organic compounds
2,4-Dichloro-N-phenethylbenzenesulfonamide
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, and dDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, India
*Correspondence e-mail: manivan_1999@yahoo.com
In the title compound, C14H13Cl2NO2S, the dihedral angle between the phenyl ring and the benzene ring is 69.94 (9)°. Two short intramolecular C—H⋯O contacts occur and a weak intermolecular C—H⋯π interaction is seen in the crystal.
Related literature
For the biological activity of et al. (2000); Misra et al. (1982); Zani & Vicini (1998); Maren (1976); Supuran et al. (1998); Renzi et al. (2000); Li et al. (1995); Yoshino et al. (1992). For related structures, see: Zhang et al. (2006); Andrighetti-Fröhner et al. (2007); For graph-set notation, see: Bernstein et al. (1995).
see: GadadExperimental
Crystal data
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Data collection: APEX2 (Bruker, 2004); cell 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
10.1107/S1600536809010927/is2402sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809010927/is2402Isup2.hkl
About 1 g (8 mmol) of 2-phenylethyl amine is dissolved in 20 ml of dichloromethane. 1.3 g (16 mmol) of pyridine is added into the reaction mass. The above mixture is stirred for 5 min. To this, 2.41 g (9.8 mmol) of 2, 4-dichlorobenzene-1-sulfonyl chloride is added and heated to 35 - 40 ° C for 6 hrs. The reaction mass is then cooled to the room temperature and 20 ml of water is added to it. The aquous layer is separated. The organic layer is washed with 10% sodium chloride solution and dried over 2 g of anhydrous sodium sulfate. The excess solvent is removed under vacuum. The crude compound is purified through
using hexane and ethyl acetate as eluants.H atoms were positioned geometrically and refined using riding model, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic C—H, C—H = 0.97 Å and Uiso(H) = 1.5Ueq(C) for CH2, and N—H = 0.86 Å and Uiso(H) = 1.2Ueq(N).
Data collection: APEX2 (Bruker, 2004); cell
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).Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms. |
C14H13Cl2NO2S | F(000) = 680 |
Mr = 330.21 | Dx = 1.433 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | θ = 1.6–27.6° |
a = 5.5618 (5) Å | µ = 0.56 mm−1 |
b = 10.9915 (8) Å | T = 295 K |
c = 25.045 (2) Å | Block, white |
V = 1531.0 (2) Å3 | 0.20 × 0.18 × 0.12 mm |
Z = 4 |
Bruker Kappa APEXII CCD diffractometer | 3511 independent reflections |
Radiation source: fine-focus sealed tube | 2955 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
ω and ϕ scans | θmax = 27.6°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −7→7 |
Tmin = 0.896, Tmax = 0.936 | k = −8→13 |
10930 measured reflections | l = −32→32 |
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-atom parameters constrained |
wR(F2) = 0.104 | w = 1/[σ2(Fo2) + (0.0546P)2 + 0.264P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
3511 reflections | Δρmax = 0.27 e Å−3 |
181 parameters | Δρmin = −0.24 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 1455 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.04 (8) |
C14H13Cl2NO2S | V = 1531.0 (2) Å3 |
Mr = 330.21 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 5.5618 (5) Å | µ = 0.56 mm−1 |
b = 10.9915 (8) Å | T = 295 K |
c = 25.045 (2) Å | 0.20 × 0.18 × 0.12 mm |
Bruker Kappa APEXII CCD diffractometer | 3511 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2955 reflections with I > 2σ(I) |
Tmin = 0.896, Tmax = 0.936 | Rint = 0.026 |
10930 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.104 | Δρmax = 0.27 e Å−3 |
S = 1.05 | Δρmin = −0.24 e Å−3 |
3511 reflections | Absolute structure: Flack (1983), 1455 Friedel pairs |
181 parameters | Absolute structure parameter: 0.04 (8) |
0 restraints |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.77658 (10) | 0.02339 (6) | 0.22502 (2) | 0.04851 (16) | |
Cl2 | 1.21110 (11) | −0.02059 (7) | 0.30970 (3) | 0.06133 (19) | |
Cl1 | 0.8648 (3) | 0.32987 (9) | 0.43460 (4) | 0.1235 (5) | |
C1 | 1.1601 (5) | 0.2812 (2) | 0.07918 (9) | 0.0492 (6) | |
C2 | 1.3486 (6) | 0.3577 (3) | 0.08766 (14) | 0.0721 (9) | |
H2 | 1.4664 | 0.3368 | 0.1123 | 0.087* | |
C3 | 1.3671 (7) | 0.4658 (4) | 0.06019 (18) | 0.0914 (11) | |
H3 | 1.4972 | 0.5170 | 0.0664 | 0.110* | |
C4 | 1.1958 (8) | 0.4980 (3) | 0.02405 (14) | 0.0816 (10) | |
H4 | 1.2091 | 0.5707 | 0.0053 | 0.098* | |
C5 | 1.0062 (7) | 0.4235 (3) | 0.01560 (11) | 0.0727 (9) | |
H5 | 0.8878 | 0.4457 | −0.0087 | 0.087* | |
C6 | 0.9872 (5) | 0.3153 (3) | 0.04272 (10) | 0.0578 (7) | |
H6 | 0.8564 | 0.2646 | 0.0364 | 0.069* | |
C7 | 1.1389 (6) | 0.1609 (3) | 0.10805 (10) | 0.0649 (8) | |
H7A | 1.0433 | 0.1056 | 0.0866 | 0.078* | |
H7B | 1.2979 | 0.1257 | 0.1119 | 0.078* | |
C8 | 1.0261 (5) | 0.1724 (2) | 0.16216 (9) | 0.0541 (6) | |
H8A | 1.1250 | 0.2242 | 0.1846 | 0.065* | |
H8B | 0.8690 | 0.2100 | 0.1588 | 0.065* | |
C9 | 0.8116 (4) | 0.1116 (2) | 0.28395 (9) | 0.0413 (5) | |
C10 | 0.9959 (5) | 0.0905 (2) | 0.32017 (9) | 0.0464 (5) | |
C11 | 1.0144 (6) | 0.1593 (3) | 0.36615 (11) | 0.0625 (7) | |
H11 | 1.1390 | 0.1460 | 0.3902 | 0.075* | |
C12 | 0.8444 (8) | 0.2484 (2) | 0.37570 (12) | 0.0683 (9) | |
C13 | 0.6653 (7) | 0.2725 (3) | 0.34033 (12) | 0.0649 (8) | |
H13 | 0.5550 | 0.3341 | 0.3472 | 0.078* | |
C14 | 0.6490 (5) | 0.2044 (2) | 0.29421 (11) | 0.0527 (6) | |
H14 | 0.5277 | 0.2209 | 0.2697 | 0.063* | |
O1 | 0.7876 (4) | −0.10180 (17) | 0.23927 (8) | 0.0660 (5) | |
O2 | 0.5657 (3) | 0.0685 (2) | 0.19918 (7) | 0.0652 (5) | |
N1 | 1.0011 (4) | 0.05205 (19) | 0.18713 (7) | 0.0525 (5) | |
H1 | 1.1075 | −0.0032 | 0.1813 | 0.063* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0474 (3) | 0.0475 (3) | 0.0506 (3) | −0.0037 (3) | −0.0090 (2) | 0.0003 (3) |
Cl2 | 0.0503 (3) | 0.0567 (4) | 0.0770 (4) | 0.0050 (3) | −0.0114 (3) | 0.0147 (3) |
Cl1 | 0.2342 (16) | 0.0666 (5) | 0.0696 (5) | 0.0090 (8) | −0.0224 (7) | −0.0190 (4) |
C1 | 0.0556 (14) | 0.0533 (14) | 0.0387 (11) | 0.0056 (12) | 0.0057 (10) | −0.0047 (10) |
C2 | 0.0584 (17) | 0.077 (2) | 0.081 (2) | 0.0036 (16) | −0.0144 (15) | −0.0071 (16) |
C3 | 0.071 (2) | 0.077 (2) | 0.127 (3) | −0.027 (2) | 0.006 (2) | −0.016 (2) |
C4 | 0.112 (3) | 0.0536 (18) | 0.079 (2) | −0.0024 (19) | 0.033 (2) | 0.0067 (15) |
C5 | 0.088 (2) | 0.075 (2) | 0.0555 (16) | 0.015 (2) | −0.0057 (16) | 0.0062 (14) |
C6 | 0.0588 (16) | 0.0628 (17) | 0.0519 (13) | −0.0051 (14) | −0.0074 (12) | 0.0016 (12) |
C7 | 0.089 (2) | 0.0573 (17) | 0.0487 (14) | 0.0127 (16) | 0.0044 (14) | 0.0025 (12) |
