4-(4-Bromo­benzene­sulfonamido)benzoic acid

Khan, I.U.; Mustafa, G.; Arshad, M.N.; Shafiq, M.; Sharif, S.

doi:10.1107/S1600536809013798

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1073

doi:10.1107/S1600536809013798

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4-(4-Bromobenzenesulfonamido)benzoic acid

Islam Ullah Khan,^a Ghulam Mustafa,^a Muhammad Nadeem Arshad,^a ^* Muhammad Shafiq ^a and Shahzad Sharif ^a

^aMaterials Chemistry Laboratory, Department of Chemistry, Government College University, Lahore, Pakistan
^*Correspondence e-mail: mnachemist@hotmail.com

(Received 3 April 2009; accepted 13 April 2009; online 18 April 2009)

The title compound, C₁₃H₁₀BrNO₄S, belongs to the sulfonamide class of organic compounds. The two aromatic rings are inclined at 34.30 (15)° to one another, and the carboxyl substituent lies in the plane of the benzene ring to which it is bound (maximum deviation = 0.004 Å). In the crystal structure, charactersitic carboxylic acid dimers are formed through O—H⋯O hydrogen bonds. These dimers are linked into rows down a by N—H⋯O interactions. Additional C—H⋯O contacts further stabilize the structure, and a close Br⋯Br(x, −y + 1, −z + 1) contact of 3.5199 (9) Å is also observed.

Related literature

For details of the biological activity and pharmaceutical applications of sulfonamide derivatives, see: Pandya et al. (2003 ); Supuran & Scozzafava (2000 ); Arshad, Khan & Zia-ur-Rehman (2008 ). For thiazine-related heterocycles, see: Arshad, Tahir et al. (2008 ). For a related structure, see: Nan & Xing (2006 ). For bond-length information, see: Allen et al. (1987 ). For the synthesis, see: Deng & Mani (2006 ).

Experimental

Crystal data

C₁₃H₁₀BrNO₄S
M_r = 356.19
Monoclinic, P 2₁ /c
a = 5.1344 (5) Å
b = 13.1713 (11) Å
c = 20.0224 (19) Å
β = 91.730 (5)°
V = 1353.4 (2) Å³
Z = 4
Mo Kα radiation
μ = 3.20 mm⁻¹
T = 296 K
0.35 × 0.21 × 0.09 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.448, T_max = 0.754
14856 measured reflections
3352 independent reflections
1838 reflections with I > 2σ(I)
R_int = 0.061

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.128
S = 1.01
3352 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 1.43 e Å⁻³
Δρ_min = −1.09 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O1ⁱ	0.82	1.80	2.606 (4)	171
N1—H1⋯O4ⁱⁱ	0.86	2.57	3.001 (3)	112
C2—H2⋯O1ⁱⁱⁱ	0.93	2.46	3.361 (5)	164
C3—H3⋯O2^iv	0.93	2.53	3.314 (5)	143
C11—H11⋯O3^v	0.93	2.58	3.395 (5)	146
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x-1, y, z; (iii) $[x-1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809013798/sj2609sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809013798/sj2609Isup2.hkl

checkCIF report

Comment top

Sulfonamide derivatives have been reported as antibacterial agents (Pandya et al., 2003) as well as enzyme inhibitors. The studies also revealed that aromatic sulfonamides are inhibitors of the growth of tumor cells (Supuran, & Scozzafava, 2000). Herein we report the structure of the title compound I, Fig, 1, as a continuation of our work on the synthesis and structure of sulfonamides (Arshad, Khan & Zia-ur-Rehman et al., 2008a) and thiazine related heterocycles (Arshad, Tahir et al., 2008b).

The structure of the title compound I can be compared with that of 4-(tosylamino)benzoic acid (Nan and Xing, 2006) which differs only in respect that I has bromo substituent in the para position instead of methyl group. The carboxylic acid substituent lies in the plane of the benzene ring to which it is bound (maximum deviation 0.004 Å) and the phenyl rings (C1—C6) and (C7—C12) are oriented at an angle of 34.30 (0.15) ° to each other. Bond lengths in the molecule are normal (Allen et al., 1987). The carboxylic acid substituent forms dimers via intermolecular O—H···O hydrogen bonds. These dimers are further linked through N–H···O hydrogen bonds between the N–H and the oxygen of the sulfonyl group (SO₂) along the a axis. Moreover the structure is further stabilized by C–H···O intermolecular interactions, Table 1, by forming seven and ten membered ring motifs Fig. 3.

