2-Chloro-N-(3-meth­oxy­benzo­yl)benzene­sulfonamide

Suchetan, P.A.; Palakshamurthy, B.S.; Mamatha, G.R.; Kumar, V.; Mohan, N.R.; Sreenivasa, S.

doi:10.1107/S1600536813018291

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 8| August 2013| Page o1215

doi:10.1107/S1600536813018291

Open

access

2-Chloro-N-(3-methoxybenzoyl)benzenesulfonamide

P. A. Suchetan,^a B. S. Palakshamurthy,^b G. R. Mamatha,^c Vijith Kumar,^d N. R. Mohan ^e and S. Sreenivasa ^e ^*

^aDepartment of Studies and Research in Chemistry, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India, ^bDepartment of Studies and Research in Physics, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India, ^cUniversity College of Science, Tumkur University, Tumkur, India, ^dSoild State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, India, and ^eDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India
^*Correspondence e-mail: drsreenivasa@yahoo.co.in

(Received 30 June 2013; accepted 2 July 2013; online 6 July 2013)

In the title compound, C₁₄H₁₂ClNO₄S, the dihedral angle between the chloro- and methoxy-substituted benzene rings is 87.40 (1)°. In the crystal, adjacent molecules form inversion-related dimers through strong N—H⋯O hydrogen bonds, generating R₂²(8) loops. The dimers are further connected through two C—H⋯O interactions that form C(11) chains and R₂²(14) loops. Aromatic π–π stacking interactions [centroid–centroid separation = 3.8574 (1) Å] are also observed.

Related literature

For a similar structure, see: Gowda et al. (2010 )

Experimental

Crystal data

C₁₄H₁₂ClNO₄S
M_r = 325.76
Triclinic, $[P \overline 1]$
a = 7.5731 (5) Å
b = 10.1861 (5) Å
c = 10.3636 (6) Å
α = 94.945 (4)°
β = 96.581 (5)°
γ = 110.974 (5)°
V = 734.56 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.42 mm⁻¹
T = 293 K
0.35 × 0.28 × 0.22 mm

Data collection

Bruker APEXII diffractometer
11351 measured reflections
2584 independent reflections
2133 reflections with I > 2σ(I)
R_int = 0.038
2 standard reflections every 1 reflections intensity decay: 10%

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.101
S = 1.05
2584 reflections
195 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN1⋯O1ⁱ	0.78 (3)	2.14 (3)	2.926 (3)	170 (3)
C5—H5⋯O3ⁱⁱ	0.93	2.53	3.417 (3)	160
C3—H3⋯O3ⁱⁱⁱ	0.93	2.60	3.338 (3)	137
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x, -y+1, -z+1; (iii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2009 ); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus and XPREP (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813018291/hg5328sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813018291/hg5328Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813018291/hg5328Isup3.cml

checkCIF report

Comment top

As a part of the efforts to study the crystal structures of N-(aroyl)-arylsulfonamides (Gowda et al., 2010), the crystal structure of the title compound (I) was determined.

In the molecule, the conformation between the N—H bond and the ortho-chloro group in the sulfonyl bound benzene ring is syn. This is similar to that observed in N-(benzoyl)-2-chlorobenzenesulfonamide (II, Gowda et al. 2010).

In the structure, the adjacent molecules form inversion related dimers through strong N—H···O hydrogen bonds, generating R₂²(8) loops. The dimers are further connected through intermolecular C3—H3···O3 and C5—H5···O3 interactions that form C(11) chains and R₂²(14) loops. Aromatic π-π stacking interactions (centroid-centroid separation = 3.8574 (1) Å) are also observed in the structure.

Related literature top

For a similar structure, see: Gowda et al. (2010)

Experimental top

The title compound was prepared by refluxing a mixture of 3-methoxybenzoic acid, 2-chlorobenzenesulfonamide and phosphorous oxychloride (POCl₃) for 2 h on a water bath. The resultant mixture was cooled and poured into ice cold water. The solid obtained was filtered and washed thoroughly with water and then dissolved in sodium bicarbonate solution. The compound was later reprecipitated by acidifying the filtered solution with dilute HCl. The filtered and dried solid was recrystallized to the constant melting point (443 K).

Colorless prisms of (I) were obtained from a slow evaporation of its ethanolic solution at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus and XPREP (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Molecular packing of (I) forming R₂²(8) loops and C(11) chains.
	Fig. 3. Molecular packing of (I) forming R₂²(14) loops.
	Fig. 4. Stacking of molecules through Cg···Cg interactions. Cg is the centroid of the methoxy substituted benzene ring.

