Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807024221/dn2171sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807024221/dn2171Isup2.hkl |
CCDC reference: 244994
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (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
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).
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.
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.
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).
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).
C6H7NO2S | F(000) = 164 |
Mr = 157.19 | Dx = 1.481 Mg m−3 |
Monoclinic, Pc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P -2yc | Cell parameters from 706 reflections |
a = 8.304 (2) Å | θ = 2.0–30.0° |
b = 5.534 (1) Å | µ = 0.39 mm−1 |
c = 8.237 (2) Å | T = 295 K |
β = 111.36 (3)° | Plate, colourless |
V = 352.52 (15) Å3 | 0.52 × 0.46 × 0.09 mm |
Z = 2 |
Oxford Diffraction Xcalibur diffractometer | 621 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.086 |
Rotation method data acquisition using ω and phi scans | θmax = 25.7°, θmin = 4.5° |
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2006; Clark & Reid, 1995) | h = −10→10 |
Tmin = 0.812, Tmax = 0.956 | k = −6→6 |
2613 measured reflections | l = −10→8 |
1003 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.074 | H-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 reflections | Δρmax = 0.19 e Å−3 |
93 parameters | Δρmin = −0.31 e Å−3 |
5 restraints | Absolute structure: Flack (1983), with 356 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.1 (3) |
C6H7NO2S | V = 352.52 (15) Å3 |
Mr = 157.19 | Z = 2 |
Monoclinic, Pc | Mo Kα radiation |
a = 8.304 (2) Å | µ = 0.39 mm−1 |
b = 5.534 (1) Å | T = 295 K |
c = 8.237 (2) Å | 0.52 × 0.46 × 0.09 mm |
β = 111.36 (3)° |
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 = 0.956 | Rint = 0.086 |
2613 measured reflections |
R[F2 > 2σ(F2)] = 0.074 | H-atom parameters constrained |
wR(F2) = 0.260 | Δρmax = 0.19 e Å−3 |
S = 1.01 | Δρmin = −0.31 e Å−3 |
1003 reflections | Absolute structure: Flack (1983), with 356 Friedel pairs |
93 parameters | Absolute structure parameter: −0.1 (3) |
5 restraints |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 1.1057 (12) | 0.6751 (12) | 0.7719 (12) | 0.124 (2) | |
O2 | 1.0908 (12) | 1.0728 (16) | 0.6495 (18) | 0.153 (4) | |
S1 | 1.0618 (2) | 0.8225 (4) | 0.6248 (2) | 0.1057 (11) | |
C1 | 0.8412 (11) | 0.7887 (19) | 0.4996 (12) | 0.095 (3) | |
C2 | 0.7597 (12) | 0.9503 (16) | 0.3760 (14) | 0.096 (2) | |
H2 | 0.8191 | 1.0812 | 0.3544 | 0.115* | |
C3 | 0.5887 (15) | 0.919 (2) | 0.2829 (17) | 0.111 (3) | |
H3 | 0.5293 | 1.0355 | 0.2016 | 0.134* | |
C4 | 0.5006 (14) | 0.717 (2) | 0.3070 (17) | 0.111 (3) | |
H4 | 0.3844 | 0.6934 | 0.2395 | 0.133* | |
C5 | 0.5888 (16) | 0.5511 (17) | 0.4325 (17) | 0.109 (3) | |
H5 | 0.5307 | 0.4170 | 0.4519 | 0.130* | |
C6 | 0.7579 (12) | 0.5802 (16) | 0.5278 (13) | 0.096 (2) | |
H6 | 0.8182 | 0.4656 | 0.6100 | 0.115* | |
N1 | 1.1731 (11) | 0.734 (3) | 0.5134 (11) | 0.149 (4) | |
H1A | 1.1665 | 0.5763 | 0.4933 | 0.179* | |
