N-{4-[(2-Meth­oxy­phen­yl)sulfamo­yl]phen­yl}acetamide

Ahmad, S.; Farrukh, M.A.; Qureshi, F.A.; Adnan, A.; Akkurt, M.

doi:10.1107/S1600536811000432

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 2| February 2011| Pages o303-o304

doi:10.1107/S1600536811000432

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N-{4-[(2-Methoxyphenyl)sulfamoyl]phenyl}acetamide

Saba Ahmad,^a Muhammad Akhyar Farrukh,^a ‡ Fahim Ashraf Qureshi,^a Ahmad Adnan ^a and Mehmet Akkurt ^b ^*

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

(Received 28 December 2010; accepted 5 January 2011; online 8 January 2011)

In the title compound, C₁₅H₁₆N₂O₄S, the S atom has a distorted tetrahedral geometry [maximum deviation: O—S—O = 118.25 (7)°]. The two aromatic rings make a dihedral angle of 62.67 (10)° with each other. An intramolecular N—H⋯O hydrogen bond forms an S(6) ring motif. In the crystal, molecules form centrosymmetric dimers via pairwise N—H⋯O interactions, forming an R₂²(8) ring motif, and these dimers are connected by N—H⋯O hydrogen bonds, generating a three-dimensional network. Furthermore, a weak C—H⋯π interaction helps to reinforce the crystal structure. The O atom in the acetamide group is disordered over two positions with major and minor occupancies of 0.52 (5) and 0.48 (5), respectively.

Related literature

For background and the biological activity of sulfonamide and its derivatives, see: Korolkovas (1988 ); Mandell & Sande (1992 ); Pandya et al. (2003 ); Supuran & Scozzafava (2001 ). For related structures, see: Aziz-ur-Rehman et al. (2010a ,b ,c); Khan et al. (2010 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₅H₁₆N₂O₄S
M_r = 320.37
Orthorhombic, P b c a
a = 15.7277 (4) Å
b = 11.8351 (3) Å
c = 16.5247 (4) Å
V = 3075.89 (13) Å³
Z = 8
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 296 K
0.24 × 0.18 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer
15586 measured reflections
3788 independent reflections
2800 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.118
S = 1.03
3788 reflections
220 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C9–C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN1⋯O3ⁱ	0.811 (19)	2.191 (19)	2.995 (2)	171.0 (19)
N2—HN2⋯O4	0.823 (18)	2.359 (19)	2.6551 (19)	102.0 (15)
N2—HN2⋯O2ⁱⁱ	0.823 (18)	2.259 (18)	3.0482 (18)	160.6 (18)
C5—H5⋯Cg2ⁱⁱⁱ	0.93	2.90	3.715 (2)	148
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z; (iii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (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/S1600536811000432/hg2782sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811000432/hg2782Isup2.hkl

checkCIF report

Comment top

Sulfonamides are very important because of their antibacterial and enzyme inhibitor properties as well as their extensive use in medicine (Pandya et al., 2003). Sulfonamides also exhibit antimicrobial activity (Korolkovas, 1988; Mandell & Sande, 1992) and have their properties to inhibit the growth of tumor cells (Supuran & Scozzafava, 2001). As a contribution to a structural study of sulfonamide derivatives (Khan et al., 2010; Aziz-ur-Rehman et al., 2010a,b,c), we report here the title compound, N-{4-[(2-methoxyphenyl)sulfamoyl]phenyl}acetamide, (I).

In the title molecule (I), (Fig. 1), the S atom has a distorted tetrahedral geometry [maximum deviation: O1—S1—O2 = 118.25 (7) °]. The molecule is twisted at the S atom, with a C1—S1—N2—C9 torsion angle of 56.88 (14) °. The dihedral angle formed between the benzene (C1–C6) and phenyl (C9–C14) rings in (I) is 62.67 (10)°.

An intramolecular N2—HN2···O4 hydrogen bond contribute to the stabilization of the molecular conformation, forming an S(6) ring motif (Table 1; Bernstein et al., 1995). In the crystal structure, the molecules of (I) are dimerized due to the intermolecular N—H···O hydrogen bonding (Table 1, Fig. 2) forming an R₂²(8) ring motif (Table 1; Bernstein et al., 1995) and these dimers are connected by N—H···O hydrogen bonds, generating a three-dimensional network (Table 1, Fig. 2).

