2-{4-[Acet­yl(eth­yl)amino]­benzene­sulfonamido}­benzoic acid

Mustafa, G.; Khan, I.U.; Khan, F.M.; Akkurt, M.

doi:10.1107/S1600536812013864

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1305

doi:10.1107/S1600536812013864

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2-{4-[Acetyl(ethyl)amino]benzenesulfonamido}benzoic acid

Ghulam Mustafa,^a Islam Ullah Khan,^a Farhan Mehmood Khan ^a and Mehmet Akkurt ^b ^*

^aDepartment of Chemistry, GC University, Lahore 54000, Pakistan, and ^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey
^*Correspondence e-mail: akkurt@erciyes.edu.tr, gmustafa884@yahoo.com

(Received 30 March 2012; accepted 30 March 2012; online 4 April 2012)

In the title compound, C₁₇H₁₈N₂O₅S, the dihedral angle between the aromatic rings is 68.59 (10)° and the C—S—N—C torsion angle is −81.84 (18)°. The molecular conformation is stabilized by an intramolecular N—H⋯O hydrogen bond, generating an S(6) ring. In the crystal, molecules are linked by C—H⋯O and O—H⋯O hydrogen bonds into a three-dimensional network.

Related literature

For related structures and background to the biological properties of sulfonamides, see: Mustafa et al. (2010 , 2011 ); Khan et al. (2011 ).

Experimental

Crystal data

C₁₇H₁₈N₂O₅S
M_r = 362.40
Orthorhombic, P n a 2₁
a = 18.0371 (7) Å
b = 12.0249 (4) Å
c = 7.8430 (2) Å
V = 1701.10 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 296 K
0.35 × 0.29 × 0.27 mm

Data collection

Bruker APEXII CCD diffractometer
9278 measured reflections
3880 independent reflections
3327 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.093
S = 0.99
3880 reflections
233 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.18 e Å⁻³
Absolute structure: Flack (1983 ), 1612 Freidel pairs
Flack parameter: 0.05 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O5ⁱ	0.82	1.82	2.599 (2)	158
N1—H1N⋯O2	0.85 (2)	1.93 (2)	2.627 (2)	138 (2)
C12—H12⋯O3ⁱⁱ	0.93	2.45	3.356 (2)	164
C15—H15C⋯O3ⁱⁱ	0.96	2.53	3.400 (3)	150
C17—H17A⋯O2ⁱⁱ	0.96	2.58	3.486 (4)	158
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z+{\script{3\over 2}}]$ ; (ii) x, y, z-1.

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 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/S1600536812013864/hb6720sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812013864/hb6720Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812013864/hb6720Isup3.cml

checkCIF report

Comment top

As part of our ongoing studies of sulfonamides with potential biological properties (Mustafa et al., 2010, 2011; Khan et al., 2011), we now describe the title compound, (I).

In the title compound (I), (Fig. 1), the C2—C7 benzene ring makes a dihedral angle of 68.59 (10)° with the C8—C13 benzene ring. All the bond lengths are similar to those of the related molecules (Mustafa et al., 2010; 2011; Khan et al., 2011). The torsion angles C3—N1—S1—C8, C11—N2—C16—C17 and C11—N2—C14—C15 are -81.84 (18), 94.2 (3), and 7.0 (3)°, respectively.

The molecular conformation of (I) is stabilized by intramolecular N—H···O hydrogen-bond interaction (Table 1), which generate one S(6) ring. In the crystal, molecules are linked by C—H···O and O—H···O hydrogen bonds to form a three- dimensional network structure (Table 1, Fig. 2).

Related literature top

For related structures and background to the biological properties of sulfonamides, see: Mustafa et al. (2010, 2011); Khan et al. (2011).

Experimental top

To an aquious solution of p-amino benzoic acid (1.0 g, 7.3 mmol), sodium carbonate (1 N) was added to adjust the pH 8. Then added 4-(acetylamino) benzenesulfonyl chloride (2.21 g, 9.48 mmol) and the mixture was stirred at room temperature keeping the pH of the mixture up to 8.0 with occasional addition of sodium carbonate solution. Progress and completion of the reaction was confirmed by TLC and conversion of suspension into clear solution. After 2 h, whole mixture was poured into a beaker and the pH was adjusted to 2.0 by 1 N HCl. Pprecipitates were produced which were filtered and washed with distilled water. The prepared sulfonamide (2-({[4-(acetylamino)phenyl]sulfonyl}amino) benzoic acid) (1.0 g, 3 mmol), DMF (10 ml) and n-hexane washed sodium hydride (0.22 g, 9.0 mmol) were stirred at room temperature for 40 min followed by the addition of ethyl iodide (0.61 g, 3.9 mmol). The whole reaction mixture was stirred till the completion of the reaction and poured into crushed ice in a beaker. The pH of the mixture was adjusted to 4.0 with 1 N HCl. Precipitates were produced, filtered and washed twice with distilled water and crystallized from chloroform solution as brown blocks.

