N-(2,3-Dichloro-phen-yl)-2-nitro-benzene-sulfonamide.

In the title compound, C12H8Cl2N2O4S, the N-C bond in the C-SO2-NH-C segment has gauche torsions with respect to the S=O bonds. Further, the N-H bond is syn to the ortho-nitro group in the sulfonyl benzene ring and also syn to both the ortho- and meta-Cl atoms in the aniline ring. The mol-ecule is twisted at the S-N bond with a torsion angle of 61.15 (18)°. The dihedral angle between the planes of the benzene rings is 68.00 (6)°. The amide H atom exhibits an intra-molecular bifurcated N-H⋯(O,O) hydrogen bond. In the crystal, pairs of N-H⋯O(S) hydrogen bonds link the mol-ecules into inversion dimers with R2(2)(8) motifs.

Related literature

For our studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Gowda & Weiss (1994 ▶), of N-aryl­sulfonamides, see: Chaithanya et al. (2012 ▶); Gowda et al. (2002 ▶) and of N-chloroaryl-sulfonamides, see: Gowda & Shetty (2004 ▶); Shetty & Gowda (2004 ▶).

Experimental

Crystal data

C12H8Cl2N2O4S

M = 347.16

Monoclinic,

a = 8.2197 (5) Å

b = 15.863 (1) Å

c = 11.0108 (6) Å

β = 93.450 (6)°

V = 1433.09 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.61 mm−1

T = 293 K

0.44 × 0.36 × 0.28 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.774, T max = 0.847

5760 measured reflections

2923 independent reflections

2304 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.092

S = 1.01

2923 reflections

193 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.34 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis n class="Disease">RED (Oxford Diffraction, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812048076/rz5027sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812048076/rz5027Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812048076/rz5027Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C12H8Cl2N2O4S	F(000) = 704
Mr = 347.16	Dx = 1.609 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2186 reflections
a = 8.2197 (5) Å	θ = 2.6–27.7°
b = 15.863 (1) Å	µ = 0.61 mm−1
c = 11.0108 (6) Å	T = 293 K
β = 93.450 (6)°	Prism, colourless
V = 1433.09 (15) Å3	0.44 × 0.36 × 0.28 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2923 independent reflections
Radiation source: fine-focus sealed tube	2304 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.013
Rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −4→10
Tmin = 0.774, Tmax = 0.847	k = −19→19
5760 measured reflections	l = −13→13

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0395P)2 + 0.7218P] where P = (Fo2 + 2Fc2)/3
2923 reflections	(Δ/σ)max = 0.002
193 parameters	Δρmax = 0.35 e Å−3
2 restraints	Δρmin = −0.34 e Å−3

Experimental. Absorption correction: CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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.

	x	y	z	Uiso*/Ueq
C1	0.1808 (2)	0.83051 (12)	0.19670 (17)	0.0339 (4)
C2	0.0312 (2)	0.80943 (13)	0.24194 (17)	0.0376 (4)
C3	0.0199 (3)	0.75308 (15)	0.3365 (2)	0.0494 (6)
H3	−0.0814	0.7382	0.3631	0.059*
C4	0.1601 (3)	0.71913 (15)	0.3910 (2)	0.0572 (6)
H4	0.1538	0.6820	0.4560	0.069*
C5	0.3075 (3)	0.73969 (15)	0.3501 (2)	0.0576 (6)
H5	0.4017	0.7171	0.3883	0.069*
C6	0.3199 (3)	0.79411 (14)	0.2517 (2)	0.0455 (5)
H6	0.4215	0.8060	0.2229	0.055*
C7	0.3264 (2)	1.02271 (12)	0.21739 (18)	0.0352 (4)
C8	0.2745 (3)	1.05973 (14)	0.32373 (19)	0.0410 (5)
C9	0.3880 (3)	1.09390 (15)	0.40794 (19)	0.0474 (5)
C10	0.5515 (3)	1.08976 (16)	0.3900 (2)	0.0573 (6)
H10	0.6272	1.1122	0.4473	0.069*
C11	0.6023 (3)	1.05199 (16)	0.2863 (2)	0.0593 (7)
H11	0.7131	1.0487	0.2742	0.071*
C12	0.4916 (3)	1.01906 (14)	0.2003 (2)	0.0459 (5)
H12	0.5280	0.9942	0.1304	0.055*
N1	0.2103 (2)	0.99427 (11)	0.12555 (16)	0.0385 (4)
H1N	0.116 (2)	1.0115 (14)	0.131 (2)	0.046*
N2	−0.1233 (2)	0.84663 (14)	0.19410 (17)	0.0477 (5)
O1	0.37021 (19)	0.88086 (10)	0.03520 (14)	0.0518 (4)
O2	0.0757 (2)	0.89329 (10)	−0.01537 (13)	0.0526 (4)
O3	−0.1264 (2)	0.92105 (13)	0.16889 (19)	0.0696 (5)
O4	−0.2424 (2)	0.80065 (14)	0.18634 (18)	0.0736 (6)
Cl1	0.06982 (8)	1.06521 (6)	0.34758 (7)	0.0781 (3)
Cl2	0.32597 (10)	1.14330 (5)	0.53734 (6)	0.0784 (3)
S1	0.21072 (6)	0.89869 (3)	0.07156 (4)	0.03673 (14)

	U11	U22	U33	U12	U13	U23
C1	0.0374 (10)	0.0298 (10)	0.0343 (9)	0.0005 (8)	−0.0010 (8)	−0.0022 (8)
C2	0.0400 (11)	0.0381 (11)	0.0346 (10)	−0.0017 (9)	0.0028 (9)	−0.0032 (8)
C3	0.0596 (14)	0.0482 (13)	0.0414 (12)	−0.0091 (11)	0.0102 (11)	0.0017 (10)
C4	0.0835 (15)	0.0432 (13)	0.0435 (12)	−0.0079 (13)	−0.0078 (12)	0.0094 (10)
C5	0.0628 (13)	0.0449 (14)	0.0621 (15)	0.0044 (11)	−0.0222 (11)	0.0079 (11)
C6	0.0398 (11)	0.0391 (12)	0.0563 (13)	0.0009 (9)	−0.0080 (10)	0.0007 (10)
C7	0.0371 (10)	0.0286 (10)	0.0397 (10)	−0.0019 (8)	0.0003 (8)	0.0034 (8)
C8	0.0383 (11)	0.0430 (12)	0.0421 (11)	−0.0025 (9)	0.0058 (9)	0.0006 (9)
C9	0.0555 (14)	0.0459 (13)	0.0405 (11)	−0.0005 (11)	0.0010 (10)	−0.0066 (10)
C10	0.0496 (14)	0.0566 (16)	0.0637 (15)	−0.0016 (12)	−0.0136 (12)	−0.0145 (12)
C11	0.0360 (12)	0.0609 (16)	0.0803 (18)	−0.0010 (11)	−0.0013 (12)	−0.0143 (14)
C12	0.0404 (11)	0.0445 (13)	0.0531 (13)	−0.0006 (10)	0.0059 (10)	−0.0082 (10)
N1	0.0361 (9)	0.0356 (10)	0.0431 (9)	0.0017 (8)	−0.0044 (8)	0.0006 (8)
N2	0.0357 (10)	0.0632 (14)	0.0450 (10)	0.0018 (9)	0.0068 (8)	−0.0006 (9)
O1	0.0524 (9)	0.0535 (10)	0.0518 (9)	−0.0029 (8)	0.0213 (8)	−0.0098 (7)
O2	0.0637 (10)	0.0515 (10)	0.0406 (8)	−0.0080 (8)	−0.0149 (7)	0.0003 (7)
O3	0.0492 (10)	0.0597 (12)	0.0991 (14)	0.0157 (9)	−0.0011 (10)	0.0076 (11)
O4	0.0416 (9)	0.0996 (16)	0.0790 (13)	−0.0178 (10)	−0.0019 (9)	0.0072 (11)
Cl1	0.0441 (4)	0.1163 (7)	0.0756 (5)	−0.0079 (4)	0.0186 (3)	−0.0316 (4)
Cl2	0.0881 (5)	0.0950 (6)	0.0527 (4)	−0.0046 (4)	0.0083 (4)	−0.0295 (4)
S1	0.0411 (3)	0.0379 (3)	0.0312 (2)	−0.0025 (2)	0.0018 (2)	−0.0019 (2)

