Literature DB >> 22219961

4-Chloro-N-(3,4-dimethyl-phen-yl)-2-methyl-benzene-sulfonamide.

Vinola Z Rodrigues, Sabine Foro, B Thimme Gowda.   

Abstract

In the title compound, C(15)H(16)ClNO(2)S, the conformation of the N-C bond in the C-SO(2)-NH-C segment is gauche with respect to the S=O bonds. Further, the N-H bond in the C-SO(2)-NH-C segment is syn with respect to the meta-methyl group in the aniline benzene ring and the ortho-methyl group in the sulfonyl benzene ring. The C-SO(2)-NH-C torsion angle is -49.72 (18)°. The sulfonyl and aniline benzene rings are tilted relative to each other by 71.6 (1)°. The crystal structure features inversion-related dimers linked by pairs of N-H⋯O hydrogen bonds.

Entities:  

Year:  2011        PMID： 22219961      PMCID： PMC3247343          DOI： 10.1107/S1600536811041341

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the preparation of the title compound, see: Savitha & Gowda (2006 ▶). For hydrogen-bonding modes of sulfonamides, see: Adsmond & Grant (2001 ▶). For studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Gowda et al. (2007a ▶), on N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007b ▶), on N-(ar­yl)-aryl­sulfonamides, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶); Rodrigues et al. (2011 ▶); Shetty & Gowda (2005 ▶) and on N-(chloro)-aryl­sulfonamides, see: Gowda et al. (2003 ▶).

Experimental

Crystal data

C15H16ClNO2S M = 309.80 Triclinic, a = 8.1321 (9) Å b = 8.1604 (9) Å c = 12.456 (1) Å α = 80.991 (9)° β = 72.903 (8)° γ = 78.979 (8)° V = 771.04 (14) Å3 Z = 2 Mo Kα radiation μ = 0.38 mm−1 T = 293 K 0.50 × 0.44 × 0.40 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.832, T max = 0.862 5220 measured reflections 3126 independent reflections 2631 reflections with I > 2σ(I) R int = 0.008

Refinement

R[F 2 > 2σ(F 2)] = 0.037 wR(F 2) = 0.109 S = 1.05 3126 reflections 187 parameters 1 restraint H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.25 e Å−3 Δρmin = −0.28 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. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811041341/nc2250sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811041341/nc2250Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811041341/nc2250Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C15H16ClNO2SZ = 2
Mr = 309.80F(000) = 324
Triclinic, P1Dx = 1.334 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.1321 (9) ÅCell parameters from 3090 reflections
b = 8.1604 (9) Åθ = 2.6–27.8°
c = 12.456 (1) ŵ = 0.38 mm−1
α = 80.991 (9)°T = 293 K
β = 72.903 (8)°Prism, colourless
γ = 78.979 (8)°0.50 × 0.44 × 0.40 mm
V = 771.04 (14) Å3
Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector3126 independent reflections
Radiation source: fine-focus sealed tube2631 reflections with I > 2σ(I)
graphiteRint = 0.008
Rotation method data acquisition using ω scansθmax = 26.4°, θmin = 2.7°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)h = −9→10
Tmin = 0.832, Tmax = 0.862k = −8→10
5220 measured reflectionsl = −14→15
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) = 0.109H atoms treated by a mixture of independent and constrained refinement
S = 1.05w = 1/[σ2(Fo2) + (0.0545P)2 + 0.2665P] where P = (Fo2 + 2Fc2)/3
3126 reflections(Δ/σ)max < 0.001
187 parametersΔρmax = 0.25 e Å−3
1 restraintΔρmin = −0.28 e Å−3
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.
xyzUiso*/Ueq
C10.2471 (2)0.8601 (2)0.62239 (14)0.0382 (4)
C20.1044 (2)0.8022 (2)0.60861 (15)0.0425 (4)
C3−0.0582 (2)0.8982 (3)0.64517 (17)0.0523 (5)
H3−0.15600.86380.63680.063*
C4−0.0766 (3)1.0436 (3)0.69355 (18)0.0562 (5)
C50.0646 (3)1.1022 (3)0.7051 (2)0.0609 (5)
H50.05061.20170.73660.073*
C60.2272 (3)1.0094 (2)0.66863 (18)0.0508 (4)
H60.32451.04700.67510.061*
C70.3843 (2)0.5413 (2)0.77995 (16)0.0470 (4)
C80.3257 (3)0.3903 (3)0.82440 (17)0.0530 (5)
H80.33250.31200.77590.064*
C90.2568 (3)0.3528 (3)0.93980 (19)0.0638 (6)
C100.2442 (3)0.4724 (3)1.01236 (19)0.0698 (6)
C110.3023 (4)0.6217 (3)0.9667 (2)0.0740 (7)
H110.29310.70141.01480.089*
C120.3742 (3)0.6588 (3)0.85186 (19)0.0639 (6)
H120.41480.76040.82360.077*
C130.1185 (3)0.6361 (3)0.55858 (18)0.0578 (5)
H13A0.15270.54280.60890.069*
H13B0.20390.63580.48650.069*
H13C0.00770.62690.54930.069*
C140.1992 (5)0.1838 (4)0.9841 (3)0.1010 (10)
H14A0.26710.12381.03330.121*
H14B0.21580.12050.92190.121*
H14C0.07830.19951.02510.121*
C150.1678 (4)0.4386 (5)1.1389 (2)0.0994 (10)
H15A0.23630.34211.16790.119*
H15B0.05030.41781.15430.119*
H15C0.16830.53441.17470.119*
N10.4560 (2)0.5674 (2)0.66087 (13)0.0489 (4)
H1N0.459 (3)0.490 (2)0.6238 (17)0.059*
O10.50734 (18)0.70770 (17)0.47026 (11)0.0528 (3)
O20.56945 (17)0.83991 (19)0.61489 (13)0.0601 (4)
Cl1−0.28370 (8)1.15422 (10)0.74513 (7)0.0927 (3)
S10.46083 (5)0.74755 (5)0.58477 (4)0.04260 (15)
U11U22U33U12U13U23
C10.0340 (8)0.0368 (8)0.0425 (9)−0.0066 (6)−0.0080 (7)−0.0035 (7)
C20.0397 (9)0.0476 (10)0.0416 (9)−0.0115 (7)−0.0112 (7)−0.0030 (7)
C30.0374 (9)0.0666 (12)0.0546 (11)−0.0082 (8)−0.0173 (8)−0.0018 (9)
C40.0414 (10)0.0598 (12)0.0581 (12)0.0088 (9)−0.0117 (9)−0.0028 (10)
C50.0567 (12)0.0448 (11)0.0783 (15)0.0036 (9)−0.0152 (10)−0.0177 (10)
C60.0441 (10)0.0429 (10)0.0679 (12)−0.0083 (8)−0.0148 (9)−0.0123 (9)
C70.0381 (9)0.0514 (10)0.0469 (10)0.0059 (8)−0.0108 (7)−0.0084 (8)
C80.0468 (10)0.0525 (11)0.0541 (11)0.0020 (8)−0.0115 (8)−0.0057 (9)
C90.0506 (12)0.0708 (14)0.0592 (13)0.0004 (10)−0.0117 (10)0.0069 (11)
C100.0596 (13)0.0875 (17)0.0487 (12)0.0105 (12)−0.0100 (10)−0.0033 (12)
C110.0895 (18)0.0761 (16)0.0506 (12)0.0070 (13)−0.0164 (12)−0.0185 (11)
C120.0746 (14)0.0592 (12)0.0561 (12)−0.0013 (11)−0.0179 (11)−0.0114 (10)
C130.0491 (11)0.0725 (13)0.0640 (12)−0.0269 (10)−0.0165 (9)−0.0197 (10)
C140.115 (3)0.095 (2)0.082 (2)−0.0341 (19)−0.0141 (18)0.0186 (17)
C150.097 (2)0.125 (3)0.0514 (14)0.0077 (19)−0.0032 (14)−0.0002 (15)
N10.0541 (9)0.0423 (8)0.0455 (9)0.0010 (7)−0.0086 (7)−0.0105 (7)
O10.0552 (8)0.0490 (7)0.0465 (7)−0.0105 (6)0.0014 (6)−0.0087 (6)
O20.0358 (7)0.0655 (9)0.0825 (10)−0.0134 (6)−0.0112 (6)−0.0214 (8)
Cl10.0543 (4)0.1043 (5)0.1042 (5)0.0281 (3)−0.0195 (3)−0.0198 (4)
S10.0331 (2)0.0432 (2)0.0493 (3)−0.00675 (17)−0.00475 (17)−0.00988 (18)
C1—C61.390 (2)C10—C111.369 (4)
C1—C21.397 (2)C10—C151.517 (3)
C1—S11.7692 (17)C11—C121.386 (3)
C2—C31.390 (3)C11—H110.9300
C2—C131.549 (3)C12—H120.9300
C3—C41.377 (3)C13—H13A0.9600
C3—H30.9300C13—H13B0.9600
C4—C51.377 (3)C13—H13C0.9600
C4—Cl11.740 (2)C14—H14A0.9600
C5—C61.378 (3)C14—H14B0.9600
C5—H50.9300C14—H14C0.9600
C6—H60.9300C15—H15A0.9600
C7—C81.381 (3)C15—H15B0.9600
C7—C121.387 (3)C15—H15C0.9600
C7—N11.423 (2)N1—S11.6202 (17)
C8—C91.389 (3)N1—H1N0.832 (16)
C8—H80.9300O1—S11.4368 (14)
C9—C101.401 (4)O2—S11.4237 (14)
C9—C141.511 (4)
C6—C1—C2121.21 (16)C12—C11—H11118.6
C6—C1—S1116.39 (13)C11—C12—C7118.6 (2)
C2—C1—S1122.39 (13)C11—C12—H12120.7
C3—C2—C1117.21 (17)C7—C12—H12120.7
C3—C2—C13119.28 (16)C2—C13—H13A109.5
C1—C2—C13123.48 (16)C2—C13—H13B109.5
C4—C3—C2120.94 (18)H13A—C13—H13B109.5
C4—C3—H3119.5C2—C13—H13C109.5
C2—C3—H3119.5H13A—C13—H13C109.5
C3—C4—C5121.76 (18)H13B—C13—H13C109.5
C3—C4—Cl1119.51 (16)C9—C14—H14A109.5
C5—C4—Cl1118.70 (17)C9—C14—H14B109.5
C4—C5—C6118.19 (19)H14A—C14—H14B109.5
C4—C5—H5120.9C9—C14—H14C109.5
C6—C5—H5120.9H14A—C14—H14C109.5
C5—C6—C1120.65 (18)H14B—C14—H14C109.5
C5—C6—H6119.7C10—C15—H15A109.5
C1—C6—H6119.7C10—C15—H15B109.5
C8—C7—C12119.48 (19)H15A—C15—H15B109.5
C8—C7—N1117.62 (18)C10—C15—H15C109.5
C12—C7—N1122.89 (19)H15A—C15—H15C109.5
C7—C8—C9121.6 (2)H15B—C15—H15C109.5
C7—C8—H8119.2C7—N1—S1125.99 (13)
C9—C8—H8119.2C7—N1—H1N117.0 (16)
C8—C9—C10119.0 (2)S1—N1—H1N112.4 (16)
C8—C9—C14119.3 (2)O2—S1—O1118.08 (9)
C10—C9—C14121.7 (2)O2—S1—N1109.61 (9)
C11—C10—C9118.6 (2)O1—S1—N1104.70 (8)
C11—C10—C15120.3 (3)O2—S1—C1106.69 (8)
C9—C10—C15121.1 (3)O1—S1—C1110.69 (8)
C10—C11—C12122.7 (2)N1—S1—C1106.56 (8)
C10—C11—H11118.6
C6—C1—C2—C3−1.3 (3)C8—C9—C10—C15179.2 (2)
S1—C1—C2—C3177.61 (13)C14—C9—C10—C15−1.5 (4)
C6—C1—C2—C13−179.45 (18)C9—C10—C11—C12−0.5 (4)
S1—C1—C2—C13−0.6 (3)C15—C10—C11—C12179.6 (2)
C1—C2—C3—C4−0.4 (3)C10—C11—C12—C71.4 (4)
C13—C2—C3—C4177.81 (19)C8—C7—C12—C11−1.1 (3)
C2—C3—C4—C51.7 (3)N1—C7—C12—C11−179.9 (2)
C2—C3—C4—Cl1−176.56 (14)C8—C7—N1—S1153.78 (15)
C3—C4—C5—C6−1.3 (3)C12—C7—N1—S1−27.4 (3)
Cl1—C4—C5—C6177.06 (16)C7—N1—S1—O265.36 (18)
C4—C5—C6—C1−0.5 (3)C7—N1—S1—O1−167.05 (16)
C2—C1—C6—C51.8 (3)C7—N1—S1—C1−49.72 (18)
S1—C1—C6—C5−177.18 (16)C6—C1—S1—O21.39 (17)
C12—C7—C8—C9−0.1 (3)C2—C1—S1—O2−177.56 (14)
N1—C7—C8—C9178.80 (17)C6—C1—S1—O1−128.29 (15)
C7—C8—C9—C101.0 (3)C2—C1—S1—O152.77 (16)
C7—C8—C9—C14−178.3 (2)C6—C1—S1—N1118.43 (15)
C8—C9—C10—C11−0.7 (3)C2—C1—S1—N1−60.51 (16)
C14—C9—C10—C11178.6 (2)
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.83 (2)2.07 (2)2.899 (2)175 (2)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1—H1N⋯O1i0.83 (2)2.07 (2)2.899 (2)175 (2)

Symmetry code: (i) .

  5 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Hydrogen bonding in sulfonamides.

Authors:  D A Adsmond; D J Grant
Journal:  J Pharm Sci       Date:  2001-12       Impact factor: 3.534

3.  Structural systematics of 4,4'-disubstituted benzenesulfonamidobenzenes. 1. Overview and dimer-based isostructures.

Authors:  Thomas Gelbrich; Michael B Hursthouse; Terence L Threlfall
Journal:  Acta Crystallogr B       Date:  2007-07-17

4.  4-Chloro-N-(2,4-dimethyl-phen-yl)-2-methyl-benzene-sulfonamide.

Authors:  Vinola Z Rodrigues; Sabine Foro; B Thimme Gowda
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-09-17

5.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  5 in total
  1 in total

1.  4-Chloro-N-(3,4-dichloro-phen-yl)-2-methyl-benzene-sulfonamide.

Authors:  Vinola Z Rodrigues; Sabine Foro; B Thimme Gowda
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-10-12
  1 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.