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 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. The molecular structure of the title compound, showing displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. View of the packing diagram and the hydrogen bonding of (I) along the c axis. Hydrogen atoms that not involved in the hydrogen-bonding (dashed lines) have been omitted for clarity.

2-{4-[Acetyl(ethyl)amino]benzenesulfonamido}benzoic acid top

Crystal data top

C₁₇H₁₈N₂O₅S	F(000) = 760
M_r = 362.40	D_x = 1.415 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 4557 reflections
a = 18.0371 (7) Å	θ = 2.3–28.2°
b = 12.0249 (4) Å	µ = 0.22 mm⁻¹
c = 7.8430 (2) Å	T = 296 K
V = 1701.10 (10) Å³	Block, brown
Z = 4	0.35 × 0.29 × 0.27 mm

Data collection top

Bruker APEXII CCD diffractometer	3327 reflections with I > 2σ(I)
Radiation source: sealed tube	R_int = 0.040
Graphite monochromator	θ_max = 28.3°, θ_min = 2.8°
ϕ and ω scans	h = −24→19
9278 measured reflections	k = −13→16
3880 independent reflections	l = −10→10

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)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.093	w = 1/[σ²(F_o²) + (0.0604P)²] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max < 0.001
3880 reflections	Δρ_max = 0.35 e Å⁻³
233 parameters	Δρ_min = −0.18 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 1612 Freidel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.05 (6)

Crystal data top

C₁₇H₁₈N₂O₅S	V = 1701.10 (10) Å³
M_r = 362.40	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 18.0371 (7) Å	µ = 0.22 mm⁻¹
b = 12.0249 (4) Å	T = 296 K
c = 7.8430 (2) Å	0.35 × 0.29 × 0.27 mm

Data collection top

Bruker APEXII CCD diffractometer	3327 reflections with I > 2σ(I)
9278 measured reflections	R_int = 0.040
3880 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.093	Δρ_max = 0.35 e Å⁻³
S = 0.99	Δρ_min = −0.18 e Å⁻³
3880 reflections	Absolute structure: Flack (1983), 1612 Freidel pairs
233 parameters	Absolute structure parameter: 0.05 (6)
2 restraints

