N-(4-Meth­oxy­phen­yl)benzene­sulfonamide

Ibrahim, S.; Tahir, M.N.; Iqbal, N.; Shahwar, D.; Raza, M.A.

doi:10.1107/S1600536811000365

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o298

doi:10.1107/S1600536811000365

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N-(4-Methoxyphenyl)benzenesulfonamide

Saba Ibrahim,^a M. Nawaz Tahir,^b ^* Nadeem Iqbal,^a Durre Shahwar ^a and Muhammad Asam Raza ^a

^aDepartment of Chemistry, Government College University, Lahore, Pakistan, and ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 3 January 2011; accepted 5 January 2011; online 8 January 2011)

In the title compound, C₁₃H₁₃NO₃S, the benzene ring of the benzenesulfonamide moiety is disordered with an occupancy ratio of 0.56 (3):0.44 (3), the disorder components being twisted at and angle of 21 (1)° to each other. The methoxybenzene group is roughly planar (r.m.s. deviation = 0.0144 Å) and the amide N atom is displaced from this plane by 0.090 (6) Å. The dihedral angles between the methoxybenzene group and the major and minor occupancy components of the disordered benzene ring are 54.6 (4) and 62.9 (5)°, respectively. In the crystal, infinite polymeric chains are formed along [100] due to intermolecular N—H⋯O hydrogen bonding. Weak C—H⋯π interactions are also present in the crystal.

Related literature

For related structures, see: Kato et al. (2006 ); Perlovich et al. (2009 ).

Experimental

Crystal data

C₁₃H₁₃NO₃S
M_r = 263.30
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.3094 (5) Å
b = 8.5309 (10) Å
c = 27.925 (3) Å
V = 1264.8 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 296 K
0.30 × 0.14 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.961, T_max = 0.970
7272 measured reflections
2457 independent reflections
1503 reflections with I > 2σ(I)
R_int = 0.060

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.131
S = 1.02
2457 reflections
138 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.28 e Å⁻³
Absolute structure: Flack (1983 ), 961 Friedel pairs
Flack parameter: 0.09 (16)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C1A–C6A, C7–C12 and C1B–C6B rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.83 (2)	2.22 (2)	3.039 (4)	170 (4)
C8—H8⋯Cg2ⁱⁱ	0.93	2.93	3.613 (5)	132
C13—H13B⋯Cg1ⁱⁱⁱ	0.96	2.98	3.766 (6)	140
C13—H13B⋯Cg3ⁱⁱⁱ	0.96	2.96	3.763 (7)	143
Symmetry codes: (i) x+1, y, z; (ii) $[x-{\script{1\over 2}}, -y+{\script{5\over 2}}, -z]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ .

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811000365/bq2272sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811000365/bq2272Isup2.hkl

checkCIF report

Comment top

The title compound (I, Fig. 1) is a part of the synthesis of sulfonamides and consequently the study of their bioactivity. The crystal structures of 4-amino-N-(4-methoxyphenyl)benzenesulfonamide (Perlovich et al., 2009) and P-(+)-N-Phenyl-4-methoxybenzenesulfonamide (Kato, et al., 2006) have been published previously which are related to the title compound (I).

In (I), the phenyl ring of benzenethiol moiety is disordered over two set of sites A (C1A—C6A) and B (C1B—C6B) with occupancy ratio of 0.56 (3):0.44 (3). The dihedral angle between A/B is 21 (1)°. The methoxybenzene group C (C7—C13/O2) is almost planar with r. m. s. deviation of 0.0144 Å and amide atom N1 is at a distance of 0.0897 (55)Å. The dihedral angle between A/C and B/C is 54.63 (35)° and 62.86 (50)°, respectively. The sulfonyl group D (S1/O1/O2) is of course planar. The dihedral angles between A/D, B/D and C/D are 53.37 (43)°, 51.65 (50)° and 24.10 (28)°, respectively. The molecules are stabilized in the form of infinite one-dimensional polymeric chains due to N—H···O type (Table 1, Fig. 2) extending along the crystallographic a-axis. The C—H···π interactions (Table 1) also play important role in stabilizing the molecules.

Related literature top

For related background and crystal structures, see: Kato et al. (2006); Perlovich et al. (2009).

Experimental top

Equal molar (10 mmol) quantity of benzene sulfonyl chloride and para anisidine was mixed in 10 ml distilled water under stirring at room temperature. During the reaction pH was adjusted at 8 using dilute solution of sodium carbonate. The reaction was monitored using TLC. On the completion of reaction the pH was made acidified using 3 N HCl. The crude product was separated by filtration, dried and recrystalized in methanol to afford white needles of (I) after 72 h.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with the atom numbering scheme having atoms of greater occupancy ratio. The thermal ellipsoids are drawn at the 50% probability level.
	Fig. 2. The partial packing (PLATON; Spek, 2009) which shows that molecules form polymeric chains extending along the a axis.

N-(4-Methoxyphenyl)benzenesulfonamide top

Crystal data top

C₁₃H₁₃NO₃S	F(000) = 552
M_r = 263.30	D_x = 1.383 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1503 reflections
a = 5.3094 (5) Å	θ = 2.5–25.2°
b = 8.5309 (10) Å	µ = 0.26 mm⁻¹
c = 27.925 (3) Å	T = 296 K
V = 1264.8 (2) Å³	Needle, white
Z = 4	0.30 × 0.14 × 0.12 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	2457 independent reflections
Radiation source: fine-focus sealed tube	1503 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.060
Detector resolution: 8.00 pixels mm^-1	θ_max = 26.0°, θ_min = 2.5°
ω scans	h = −4→6
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −9→10
T_min = 0.961, T_max = 0.970	l = −32→31
7272 measured reflections

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)] = 0.061	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.131	w = 1/[σ²(F_o²) + (0.0506P)² + 0.2719P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
2457 reflections	Δρ_max = 0.41 e Å⁻³
138 parameters	Δρ_min = −0.28 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 961 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.09 (16)

Crystal data top

C₁₃H₁₃NO₃S	V = 1264.8 (2) Å³
M_r = 263.30	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.3094 (5) Å	µ = 0.26 mm⁻¹
b = 8.5309 (10) Å	T = 296 K
c = 27.925 (3) Å	0.30 × 0.14 × 0.12 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	2457 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1503 reflections with I > 2σ(I)
T_min = 0.961, T_max = 0.970	R_int = 0.060
7272 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.131	Δρ_max = 0.41 e Å⁻³
S = 1.02	Δρ_min = −0.28 e Å⁻³
2457 reflections	Absolute structure: Flack (1983), 961 Friedel pairs
138 parameters	Absolute structure parameter: 0.09 (16)
1 restraint

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	Occ. (<1)
S1	0.5888 (2)	1.17782 (15)	0.14716 (4)	0.0434 (4)
O1	0.6723 (6)	1.2938 (4)	0.18015 (10)	0.0615 (14)
O2	0.3371 (4)	1.1850 (4)	0.12785 (9)	0.0549 (13)
O3	0.7036 (6)	0.8660 (4)	−0.07098 (11)	0.0570 (12)
N1	0.7813 (6)	1.1858 (5)	0.10190 (12)	0.0427 (14)
C1A	0.6261 (14)	0.9927 (7)	0.1750 (2)	0.0500 (19)	0.56 (3)
C2A	0.7618 (19)	0.9727 (8)	0.2171 (3)	0.0500 (19)	0.56 (3)
C3A	0.786 (2)	0.8243 (10)	0.2371 (2)	0.0500 (19)	0.56 (3)
C4A	0.6743 (17)	0.6959 (8)	0.2150 (2)	0.0500 (19)	0.56 (3)
C5A	0.5386 (12)	0.7159 (8)	0.1729 (3)	0.0500 (19)	0.56 (3)
C6A	0.5145 (17)	0.8643 (9)	0.1529 (3)	0.0500 (19)	0.56 (3)
C7	0.7490 (7)	1.0996 (5)	0.05846 (15)	0.0353 (16)
C8	0.5531 (8)	1.1329 (5)	0.02810 (14)	0.0403 (16)
C9	0.5314 (8)	1.0566 (5)	−0.01519 (16)	0.0413 (17)
C10	0.7056 (8)	0.9465 (6)	−0.02856 (16)	0.0407 (17)
C11	0.9050 (9)	0.9139 (5)	0.00183 (17)	0.0490 (17)
C12	0.9241 (9)	0.9870 (6)	0.04544 (16)	0.0473 (16)
C13	0.4974 (11)	0.8934 (7)	−0.10251 (17)	0.075 (3)
C3B	0.879 (3)	0.8430 (11)	0.2267 (4)	0.054 (3)	0.44 (3)
C4B	0.726 (2)	0.7133 (10)	0.2186 (3)	0.054 (3)	0.44 (3)
C5B	0.5220 (14)	0.7245 (11)	0.1876 (6)	0.054 (3)	0.44 (3)
C6B	0.4708 (16)	0.8655 (12)	0.1646 (5)	0.054 (3)	0.44 (3)
C2B	0.827 (3)	0.9840 (9)	0.2037 (5)	0.054 (3)	0.44 (3)
C1B	0.6235 (18)	0.9952 (10)	0.1726 (3)	0.054 (3)	0.44 (3)
H6A	0.42369	0.87769	0.12470	0.0601*	0.56 (3)
H5A	0.46390	0.62998	0.15812	0.0601*	0.56 (3)
H11	1.02714	0.84188	−0.00742	0.0589*
H12	1.05444	0.96101	0.06623	0.0569*
H13A	0.34217	0.88310	−0.08517	0.1122*
H13B	0.50147	0.81823	−0.12809	0.1122*
H13C	0.50967	0.99726	−0.11552	0.1122*
H8	0.43398	1.20759	0.03680	0.0480*
H9	0.39767	1.08001	−0.03547	0.0494*
H1	0.930 (4)	1.197 (5)	0.1105 (13)	0.0514*
H2A	0.83652	1.05863	0.23189	0.0601*	0.56 (3)
H3A	0.87672	0.81092	0.26532	0.0601*	0.56 (3)
H4A	0.69041	0.59660	0.22843	0.0601*	0.56 (3)
H2B	0.92955	1.07075	0.20904	0.0646*	0.44 (3)
H3B	1.01505	0.83549	0.24742	0.0646*	0.44 (3)
H4B	0.76021	0.61899	0.23400	0.0646*	0.44 (3)
H5B	0.41988	0.63775	0.18221	0.0646*	0.44 (3)
H6B	0.33438	0.87301	0.14384	0.0646*	0.44 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0335 (6)	0.0474 (8)	0.0494 (7)	0.0026 (6)	−0.0036 (5)	−0.0007 (7)
O1	0.060 (2)	0.060 (3)	0.0646 (19)	−0.0021 (18)	−0.0064 (16)	−0.022 (2)
O2	0.0254 (16)	0.075 (3)	0.0642 (18)	0.0085 (17)	−0.0046 (13)	0.004 (2)
O3	0.056 (2)	0.057 (2)	0.058 (2)	0.0110 (17)	0.0010 (17)	−0.0093 (18)
N1	0.0250 (19)	0.054 (3)	0.049 (2)	−0.005 (2)	−0.0056 (17)	0.005 (2)
C1A	0.042 (3)	0.056 (4)	0.052 (3)	−0.004 (2)	−0.001 (2)	0.014 (2)
C2A	0.042 (3)	0.056 (4)	0.052 (3)	−0.004 (2)	−0.001 (2)	0.014 (2)
C3A	0.042 (3)	0.056 (4)	0.052 (3)	−0.004 (2)	−0.001 (2)	0.014 (2)
C4A	0.042 (3)	0.056 (4)	0.052 (3)	−0.004 (2)	−0.001 (2)	0.014 (2)
C5A	0.042 (3)	0.056 (4)	0.052 (3)	−0.004 (2)	−0.001 (2)	0.014 (2)
C6A	0.042 (3)	0.056 (4)	0.052 (3)	−0.004 (2)	−0.001 (2)	0.014 (2)
C7	0.025 (2)	0.034 (3)	0.047 (3)	−0.0053 (19)	0.005 (2)	0.004 (2)
C8	0.026 (2)	0.046 (3)	0.049 (3)	0.007 (2)	−0.003 (2)	0.007 (2)
C9	0.036 (3)	0.041 (3)	0.047 (3)	0.006 (2)	−0.003 (2)	0.007 (2)
C10	0.033 (3)	0.037 (3)	0.052 (3)	−0.004 (2)	0.002 (2)	0.003 (2)
C11	0.035 (3)	0.041 (3)	0.071 (3)	0.006 (2)	0.000 (3)	0.005 (3)
C12	0.028 (2)	0.053 (3)	0.061 (3)	0.003 (2)	−0.006 (2)	0.010 (3)
C13	0.088 (5)	0.081 (5)	0.055 (3)	0.018 (3)	−0.017 (3)	−0.017 (3)
C3B	0.055 (4)	0.055 (5)	0.052 (4)	−0.021 (3)	−0.010 (3)	0.010 (3)
C4B	0.055 (4)	0.055 (5)	0.052 (4)	−0.021 (3)	−0.010 (3)	0.010 (3)
C5B	0.055 (4)	0.055 (5)	0.052 (4)	−0.021 (3)	−0.010 (3)	0.010 (3)
C6B	0.055 (4)	0.055 (5)	0.052 (4)	−0.021 (3)	−0.010 (3)	0.010 (3)
C2B	0.055 (4)	0.055 (5)	0.052 (4)	−0.021 (3)	−0.010 (3)	0.010 (3)
C1B	0.055 (4)	0.055 (5)	0.052 (4)	−0.021 (3)	−0.010 (3)	0.010 (3)

Geometric parameters (Å, º) top

S1—O1	1.423 (3)	C7—C12	1.385 (6)
S1—O2	1.442 (2)	C8—C9	1.378 (6)
S1—N1	1.627 (3)	C9—C10	1.370 (6)
S1—C1A	1.771 (6)	C10—C11	1.385 (6)
S1—C1B	1.722 (9)	C11—C12	1.372 (7)
O3—C10	1.369 (6)	C2A—H2A	0.9300
O3—C13	1.424 (6)	C2B—H2B	0.9300
N1—C7	1.429 (6)	C3A—H3A	0.9300
N1—H1	0.83 (2)	C3B—H3B	0.9300
C1A—C6A	1.390 (10)	C4A—H4A	0.9300
C1A—C2A	1.389 (11)	C4B—H4B	0.9300
C1B—C2B	1.390 (18)	C5A—H5A	0.9300
C1B—C6B	1.390 (13)	C5B—H5B	0.9300
C2A—C3A	1.390 (11)	C6A—H6A	0.9300
C2B—C3B	1.391 (14)	C6B—H6B	0.9300
C3A—C4A	1.390 (11)	C8—H8	0.9300
C3B—C4B	1.391 (15)	C9—H9	0.9300
C4A—C5A	1.389 (10)	C11—H11	0.9300
C4B—C5B	1.390 (15)	C12—H12	0.9300
C5A—C6A	1.390 (11)	C13—H13B	0.9600
C5B—C6B	1.390 (16)	C13—H13C	0.9600
C7—C8	1.372 (6)	C13—H13A	0.9600

S1···H8	3.2000	C9···H8^viii	3.0000
O1···C3Aⁱ	3.366 (9)	C10···H11^vi	2.8200
O2···C8	3.045 (5)	C11···H11^vi	2.9700
O2···N1ⁱⁱ	3.039 (4)	C13···H5A^v	2.9300
O1···H4Aⁱⁱⁱ	2.9200	C13···H9	2.5100
O1···H2B	2.4800	H1···O2^vii	2.22 (2)
O1···H3A^iv	2.8400	H1···H12	2.4500
O1···H3B^iv	2.6400	H2A···O1	2.6200
O1···H2A	2.6200	H2B···O1	2.4800
O2···H1ⁱⁱ	2.22 (2)	H2B···H4B^iv	2.3300
O2···H6A	2.6600	H2B···C4B^iv	2.9800
O2···H8	2.6000	H2B···H3B^iv	2.5800
O2···H6B	2.7000	H3A···O1^xi	2.8400
O3···H5A^v	2.8000	H3B···O1^xi	2.6400
O3···H6A^v	2.8200	H3B···H2B^xi	2.5800
O3···H12^vi	2.9000	H4A···O1^xii	2.9200
N1···O2^vii	3.039 (4)	H4A···C2A^ix	3.0300
N1···H9^viii	2.8000	H4B···C2B^xi	3.0300
C2A···C4Aⁱ	3.547 (12)	H4B···H2B^xi	2.3300
C3A···O1^ix	3.366 (9)	H5A···O3^vi	2.8000
C3B···C6B^vii	3.594 (18)	H5A···C13^vi	2.9300
C4A···C2A^ix	3.547 (12)	H6A···O3^vi	2.8200
C5A···C13^v	3.266 (9)	H6A···O2	2.6600
C6A···C7	3.540 (9)	H6B···H13B^vi	2.4500
C6B···C3Bⁱⁱ	3.594 (18)	H6B···O2	2.7000
C7···C9^viii	3.509 (6)	H8···S1	3.2000
C7···C6A	3.540 (9)	H8···O2	2.6000
C8···C12ⁱⁱ	3.597 (6)	H8···C8^x	3.0400
C8···O2	3.045 (5)	H8···C9^x	3.0000
C9···C7^x	3.509 (6)	H9···C13	2.5100
C9···C11ⁱⁱ	3.573 (6)	H9···H13A	2.2000
C10···C11^vi	3.544 (7)	H9···H13C	2.4200
C11···C10^v	3.544 (7)	H9···N1^x	2.8000
C11···C9^vii	3.573 (6)	H9···C7^x	2.9200
C12···C8^vii	3.597 (6)	H9···C8^x	3.0600
C13···C5A^vi	3.266 (9)	H11···C11^v	2.9700
C2A···H4Aⁱ	3.0300	H11···C10^v	2.8200
C2B···H4B^iv	3.0300	H12···O3^v	2.9000
C4A···H13B^v	2.9900	H12···H1	2.4500
C4B···H13B^v	2.9300	H13A···C9	2.6500
C4B···H2B^xi	2.9800	H13A···C5A^vi	3.0500
C5A···H13A^v	3.0500	H13A···H9	2.2000
C5A···H13B^v	2.7700	H13B···C4A^vi	2.9900
C5B···H13B^v	3.0600	H13B···C6A^vi	3.1000
C6A···H13B^v	3.1000	H13B···C4B^vi	2.9300
C7···H9^viii	2.9200	H13B···C5B^vi	3.0600
C8···H8^viii	3.0400	H13B···H6B^v	2.4500
C8···H9^viii	3.0600	H13B···C5A^vi	2.7700
C9···H13C	2.8500	H13C···C9	2.8500
C9···H13A	2.6500	H13C···H9	2.4200

O1—S1—O2	120.1 (2)	C10—C11—C12	120.6 (4)
O1—S1—N1	106.2 (2)	C7—C12—C11	119.9 (4)
O1—S1—C1A	107.5 (2)	C1A—C2A—H2A	120.00
O1—S1—C1B	109.2 (3)	C3A—C2A—H2A	120.00
O2—S1—N1	106.85 (17)	C1B—C2B—H2B	120.00
O2—S1—C1A	107.8 (3)	C3B—C2B—H2B	120.00
O2—S1—C1B	107.0 (3)	C4A—C3A—H3A	120.00
N1—S1—C1A	107.9 (3)	C2A—C3A—H3A	120.00
N1—S1—C1B	106.9 (3)	C4B—C3B—H3B	120.00
C10—O3—C13	117.3 (4)	C2B—C3B—H3B	120.00
S1—N1—C7	124.2 (3)	C3A—C4A—H4A	120.00
S1—N1—H1	112 (2)	C5A—C4A—H4A	120.00
C7—N1—H1	115 (3)	C5B—C4B—H4B	120.00
S1—C1A—C2A	122.6 (5)	C3B—C4B—H4B	120.00
S1—C1A—C6A	117.4 (5)	C6A—C5A—H5A	120.00
C2A—C1A—C6A	120.0 (6)	C4A—C5A—H5A	120.00
S1—C1B—C2B	113.8 (7)	C4B—C5B—H5B	120.00
C2B—C1B—C6B	120.0 (8)	C6B—C5B—H5B	120.00
S1—C1B—C6B	126.3 (8)	C1A—C6A—H6A	120.00
C1A—C2A—C3A	120.0 (7)	C5A—C6A—H6A	120.00
C1B—C2B—C3B	120.2 (11)	C5B—C6B—H6B	120.00
C2A—C3A—C4A	120.0 (7)	C1B—C6B—H6B	120.00
C2B—C3B—C4B	119.8 (12)	C9—C8—H8	120.00
C3A—C4A—C5A	120.0 (6)	C7—C8—H8	120.00
C3B—C4B—C5B	120.1 (9)	C8—C9—H9	120.00
C4A—C5A—C6A	120.0 (7)	C10—C9—H9	120.00
C4B—C5B—C6B	120.0 (8)	C12—C11—H11	120.00
C1A—C6A—C5A	120.0 (7)	C10—C11—H11	120.00
C1B—C6B—C5B	120.0 (10)	C11—C12—H12	120.00
N1—C7—C12	119.9 (4)	C7—C12—H12	120.00
N1—C7—C8	120.6 (4)	O3—C13—H13C	109.00
C8—C7—C12	119.4 (4)	O3—C13—H13B	109.00
C7—C8—C9	120.5 (4)	H13B—C13—H13C	109.00
C8—C9—C10	120.4 (4)	H13A—C13—H13B	109.00
O3—C10—C11	115.8 (4)	H13A—C13—H13C	109.00
O3—C10—C9	125.1 (4)	O3—C13—H13A	109.00
C9—C10—C11	119.1 (4)

O1—S1—N1—C7	−173.2 (3)	C2A—C1A—C6A—C5A	0.0 (12)
O2—S1—N1—C7	−43.9 (4)	C1A—C2A—C3A—C4A	−0.1 (14)
C1A—S1—N1—C7	71.8 (4)	C2A—C3A—C4A—C5A	0.0 (13)
O1—S1—C1A—C2A	−11.8 (7)	C3A—C4A—C5A—C6A	0.0 (12)
O1—S1—C1A—C6A	168.6 (6)	C4A—C5A—C6A—C1A	0.0 (12)
O2—S1—C1A—C2A	−142.6 (7)	N1—C7—C8—C9	175.8 (4)
O2—S1—C1A—C6A	37.8 (6)	C12—C7—C8—C9	−0.7 (6)
N1—S1—C1A—C2A	102.3 (7)	N1—C7—C12—C11	−174.4 (4)
N1—S1—C1A—C6A	−77.3 (6)	C8—C7—C12—C11	2.2 (7)
C13—O3—C10—C9	−3.3 (7)	C7—C8—C9—C10	−0.1 (7)
C13—O3—C10—C11	178.3 (4)	C8—C9—C10—O3	−178.9 (4)
S1—N1—C7—C8	67.4 (5)	C8—C9—C10—C11	−0.6 (7)
S1—N1—C7—C12	−116.2 (4)	O3—C10—C11—C12	−179.4 (4)
S1—C1A—C2A—C3A	−179.6 (7)	C9—C10—C11—C12	2.1 (7)
C6A—C1A—C2A—C3A	0.0 (13)	C10—C11—C12—C7	−2.9 (7)
S1—C1A—C6A—C5A	179.6 (6)

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x−1, y, z; (iii) x, y+1, z; (iv) −x+2, y+1/2, −z+1/2; (v) x+1/2, −y+3/2, −z; (vi) x−1/2, −y+3/2, −z; (vii) x+1, y, z; (viii) x+1/2, −y+5/2, −z; (ix) −x+1, y−1/2, −z+1/2; (x) x−1/2, −y+5/2, −z; (xi) −x+2, y−1/2, −z+1/2; (xii) x, y−1, z.

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg3 are the centroids of the C1A–C6A, C7–C12 and C1B–C6B rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^vii	0.83 (2)	2.22 (2)	3.039 (4)	170 (4)
C8—H8···Cg2^x	0.93	2.93	3.613 (5)	132
C13—H13B···Cg1^vi	0.96	2.98	3.766 (6)	140
C13—H13B···Cg3^vi	0.96	2.96	3.763 (7)	143

Symmetry codes: (vi) x−1/2, −y+3/2, −z; (vii) x+1, y, z; (x) x−1/2, −y+5/2, −z.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₃NO₃S
M_r	263.30
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	5.3094 (5), 8.5309 (10), 27.925 (3)
V (Å³)	1264.8 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.30 × 0.14 × 0.12

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.961, 0.970
No. of measured, independent and observed [I > 2σ(I)] reflections	7272, 2457, 1503
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.131, 1.02
No. of reflections	2457
No. of parameters	138
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.28
Absolute structure	Flack (1983), 961 Friedel pairs
Absolute structure parameter	0.09 (16)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg3 are the centroids of the C1A–C6A, C7–C12 and C1B–C6B rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.83 (2)	2.22 (2)	3.039 (4)	170 (4)
C8—H8···Cg2ⁱⁱ	0.93	2.93	3.613 (5)	132
C13—H13B···Cg1ⁱⁱⁱ	0.96	2.98	3.766 (6)	140
C13—H13B···Cg3ⁱⁱⁱ	0.96	2.96	3.763 (7)	143

Symmetry codes: (i) x+1, y, z; (ii) x−1/2, −y+5/2, −z; (iii) x−1/2, −y+3/2, −z.

Acknowledgements

The authors are grateful to Professor Dr Islam Ullah Khan for providing research facilities at Government College University, Lahore, Pakistan.

References

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Volume 67| Part 2| February 2011| Page o298

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