N-(2-Meth­oxy­phen­yl)benzene­sulfonamide

Aziz-ur-Rehman; Sajjad, M.A.; Akkurt, M.; Sharif, S.; Abbasi, M.A.; Khan, I.U.

doi:10.1107/S1600536810023871

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1769

doi:10.1107/S1600536810023871

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N-(2-Methoxyphenyl)benzenesulfonamide

Aziz-ur-Rehman,^a ^* Muhammad Arif Sajjad,^a Mehmet Akkurt,^b ^* Shahzad Sharif,^a Muhammad Athar Abbasi ^a and Islam Ullah Khan ^a

^aDepartment of Chemistry, Government College University, Lahore 54000, Pakistan, and ^bDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey
^*Correspondence e-mail: azizhej@hotmail.com, akkurt@erciyes.edu.tr

(Received 15 June 2010; accepted 19 June 2010; online 26 June 2010)

The asymmetric unit of the title compound, C₁₃H₁₃NO₃S, contains two crystallographically independent molecules in which the dihedral angles between the phenyl and benzene rings are 88.16 (12) and 44.50 (12)°. One of the molecules features an intramolecular N—H⋯O hydrogen bond. In the crystal, the molecules are linked into dimers by pairs of N—H⋯O hydrogen bonds. The dimers are further connected by C—H⋯O and C—H⋯π interactions, forming a three-dimensional network.

Related literature

For the biological activity of sulfonamides, see: Arshad et al. (2008 ); Gennarti et al. (1994 ); Kayser et al. (2004 ); Rough et al. (1998 ).

Experimental

Crystal data

C₁₃H₁₃NO₃S
M_r = 263.31
Monoclinic, P 2₁ /n
a = 8.7705 (2) Å
b = 28.1684 (7) Å
c = 10.7256 (3) Å
β = 105.968 (1)°
V = 2547.53 (11) Å³
Z = 8
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 296 K
0.25 × 0.17 × 0.07 mm

Data collection

Bruker APEXII CCD diffractometer
24823 measured reflections
6318 independent reflections
4145 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.113
S = 1.02
6318 reflections
333 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C7′–C12′ phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1′—H1N′⋯O2	0.828 (18)	2.310 (17)	3.074 (2)	153.6 (17)
N1—H1N⋯O1′	0.843 (17)	2.129 (17)	2.961 (2)	168.7 (17)
N1—H1N⋯O3	0.843 (17)	2.258 (18)	2.592 (2)	103.8 (14)
C4—H4⋯O2′ⁱ	0.93	2.47	3.377 (3)	167
C4′—H4′⋯Cg4ⁱⁱ	0.93	2.85	3.601 (2)	138
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x, -y+2, -z.

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: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810023871/hb5501sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810023871/hb5501Isup2.hkl

checkCIF report

Comment top

Sulfonamides are well known for their enormous potential as biologically active molecules (Rough et al., 1998) in areas such as anti-microbial (Kayser et al., 2004), anti-convulsant (Arshad et al., 2008), anti-cancer agents and for the treatment of inflammatory rheumatic and non-rheumatic processes including onsets and traumatologic lesions (Gennarti et al., 1994). In the present paper, the structure of N-(2-methoxyphenyl)benzene sulfonamide has been determined as part of a research program involving the synthesis and biological evaluation of sulfur containing compounds.

In the crystal structure of the title compound (I), (Fig. 1), there exist two independent molecules, A (with S1) and B (with S1'). Both independent molecules are bent at their S atoms with the C—S—N(H)—C torsion angles of 67.25 (15)° in molecule A and -81.17 (16)° in molecule B. The dihedral angles between the phenyl and benzene rings is 88.16 (12)° in molecule A and 44.50 (12)° in molecule B.

Molecular packing of (I) is stabilized by N–H···O, C—H···O interactions and C—H···π interactions, forming a three dimensional network (Table 1). Fig. 2 shows N—H···O hydrogen bonds between the molecules A and B in the asymmetric unit.

Related literature top

For the biological activity of sulfonamides, see: Arshad et al. (2008); Gennarti et al. (1994); Kayser et al. (2004); Rough et al. (1998).

