4-[(2-Hy-droxy-5-nitro-benzyl-idene)amino]-benzene-sulfonamide.

The title Schiff base compound, C(13)H(11)N(3)O(5)S, exists in an E configuration with respect to the C=N double bond. The benzene rings are almost coplanar, making a dihedral angle of 2.82 (6). The sulfonamide group is twisted away from the attached phenyl ring with an N-S-C-C torsion angle of 64.84 (11)°. An intra-molecular O-H⋯N hydrogen bond stabilizes the mol-ecule, generating an S(6) ring motif. In the crystal, inter-molecular N-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network.

Related literature

For background and the biological activity of sulfonamide and its derivatives, see: Kremer et al. (2006 ▶); Chumakov et al. (2006 ▶); Mohamed & Sharaby (2007 ▶); Wang et al. (2010 ▶); Sharaby (2007 ▶); Aziz-ur-Rehman et al. (2010 ▶); Subashini et al. (2009 ▶); Loughrey et al. (2009 ▶). For a related structure, see: Fun et al. (2010 ▶). For bond-length data, see: Allen et al. (1987 ▶). For n class="Chemical">hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C13H11N3O5S

M = 321.31

Monoclinic,

a = 6.7698 (1) Å

b = 26.4754 (3) Å

c = 9.9683 (1) Å

β = 131.544 (1)°

V = 1337.21 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 100 K

0.41 × 0.27 × 0.06 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.896, T max = 0.985

29377 measured reflections

4825 independent reflections

4104 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.110

S = 1.06

4825 reflections

211 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.60 e Å−3

Δρmin = −0.43 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810036949/sj5036sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810036949/sj5036Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C13H11N3O5S	F(000) = 664
Mr = 321.31	Dx = 1.596 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9950 reflections
a = 6.7698 (1) Å	θ = 2.8–35.5°
b = 26.4754 (3) Å	µ = 0.27 mm−1
c = 9.9683 (1) Å	T = 100 K
β = 131.544 (1)°	Plate, orange
V = 1337.21 (3) Å3	0.41 × 0.27 × 0.06 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	4825 independent reflections
Radiation source: fine-focus sealed tube	4104 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 32.5°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
Tmin = 0.896, Tmax = 0.985	k = −40→36
29377 measured reflections	l = −15→15

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0528P)2 + 0.7191P] where P = (Fo2 + 2Fc2)/3
4825 reflections	(Δ/σ)max = 0.002
211 parameters	Δρmax = 0.60 e Å−3
0 restraints	Δρmin = −0.43 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

