organic compounds
2-Chloro-N-(3-chlorobenzoyl)benzenesulfonamide
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
The 13H9Cl2NO3S, contains two independent molecules. The conformation of the C=O bond is anti to the meta-Cl group in the chlorobenzoyl group of one of the molecules and syn in the other. The dihedral angles between the sulfonyl and benzoyl benzene rings are 77.8 (1) and 83.5 (1)°. In the two pairs of independent molecules are linked into a tetramer by N—H⋯O hydrogen bonds.
of the title compound, CRelated literature
For background literature and related structures, see: Gowda et al. (2009, 2010); Suchetan et al. (2010a,b).
Experimental
Crystal data
|
Refinement
|
Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell 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.
Supporting information
https://doi.org/10.1107/S1600536810016909/ci5091sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810016909/ci5091Isup2.hkl
The title compound was prepared by refluxing a mixture of 3-chlorobenzoic acid, 2-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. 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.
The H atoms of the NH groups were located in a difference map and refined with the a N–H distance restraint of 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 Ueq of the parent atom). The residual electron-density features are located in the region of H25 and Cl4. The highest peak is 0.98 Å from H25 and the deepest hole is 0.68 Å from Cl4.
As a part of studying the effect of ring and the side chain substitutions on the crystal structures of N-aryl ═O bonds (Fig.1), similar to those observed in 2-chloro-N- (3-methylbenzoyl)-benzenesulfonamide (II) (Suchetan et al., 2010b), 2-methyl-N-(3-methylbenzoyl)-benzenesulfonamide (III) (Gowda et al., 2010), 2-chloro-N-(2-chlorobenzoyl)- benzenesulfonamide (IV)(Suchetan et al., 2010a), N-(benzoyl)-benzenesulfonamide (V) (Gowda et al., 2009).
(Gowda et al., 2009, 2010; Suchetan et al., 2010a,b), the structure of 2-chloro-N-(3-chlorobenzoyl)-benzenesulfonamide (I) has been determined. The of (I) contains two independent molecules. In the C—SO2—NH—C(O) segments, the N—H bonds are anti to the CThe conformation of the C═O bond is anti to the meta-Cl group in the benzoyl ring of one of the molecules and syn in the other, compared to the anti conformation observed between C═O bond and meta- methyl group in the benzoyl ring of (II).
The chlorobenzoyl and sulfonyl-bound chlorophenyl units in the two molecules of (I) are twisted with respect to the S—N bond, with torsional angles of -62.6 (3)° [C7—N1—S1—C1] and -62.6 (3)° [C20—N2—S2—C14], compared to those of -66.5 (2)° in (II), -66.2 (3)° in (III), -66.5 (2)° in (IV) and -66.9 (3)° in (V). The dihedral angles between the sulfonyl and the benzoyl- bound benzene rings are 77.8 (1)° (molecule 1) and 83.5 (1)° (molecule 2), compared to the values of 74.7 (1)° in (II), 74.8 (1)° in (III), 76.9 (1) in (IV) and 80.3 (1)° in (V).
For background literature and related structures, see: Gowda et al. (2009, 2010); Suchetan et al. (2010a,b).
Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell
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).Fig. 1. The two independent molecules of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. |
C13H9Cl2NO3S | Z = 4 |
Mr = 330.17 | F(000) = 672 |
Triclinic, P1 | Dx = 1.561 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.4399 (6) Å | Cell parameters from 3572 reflections |
b = 11.679 (1) Å | θ = 2.5–27.8° |
c = 17.138 (2) Å | µ = 0.62 mm−1 |
α = 75.346 (7)° | T = 299 K |
β = 83.188 (8)° | Rod, colourless |
γ = 77.732 (7)° | 0.20 × 0.14 × 0.08 mm |
V = 1404.5 (2) Å3 |
Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector | 5694 independent reflections |
Radiation source: fine-focus sealed tube | 4267 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
Rotation method data acquisition using ω and φ scans | θmax = 26.4°, θmin = 2.5° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | h = −9→5 |
Tmin = 0.887, Tmax = 0.952 | k = −14→14 |
9768 measured reflections | l = −19→21 |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.154 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0682P)2 + 1.64P] where P = (Fo2 + 2Fc2)/3 |
5694 reflections | (Δ/σ)max = 0.014 |
367 parameters | Δρmax = 1.10 e Å−3 |
2 restraints | Δρmin = −0.50 e Å−3 |
C13H9Cl2NO3S | γ = 77.732 (7)° |
Mr = 330.17 | V = 1404.5 (2) Å3 |
Triclinic, P1 | Z = 4 |
a = 7.4399 (6) Å | Mo Kα radiation |
b = 11.679 (1) Å | µ = 0.62 mm−1 |
c = 17.138 (2) Å | T = 299 K |
α = 75.346 (7)° | 0.20 × 0.14 × 0.08 mm |
β = 83.188 (8)° |
Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector | 5694 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | 4267 reflections with I > 2σ(I) |
Tmin = 0.887, Tmax = 0.952 | Rint = 0.018 |
9768 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 2 restraints |
wR(F2) = 0.154 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 1.10 e Å−3 |
5694 reflections | Δρmin = −0.50 e Å−3 |
367 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.2455 (4) | 1.0034 (3) | 0.13610 (19) | 0.0380 (7) | |
C2 | 0.4149 (4) | 1.0391 (3) | 0.1159 (2) | 0.0432 (8) | |
C3 | 0.4422 (5) | 1.1225 (3) | 0.0442 (2) | 0.0543 (9) | |
H3 | 0.5556 | 1.1464 | 0.0304 | 0.065* | |
C4 | 0.3009 (6) | 1.1700 (4) | −0.0067 (2) | 0.0594 (10) | |
H4 | 0.3199 | 1.2258 | −0.0548 | 0.071* | |
C5 | 0.1320 (5) | 1.1358 (3) | 0.0128 (2) | 0.0564 (10) | |
H5 | 0.0372 | 1.1690 | −0.0217 | 0.068* | |
C6 | 0.1041 (5) | 1.0522 (3) | 0.0839 (2) | 0.0473 (8) | |
H6 | −0.0095 | 1.0283 | 0.0970 | 0.057* | |
C7 | 0.3347 (4) | 0.7053 (3) | 0.1700 (2) | 0.0421 (7) | |
C8 | 0.4322 (4) | 0.5771 (3) | 0.1922 (2) | 0.0403 (7) | |
C9 | 0.5166 (5) | 0.5225 (3) | 0.1304 (2) | 0.0488 (8) | |
H9 | 0.5157 | 0.5659 | 0.0768 | 0.059* | |
C10 | 0.6012 (5) | 0.4034 (4) | 0.1500 (3) | 0.0539 (9) | |
C11 | 0.5995 (5) | 0.3361 (4) | 0.2282 (3) | 0.0596 (10) | |
H11 | 0.6549 | 0.2550 | 0.2399 | 0.072* | |
C12 | 0.5148 (6) | 0.3901 (4) | 0.2892 (3) | 0.0614 (10) | |
H12 | 0.5135 | 0.3450 | 0.3424 | 0.074* | |
C13 | 0.4315 (5) | 0.5106 (3) | 0.2723 (2) | 0.0487 (8) | |
H13 | 0.3757 | 0.5468 | 0.3138 | 0.058* | |
N1 | 0.3355 (4) | 0.7713 (2) | 0.22646 (18) | 0.0434 (7) | |
H1N | 0.423 (4) | 0.755 (3) | 0.2573 (19) | 0.052* | |
O1 | 0.0127 (3) | 0.8835 (2) | 0.22699 (17) | 0.0600 (7) | |
O2 | 0.2495 (4) | 0.9355 (2) | 0.29433 (14) | 0.0529 (6) | |
O3 | 0.2575 (4) | 0.7488 (2) | 0.10731 (15) | 0.0548 (6) | |
S1 | 0.19546 (11) | 0.90062 (8) | 0.22791 (5) | 0.0418 (2) | |
Cl1 | 0.59757 (13) | 0.98058 (10) | 0.17710 (6) | 0.0621 (3) | |
Cl2 | 0.71150 (19) | 0.33696 (12) | 0.07272 (9) | 0.0864 (4) | |
C14 | 0.7395 (4) | 0.7963 (3) | 0.4444 (2) | 0.0418 (7) | |
C15 | 0.9034 (5) | 0.8353 (3) | 0.4444 (2) | 0.0469 (8) | |
C16 | 0.9072 (6) | 0.9573 (4) | 0.4233 (2) | 0.0573 (10) | |
H16 | 1.0162 | 0.9838 | 0.4240 | 0.069* | |
C17 | 0.7485 (7) | 1.0391 (4) | 0.4014 (3) | 0.0648 (11) | |
H17 | 0.7510 | 1.1211 | 0.3875 | 0.078* | |
C18 | 0.5875 (6) | 1.0018 (4) | 0.3996 (3) | 0.0633 (11) | |
H18 | 0.4816 | 1.0582 | 0.3841 | 0.076* | |
C19 | 0.5817 (5) | 0.8804 (3) | 0.4208 (2) | 0.0506 (9) | |
H19 | 0.4722 | 0.8550 | 0.4193 | 0.061* | |
C20 | 0.7982 (5) | 0.6143 (3) | 0.3232 (2) | 0.0473 (8) | |
C21 | 0.9079 (5) | 0.5420 (3) | 0.2688 (2) | 0.0470 (8) | |
C22 | 0.9803 (5) | 0.4209 (3) | 0.2962 (2) | 0.0511 (9) | |
H22 | 0.9681 | 0.3831 | 0.3507 | 0.061* | |
C23 | 1.0719 (5) | 0.3567 (4) | 0.2401 (3) | 0.0597 (10) | |
C24 | 1.0906 (6) | 0.4131 (5) | 0.1593 (3) | 0.0659 (11) | |
H24 | 1.1511 | 0.3691 | 0.1225 | 0.079* | |
C25 | 1.0212 (6) | 0.5326 (5) | 0.1332 (3) | 0.0721 (12) | |
H25 | 1.0363 | 0.5703 | 0.0788 | 0.087* | |
C26 | 0.9289 (5) | 0.5978 (4) | 0.1869 (2) | 0.0587 (10) | |
H26 | 0.8803 | 0.6793 | 0.1687 | 0.070* | |
N2 | 0.8416 (4) | 0.5803 (3) | 0.40323 (18) | 0.0477 (7) | |
H2N | 0.946 (3) | 0.537 (3) | 0.415 (2) | 0.057* | |
O4 | 0.5315 (3) | 0.6379 (3) | 0.4726 (2) | 0.0700 (8) | |
O5 | 0.8139 (3) | 0.5845 (2) | 0.54567 (15) | 0.0547 (6) | |
O6 | 0.6750 (4) | 0.6993 (2) | 0.30102 (18) | 0.0620 (8) | |
S2 | 0.71956 (11) | 0.64315 (8) | 0.47362 (6) | 0.0466 (2) | |
Cl3 | 1.10996 (13) | 0.73583 (10) | 0.46678 (7) | 0.0686 (3) | |
Cl4 | 1.1539 (2) | 0.20474 (11) | 0.27335 (10) | 0.0915 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0388 (16) | 0.0328 (16) | 0.0392 (17) | −0.0003 (13) | −0.0070 (13) | −0.0059 (13) |
C2 | 0.0401 (18) | 0.0421 (18) | 0.0462 (19) | −0.0046 (14) | −0.0122 (14) | −0.0067 (15) |
C3 | 0.054 (2) | 0.054 (2) | 0.053 (2) | −0.0187 (18) | −0.0060 (17) | −0.0012 (17) |
C4 | 0.075 (3) | 0.048 (2) | 0.049 (2) | −0.0125 (19) | −0.0116 (19) | 0.0042 (17) |
C5 | 0.058 (2) | 0.050 (2) | 0.053 (2) | −0.0010 (18) | −0.0241 (18) | 0.0023 (17) |
C6 | 0.0389 (18) | 0.0459 (19) | 0.055 (2) | −0.0031 (15) | −0.0151 (15) | −0.0060 (16) |
C7 | 0.0380 (17) | 0.0400 (18) | 0.0467 (19) | −0.0116 (14) | −0.0031 (14) | −0.0040 (14) |
C8 | 0.0340 (16) | 0.0381 (17) | 0.0496 (19) | −0.0107 (13) | −0.0064 (14) | −0.0067 (14) |
C9 | 0.050 (2) | 0.048 (2) | 0.051 (2) | −0.0133 (16) | −0.0048 (16) | −0.0118 (16) |
C10 | 0.047 (2) | 0.051 (2) | 0.069 (3) | −0.0105 (17) | −0.0015 (18) | −0.0247 (19) |
C11 | 0.054 (2) | 0.042 (2) | 0.078 (3) | −0.0032 (17) | −0.006 (2) | −0.0086 (19) |
C12 | 0.063 (2) | 0.047 (2) | 0.062 (3) | −0.0045 (19) | −0.003 (2) | 0.0032 (19) |
C13 | 0.0467 (19) | 0.0434 (19) | 0.052 (2) | −0.0079 (15) | −0.0009 (16) | −0.0050 (16) |
N1 | 0.0409 (15) | 0.0375 (15) | 0.0500 (17) | −0.0019 (12) | −0.0174 (12) | −0.0052 (13) |
O1 | 0.0351 (13) | 0.0638 (17) | 0.0706 (18) | −0.0073 (12) | −0.0041 (12) | 0.0016 (13) |
O2 | 0.0630 (16) | 0.0529 (15) | 0.0388 (13) | −0.0027 (12) | −0.0037 (11) | −0.0104 (11) |
O3 | 0.0632 (16) | 0.0486 (14) | 0.0504 (15) | −0.0082 (12) | −0.0212 (12) | −0.0019 (11) |
S1 | 0.0359 (4) | 0.0405 (4) | 0.0432 (5) | −0.0018 (3) | −0.0037 (3) | −0.0033 (3) |
Cl1 | 0.0421 (5) | 0.0781 (7) | 0.0618 (6) | −0.0153 (4) | −0.0194 (4) | 0.0017 (5) |
Cl2 | 0.0947 (9) | 0.0792 (8) | 0.0946 (9) | −0.0088 (7) | 0.0062 (7) | −0.0494 (7) |
C14 | 0.0397 (17) | 0.0442 (18) | 0.0381 (17) | −0.0008 (14) | −0.0055 (13) | −0.0082 (14) |
C15 | 0.0420 (18) | 0.058 (2) | 0.0384 (18) | −0.0080 (16) | −0.0051 (14) | −0.0075 (16) |
C16 | 0.063 (2) | 0.062 (2) | 0.051 (2) | −0.022 (2) | −0.0014 (18) | −0.0133 (18) |
C17 | 0.087 (3) | 0.046 (2) | 0.059 (2) | −0.008 (2) | −0.006 (2) | −0.0116 (18) |
C18 | 0.066 (3) | 0.052 (2) | 0.067 (3) | 0.008 (2) | −0.017 (2) | −0.014 (2) |
C19 | 0.0440 (19) | 0.052 (2) | 0.056 (2) | 0.0047 (16) | −0.0138 (16) | −0.0199 (17) |
