2-(4-Acetamido­benzene­sulfonamido)­benzoic acid

Sharif, S.; Khan, I.U.; Mahmood, T.; Kang, S.K.

doi:10.1107/S1600536811020307

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1570

doi:10.1107/S1600536811020307

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2-(4-Acetamidobenzenesulfonamido)benzoic acid

Shahzad Sharif,^a Islam Ullah Khan,^a Tariq Mahmood ^b and Sung Kwon Kang ^c ^*

^aMaterials Chemistry Laboratory, Department of Chemistry, Government College University, Lahore 54000, Pakistan, ^bGlaxo Smith Kline, 18 KM Feroze Pur Road, Lahore 54000, Pakistan, and ^cDepartment of Chemistry, Chungnam National University, Daejeon 305-764, Republic of Korea
^*Correspondence e-mail: skkang@cnu.ac.kr

(Received 19 May 2011; accepted 27 May 2011; online 4 June 2011)

In the title compound, C₁₅H₁₄N₂O₅S, two similar molecules comprise the asymmetric unit, which are linked by strong intermolecular C—H⋯π interactions. Both molecules are bent, with dihedral angles of 71.94 (16) and 74.62 (15)° between the benzene rings. An intramolecular N—H⋯O hydrogen bond occurs in each molecule. In the crystal, intermolecular N—H⋯O and O—H⋯O hydrogen bonds link the molecules into a three-dimensional network.

Related literature

For our previous studies on sulfonamide derivatives, see: Khan et al. (2011 ); Sharif et al. (2010 ). For background to the pharmacological use of sulfonamides, see: Korolkovas (1988 ); Mandell & Sande (1992 ).

Experimental

Crystal data

C₁₅H₁₄N₂O₅S
M_r = 334.34
Monoclinic, P 2₁
a = 9.3721 (19) Å
b = 13.036 (3) Å
c = 13.132 (3) Å
β = 109.47 (3)°
V = 1512.7 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 296 K
0.25 × 0.12 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.92, T_max = 0.931
2926 measured reflections
2926 independent reflections
1470 reflections with I > 2σ(I)

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.092
S = 0.82
2926 reflections
415 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C37–C42 and C14–C19 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O9—H9⋯O22ⁱ	0.82	1.84	2.649 (6)	168
N10—H10⋯O8	0.86	2.13	2.624 (7)	116
N20—H20⋯O13ⁱⁱ	0.86	2.24	3.073 (6)	164
O31—H31⋯O45ⁱⁱⁱ	0.82	1.81	2.623 (6)	174
N33—H33⋯O32	0.86	2.17	2.641 (7)	114
N43—H43⋯O36ⁱ	0.86	2.11	2.958 (7)	168
C23—H23B⋯Cg1	0.96	2.74	3.6110 (15)	151
C46—H46C⋯Cg2	0.96	2.71	3.5821 (13)	151
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+1]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z]$ ; (iii) x-1, y, 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 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811020307/tk2747sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811020307/tk2747Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811020307/tk2747Isup3.cml

checkCIF report

Comment top

In continuation of our structural studies of sulfonamides (Khan et al., 2011; Sharif et al., 2010) of the interest owing to their potential as biologically active molecules (Korolkovas, 1988; Mandell & Sande, 1992), herein, we report the crystal structure of the title compound, (I).

Two independent but similar molecules comprise the asymmetric unit, Fig. 1. The phenyl carboxyl moieties are almost planar with r.m.s. deviations of 0.012 and 0.023 Å from the corresponding least-squares plane defined by the eight constituent atoms. The dihedral angles between the benzene rings are 71.94 (16) and 74.62 (15) °. The two independent molecules are linked by intermolecular C—H···π interactions (centroid—H distance = 2.711 (3) and 2.740 (3) Å) (Fig. 1). In the crystal, intermolecular N—H···O and O—H···O hydrogen bonds link the molecules into a three-dimensional network (Table 1, Fig. 2).

Related literature top

For our previous studies on sulfonamide derivatives, see: Khan et al. (2011); Sharif et al. (2010). For background to the pharmacological use of sulfonamides, see: Korolkovas (1988); Mandell & Sande (1992).

Experimental top

To anthranilic acid (137 mg, 1 mmol) in distilled water (10 ml) was added 4-acetamidobenzenesulfonyl chloride (234 mg, 1 mmol). The pH = 8 was maintained by 3% Na₂CO₃ with stirring at room temperature. The reaction was monitored by TLC. After completion of reaction, the solution was adjusted to pH =3 with 3 N HCl solution. The white precipitate that formed was filtered and washed with water. Crystallization was from 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: SHELXS97 (Sheldrick, 2008); 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 publication routines (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structures of the two independent molecules of (I) showing the atom-numbering scheme and 30% probability ellipsoids. The C—H···π interactions are shown as dashed lines.
	Fig. 2. Part of the crystal structure of (I), viewed normal to (0 0 1), illustrating the 3-D network of molecules linked by intermolecular N—H···O and O—H···O hydrogen bonds (dashed lines).

2-(4-Acetamidobenzenesulfonamido)benzoic acid top

Crystal data top

C₁₅H₁₄N₂O₅S	F(000) = 696
M_r = 334.34	D_x = 1.468 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1295 reflections
a = 9.3721 (19) Å	θ = 2.8–18.7°
b = 13.036 (3) Å	µ = 0.24 mm⁻¹
c = 13.132 (3) Å	T = 296 K
β = 109.47 (3)°	Block, violet
V = 1512.7 (5) Å³	0.25 × 0.12 × 0.09 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	2926 independent reflections
Graphite monochromator	1470 reflections with I > 2σ(I)
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −11→10
T_min = 0.92, T_max = 0.931	k = 0→15
2926 measured reflections	l = 0→15

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H-atom parameters constrained
S = 0.82	w = 1/[σ²(F_o²) + (0.0338P)²] where P = (F_o² + 2F_c²)/3
2926 reflections	(Δ/σ)_max < 0.001
415 parameters	Δρ_max = 0.26 e Å⁻³
1 restraint	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₅H₁₄N₂O₅S	V = 1512.7 (5) Å³
M_r = 334.34	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 9.3721 (19) Å	µ = 0.24 mm⁻¹
b = 13.036 (3) Å	T = 296 K
c = 13.132 (3) Å	0.25 × 0.12 × 0.09 mm
β = 109.47 (3)°

Data collection top

Bruker APEXII CCD diffractometer	2926 measured reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2926 independent reflections
T_min = 0.92, T_max = 0.931	1470 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.045	1 restraint
wR(F²) = 0.092	H-atom parameters constrained
S = 0.82	Δρ_max = 0.26 e Å⁻³
2926 reflections	Δρ_min = −0.24 e Å⁻³
415 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

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 > 2σ(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
C1	0.9116 (7)	0.1951 (5)	0.4462 (5)	0.0489 (17)
C2	0.8856 (6)	0.1876 (4)	0.3361 (5)	0.0378 (15)
C3	0.9664 (8)	0.2491 (5)	0.2895 (6)	0.069 (2)
H3	0.9489	0.2433	0.2157	0.082*
C4	1.0705 (8)	0.3179 (6)	0.3474 (7)	0.068 (2)
H4	1.124	0.3585	0.3143	0.081*
C5	1.0948 (8)	0.3260 (6)	0.4565 (7)	0.078 (2)
H5	1.1645	0.3736	0.4972	0.094*
C6	1.0181 (8)	0.2652 (6)	0.5064 (6)	0.0547 (18)
H6	1.0374	0.271	0.5804	0.066*
C7	0.8274 (7)	0.1297 (5)	0.4990 (5)	0.0444 (16)
O8	0.7297 (6)	0.0692 (4)	0.4533 (4)	0.0761 (16)
O9	0.8716 (5)	0.1415 (4)	0.6050 (4)	0.0753 (14)
H9	0.8211	0.1043	0.63	0.113*
N10	0.7746 (6)	0.1191 (4)	0.2728 (4)	0.0556 (15)
H10	0.7657	0.0613	0.3017	0.067*
S11	0.6629 (2)	0.13965 (13)	0.15141 (13)	0.0496 (5)
O12	0.5537 (5)	0.0600 (3)	0.1345 (3)	0.0650 (13)
O13	0.7415 (4)	0.1479 (3)	0.0766 (3)	0.0601 (12)
C14	0.5771 (6)	0.2586 (5)	0.1545 (5)	0.0409 (16)
C15	0.5660 (7)	0.3302 (5)	0.0747 (5)	0.0505 (18)
H15	0.6111	0.3183	0.0225	0.061*
C16	0.4882 (7)	0.4181 (5)	0.0734 (5)	0.0523 (19)
H16	0.48	0.4663	0.0196	0.063*
C17	0.4204 (6)	0.4379 (5)	0.1504 (5)	0.0374 (15)
C18	0.4315 (7)	0.3678 (5)	0.2282 (5)	0.0485 (18)
H18	0.3873	0.3809	0.2806	0.058*
C19	0.5082 (7)	0.2768 (5)	0.2307 (5)	0.0479 (17)
H19	0.5134	0.228	0.2834	0.057*
N20	0.3395 (5)	0.5312 (4)	0.1386 (4)	0.0434 (13)
H20	0.3362	0.5668	0.0827	0.052*
C21	0.2673 (6)	0.5729 (5)	0.2010 (5)	0.0411 (16)
O22	0.2672 (5)	0.5316 (3)	0.2864 (3)	0.0580 (13)
C23	0.1884 (7)	0.6728 (4)	0.1635 (5)	0.059 (2)
H23A	0.2015	0.6925	0.0967	0.088*
H23B	0.2307	0.7246	0.217	0.088*
H23C	0.0825	0.6653	0.1527	0.088*
C24	−0.0124 (7)	0.9059 (5)	0.1004 (5)	0.0449 (16)
C25	0.0910 (7)	0.9800 (5)	0.1592 (5)	0.0437 (17)
C26	0.1722 (7)	1.0380 (5)	0.1075 (6)	0.061 (2)
H26	0.2361	1.09	0.1449	0.074*
C27	0.1581 (7)	1.0185 (6)	0.0021 (6)	0.064 (2)
H27	0.2137	1.0569	−0.0312	0.077*
C28	0.0617 (8)	0.9422 (6)	−0.0555 (6)	0.071 (2)
H28	0.0553	0.9272	−0.1261	0.085*
C29	−0.0240 (7)	0.8892 (5)	−0.0065 (6)	0.0510 (18)
H29	−0.0924	0.8405	−0.0463	0.061*
C30	−0.1013 (7)	0.8458 (5)	0.1504 (6)	0.0479 (17)
O31	−0.1843 (5)	0.7725 (4)	0.0872 (4)	0.0677 (14)
H31	−0.2313	0.7413	0.12	0.101*
O32	−0.1066 (5)	0.8583 (4)	0.2407 (4)	0.0691 (15)
N33	0.1094 (5)	0.9963 (4)	0.2685 (4)	0.0555 (15)
H33	0.0295	0.9965	0.2869	0.067*
S34	0.2731 (2)	1.01499 (13)	0.36347 (14)	0.0574 (5)
O35	0.3439 (5)	1.1036 (3)	0.3377 (4)	0.0690 (14)
O36	0.2365 (5)	1.0137 (4)	0.4614 (3)	0.0713 (13)
C37	0.3874 (7)	0.9084 (5)	0.3622 (5)	0.0471 (17)
C38	0.4644 (7)	0.9058 (5)	0.2911 (6)	0.059 (2)
H38	0.4576	0.9616	0.2457	0.07*
C39	0.5520 (7)	0.8235 (6)	0.2842 (6)	0.0584 (19)
H39	0.6053	0.8234	0.2358	0.07*
C40	0.5584 (7)	0.7408 (5)	0.3516 (5)	0.0498 (18)
C41	0.4833 (7)	0.7435 (5)	0.4263 (5)	0.0540 (19)
H41	0.4912	0.6889	0.4733	0.065*
C42	0.3979 (7)	0.8271 (5)	0.4301 (5)	0.0530 (18)
H42	0.3462	0.8289	0.4794	0.064*
N43	0.6463 (5)	0.6529 (4)	0.3513 (4)	0.0563 (15)
H43	0.6701	0.6161	0.4089	0.068*
C44	0.6993 (7)	0.6179 (6)	0.2710 (6)	0.0548 (19)
O45	0.6655 (5)	0.6604 (4)	0.1829 (4)	0.0682 (14)
C46	0.7926 (7)	0.5216 (6)	0.2971 (5)	0.071 (2)
H46A	0.8045	0.5004	0.3695	0.106*
H46B	0.8903	0.5345	0.291	0.106*
H46C	0.7426	0.4684	0.2475	0.106*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.055 (4)	0.049 (5)	0.045 (4)	0.016 (4)	0.019 (4)	0.011 (4)
C2	0.038 (4)	0.027 (4)	0.051 (4)	0.014 (3)	0.019 (4)	0.012 (4)
C3	0.077 (6)	0.060 (5)	0.071 (6)	−0.005 (4)	0.027 (5)	0.003 (4)
C4	0.050 (5)	0.063 (6)	0.081 (6)	−0.001 (4)	0.009 (5)	0.017 (5)
C5	0.063 (6)	0.059 (6)	0.094 (7)	−0.003 (4)	0.002 (5)	0.006 (5)
C6	0.049 (4)	0.051 (5)	0.057 (5)	−0.004 (4)	0.007 (4)	0.004 (4)
C7	0.050 (4)	0.048 (4)	0.035 (4)	0.010 (4)	0.013 (3)	0.004 (4)
O8	0.091 (4)	0.081 (4)	0.056 (3)	−0.030 (3)	0.023 (3)	0.005 (3)
O9	0.083 (4)	0.088 (4)	0.054 (3)	−0.007 (3)	0.022 (3)	0.003 (3)
N10	0.081 (4)	0.034 (3)	0.046 (3)	0.006 (3)	0.014 (3)	0.008 (3)
S11	0.0681 (12)	0.0425 (11)	0.0387 (10)	−0.0015 (10)	0.0186 (9)	−0.0069 (9)
O12	0.101 (4)	0.038 (3)	0.063 (3)	−0.023 (3)	0.038 (3)	−0.013 (2)
O13	0.079 (3)	0.056 (3)	0.057 (3)	−0.001 (3)	0.038 (3)	−0.010 (3)
C14	0.044 (4)	0.036 (4)	0.041 (4)	0.002 (3)	0.011 (3)	0.001 (3)
C15	0.073 (5)	0.053 (5)	0.038 (4)	0.003 (4)	0.035 (4)	0.007 (4)
C16	0.065 (5)	0.054 (5)	0.040 (4)	0.011 (4)	0.020 (4)	0.015 (3)
C17	0.041 (4)	0.033 (4)	0.039 (4)	0.001 (3)	0.014 (3)	0.002 (3)
C18	0.055 (4)	0.052 (5)	0.051 (4)	0.010 (3)	0.033 (4)	0.018 (4)
C19	0.064 (4)	0.052 (5)	0.033 (4)	−0.004 (4)	0.023 (4)	0.013 (4)
N20	0.051 (3)	0.048 (4)	0.037 (3)	0.004 (3)	0.023 (3)	0.012 (3)
C21	0.043 (4)	0.042 (4)	0.034 (4)	−0.011 (3)	0.006 (3)	−0.005 (3)
O22	0.077 (3)	0.058 (3)	0.051 (3)	0.004 (3)	0.036 (3)	0.001 (3)
C23	0.069 (5)	0.052 (5)	0.052 (4)	0.014 (4)	0.017 (4)	−0.008 (4)
C24	0.043 (4)	0.048 (4)	0.045 (4)	0.004 (3)	0.016 (3)	0.011 (4)
C25	0.046 (4)	0.048 (5)	0.042 (4)	0.013 (3)	0.020 (4)	0.009 (3)
C26	0.065 (5)	0.061 (5)	0.058 (5)	−0.001 (4)	0.022 (4)	−0.004 (4)
C27	0.065 (5)	0.064 (6)	0.063 (5)	0.008 (4)	0.023 (4)	0.026 (5)
C28	0.068 (5)	0.089 (7)	0.053 (5)	−0.002 (5)	0.017 (4)	0.008 (5)
C29	0.055 (5)	0.056 (5)	0.043 (4)	0.007 (4)	0.017 (4)	0.004 (4)
C30	0.052 (5)	0.046 (5)	0.048 (5)	0.013 (4)	0.021 (4)	0.010 (4)
O31	0.071 (3)	0.070 (3)	0.064 (3)	−0.015 (3)	0.025 (3)	−0.010 (3)
O32	0.080 (4)	0.076 (4)	0.065 (3)	−0.010 (3)	0.041 (3)	0.000 (3)
N33	0.051 (3)	0.070 (4)	0.046 (3)	0.009 (3)	0.016 (3)	−0.011 (3)
S34	0.0712 (13)	0.0507 (13)	0.0499 (11)	−0.0118 (10)	0.0194 (10)	−0.0137 (10)
O35	0.088 (4)	0.042 (3)	0.079 (3)	−0.022 (3)	0.029 (3)	−0.008 (3)
O36	0.101 (4)	0.064 (3)	0.056 (3)	−0.014 (3)	0.037 (3)	−0.017 (3)
C37	0.055 (5)	0.047 (5)	0.038 (4)	−0.011 (3)	0.013 (4)	−0.002 (4)
C38	0.064 (5)	0.052 (5)	0.062 (5)	−0.010 (4)	0.024 (4)	0.024 (4)
C39	0.052 (5)	0.067 (5)	0.062 (5)	0.007 (4)	0.027 (4)	0.026 (4)
C40	0.041 (4)	0.065 (5)	0.045 (4)	−0.001 (4)	0.015 (4)	0.008 (4)
C41	0.058 (5)	0.065 (6)	0.038 (4)	−0.002 (4)	0.014 (4)	0.010 (4)
C42	0.063 (5)	0.059 (5)	0.042 (4)	−0.004 (4)	0.025 (4)	−0.012 (4)
N43	0.058 (4)	0.062 (4)	0.045 (3)	0.003 (3)	0.012 (3)	0.019 (3)
C44	0.047 (4)	0.066 (6)	0.048 (5)	−0.021 (4)	0.013 (4)	−0.005 (4)
O45	0.098 (4)	0.065 (4)	0.050 (3)	−0.020 (3)	0.036 (3)	−0.006 (3)
C46	0.057 (5)	0.084 (6)	0.066 (5)	0.004 (5)	0.014 (4)	−0.015 (5)

Geometric parameters (Å, º) top

C1—C2	1.387 (8)	C24—C29	1.389 (8)
C1—C6	1.389 (9)	C24—C25	1.403 (8)
C1—C7	1.482 (8)	C24—C30	1.450 (8)
C2—C3	1.379 (8)	C25—C26	1.399 (8)
C2—N10	1.412 (7)	C25—N33	1.402 (7)
C3—C4	1.356 (9)	C26—C27	1.370 (8)
C3—H3	0.93	C26—H26	0.93
C4—C5	1.378 (9)	C27—C28	1.386 (9)
C4—H4	0.93	C27—H27	0.93
C5—C6	1.374 (9)	C28—C29	1.372 (9)
C5—H5	0.93	C28—H28	0.93
C6—H6	0.93	C29—H29	0.93
C7—O8	1.206 (7)	C30—O32	1.215 (7)
C7—O9	1.322 (7)	C30—O31	1.332 (8)
O9—H9	0.82	O31—H31	0.82
N10—S11	1.611 (5)	N33—S34	1.641 (5)
N10—H10	0.86	N33—H33	0.86
S11—O13	1.415 (4)	S34—O35	1.429 (4)
S11—O12	1.423 (4)	S34—O36	1.438 (4)
S11—C14	1.754 (6)	S34—C37	1.758 (7)
C14—C19	1.380 (7)	C37—C38	1.358 (8)
C14—C15	1.382 (8)	C37—C42	1.366 (8)
C15—C16	1.355 (8)	C38—C39	1.371 (9)
C15—H15	0.93	C38—H38	0.93
C16—C17	1.386 (7)	C39—C40	1.383 (8)
C16—H16	0.93	C39—H39	0.93
C17—C18	1.348 (8)	C40—C41	1.385 (8)
C17—N20	1.414 (7)	C40—N43	1.412 (7)
C18—C19	1.382 (8)	C41—C42	1.363 (8)
C18—H18	0.93	C41—H41	0.93
C19—H19	0.93	C42—H42	0.93
N20—C21	1.340 (7)	N43—C44	1.385 (8)
N20—H20	0.86	N43—H43	0.86
C21—O22	1.244 (6)	C44—O45	1.224 (7)
C21—C23	1.497 (8)	C44—C46	1.503 (9)
C23—H23A	0.96	C46—H46A	0.96
C23—H23B	0.96	C46—H46B	0.96
C23—H23C	0.96	C46—H46C	0.96

C2—C1—C6	118.9 (7)	C29—C24—C25	118.1 (6)
C2—C1—C7	120.8 (6)	C29—C24—C30	120.7 (7)
C6—C1—C7	120.3 (7)	C25—C24—C30	121.2 (6)
C3—C2—C1	119.3 (6)	C26—C25—N33	120.9 (6)
C3—C2—N10	120.8 (6)	C26—C25—C24	119.5 (6)
C1—C2—N10	119.8 (6)	N33—C25—C24	119.6 (6)
C4—C3—C2	122.3 (7)	C27—C26—C25	120.4 (6)
C4—C3—H3	118.9	C27—C26—H26	119.8
C2—C3—H3	118.9	C25—C26—H26	119.8
C3—C4—C5	118.2 (8)	C26—C27—C28	120.7 (7)
C3—C4—H4	120.9	C26—C27—H27	119.7
C5—C4—H4	120.9	C28—C27—H27	119.7
C6—C5—C4	121.3 (7)	C29—C28—C27	118.8 (7)
C6—C5—H5	119.3	C29—C28—H28	120.6
C4—C5—H5	119.3	C27—C28—H28	120.6
C5—C6—C1	119.9 (7)	C28—C29—C24	122.4 (7)
C5—C6—H6	120.1	C28—C29—H29	118.8
C1—C6—H6	120.1	C24—C29—H29	118.8
O8—C7—O9	121.3 (6)	O32—C30—O31	120.0 (6)
O8—C7—C1	125.3 (6)	O32—C30—C24	125.8 (7)
O9—C7—C1	113.4 (6)	O31—C30—C24	114.2 (6)
C7—O9—H9	109.5	C30—O31—H31	109.5
C2—N10—S11	125.8 (4)	C25—N33—S34	124.4 (4)
C2—N10—H10	117.1	C25—N33—H33	117.8
S11—N10—H10	117.1	S34—N33—H33	117.8
O13—S11—O12	117.5 (3)	O35—S34—O36	119.3 (3)
O13—S11—N10	112.5 (3)	O35—S34—N33	109.3 (3)
O12—S11—N10	103.2 (3)	O36—S34—N33	103.7 (3)
O13—S11—C14	107.3 (3)	O35—S34—C37	107.7 (3)
O12—S11—C14	109.7 (3)	O36—S34—C37	109.1 (3)
N10—S11—C14	106.0 (3)	N33—S34—C37	107.1 (3)
C19—C14—C15	119.9 (6)	C38—C37—C42	119.3 (6)
C19—C14—S11	119.9 (5)	C38—C37—S34	119.4 (6)
C15—C14—S11	119.9 (5)	C42—C37—S34	121.2 (5)
C16—C15—C14	119.0 (6)	C37—C38—C39	122.1 (6)
C16—C15—H15	120.5	C37—C38—H38	118.9
C14—C15—H15	120.5	C39—C38—H38	118.9
C15—C16—C17	121.7 (6)	C38—C39—C40	117.8 (6)
C15—C16—H16	119.2	C38—C39—H39	121.1
C17—C16—H16	119.2	C40—C39—H39	121.1
C18—C17—C16	119.2 (6)	C39—C40—C41	120.6 (7)
C18—C17—N20	124.7 (5)	C39—C40—N43	122.2 (6)
C16—C17—N20	116.1 (5)	C41—C40—N43	117.2 (6)
C17—C18—C19	120.5 (6)	C42—C41—C40	119.3 (6)
C17—C18—H18	119.7	C42—C41—H41	120.3
C19—C18—H18	119.7	C40—C41—H41	120.3
C14—C19—C18	119.7 (6)	C41—C42—C37	120.8 (6)
C14—C19—H19	120.1	C41—C42—H42	119.6
C18—C19—H19	120.1	C37—C42—H42	119.6
C21—N20—C17	130.0 (5)	C44—N43—C40	128.8 (6)
C21—N20—H20	115	C44—N43—H43	115.6
C17—N20—H20	115	C40—N43—H43	115.6
O22—C21—N20	121.9 (6)	O45—C44—N43	121.7 (7)
O22—C21—C23	121.6 (6)	O45—C44—C46	122.7 (7)
N20—C21—C23	116.5 (6)	N43—C44—C46	115.5 (6)
C21—C23—H23A	109.5	C44—C46—H46A	109.5
C21—C23—H23B	109.5	C44—C46—H46B	109.5
H23A—C23—H23B	109.5	H46A—C46—H46B	109.5
C21—C23—H23C	109.5	C44—C46—H46C	109.5
H23A—C23—H23C	109.5	H46A—C46—H46C	109.5
H23B—C23—H23C	109.5	H46B—C46—H46C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9···O22ⁱ	0.82	1.84	2.649 (6)	168
N10—H10···O8	0.86	2.13	2.624 (7)	116
N20—H20···O13ⁱⁱ	0.86	2.24	3.073 (6)	164
O31—H31···O45ⁱⁱⁱ	0.82	1.81	2.623 (6)	174
N33—H33···O32	0.86	2.17	2.641 (7)	114
N43—H43···O36ⁱ	0.86	2.11	2.958 (7)	168
C23—H23B···Cg1	0.96	2.74	3.6110 (15)	151
C46—H46C···Cg2	0.96	2.71	3.5821 (13)	151

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄N₂O₅S
M_r	334.34
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	9.3721 (19), 13.036 (3), 13.132 (3)
β (°)	109.47 (3)
V (Å³)	1512.7 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.25 × 0.12 × 0.09

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.92, 0.931
No. of measured, independent and observed [I > 2σ(I)] reflections	2926, 2926, 1470
R_int	?
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.092, 0.82
No. of reflections	2926
No. of parameters	415
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.24

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX publication routines (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9···O22ⁱ	0.82	1.84	2.649 (6)	168
N10—H10···O8	0.86	2.13	2.624 (7)	116
N20—H20···O13ⁱⁱ	0.86	2.24	3.073 (6)	164
O31—H31···O45ⁱⁱⁱ	0.82	1.81	2.623 (6)	174
N33—H33···O32	0.86	2.17	2.641 (7)	114
N43—H43···O36ⁱ	0.86	2.11	2.958 (7)	168
C23—H23B···Cg1	0.96	2.74	3.6110 (15)	151
C46—H46C···Cg2	0.96	2.71	3.5821 (13)	151

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

References

Bruker (2007). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Khan, I. U., Bibi, S., Mariam, I., Sharif, S. & Kang, S. K. (2011). Acta Cryst. E67, o369. Web of Science CSD CrossRef IUCr Journals Google Scholar
Korolkovas, A. (1988). Essentials of Medicinal Chemistry, 2nd ed, pp. 699–716. New York: Wiley. Google Scholar
Mandell, G. L. & Sande, M. A. (1992). Goodman and Gilman, The Pharmacological Basis of Therapeutics 2, edited by A. Gilman, T. W. Rall, A. S. Nies & P. Taylor, 8th ed., pp. 1047–1057. Singapore: McGraw-Hill. Google Scholar
Sharif, S., Iqbal, H., Khan, I. U., John, P. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o1288. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 7| July 2011| Page o1570

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