


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680701598X/lw2006sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S160053680701598X/lw2006Isup2.hkl |
CCDC reference: 614581
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(CH3).
The alkyl sulfonanilide 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, is of interest in explaining their biological activity. This biological activity is thought to be due to the H atom of the phenyl N—H portion of the sulfonanilide molecules, as it can align itself in relation to a receptor site. Therefore, structural studies of sulfonanilides are of interest. In the present work, the structure of the title compound (4NPMSA) has been determined to explore the substituent effects of polar groups on the structures of anilides and sulfonanilides (Gowda et al., 2007a,b; Gowda et al., 2000; Gowda, Kozisek et al., 2007).
The substitution of a nitro group at the para position of N-(phenyl)methanesulfonamide (PMSA) does not change the space group, unlike in the case of meta substitution (3NPMSA), where it changes from monoclinic P21/c (Klug, 1968) to triclinic P1 (Gowda et al., 2007c).
The N—H H atom projects alone on one side of the plane of the phenyl group, while the whole methanesulfonyl group is on the opposite side of the plane (Fig. 1), similar to what was observed in PMSA (Klug, 1968) and 3NPMSA (Gowda et al., 2007c). The amide H atom is thus available to a receptor molecule during biological activity.
An N—H···O hydrogen bond links the molecules of (I) into centrosymmetric dimers (Table 1 and Fig. 2).
For related literature, see: Gowda et al. (2000); Gowda, Kozisek et al., (2007); Gowda et al., (2007a), (2007b), (2007c); 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.
C7H8N2O4S | F(000) = 448 |
Mr = 216.21 | Dx = 1.561 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 10.879 (2) Å | θ = 4.3–24.4° |
b = 10.336 (2) Å | µ = 3.12 mm−1 |
c = 8.715 (1) Å | T = 299 K |
β = 110.13 (1)° | Laminar, grey |
V = 920.1 (3) Å3 | 0.17 × 0.15 × 0.03 mm |
Z = 4 |
Enraf–Nonius CAD-4 diffractometer | 1149 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.035 |
Graphite monochromator | θmax = 66.9°, θmin = 4.3° |
ω/2θ scans | h = −12→12 |
Absorption correction: ψ scan (North et al., 1968) | k = −12→1 |
Tmin = 0.547, Tmax = 0.778 | l = −10→0 |
1780 measured reflections | 3 standard reflections every 120 min |
1642 independent reflections | intensity decay: 3.5% |
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)] = 0.060 | H-atom parameters constrained |
wR(F2) = 0.182 | w = 1/[σ2(Fo2) + (0.1074P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
1642 reflections | Δρmax = 0.56 e Å−3 |
128 parameters | Δρmin = −0.61 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: 0.0089 (16) |
C7H8N2O4S | V = 920.1 (3) Å3 |
Mr = 216.21 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 10.879 (2) Å | µ = 3.12 mm−1 |
b = 10.336 (2) Å | T = 299 K |
c = 8.715 (1) Å | 0.17 × 0.15 × 0.03 mm |
β = 110.13 (1)° |
Enraf–Nonius CAD-4 diffractometer | 1149 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.035 |
Tmin = 0.547, Tmax = 0.778 | 3 standard reflections every 120 min |
1780 measured reflections | intensity decay: 3.5% |
1642 independent reflections |
R[F2 > 2σ(F2)] = 0.060 | 0 restraints |
wR(F2) = 0.182 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.56 e Å−3 |
1642 reflections | Δρmin = −0.61 e Å−3 |
128 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 | 0.6245 (5) | 0.4037 (5) | 0.4016 (5) | 0.0484 (12) | |
H1A | 0.5738 | 0.3869 | 0.4705 | 0.058* | |
H1B | 0.6365 | 0.4953 | 0.3951 | 0.058* | |
H1C | 0.7083 | 0.3624 | 0.4465 | 0.058* | |
C6 | 0.2974 (4) | 0.4055 (4) | 0.1995 (5) | 0.0383 (10) | |
C7 | 0.2810 (5) | 0.2996 (4) | 0.2895 (6) | 0.0454 (11) | |
H7 | 0.3418 | 0.2326 | 0.3160 | 0.054* | |
C8 | 0.1728 (5) | 0.2953 (5) | 0.3392 (6) | 0.0486 (12) | |
H8 | 0.1603 | 0.2248 | 0.3985 | 0.058* | |
C9 | 0.0845 (4) | 0.3948 (5) | 0.3008 (6) | 0.0467 (12) | |
C10 | 0.1012 (5) | 0.5004 (5) | 0.2138 (6) | 0.0521 (12) | |
H10 | 0.0406 | 0.5675 | 0.1892 | 0.063* | |
C11 | 0.2070 (4) | 0.5065 (5) | 0.1636 (6) | 0.0473 (11) | |
H11 | 0.2187 | 0.5781 | 0.1055 | 0.057* | |
N5 | 0.4013 (4) | 0.4164 (4) | 0.1407 (5) | 0.0429 (9) | |
H5N | 0.3894 | 0.4683 | 0.0598 | 0.051* | |
N12 | −0.0295 (4) | 0.3886 (5) | 0.3520 (6) | 0.0596 (12) | |
O3 | 0.6074 (3) | 0.3835 (3) | 0.0984 (4) | 0.0535 (9) | |
O4 | 0.5206 (4) | 0.2075 (3) | 0.2198 (4) | 0.0534 (9) | |
O13 | −0.0451 (4) | 0.2933 (4) | 0.4271 (6) | 0.0816 (14) | |
O14 | −0.1055 (4) | 0.4809 (5) | 0.3203 (6) | 0.0847 (14) | |
S2 | 0.54234 (11) | 0.34283 (10) | 0.20640 (13) | 0.0386 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.053 (3) | 0.055 (3) | 0.040 (3) | −0.008 (2) | 0.019 (2) | −0.003 (2) |
C6 | 0.039 (2) | 0.037 (2) | 0.036 (2) | −0.0042 (18) | 0.0099 (19) | −0.0023 (18) |
C7 | 0.044 (3) | 0.039 (2) | 0.056 (3) | 0.001 (2) | 0.020 (2) | 0.008 (2) |
C8 | 0.044 (3) | 0.048 (3) | 0.057 (3) | −0.008 (2) | 0.021 (2) | 0.003 (2) |
C9 | 0.037 (2) | 0.050 (3) | 0.055 (3) | −0.008 (2) | 0.017 (2) | −0.009 (2) |
C10 | 0.045 (2) | 0.044 (3) | 0.069 (3) | 0.004 (2) | 0.021 (2) | 0.005 (2) |
C11 | 0.045 (2) | 0.037 (2) | 0.059 (3) | 0.000 (2) | 0.018 (2) | 0.008 (2) |
N5 | 0.045 (2) | 0.042 (2) | 0.046 (2) | 0.0050 (17) | 0.0208 (18) | 0.0135 (17) |
N12 | 0.048 (2) | 0.062 (3) | 0.074 (3) | −0.015 (2) | 0.026 (2) | −0.016 (2) |
O3 | 0.058 (2) | 0.065 (2) | 0.0493 (19) | 0.0109 (17) | 0.0337 (17) | 0.0111 (16) |
O4 | 0.070 (2) | 0.0342 (17) | 0.057 (2) | 0.0042 (16) | 0.0222 (18) | −0.0036 (15) |
O13 | 0.086 (3) | 0.066 (3) | 0.117 (4) | −0.018 (2) | 0.066 (3) | −0.004 (3) |
O14 | 0.051 (2) | 0.085 (3) | 0.129 (4) | 0.006 (2) | 0.045 (3) | −0.003 (3) |
S2 | 0.0457 (6) | 0.0369 (6) | 0.0377 (6) | 0.0035 (5) | 0.0202 (4) | 0.0006 (5) |
C1—S2 | 1.744 (5) | C9—C10 | 1.377 (7) |
C1—H1A | 0.9600 | C9—N12 | 1.457 (6) |
C1—H1B | 0.9600 | C10—C11 | 1.366 (6) |
C1—H1C | 0.9600 | C10—H10 | 0.9300 |
C6—C11 | 1.394 (6) | C11—H11 | 0.9300 |
C6—C7 | 1.394 (6) | N5—S2 | 1.629 (4) |
C6—N5 | 1.398 (5) | N5—H5N | 0.8600 |
C7—C8 | 1.388 (7) | N12—O13 | 1.226 (6) |
C7—H7 | 0.9300 | N12—O14 | 1.230 (6) |
C8—C9 | 1.368 (7) | O3—S2 | 1.422 (3) |
C8—H8 | 0.9300 | O4—S2 | 1.431 (3) |
S2—C1—H1A | 109.5 | C11—C10—C9 | 119.9 (5) |
S2—C1—H1B | 109.5 | C11—C10—H10 | 120.0 |
H1A—C1—H1B | 109.5 | C9—C10—H10 | 120.0 |
S2—C1—H1C | 109.5 | C10—C11—C6 | 120.0 (4) |
H1A—C1—H1C | 109.5 | C10—C11—H11 | 120.0 |
H1B—C1—H1C | 109.5 | C6—C11—H11 | 120.0 |
C11—C6—C7 | 119.9 (4) | C6—N5—S2 | 128.1 (3) |
