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The structure of the title compound (BSA), C6H7NO2S, closely resembles those of other aryl sulfonamides. The geometric parameters in BSA are similar except for some difference in the S=O bond lengths. Mol­ecules are connected by N—H...O hydrogen bonds into layers parallel to the bc plane, with an inter­layer distance of 7.734 (2) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807024221/dn2171sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807024221/dn2171Isup2.hkl
Contains datablock I

CCDC reference: 244994

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.016 Å
  • R factor = 0.074
  • wR factor = 0.260
  • Data-to-parameter ratio = 11.3

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT340_ALERT_3_B Low Bond Precision on C-C Bonds (x 1000) Ang ... 16
Alert level C RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25 Weighted R factor given 0.260 PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro . ? PLAT084_ALERT_2_C High R2 Value .................................. 0.26 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for S1 PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C1 -C6 1.37 Ang.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.66 From the CIF: _reflns_number_total 1003 Count of symmetry unique reflns 668 Completeness (_total/calc) 150.15% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 335 Fraction of Friedel pairs measured 0.501 Are heavy atom types Z>Si present yes PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 5
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The chemistry of sulfonamides is of interest as they show distinct physical, chemical and biological properties. Many arylsulfonamides and their N-halo compounds exhibit pharmacological, fungicidal and herbicidal activities due to their oxidizing action in aqueous, partial aqueous and non-aqueous media. Thus N-halo arylsulfonamides are of interest in synthetic, mechanistic, analytical and biological chemistry (Gowda et al., 2002; 2003; 2005; 2007; Gowda & Shetty, 2004). In the present work, the structure of benzenesulfonamde (BSA) has been determined to explore the substituent effects on the solid state structures of sulfonamides and N-halo arylsulfonamides (Gowda et al., 2003, 2007). The structure of BSA (Fig. 1) closely resembles those of other aryl sulfonamides (Gowda et al., 2003; Jones & Weinkauf, 1993; Kumar et al., 1992; O'Connor & Maslen, 1965). The parent sulphonamide, BSA crystallizes in monoclinic Pc space group in contrast to orthorhombic Pbca space group observed with 4-fluorobenzenesulfonamide (Jones & Weinkauf, 1993) and 4-aminobenzenesulfonamide (O'Connor & Maslen, 1965) and monoclinic P21/n space group observed with 4-chlorobenzenesulfonamide and 4-bromobenzenesulfonamide (Gowda et al., 2003), and 4-methylbenzenesulfonamide (Kumar et al., 1992). The bond parameters in BSA are similar except for some slight differences in the S—O bond lengths.

Molecules are connected by N—H···O hydrogen bonds into layers parallel to the bc-plane (Fig.2), with interlayer distance 7.734 (2) Å.

Related literature top

For related literature, see: Gowda & Shetty (2004); Gowda et al. (2002, 2003, 2005, 2007); Jones & Weinkauf (1993); Kumar et al. (1992); O'Connor & Maslen (1965).

Experimental top

The title compound was prepared according to the literature method (Gowda et al., 2002, 2003). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra (Gowda et al., 2002). Single crystals of the title compound were obtained from a slow evaporation of its ethanolic solution and used for X-ray diffraction studies at room temperature.

Refinement top

Monoclinic crystal (1) was refined as twinned, with two twin domains (fractional contributions 84 and 16 percent). The non-merohedral twinning was analysed using TwinRotMat routine within WinGX package. It was found that 22 percent of total reflections were overlapped with rotation matrix (1.000 0.000 0.734) (0.000 - 1.000 0.000) (0.000 0.000 - 1.000) Using the above twin matrix a HKLF5 file was generated which was subsequenly used in the SHELXL97 refinement of the structure. The BASF parameter was refined to final value 0.154.

Hydrogen atoms attached to carbons were positioned geometrically and treated as riding with C–H = 0.93 Å. H atoms attached to N1 atom were placed in positions with N–H bond distance restrained to 0.89 (2)Å and H–H restrained to 1.50 (3) Å. In the last stage of refinement, these H were treated as riding on their parent N atom with Uiso(H)=1.2 Ueq(N).

Although the N atom has an elongated ellipsoids, no reasonable disordered model could be defined.

Owing to the poor quality of the data, the absolute structure couldn't be reliably defined and any references to the Flack parameter have been omitted. The Friedel pairs were merged.

