3089 independent reflections
2972 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.088
S = 1.03
3089 reflections
243 parameters
11 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯N2	0.84 (1)	1.86 (1)	2.628 (1)	153 (2)
N3—H3n⋯O3ⁱ	0.88 (1)	2.13 (1)	2.978 (1)	163 (2)
Symmetry code: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2008 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808022691/im2077sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808022691/im2077Isup2.hkl

checkCIF report

Comment top

The molecules of benzenesulfonic acid-(2-hydroxy-5-nitro-benzylidene)-hydrazide adopt a linear chain-like structure in which the individual molecules are linked by N–H···O hydrogen bonds [3.093 (3) Å] (Tai et al., 2008). The title compound exhibits a phenyl group and an almost planar, intramolecularly hydrogen-bonded (2-hydroxy-5-phenyl)ethylidenehydrazidyl group disposed about the sulfur atom. The nitro group is situated para with respect to the OH donor site (Scheme I, Fig. 1). The nitro group also acts as an acceptor towards the amino group of an adjacent molecule to furnish a chain-like structure that runs along the b-axis of the unit cell (Fig. 2).

Related literature top

For 2'-[1-(2-hydroxyphenyl)ethylidene]benzenesulfonohydrazide, see: Tai et al. (2008).

Experimental top

2-Hydroxy-5-nitrobenzaldehyde (0.50 g, 3 mmol) and benzene sulfonylhydrazide (0.52 g, 0.3 mmol) were condensed in refluxing ethanol (100 ml) for two hours. The solvent was removed to give the Schiff base, which was collected in nearly quantative yield. and dried. Crystals were obtained by recrystallization from ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top

	Fig. 1. Thermal ellipsoid plot (Barbour, 2001) plot of C₁₃H₁₁N₃O₅S at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Hydrogen-bonded chain structure. Hydrogen bonds are denoted by dashed lines.

N'-(2-Hydroxy-5-nitrobenzylidene)benzenesulfonohydrazide top

Crystal data top

C₁₃H₁₁N₃O₅S	F(000) = 664
M_r = 321.31	D_x = 1.587 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9991 reflections
a = 7.8188 (1) Å	θ = 2.4–30.4°
b = 14.5904 (2) Å	µ = 0.27 mm⁻¹
c = 11.9083 (1) Å	T = 100 K
β = 98.159 (1)°	Triangular plate, yellow
V = 1344.74 (3) Å³	0.47 × 0.40 × 0.33 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	3089 independent reflections
Radiation source: fine-focus sealed tube	2972 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω scans	θ_max = 27.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→9
T_min = 0.883, T_max = 0.916	k = −18→18
16761 measured reflections	l = −14→15

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0521P)² + 0.7306P] where P = (F_o² + 2F_c²)/3
3089 reflections	(Δ/σ)_max = 0.001
243 parameters	Δρ_max = 0.42 e Å⁻³
11 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

C₁₃H₁₁N₃O₅S	V = 1344.74 (3) Å³
M_r = 321.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.8188 (1) Å	µ = 0.27 mm⁻¹
b = 14.5904 (2) Å	T = 100 K
c = 11.9083 (1) Å	0.47 × 0.40 × 0.33 mm
β = 98.159 (1)°

Data collection top

Bruker SMART APEX diffractometer	3089 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2972 reflections with I > 2σ(I)
T_min = 0.883, T_max = 0.916	R_int = 0.024
16761 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	11 restraints
wR(F²) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.42 e Å⁻³
3089 reflections	Δρ_min = −0.51 e Å⁻³
243 parameters

