2-Chloro-N-(4-chloro-benzo-yl)benzene-sulfonamide toluene hemisolvate.

The unit cell of the title compound, C(13)H(9)Cl(2)NO(3)S·0.5C(7)H(8), contains two mol-ecules of 2-chloro-N-(4-chloro-benzo-yl)benzene-sulfonamide and one toluene mol-ecule, which is disordered about a centre of inversion. The dihedral angle between the two aromatic rings is 85.7 (1)°. In the crystal, mol-ecules are linked by pairs of N-H⋯O(S) hydrogen bonds, forming centrosymmetric dimers.

Related literature

For background to our study of the effect of ring and side-chain substitutions on the crystal structures of N-aryl sulfon­amides and for similar structures, see: Gowda et al. (2010a ▶,b ▶); Suchetan et al. (2010 ▶).

Experimental

Crystal data

C13H9Cl2NO3S·0.5C7H8

M = 376.24

Triclinic,

a = 7.5992 (9) Å

b = 10.876 (1) Å

c = 11.346 (1) Å

α = 73.868 (8)°

β = 75.927 (9)°

γ = 70.994 (8)°

V = 839.58 (15) Å3

Z = 2

Mo Kα radiation

μ = 0.53 mm−1

T = 299 K

0.44 × 0.44 × 0.36 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.802, T max = 0.834

5654 measured reflections

3405 independent reflections

2941 reflections with I > 2σ(I)

R int = 0.009

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.099

S = 1.06

3405 reflections

229 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.43 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; 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 I, global. DOI: 10.1107/S1600536810052281/bt5432sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052281/bt5432Isup2.hkl

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

C13H9Cl2NO3S·0.5C7H8	Z = 2
Mr = 376.24	F(000) = 386
Triclinic, P1	Dx = 1.488 Mg m−3
Hall symbol: -p 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5992 (9) Å	Cell parameters from 3881 reflections
b = 10.876 (1) Å	θ = 2.9–27.8°
c = 11.346 (1) Å	µ = 0.53 mm−1
α = 73.868 (8)°	T = 299 K
β = 75.927 (9)°	Prism, colourless
γ = 70.994 (8)°	0.44 × 0.44 × 0.36 mm
V = 839.58 (15) Å3

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	3405 independent reflections
Radiation source: fine-focus sealed tube	2941 reflections with I > 2σ(I)
graphite	Rint = 0.009
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −9→9
Tmin = 0.802, Tmax = 0.834	k = −13→13
5654 measured reflections	l = −13→14

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0428P)2 + 0.4443P] where P = (Fo2 + 2Fc2)/3
3405 reflections	(Δ/σ)max = 0.001
229 parameters	Δρmax = 0.24 e Å−3
3 restraints	Δρmin = −0.43 e Å−3

