4-Bromo-3-{N-[2-(3,4-dimethoxy-phen-yl)eth-yl]-N-methyl-sulfamo-yl}-5-methyl-benzoic acid monohydrate.

In the title compound, C(19)H(22)BrNO(6)S·H(2)O, the dihedral angle between the planes of the two benzene rings is 3.1 (1)°. These rings are stacked over one another with their centroids separated by 3.769 (2) Å, indicating weak π-π inter-actions. In the crystal structure, mol-ecules are linked by O-H⋯O and O-H⋯(O,O) hydrogen bonds involving the water mol-ecule, forming a two-dimensional network parallel to (001).

Related literature

For the biological activity of sulfonamides, see: Cates (1986 ▶); Steele & Beran (1984 ▶); Benedetti (1987 ▶); Mengelers et al. (1997 ▶). For related structures, see: Babu et al. (2009a ▶,b ▶); Shad et al. (2009 ▶); For graph-set notation, see: Bernstein et al. (1995 ▶)

Experimental

Crystal data

C19H22BrNO6S·H2O

M = 490.36

Orthorhombic,

a = 7.7938 (2) Å

b = 7.8280 (2) Å

c = 34.6549 (8) Å

V = 2114.29 (9) Å3

Z = 4

Mo Kα radiation

μ = 2.08 mm−1

T = 295 K

0.15 × 0.12 × 0.10 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.745, T max = 0.819

12583 measured reflections

4619 independent reflections

3427 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.107

S = 1.05

4619 reflections

275 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.30 e Å−3

Absolute structure: Flack (1983 ▶), 1915 Friedel pairs

Flack parameter: −0.004 (10)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809022041/ci2818sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022041/ci2818Isup2.hkl

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

C19H22BrNO6S·H2O	F(000) = 1008
Mr = 490.36	Dx = 1.540 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 12583 reflections
a = 7.7938 (2) Å	θ = 1.2–27.2°
b = 7.8280 (2) Å	µ = 2.08 mm−1
c = 34.6549 (8) Å	T = 295 K
V = 2114.29 (9) Å3	Block, colourless
Z = 4	0.15 × 0.12 × 0.10 mm

Bruker Kappa APEXII area-detector diffractometer	4619 independent reflections
Radiation source: fine-focus sealed tube	3427 reflections with I > 2σ(I)
graphite	Rint = 0.028
ω and φ scans	θmax = 27.2°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→6
Tmin = 0.745, Tmax = 0.819	k = −9→10
12583 measured reflections	l = −44→44

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)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.107	w = 1/[σ2(Fo2) + (0.0512P)2] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
4619 reflections	Δρmax = 0.36 e Å−3
275 parameters	Δρmin = −0.29 e Å−3
3 restraints	Absolute structure: Flack (1983), 1915 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.004 (10)

	x	y	z	Uiso*/Ueq
C1	0.4622 (4)	−0.0786 (5)	0.33480 (10)	0.0437 (9)
C2	0.4708 (4)	−0.1063 (5)	0.37399 (10)	0.0409 (8)
H2	0.5171	−0.2075	0.3835	0.049*
C3	0.4107 (4)	0.0161 (4)	0.39913 (9)	0.0379 (8)
C4	0.3406 (4)	0.1659 (5)	0.38498 (10)	0.0428 (8)
C5	0.3306 (5)	0.1973 (5)	0.34527 (11)	0.0490 (9)
C6	0.3940 (5)	0.0735 (5)	0.32070 (11)	0.0495 (9)
H6	0.3910	0.0921	0.2942	0.059*
C7	0.5272 (5)	−0.2101 (5)	0.30749 (10)	0.0500 (9)
C8	0.2547 (7)	0.3601 (5)	0.32931 (12)	0.0714 (12)
H8A	0.1351	0.3657	0.3358	0.107*
H8B	0.2674	0.3615	0.3018	0.107*
H8C	0.3133	0.4566	0.3402	0.107*
C9	0.1792 (6)	0.0519 (6)	0.49724 (11)	0.0665 (12)
H9A	0.0653	0.0908	0.4915	0.100*
H9B	0.2535	0.1485	0.5007	0.100*
H9C	0.1774	−0.0148	0.5205	0.100*
C10	0.1537 (5)	−0.2158 (5)	0.45884 (11)	0.0529 (10)
H10A	0.1564	−0.2827	0.4824	0.063*
H10B	0.2153	−0.2791	0.4392	0.063*
C11	−0.0297 (5)	−0.1940 (6)	0.44630 (12)	0.0606 (11)
H11A	−0.0842	−0.3054	0.4459	0.073*
H11B	−0.0889	−0.1251	0.4654	0.073*
C12	−0.0524 (5)	−0.1125 (5)	0.40751 (11)	0.0511 (10)
C13	−0.0043 (5)	−0.1982 (6)	0.37419 (13)	0.0625 (11)
H13	0.0431	−0.3069	0.3762	0.075*
C14	−0.0251 (5)	−0.1263 (6)	0.33830 (12)	0.0579 (11)
H14	0.0064	−0.1866	0.3163	0.069*
C15	−0.0922 (5)	0.0336 (6)	0.33519 (10)	0.0527 (10)
C16	−0.1403 (4)	0.1245 (5)	0.36809 (11)	0.0484 (9)
C17	−0.1194 (4)	0.0509 (5)	0.40371 (10)	0.0481 (9)
H17	−0.1507	0.1116	0.4257	0.058*
C18	−0.0805 (8)	0.0331 (7)	0.26626 (12)	0.0896 (16)
H18A	0.0405	0.0099	0.2655	0.134*
H18B	−0.1111	0.1043	0.2448	0.134*
H18C	−0.1428	−0.0725	0.2648	0.134*
C19	−0.2491 (6)	0.3849 (5)	0.39391 (12)	0.0633 (10)
H19A	−0.3342	0.3264	0.4089	0.095*
H19B	−0.2942	0.4926	0.3854	0.095*
H19C	−0.1489	0.4042	0.4094	0.095*
N1	0.2420 (5)	−0.0523 (4)	0.46561 (7)	0.0491 (7)
O1	0.5144 (5)	−0.1988 (5)	0.27278 (7)	0.0826 (10)
O2	0.5954 (4)	−0.3405 (4)	0.32450 (7)	0.0634 (7)
H2A	0.6330	−0.4068	0.3082	0.095*
O3	0.5148 (4)	0.1079 (4)	0.46804 (8)	0.0690 (8)
O4	0.5175 (4)	−0.1965 (4)	0.45044 (7)	0.0609 (8)
O5	−0.2047 (4)	0.2842 (4)	0.36146 (7)	0.0624 (8)
O6	−0.1214 (4)	0.1172 (4)	0.30090 (7)	0.0683 (8)
S1	0.43421 (12)	−0.03348 (13)	0.44937 (2)	0.0467 (2)
Br1	0.25758 (6)	0.33631 (5)	0.418916 (12)	0.06382 (16)
O1W	0.7092 (5)	−0.5755 (5)	0.28115 (11)	0.0720 (10)
H2W	0.749 (6)	−0.644 (5)	0.2931 (13)	0.074 (18)*
H1W	0.641 (6)	−0.627 (7)	0.2690 (14)	0.09 (2)*