C1—C6	1.387 (3)	C8—C9	1.386 (3)
C1—C2	1.395 (3)	C8—Cl1	1.721 (2)
C1—S1	1.780 (2)	C9—C10	1.371 (3)
C2—C3	1.379 (3)	C9—Cl2	1.730 (2)
C2—N2	1.469 (3)	C10—C11	1.376 (4)
C3—C4	1.376 (3)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.377 (3)
C4—C5	1.358 (4)	C11—H11	0.9300
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.394 (3)	N1—S1	1.6287 (18)
C5—H5	0.9300	N1—H1N	0.827 (16)
C6—H6	0.9300	N2—O3	1.213 (3)
C7—C12	1.384 (3)	N2—O4	1.220 (2)
C7—C8	1.399 (3)	O1—S1	1.4221 (16)
C7—N1	1.422 (3)	O2—S1	1.4236 (16)
C6—C1—C2	117.74 (19)	C10—C9—C8	120.7 (2)
C6—C1—S1	116.24 (16)	C10—C9—Cl2	118.70 (18)
C2—C1—S1	126.01 (15)	C8—C9—Cl2	120.55 (18)
C3—C2—C1	121.7 (2)	C9—C10—C11	119.3 (2)
C3—C2—N2	115.78 (19)	C9—C10—H10	120.4
C1—C2—N2	122.49 (18)	C11—C10—H10	120.4
C4—C3—C2	119.4 (2)	C12—C11—C10	121.0 (2)
C4—C3—H3	120.3	C12—C11—H11	119.5
C2—C3—H3	120.3	C10—C11—H11	119.5
C5—C4—C3	120.1 (2)	C11—C12—C7	120.3 (2)
C5—C4—H4	119.9	C11—C12—H12	119.9
C3—C4—H4	119.9	C7—C12—H12	119.9
C4—C5—C6	121.0 (2)	C7—N1—S1	122.60 (14)
C4—C5—H5	119.5	C7—N1—H1N	115.9 (16)
C6—C5—H5	119.5	S1—N1—H1N	110.9 (17)
C1—C6—C5	120.0 (2)	O3—N2—O4	124.1 (2)
C1—C6—H6	120.0	O3—N2—C2	118.64 (19)
C5—C6—H6	120.0	O4—N2—C2	117.2 (2)
C12—C7—C8	118.85 (19)	O1—S1—O2	119.54 (10)
C12—C7—N1	120.83 (19)	O1—S1—N1	108.08 (10)
C8—C7—N1	120.21 (18)	O2—S1—N1	106.41 (9)
C9—C8—C7	119.83 (19)	O1—S1—C1	105.65 (10)
C9—C8—Cl1	120.22 (17)	O2—S1—C1	110.21 (9)
C7—C8—Cl1	119.92 (16)	N1—S1—C1	106.24 (9)
C6—C1—C2—C3	−1.3 (3)	Cl2—C9—C10—C11	−178.8 (2)
S1—C1—C2—C3	177.24 (17)	C9—C10—C11—C12	0.5 (4)
C6—C1—C2—N2	177.51 (19)	C10—C11—C12—C7	−0.6 (4)
S1—C1—C2—N2	−4.0 (3)	C8—C7—C12—C11	−0.5 (3)
C1—C2—C3—C4	2.6 (3)	N1—C7—C12—C11	175.6 (2)
N2—C2—C3—C4	−176.3 (2)	C12—C7—N1—S1	57.5 (3)
C2—C3—C4—C5	−1.4 (4)	C8—C7—N1—S1	−126.45 (18)
C3—C4—C5—C6	−1.0 (4)	C3—C2—N2—O3	138.7 (2)
C2—C1—C6—C5	−1.1 (3)	C1—C2—N2—O3	−40.2 (3)
S1—C1—C6—C5	−179.79 (18)	C3—C2—N2—O4	−38.8 (3)
C4—C5—C6—C1	2.3 (4)	C1—C2—N2—O4	142.3 (2)
C12—C7—C8—C9	1.7 (3)	C7—N1—S1—O1	−51.85 (19)
N1—C7—C8—C9	−174.38 (19)	C7—N1—S1—O2	178.59 (16)
C12—C7—C8—Cl1	179.99 (17)	C7—N1—S1—C1	61.15 (18)
N1—C7—C8—Cl1	3.9 (3)	C6—C1—S1—O1	16.35 (18)
C7—C8—C9—C10	−1.9 (3)	C2—C1—S1—O1	−162.21 (17)
Cl1—C8—C9—C10	179.9 (2)	C6—C1—S1—O2	146.80 (16)
C7—C8—C9—Cl2	177.68 (17)	C2—C1—S1—O2	−31.8 (2)
Cl1—C8—C9—Cl2	−0.6 (3)	C6—C1—S1—N1	−98.31 (17)
C8—C9—C10—C11	0.7 (4)	C2—C1—S1—N1	83.13 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.83 (2)	2.48 (2)	3.136 (2)	137 (2)
N1—H1N···O3	0.83 (2)	2.51 (2)	3.065 (3)	125 (2)
N1—H1N···Cl1	0.83 (2)	2.58 (2)	2.9858 (19)	111 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.83 (2)	2.48 (2)	3.136 (2)	137 (2)
N1—H1N⋯O3	0.83 (2)	2.51 (2)	3.065 (3)	125 (2)

Symmetry code: (i) .