4-(4-Meth­oxy­benzene­sulfonamido)­benzoic acid

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

doi:10.1107/S1600536811025098

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1857

doi:10.1107/S1600536811025098

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4-(4-Methoxybenzenesulfonamido)benzoic acid

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

^aMaterials Chemistry Laboratory, Department of Chemistry, GC University, Lahore 54000, Pakistan, and ^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey
^*Correspondence e-mail: iukhan@gcu.edu.pk, akkurt@erciyes.edu.tr

(Received 23 June 2011; accepted 26 June 2011; online 30 June 2011)

The asymmetric unit of the title compound, C₁₄H₁₃NO₅S, contains two independent molecules in which the dihedral angles between the aromatic rings are 83.45 (11) and 86.65 (9)°. In the crystal, the independent molecules are connected by N—H⋯O and O—H⋯O hydrogen bonds, forming a double-chain structure along [401]. A weak π–π stacking interaction with a centroid–centroid distance of 3.7509 (13) Å and C—H⋯O hydrogen bonds are also observed.

Related literature

For background to the biological activity of sulfonamides, see: Hanson et al. (1999 ). For related structures, see: Mustafa et al. (2010 , 2011 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₄H₁₃NO₅S
M_r = 307.32
Monoclinic, P 2₁ /c
a = 8.6980 (3) Å
b = 21.7471 (8) Å
c = 14.5824 (6) Å
β = 95.153 (2)°
V = 2747.21 (18) Å³
Z = 8
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 296 K
0.38 × 0.31 × 0.28 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker 2007 ) T_min = 0.909, T_max = 0.931
25188 measured reflections
6806 independent reflections
5475 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.120
S = 1.04
6806 reflections
394 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN1⋯O8ⁱ	0.84 (2)	2.31 (2)	3.122 (2)	165 (2)
O2—HO1⋯O7ⁱⁱ	0.81 (2)	1.78 (2)	2.583 (2)	172 (2)
N2—HN2⋯O3ⁱⁱⁱ	0.82 (2)	2.15 (2)	2.959 (2)	173 (2)
O6—HO2⋯O1^iv	0.82 (2)	2.02 (2)	2.8338 (19)	173 (2)
C4—H4⋯O4	0.93	2.54	3.149 (2)	123
C9—H9⋯O7	0.93	2.32	3.224 (3)	165
C13—H13⋯O10^v	0.93	2.57	3.381 (3)	146
C14—H14A⋯O8^iv	0.96	2.42	3.370 (3)	169
C23—H23⋯O2	0.93	2.52	3.286 (2)	140
C26—H26⋯O1^vi	0.93	2.57	3.197 (2)	125
Symmetry codes: (i) x-1, y, z; (ii) $[x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) x+1, y, z; (iv) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (v) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (vi) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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/S1600536811025098/is2741sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811025098/is2741Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811025098/is2741Isup3.cml

checkCIF report

Comment top

Sulfonamides are well known for their various types of biological activities (e.g. Hanson et al., 1999). In the present paper, the structure of the title compound, (I), is reported.

As shown in Fig. 1, the asymmetric unit of the title compound (I) contains two crystallographically independent molecules A (with S1) and B (with S2). All the bond lengths (Allen et al., 1987) and angles are within normal ranges and they are similar to those of the related molecules (Mustafa et al., 2010, 2011). The dihedral angles between the aromatic rings of (I) is 83.45 (11)° for molecule A and 86.65 (9)° for molecule B.

The crystal packing (Fig. 2, Table 1) is stabilized by C—H···O, N—H···O and O—H···O hydrogen bonds and a weak π–π interaction between the benzene rings attached with the methoxy group of the symmetry independent molecules [Cg2···Cg4^iv = 3.7509 (13) Å; symmetry code: (iv) x - 1, -y + 1/2, z - 1/2; Cg2 and Cg4 are the centroid of the C8–C13 and C22–C27 benzene rings, respectively].

