Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807016443/bt2331sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807016443/bt2331Isup2.hkl |
CCDC reference: 614628
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean (C-C) = 0.006 Å
- R factor = 0.048
- wR factor = 0.124
- Data-to-parameter ratio = 13.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.07 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 1.070 Tmax scaled 0.918 Tmin scaled 0.666
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 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 et al. (2007); Gowda et al. (2007a); Gowda et al. (2007b); Gowda et al. (2000); Jayalakshmi & Gowda (2004); Klug (1968).
The title compound was prepared according to the literature method (Jayalakshmi & Gowda, 2004). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra (Jayalakshmi & Gowda, 2004). Single crystals of the title compound were obtained from a slow evaporation of its ethanolic solution.
Methyl groups were refined as riding with C—H = 0.96Å and Uiso(H) = 1.2 Ueq(C). The coordinates of the remaining H atoms were refined with Uiso(H) = 1.2 Ueq(C,N).
The stereochemistry of biologically important alkyl sulfonanilides is of interest in explaining their biological activity. The biological activity may be due to N—H group. Therefore the structural studies of sulfonanilides are of interest. In the present work, the structure of N-(3-methylphenyl)-methanesulfonamde (3MPMSA) has been determined to explore the substituent effects on the structures of anilides and sulfonanilides (Gowda et al., 2000, 2007, 2007a,b). The conformation of the N—H bond in the structure of 3MPMSA, is anti to the meta-methyl substituent (Fig.1), similar to that observed in the corresponding meta- nitro substituted sulfonanilide (3NPMSA)(Gowda et al., 2007b). The bond parameters in the 3 compounds, PMSA (Klug, 1968), 3MPMSA and 3NPMSA are similar except in the S—N—C bond angle [120.0 (1)° (PMSA); 121.2 (2)° (3MPMSA); 126.3 (3)° (3NPMSA)] and in the S—N—C—C torsion angles [S2—N5—C6—C7 and S2—N5—C6—C11: 75.5 (2)° and -106.6 (2)° (PMSA); 68.1 (4)° and -114.3 (3)° (3MPMSA); 41.1 (3)°, -140.8 (2)° (3NPMSA)]. The molecules are linked in chains in the direction of c axis through N—H···O hydrogen bonds. (Table 1 and Fig. 2).
For related literature, see: Gowda et al. (2007); Gowda et al. (2007a); Gowda et al. (2007b); Gowda et al. (2000); Jayalakshmi & Gowda (2004); Klug (1968).
Data collection: CAD-4-PC (Enraf–Nonius, 1996); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
C8H11NO2S | F(000) = 784 |
Mr = 185.24 | Dx = 1.348 Mg m−3 |
Orthorhombic, Pccn | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: -P 2ab 2ac | Cell parameters from 25 reflections |
a = 23.218 (2) Å | θ = 3.8–22.8° |
b = 8.4933 (7) Å | µ = 2.84 mm−1 |
c = 9.2561 (8) Å | T = 299 K |
V = 1825.3 (3) Å3 | Laminar, colourless |
Z = 8 | 0.25 × 0.10 × 0.03 mm |
Enraf–Nonius CAD-4 diffractometer | 975 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.044 |
Graphite monochromator | θmax = 66.8°, θmin = 3.8° |
ω/2θ scans | h = −27→0 |
Absorption correction: psi-scan (North et al., 1968) | k = −10→2 |
Tmin = 0.623, Tmax = 0.859 | l = −11→0 |
1875 measured reflections | 3 standard reflections every 120 min |
1618 independent reflections | intensity decay: 2.2% |
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: difference Fourier map |
wR(F2) = 0.124 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0551P)2] where P = (Fo2 + 2Fc2)/3 |
1618 reflections | (Δ/σ)max < 0.001 |
124 parameters | Δρmax = 0.20 e Å−3 |
1 restraint | Δρmin = −0.36 e Å−3 |
C8H11NO2S | V = 1825.3 (3) Å3 |
Mr = 185.24 | Z = 8 |
Orthorhombic, Pccn | Cu Kα radiation |
a = 23.218 (2) Å | µ = 2.84 mm−1 |
b = 8.4933 (7) Å | T = 299 K |
c = 9.2561 (8) Å | 0.25 × 0.10 × 0.03 mm |
Enraf–Nonius CAD-4 diffractometer | 975 reflections with I > 2σ(I) |
Absorption correction: psi-scan (North et al., 1968) | Rint = 0.044 |
Tmin = 0.623, Tmax = 0.859 | 3 standard reflections every 120 min |
1875 measured reflections | intensity decay: 2.2% |
1618 independent reflections |
R[F2 > 2σ(F2)] = 0.048 | 1 restraint |
wR(F2) = 0.124 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.20 e Å−3 |
1618 reflections | Δρmin = −0.36 e Å−3 |
124 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 | 0.49810 (16) | 0.2700 (5) | 0.0568 (4) | 0.0565 (10) | |
H1A | 0.5140 | 0.3265 | 0.1373 | 0.068* | |
H1B | 0.4865 | 0.3432 | −0.0166 | 0.068* | |
H1C | 0.5267 | 0.1999 | 0.0183 | 0.068* | |
C6 | 0.37038 (14) | 0.4150 (4) | 0.1081 (4) | 0.0370 (8) | |
C7 | 0.33344 (16) | 0.3904 (5) | −0.0062 (4) | 0.0435 (9) | |
H7 | 0.3240 (15) | 0.295 (4) | −0.033 (4) | 0.052* | |
C8 | 0.31135 (16) | 0.5164 (5) | −0.0843 (4) | 0.0492 (10) | |
C9 | 0.32608 (18) | 0.6653 (6) | −0.0410 (5) | 0.0575 (11) | |
H9 | 0.3117 (16) | 0.744 (6) | −0.089 (5) | 0.069* | |
C10 | 0.36123 (19) | 0.6921 (5) | 0.0767 (5) | 0.0567 (12) | |
H10 | 0.3701 (16) | 0.791 (5) | 0.105 (5) | 0.068* | |
C11 | 0.38420 (17) | 0.5653 (5) | 0.1511 (4) | 0.0487 (10) | |
H11 | 0.4078 (16) | 0.577 (5) | 0.230 (4) | 0.058* | |
C12 | 0.27302 (19) | 0.4873 (6) | −0.2119 (5) | 0.0807 (16) | |
H12A | 0.2589 | 0.5860 | −0.2480 | 0.097* | |
H12B | 0.2411 | 0.4226 | −0.1831 | 0.097* | |
H12C | 0.2945 | 0.4348 | −0.2863 | 0.097* | |
N5 | 0.39317 (13) | 0.2824 (4) | 0.1876 (3) | 0.0431 (8) | |
H5N | 0.4022 (15) | 0.309 (4) | 0.2740 (17) | 0.052* | |
O3 | 0.41179 (11) | 0.0963 (3) | −0.0128 (2) | 0.0502 (7) | |
O4 | 0.45564 (12) | 0.0557 (3) | 0.2256 (3) | 0.0597 (8) | |
S2 | 0.43830 (4) | 0.16131 (9) | 0.11400 (8) | 0.0400 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.060 (2) | 0.046 (2) | 0.063 (2) | −0.005 (2) | −0.002 (2) | −0.004 (2) |
C6 | 0.0430 (19) | 0.0377 (17) | 0.0302 (16) | 0.0040 (16) | 0.0050 (16) | 0.0004 (18) |
C7 | 0.048 (2) | 0.043 (2) | 0.0400 (19) | 0.0059 (18) | −0.0015 (18) | −0.0052 (19) |
C8 | 0.047 (2) | 0.053 (2) | 0.048 (2) | 0.0124 (19) | −0.0021 (19) | 0.005 (2) |
C9 | 0.053 (3) | 0.055 (3) | 0.064 (3) | 0.012 (2) | 0.002 (2) | 0.018 (3) |
C10 | 0.052 (2) | 0.037 (2) | 0.081 (3) | −0.0026 (19) | 0.007 (2) | 0.000 (2) |
C11 | 0.053 (2) | 0.046 (2) | 0.046 (2) | 0.000 (2) | −0.0027 (19) | −0.003 (2) |
C12 | 0.086 (3) | 0.084 (4) | 0.072 (3) | 0.028 (3) | −0.034 (3) | −0.005 (3) |
N5 | 0.0595 (19) | 0.0441 (18) | 0.0256 (14) | 0.0099 (16) | −0.0017 (15) | 0.0024 (14) |
O3 | 0.0723 (17) | 0.0407 (14) | 0.0375 (13) | 0.0003 (14) | −0.0112 (12) | −0.0093 (12) |
O4 | 0.088 (2) | 0.0473 (15) | 0.0436 (14) | 0.0134 (15) | −0.0116 (14) | 0.0162 (13) |
S2 | 0.0588 (5) | 0.0311 (4) | 0.0302 (4) | 0.0028 (4) | −0.0063 (4) | 0.0011 (4) |
C1—S2 | 1.749 (4) | C9—H9 | 0.87 (4) |
C1—H1A | 0.9600 | C10—C11 | 1.385 (5) |
C1—H1B | 0.9600 | C10—H10 | 0.90 (4) |
C1—H1C | 0.9600 | C11—H11 | 0.92 (4) |
C6—C11 | 1.375 (5) | C12—H12A | 0.9600 |
C6—C7 | 1.378 (5) | C12—H12B | 0.9600 |
C6—N5 | 1.446 (4) | C12—H12C | 0.9600 |
C7—C8 | 1.389 (5) | N5—S2 | 1.618 (3) |
C7—H7 | 0.87 (4) | N5—H5N | 0.856 (10) |
C8—C9 | 1.370 (6) | O3—S2 | 1.436 (2) |
C8—C12 | 1.500 (5) | O4—S2 | 1.426 (2) |
C9—C10 | 1.380 (6) | ||
S2—C1—H1A | 109.5 | C11—C10—H10 | 119 (3) |
