N-(4-Bromo­phen­yl)methane­sulfonamide

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.

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

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

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S1. Comment

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

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

S2. Experimental

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.

S3. Refinement

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 U_iso(H) = 1.2 U_eq(C,N) or U_iso(H) = 1.5 U_eq(C_methyl). 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.

Computing details

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

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

Crystal data

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) Å^3	0.28 × 0.25 × 0.15 mm
Z = 4

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.026	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.072	w = 1/[σ^2(Fo^2) + (0.0343P)^2 + 0.7498P] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0106 (4)

Special details

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 (Ų)

	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)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5N···O3^i	0.85 (1)	2.23 (2)	3.027 (3)	155 (3)

Symmetry code: (i) −x+2, y+1/2, −z+1/2.