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The structures of three substituted arenesulfonamides have been solved from laboratory X-ray powder diffraction data, using a new direct-space structure solution method based on a differential evolution algorithm, and refined by the Rietveld method. In 2-toluenesulfonamide, C7H9NO2S (I) (tetragonal I41/a, Z = 16), the molecules are linked by N—H...O=S hydrogen bonds into a three-dimensional framework. In 3-nitrobenzenesulfonamide, C6H6N2O4S (II) (monoclinic P21, Z = 2), N—H...O=S hydrogen bonds produce molecular ladders, which are linked into sheets by C—H...O=S hydrogen bonds: the nitro group does not participate in the hydrogen bonding. Molecules of 4-nitrobenzenesulfonamide, C6H6N2O4S (III) (monoclinic P21/n, Z = 4), are linked into sheets by four types of hydrogen bond, N—H...O=S, N—H...O(nitro), C—H...O=S and C—H...O(nitro), and the sheets are weakly linked by aromatic π...π stacking interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768102011928/bm0052sup1.cif
Contains datablocks global, otols, 4NBS, 3NBS

rtv

Rietveld powder data file (CIF format) https://doi.org/10.1107/S0108768102011928/bm0052otolssup2.rtv
Contains datablock otols

rtv

Rietveld powder data file (CIF format) https://doi.org/10.1107/S0108768102011928/bm00524NBSsup3.rtv
Contains datablock 4NBS

rtv

Rietveld powder data file (CIF format) https://doi.org/10.1107/S0108768102011928/bm00523NBSsup4.rtv
Contains datablock 3NBS

CCDC references: 195799; 195800; 195801

Computing details top

For all compounds, data collection: Diffrac-AT (Siemens). Program(s) used to solve structure: POSSUM (Seaton et al. 2002) for otols; POSSUM (Tremayne, Seaton 2002) for 4NBS, 3NBS. For all compounds, program(s) used to refine structure: GSAS (Larson et al. 1994).