S2—C1—H1B | 109.5 | C6—C11—C10 | 119.2 (4) |
H1A—C1—H1B | 109.5 | C6—C11—H11 | 118 (3) |
S2—C1—H1C | 109.5 | C10—C11—H11 | 123 (3) |
H1A—C1—H1C | 109.5 | C8—C12—H12A | 109.5 |
H1B—C1—H1C | 109.5 | C8—C12—H12B | 109.5 |
C11—C6—C7 | 120.6 (3) | H12A—C12—H12B | 109.5 |
C11—C6—N5 | 119.4 (3) | C8—C12—H12C | 109.5 |
C7—C6—N5 | 120.0 (3) | H12A—C12—H12C | 109.5 |
C6—C7—C8 | 120.8 (4) | H12B—C12—H12C | 109.5 |
C6—C7—H7 | 121 (3) | C6—N5—S2 | 121.2 (2) |
C8—C7—H7 | 118 (3) | C6—N5—H5N | 111 (2) |
C9—C8—C7 | 117.8 (4) | S2—N5—H5N | 114 (2) |
C9—C8—C12 | 122.0 (4) | O4—S2—O3 | 118.09 (16) |
C7—C8—C12 | 120.2 (4) | O4—S2—N5 | 106.12 (15) |
C8—C9—C10 | 122.0 (4) | O3—S2—N5 | 108.12 (16) |
C8—C9—H9 | 118 (3) | O4—S2—C1 | 109.09 (18) |
C10—C9—H9 | 120 (3) | O3—S2—C1 | 107.21 (17) |
C9—C10—C11 | 119.5 (4) | N5—S2—C1 | 107.82 (18) |
C9—C10—H10 | 121 (3) | ||
C11—C6—C7—C8 | 2.8 (6) | N5—C6—C11—C10 | −178.5 (4) |
N5—C6—C7—C8 | −179.7 (3) | C9—C10—C11—C6 | −1.5 (6) |
C6—C7—C8—C9 | −2.0 (6) | C11—C6—N5—S2 | −114.3 (3) |
C6—C7—C8—C12 | 177.6 (4) | C7—C6—N5—S2 | 68.2 (4) |
C7—C8—C9—C10 | −0.6 (6) | C6—N5—S2—O4 | 174.6 (3) |
C12—C8—C9—C10 | 179.8 (4) | C6—N5—S2—O3 | −57.7 (3) |
C8—C9—C10—C11 | 2.3 (7) | C6—N5—S2—C1 | 57.9 (3) |
C7—C6—C11—C10 | −1.0 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5N···O3i | 0.86 (1) | 2.14 (1) | 2.990 (4) | 169 (3) |
Symmetry code: (i) x, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C8H11NO2S |
Mr | 185.24 |
Crystal system, space group | Orthorhombic, Pccn |
Temperature (K) | 299 |
a, b, c (Å) | 23.218 (2), 8.4933 (7), 9.2561 (8) |
V (Å3) | 1825.3 (3) |
Z | 8 |
Radiation type | Cu Kα |
µ (mm−1) | 2.84 |
Crystal size (mm) | 0.25 × 0.10 × 0.03 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 |
Absorption correction | Psi-scan (North et al., 1968) |
Tmin, Tmax | 0.623, 0.859 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 1875, 1618, 975 |
Rint | 0.044 |
(sin θ/λ)max (Å−1) | 0.596 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.124, 1.02 |
No. of reflections | 1618 |
No. of parameters | 124 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.20, −0.36 |
Computer programs: CAD-4-PC (Enraf–Nonius, 1996), CAD-4-PC, REDU4 (Stoe & Cie, 1987), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5N···O3i | 0.856 (10) | 2.144 (12) | 2.990 (4) | 169 (3) |
Symmetry code: (i) x, −y+1/2, z+1/2. |
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The stereochemistry of biologically important alkyl sulfonanilides is of interest in explaining their biological activity. The biological activity may be due to N—H group. Therefore the structural studies of sulfonanilides are of interest. In the present work, the structure of N-(3-methylphenyl)-methanesulfonamde (3MPMSA) has been determined to explore the substituent effects on the structures of anilides and sulfonanilides (Gowda et al., 2000, 2007, 2007a,b). The conformation of the N—H bond in the structure of 3MPMSA, is anti to the meta-methyl substituent (Fig.1), similar to that observed in the corresponding meta- nitro substituted sulfonanilide (3NPMSA)(Gowda et al., 2007b). The bond parameters in the 3 compounds, PMSA (Klug, 1968), 3MPMSA and 3NPMSA are similar except in the S—N—C bond angle [120.0 (1)° (PMSA); 121.2 (2)° (3MPMSA); 126.3 (3)° (3NPMSA)] and in the S—N—C—C torsion angles [S2—N5—C6—C7 and S2—N5—C6—C11: 75.5 (2)° and -106.6 (2)° (PMSA); 68.1 (4)° and -114.3 (3)° (3MPMSA); 41.1 (3)°, -140.8 (2)° (3NPMSA)]. The molecules are linked in chains in the direction of c axis through N—H···O hydrogen bonds. (Table 1 and Fig. 2).