Experimental top

A mixture benzenesulfonyl chloride (10.0 mmol; 1.45 ml), ortho-methoxy aniline (o-anisidine) (10.0 mmol; 1.12 ml), aqueous sodium carbonate (10%; 15.0 ml) and water (25 ml) was stirred for one hour at room temperature. The crude mixture was washed with water and dried. The product was dissolved in methanol and recrystallized by slow evaporation of the solvent, to generate colourless blocks of (I) in 74% yield.

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: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the two independent molecules in the asymmetric unit of (I0 with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. View of N—H···O hydrogen bonds shown as dashed lines between the two independent molecules in the asymmetric unit.

N-(2-Methoxyphenyl)benzenesulfonamide top

Crystal data top

C₁₃H₁₃NO₃S	F(000) = 1104
M_r = 263.31	D_x = 1.373 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5117 reflections
a = 8.7705 (2) Å	θ = 2.5–23.9°
b = 28.1684 (7) Å	µ = 0.25 mm⁻¹
c = 10.7256 (3) Å	T = 296 K
β = 105.968 (1)°	Block, colourless
V = 2547.53 (11) Å³	0.25 × 0.17 × 0.07 mm
Z = 8

Data collection top

Bruker APEXII CCD diffractometer	4145 reflections with I > 2σ(I)
Radiation source: sealed tube	R_int = 0.043
Graphite monochromator	θ_max = 28.3°, θ_min = 3.3°
ϕ and ω scans	h = −11→11
24823 measured reflections	k = −37→37
6318 independent reflections	l = −14→14

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0488P)² + 0.3381P] where P = (F_o² + 2F_c²)/3
6318 reflections	(Δ/σ)_max = 0.001
333 parameters	Δρ_max = 0.29 e Å⁻³
2 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₃H₁₃NO₃S	V = 2547.53 (11) Å³
M_r = 263.31	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.7705 (2) Å	µ = 0.25 mm⁻¹
b = 28.1684 (7) Å	T = 296 K
c = 10.7256 (3) Å	0.25 × 0.17 × 0.07 mm
β = 105.968 (1)°

Data collection top

Bruker APEXII CCD diffractometer	4145 reflections with I > 2σ(I)
24823 measured reflections	R_int = 0.043
6318 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	2 restraints
wR(F²) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.29 e Å⁻³
6318 reflections	Δρ_min = −0.29 e Å⁻³
333 parameters

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 on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.33115 (5)	0.81887 (2)	0.56961 (5)	0.0412 (2)
O1	0.29814 (16)	0.77142 (5)	0.59898 (15)	0.0561 (5)
O2	0.21225 (14)	0.84480 (5)	0.47617 (14)	0.0518 (5)
O3	0.68975 (15)	0.82034 (5)	0.38159 (14)	0.0507 (5)
N1	0.48440 (18)	0.81979 (6)	0.51516 (16)	0.0430 (5)
C1	0.3503 (3)	0.83266 (9)	0.8243 (2)	0.0681 (9)
C2	0.3878 (4)	0.85873 (11)	0.9379 (3)	0.0865 (11)
C3	0.4523 (3)	0.90282 (11)	0.9397 (3)	0.0764 (10)
C4	0.4848 (3)	0.92123 (8)	0.8326 (3)	0.0663 (9)
C5	0.4496 (2)	0.89536 (7)	0.7189 (2)	0.0511 (7)
C6	0.3823 (2)	0.85108 (7)	0.71581 (19)	0.0424 (6)
C7	0.6322 (2)	0.79744 (6)	0.57144 (18)	0.0388 (6)
C8	0.6717 (3)	0.77602 (7)	0.6914 (2)	0.0536 (7)
C9	0.8209 (3)	0.75621 (9)	0.7392 (3)	0.0681 (9)
C10	0.9276 (3)	0.75748 (9)	0.6684 (3)	0.0728 (9)
C11	0.8897 (2)	0.77854 (8)	0.5478 (3)	0.0596 (8)
C12	0.7411 (2)	0.79839 (6)	0.4983 (2)	0.0417 (6)
C13	0.7966 (3)	0.82674 (9)	0.3050 (2)	0.0653 (9)
S1'	0.31232 (5)	0.92918 (2)	0.25688 (5)	0.0434 (2)
O1'	0.41671 (16)	0.89021 (5)	0.30204 (16)	0.0599 (5)
O2'	0.37153 (17)	0.97058 (5)	0.21000 (15)	0.0587 (5)
O3'	−0.07087 (16)	0.95549 (5)	0.29180 (16)	0.0619 (5)
N1'	0.24881 (18)	0.94574 (6)	0.37937 (16)	0.0432 (6)
C1'	0.1023 (3)	0.86096 (7)	0.1393 (2)	0.0540 (7)
C2'	−0.0250 (3)	0.84437 (9)	0.0434 (3)	0.0675 (9)
C3'	−0.1041 (3)	0.87391 (10)	−0.0551 (2)	0.0720 (10)
C4'	−0.0567 (3)	0.92019 (9)	−0.0586 (2)	0.0687 (9)
C5'	0.0710 (3)	0.93721 (8)	0.0355 (2)	0.0542 (7)
C6'	0.1504 (2)	0.90740 (7)	0.13445 (18)	0.0412 (6)
C7'	0.1746 (2)	0.99118 (7)	0.37841 (18)	0.0415 (6)
C8'	0.2668 (3)	1.02998 (7)	0.4245 (2)	0.0570 (8)
C9'	0.1992 (3)	1.07399 (8)	0.4279 (3)	0.0711 (10)
C10'	0.0390 (3)	1.07863 (9)	0.3853 (3)	0.0694 (10)
C11'	−0.0561 (3)	1.04027 (8)	0.3392 (2)	0.0593 (8)
C12'	0.0103 (2)	0.99586 (7)	0.33485 (19)	0.0453 (7)
C13'	−0.2368 (3)	0.95970 (11)	0.2309 (3)	0.0931 (13)
H1	0.30370	0.80290	0.82150	0.0820*
H1N	0.476 (2)	0.8381 (6)	0.4514 (17)	0.0520*
H2	0.36910	0.84620	1.01260	0.1040*
H3	0.47460	0.92060	1.01560	0.0910*
H4	0.53060	0.95110	0.83600	0.0800*
H5	0.47120	0.90770	0.64510	0.0610*
H8	0.59870	0.77490	0.74000	0.0640*
H9	0.84830	0.74190	0.82050	0.0820*
H10	1.02730	0.74400	0.70170	0.0870*
H11	0.96360	0.77940	0.50010	0.0710*
H13A	0.88270	0.84670	0.35050	0.0980*
H13B	0.74210	0.84140	0.22420	0.0980*
H13C	0.83730	0.79650	0.28840	0.0980*
H1'	0.15550	0.84110	0.20650	0.0650*
H1N'	0.210 (2)	0.9225 (6)	0.4068 (19)	0.0520*
H2'	−0.05770	0.81300	0.04530	0.0810*
H3'	−0.19020	0.86250	−0.11970	0.0860*
H4'	−0.11130	0.94010	−0.12520	0.0820*
H5'	0.10370	0.96850	0.03280	0.0650*
H8'	0.37640	1.02660	0.45380	0.0680*
H9'	0.26260	1.10020	0.45910	0.0850*
H10'	−0.00680	1.10830	0.38740	0.0830*
H11'	−0.16560	1.04410	0.31080	0.0710*
H13D	−0.28950	0.97050	0.29310	0.1400*