Related literature top

For details of the biological activity and pharmaceutical applications of sulfonamide derivatives, see: Pandya et al. (2003); Supuran & Scozzafava (2000); Arshad, Khan & Zia-ur-Rehman (2008). For thiazine-related heterocycles, see: Arshad, Tahir et al. (2008). For a related structure, see: Nan & Xing (2006). For bond-length information, see: Allen et al. (1987). For the synthesis, see: Deng & Mani (2006).

Experimental top

The title compound was synthesized following the method (Deng & Mani, 2006). and recrystallized from ethanol for X-ray studies.

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) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The structure of (I) with displacement ellipsoids for the non-hydrogenatoms drawn at the 50% probability level.
	Fig. 2. Crystal packing for (I) showing the formation of rows of dimers with hydrogen bonds drawn as dashed lines and H atoms not involved in hydrogen bonding omitted.
	Fig. 3. Unit cell packing for (I) showing additional C–H···O hydrogen bonds drawn as dashed lines and H atoms not involved in hydrogen bonding omitted.

4-(4-Bromobenzenesulfonamido)benzoic acid top

Crystal data top

C₁₃H₁₀BrNO₄S	F(000) = 712
M_r = 356.19	D_x = 1.748 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc 1	Cell parameters from 2704 reflections
a = 5.1344 (5) Å	θ = 2.6–22.0°
b = 13.1713 (11) Å	µ = 3.20 mm⁻¹
c = 20.0224 (19) Å	T = 296 K
β = 91.730 (5)°	Irregular fragment, white
V = 1353.4 (2) Å³	0.35 × 0.21 × 0.09 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	3352 independent reflections
Radiation source: fine-focus sealed tube	1838 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −6→6
T_min = 0.448, T_max = 0.754	k = −17→10
14856 measured reflections	l = −26→23

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.128	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0594P)² + 0.1787P] where P = (F_o² + 2F_c²)/3
3352 reflections	(Δ/σ)_max < 0.001
182 parameters	Δρ_max = 1.43 e Å⁻³
0 restraints	Δρ_min = −1.09 e Å⁻³