Related literature top

For background to the biological activity of sulfonamides, see: Hanson et al. (1999). For related structures, see: Mustafa et al. (2010, 2011). For bond-length data, see: Allen et al. (1987).

Experimental top

To a mixture of p-amino benzoic acid (1.0 g, 7.3 mmoles) and distilled water (10 ml) in a round bottomflask (25 ml) 1M aqueous sodium carbonate solution was added to maintain the pH between 8–9. 4-Methoxy benzenesulfonyl chloride (1.51 g, 7.3 mmol) was added to this solution and was kept stirred at room temperature for 5 h. pH of the reaction mixture was adjusted to 1–2, using 1 N HCl and the precipitates obtained were filtered, washed with distilled water, dried and recrystallized from methanol to yield light brown crystals of (I).

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. The asymmetric unit of the title compound, showing the labelling of all non-H atoms. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
	Fig. 2. A packing diagram of the title compound with hydrogen bonds, viewed down a axis. Hydrogen atoms that not involved in the hydrogen-bonding (dashed lines) have been omitted for clarity.

4-(4-Methoxybenzenesulfonamido)benzoic acid top

Crystal data top

C₁₄H₁₃NO₅S	F(000) = 1280
M_r = 307.32	D_x = 1.486 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9988 reflections
a = 8.6980 (3) Å	θ = 2.4–28.4°
b = 21.7471 (8) Å	µ = 0.26 mm⁻¹
c = 14.5824 (6) Å	T = 296 K
β = 95.153 (2)°	Block, light brown
V = 2747.21 (18) Å³	0.38 × 0.31 × 0.28 mm
Z = 8

Data collection top

Bruker APEXII CCD diffractometer	6806 independent reflections
Radiation source: sealed tube	5475 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ϕ and ω scans	θ_max = 28.4°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker 2007)	h = −11→11
T_min = 0.909, T_max = 0.931	k = −24→28
25188 measured reflections	l = −14→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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0499P)² + 1.497P] where P = (F_o² + 2F_c²)/3
6806 reflections	(Δ/σ)_max = 0.001
394 parameters	Δρ_max = 0.45 e Å⁻³
4 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₄H₁₃NO₅S	V = 2747.21 (18) Å³
M_r = 307.32	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.6980 (3) Å	µ = 0.26 mm⁻¹
b = 21.7471 (8) Å	T = 296 K
c = 14.5824 (6) Å	0.38 × 0.31 × 0.28 mm
β = 95.153 (2)°

