Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807016273/lw2008sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807016273/lw2008Isup2.hkl |
CCDC reference: 614627
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean (C-C) = 0.004 Å
- R factor = 0.039
- wR factor = 0.098
- Data-to-parameter ratio = 11.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.95 PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 1000 Deg. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 5 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for S2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 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); Gowda, Kozisek et al. (2007); Gowda et al. (2000); Jayalakshmi & Gowda (2004); Klug (1968).
The title compound was prepared according to the literature method of Jayalakshmi & Gowda (2004). The purity of the compound was checked by determining its melting point. It was characterized by recording its IR and NMR
spectra (Jayalakshmi & Gowda, 2004). Single crystals of the title compound were obtained by slow evaporation of an ethanolic solution and used for X-ray diffraction studied at room temperature.
All H atoms attached to C and N atoms were positioned geometrically and treated as riding, with C—H = 0.93 Å (CH aromatic) or 0.96 Å (CH3) and N—H = 0.86 Å, and with Uiso(H) = 1.2Ueq(C,N) or 1.5Ueq(C) for methyl H. [This does not match the data in the CIF, where coordinates have been refined - please provide correct text]
The biological activity of alkyl sulfonanilides is thought to be due to the H atom of the phenyl N—H portion of the sulfonanilide molecule, 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-methylphenyl)methanesulfonamde (2MPMSA), (I), has been determined to explore the substituent effects on the solid-state structures of anilides and sulfonanilides (Gowda et al., 2007a,b,c,d; Gowda, Kozisek et al., 2007; Gowda et al., 2000).
The conformation of the N—H bond in the structure of 2MPMSA is syn to the ortho-methyl substituent (Fig. 1), in contrast with the anti conformation observed for the meta-methyl-substituted compound (3MPMSA) (Gowda et al., 2007c). The ortho-substitution of the methyl group in N-(phenyl)methanesulfonamde (PMSA) changes its space group from monoclinic P21/c (Klug, 1968) to triclinic P1, compared with the change from monoclinic P21/c to orthorhombic Pccn on meta-methyl substitution (Gowda et al., 2007c).
The bond parameters in PMSA (Klug, 1968), 2MPMSA and 3MPMSA (Gowda et al., 2007c) are similar except for the torsion angles C1—S2—N5—C6, S2—N5—C6—C7, S2—N5—C6—C11, which have the following values: 62.2 (2), 75.5 (2) and -106.6 (2)°, respectively, in PMSA; -64.5 (2), 117.1 (2) and -65.3 (3)°, respectively, in 2MPMSA; 57.9 (3), 68.1 (4) and -114.3 (3)°, respectively, in 3MPMSA. The data included for PMSA are the values determined under the present conditions as the literature values were determined in [Meaning not clear. Text missing?] (Klug, 1968).
The N—H H atom lies 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 what was observed in PMSA and 3MPMSA. Thus, the amide H atom is available to
a receptor molecule during biological activity.
The molecules in the title compound form centrosymmetric dimers via an N5—H5N···O3(1 - x,-y, 1 - z) hydrogen bond (Table 1 and Fig. 2).
For related literature, see: Gowda et al. (2007a,b,c,d); Gowda, Kozisek et al. (2007); 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 | Z = 2 |
Mr = 185.24 | F(000) = 196 |
Triclinic, P1 | Dx = 1.361 Mg m−3 |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.54180 Å |
a = 5.719 (1) Å | Cell parameters from 25 reflections |
b = 9.041 (1) Å | θ = 7.7–23.7° |
c = 9.225 (2) Å | µ = 2.87 mm−1 |
α = 79.53 (1)° | T = 299 K |
β = 87.36 (1)° | Block, grey |
γ = 74.44 (1)° | 0.13 × 0.13 × 0.10 mm |
V = 451.85 (14) Å3 |
Enraf–Nonius CAD-4 diffractometer | 1259 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.036 |
Graphite monochromator | θmax = 66.9°, θmin = 4.9° |
ω/2θ scans | h = −6→6 |
Absorption correction: ψ scan (North et al., 1968) | k = −10→10 |
Tmin = 0.731, Tmax = 0.789 | l = 0→10 |
1713 measured reflections | 3 standard reflections every 120 min |
1606 independent reflections | intensity decay: 1.8% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.039 | Only H-atom coordinates refined |
wR(F2) = 0.098 | w = 1/[σ2(Fo2) + (0.0411P)2 + 0.0954P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
1606 reflections | Δρmax = 0.17 e Å−3 |
143 parameters | Δρmin = −0.26 e Å−3 |
1 restraint | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0117 (14) |
C8H11NO2S | γ = 74.44 (1)° |
Mr = 185.24 | V = 451.85 (14) Å3 |
Triclinic, P1 | Z = 2 |
a = 5.719 (1) Å | Cu Kα radiation |
b = 9.041 (1) Å | µ = 2.87 mm−1 |
c = 9.225 (2) Å | T = 299 K |
α = 79.53 (1)° | 0.13 × 0.13 × 0.10 mm |
β = 87.36 (1)° |
Enraf–Nonius CAD-4 diffractometer | 1259 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.036 |
Tmin = 0.731, Tmax = 0.789 | 3 standard reflections every 120 min |
1713 measured reflections | intensity decay: 1.8% |
1606 independent reflections |
R[F2 > 2σ(F2)] = 0.039 | 1 restraint |
wR(F2) = 0.098 | Only H-atom coordinates refined |
S = 1.08 | Δρmax = 0.17 e Å−3 |
1606 reflections | Δρmin = −0.26 e Å−3 |
143 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 | 0.2073 (7) | 0.0168 (4) | 0.1937 (4) | 0.0679 (9) | |
H1A | 0.265 (6) | −0.052 (4) | 0.124 (4) | 0.081* | |
H1B | 0.142 (6) | −0.028 (4) | 0.276 (4) | 0.081* | |
H1C | 0.094 (6) | 0.114 (4) | 0.145 (4) | 0.081* | |
C6 | 0.1994 (4) | 0.3574 (3) | 0.2840 (3) | 0.0404 (5) | |
C7 | 0.2887 (5) | 0.4558 (3) | 0.1760 (3) | 0.0511 (7) | |
H7 | 0.447 (5) | 0.424 (3) | 0.142 (3) | 0.061* | |
C8 | 0.1438 (6) | 0.6009 (3) | 0.1180 (3) | 0.0623 (8) | |
H8 | 0.207 (5) | 0.668 (4) | 0.042 (3) | 0.075* | |
C9 | −0.0875 (6) | 0.6489 (4) | 0.1688 (3) | 0.0648 (8) | |
H9 | −0.194 (6) | 0.749 (4) | 0.136 (3) | 0.078* | |
C10 | −0.1738 (5) | 0.5531 (4) | 0.2789 (3) | 0.0589 (7) | |
H10 | −0.331 (6) | 0.586 (4) | 0.316 (3) | 0.071* | |
C11 | −0.0351 (4) | 0.4046 (3) | 0.3388 (3) | 0.0445 (6) | |
C12 | −0.1334 (6) | 0.3018 (4) | 0.4577 (4) | 0.0625 (8) | |
H12A | −0.128 (6) | 0.210 (4) | 0.430 (4) | 0.075* | |
H12B | −0.042 (6) | 0.279 (4) | 0.546 (4) | 0.075* | |
H12C | −0.289 (6) | 0.348 (4) | 0.476 (3) | 0.075* | |
N5 | 0.3555 (4) | 0.2077 (2) | 0.3434 (2) | 0.0468 (5) | |
H5N | 0.348 (5) | 0.164 (3) | 0.4324 (15) | 0.056* | |
O3 | 0.6064 (4) | −0.0557 (2) | 0.3450 (2) | 0.0789 (7) | |
O4 | 0.5642 (4) | 0.1338 (2) | 0.1154 (2) | 0.0607 (5) | |
S2 | 0.45723 (12) | 0.07166 (7) | 0.24662 (7) | 0.0469 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.081 (2) | 0.066 (2) | 0.067 (2) | −0.0319 (18) | 0.0114 (18) | −0.0207 (17) |
C6 | 0.0437 (13) | 0.0398 (12) | 0.0373 (12) | −0.0079 (10) | −0.0027 (10) | −0.0098 (10) |
C7 | 0.0554 (16) | 0.0479 (14) | 0.0484 (15) | −0.0124 (12) | 0.0083 (13) | −0.0083 (12) |
C8 | 0.083 (2) | 0.0462 (15) | 0.0524 (17) | −0.0124 (15) | 0.0093 (15) | −0.0053 (13) |
C9 | 0.079 (2) | 0.0470 (16) | 0.0564 (17) | 0.0033 (15) | −0.0053 (16) | −0.0070 (14) |
C10 | 0.0462 (16) | 0.0626 (18) | 0.0629 (18) | −0.0006 (13) | −0.0016 (13) | −0.0190 (15) |
C11 | 0.0422 (14) | 0.0506 (14) | 0.0420 (13) | −0.0117 (11) | −0.0021 (10) | −0.0123 (11) |
C12 | 0.0543 (18) | 0.073 (2) | 0.0635 (19) | −0.0230 (16) | 0.0117 (15) | −0.0131 (17) |
N5 | 0.0536 (13) | 0.0458 (12) | 0.0336 (11) | −0.0021 (10) | −0.0019 (9) | −0.0041 (9) |
O3 | 0.0951 (16) | 0.0603 (12) | 0.0507 (12) | 0.0292 (11) | −0.0059 (11) | −0.0045 (10) |
O4 | 0.0651 (12) | 0.0637 (12) | 0.0509 (11) | −0.0162 (10) | 0.0203 (9) | −0.0105 (9) |
S2 | 0.0516 (4) | 0.0431 (4) | 0.0376 (3) | −0.0008 (3) | 0.0031 (2) | −0.0037 (2) |
C1—S2 | 1.749 (4) | C9—H9 | 0.95 (3) |
C1—H1A | 0.96 (3) | C10—C11 | 1.392 (4) |
C1—H1B | 0.91 (3) | C10—H10 | 0.94 (3) |
C1—H1C | 0.99 (3) | C11—C12 | 1.495 (4) |
C6—C7 | 1.386 (3) | C12—H12A | 0.90 (3) |
C6—C11 | 1.395 (3) | C12—H12B | 0.95 (3) |
C6—N5 | 1.434 (3) | C12—H12C | 0.90 (3) |
C7—C8 | 1.377 (4) | N5—S2 | 1.617 (2) |
C7—H7 | 0.93 (3) | N5—H5N | 0.848 (10) |
C8—C9 | 1.366 (4) | O3—S2 | 1.4286 (19) |
C8—H8 | 0.96 (3) | O4—S2 | 1.4225 (19) |
C9—C10 | 1.374 (4) | ||
S2—C1—H1A | 107 (2) | C11—C10—H10 | 117.6 (19) |
S2—C1—H1B | 108 (2) | C10—C11—C6 | 116.9 (2) |
H1A—C1—H1B | 114 (3) | C10—C11—C12 | 121.2 (3) |
S2—C1—H1C | 106 (2) | C6—C11—C12 | 121.9 (2) |
H1A—C1—H1C | 110 (3) | C11—C12—H12A | 111 (2) |
H1B—C1—H1C | 112 (3) | C11—C12—H12B | 112 (2) |
C7—C6—C11 | 120.9 (2) | H12A—C12—H12B | 107 (3) |
C7—C6—N5 | 118.9 (2) | C11—C12—H12C | 110 (2) |
C11—C6—N5 | 120.1 (2) | H12A—C12—H12C | 108 (3) |
C8—C7—C6 | 120.2 (3) | H12B—C12—H12C | 109 (3) |
C8—C7—H7 | 119.5 (18) | C6—N5—S2 | 123.02 (16) |
C6—C7—H7 | 120.3 (18) | C6—N5—H5N | 122.6 (19) |
C9—C8—C7 | 119.9 (3) | S2—N5—H5N | 108 (2) |
C9—C8—H8 | 120.6 (19) | O4—S2—O3 | 118.19 (13) |
C7—C8—H8 | 119.5 (19) | O4—S2—N5 | 109.11 (12) |
C8—C9—C10 | 119.9 (3) | O3—S2—N5 | 105.40 (12) |
C8—C9—H9 | 123.7 (19) | O4—S2—C1 | 107.17 (15) |
C10—C9—H9 | 116 (2) | O3—S2—C1 | 109.20 (17) |
C9—C10—C11 | 122.1 (3) | N5—S2—C1 | 107.33 (15) |
C9—C10—H10 | 120.3 (19) | ||
C11—C6—C7—C8 | −1.8 (4) | N5—C6—C11—C10 | 178.2 (2) |
N5—C6—C7—C8 | −179.3 (2) | C7—C6—C11—C12 | −178.6 (3) |
C6—C7—C8—C9 | 1.0 (5) | N5—C6—C11—C12 | −1.1 (4) |
C7—C8—C9—C10 | 0.9 (5) | C7—C6—N5—S2 | −65.4 (3) |
C8—C9—C10—C11 | −2.0 (5) | C11—C6—N5—S2 | 117.1 (2) |
C9—C10—C11—C6 | 1.2 (4) | C6—N5—S2—O4 | 51.3 (2) |
C9—C10—C11—C12 | −179.5 (3) | C6—N5—S2—O3 | 179.2 (2) |
C7—C6—C11—C10 | 0.7 (4) | C6—N5—S2—C1 | −64.5 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5N···O3i | 0.85 (1) | 2.10 (1) | 2.943 (3) | 170 (3) |
Symmetry code: (i) −x+1, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C8H11NO2S |
Mr | 185.24 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 299 |
a, b, c (Å) | 5.719 (1), 9.041 (1), 9.225 (2) |
α, β, γ (°) | 79.53 (1), 87.36 (1), 74.44 (1) |
V (Å3) | 451.85 (14) |
Z | 2 |
Radiation type | Cu Kα |
µ (mm−1) | 2.87 |
Crystal size (mm) | 0.13 × 0.13 × 0.10 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.731, 0.789 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 1713, 1606, 1259 |
Rint | 0.036 |
(sin θ/λ)max (Å−1) | 0.597 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.098, 1.08 |
No. of reflections | 1606 |
No. of parameters | 143 |
No. of restraints | 1 |
H-atom treatment | Only H-atom coordinates refined |
Δρmax, Δρmin (e Å−3) | 0.17, −0.26 |
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 | 0.848 (10) | 2.104 (12) | 2.943 (3) | 170 (3) |
Symmetry code: (i) −x+1, −y, −z+1. |
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The biological activity of alkyl sulfonanilides is thought to be due to the H atom of the phenyl N—H portion of the sulfonanilide molecule, 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-methylphenyl)methanesulfonamde (2MPMSA), (I), has been determined to explore the substituent effects on the solid-state structures of anilides and sulfonanilides (Gowda et al., 2007a,b,c,d; Gowda, Kozisek et al., 2007; Gowda et al., 2000).
The conformation of the N—H bond in the structure of 2MPMSA is syn to the ortho-methyl substituent (Fig. 1), in contrast with the anti conformation observed for the meta-methyl-substituted compound (3MPMSA) (Gowda et al., 2007c). The ortho-substitution of the methyl group in N-(phenyl)methanesulfonamde (PMSA) changes its space group from monoclinic P21/c (Klug, 1968) to triclinic P1, compared with the change from monoclinic P21/c to orthorhombic Pccn on meta-methyl substitution (Gowda et al., 2007c).
The bond parameters in PMSA (Klug, 1968), 2MPMSA and 3MPMSA (Gowda et al., 2007c) are similar except for the torsion angles C1—S2—N5—C6, S2—N5—C6—C7, S2—N5—C6—C11, which have the following values: 62.2 (2), 75.5 (2) and -106.6 (2)°, respectively, in PMSA; -64.5 (2), 117.1 (2) and -65.3 (3)°, respectively, in 2MPMSA; 57.9 (3), 68.1 (4) and -114.3 (3)°, respectively, in 3MPMSA. The data included for PMSA are the values determined under the present conditions as the literature values were determined in [Meaning not clear. Text missing?] (Klug, 1968).
The N—H H atom lies 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 what was observed in PMSA and 3MPMSA. Thus, the amide H atom is available to
a receptor molecule during biological activity.
The molecules in the title compound form centrosymmetric dimers via an N5—H5N···O3(1 - x,-y, 1 - z) hydrogen bond (Table 1 and Fig. 2).