| 4-Chloro-N-(3,5-dichloro-phenyl)benzene-sulfonamide. | |
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PMID: 21754517 Owner: NLM Status: PubMed-not-MEDLINE |
Abstract/OtherAbstract:
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In the title compound, C(12)H(8)Cl(3)NO(2)S, the dihedral angle between the aromatic rings is 87.9 (1)° and the C-S-N-C torsion angle is 77.8 (2)°. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds occur. |
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Authors:
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K Shakuntala; Sabine Foro; B Thimme Gowda |
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Publication Detail:
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Type: Journal Article Date: 2011-04-29 |
Journal Detail:
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Title: Acta crystallographica. Section E, Structure reports online Volume: 67 ISSN: 1600-5368 ISO Abbreviation: Acta Crystallogr Sect E Struct Rep Online Publication Date: 2011 May |
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Created Date: 2011-07-14 Completed Date: 2011-07-14 Revised Date: 2013-03-29 |
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Nlm Unique ID: 101089178 Medline TA: Acta Crystallogr Sect E Struct Rep Online Country: England |
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Languages: eng Pagination: o1219 Citation Subset: - |
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Journal Information Journal ID (nlm-ta): Acta Crystallogr Sect E Struct Rep Online Journal ID (publisher-id): Acta Cryst. E ISSN: 1600-5368 Publisher: International Union of Crystallography |
Article Information Download PDF  A full version of this article is available from Crystallography Journals Online.© Shakuntala et al. 2011 open-access: Received Day: 16 Month: 4 Year: 2011 Accepted Day: 19 Month: 4 Year: 2011 collection publication date: Day: 01 Month: 5 Year: 2011 Electronic publication date: Day: 29 Month: 4 Year: 2011 pmc-release publication date: Day: 29 Month: 4 Year: 2011 Volume: 67 Issue: Pt 5 First Page: o1219 Last Page: o1219 ID: 3089164 PubMed Id: 21754517 Publisher Id: bq2298 DOI: 10.1107/S160053681101470X Coden: ACSEBH Publisher Item Identifier: S160053681101470X |
| 4-Chloro-N-(3,5-dichlorophenyl)benzenesulfonamide Alternate Title:C12H8Cl3NO2S | |
| K. Shakuntalaa | |
| Sabine Forob | |
| B. Thimme Gowdaa* | |
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aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India |
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bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany |
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| Correspondence: Correspondence e-mail: gowdabt@yahoo.com |
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For hydrogen-bonding preferences of sulfonamides, see; Adsmond & Grant (2001 ▶). For our study of the effect of substituents on the structures of N-(aryl)-amides, see: Gowda et al. (2004 ▶); on the structures of N-(aryl)arylsulfonamides, see: Shakuntala et al. (2011a ▶,b ▶); and on the oxidative strengths of N-chloro-N-arylsulfonamides, see: Gowda & Kumar (2003 ▶).[Chemical Structure ID: scheme1]
- C12H8Cl3NO2S
- Mr = 336.60
- Triclinic,
- a = 4.935 (1) Å
- b = 11.630 (2) Å
- c = 13.115 (2) Å
- α = 113.52 (2)°
- β = 90.49 (1)°
- γ = 96.50 (1)°
- V = 684.6 (2) Å3
- Z = 2
- Mo Kα radiation
- μ = 0.82 mm−1
- T = 293 K
- 0.32 × 0.20 × 0.10 mm
- Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
- Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) Tmin = 0.780, Tmax = 0.923
- 4440 measured reflections
- 2785 independent reflections
- 2236 reflections with I > 2σ(I)
- Rint = 0.013
- R[F2 > 2σ(F2)] = 0.034
- wR(F2) = 0.086
- S = 1.03
- 2785 reflections
- 175 parameters
- 1 restraint
- H atoms treated by a mixture of independent and constrained refinement
- Δρmax = 0.36 e Å−3
- Δρmin = −0.33 e Å−3
Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: 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.
Notes
fnu1Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2298).
KS thanks the University Grants Commission, Government of India, New Delhi, for the award of a research fellowship under its faculty improvement programme.
The amide and sulfonamide moieties are important constituents of many biologically important compounds. As a part of studying the substituent effects on the structures and other aspects of this class of compounds (Gowda & Kumar, 2003; Gowda et al., 2004; Shakuntala et al., 2011a,b), in the present work, the crystal structure of 4-chloro-N-(3,5-dichlorophenyl)benzenesulfonamide (I) has been determined (Fig. 1). The molecule is twisted at the S atom with the C—SO2—NH—C torsion angle of 77.8 (2)°, compared to the values of -58.4 (3)° in 4-chloro-N-(3-chlorophenyl)benzenesulfonamide (II) (Shakuntala et al., 2011b) and -56.7 (2)° in 4-chloro-N-(2,3-dichlorophenyl)-benzenesulfonamide (III) (Shakuntala et al., 2011a). The conformation of the N—H bond is anti to one of the meta-chloro group in the anilino benzene ring and syn to the other.
The sulfonyl and the anilino benzene rings in (I) are tilted relative to each other by 87.9 (1)°, compared to the values of 77.1 (1)° in (II) and 56.5 (1)° in (III).
Intermolecular N—H···O(S) hydrogen bonding interactions generate inversion related dimers which are further packed via van der Waals interactions in the crystal structure (Fig. 2).
The solution of chlorobenzene (10 ml) in chloroform (40 ml) was added dropwise with chlorosulfonic acid (25 ml) at 0° C. After the initial evolution of hydrogen chloride subsided, the reaction mixture was brought to room temperature and poured into crushed ice in a beaker. The chloroform layer was separated, washed with cold water and allowed to evaporate slowly. The residual 4-chlorobenzenesulfonylchloride was treated with 3,5-dichloroaniline in the stoichiometric ratio and boiled for 15 min. The reaction mixture was then cooled to room temperature and added to ice cold water (100 ml). The resultant 4-chloro-N-(3,5-dichlorophenyl)-benzenesulfonamide was filtered under suction and washed thoroughly with cold water. It was then recrystallized to constant melting point from dilute ethanol. The compound was characterized by FT–IR and NMR spectra.
Prism like colorless single crystals used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation at room temperature.
The H atom of the NH group was located in a difference map and later restrained to the distance N—H = 0.86 (2) Å. 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).
Symmetry codes: (i) −x+1, −y+1, −z.
References
| Adsmond, D. A. & Grant, D. J. W. (2001). J. Pharm. Sci.90, 2058–2077. | |
| Gowda, B. T. & Kumar, B. H. A. (2003). Oxid. Commun.26, 403–425. | |
| Gowda, B. T., Svoboda, I. & Fuess, H. (2004). Z. Naturforsch. Teil A, 55, 845–852. | |
| Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED Oxford Diffraction Ltd, Yarnton, Oxfordshire, England. | |
| Shakuntala, K., Foro, S. & Gowda, B. T. (2011a). Acta Cryst. E67, o232. | |
| Shakuntala, K., Foro, S. & Gowda, B. T. (2011b). Acta Cryst. E67, o1017. | |
| Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. | |
| Spek, A. L. (2009). Acta Cryst. D65, 148–155. |
Figures
[Figure ID: Fap1] |
Fig. 1.
Molecular structure of (I), showing the atom labeling scheme and displacement ellipsoids are drawn at the 50% probability level. |
[Figure ID: Fap2] |
Fig. 2.
Molecular packing of (I) with hydrogen bonding shown as dashed lines. |
Tables
| C12H8Cl3NO2S | Z = 2 |
| Mr = 336.60 | F(000) = 340 |
| Triclinic, P1 | Dx = 1.633 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 4.935 (1) Å | Cell parameters from 1578 reflections |
| b = 11.630 (2) Å | θ = 3.0–27.8° |
| c = 13.115 (2) Å | µ = 0.82 mm−1 |
| α = 113.52 (2)° | T = 293 K |
| β = 90.49 (1)° | Prism, colourless |
| γ = 96.50 (1)° | 0.32 × 0.20 × 0.10 mm |
| V = 684.6 (2) Å3 |
| Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector | 2785 independent reflections |
| Radiation source: fine-focus sealed tube | 2236 reflections with I > 2σ(I) |
| graphite | Rint = 0.013 |
| Rotation method data acquisition using ω and φ scans | θmax = 26.4°, θmin = 3.0° |
| Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | h = −6→4 |
| Tmin = 0.780, Tmax = 0.923 | k = −14→14 |
| 4440 measured reflections | l = −15→16 |
| 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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.086 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.03 | w = 1/[σ2(Fo2) + (0.0393P)2 + 0.3103P] where P = (Fo2 + 2Fc2)/3 |
| 2785 reflections | (Δ/σ)max = 0.005 |
| 175 parameters | Δρmax = 0.36 e Å−3 |
| 1 restraint | Δρmin = −0.33 e Å−3 |
| Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
| 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. |
| x | y | z | Uiso*/Ueq | ||
| C1 | 0.7071 (4) | 0.7199 (2) | 0.24024 (17) | 0.0357 (5) | |
| C2 | 0.8325 (5) | 0.7573 (2) | 0.34566 (19) | 0.0443 (5) | |
| H2 | 0.7746 | 0.7164 | 0.3913 | 0.053* | |
| C3 | 1.0431 (5) | 0.8552 (2) | 0.3823 (2) | 0.0506 (6) | |
| H3 | 1.1295 | 0.8807 | 0.4525 | 0.061* | |
| C4 | 1.1242 (5) | 0.9149 (2) | 0.3139 (2) | 0.0466 (6) | |
| C5 | 0.9996 (5) | 0.8800 (2) | 0.2095 (2) | 0.0507 (6) | |
| H5 | 1.0565 | 0.9221 | 0.1648 | 0.061* | |
| C6 | 0.7896 (5) | 0.7817 (2) | 0.17258 (19) | 0.0454 (5) | |
| H6 | 0.7035 | 0.7569 | 0.1024 | 0.055* | |
| C7 | 0.7357 (4) | 0.39831 (19) | 0.18639 (16) | 0.0330 (4) | |
| C8 | 0.6937 (4) | 0.4095 (2) | 0.29448 (17) | 0.0388 (5) | |
| H8 | 0.5776 | 0.4644 | 0.3387 | 0.047* | |
| C9 | 0.8290 (5) | 0.3369 (2) | 0.33442 (18) | 0.0416 (5) | |
| C10 | 1.0005 (5) | 0.2536 (2) | 0.27211 (19) | 0.0463 (6) | |
| H10 | 1.0892 | 0.2057 | 0.3010 | 0.056* | |
| C11 | 1.0357 (4) | 0.2439 (2) | 0.16442 (19) | 0.0400 (5) | |
| C12 | 0.9083 (4) | 0.3151 (2) | 0.12094 (18) | 0.0365 (5) | |
| H12 | 0.9373 | 0.3077 | 0.0487 | 0.044* | |
| N1 | 0.5991 (4) | 0.46264 (17) | 0.13400 (14) | 0.0382 (4) | |
| H1N | 0.645 (5) | 0.452 (2) | 0.0694 (15) | 0.046* | |
| O1 | 0.3111 (3) | 0.58358 (15) | 0.28347 (12) | 0.0442 (4) | |
| O2 | 0.2996 (3) | 0.59558 (15) | 0.09918 (12) | 0.0442 (4) | |
| Cl1 | 1.39180 (14) | 1.03860 (7) | 0.36017 (7) | 0.0681 (2) | |
| Cl2 | 0.77531 (16) | 0.35067 (7) | 0.46970 (5) | 0.0603 (2) | |
| Cl3 | 1.24838 (13) | 0.13818 (6) | 0.08193 (6) | 0.05370 (18) | |
| S1 | 0.45009 (11) | 0.58943 (5) | 0.19092 (4) | 0.03502 (14) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0393 (11) | 0.0375 (11) | 0.0312 (10) | 0.0088 (9) | 0.0033 (9) | 0.0137 (9) |
| C2 | 0.0567 (14) | 0.0441 (13) | 0.0365 (12) | 0.0058 (11) | −0.0029 (10) | 0.0210 (10) |
| C3 | 0.0594 (15) | 0.0460 (13) | 0.0460 (14) | 0.0057 (11) | −0.0123 (11) | 0.0187 (11) |
| C4 | 0.0438 (13) | 0.0368 (12) | 0.0563 (15) | 0.0068 (10) | −0.0006 (11) | 0.0154 (11) |
| C5 | 0.0588 (15) | 0.0504 (14) | 0.0501 (14) | 0.0054 (12) | 0.0082 (12) | 0.0279 (12) |
| C6 | 0.0553 (14) | 0.0514 (14) | 0.0321 (11) | 0.0054 (11) | 0.0030 (10) | 0.0197 (10) |
| C7 | 0.0362 (11) | 0.0341 (11) | 0.0301 (10) | −0.0015 (8) | −0.0025 (8) | 0.0159 (8) |
| C8 | 0.0454 (12) | 0.0407 (12) | 0.0311 (11) | 0.0013 (9) | 0.0002 (9) | 0.0164 (9) |
| C9 | 0.0505 (13) | 0.0444 (12) | 0.0329 (11) | −0.0039 (10) | −0.0028 (10) | 0.0212 (10) |
| C10 | 0.0528 (14) | 0.0444 (13) | 0.0480 (14) | 0.0032 (11) | −0.0076 (11) | 0.0263 (11) |
| C11 | 0.0390 (12) | 0.0362 (11) | 0.0423 (12) | 0.0001 (9) | −0.0002 (9) | 0.0145 (10) |
| C12 | 0.0388 (11) | 0.0382 (11) | 0.0327 (11) | −0.0005 (9) | 0.0000 (9) | 0.0160 (9) |
| N1 | 0.0495 (11) | 0.0440 (10) | 0.0249 (9) | 0.0105 (8) | 0.0057 (8) | 0.0166 (8) |
| O1 | 0.0453 (9) | 0.0560 (10) | 0.0342 (8) | 0.0078 (7) | 0.0101 (7) | 0.0206 (7) |
| O2 | 0.0448 (9) | 0.0574 (10) | 0.0330 (8) | 0.0125 (7) | −0.0027 (7) | 0.0194 (7) |
| Cl1 | 0.0579 (4) | 0.0520 (4) | 0.0911 (6) | −0.0058 (3) | −0.0129 (4) | 0.0292 (4) |
| Cl2 | 0.0874 (5) | 0.0668 (4) | 0.0378 (3) | 0.0071 (3) | 0.0023 (3) | 0.0333 (3) |
| Cl3 | 0.0543 (4) | 0.0469 (3) | 0.0610 (4) | 0.0135 (3) | 0.0063 (3) | 0.0209 (3) |
| S1 | 0.0375 (3) | 0.0434 (3) | 0.0262 (3) | 0.0081 (2) | 0.0021 (2) | 0.0154 (2) |
| C1—C6 | 1.385 (3) | C7—N1 | 1.415 (3) |
| C1—C2 | 1.389 (3) | C8—C9 | 1.381 (3) |
| C1—S1 | 1.760 (2) | C8—H8 | 0.9300 |
| C2—C3 | 1.376 (3) | C9—C10 | 1.375 (3) |
| C2—H2 | 0.9300 | C9—Cl2 | 1.742 (2) |
| C3—C4 | 1.373 (4) | C10—C11 | 1.385 (3) |
| C3—H3 | 0.9300 | C10—H10 | 0.9300 |
| C4—C5 | 1.379 (3) | C11—C12 | 1.377 (3) |
| C4—Cl1 | 1.744 (2) | C11—Cl3 | 1.742 (2) |
| C5—C6 | 1.376 (3) | C12—H12 | 0.9300 |
| C5—H5 | 0.9300 | N1—S1 | 1.6274 (19) |
| C6—H6 | 0.9300 | N1—H1N | 0.844 (16) |
| C7—C12 | 1.391 (3) | O1—S1 | 1.4207 (16) |
| C7—C8 | 1.390 (3) | O2—S1 | 1.4387 (15) |
| C6—C1—C2 | 120.5 (2) | C7—C8—H8 | 120.9 |
| C6—C1—S1 | 120.01 (17) | C10—C9—C8 | 123.1 (2) |
| C2—C1—S1 | 119.48 (17) | C10—C9—Cl2 | 118.69 (17) |
| C3—C2—C1 | 119.6 (2) | C8—C9—Cl2 | 118.17 (19) |
| C3—C2—H2 | 120.2 | C9—C10—C11 | 117.1 (2) |
| C1—C2—H2 | 120.2 | C9—C10—H10 | 121.4 |
| C2—C3—C4 | 119.2 (2) | C11—C10—H10 | 121.4 |
| C2—C3—H3 | 120.4 | C12—C11—C10 | 122.1 (2) |
| C4—C3—H3 | 120.4 | C12—C11—Cl3 | 119.20 (18) |
| C3—C4—C5 | 121.8 (2) | C10—C11—Cl3 | 118.70 (18) |
| C3—C4—Cl1 | 119.2 (2) | C11—C12—C7 | 119.2 (2) |
| C5—C4—Cl1 | 119.0 (2) | C11—C12—H12 | 120.4 |
| C6—C5—C4 | 119.0 (2) | C7—C12—H12 | 120.4 |
| C6—C5—H5 | 120.5 | C7—N1—S1 | 128.77 (14) |
| C4—C5—H5 | 120.5 | C7—N1—H1N | 116.4 (17) |
| C5—C6—C1 | 119.8 (2) | S1—N1—H1N | 111.1 (17) |
| C5—C6—H6 | 120.1 | O1—S1—O2 | 120.01 (10) |
| C1—C6—H6 | 120.1 | O1—S1—N1 | 108.60 (10) |
| C12—C7—C8 | 120.25 (19) | O2—S1—N1 | 104.03 (9) |
| C12—C7—N1 | 116.01 (18) | O1—S1—C1 | 108.36 (10) |
| C8—C7—N1 | 123.65 (19) | O2—S1—C1 | 107.64 (10) |
| C9—C8—C7 | 118.2 (2) | N1—S1—C1 | 107.59 (10) |
| C9—C8—H8 | 120.9 | ||
| C6—C1—C2—C3 | −1.0 (3) | C9—C10—C11—Cl3 | −179.32 (18) |
| S1—C1—C2—C3 | 176.71 (18) | C10—C11—C12—C7 | −0.9 (3) |
| C1—C2—C3—C4 | 0.5 (4) | Cl3—C11—C12—C7 | 179.18 (16) |
| C2—C3—C4—C5 | 0.4 (4) | C8—C7—C12—C11 | 0.3 (3) |
| C2—C3—C4—Cl1 | −179.78 (18) | N1—C7—C12—C11 | −176.30 (19) |
| C3—C4—C5—C6 | −0.6 (4) | C12—C7—N1—S1 | −162.46 (16) |
| Cl1—C4—C5—C6 | 179.53 (18) | C8—C7—N1—S1 | 21.1 (3) |
| C4—C5—C6—C1 | 0.0 (4) | C7—N1—S1—O1 | −39.3 (2) |
| C2—C1—C6—C5 | 0.8 (3) | C7—N1—S1—O2 | −168.24 (18) |
| S1—C1—C6—C5 | −176.95 (18) | C7—N1—S1—C1 | 77.8 (2) |
| C12—C7—C8—C9 | 0.5 (3) | C6—C1—S1—O1 | −151.25 (18) |
| N1—C7—C8—C9 | 176.8 (2) | C2—C1—S1—O1 | 31.0 (2) |
| C7—C8—C9—C10 | −0.6 (3) | C6—C1—S1—O2 | −20.1 (2) |
| C7—C8—C9—Cl2 | −179.79 (16) | C2—C1—S1—O2 | 162.20 (17) |
| C8—C9—C10—C11 | 0.0 (4) | C6—C1—S1—N1 | 91.51 (19) |
| Cl2—C9—C10—C11 | 179.18 (17) | C2—C1—S1—N1 | −86.23 (19) |
| C9—C10—C11—C12 | 0.8 (3) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1N···O2i | 0.84 (2) | 2.08 (2) | 2.917 (2) | 170 (2) |
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