Data collection top

Bruker APEXII CCD diffractometer	6806 independent reflections
Absorption correction: multi-scan (SADABS; Bruker 2007)	5475 reflections with I > 2σ(I)
T_min = 0.909, T_max = 0.931	R_int = 0.018
25188 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	4 restraints
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.45 e Å⁻³
6806 reflections	Δρ_min = −0.30 e Å⁻³
394 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	−0.24733 (5)	0.16859 (2)	0.57376 (4)	0.0419 (1)
O1	0.53350 (14)	0.11383 (6)	0.80744 (9)	0.0418 (4)
O2	0.57070 (16)	0.21434 (6)	0.79480 (13)	0.0606 (5)
O3	−0.36648 (15)	0.20947 (6)	0.53547 (12)	0.0562 (5)
O4	−0.28249 (17)	0.12512 (7)	0.64187 (11)	0.0564 (5)
O5	−0.0035 (3)	0.02617 (9)	0.27559 (14)	0.0870 (8)
N1	−0.11308 (18)	0.21531 (7)	0.61562 (13)	0.0469 (5)
C1	0.4873 (2)	0.16478 (8)	0.78203 (12)	0.0373 (5)
C2	0.33184 (19)	0.17603 (8)	0.73538 (12)	0.0349 (5)
C3	0.2252 (2)	0.12892 (8)	0.72183 (12)	0.0371 (5)
C4	0.0773 (2)	0.14010 (8)	0.68239 (13)	0.0407 (5)
C5	0.03454 (19)	0.19958 (8)	0.65561 (12)	0.0361 (5)
C6	0.1406 (2)	0.24698 (8)	0.66846 (13)	0.0417 (5)
C7	0.2870 (2)	0.23542 (9)	0.70806 (14)	0.0444 (6)
C8	−0.1707 (2)	0.12793 (8)	0.48507 (13)	0.0396 (5)
C9	−0.1128 (2)	0.15868 (9)	0.41275 (16)	0.0511 (7)
C10	−0.0545 (3)	0.12605 (11)	0.34123 (16)	0.0567 (7)
C11	−0.0575 (3)	0.06309 (11)	0.34217 (17)	0.0599 (8)
C12	−0.1172 (4)	0.03327 (11)	0.4127 (2)	0.0762 (10)
C13	−0.1732 (3)	0.06474 (10)	0.48410 (17)	0.0612 (8)
C14	0.0691 (3)	0.05350 (15)	0.20391 (19)	0.0827 (10)
S2	0.65408 (5)	0.38949 (2)	0.58411 (3)	0.0410 (1)
O6	−0.15326 (16)	0.40548 (7)	0.37226 (11)	0.0520 (5)
O7	−0.15559 (17)	0.30391 (7)	0.37416 (16)	0.0794 (7)
O8	0.79224 (15)	0.35378 (7)	0.60408 (11)	0.0537 (5)
O9	0.65854 (17)	0.44420 (7)	0.53070 (11)	0.0550 (5)
O10	0.3728 (2)	0.45077 (9)	0.92259 (12)	0.0764 (7)
N2	0.53708 (18)	0.34000 (7)	0.53111 (12)	0.0440 (5)
C15	−0.0880 (2)	0.35269 (9)	0.38936 (14)	0.0433 (5)
C16	0.07422 (19)	0.35329 (8)	0.42858 (12)	0.0369 (5)
C17	0.1530 (2)	0.40609 (8)	0.45785 (13)	0.0419 (5)
C18	0.3058 (2)	0.40391 (8)	0.49278 (14)	0.0435 (6)
C19	0.38196 (19)	0.34749 (8)	0.49887 (11)	0.0347 (5)
C20	0.3038 (2)	0.29444 (8)	0.46977 (13)	0.0395 (5)
C21	0.1526 (2)	0.29756 (8)	0.43499 (14)	0.0429 (5)
C22	0.57550 (19)	0.40798 (8)	0.68678 (13)	0.0375 (5)
C23	0.5632 (2)	0.36265 (8)	0.75171 (14)	0.0430 (5)
C24	0.4966 (2)	0.37489 (9)	0.83181 (14)	0.0468 (6)
C25	0.4431 (2)	0.43392 (10)	0.84718 (14)	0.0496 (6)
C26	0.4594 (3)	0.48007 (9)	0.78309 (15)	0.0513 (7)
C27	0.5238 (2)	0.46746 (8)	0.70259 (14)	0.0444 (6)
C28	0.3489 (4)	0.40625 (16)	0.9901 (2)	0.1000 (14)
HN1	−0.129 (3)	0.2526 (7)	0.6033 (15)	0.0500*
HO1	0.654 (2)	0.2050 (11)	0.8197 (16)	0.0630*
H3	0.25340	0.08910	0.73950	0.0450*
H4	0.00680	0.10800	0.67380	0.0490*
H6	0.11270	0.28670	0.65020	0.0500*
H7	0.35730	0.26760	0.71680	0.0530*
H9	−0.11280	0.20140	0.41180	0.0610*
H10	−0.01380	0.14690	0.29320	0.0680*
H12	−0.12010	−0.00950	0.41260	0.0910*
H13	−0.21280	0.04330	0.53190	0.0730*
H14A	−0.00400	0.07850	0.16740	0.1240*
H14B	0.10790	0.02210	0.16600	0.1240*
H14C	0.15310	0.07870	0.22920	0.1240*
HN2	0.571 (2)	0.3049 (8)	0.5344 (15)	0.0490*
HO2	−0.245 (2)	0.3998 (11)	0.3583 (17)	0.0610*
H17	0.10200	0.44370	0.45390	0.0500*
H18	0.35740	0.43970	0.51200	0.0520*
H20	0.35420	0.25670	0.47390	0.0470*
H21	0.10130	0.26170	0.41530	0.0520*