H13E	−0.27860	0.92930	0.19770	0.1400*
H13F	−0.25390	0.98210	0.16090	0.1400*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0350 (2)	0.0431 (3)	0.0485 (3)	0.0004 (2)	0.0165 (2)	−0.0006 (2)
O1	0.0577 (9)	0.0437 (8)	0.0721 (11)	−0.0080 (7)	0.0265 (8)	−0.0027 (7)
O2	0.0329 (7)	0.0658 (9)	0.0574 (9)	0.0070 (6)	0.0137 (6)	0.0053 (7)
O3	0.0403 (7)	0.0654 (9)	0.0508 (8)	0.0048 (7)	0.0200 (6)	0.0008 (7)
N1	0.0351 (8)	0.0546 (10)	0.0419 (9)	0.0105 (7)	0.0148 (7)	0.0079 (7)
C1	0.0940 (18)	0.0595 (15)	0.0663 (16)	−0.0063 (13)	0.0479 (14)	−0.0035 (12)
C2	0.114 (2)	0.098 (2)	0.0639 (18)	0.0013 (19)	0.0522 (17)	−0.0102 (16)
C3	0.0722 (17)	0.093 (2)	0.0642 (17)	0.0062 (15)	0.0193 (14)	−0.0275 (15)
C4	0.0516 (13)	0.0576 (15)	0.0858 (19)	−0.0042 (11)	0.0126 (13)	−0.0189 (13)
C5	0.0466 (11)	0.0494 (12)	0.0588 (14)	−0.0019 (10)	0.0169 (10)	0.0001 (10)
C6	0.0410 (10)	0.0436 (11)	0.0469 (11)	0.0050 (8)	0.0195 (9)	0.0004 (9)
C7	0.0333 (9)	0.0354 (10)	0.0463 (11)	0.0035 (8)	0.0084 (8)	−0.0031 (8)
C8	0.0521 (12)	0.0505 (13)	0.0560 (13)	0.0049 (10)	0.0114 (10)	0.0089 (10)
C9	0.0635 (15)	0.0601 (15)	0.0686 (16)	0.0082 (12)	−0.0022 (13)	0.0190 (12)
C10	0.0448 (12)	0.0618 (16)	0.101 (2)	0.0167 (11)	0.0017 (13)	0.0162 (14)
C11	0.0365 (11)	0.0537 (13)	0.0886 (18)	0.0076 (10)	0.0174 (11)	−0.0007 (12)
C12	0.0328 (9)	0.0362 (10)	0.0543 (12)	0.0000 (8)	0.0091 (8)	−0.0062 (9)
C13	0.0596 (13)	0.0753 (16)	0.0730 (16)	−0.0073 (12)	0.0383 (13)	−0.0062 (13)
S1'	0.0351 (2)	0.0419 (3)	0.0543 (3)	0.0050 (2)	0.0143 (2)	0.0066 (2)
O1'	0.0452 (8)	0.0579 (9)	0.0768 (11)	0.0199 (7)	0.0172 (7)	0.0121 (8)
O2'	0.0542 (8)	0.0521 (9)	0.0770 (11)	−0.0079 (7)	0.0304 (8)	0.0062 (8)
O3'	0.0368 (7)	0.0664 (10)	0.0780 (11)	−0.0051 (7)	0.0085 (7)	−0.0066 (8)
N1'	0.0405 (9)	0.0425 (10)	0.0463 (10)	0.0013 (7)	0.0113 (7)	0.0067 (7)
C1'	0.0641 (13)	0.0433 (12)	0.0555 (13)	0.0007 (10)	0.0178 (11)	0.0076 (10)
C2'	0.0769 (16)	0.0555 (15)	0.0686 (16)	−0.0142 (12)	0.0174 (14)	−0.0068 (12)
C3'	0.0709 (16)	0.0831 (19)	0.0549 (15)	−0.0082 (14)	0.0053 (12)	−0.0136 (13)
C4'	0.0729 (16)	0.0741 (17)	0.0503 (14)	0.0100 (13)	0.0023 (12)	0.0064 (12)
C5'	0.0635 (13)	0.0466 (12)	0.0515 (13)	0.0081 (10)	0.0141 (11)	0.0089 (10)
C6'	0.0431 (10)	0.0406 (11)	0.0429 (11)	0.0061 (8)	0.0168 (9)	0.0027 (8)
C7'	0.0403 (10)	0.0456 (11)	0.0391 (10)	0.0035 (8)	0.0120 (8)	0.0001 (8)
C8'	0.0460 (11)	0.0542 (13)	0.0696 (15)	−0.0039 (10)	0.0141 (11)	−0.0114 (11)
C9'	0.0695 (16)	0.0507 (14)	0.094 (2)	−0.0067 (12)	0.0242 (14)	−0.0202 (13)
C10'	0.0766 (17)	0.0563 (15)	0.0807 (18)	0.0155 (13)	0.0306 (14)	−0.0106 (13)
C11'	0.0474 (12)	0.0714 (16)	0.0611 (15)	0.0170 (11)	0.0183 (11)	−0.0006 (12)
C12'	0.0389 (10)	0.0543 (13)	0.0433 (11)	0.0013 (9)	0.0122 (9)	−0.0005 (9)
C13'	0.0414 (13)	0.098 (2)	0.123 (3)	−0.0113 (13)	−0.0060 (14)	−0.0054 (18)