Crystal data top

C₁₃H₁₀BrNO₄S	V = 1353.4 (2) Å³
M_r = 356.19	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.1344 (5) Å	µ = 3.20 mm⁻¹
b = 13.1713 (11) Å	T = 296 K
c = 20.0224 (19) Å	0.35 × 0.21 × 0.09 mm
β = 91.730 (5)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3352 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	1838 reflections with I > 2σ(I)
T_min = 0.448, T_max = 0.754	R_int = 0.061
14856 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.128	H-atom parameters constrained
S = 1.01	Δρ_max = 1.43 e Å⁻³
3352 reflections	Δρ_min = −1.09 e Å⁻³
182 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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
Br1	0.06086 (10)	0.39989 (3)	0.44439 (2)	0.0693 (2)
S1	0.41495 (17)	0.01866 (7)	0.27290 (5)	0.0348 (2)
O1	0.6125 (5)	0.38278 (19)	0.01376 (14)	0.0509 (8)
O2	0.2589 (5)	0.4559 (2)	0.05304 (15)	0.0528 (8)
H2A	0.3084	0.5024	0.0293	0.079*
O3	0.3343 (5)	−0.07285 (18)	0.30378 (14)	0.0459 (7)
O4	0.6772 (4)	0.0308 (2)	0.25256 (13)	0.0458 (7)
N1	0.2274 (5)	0.0325 (2)	0.20612 (15)	0.0353 (7)
H1	0.1085	−0.0116	0.1965	0.042*
C1	0.1820 (8)	0.2852 (3)	0.3973 (2)	0.0448 (10)
C2	0.0653 (8)	0.1929 (3)	0.4067 (2)	0.0498 (11)
H2	−0.0666	0.1862	0.4372	0.060*
C3	0.1449 (7)	0.1108 (3)	0.3707 (2)	0.0434 (10)
H3	0.0678	0.0478	0.3770	0.052*
C4	0.3401 (6)	0.1213 (3)	0.32476 (18)	0.0339 (9)
C5	0.4571 (8)	0.2152 (3)	0.3160 (2)	0.0472 (10)
H5	0.5886	0.2222	0.2854	0.057*
C6	0.3796 (8)	0.2975 (3)	0.3523 (2)	0.0548 (12)
H6	0.4582	0.3604	0.3468	0.066*
C7	0.2632 (6)	0.1189 (2)	0.16378 (18)	0.0310 (8)
C8	0.4623 (7)	0.1184 (3)	0.1193 (2)	0.0399 (9)
H8	0.5652	0.0608	0.1148	0.048*
C9	0.5087 (7)	0.2035 (3)	0.08134 (19)	0.0398 (9)
H9	0.6459	0.2037	0.0521	0.048*
C10	0.3537 (7)	0.2881 (3)	0.08650 (18)	0.0324 (8)
C11	0.1471 (7)	0.2863 (3)	0.1297 (2)	0.0412 (10)
H11	0.0378	0.3424	0.1326	0.049*
C12	0.1038 (7)	0.2019 (3)	0.16820 (19)	0.0411 (9)
H12	−0.0340	0.2011	0.1973	0.049*
C13	0.4143 (7)	0.3801 (3)	0.04823 (18)	0.0372 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0983 (4)	0.0484 (3)	0.0624 (4)	0.0061 (2)	0.0194 (3)	−0.0097 (2)
S1	0.0293 (5)	0.0328 (5)	0.0428 (6)	0.0016 (4)	0.0084 (4)	0.0072 (4)
O1	0.0523 (17)	0.0412 (16)	0.061 (2)	0.0101 (12)	0.0304 (15)	0.0144 (13)
O2	0.0589 (17)	0.0363 (16)	0.065 (2)	0.0145 (14)	0.0293 (15)	0.0186 (14)
O3	0.0485 (16)	0.0331 (15)	0.0567 (19)	0.0037 (12)	0.0135 (13)	0.0141 (13)
O4	0.0271 (13)	0.0532 (18)	0.0579 (19)	0.0035 (11)	0.0117 (12)	0.0064 (13)
N1	0.0321 (16)	0.0332 (17)	0.041 (2)	−0.0093 (12)	0.0037 (14)	0.0058 (14)
C1	0.056 (3)	0.040 (2)	0.039 (2)	0.0045 (19)	0.0048 (19)	−0.0047 (18)
C2	0.053 (3)	0.051 (3)	0.047 (3)	−0.003 (2)	0.021 (2)	0.001 (2)
C3	0.047 (2)	0.037 (2)	0.047 (3)	−0.0076 (17)	0.014 (2)	0.0067 (18)
C4	0.0300 (19)	0.034 (2)	0.038 (2)	−0.0021 (15)	0.0045 (16)	0.0050 (16)
C5	0.048 (2)	0.044 (2)	0.051 (3)	−0.0081 (18)	0.019 (2)	0.001 (2)
C6	0.064 (3)	0.037 (2)	0.064 (3)	−0.014 (2)	0.017 (2)	0.000 (2)
C7	0.0308 (18)	0.0265 (19)	0.036 (2)	−0.0010 (14)	0.0040 (16)	0.0025 (15)
C8	0.044 (2)	0.031 (2)	0.046 (2)	0.0101 (16)	0.0135 (18)	0.0014 (17)
C9	0.043 (2)	0.035 (2)	0.042 (2)	0.0037 (17)	0.0171 (18)	0.0011 (18)
C10	0.0332 (19)	0.030 (2)	0.034 (2)	−0.0001 (15)	0.0058 (16)	0.0006 (16)
C11	0.035 (2)	0.034 (2)	0.056 (3)	0.0119 (15)	0.0147 (18)	0.0088 (19)
C12	0.034 (2)	0.042 (2)	0.048 (3)	0.0069 (16)	0.0162 (18)	0.0083 (19)
C13	0.036 (2)	0.035 (2)	0.040 (2)	−0.0002 (17)	0.0072 (18)	0.0029 (17)

Geometric parameters (Å, º) top

Br1—C1	1.896 (4)	C4—C5	1.388 (5)
S1—O3	1.422 (2)	C5—C6	1.370 (5)
S1—O4	1.427 (2)	C5—H5	0.9300
S1—N1	1.634 (3)	C6—H6	0.9300
S1—C4	1.754 (4)	C7—C12	1.370 (5)
O1—C13	1.247 (4)	C7—C8	1.376 (5)
O2—C13	1.284 (4)	C8—C9	1.379 (5)
O2—H2A	0.8200	C8—H8	0.9300
N1—C7	1.434 (4)	C9—C10	1.374 (5)
N1—H1	0.8600	C9—H9	0.9300
C1—C2	1.371 (5)	C10—C11	1.389 (5)
C1—C6	1.387 (5)	C10—C13	1.472 (5)
C2—C3	1.370 (5)	C11—C12	1.375 (5)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.388 (5)	C12—H12	0.9300
C3—H3	0.9300

