Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807025202/lw2017sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807025202/lw2017Isup2.hkl |
CCDC reference: 614672
Key indicators
- Single-crystal X-ray study
- T = 301 K
- Mean (C-C) = 0.005 Å
- R factor = 0.054
- wR factor = 0.130
- Data-to-parameter ratio = 16.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 6
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 26.36 From the CIF: _reflns_number_total 2023 Count of symmetry unique reflns 1242 Completeness (_total/calc) 162.88% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 781 Fraction of Friedel pairs measured 0.629 Are heavy atom types Z>Si present yes PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 2 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. (2007a,b,c,d,e,f,g); 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 and used for X-ray diffraction studied at room temperature.
The H atom of the NH group was located in a diffrerence map and its position refined. The carbon-bound H atoms were positioned with idealized geometry and refined using a riding model with C—H = 0.93 Å (CH aromatic) or 0.96 Å (CH3). Isotropic displacement parameters for all H atoms were set equal to 1.2 Ueq (parent atom).
The biological activity of alkyl sulfonanilides is thought to be due to the hydrogen of the phenyl N—H portion of the sulfonanilide molecules as it can align itself, in relation to a receptor site. Therefore the structural studies of sulfonanilides are of interest. In the present work, the structure of N-(2,3-dimethylphenyl)-methanesulfonamide (23DMPMSA) has been determined to explore the substituent effects on the solid state structures of sulfonanilides (Gowda et al., 2007a-g). The structure of 23DMPMSA (Fig. 1) resembles those of N-(phenyl)-methanesulfonamide (PMSA) (Klug, 1968), N-(2-methylphenyl)-methanesulfonamide (2MPMSA) (Gowda et al., 2007d), N-(3-methylphenyl)- methanesulfonamide (3MPMSA)(Gowda et al., 2007b) and other alkyl sulfonanilides (Gowda et al., 2007a,c,e-g). The conformation of the N—H bond lies between syn and anti conformations to the methyl substituents at ortho and meta positions, in contrast to the syn and anti conformations observed, respectively, for the 2MPMSA and 3MPMSA. Dimethyl substitutions at both ortho and meta positions in PMSA changes its space group from monoclinic P21/c to orthorhombic P212121, compared to the change over from monoclinic P21/c to triclinic P-1 on ortho methyl substitution in PMSA and from monoclinic P21/c to orthorhombic Pccn on meta substitution in PMSA. The geometric parameters in PMSA, 2MPMSA, 3MPMSA and 23DMPMSA are similar except for some difference in the torsional angles, C1S2N5C6, S2N5C6C7, S2N5C6C11, O3S2N5C6, O4S2N5C6: 62.2 (2)°, 75.5 (2)°, -106.6 (2)°, -54.4 (2)°, 177.7 (2)° (PMSA); -64.5 (2)°, 117.1 (2)°, -65.3 (3)°, 51.3 (2)°, 179.1 (2)° (2MPMSA); 57.9 (3)°, 68.1 (4)°, -114.3 (3)°, -57.7 (3)°, 174.7 (3)° (3MPMSA); 71.4 (3)°, 70.1 (4)°, -110.8 (3)°, -44.9 (3)°, -172.6 (3)° (23DMPMSA), respectively. The data included for PMSA are the values determined under the present conditions as the literature values were determined in Klug, 1968. The N—H hydrogen sits alone on one side of the plane of the phenyl group, while the whole methanesulfonyl group is on the opposite side of the plane, similar to that in PMSA, 2MPMSA and 3MPMSA. The amide hydrogen is thus available to a receptor molecule during its biological activity. The molecules in 23DMPMSA are packed into chains in the direction of b axis (Fig. 2) through N—H···O hydrogen bonds (Fig. 3 and Table 1).
For related literature, see: Gowda et al. (2007a,b,c,d,e,f,g); Jayalakshmi & Gowda (2004); Klug (1968).
Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2004); 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.