Geometric parameters (Å, º) top

S1—O1	1.4212 (15)	C5—H5	0.9300
S1—O2	1.4319 (15)	C8—H8	0.9300
S1—N1	1.6063 (17)	C9—H9	0.9300
S1—C6	1.760 (2)	C10—H10	0.9300
S1'—C6'	1.7582 (19)	C11—H11	0.9300
S1'—N1'	1.6299 (17)	C13—H13A	0.9600
S1'—O1'	1.4260 (15)	C13—H13C	0.9600
S1'—O2'	1.4235 (15)	C13—H13B	0.9600
O3—C12	1.357 (2)	C1'—C2'	1.375 (4)
O3—C13	1.417 (3)	C1'—C6'	1.380 (3)
O3'—C12'	1.354 (2)	C2'—C3'	1.374 (4)
O3'—C13'	1.427 (3)	C3'—C4'	1.372 (4)
N1—C7	1.418 (2)	C4'—C5'	1.372 (3)
N1—H1N	0.843 (17)	C5'—C6'	1.382 (3)
N1'—C7'	1.435 (3)	C7'—C12'	1.394 (3)
N1'—H1N'	0.828 (18)	C7'—C8'	1.369 (3)
C1—C2	1.383 (4)	C8'—C9'	1.379 (3)
C1—C6	1.372 (3)	C9'—C10'	1.359 (4)
C2—C3	1.363 (4)	C10'—C11'	1.371 (4)
C3—C4	1.360 (4)	C11'—C12'	1.386 (3)
C4—C5	1.381 (4)	C1'—H1'	0.9300
C5—C6	1.376 (3)	C2'—H2'	0.9300
C7—C12	1.393 (3)	C3'—H3'	0.9300
C7—C8	1.376 (3)	C4'—H4'	0.9300
C8—C9	1.385 (4)	C5'—H5'	0.9300
C9—C10	1.358 (4)	C8'—H8'	0.9300
C10—C11	1.378 (4)	C9'—H9'	0.9300
C11—C12	1.383 (3)	C10'—H10'	0.9300
C1—H1	0.9300	C11'—H11'	0.9300
C2—H2	0.9300	C13'—H13D	0.9600
C3—H3	0.9300	C13'—H13E	0.9600
C4—H4	0.9300	C13'—H13F	0.9600