Structure description top

The chemistry of sulfonamides is of interest as they show distinct physical, chemical and biological properties. Many arylsulfonamides and their N-halo compounds exhibit pharmacological, fungicidal and herbicidal activities due to their oxidizing action in aqueous, partial aqueous and non-aqueous media. Thus N-halo arylsulfonamides are of interest in synthetic, mechanistic, analytical and biological chemistry (Gowda et al., 2002; 2003; 2005; 2007; Gowda & Shetty, 2004). In the present work, the structure of benzenesulfonamde (BSA) has been determined to explore the substituent effects on the solid state structures of sulfonamides and N-halo arylsulfonamides (Gowda et al., 2003, 2007). The structure of BSA (Fig. 1) closely resembles those of other aryl sulfonamides (Gowda et al., 2003; Jones & Weinkauf, 1993; Kumar et al., 1992; O'Connor & Maslen, 1965). The parent sulphonamide, BSA crystallizes in monoclinic Pc space group in contrast to orthorhombic Pbca space group observed with 4-fluorobenzenesulfonamide (Jones & Weinkauf, 1993) and 4-aminobenzenesulfonamide (O'Connor & Maslen, 1965) and monoclinic P21/n space group observed with 4-chlorobenzenesulfonamide and 4-bromobenzenesulfonamide (Gowda et al., 2003), and 4-methylbenzenesulfonamide (Kumar et al., 1992). The bond parameters in BSA are similar except for some slight differences in the S—O bond lengths.

Molecules are connected by N—H···O hydrogen bonds into layers parallel to the bc-plane (Fig.2), with interlayer distance 7.734 (2) Å.

For related literature, see: Gowda & Shetty (2004); Gowda et al. (2002, 2003, 2005, 2007); Jones & Weinkauf (1993); Kumar et al. (1992); O'Connor & Maslen (1965).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003) and WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. ORTEP view of the title compound showing the atom labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
[Figure 2] Fig. 2. Packing of the title compound viewed down the b axis, showing molecular layers parallel to the bc-plane. Within a layer the molecules are connected by N—H···O hydrogen bonds (dashed lines). H atoms not involved in hydrogen bondings have been omitted for clarity.
Benzenesulfonamide top
Crystal data top
C6H7NO2SF(000) = 164
Mr = 157.19Dx = 1.481 Mg m3
Monoclinic, PcMo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2ycCell parameters from 706 reflections
a = 8.304 (2) Åθ = 2.0–30.0°
b = 5.534 (1) ŵ = 0.39 mm1
c = 8.237 (2) ÅT = 295 K
β = 111.36 (3)°Plate, colourless
V = 352.52 (15) Å30.52 × 0.46 × 0.09 mm
Z = 2
Data collection top
Oxford Diffraction Xcalibur
diffractometer
621 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.086
Rotation method data acquisition using ω and phi scansθmax = 25.7°, θmin = 4.5°
Absorption correction: analytical
(CrysAlis RED; Oxford Diffraction, 2006; Clark & Reid, 1995)
h = 1010
Tmin = 0.812, Tmax = 0.956k = 66
2613 measured reflectionsl = 108
1003 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.074H-atom parameters constrained
wR(F2) = 0.260 w = 1/[σ2(Fo2) + (0.1777P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
1003 reflectionsΔρmax = 0.19 e Å3
93 parametersΔρmin = 0.31 e Å3
5 restraintsAbsolute structure: Flack (1983), with 356 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.1 (3)
Crystal data top
C6H7NO2SV = 352.52 (15) Å3
Mr = 157.19Z = 2
Monoclinic, PcMo Kα radiation
a = 8.304 (2) ŵ = 0.39 mm1
b = 5.534 (1) ÅT = 295 K
c = 8.237 (2) Å0.52 × 0.46 × 0.09 mm
β = 111.36 (3)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer
1003 independent reflections
Absorption correction: analytical
(CrysAlis RED; Oxford Diffraction, 2006; Clark & Reid, 1995)
621 reflections with I > 2σ(I)
Tmin = 0.812, Tmax = 0.956Rint = 0.086
2613 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.074H-atom parameters constrained
wR(F2) = 0.260Δρmax = 0.19 e Å3
S = 1.01Δρmin = 0.31 e Å3
1003 reflectionsAbsolute structure: Flack (1983), with 356 Friedel pairs
93 parametersAbsolute structure parameter: 0.1 (3)
5 restraints
Special details top

Experimental. Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid, 1995).

