4-Bromo-3-{N-[2-(3,4-dimethoxy­phen­yl)eth­yl]-N-methyl­sulfamo­yl}-5-methyl­benzoic acid monohydrate

Babu, C.S.M.; Kavitha, H.P.; Vennila, J.P.; Chakkaravarthi, G.; Manivannan, V.

doi:10.1107/S1600536809022041

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1568

doi:10.1107/S1600536809022041

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4-Bromo-3-{N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methylsulfamoyl}-5-methylbenzoic acid monohydrate

C. Suneel Manohar Babu,^a Helen P. Kavitha,^b Jasmine P. Vennila,^c G. Chakkaravarthi ^d and V. Manivannan ^e ^*

^aNicholas Piramal Research Centre, Nicholas Piramal India Limited, Mumbai 400 063, India, ^bDepartment of Chemistry, SRM University, Ramapuram, Chennai 600 089, India, ^cDepartment of Physics, Panimalar Institute of Technology, Chennai 600 095, India, ^dDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, and ^eDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
^*Correspondence e-mail: manivan_1999@yahoo.com

(Received 30 May 2009; accepted 10 June 2009; online 13 June 2009)

In the title compound, C₁₉H₂₂BrNO₆S·H₂O, 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 interactions. In the crystal structure, molecules are linked by O—H⋯O and O—H⋯(O,O) hydrogen bonds involving the water molecule, 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_r = 490.36
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.040
wR(F²) = 0.107
S = 1.05
4619 reflections
275 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.30 e Å⁻³
Absolute structure: Flack (1983 ), 1915 Friedel pairs
Flack parameter: −0.004 (10)

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) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x+1, y-1, z.

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.

Supporting information

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

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

checkCIF report

Comment top

Sulfonamides are a class of anti-microbial agents that have seen extensive use in medicine. They are the first agents to be used for the treatment of bacterial infection (Cates, 1986). Sulfonamides are used to treat atrophic rhinitis in swine and heart water in cattle and many other diseases in a variety of animals (Steele & Beran, 1984). In adition sulfonamides have a variety of biological activities such as antibacterial, antimalarial and antileprotic agents (Benedetti, 1987; Mengelers et al., 1997).

The geometric parameters of the title molecule agree well with those reported for similar structures (Babu et al., 2009a,b; Shad et al., 2009). In the molecular structure, the two benzene rings are stacked over one another with their centroids separated by 3.769 (2) Å, indicating a weak π-π interaction. The dihedral angle between the two benzene rings is 3.1 (1)°. A distorted tetrahedral geometry [O3—S1—O4 = 118.7 (2)° and O3—S1—N1 = 108.8 (2) °] is observed around S1 atom.

In the crystal structure, O—H···O hydrogen bonds (Table 1) link the molecules into a two-dimensional network parallel to the (0 0 1). The O1W—H2W···O5 and O1W—H2W···O6 bifurcated donar bonds generate an R₁²(5) ring motif (Bernstein et al., 1995).

Related literature top

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 top

A solution of 2-(3,4-dimethoxyphenyl)-N-methyl ethanamine (1 g, 0.0051 mol) in ethyl acetate (20 ml) was charged into a round bottom flask equipped with thermometer pocket, condenser and guard tube. Then, pyridine (0.81 g, 0.0102 mol) was added at 25–30°C. After 5 min stirring, 2-bromo-5-(chlorosulfonyl)-3-methylbenzoic acid (0.96 g, 0.00307 mol) was charged into the reaction mass and heated to 45-50°C and maintained for 5-6 h. The completion of the reaction was checked by thin layer chromatography (1:1 hexane-ethyl acetate) and the reaction mass was cooled to 25–30 °C and quenched with 20 ml of water. Then, the aqueous layer was separated and the ethyl acetate layer was washed twice with 10% sodium chloride solution and dried over 2 g of anhydrous sodium sulfate. The solvent was distilled under vacuum at 35-40°C and the crude compound isolated. The crude compound was purified through column chromatography using hexane and ethyl acetate as eluents.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms. The dashed line denotes a hydrogen bond.

4-Bromo-3-{N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methylsulfamoyl}- 5-methylbenzoic acid monohydrate top

Crystal data top

C₁₉H₂₂BrNO₆S·H₂O	F(000) = 1008
M_r = 490.36	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0512P)²] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
4619 reflections	Δρ_max = 0.36 e Å⁻³
275 parameters	Δρ_min = −0.30 e Å⁻³
3 restraints	Absolute structure: Flack (1983), 1915 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.004 (10)

Crystal data top

C₁₉H₂₂BrNO₆S·H₂O	V = 2114.29 (9) Å³
M_r = 490.36	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.7938 (2) Å	µ = 2.08 mm⁻¹
b = 7.8280 (2) Å	T = 295 K
c = 34.6549 (8) Å	0.15 × 0.12 × 0.10 mm

Data collection top

Bruker Kappa APEXII area-detector diffractometer	4619 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3427 reflections with I > 2σ(I)
T_min = 0.745, T_max = 0.819	R_int = 0.028
12583 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.107	Δρ_max = 0.36 e Å⁻³
S = 1.05	Δρ_min = −0.30 e Å⁻³
4619 reflections	Absolute structure: Flack (1983), 1915 Friedel pairs
275 parameters	Absolute structure parameter: −0.004 (10)
3 restraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, y−1/2, −z+1/2; (ii) x+1, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₂BrNO₆S·H₂O
M_r	490.36
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	295
a, b, c (Å)	7.7938 (2), 7.8280 (2), 34.6549 (8)
V (Å³)	2114.29 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.08
Crystal size (mm)	0.15 × 0.12 × 0.10

Data collection
Diffractometer	Bruker Kappa APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.745, 0.819
No. of measured, independent and observed [I > 2σ(I)] reflections	12583, 4619, 3427
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.642

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.107, 1.05
No. of reflections	4619
No. of parameters	275
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.30
Absolute structure	Flack (1983), 1915 Friedel pairs
Absolute structure parameter	−0.004 (10)

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x+1, y−1/2, −z+1/2; (ii) x+1, y−1, z.

Acknowledgements

The authors acknowledge the Sophisticated Analytical Instrument Facility, Indian Institute of Technology-Madras, Chennai, for the data collection.

References

Babu, C. S. M., Kavitha, H. P., Arulmozhi, R., Vennila, J. P. & Manivannan, V. (2009a). Acta Cryst. E65, o1098. Web of Science CSD CrossRef IUCr Journals Google Scholar
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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4-Bromo-3-{N-[2-(3,4-di­meth­oxy­phen­yl)eth­yl]-N-methyl­sulfamo­yl}-5-methyl­benzoic acid monohydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-Bromo-3-{N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methylsulfamoyl}-5-methylbenzoic acid monohydrate