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

Suchetan, P.A.; Foro, S.; Gowda, B.T.

doi:10.1107/S1600536810050087

organic compounds

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ISSN: 2056-9890

Volume 67| Part 1| January 2011| Page o22

https://doi.org/10.1107/S1600536810050087

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

P. A. Suchetan,^a Sabine Foro ^b and B. Thimme Gowda ^a ^*

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 29 November 2010; accepted 30 November 2010; online 4 December 2010)

In the title compound, C₁₄H₁₂ClNO₃S, the conformation of the N—H bond in the C—SO₂—NH—C(O) segment is anti to the C=O bond. The two aromatic rings are tilted relative to each other by 57.7 (1)°. In the crystal, molecules 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 substituents on the crystal structures of N-aromatic sulfonamides and for similar structures, see: Gowda et al. (2010a ,b ); Suchetan et al. (2010 ).

Experimental

Crystal data

C₁₄H₁₂ClNO₃S
M_r = 309.76
Triclinic, $[P \overline 1]$
a = 6.4328 (9) Å
b = 10.343 (1) Å
c = 11.207 (1) Å
α = 78.78 (1)°
β = 73.84 (1)°
γ = 84.62 (1)°
V = 701.88 (13) Å³
Z = 2
Cu Kα radiation
μ = 3.86 mm⁻¹
T = 299 K
0.40 × 0.15 × 0.15 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
4317 measured reflections
2502 independent reflections
2283 reflections with I > 2σ(I)
R_int = 0.039
3 standard reflections every 120 min intensity decay: 0.5%

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.147
S = 1.04
2502 reflections
186 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.76 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.82 (2)	2.15 (2)	2.925 (3)	157 (3)
Symmetry code: (i) -x, -y+1, -z+2.

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ); 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

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810050087/bt5427sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810050087/bt5427Isup2.hkl

checkCIF report

Comment top

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., 2010a,b; Suchetan et al., 2010), the structure of 4-Chloro-N-(2-methylbenzoyl)benzenesulfonamide (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)-4-chlorobenzenesulfonamide (II)(Gowda et al., 2010a), N-(2-methylbenzoyl)-4-methylbenzenesulfonamide (III) (Gowda et al., 2010b) and N-(2-methylbenzoyl)- 2-chlorobenzenesulfonamide (IV) (Suchetan et al., 2010).

The molecules are twisted at the S atom with the torsional angle of -69.2 (2)°, compared to those of 65.7 (2)° in (II), 67.7 (2)° in (III) and -64.0 (2)° in (IV).

The dihedral angles between the sulfonyl benzene ring and the —SO₂—NH—C—O segment is 87.2 (1)°, compared to the values of 88.5 (1)° in (II), 87.1 (1)° in (III) and 88.4 (1)° in (IV).

Furthermore, the dihedral angle between the sulfonyl and the benzoyl benzene rings is 57.7 (1)°, compared to the values of 58.0 (1)° in (II), 58.2 (1)° in (III) and 78.7 (1)° in (IV)

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

Related literature top

Experimental top

The title compound was prepared by refluxing a mixture of 2-methylbenzoic 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, N-(2-methylbenzoyl)-4-chlorobenzenesulfonamide 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.

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

Structure description top

The molecules are twisted at the S atom with the torsional angle of -69.2 (2)°, compared to those of 65.7 (2)° in (II), 67.7 (2)° in (III) and -64.0 (2)° in (IV).

The dihedral angles between the sulfonyl benzene ring and the —SO₂—NH—C—O segment is 87.2 (1)°, compared to the values of 88.5 (1)° in (II), 87.1 (1)° in (III) and 88.4 (1)° in (IV).

Furthermore, the dihedral angle between the sulfonyl and the benzoyl benzene rings is 57.7 (1)°, compared to the values of 58.0 (1)° in (II), 58.2 (1)° in (III) and 78.7 (1)° in (IV)

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

Computing details top

Data collection: CAD-4-PC (Enraf–Nonius, 1996); cell refinement: CAD-4-PC (Enraf–Nonius, 1996); data reduction: REDU4 (Stoe & Cie, 1987); 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 top

	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-methylbenzoyl)benzenesulfonamide top