O1—S1—O2	118.77 (9)	C9—C10—H10	120.00
O1—S1—N1	109.73 (9)	C11—C10—H10	120.00
O1—S1—C6	107.75 (9)	C10—C11—H11	120.00
O2—S1—N1	104.98 (9)	C12—C11—H11	120.00
O2—S1—C6	108.59 (9)	O3—C13—H13A	109.00
N1—S1—C6	106.38 (9)	H13A—C13—H13C	109.00
O1'—S1'—O2'	119.21 (9)	H13B—C13—H13C	109.00
O1'—S1'—N1'	106.05 (9)	H13A—C13—H13B	109.00
O1'—S1'—C6'	107.24 (9)	O3—C13—H13B	109.00
O2'—S1'—N1'	106.80 (9)	O3—C13—H13C	110.00
O2'—S1'—C6'	108.68 (9)	C2'—C1'—C6'	119.2 (2)
N1'—S1'—C6'	108.48 (9)	C1'—C2'—C3'	120.3 (2)
C12—O3—C13	119.21 (16)	C2'—C3'—C4'	120.3 (2)
C12'—O3'—C13'	117.44 (18)	C3'—C4'—C5'	120.3 (2)
S1—N1—C7	126.62 (14)	C4'—C5'—C6'	119.3 (2)
C7—N1—H1N	118.8 (12)	S1'—C6'—C5'	119.63 (16)
S1—N1—H1N	114.2 (12)	C1'—C6'—C5'	120.68 (19)
S1'—N1'—C7'	120.30 (13)	S1'—C6'—C1'	119.68 (15)
C7'—N1'—H1N'	118.5 (13)	C8'—C7'—C12'	119.96 (19)
S1'—N1'—H1N'	109.0 (13)	N1'—C7'—C8'	119.22 (18)
C2—C1—C6	119.5 (2)	N1'—C7'—C12'	120.80 (17)
C1—C2—C3	119.6 (3)	C7'—C8'—C9'	120.8 (2)
C2—C3—C4	121.2 (3)	C8'—C9'—C10'	119.3 (2)
C3—C4—C5	119.8 (2)	C9'—C10'—C11'	121.0 (2)
C4—C5—C6	119.3 (2)	C10'—C11'—C12'	120.3 (2)
C1—C6—C5	120.58 (19)	C7'—C12'—C11'	118.65 (19)
S1—C6—C1	119.96 (16)	O3'—C12'—C7'	115.67 (17)
S1—C6—C5	119.42 (15)	O3'—C12'—C11'	125.68 (18)
C8—C7—C12	119.97 (19)	C2'—C1'—H1'	120.00
N1—C7—C8	123.93 (19)	C6'—C1'—H1'	120.00
N1—C7—C12	116.10 (16)	C1'—C2'—H2'	120.00
C7—C8—C9	119.5 (2)	C3'—C2'—H2'	120.00
C8—C9—C10	120.6 (3)	C2'—C3'—H3'	120.00
C9—C10—C11	120.7 (3)	C4'—C3'—H3'	120.00
C10—C11—C12	119.5 (2)	C3'—C4'—H4'	120.00
C7—C12—C11	119.7 (2)	C5'—C4'—H4'	120.00
O3—C12—C7	115.04 (16)	C4'—C5'—H5'	120.00
O3—C12—C11	125.23 (19)	C6'—C5'—H5'	120.00
C6—C1—H1	120.00	C7'—C8'—H8'	120.00
C2—C1—H1	120.00	C9'—C8'—H8'	120.00
C3—C2—H2	120.00	C8'—C9'—H9'	120.00
C1—C2—H2	120.00	C10'—C9'—H9'	120.00
C4—C3—H3	119.00	C9'—C10'—H10'	119.00
C2—C3—H3	119.00	C11'—C10'—H10'	120.00
C5—C4—H4	120.00	C10'—C11'—H11'	120.00
C3—C4—H4	120.00	C12'—C11'—H11'	120.00
C4—C5—H5	120.00	O3'—C13'—H13D	109.00
C6—C5—H5	120.00	O3'—C13'—H13E	109.00
C7—C8—H8	120.00	O3'—C13'—H13F	109.00
C9—C8—H8	120.00	H13D—C13'—H13E	109.00
C10—C9—H9	120.00	H13D—C13'—H13F	109.00
C8—C9—H9	120.00	H13E—C13'—H13F	110.00

O1—S1—N1—C7	−49.05 (18)	C4—C5—C6—S1	177.86 (17)
O2—S1—N1—C7	−177.75 (15)	C4—C5—C6—C1	0.0 (3)
C6—S1—N1—C7	67.25 (18)	C12—C7—C8—C9	1.0 (3)
O1—S1—C6—C1	−14.8 (2)	N1—C7—C12—O3	−0.7 (2)
O1—S1—C6—C5	167.32 (15)	N1—C7—C8—C9	−178.4 (2)
O2—S1—C6—C1	115.07 (18)	C8—C7—C12—O3	179.93 (17)
O2—S1—C6—C5	−62.83 (17)	C8—C7—C12—C11	−1.2 (3)
N1—S1—C6—C1	−132.41 (18)	N1—C7—C12—C11	178.21 (18)
N1—S1—C6—C5	49.70 (18)	C7—C8—C9—C10	−0.5 (4)
N1'—S1'—C6'—C5'	95.33 (18)	C8—C9—C10—C11	0.1 (4)
O1'—S1'—N1'—C7'	163.92 (14)	C9—C10—C11—C12	−0.3 (4)
O2'—S1'—N1'—C7'	35.80 (17)	C10—C11—C12—C7	0.8 (3)
C6'—S1'—N1'—C7'	−81.17 (16)	C10—C11—C12—O3	179.6 (2)
O1'—S1'—C6'—C1'	30.5 (2)	C6'—C1'—C2'—C3'	−0.7 (4)
O1'—S1'—C6'—C5'	−150.54 (17)	C2'—C1'—C6'—S1'	179.66 (19)
O2'—S1'—C6'—C1'	160.64 (17)	C2'—C1'—C6'—C5'	0.7 (3)
O2'—S1'—C6'—C5'	−20.4 (2)	C1'—C2'—C3'—C4'	0.0 (4)
N1'—S1'—C6'—C1'	−83.61 (19)	C2'—C3'—C4'—C5'	0.7 (4)
C13—O3—C12—C7	174.60 (17)	C3'—C4'—C5'—C6'	−0.6 (4)
C13—O3—C12—C11	−4.2 (3)	C4'—C5'—C6'—S1'	−179.01 (18)
C13'—O3'—C12'—C7'	−172.1 (2)	C4'—C5'—C6'—C1'	−0.1 (3)
C13'—O3'—C12'—C11'	8.2 (3)	N1'—C7'—C8'—C9'	−178.5 (2)
S1—N1—C7—C8	−8.1 (3)	C12'—C7'—C8'—C9'	−0.3 (3)
S1—N1—C7—C12	172.47 (14)	N1'—C7'—C12'—O3'	−1.5 (3)
S1'—N1'—C7'—C8'	−88.1 (2)	N1'—C7'—C12'—C11'	178.22 (18)
S1'—N1'—C7'—C12'	93.8 (2)	C8'—C7'—C12'—O3'	−179.62 (18)
C2—C1—C6—C5	−0.7 (4)	C8'—C7'—C12'—C11'	0.1 (3)
C6—C1—C2—C3	1.6 (4)	C7'—C8'—C9'—C10'	0.3 (4)
C2—C1—C6—S1	−178.6 (2)	C8'—C9'—C10'—C11'	0.1 (4)
C1—C2—C3—C4	−1.9 (5)	C9'—C10'—C11'—C12'	−0.3 (4)
C2—C3—C4—C5	1.2 (4)	C10'—C11'—C12'—O3'	179.9 (2)
C3—C4—C5—C6	−0.2 (4)	C10'—C11'—C12'—C7'	0.2 (3)

Hydrogen-bond geometry (Å, º) top

Cg4 is the centroid of the C7'–C12' phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1′—H1N′···O2	0.828 (18)	2.310 (17)	3.074 (2)	153.6 (17)
N1—H1N···O1′	0.843 (17)	2.129 (17)	2.961 (2)	168.7 (17)
N1—H1N···O3	0.843 (17)	2.258 (18)	2.592 (2)	103.8 (14)
C4—H4···O2′ⁱ	0.93	2.47	3.377 (3)	167
C4′—H4′···Cg4ⁱⁱ	0.93	2.85	3.601 (2)	138

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₃NO₃S
M_r	263.31
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	8.7705 (2), 28.1684 (7), 10.7256 (3)
β (°)	105.968 (1)
V (Å³)	2547.53 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.25 × 0.17 × 0.07

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	24823, 6318, 4145
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.113, 1.02
No. of reflections	6318
No. of parameters	333
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.29

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg4 is the centroid of the C7'–C12' phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1'—H1N'···O2	0.828 (18)	2.310 (17)	3.074 (2)	153.6 (17)
N1—H1N···O1'	0.843 (17)	2.129 (17)	2.961 (2)	168.7 (17)
N1—H1N···O3	0.843 (17)	2.258 (18)	2.592 (2)	103.8 (14)
C4—H4···O2'ⁱ	0.93	2.47	3.377 (3)	167
C4'—H4'···Cg4ⁱⁱ	0.93	2.85	3.601 (2)	138

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

Acknowledgements

The authors are grateful to the Higher Education Commission of Pakistan for financial support to purchase the diffractometer.

References

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