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

	x	y	z	U_iso*/U_eq
S1	0.78969 (4)	0.172790 (19)	0.37657 (2)	0.01358 (10)
N1	0.89489 (14)	0.67461 (7)	0.75588 (9)	0.0169 (2)
N2	0.82479 (13)	0.33431 (7)	0.46383 (9)	0.0149 (2)
N3	0.89849 (13)	0.24787 (7)	0.46141 (9)	0.0150 (2)
O1	0.65151 (13)	0.47538 (6)	0.36923 (8)	0.0233 (2)
O2	0.84138 (13)	0.75301 (6)	0.76435 (8)	0.0239 (2)
O3	1.00400 (12)	0.63904 (7)	0.82771 (8)	0.0224 (2)
O4	0.74085 (13)	0.21585 (7)	0.26881 (7)	0.0230 (2)
O5	0.89964 (11)	0.09391 (6)	0.38421 (8)	0.01914 (19)
C1	0.70881 (16)	0.52031 (8)	0.46569 (10)	0.0166 (2)
C2	0.66093 (17)	0.61234 (9)	0.47357 (11)	0.0202 (3)
C3	0.71928 (16)	0.66280 (8)	0.56918 (11)	0.0181 (2)
C4	0.82690 (15)	0.62056 (8)	0.65697 (10)	0.0150 (2)
C5	0.87528 (15)	0.52972 (8)	0.65268 (10)	0.0146 (2)
C6	0.81634 (15)	0.47794 (8)	0.55664 (10)	0.0143 (2)
C7	0.87482 (15)	0.38342 (8)	0.55157 (10)	0.0149 (2)
C8	0.60116 (14)	0.14633 (8)	0.43497 (10)	0.0129 (2)
C9	0.58974 (16)	0.16378 (8)	0.54832 (10)	0.0157 (2)
C10	0.44273 (17)	0.13509 (9)	0.59181 (11)	0.0208 (3)
C11	0.31115 (16)	0.08982 (9)	0.52296 (13)	0.0231 (3)
C12	0.32481 (16)	0.07308 (9)	0.41038 (13)	0.0231 (3)
C13	0.47021 (16)	0.10120 (9)	0.36497 (11)	0.0189 (2)
H1O	0.692 (3)	0.4223 (8)	0.3795 (18)	0.043 (6)*
H3N	0.944 (2)	0.2249 (12)	0.5268 (10)	0.027 (4)*
H2	0.587 (2)	0.6401 (12)	0.4127 (12)	0.028 (4)*
H3	0.691 (2)	0.7249 (7)	0.5788 (15)	0.025 (4)*
H5	0.9475 (18)	0.5022 (10)	0.7134 (11)	0.019 (4)*
H7	0.9524 (18)	0.3611 (11)	0.6142 (10)	0.019 (4)*
H9	0.6803 (17)	0.1930 (11)	0.5961 (12)	0.023 (4)*
H10	0.431 (2)	0.1463 (13)	0.6687 (9)	0.033 (5)*
H11	0.2133 (16)	0.0685 (11)	0.5530 (14)	0.026 (4)*
H12	0.2367 (19)	0.0410 (11)	0.3635 (13)	0.030 (4)*
H13	0.482 (2)	0.0875 (11)	0.2882 (9)	0.025 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01629 (16)	0.01318 (16)	0.01162 (15)	−0.00058 (9)	0.00324 (11)	−0.00033 (9)
N1	0.0174 (5)	0.0180 (5)	0.0160 (5)	−0.0050 (4)	0.0042 (4)	−0.0018 (4)
N2	0.0170 (5)	0.0106 (4)	0.0175 (5)	−0.0002 (3)	0.0038 (4)	0.0021 (3)
N3	0.0161 (5)	0.0110 (4)	0.0174 (5)	−0.0007 (4)	0.0006 (4)	0.0002 (4)
O1	0.0356 (5)	0.0154 (4)	0.0158 (4)	0.0037 (4)	−0.0069 (4)	−0.0016 (3)
O2	0.0272 (5)	0.0183 (4)	0.0260 (5)	−0.0003 (4)	0.0035 (4)	−0.0078 (4)
O3	0.0245 (5)	0.0236 (5)	0.0174 (4)	−0.0045 (4)	−0.0028 (4)	−0.0012 (3)
O4	0.0299 (5)	0.0266 (5)	0.0125 (4)	−0.0012 (4)	0.0028 (4)	0.0040 (3)
O5	0.0187 (4)	0.0158 (4)	0.0240 (5)	0.0009 (3)	0.0067 (3)	−0.0037 (3)
C1	0.0203 (6)	0.0150 (6)	0.0139 (5)	−0.0006 (4)	0.0003 (4)	0.0002 (4)
C2	0.0250 (6)	0.0160 (6)	0.0180 (6)	0.0030 (5)	−0.0024 (5)	0.0018 (4)
C3	0.0205 (6)	0.0133 (5)	0.0204 (6)	0.0012 (4)	0.0026 (5)	0.0000 (4)
C4	0.0162 (5)	0.0153 (5)	0.0137 (5)	−0.0037 (4)	0.0031 (4)	−0.0018 (4)
C5	0.0149 (5)	0.0158 (5)	0.0132 (5)	−0.0022 (4)	0.0020 (4)	0.0023 (4)
C6	0.0156 (5)	0.0132 (5)	0.0142 (5)	−0.0016 (4)	0.0028 (4)	0.0018 (4)
C7	0.0156 (5)	0.0136 (5)	0.0158 (5)	−0.0012 (4)	0.0027 (4)	0.0034 (4)
C8	0.0132 (5)	0.0109 (5)	0.0148 (5)	0.0008 (4)	0.0023 (4)	0.0007 (4)
C9	0.0162 (5)	0.0163 (5)	0.0147 (5)	0.0007 (4)	0.0020 (4)	0.0001 (4)
C10	0.0210 (6)	0.0215 (6)	0.0214 (6)	0.0038 (5)	0.0084 (5)	0.0036 (5)
C11	0.0156 (6)	0.0169 (6)	0.0383 (8)	0.0020 (4)	0.0090 (5)	0.0046 (5)
C12	0.0154 (6)	0.0164 (6)	0.0359 (7)	−0.0010 (4)	−0.0020 (5)	−0.0038 (5)
C13	0.0183 (6)	0.0172 (6)	0.0199 (6)	0.0012 (4)	−0.0020 (4)	−0.0036 (4)

