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The structure of the title compound, C7H8BrNO2S, closely resembles those of other alkyl sulfonanilides. The mol­ecules in the crystal structure are linked into zigzag chains in the b-axis direction via N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807019009/bt2338sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807019009/bt2338Isup2.hkl
Contains datablock I

CCDC reference: 614615

Key indicators

  • Single-crystal X-ray study
  • T = 299 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.026
  • wR factor = 0.072
  • Data-to-parameter ratio = 14.3

checkCIF/PLATON results

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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

Comment top

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.

Related literature top

For related literature, see: Gowda et al. (2000, 2007, 2007a,b,c,d,e,f); Jayalakshmi & Gowda (2004); Klug (1968).

Experimental top

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.

Refinement top

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.

Structure description top

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).

Computing details top

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.

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound showing the atom labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
N-(4-Bromophenyl)methanesulfonamide top
Crystal data top
C7H8BrNO2SF(000) = 496
Mr = 250.11Dx = 1.819 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 9.7474 (6) Åθ = 9.2–25.4°
b = 5.7660 (3) ŵ = 7.97 mm1
c = 16.378 (1) ÅT = 299 K
β = 97.272 (6)°Prism, grey
V = 913.10 (9) Å30.28 × 0.25 × 0.15 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer
1508 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.030
Graphite monochromatorθmax = 67.0°, θmin = 4.6°
ω/2θ scansh = 1111
Absorption correction: ψ scan
(North et al., 1968)
k = 06
Tmin = 0.182, Tmax = 0.344l = 193
1972 measured reflections3 standard reflections every 120 min
1625 independent reflections intensity decay: 4.0%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.026H 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 reflectionsΔρmax = 0.27 e Å3
114 parametersΔρmin = 0.50 e Å3
1 restraintExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0106 (4)
Crystal data top
C7H8BrNO2SV = 913.10 (9) Å3
Mr = 250.11Z = 4
Monoclinic, P21/cCu Kα radiation
a = 9.7474 (6) ŵ = 7.97 mm1
b = 5.7660 (3) ÅT = 299 K
c = 16.378 (1) Å0.28 × 0.25 × 0.15 mm
β = 97.272 (6)°
Data collection top
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 = 0.3443 standard reflections every 120 min
1972 measured reflections intensity decay: 4.0%
1625 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0261 restraint
wR(F2) = 0.072H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.27 e Å3
1625 reflectionsΔρmin = 0.50 e Å3
114 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.9894 (4)0.2605 (7)0.1006 (2)0.0638 (9)
H1A1.05070.21750.06160.077*
H1B1.04150.33350.14730.077*
H1C0.92110.36670.07520.077*
C60.6817 (3)0.2435 (5)0.16508 (14)0.0321 (5)
C70.6694 (3)0.4593 (5)0.20045 (15)0.0377 (6)
H70.74070.51620.23820.045*
C80.5514 (3)0.5904 (5)0.17978 (16)0.0381 (6)
H80.54150.73370.20450.046*
C90.4487 (3)0.5057 (5)0.12209 (15)0.0353 (5)
C100.4604 (3)0.2940 (5)0.08516 (16)0.0401 (6)
H100.39050.24080.04570.048*
C110.5773 (3)0.1603 (5)0.10720 (16)0.0383 (6)
H110.58560.01560.08330.046*
Br120.28668 (3)0.68488 (6)0.093223 (19)0.05147 (17)
N50.7988 (2)0.1016 (4)0.19397 (13)0.0386 (5)
H5N0.842 (3)0.153 (5)0.2390 (11)0.046*
O31.0074 (2)0.1222 (5)0.18364 (14)0.0638 (6)
O40.8323 (2)0.0930 (4)0.06242 (12)0.0517 (5)
S20.90772 (6)0.01280 (12)0.13265 (4)0.0390 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.062 (2)0.073 (2)0.059 (2)0.0159 (19)0.0183 (16)0.0057 (18)
C60.0311 (12)0.0384 (13)0.0274 (11)0.0015 (10)0.0053 (9)0.0013 (10)
C70.0338 (13)0.0419 (14)0.0358 (12)0.0028 (11)0.0014 (10)0.0026 (11)
C80.0402 (14)0.0352 (13)0.0385 (13)0.0017 (11)0.0040 (11)0.0026 (11)
C90.0312 (12)0.0428 (14)0.0321 (12)0.0049 (11)0.0047 (10)0.0056 (10)
C100.0348 (13)0.0487 (16)0.0352 (13)0.0005 (12)0.0017 (10)0.0038 (11)
C110.0369 (13)0.0412 (15)0.0359 (13)0.0020 (11)0.0007 (10)0.0063 (11)
Br120.0401 (2)0.0586 (3)0.0540 (2)0.01533 (13)0.00079 (13)0.00234 (14)
N50.0357 (12)0.0502 (13)0.0287 (10)0.0085 (10)0.0003 (8)0.0006 (10)
O30.0501 (13)0.0814 (16)0.0569 (13)0.0321 (12)0.0044 (10)0.0007 (12)
O40.0473 (11)0.0620 (13)0.0441 (11)0.0060 (10)0.0006 (9)0.0187 (10)
S20.0326 (3)0.0485 (4)0.0350 (3)0.0082 (3)0.0002 (2)0.0043 (3)
Geometric parameters (Å, º) top
C1—S21.748 (4)C8—H80.9300
C1—H1A0.9600C9—C101.374 (4)
C1—H1B0.9600C9—Br121.897 (2)
C1—H1C0.9600C10—C111.384 (4)
C6—C71.384 (4)C10—H100.9300
C6—C111.386 (4)C11—H110.9300
C6—N51.435 (3)N5—S21.634 (2)
C7—C81.382 (4)N5—H5N0.854 (10)
C7—H70.9300O3—S21.429 (2)
C8—C91.376 (4)O4—S21.422 (2)
S2—C1—H1A109.5C8—C9—Br12119.2 (2)
S2—C1—H1B109.5C9—C10—C11119.4 (2)
H1A—C1—H1B109.5C9—C10—H10120.3
S2—C1—H1C109.5C11—C10—H10120.3
H1A—C1—H1C109.5C10—C11—C6119.6 (2)
H1B—C1—H1C109.5C10—C11—H11120.2
C7—C6—C11120.1 (2)C6—C11—H11120.2
C7—C6—N5118.8 (2)C6—N5—S2121.86 (16)
C11—C6—N5120.9 (2)C6—N5—H5N112 (2)
C8—C7—C6120.2 (2)S2—N5—H5N111 (2)
C8—C7—H7119.9O4—S2—O3118.86 (15)
C6—C7—H7119.9O4—S2—N5108.81 (12)
C9—C8—C7119.0 (2)O3—S2—N5104.97 (12)
C9—C8—H8120.5O4—S2—C1108.44 (16)
C7—C8—H8120.5O3—S2—C1108.57 (19)
C10—C9—C8121.6 (2)N5—S2—C1106.54 (16)
C10—C9—Br12119.18 (19)
C11—C6—C7—C81.6 (4)C7—C6—C11—C100.2 (4)
N5—C6—C7—C8173.7 (2)N5—C6—C11—C10175.0 (2)
C6—C7—C8—C91.7 (4)C7—C6—N5—S2120.9 (2)
C7—C8—C9—C100.4 (4)C11—C6—N5—S263.8 (3)
C7—C8—C9—Br12179.9 (2)C6—N5—S2—O451.5 (3)
C8—C9—C10—C111.0 (4)C6—N5—S2—O3179.7 (2)
Br12—C9—C10—C11178.7 (2)C6—N5—S2—C165.2 (3)
C9—C10—C11—C61.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5N···O3i0.85 (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 formulaC7H8BrNO2S
Mr250.11
Crystal system, space groupMonoclinic, P21/c
Temperature (K)299
a, b, c (Å)9.7474 (6), 5.7660 (3), 16.378 (1)
β (°) 97.272 (6)
V3)913.10 (9)
Z4
Radiation typeCu Kα
µ (mm1)7.97
Crystal size (mm)0.28 × 0.25 × 0.15
Data collection
DiffractometerEnraf–Nonius CAD-4
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.182, 0.344
No. of measured, independent and
observed [I > 2σ(I)] reflections
1972, 1625, 1508
Rint0.030
(sin θ/λ)max1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.026, 0.072, 1.08
No. of reflections1625
No. of parameters114
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5N···O3i0.854 (10)2.229 (16)3.027 (3)155 (3)
Symmetry code: (i) x+2, y+1/2, z+1/2.
 

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