H1B | 1.1408 | 0.8270 | 0.4185 | 0.179* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.131 (6) | 0.116 (5) | 0.115 (5) | 0.014 (4) | 0.035 (5) | −0.001 (4) |
O2 | 0.092 (5) | 0.168 (7) | 0.185 (9) | −0.035 (5) | 0.036 (6) | −0.078 (7) |
S1 | 0.0844 (13) | 0.126 (2) | 0.1070 (17) | 0.0067 (16) | 0.0350 (11) | −0.0243 (18) |
C1 | 0.071 (4) | 0.122 (7) | 0.094 (6) | 0.000 (5) | 0.032 (4) | −0.032 (5) |
C2 | 0.083 (5) | 0.098 (6) | 0.114 (7) | 0.003 (4) | 0.045 (5) | 0.011 (5) |
C3 | 0.099 (6) | 0.116 (7) | 0.121 (7) | 0.026 (6) | 0.043 (6) | 0.007 (7) |
C4 | 0.082 (5) | 0.126 (7) | 0.129 (9) | 0.000 (5) | 0.044 (5) | −0.029 (7) |
C5 | 0.114 (8) | 0.088 (6) | 0.137 (10) | −0.008 (5) | 0.062 (7) | 0.005 (6) |
C6 | 0.092 (6) | 0.087 (5) | 0.109 (7) | −0.003 (4) | 0.036 (5) | −0.006 (5) |
N1 | 0.067 (4) | 0.283 (13) | 0.097 (6) | 0.045 (7) | 0.029 (4) | −0.020 (7) |
O1—S1 | 1.394 (8) | C3—H3 | 0.9300 |
O2—S1 | 1.408 (9) | C4—C5 | 1.376 (16) |
S1—N1 | 1.597 (8) | C4—H4 | 0.9300 |
S1—C1 | 1.755 (9) | C5—C6 | 1.346 (15) |
C1—C2 | 1.339 (13) | C5—H5 | 0.9300 |
C1—C6 | 1.407 (15) | C6—H6 | 0.9300 |
C2—C3 | 1.356 (16) | N1—H1A | 0.8885 |
C2—H2 | 0.9300 | N1—H1B | 0.8901 |
C3—C4 | 1.393 (18) | ||
O1—S1—O2 | 118.2 (7) | C4—C3—H3 | 119.4 |
O1—S1—N1 | 107.3 (6) | C5—C4—C3 | 118.7 (10) |
O2—S1—N1 | 106.2 (8) | C5—C4—H4 | 120.7 |
O1—S1—C1 | 109.5 (5) | C3—C4—H4 | 120.7 |
O2—S1—C1 | 106.1 (6) | C6—C5—C4 | 121.0 (9) |
N1—S1—C1 | 109.2 (4) | C6—C5—H5 | 119.5 |
C2—C1—C6 | 122.0 (9) | C4—C5—H5 | 119.5 |
C2—C1—S1 | 120.4 (8) | C5—C6—C1 | 118.3 (9) |
C6—C1—S1 | 117.5 (8) | C5—C6—H6 | 120.9 |
C1—C2—C3 | 118.7 (9) | C1—C6—H6 | 120.9 |
C1—C2—H2 | 120.6 | S1—N1—H1A | 113.4 |
C3—C2—H2 | 120.6 | S1—N1—H1B | 106.0 |
C2—C3—C4 | 121.2 (10) | H1A—N1—H1B | 115.1 |
C2—C3—H3 | 119.4 |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1i | 0.89 | 2.20 | 2.932 (14) | 139 |
N1—H1B···O2ii | 0.89 | 2.17 | 3.016 (17) | 158 |
Symmetry codes: (i) x, −y+1, z−1/2; (ii) x, −y+2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C6H7NO2S |
Mr | 157.19 |
Crystal system, space group | Monoclinic, Pc |
Temperature (K) | 295 |
a, b, c (Å) | 8.304 (2), 5.534 (1), 8.237 (2) |
β (°) | 111.36 (3) |
V (Å3) | 352.52 (15) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.39 |
Crystal size (mm) | 0.52 × 0.46 × 0.09 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur |
Absorption correction | Analytical (CrysAlis RED; Oxford Diffraction, 2006; Clark & Reid, 1995) |
Tmin, Tmax | 0.812, 0.956 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2613, 1003, 621 |
Rint | 0.086 |
(sin θ/λ)max (Å−1) | 0.609 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.074, 0.260, 1.01 |
No. of reflections | 1003 |
No. of parameters | 93 |
No. of restraints | 5 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.31 |
Absolute structure | Flack (1983), with 356 Friedel pairs |
Absolute structure parameter | −0.1 (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).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1i | 0.89 | 2.20 | 2.932 (14) | 139.1 |
N1—H1B···O2ii | 0.89 | 2.17 | 3.016 (17) | 158.0 |
Symmetry codes: (i) x, −y+1, z−1/2; (ii) x, −y+2, z−1/2. |
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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.