C9H13NO2S | F(000) = 424 |
Mr = 199.26 | Dx = 1.338 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 2323 reflections |
a = 5.2259 (6) Å | θ = 3.6–23.2° |
b = 5.5567 (8) Å | µ = 0.30 mm−1 |
c = 34.056 (1) Å | T = 301 K |
V = 988.94 (18) Å3 | Prism, gray |
Z = 4 | 0.50 × 0.44 × 0.22 mm |
Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector | 1831 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.068 |
Graphite monochromator | θmax = 26.4°, θmin = 4.1° |
Rotation method data acquisition using ω scans | h = −6→5 |
6529 measured reflections | k = −6→6 |
2023 independent reflections | l = −40→42 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.054 | w = 1/[σ2(Fo2) + (0.0485P)2 + 0.7116P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.130 | (Δ/σ)max = 0.035 |
S = 1.07 | Δρmax = 0.27 e Å−3 |
2023 reflections | Δρmin = −0.24 e Å−3 |
122 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.016 (4) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 781 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.22 (16) |
C9H13NO2S | V = 988.94 (18) Å3 |
Mr = 199.26 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 5.2259 (6) Å | µ = 0.30 mm−1 |
b = 5.5567 (8) Å | T = 301 K |
c = 34.056 (1) Å | 0.50 × 0.44 × 0.22 mm |
Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector | 1831 reflections with I > 2σ(I) |
6529 measured reflections | Rint = 0.068 |
2023 independent reflections |
R[F2 > 2σ(F2)] = 0.054 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.130 | Δρmax = 0.27 e Å−3 |
S = 1.07 | Δρmin = −0.24 e Å−3 |
2023 reflections | Absolute structure: Flack (1983), 781 Friedel pairs |
122 parameters | Absolute structure parameter: 0.22 (16) |
1 restraint |
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 | ||
S2 | 0.70935 (16) | 0.32902 (18) | 0.19688 (2) | 0.0436 (3) | |
O3 | 0.4634 (4) | 0.4002 (5) | 0.18247 (8) | 0.0547 (7) | |
O4 | 0.8125 (6) | 0.4515 (5) | 0.22983 (8) | 0.0623 (8) | |
N5 | 0.9112 (5) | 0.3672 (6) | 0.16118 (8) | 0.0415 (7) | |
H5N | 1.067 (3) | 0.383 (8) | 0.1683 (10) | 0.050* | |
C1 | 0.7014 (10) | 0.0208 (8) | 0.20732 (12) | 0.0621 (11) | |
H1A | 0.8676 | −0.0311 | 0.2158 | 0.075* | |
H1B | 0.6534 | −0.0665 | 0.1841 | 0.075* | |
H1C | 0.5787 | −0.0093 | 0.2277 | 0.075* | |
C6 | 0.8579 (6) | 0.2927 (6) | 0.12190 (9) | 0.0404 (8) | |
C7 | 0.9912 (6) | 0.0995 (6) | 0.10470 (10) | 0.0422 (8) | |
C8 | 0.9385 (8) | 0.0450 (7) | 0.06527 (11) | 0.0518 (9) | |
C9 | 0.7513 (7) | 0.1698 (10) | 0.04547 (11) | 0.0622 (11) | |
H9 | 0.7136 | 0.1287 | 0.0196 | 0.075* | |
C10 | 0.6192 (8) | 0.3537 (10) | 0.06313 (11) | 0.0643 (12) | |
H10 | 0.4922 | 0.4348 | 0.0493 | 0.077* | |
C11 | 0.6736 (7) | 0.4186 (7) | 0.10106 (11) | 0.0526 (9) | |
H11 | 0.5873 | 0.5463 | 0.1127 | 0.063* | |
C12 | 1.0809 (9) | −0.1528 (10) | 0.04468 (13) | 0.0711 (12) | |
H12A | 1.0426 | −0.3040 | 0.0570 | 0.085* | |
H12B | 1.2615 | −0.1226 | 0.0462 | 0.085* | |
H12C | 1.0295 | −0.1583 | 0.0176 | 0.085* | |
C13 | 1.1869 (8) | −0.0438 (7) | 0.12723 (11) | 0.0530 (9) | |
H13A | 1.1731 | −0.0073 | 0.1547 | 0.064* | |
H13B | 1.3553 | −0.0031 | 0.1181 | 0.064* | |
H13C | 1.1571 | −0.2125 | 0.1232 | 0.064* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S2 | 0.0330 (4) | 0.0514 (5) | 0.0465 (4) | 0.0027 (4) | −0.0021 (3) | −0.0061 (4) |
O3 | 0.0293 (12) | 0.0688 (18) | 0.0659 (16) | 0.0086 (12) | −0.0012 (11) | −0.0061 (13) |
O4 | 0.0571 (16) | 0.0693 (18) | 0.0606 (15) | 0.0058 (16) | −0.0078 (14) | −0.0272 (14) |
N5 | 0.0264 (12) | 0.0488 (17) | 0.0492 (16) | −0.0008 (14) | −0.0008 (11) | −0.0026 (13) |
C1 | 0.068 (3) | 0.063 (2) | 0.056 (2) | −0.003 (2) | 0.001 (2) | 0.0135 (18) |
C6 | 0.0276 (15) | 0.0455 (19) | 0.0480 (17) | −0.0013 (14) | 0.0009 (13) | 0.0069 (15) |
C7 | 0.0344 (17) | 0.0362 (17) | 0.056 (2) | −0.0033 (14) | 0.0031 (15) | 0.0020 (14) |
C8 | 0.048 (2) | 0.051 (2) | 0.056 (2) | −0.0109 (18) | 0.0101 (18) | −0.0011 (18) |
C9 | 0.055 (2) | 0.085 (3) | 0.0461 (18) | −0.008 (3) | −0.0027 (17) | 0.003 (2) |
C10 | 0.054 (2) | 0.087 (3) | 0.052 (2) | 0.014 (2) | −0.0065 (17) | 0.021 (2) |
C11 | 0.047 (2) | 0.052 (2) | 0.059 (2) | 0.0118 (18) | 0.0027 (18) | 0.0139 (17) |
C12 | 0.068 (3) | 0.075 (3) | 0.070 (3) | −0.008 (3) | 0.016 (2) | −0.021 (2) |
C13 | 0.045 (2) | 0.047 (2) | 0.067 (2) | 0.0093 (19) | −0.0044 (19) | −0.0040 (17) |
S2—O4 | 1.419 (3) | C8—C9 | 1.376 (6) |
S2—O3 | 1.432 (2) | C8—C12 | 1.501 (6) |
S2—N5 | 1.623 (3) | C9—C10 | 1.373 (6) |
S2—C1 | 1.750 (4) | C9—H9 | 0.9300 |
N5—C6 | 1.428 (4) | C10—C11 | 1.371 (6) |
N5—H5N | 0.854 (10) | C10—H10 | 0.9300 |
C1—H1A | 0.9600 | C11—H11 | 0.9300 |
C1—H1B | 0.9600 | C12—H12A | 0.9600 |
C1—H1C | 0.9600 | C12—H12B | 0.9600 |
C6—C11 | 1.386 (5) | C12—H12C | 0.9600 |
C6—C7 | 1.408 (5) | C13—H13A | 0.9600 |
C7—C8 | 1.404 (5) | C13—H13B | 0.9600 |
C7—C13 | 1.506 (5) | C13—H13C | 0.9600 |
O4—S2—O3 | 118.66 (18) | C7—C8—C12 | 120.5 (4) |
O4—S2—N5 | 106.41 (17) | C10—C9—C8 | 121.2 (4) |
O3—S2—N5 | 106.90 (15) | C10—C9—H9 | 119.4 |
O4—S2—C1 | 108.5 (2) | C8—C9—H9 | 119.4 |
O3—S2—C1 | 108.6 (2) | C11—C10—C9 | 120.3 (4) |
N5—S2—C1 | 107.20 (19) | C11—C10—H10 | 119.9 |
C6—N5—S2 | 122.5 (2) | C9—C10—H10 | 119.9 |
C6—N5—H5N | 119 (3) | C10—C11—C6 | 119.6 (4) |
S2—N5—H5N | 115 (2) | C10—C11—H11 | 120.2 |
S2—C1—H1A | 109.5 | C6—C11—H11 | 120.2 |
S2—C1—H1B | 109.5 | C8—C12—H12A | 109.5 |
H1A—C1—H1B | 109.5 | C8—C12—H12B | 109.5 |
S2—C1—H1C | 109.5 | H12A—C12—H12B | 109.5 |
H1A—C1—H1C | 109.5 | C8—C12—H12C | 109.5 |
H1B—C1—H1C | 109.5 | H12A—C12—H12C | 109.5 |
C11—C6—C7 | 121.1 (3) | H12B—C12—H12C | 109.5 |
C11—C6—N5 | 118.0 (3) | C7—C13—H13A | 109.5 |
C7—C6—N5 | 121.0 (3) | C7—C13—H13B | 109.5 |
C8—C7—C6 | 117.7 (3) | H13A—C13—H13B | 109.5 |
C8—C7—C13 | 120.4 (3) | C7—C13—H13C | 109.5 |
C6—C7—C13 | 121.8 (3) | H13A—C13—H13C | 109.5 |
C9—C8—C7 | 120.0 (4) | H13B—C13—H13C | 109.5 |
C9—C8—C12 | 119.5 (4) | ||
O4—S2—N5—C6 | −172.6 (3) | C13—C7—C8—C9 | 177.1 (4) |
O3—S2—N5—C6 | −44.9 (3) | C6—C7—C8—C12 | 177.7 (3) |
C1—S2—N5—C6 | 71.4 (3) | C13—C7—C8—C12 | −1.5 (5) |
S2—N5—C6—C11 | 70.1 (4) | C7—C8—C9—C10 | 2.2 (6) |
S2—N5—C6—C7 | −110.8 (3) | C12—C8—C9—C10 | −179.2 (4) |
C11—C6—C7—C8 | 2.5 (5) | C8—C9—C10—C11 | 0.6 (7) |
N5—C6—C7—C8 | −176.5 (3) | C9—C10—C11—C6 | −1.9 (6) |
C11—C6—C7—C13 | −178.3 (3) | C7—C6—C11—C10 | 0.2 (5) |
N5—C6—C7—C13 | 2.7 (5) | N5—C6—C11—C10 | 179.3 (3) |
C6—C7—C8—C9 | −3.7 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5N···O3i | 0.85 (1) | 2.13 (1) | 2.981 (4) | 175 (4) |
Symmetry code: (i) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C9H13NO2S |
Mr | 199.26 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 301 |
a, b, c (Å) | 5.2259 (6), 5.5567 (8), 34.056 (1) |
V (Å3) | 988.94 (18) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.30 |
Crystal size (mm) | 0.50 × 0.44 × 0.22 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6529, 2023, 1831 |
Rint | 0.068 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.130, 1.07 |
No. of reflections | 2023 |
No. of parameters | 122 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.27, −0.24 |
Absolute structure | Flack (1983), 781 Friedel pairs |
Absolute structure parameter | 0.22 (16) |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2004), CrysAlis CCD, CrysAlis RED (Oxford Diffraction, 2004), 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 | 0.854 (10) | 2.130 (11) | 2.981 (4) | 175 (4) |
Symmetry code: (i) x+1, y, z. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
The biological activity of alkyl sulfonanilides is thought to be due to the hydrogen of the phenyl N—H portion of the sulfonanilide molecules as it can align itself, in relation to a receptor site. Therefore the structural studies of sulfonanilides are of interest. In the present work, the structure of N-(2,3-dimethylphenyl)-methanesulfonamide (23DMPMSA) has been determined to explore the substituent effects on the solid state structures of sulfonanilides (Gowda et al., 2007a-g). The structure of 23DMPMSA (Fig. 1) resembles those of N-(phenyl)-methanesulfonamide (PMSA) (Klug, 1968), N-(2-methylphenyl)-methanesulfonamide (2MPMSA) (Gowda et al., 2007d), N-(3-methylphenyl)- methanesulfonamide (3MPMSA)(Gowda et al., 2007b) and other alkyl sulfonanilides (Gowda et al., 2007a,c,e-g). The conformation of the N—H bond lies between syn and anti conformations to the methyl substituents at ortho and meta positions, in contrast to the syn and anti conformations observed, respectively, for the 2MPMSA and 3MPMSA. Dimethyl substitutions at both ortho and meta positions in PMSA changes its space group from monoclinic P21/c to orthorhombic P212121, compared to the change over from monoclinic P21/c to triclinic P-1 on ortho methyl substitution in PMSA and from monoclinic P21/c to orthorhombic Pccn on meta substitution in PMSA. The geometric parameters in PMSA, 2MPMSA, 3MPMSA and 23DMPMSA are similar except for some difference in the torsional angles, C1S2N5C6, S2N5C6C7, S2N5C6C11, O3S2N5C6, O4S2N5C6: 62.2 (2)°, 75.5 (2)°, -106.6 (2)°, -54.4 (2)°, 177.7 (2)° (PMSA); -64.5 (2)°, 117.1 (2)°, -65.3 (3)°, 51.3 (2)°, 179.1 (2)° (2MPMSA); 57.9 (3)°, 68.1 (4)°, -114.3 (3)°, -57.7 (3)°, 174.7 (3)° (3MPMSA); 71.4 (3)°, 70.1 (4)°, -110.8 (3)°, -44.9 (3)°, -172.6 (3)° (23DMPMSA), respectively. The data included for PMSA are the values determined under the present conditions as the literature values were determined in Klug, 1968. The N—H hydrogen sits alone on one side of the plane of the phenyl group, while the whole methanesulfonyl group is on the opposite side of the plane, similar to that in PMSA, 2MPMSA and 3MPMSA. The amide hydrogen is thus available to a receptor molecule during its biological activity. The molecules in 23DMPMSA are packed into chains in the direction of b axis (Fig. 2) through N—H···O hydrogen bonds (Fig. 3 and Table 1).