4-Chloro-N-(2-chloro­benzo­yl)benzene­sulfonamide

In the structure of the title compound, C₁₃H₉Cl₂NO₃S, the conformation of the N—H bond in the C—SO₂—NH—C(O) segment is anti to the C=O bond. The mol­ecule is twisted at the S atom with a torsion angle of 65.7 (2)°. The dihedral angle between the sulfonyl benzene ring and the —SO₂—NH—C—O segment is 88.5 (1)°, and that between the sulfonyl and the benzoyl benzene rings is 58.0 (1)°. In the crystal, mol­ecules are linked by pairs of N—H...O hydrogen bonds, forming inversion dimers.

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.039
• wR factor = 0.107
• Data-to-parameter ratio = 15.4

checkCIF/PLATON results

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S1. Comment

As a part of studying the effect of ring and the side chain substituents on the crystal structures of N-aromatic sulfonamides (Gowda et al., 2010; Suchetan et al., 2010a,b,c), the structure of N-(2-chlorobenzoyl)-4-chlorobenzenesulfonamide (I) has been determined. The conformation of the N—H bond in the C—SO₂—NH—C(O) segment is anti to the C=O bond (Fig. 1), similar to those observed in N-(2-chlorobenzoyl)-benzenesulfonamide (II) (Gowda et al., 2010), N-(benzoyl)-4-chlorobenzenesulfonamide (III) (Suchetan et al., 2010a), N-(2-chlorobenzoyl)-2-chlorobenzenesulfonamide (IV) (Suchetan et al., 2010b) and N-(4-chlorobenzoyl)-4- chlorobenzenesulfonamide (V) (Suchetan et al., 2010c).

Further, the conformation of the C=O bond in the C—SO₂—NH—C(O) segment of (I) is syn to the ortho-Cl in the benzoyl ring, similar to that observed in (II) and (IV).

The molecules are twisted at the S atom with the torsional angle of 65.7 (2)°, compared to those of -59.0 (2)° (molecule 1) and -67.3 (2)° (molecule 2) in (II), -70.0 (2)°, 61.3 (2)° in the two independent molecules of (III), 66.5 (2)° in (IV) and 67.5 (3)° in (V).

The dihedral angle between the sulfonyl benzene ring and the —SO₂—NH—C—O segment is 88.5 (1)°, compared to the values of 87.3 (1)° (molecule 1) and 73.3 (1)° (molecule 2) in (II), 72.0 (1)° & 77.3 (1)° in the two molecules of (III), 86.9 (1)° in (IV) and 79.0 (1)° in (V).

Furthermore, the dihedral angle between the sulfonyl and the benzoyl benzene rings is 58.0 (1)°, compared to the values of 69.8 (1)° (molecule 1) and 89.8 (1)° (molecule 2) in (II), 62.8 (1)° (molecule 1) and 78.6 (1)° (molecule 2) of (III), 76.9 (1)° in (IV) and 85.6 (1)° in (V)

The packing of molecules linked by of N—H···O(S) hydrogen bonds (Table 1) is shown in Fig. 2.

Related literature

For our study of the effect of ring and side-chain substituents on the crystal structures of N-aromatic sulfonamides and for related structures, see: Gowda et al. (2010); Suchetan et al. (2010a,b,c).

S2. Experimental

The title compound was prepared by refluxing a mixture of 2-chlorobenzoic acid, 4-chlorobenzenesulfonamide and phosphorous oxy chloride for 3 h on a water bath. The resultant mixture was cooled and poured into ice cold water. The solid obtained was filtered, washed thoroughly with water and then dissolved in sodium bicarbonate solution. The compound was later reprecipitated by acidifying the filtered solution with dilute HCl. It was filtered, dried and recrystallized.

Prism like colourless single crystals of the title compound used in X-ray diffraction studies were obtained by slow evaporation of its toluene solution at room temperature.

