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ISSN: 2056-9890

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

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 ππ stacking inter­actions [centroid–centroid separation = 3.8574 (1) Å] are also observed.

Related literature

For a similar structure, see: Gowda et al. (2010[Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2010). Acta Cryst. E66, o794.])

[Scheme 1]

Experimental

Crystal data
  • C14H12ClNO4S

  • Mr = 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)

  • Rint = 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

  • Δρmax = 0.19 e Å−3

  • Δρmin = −0.30 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (2009). APEX2, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009[Bruker (2009). APEX2, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus and XPREP (Bruker, 2009[Bruker (2009). APEX2, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: Mercury (Macrae et al., 2008[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.]); software used to prepare material for publication: SHELXL97.

Supporting information


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.

Refinement top

The H atom of the NH group was located in a difference map and later refined freely. 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 or 1.5 times of the Ueq of the parent atom).

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
[Figure 1] Fig. 1. Molecular structure of the title compound, showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Molecular packing of (I) forming R22(8) loops and C(11) chains.
[Figure 3] Fig. 3. Molecular packing of (I) forming R22(14) loops.
[Figure 4] 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
C14H12ClNO4SF(000) = 336
Mr = 325.76Prism
Triclinic, P1Dx = 1.473 Mg m3
Hall symbol: -P 1Melting point: 443 K
a = 7.5731 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.1861 (5) ÅCell parameters from 1029 reflections
c = 10.3636 (6) Åθ = 2.7–25.0°
α = 94.945 (4)°µ = 0.42 mm1
β = 96.581 (5)°T = 293 K
γ = 110.974 (5)°Prism, colourless
V = 734.56 (7) Å30.35 × 0.28 × 0.22 mm
Z = 2
Data collection top
Bruker APEXII
diffractometer
Rint = 0.038
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 2.7°
Graphite monochromatorh = 88
phi and ω scansk = 1212
11351 measured reflectionsl = 1212
2584 independent reflections2 standard reflections every 1 reflections
2133 reflections with I > 2σ(I) intensity decay: 10%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0499P)2 + 0.1773P]
where P = (Fo2 + 2Fc2)/3
2584 reflections(Δ/σ)max = 0.006
195 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.30 e Å3
Crystal data top
C14H12ClNO4Sγ = 110.974 (5)°
Mr = 325.76V = 734.56 (7) Å3
Triclinic, P1Z = 2
a = 7.5731 (5) ÅMo Kα radiation
b = 10.1861 (5) ŵ = 0.42 mm1
c = 10.3636 (6) ÅT = 293 K
α = 94.945 (4)°0.35 × 0.28 × 0.22 mm
β = 96.581 (5)°
Data collection top
Bruker APEXII
diffractometer
Rint = 0.038
11351 measured reflections2 standard reflections every 1 reflections
2584 independent reflections intensity decay: 10%
2133 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.101H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.19 e Å3