Crystal data top

C₁₄H₁₂ClNO₃S	Z = 2
M_r = 309.76	F(000) = 320
Triclinic, P1	D_x = 1.466 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54180 Å
a = 6.4328 (9) Å	Cell parameters from 25 reflections
b = 10.343 (1) Å	θ = 4.2–22.5°
c = 11.207 (1) Å	µ = 3.86 mm⁻¹
α = 78.78 (1)°	T = 299 K
β = 73.84 (1)°	Rod, colourless
γ = 84.62 (1)°	0.40 × 0.15 × 0.15 mm
V = 701.88 (13) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.039
Radiation source: fine-focus sealed tube	θ_max = 66.9°, θ_min = 4.2°
Graphite monochromator	h = −7→4
ω/2θ scans	k = −12→12
4317 measured reflections	l = −13→13
2502 independent reflections	3 standard reflections every 120 min
2283 reflections with I > 2σ(I)	intensity decay: 0.5%

Refinement top

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)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.147	w = 1/[σ²(F_o²) + (0.1004P)² + 0.2209P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2502 reflections	Δρ_max = 0.76 e Å⁻³
186 parameters	Δρ_min = −0.56 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.038 (3)

Crystal data top

C₁₄H₁₂ClNO₃S	γ = 84.62 (1)°
M_r = 309.76	V = 701.88 (13) Å³
Triclinic, P1	Z = 2
a = 6.4328 (9) Å	Cu Kα radiation
b = 10.343 (1) Å	µ = 3.86 mm⁻¹
c = 11.207 (1) Å	T = 299 K
α = 78.78 (1)°	0.40 × 0.15 × 0.15 mm
β = 73.84 (1)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.039
4317 measured reflections	3 standard reflections every 120 min
2502 independent reflections	intensity decay: 0.5%
2283 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.052	1 restraint
wR(F²) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.76 e Å⁻³
2502 reflections	Δρ_min = −0.56 e Å⁻³
186 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.2014 (3)	0.2235 (2)	0.92052 (19)	0.0403 (5)
C2	0.3302 (4)	0.1107 (2)	0.9031 (2)	0.0505 (5)
H2	0.4576	0.0973	0.9285	0.061*
C3	0.2687 (5)	0.0180 (2)	0.8478 (3)	0.0605 (7)
H3	0.3518	−0.0596	0.8373	0.073*
C4	0.0816 (5)	0.0425 (2)	0.8083 (2)	0.0573 (6)
C5	−0.0465 (4)	0.1555 (3)	0.8239 (3)	0.0585 (6)
H5	−0.1709	0.1703	0.7955	0.070*
C6	0.0124 (4)	0.2463 (2)	0.8821 (2)	0.0512 (6)
H6	−0.0739	0.3222	0.8955	0.061*
C7	0.4960 (3)	0.4841 (2)	0.7696 (2)	0.0429 (5)
C8	0.4849 (4)	0.6049 (2)	0.6737 (2)	0.0439 (5)
C9	0.3391 (4)	0.6163 (2)	0.6007 (2)	0.0509 (6)
C10	0.3493 (5)	0.7283 (3)	0.5067 (2)	0.0686 (8)