Related literature top

For background and the biological activity of sulfonamide and its derivatives, see: Korolkovas (1988); Mandell & Sande (1992); Pandya et al. (2003); Supuran & Scozzafava (2001). For related structures, see: Aziz-ur-Rehman et al. (2010a,b,c); Khan et al. (2010). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

5 mmol of 2-methoxyaniline was dissolved in 20 ml of distilled water then 5 mmol of 4-acetamidobenzenesulfonyl chloride was addedd. The reaction mixture was stirred for about 2–3 h while the pH of the reaction mixture was maintained between 8–10 using 3% Na₂CO₃. The reaction was monitored by TLC. The precipitate formed was filtered, washed with distilled water, dried and recrystallized by using methanol.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); 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. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level. Only the major component of the disorder is shown.
	Fig. 2. View of the dimeric N—H···O interactions between the molecules and the other hydrogen bonding interactions in the unit cell. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity and only the major component of the disorder is shown.

N-{4-[(2-Methoxyphenyl)sulfamoyl]phenyl}acetamide top

Crystal data top

C₁₅H₁₆N₂O₄S	F(000) = 1344
M_r = 320.37	D_x = 1.384 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4792 reflections
a = 15.7277 (4) Å	θ = 2.5–27.6°
b = 11.8351 (3) Å	µ = 0.23 mm⁻¹
c = 16.5247 (4) Å	T = 296 K
V = 3075.89 (13) Å³	Block, colourless
Z = 8	0.24 × 0.18 × 0.09 mm

Data collection top

Bruker APEXII CCD diffractometer	2800 reflections with I > 2σ(I)
Radiation source: sealed tube	R_int = 0.035
Graphite monochromator	θ_max = 28.3°, θ_min = 3.4°
ϕ and ω scans	h = −17→20
15586 measured reflections	k = −14→15
3788 independent reflections	l = −22→19

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0648P)² + 0.4113P] where P = (F_o² + 2F_c²)/3
3788 reflections	(Δ/σ)_max < 0.001
220 parameters	Δρ_max = 0.35 e Å⁻³
2 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₅H₁₆N₂O₄S	V = 3075.89 (13) Å³
M_r = 320.37	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 15.7277 (4) Å	µ = 0.23 mm⁻¹
b = 11.8351 (3) Å	T = 296 K
c = 16.5247 (4) Å	0.24 × 0.18 × 0.09 mm