C11—C6—N5 | 117.1 (4) | C6—N5—H5N | 116.0 |
C7—C6—N5 | 123.1 (4) | S2—N5—H5N | 116.0 |
C8—C7—C6 | 119.2 (4) | O13—N12—O14 | 122.5 (5) |
C8—C7—H7 | 120.4 | O13—N12—C9 | 119.2 (5) |
C6—C7—H7 | 120.4 | O14—N12—C9 | 118.3 (5) |
C9—C8—C7 | 119.9 (5) | O3—S2—O4 | 118.5 (2) |
C9—C8—H8 | 120.0 | O3—S2—N5 | 104.6 (2) |
C7—C8—H8 | 120.0 | O4—S2—N5 | 108.9 (2) |
C8—C9—C10 | 121.1 (5) | O3—S2—C1 | 109.5 (2) |
C8—C9—N12 | 119.5 (5) | O4—S2—C1 | 108.5 (2) |
C10—C9—N12 | 119.4 (5) | N5—S2—C1 | 106.2 (2) |
C11—C6—C7—C8 | 1.3 (7) | C11—C6—N5—S2 | 158.9 (4) |
N5—C6—C7—C8 | −178.2 (4) | C7—C6—N5—S2 | −21.5 (6) |
C6—C7—C8—C9 | −0.6 (7) | C8—C9—N12—O13 | −0.9 (7) |
C7—C8—C9—C10 | −0.3 (8) | C10—C9—N12—O13 | 178.7 (5) |
C7—C8—C9—N12 | 179.3 (4) | C8—C9—N12—O14 | 177.9 (5) |
C8—C9—C10—C11 | 0.4 (8) | C10—C9—N12—O14 | −2.4 (7) |
N12—C9—C10—C11 | −179.3 (5) | C6—N5—S2—O3 | 177.0 (4) |
C9—C10—C11—C6 | 0.4 (8) | C6—N5—S2—O4 | 49.4 (4) |
C7—C6—C11—C10 | −1.3 (7) | C6—N5—S2—C1 | −67.2 (4) |
N5—C6—C11—C10 | 178.3 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5N···O3i | 0.86 | 2.07 | 2.914 (5) | 168 |
Symmetry code: (i) −x+1, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C7H8N2O4S |
Mr | 216.21 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 299 |
a, b, c (Å) | 10.879 (2), 10.336 (2), 8.715 (1) |
β (°) | 110.13 (1) |
V (Å3) | 920.1 (3) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 3.12 |
Crystal size (mm) | 0.17 × 0.15 × 0.03 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.547, 0.778 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 1780, 1642, 1149 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.597 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.060, 0.182, 1.09 |
No. of reflections | 1642 |
No. of parameters | 128 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.56, −0.61 |
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 | 0.86 | 2.07 | 2.914 (5) | 167.5 |
Symmetry code: (i) −x+1, −y+1, −z. |
The alkyl sulfonanilide 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, is of interest in explaining their biological activity. This biological activity is thought to be due to the H atom of the phenyl N—H portion of the sulfonanilide molecules, as it can align itself in relation to a receptor site. Therefore, structural studies of sulfonanilides are of interest. In the present work, the structure of the title compound (4NPMSA) has been determined to explore the substituent effects of polar groups on the structures of anilides and sulfonanilides (Gowda et al., 2007a,b; Gowda et al., 2000; Gowda, Kozisek et al., 2007).
The substitution of a nitro group at the para position of N-(phenyl)methanesulfonamide (PMSA) does not change the space group, unlike in the case of meta substitution (3NPMSA), where it changes from monoclinic P21/c (Klug, 1968) to triclinic P1 (Gowda et al., 2007c).
The N—H H atom projects alone on one side of the plane of the phenyl group, while the whole methanesulfonyl group is on the opposite side of the plane (Fig. 1), similar to what was observed in PMSA (Klug, 1968) and 3NPMSA (Gowda et al., 2007c). The amide H atom is thus available to a receptor molecule during biological activity.
An N—H···O hydrogen bond links the molecules of (I) into centrosymmetric dimers (Table 1 and Fig. 2).