Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680702555X/lw2022sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680702555X/lw2022Isup2.hkl |
CCDC reference: 614679
Key indicators
- Single-crystal X-ray study
- T = 303 K
- Mean (C-C) = 0.004 Å
- R factor = 0.054
- wR factor = 0.152
- Data-to-parameter ratio = 15.9
checkCIF/PLATON results
No syntax errors found
Alert level C 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 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
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 1.2Ueq (parent atom).
The structural studies of alkyl sulphonanilides are of interest as their biological activity is thought to be due to the hydrogen of the phenyl N—H portion of the sulphonanilide molecules as it can align itself, in relation to a receptor site. In the present work, the structure of N-(2,3-dichlorophenyl)-methanesulfonamide (23DCPMSA) has been determined to explore the substituent effects on the solid state structures of sulfonanilides (Gowda et al., 2007a-k). The structure of 23DCPMSA (Fig. 1) resembles those of N-(phenyl)-methanesulfonamide (PMSA) (Klug, 1968) and other methylsulfonanilides (Gowda et al., 2007a-k). The conformation of the N—H bond in 23DCPMSA is syn to both ortho and meta chloro substituents, in contrast to it lying between syn and anti conformations to the methyl substituents at ortho and meta positions, in N-(2,3-dimethylphenyl)-methanesulfonamide (23DMPMSA)(Gowda et al., 2007h) and chloro substituents in N-(2-chlorophenyl)- methanesulfonamide (2CPMSA)(Gowda et al., 2007k) and N-(3-chlorophenyl)-methanesulfonamide (3CPMSA)(Gowda et al., 2007e). Chloro substitutions at both ortho and meta positions in PMSA do not change its space group, in contrast to change over from monoclinic P21/c to orthorhombic P212121 space group on methyl substitutions at both ortho and meta positions in PMSA to form 23DMPMSA (Gowda et al., 2007h). The bond parameters in 23DCPMSA are similar to those in PMSA, 23DMPMSA and other methylsulfonanilides, except for some difference in the bond and torsional angles. The amide hydrogen is available to a receptor molecule during its biological activity as it 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 other methylsulfonanilides. The molecules in 23DCPMSA 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,h,i,j,k); Jayalakshmi & Gowda (2004); Klug (1968); Spek (2003).
Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2003); 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.
C7H7Cl2NO2S | F(000) = 488 |
Mr = 240.10 | Dx = 1.650 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2484 reflections |
a = 11.1299 (9) Å | θ = 2.8–26.5° |
b = 5.1365 (6) Å | µ = 0.85 mm−1 |
c = 16.908 (1) Å | T = 303 K |
β = 90.038 (6)° | Long prism, colourless |
V = 966.61 (15) Å3 | 0.50 × 0.15 × 0.15 mm |
Z = 4 |
Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector | 1694 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.058 |
Graphite monochromator | θmax = 26.4°, θmin = 4.2° |
Rotation method data acquisition using ω scans | h = −13→13 |
5750 measured reflections | k = −3→6 |
1939 independent reflections | l = −21→21 |
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)] = 0.054 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.152 | w = 1/[σ2(Fo2) + (0.1248P)2 + 0.7632P] where P = (Fo2 + 2Fc2)/3 |
S = 0.87 | (Δ/σ)max = 0.011 |
1939 reflections | Δρmax = 0.57 e Å−3 |
122 parameters | Δρmin = −0.71 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.016 (4) |
C7H7Cl2NO2S | V = 966.61 (15) Å3 |
Mr = 240.10 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.1299 (9) Å | µ = 0.85 mm−1 |
b = 5.1365 (6) Å | T = 303 K |
c = 16.908 (1) Å | 0.50 × 0.15 × 0.15 mm |
β = 90.038 (6)° |
Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector | 1694 reflections with I > 2σ(I) |
5750 measured reflections | Rint = 0.058 |
1939 independent reflections |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.152 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.87 | Δρmax = 0.57 e Å−3 |
1939 reflections | Δρmin = −0.71 e Å−3 |
122 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 | 0.1880 (4) | 0.2088 (7) | −0.08851 (19) | 0.0657 (10) | |
H1A | 0.1995 | 0.1405 | −0.1408 | 0.099* | |
H1B | 0.2505 | 0.3317 | −0.0768 | 0.099* | |
H1C | 0.1114 | 0.2940 | −0.0855 | 0.099* | |
C6 | 0.2632 (2) | 0.2694 (5) | 0.10012 (14) | 0.0341 (5) | |
C7 | 0.3847 (3) | 0.2686 (6) | 0.08165 (17) | 0.0439 (6) | |
H7 | 0.4140 | 0.1514 | 0.0444 | 0.053* | |
C8 | 0.4626 (3) | 0.4409 (6) | 0.1182 (2) | 0.0520 (8) | |
H8 | 0.5438 | 0.4368 | 0.1054 | 0.062* | |
C9 | 0.4221 (3) | 0.6189 (6) | 0.17337 (18) | 0.0485 (7) | |
H9 | 0.4750 | 0.7356 | 0.1970 | 0.058* | |
C10 | 0.3017 (3) | 0.6200 (5) | 0.19266 (15) | 0.0382 (6) | |
C11 | 0.2221 (2) | 0.4472 (5) | 0.15705 (14) | 0.0324 (5) | |
Cl12 | 0.07252 (6) | 0.44392 (16) | 0.18443 (4) | 0.0490 (3) | |
Cl13 | 0.24995 (7) | 0.84109 (15) | 0.26233 (4) | 0.0517 (3) | |
N5 | 0.1792 (2) | 0.0930 (5) | 0.06667 (14) | 0.0425 (6) | |
H5N | 0.107 (3) | 0.137 (6) | 0.077 (2) | 0.051* | |
O3 | 0.0884 (2) | −0.2047 (4) | −0.02830 (14) | 0.0581 (6) | |
O4 | 0.3061 (2) | −0.1694 (4) | −0.02436 (14) | 0.0543 (6) | |
S2 | 0.19291 (6) | −0.04550 (12) | −0.02004 (4) | 0.0371 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.106 (3) | 0.0489 (17) | 0.0418 (16) | 0.0056 (18) | −0.0132 (18) | 0.0018 (14) |
C6 | 0.0320 (12) | 0.0386 (12) | 0.0318 (11) | 0.0000 (10) | −0.0014 (9) | −0.0023 (10) |
C7 | 0.0360 (14) | 0.0521 (16) | 0.0437 (14) | 0.0054 (11) | 0.0032 (11) | −0.0111 (12) |
C8 | 0.0297 (14) | 0.067 (2) | 0.0591 (19) | 0.0001 (12) | 0.0020 (13) | −0.0091 (15) |
C9 | 0.0394 (15) | 0.0577 (17) | 0.0485 (17) | −0.0056 (13) | −0.0093 (12) | −0.0050 (13) |
C10 | 0.0453 (14) | 0.0405 (13) | 0.0288 (12) | 0.0036 (11) | −0.0034 (10) | −0.0032 (10) |
C11 | 0.0302 (12) | 0.0393 (13) | 0.0276 (11) | 0.0039 (9) | −0.0001 (9) | 0.0024 (9) |
Cl12 | 0.0334 (4) | 0.0687 (5) | 0.0449 (5) | 0.0027 (3) | 0.0076 (3) | −0.0140 (3) |
Cl13 | 0.0633 (5) | 0.0521 (5) | 0.0395 (4) | 0.0029 (3) | −0.0015 (3) | −0.0138 (3) |
N5 | 0.0334 (12) | 0.0530 (13) | 0.0412 (12) | −0.0036 (10) | 0.0063 (10) | −0.0162 (10) |
O3 | 0.0481 (12) | 0.0551 (12) | 0.0711 (15) | −0.0108 (10) | 0.0010 (10) | −0.0263 (11) |
O4 | 0.0479 (12) | 0.0562 (12) | 0.0588 (13) | 0.0178 (10) | −0.0010 (10) | −0.0168 (10) |
S2 | 0.0386 (4) | 0.0353 (4) | 0.0373 (4) | 0.0039 (2) | −0.0014 (3) | −0.0079 (2) |
C1—S2 | 1.746 (3) | C8—H8 | 0.9300 |
C1—H1A | 0.9600 | C9—C10 | 1.380 (4) |
C1—H1B | 0.9600 | C9—H9 | 0.9300 |
C1—H1C | 0.9600 | C10—C11 | 1.390 (4) |
C6—C7 | 1.388 (4) | C10—Cl13 | 1.735 (3) |
C6—C11 | 1.404 (3) | C11—Cl12 | 1.729 (3) |
C6—N5 | 1.420 (3) | N5—S2 | 1.637 (2) |
C7—C8 | 1.384 (4) | N5—H5N | 0.86 (4) |
C7—H7 | 0.9300 | O3—S2 | 1.428 (2) |
C8—C9 | 1.382 (4) | O4—S2 | 1.413 (2) |
S2—C1—H1A | 109.5 | C10—C9—H9 | 120.7 |
S2—C1—H1B | 109.5 | C11—C10—C9 | 120.9 (2) |
H1A—C1—H1B | 109.5 | C11—C10—Cl13 | 120.0 (2) |
S2—C1—H1C | 109.5 | C9—C10—Cl13 | 119.1 (2) |
H1A—C1—H1C | 109.5 | C10—C11—C6 | 120.3 (2) |
H1B—C1—H1C | 109.5 | C10—C11—Cl12 | 120.22 (19) |
C7—C6—C11 | 118.3 (2) | C6—C11—Cl12 | 119.45 (19) |
C7—C6—N5 | 123.4 (2) | C6—N5—S2 | 124.90 (19) |
C11—C6—N5 | 118.3 (2) | C6—N5—H5N | 112 (2) |
C6—C7—C8 | 120.5 (3) | S2—N5—H5N | 113 (2) |
C6—C7—H7 | 119.8 | O4—S2—O3 | 117.55 (14) |