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(otols) ortho-toluenesulfonamide top
Crystal data top
C7H9NO2SZ = 16
Mr = 171.22Cu Kα1 radiation, λ = 1.54056 Å
Tetragonal, I41/aT = 273 K
a = 18.7407 (8) Åwhite
c = 9.1004 (4) Åplate, 30 × 0.5 mm
V = 3196.2 (3) Å3
Data collection top
Position sensitive detector
diffractometer
Specimen mounting: disc
Radiation source: sealed X-ray tubeData collection mode: transmission
Ge monochromator2θmin = 4.00°, 2θmax = 53.971°, 2θstep = 0.019°
Refinement top
Rp = 0.077Profile function: pseudovoigt
Rwp = 0.09846 parameters
Rexp = ?39 restraints
R(F2) = 0.1078H-atom parameters constrained
χ2 = 11.676
? data pointsPreferred orientation correction: none
Crystal data top
C7H9NO2SV = 3196.2 (3) Å3
Mr = 171.22Z = 16
Tetragonal, I41/aCu Kα1 radiation, λ = 1.54056 Å
a = 18.7407 (8) ÅT = 273 K
c = 9.1004 (4) Åplate, 30 × 0.5 mm
Data collection top
Position sensitive detector
diffractometer
Data collection mode: transmission
Specimen mounting: disc2θmin = 4.00°, 2θmax = 53.971°, 2θstep = 0.019°
Refinement top
Rp = 0.077? data points
Rwp = 0.09846 parameters
Rexp = ?39 restraints
R(F2) = 0.1078H-atom parameters constrained
χ2 = 11.676
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.3646 (4)0.6256 (4)0.7649 (7)0.028 (3)*
N10.4060 (7)0.5904 (7)0.629 (1)0.020 (9)*
O110.2905 (6)0.6025 (7)0.748 (1)0.064 (5)*
O120.3800 (9)0.7016 (5)0.758 (2)0.063 (5)*
C10.4016 (6)0.5867 (8)0.927 (1)0.020 (4)*
C20.4661 (8)0.609 (1)0.989 (2)0.020 (4)*
C30.4914 (8)0.579 (1)1.122 (2)0.020 (4)*
C40.4440 (9)0.541 (1)1.212 (1)0.020 (4)*
C50.375 (1)0.528 (1)1.154 (2)0.020 (4)*
C60.3519 (7)0.550 (1)1.014 (2)0.020 (4)*
C70.5200 (8)0.651 (1)0.902 (2)0.075 (1)*
H30.542 (3)0.598 (5)1.171 (6)0.05*
H40.464 (2)0.512 (5)1.307 (7)0.05*
H50.340 (3)0.494 (6)1.221 (7)0.05*
H60.2947 (8)0.561 (4)0.997 (6)0.05*
H110.38730.54270.57900.05*
H120.45400.60260.58090.05*
H710.49050.67490.82460.05*
H720.54000.68500.97580.05*
H730.55700.61740.86330.05*
Geometric parameters (Å, º) top
C1—C21.397 (8)C4—C51.407 (8)
C1—C61.406 (8)C5—C61.410 (8)
C1—S11.783 (7)S1—N11.599 (7)
C2—C31.418 (8)S1—O111.463 (7)
C2—C71.506 (8)S1—O121.454 (7)
C3—C41.397 (8)
C2—C1—C6119 (1)C4—C5—C6125 (1)
C2—C1—S1123 (1)C1—C6—C5116 (1)
C6—C1—S1114 (1)C1—S1—N1106 (1)
C1—C2—C3121 (1)C1—S1—O11110 (1)
C1—C2—C7122 (1)C1—S1—O12111 (1)
C3—C2—C7116 (1)N1—S1—O11105 (1)
C2—C3—C4119 (1)N1—S1—O12106 (1)
C3—C4—C5117 (1)O11—S1—O12118 (1)
(4NBS) "4-nitrobenzenesulfonamide" top
Crystal data top
C6H6N2O4SV = 829.9 (2) Å3
Mr = 202.20Z = 4
Monoclinic, P21/nCu Kα radiation, λ = 1.54056 Å
a = 8.8424 (3) ÅT = 273 K
b = 13.4933 (4) Åorange
c = 7.0732 (2) Åplate, 30 × 0.5 mm
β = 100.466 (2)°
Data collection top
Position sensitive detector
diffractometer
Specimen mounting: disc
Radiation source: sealed X-ray tubeData collection mode: transmission
Ge monochromator2θmin = 4.00°, 2θmax = 53.974°, 2θstep = 0.019°
Refinement top
Rp = 0.072Profile function: pseudovoigt
Rwp = 0.05358 parameters
Rexp = ?46 restraints
R(F2) = 0.1646H-atom parameters constrained
χ2 = 33.779
? data pointsPreferred orientation correction: none
Crystal data top
C6H6N2O4Sβ = 100.466 (2)°
Mr = 202.20V = 829.9 (2) Å3
Monoclinic, P21/nZ = 4
a = 8.8424 (3) ÅCu Kα radiation, λ = 1.54056 Å
b = 13.4933 (4) ÅT = 273 K
c = 7.0732 (2) Åplate, 30 × 0.5 mm
Data collection top
Position sensitive detector
diffractometer
Data collection mode: transmission
Specimen mounting: disc2θmin = 4.00°, 2θmax = 53.974°, 2θstep = 0.019°
Refinement top
Rp = 0.072? data points
Rwp = 0.05358 parameters
Rexp = ?46 restraints
R(F2) = 0.1646H-atom parameters constrained
χ2 = 33.779
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.5590 (7)0.7705 (4)0.8930 (8)0.033 (3)*