2-Chloro-N-(3-methoxybenzoyl)benzenesulfonamide top

Crystal data top

C₁₄H₁₂ClNO₄S	F(000) = 336
M_r = 325.76	Prism
Triclinic, P1	D_x = 1.473 Mg m⁻³
Hall symbol: -P 1	Melting point: 443 K
a = 7.5731 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.1861 (5) Å	Cell parameters from 1029 reflections
c = 10.3636 (6) Å	θ = 2.7–25.0°
α = 94.945 (4)°	µ = 0.42 mm⁻¹
β = 96.581 (5)°	T = 293 K
γ = 110.974 (5)°	Prism, colourless
V = 734.56 (7) Å³	0.35 × 0.28 × 0.22 mm
Z = 2

Data collection top

Bruker APEXII diffractometer	R_int = 0.038
Radiation source: fine-focus sealed tube	θ_max = 25.0°, θ_min = 2.7°
Graphite monochromator	h = −8→8
phi and ω scans	k = −12→12
11351 measured reflections	l = −12→12
2584 independent reflections	2 standard reflections every 1 reflections
2133 reflections with I > 2σ(I)	intensity decay: 10%

Refinement top

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0499P)² + 0.1773P] where P = (F_o² + 2F_c²)/3
2584 reflections	(Δ/σ)_max = 0.006
195 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₄H₁₂ClNO₄S	γ = 110.974 (5)°
M_r = 325.76	V = 734.56 (7) Å³
Triclinic, P1	Z = 2
a = 7.5731 (5) Å	Mo Kα radiation
b = 10.1861 (5) Å	µ = 0.42 mm⁻¹
c = 10.3636 (6) Å	T = 293 K
α = 94.945 (4)°	0.35 × 0.28 × 0.22 mm
β = 96.581 (5)°

Data collection top

Bruker APEXII diffractometer	R_int = 0.038
11351 measured reflections	2 standard reflections every 1 reflections
2584 independent reflections	intensity decay: 10%
2133 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.19 e Å⁻³
2584 reflections	Δρ_min = −0.30 e Å⁻³
195 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
HN1	0.513 (4)	0.639 (3)	0.931 (3)	0.057 (8)*
C1	0.2590 (3)	0.4163 (2)	0.67778 (18)	0.0355 (5)
C2	0.4118 (3)	0.3814 (2)	0.6470 (2)	0.0404 (5)
C3	0.4049 (4)	0.3179 (3)	0.5217 (2)	0.0514 (6)
H3	0.5072	0.2947	0.5005	0.062*
C4	0.2458 (4)	0.2894 (3)	0.4285 (2)	0.0566 (7)
H4	0.2411	0.2460	0.3448	0.068*
C5	0.0939 (4)	0.3242 (3)	0.4578 (2)	0.0547 (6)
H5	−0.0122	0.3051	0.3940	0.066*
C6	0.0999 (3)	0.3876 (2)	0.5822 (2)	0.0450 (5)
H6	−0.0025	0.4111	0.6024	0.054*
C7	0.4531 (3)	0.7563 (2)	0.8139 (2)	0.0385 (5)
C8	0.6044 (3)	0.8929 (2)	0.8800 (2)	0.0390 (5)
C9	0.6794 (3)	0.9116 (2)	1.0120 (2)	0.0402 (5)
H9	0.6398	0.8371	1.0612	0.048*
C10	0.8142 (3)	1.0429 (2)	1.0698 (2)	0.0450 (5)
C11	0.8727 (3)	1.1534 (2)	0.9965 (3)	0.0533 (6)