H23	0.60040	0.32340	0.74130	0.0520*
H24	0.48740	0.34410	0.87520	0.0560*
H26	0.42660	0.51980	0.79470	0.0620*
H27	0.53290	0.49820	0.65910	0.0530*
H28A	0.28250	0.37450	0.96350	0.1500*
H28B	0.30170	0.42530	1.04000	0.1500*
H28C	0.44620	0.38870	1.01290	0.1500*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0310 (2)	0.0358 (2)	0.0574 (3)	0.0010 (2)	−0.0046 (2)	−0.0053 (2)
O1	0.0374 (6)	0.0350 (6)	0.0519 (8)	0.0030 (5)	−0.0018 (5)	−0.0010 (5)
O2	0.0371 (7)	0.0354 (7)	0.1042 (13)	−0.0012 (6)	−0.0225 (8)	0.0033 (8)
O3	0.0364 (7)	0.0425 (7)	0.0860 (11)	0.0076 (6)	−0.0154 (7)	−0.0127 (7)
O4	0.0517 (8)	0.0546 (9)	0.0638 (9)	−0.0061 (7)	0.0110 (7)	0.0009 (7)
O5	0.1154 (16)	0.0666 (11)	0.0801 (13)	0.0167 (11)	0.0143 (12)	−0.0180 (10)
N1	0.0376 (8)	0.0318 (7)	0.0680 (11)	0.0034 (6)	−0.0133 (7)	−0.0069 (7)
C1	0.0345 (8)	0.0343 (8)	0.0424 (9)	0.0017 (7)	−0.0001 (7)	−0.0041 (7)
C2	0.0330 (8)	0.0352 (8)	0.0358 (8)	0.0011 (6)	−0.0003 (6)	−0.0031 (7)
C3	0.0395 (9)	0.0312 (8)	0.0399 (9)	0.0027 (7)	−0.0009 (7)	−0.0030 (7)
C4	0.0392 (9)	0.0318 (8)	0.0499 (10)	−0.0025 (7)	−0.0032 (7)	−0.0062 (7)
C5	0.0335 (8)	0.0373 (9)	0.0365 (8)	0.0020 (7)	−0.0022 (6)	−0.0059 (7)
C6	0.0423 (9)	0.0312 (8)	0.0500 (10)	0.0009 (7)	−0.0052 (8)	0.0028 (7)
C7	0.0391 (9)	0.0354 (9)	0.0568 (11)	−0.0057 (7)	−0.0061 (8)	0.0014 (8)
C8	0.0355 (8)	0.0331 (8)	0.0481 (10)	0.0000 (7)	−0.0082 (7)	−0.0018 (7)
C9	0.0476 (11)	0.0381 (10)	0.0661 (13)	−0.0008 (8)	−0.0028 (9)	0.0036 (9)
C10	0.0500 (11)	0.0632 (14)	0.0565 (13)	0.0019 (10)	0.0026 (9)	0.0046 (11)
C11	0.0631 (13)	0.0512 (12)	0.0633 (14)	0.0103 (10)	−0.0055 (11)	−0.0105 (11)
C12	0.112 (2)	0.0380 (12)	0.0800 (18)	0.0057 (13)	0.0163 (16)	−0.0088 (11)
C13	0.0842 (16)	0.0351 (10)	0.0653 (14)	0.0013 (10)	0.0117 (12)	0.0018 (10)
C14	0.0737 (17)	0.108 (2)	0.0657 (17)	0.0365 (17)	0.0026 (13)	−0.0108 (16)
S2	0.0325 (2)	0.0355 (2)	0.0537 (3)	−0.0009 (2)	−0.0035 (2)	−0.0059 (2)
O6	0.0353 (7)	0.0463 (8)	0.0725 (10)	0.0065 (6)	−0.0051 (6)	0.0095 (7)
O7	0.0405 (8)	0.0438 (8)	0.1466 (18)	−0.0054 (6)	−0.0317 (9)	0.0155 (10)
O8	0.0321 (6)	0.0509 (8)	0.0756 (10)	0.0035 (6)	−0.0081 (6)	−0.0153 (7)
O9	0.0607 (9)	0.0432 (8)	0.0621 (9)	−0.0048 (7)	0.0111 (7)	0.0019 (7)
O10	0.1012 (14)	0.0737 (11)	0.0574 (10)	0.0305 (10)	0.0240 (9)	0.0128 (9)
N2	0.0356 (8)	0.0331 (8)	0.0602 (10)	0.0064 (6)	−0.0130 (7)	−0.0107 (7)
C15	0.0335 (8)	0.0392 (9)	0.0564 (11)	0.0020 (7)	−0.0007 (8)	0.0085 (8)
C16	0.0310 (8)	0.0389 (9)	0.0403 (9)	0.0020 (7)	0.0004 (7)	0.0061 (7)
C17	0.0392 (9)	0.0365 (9)	0.0489 (10)	0.0081 (7)	−0.0027 (8)	−0.0012 (8)
C18	0.0419 (9)	0.0331 (9)	0.0532 (11)	0.0028 (7)	−0.0077 (8)	−0.0069 (8)
C19	0.0319 (8)	0.0375 (9)	0.0338 (8)	0.0014 (6)	−0.0020 (6)	−0.0020 (7)
C20	0.0347 (8)	0.0300 (8)	0.0527 (10)	0.0043 (6)	−0.0024 (7)	0.0009 (7)
C21	0.0345 (8)	0.0345 (9)	0.0583 (11)	−0.0032 (7)	−0.0043 (8)	0.0023 (8)
C22	0.0338 (8)	0.0303 (8)	0.0464 (10)	−0.0015 (6)	−0.0078 (7)	−0.0021 (7)
C23	0.0412 (9)	0.0286 (8)	0.0571 (11)	0.0022 (7)	−0.0072 (8)	0.0017 (8)
C24	0.0454 (10)	0.0399 (10)	0.0534 (11)	0.0013 (8)	−0.0046 (8)	0.0109 (8)
C25	0.0498 (11)	0.0488 (11)	0.0490 (11)	0.0076 (9)	−0.0020 (9)	0.0021 (9)
C26	0.0661 (13)	0.0323 (9)	0.0548 (12)	0.0104 (9)	0.0021 (10)	−0.0009 (8)
C27	0.0541 (11)	0.0288 (8)	0.0494 (11)	0.0010 (7)	−0.0010 (8)	0.0017 (7)
C28	0.110 (2)	0.119 (3)	0.0770 (19)	0.058 (2)	0.0408 (18)	0.0445 (19)

