Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026724/dn2186sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026724/dn2186Isup2.hkl |
CCDC reference: 614682
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 compound were obtained from a slow evaporation of its ethanolic solution and used for X-ray diffraction studies at room temperature.
H atoms attached to C atoms were fixed geometrically and treated as riding, with C—H = 0.93 Å (aromatic) or 0.96 Å (CH3) and with Uiso(H) = 1.2Ueq(aromatic) or Uiso(H) = 1.5Ueq(CH3). H atom attched to N was refined using a N—H restraint of 0.85 (1) Å.
The biological activity of sulfonanilides is thought to be due to the amide hydrogen portion of the molecules as it can align itself in relation to a receptor site. Thus the structural studies of sulfonanilides are of interest. In the present work, the structure of N-(3,5-dichlorophenyl)-methanesulfonamde (35DCPMSA) has been determined as part of our study of the substituent effects on the solid state structures of methanesulfonanilides (Gowda et al., 2007a, b). The structure of 35DCPMSA (Fig. 1) is similar to those of other methanesulfonanilides (Gowda et al., 2007a, b). 35DCPMSA crystallizes in monoclinic P21/c space group in contrast to the monoclinc P21/c, monoclinic P21/n, triclinic P-1 and triclinic P-1 space groups observed for N-(2,3-dichlorophenyl)-methanesulfonamide (23DCPMSA), N-(2,4-dichlorophenyl)-methanesulfonamide (24DCPMSA), N-(2,5-dichlorophenyl)-methanesulfonamide (25DCPMSA), N-(3,4-dichlorophenyl)-methanesulfonamide (34DCPMSA)(Gowda et al., 2007b), respectively. The substitution of a Cl atom at the meta position of N-(phenyl)-methanesulfonamde (PMSA) (Klug, 1968) to produce N-(3-chlorophenyl)-methanesulfonamide (3CPMSA) changes its space group from monoclinic P21/c to C 2/c (Gowda et al., 2007a). The substitution of an additional chloro group either at ortho, para or meta position of 3CPMSA to produce 23DCPMSA, 34DCPMSA or 35DCPMSA, respectively, changes the space group from monoclinc C 2/c to monoclinic P21/c with 23DCPMSA, triclinic P-1 with 34DCPMSA and monoclinic P21/c with 35DCPMSA. The geometric parameters in 35DCPMSA are similar to those in other methanesulfonanilides except for some difference in the bond and torsional angles. The N—H is roughly in the plane of the dichlorophenyl group with a deviation of -0.021 (7) Å from the plane, whereas the S atom is slightly above with a deviation of 0.285 (9) Å. The dihedral angle between the benzene ring and the C6—N5—S2 plane is 14.4 (5)°. The N—H···O hydrogen bonds (Table 1) build up chains which are further connected through weak C—H (methyl)···O interactions (Fig. 2).
For related literature, see: Gowda et al. (2007a, 2007b); Jayalakshmi & Gowda (2004); Klug (1968).
Data collection: CAD-4-PC Software (Enraf–Nonius, 1996); cell refinement: CAD-4-PC Software; 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: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
C7H7Cl2NO2S | F(000) = 488 |
Mr = 240.10 | Dx = 1.627 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 16.076 (3) Å | θ = 2.8–19.9° |
b = 5.053 (2) Å | µ = 7.70 mm−1 |
c = 12.148 (3) Å | T = 299 K |
β = 96.60 (2)° | Long laminar, colourless |
V = 980.3 (5) Å3 | 0.75 × 0.30 × 0.03 mm |
Z = 4 |
Enraf–Nonius CAD4 diffractometer | 1424 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.059 |
Graphite monochromator | θmax = 67.1°, θmin = 2.8° |
ω scans | h = −19→19 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→6 |
Tmin = 0.043, Tmax = 0.597 | l = −14→1 |
1828 measured reflections | 3 standard reflections every 120 min |
1731 independent reflections | intensity decay: 2.5% |
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)] = 0.092 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.255 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | w = 1/[σ2(Fo2) + (0.2P)2] where P = (Fo2 + 2Fc2)/3 |
1731 reflections | (Δ/σ)max < 0.001 |
123 parameters | Δρmax = 1.17 e Å−3 |
1 restraint | Δρmin = −0.70 e Å−3 |
C7H7Cl2NO2S | V = 980.3 (5) Å3 |
Mr = 240.10 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 16.076 (3) Å | µ = 7.70 mm−1 |
b = 5.053 (2) Å | T = 299 K |
c = 12.148 (3) Å | 0.75 × 0.30 × 0.03 mm |
β = 96.60 (2)° |
Enraf–Nonius CAD4 diffractometer | 1424 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.059 |
Tmin = 0.043, Tmax = 0.597 | 3 standard reflections every 120 min |
1828 measured reflections | intensity decay: 2.5% |
1731 independent reflections |
R[F2 > 2σ(F2)] = 0.092 | 1 restraint |
wR(F2) = 0.255 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | Δρmax = 1.17 e Å−3 |
1731 reflections | Δρmin = −0.70 e Å−3 |
123 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 | 0.6079 (3) | 0.3484 (10) | 1.0081 (4) | 0.0512 (12) | |
H1A | 0.5810 | 0.2657 | 1.0658 | 0.077* | |
H1B | 0.5894 | 0.5286 | 0.9994 | 0.077* | |
H1C | 0.6675 | 0.3447 | 1.0275 | 0.077* | |
C6 | 0.7071 (3) | 0.3919 (9) | 0.7811 (3) | 0.0415 (10) | |
C7 | 0.7711 (3) | 0.2524 (11) | 0.8417 (4) | 0.0525 (12) | |
H7 | 0.7596 | 0.1182 | 0.8901 | 0.063* | |
C8 | 0.8527 (4) | 0.3193 (11) | 0.8280 (5) | 0.0587 (13) | |
C9 | 0.8727 (3) | 0.5086 (12) | 0.7540 (5) | 0.0611 (13) | |
H9 | 0.9281 | 0.5488 | 0.7456 | 0.073* | |
C10 | 0.8076 (4) | 0.6353 (11) | 0.6932 (5) | 0.0562 (12) | |
C11 | 0.7251 (3) | 0.5846 (9) | 0.7054 (4) | 0.0482 (11) | |
H11 | 0.6822 | 0.6770 | 0.6641 | 0.058* | |
N5 | 0.6212 (2) | 0.3432 (8) | 0.7865 (3) | 0.0437 (9) | |
O3 | 0.4928 (2) | 0.1929 (7) | 0.8545 (3) | 0.0532 (9) | |
O4 | 0.6204 (2) | −0.0779 (7) | 0.8935 (3) | 0.0618 (10) | |
S2 | 0.58202 (7) | 0.1770 (2) | 0.88336 (8) | 0.0415 (5) | |
Cl12 | 0.83015 (11) | 0.8707 (3) | 0.59639 (16) | 0.0837 (6) | |
Cl13 | 0.93272 (10) | 0.1532 (5) | 0.90719 (17) | 0.0962 (8) | |
H5 | 0.586 (2) | 0.451 (7) | 0.754 (3) | 0.033 (11)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.063 (3) | 0.046 (3) | 0.043 (2) | −0.002 (2) | 0.003 (2) | −0.0037 (19) |
C6 | 0.046 (2) | 0.035 (2) | 0.043 (2) | 0.0028 (18) | 0.0066 (17) | −0.0026 (17) |
C7 | 0.056 (3) | 0.051 (3) | 0.051 (2) | 0.007 (2) | 0.008 (2) | 0.006 (2) |
C8 | 0.053 (3) | 0.061 (3) | 0.061 (3) | 0.006 (2) | 0.003 (2) | 0.006 (2) |
C9 | 0.051 (3) | 0.060 (3) | 0.074 (3) | −0.006 (2) | 0.017 (2) | 0.002 (3) |
C10 | 0.063 (3) | 0.046 (3) | 0.063 (3) | −0.001 (2) | 0.022 (2) | 0.005 (2) |
C11 | 0.056 (2) | 0.036 (2) | 0.053 (2) | 0.004 (2) | 0.012 (2) | 0.0040 (19) |
N5 | 0.043 (2) | 0.045 (2) | 0.0418 (19) | 0.0047 (15) | 0.0016 (16) | 0.0088 (15) |
O3 | 0.0509 (18) | 0.048 (2) | 0.0596 (19) | −0.0087 (14) | 0.0031 (15) | −0.0066 (14) |
O4 | 0.076 (2) | 0.0288 (18) | 0.082 (2) | 0.0097 (17) | 0.0151 (19) | 0.0060 (16) |
S2 | 0.0479 (7) | 0.0299 (7) | 0.0466 (7) | −0.0017 (4) | 0.0061 (5) | −0.0010 (4) |
Cl12 | 0.0841 (11) | 0.0712 (11) | 0.1022 (12) | −0.0009 (8) | 0.0379 (9) | 0.0311 (9) |
Cl13 | 0.0531 (9) | 0.1287 (19) | 0.1048 (13) | 0.0228 (8) | 0.0006 (8) | 0.0388 (11) |
C1—S2 | 1.754 (5) | C8—Cl13 | 1.732 (6) |
C1—H1A | 0.9600 | C9—C10 | 1.369 (8) |
C1—H1B | 0.9600 | C9—H9 | 0.9300 |
C1—H1C | 0.9600 | C10—C11 | 1.376 (7) |
C6—C7 | 1.387 (7) | C10—Cl12 | 1.740 (5) |
C6—C11 | 1.392 (7) | C11—H11 | 0.9300 |
C6—N5 | 1.412 (6) | N5—S2 | 1.630 (4) |
C7—C8 | 1.382 (8) | N5—H5 | 0.85 (3) |
C7—H7 | 0.9300 | O3—S2 | 1.439 (4) |
C8—C9 | 1.376 (8) | O4—S2 | 1.427 (4) |
S2—C1—H1A | 109.5 | C8—C9—H9 | 121.4 |
S2—C1—H1B | 109.5 | C9—C10—C11 | 122.8 (5) |
H1A—C1—H1B | 109.5 | C9—C10—Cl12 | 118.6 (4) |
S2—C1—H1C | 109.5 | C11—C10—Cl12 | 118.6 (4) |
H1A—C1—H1C | 109.5 | C10—C11—C6 | 118.5 (5) |
H1B—C1—H1C | 109.5 | C10—C11—H11 | 120.7 |
C7—C6—C11 | 120.6 (4) | C6—C11—H11 | 120.7 |
C7—C6—N5 | 123.8 (4) | C6—N5—S2 | 125.8 (3) |
C11—C6—N5 | 115.5 (4) | C6—N5—H5 | 118 (3) |
C8—C7—C6 | 117.9 (5) | S2—N5—H5 | 112 (3) |
C8—C7—H7 | 121.1 | O4—S2—O3 | 118.7 (2) |
C6—C7—H7 | 121.1 | O4—S2—N5 | 109.2 (2) |
C9—C8—C7 | 123.0 (5) | O3—S2—N5 | 104.6 (2) |
C9—C8—Cl13 | 119.0 (4) | O4—S2—C1 | 108.3 (2) |
C7—C8—Cl13 | 117.9 (4) | O3—S2—C1 | 108.3 (2) |
C10—C9—C8 | 117.1 (5) | N5—S2—C1 | 107.2 (2) |
C10—C9—H9 | 121.4 |
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5···O3i | 0.85 (3) | 2.11 (4) | 2.949 (5) | 170 (4) |
C1—H1B···O4ii | 0.96 | 2.45 | 3.233 (6) | 138 |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C7H7Cl2NO2S |
Mr | 240.10 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 299 |
a, b, c (Å) | 16.076 (3), 5.053 (2), 12.148 (3) |
β (°) | 96.60 (2) |
V (Å3) | 980.3 (5) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 7.70 |
Crystal size (mm) | 0.75 × 0.30 × 0.03 |
Data collection | |
Diffractometer | Enraf–Nonius CAD4 |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.043, 0.597 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 1828, 1731, 1424 |
Rint | 0.059 |
(sin θ/λ)max (Å−1) | 0.597 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.092, 0.255, 1.09 |
No. of reflections | 1731 |
No. of parameters | 123 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 1.17, −0.70 |
Computer programs: CAD-4-PC Software (Enraf–Nonius, 1996), CAD-4-PC Software, REDU4 (Stoe & Cie, 1987), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5···O3i | 0.85 (3) | 2.11 (4) | 2.949 (5) | 170 (4) |
C1—H1B···O4ii | 0.96 | 2.45 | 3.233 (6) | 138.4 |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x, y+1, z. |
The biological activity of sulfonanilides is thought to be due to the amide hydrogen portion of the molecules as it can align itself in relation to a receptor site. Thus the structural studies of sulfonanilides are of interest. In the present work, the structure of N-(3,5-dichlorophenyl)-methanesulfonamde (35DCPMSA) has been determined as part of our study of the substituent effects on the solid state structures of methanesulfonanilides (Gowda et al., 2007a, b). The structure of 35DCPMSA (Fig. 1) is similar to those of other methanesulfonanilides (Gowda et al., 2007a, b). 35DCPMSA crystallizes in monoclinic P21/c space group in contrast to the monoclinc P21/c, monoclinic P21/n, triclinic P-1 and triclinic P-1 space groups observed for N-(2,3-dichlorophenyl)-methanesulfonamide (23DCPMSA), N-(2,4-dichlorophenyl)-methanesulfonamide (24DCPMSA), N-(2,5-dichlorophenyl)-methanesulfonamide (25DCPMSA), N-(3,4-dichlorophenyl)-methanesulfonamide (34DCPMSA)(Gowda et al., 2007b), respectively. The substitution of a Cl atom at the meta position of N-(phenyl)-methanesulfonamde (PMSA) (Klug, 1968) to produce N-(3-chlorophenyl)-methanesulfonamide (3CPMSA) changes its space group from monoclinic P21/c to C 2/c (Gowda et al., 2007a). The substitution of an additional chloro group either at ortho, para or meta position of 3CPMSA to produce 23DCPMSA, 34DCPMSA or 35DCPMSA, respectively, changes the space group from monoclinc C 2/c to monoclinic P21/c with 23DCPMSA, triclinic P-1 with 34DCPMSA and monoclinic P21/c with 35DCPMSA. The geometric parameters in 35DCPMSA are similar to those in other methanesulfonanilides except for some difference in the bond and torsional angles. The N—H is roughly in the plane of the dichlorophenyl group with a deviation of -0.021 (7) Å from the plane, whereas the S atom is slightly above with a deviation of 0.285 (9) Å. The dihedral angle between the benzene ring and the C6—N5—S2 plane is 14.4 (5)°. The N—H···O hydrogen bonds (Table 1) build up chains which are further connected through weak C—H (methyl)···O interactions (Fig. 2).