H11	0.9626	1.2412	1.0355	0.064*
C12	0.7984 (4)	1.1338 (3)	0.8665 (3)	0.0585 (7)
H12	0.8384	1.2087	0.8177	0.070*
C13	0.6639 (3)	1.0035 (2)	0.8062 (2)	0.0506 (6)
H13	0.6146	0.9907	0.7176	0.061*
C14	0.8344 (4)	0.9647 (3)	1.2797 (3)	0.0710 (8)
H14A	0.6997	0.9395	1.2805	0.106*
H14B	0.9025	0.9995	1.3673	0.106*
H14C	0.8580	0.8825	1.2465	0.106*
O1	0.2842 (2)	0.39742 (15)	0.92753 (14)	0.0450 (4)
O2	0.0743 (2)	0.51231 (17)	0.83161 (15)	0.0508 (4)
O3	0.3527 (2)	0.74552 (17)	0.70992 (15)	0.0526 (4)
O4	0.8980 (3)	1.07160 (17)	1.19821 (17)	0.0628 (5)
S1	0.24743 (7)	0.48701 (5)	0.83723 (5)	0.03761 (17)
N1	0.4298 (3)	0.63820 (18)	0.87817 (18)	0.0398 (4)
Cl1	0.61560 (9)	0.41609 (7)	0.75991 (6)	0.0578 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0390 (12)	0.0294 (10)	0.0326 (10)	0.0097 (9)	−0.0032 (9)	0.0000 (8)
C2	0.0387 (13)	0.0383 (12)	0.0398 (11)	0.0116 (10)	−0.0013 (9)	0.0044 (9)
C3	0.0547 (15)	0.0508 (14)	0.0481 (13)	0.0199 (12)	0.0083 (11)	0.0019 (11)
C4	0.0656 (18)	0.0565 (15)	0.0368 (12)	0.0152 (13)	−0.0003 (11)	−0.0072 (11)
C5	0.0583 (16)	0.0535 (15)	0.0409 (13)	0.0166 (13)	−0.0149 (11)	−0.0053 (11)
C6	0.0412 (13)	0.0404 (12)	0.0469 (13)	0.0134 (10)	−0.0088 (10)	0.0000 (10)
C7	0.0385 (12)	0.0381 (12)	0.0400 (11)	0.0164 (10)	0.0054 (9)	0.0027 (9)
C8	0.0383 (12)	0.0318 (11)	0.0489 (12)	0.0145 (9)	0.0096 (10)	0.0056 (9)
C9	0.0384 (12)	0.0303 (11)	0.0499 (13)	0.0110 (9)	0.0064 (10)	0.0030 (9)
C10	0.0380 (13)	0.0344 (12)	0.0598 (14)	0.0123 (10)	0.0065 (10)	−0.0022 (10)
C11	0.0426 (14)	0.0327 (12)	0.0795 (18)	0.0084 (10)	0.0126 (12)	0.0023 (12)
C12	0.0550 (16)	0.0392 (13)	0.0849 (19)	0.0141 (12)	0.0252 (14)	0.0237 (13)
C13	0.0508 (15)	0.0462 (14)	0.0584 (14)	0.0196 (12)	0.0124 (11)	0.0142 (11)
C14	0.079 (2)	0.0590 (17)	0.0580 (16)	0.0125 (15)	−0.0047 (14)	−0.0001 (13)
O1	0.0472 (9)	0.0376 (8)	0.0398 (8)	0.0055 (7)	−0.0025 (7)	0.0085 (6)
O2	0.0379 (9)	0.0558 (10)	0.0545 (9)	0.0164 (8)	0.0025 (7)	−0.0040 (8)
O3	0.0556 (10)	0.0529 (10)	0.0475 (9)	0.0212 (8)	−0.0036 (8)	0.0079 (7)
O4	0.0652 (12)	0.0421 (10)	0.0614 (11)	0.0051 (9)	−0.0064 (9)	−0.0090 (8)
S1	0.0354 (3)	0.0351 (3)	0.0362 (3)	0.0091 (2)	−0.0017 (2)	0.0003 (2)
N1	0.0388 (11)	0.0319 (10)	0.0411 (10)	0.0091 (8)	−0.0079 (8)	0.0010 (8)
Cl1	0.0433 (4)	0.0770 (5)	0.0540 (4)	0.0283 (3)	−0.0046 (3)	0.0028 (3)

Geometric parameters (Å, º) top

C1—C2	1.388 (3)	C9—C10	1.390 (3)
C1—C6	1.394 (3)	C9—H9	0.9300
C1—S1	1.769 (2)	C10—O4	1.365 (3)
C2—C3	1.387 (3)	C10—C11	1.382 (3)
C2—Cl1	1.732 (2)	C11—C12	1.368 (4)
C3—C4	1.379 (3)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.390 (3)
C4—C5	1.376 (4)	C12—H12	0.9300
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.380 (3)	C14—O4	1.417 (3)
C5—H5	0.9300	C14—H14A	0.9600
C6—H6	0.9300	C14—H14B	0.9600
C7—O3	1.218 (2)	C14—H14C	0.9600
C7—N1	1.391 (3)	O1—S1	1.4337 (14)
C7—C8	1.494 (3)	O2—S1	1.4200 (16)
C8—C13	1.386 (3)	S1—N1	1.6402 (18)
C8—C9	1.389 (3)	N1—HN1	0.79 (3)

C2—C1—C6	119.67 (19)	O4—C10—C9	123.9 (2)
C2—C1—S1	123.23 (15)	C11—C10—C9	120.2 (2)
C6—C1—S1	116.98 (17)	C12—C11—C10	120.0 (2)
C3—C2—C1	119.8 (2)	C12—C11—H11	120.0
C3—C2—Cl1	117.89 (18)	C10—C11—H11	120.0
C1—C2—Cl1	122.28 (16)	C11—C12—C13	120.9 (2)
C4—C3—C2	119.8 (2)	C11—C12—H12	119.5
C4—C3—H3	120.1	C13—C12—H12	119.5
C2—C3—H3	120.1	C8—C13—C12	119.1 (2)
C5—C4—C3	120.9 (2)	C8—C13—H13	120.5
C5—C4—H4	119.5	C12—C13—H13	120.5
C3—C4—H4	119.5	O4—C14—H14A	109.5
C4—C5—C6	119.7 (2)	O4—C14—H14B	109.5
C4—C5—H5	120.2	H14A—C14—H14B	109.5
C6—C5—H5	120.2	O4—C14—H14C	109.5
C5—C6—C1	120.2 (2)	H14A—C14—H14C	109.5
C5—C6—H6	119.9	H14B—C14—H14C	109.5
C1—C6—H6	119.9	C10—O4—C14	118.15 (18)
O3—C7—N1	120.3 (2)	O2—S1—O1	119.16 (10)
O3—C7—C8	123.37 (19)	O2—S1—N1	109.37 (10)
N1—C7—C8	116.29 (18)	O1—S1—N1	104.24 (9)
C13—C8—C9	120.4 (2)	O2—S1—C1	107.73 (10)
C13—C8—C7	117.8 (2)	O1—S1—C1	108.22 (9)
C9—C8—C7	121.78 (19)	N1—S1—C1	107.61 (10)
C8—C9—C10	119.4 (2)	C7—N1—S1	123.60 (15)
C8—C9—H9	120.3	C7—N1—HN1	119.7 (19)
C10—C9—H9	120.3	S1—N1—HN1	116.2 (19)
O4—C10—C11	115.9 (2)

C6—C1—C2—C3	−0.1 (3)	O4—C10—C11—C12	179.1 (2)
S1—C1—C2—C3	175.85 (17)	C9—C10—C11—C12	−0.2 (4)
C6—C1—C2—Cl1	179.10 (16)	C10—C11—C12—C13	0.0 (4)
S1—C1—C2—Cl1	−4.9 (3)	C9—C8—C13—C12	−0.6 (3)
C1—C2—C3—C4	−0.3 (3)	C7—C8—C13—C12	177.2 (2)
Cl1—C2—C3—C4	−179.55 (18)	C11—C12—C13—C8	0.4 (4)
C2—C3—C4—C5	0.6 (4)	C11—C10—O4—C14	176.2 (2)
C3—C4—C5—C6	−0.5 (4)	C9—C10—O4—C14	−4.5 (3)
C4—C5—C6—C1	0.1 (4)	C2—C1—S1—O2	178.82 (17)
C2—C1—C6—C5	0.2 (3)	C6—C1—S1—O2	−5.11 (19)
S1—C1—C6—C5	−175.99 (18)	C2—C1—S1—O1	−51.1 (2)
O3—C7—C8—C13	−15.7 (3)	C6—C1—S1—O1	124.97 (16)
N1—C7—C8—C13	164.6 (2)	C2—C1—S1—N1	60.99 (19)
O3—C7—C8—C9	162.0 (2)	C6—C1—S1—N1	−122.94 (17)
N1—C7—C8—C9	−17.6 (3)	O3—C7—N1—S1	−11.6 (3)
C13—C8—C9—C10	0.4 (3)	C8—C7—N1—S1	167.99 (15)
C7—C8—C9—C10	−177.34 (19)	O2—S1—N1—C7	−52.2 (2)
C8—C9—C10—O4	−179.3 (2)	O1—S1—N1—C7	179.30 (18)
C8—C9—C10—C11	0.0 (3)	C1—S1—N1—C7	64.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O1ⁱ	0.78 (3)	2.14 (3)	2.926 (3)	170 (3)
C5—H5···O3ⁱⁱ	0.93	2.53	3.417 (3)	160
C3—H3···O3ⁱⁱⁱ	0.93	2.60	3.338 (3)	137

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x, −y+1, −z+1; (iii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂ClNO₄S
M_r	325.76
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.5731 (5), 10.1861 (5), 10.3636 (6)
α, β, γ (°)	94.945 (4), 96.581 (5), 110.974 (5)
V (Å³)	734.56 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.42
Crystal size (mm)	0.35 × 0.28 × 0.22

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	11351, 2584, 2133
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.101, 1.05
No. of reflections	2584
No. of parameters	195
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.30

Computer programs: APEX2 (Bruker, 2009), APEX2 and SAINT-Plus (Bruker, 2009), SAINT-Plus and XPREP (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O1ⁱ	0.78 (3)	2.14 (3)	2.926 (3)	170 (3)
C5—H5···O3ⁱⁱ	0.93	2.53	3.417 (3)	160
C3—H3···O3ⁱⁱⁱ	0.93	2.60	3.338 (3)	137.1

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x, −y+1, −z+1; (iii) −x+1, −y+1, −z+1.

Acknowledgements

PAS thanks the University Grants Commission (UGC), India, for financial support under its Minor Research Project scheme.

References

Bruker (2009). APEX2, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2010). Acta Cryst. E66, o794. Web of Science CrossRef IUCr Journals Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar