organic compounds
2,5-Dichloro-N-(4-methoxyphenyl)benzensulfonamide
aMaterials Chemistry Laboratory, Department of Chemistry, Government College University, Lahore 54000, Pakistan, and bDepartment of Chemistry, Chungnam National University, Daejeon 305-764, Republic of Korea
*Correspondence e-mail: skkang@cnu.ac.kr
In the title compound, C13H11Cl2NO3S, the dihedral angle between the benzene rings is 74.37 (3)°. In the crystal, intermolecular N—H⋯O hydrogen bonds link the molecules into chains along the b axis.
Related literature
For our previous studies on sulfonamide derivatives, see: Khan et al. (2010); Sharif et al. (2010). For background to the pharmacological uses of see: Korolkovas (1988); Mandell & Sande (1992).
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: APEX2 (Bruker, 2007); cell 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); software used to prepare material for publication: WinGX (Farrugia, 1999).
Supporting information
10.1107/S1600536811000936/jh2254sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536811000936/jh2254Isup2.hkl
To para-anisidine (123 mg, 1 mmol) in distilled water (10 ml) was added 2,5-dichloro benzene sulfonyl chloride (0.245 mg, 1 mmol) with stirring at room temperature while maintaining the pH = 8 using 3% sodium carbonate. The progress of the reaction was monitored by TLC. The precipitate formed in this way was washed with water, dried and crystallized from methanol.
The H atom of the NH group was located in a difference Fourier map and refined freely. The remaining H atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.96 Å, and with Uiso(H) = 1.2Ueq (C) for aromatic and 1.5Ueq(C) for methyl H atoms.
Data collection: APEX2 (Bruker, 2007); cell
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); software used to prepare material for publication: WinGX (Farrugia, 1999).C13H11Cl2NO3S | F(000) = 680 |
Mr = 332.19 | Dx = 1.582 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4792 reflections |
a = 13.1599 (4) Å | θ = 2.9–28.0° |
b = 7.8179 (2) Å | µ = 0.62 mm−1 |
c = 14.4830 (5) Å | T = 296 K |
β = 110.566 (1)° | Block, colourless |
V = 1395.09 (7) Å3 | 0.25 × 0.17 × 0.12 mm |
Z = 4 |
Bruker APEXII CCD diffractometer | Rint = 0.030 |
ϕ and ω scans | θmax = 28.3°, θmin = 3.0° |
13132 measured reflections | h = −17→17 |
3456 independent reflections | k = −10→10 |
2690 reflections with I > 2σ(I) | l = −18→19 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.039 | w = 1/[σ2(Fo2) + (0.045P)2 + 0.6614P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.108 | (Δ/σ)max = 0.001 |
S = 1.06 | Δρmax = 0.46 e Å−3 |
3456 reflections | Δρmin = −0.31 e Å−3 |
186 parameters |
C13H11Cl2NO3S | V = 1395.09 (7) Å3 |
Mr = 332.19 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.1599 (4) Å | µ = 0.62 mm−1 |
b = 7.8179 (2) Å | T = 296 K |
c = 14.4830 (5) Å | 0.25 × 0.17 × 0.12 mm |
β = 110.566 (1)° |
Bruker APEXII CCD diffractometer | 2690 reflections with I > 2σ(I) |
13132 measured reflections | Rint = 0.030 |
3456 independent reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.108 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.46 e Å−3 |
3456 reflections | Δρmin = −0.31 e Å−3 |
186 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.72780 (4) | 0.85926 (6) | 0.82650 (3) | 0.03916 (14) | |
O2 | 0.73299 (14) | 1.04147 (19) | 0.82443 (12) | 0.0552 (4) | |
O3 | 0.69500 (12) | 0.7655 (2) | 0.73648 (10) | 0.0493 (4) | |
C4 | 0.85981 (16) | 0.7804 (2) | 0.89567 (14) | 0.0369 (4) | |
C5 | 0.91579 (17) | 0.8160 (3) | 0.99528 (15) | 0.0419 (4) | |
C6 | 1.02137 (18) | 0.7615 (3) | 1.03996 (17) | 0.0509 (5) | |
H6 | 1.0576 | 0.7843 | 1.1065 | 0.061* | |
C7 | 1.07387 (19) | 0.6737 (3) | 0.98749 (18) | 0.0539 (6) | |
H7 | 1.1455 | 0.6385 | 1.0176 | 0.065* | |
C8 | 1.01785 (18) | 0.6389 (3) | 0.88887 (17) | 0.0485 (5) | |
C9 | 0.91210 (17) | 0.6898 (3) | 0.84328 (15) | 0.0427 (4) | |
H9 | 0.8756 | 0.6635 | 0.7772 | 0.051* | |
Cl10 | 0.85599 (5) | 0.93075 (8) | 1.06480 (4) | 0.05536 (17) | |
Cl11 | 1.08144 (6) | 0.53037 (11) | 0.82003 (6) | 0.0786 (2) | |
N12 | 0.64500 (14) | 0.8123 (2) | 0.88365 (13) | 0.0398 (4) | |
H12 | 0.6441 (19) | 0.888 (3) | 0.9181 (17) | 0.046 (7)* | |
C13 | 0.63424 (15) | 0.6413 (2) | 0.91467 (13) | 0.0350 (4) | |
C14 | 0.65129 (17) | 0.6093 (3) | 1.01225 (14) | 0.0412 (4) | |
H14 | 0.6706 | 0.6986 | 1.0575 | 0.049* | |
C15 | 0.64003 (17) | 0.4456 (3) | 1.04402 (15) | 0.0423 (5) | |
H15 | 0.6504 | 0.4257 | 1.11 | 0.051* | |
C16 | 0.61338 (16) | 0.3123 (3) | 0.97760 (15) | 0.0405 (4) | |
C17 | 0.59349 (19) | 0.3448 (3) | 0.87865 (15) | 0.0476 (5) | |
H17 | 0.5737 | 0.2557 | 0.8333 | 0.057* | |
C18 | 0.60287 (18) | 0.5083 (3) | 0.84720 (15) | 0.0448 (5) | |
H18 | 0.5881 | 0.5295 | 0.7806 | 0.054* | |
O19 | 0.60296 (14) | 0.1448 (2) | 1.00210 (12) | 0.0560 (4) | |
C20 | 0.6237 (2) | 0.1095 (3) | 1.10353 (19) | 0.0610 (6) | |
H20A | 0.6977 | 0.138 | 1.1414 | 0.091* | |
H20B | 0.6117 | −0.0098 | 1.1116 | 0.091* | |
H20C | 0.5759 | 0.1765 | 1.126 | 0.091* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0448 (3) | 0.0397 (3) | 0.0347 (2) | 0.0049 (2) | 0.0162 (2) | 0.00713 (19) |
O2 | 0.0669 (10) | 0.0399 (8) | 0.0638 (10) | 0.0066 (7) | 0.0292 (9) | 0.0140 (7) |
O3 | 0.0502 (8) | 0.0672 (10) | 0.0303 (7) | 0.0043 (7) | 0.0137 (6) | 0.0024 (7) |
C4 | 0.0414 (10) | 0.0341 (9) | 0.0361 (9) | −0.0023 (8) | 0.0147 (8) | 0.0044 (7) |
C5 | 0.0504 (11) | 0.0387 (10) | 0.0371 (10) | −0.0093 (9) | 0.0158 (9) | 0.0011 (8) |
C6 | 0.0489 (12) | 0.0532 (13) | 0.0423 (11) | −0.0122 (10) | 0.0056 (10) | 0.0042 (10) |
C7 | 0.0414 (11) | 0.0580 (14) | 0.0583 (14) | −0.0021 (10) | 0.0128 (10) | 0.0121 (11) |
C8 | 0.0474 (12) | 0.0490 (12) | 0.0533 (12) | 0.0055 (9) | 0.0231 (10) | 0.0097 (10) |
C9 | 0.0471 (11) | 0.0426 (11) | 0.0404 (10) | 0.0018 (9) | 0.0178 (9) | 0.0049 (8) |
Cl10 | 0.0707 (4) | 0.0531 (3) | 0.0446 (3) | −0.0098 (3) | 0.0231 (3) | −0.0122 (2) |
Cl11 | 0.0661 (4) | 0.1040 (6) | 0.0740 (5) | 0.0343 (4) | 0.0349 (4) | 0.0095 (4) |
N12 | 0.0480 (10) | 0.0371 (9) | 0.0386 (9) | 0.0037 (7) | 0.0205 (8) | −0.0011 (7) |
C13 | 0.0340 (9) | 0.0368 (10) | 0.0363 (9) | 0.0017 (7) | 0.0151 (8) | −0.0002 (8) |
C14 | 0.0475 (11) | 0.0427 (11) | 0.0356 (10) | −0.0059 (8) | 0.0175 (9) | −0.0070 (8) |
C15 | 0.0475 (11) | 0.0487 (12) | 0.0332 (10) | −0.0065 (9) | 0.0172 (9) | −0.0002 (8) |
C16 | 0.0415 (10) | 0.0391 (10) | 0.0427 (11) | −0.0018 (8) | 0.0171 (9) | 0.0011 (8) |
C17 | 0.0629 (13) | 0.0414 (11) | 0.0390 (11) | −0.0044 (9) | 0.0185 (10) | −0.0090 (9) |
C18 | 0.0574 (13) | 0.0449 (11) | 0.0312 (9) | −0.0003 (9) | 0.0146 (9) | −0.0023 (8) |
O19 | 0.0776 (11) | 0.0403 (8) | 0.0550 (9) | −0.0060 (7) | 0.0290 (8) | 0.0021 (7) |
C20 | 0.0800 (17) | 0.0519 (14) | 0.0613 (15) | 0.0073 (12) | 0.0377 (13) | 0.0149 (12) |
S1—O3 | 1.4243 (15) | N12—H12 | 0.78 (2) |
S1—O2 | 1.4269 (16) | C13—C14 | 1.374 (3) |
S1—N12 | 1.6250 (17) | C13—C18 | 1.387 (3) |
S1—C4 | 1.783 (2) | C14—C15 | 1.386 (3) |
C4—C9 | 1.385 (3) | C14—H14 | 0.93 |
C4—C5 | 1.398 (3) | C15—C16 | 1.377 (3) |
C5—C6 | 1.378 (3) | C15—H15 | 0.93 |
C5—Cl10 | 1.731 (2) | C16—O19 | 1.376 (2) |
C6—C7 | 1.377 (3) | C16—C17 | 1.387 (3) |
C6—H6 | 0.93 | C17—C18 | 1.377 (3) |
C7—C8 | 1.385 (3) | C17—H17 | 0.93 |
C7—H7 | 0.93 | C18—H18 | 0.93 |
C8—C9 | 1.373 (3) | O19—C20 | 1.424 (3) |
C8—Cl11 | 1.732 (2) | C20—H20A | 0.96 |
C9—H9 | 0.93 | C20—H20B | 0.96 |
N12—C13 | 1.433 (3) | C20—H20C | 0.96 |
O3—S1—O2 | 119.74 (10) | S1—N12—H12 | 108.5 (18) |
O3—S1—N12 | 107.95 (10) | C14—C13—C18 | 119.27 (18) |
O2—S1—N12 | 106.36 (10) | C14—C13—N12 | 119.59 (17) |
O3—S1—C4 | 104.98 (9) | C18—C13—N12 | 121.09 (17) |
O2—S1—C4 | 108.22 (10) | C13—C14—C15 | 120.78 (18) |
N12—S1—C4 | 109.34 (9) | C13—C14—H14 | 119.6 |
C9—C4—C5 | 118.95 (19) | C15—C14—H14 | 119.6 |
C9—C4—S1 | 116.27 (15) | C16—C15—C14 | 119.84 (18) |
C5—C4—S1 | 124.56 (16) | C16—C15—H15 | 120.1 |
C6—C5—C4 | 120.1 (2) | C14—C15—H15 | 120.1 |
C6—C5—Cl10 | 118.46 (17) | O19—C16—C15 | 124.31 (18) |
C4—C5—Cl10 | 121.40 (16) | O19—C16—C17 | 116.17 (18) |
C7—C6—C5 | 120.9 (2) | C15—C16—C17 | 119.51 (19) |
C7—C6—H6 | 119.5 | C18—C17—C16 | 120.37 (19) |
C5—C6—H6 | 119.5 | C18—C17—H17 | 119.8 |
C6—C7—C8 | 118.6 (2) | C16—C17—H17 | 119.8 |
C6—C7—H7 | 120.7 | C17—C18—C13 | 120.14 (18) |
C8—C7—H7 | 120.7 | C17—C18—H18 | 119.9 |
C9—C8—C7 | 121.4 (2) | C13—C18—H18 | 119.9 |
C9—C8—Cl11 | 118.56 (18) | C16—O19—C20 | 116.76 (18) |
C7—C8—Cl11 | 120.00 (18) | O19—C20—H20A | 109.5 |
C8—C9—C4 | 120.0 (2) | O19—C20—H20B | 109.5 |
C8—C9—H9 | 120 | H20A—C20—H20B | 109.5 |
C4—C9—H9 | 120 | O19—C20—H20C | 109.5 |
C13—N12—S1 | 121.87 (14) | H20A—C20—H20C | 109.5 |
C13—N12—H12 | 119.1 (18) | H20B—C20—H20C | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
N12—H12···O19i | 0.78 (2) | 2.50 (3) | 3.267 (2) | 168 (2) |
Symmetry code: (i) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C13H11Cl2NO3S |
Mr | 332.19 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 13.1599 (4), 7.8179 (2), 14.4830 (5) |
β (°) | 110.566 (1) |
V (Å3) | 1395.09 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.62 |
Crystal size (mm) | 0.25 × 0.17 × 0.12 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13132, 3456, 2690 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.108, 1.06 |
No. of reflections | 3456 |
No. of parameters | 186 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.46, −0.31 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N12—H12···O19i | 0.78 (2) | 2.50 (3) | 3.267 (2) | 168 (2) |
Symmetry code: (i) x, y+1, z. |
References
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Khan, I. U., Akkurt, M., Sharif, S. & Ahmad, W. (2010). Acta Cryst. E66, o3053. Web of Science CSD CrossRef IUCr Journals Google Scholar
Korolkovas, A. (1988). Essentials of Medicinal Chemistry, 2nd ed., pp. 699–716. New York: Wiley. Google Scholar
Mandell, G. L. & Sande, M. A. (1992). Goodman and Gilman, The Pharmacological Basis of Therapeutics 2, edited by A. Gilman, T. W. Rall, A. S. Nies & P. Taylor, 8th ed., pp. 1047–1057. Singapore: McGraw-Hill. Google Scholar
Sharif, S., Iqbal, H., Khan, I. U., John, P. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o1288. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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In continuation of our studies of sulfonamides synthesis (Khan et al., 2010; Sharif et al., 2010), of interest owing to their biological properties (Korolkovas, 1988; Mandell & Sande, 1992). Herein, the crystal structure of (I) is described
In the title compound (I), (Fig. 1), the 4-methoxyphenyl moiety is almost planar with r.m.s. deviation of 0.018 Å from the corresponding least-squares plane defined by the nine constituent atoms. The dihedral angle between the benzene rings is 74.37 (3) °. In the crystal, intermolecular N—H···O hydrogen bonds link the molecules into chains along the b axis (Table 1, Fig. 2).