	U11	U22	U33	U12	U13	U23
C1	0.0415 (18)	0.050 (2)	0.0399 (18)	−0.0069 (17)	−0.0028 (15)	−0.0013 (17)
C2	0.0412 (17)	0.040 (2)	0.0419 (18)	−0.0027 (15)	−0.0011 (15)	0.0009 (17)
C3	0.0372 (16)	0.042 (2)	0.0350 (16)	−0.0057 (15)	−0.0030 (14)	0.0002 (16)
C4	0.0365 (16)	0.0367 (19)	0.055 (2)	−0.0073 (16)	0.0003 (15)	−0.0056 (18)
C5	0.0495 (19)	0.042 (2)	0.056 (2)	−0.0081 (17)	−0.0055 (17)	0.0097 (19)
C6	0.057 (2)	0.054 (2)	0.0380 (18)	−0.0078 (19)	−0.0009 (16)	0.0117 (19)
C7	0.055 (2)	0.057 (2)	0.038 (2)	−0.0041 (16)	0.0011 (16)	−0.0068 (16)
C8	0.084 (3)	0.059 (3)	0.072 (3)	0.001 (3)	−0.001 (3)	0.021 (2)
C9	0.089 (3)	0.063 (3)	0.048 (2)	0.005 (2)	0.016 (2)	−0.013 (2)
C10	0.073 (3)	0.043 (2)	0.043 (2)	−0.0030 (19)	0.0064 (18)	0.0065 (17)
C11	0.061 (2)	0.064 (3)	0.057 (2)	−0.008 (2)	0.008 (2)	0.011 (2)
C12	0.0433 (18)	0.058 (3)	0.052 (2)	−0.0118 (18)	0.0007 (18)	−0.0030 (19)
C13	0.063 (2)	0.056 (3)	0.068 (3)	−0.003 (2)	0.003 (2)	−0.011 (2)
C14	0.063 (2)	0.060 (3)	0.050 (2)	0.000 (2)	0.0018 (19)	−0.015 (2)
C15	0.051 (2)	0.066 (3)	0.0408 (19)	0.000 (2)	−0.0015 (16)	−0.010 (2)
C16	0.0401 (18)	0.057 (3)	0.048 (2)	0.0007 (17)	−0.0030 (16)	−0.012 (2)
C17	0.0434 (19)	0.063 (3)	0.0382 (18)	−0.0067 (18)	0.0028 (15)	−0.0125 (19)
C18	0.127 (4)	0.097 (4)	0.045 (2)	0.009 (4)	0.014 (3)	−0.014 (3)
C19	0.066 (2)	0.063 (2)	0.062 (2)	0.007 (3)	0.001 (2)	−0.014 (2)
N1	0.0617 (17)	0.0490 (16)	0.0367 (14)	−0.0005 (19)	0.0051 (16)	−0.0077 (13)
O1	0.117 (3)	0.096 (3)	0.0341 (14)	0.021 (2)	−0.0022 (16)	−0.0001 (15)
O2	0.085 (2)	0.0635 (18)	0.0413 (13)	0.0139 (16)	−0.0039 (13)	−0.0106 (13)
O3	0.0662 (17)	0.086 (2)	0.0551 (15)	−0.0162 (16)	−0.0150 (13)	−0.0185 (16)
O4	0.0693 (17)	0.073 (2)	0.0410 (13)	0.0241 (15)	−0.0093 (13)	0.0071 (15)
O5	0.077 (2)	0.0691 (18)	0.0412 (14)	0.0187 (15)	0.0002 (13)	−0.0074 (13)
O6	0.087 (2)	0.078 (2)	0.0400 (14)	0.0153 (17)	−0.0033 (14)	−0.0105 (15)
S1	0.0499 (5)	0.0569 (6)	0.0334 (4)	0.0032 (5)	−0.0070 (4)	−0.0053 (4)
Br1	0.0684 (3)	0.0479 (2)	0.0752 (3)	0.0062 (2)	0.0019 (3)	−0.01215 (19)
O1W	0.089 (3)	0.072 (2)	0.0551 (19)	0.017 (2)	−0.0025 (18)	−0.0076 (19)

C1—C2	1.377 (5)	C11—H11B	0.97
C1—C6	1.392 (6)	C12—C13	1.387 (6)
C1—C7	1.487 (5)	C12—C17	1.388 (6)
C2—C3	1.377 (5)	C13—C14	1.375 (6)
C2—H2	0.93	C13—H13	0.93
C3—C4	1.383 (5)	C14—C15	1.361 (6)
C3—S1	1.793 (3)	C14—H14	0.93
C4—C5	1.400 (5)	C15—O6	1.375 (5)
C4—Br1	1.893 (4)	C15—C16	1.395 (5)
C5—C6	1.381 (6)	C16—O5	1.366 (5)
C5—C8	1.510 (5)	C16—C17	1.372 (5)
C6—H6	0.93	C17—H17	0.93
C7—O1	1.210 (4)	C18—O6	1.406 (5)
C7—O2	1.293 (5)	C18—H18A	0.96
C8—H8A	0.96	C18—H18B	0.96
C8—H8B	0.96	C18—H18C	0.96
C8—H8C	0.96	C19—O5	1.417 (5)
C9—N1	1.451 (5)	C19—H19A	0.96
C9—H9A	0.96	C19—H19B	0.96
C9—H9B	0.96	C19—H19C	0.96
C9—H9C	0.96	N1—S1	1.607 (4)
C10—N1	1.472 (5)	O2—H2A	0.82
C10—C11	1.504 (6)	O3—S1	1.428 (3)
C10—H10A	0.97	O4—S1	1.432 (3)
C10—H10B	0.97	O1W—H2W	0.75 (3)
C11—C12	1.498 (6)	O1W—H1W	0.79 (3)
C11—H11A	0.97
C2—C1—C6	120.0 (3)	H11A—C11—H11B	107.5
C2—C1—C7	120.1 (3)	C13—C12—C17	117.9 (4)
C6—C1—C7	119.9 (3)	C13—C12—C11	120.6 (4)
C3—C2—C1	119.9 (3)	C17—C12—C11	121.5 (4)
C3—C2—H2	120.1	C14—C13—C12	121.5 (4)
C1—C2—H2	120.1	C14—C13—H13	119.2
C2—C3—C4	120.0 (3)	C12—C13—H13	119.2
C2—C3—S1	115.4 (3)	C15—C14—C13	119.6 (4)
C4—C3—S1	124.6 (3)	C15—C14—H14	120.2
C3—C4—C5	121.3 (3)	C13—C14—H14	120.2
C3—C4—Br1	120.8 (3)	C14—C15—O6	124.7 (4)
C5—C4—Br1	117.9 (3)	C14—C15—C16	120.5 (4)
C6—C5—C4	117.6 (3)	O6—C15—C16	114.8 (4)
C6—C5—C8	120.4 (4)	O5—C16—C17	125.4 (3)
C4—C5—C8	122.0 (4)	O5—C16—C15	115.3 (3)
C5—C6—C1	121.3 (3)	C17—C16—C15	119.3 (4)
C5—C6—H6	119.3	C16—C17—C12	121.1 (4)
C1—C6—H6	119.3	C16—C17—H17	119.4
O1—C7—O2	123.0 (4)	C12—C17—H17	119.4
O1—C7—C1	123.6 (4)	O6—C18—H18A	109.5
O2—C7—C1	113.4 (3)	O6—C18—H18B	109.5
C5—C8—H8A	109.5	H18A—C18—H18B	109.5
C5—C8—H8B	109.5	O6—C18—H18C	109.5
H8A—C8—H8B	109.5	H18A—C18—H18C	109.5
C5—C8—H8C	109.5	H18B—C18—H18C	109.5
H8A—C8—H8C	109.5	O5—C19—H19A	109.5
H8B—C8—H8C	109.5	O5—C19—H19B	109.5
N1—C9—H9A	109.5	H19A—C19—H19B	109.5
N1—C9—H9B	109.5	O5—C19—H19C	109.5
H9A—C9—H9B	109.5	H19A—C19—H19C	109.5
N1—C9—H9C	109.5	H19B—C19—H19C	109.5
H9A—C9—H9C	109.5	C9—N1—C10	116.8 (3)
H9B—C9—H9C	109.5	C9—N1—S1	121.8 (3)
N1—C10—C11	113.0 (3)	C10—N1—S1	117.3 (2)
N1—C10—H10A	109.0	C7—O2—H2A	109.5
C11—C10—H10A	109.0	C16—O5—C19	117.7 (3)
N1—C10—H10B	109.0	C15—O6—C18	118.5 (4)
C11—C10—H10B	109.0	O3—S1—O4	118.65 (17)
H10A—C10—H10B	107.8	O3—S1—N1	108.82 (16)
C12—C11—C10	114.8 (3)	O4—S1—N1	109.40 (17)
C12—C11—H11A	108.6	O3—S1—C3	108.50 (17)
C10—C11—H11A	108.6	O4—S1—C3	105.31 (16)
C12—C11—H11B	108.6	N1—S1—C3	105.34 (15)
C10—C11—H11B	108.6	H2W—O1W—H1W	102 (6)
C6—C1—C2—C3	0.5 (5)	C13—C14—C15—C16	−0.3 (6)
C7—C1—C2—C3	179.9 (3)	C14—C15—C16—O5	179.5 (4)
C1—C2—C3—C4	0.5 (5)	O6—C15—C16—O5	−1.7 (5)
C1—C2—C3—S1	−178.5 (3)	C14—C15—C16—C17	0.0 (6)
C2—C3—C4—C5	−0.6 (5)	O6—C15—C16—C17	178.8 (3)
S1—C3—C4—C5	178.3 (3)	O5—C16—C17—C12	−179.9 (3)
C2—C3—C4—Br1	−179.8 (2)	C15—C16—C17—C12	−0.5 (5)
S1—C3—C4—Br1	−0.9 (4)	C13—C12—C17—C16	1.1 (5)
C3—C4—C5—C6	−0.2 (5)	C11—C12—C17—C16	−179.8 (3)
Br1—C4—C5—C6	179.0 (3)	C11—C10—N1—C9	65.3 (4)
C3—C4—C5—C8	−179.9 (4)	C11—C10—N1—S1	−136.7 (3)
Br1—C4—C5—C8	−0.7 (5)	C17—C16—O5—C19	2.0 (5)
C4—C5—C6—C1	1.2 (5)	C15—C16—O5—C19	−177.4 (3)
C8—C5—C6—C1	−179.1 (4)	C14—C15—O6—C18	0.3 (6)
C2—C1—C6—C5	−1.4 (5)	C16—C15—O6—C18	−178.5 (4)
C7—C1—C6—C5	179.2 (3)	C9—N1—S1—O3	−6.1 (4)
C2—C1—C7—O1	175.4 (4)	C10—N1—S1—O3	−163.0 (3)
C6—C1—C7—O1	−5.1 (6)	C9—N1—S1—O4	124.9 (3)
C2—C1—C7—O2	−3.0 (5)	C10—N1—S1—O4	−31.9 (3)
C6—C1—C7—O2	176.4 (3)	C9—N1—S1—C3	−122.3 (3)
N1—C10—C11—C12	66.2 (5)	C10—N1—S1—C3	80.9 (3)
C10—C11—C12—C13	68.6 (5)	C2—C3—S1—O3	129.1 (3)
C10—C11—C12—C17	−110.5 (4)	C4—C3—S1—O3	−49.9 (3)
C17—C12—C13—C14	−1.4 (6)	C2—C3—S1—O4	1.1 (3)
C11—C12—C13—C14	179.5 (4)	C4—C3—S1—O4	−177.9 (3)
C12—C13—C14—C15	1.0 (6)	C2—C3—S1—N1	−114.5 (3)
C13—C14—C15—O6	−178.9 (4)	C4—C3—S1—N1	66.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1W	0.82	1.73	2.535 (4)	169
O1W—H1W···O1i	0.79 (3)	1.97 (4)	2.732 (5)	162 (6)
O1W—H2W···O5ii	0.75 (3)	2.46 (4)	3.066 (5)	139 (5)
O1W—H2W···O6ii	0.75 (3)	2.14 (4)	2.828 (5)	154 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O1W	0.82	1.73	2.535 (4)	169
O1W—H1W⋯O1i	0.79 (3)	1.97 (4)	2.732 (5)	162 (6)
O1W—H2W⋯O5ii	0.75 (3)	2.46 (4)	3.066 (5)	139 (5)
O1W—H2W⋯O6ii	0.75 (3)	2.14 (4)	2.828 (5)	154 (5)

Symmetry codes: (i) ; (ii) .