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	0.09768 (2)	1.03872 (4)	1.00764 (6)	0.0403 (1)
O1	0.06408 (9)	0.65010 (13)	1.42241 (19)	0.0555 (5)
O2	0.12860 (8)	0.80244 (12)	1.3690 (2)	0.0570 (5)
O3	0.13309 (9)	1.10513 (13)	1.13429 (18)	0.0551 (5)
O4	0.02644 (8)	1.06853 (14)	0.9452 (2)	0.0568 (5)
O5	0.36221 (10)	1.08713 (16)	0.1903 (2)	0.0660 (6)
N1	0.09488 (10)	0.91519 (15)	1.0928 (2)	0.0473 (6)
N2	0.30964 (11)	1.02317 (15)	0.4272 (3)	0.0544 (6)
C1	0.08374 (10)	0.73379 (15)	1.3240 (2)	0.0402 (5)
C2	0.04690 (9)	0.73281 (15)	1.1545 (2)	0.0376 (5)
C3	0.05278 (10)	0.82314 (14)	1.0418 (2)	0.0371 (5)
C4	0.01818 (12)	0.81716 (18)	0.8837 (3)	0.0494 (6)
C5	−0.02159 (13)	0.72412 (18)	0.8387 (3)	0.0569 (8)
C6	−0.02717 (13)	0.63543 (19)	0.9473 (3)	0.0584 (7)
C7	0.00674 (11)	0.63937 (17)	1.1041 (3)	0.0486 (6)
C8	0.15845 (10)	1.03090 (13)	0.8330 (2)	0.0347 (5)
C9	0.23390 (11)	1.02380 (17)	0.8644 (3)	0.0461 (6)
C10	0.28288 (12)	1.02284 (18)	0.7301 (3)	0.0497 (7)
C11	0.25724 (11)	1.02912 (16)	0.5651 (2)	0.0428 (6)
C12	0.18157 (11)	1.03649 (16)	0.5338 (2)	0.0456 (6)
C13	0.13254 (11)	1.03771 (17)	0.6682 (2)	0.0428 (6)
C14	0.32075 (12)	1.10446 (17)	0.3124 (3)	0.0479 (6)
C15	0.28352 (13)	1.21419 (17)	0.3350 (4)	0.0609 (8)
C16	0.35281 (15)	0.9186 (2)	0.4124 (4)	0.0765 (10)
C17	0.3174 (2)	0.8394 (3)	0.2929 (7)	0.1147 (17)
H1	0.09620	0.63950	1.49470	0.0830*
H1N	0.1178 (11)	0.9097 (19)	1.187 (2)	0.047 (6)*
H4	0.02200	0.87640	0.80800	0.0590*
H5	−0.04500	0.72140	0.73310	0.0680*
H6	−0.05380	0.57270	0.91500	0.0700*
H7	0.00280	0.57890	1.17760	0.0580*
H9	0.25130	1.01970	0.97580	0.0550*
H10	0.33350	1.01790	0.75080	0.0600*
H12	0.16410	1.04060	0.42240	0.0550*
H13	0.08190	1.04310	0.64770	0.0510*
H15A	0.31060	1.27030	0.27400	0.0910*
H15B	0.28220	1.23280	0.45390	0.0910*
H15C	0.23380	1.21010	0.29150	0.0910*
H16A	0.40250	0.93560	0.37260	0.0920*
H16B	0.35700	0.88430	0.52390	0.0920*
H17A	0.27050	0.81600	0.33830	0.1720*
H17B	0.34890	0.77570	0.27820	0.1720*
H17C	0.30990	0.87500	0.18470	0.1720*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0487 (2)	0.0385 (2)	0.0338 (2)	−0.0018 (2)	0.0058 (2)	0.0024 (2)
O1	0.0657 (9)	0.0549 (8)	0.0460 (8)	−0.0130 (7)	−0.0115 (7)	0.0178 (7)
O2	0.0614 (9)	0.0576 (8)	0.0520 (8)	−0.0156 (7)	−0.0192 (7)	0.0128 (7)
O3	0.0783 (10)	0.0481 (8)	0.0388 (7)	−0.0115 (7)	0.0075 (7)	−0.0068 (6)
O4	0.0479 (8)	0.0636 (9)	0.0590 (9)	0.0107 (7)	0.0093 (7)	0.0114 (8)
O5	0.0780 (12)	0.0699 (11)	0.0501 (9)	−0.0151 (8)	0.0208 (8)	0.0087 (8)
N1	0.0584 (11)	0.0472 (9)	0.0363 (9)	−0.0136 (8)	−0.0088 (8)	0.0139 (8)
N2	0.0615 (11)	0.0523 (10)	0.0495 (10)	0.0049 (8)	0.0198 (9)	0.0117 (9)
C1	0.0401 (9)	0.0410 (9)	0.0394 (9)	0.0035 (7)	−0.0001 (7)	0.0065 (8)
C2	0.0317 (8)	0.0421 (9)	0.0390 (9)	0.0000 (7)	0.0032 (7)	0.0026 (8)
C3	0.0350 (9)	0.0390 (8)	0.0374 (10)	−0.0010 (7)	0.0016 (7)	0.0016 (7)
C4	0.0558 (12)	0.0521 (11)	0.0402 (10)	−0.0040 (9)	−0.0063 (9)	0.0083 (9)
C5	0.0664 (14)	0.0582 (13)	0.0462 (12)	−0.0054 (10)	−0.0154 (10)	−0.0039 (10)
C6	0.0641 (13)	0.0492 (12)	0.0618 (13)	−0.0110 (10)	−0.0135 (11)	−0.0042 (10)
C7	0.0503 (11)	0.0422 (10)	0.0534 (12)	−0.0061 (8)	−0.0039 (9)	0.0050 (9)
C8	0.0404 (10)	0.0322 (8)	0.0315 (8)	−0.0021 (6)	0.0018 (7)	0.0012 (7)
C9	0.0462 (11)	0.0583 (12)	0.0339 (9)	−0.0017 (9)	−0.0074 (8)	0.0039 (9)
C10	0.0383 (11)	0.0615 (12)	0.0494 (12)	−0.0003 (9)	−0.0015 (9)	0.0063 (10)
C11	0.0455 (11)	0.0425 (10)	0.0405 (10)	−0.0007 (7)	0.0081 (8)	0.0031 (8)
C12	0.0526 (11)	0.0530 (11)	0.0312 (10)	−0.0037 (9)	−0.0065 (8)	0.0027 (8)
C13	0.0378 (10)	0.0531 (11)	0.0376 (10)	−0.0022 (8)	−0.0065 (8)	0.0040 (8)
C14	0.0513 (11)	0.0468 (10)	0.0457 (11)	−0.0119 (8)	0.0002 (9)	0.0054 (9)
C15	0.0686 (15)	0.0468 (11)	0.0673 (15)	−0.0098 (10)	−0.0047 (12)	0.0065 (11)
C16	0.0816 (19)	0.0763 (17)	0.0716 (17)	0.0207 (14)	0.0323 (14)	0.0162 (15)
C17	0.117 (3)	0.0541 (16)	0.173 (4)	−0.0027 (17)	0.033 (3)	−0.008 (2)