C8 | 0.0655 (16) | 0.0460 (14) | 0.0509 (13) | 0.0075 (13) | 0.0051 (12) | −0.0006 (11) |
C9 | 0.0406 (11) | 0.0402 (12) | 0.0431 (11) | −0.0074 (9) | −0.0018 (9) | 0.0066 (9) |
C10 | 0.0468 (13) | 0.0409 (13) | 0.0514 (12) | −0.0059 (10) | −0.0047 (11) | 0.0113 (10) |
C11 | 0.083 (2) | 0.0507 (16) | 0.0538 (14) | −0.0166 (15) | −0.0199 (14) | 0.0106 (12) |
C12 | 0.111 (3) | 0.0363 (14) | 0.0576 (15) | −0.0069 (15) | −0.0049 (18) | 0.0012 (11) |
C13 | 0.084 (2) | 0.0424 (15) | 0.0684 (17) | 0.0063 (14) | 0.0066 (16) | 0.0037 (13) |
C14 | 0.0527 (14) | 0.0469 (14) | 0.0584 (14) | 0.0022 (11) | 0.0003 (11) | 0.0085 (11) |
O1 | 0.0804 (14) | 0.0448 (10) | 0.0729 (12) | −0.0147 (10) | −0.0121 (11) | 0.0008 (8) |
O2 | 0.0520 (10) | 0.0814 (14) | 0.0622 (11) | −0.0011 (9) | −0.0156 (9) | −0.0014 (10) |
N1 | 0.0615 (13) | 0.0455 (12) | 0.0505 (11) | 0.0137 (10) | 0.0049 (10) | 0.0022 (9) |
S1—O1 | 1.423 (2) | C6—H6 | 0.9300 |
S1—O2 | 1.429 (2) | C7—C8 | 1.499 (4) |
S1—N1 | 1.600 (2) | C7—H7A | 0.9700 |
S1—C9 | 1.777 (2) | C7—H7B | 0.9700 |
Cl2—C10 | 1.730 (3) | C8—N1 | 1.470 (3) |
Cl1—C12 | 1.730 (3) | C8—H8A | 0.9700 |
C1—C2 | 1.361 (4) | C8—H8B | 0.9700 |
C1—C6 | 1.378 (4) | C9—C14 | 1.387 (3) |
C1—C7 | 1.512 (4) | C9—C10 | 1.388 (3) |
C2—C3 | 1.376 (5) | C10—C11 | 1.382 (4) |
C2—H2 | 0.9300 | C11—C12 | 1.382 (5) |
C3—C4 | 1.361 (5) | C11—H11 | 0.9300 |
C3—H3 | 0.9300 | C12—C13 | 1.359 (5) |
C4—C5 | 1.351 (5) | C13—C14 | 1.379 (4) |
C4—H4 | 0.9300 | C13—H13 | 0.9300 |
C5—C6 | 1.374 (4) | C14—H14 | 0.9300 |
C5—H5 | 0.9300 | N1—H1 | 0.8600 |
O1—S1—O2 | 119.00 (13) | H7A—C7—H7B | 107.8 |
O1—S1—N1 | 107.80 (12) | N1—C8—C7 | 110.4 (2) |
O2—S1—N1 | 107.69 (11) | N1—C8—H8A | 109.6 |
O1—S1—C9 | 108.35 (11) | C7—C8—H8A | 109.6 |
O2—S1—C9 | 106.06 (11) | N1—C8—H8B | 109.6 |
N1—S1—C9 | 107.44 (11) | C7—C8—H8B | 109.6 |
C2—C1—C6 | 118.2 (3) | H8A—C8—H8B | 108.1 |
C2—C1—C7 | 121.8 (3) | C14—C9—C10 | 118.9 (2) |
C6—C1—C7 | 120.0 (3) | C14—C9—S1 | 118.93 (18) |
C1—C2—C3 | 120.9 (3) | C10—C9—S1 | 122.15 (19) |
C1—C2—H2 | 119.6 | C11—C10—C9 | 120.5 (3) |
C3—C2—H2 | 119.6 | C11—C10—Cl2 | 117.5 (2) |
C4—C3—C2 | 120.3 (3) | C9—C10—Cl2 | 122.02 (19) |
C4—C3—H3 | 119.8 | C12—C11—C10 | 118.8 (3) |
C2—C3—H3 | 119.8 | C12—C11—H11 | 120.6 |
C5—C4—C3 | 119.5 (3) | C10—C11—H11 | 120.6 |
C5—C4—H4 | 120.2 | C13—C12—C11 | 121.8 (3) |
C3—C4—H4 | 120.2 | C13—C12—Cl1 | 120.2 (3) |
C4—C5—C6 | 120.5 (3) | C11—C12—Cl1 | 118.0 (3) |
C4—C5—H5 | 119.8 | C12—C13—C14 | 119.2 (3) |
C6—C5—H5 | 119.8 | C12—C13—H13 | 120.4 |
C5—C6—C1 | 120.6 (3) | C14—C13—H13 | 120.4 |
C5—C6—H6 | 119.7 | C13—C14—C9 | 120.7 (3) |
C1—C6—H6 | 119.7 | C13—C14—H14 | 119.6 |
C8—C7—C1 | 113.0 (2) | C9—C14—H14 | 119.6 |
C8—C7—H7A | 109.0 | C8—N1—S1 | 120.22 (17) |
C1—C7—H7A | 109.0 | C8—N1—H1 | 119.9 |
C8—C7—H7B | 109.0 | S1—N1—H1 | 119.9 |
C1—C7—H7B | 109.0 | ||
C6—C1—C2—C3 | −0.6 (5) | C14—C9—C10—C11 | 1.1 (3) |
C7—C1—C2—C3 | 178.7 (3) | S1—C9—C10—C11 | −178.63 (19) |
C1—C2—C3—C4 | 0.2 (6) | C14—C9—C10—Cl2 | −178.26 (18) |
C2—C3—C4—C5 | 0.5 (6) | S1—C9—C10—Cl2 | 2.0 (3) |
C3—C4—C5—C6 | −0.8 (5) | C9—C10—C11—C12 | 0.9 (4) |
C4—C5—C6—C1 | 0.4 (5) | Cl2—C10—C11—C12 | −179.7 (2) |
C2—C1—C6—C5 | 0.3 (4) | C10—C11—C12—C13 | −2.3 (5) |
C7—C1—C6—C5 | −179.0 (3) | C10—C11—C12—Cl1 | 177.8 (2) |
C2—C1—C7—C8 | 84.4 (4) | C11—C12—C13—C14 | 1.6 (5) |
C6—C1—C7—C8 | −96.4 (3) | Cl1—C12—C13—C14 | −178.5 (2) |
C1—C7—C8—N1 | 177.6 (2) | C12—C13—C14—C9 | 0.5 (4) |
O1—S1—C9—C14 | −130.6 (2) | C10—C9—C14—C13 | −1.8 (4) |
O2—S1—C9—C14 | −1.7 (2) | S1—C9—C14—C13 | 177.9 (2) |
N1—S1—C9—C14 | 113.21 (19) | C7—C8—N1—S1 | −146.0 (2) |
O1—S1—C9—C10 | 49.2 (2) | O1—S1—N1—C8 | 174.72 (19) |
O2—S1—C9—C10 | 178.00 (18) | O2—S1—N1—C8 | 45.2 (2) |
N1—S1—C9—C10 | −67.0 (2) | C9—S1—N1—C8 | −68.7 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8B···O2 | 0.97 | 2.51 | 2.953 (3) | 108 |
C14—H14···O2 | 0.93 | 2.44 | 2.848 (3) | 106 |
C6—H6···Cg1i | 0.93 | 2.96 | 3.694 (3) | 137 |
Symmetry code: (i) −x−1, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C14H13Cl2NO2S |
Mr | 330.21 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 295 |
a, b, c (Å) | 5.5618 (5), 10.9915 (8), 25.045 (2) |
V (Å3) | 1531.0 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.56 |
Crystal size (mm) | 0.20 × 0.18 × 0.12 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.896, 0.936 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10930, 3511, 2955 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.652 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.104, 1.05 |
No. of reflections | 3511 |
No. of parameters | 181 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.27, −0.24 |
Absolute structure | Flack (1983), 1455 Friedel pairs |
Absolute structure parameter | 0.04 (8) |
Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8B···O2 | 0.97 | 2.51 | 2.953 (3) | 108 |
C14—H14···O2 | 0.93 | 2.44 | 2.848 (3) | 106 |
C6—H6···Cg1i | 0.93 | 2.96 | 3.694 (3) | 137 |
Symmetry code: (i) −x−1, y+1/2, −z+1/2. |
Acknowledgements
The authors acknowledge SAIF IIT, Chennai, for the data collection.
References
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Sulfonamides have a variety of biological activities such as antibacterial (Gadad et al., 2000; Misra et al., 1982; Zani & Vicini, 1998), insulin releasing (Maren, 1976), carbonic anhydrase inhibitory (Supuran et al., 1998; Renzi et al., 2000), anti-inflammatory (Li et al., 1995) and antitumor (Yoshino et al., 1992) activities.
The geometric parameters in the title compound, (I), agree with the reported values of similar structure (Zhang et al., 2006; Andrighetti-Fröhner et al., 2007). The dihedral angle between the phenyl ring (C9—C14) and benzene ring (C1—C6) is 69.94 (9)°. The geometry around the S1 atom is distorted from a regular tetrahedron, with the largest deviations observed for O—S—O [O1—S1—O2 118.92 (14)°] and O—S—N [O1—S1—N1 107.87 (14) °] angles. The widening of the angles may be due to repulsive interactions between the two short S=O bonds.
The crystal structure is stabilized by weak intramolecular C—H···O interaction. The C8—H8B···O2 and C14—H14···O2 interactions each generate an S(5) graph set motif, and C8—H8B···O2 and C14—H14···O2 interactions together constitute a pair of bifurcated acceptor bonds, generating an R21(8) motif (Bernstein et al., 1995). The crystal packing is stabilized by a weak C—H···π (Table 1) interaction and a π–π interaction [Cg1···Cg2 (2 - x, 1/2 + y, 1/2 - z) distance of 4.3598 (18) Å; Cg1 and Cg2 are the centroids of rings C1—C6 and C9—C14, respectively].