organic compounds
N-(2,3-Dimethylphenyl)-4-fluoro-N-[(4-fluorophenyl)sulfonyl]benzenesulfonamide
aMaterials Chemistry Laboratry, Department of Chemistry, GC University, Lahore 54000, Pakistan, bDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland, cQuestioned Documents Unit, Punjab Forensic Science Agency, Home Department, Lahore, Pakistan, and dDepartment of Physics, University of Sargodha, Punjab, Pakistan
*Correspondence e-mail: koolmuneeb@yahoo.com
In the title compound, C20H17F2NO4S2, the dihedral angles between the o-xylene ring and the fluorobenzene rings are 31.7 (1) and 32.8 (1)°, and the dihedral angle between the fluorobenzene rings is 50.9 (1)°. The C—N—S—C torsion angles are 76.7 (2) and 101.8 (2)°. In the crystal, molecules are connected by C—H⋯O interactions into sheets in the ab plane.
Related literature
For related crystal structures, see: Hanson & Hitchcock (2004); Low et al. (2006); Mughal et al. (2012).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
Supporting information
https://doi.org/10.1107/S1600536812039402/ld2072sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812039402/ld2072Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812039402/ld2072Isup3.cml
0.10 g of 2,3-dimethyl aniline was dissolved in 15 ml dichloromethane, and 0.16 g of 4-fluoro benzene sulfonyl chloride was added. The mixture was stirred at room temperature overnight and its pH was maintained at 8–9 with triethylamine. On completion of the reaction (after TLC), 1M HCl solution was added, the organic fraction was separated, and the solvent was evaporated at room temperature to generate dark brown crystals in 94% yield. Yellow blocks were recrystallized from ethanol solution.
The H atoms were placed in calculated positions (C—H = 0.93–0.96 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). The methyl groups were allowed to rotate to fit the electron density.
Rather than the intended 4-fluoro-N-(2,3-dimethylphenyl)benzenesulfonamide, the title `double' sulfonamide (I), (Fig. 1) was unexpectedly obtained in our ongoing studies (Mughal et al., 2012). The related structures of 4-chloroaniline-N,N-ditoluene-p-sulfonamide, (II) (Hanson & Hitchcock, 2004) and 4-iodo-N,N-bis-(2-nitrophenylsulfonyl)aniline, (III) (Low et al., 2006) have been described previously.
The molecule of (I) cannot possess any
due to the two methyl groups of the xylene ring. Without them, the rest of the moleucle possesses approximate local twofold symmetry about the C1—N1 axis.The sulfonamide C—N—S—C torsion angles in (I) [76.7 (2) and 101.8 (2)°] compare well to the corresponding value of 80.2° reported in (II), where the molecule posesses a crystallographic twofold symmetry. The respective values in (III) are 98.9 (2) and 94.3 (2)°. The bond-angle sum for the N atom in (I) of 359.7° implies sp2
for the N atom.In the crystal of (I), there are weak C—H···O hydrogen bonds between the molecules (Table 1). The C8 bond results in translational chains along [100] and the C19 bond results in helices along [010]. Together these generate (001) sheets.
For related crystal structures, see: Hanson & Hitchcock (2004); Low et al. (2006); Mughal et al. (2012).