N10.6911 (9)0.7149 (3)1.034 (1)0.010 (7)*
O110.587 (1)0.8316 (7)0.737 (1)0.028 (5)*
O120.466 (1)0.6857 (7)0.817 (1)0.028 (5)*
C10.448 (2)0.849 (1)1.022 (2)0.025 (4)*
C20.333 (2)0.910 (1)0.920 (2)0.025 (4)*
C30.257 (2)0.978 (1)1.022 (2)0.025 (4)*
C40.275 (2)0.967 (2)1.221 (2)0.025 (4)*
C50.396 (2)0.910 (2)1.325 (2)0.025 (4)*
C60.483 (2)0.851 (2)1.223 (2)0.025 (4)*
N40.176 (2)1.023 (1)1.337 (2)0.010 (8)*
O410.222 (1)1.0171 (9)1.506 (2)0.015 (5)*
O420.089 (1)1.0712 (9)1.225 (1)0.015 (5)*
H210.33 (1)0.919 (6)0.764 (3)0.05*
H310.22 (1)1.050 (3)0.957 (6)0.05*
H510.431 (9)0.921 (6)1.481 (3)0.05*
H610.57 (1)0.804 (8)1.302 (4)0.05*
H110.7770.7461.1240.05*
H120.7000.6401.0250.05*
Geometric parameters (Å, º) top
C1—C21.403 (4)C5—C61.396 (4)
C1—C61.401 (4)S1—N11.579 (4)
C1—S11.797 (4)S1—O111.435 (4)
C2—C31.408 (4)S1—O121.453 (4)
C3—C41.402 (4)N4—O411.193 (4)
C4—C51.403 (4)N4—O421.192 (4)
C4—N41.511 (4)
C2—C1—C6120 (1)C1—S1—N1112 (1)
C2—C1—S1120 (1)C1—S1—O11104 (1)
C6—C1—S1119 (1)C1—S1—O12109 (1)
C1—C2—C3120 (1)N1—S1—O11123 (1)
C2—C3—C4118 (1)N1—S1—O1299 (1)
C3—C4—C5120 (1)O11—S1—O12109 (1)
C3—C4—N4121 (1)C4—N4—O41112 (1)
C5—C4—N4117 (1)C4—N4—O42107 (1)
C4—C5—C6118 (1)O41—N4—O42140 (1)
C1—C6—C5120 (1)
(3NBS) "3-nitrobenzenesulfonamide" top
Crystal data top
C6H6N2O4SV = 409.93 (2) Å3
Mr = 202.20Z = 2
Monoclinic, P21Cu Kα radiation, λ = 1.5418 Å
a = 7.7169 (2) ÅT = 273 K
b = 8.0514 (2) Åwhite
c = 7.0334 (2) Åplate, 30 × 0.5 mm
β = 110.274 (1)°
Data collection top
Position sensitive detector
diffractometer
Specimen mounting: capillary
Radiation source: sealed X-ray tubeData collection mode: transmission
None monochromator2θmin = 8.00°, 2θmax = 50.021°, 2θstep = 0.019°
Refinement top
Rp = 0.063Profile function: pseudovoigt
Rwp = 0.04759 parameters
Rexp = ?46 restraints
R(F2) = 0.0565H-atom parameters constrained
χ2 = ?
? data pointsPreferred orientation correction: none
Crystal data top
C6H6N2O4Sβ = 110.274 (1)°
Mr = 202.20V = 409.93 (2) Å3
Monoclinic, P21Z = 2
a = 7.7169 (2) ÅCu Kα radiation, λ = 1.5418 Å
b = 8.0514 (2) ÅT = 273 K
c = 7.0334 (2) Åplate, 30 × 0.5 mm
Data collection top
Position sensitive detector
diffractometer
Data collection mode: transmission
Specimen mounting: capillary2θmin = 8.00°, 2θmax = 50.021°, 2θstep = 0.019°
Refinement top
Rp = 0.063? data points
Rwp = 0.04759 parameters
Rexp = ?46 restraints
R(F2) = 0.0565H-atom parameters constrained
χ2 = ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S11.023 (1)0.645 (3)0.370 (1)0.070 (3)*
N10.935 (2)0.6586 (6)0.548 (2)0.013 (6)*
O111.133 (2)0.791 (3)0.384 (2)0.035 (4)*
O121.165 (2)0.522 (3)0.432 (2)0.035 (4)*
C10.875 (2)0.618 (4)0.121 (2)0.020 (4)*
C20.796 (3)0.463 (3)0.090 (2)0.020 (4)*
C30.658 (3)0.446 (3)0.099 (3)0.020 (4)*
C40.580 (3)0.581 (3)0.229 (2)0.020 (4)*
C50.650 (3)0.739 (3)0.150 (2)0.020 (4)*
C60.805 (3)0.767 (3)0.027 (2)0.020 (4)*
N30.627 (2)0.267 (3)0.179 (2)0.039 (9)*
O310.683 (1)0.144 (3)0.055 (2)0.049 (4)*
O320.464 (2)0.251 (3)0.313 (2)0.049 (4)*
H210.888 (8)0.354 (6)0.14 (1)0.05*
H410.49 (1)0.567 (6)0.388 (6)0.05*
H510.56 (1)0.845 (5)0.22 (1)0.05*
H610.906 (7)0.868 (6)0.053 (9)0.05*
H110.9130.5390.5760.05*
H120.9040.7790.5610.05*
Geometric parameters (Å, º) top
C1—C21.378 (6)C5—C61.413 (6)
C1—C61.384 (6)S1—N11.619 (5)
C1—S11.741 (6)S1—O111.430 (6)
C2—C31.394 (6)S1—O121.433 (6)
C3—C41.410 (6)N3—O311.288 (6)
C3—N31.540 (6)N3—O321.292 (6)
C4—C51.418 (6)
C2—C1—C6129 (1)C1—S1—N1119 (1)
C2—C1—S1112 (1)C1—S1—O11110 (1)
C6—C1—S1112 (1)C1—S1—O12113 (1)
C1—C2—C3113 (1)N1—S1—O11107 (1)
C2—C3—C4124 (1)N1—S1—O12107 (1)
C2—C3—N3114 (1)O11—S1—O12100 (1)
C4—C3—N3121 (1)C3—N3—O31120 (1)
C3—C4—C5115 (1)C3—N3—O32110 (1)
C4—C5—C6125 (1)O31—N3—O32116 (1)
C1—C6—C5111 (1)