C8—C7—H7 | 119.8 | O4—S2—N5 | 109.03 (13) |
C9—C8—C7 | 121.3 (3) | O3—S2—N5 | 105.07 (12) |
C9—C8—H8 | 119.3 | O4—S2—C1 | 109.26 (18) |
C7—C8—H8 | 119.3 | O3—S2—C1 | 109.79 (18) |
C8—C9—C10 | 118.6 (3) | N5—S2—C1 | 105.41 (15) |
C8—C9—H9 | 120.7 | ||
C11—C6—C7—C8 | −0.6 (4) | C7—C6—C11—C10 | 1.0 (4) |
N5—C6—C7—C8 | −178.0 (3) | N5—C6—C11—C10 | 178.6 (2) |
C6—C7—C8—C9 | −0.4 (5) | C7—C6—C11—Cl12 | −177.3 (2) |
C7—C8—C9—C10 | 1.0 (5) | N5—C6—C11—Cl12 | 0.3 (3) |
C8—C9—C10—C11 | −0.5 (4) | C7—C6—N5—S2 | −27.1 (4) |
C8—C9—C10—Cl13 | 179.6 (2) | C11—C6—N5—S2 | 155.4 (2) |
C9—C10—C11—C6 | −0.5 (4) | C6—N5—S2—O4 | 53.1 (3) |
Cl13—C10—C11—C6 | 179.42 (19) | C6—N5—S2—O3 | 179.9 (2) |
C9—C10—C11—Cl12 | 177.8 (2) | C6—N5—S2—C1 | −64.1 (3) |
Cl13—C10—C11—Cl12 | −2.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5N···O3i | 0.86 (4) | 2.35 (4) | 3.101 (3) | 147 (3) |
N5—H5N···Cl12 | 0.86 (4) | 2.43 (3) | 2.937 (2) | 118 (3) |
Symmetry code: (i) −x, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C7H7Cl2NO2S |
Mr | 240.10 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 303 |
a, b, c (Å) | 11.1299 (9), 5.1365 (6), 16.908 (1) |
β (°) | 90.038 (6) |
V (Å3) | 966.61 (15) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.85 |
Crystal size (mm) | 0.50 × 0.15 × 0.15 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5750, 1939, 1694 |
Rint | 0.058 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.152, 0.87 |
No. of reflections | 1939 |
No. of parameters | 122 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.57, −0.71 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2003), CrysAlis CCD, CrysAlis RED (Oxford Diffraction, 2003), 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 | 0.86 (4) | 2.35 (4) | 3.101 (3) | 147 (3) |
N5—H5N···Cl12 | 0.86 (4) | 2.43 (3) | 2.937 (2) | 118 (3) |
Symmetry code: (i) −x, −y, −z. |
The structural studies of alkyl sulphonanilides are of interest as their biological activity is thought to be due to the hydrogen of the phenyl N—H portion of the sulphonanilide molecules as it can align itself, in relation to a receptor site. In the present work, the structure of N-(2,3-dichlorophenyl)-methanesulfonamide (23DCPMSA) has been determined to explore the substituent effects on the solid state structures of sulfonanilides (Gowda et al., 2007a-k). The structure of 23DCPMSA (Fig. 1) resembles those of N-(phenyl)-methanesulfonamide (PMSA) (Klug, 1968) and other methylsulfonanilides (Gowda et al., 2007a-k). The conformation of the N—H bond in 23DCPMSA is syn to both ortho and meta chloro substituents, in contrast to it lying between syn and anti conformations to the methyl substituents at ortho and meta positions, in N-(2,3-dimethylphenyl)-methanesulfonamide (23DMPMSA)(Gowda et al., 2007h) and chloro substituents in N-(2-chlorophenyl)- methanesulfonamide (2CPMSA)(Gowda et al., 2007k) and N-(3-chlorophenyl)-methanesulfonamide (3CPMSA)(Gowda et al., 2007e). Chloro substitutions at both ortho and meta positions in PMSA do not change its space group, in contrast to change over from monoclinic P21/c to orthorhombic P212121 space group on methyl substitutions at both ortho and meta positions in PMSA to form 23DMPMSA (Gowda et al., 2007h). The bond parameters in 23DCPMSA are similar to those in PMSA, 23DMPMSA and other methylsulfonanilides, except for some difference in the bond and torsional angles. The amide hydrogen is available to a receptor molecule during its biological activity as it 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 other methylsulfonanilides. The molecules in 23DCPMSA are packed into chains in the direction of b axis (Fig. 2) through N—H···O hydrogen bonds (Fig. 3 and Table 1).