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) top
xyzUiso*/Ueq
O11.1057 (12)0.6751 (12)0.7719 (12)0.124 (2)
O21.0908 (12)1.0728 (16)0.6495 (18)0.153 (4)
S11.0618 (2)0.8225 (4)0.6248 (2)0.1057 (11)
C10.8412 (11)0.7887 (19)0.4996 (12)0.095 (3)
C20.7597 (12)0.9503 (16)0.3760 (14)0.096 (2)
H20.81911.08120.35440.115*
C30.5887 (15)0.919 (2)0.2829 (17)0.111 (3)
H30.52931.03550.20160.134*
C40.5006 (14)0.717 (2)0.3070 (17)0.111 (3)
H40.38440.69340.23950.133*
C50.5888 (16)0.5511 (17)0.4325 (17)0.109 (3)
H50.53070.41700.45190.130*
C60.7579 (12)0.5802 (16)0.5278 (13)0.096 (2)
H60.81820.46560.61000.115*
N11.1731 (11)0.734 (3)0.5134 (11)0.149 (4)
H1A1.16650.57630.49330.179*
H1B1.14080.82700.41850.179*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.131 (6)0.116 (5)0.115 (5)0.014 (4)0.035 (5)0.001 (4)
O20.092 (5)0.168 (7)0.185 (9)0.035 (5)0.036 (6)0.078 (7)
S10.0844 (13)0.126 (2)0.1070 (17)0.0067 (16)0.0350 (11)0.0243 (18)
C10.071 (4)0.122 (7)0.094 (6)0.000 (5)0.032 (4)0.032 (5)
C20.083 (5)0.098 (6)0.114 (7)0.003 (4)0.045 (5)0.011 (5)
C30.099 (6)0.116 (7)0.121 (7)0.026 (6)0.043 (6)0.007 (7)
C40.082 (5)0.126 (7)0.129 (9)0.000 (5)0.044 (5)0.029 (7)
C50.114 (8)0.088 (6)0.137 (10)0.008 (5)0.062 (7)0.005 (6)
C60.092 (6)0.087 (5)0.109 (7)0.003 (4)0.036 (5)0.006 (5)
N10.067 (4)0.283 (13)0.097 (6)0.045 (7)0.029 (4)0.020 (7)
Geometric parameters (Å, º) top
O1—S11.394 (8)C3—H30.9300
O2—S11.408 (9)C4—C51.376 (16)
S1—N11.597 (8)C4—H40.9300
S1—C11.755 (9)C5—C61.346 (15)
C1—C21.339 (13)C5—H50.9300
C1—C61.407 (15)C6—H60.9300
C2—C31.356 (16)N1—H1A0.8885
C2—H20.9300N1—H1B0.8901
C3—C41.393 (18)
O1—S1—O2118.2 (7)C4—C3—H3119.4
O1—S1—N1107.3 (6)C5—C4—C3118.7 (10)
O2—S1—N1106.2 (8)C5—C4—H4120.7
O1—S1—C1109.5 (5)C3—C4—H4120.7
O2—S1—C1106.1 (6)C6—C5—C4121.0 (9)
N1—S1—C1109.2 (4)C6—C5—H5119.5
C2—C1—C6122.0 (9)C4—C5—H5119.5
C2—C1—S1120.4 (8)C5—C6—C1118.3 (9)
C6—C1—S1117.5 (8)C5—C6—H6120.9
C1—C2—C3118.7 (9)C1—C6—H6120.9
C1—C2—H2120.6S1—N1—H1A113.4
C3—C2—H2120.6S1—N1—H1B106.0
C2—C3—C4121.2 (10)H1A—N1—H1B115.1
C2—C3—H3119.4
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.892.202.932 (14)139
N1—H1B···O2ii0.892.173.016 (17)158
Symmetry codes: (i) x, y+1, z1/2; (ii) x, y+2, z1/2.

Experimental details

Crystal data
Chemical formulaC6H7NO2S
Mr157.19
Crystal system, space groupMonoclinic, Pc
Temperature (K)295
a, b, c (Å)8.304 (2), 5.534 (1), 8.237 (2)
β (°) 111.36 (3)
V3)352.52 (15)
Z2
Radiation typeMo Kα
µ (mm1)0.39
Crystal size (mm)0.52 × 0.46 × 0.09
Data collection
DiffractometerOxford Diffraction Xcalibur
Absorption correctionAnalytical
(CrysAlis RED; Oxford Diffraction, 2006; Clark & Reid, 1995)
Tmin, Tmax0.812, 0.956
No. of measured, independent and
observed [I > 2σ(I)] reflections
2613, 1003, 621
Rint0.086
(sin θ/λ)max1)0.609
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.074, 0.260, 1.01
No. of reflections1003
No. of parameters93
No. of restraints5
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.19, 0.31
Absolute structureFlack (1983), with 356 Friedel pairs
Absolute structure parameter0.1 (3)

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003) and WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.892.202.932 (14)139.1
N1—H1B···O2ii0.892.173.016 (17)158.0
Symmetry codes: (i) x, y+1, z1/2; (ii) x, y+2, z1/2.
 

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