Experimental details

(otols)(4NBS)(3NBS)
Crystal data
Chemical formulaC7H9NO2SC6H6N2O4SC6H6N2O4S
Mr171.22202.20202.20
Crystal system, space groupTetragonal, I41/aMonoclinic, P21/nMonoclinic, P21
Temperature (K)273273273
a, b, c (Å)18.7407 (8), 18.7407 (8), 9.1004 (4)8.8424 (3), 13.4933 (4), 7.0732 (2)7.7169 (2), 8.0514 (2), 7.0334 (2)
α, β, γ (°)90, 90, 9090, 100.466 (2), 9090, 110.274 (1), 90
V3)3196.2 (3)829.9 (2)409.93 (2)
Z1642
Radiation typeCu Kα1, λ = 1.54056 ÅCu Kα, λ = 1.54056 ÅCu Kα, λ = 1.5418 Å
µ (mm1)???
Specimen shape, size (mm)Plate, 30 × 0.5Plate, 30 × 0.5Plate, 30 × 0.5
Data collection
DiffractometerPosition sensitive detector
diffractometer
Position sensitive detector
diffractometer
Position sensitive detector
diffractometer
Specimen mountingDiscDiscCapillary
Data collection modeTransmissionTransmissionTransmission
Scan method???
2θ values (°)2θmin = 4.00 2θmax = 53.971 2θstep = 0.0192θmin = 4.00 2θmax = 53.974 2θstep = 0.0192θmin = 8.00 2θmax = 50.021 2θstep = 0.019
Refinement
R factors and goodness of fitRp = 0.077, Rwp = 0.098, Rexp = ?, R(F2) = 0.1078, χ2 = 11.676Rp = 0.072, Rwp = 0.053, Rexp = ?, R(F2) = 0.1646, χ2 = 33.779Rp = 0.063, Rwp = 0.047, Rexp = ?, R(F2) = 0.0565, χ2 = ?
No. of data points???
No. of parameters465859
No. of restraints394646
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained

Computer programs: Diffrac-AT (Siemens), POSSUM (Seaton et al. 2002), POSSUM (Tremayne, Seaton 2002), GSAS (Larson et al. 1994).

 

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