3,4-Dichloro­benzene­sulfonamide

The structure of the title compound, C₆H₅Cl₂NO₂S, resembles those of other aryl­sulfonamides, with similar geometric parameters. The mol­ecules in the title compound are packed into a layered structure parallel to the (100) plane via N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 302 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.031
• wR factor = 0.089
• Data-to-parameter ratio = 15.4

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S1. Comment

Several arylsulfonamides and their N-halo compounds exhibit distinct physical, chemical and biological properties. Thus these compounds are of interest in synthetic, mechanistic, analytical and biological chemistry. In the present work, the structure of 3,4-dichlorobenzenesulfonamde (34DCBSA) has been determined to study the effect of substituents on the solid state structures of sulfonamides and N-halo arylsulfonamides (Gowda et al., 2003; Gowda, Nayak, Kožíšek et al., 2007; Gowda, Nayak, Foro et al., 2007; Gowda, Srilatha et al., 2007). The structure of 34DCBSA (Fig. 1) resembles those of other arylsulfonamides (Gowda et al., 2003, Gowda, Nayak, Kožíšek et al., 2007; Gowda, Nayak, Foro et al., 2007; Gowda, Srilatha et al., 2007); Jones & Weinkauf, 1993; Kumar et al., 1992).

The bond parameters in 34DCBSA are similar to those in other arylsulfonamides. The molecules in the title compound are packed into layered structure developping parallel to the (1 0 0) plane via N—H···O hydrogen bonds (Table 1, Fig. 2).

Related literature

For related literature, see: Gowda et al. (2002, 2003); Gowda, Nayak, Kožíšek et al. (2007); Gowda, Nayak, Foro et al. (2007); Gowda, Srilatha et al. (2007); Jones & Weinkauf (1993); Kumar et al. (1992).

S2. Experimental

The title compound was prepared according to the literature method (Gowda et al., 2002). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra (Gowda et al., 2002). 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.

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. Molecular structure of the title compound showing the atom labeling 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 layered structure through N—H···O hydrogen bonds. H bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity. [Symmetry codes: (i) 1 - x, -y, 2 - z; (ii) 1 - x, 1/2 + y, 3/2 - z].

3,4-Dichlorobenzenesulfonamide

Crystal data

C6H5Cl2NO2S	F(000) = 456
Mr = 226.07	Dx = 1.718 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2408 reflections
a = 11.353 (2) Å	θ = 3.1–25.8°
b = 5.9629 (7) Å	µ = 0.94 mm^−1
c = 13.452 (2) Å	T = 302 K
β = 106.26 (1)°	Prism, colourless
V = 874.2 (2) Å^3	0.40 × 0.40 × 0.08 mm
Z = 4

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	1774 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1297 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
Rotation method data acquisition using ω and phi scans.	θmax = 26.4°, θmin = 3.2°
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2006) (Clark & Reid, 1995)	h = −11→14
Tmin = 0.706, Tmax = 0.929	k = −7→6
5809 measured reflections	l = −16→16