Data collection top

Bruker APEXII CCD diffractometer	2800 reflections with I > 2σ(I)
15586 measured reflections	R_int = 0.035
3788 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	2 restraints
wR(F²) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.35 e Å⁻³
3788 reflections	Δρ_min = −0.28 e Å⁻³
220 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	Occ. (<1)
S1	0.56431 (2)	0.08868 (3)	0.10743 (2)	0.0342 (1)
O1A	0.1823 (9)	0.3615 (19)	0.1605 (11)	0.071 (3)	0.52 (5)
O2	0.52415 (8)	−0.01701 (9)	0.09026 (8)	0.0464 (4)
O3	0.63163 (8)	0.09054 (10)	0.16600 (8)	0.0464 (4)
O4	0.52707 (9)	0.29215 (11)	−0.06451 (9)	0.0603 (5)
N1	0.30275 (9)	0.40934 (13)	0.22401 (10)	0.0439 (5)
N2	0.60326 (9)	0.13213 (11)	0.02165 (8)	0.0354 (4)
C1	0.48747 (10)	0.18646 (13)	0.13933 (9)	0.0336 (5)
C2	0.50585 (11)	0.26178 (14)	0.20091 (11)	0.0436 (5)
C3	0.44366 (11)	0.33454 (15)	0.22693 (12)	0.0472 (6)
C4	0.36276 (10)	0.33370 (13)	0.19280 (10)	0.0367 (5)
C5	0.34562 (11)	0.25968 (15)	0.12988 (11)	0.0462 (6)
C6	0.40841 (12)	0.18647 (16)	0.10356 (11)	0.0453 (6)
C7	0.21664 (12)	0.40990 (17)	0.21306 (12)	0.0521 (6)
C8	0.17075 (13)	0.49861 (19)	0.26052 (14)	0.0639 (8)
C9	0.64089 (10)	0.24249 (13)	0.01705 (10)	0.0374 (5)
C10	0.60126 (13)	0.32392 (14)	−0.03012 (12)	0.0474 (6)
C11	0.64036 (18)	0.42861 (17)	−0.03904 (15)	0.0696 (9)
C12	0.71585 (18)	0.4507 (2)	0.00053 (17)	0.0790 (10)
C13	0.75310 (15)	0.3717 (2)	0.04807 (14)	0.0687 (8)
C14	0.71651 (12)	0.26592 (17)	0.05603 (12)	0.0511 (6)
C15	0.4802 (2)	0.3729 (2)	−0.10987 (18)	0.0967 (13)
O1B	0.1793 (9)	0.326 (2)	0.1809 (15)	0.083 (3)	0.48 (5)
HN1	0.3247 (12)	0.4533 (16)	0.2553 (11)	0.055 (6)*
HN2	0.5717 (11)	0.1143 (16)	−0.0160 (11)	0.047 (6)*
H3	0.45580	0.38550	0.26820	0.0570*
H5	0.29230	0.25920	0.10550	0.0550*
H6	0.39710	0.13680	0.06130	0.0540*
H8A	0.20100	0.56890	0.25660	0.0960*
H8B	0.16740	0.47600	0.31620	0.0960*
H8C	0.11440	0.50790	0.23920	0.0960*
H10D	0.46860	0.43760	−0.07660	0.1450*
H10E	0.42760	0.33990	−0.12750	0.1450*
H10F	0.51290	0.39580	−0.15620	0.1450*
H11	0.61570	0.48360	−0.07160	0.0840*
H12	0.74150	0.52090	−0.00560	0.0950*
H13	0.80320	0.38860	0.07540	0.0820*
H14	0.74270	0.21090	0.08750	0.0610*
H2	0.55960	0.26310	0.22430	0.0520*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0362 (2)	0.0288 (2)	0.0376 (2)	0.0018 (2)	−0.0030 (2)	0.0035 (2)
O1A	0.037 (4)	0.095 (7)	0.082 (5)	0.008 (3)	−0.019 (3)	−0.040 (5)
O2	0.0568 (8)	0.0291 (6)	0.0532 (7)	−0.0046 (5)	−0.0027 (6)	0.0050 (5)
O3	0.0457 (7)	0.0455 (7)	0.0480 (7)	0.0078 (5)	−0.0120 (6)	0.0032 (5)
O4	0.0614 (9)	0.0490 (8)	0.0704 (10)	0.0066 (7)	−0.0070 (7)	0.0153 (7)
N1	0.0383 (8)	0.0469 (9)	0.0464 (8)	0.0019 (6)	−0.0032 (6)	−0.0141 (7)
N2	0.0367 (7)	0.0320 (7)	0.0374 (7)	−0.0013 (6)	0.0001 (6)	−0.0036 (6)
C1	0.0340 (8)	0.0343 (8)	0.0325 (8)	−0.0002 (6)	0.0015 (6)	0.0006 (6)
C2	0.0345 (8)	0.0467 (9)	0.0497 (10)	−0.0020 (7)	−0.0064 (7)	−0.0103 (8)
C3	0.0407 (9)	0.0509 (10)	0.0499 (10)	−0.0020 (8)	−0.0048 (8)	−0.0192 (8)
C4	0.0359 (8)	0.0394 (8)	0.0348 (8)	−0.0011 (7)	0.0014 (6)	−0.0026 (6)
C5	0.0377 (9)	0.0560 (11)	0.0449 (9)	0.0068 (8)	−0.0111 (7)	−0.0119 (8)
C6	0.0431 (9)	0.0524 (11)	0.0403 (9)	0.0058 (8)	−0.0092 (7)	−0.0143 (8)
C7	0.0390 (9)	0.0689 (13)	0.0483 (10)	0.0050 (9)	0.0014 (8)	−0.0119 (9)
C8	0.0514 (12)	0.0760 (14)	0.0644 (13)	0.0240 (11)	−0.0038 (10)	−0.0101 (11)
C9	0.0393 (8)	0.0345 (8)	0.0384 (8)	−0.0053 (7)	0.0122 (7)	−0.0070 (7)
C10	0.0567 (11)	0.0363 (9)	0.0493 (10)	−0.0026 (8)	0.0133 (9)	−0.0009 (8)
C11	0.1000 (19)	0.0387 (11)	0.0702 (14)	−0.0098 (11)	0.0275 (13)	0.0028 (10)
C12	0.102 (2)	0.0542 (13)	0.0809 (17)	−0.0404 (14)	0.0384 (16)	−0.0221 (13)
C13	0.0634 (14)	0.0780 (15)	0.0647 (13)	−0.0357 (12)	0.0228 (11)	−0.0303 (13)
C14	0.0432 (10)	0.0601 (12)	0.0499 (10)	−0.0109 (9)	0.0097 (8)	−0.0145 (9)
C15	0.128 (3)	0.0751 (16)	0.087 (2)	0.0394 (18)	−0.0316 (18)	0.0058 (14)
O1B	0.050 (3)	0.091 (7)	0.109 (7)	−0.021 (4)	0.023 (4)	−0.047 (5)