H10	0.2534	0.7394	0.4565	0.082*
C11	0.4987 (6)	0.8224 (3)	0.4870 (3)	0.0790 (9)
H11	0.5026	0.8959	0.4237	0.095*
C12	0.6422 (6)	0.8090 (3)	0.5598 (3)	0.0768 (9)
H12	0.7427	0.8730	0.5460	0.092*
C13	0.6361 (5)	0.7005 (3)	0.6529 (3)	0.0604 (6)
H13	0.7331	0.6907	0.7023	0.073*
C14	0.1835 (4)	0.5118 (3)	0.6165 (3)	0.0661 (7)
H14A	0.0593	0.5222	0.6857	0.079*
H14B	0.2528	0.4265	0.6336	0.079*
H14C	0.1385	0.5197	0.5405	0.079*
N1	0.3253 (3)	0.47376 (17)	0.87777 (17)	0.0434 (4)
H1N	0.229 (4)	0.532 (2)	0.883 (2)	0.052*
O1	0.0959 (3)	0.38337 (16)	1.08307 (14)	0.0554 (5)
O2	0.4730 (3)	0.29640 (17)	1.02583 (16)	0.0581 (5)
O3	0.6391 (3)	0.4000 (2)	0.75586 (18)	0.0674 (5)
Cl1	0.00535 (19)	−0.07131 (8)	0.73539 (8)	0.0981 (4)
S1	0.27927 (8)	0.34281 (5)	0.99049 (5)	0.0427 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0376 (10)	0.0380 (10)	0.0435 (10)	−0.0018 (8)	−0.0103 (8)	−0.0029 (8)
C2	0.0508 (12)	0.0421 (11)	0.0553 (13)	0.0059 (9)	−0.0157 (10)	−0.0023 (9)
C3	0.0726 (17)	0.0405 (12)	0.0620 (15)	0.0046 (11)	−0.0101 (13)	−0.0089 (10)
C4	0.0726 (16)	0.0482 (13)	0.0489 (13)	−0.0211 (11)	−0.0081 (11)	−0.0063 (10)
C5	0.0505 (13)	0.0616 (15)	0.0664 (15)	−0.0146 (11)	−0.0199 (12)	−0.0062 (12)
C6	0.0405 (11)	0.0467 (12)	0.0681 (14)	0.0009 (9)	−0.0176 (10)	−0.0111 (10)
C7	0.0394 (10)	0.0468 (11)	0.0468 (11)	−0.0035 (9)	−0.0170 (9)	−0.0094 (9)
C8	0.0441 (11)	0.0461 (11)	0.0410 (10)	−0.0014 (9)	−0.0094 (9)	−0.0094 (8)
C9	0.0502 (12)	0.0609 (13)	0.0424 (11)	0.0084 (10)	−0.0136 (9)	−0.0144 (10)
C10	0.0818 (19)	0.0769 (18)	0.0469 (13)	0.0194 (15)	−0.0237 (13)	−0.0114 (12)
C11	0.112 (3)	0.0580 (16)	0.0533 (15)	0.0025 (16)	−0.0111 (16)	0.0036 (12)
C12	0.101 (2)	0.0567 (15)	0.0668 (17)	−0.0248 (15)	−0.0129 (17)	0.0003 (13)
C13	0.0670 (16)	0.0575 (14)	0.0588 (14)	−0.0147 (12)	−0.0176 (12)	−0.0082 (11)
C14	0.0479 (13)	0.095 (2)	0.0652 (16)	−0.0053 (13)	−0.0244 (12)	−0.0223 (14)
N1	0.0451 (10)	0.0387 (9)	0.0464 (10)	0.0006 (7)	−0.0129 (8)	−0.0073 (7)
O1	0.0640 (10)	0.0536 (9)	0.0427 (8)	0.0038 (8)	−0.0078 (7)	−0.0068 (7)
O2	0.0553 (10)	0.0641 (10)	0.0617 (10)	−0.0003 (8)	−0.0330 (8)	−0.0027 (8)
O3	0.0527 (10)	0.0709 (11)	0.0668 (11)	0.0169 (9)	−0.0106 (9)	−0.0015 (9)
Cl1	0.1417 (9)	0.0778 (6)	0.0845 (6)	−0.0445 (5)	−0.0243 (6)	−0.0269 (4)
S1	0.0446 (4)	0.0425 (4)	0.0418 (3)	0.0002 (2)	−0.0153 (2)	−0.0046 (2)

