2-{4-[Acet-yl(eth-yl)amino]-benzene-sulfonamido}-benzoic acid.

In the title compound, C(17)H(18)N(2)O(5)S, the dihedral angle between the aromatic rings is 68.59 (10)° and the C-S-N-C torsion angle is -81.84 (18)°. The mol-ecular conformation is stabilized by an intra-molecular N-H⋯O hydrogen bond, generating an S(6) ring. In the crystal, mol-ecules 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 = 362.40

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.093

S = 0.99

3880 reflections

233 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.18 e Å−3

Absolute structure: Flack (1983 ▶), 1612 Freidel pairs

Flack parameter: 0.05 (6)

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812013864/hb6720sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812013864/hb6720Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H18N2O5S	F(000) = 760
Mr = 362.40	Dx = 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

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

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(Fo2) + (0.0604P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max < 0.001
3880 reflections	Δρmax = 0.35 e Å−3
233 parameters	Δρmin = −0.18 e Å−3
2 restraints	Absolute structure: Flack (1983), 1612 Freidel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.05 (6)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .