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Acta Crystallogr Sect E Struct Rep Online. 2008 April 1; 64(Pt 4): o744.
Published online 2008 March 29. doi:  10.1107/S1600536808007447
PMCID: PMC2960949

2-Amino-N-(4-methyl­phenyl­sulfon­yl)-N-phenyl­benzene­sulfonamide

Abstract

In the title mol­ecule, C19H18N2O4S2, the phenyl ring makes dihedral angles of 33.99 (2) and 43.70 (3)° with the two methyl-substituted benzene rings. Inter­molecular N—H(...)O hydrogen bonds link the mol­ecules into centrosymmetric dimers. The crystal packing exhibits weak inter­molecular C—H(...)O hydrogen bonds.

Related literature

For the crystal structures of related compounds, see: Henschel et al. (1996 [triangle]). For details of the biological activities of sulfon­amide-containing compounds, see: Kamoshita et al. (1987 [triangle]). For related literature, see: Allen et al. (1987 [triangle]); Zhang et al. (2007 [triangle]).

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Object name is e-64-0o744-scheme1.jpg

Experimental

Crystal data

  • C19H18N2O4S2
  • M r = 402.47
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o744-efi1.jpg
  • a = 14.6245 (3) Å
  • b = 10.0454 (2) Å
  • c = 13.4735 (4) Å
  • β = 107.478 (2)°
  • V = 1887.99 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.31 mm−1
  • T = 293 (2) K
  • 0.52 × 0.32 × 0.25 mm

Data collection

  • Rigaku R-AXIS RAPID IP area-detector diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi 1995 [triangle]) T min = 0.855, T max = 0.926
  • 17437 measured reflections
  • 4312 independent reflections
  • 3531 reflections with I > 2σ(I)
  • R int = 0.038

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.121
  • S = 1.07
  • 4312 reflections
  • 245 parameters
  • H-atom parameters constrained
  • Δρmax = 0.40 e Å−3
  • Δρmin = −0.26 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2004 [triangle]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808007447/cv2388sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808007447/cv2388Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

Many compounds containing sulfonimide groups possess a broad spectrum of biological activities and can be used as herbicides (Kamoshita et al., 1987). In addition, some compounds containing sulfonimide groups can be used as catalysts (Zhang et al., 2007). Herein we report the crystal structure of the title compound, (I).

In (I) (Fig. 1), all bond lengths and angles are normal (Allen et al., 1987) and in a good agreement with those reported previously (Henschel et al., 1996). The phenyl ring (C7—C12) makes the dihedral angles of 33.99 (2) and 43.70 (3)°, respectively, with two benzene rings (C1—C6/N1 and C13—C19). The intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers. The crystal packing exhibits also weak intermolecular C—H···O hydrogen bonds (Table 1).

Experimental

A solution of methylsulfonyl chloride (1 mmol) was dissolved in anhydrous CH2Cl2 (10 ml), and dropwise added over a period of 10 min to a solution of 2-amino-N-methyl-benzenesulfonamide (1 mmol) and DMAP2 (3 mmol) in CH2Cl2 (10 ml) at 273 K. The mixture was stirred for 4 h at room temperature. The organic phase was washed with 2 N HCl twice, and dried over anhydrous Na2SO4. The solvent was removed and the residue was purified by flash chromatography (1:1 cyclohexane:dichloromethane) to give (I) as a white solid (294 mg, 73%). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethanol and dichloromethane at room temperature.

Refinement

H atoms were positioned geometrically with C—H = 0.93 or 0.96 Å, N—H=0.86 Å, and refined using a riding model, with Uiso(H) = 1.2 (1.5 for methyl groups) times Ueq(C, N).

Figures

Fig. 1.
The molecular structure of (I) showing the atomic numbering and 40% probability displacement ellipsoids.

Crystal data

C19H18N2O4S2F(000) = 840
Mr = 402.47Dx = 1.416 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2652 reflections
a = 14.6245 (3) Åθ = 2.6–25.6°
b = 10.0454 (2) ŵ = 0.31 mm1
c = 13.4735 (4) ÅT = 293 K
β = 107.478 (2)°Platelet, yellow
V = 1887.99 (7) Å30.52 × 0.32 × 0.25 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer4312 independent reflections
Radiation source: Rotating Anode3531 reflections with I > 2σ(I)
graphiteRint = 0.038
ω oscillation scansθmax = 27.5°, θmin = 1.5°
Absorption correction: multi-scan (ABSCOR; Higashi 1995)h = −18→18
Tmin = 0.855, Tmax = 0.927k = −13→13
17437 measured reflectionsl = −17→17

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.0647P)2 + 0.3731P] where P = (Fo2 + 2Fc2)/3
4312 reflections(Δ/σ)max = 0.001
245 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = −0.26 e Å3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
S10.18008 (3)0.28081 (5)0.24068 (4)0.04085 (14)
S20.24948 (3)0.51762 (5)0.14469 (3)0.04136 (14)
O10.24248 (10)0.20876 (14)0.32523 (12)0.0550 (4)
O20.16312 (11)0.23184 (16)0.13781 (11)0.0573 (4)
O30.18520 (10)0.46901 (19)0.05005 (10)0.0595 (4)
O40.24789 (12)0.65454 (14)0.17142 (12)0.0571 (4)
N10.22958 (11)0.43445 (16)0.24350 (11)0.0386 (3)
N2−0.00565 (13)0.3985 (2)0.09409 (13)0.0651 (6)
H2B−0.05420.43710.05150.078*
H2C0.04150.37270.07310.078*
C1−0.00348 (13)0.3782 (2)0.19378 (15)0.0431 (4)
C2−0.08053 (14)0.4204 (2)0.22702 (18)0.0541 (5)
H2D−0.13320.45990.17940.065*
C3−0.08033 (17)0.4052 (3)0.3272 (2)0.0667 (6)
H3B−0.13260.43460.34690.080*
C4−0.00295 (18)0.3463 (3)0.4010 (2)0.0691 (7)
H4B−0.00340.33700.46960.083*
C50.07352 (16)0.3022 (2)0.37162 (16)0.0540 (5)
H5A0.12510.26180.42020.065*
C60.07447 (12)0.31772 (19)0.26886 (14)0.0399 (4)
C70.25885 (13)0.49745 (18)0.34475 (13)0.0375 (4)
C80.19747 (14)0.5849 (2)0.37156 (16)0.0459 (4)
H8A0.13930.60760.32340.055*
C90.22318 (18)0.6384 (2)0.47042 (19)0.0586 (6)
H9A0.18210.69700.48940.070*
C100.3098 (2)0.6048 (3)0.54093 (18)0.0650 (6)
H10A0.32680.64060.60770.078*
C110.37175 (19)0.5185 (3)0.51344 (18)0.0640 (6)
H11A0.43020.49690.56150.077*
C120.34685 (14)0.4643 (2)0.41479 (15)0.0497 (5)
H12A0.38830.40660.39560.060*
C130.36661 (12)0.47731 (19)0.14622 (13)0.0384 (4)
C140.44113 (15)0.5618 (2)0.19508 (16)0.0514 (5)
H14A0.43010.63700.23010.062*
C150.53243 (15)0.5326 (2)0.19103 (18)0.0562 (5)
H15A0.58290.58900.22390.067*
C160.55032 (14)0.4216 (2)0.13933 (16)0.0494 (5)
C170.47460 (17)0.3389 (2)0.09216 (19)0.0590 (6)
H17A0.48600.26350.05760.071*
C180.38235 (15)0.3642 (2)0.09434 (18)0.0523 (5)
H18A0.33220.30710.06200.063*
C190.64941 (17)0.3926 (3)0.1334 (2)0.0718 (7)
H19A0.68500.47420.14020.108*
H19B0.64510.35210.06760.108*
H19C0.68150.33310.18870.108*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0370 (2)0.0369 (2)0.0459 (3)0.00456 (18)0.00835 (18)−0.00020 (18)
S20.0365 (2)0.0506 (3)0.0373 (2)0.00913 (19)0.01168 (18)0.00992 (19)
O10.0466 (8)0.0449 (8)0.0664 (9)0.0112 (6)0.0064 (7)0.0118 (7)
O20.0573 (9)0.0564 (9)0.0567 (8)0.0020 (7)0.0148 (7)−0.0172 (7)
O30.0401 (7)0.0969 (12)0.0360 (7)0.0060 (8)0.0031 (6)0.0088 (7)
O40.0668 (10)0.0444 (8)0.0697 (9)0.0160 (7)0.0354 (8)0.0182 (7)
N10.0390 (8)0.0422 (8)0.0361 (7)−0.0013 (6)0.0133 (6)0.0008 (6)
N20.0426 (9)0.1027 (17)0.0438 (9)0.0165 (10)0.0037 (7)0.0140 (10)
C10.0340 (8)0.0449 (10)0.0468 (10)−0.0028 (8)0.0067 (7)0.0042 (8)
C20.0347 (9)0.0589 (13)0.0679 (13)0.0040 (9)0.0145 (9)0.0136 (11)
C30.0513 (12)0.0765 (16)0.0834 (16)0.0059 (12)0.0371 (12)0.0146 (14)
C40.0654 (15)0.0889 (19)0.0633 (14)0.0073 (14)0.0350 (12)0.0226 (13)
C50.0492 (11)0.0615 (13)0.0510 (11)0.0031 (10)0.0147 (9)0.0201 (10)
C60.0326 (8)0.0389 (9)0.0460 (9)−0.0015 (7)0.0085 (7)0.0053 (8)
C70.0395 (9)0.0388 (9)0.0352 (8)−0.0038 (7)0.0128 (7)−0.0001 (7)
C80.0444 (10)0.0430 (10)0.0532 (11)0.0009 (8)0.0189 (8)−0.0003 (8)
C90.0690 (14)0.0522 (12)0.0646 (13)−0.0004 (11)0.0353 (11)−0.0124 (10)
C100.0861 (18)0.0632 (14)0.0464 (12)−0.0049 (13)0.0208 (11)−0.0143 (10)
C110.0643 (14)0.0713 (15)0.0459 (11)0.0031 (12)0.0005 (10)−0.0055 (11)
C120.0429 (10)0.0574 (12)0.0459 (10)0.0052 (9)0.0089 (8)−0.0034 (9)
C130.0341 (8)0.0462 (10)0.0355 (8)0.0042 (7)0.0116 (7)0.0048 (7)
C140.0454 (11)0.0551 (12)0.0541 (11)−0.0023 (9)0.0157 (9)−0.0107 (10)
C150.0390 (10)0.0646 (14)0.0620 (13)−0.0083 (10)0.0104 (9)−0.0056 (11)
C160.0384 (10)0.0553 (12)0.0573 (12)0.0063 (9)0.0189 (9)0.0121 (9)
C170.0546 (12)0.0540 (12)0.0748 (15)0.0035 (10)0.0291 (11)−0.0118 (11)
C180.0416 (10)0.0533 (12)0.0627 (12)−0.0037 (9)0.0168 (9)−0.0106 (10)
C190.0484 (12)0.0763 (17)0.100 (2)0.0100 (12)0.0359 (13)0.0127 (15)

Geometric parameters (Å, °)

S1—O21.4206 (15)C8—C91.379 (3)
S1—O11.4248 (14)C8—H8A0.9300
S1—N11.7002 (16)C9—C101.378 (3)
S1—C61.7378 (19)C9—H9A0.9300
S2—O41.4237 (16)C10—C111.382 (4)
S2—O31.4241 (15)C10—H10A0.9300
S2—N11.6698 (15)C11—C121.380 (3)
S2—C131.7543 (18)C11—H11A0.9300
N1—C71.447 (2)C12—H12A0.9300
N2—C11.349 (3)C13—C141.382 (3)
N2—H2B0.8600C13—C181.389 (3)
N2—H2C0.8600C14—C151.384 (3)
C1—C21.398 (3)C14—H14A0.9300
C1—C61.414 (2)C15—C161.380 (3)
C2—C31.357 (3)C15—H15A0.9300
C2—H2D0.9300C16—C171.377 (3)
C3—C41.394 (3)C16—C191.504 (3)
C3—H3B0.9300C17—C181.382 (3)
C4—C51.367 (3)C17—H17A0.9300
C4—H4B0.9300C18—H18A0.9300
C5—C61.397 (3)C19—H19A0.9600
C5—H5A0.9300C19—H19B0.9600
C7—C81.380 (3)C19—H19C0.9600
C7—C121.389 (3)
O2—S1—O1119.11 (10)C9—C8—C7119.4 (2)
O2—S1—N1106.54 (9)C9—C8—H8A120.3
O1—S1—N1106.09 (8)C7—C8—H8A120.3
O2—S1—C6112.39 (9)C10—C9—C8119.9 (2)
O1—S1—C6109.36 (9)C10—C9—H9A120.1
N1—S1—C6101.64 (8)C8—C9—H9A120.1
O4—S2—O3120.08 (10)C9—C10—C11120.6 (2)
O4—S2—N1105.17 (8)C9—C10—H10A119.7
O3—S2—N1108.43 (9)C11—C10—H10A119.7
O4—S2—C13108.07 (9)C12—C11—C10120.1 (2)
O3—S2—C13108.12 (9)C12—C11—H11A120.0
N1—S2—C13106.17 (8)C10—C11—H11A120.0
C7—N1—S2117.37 (12)C11—C12—C7118.8 (2)
C7—N1—S1114.93 (11)C11—C12—H12A120.6
S2—N1—S1127.69 (9)C7—C12—H12A120.6
C1—N2—H2B120.0C14—C13—C18121.05 (18)
C1—N2—H2C120.0C14—C13—S2119.43 (15)
H2B—N2—H2C120.0C18—C13—S2119.45 (15)
N2—C1—C2119.54 (18)C13—C14—C15118.9 (2)
N2—C1—C6123.36 (18)C13—C14—H14A120.6
C2—C1—C6117.10 (18)C15—C14—H14A120.6
C3—C2—C1121.5 (2)C16—C15—C14121.5 (2)
C3—C2—H2D119.2C16—C15—H15A119.3
C1—C2—H2D119.2C14—C15—H15A119.3
C2—C3—C4121.1 (2)C17—C16—C15118.16 (19)
C2—C3—H3B119.5C17—C16—C19120.9 (2)
C4—C3—H3B119.5C15—C16—C19121.0 (2)
C5—C4—C3119.3 (2)C16—C17—C18122.3 (2)
C5—C4—H4B120.3C16—C17—H17A118.9
C3—C4—H4B120.3C18—C17—H17A118.9
C4—C5—C6120.2 (2)C17—C18—C13118.12 (19)
C4—C5—H5A119.9C17—C18—H18A120.9
C6—C5—H5A119.9C13—C18—H18A120.9
C5—C6—C1120.73 (18)C16—C19—H19A109.5
C5—C6—S1117.82 (14)C16—C19—H19B109.5
C1—C6—S1120.92 (14)H19A—C19—H19B109.5
C8—C7—C12121.20 (18)C16—C19—H19C109.5
C8—C7—N1119.59 (16)H19A—C19—H19C109.5
C12—C7—N1119.15 (17)H19B—C19—H19C109.5
O4—S2—N1—C7−27.73 (15)S2—N1—C7—C885.99 (19)
O3—S2—N1—C7−157.36 (13)S1—N1—C7—C8−95.07 (18)
C13—S2—N1—C786.67 (14)S2—N1—C7—C12−96.67 (19)
O4—S2—N1—S1153.48 (12)S1—N1—C7—C1282.28 (19)
O3—S2—N1—S123.85 (15)C12—C7—C8—C9−1.3 (3)
C13—S2—N1—S1−92.12 (13)N1—C7—C8—C9176.02 (18)
O2—S1—N1—C7−175.64 (13)C7—C8—C9—C100.4 (3)
O1—S1—N1—C7−47.78 (15)C8—C9—C10—C110.4 (4)
C6—S1—N1—C766.53 (14)C9—C10—C11—C12−0.4 (4)
O2—S1—N1—S23.18 (14)C10—C11—C12—C7−0.4 (4)
O1—S1—N1—S2131.04 (12)C8—C7—C12—C111.2 (3)
C6—S1—N1—S2−114.65 (12)N1—C7—C12—C11−176.1 (2)
N2—C1—C2—C3−178.3 (2)O4—S2—C13—C1416.10 (18)
C6—C1—C2—C30.6 (3)O3—S2—C13—C14147.52 (16)
C1—C2—C3—C4−0.2 (4)N1—S2—C13—C14−96.30 (17)
C2—C3—C4—C5−0.6 (4)O4—S2—C13—C18−161.03 (16)
C3—C4—C5—C60.8 (4)O3—S2—C13—C18−29.62 (19)
C4—C5—C6—C1−0.4 (3)N1—S2—C13—C1886.56 (17)
C4—C5—C6—S1171.3 (2)C18—C13—C14—C150.5 (3)
N2—C1—C6—C5178.5 (2)S2—C13—C14—C15−176.61 (17)
C2—C1—C6—C5−0.3 (3)C13—C14—C15—C160.1 (3)
N2—C1—C6—S17.1 (3)C14—C15—C16—C17−0.6 (3)
C2—C1—C6—S1−171.74 (16)C14—C15—C16—C19178.6 (2)
O2—S1—C6—C5148.79 (17)C15—C16—C17—C180.6 (4)
O1—S1—C6—C514.18 (19)C19—C16—C17—C18−178.7 (2)
N1—S1—C6—C5−97.68 (17)C16—C17—C18—C130.0 (4)
O2—S1—C6—C1−39.51 (19)C14—C13—C18—C17−0.5 (3)
O1—S1—C6—C1−174.13 (15)S2—C13—C18—C17176.55 (17)
N1—S1—C6—C174.01 (17)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2B···O3i0.862.203.062 (2)176.
C19—H19A···O1ii0.962.573.517 (3)169.
C19—H19C···O4iii0.962.583.538 (3)174.
N2—H2C···O20.862.232.893 (2)133.

Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+1, y−1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2388).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Henschel, D., Hiemisch, O., Blaschette, A. & Jones, P. G. (1996). Z. Naturforsch. Teil B, 51, 1313–1315.
  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Kamoshita, K., Matsumoto, H. & Nagano, E. (1987). US Patent 4 670 046.
  • Rigaku (2004). RAPID-AUTO Version 3.0. Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Zhang, Z. B., Zhou, S. Y. & Nie, J. (2007). J. Mol. Catal. A Chem 265, 9–14.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography