2,4-Dichloro-N-phenethyl-benzene-sulfonamide.

In the title compound, C(14)H(13)Cl(2)NO(2)S, the dihedral angle between the phenyl ring and the benzene ring is 69.94 (9)°. Two short intra-molecular C-H⋯O contacts occur and a weak inter-molecular C-H⋯π inter-action is seen in the crystal.

Related literature

For the biological activity of sulfonamides, see: Gadad 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 ▶).

Experimental

Crystal data

C14H13Cl2NO2S

M = 330.21

Orthorhombic,

a = 5.5618 (5) Å

b = 10.9915 (8) Å

c = 25.045 (2) Å

V = 1531.0 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.56 mm−1

T = 295 K

0.20 × 0.18 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (; Sheldrick, 1996 ▶) T min = 0.896, T max = 0.936

10930 measured reflections

3511 independent reflections

2955 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.104

S = 1.05

3511 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.24 e Å−3

Absolute structure: Flack (1983 ▶), 1455 Friedel pairs

Flack parameter: 0.04 (8)

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/S1600536809010927/is2402sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010927/is2402Isup2.hkl

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

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	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 = −0.23 e Å−3
0 restraints	Absolute structure: Flack (1983), 1455 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.04 (8)

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

Table 1

Hydrogen-bond geometry (Å, °)

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) . Cg1 is the centroid of the C1–C6 ring.