4-[(2-Hy­droxy-5-nitro­benzyl­idene)amino]­benzene­sulfonamide

Tan, Y.-H.; Teoh, S.G.; Loh, W.-S.; Fun, H.-K.

doi:10.1107/S1600536810036949

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Pages o2610-o2611

doi:10.1107/S1600536810036949

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4-[(2-Hydroxy-5-nitrobenzylidene)amino]benzenesulfonamide

Yi-Han Tan,^a Siang Guan Teoh,^a Wan-Sin Loh ^b ‡ and Hoong-Kun Fun ^b ^*§

^aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 8 September 2010; accepted 15 September 2010; online 25 September 2010)

The title Schiff base compound, C₁₃H₁₁N₃O₅S, 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 intramolecular O—H⋯N hydrogen bond stabilizes the molecule, generating an S(6) ring motif. In the crystal, intermolecular N—H⋯O and C—H⋯O hydrogen bonds link the molecules 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 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_r = 321.31
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.039
wR(F²) = 0.110
S = 1.06
4825 reflections
211 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.43 e Å⁻³

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⋯O3^iv	0.93	2.55	3.3350 (17)	143
C7—H7A⋯O3^iv	0.93	2.36	3.187 (2)	148
C10—H10A⋯O1^v	0.93	2.58	3.1861 (19)	123
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y+2, -z; (iii) $[x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iv) -x+2, -y+2, -z; (v) -x+1, -y+2, -z+1.

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 ).

Supporting information

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

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

checkCIF report

Comment top

Sulfanilamide which is also known as sulfonamide and its derivatives are extensively used in medicine as they possess a wide range of medicinal, pharmacological and antimicrobial properties (Kremer et al., 2006, Chumakov et al., 2006). Sulfanilamide was the first drug that had been found to be used as a preventive and therapeutic agent towards a variety of diseases or bacterial infections in human biological systems. Schiff bases derived from sulfanilamide exhibit various pharmacological activities including antibacterial, antifungal, antiviral, antimicrobial, anticonvulsant, antitumor, antiulcer, anti-neoplastic, and anti-inflammatory properties as well as acting as enzymatic inhibitors (Wang et al., 2010, Sharaby, 2007, Kremer et al., 2006, Chumakov et al., 2006, Aziz-ur-Rehman et al., 2010, Subashini et al., 2009, Loughrey et al., 2009). The biological activity could be increased by the complexation with metal ions (Mohamed & Sharaby, 2007; Kremer et al., 2006).

The title Schiff base compound (Fig. 1) exists in an E configuration with respect to the C7═N1 double bond. The phenyl rings (C1–C6 & C8–C13) are almost coplanar with each other with a dihedral angle of 2.82 (6)°. The sulfonamide group (S1/O3/O4/N2) is twisted away from the attached phenyl ring with the torsion angle between N2–S1–C11–C12 being 64.84 (11)°. An intramolecular O1—H1O1···N1 hydrogen bond stabilized the molecule, generating an S(6) ring motif (Bernstein et al., 1995). Bond lengths (Allen et al., 1987) and angles are within the normal ranges and are comparable to the related structure (Fun et al., 2010).

In the crystal packing (Fig. 2), intermolecular N2—H2N2···O5, N2—H1N2···O2, N2—H1N2···O4, C5—H5A···O3, C7—H7A···O3 and C10—H10A···O1 hydrogen bonds (Table 1) link the molecules into three-dimensional network.

Related literature top

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 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 top

The title compound was synthesized by the general method of condensation of sulfanilamide with 2-hydroxy-5-nitrobenzaldehyde. To a methanolic solution (10 ml) of sulfanilamide (0.3444 g, 2 mmol), sodium acetate (0.1641 g, 2 mmol) was added. The resulting solution was heated to reflux on a water bath. A methanolic solution (10 ml) of 2-hydroxy-5-nitrobenzaldehyde (0.3342 g, 2 mmol) was then added dropwise to the solution. The solution was left under reflux (65–70°C) for 1 h. After half an hour, yellowish orange precipitate started to form during refluxing. The resulting mixture was filtered and the filtrate was left to evaporate slowly at room temperature. Orange crystals of the title compound suitable for X-ray diffraction were obtained after 1 week.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme. The dashed line indicates the intramolecular hydrogen bond.
	Fig. 2. The crystal packing of the title compound, viewed along the a axis, showing the three-dimensional network. Intermolecular interactions are shown as dashed lines. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

4-[(2-Hydroxy-5-nitrobenzylidene)amino]benzenesulfonamide top

Crystal data top

C₁₃H₁₁N₃O₅S	F(000) = 664
M_r = 321.31	D_x = 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

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4825 independent reflections
Radiation source: fine-focus sealed tube	4104 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ϕ and ω scans	θ_max = 32.5°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
T_min = 0.896, T_max = 0.985	k = −40→36
29377 measured reflections	l = −15→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)] = 0.039	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(F_o²) + (0.0528P)² + 0.7191P] where P = (F_o² + 2F_c²)/3
4825 reflections	(Δ/σ)_max = 0.002
211 parameters	Δρ_max = 0.60 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₁₃H₁₁N₃O₅S	V = 1337.21 (3) Å³
M_r = 321.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.7698 (1) Å	µ = 0.27 mm⁻¹
b = 26.4754 (3) Å	T = 100 K
c = 9.9683 (1) Å	0.41 × 0.27 × 0.06 mm
β = 131.544 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4825 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4104 reflections with I > 2σ(I)
T_min = 0.896, T_max = 0.985	R_int = 0.031
29377 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.60 e Å⁻³
4825 reflections	Δρ_min = −0.43 e Å⁻³
211 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O3^iv	0.93	2.55	3.3350 (17)	143
C7—H7A···O3^iv	0.93	2.36	3.187 (2)	148
C10—H10A···O1^v	0.93	2.58	3.1861 (19)	123

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

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)	6.7698 (1), 26.4754 (3), 9.9683 (1)
β (°)	131.544 (1)
V (Å³)	1337.21 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.41 × 0.27 × 0.06

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.896, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	29377, 4825, 4104
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.756

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.110, 1.06
No. of reflections	4825
No. of parameters	211
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.60, −0.43

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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···O3^iv	0.93	2.55	3.3350 (17)	143
C7—H7A···O3^iv	0.93	2.36	3.187 (2)	148
C10—H10A···O1^v	0.93	2.58	3.1861 (19)	123

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

Footnotes

‡Thomson Reuters ResearcherID: C-7581-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for the RU research grant (PKIMIA/815002). HKF and WSL thank USM for the Research University Grant (1001/PFIZIK/811160). YHT and WSL are grateful for the award of USM fellowships for financial assistance.

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