S3. Refinement

The H atoms of the NH groups were located in a difference map and later restrained to N—H = 0.86 (2) %A. The other H atoms were positioned with idealized geometry using a riding model with C—H = 0.93 Å. All H atoms were refined with isotropic displacement parameters (set to 1.2 times of the U_eq of the parent atom).

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); 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).

Figures

	Fig. 1. Molecular structure of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Molecular packing in the title compound. Hydrogen bonds are shown as dashed lines.

4-Chloro-N-(2-chlorobenzoyl)benzenesulfonamide

Crystal data

C13H9Cl2NO3S	Z = 2
Mr = 330.17	F(000) = 336
Triclinic, P1	Dx = 1.577 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.3882 (9) Å	Cell parameters from 2339 reflections
b = 10.311 (1) Å	θ = 2.5–27.8°
c = 11.171 (1) Å	µ = 0.62 mm^−1
α = 79.01 (1)°	T = 299 K
β = 74.47 (1)°	Prism, colourless
γ = 84.76 (1)°	0.24 × 0.20 × 0.14 mm
V = 695.32 (13) Å^3

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2825 independent reflections
Radiation source: fine-focus sealed tube	2378 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
ω and φ scans	θmax = 26.4°, θmin = 2.5°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −7→7
Tmin = 0.865, Tmax = 0.918	k = −12→11
4417 measured reflections	l = −13→13