Geometric parameters (Å, º) top

S1—O4	1.4312 (9)	C3—H3	0.943 (9)
S1—O5	1.4316 (9)	C4—C5	1.3812 (17)
S1—N3	1.6434 (10)	C5—C6	1.3934 (16)
S1—C8	1.7597 (12)	C5—H5	0.942 (9)
N1—O2	1.2271 (14)	C6—C7	1.4569 (16)
N1—O3	1.2336 (14)	C7—H7	0.950 (9)
N1—C4	1.4540 (15)	C8—C9	1.3889 (16)
N2—C7	1.2815 (16)	C8—C13	1.3908 (16)
N2—N3	1.3886 (13)	C9—C10	1.3905 (17)
N3—H3N	0.875 (9)	C9—H9	0.945 (9)
O1—C1	1.3431 (14)	C10—C11	1.3884 (19)
O1—H1O	0.838 (9)	C10—H10	0.947 (9)
C1—C2	1.4006 (17)	C11—C12	1.382 (2)
C1—C6	1.4155 (16)	C11—H11	0.942 (9)
C2—C3	1.3780 (17)	C12—C13	1.3884 (19)
C2—H2	0.952 (9)	C12—H12	0.947 (9)
C3—C4	1.3897 (17)	C13—H13	0.953 (9)

O4—S1—O5	119.43 (6)	C4—C5—H5	121.2 (10)
O4—S1—N3	107.91 (6)	C6—C5—H5	119.4 (10)
O5—S1—N3	104.06 (5)	C5—C6—C1	118.86 (11)
O4—S1—C8	108.59 (6)	C5—C6—C7	118.56 (10)
O5—S1—C8	109.12 (5)	C1—C6—C7	122.52 (11)
N3—S1—C8	107.03 (5)	N2—C7—C6	120.12 (11)
O2—N1—O3	123.06 (11)	N2—C7—H7	122.4 (10)
O2—N1—C4	118.84 (10)	C6—C7—H7	117.4 (10)
O3—N1—C4	118.09 (10)	C9—C8—C13	121.73 (11)
C7—N2—N3	116.43 (10)	C9—C8—S1	121.12 (9)
N2—N3—S1	115.98 (8)	C13—C8—S1	116.98 (9)
N2—N3—H3N	116.5 (12)	C8—C9—C10	118.51 (11)
S1—N3—H3N	113.7 (12)	C8—C9—H9	121.5 (10)
C1—O1—H1O	104.7 (15)	C10—C9—H9	120.0 (10)
O1—C1—C2	117.73 (10)	C11—C10—C9	120.38 (12)
O1—C1—C6	122.07 (11)	C11—C10—H10	119.2 (12)
C2—C1—C6	120.18 (11)	C9—C10—H10	120.4 (12)
C3—C2—C1	120.48 (11)	C12—C11—C10	120.28 (12)
C3—C2—H2	119.8 (11)	C12—C11—H11	119.3 (11)
C1—C2—H2	119.7 (11)	C10—C11—H11	120.4 (11)
C2—C3—C4	118.60 (11)	C11—C12—C13	120.40 (12)
C2—C3—H3	123.8 (11)	C11—C12—H12	120.7 (11)
C4—C3—H3	117.6 (11)	C13—C12—H12	118.9 (11)
C5—C4—C3	122.51 (11)	C12—C13—C8	118.71 (12)
C5—C4—N1	118.68 (10)	C12—C13—H13	120.5 (11)
C3—C4—N1	118.79 (11)	C8—C13—H13	120.8 (11)
C4—C5—C6	119.35 (11)

C7—N2—N3—S1	158.80 (9)	O1—C1—C6—C7	1.05 (19)
O4—S1—N3—N2	47.89 (10)	C2—C1—C6—C7	−177.91 (11)
O5—S1—N3—N2	175.72 (8)	N3—N2—C7—C6	174.40 (10)
C8—S1—N3—N2	−68.82 (9)	C5—C6—C7—N2	−179.10 (11)
O1—C1—C2—C3	−178.31 (12)	C1—C6—C7—N2	−2.18 (18)
C6—C1—C2—C3	0.69 (19)	O4—S1—C8—C9	−135.67 (10)
C1—C2—C3—C4	0.3 (2)	O5—S1—C8—C9	92.63 (10)
C2—C3—C4—C5	−1.02 (19)	N3—S1—C8—C9	−19.41 (11)
C2—C3—C4—N1	177.34 (11)	O4—S1—C8—C13	48.99 (11)
O2—N1—C4—C5	−174.10 (11)	O5—S1—C8—C13	−82.72 (10)
O3—N1—C4—C5	5.76 (16)	N3—S1—C8—C13	165.25 (9)
O2—N1—C4—C3	7.48 (17)	C13—C8—C9—C10	−0.06 (18)
O3—N1—C4—C3	−172.65 (11)	S1—C8—C9—C10	−175.19 (9)
C3—C4—C5—C6	0.71 (18)	C8—C9—C10—C11	0.18 (18)
N1—C4—C5—C6	−177.64 (10)	C9—C10—C11—C12	−0.20 (19)
C4—C5—C6—C1	0.30 (17)	C10—C11—C12—C13	0.1 (2)
C4—C5—C6—C7	177.34 (10)	C11—C12—C13—C8	0.03 (19)
O1—C1—C6—C5	177.97 (11)	C9—C8—C13—C12	−0.04 (18)
C2—C1—C6—C5	−0.99 (18)	S1—C8—C13—C12	175.28 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N2	0.84 (1)	1.86 (1)	2.628 (1)	153 (2)
N3—H3n···O3ⁱ	0.88 (1)	2.13 (1)	2.978 (1)	163 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₁N₃O₅S
M_r	321.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	7.8188 (1), 14.5904 (2), 11.9083 (1)
β (°)	98.159 (1)
V (Å³)	1344.74 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.47 × 0.40 × 0.33

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.883, 0.916
No. of measured, independent and observed [I > 2σ(I)] reflections	16761, 3089, 2972
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.088, 1.04
No. of reflections	3089
No. of parameters	243
No. of restraints	11
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.51

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N2	0.84 (1)	1.86 (1)	2.628 (1)	153 (2)
N3—H3n···O3ⁱ	0.88 (1)	2.13 (1)	2.978 (1)	163 (2)

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

Acknowledgements

We thank the Science Fund (12–02-03–2031, 12–02-03–2051) and the University of Malaya (PJP) for supporting this study. We are grateful to the University of Malaya for the purchase of the diffractometer.

References

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