Geometric parameters (Å, º) top

S1—O2	1.4297 (12)	C9—C14	1.381 (2)
S1—O3	1.4347 (13)	C9—C10	1.387 (2)
S1—N2	1.6276 (14)	C10—C11	1.391 (3)
S1—C1	1.7543 (16)	C11—C12	1.380 (4)
O1A—C7	1.172 (19)	C12—C13	1.355 (4)
O1B—C7	1.27 (2)	C13—C14	1.384 (3)
O4—C15	1.421 (3)	C2—H2	0.9300
O4—C10	1.351 (2)	C3—H3	0.9300
N1—C4	1.399 (2)	C5—H5	0.9300
N1—C7	1.366 (2)	C6—H6	0.9300
N2—C9	1.436 (2)	C8—H8A	0.9600
N1—HN1	0.811 (19)	C8—H8B	0.9600
N2—HN2	0.823 (18)	C8—H8C	0.9600
C1—C2	1.383 (2)	C11—H11	0.9300
C1—C6	1.377 (2)	C12—H12	0.9300
C2—C3	1.372 (2)	C13—H13	0.9300
C3—C4	1.392 (2)	C14—H14	0.9300
C4—C5	1.386 (2)	C15—H10D	0.9600
C5—C6	1.384 (3)	C15—H10E	0.9600
C7—C8	1.496 (3)	C15—H10F	0.9600