Data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).Fig. 1. The molecular structure of (I), showing displacement ellipsoids at the 50% probability level. |
C20H17F2NO4S2 | Dx = 1.488 Mg m−3 |
Mr = 437.47 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 202 reflections |
a = 9.9493 (5) Å | θ = 3.2–20.5° |
b = 14.7107 (8) Å | µ = 0.32 mm−1 |
c = 26.6871 (17) Å | T = 296 K |
V = 3906.0 (4) Å3 | Block, yellow |
Z = 8 | 0.28 × 0.25 × 0.23 mm |
F(000) = 1808 |
Bruker APEXII CCD diffractometer | 4352 independent reflections |
Radiation source: fine-focus sealed tube | 2943 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.046 |
ω scans | θmax = 27.3°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2008) | h = −12→12 |
Tmin = 0.916, Tmax = 0.930 | k = −18→14 |
31734 measured reflections | l = −34→34 |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.133 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0524P)2 + 2.7378P] where P = (Fo2 + 2Fc2)/3 |
4352 reflections | (Δ/σ)max < 0.001 |
264 parameters | Δρmax = 0.47 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
C20H17F2NO4S2 | V = 3906.0 (4) Å3 |
Mr = 437.47 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 9.9493 (5) Å | µ = 0.32 mm−1 |
b = 14.7107 (8) Å | T = 296 K |
c = 26.6871 (17) Å | 0.28 × 0.25 × 0.23 mm |
Bruker APEXII CCD diffractometer | 4352 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2008) | 2943 reflections with I > 2σ(I) |
Tmin = 0.916, Tmax = 0.930 | Rint = 0.046 |
31734 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.133 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.47 e Å−3 |
4352 reflections | Δρmin = −0.29 e Å−3 |
264 parameters |
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 | 0.6678 (3) | 0.45285 (18) | 0.13773 (11) | 0.0504 (7) | |
C2 | 0.7555 (3) | 0.48512 (18) | 0.10252 (10) | 0.0540 (7) | |
C3 | 0.8910 (3) | 0.4952 (2) | 0.11660 (13) | 0.0616 (8) | |
C4 | 0.9311 (4) | 0.4696 (2) | 0.16383 (14) | 0.0717 (9) | |
H4 | 1.0208 | 0.4763 | 0.1729 | 0.086* | |
C5 | 0.8414 (4) | 0.4343 (2) | 0.19804 (14) | 0.0765 (10) | |
H5 | 0.8715 | 0.4167 | 0.2296 | 0.092* | |
C6 | 0.7092 (3) | 0.4250 (2) | 0.18605 (11) | 0.0595 (8) | |
H6 | 0.6480 | 0.4011 | 0.2089 | 0.071* | |
C7 | 0.7112 (3) | 0.5083 (2) | 0.05128 (11) | 0.0666 (9) | |
H7A | 0.7561 | 0.4696 | 0.0276 | 0.100* | |
H7B | 0.7328 | 0.5706 | 0.0443 | 0.100* | |
H7C | 0.6158 | 0.4996 | 0.0486 | 0.100* | |
C8 | 0.9920 (4) | 0.5330 (3) | 0.08077 (16) | 0.0961 (13) | |
H8A | 1.0796 | 0.5312 | 0.0958 | 0.144* | |
H8B | 0.9691 | 0.5947 | 0.0729 | 0.144* | |
H8C | 0.9922 | 0.4973 | 0.0506 | 0.144* | |
C9 | 0.4640 (3) | 0.62628 (17) | 0.11107 (10) | 0.0451 (6) | |
C10 | 0.5733 (3) | 0.68129 (19) | 0.12047 (12) | 0.0571 (7) | |
H10 | 0.6275 | 0.6707 | 0.1483 | 0.069* | |
C11 | 0.6018 (4) | 0.7518 (2) | 0.08853 (14) | 0.0733 (9) | |
H11 | 0.6744 | 0.7902 | 0.0943 | 0.088* | |
C12 | 0.5205 (4) | 0.7638 (2) | 0.04815 (14) | 0.0768 (10) | |
C13 | 0.4101 (4) | 0.7119 (2) | 0.03854 (12) | 0.0749 (10) | |
H13 | 0.3554 | 0.7241 | 0.0111 | 0.090* | |
C14 | 0.3816 (3) | 0.6414 (2) | 0.07036 (10) | 0.0583 (7) | |
H14 | 0.3077 | 0.6041 | 0.0646 | 0.070* | |
C15 | 0.3779 (3) | 0.29685 (18) | 0.14708 (9) | 0.0449 (6) | |
C16 | 0.2445 (3) | 0.31051 (19) | 0.15903 (10) | 0.0517 (7) | |
H16 | 0.1919 | 0.3501 | 0.1402 | 0.062* | |
C17 | 0.1902 (3) | 0.2645 (2) | 0.19928 (11) | 0.0557 (7) | |
H17 | 0.1007 | 0.2728 | 0.2083 | 0.067* | |
C18 | 0.2703 (3) | 0.2067 (2) | 0.22544 (10) | 0.0542 (7) | |
C19 | 0.4012 (3) | 0.1897 (2) | 0.21330 (11) | 0.0569 (7) | |
H19 | 0.4518 | 0.1480 | 0.2314 | 0.068* | |
C20 | 0.4558 (3) | 0.23611 (19) | 0.17354 (10) | 0.0518 (7) | |
H20 | 0.5450 | 0.2265 | 0.1645 | 0.062* | |
S1 | 0.43137 (7) | 0.53555 (5) | 0.15106 (3) | 0.0483 (2) | |
S2 | 0.45376 (7) | 0.35921 (5) | 0.09885 (2) | 0.0494 (2) | |
F1 | 0.5499 (3) | 0.83173 (15) | 0.01607 (9) | 0.1272 (10) | |
F2 | 0.21844 (19) | 0.16374 (13) | 0.26576 (7) | 0.0773 (6) | |
O1 | 0.4877 (2) | 0.55627 (14) | 0.19840 (7) | 0.0654 (6) | |
O2 | 0.29538 (19) | 0.50962 (14) | 0.14719 (9) | 0.0677 (6) | |
O3 | 0.3540 (2) | 0.39068 (16) | 0.06534 (7) | 0.0704 (6) | |
O4 | 0.5668 (2) | 0.30948 (14) | 0.08134 (7) | 0.0622 (5) | |
N1 | 0.5226 (2) | 0.44974 (14) | 0.12742 (8) | 0.0444 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0518 (16) | 0.0389 (14) | 0.0604 (17) | −0.0005 (12) | 0.0075 (13) | −0.0049 (12) |
C2 | 0.0611 (17) | 0.0435 (16) | 0.0574 (17) | 0.0019 (13) | 0.0051 (14) | −0.0018 (13) |
C3 | 0.0486 (16) | 0.0509 (17) | 0.085 (2) | 0.0025 (14) | −0.0022 (16) | −0.0086 (16) |
C4 | 0.064 (2) | 0.063 (2) | 0.088 (2) | −0.0010 (17) | 0.0044 (19) | −0.0038 (18) |
C5 | 0.081 (2) | 0.080 (2) | 0.068 (2) | 0.006 (2) | −0.0230 (19) | 0.0015 (18) |
C6 | 0.0580 (18) | 0.0585 (18) | 0.0619 (18) | −0.0002 (15) | −0.0060 (14) | 0.0022 (14) |
C7 | 0.083 (2) | 0.0597 (19) | 0.0573 (18) | 0.0066 (17) | 0.0038 (16) | 0.0049 (15) |
C8 | 0.071 (2) | 0.105 (3) | 0.112 (3) | −0.021 (2) | 0.015 (2) | 0.003 (3) |
C9 | 0.0491 (15) | 0.0359 (13) | 0.0502 (14) | −0.0006 (12) | 0.0011 (12) | −0.0053 (11) |
C10 | 0.0583 (18) | 0.0478 (16) | 0.0653 (18) | −0.0045 (14) | −0.0030 (15) | −0.0058 (14) |
C11 | 0.082 (2) | 0.0494 (18) | 0.089 (3) | −0.0206 (17) | 0.008 (2) | −0.0050 (17) |
C12 | 0.115 (3) | 0.0473 (18) | 0.068 (2) | −0.007 (2) | 0.017 (2) | 0.0057 (16) |
C13 | 0.109 (3) | 0.068 (2) | 0.0487 (17) | 0.008 (2) | −0.0091 (18) | 0.0019 (16) |
C14 | 0.0642 (18) | 0.0571 (18) | 0.0534 (17) | −0.0027 (15) | −0.0054 (14) | −0.0081 (14) |
C15 | 0.0503 (15) | 0.0404 (14) | 0.0440 (14) | −0.0087 (12) | −0.0049 (12) | −0.0045 (11) |
C16 | 0.0473 (15) | 0.0484 (16) | 0.0594 (17) | −0.0078 (13) | −0.0102 (13) | 0.0035 (13) |
C17 | 0.0451 (15) | 0.0568 (17) | 0.0651 (18) | −0.0104 (14) | 0.0022 (14) | −0.0016 (14) |
C18 | 0.0577 (18) | 0.0554 (17) | 0.0496 (15) | −0.0180 (14) | −0.0034 (13) | 0.0017 (13) |
C19 | 0.0578 (18) | 0.0541 (17) | 0.0588 (17) | −0.0048 (14) | −0.0106 (14) | 0.0102 (14) |
C20 | 0.0458 (15) | 0.0510 (16) | 0.0585 (17) | −0.0007 (13) | −0.0005 (13) | 0.0005 (13) |
S1 | 0.0486 (4) | 0.0448 (4) | 0.0516 (4) | 0.0001 (3) | 0.0086 (3) | −0.0025 (3) |
S2 | 0.0592 (4) | 0.0494 (4) | 0.0397 (3) | −0.0057 (3) | −0.0004 (3) | −0.0028 (3) |
F1 | 0.209 (3) | 0.0732 (14) | 0.0998 (17) | −0.0283 (17) | 0.0147 (18) | 0.0319 (13) |
F2 | 0.0742 (12) | 0.0903 (14) | 0.0672 (11) | −0.0198 (10) | 0.0045 (10) | 0.0228 (10) |
O1 | 0.0839 (15) | 0.0678 (13) | 0.0445 (11) | 0.0104 (12) | 0.0046 (10) | −0.0086 (9) |
O2 | 0.0462 (11) | 0.0566 (13) | 0.1003 (17) | −0.0017 (10) | 0.0155 (11) | 0.0027 (11) |
O3 | 0.0764 (15) | 0.0838 (15) | 0.0510 (11) | −0.0119 (12) | −0.0174 (11) | 0.0096 (11) |
O4 | 0.0746 (14) | 0.0565 (12) | 0.0556 (12) | −0.0007 (11) | 0.0155 (10) | −0.0153 (10) |
N1 | 0.0429 (11) | 0.0399 (12) | 0.0503 (12) | −0.0012 (9) | 0.0031 (10) | −0.0043 (10) |
C1—C2 | 1.367 (4) | C11—H11 | 0.9300 |
C1—C6 | 1.414 (4) | C12—F1 | 1.348 (4) |
C1—N1 | 1.471 (4) | C12—C13 | 1.362 (5) |
C2—C3 | 1.407 (4) | C13—C14 | 1.371 (4) |
C2—C7 | 1.476 (4) | C13—H13 | 0.9300 |
C3—C4 | 1.375 (5) | C14—H14 | 0.9300 |
C3—C8 | 1.495 (5) | C15—C20 | 1.377 (4) |
C4—C5 | 1.378 (5) | C15—C16 | 1.380 (4) |
C4—H4 | 0.9300 | C15—S2 | 1.751 (3) |
C5—C6 | 1.361 (4) | C16—C17 | 1.380 (4) |
C5—H5 | 0.9300 | C16—H16 | 0.9300 |
C6—H6 | 0.9300 | C17—C18 | 1.358 (4) |
C7—H7A | 0.9600 | C17—H17 | 0.9300 |
C7—H7B | 0.9600 | C18—F2 | 1.350 (3) |
C7—H7C | 0.9600 | C18—C19 | 1.365 (4) |
C8—H8A | 0.9600 | C19—C20 | 1.374 (4) |
C8—H8B | 0.9600 | C19—H19 | 0.9300 |
C8—H8C | 0.9600 | C20—H20 | 0.9300 |
C9—C10 | 1.378 (4) | S1—O2 | 1.410 (2) |
C9—C14 | 1.379 (4) | S1—O1 | 1.415 (2) |
C9—S1 | 1.739 (3) | S1—N1 | 1.678 (2) |
C10—C11 | 1.373 (4) | S2—O3 | 1.414 (2) |
C10—H10 | 0.9300 | S2—O4 | 1.421 (2) |
C11—C12 | 1.359 (5) | S2—N1 | 1.681 (2) |
C2—C1—C6 | 122.8 (3) | C11—C12—C13 | 123.8 (3) |
C2—C1—N1 | 120.6 (3) | C12—C13—C14 | 118.3 (3) |
C6—C1—N1 | 116.6 (2) | C12—C13—H13 | 120.8 |
C1—C2—C3 | 117.6 (3) | C14—C13—H13 | 120.8 |
C1—C2—C7 | 121.8 (3) | C13—C14—C9 | 119.1 (3) |
C3—C2—C7 | 120.6 (3) | C13—C14—H14 | 120.4 |
C4—C3—C2 | 119.6 (3) | C9—C14—H14 | 120.4 |
C4—C3—C8 | 119.5 (3) | C20—C15—C16 | 121.1 (3) |
C2—C3—C8 | 120.8 (3) | C20—C15—S2 | 118.3 (2) |
C3—C4—C5 | 121.5 (3) | C16—C15—S2 | 120.5 (2) |
C3—C4—H4 | 119.3 | C17—C16—C15 | 119.0 (3) |
C5—C4—H4 | 119.3 | C17—C16—H16 | 120.5 |
C6—C5—C4 | 120.6 (3) | C15—C16—H16 | 120.5 |
C6—C5—H5 | 119.7 | C18—C17—C16 | 118.5 (3) |
C4—C5—H5 | 119.7 | C18—C17—H17 | 120.7 |
C5—C6—C1 | 117.8 (3) | C16—C17—H17 | 120.7 |
C5—C6—H6 | 121.1 | F2—C18—C17 | 118.6 (3) |
C1—C6—H6 | 121.1 | F2—C18—C19 | 117.9 (3) |
C2—C7—H7A | 109.5 | C17—C18—C19 | 123.5 (3) |
C2—C7—H7B | 109.5 | C18—C19—C20 | 118.0 (3) |
H7A—C7—H7B | 109.5 | C18—C19—H19 | 121.0 |
C2—C7—H7C | 109.5 | C20—C19—H19 | 121.0 |
H7A—C7—H7C | 109.5 | C19—C20—C15 | 119.7 (3) |
H7B—C7—H7C | 109.5 | C19—C20—H20 | 120.1 |
C3—C8—H8A | 109.5 | C15—C20—H20 | 120.1 |
C3—C8—H8B | 109.5 | O2—S1—O1 | 120.26 (14) |
H8A—C8—H8B | 109.5 | O2—S1—N1 | 106.76 (12) |
C3—C8—H8C | 109.5 | O1—S1—N1 | 106.45 (12) |
H8A—C8—H8C | 109.5 | O2—S1—C9 | 110.01 (13) |
H8B—C8—H8C | 109.5 | O1—S1—C9 | 107.96 (13) |
C10—C9—C14 | 121.2 (3) | N1—S1—C9 | 104.21 (11) |
C10—C9—S1 | 119.1 (2) | O3—S2—O4 | 121.08 (13) |
C14—C9—S1 | 119.7 (2) | O3—S2—N1 | 108.28 (13) |
C11—C10—C9 | 119.6 (3) | O4—S2—N1 | 103.57 (11) |
C11—C10—H10 | 120.2 | O3—S2—C15 | 109.50 (13) |
C9—C10—H10 | 120.2 | O4—S2—C15 | 108.24 (13) |
C12—C11—C10 | 117.9 (3) | N1—S2—C15 | 104.92 (11) |
C12—C11—H11 | 121.0 | C1—N1—S1 | 115.94 (17) |
C10—C11—H11 | 121.0 | C1—N1—S2 | 120.65 (17) |
F1—C12—C11 | 118.1 (4) | S1—N1—S2 | 123.10 (13) |
F1—C12—C13 | 118.1 (4) | ||
C6—C1—C2—C3 | −3.5 (4) | C18—C19—C20—C15 | −0.7 (4) |
N1—C1—C2—C3 | 173.5 (2) | C16—C15—C20—C19 | −1.6 (4) |
C6—C1—C2—C7 | 176.0 (3) | S2—C15—C20—C19 | 176.6 (2) |
N1—C1—C2—C7 | −6.9 (4) | C10—C9—S1—O2 | 158.3 (2) |
C1—C2—C3—C4 | 2.3 (4) | C14—C9—S1—O2 | −22.4 (3) |
C7—C2—C3—C4 | −177.3 (3) | C10—C9—S1—O1 | 25.3 (3) |
C1—C2—C3—C8 | −177.9 (3) | C14—C9—S1—O1 | −155.4 (2) |
C7—C2—C3—C8 | 2.5 (5) | C10—C9—S1—N1 | −87.6 (2) |
C2—C3—C4—C5 | −0.2 (5) | C14—C9—S1—N1 | 91.7 (2) |
C8—C3—C4—C5 | −179.9 (3) | C20—C15—S2—O3 | 158.7 (2) |
C3—C4—C5—C6 | −0.9 (5) | C16—C15—S2—O3 | −23.2 (3) |
C4—C5—C6—C1 | −0.2 (5) | C20—C15—S2—O4 | 24.8 (2) |
C2—C1—C6—C5 | 2.5 (5) | C16—C15—S2—O4 | −157.1 (2) |
N1—C1—C6—C5 | −174.6 (3) | C20—C15—S2—N1 | −85.3 (2) |
C14—C9—C10—C11 | −0.7 (4) | C16—C15—S2—N1 | 92.8 (2) |
S1—C9—C10—C11 | 178.6 (2) | C2—C1—N1—S1 | −98.9 (3) |
C9—C10—C11—C12 | −0.8 (5) | C6—C1—N1—S1 | 78.3 (3) |
C10—C11—C12—F1 | −178.5 (3) | C2—C1—N1—S2 | 87.2 (3) |
C10—C11—C12—C13 | 2.4 (6) | C6—C1—N1—S2 | −95.6 (3) |
F1—C12—C13—C14 | 178.4 (3) | O2—S1—N1—C1 | −166.84 (19) |
C11—C12—C13—C14 | −2.5 (6) | O1—S1—N1—C1 | −37.2 (2) |
C12—C13—C14—C9 | 0.9 (5) | C9—S1—N1—C1 | 76.7 (2) |
C10—C9—C14—C13 | 0.6 (4) | O2—S1—N1—S2 | 6.85 (19) |
S1—C9—C14—C13 | −178.6 (2) | O1—S1—N1—S2 | 136.46 (16) |
C20—C15—C16—C17 | 2.2 (4) | C9—S1—N1—S2 | −109.56 (16) |
S2—C15—C16—C17 | −175.9 (2) | O3—S2—N1—C1 | −141.3 (2) |
C15—C16—C17—C18 | −0.5 (4) | O4—S2—N1—C1 | −11.6 (2) |
C16—C17—C18—F2 | 178.0 (2) | C15—S2—N1—C1 | 101.8 (2) |
C16—C17—C18—C19 | −1.8 (4) | O3—S2—N1—S1 | 45.28 (19) |
F2—C18—C19—C20 | −177.4 (2) | O4—S2—N1—S1 | 175.00 (15) |
C17—C18—C19—C20 | 2.4 (4) | C15—S2—N1—S1 | −71.57 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8A···O2i | 0.96 | 2.57 | 3.517 (5) | 170 |
C19—H19···O1ii | 0.93 | 2.39 | 3.260 (4) | 157 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C20H17F2NO4S2 |
Mr | 437.47 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 296 |
a, b, c (Å) | 9.9493 (5), 14.7107 (8), 26.6871 (17) |
V (Å3) | 3906.0 (4) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.32 |
Crystal size (mm) | 0.28 × 0.25 × 0.23 |
Data collection | |
Diffractometer | Bruker APEXII CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2008) |
Tmin, Tmax | 0.916, 0.930 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 31734, 4352, 2943 |
Rint | 0.046 |
(sin θ/λ)max (Å−1) | 0.644 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.133, 1.02 |
No. of reflections | 4352 |
No. of parameters | 264 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.47, −0.29 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8A···O2i | 0.96 | 2.57 | 3.517 (5) | 170 |
C19—H19···O1ii | 0.93 | 2.39 | 3.260 (4) | 157 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, y−1/2, −z+1/2. |
Acknowledgements
The authors are grateful to the Higher Education Commission of Pakistan for providing a grant under a project strengthening the Materials Chemistry Laboratory at GC University, Lahore.
References
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Hanson, J. R. & Hitchcock, P. B. (2004). J. Chem. Res. p. 614. CrossRef Google Scholar
Low, J. N., Skakle, J. M. S., Wardell, J. L. & Glidewell, C. (2006). Acta Cryst. C62, o423–o425. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Mughal, S. Y., Khan, I. U., Harrison, W. T. A., Khan, M. H. & Arshad, M. N. (2012). Acta Cryst. E68, o2433. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS 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.
Rather than the intended 4-fluoro-N-(2,3-dimethylphenyl)benzenesulfonamide, the title `double' sulfonamide (I), (Fig. 1) was unexpectedly obtained in our ongoing studies (Mughal et al., 2012). The related structures of 4-chloroaniline-N,N-ditoluene-p-sulfonamide, (II) (Hanson & Hitchcock, 2004) and 4-iodo-N,N-bis-(2-nitrophenylsulfonyl)aniline, (III) (Low et al., 2006) have been described previously.
The molecule of (I) cannot possess any local symmetry due to the two methyl groups of the xylene ring. Without them, the rest of the moleucle possesses approximate local twofold symmetry about the C1—N1 axis.
The sulfonamide C—N—S—C torsion angles in (I) [76.7 (2) and 101.8 (2)°] compare well to the corresponding value of 80.2° reported in (II), where the molecule posesses a crystallographic twofold symmetry. The respective values in (III) are 98.9 (2) and 94.3 (2)°. The bond-angle sum for the N atom in (I) of 359.7° implies sp2 hybridization for the N atom.
In the crystal of (I), there are weak C—H···O hydrogen bonds between the molecules (Table 1). The C8 bond results in translational chains along [100] and the C19 bond results in helices along [010]. Together these generate (001) sheets.