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0603P)^2 + 0.1863P] where P = (Fo^2 + 2Fc^2)/3
2825 reflections	(Δ/σ)max = 0.022
184 parameters	Δρmax = 0.25 e Å^−3
1 restraint	Δρmin = −0.52 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.3004 (3)	0.27841 (17)	0.07988 (17)	0.0364 (4)
C2	0.1714 (3)	0.39202 (19)	0.0968 (2)	0.0464 (5)
H2	0.0437	0.4059	0.0703	0.056*
C3	0.2338 (4)	0.4844 (2)	0.1532 (2)	0.0561 (6)
H3	0.1510	0.5624	0.1634	0.067*
C4	0.4198 (4)	0.4596 (2)	0.1942 (2)	0.0520 (5)
C5	0.5482 (4)	0.3465 (2)	0.1791 (2)	0.0543 (5)
H5	0.6730	0.3317	0.2085	0.065*
C6	0.4895 (3)	0.2553 (2)	0.1198 (2)	0.0478 (5)
H6	0.5760	0.1791	0.1068	0.057*
C7	0.0089 (3)	0.02215 (18)	0.22952 (18)	0.0384 (4)
C8	0.0163 (3)	−0.09961 (18)	0.32606 (17)	0.0396 (4)
C9	0.1632 (3)	−0.1155 (2)	0.39978 (18)	0.0451 (4)
C10	0.1579 (5)	−0.2246 (3)	0.4941 (2)	0.0641 (7)
H10	0.2565	−0.2347	0.5436	0.077*
C11	0.0073 (6)	−0.3171 (3)	0.5141 (2)	0.0757 (8)
H11	0.0043	−0.3908	0.5771	0.091*
C12	−0.1402 (5)	−0.3025 (3)	0.4422 (3)	0.0730 (7)
H12	−0.2424	−0.3663	0.4568	0.088*
C13	−0.1370 (4)	−0.1940 (2)	0.3487 (2)	0.0554 (5)
H13	−0.2378	−0.1840	0.3007	0.066*
Cl1	0.34983 (10)	0.00381 (7)	0.37663 (6)	0.0664 (2)
Cl2	0.49683 (16)	0.57327 (7)	0.26873 (8)	0.0938 (3)
N1	0.1748 (3)	0.02815 (15)	0.12059 (15)	0.0398 (4)
H1N	0.276 (3)	−0.0255 (19)	0.114 (2)	0.048*
O1	0.0294 (3)	0.20637 (15)	−0.02823 (14)	0.0550 (4)
O2	0.4074 (3)	0.11865 (14)	−0.08329 (13)	0.0537 (4)
O3	−0.1307 (2)	0.10807 (16)	0.24443 (16)	0.0602 (4)
S1	0.22277 (8)	0.15972 (4)	0.00846 (4)	0.04047 (15)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0364 (9)	0.0325 (8)	0.0360 (9)	−0.0001 (7)	−0.0058 (7)	−0.0008 (7)
C2	0.0448 (11)	0.0390 (10)	0.0503 (11)	0.0069 (8)	−0.0122 (9)	0.0006 (8)
C3	0.0695 (14)	0.0344 (10)	0.0568 (13)	0.0062 (9)	−0.0075 (11)	−0.0055 (9)
C4	0.0665 (14)	0.0424 (11)	0.0432 (11)	−0.0177 (9)	−0.0044 (10)	−0.0045 (8)
C5	0.0468 (11)	0.0561 (13)	0.0610 (13)	−0.0108 (9)	−0.0159 (10)	−0.0051 (10)
C6	0.0382 (10)	0.0431 (10)	0.0617 (13)	0.0040 (8)	−0.0140 (9)	−0.0091 (9)
C7	0.0365 (9)	0.0413 (9)	0.0406 (9)	−0.0023 (7)	−0.0146 (7)	−0.0076 (7)
C8	0.0430 (10)	0.0399 (9)	0.0342 (9)	0.0004 (7)	−0.0076 (7)	−0.0064 (7)
C9	0.0464 (10)	0.0529 (11)	0.0364 (10)	0.0068 (8)	−0.0111 (8)	−0.0120 (8)
C10	0.0786 (16)	0.0707 (15)	0.0399 (11)	0.0199 (13)	−0.0188 (11)	−0.0076 (10)
C11	0.112 (2)	0.0556 (14)	0.0457 (13)	0.0047 (14)	−0.0087 (14)	0.0059 (11)
C12	0.095 (2)	0.0539 (14)	0.0628 (16)	−0.0230 (13)	−0.0095 (14)	0.0015 (12)
C13	0.0615 (13)	0.0548 (12)	0.0500 (12)	−0.0148 (10)	−0.0127 (10)	−0.0059 (10)
Cl1	0.0571 (4)	0.0895 (4)	0.0633 (4)	−0.0126 (3)	−0.0273 (3)	−0.0178 (3)
Cl2	0.1363 (7)	0.0706 (5)	0.0834 (5)	−0.0386 (4)	−0.0236 (5)	−0.0259 (4)
N1	0.0441 (9)	0.0340 (8)	0.0394 (8)	0.0013 (6)	−0.0095 (7)	−0.0049 (6)
O1	0.0577 (9)	0.0586 (9)	0.0546 (9)	0.0005 (7)	−0.0303 (7)	−0.0030 (7)
O2	0.0656 (9)	0.0503 (8)	0.0367 (7)	0.0079 (7)	−0.0037 (6)	−0.0050 (6)
O3	0.0483 (8)	0.0617 (9)	0.0603 (10)	0.0152 (7)	−0.0092 (7)	−0.0008 (7)
S1	0.0464 (3)	0.0387 (3)	0.0356 (3)	0.00192 (18)	−0.01273 (19)	−0.00320 (18)

Geometric parameters (Å, º)

C1—C6	1.382 (3)	C8—C13	1.385 (3)
C1—C2	1.383 (3)	C8—C9	1.386 (3)
C1—S1	1.7537 (19)	C9—C10	1.382 (3)
C2—C3	1.377 (3)	C9—Cl1	1.727 (2)
C2—H2	0.9300	C10—C11	1.363 (4)
C3—C4	1.370 (3)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.375 (4)
C4—C5	1.374 (3)	C11—H11	0.9300
C4—Cl2	1.733 (2)	C12—C13	1.375 (3)
C5—C6	1.379 (3)	C12—H12	0.9300
C5—H5	0.9300	C13—H13	0.9300
C6—H6	0.9300	N1—S1	1.6510 (16)
C7—O3	1.200 (2)	N1—H1N	0.810 (15)
C7—N1	1.379 (3)	O1—S1	1.4185 (15)
C7—C8	1.497 (3)	O2—S1	1.4311 (15)
C6—C1—C2	121.20 (18)	C10—C9—C8	120.5 (2)
C6—C1—S1	118.92 (14)	C10—C9—Cl1	119.64 (18)
C2—C1—S1	119.87 (15)	C8—C9—Cl1	119.82 (16)
C3—C2—C1	119.35 (19)	C11—C10—C9	119.6 (2)
C3—C2—H2	120.3	C11—C10—H10	120.2
C1—C2—H2	120.3	C9—C10—H10	120.2
C4—C3—C2	119.03 (19)	C10—C11—C12	120.7 (2)
C4—C3—H3	120.5	C10—C11—H11	119.7
C2—C3—H3	120.5	C12—C11—H11	119.7
C3—C4—C5	122.2 (2)	C13—C12—C11	120.2 (2)
C3—C4—Cl2	119.51 (17)	C13—C12—H12	119.9
C5—C4—Cl2	118.31 (18)	C11—C12—H12	119.9
C4—C5—C6	119.0 (2)	C12—C13—C8	120.0 (2)
C4—C5—H5	120.5	C12—C13—H13	120.0
C6—C5—H5	120.5	C8—C13—H13	120.0
C5—C6—C1	119.17 (18)	C7—N1—S1	124.25 (13)
C5—C6—H6	120.4	C7—N1—H1N	121.9 (16)
C1—C6—H6	120.4	S1—N1—H1N	112.1 (16)
O3—C7—N1	122.05 (18)	O1—S1—O2	119.26 (9)
O3—C7—C8	123.12 (18)	O1—S1—N1	110.18 (9)
N1—C7—C8	114.82 (15)	O2—S1—N1	103.74 (8)
C13—C8—C9	119.07 (19)	O1—S1—C1	108.96 (9)
C13—C8—C7	119.35 (17)	O2—S1—C1	109.21 (9)
C9—C8—C7	121.40 (17)	N1—S1—C1	104.43 (8)
C6—C1—C2—C3	0.7 (3)	C8—C9—C10—C11	0.2 (3)
S1—C1—C2—C3	179.87 (16)	Cl1—C9—C10—C11	178.50 (19)
C1—C2—C3—C4	−1.7 (3)	C9—C10—C11—C12	−0.5 (4)
C2—C3—C4—C5	1.0 (3)	C10—C11—C12—C13	0.1 (4)
C2—C3—C4—Cl2	−178.50 (16)	C11—C12—C13—C8	0.6 (4)
C3—C4—C5—C6	0.6 (3)	C9—C8—C13—C12	−0.9 (3)
Cl2—C4—C5—C6	−179.85 (17)	C7—C8—C13—C12	−176.2 (2)
C4—C5—C6—C1	−1.6 (3)	O3—C7—N1—S1	9.1 (3)
C2—C1—C6—C5	0.9 (3)	C8—C7—N1—S1	−171.37 (13)
S1—C1—C6—C5	−178.23 (16)	C7—N1—S1—O1	−51.19 (18)
O3—C7—C8—C13	70.4 (3)	C7—N1—S1—O2	−179.94 (15)
N1—C7—C8—C13	−109.1 (2)	C7—N1—S1—C1	65.68 (17)
O3—C7—C8—C9	−104.8 (2)	C6—C1—S1—O1	−178.06 (15)
N1—C7—C8—C9	75.7 (2)	C2—C1—S1—O1	2.78 (18)
C13—C8—C9—C10	0.4 (3)	C6—C1—S1—O2	−46.22 (18)
C7—C8—C9—C10	175.66 (18)	C2—C1—S1—O2	134.61 (15)
C13—C8—C9—Cl1	−177.81 (16)	C6—C1—S1—N1	64.23 (17)
C7—C8—C9—Cl1	−2.6 (3)	C2—C1—S1—N1	−114.93 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2^i	0.81 (2)	2.13 (2)	2.914 (2)	164 (2)

Symmetry code: (i) −x+1, −y, −z.