C20 | 0.0471 (19) | 0.0395 (18) | 0.059 (2) | −0.0079 (15) | −0.0202 (16) | −0.0107 (16) |
C21 | 0.0423 (18) | 0.0457 (19) | 0.056 (2) | −0.0091 (15) | −0.0205 (16) | −0.0082 (16) |
C22 | 0.052 (2) | 0.046 (2) | 0.058 (2) | −0.0081 (16) | −0.0127 (17) | −0.0133 (17) |
C23 | 0.051 (2) | 0.051 (2) | 0.083 (3) | −0.0113 (18) | −0.012 (2) | −0.022 (2) |
C24 | 0.057 (2) | 0.086 (3) | 0.066 (3) | −0.024 (2) | 0.001 (2) | −0.032 (2) |
C25 | 0.072 (3) | 0.086 (3) | 0.060 (3) | −0.027 (3) | −0.006 (2) | −0.010 (2) |
C26 | 0.056 (2) | 0.060 (2) | 0.060 (2) | −0.0166 (19) | −0.0180 (19) | −0.0027 (19) |
N2 | 0.0421 (16) | 0.0456 (17) | 0.0520 (18) | 0.0066 (13) | −0.0206 (13) | −0.0100 (13) |
O4 | 0.0343 (13) | 0.0585 (17) | 0.112 (2) | −0.0072 (12) | −0.0075 (14) | −0.0100 (16) |
O5 | 0.0500 (14) | 0.0572 (15) | 0.0441 (14) | 0.0009 (12) | −0.0030 (11) | 0.0020 (11) |
O6 | 0.0612 (16) | 0.0461 (15) | 0.0787 (19) | 0.0104 (12) | −0.0416 (14) | −0.0149 (13) |
S2 | 0.0334 (4) | 0.0445 (5) | 0.0555 (5) | −0.0009 (3) | −0.0062 (4) | −0.0041 (4) |
Cl3 | 0.0357 (5) | 0.0757 (7) | 0.0822 (7) | −0.0091 (4) | −0.0112 (4) | 0.0057 (5) |
Cl4 | 0.1048 (10) | 0.0482 (6) | 0.1177 (11) | 0.0030 (6) | −0.0070 (8) | −0.0277 (7) |
C1—C2 | 1.389 (5) | C14—C19 | 1.388 (5) |
C1—C6 | 1.394 (4) | C14—C15 | 1.390 (5) |
C1—S1 | 1.775 (3) | C14—S2 | 1.765 (4) |
C2—C3 | 1.386 (5) | C15—C16 | 1.384 (5) |
C2—Cl1 | 1.730 (3) | C15—Cl3 | 1.736 (4) |
C3—C4 | 1.377 (5) | C16—C17 | 1.375 (6) |
C3—H3 | 0.93 | C16—H16 | 0.93 |
C4—C5 | 1.377 (6) | C17—C18 | 1.365 (6) |
C4—H4 | 0.93 | C17—H17 | 0.93 |
C5—C6 | 1.381 (5) | C18—C19 | 1.380 (6) |
C5—H5 | 0.93 | C18—H18 | 0.93 |
C6—H6 | 0.93 | C19—H19 | 0.93 |
C7—O3 | 1.220 (4) | C20—O6 | 1.214 (4) |
C7—N1 | 1.382 (4) | C20—N2 | 1.384 (5) |
C7—C8 | 1.493 (5) | C20—C21 | 1.475 (5) |
C8—C9 | 1.391 (5) | C21—C22 | 1.382 (5) |
C8—C13 | 1.396 (5) | C21—C26 | 1.396 (5) |
C9—C10 | 1.374 (5) | C22—C23 | 1.393 (6) |
C9—H9 | 0.93 | C22—H22 | 0.93 |
C10—C11 | 1.372 (6) | C23—C24 | 1.379 (6) |
C10—Cl2 | 1.738 (4) | C23—Cl4 | 1.719 (4) |
C11—C12 | 1.377 (6) | C24—C25 | 1.359 (7) |
C11—H11 | 0.93 | C24—H24 | 0.93 |
C12—C13 | 1.383 (5) | C25—C26 | 1.371 (6) |
C12—H12 | 0.93 | C25—H25 | 0.93 |
C13—H13 | 0.93 | C26—H26 | 0.93 |
N1—S1 | 1.647 (3) | N2—S2 | 1.650 (3) |
N1—H1N | 0.845 (18) | N2—H2N | 0.846 (19) |
O1—S1 | 1.418 (3) | O4—S2 | 1.416 (3) |
O2—S1 | 1.427 (3) | O5—S2 | 1.435 (3) |
C2—C1—C6 | 119.5 (3) | C19—C14—C15 | 119.4 (3) |
C2—C1—S1 | 123.1 (2) | C19—C14—S2 | 117.3 (3) |
C6—C1—S1 | 117.3 (3) | C15—C14—S2 | 123.2 (3) |
C3—C2—C1 | 119.9 (3) | C16—C15—C14 | 120.0 (3) |
C3—C2—Cl1 | 118.1 (3) | C16—C15—Cl3 | 117.6 (3) |
C1—C2—Cl1 | 122.0 (3) | C14—C15—Cl3 | 122.4 (3) |
C4—C3—C2 | 119.9 (4) | C17—C16—C15 | 119.5 (4) |
C4—C3—H3 | 120.1 | C17—C16—H16 | 120.2 |
C2—C3—H3 | 120.1 | C15—C16—H16 | 120.2 |
C5—C4—C3 | 120.8 (4) | C18—C17—C16 | 121.0 (4) |
C5—C4—H4 | 119.6 | C18—C17—H17 | 119.5 |
C3—C4—H4 | 119.6 | C16—C17—H17 | 119.5 |
C4—C5—C6 | 119.7 (3) | C17—C18—C19 | 120.0 (4) |
C4—C5—H5 | 120.1 | C17—C18—H18 | 120.0 |
C6—C5—H5 | 120.1 | C19—C18—H18 | 120.0 |
C5—C6—C1 | 120.2 (3) | C18—C19—C14 | 120.0 (4) |
C5—C6—H6 | 119.9 | C18—C19—H19 | 120.0 |
C1—C6—H6 | 119.9 | C14—C19—H19 | 120.0 |
O3—C7—N1 | 122.1 (3) | O6—C20—N2 | 120.3 (3) |
O3—C7—C8 | 122.8 (3) | O6—C20—C21 | 123.3 (3) |
N1—C7—C8 | 115.0 (3) | N2—C20—C21 | 116.4 (3) |
C9—C8—C13 | 120.1 (3) | C22—C21—C26 | 120.2 (4) |
C9—C8—C7 | 118.4 (3) | C22—C21—C20 | 121.8 (3) |
C13—C8—C7 | 121.4 (3) | C26—C21—C20 | 117.9 (3) |
C10—C9—C8 | 118.8 (4) | C21—C22—C23 | 118.5 (4) |
C10—C9—H9 | 120.6 | C21—C22—H22 | 120.8 |
C8—C9—H9 | 120.6 | C23—C22—H22 | 120.8 |
C9—C10—C11 | 121.9 (4) | C24—C23—C22 | 120.6 (4) |
C9—C10—Cl2 | 118.5 (3) | C24—C23—Cl4 | 120.8 (4) |
C11—C10—Cl2 | 119.6 (3) | C22—C23—Cl4 | 118.6 (3) |
C12—C11—C10 | 119.2 (4) | C25—C24—C23 | 120.5 (4) |
C12—C11—H11 | 120.4 | C25—C24—H24 | 119.7 |
C10—C11—H11 | 120.4 | C23—C24—H24 | 119.7 |
C11—C12—C13 | 120.8 (4) | C24—C25—C26 | 120.2 (4) |
C11—C12—H12 | 119.6 | C24—C25—H25 | 119.9 |
C13—C12—H12 | 119.6 | C26—C25—H25 | 119.9 |
C12—C13—C8 | 119.2 (4) | C25—C26—C21 | 120.1 (4) |
C12—C13—H13 | 120.4 | C25—C26—H26 | 119.9 |
C8—C13—H13 | 120.4 | C21—C26—H26 | 119.9 |
C7—N1—S1 | 123.8 (2) | C20—N2—S2 | 122.5 (2) |
C7—N1—H1N | 121 (3) | C20—N2—H2N | 119 (3) |
S1—N1—H1N | 114 (3) | S2—N2—H2N | 117 (3) |
O1—S1—O2 | 120.43 (17) | O4—S2—O5 | 119.14 (18) |
O1—S1—N1 | 107.77 (16) | O4—S2—N2 | 109.45 (18) |
O2—S1—N1 | 103.83 (15) | O5—S2—N2 | 104.14 (15) |
O1—S1—C1 | 107.48 (16) | O4—S2—C14 | 107.70 (16) |
O2—S1—C1 | 109.82 (15) | O5—S2—C14 | 110.08 (16) |
N1—S1—C1 | 106.73 (15) | N2—S2—C14 | 105.52 (16) |
C6—C1—C2—C3 | −0.2 (5) | C19—C14—C15—C16 | 2.0 (5) |
S1—C1—C2—C3 | −178.1 (3) | S2—C14—C15—C16 | −177.8 (3) |
C6—C1—C2—Cl1 | −179.0 (3) | C19—C14—C15—Cl3 | −175.8 (3) |
S1—C1—C2—Cl1 | 3.1 (4) | S2—C14—C15—Cl3 | 4.5 (4) |
C1—C2—C3—C4 | 0.2 (6) | C14—C15—C16—C17 | −1.0 (6) |
Cl1—C2—C3—C4 | 179.1 (3) | Cl3—C15—C16—C17 | 176.9 (3) |
C2—C3—C4—C5 | 0.2 (6) | C15—C16—C17—C18 | −0.4 (6) |
C3—C4—C5—C6 | −0.6 (6) | C16—C17—C18—C19 | 0.6 (7) |
C4—C5—C6—C1 | 0.7 (6) | C17—C18—C19—C14 | 0.4 (6) |
C2—C1—C6—C5 | −0.3 (5) | C15—C14—C19—C18 | −1.7 (5) |
S1—C1—C6—C5 | 177.7 (3) | S2—C14—C19—C18 | 178.1 (3) |
O3—C7—C8—C9 | 31.9 (5) | O6—C20—C21—C22 | −149.0 (4) |
N1—C7—C8—C9 | −149.0 (3) | N2—C20—C21—C22 | 30.7 (5) |
O3—C7—C8—C13 | −144.7 (4) | O6—C20—C21—C26 | 27.5 (5) |
N1—C7—C8—C13 | 34.4 (4) | N2—C20—C21—C26 | −152.8 (3) |
C13—C8—C9—C10 | −1.1 (5) | C26—C21—C22—C23 | −0.7 (5) |
C7—C8—C9—C10 | −177.8 (3) | C20—C21—C22—C23 | 175.8 (3) |
C8—C9—C10—C11 | 2.2 (6) | C21—C22—C23—C24 | 0.4 (6) |
C8—C9—C10—Cl2 | −178.3 (3) | C21—C22—C23—Cl4 | −177.4 (3) |
C9—C10—C11—C12 | −1.7 (6) | C22—C23—C24—C25 | 0.5 (6) |
Cl2—C10—C11—C12 | 178.8 (3) | Cl4—C23—C24—C25 | 178.3 (3) |
C10—C11—C12—C13 | 0.2 (6) | C23—C24—C25—C26 | −1.1 (7) |
C11—C12—C13—C8 | 0.8 (6) | C24—C25—C26—C21 | 0.8 (6) |
C9—C8—C13—C12 | −0.3 (5) | C22—C21—C26—C25 | 0.1 (5) |
C7—C8—C13—C12 | 176.3 (3) | C20—C21—C26—C25 | −176.5 (3) |
O3—C7—N1—S1 | 15.6 (5) | O6—C20—N2—S2 | 5.7 (5) |
C8—C7—N1—S1 | −163.5 (2) | C21—C20—N2—S2 | −173.9 (2) |
C7—N1—S1—O1 | 52.6 (3) | C20—N2—S2—O4 | 53.1 (3) |
C7—N1—S1—O2 | −178.6 (3) | C20—N2—S2—O5 | −178.5 (3) |
C7—N1—S1—C1 | −62.6 (3) | C20—N2—S2—C14 | −62.6 (3) |
C2—C1—S1—O1 | −178.8 (3) | C19—C14—S2—O4 | −4.5 (3) |
C6—C1—S1—O1 | 3.3 (3) | C15—C14—S2—O4 | 175.2 (3) |
C2—C1—S1—O2 | 48.6 (3) | C19—C14—S2—O5 | −135.9 (3) |
C6—C1—S1—O2 | −129.4 (3) | C15—C14—S2—O5 | 43.9 (3) |
C2—C1—S1—N1 | −63.4 (3) | C19—C14—S2—N2 | 112.3 (3) |
C6—C1—S1—N1 | 118.7 (3) | C15—C14—S2—N2 | −67.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O6 | 0.84 (2) | 2.02 (2) | 2.836 (4) | 162 (4) |
N2—H2N···O5i | 0.85 (2) | 2.10 (2) | 2.937 (4) | 173 (4) |
Symmetry code: (i) −x+2, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C13H9Cl2NO3S |
Mr | 330.17 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 299 |
a, b, c (Å) | 7.4399 (6), 11.679 (1), 17.138 (2) |
α, β, γ (°) | 75.346 (7), 83.188 (8), 77.732 (7) |
V (Å3) | 1404.5 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.62 |
Crystal size (mm) | 0.20 × 0.14 × 0.08 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2009) |
Tmin, Tmax | 0.887, 0.952 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9768, 5694, 4267 |
Rint | 0.018 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.154, 1.04 |
No. of reflections | 5694 |
