Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807019009/bt2338sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807019009/bt2338Isup2.hkl |
CCDC reference: 614615
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean (C-C) = 0.004 Å
- R factor = 0.026
- wR factor = 0.072
- Data-to-parameter ratio = 14.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.88
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.880 Tmax scaled 0.303 Tmin scaled 0.160
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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. (2000, 2007, 2007a,b,c,d,e,f); Jayalakshmi & Gowda (2004); Klug (1968).
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.
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) and Uiso(H) = 1.2 Ueq(C,N) or Uiso(H) = 1.5 Ueq(Cmethyl). The methyl group was allowed to rotate but not to tip. The coordinates of the H atom bonded to N were refined with distance restraint of 0.86 (1) Å.
The alkyl sulfonanilides are an important class of biologically significant compounds. The stereochemistry of these compounds particularly in the vicinity of the phenyl-N—H portion is of interest as it helps in explaining their biological activity. In the present work, the structure of N-(4-bromophenyl)-methanesulfonamde has been determined (Fig. 1) to explore the substituent effects on the structures of anilides and sulfonanilides (Gowda et al., 2007a-f; Gowda, Kozisek et al., 2007; Gowda, Paulus et al., 2000). Geometric parameters in these structures are similar. Like in other alkyl sulfonanilides (Gowda et al., 2007b-f), the amide hydrogen is available to a receptor molecule. The molecules in the title compound are packed zigzag chains in the direction of the b axis via N—H···O hydrogen bonds.
For related literature, see: Gowda et al. (2000, 2007, 2007a,b,c,d,e,f); Jayalakshmi & Gowda (2004); Klug (1968).
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.
C7H8BrNO2S | F(000) = 496 |
Mr = 250.11 | Dx = 1.819 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 9.7474 (6) Å | θ = 9.2–25.4° |
b = 5.7660 (3) Å | µ = 7.97 mm−1 |
c = 16.378 (1) Å | T = 299 K |
β = 97.272 (6)° | Prism, grey |
V = 913.10 (9) Å3 | 0.28 × 0.25 × 0.15 mm |
Z = 4 |
Enraf–Nonius CAD-4 diffractometer | 1508 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.030 |
Graphite monochromator | θmax = 67.0°, θmin = 4.6° |
ω/2θ scans | h = −11→11 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→6 |
Tmin = 0.182, Tmax = 0.344 | l = −19→3 |
1972 measured reflections | 3 standard reflections every 120 min |
1625 independent reflections | intensity decay: 4.0% |
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)] = 0.026 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.072 | w = 1/[σ2(Fo2) + (0.0343P)2 + 0.7498P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
1625 reflections | Δρmax = 0.27 e Å−3 |
114 parameters | Δρmin = −0.50 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: 0.0106 (4) |
C7H8BrNO2S | V = 913.10 (9) Å3 |
Mr = 250.11 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 9.7474 (6) Å | µ = 7.97 mm−1 |
b = 5.7660 (3) Å | T = 299 K |
c = 16.378 (1) Å | 0.28 × 0.25 × 0.15 mm |
β = 97.272 (6)° |
Enraf–Nonius CAD-4 diffractometer | 1508 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.030 |
Tmin = 0.182, Tmax = 0.344 | 3 standard reflections every 120 min |
1972 measured reflections | intensity decay: 4.0% |
1625 independent reflections |
R[F2 > 2σ(F2)] = 0.026 | 1 restraint |
wR(F2) = 0.072 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.27 e Å−3 |
1625 reflections | Δρmin = −0.50 e Å−3 |
114 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 | 0.9894 (4) | 0.2605 (7) | 0.1006 (2) | 0.0638 (9) | |
H1A | 1.0507 | 0.2175 | 0.0616 | 0.077* | |
H1B | 1.0415 | 0.3335 | 0.1473 | 0.077* | |
H1C | 0.9211 | 0.3667 | 0.0752 | 0.077* | |
C6 | 0.6817 (3) | 0.2435 (5) | 0.16508 (14) | 0.0321 (5) | |
C7 | 0.6694 (3) | 0.4593 (5) | 0.20045 (15) | 0.0377 (6) | |
H7 | 0.7407 | 0.5162 | 0.2382 | 0.045* | |
C8 | 0.5514 (3) | 0.5904 (5) | 0.17978 (16) | 0.0381 (6) | |
H8 | 0.5415 | 0.7337 | 0.2045 | 0.046* | |
C9 | 0.4487 (3) | 0.5057 (5) | 0.12209 (15) | 0.0353 (5) | |
C10 | 0.4604 (3) | 0.2940 (5) | 0.08516 (16) | 0.0401 (6) | |
H10 | 0.3905 | 0.2408 | 0.0457 | 0.048* | |
C11 | 0.5773 (3) | 0.1603 (5) | 0.10720 (16) | 0.0383 (6) | |
H11 | 0.5856 | 0.0156 | 0.0833 | 0.046* | |
Br12 | 0.28668 (3) | 0.68488 (6) | 0.093223 (19) | 0.05147 (17) | |
N5 | 0.7988 (2) | 0.1016 (4) | 0.19397 (13) | 0.0386 (5) | |
H5N | 0.842 (3) | 0.153 (5) | 0.2390 (11) | 0.046* | |
O3 | 1.0074 (2) | −0.1222 (5) | 0.18364 (14) | 0.0638 (6) | |
O4 | 0.8323 (2) | −0.0930 (4) | 0.06242 (12) | 0.0517 (5) | |
S2 | 0.90772 (6) | 0.01280 (12) | 0.13265 (4) | 0.0390 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.062 (2) | 0.073 (2) | 0.059 (2) | −0.0159 (19) | 0.0183 (16) | −0.0057 (18) |
C6 | 0.0311 (12) | 0.0384 (13) | 0.0274 (11) | 0.0015 (10) | 0.0053 (9) | 0.0013 (10) |
C7 | 0.0338 (13) | 0.0419 (14) | 0.0358 (12) | −0.0028 (11) | −0.0014 (10) | −0.0026 (11) |
C8 | 0.0402 (14) | 0.0352 (13) | 0.0385 (13) | 0.0017 (11) | 0.0040 (11) | −0.0026 (11) |
C9 | 0.0312 (12) | 0.0428 (14) | 0.0321 (12) | 0.0049 (11) | 0.0047 (10) | 0.0056 (10) |
C10 | 0.0348 (13) | 0.0487 (16) | 0.0352 (13) | 0.0005 (12) | −0.0017 (10) | −0.0038 (11) |
C11 | 0.0369 (13) | 0.0412 (15) | 0.0359 (13) | 0.0020 (11) | 0.0007 (10) | −0.0063 (11) |
Br12 | 0.0401 (2) | 0.0586 (3) | 0.0540 (2) | 0.01533 (13) | −0.00079 (13) | 0.00234 (14) |
N5 | 0.0357 (12) | 0.0502 (13) | 0.0287 (10) | 0.0085 (10) | −0.0003 (8) | −0.0006 (10) |
O3 | 0.0501 (13) | 0.0814 (16) | 0.0569 (13) | 0.0321 (12) | −0.0044 (10) | 0.0007 (12) |
O4 | 0.0473 (11) | 0.0620 (13) | 0.0441 (11) | 0.0060 (10) | −0.0006 (9) | −0.0187 (10) |
S2 | 0.0326 (3) | 0.0485 (4) | 0.0350 (3) | 0.0082 (3) | 0.0002 (2) | −0.0043 (3) |
C1—S2 | 1.748 (4) | C8—H8 | 0.9300 |
C1—H1A | 0.9600 | C9—C10 | 1.374 (4) |
C1—H1B | 0.9600 | C9—Br12 | 1.897 (2) |
C1—H1C | 0.9600 | C10—C11 | 1.384 (4) |
C6—C7 | 1.384 (4) | C10—H10 | 0.9300 |
C6—C11 | 1.386 (4) | C11—H11 | 0.9300 |
C6—N5 | 1.435 (3) | N5—S2 | 1.634 (2) |
C7—C8 | 1.382 (4) | N5—H5N | 0.854 (10) |
C7—H7 | 0.9300 | O3—S2 | 1.429 (2) |
C8—C9 | 1.376 (4) | O4—S2 | 1.422 (2) |
S2—C1—H1A | 109.5 | C8—C9—Br12 | 119.2 (2) |
S2—C1—H1B | 109.5 | C9—C10—C11 | 119.4 (2) |
H1A—C1—H1B | 109.5 | C9—C10—H10 | 120.3 |
S2—C1—H1C | 109.5 | C11—C10—H10 | 120.3 |
H1A—C1—H1C | 109.5 | C10—C11—C6 | 119.6 (2) |
H1B—C1—H1C | 109.5 | C10—C11—H11 | 120.2 |
C7—C6—C11 | 120.1 (2) | C6—C11—H11 | 120.2 |
C7—C6—N5 | 118.8 (2) | C6—N5—S2 | 121.86 (16) |
C11—C6—N5 | 120.9 (2) | C6—N5—H5N | 112 (2) |
C8—C7—C6 | 120.2 (2) | S2—N5—H5N | 111 (2) |
C8—C7—H7 | 119.9 | O4—S2—O3 | 118.86 (15) |
C6—C7—H7 | 119.9 | O4—S2—N5 | 108.81 (12) |
C9—C8—C7 | 119.0 (2) | O3—S2—N5 | 104.97 (12) |
C9—C8—H8 | 120.5 | O4—S2—C1 | 108.44 (16) |
C7—C8—H8 | 120.5 | O3—S2—C1 | 108.57 (19) |
C10—C9—C8 | 121.6 (2) | N5—S2—C1 | 106.54 (16) |
C10—C9—Br12 | 119.18 (19) | ||
C11—C6—C7—C8 | 1.6 (4) | C7—C6—C11—C10 | −0.2 (4) |
N5—C6—C7—C8 | −173.7 (2) | N5—C6—C11—C10 | 175.0 (2) |
C6—C7—C8—C9 | −1.7 (4) | C7—C6—N5—S2 | −120.9 (2) |
C7—C8—C9—C10 | 0.4 (4) | C11—C6—N5—S2 | 63.8 (3) |
C7—C8—C9—Br12 | −179.9 (2) | C6—N5—S2—O4 | −51.5 (3) |
C8—C9—C10—C11 | 1.0 (4) | C6—N5—S2—O3 | −179.7 (2) |
Br12—C9—C10—C11 | −178.7 (2) | C6—N5—S2—C1 | 65.2 (3) |
C9—C10—C11—C6 | −1.1 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5N···O3i | 0.85 (1) | 2.23 (2) | 3.027 (3) | 155 (3) |
Symmetry code: (i) −x+2, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C7H8BrNO2S |
Mr | 250.11 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 299 |
a, b, c (Å) | 9.7474 (6), 5.7660 (3), 16.378 (1) |
β (°) | 97.272 (6) |
V (Å3) | 913.10 (9) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 7.97 |
Crystal size (mm) | 0.28 × 0.25 × 0.15 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.182, 0.344 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 1972, 1625, 1508 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.597 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.026, 0.072, 1.08 |
No. of reflections | 1625 |
No. of parameters | 114 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.27, −0.50 |
Computer programs: CAD-4-PC (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 | 0.854 (10) | 2.229 (16) | 3.027 (3) | 155 (3) |
Symmetry code: (i) −x+2, y+1/2, −z+1/2. |
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The alkyl sulfonanilides are an important class of biologically significant compounds. The stereochemistry of these compounds particularly in the vicinity of the phenyl-N—H portion is of interest as it helps in explaining their biological activity. In the present work, the structure of N-(4-bromophenyl)-methanesulfonamde has been determined (Fig. 1) to explore the substituent effects on the structures of anilides and sulfonanilides (Gowda et al., 2007a-f; Gowda, Kozisek et al., 2007; Gowda, Paulus et al., 2000). Geometric parameters in these structures are similar. Like in other alkyl sulfonanilides (Gowda et al., 2007b-f), the amide hydrogen is available to a receptor molecule. The molecules in the title compound are packed zigzag chains in the direction of the b axis via N—H···O hydrogen bonds.