2584 reflectionsΔρmin = 0.30 e Å3
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
xyzUiso*/Ueq
HN10.513 (4)0.639 (3)0.931 (3)0.057 (8)*
C10.2590 (3)0.4163 (2)0.67778 (18)0.0355 (5)
C20.4118 (3)0.3814 (2)0.6470 (2)0.0404 (5)
C30.4049 (4)0.3179 (3)0.5217 (2)0.0514 (6)
H30.50720.29470.50050.062*
C40.2458 (4)0.2894 (3)0.4285 (2)0.0566 (7)
H40.24110.24600.34480.068*
C50.0939 (4)0.3242 (3)0.4578 (2)0.0547 (6)
H50.01220.30510.39400.066*
C60.0999 (3)0.3876 (2)0.5822 (2)0.0450 (5)
H60.00250.41110.60240.054*
C70.4531 (3)0.7563 (2)0.8139 (2)0.0385 (5)
C80.6044 (3)0.8929 (2)0.8800 (2)0.0390 (5)
C90.6794 (3)0.9116 (2)1.0120 (2)0.0402 (5)
H90.63980.83711.06120.048*
C100.8142 (3)1.0429 (2)1.0698 (2)0.0450 (5)
C110.8727 (3)1.1534 (2)0.9965 (3)0.0533 (6)
H110.96261.24121.03550.064*
C120.7984 (4)1.1338 (3)0.8665 (3)0.0585 (7)
H120.83841.20870.81770.070*
C130.6639 (3)1.0035 (2)0.8062 (2)0.0506 (6)
H130.61460.99070.71760.061*
C140.8344 (4)0.9647 (3)1.2797 (3)0.0710 (8)
H14A0.69970.93951.28050.106*
H14B0.90250.99951.36730.106*
H14C0.85800.88251.24650.106*
O10.2842 (2)0.39742 (15)0.92753 (14)0.0450 (4)
O20.0743 (2)0.51231 (17)0.83161 (15)0.0508 (4)
O30.3527 (2)0.74552 (17)0.70992 (15)0.0526 (4)
O40.8980 (3)1.07160 (17)1.19821 (17)0.0628 (5)
S10.24743 (7)0.48701 (5)0.83723 (5)0.03761 (17)
N10.4298 (3)0.63820 (18)0.87817 (18)0.0398 (4)
Cl10.61560 (9)0.41609 (7)0.75991 (6)0.0578 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0390 (12)0.0294 (10)0.0326 (10)0.0097 (9)0.0032 (9)0.0000 (8)
C20.0387 (13)0.0383 (12)0.0398 (11)0.0116 (10)0.0013 (9)0.0044 (9)
C30.0547 (15)0.0508 (14)0.0481 (13)0.0199 (12)0.0083 (11)0.0019 (11)
C40.0656 (18)0.0565 (15)0.0368 (12)0.0152 (13)0.0003 (11)0.0072 (11)
C50.0583 (16)0.0535 (15)0.0409 (13)0.0166 (13)0.0149 (11)0.0053 (11)
C60.0412 (13)0.0404 (12)0.0469 (13)0.0134 (10)0.0088 (10)0.0000 (10)
C70.0385 (12)0.0381 (12)0.0400 (11)0.0164 (10)0.0054 (9)0.0027 (9)
C80.0383 (12)0.0318 (11)0.0489 (12)0.0145 (9)0.0096 (10)0.0056 (9)
C90.0384 (12)0.0303 (11)0.0499 (13)0.0110 (9)0.0064 (10)0.0030 (9)
C100.0380 (13)0.0344 (12)0.0598 (14)0.0123 (10)0.0065 (10)0.0022 (10)
C110.0426 (14)0.0327 (12)0.0795 (18)0.0084 (10)0.0126 (12)0.0023 (12)
C120.0550 (16)0.0392 (13)0.0849 (19)0.0141 (12)0.0252 (14)0.0237 (13)
C130.0508 (15)0.0462 (14)0.0584 (14)0.0196 (12)0.0124 (11)0.0142 (11)
C140.079 (2)0.0590 (17)0.0580 (16)0.0125 (15)0.0047 (14)0.0001 (13)
O10.0472 (9)0.0376 (8)0.0398 (8)0.0055 (7)0.0025 (7)0.0085 (6)
O20.0379 (9)0.0558 (10)0.0545 (9)0.0164 (8)0.0025 (7)0.0040 (8)
O30.0556 (10)0.0529 (10)0.0475 (9)0.0212 (8)0.0036 (8)0.0079 (7)
O40.0652 (12)0.0421 (10)0.0614 (11)0.0051 (9)0.0064 (9)0.0090 (8)
S10.0354 (3)0.0351 (3)0.0362 (3)0.0091 (2)0.0017 (2)0.0003 (2)
N10.0388 (11)0.0319 (10)0.0411 (10)0.0091 (8)0.0079 (8)0.0010 (8)
Cl10.0433 (4)0.0770 (5)0.0540 (4)0.0283 (3)0.0046 (3)0.0028 (3)
Geometric parameters (Å, º) top
C1—C21.388 (3)C9—C101.390 (3)
C1—C61.394 (3)C9—H90.9300
C1—S11.769 (2)C10—O41.365 (3)
C2—C31.387 (3)C10—C111.382 (3)
C2—Cl11.732 (2)C11—C121.368 (4)
C3—C41.379 (3)C11—H110.9300
C3—H30.9300C12—C131.390 (3)
C4—C51.376 (4)C12—H120.9300
C4—H40.9300C13—H130.9300
C5—C61.380 (3)C14—O41.417 (3)
C5—H50.9300C14—H14A0.9600