S1···H14	3.1700	C8···H10E^ix	3.0800
S1···H3ⁱ	3.1800	C11···H10F	2.8100
S1···H13ⁱⁱ	3.2000	C11···H10D	2.7700
O1A···C5	2.882 (16)	C11···H10D^xii	3.0200
O1A···C10ⁱⁱⁱ	3.33 (2)	C13···H8B^xiii	2.8900
O1A···N2ⁱⁱⁱ	3.257 (18)	C13···H5^vii	3.0400
O1A···C9ⁱⁱⁱ	3.248 (19)	C13···H6^vii	2.9000
O1B···C5	2.858 (16)	C14···H5^vii	2.9400
O1B···C10ⁱⁱⁱ	3.30 (2)	C15···H11	2.5800
O2···N2^iv	3.0482 (18)	HN1···H8A	2.3800
O2···O2^iv	3.1045 (19)	HN1···O3^vi	2.191 (19)
O3···N1ⁱ	2.995 (2)	HN1···H3	2.2200
O3···C14	3.065 (2)	H2···O1B^xiii	2.5600
O4···N2	2.6551 (19)	H2···O3	2.5300
O1A···H5	2.3000	HN2···O4	2.359 (19)
O1B···H2^v	2.5600	HN2···O2^iv	2.259 (18)
O1B···H5	2.3100	H3···S1^vi	3.1800
O2···H3ⁱ	2.6300	H3···O2^vi	2.6300
O2···HN2^iv	2.259 (18)	H3···HN1	2.2200
O2···H6	2.7500	H5···O1A	2.3000
O3···H14	2.6000	H5···C7	2.7800
O3···H2	2.5300	H5···O1B	2.3100
O3···HN1ⁱ	2.191 (19)	H5···C13ⁱⁱⁱ	3.0400
O4···HN2	2.359 (19)	H5···C14ⁱⁱⁱ	2.9400
N1···O3^vi	2.995 (2)	H6···C13ⁱⁱⁱ	2.9000
N2···O1A^vii	3.257 (18)	H6···O2	2.7500
N2···O2^iv	3.0482 (18)	H8A···HN1	2.3800
N2···O4	2.6551 (19)	H8B···C13^v	2.8900
N2···H12ⁱⁱ	2.8100	H10D···C11^xii	3.0200
C2···C15^viii	3.533 (3)	H10D···C11	2.7700
C5···O1A	2.882 (16)	H10D···H11	2.3800
C5···O1B	2.858 (16)	H10E···C8^xi	3.0800
C6···C13ⁱⁱⁱ	3.566 (3)	H10F···H11	2.3800
C8···C15^ix	3.541 (4)	H10F···C2^x	3.0100
C9···O1A^vii	3.248 (19)	H10F···C11	2.8100
C10···O1A^vii	3.33 (2)	H11···C15	2.5800
C10···O1B^vii	3.30 (2)	H11···H10D	2.3800
C13···C6^vii	3.566 (3)	H11···H10F	2.3800
C14···O3	3.065 (2)	H11···C4^xii	2.9700
C15···C2^x	3.533 (3)	H12···N2^xiv	2.8100
C15···C8^xi	3.541 (4)	H13···S1^xiv	3.2000
C2···H10F^viii	3.0100	H14···S1	3.1700
C4···H11^xii	2.9700	H14···O3	2.6000
C7···H5	2.7800

O2—S1—O3	118.25 (7)	C9—C10—C11	118.66 (19)
O2—S1—N2	105.66 (7)	C10—C11—C12	119.9 (2)
O2—S1—C1	109.42 (7)	C11—C12—C13	121.1 (2)
O3—S1—N2	107.75 (7)	C12—C13—C14	120.0 (2)
O3—S1—C1	107.19 (7)	C9—C14—C13	119.70 (18)
N2—S1—C1	108.21 (7)	C1—C2—H2	120.00
C10—O4—C15	118.87 (16)	C3—C2—H2	120.00
C4—N1—C7	128.52 (16)	C2—C3—H3	119.00
S1—N2—C9	119.25 (11)	C4—C3—H3	119.00
C4—N1—HN1	111.0 (13)	C4—C5—H5	120.00
C7—N1—HN1	120.2 (13)	C6—C5—H5	120.00
S1—N2—HN2	110.5 (13)	C1—C6—H6	120.00
C9—N2—HN2	116.2 (13)	C5—C6—H6	120.00
S1—C1—C6	119.55 (13)	C7—C8—H8A	109.00
C2—C1—C6	120.30 (15)	C7—C8—H8B	109.00
S1—C1—C2	120.14 (12)	C7—C8—H8C	109.00
C1—C2—C3	119.07 (16)	H8A—C8—H8B	109.00
C2—C3—C4	121.34 (17)	H8A—C8—H8C	109.00
N1—C4—C3	117.56 (15)	H8B—C8—H8C	109.00
C3—C4—C5	119.10 (15)	C10—C11—H11	120.00
N1—C4—C5	123.34 (15)	C12—C11—H11	120.00
C4—C5—C6	119.52 (16)	C11—C12—H12	119.00
C1—C6—C5	120.64 (17)	C13—C12—H12	120.00
O1B—C7—C8	123.0 (8)	C12—C13—H13	120.00
O1A—C7—N1	123.5 (8)	C14—C13—H13	120.00
O1A—C7—C8	120.6 (9)	C9—C14—H14	120.00
N1—C7—C8	114.34 (17)	C13—C14—H14	120.00
O1B—C7—N1	120.7 (8)	O4—C15—H10D	109.00
N2—C9—C14	120.87 (15)	O4—C15—H10E	109.00
C10—C9—C14	120.64 (16)	O4—C15—H10F	109.00
N2—C9—C10	118.45 (15)	H10D—C15—H10E	110.00
O4—C10—C9	115.53 (15)	H10D—C15—H10F	109.00
O4—C10—C11	125.81 (18)	H10E—C15—H10F	110.00

O2—S1—N2—C9	173.98 (12)	S1—C1—C6—C5	177.38 (14)
O3—S1—N2—C9	−58.72 (13)	C6—C1—C2—C3	1.4 (3)
C1—S1—N2—C9	56.88 (14)	C1—C2—C3—C4	0.2 (3)
O2—S1—C1—C2	141.15 (13)	C2—C3—C4—C5	−1.7 (3)
O3—S1—C1—C2	11.77 (15)	C2—C3—C4—N1	178.84 (16)
N2—S1—C1—C2	−104.20 (14)	C3—C4—C5—C6	1.5 (3)
O2—S1—C1—C6	−37.82 (16)	N1—C4—C5—C6	−179.03 (16)
O3—S1—C1—C6	−167.20 (13)	C4—C5—C6—C1	0.1 (3)
N2—S1—C1—C6	76.84 (15)	N2—C9—C10—C11	−175.85 (18)
C15—O4—C10—C9	176.41 (19)	C14—C9—C10—O4	−179.16 (17)
C15—O4—C10—C11	−4.5 (3)	N2—C9—C14—C13	177.52 (17)
C7—N1—C4—C5	15.0 (3)	C10—C9—C14—C13	0.1 (3)
C4—N1—C7—C8	175.71 (18)	C14—C9—C10—C11	1.7 (3)
C4—N1—C7—O1A	−18.4 (13)	N2—C9—C10—O4	3.3 (2)
C7—N1—C4—C3	−165.53 (18)	O4—C10—C11—C12	179.1 (2)
S1—N2—C9—C14	68.93 (19)	C9—C10—C11—C12	−1.8 (3)
S1—N2—C9—C10	−113.58 (16)	C10—C11—C12—C13	0.2 (4)
C2—C1—C6—C5	−1.6 (3)	C11—C12—C13—C14	1.6 (4)
S1—C1—C2—C3	−177.52 (13)	C12—C13—C14—C9	−1.7 (3)

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

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C9–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O3^vi	0.811 (19)	2.191 (19)	2.995 (2)	171.0 (19)
N2—HN2···O4	0.823 (18)	2.359 (19)	2.6551 (19)	102.0 (15)
N2—HN2···O2^iv	0.823 (18)	2.259 (18)	3.0482 (18)	160.6 (18)
C2—H2···O3	0.93	2.53	2.890 (2)	104
C5—H5···O1A	0.93	2.30	2.882 (16)	120
C5—H5···Cg2ⁱⁱⁱ	0.93	2.90	3.715 (2)	148

Symmetry codes: (iii) x−1/2, −y+1/2, −z; (iv) −x+1, −y, −z; (vi) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₆N₂O₄S
M_r	320.37
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	15.7277 (4), 11.8351 (3), 16.5247 (4)
V (Å³)	3075.89 (13)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.24 × 0.18 × 0.09

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	15586, 3788, 2800
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.118, 1.03
No. of reflections	3788
No. of parameters	220
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)	0.35, −0.28

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C9–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O3ⁱ	0.811 (19)	2.191 (19)	2.995 (2)	171.0 (19)
N2—HN2···O4	0.823 (18)	2.359 (19)	2.6551 (19)	102.0 (15)
N2—HN2···O2ⁱⁱ	0.823 (18)	2.259 (18)	3.0482 (18)	160.6 (18)
C5—H5···Cg2ⁱⁱⁱ	0.93	2.90	3.715 (2)	148

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

Footnotes

‡Additional correspondence author, e-mail: akhyar@gcu.edu.pk.

Acknowledgements

The authors are grateful to the Higher Education Commission (HEC), Pakistan, for providing funds for the single-crystal XRD facilities at GC University, Lahore.

References

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Volume 67| Part 2| February 2011| Pages o303-o304

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