Geometric parameters (Å, º) top

C1—C2	1.379 (3)	C9—C10	1.399 (4)
C1—C6	1.385 (3)	C9—C14	1.493 (4)
C1—S1	1.760 (2)	C10—C11	1.376 (5)
C2—C3	1.378 (4)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.373 (5)
C3—C4	1.381 (4)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.371 (4)
C4—C5	1.377 (4)	C12—H12	0.9300
C4—Cl1	1.732 (2)	C13—H13	0.9300
C5—C6	1.376 (4)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—H6	0.9300	C14—H14C	0.9600
C7—O3	1.205 (3)	N1—S1	1.6489 (18)
C7—N1	1.385 (3)	N1—H1N	0.819 (17)
C7—C8	1.491 (3)	O1—S1	1.4280 (17)
C8—C9	1.389 (3)	O2—S1	1.4243 (17)
C8—C13	1.394 (3)

C2—C1—C6	121.3 (2)	C11—C10—C9	121.2 (3)
C2—C1—S1	119.81 (17)	C11—C10—H10	119.4
C6—C1—S1	118.90 (17)	C9—C10—H10	119.4
C3—C2—C1	119.5 (2)	C12—C11—C10	120.7 (3)
C3—C2—H2	120.3	C12—C11—H11	119.7
C1—C2—H2	120.3	C10—C11—H11	119.7
C2—C3—C4	118.8 (2)	C13—C12—C11	119.5 (3)
C2—C3—H3	120.6	C13—C12—H12	120.2
C4—C3—H3	120.6	C11—C12—H12	120.2
C5—C4—C3	122.1 (2)	C12—C13—C8	120.2 (3)
C5—C4—Cl1	118.6 (2)	C12—C13—H13	119.9
C3—C4—Cl1	119.3 (2)	C8—C13—H13	119.9
C6—C5—C4	119.0 (2)	C9—C14—H14A	109.5
C6—C5—H5	120.5	C9—C14—H14B	109.5
C4—C5—H5	120.5	H14A—C14—H14B	109.5
C5—C6—C1	119.3 (2)	C9—C14—H14C	109.5
C5—C6—H6	120.3	H14A—C14—H14C	109.5
C1—C6—H6	120.3	H14B—C14—H14C	109.5
O3—C7—N1	121.3 (2)	C7—N1—S1	125.08 (16)
O3—C7—C8	123.9 (2)	C7—N1—H1N	118.8 (19)
N1—C7—C8	114.76 (18)	S1—N1—H1N	115.6 (19)
C9—C8—C13	121.2 (2)	O2—S1—O1	119.23 (11)
C9—C8—C7	120.7 (2)	O2—S1—N1	110.43 (10)
C13—C8—C7	118.0 (2)	O1—S1—N1	103.74 (10)
C8—C9—C10	117.2 (2)	O2—S1—C1	108.92 (10)
C8—C9—C14	122.2 (2)	O1—S1—C1	109.13 (11)
C10—C9—C14	120.5 (2)	N1—S1—C1	104.33 (9)

C6—C1—C2—C3	−0.8 (4)	C8—C9—C10—C11	0.5 (4)
S1—C1—C2—C3	−179.73 (18)	C14—C9—C10—C11	−176.9 (3)
C1—C2—C3—C4	1.6 (4)	C9—C10—C11—C12	−0.2 (5)
C2—C3—C4—C5	−0.8 (4)	C10—C11—C12—C13	0.0 (5)
C2—C3—C4—Cl1	178.54 (18)	C11—C12—C13—C8	−0.2 (5)
C3—C4—C5—C6	−0.8 (4)	C9—C8—C13—C12	0.5 (4)
Cl1—C4—C5—C6	179.78 (19)	C7—C8—C13—C12	175.5 (2)
C4—C5—C6—C1	1.7 (4)	O3—C7—N1—S1	−7.6 (3)
C2—C1—C6—C5	−0.9 (4)	C8—C7—N1—S1	171.71 (15)
S1—C1—C6—C5	178.06 (18)	C7—N1—S1—O2	47.7 (2)
O3—C7—C8—C9	105.2 (3)	C7—N1—S1—O1	176.59 (17)
N1—C7—C8—C9	−74.1 (3)	C7—N1—S1—C1	−69.16 (19)
O3—C7—C8—C13	−69.9 (3)	C2—C1—S1—O2	−3.0 (2)
N1—C7—C8—C13	110.9 (2)	C6—C1—S1—O2	178.07 (18)
C13—C8—C9—C10	−0.7 (3)	C2—C1—S1—O1	−134.65 (18)
C7—C8—C9—C10	−175.5 (2)	C6—C1—S1—O1	46.4 (2)
C13—C8—C9—C14	176.7 (2)	C2—C1—S1—N1	114.98 (19)
C7—C8—C9—C14	1.8 (3)	C6—C1—S1—N1	−64.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.82 (2)	2.15 (2)	2.925 (3)	157 (3)

Symmetry code: (i) −x, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂ClNO₃S
M_r	309.76
Crystal system, space group	Triclinic, P1
Temperature (K)	299
a, b, c (Å)	6.4328 (9), 10.343 (1), 11.207 (1)
α, β, γ (°)	78.78 (1), 73.84 (1), 84.62 (1)
V (Å³)	701.88 (13)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	3.86
Crystal size (mm)	0.40 × 0.15 × 0.15

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4317, 2502, 2283
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.147, 1.04
No. of reflections	2502
No. of parameters	186
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.76, −0.56

Computer programs: CAD-4-PC (Enraf–Nonius, 1996), REDU4 (Stoe & Cie, 1987), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.819 (17)	2.15 (2)	2.925 (3)	157 (3)

Symmetry code: (i) −x, −y+1, −z+2.

Acknowledgements

PAS thanks the Council of Scientific and Industrial Research (CSIR), Government of India, New Delhi, for the award of a research fellowship.

References

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