C6—H60.9300C14—H14B0.9600
C7—O31.218 (2)C14—H14C0.9600
C7—N11.391 (3)O1—S11.4337 (14)
C7—C81.494 (3)O2—S11.4200 (16)
C8—C131.386 (3)S1—N11.6402 (18)
C8—C91.389 (3)N1—HN10.79 (3)
C2—C1—C6119.67 (19)O4—C10—C9123.9 (2)
C2—C1—S1123.23 (15)C11—C10—C9120.2 (2)
C6—C1—S1116.98 (17)C12—C11—C10120.0 (2)
C3—C2—C1119.8 (2)C12—C11—H11120.0
C3—C2—Cl1117.89 (18)C10—C11—H11120.0
C1—C2—Cl1122.28 (16)C11—C12—C13120.9 (2)
C4—C3—C2119.8 (2)C11—C12—H12119.5
C4—C3—H3120.1C13—C12—H12119.5
C2—C3—H3120.1C8—C13—C12119.1 (2)
C5—C4—C3120.9 (2)C8—C13—H13120.5
C5—C4—H4119.5C12—C13—H13120.5
C3—C4—H4119.5O4—C14—H14A109.5
C4—C5—C6119.7 (2)O4—C14—H14B109.5
C4—C5—H5120.2H14A—C14—H14B109.5
C6—C5—H5120.2O4—C14—H14C109.5
C5—C6—C1120.2 (2)H14A—C14—H14C109.5
C5—C6—H6119.9H14B—C14—H14C109.5
C1—C6—H6119.9C10—O4—C14118.15 (18)
O3—C7—N1120.3 (2)O2—S1—O1119.16 (10)
O3—C7—C8123.37 (19)O2—S1—N1109.37 (10)
N1—C7—C8116.29 (18)O1—S1—N1104.24 (9)
C13—C8—C9120.4 (2)O2—S1—C1107.73 (10)
C13—C8—C7117.8 (2)O1—S1—C1108.22 (9)
C9—C8—C7121.78 (19)N1—S1—C1107.61 (10)
C8—C9—C10119.4 (2)C7—N1—S1123.60 (15)
C8—C9—H9120.3C7—N1—HN1119.7 (19)
C10—C9—H9120.3S1—N1—HN1116.2 (19)
O4—C10—C11115.9 (2)
C6—C1—C2—C30.1 (3)O4—C10—C11—C12179.1 (2)
S1—C1—C2—C3175.85 (17)C9—C10—C11—C120.2 (4)
C6—C1—C2—Cl1179.10 (16)C10—C11—C12—C130.0 (4)
S1—C1—C2—Cl14.9 (3)C9—C8—C13—C120.6 (3)
C1—C2—C3—C40.3 (3)C7—C8—C13—C12177.2 (2)
Cl1—C2—C3—C4179.55 (18)C11—C12—C13—C80.4 (4)
C2—C3—C4—C50.6 (4)C11—C10—O4—C14176.2 (2)
C3—C4—C5—C60.5 (4)C9—C10—O4—C144.5 (3)
C4—C5—C6—C10.1 (4)C2—C1—S1—O2178.82 (17)
C2—C1—C6—C50.2 (3)C6—C1—S1—O25.11 (19)
S1—C1—C6—C5175.99 (18)C2—C1—S1—O151.1 (2)
O3—C7—C8—C1315.7 (3)C6—C1—S1—O1124.97 (16)
N1—C7—C8—C13164.6 (2)C2—C1—S1—N160.99 (19)
O3—C7—C8—C9162.0 (2)C6—C1—S1—N1122.94 (17)
N1—C7—C8—C917.6 (3)O3—C7—N1—S111.6 (3)
C13—C8—C9—C100.4 (3)C8—C7—N1—S1167.99 (15)
C7—C8—C9—C10177.34 (19)O2—S1—N1—C752.2 (2)
C8—C9—C10—O4179.3 (2)O1—S1—N1—C7179.30 (18)
C8—C9—C10—C110.0 (3)C1—S1—N1—C764.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—HN1···O1i0.78 (3)2.14 (3)2.926 (3)170 (3)
C5—H5···O3ii0.932.533.417 (3)160
C3—H3···O3iii0.932.603.338 (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 formulaC14H12ClNO4S
Mr325.76
Crystal system, space groupTriclinic, 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)
V3)734.56 (7)
Z2
Radiation typeMo Kα
µ (mm1)0.42
Crystal size (mm)0.35 × 0.28 × 0.22
Data collection
DiffractometerBruker APEXII
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
11351, 2584, 2133
Rint0.038
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.101, 1.05
No. of reflections2584
No. of parameters195
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
N1—HN1···O1i0.78 (3)2.14 (3)2.926 (3)170 (3)
C5—H5···O3ii0.932.533.417 (3)160
C3—H3···O3iii0.932.603.338 (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

First citationBruker (2009). APEX2, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationGowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2010). Acta Cryst. E66, o794.  Web of Science CrossRef IUCr Journals
First citationMacrae, 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
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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