No. of parameters | 367 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 1.10, −0.50 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O6 | 0.84 (2) | 2.02 (2) | 2.836 (4) | 162 (4) |
N2—H2N···O5i | 0.85 (2) | 2.10 (2) | 2.937 (4) | 173 (4) |
Symmetry code: (i) −x+2, −y+1, −z+1. |
Acknowledgements
PAS thanks the Council of Scientific and Industrial Research (CSIR), Government of India, New Delhi, for the award of a research fellowship.
References
Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2009). Acta Cryst. E65, o2516. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2010). Acta Cryst. E66, o433. Web of Science CSD CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Suchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2010a). Acta Cryst. E66, o1040. Web of Science CSD CrossRef IUCr Journals Google Scholar
Suchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2010b). Acta Cryst. E66, o1292. Web of Science CSD CrossRef IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
As a part of studying the effect of ring and the side chain substitutions on the crystal structures of N-aryl sulfonamides (Gowda et al., 2009, 2010; Suchetan et al., 2010a,b), the structure of 2-chloro-N-(3-chlorobenzoyl)-benzenesulfonamide (I) has been determined. The asymmetric unit of (I) contains two independent molecules. In the C—SO2—NH—C(O) segments, the N—H bonds are anti to the C═O bonds (Fig.1), similar to those observed in 2-chloro-N- (3-methylbenzoyl)-benzenesulfonamide (II) (Suchetan et al., 2010b), 2-methyl-N-(3-methylbenzoyl)-benzenesulfonamide (III) (Gowda et al., 2010), 2-chloro-N-(2-chlorobenzoyl)- benzenesulfonamide (IV)(Suchetan et al., 2010a), N-(benzoyl)-benzenesulfonamide (V) (Gowda et al., 2009).
The conformation of the C═O bond is anti to the meta-Cl group in the benzoyl ring of one of the molecules and syn in the other, compared to the anti conformation observed between C═O bond and meta- methyl group in the benzoyl ring of (II).
The chlorobenzoyl and sulfonyl-bound chlorophenyl units in the two molecules of (I) are twisted with respect to the S—N bond, with torsional angles of -62.6 (3)° [C7—N1—S1—C1] and -62.6 (3)° [C20—N2—S2—C14], compared to those of -66.5 (2)° in (II), -66.2 (3)° in (III), -66.5 (2)° in (IV) and -66.9 (3)° in (V). The dihedral angles between the sulfonyl and the benzoyl- bound benzene rings are 77.8 (1)° (molecule 1) and 83.5 (1)° (molecule 2), compared to the values of 74.7 (1)° in (II), 74.8 (1)° in (III), 76.9 (1) in (IV) and 80.3 (1)° in (V).