N-(3,5-Dichloro­phen­yl)methane­sulfonamide

The structure of the title compound, C₇H₇Cl₂NO₂S, resembles those of other methane­sulfonanilides, with similar geometric parameters. The amide H atom is roughly in the plane of the dichloro­phenyl group with a deviation of −0.021 (7) Å, while the S atom is slightly above the plane with a deviation of 0.285 (9) Å. The dihedral angle between the benzene ring and the C—N—S plane is 14.4 (5)°. The mol­ecules are packed into chains through N—H...O hydrogen bonds and weak (methyl)C—H...O inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.092
• wR factor = 0.255
• Data-to-parameter ratio = 14.1

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   0.255
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       1.33
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.75 mm
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          8

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      1.330
            Tmax scaled      0.794 Tmin scaled      0.057
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   2 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
   5 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 biological activity of sulfonanilides is thought to be due to the amide hydrogen portion of the molecules as it can align itself in relation to a receptor site. Thus the structural studies of sulfonanilides are of interest. In the present work, the structure of N-(3,5-dichlorophenyl)-methanesulfonamde (35DCPMSA) has been determined as part of our study of the substituent effects on the solid state structures of methanesulfonanilides (Gowda et al., 2007a, b). The structure of 35DCPMSA (Fig. 1) is similar to those of other methanesulfonanilides (Gowda et al., 2007a, b). 35DCPMSA crystallizes in monoclinic P2₁/c space group in contrast to the monoclinc P2₁/c, monoclinic P2₁/n, triclinic P-1 and triclinic P-1 space groups observed for N-(2,3-dichlorophenyl)-methanesulfonamide (23DCPMSA), N-(2,4-dichlorophenyl)-methanesulfonamide (24DCPMSA), N-(2,5-dichlorophenyl)-methanesulfonamide (25DCPMSA), N-(3,4-dichlorophenyl)-methanesulfonamide (34DCPMSA)(Gowda et al., 2007b), respectively. The substitution of a Cl atom at the meta position of N-(phenyl)-methanesulfonamde (PMSA) (Klug, 1968) to produce N-(3-chlorophenyl)-methanesulfonamide (3CPMSA) changes its space group from monoclinic P2₁/c to C 2/c (Gowda et al., 2007a). The substitution of an additional chloro group either at ortho, para or meta position of 3CPMSA to produce 23DCPMSA, 34DCPMSA or 35DCPMSA, respectively, changes the space group from monoclinc C 2/c to monoclinic P2₁/c with 23DCPMSA, triclinic P-1 with 34DCPMSA and monoclinic P2₁/c with 35DCPMSA. The geometric parameters in 35DCPMSA are similar to those in other methanesulfonanilides except for some difference in the bond and torsional angles. The N—H is roughly in the plane of the dichlorophenyl group with a deviation of -0.021 (7) Å from the plane, whereas the S atom is slightly above with a deviation of 0.285 (9) Å. The dihedral angle between the benzene ring and the C6—N5—S2 plane is 14.4 (5)°. The N—H···O hydrogen bonds (Table 1) build up chains which are further connected through weak C—H (methyl)···O interactions (Fig. 2).

Related literature

For related literature, see: Gowda et al. (2007a, 2007b); 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 compound were obtained from a slow evaporation of its ethanolic solution and used for X-ray diffraction studies at room temperature.

S3. Refinement

H atoms attached to C atoms were fixed geometrically and treated as riding, with C—H = 0.93 Å (aromatic) or 0.96 Å (CH₃) and with U_iso(H) = 1.2U_eq(aromatic) or U_iso(H) = 1.5U_eq(CH₃). H atom attched to N was refined using a N—H restraint of 0.85 (1) Å.

Computing details

Data collection: CAD-4-PC Software (Enraf–Nonius, 1996); cell refinement: CAD-4-PC Software; 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: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

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. Partial packing view showing the formation of the hydrogen bond network through N—H···O and C—H···O hydrogen bonding interactions. H bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity. [Symmetry code: (i) -x + 1, 1/2 + y, 3/2 - z; (ii) x, 1 + y, z].

N-(3,5-dichlorophenyl)methanesulfonamide

Crystal data

C7H7Cl2NO2S	F(000) = 488
Mr = 240.10	Dx = 1.627 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 16.076 (3) Å	θ = 2.8–19.9°
b = 5.053 (2) Å	µ = 7.70 mm^−1
c = 12.148 (3) Å	T = 299 K
β = 96.60 (2)°	Long laminar, colourless
V = 980.3 (5) Å^3	0.75 × 0.30 × 0.03 mm
Z = 4

Data collection

Enraf–Nonius CAD4 diffractometer	1424 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.059
Graphite monochromator	θmax = 67.1°, θmin = 2.8°
ω scans	h = −19→19
Absorption correction: ψ scan (North et al., 1968)	k = 0→6
Tmin = 0.043, Tmax = 0.597	l = −14→1
1828 measured reflections	3 standard reflections every 120 min
1731 independent reflections	intensity decay: 2.5%

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)] = 0.092	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.255	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ^2(Fo^2) + (0.2P)^2] where P = (Fo^2 + 2Fc^2)/3
1731 reflections	(Δ/σ)max < 0.001
123 parameters	Δρmax = 1.17 e Å^−3
1 restraint	Δρmin = −0.70 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	0.6079 (3)	0.3484 (10)	1.0081 (4)	0.0512 (12)
H1A	0.5810	0.2657	1.0658	0.077*
H1B	0.5894	0.5286	0.9994	0.077*
H1C	0.6675	0.3447	1.0275	0.077*
C6	0.7071 (3)	0.3919 (9)	0.7811 (3)	0.0415 (10)
C7	0.7711 (3)	0.2524 (11)	0.8417 (4)	0.0525 (12)
H7	0.7596	0.1182	0.8901	0.063*
C8	0.8527 (4)	0.3193 (11)	0.8280 (5)	0.0587 (13)
C9	0.8727 (3)	0.5086 (12)	0.7540 (5)	0.0611 (13)
H9	0.9281	0.5488	0.7456	0.073*
C10	0.8076 (4)	0.6353 (11)	0.6932 (5)	0.0562 (12)
C11	0.7251 (3)	0.5846 (9)	0.7054 (4)	0.0482 (11)
H11	0.6822	0.6770	0.6641	0.058*
N5	0.6212 (2)	0.3432 (8)	0.7865 (3)	0.0437 (9)
O3	0.4928 (2)	0.1929 (7)	0.8545 (3)	0.0532 (9)
O4	0.6204 (2)	−0.0779 (7)	0.8935 (3)	0.0618 (10)
S2	0.58202 (7)	0.1770 (2)	0.88336 (8)	0.0415 (5)
Cl12	0.83015 (11)	0.8707 (3)	0.59639 (16)	0.0837 (6)
Cl13	0.93272 (10)	0.1532 (5)	0.90719 (17)	0.0962 (8)
H5	0.586 (2)	0.451 (7)	0.754 (3)	0.033 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.063 (3)	0.046 (3)	0.043 (2)	−0.002 (2)	0.003 (2)	−0.0037 (19)
C6	0.046 (2)	0.035 (2)	0.043 (2)	0.0028 (18)	0.0066 (17)	−0.0026 (17)
C7	0.056 (3)	0.051 (3)	0.051 (2)	0.007 (2)	0.008 (2)	0.006 (2)
C8	0.053 (3)	0.061 (3)	0.061 (3)	0.006 (2)	0.003 (2)	0.006 (2)
C9	0.051 (3)	0.060 (3)	0.074 (3)	−0.006 (2)	0.017 (2)	0.002 (3)
C10	0.063 (3)	0.046 (3)	0.063 (3)	−0.001 (2)	0.022 (2)	0.005 (2)
C11	0.056 (2)	0.036 (2)	0.053 (2)	0.004 (2)	0.012 (2)	0.0040 (19)
N5	0.043 (2)	0.045 (2)	0.0418 (19)	0.0047 (15)	0.0016 (16)	0.0088 (15)
O3	0.0509 (18)	0.048 (2)	0.0596 (19)	−0.0087 (14)	0.0031 (15)	−0.0066 (14)
O4	0.076 (2)	0.0288 (18)	0.082 (2)	0.0097 (17)	0.0151 (19)	0.0060 (16)
S2	0.0479 (7)	0.0299 (7)	0.0466 (7)	−0.0017 (4)	0.0061 (5)	−0.0010 (4)
Cl12	0.0841 (11)	0.0712 (11)	0.1022 (12)	−0.0009 (8)	0.0379 (9)	0.0311 (9)
Cl13	0.0531 (9)	0.1287 (19)	0.1048 (13)	0.0228 (8)	0.0006 (8)	0.0388 (11)

Geometric parameters (Å, º)

C1—S2	1.754 (5)	C8—Cl13	1.732 (6)
C1—H1A	0.9600	C9—C10	1.369 (8)
C1—H1B	0.9600	C9—H9	0.9300
C1—H1C	0.9600	C10—C11	1.376 (7)
C6—C7	1.387 (7)	C10—Cl12	1.740 (5)
C6—C11	1.392 (7)	C11—H11	0.9300
C6—N5	1.412 (6)	N5—S2	1.630 (4)
C7—C8	1.382 (8)	N5—H5	0.85 (3)
C7—H7	0.9300	O3—S2	1.439 (4)
C8—C9	1.376 (8)	O4—S2	1.427 (4)
S2—C1—H1A	109.5	C8—C9—H9	121.4
S2—C1—H1B	109.5	C9—C10—C11	122.8 (5)
H1A—C1—H1B	109.5	C9—C10—Cl12	118.6 (4)
S2—C1—H1C	109.5	C11—C10—Cl12	118.6 (4)
H1A—C1—H1C	109.5	C10—C11—C6	118.5 (5)
H1B—C1—H1C	109.5	C10—C11—H11	120.7
C7—C6—C11	120.6 (4)	C6—C11—H11	120.7
C7—C6—N5	123.8 (4)	C6—N5—S2	125.8 (3)
C11—C6—N5	115.5 (4)	C6—N5—H5	118 (3)
C8—C7—C6	117.9 (5)	S2—N5—H5	112 (3)
C8—C7—H7	121.1	O4—S2—O3	118.7 (2)
C6—C7—H7	121.1	O4—S2—N5	109.2 (2)
C9—C8—C7	123.0 (5)	O3—S2—N5	104.6 (2)
C9—C8—Cl13	119.0 (4)	O4—S2—C1	108.3 (2)
C7—C8—Cl13	117.9 (4)	O3—S2—C1	108.3 (2)
C10—C9—C8	117.1 (5)	N5—S2—C1	107.2 (2)
C10—C9—H9	121.4

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···O3^i	0.85 (3)	2.11 (4)	2.949 (5)	170 (4)
C1—H1B···O4^ii	0.96	2.45	3.233 (6)	138

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x, y+1, z.