Geometric parameters (Å, º) top

S1—O3	1.4395 (15)	C3—H3	0.9300
S1—O4	1.4242 (16)	C4—H4	0.9300
S1—N1	1.6249 (17)	C6—H6	0.9300
S1—C8	1.7475 (19)	C7—H7	0.9300
S2—O8	1.4385 (15)	C9—H9	0.9300
S2—O9	1.4245 (16)	C10—H10	0.9300
S2—N2	1.6279 (17)	C12—H12	0.9300
S2—C22	1.7476 (19)	C13—H13	0.9300
O1—C1	1.225 (2)	C14—H14A	0.9600
O2—C1	1.303 (2)	C14—H14B	0.9600
O5—C11	1.375 (3)	C14—H14C	0.9600
O5—C14	1.401 (4)	C15—C16	1.474 (2)
O2—HO1	0.807 (19)	C16—C21	1.390 (2)
O6—C15	1.295 (2)	C16—C17	1.385 (2)
O7—C15	1.223 (2)	C17—C18	1.381 (3)
O10—C25	1.356 (3)	C18—C19	1.393 (2)
O10—C28	1.409 (4)	C19—C20	1.386 (2)
O6—HO2	0.815 (18)	C20—C21	1.368 (3)
N1—C5	1.404 (2)	C22—C27	1.395 (2)
N1—HN1	0.839 (16)	C22—C23	1.378 (3)
N2—C19	1.398 (2)	C23—C24	1.376 (3)
N2—HN2	0.818 (18)	C24—C25	1.391 (3)
C1—C2	1.478 (2)	C25—C26	1.387 (3)
C2—C7	1.397 (3)	C26—C27	1.373 (3)
C2—C3	1.384 (2)	C17—H17	0.9300
C3—C4	1.383 (2)	C18—H18	0.9300
C4—C5	1.392 (2)	C20—H20	0.9300
C5—C6	1.385 (2)	C21—H21	0.9300
C6—C7	1.373 (3)	C23—H23	0.9300
C8—C9	1.382 (3)	C24—H24	0.9300
C8—C13	1.374 (3)	C26—H26	0.9300
C9—C10	1.394 (3)	C27—H27	0.9300
C10—C11	1.370 (3)	C28—H28A	0.9600
C11—C12	1.358 (4)	C28—H28B	0.9600
C12—C13	1.371 (4)	C28—H28C	0.9600

O3—S1—O4	119.23 (9)	C11—C10—H10	120.00
O3—S1—N1	103.16 (8)	C11—C12—H12	119.00
O3—S1—C8	109.55 (10)	C13—C12—H12	119.00
O4—S1—N1	110.19 (10)	C12—C13—H13	120.00
O4—S1—C8	107.48 (9)	C8—C13—H13	120.00
N1—S1—C8	106.58 (9)	H14A—C14—H14C	109.00
O9—S2—N2	109.83 (9)	H14B—C14—H14C	109.00
O9—S2—C22	107.95 (9)	O5—C14—H14A	109.00
N2—S2—C22	106.44 (8)	H14A—C14—H14B	109.00
O8—S2—C22	109.55 (9)	O5—C14—H14B	109.00
O8—S2—O9	119.89 (9)	O5—C14—H14C	110.00
O8—S2—N2	102.38 (8)	O6—C15—O7	122.59 (17)
C11—O5—C14	119.0 (2)	O6—C15—C16	117.04 (16)
C1—O2—HO1	108.8 (17)	O7—C15—C16	120.37 (17)
C25—O10—C28	119.1 (2)	C15—C16—C21	117.72 (16)
C15—O6—HO2	108.4 (17)	C15—C16—C17	123.83 (16)
S1—N1—C5	127.10 (13)	C17—C16—C21	118.44 (16)
C5—N1—HN1	116.8 (17)	C16—C17—C18	121.23 (16)
S1—N1—HN1	115.1 (17)	C17—C18—C19	119.35 (16)
S2—N2—C19	128.76 (13)	C18—C19—C20	119.74 (16)
C19—N2—HN2	117.4 (13)	N2—C19—C18	124.27 (16)
S2—N2—HN2	112.5 (13)	N2—C19—C20	115.98 (15)
O1—C1—O2	122.80 (16)	C19—C20—C21	120.06 (16)
O1—C1—C2	123.41 (16)	C16—C21—C20	121.18 (16)
O2—C1—C2	113.78 (15)	S2—C22—C23	118.99 (14)
C3—C2—C7	118.51 (16)	S2—C22—C27	120.76 (14)
C1—C2—C7	120.31 (16)	C23—C22—C27	120.24 (17)
C1—C2—C3	121.11 (16)	C22—C23—C24	120.65 (17)
C2—C3—C4	121.04 (16)	C23—C24—C25	119.21 (18)
C3—C4—C5	119.68 (16)	O10—C25—C26	115.58 (19)
N1—C5—C6	116.62 (15)	O10—C25—C24	124.20 (19)
N1—C5—C4	123.66 (16)	C24—C25—C26	120.22 (19)
C4—C5—C6	119.72 (16)	C25—C26—C27	120.38 (18)
C5—C6—C7	120.13 (17)	C22—C27—C26	119.25 (18)
C2—C7—C6	120.92 (17)	C16—C17—H17	119.00
C9—C8—C13	118.86 (19)	C18—C17—H17	119.00
S1—C8—C13	120.45 (16)	C17—C18—H18	120.00
S1—C8—C9	120.63 (14)	C19—C18—H18	120.00
C8—C9—C10	120.45 (19)	C19—C20—H20	120.00
C9—C10—C11	119.5 (2)	C21—C20—H20	120.00
O5—C11—C10	124.7 (2)	C16—C21—H21	119.00
C10—C11—C12	119.6 (2)	C20—C21—H21	119.00
O5—C11—C12	115.7 (2)	C22—C23—H23	120.00
C11—C12—C13	121.5 (2)	C24—C23—H23	120.00
C8—C13—C12	120.0 (2)	C23—C24—H24	120.00
C4—C3—H3	119.00	C25—C24—H24	120.00
C2—C3—H3	120.00	C25—C26—H26	120.00
C3—C4—H4	120.00	C27—C26—H26	120.00
C5—C4—H4	120.00	C22—C27—H27	120.00
C7—C6—H6	120.00	C26—C27—H27	120.00
C5—C6—H6	120.00	O10—C28—H28A	109.00
C2—C7—H7	120.00	O10—C28—H28B	109.00
C6—C7—H7	120.00	O10—C28—H28C	110.00
C10—C9—H9	120.00	H28A—C28—H28B	110.00
C8—C9—H9	120.00	H28A—C28—H28C	109.00
C9—C10—H10	120.00	H28B—C28—H28C	109.00

O3—S1—N1—C5	−175.24 (17)	N1—C5—C6—C7	179.32 (18)
O4—S1—N1—C5	56.43 (19)	C4—C5—C6—C7	−0.5 (3)
C8—S1—N1—C5	−59.89 (19)	C5—C6—C7—C2	0.4 (3)
N1—S1—C8—C9	−56.08 (18)	S1—C8—C9—C10	−178.76 (17)
O3—S1—C8—C9	54.89 (17)	C13—C8—C9—C10	−1.6 (3)
O4—S1—C8—C9	−174.20 (15)	S1—C8—C13—C12	178.0 (2)
N1—S1—C8—C13	126.77 (18)	C9—C8—C13—C12	0.7 (4)
O3—S1—C8—C13	−122.27 (18)	C8—C9—C10—C11	1.2 (3)
O4—S1—C8—C13	8.7 (2)	C9—C10—C11—O5	180.0 (2)
O8—S2—C22—C23	−46.00 (17)	C9—C10—C11—C12	0.0 (4)
O8—S2—C22—C27	134.90 (15)	C10—C11—C12—C13	−0.8 (5)
O9—S2—C22—C23	−178.14 (14)	O5—C11—C12—C13	179.2 (3)
N2—S2—C22—C23	64.00 (16)	C11—C12—C13—C8	0.5 (4)
C22—S2—N2—C19	61.60 (18)	O7—C15—C16—C17	−172.0 (2)
O9—S2—C22—C27	2.76 (17)	O6—C15—C16—C17	8.0 (3)
N2—S2—C22—C27	−115.10 (15)	O6—C15—C16—C21	−170.94 (18)
O9—S2—N2—C19	−55.01 (19)	O7—C15—C16—C21	9.0 (3)
O8—S2—N2—C19	176.56 (16)	C21—C16—C17—C18	−0.1 (3)
C14—O5—C11—C10	4.3 (4)	C17—C16—C21—C20	0.4 (3)
C14—O5—C11—C12	−175.8 (3)	C15—C16—C17—C18	−179.01 (18)
C28—O10—C25—C24	−1.0 (3)	C15—C16—C21—C20	179.36 (18)
C28—O10—C25—C26	178.7 (2)	C16—C17—C18—C19	−0.2 (3)
S1—N1—C5—C4	−13.7 (3)	C17—C18—C19—C20	0.1 (3)
S1—N1—C5—C6	166.56 (15)	C17—C18—C19—N2	178.53 (17)
S2—N2—C19—C20	−169.78 (14)	N2—C19—C20—C21	−178.38 (17)
S2—N2—C19—C18	11.7 (3)	C18—C19—C20—C21	0.2 (3)
O1—C1—C2—C7	−179.84 (17)	C19—C20—C21—C16	−0.4 (3)
O2—C1—C2—C3	−175.85 (17)	S2—C22—C27—C26	178.50 (16)
O2—C1—C2—C7	1.0 (3)	C23—C22—C27—C26	−0.6 (3)
O1—C1—C2—C3	3.4 (3)	S2—C22—C23—C24	−177.51 (14)
C3—C2—C7—C6	−0.1 (3)	C27—C22—C23—C24	1.6 (3)
C1—C2—C3—C4	176.70 (17)	C22—C23—C24—C25	−0.7 (3)
C7—C2—C3—C4	−0.2 (3)	C23—C24—C25—C26	−1.1 (3)
C1—C2—C7—C6	−177.01 (17)	C23—C24—C25—O10	178.56 (18)
C2—C3—C4—C5	0.1 (3)	O10—C25—C26—C27	−177.6 (2)
C3—C4—C5—C6	0.2 (3)	C24—C25—C26—C27	2.2 (3)
C3—C4—C5—N1	−179.58 (17)	C25—C26—C27—C22	−1.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O8ⁱ	0.84 (2)	2.31 (2)	3.122 (2)	165 (2)
O2—HO1···O7ⁱⁱ	0.81 (2)	1.78 (2)	2.583 (2)	172 (2)
N2—HN2···O3ⁱⁱⁱ	0.82 (2)	2.15 (2)	2.959 (2)	173 (2)
O6—HO2···O1^iv	0.82 (2)	2.02 (2)	2.8338 (19)	173 (2)
C4—H4···O4	0.93	2.54	3.149 (2)	123
C7—H7···O2	0.93	2.39	2.709 (2)	100
C9—H9···O7	0.93	2.32	3.224 (3)	165
C13—H13···O4	0.93	2.51	2.883 (3)	105
C13—H13···O10^v	0.93	2.57	3.381 (3)	146
C14—H14A···O8^iv	0.96	2.42	3.370 (3)	169
C23—H23···O2	0.93	2.52	3.286 (2)	140
C26—H26···O1^vi	0.93	2.57	3.197 (2)	125
C27—H27···O9	0.93	2.54	2.905 (3)	104

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃NO₅S
M_r	307.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	8.6980 (3), 21.7471 (8), 14.5824 (6)
β (°)	95.153 (2)
V (Å³)	2747.21 (18)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.38 × 0.31 × 0.28

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker 2007)
T_min, T_max	0.909, 0.931
No. of measured, independent and observed [I > 2σ(I)] reflections	25188, 6806, 5475
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.120, 1.04
No. of reflections	6806
No. of parameters	394
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.30

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

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O8ⁱ	0.839 (16)	2.305 (17)	3.122 (2)	165 (2)
O2—HO1···O7ⁱⁱ	0.807 (19)	1.782 (19)	2.583 (2)	172 (2)
N2—HN2···O3ⁱⁱⁱ	0.818 (18)	2.145 (17)	2.959 (2)	173.1 (19)
O6—HO2···O1^iv	0.815 (18)	2.023 (19)	2.8338 (19)	173 (2)
C4—H4···O4	0.93	2.54	3.149 (2)	123
C9—H9···O7	0.93	2.32	3.224 (3)	165
C13—H13···O10^v	0.93	2.57	3.381 (3)	146
C14—H14A···O8^iv	0.96	2.42	3.370 (3)	169
C23—H23···O2	0.93	2.52	3.286 (2)	140
C26—H26···O1^vi	0.93	2.57	3.197 (2)	125

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

Acknowledgements

The authors are grateful to Mr Shahzad Shrif for his assistance and the Higher Education Commission (HEC), Pakistan, for financial support under the project to strengthen the Materials Chemistry Laboratory at GCUL.

References

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