O3—S1—O4	120.55 (15)	C5—C6—C1	118.8 (4)
O3—S1—N1	106.15 (15)	C5—C6—H6	120.6
O4—S1—N1	106.97 (15)	C1—C6—H6	120.6
O3—S1—C4	108.90 (16)	C12—C7—C8	120.2 (3)
O4—S1—C4	107.95 (16)	C12—C7—N1	120.5 (3)
N1—S1—C4	105.33 (16)	C8—C7—N1	119.3 (3)
C13—O2—H2A	109.5	C7—C8—C9	119.8 (3)
C7—N1—S1	119.3 (2)	C7—C8—H8	120.1
C7—N1—H1	120.4	C9—C8—H8	120.1
S1—N1—H1	120.4	C10—C9—C8	120.5 (3)
C2—C1—C6	121.6 (4)	C10—C9—H9	119.8
C2—C1—Br1	119.1 (3)	C8—C9—H9	119.8
C6—C1—Br1	119.2 (3)	C9—C10—C11	119.2 (3)
C3—C2—C1	119.3 (4)	C9—C10—C13	119.7 (3)
C3—C2—H2	120.3	C11—C10—C13	121.0 (3)
C1—C2—H2	120.3	C12—C11—C10	120.1 (3)
C2—C3—C4	120.2 (3)	C12—C11—H11	119.9
C2—C3—H3	119.9	C10—C11—H11	119.9
C4—C3—H3	119.9	C7—C12—C11	120.1 (3)
C5—C4—C3	119.8 (3)	C7—C12—H12	119.9
C5—C4—S1	120.6 (3)	C11—C12—H12	119.9
C3—C4—S1	119.4 (3)	O1—C13—O2	122.6 (3)
C6—C5—C4	120.3 (4)	O1—C13—C10	120.0 (3)
C6—C5—H5	119.8	O2—C13—C10	117.4 (3)
C4—C5—H5	119.8

O3—S1—N1—C7	−179.7 (2)	Br1—C1—C6—C5	−176.8 (3)
O4—S1—N1—C7	−49.8 (3)	S1—N1—C7—C12	−99.7 (4)
C4—S1—N1—C7	64.9 (3)	S1—N1—C7—C8	79.3 (4)
C6—C1—C2—C3	−0.2 (7)	C12—C7—C8—C9	3.0 (6)
Br1—C1—C2—C3	177.3 (3)	N1—C7—C8—C9	−175.9 (3)
C1—C2—C3—C4	−0.5 (6)	C7—C8—C9—C10	−1.5 (6)
C2—C3—C4—C5	0.8 (6)	C8—C9—C10—C11	−0.9 (6)
C2—C3—C4—S1	−173.2 (3)	C8—C9—C10—C13	176.9 (4)
O3—S1—C4—C5	162.7 (3)	C9—C10—C11—C12	1.9 (6)
O4—S1—C4—C5	30.2 (4)	C13—C10—C11—C12	−175.8 (4)
N1—S1—C4—C5	−83.8 (3)	C8—C7—C12—C11	−2.0 (6)
O3—S1—C4—C3	−23.2 (3)	N1—C7—C12—C11	176.9 (3)
O4—S1—C4—C3	−155.7 (3)	C10—C11—C12—C7	−0.5 (6)
N1—S1—C4—C3	90.3 (3)	C9—C10—C13—O1	−3.4 (6)
C3—C4—C5—C6	−0.3 (6)	C11—C10—C13—O1	174.4 (3)
S1—C4—C5—C6	173.7 (3)	C9—C10—C13—O2	177.8 (4)
C4—C5—C6—C1	−0.4 (6)	C11—C10—C13—O2	−4.5 (5)
C2—C1—C6—C5	0.7 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1ⁱ	0.82	1.80	2.606 (4)	171
N1—H1···O4ⁱⁱ	0.86	2.57	3.001 (3)	112
C2—H2···O1ⁱⁱⁱ	0.93	2.46	3.361 (5)	164
C3—H3···O2^iv	0.93	2.53	3.314 (5)	143
C11—H11···O3^v	0.93	2.58	3.395 (5)	146

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₀BrNO₄S
M_r	356.19
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	5.1344 (5), 13.1713 (11), 20.0224 (19)
β (°)	91.730 (5)
V (Å³)	1353.4 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.20
Crystal size (mm)	0.35 × 0.21 × 0.09

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.448, 0.754
No. of measured, independent and observed [I > 2σ(I)] reflections	14856, 3352, 1838
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.128, 1.01
No. of reflections	3352
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.43, −1.09

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1ⁱ	0.82	1.80	2.606 (4)	170.64
N1—H1···O4ⁱⁱ	0.86	2.57	3.001 (3)	111.70
C2—H2···O1ⁱⁱⁱ	0.93	2.46	3.361 (5)	163.8
C3—H3···O2^iv	0.93	2.53	3.314 (5)	142.7
C11—H11···O3^v	0.93	2.58	3.395 (5)	146.2

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

Acknowledgements

MNA acknowledges the Higher Education Commission, Pakistan, for providing a PhD Scholarship under the PIN 042-120607-PS2-183 scheme and also acknowledges Professor Dr M. Nawaz Tahir, Chairman, Department of Physics, University of Sargodha, Pakistan, for his kind guidance in crystallography.

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