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	Occ. (<1)
Cl1	0.82406 (9)	0.59662 (6)	0.34975 (6)	0.06376 (18)
Cl2	0.89482 (11)	−0.27177 (6)	0.59894 (6)	0.0726 (2)
S1	0.46063 (7)	0.54050 (5)	0.28910 (4)	0.04093 (14)
O1	0.4019 (2)	0.61891 (14)	0.38181 (13)	0.0523 (4)
O2	0.3219 (2)	0.53244 (17)	0.22960 (15)	0.0594 (4)
O3	0.6558 (3)	0.30065 (15)	0.19122 (13)	0.0597 (4)
N1	0.5639 (2)	0.38940 (16)	0.36235 (15)	0.0428 (4)
H1N	0.579 (3)	0.386 (2)	0.433 (2)	0.051*
C1	0.6378 (3)	0.59331 (18)	0.17244 (17)	0.0395 (4)
C2	0.7921 (3)	0.61655 (19)	0.19841 (19)	0.0456 (4)
C3	0.9255 (3)	0.6578 (2)	0.1010 (3)	0.0635 (6)
H3	1.0305	0.6722	0.1173	0.076*
C4	0.9015 (4)	0.6773 (3)	−0.0197 (3)	0.0745 (8)
H4	0.9911	0.7050	−0.0848	0.089*
C5	0.7480 (4)	0.6567 (3)	−0.0455 (2)	0.0682 (7)
H5	0.7325	0.6719	−0.1277	0.082*
C6	0.6166 (3)	0.6134 (2)	0.04986 (19)	0.0523 (5)
H6	0.5136	0.5977	0.0323	0.063*
C7	0.6431 (3)	0.28362 (19)	0.30279 (18)	0.0421 (4)
C8	0.7089 (3)	0.14941 (18)	0.38331 (18)	0.0404 (4)
C9	0.6374 (3)	0.1159 (2)	0.50887 (19)	0.0485 (5)
H9	0.5501	0.1807	0.5485	0.058*
C10	0.6955 (3)	−0.0136 (2)	0.5754 (2)	0.0536 (5)
H10	0.6468	−0.0362	0.6595	0.064*
C11	0.8254 (3)	−0.1085 (2)	0.5167 (2)	0.0478 (5)
C12	0.9002 (3)	−0.0773 (2)	0.3927 (2)	0.0581 (6)
H12	0.9893	−0.1421	0.3541	0.070*
C13	0.8411 (3)	0.0512 (2)	0.3268 (2)	0.0549 (5)
H13	0.8906	0.0729	0.2427	0.066*
C14	0.4143 (9)	−0.0335 (6)	1.0155 (6)	0.0821 (17)	0.50
C15	0.4774 (7)	0.0445 (4)	0.8986 (3)	0.0963 (11)
H15A	0.4031	0.0715	0.8369	0.116*	0.50
H15B	0.5192	0.0831	0.8135	0.116*	0.50
C16	0.6245 (14)	0.0797 (6)	0.8707 (7)	0.1058 (17)	0.50
H16A	0.6644	0.1127	0.7870	0.127*	0.50
C17	0.7412 (8)	0.0691 (6)	0.9649 (7)	0.1470 (19)
H17A	0.8390	0.1082	0.9492	0.176*	0.50
H17B	0.7570	0.1193	0.8808	0.176*	0.50
H17C	0.8486	−0.0073	0.9758	0.176*	0.50
H17D	0.7303	0.1239	1.0210	0.176*	0.50
C18	0.6696 (18)	−0.0094 (9)	1.0854 (11)	0.126 (4)	0.50
H18A	0.7398	−0.0358	1.1493	0.151*	0.50

	U11	U22	U33	U12	U13	U23
Cl1	0.0641 (4)	0.0659 (4)	0.0699 (4)	−0.0150 (3)	−0.0330 (3)	−0.0130 (3)
Cl2	0.1049 (5)	0.0385 (3)	0.0687 (4)	−0.0145 (3)	−0.0255 (3)	0.0005 (3)
S1	0.0408 (2)	0.0379 (2)	0.0415 (3)	−0.00830 (18)	−0.00962 (19)	−0.00531 (19)
O1	0.0585 (9)	0.0427 (8)	0.0456 (8)	−0.0038 (6)	−0.0031 (6)	−0.0105 (6)
O2	0.0473 (8)	0.0649 (10)	0.0689 (10)	−0.0177 (7)	−0.0222 (7)	−0.0057 (8)
O3	0.0875 (12)	0.0494 (9)	0.0409 (8)	−0.0161 (8)	−0.0134 (7)	−0.0091 (6)
N1	0.0553 (10)	0.0353 (8)	0.0373 (8)	−0.0109 (7)	−0.0111 (7)	−0.0061 (7)
C1	0.0434 (10)	0.0313 (9)	0.0408 (9)	−0.0071 (7)	−0.0082 (8)	−0.0061 (7)
C2	0.0445 (10)	0.0347 (9)	0.0534 (11)	−0.0061 (8)	−0.0116 (9)	−0.0057 (8)
C3	0.0464 (12)	0.0493 (13)	0.0864 (18)	−0.0130 (10)	−0.0034 (11)	−0.0085 (12)
C4	0.0755 (17)	0.0581 (15)	0.0659 (16)	−0.0184 (13)	0.0197 (13)	−0.0034 (12)
C5	0.0890 (19)	0.0590 (15)	0.0431 (12)	−0.0150 (13)	0.0013 (12)	−0.0073 (10)
C6	0.0681 (14)	0.0454 (11)	0.0419 (11)	−0.0128 (10)	−0.0128 (10)	−0.0076 (9)
C7	0.0469 (10)	0.0404 (10)	0.0419 (10)	−0.0162 (8)	−0.0067 (8)	−0.0093 (8)
C8	0.0457 (10)	0.0373 (9)	0.0419 (10)	−0.0161 (8)	−0.0070 (8)	−0.0092 (8)
C9	0.0587 (12)	0.0393 (10)	0.0455 (11)	−0.0127 (9)	−0.0030 (9)	−0.0119 (8)
C10	0.0746 (15)	0.0443 (11)	0.0410 (11)	−0.0202 (10)	−0.0058 (10)	−0.0071 (9)
C11	0.0595 (12)	0.0348 (10)	0.0518 (11)	−0.0156 (9)	−0.0158 (9)	−0.0049 (8)
C12	0.0641 (14)	0.0410 (11)	0.0603 (13)	−0.0096 (10)	0.0025 (11)	−0.0143 (10)
C13	0.0694 (14)	0.0432 (11)	0.0449 (11)	−0.0159 (10)	0.0041 (10)	−0.0097 (9)
C14	0.078 (4)	0.068 (4)	0.085 (4)	0.015 (3)	−0.007 (3)	−0.041 (3)
C15	0.125 (3)	0.082 (2)	0.0583 (18)	0.014 (2)	−0.021 (2)	−0.0238 (17)
C16	0.146 (5)	0.051 (3)	0.079 (4)	−0.001 (4)	0.022 (3)	−0.016 (3)
C17	0.113 (4)	0.114 (4)	0.198 (6)	0.002 (3)	−0.018 (3)	−0.057 (4)
C18	0.164 (9)	0.088 (5)	0.154 (9)	−0.001 (6)	−0.108 (8)	−0.042 (5)

Cl1—C2	1.737 (2)	C12—H12	0.9300
Cl2—C11	1.735 (2)	C13—H13	0.9300
S1—O2	1.4191 (15)	C14—C16i	1.248 (10)
S1—O1	1.4336 (15)	C14—C17i	1.311 (8)
S1—N1	1.6508 (17)	C14—C18i	1.342 (10)
S1—C1	1.763 (2)	C14—C15i	1.379 (8)
O3—C7	1.212 (2)	C14—C15	1.428 (8)
N1—C7	1.388 (2)	C14—C14i	1.613 (16)
N1—H1N	0.82 (2)	C15—C16	1.239 (10)
C1—C6	1.387 (3)	C15—C18i	1.252 (11)
C1—C2	1.389 (3)	C15—C14i	1.379 (8)
C2—C3	1.388 (3)	C15—H15A	0.9300
C3—C4	1.374 (4)	C15—H15B	0.9601
C3—H3	0.9300	C16—C14i	1.248 (10)
C4—C5	1.368 (4)	C16—C17	1.506 (11)
C4—H4	0.9300	C16—H15B	1.1326
C5—C6	1.373 (3)	C16—H16A	0.9300
C5—H5	0.9300	C16—H17B	1.2556
C6—H6	0.9300	C17—C14i	1.311 (8)
C7—C8	1.490 (3)	C17—C18	1.478 (13)
C8—C9	1.386 (3)	C17—H17A	0.9299
C8—C13	1.389 (3)	C17—H17B	0.9600
C9—C10	1.384 (3)	C17—H17C	0.9600
C9—H9	0.9300	C17—H17D	0.9599
C10—C11	1.371 (3)	C18—C15i	1.252 (11)
C10—H10	0.9300	C18—C14i	1.342 (10)
C11—C12	1.375 (3)	C18—H18A	0.9300
C12—C13	1.374 (3)
O2—S1—O1	118.68 (10)	C18i—C14—C14i	106.8 (10)
O2—S1—N1	108.83 (9)	C15i—C14—C14i	56.4 (5)
O1—S1—N1	104.52 (9)	C15—C14—C14i	53.5 (5)
O2—S1—C1	107.90 (9)	C16—C15—C18i	173.8 (7)
O1—S1—C1	110.14 (9)	C16—C15—C14i	56.6 (5)
N1—S1—C1	106.05 (9)	C18i—C15—C14i	129.3 (7)
C7—N1—S1	122.20 (14)	C16—C15—C14	125.8 (6)
C7—N1—H1N	123.3 (17)	C18i—C15—C14	59.7 (6)
S1—N1—H1N	113.9 (17)	C14i—C15—C14	70.1 (6)
C6—C1—C2	119.90 (19)	C16—C15—H15A	116.1
C6—C1—S1	116.98 (16)	C18i—C15—H15A	58.4
C2—C1—S1	123.11 (15)	C14i—C15—H15A	167.6
C3—C2—C1	119.4 (2)	C14—C15—H15A	118.0
C3—C2—Cl1	118.42 (18)	C16—C15—H15B	60.4
C1—C2—Cl1	122.13 (16)	C18i—C15—H15B	113.7
C4—C3—C2	119.7 (2)	C14i—C15—H15B	117.0
C4—C3—H3	120.2	C14—C15—H15B	168.8
C2—C3—H3	120.2	H15A—C15—H15B	56.6
C5—C4—C3	121.0 (2)	C15—C16—C14i	67.3 (6)
C5—C4—H4	119.5	C15—C16—C17	123.2 (6)
C3—C4—H4	119.5	C14i—C16—C17	55.9 (5)
C4—C5—C6	120.0 (2)	C15—C16—H15B	47.5
C4—C5—H5	120.0	C14i—C16—H15B	114.8
C6—C5—H5	120.0	C17—C16—H15B	170.6
C5—C6—C1	120.0 (2)	C15—C16—H16A	117.5
C5—C6—H6	120.0	C14i—C16—H16A	174.9
C1—C6—H6	120.0	C17—C16—H16A	119.3
O3—C7—N1	121.13 (18)	H15B—C16—H16A	70.1
O3—C7—C8	122.36 (18)	C15—C16—H17B	160.2
N1—C7—C8	116.50 (16)	C14i—C16—H17B	94.6
C9—C8—C13	118.74 (18)	C17—C16—H17B	39.4
C9—C8—C7	123.58 (18)	H15B—C16—H17B	149.2
C13—C8—C7	117.56 (17)	H16A—C16—H17B	80.9
C10—C9—C8	120.19 (19)	C14i—C17—C18	57.1 (5)
C10—C9—H9	119.9	C14i—C17—C16	52.0 (5)
C8—C9—H9	119.9	C18—C17—C16	108.5 (6)
C11—C10—C9	119.68 (19)	C14i—C17—H17A	170.8
C11—C10—H10	120.2	C18—C17—H17A	126.6
C9—C10—H10	120.2	C16—C17—H17A	124.9
C10—C11—C12	121.18 (19)	C14i—C17—H17B	107.2
C10—C11—Cl2	119.84 (17)	C18—C17—H17B	164.3
C12—C11—Cl2	118.97 (17)	C16—C17—H17B	56.1
C11—C12—C13	119.0 (2)	H17A—C17—H17B	68.8
C11—C12—H12	120.5	C14i—C17—H17C	111.2
C13—C12—H12	120.5	C18—C17—H17C	79.3
C12—C13—C8	121.2 (2)	C16—C17—H17C	117.5
C12—C13—H13	119.4	H17A—C17—H17C	78.0
C8—C13—H13	119.4	H17B—C17—H17C	109.5
C16i—C14—C17i	72.1 (7)	C14i—C17—H17D	110.0
C16i—C14—C18i	138.6 (10)	C18—C17—H17D	78.3
C17i—C14—C18i	67.7 (7)	C16—C17—H17D	133.0
C16i—C14—C15i	56.1 (6)	H17A—C17—H17D	65.1
C17i—C14—C15i	128.1 (7)	H17B—C17—H17D	109.5
C18i—C14—C15i	162.3 (9)	H17C—C17—H17D	109.5
C16i—C14—C15	163.1 (8)	C15i—C18—C14i	66.7 (6)
C17i—C14—C15	121.3 (6)	C15i—C18—C17	121.8 (7)
C18i—C14—C15	53.6 (6)	C14i—C18—C17	55.2 (6)
C15i—C14—C15	109.9 (6)	C15i—C18—H18A	120.0
C16i—C14—C14i	111.7 (9)	C14i—C18—H18A	173.2
C17i—C14—C14i	171.1 (7)	C17—C18—H18A	118.2
O2—S1—N1—C7	53.15 (18)	C9—C10—C11—Cl2	−178.61 (17)
O1—S1—N1—C7	−179.10 (15)	C10—C11—C12—C13	−0.8 (4)
C1—S1—N1—C7	−62.70 (17)	Cl2—C11—C12—C13	178.16 (19)
O2—S1—C1—C6	−1.61 (18)	C11—C12—C13—C8	0.4 (4)
O1—S1—C1—C6	−132.58 (15)	C9—C8—C13—C12	0.5 (3)
N1—S1—C1—C6	114.87 (16)	C7—C8—C13—C12	−175.8 (2)
O2—S1—C1—C2	177.49 (16)	C16i—C14—C15—C16	42 (2)
O1—S1—C1—C2	46.52 (18)	C17i—C14—C15—C16	−178.0 (6)
N1—S1—C1—C2	−66.03 (18)	C18i—C14—C15—C16	−176.6 (7)
C6—C1—C2—C3	−1.0 (3)	C15i—C14—C15—C16	10.8 (6)
S1—C1—C2—C3	179.91 (16)	C14i—C14—C15—C16	10.8 (6)
C6—C1—C2—Cl1	178.61 (15)	C16i—C14—C15—C18i	−141 (2)
S1—C1—C2—Cl1	−0.5 (2)	C17i—C14—C15—C18i	−1.4 (7)
C1—C2—C3—C4	1.1 (3)	C15i—C14—C15—C18i	−172.6 (6)
Cl1—C2—C3—C4	−178.52 (19)	C14i—C14—C15—C18i	−172.6 (6)
C2—C3—C4—C5	0.0 (4)	C16i—C14—C15—C14i	31 (2)
C3—C4—C5—C6	−1.2 (4)	C17i—C14—C15—C14i	171.2 (7)
C4—C5—C6—C1	1.3 (4)	C18i—C14—C15—C14i	172.6 (6)
C2—C1—C6—C5	−0.2 (3)	C15i—C14—C15—C14i	0.0
S1—C1—C6—C5	178.95 (18)	C18i—C15—C16—C14i	−164 (5)
S1—N1—C7—O3	7.2 (3)	C14—C15—C16—C14i	−12.2 (7)
S1—N1—C7—C8	−172.21 (14)	C18i—C15—C16—C17	−164 (5)
O3—C7—C8—C9	−154.7 (2)	C14i—C15—C16—C17	−0.8 (5)
N1—C7—C8—C9	24.7 (3)	C14—C15—C16—C17	−12.9 (9)
O3—C7—C8—C13	21.4 (3)	C15—C16—C17—C14i	0.9 (5)
N1—C7—C8—C13	−159.19 (19)	C15—C16—C17—C18	9.8 (8)
C13—C8—C9—C10	−0.9 (3)	C14i—C16—C17—C18	8.9 (6)
C7—C8—C9—C10	175.12 (19)	C14i—C17—C18—C15i	1.4 (7)
C8—C9—C10—C11	0.5 (3)	C16—C17—C18—C15i	−7.0 (10)
C9—C10—C11—C12	0.4 (3)	C16—C17—C18—C14i	−8.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ii	0.82 (2)	2.13 (2)	2.951 (2)	176 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.82 (2)	2.13 (2)	2.951 (2)	176 (2)

Symmetry code: (i) .