N-(4-Fluoro­phen­yl)methane­sulfonamide

The structure of the title compound (4FPMSA), C₇H₈FNO₂S, closely resembles those of N-phenyl­methane­sulfonamde (PMSA) and other alkyl sulfonanilides. The substitution of either the fluoro, bromo or nitro group at the para position of PMSA does not change the space group, unlike in the case of meta substitutions in PMSA. The geometric parameters in PMSA, 4FPMSA, 4BPMSA and 4NPMSA are similar except for some difference in the angle S2—N5—C6 and some torsional angles. As in other alkyl sulfonanilides, the amide hydrogen sits alone on one side of the plane of the benzene ring, while the whole methane­sulfonyl group is on the opposite side of the plane. It is thus available to a receptor mol­ecule during biological activity. The mol­ecules in the title compound are packed into a layer structure in the a-axis direction via N—H...O hydrogen bonds [H...O = 2.08 (2), N...O = 2.911 (6) Å and N—H...O = 164 (6)°].

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.010 Å
• R factor = 0.097
• wR factor = 0.262
• Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level C
RFACR01_ALERT_3_C  The value of the weighted R factor is > 0.25
            Weighted R factor given   0.262
PLAT084_ALERT_2_C High R2 Value ..................................       0.26
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         S2
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10
PLAT731_ALERT_1_C Bond    Calc     0.86(4), Rep   0.859(10) ......       4.00 su-Ra
              N5   -H5N     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.86(4), Rep   0.859(10) ......       4.00 su-Ra
              N5   -H5N     1.555   1.555

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

The stereochemistry of biologically significant alkyl sulfonanilides, particularly in the vicinity of the phenyl–NH portion is of interest as it helps in explaining their biological activity. In the present work, the structure of N-(4-fluorophenyl)-methanesulfonamde (4FPMSA) has been determined (Fig. 1) to explore the substituent effects on the structures of sulphonanilides (Gowda et al., 2007a-c). The substitution of either the fluoro or nitro group at the para position of N- (phenyl)-methanesulfonamde (PMSA),(Klug, 1968) does not change the space group (Gowda et al., 2007a), unlike in the case of meta substitutions in PMSA (Gowda et al., 2007b,c). The bond parameters in PMSA, 4FPMSA and N-(4-nitrophenyl)-methanesulfonamde (4NPMSA)are similar except some changes in the angle, S2N5C6: 120.0 (1)° (PMSA); 120.2 (3)° (4FPMSA) and 128.1 (3)° (4NPMSA), respectively, and in torsional angles, C1—S2—N5—C6, S2—N5—C6—C7, S2—N5—C6—C11: 62.2 (2)°, 75.5 (2)°, -106.6 (2)° (PMSA); -70.7 (4)°, 102.8 (5)°, -78.1 (6)° (4FPMSA) & -67.2 (4)°, -21.5 (6)%, 158.9 (4)° (4NPMSA), respectively. The amide hydrogen sits alone on one side of the plane of the phenyl group, while the whole methanesulfonyl group is on the opposite side of the plane similar to that observed in other alkyl sulfonanilides (Gowda et al., 2007a-c). It is thus available to a receptor molecule during its biological activity. The molecules in the title compound are packed into layer structure (Fig. 2) in the direction of a axis via N—H···O hydrogen bonds(Table 1).

Related literature

For related literature, see: Gowda et al. (2007a,b,c); Jayalakshmi & Gowda (2004); Klug (1968); Clark & Reid (1995).

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 studies at room temperature.

S3. Refinement

The H atom of the NH group was located in a diffrerence map and its position refined. The carbon-bound H atoms were positioned with idealized geometry and refined using a riding model with C—H = 0.93 Å (CH aromatic) or 0.96 Å (CH₃). Isotropic displacement parameters for all H atoms were set equal to 1.2U_eq (parent atom).

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2004); 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 (Sheldrick, 1997).

Figures

	Fig. 1. 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.
	Fig. 2. Hydrogen bonding in the title compound. Hydrogen bonds are shown as dashed lines.

N-(4-Fluorophenyl)methanesulfonamide

Crystal data

C7H8FNO2S	F(000) = 392
Mr = 189.20	Dx = 1.448 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2243 reflections
a = 17.272 (3) Å	θ = 3.6–22.0°
b = 5.059 (1) Å	µ = 0.35 mm^−1
c = 10.140 (2) Å	T = 293 K
β = 101.65 (1)°	Plate, colourless
V = 867.8 (3) Å^3	0.50 × 0.48 × 0.03 mm
Z = 4

Data collection

Oxford Diffraction Xcalibur Diffractometer with Sapphire CCD detector	1757 independent reflections
Radiation source: fine-focus sealed tube	1471 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.087
Rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 4.1°
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2004)	h = −21→21
Tmin = 0.852, Tmax = 0.988	k = −6→6
4986 measured reflections	l = −7→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.098	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.262	H atoms treated by a mixture of independent and constrained refinement
S = 1.20	w = 1/[σ^2(Fo^2) + (0.1115P)^2 + 1.0115P] where P = (Fo^2 + 2Fc^2)/3
1757 reflections	(Δ/σ)max = 0.001
112 parameters	Δρmax = 0.50 e Å^−3
1 restraint	Δρmin = −0.54 e Å^−3

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	0.5825 (4)	0.0142 (13)	0.4135 (6)	0.0720 (16)
H1A	0.5800	−0.1721	0.4302	0.086*
H1B	0.5303	0.0880	0.3990	0.086*
H1C	0.6152	0.0981	0.4898	0.086*
C6	0.7729 (3)	−0.0529 (9)	0.3838 (5)	0.0558 (13)
C7	0.7940 (4)	−0.1872 (12)	0.5050 (6)	0.0697 (15)
H7	0.7612	−0.3199	0.5258	0.084*
C8	0.8630 (4)	−0.1275 (15)	0.5955 (7)	0.0833 (19)
H8	0.8784	−0.2233	0.6748	0.100*
C9	0.9079 (4)	0.0773 (16)	0.5645 (8)	0.084 (2)
C10	0.8894 (4)	0.2161 (14)	0.4461 (8)	0.0833 (19)
H10	0.9224	0.3510	0.4283	0.100*
C11	0.8209 (4)	0.1538 (12)	0.3523 (7)	0.0716 (16)
H11	0.8073	0.2459	0.2716	0.086*
N5	0.7032 (3)	−0.1189 (9)	0.2855 (5)	0.0605 (12)
H5N	0.683 (3)	−0.271 (6)	0.294 (6)	0.073*
O3	0.6484 (3)	0.3356 (7)	0.2684 (4)	0.0803 (13)
O4	0.5695 (3)	−0.0318 (8)	0.1535 (4)	0.0776 (13)
F12	0.9756 (3)	0.1488 (12)	0.6532 (6)	0.1259 (18)
S2	0.62315 (9)	0.0664 (2)	0.26953 (12)	0.0555 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.082 (4)	0.076 (4)	0.063 (3)	0.015 (3)	0.029 (3)	0.007 (3)
C6	0.070 (3)	0.040 (3)	0.064 (3)	−0.002 (2)	0.032 (3)	−0.009 (2)
C7	0.079 (4)	0.061 (4)	0.073 (4)	0.000 (3)	0.026 (3)	0.004 (3)
C8	0.089 (5)	0.089 (5)	0.073 (4)	0.013 (4)	0.019 (4)	0.002 (3)
C9	0.062 (4)	0.096 (5)	0.094 (5)	0.010 (3)	0.017 (3)	−0.030 (4)
C10	0.068 (4)	0.077 (4)	0.113 (5)	−0.011 (3)	0.036 (4)	−0.018 (4)
C11	0.076 (4)	0.063 (4)	0.083 (4)	−0.014 (3)	0.034 (3)	−0.002 (3)
N5	0.079 (3)	0.041 (2)	0.069 (3)	−0.008 (2)	0.031 (2)	−0.010 (2)
O3	0.107 (3)	0.0325 (19)	0.096 (3)	−0.012 (2)	0.008 (3)	0.0096 (19)
O4	0.112 (3)	0.063 (3)	0.049 (2)	−0.018 (2)	−0.004 (2)	−0.0031 (17)
F12	0.077 (3)	0.160 (5)	0.132 (4)	0.001 (3)	0.002 (3)	−0.043 (3)
S2	0.0833 (10)	0.0364 (7)	0.0463 (7)	−0.0082 (6)	0.0115 (6)	0.0026 (5)

Geometric parameters (Å, º)

C1—S2	1.763 (5)	C8—H8	0.9300
C1—H1A	0.9600	C9—C10	1.371 (10)
C1—H1B	0.9600	C9—F12	1.372 (8)
C1—H1C	0.9600	C10—C11	1.397 (9)
C6—C7	1.387 (8)	C10—H10	0.9300
C6—C11	1.410 (7)	C11—H11	0.9300
C6—N5	1.439 (7)	N5—S2	1.651 (5)
C7—C8	1.383 (9)	N5—H5N	0.859 (10)
C7—H7	0.9300	O3—S2	1.431 (4)
C8—C9	1.368 (10)	O4—S2	1.432 (4)
S2—C1—H1A	109.5	C10—C9—F12	117.1 (7)
S2—C1—H1B	109.5	C9—C10—C11	119.7 (6)
H1A—C1—H1B	109.5	C9—C10—H10	120.1
S2—C1—H1C	109.5	C11—C10—H10	120.1
H1A—C1—H1C	109.5	C10—C11—C6	118.0 (6)
H1B—C1—H1C	109.5	C10—C11—H11	121.0
C7—C6—C11	120.2 (6)	C6—C11—H11	121.0
C7—C6—N5	122.3 (5)	C6—N5—S2	120.2 (3)
C11—C6—N5	117.6 (5)	C6—N5—H5N	116 (4)
C8—C7—C6	121.2 (6)	S2—N5—H5N	100 (4)
C8—C7—H7	119.4	O3—S2—O4	118.2 (3)
C6—C7—H7	119.4	O3—S2—N5	106.9 (3)
C9—C8—C7	117.7 (7)	O4—S2—N5	105.9 (3)
C9—C8—H8	121.1	O3—S2—C1	108.8 (3)
C7—C8—H8	121.1	O4—S2—C1	109.2 (3)
C8—C9—C10	123.2 (7)	N5—S2—C1	107.4 (3)
C8—C9—F12	119.7 (8)
C11—C6—C7—C8	−1.8 (9)	C7—C6—C11—C10	0.2 (8)
N5—C6—C7—C8	177.3 (5)	N5—C6—C11—C10	−178.8 (5)
C6—C7—C8—C9	3.1 (9)	C7—C6—N5—S2	102.8 (5)
C7—C8—C9—C10	−3.1 (10)	C11—C6—N5—S2	−78.1 (6)
C7—C8—C9—F12	178.0 (5)	C6—N5—S2—O3	45.9 (4)
C8—C9—C10—C11	1.6 (10)	C6—N5—S2—O4	172.7 (4)
F12—C9—C10—C11	−179.4 (5)	C6—N5—S2—C1	−70.7 (4)
C9—C10—C11—C6	−0.1 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5N···O3^i	0.86 (1)	2.08 (2)	2.911 (6)	164 (6)

Symmetry code: (i) x, y−1, z.