	x	y	z	Uiso*/Ueq
S1	0.25811 (6)	0.770137 (11)	0.29838 (4)	0.01433 (8)
O1	0.69814 (19)	1.06412 (4)	0.38905 (13)	0.01833 (18)
O2	1.2322 (2)	1.14670 (4)	0.11034 (15)	0.0251 (2)
O3	1.1687 (2)	1.06896 (4)	0.02207 (13)	0.0217 (2)
O4	0.46897 (19)	0.73446 (4)	0.38253 (15)	0.0264 (2)
O5	0.1385 (2)	0.77870 (4)	0.37367 (14)	0.0243 (2)
N1	0.6474 (2)	0.97162 (4)	0.29501 (13)	0.01443 (19)
N2	0.0283 (2)	0.75128 (4)	0.09717 (14)	0.01538 (19)
N3	1.1534 (2)	1.10368 (4)	0.09747 (14)	0.0166 (2)
C1	0.8033 (2)	1.07306 (5)	0.31518 (15)	0.0146 (2)
C2	0.8745 (2)	1.12251 (5)	0.31389 (16)	0.0169 (2)
H2A	0.8429	1.1487	0.3599	0.020*
C3	0.9919 (2)	1.13262 (5)	0.24433 (16)	0.0167 (2)
H3A	1.0412	1.1654	0.2442	0.020*
C4	1.0352 (2)	1.09290 (5)	0.17442 (15)	0.0142 (2)
C5	0.9623 (2)	1.04378 (5)	0.17048 (15)	0.0146 (2)
H5A	0.9913	1.0181	0.1215	0.018*
C6	0.8442 (2)	1.03309 (5)	0.24119 (15)	0.0139 (2)
C7	0.7632 (2)	0.98178 (5)	0.23515 (16)	0.0158 (2)
H7A	0.7949	0.9561	0.1879	0.019*
C8	0.5618 (2)	0.92230 (5)	0.29004 (15)	0.0135 (2)
C9	0.4354 (2)	0.91795 (5)	0.35687 (16)	0.0152 (2)
H9A	0.4130	0.9465	0.4000	0.018*
C10	0.3425 (2)	0.87159 (5)	0.35986 (16)	0.0158 (2)
H10A	0.2583	0.8689	0.4045	0.019*
C11	0.3773 (2)	0.82917 (5)	0.29516 (15)	0.0139 (2)
C12	0.5046 (2)	0.83273 (5)	0.22825 (16)	0.0163 (2)
H12A	0.5280	0.8040	0.1862	0.020*
C13	0.5958 (2)	0.87914 (5)	0.22483 (16)	0.0164 (2)
H13A	0.6792	0.8818	0.1796	0.020*
H2N2	0.074 (4)	0.7439 (7)	0.041 (3)	0.028 (5)*
H1N2	−0.119 (4)	0.7655 (8)	0.038 (3)	0.030 (5)*
H1O1	0.655 (5)	1.0290 (11)	0.368 (4)	0.068 (8)*

	U11	U22	U33	U12	U13	U23
S1	0.01492 (14)	0.01229 (14)	0.01464 (13)	−0.00158 (10)	0.00933 (11)	0.00082 (9)
O1	0.0243 (5)	0.0160 (5)	0.0229 (4)	0.0000 (4)	0.0191 (4)	−0.0007 (3)
O2	0.0303 (5)	0.0155 (5)	0.0373 (5)	−0.0009 (4)	0.0257 (5)	0.0052 (4)
O3	0.0270 (5)	0.0219 (5)	0.0227 (4)	−0.0038 (4)	0.0192 (4)	−0.0036 (4)
O4	0.0152 (4)	0.0161 (5)	0.0320 (5)	0.0019 (4)	0.0090 (4)	0.0079 (4)
O5	0.0372 (6)	0.0225 (5)	0.0267 (5)	−0.0090 (4)	0.0268 (5)	−0.0048 (4)
N1	0.0162 (4)	0.0123 (5)	0.0157 (4)	−0.0014 (4)	0.0110 (4)	−0.0003 (3)
N2	0.0137 (4)	0.0156 (5)	0.0161 (4)	−0.0005 (4)	0.0096 (4)	−0.0019 (4)
N3	0.0167 (5)	0.0155 (5)	0.0175 (4)	0.0006 (4)	0.0112 (4)	0.0032 (4)
C1	0.0147 (5)	0.0149 (5)	0.0142 (4)	0.0010 (4)	0.0096 (4)	0.0005 (4)
C2	0.0200 (5)	0.0117 (5)	0.0197 (5)	0.0014 (4)	0.0134 (5)	−0.0002 (4)
C3	0.0170 (5)	0.0134 (5)	0.0181 (5)	0.0001 (4)	0.0110 (5)	0.0010 (4)
C4	0.0148 (5)	0.0132 (5)	0.0146 (5)	−0.0003 (4)	0.0098 (4)	0.0011 (4)
C5	0.0179 (5)	0.0118 (5)	0.0154 (5)	−0.0005 (4)	0.0116 (4)	−0.0002 (4)
C6	0.0165 (5)	0.0118 (5)	0.0143 (4)	−0.0007 (4)	0.0105 (4)	−0.0006 (4)
C7	0.0195 (5)	0.0134 (5)	0.0171 (5)	−0.0009 (4)	0.0132 (5)	−0.0005 (4)
C8	0.0136 (5)	0.0122 (5)	0.0137 (4)	−0.0007 (4)	0.0087 (4)	−0.0002 (4)
C9	0.0183 (5)	0.0127 (5)	0.0185 (5)	−0.0005 (4)	0.0138 (5)	−0.0016 (4)
C10	0.0173 (5)	0.0158 (6)	0.0178 (5)	−0.0015 (4)	0.0132 (5)	−0.0012 (4)
C11	0.0143 (5)	0.0129 (5)	0.0139 (4)	−0.0017 (4)	0.0091 (4)	−0.0005 (4)
C12	0.0196 (5)	0.0138 (5)	0.0187 (5)	−0.0021 (4)	0.0140 (5)	−0.0030 (4)
C13	0.0202 (5)	0.0146 (6)	0.0199 (5)	−0.0020 (4)	0.0157 (5)	−0.0022 (4)

S1—O4	1.4301 (10)	C3—C4	1.3958 (17)
S1—O5	1.4408 (10)	C3—H3A	0.9300
S1—N2	1.5980 (11)	C4—C5	1.3822 (17)
S1—C11	1.7689 (12)	C5—C6	1.4014 (15)
O1—C1	1.3417 (14)	C5—H5A	0.9300
O1—H1O1	0.96 (3)	C6—C7	1.4513 (17)
O2—N3	1.2278 (14)	C7—H7A	0.9300
O3—N3	1.2345 (14)	C8—C9	1.3951 (15)
N1—C7	1.2892 (15)	C8—C13	1.4068 (16)
N1—C8	1.4160 (16)	C9—C10	1.3881 (17)
N2—H2N2	0.83 (2)	C9—H9A	0.9300
N2—H1N2	0.84 (2)	C10—C11	1.3908 (17)
N3—C4	1.4576 (15)	C10—H10A	0.9300
C1—C2	1.3982 (17)	C11—C12	1.3999 (16)
C1—C6	1.4181 (16)	C12—C13	1.3855 (17)
C2—C3	1.3837 (17)	C12—H12A	0.9300
C2—H2A	0.9300	C13—H13A	0.9300
O4—S1—O5	119.05 (7)	C4—C5—H5A	120.4
O4—S1—N2	106.97 (6)	C6—C5—H5A	120.4
O5—S1—N2	106.71 (6)	C5—C6—C1	118.97 (11)
O4—S1—C11	107.71 (6)	C5—C6—C7	119.61 (10)
O5—S1—C11	106.92 (6)	C1—C6—C7	121.42 (10)
N2—S1—C11	109.23 (6)	N1—C7—C6	120.34 (11)
C1—O1—H1O1	104.2 (17)	N1—C7—H7A	119.8
C7—N1—C8	122.45 (11)	C6—C7—H7A	119.8
S1—N2—H2N2	115.9 (13)	C9—C8—C13	119.57 (11)
S1—N2—H1N2	117.2 (14)	C9—C8—N1	115.21 (10)
H2N2—N2—H1N2	115.7 (19)	C13—C8—N1	125.21 (10)
O2—N3—O3	123.25 (11)	C10—C9—C8	120.88 (11)
O2—N3—C4	118.61 (11)	C10—C9—H9A	119.6
O3—N3—C4	118.14 (10)	C8—C9—H9A	119.6
O1—C1—C2	118.81 (11)	C9—C10—C11	119.06 (10)
O1—C1—C6	120.75 (11)	C9—C10—H10A	120.5
C2—C1—C6	120.44 (11)	C11—C10—H10A	120.5
C3—C2—C1	120.11 (11)	C10—C11—C12	120.90 (11)
C3—C2—H2A	119.9	C10—C11—S1	119.05 (9)
C1—C2—H2A	119.9	C12—C11—S1	120.04 (9)
C2—C3—C4	119.01 (11)	C13—C12—C11	119.77 (11)
C2—C3—H3A	120.5	C13—C12—H12A	120.1
C4—C3—H3A	120.5	C11—C12—H12A	120.1
C5—C4—C3	122.27 (11)	C12—C13—C8	119.81 (10)
C5—C4—N3	118.65 (11)	C12—C13—H13A	120.1
C3—C4—N3	119.05 (11)	C8—C13—H13A	120.1
C4—C5—C6	119.17 (11)
O1—C1—C2—C3	177.73 (11)	C1—C6—C7—N1	1.12 (18)
C6—C1—C2—C3	−1.66 (18)	C7—N1—C8—C9	−178.76 (11)
C1—C2—C3—C4	0.62 (18)	C7—N1—C8—C13	1.41 (19)
C2—C3—C4—C5	0.68 (19)	C13—C8—C9—C10	−0.02 (18)
C2—C3—C4—N3	178.64 (11)	N1—C8—C9—C10	−179.86 (11)
O2—N3—C4—C5	−175.78 (11)	C8—C9—C10—C11	0.06 (19)
O3—N3—C4—C5	4.36 (16)	C9—C10—C11—C12	0.21 (18)
O2—N3—C4—C3	6.19 (17)	C9—C10—C11—S1	−179.82 (9)
O3—N3—C4—C3	−173.67 (11)	O4—S1—C11—C10	−128.97 (10)
C3—C4—C5—C6	−0.92 (18)	O5—S1—C11—C10	0.07 (12)
N3—C4—C5—C6	−178.88 (10)	N2—S1—C11—C10	115.18 (10)
C4—C5—C6—C1	−0.13 (17)	O4—S1—C11—C12	51.00 (12)
C4—C5—C6—C7	179.03 (11)	O5—S1—C11—C12	−179.95 (10)
O1—C1—C6—C5	−177.97 (11)	N2—S1—C11—C12	−64.84 (11)
C2—C1—C6—C5	1.41 (18)	C10—C11—C12—C13	−0.51 (18)
O1—C1—C6—C7	2.88 (18)	S1—C11—C12—C13	179.51 (10)
C2—C1—C6—C7	−177.74 (11)	C11—C12—C13—C8	0.55 (19)
C8—N1—C7—C6	179.21 (11)	C9—C8—C13—C12	−0.29 (18)
C5—C6—C7—N1	−178.02 (11)	N1—C8—C13—C12	179.54 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N2···O5i	0.82 (3)	2.07 (3)	2.891 (2)	172 (3)
N2—H1N2···O2ii	0.84 (3)	2.58 (2)	3.1378 (15)	125 (2)
N2—H1N2···O4iii	0.84 (3)	2.11 (3)	2.883 (2)	153 (2)
O1—H1O1···N1	0.96 (3)	1.67 (3)	2.5626 (15)	154 (4)
C5—H5A···O3iv	0.93	2.55	3.3350 (17)	143
C7—H7A···O3iv	0.93	2.36	3.187 (2)	148
C10—H10A···O1v	0.93	2.58	3.1861 (19)	123

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N2⋯O5i	0.82 (3)	2.07 (3)	2.891 (2)	172 (3)
N2—H1N2⋯O2ii	0.84 (3)	2.58 (2)	3.1378 (15)	125 (2)
N2—H1N2⋯O4iii	0.84 (3)	2.11 (3)	2.883 (2)	153 (2)
O1—H1O1⋯N1	0.96 (3)	1.67 (3)	2.5626 (15)	154 (4)
C5—H5A⋯O3iv	0.93	2.55	3.3350 (17)	143
C7—H7A⋯O3iv	0.93	2.36	3.187 (2)	148
C10—H10A⋯O1v	0.93	2.58	3.1861 (19)	123

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .