N-{4-[(2-Meth-oxy-phen-yl)sulfamo-yl]phen-yl}acetamide.

In the title compound, C(15)H(16)N(2)O(4)S, the S atom has a distorted tetra-hedral 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 intra-molecular N-H⋯O hydrogen bond forms an S(6) ring motif. In the crystal, mol-ecules form centrosymmetric dimers via pairwise N-H⋯O inter-actions, forming an R(2) (2)(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 inter-action 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 ▶, ▶); Khan et al. (2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H16N2O4S

M = 320.37

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.118

S = 1.03

3788 reflections

220 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.28 e Å−3

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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811000432/hg2782sup1.cif

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

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

C15H16N2O4S	F(000) = 1344
Mr = 320.37	Dx = 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

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

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(Fo2) + (0.0648P)2 + 0.4113P] where P = (Fo2 + 2Fc2)/3
3788 reflections	(Δ/σ)max < 0.001
220 parameters	Δρmax = 0.35 e Å−3
2 restraints	Δρmin = −0.28 e Å−3

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	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*

	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)

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···H10Eix	3.0800
S1···H3i	3.1800	C11···H10F	2.8100
S1···H13ii	3.2000	C11···H10D	2.7700
O1A···C5	2.882 (16)	C11···H10Dxii	3.0200
O1A···C10iii	3.33 (2)	C13···H8Bxiii	2.8900
O1A···N2iii	3.257 (18)	C13···H5vii	3.0400
O1A···C9iii	3.248 (19)	C13···H6vii	2.9000
O1B···C5	2.858 (16)	C14···H5vii	2.9400
O1B···C10iii	3.30 (2)	C15···H11	2.5800
O2···N2iv	3.0482 (18)	HN1···H8A	2.3800
O2···O2iv	3.1045 (19)	HN1···O3vi	2.191 (19)
O3···N1i	2.995 (2)	HN1···H3	2.2200
O3···C14	3.065 (2)	H2···O1Bxiii	2.5600
O4···N2	2.6551 (19)	H2···O3	2.5300
O1A···H5	2.3000	HN2···O4	2.359 (19)
O1B···H2v	2.5600	HN2···O2iv	2.259 (18)
O1B···H5	2.3100	H3···S1vi	3.1800
O2···H3i	2.6300	H3···O2vi	2.6300
O2···HN2iv	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···O3vi	2.995 (2)	H6···C13iii	2.9000
N2···O1Avii	3.257 (18)	H6···O2	2.7500
N2···O2iv	3.0482 (18)	H8A···HN1	2.3800
N2···O4	2.6551 (19)	H8B···C13v	2.8900
N2···H12ii	2.8100	H10D···C11xii	3.0200
C2···C15viii	3.533 (3)	H10D···C11	2.7700
C5···O1A	2.882 (16)	H10D···H11	2.3800
C5···O1B	2.858 (16)	H10E···C8xi	3.0800
C6···C13iii	3.566 (3)	H10F···H11	2.3800
C8···C15ix	3.541 (4)	H10F···C2x	3.0100
C9···O1Avii	3.248 (19)	H10F···C11	2.8100
C10···O1Avii	3.33 (2)	H11···C15	2.5800
C10···O1Bvii	3.30 (2)	H11···H10D	2.3800
C13···C6vii	3.566 (3)	H11···H10F	2.3800
C14···O3	3.065 (2)	H11···C4xii	2.9700
C15···C2x	3.533 (3)	H12···N2xiv	2.8100
C15···C8xi	3.541 (4)	H13···S1xiv	3.2000
C2···H10Fviii	3.0100	H14···S1	3.1700
C4···H11xii	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)

Cg2 is the centroid of the C9–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O3vi	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···O2iv	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

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) ; (ii) ; (iii) .