Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807015693/bt2328sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807015693/bt2328Isup2.hkl |
CCDC reference: 614580
The title compound was prepared according to a 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 an ethanolic solution and used for X-ray diffraction studied at room temperature.
All H atoms attached to C atoms were fixed geometrically and treated as riding with C—H = 0.93 Å (CH aromatic) or 0.96 Å (CH3) with Uiso(H) = 1.2 Ueq(C) or Uiso(H) = 1.5 Ueq(Cmethyl). The coordinates of the H atom bonded to N were refined with a distance restraint [N–H = 0.86 (1) Å] and Uiso(H) = 1.2 Ueq(N).
Methanesulfonanilides are of interest due to their distinct chemical and physical properties. The alkyl sulfonanilido moiety is an important constituent of many biologically significant compounds. The stereochemistry of these molecules, particularly in the vicinity of the phenyl-N—H portion would be of extreme interest in formulating an explanation of their biological activity similar to phenolic derivatives. The biological activity 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. Thus the structural studies of sulfonanilides are of interest. In the present work, the structure of N-(3-nitrophenyl)-methanesulfonamde (3NPMSA) has been determined to explore the substituent effects of polar groups on the structures of anilides and sulfonanilides as part of a study on the systematization of the crystal structures of this class of compounds in general (Gowda et al., 2000; Gowda et al., 2007a,b,c). In the structure of 3NPMSA the conformation of the N—H bond is anti to the meta-nitro substituent (Fig.1). The amide hydrogen is thus available to a receptor molecule during biological activity. Selected geometric parameters are shown in Table 1. The molecules are linked into centrosymmetric dimers (Fig. 2) through a N—H···O hydrogen bond (Table 2).
For related literature, see: Gowda et al. (2000); Gowda et al. (2007); Gowda et al. (2007a); Gowda et al. (2007b); Jayalakshmi & Gowda (2004).
Data collection: CAD-4-PC (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.
C7H8N2O4S | Z = 2 |
Mr = 216.21 | F(000) = 224 |
Triclinic, P1 | Dx = 1.592 Mg m−3 |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.54180 Å |
a = 6.959 (1) Å | Cell parameters from 25 reflections |
b = 8.207 (1) Å | θ = 5.5–25.3° |
c = 8.759 (1) Å | µ = 3.18 mm−1 |
α = 96.93 (1)° | T = 299 K |
β = 111.05 (1)° | Prism, orange |
γ = 99.78 (1)° | 0.25 × 0.20 × 0.20 mm |
V = 451.02 (10) Å3 |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.071 |
Radiation source: fine-focus sealed tube | θmax = 66.9°, θmin = 5.5° |
Graphite monochromator | h = −8→8 |
ω/2θ scans | k = −9→5 |
2782 measured reflections | l = −10→10 |
1611 independent reflections | 3 standard reflections every 120 min |
1427 reflections with I > 2σ(I) | intensity decay: 5% |
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)] = 0.042 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.105 | w = 1/[σ2(Fo2) + (0.0588P)2 + 0.0989P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
1611 reflections | Δρmax = 0.49 e Å−3 |
143 parameters | Δρmin = −0.49 e Å−3 |
1 restraint | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.091 (5) |
C7H8N2O4S | γ = 99.78 (1)° |
Mr = 216.21 | V = 451.02 (10) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.959 (1) Å | Cu Kα radiation |
b = 8.207 (1) Å | µ = 3.18 mm−1 |
c = 8.759 (1) Å | T = 299 K |
α = 96.93 (1)° | 0.25 × 0.20 × 0.20 mm |
β = 111.05 (1)° |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.071 |
2782 measured reflections | 3 standard reflections every 120 min |