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0437P)^2 + 0.2808P] where P = (Fo^2 + 2Fc^2)/3
1774 reflections	(Δ/σ)max = 0.001
115 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.22 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	0.3139 (2)	0.3022 (4)	0.86230 (15)	0.0351 (5)
C2	0.2565 (2)	0.4551 (4)	0.78694 (15)	0.0387 (5)
H2	0.2722	0.4538	0.7227	0.046*
C3	0.1767 (2)	0.6082 (4)	0.80752 (16)	0.0380 (5)
C4	0.1528 (2)	0.6091 (4)	0.90318 (17)	0.0411 (5)
C5	0.2108 (2)	0.4574 (5)	0.97803 (17)	0.0485 (6)
H5	0.1955	0.4597	1.0424	0.058*
C6	0.2913 (2)	0.3024 (4)	0.95846 (17)	0.0437 (6)
H6	0.3299	0.1992	1.0089	0.052*
N1	0.5551 (2)	0.2049 (4)	0.88648 (17)	0.0451 (5)
H1A	0.573 (2)	0.202 (4)	0.948 (2)	0.054*
H1B	0.568 (2)	0.321 (5)	0.858 (2)	0.054*
O1	0.41096 (15)	−0.0934 (3)	0.89211 (12)	0.0458 (4)
O2	0.40003 (16)	0.1024 (3)	0.72771 (11)	0.0488 (4)
S1	0.41992 (5)	0.10901 (9)	0.83756 (4)	0.03697 (18)
Cl1	0.10759 (7)	0.80068 (14)	0.71418 (5)	0.0653 (2)
Cl2	0.05152 (7)	0.79949 (14)	0.92960 (6)	0.0701 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0384 (12)	0.0349 (12)	0.0322 (10)	−0.0044 (11)	0.0104 (9)	−0.0055 (9)
C2	0.0435 (13)	0.0429 (14)	0.0307 (10)	−0.0046 (11)	0.0121 (9)	−0.0018 (10)
C3	0.0375 (12)	0.0368 (13)	0.0383 (11)	−0.0018 (11)	0.0084 (9)	0.0009 (10)
C4	0.0377 (12)	0.0456 (14)	0.0408 (12)	−0.0008 (11)	0.0125 (9)	−0.0088 (11)
C5	0.0548 (15)	0.0610 (17)	0.0336 (11)	0.0009 (13)	0.0187 (10)	−0.0027 (11)
C6	0.0532 (15)	0.0466 (14)	0.0329 (11)	0.0064 (13)	0.0150 (10)	0.0042 (10)
N1	0.0483 (13)	0.0456 (13)	0.0422 (11)	−0.0059 (11)	0.0143 (9)	0.0090 (10)
O1	0.0580 (11)	0.0332 (9)	0.0467 (9)	−0.0045 (8)	0.0157 (8)	0.0015 (7)
O2	0.0675 (11)	0.0475 (10)	0.0329 (8)	0.0081 (9)	0.0164 (7)	−0.0042 (7)
S1	0.0467 (3)	0.0338 (3)	0.0318 (3)	−0.0009 (3)	0.0132 (2)	−0.0016 (2)
Cl1	0.0719 (5)	0.0671 (5)	0.0566 (4)	0.0228 (4)	0.0173 (3)	0.0205 (3)
Cl2	0.0712 (5)	0.0779 (6)	0.0666 (4)	0.0264 (4)	0.0282 (4)	−0.0060 (4)

Geometric parameters (Å, º)

C1—C2	1.383 (3)	C5—C6	1.376 (3)
C1—C6	1.388 (3)	C5—H5	0.9300
C1—S1	1.764 (2)	C6—H6	0.9300
C2—C3	1.368 (3)	N1—S1	1.597 (2)
C2—H2	0.9300	N1—H1A	0.79 (3)
C3—C4	1.387 (3)	N1—H1B	0.82 (3)
C3—Cl1	1.720 (2)	O1—S1	1.4310 (16)
C4—C5	1.376 (3)	O2—S1	1.4315 (15)
C4—Cl2	1.722 (2)
C2—C1—C6	120.7 (2)	C4—C5—H5	119.7
C2—C1—S1	119.88 (16)	C5—C6—C1	119.0 (2)
C6—C1—S1	119.38 (17)	C5—C6—H6	120.5
C3—C2—C1	119.60 (19)	C1—C6—H6	120.5
C3—C2—H2	120.2	S1—N1—H1A	111 (2)
C1—C2—H2	120.2	S1—N1—H1B	112.4 (18)
C2—C3—C4	120.2 (2)	H1A—N1—H1B	118 (3)
C2—C3—Cl1	119.35 (17)	O1—S1—O2	119.53 (9)
C4—C3—Cl1	120.46 (18)	O1—S1—N1	106.80 (11)
C5—C4—C3	119.9 (2)	O2—S1—N1	106.91 (11)
C5—C4—Cl2	119.51 (18)	O1—S1—C1	107.70 (10)
C3—C4—Cl2	120.60 (19)	O2—S1—C1	107.10 (10)
C6—C5—C4	120.6 (2)	N1—S1—C1	108.42 (11)
C6—C5—H5	119.7
C6—C1—C2—C3	0.0 (3)	C4—C5—C6—C1	0.5 (4)
S1—C1—C2—C3	−178.39 (17)	C2—C1—C6—C5	−0.1 (4)
C1—C2—C3—C4	−0.4 (3)	S1—C1—C6—C5	178.35 (19)
C1—C2—C3—Cl1	178.96 (17)	C2—C1—S1—O1	−147.14 (18)
C2—C3—C4—C5	0.8 (4)	C6—C1—S1—O1	34.4 (2)
Cl1—C3—C4—C5	−178.54 (19)	C2—C1—S1—O2	−17.4 (2)
C2—C3—C4—Cl2	−179.46 (18)	C6—C1—S1—O2	164.16 (18)
Cl1—C3—C4—Cl2	1.2 (3)	C2—C1—S1—N1	97.6 (2)
C3—C4—C5—C6	−0.9 (4)	C6—C1—S1—N1	−80.8 (2)
Cl2—C4—C5—C6	179.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1^i	0.79 (3)	2.21 (3)	2.970 (3)	161 (3)
N1—H1B···O2^ii	0.82 (3)	2.13 (3)	2.945 (3)	174 (3)

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