Geometric parameters (Å, º) top

S1—O3	1.4256 (16)	C9—C10	1.375 (3)
S1—O4	1.4211 (15)	C10—C11	1.376 (3)
S1—N1	1.6295 (18)	C11—C12	1.390 (3)
S1—C8	1.7568 (17)	C12—C13	1.376 (2)
O1—C1	1.317 (2)	C14—C15	1.491 (3)
O2—C1	1.209 (2)	C16—C17	1.481 (5)
O5—C14	1.233 (3)	C4—H4	0.9300
O1—H1	0.8200	C5—H5	0.9300
N1—C3	1.401 (2)	C6—H6	0.9300
N2—C14	1.344 (3)	C7—H7	0.9300
N2—C16	1.484 (3)	C9—H9	0.9300
N2—C11	1.438 (3)	C10—H10	0.9300
N1—H1N	0.849 (17)	C12—H12	0.9300
C1—C2	1.486 (2)	C13—H13	0.9300
C2—C3	1.404 (2)	C15—H15A	0.9600
C2—C7	1.394 (3)	C15—H15B	0.9600
C3—C4	1.390 (3)	C15—H15C	0.9600
C4—C5	1.375 (3)	C16—H16A	0.9700
C5—C6	1.369 (3)	C16—H16B	0.9700
C6—C7	1.374 (3)	C17—H17A	0.9600
C8—C9	1.386 (3)	C17—H17B	0.9600
C8—C13	1.377 (2)	C17—H17C	0.9600

O3—S1—O4	120.26 (10)	O5—C14—C15	121.0 (2)
O3—S1—N1	103.82 (9)	N2—C14—C15	119.8 (2)
O3—S1—C8	107.08 (9)	N2—C16—C17	111.6 (2)
O4—S1—N1	110.07 (9)	C3—C4—H4	120.00
O4—S1—C8	108.00 (9)	C5—C4—H4	120.00
N1—S1—C8	106.87 (8)	C4—C5—H5	120.00
C1—O1—H1	109.00	C6—C5—H5	120.00
S1—N1—C3	128.33 (13)	C5—C6—H6	120.00
C11—N2—C16	116.48 (19)	C7—C6—H6	120.00
C14—N2—C16	119.1 (2)	C2—C7—H7	120.00
C11—N2—C14	124.45 (18)	C6—C7—H7	120.00
C3—N1—H1N	116.8 (15)	C8—C9—H9	120.00
S1—N1—H1N	114.4 (15)	C10—C9—H9	120.00
O1—C1—C2	113.44 (16)	C9—C10—H10	120.00
O1—C1—O2	122.08 (16)	C11—C10—H10	120.00
O2—C1—C2	124.47 (16)	C11—C12—H12	120.00
C1—C2—C3	121.54 (15)	C13—C12—H12	120.00
C1—C2—C7	119.49 (17)	C8—C13—H13	120.00
C3—C2—C7	118.96 (16)	C12—C13—H13	120.00
C2—C3—C4	119.18 (16)	C14—C15—H15A	109.00
N1—C3—C2	118.19 (15)	C14—C15—H15B	109.00
N1—C3—C4	122.62 (16)	C14—C15—H15C	109.00
C3—C4—C5	120.4 (2)	H15A—C15—H15B	109.00
C4—C5—C6	120.8 (2)	H15A—C15—H15C	109.00
C5—C6—C7	119.8 (2)	H15B—C15—H15C	110.00
C2—C7—C6	120.85 (19)	N2—C16—H16A	109.00
C9—C8—C13	120.26 (17)	N2—C16—H16B	109.00
S1—C8—C13	121.13 (14)	C17—C16—H16A	109.00
S1—C8—C9	118.52 (14)	C17—C16—H16B	109.00
C8—C9—C10	119.7 (2)	H16A—C16—H16B	108.00
C9—C10—C11	120.3 (2)	C16—C17—H17A	109.00
N2—C11—C10	118.92 (19)	C16—C17—H17B	109.00
N2—C11—C12	121.05 (16)	C16—C17—H17C	109.00
C10—C11—C12	119.98 (17)	H17A—C17—H17B	109.00
C11—C12—C13	119.78 (15)	H17A—C17—H17C	110.00
C8—C13—C12	120.02 (18)	H17B—C17—H17C	109.00
O5—C14—N2	119.2 (2)

O3—S1—N1—C3	165.17 (17)	O2—C1—C2—C3	−10.4 (3)
O4—S1—N1—C3	35.20 (19)	O1—C1—C2—C7	−10.4 (2)
C8—S1—N1—C3	−81.84 (18)	C1—C2—C7—C6	−179.19 (19)
N1—S1—C8—C13	109.88 (16)	C7—C2—C3—C4	0.3 (3)
N1—S1—C8—C9	−73.62 (16)	C7—C2—C3—N1	−178.43 (17)
O3—S1—C8—C9	37.13 (17)	C1—C2—C3—C4	178.99 (17)
O4—S1—C8—C9	167.99 (15)	C3—C2—C7—C6	−0.5 (3)
O3—S1—C8—C13	−139.37 (15)	C1—C2—C3—N1	0.3 (2)
O4—S1—C8—C13	−8.52 (18)	C2—C3—C4—C5	0.3 (3)
S1—N1—C3—C2	−166.53 (14)	N1—C3—C4—C5	178.98 (19)
S1—N1—C3—C4	14.8 (3)	C3—C4—C5—C6	−0.8 (3)
C14—N2—C11—C12	64.0 (3)	C4—C5—C6—C7	0.6 (4)
C16—N2—C14—C15	−174.0 (2)	C5—C6—C7—C2	0.0 (3)
C16—N2—C11—C10	62.2 (3)	S1—C8—C9—C10	−176.96 (16)
C11—N2—C14—C15	7.0 (3)	C9—C8—C13—C12	0.6 (3)
C14—N2—C16—C17	−85.0 (3)	C13—C8—C9—C10	−0.4 (3)
C11—N2—C16—C17	94.2 (3)	S1—C8—C13—C12	177.02 (15)
C11—N2—C14—O5	−173.6 (2)	C8—C9—C10—C11	0.1 (3)
C14—N2—C11—C10	−118.7 (2)	C9—C10—C11—C12	0.0 (3)
C16—N2—C14—O5	5.5 (3)	C9—C10—C11—N2	−177.39 (19)
C16—N2—C11—C12	−115.1 (2)	C10—C11—C12—C13	0.1 (3)
O2—C1—C2—C7	168.24 (18)	N2—C11—C12—C13	177.48 (18)
O1—C1—C2—C3	170.93 (16)	C11—C12—C13—C8	−0.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O5ⁱ	0.82	1.82	2.599 (2)	158
N1—H1N···O2	0.85 (2)	1.93 (2)	2.627 (2)	138 (2)
C12—H12···O3ⁱⁱ	0.93	2.45	3.356 (2)	164
C15—H15C···O3ⁱⁱ	0.96	2.53	3.400 (3)	150
C17—H17A···O2ⁱⁱ	0.96	2.58	3.486 (4)	158

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₈N₂O₅S
M_r	362.40
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	296
a, b, c (Å)	18.0371 (7), 12.0249 (4), 7.8430 (2)
V (Å³)	1701.10 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.35 × 0.29 × 0.27

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9278, 3880, 3327
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.093, 0.99
No. of reflections	3880
No. of parameters	233
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, −0.18
Absolute structure	Flack (1983), 1612 Freidel pairs
Absolute structure parameter	0.05 (6)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), 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

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O5ⁱ	0.82	1.82	2.599 (2)	158
N1—H1N···O2	0.849 (17)	1.934 (19)	2.627 (2)	138 (2)
C12—H12···O3ⁱⁱ	0.93	2.45	3.356 (2)	164
C15—H15C···O3ⁱⁱ	0.96	2.53	3.400 (3)	150
C17—H17A···O2ⁱⁱ	0.96	2.58	3.486 (4)	158

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

Acknowledgements

The authors are grateful to Mr Muhammad Nadeem Arshad for his assistance and the Higher Education Commission (HEC), Pakistan, for financial support.

References

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