1611 independent reflections | intensity decay: 5% |
1427 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.042 | 1 restraint |
wR(F2) = 0.105 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.49 e Å−3 |
1611 reflections | Δρmin = −0.49 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 | 0.0954 (4) | 0.8080 (3) | 0.6291 (3) | 0.0525 (6) | |
H1A | 0.1469 | 0.9231 | 0.6882 | 0.063* | |
H1B | 0.1232 | 0.7341 | 0.7074 | 0.063* | |
H1C | −0.0542 | 0.7869 | 0.5660 | 0.063* | |
C6 | 0.5674 (3) | 0.7198 (2) | 0.7373 (2) | 0.0362 (4) | |
C7 | 0.5029 (3) | 0.5475 (3) | 0.7208 (2) | 0.0390 (4) | |
H7 | 0.398 (4) | 0.479 (3) | 0.622 (3) | 0.047* | |
C8 | 0.6099 (3) | 0.4749 (2) | 0.8503 (2) | 0.0386 (4) | |
C9 | 0.7761 (3) | 0.5638 (3) | 0.9932 (3) | 0.0447 (5) | |
H9 | 0.838 (4) | 0.505 (4) | 1.075 (3) | 0.054* | |
C10 | 0.8369 (3) | 0.7366 (3) | 1.0067 (3) | 0.0501 (5) | |
H10 | 0.947 (4) | 0.796 (4) | 1.100 (4) | 0.060* | |
C11 | 0.7328 (3) | 0.8137 (3) | 0.8807 (3) | 0.0456 (5) | |
H11 | 0.770 (4) | 0.938 (4) | 0.890 (3) | 0.055* | |
N5 | 0.4746 (3) | 0.8055 (2) | 0.6095 (2) | 0.0478 (5) | |
H5N | 0.539 (4) | 0.9067 (17) | 0.621 (3) | 0.057* | |
N12 | 0.5437 (3) | 0.2912 (2) | 0.8337 (2) | 0.0515 (5) | |
O3 | 0.2113 (2) | 0.8999 (2) | 0.39469 (18) | 0.0530 (4) | |
O4 | 0.1475 (2) | 0.59956 (19) | 0.41044 (18) | 0.0507 (4) | |
O13 | 0.6464 (3) | 0.2257 (2) | 0.9437 (3) | 0.0758 (6) | |
O14 | 0.3897 (4) | 0.2133 (2) | 0.7117 (2) | 0.0742 (6) | |
S2 | 0.22342 (7) | 0.77189 (6) | 0.49366 (5) | 0.0378 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0592 (13) | 0.0449 (12) | 0.0550 (12) | 0.0107 (10) | 0.0241 (10) | 0.0113 (10) |
C6 | 0.0321 (9) | 0.0376 (10) | 0.0367 (9) | 0.0036 (7) | 0.0118 (7) | 0.0111 (8) |
C7 | 0.0412 (10) | 0.0353 (10) | 0.0350 (9) | 0.0021 (8) | 0.0117 (8) | 0.0062 (8) |
C8 | 0.0439 (10) | 0.0349 (10) | 0.0435 (10) | 0.0106 (8) | 0.0225 (8) | 0.0115 (8) |
C9 | 0.0390 (10) | 0.0542 (12) | 0.0437 (11) | 0.0151 (9) | 0.0142 (8) | 0.0192 (9) |
C10 | 0.0378 (10) | 0.0538 (13) | 0.0434 (11) | 0.0019 (9) | 0.0022 (9) | 0.0091 (10) |
C11 | 0.0384 (10) | 0.0386 (11) | 0.0479 (11) | −0.0021 (8) | 0.0075 (8) | 0.0095 (9) |
N5 | 0.0372 (9) | 0.0424 (9) | 0.0494 (10) | −0.0069 (7) | 0.0029 (7) | 0.0230 (8) |
N12 | 0.0689 (12) | 0.0380 (10) | 0.0583 (11) | 0.0180 (9) | 0.0324 (10) | 0.0162 (9) |
O3 | 0.0497 (8) | 0.0513 (9) | 0.0454 (8) | −0.0002 (7) | 0.0041 (6) | 0.0257 (7) |
O4 | 0.0506 (8) | 0.0392 (8) | 0.0468 (8) | −0.0013 (6) | 0.0087 (6) | 0.0006 (7) |
O13 | 0.0925 (14) | 0.0541 (11) | 0.0904 (14) | 0.0316 (10) | 0.0319 (12) | 0.0393 (11) |
O14 | 0.1008 (15) | 0.0382 (9) | 0.0638 (11) | −0.0025 (9) | 0.0188 (10) | 0.0045 (8) |
S2 | 0.0367 (3) | 0.0330 (3) | 0.0339 (3) | −0.00126 (19) | 0.0055 (2) | 0.00977 (19) |
C1—S2 | 1.747 (2) | C9—C10 | 1.387 (3) |
C1—H1A | 0.9600 | C9—H9 | 0.93 (3) |
C1—H1B | 0.9600 | C10—C11 | 1.376 (3) |
C1—H1C | 0.9600 | C10—H10 | 0.91 (3) |
C6—C7 | 1.382 (3) | C11—H11 | 1.00 (3) |
C6—C11 | 1.387 (3) | N5—S2 | 1.6293 (17) |
C6—N5 | 1.411 (2) | N5—H5N | 0.849 (10) |
C7—C8 | 1.380 (3) | N12—O14 | 1.216 (3) |
C7—H7 | 0.94 (3) | N12—O13 | 1.221 (3) |
C8—C9 | 1.375 (3) | O3—S2 | 1.4351 (15) |
C8—N12 | 1.472 (3) | O4—S2 | 1.4254 (15) |
S2—C1—H1A | 109.5 | C11—C10—C9 | 120.5 (2) |
S2—C1—H1B | 109.5 | C11—C10—H10 | 121.6 (19) |
H1A—C1—H1B | 109.5 | C9—C10—H10 | 117.9 (19) |
S2—C1—H1C | 109.5 | C10—C11—C6 | 120.6 (2) |
H1A—C1—H1C | 109.5 | C10—C11—H11 | 121.9 (15) |
H1B—C1—H1C | 109.5 | C6—C11—H11 | 117.4 (15) |
C7—C6—C11 | 120.16 (19) | C6—N5—S2 | 126.27 (13) |
C7—C6—N5 | 122.12 (17) | C6—N5—H5N | 116.1 (19) |
C11—C6—N5 | 117.69 (18) | S2—N5—H5N | 111.8 (19) |
C8—C7—C6 | 117.54 (18) | O14—N12—O13 | 123.6 (2) |
C8—C7—H7 | 120.1 (15) | O14—N12—C8 | 118.38 (19) |
C6—C7—H7 | 122.1 (15) | O13—N12—C8 | 118.0 (2) |
C9—C8—C7 | 123.82 (19) | O4—S2—O3 | 118.55 (9) |
C9—C8—N12 | 118.12 (19) | O4—S2—N5 | 109.14 (10) |
C7—C8—N12 | 118.06 (19) | O3—S2—N5 | 104.09 (9) |
C8—C9—C10 | 117.39 (19) | O4—S2—C1 | 108.26 (10) |
C8—C9—H9 | 118.3 (16) | O3—S2—C1 | 109.55 (12) |
C10—C9—H9 | 124.3 (16) | N5—S2—C1 | 106.62 (11) |
C11—C6—C7—C8 | −0.6 (3) | C7—C6—N5—S2 | 41.2 (3) |
N5—C6—C7—C8 | 177.35 (18) | C11—C6—N5—S2 | −140.83 (19) |
C6—C7—C8—C9 | −0.2 (3) | C9—C8—N12—O14 | 176.1 (2) |
C6—C7—C8—N12 | −179.54 (17) | C7—C8—N12—O14 | −4.6 (3) |
C7—C8—C9—C10 | 0.5 (3) | C9—C8—N12—O13 | −3.6 (3) |
N12—C8—C9—C10 | 179.83 (19) | C7—C8—N12—O13 | 175.7 (2) |
C8—C9—C10—C11 | 0.0 (4) | C6—N5—S2—O4 | −57.2 (2) |
C9—C10—C11—C6 | −0.8 (4) | C6—N5—S2—O3 | 175.34 (19) |
C7—C6—C11—C10 | 1.1 (3) | C6—N5—S2—C1 | 59.6 (2) |
N5—C6—C11—C10 | −176.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5N···O3i | 0.85 (1) | 2.20 (2) | 2.984 (2) | 153 (3) |
Symmetry code: (i) −x+1, −y+2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C7H8N2O4S |
Mr | 216.21 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 299 |
a, b, c (Å) | 6.959 (1), 8.207 (1), 8.759 (1) |
α, β, γ (°) | 96.93 (1), 111.05 (1), 99.78 (1) |
V (Å3) | 451.02 (10) |
Z | 2 |
Radiation type | Cu Kα |
µ (mm−1) | 3.18 |
Crystal size (mm) | 0.25 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2782, 1611, 1427 |
Rint | 0.071 |
(sin θ/λ)max (Å−1) | 0.597 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.105, 1.08 |
No. of reflections | 1611 |
No. of parameters | 143 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.49, −0.49 |
Computer programs: CAD-4-PC (Nonius, 1996), CAD-4-PC, REDU4 (Stoe & Cie, 1987), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97.
C1—S2 | 1.747 (2) | O3—S2 | 1.4351 (15) |
C6—N5 | 1.411 (2) | O4—S2 | 1.4254 (15) |
N5—S2 | 1.6293 (17) | ||
C7—C6—N5 | 122.12 (17) | O4—S2—N5 | 109.14 (10) |
C11—C6—N5 | 117.69 (18) | O3—S2—N5 | 104.09 (9) |
C6—N5—S2 | 126.27 (13) | N5—S2—C1 | 106.62 (11) |
O4—S2—O3 | 118.55 (9) | ||
C7—C6—N5—S2 | 41.2 (3) | C6—N5—S2—O3 | 175.34 (19) |
C11—C6—N5—S2 | −140.83 (19) | C6—N5—S2—C1 | 59.6 (2) |
C6—N5—S2—O4 | −57.2 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5N···O3i | 0.849 (10) | 2.203 (16) | 2.984 (2) | 153 (3) |
Symmetry code: (i) −x+1, −y+2, −z+1. |
Methanesulfonanilides are of interest due to their distinct chemical and physical properties. The alkyl sulfonanilido moiety is an important constituent of many biologically significant compounds. The stereochemistry of these molecules, particularly in the vicinity of the phenyl-N—H portion would be of extreme interest in formulating an explanation of their biological activity similar to phenolic derivatives. The biological activity 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. Thus the structural studies of sulfonanilides are of interest. In the present work, the structure of N-(3-nitrophenyl)-methanesulfonamde (3NPMSA) has been determined to explore the substituent effects of polar groups on the structures of anilides and sulfonanilides as part of a study on the systematization of the crystal structures of this class of compounds in general (Gowda et al., 2000; Gowda et al., 2007a,b,c). In the structure of 3NPMSA the conformation of the N—H bond is anti to the meta-nitro substituent (Fig.1). The amide hydrogen is thus available to a receptor molecule during biological activity. Selected geometric parameters are shown in Table 1. The molecules are linked into centrosymmetric dimers (Fig. 2) through a N—H···O hydrogen bond (Table 2).