N-(3,5-Dichloro-phen-yl)-2-nitro-benzene-sulfonamide.

In the title compound, C12H8Cl2N2O4S, the C-S-N-C torsion angle is 49.34 (18)° and the dihedral angle between the benzene rings is 71.92 (10)°. The amide H atom exhibits bifurcated hydrogen bonding. The N-H bond is syn to the ortho-nitro group enabling the formation of an S(7) loop. In the crystal, pairs of N-H⋯O(S) hydrogen bonds link the mol-ecules into inversion dimers via R2(2)(8) rings.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Gowda & Weiss (1994 ▶); Shahwar et al. (2012 ▶), of N-aryl­sulfonamides, see: Chaithanya et al. (2012 ▶) and of N-chloro­aryl­sulfonamides, see: Shetty & Gowda (2004 ▶). For hydrogen-bonding patterns and motifs, see: Adsmond et al. (2001 ▶).

Experimental

Crystal data

C12H8Cl2N2O4S

M = 347.16

Triclinic,

a = 8.2823 (8) Å

b = 8.3436 (9) Å

c = 10.670 (1) Å

α = 76.730 (8)°

β = 89.298 (9)°

γ = 86.875 (9)°

V = 716.59 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.61 mm−1

T = 293 K

0.44 × 0.40 × 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

4766 measured reflections

2925 independent reflections

2600 reflections with I > 2σ(I)

R int = 0.009

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.092

S = 1.04

2925 reflections

194 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.49 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis 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/S1600536812048283/tk5173sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812048283/tk5173Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812048283/tk5173Isup3.cml

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

C12H8Cl2N2O4S	Z = 2
Mr = 347.16	F(000) = 352
Triclinic, P1	Dx = 1.609 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2823 (8) Å	Cell parameters from 3256 reflections
b = 8.3436 (9) Å	θ = 3.1–27.7°
c = 10.670 (1) Å	µ = 0.61 mm−1
α = 76.730 (8)°	T = 293 K
β = 89.298 (9)°	Prism, colourless
γ = 86.875 (9)°	0.44 × 0.40 × 0.28 mm
V = 716.59 (12) Å3

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2925 independent reflections
Radiation source: fine-focus sealed tube	2600 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.009
Rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 3.2°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −8→10
Tmin = 0.774, Tmax = 0.847	k = −9→10
4766 measured reflections	l = −7→13

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.092	w = 1/[σ2(Fo2) + (0.0408P)2 + 0.4244P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2925 reflections	Δρmax = 0.44 e Å−3
194 parameters	Δρmin = −0.49 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.100 (5)

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	0.3367 (2)	0.2350 (2)	0.37443 (17)	0.0340 (4)
C2	0.2649 (2)	0.3607 (2)	0.42524 (17)	0.0371 (4)
C3	0.3229 (3)	0.5157 (2)	0.4011 (2)	0.0459 (5)
H3	0.2729	0.5973	0.4369	0.055*
C4	0.4565 (3)	0.5488 (3)	0.3228 (2)	0.0492 (5)
H4	0.4964	0.6537	0.3046	0.059*
C5	0.5305 (2)	0.4268 (3)	0.2718 (2)	0.0498 (5)
H5	0.6207	0.4496	0.2192	0.060*
C6	0.4721 (2)	0.2700 (2)	0.29780 (19)	0.0419 (4)
H6	0.5241	0.1880	0.2636	0.050*
C7	0.0975 (2)	0.1026 (2)	0.19048 (18)	0.0380 (4)
C8	0.2129 (2)	0.0663 (3)	0.1044 (2)	0.0448 (4)
H8	0.3031	−0.0032	0.1331	0.054*
C9	0.1901 (3)	0.1361 (3)	−0.0251 (2)	0.0495 (5)
C10	0.0575 (3)	0.2374 (3)	−0.0718 (2)	0.0560 (6)
H10	0.0443	0.2824	−0.1594	0.067*
C11	−0.0553 (3)	0.2695 (3)	0.0166 (2)	0.0549 (5)
C12	−0.0370 (2)	0.2058 (3)	0.14680 (19)	0.0472 (5)
H12	−0.1136	0.2315	0.2046	0.057*
N1	0.10830 (19)	0.0311 (2)	0.32445 (15)	0.0403 (4)
H1N	0.024 (2)	0.045 (3)	0.367 (2)	0.048*
N2	0.1200 (2)	0.3345 (2)	0.50690 (17)	0.0481 (4)
O1	0.39505 (17)	−0.06691 (17)	0.36502 (15)	0.0478 (3)
O2	0.21976 (16)	−0.01250 (17)	0.54098 (13)	0.0438 (3)
O3	0.00227 (19)	0.2822 (2)	0.4655 (2)	0.0675 (5)
O4	0.1245 (3)	0.3732 (2)	0.60935 (17)	0.0764 (6)
Cl1	0.33194 (8)	0.08990 (10)	−0.13460 (6)	0.0734 (2)
Cl2	−0.22590 (10)	0.39424 (13)	−0.03893 (7)	0.0972 (3)
S1	0.27077 (5)	0.03037 (5)	0.40942 (4)	0.03530 (15)

	U11	U22	U33	U12	U13	U23
C1	0.0303 (8)	0.0350 (9)	0.0351 (9)	−0.0007 (7)	0.0013 (7)	−0.0052 (7)
C2	0.0361 (9)	0.0384 (9)	0.0349 (9)	0.0005 (7)	0.0055 (7)	−0.0054 (7)
C3	0.0510 (11)	0.0397 (10)	0.0480 (11)	−0.0017 (8)	0.0055 (9)	−0.0121 (8)
C4	0.0502 (11)	0.0416 (10)	0.0550 (12)	−0.0117 (9)	0.0049 (9)	−0.0074 (9)
C5	0.0388 (10)	0.0546 (12)	0.0541 (12)	−0.0114 (9)	0.0127 (9)	−0.0074 (10)
C6	0.0343 (9)	0.0461 (11)	0.0452 (10)	−0.0008 (8)	0.0080 (8)	−0.0113 (8)
C7	0.0370 (9)	0.0437 (10)	0.0349 (9)	−0.0102 (8)	0.0032 (7)	−0.0104 (8)
C8	0.0386 (10)	0.0517 (11)	0.0449 (11)	−0.0060 (8)	0.0070 (8)	−0.0123 (9)
C9	0.0472 (11)	0.0633 (13)	0.0411 (11)	−0.0130 (10)	0.0143 (9)	−0.0171 (10)
C10	0.0607 (13)	0.0719 (15)	0.0347 (10)	−0.0075 (11)	0.0036 (9)	−0.0101 (10)
C11	0.0515 (12)	0.0702 (15)	0.0413 (11)	0.0051 (11)	−0.0041 (9)	−0.0105 (10)
C12	0.0415 (10)	0.0637 (13)	0.0375 (10)	0.0027 (9)	0.0026 (8)	−0.0152 (9)
N1	0.0330 (8)	0.0512 (9)	0.0356 (8)	−0.0068 (7)	0.0055 (6)	−0.0070 (7)
N2	0.0528 (10)	0.0374 (9)	0.0497 (10)	0.0056 (7)	0.0200 (8)	−0.0040 (7)
O1	0.0430 (7)	0.0395 (7)	0.0611 (9)	0.0055 (6)	0.0042 (6)	−0.0141 (6)
O2	0.0438 (7)	0.0464 (8)	0.0363 (7)	−0.0034 (6)	0.0012 (6)	0.0008 (6)
O3	0.0427 (8)	0.0656 (11)	0.0972 (14)	−0.0082 (8)	0.0266 (9)	−0.0246 (10)
O4	0.0956 (14)	0.0836 (13)	0.0489 (10)	0.0012 (11)	0.0302 (9)	−0.0156 (9)
Cl1	0.0674 (4)	0.0992 (5)	0.0540 (4)	−0.0063 (3)	0.0297 (3)	−0.0193 (3)
Cl2	0.0839 (5)	0.1405 (8)	0.0550 (4)	0.0480 (5)	−0.0145 (3)	−0.0092 (4)
S1	0.0331 (2)	0.0330 (2)	0.0379 (3)	0.00006 (16)	0.00272 (17)	−0.00480 (17)

C1—C6	1.384 (2)	C8—C9	1.382 (3)
C1—C2	1.390 (3)	C8—H8	0.9300
C1—S1	1.7763 (18)	C9—C10	1.374 (3)
C2—C3	1.372 (3)	C9—Cl1	1.737 (2)
C2—N2	1.470 (2)	C10—C11	1.378 (3)
C3—C4	1.379 (3)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.376 (3)
C4—C5	1.374 (3)	C11—Cl2	1.735 (2)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.386 (3)	N1—S1	1.6308 (16)
C5—H5	0.9300	N1—H1N	0.848 (16)
C6—H6	0.9300	N2—O4	1.210 (2)
C7—C8	1.387 (3)	N2—O3	1.217 (3)
C7—C12	1.387 (3)	O1—S1	1.4200 (14)
C7—N1	1.419 (2)	O2—S1	1.4312 (14)
C6—C1—C2	117.76 (17)	C10—C9—C8	122.82 (19)
C6—C1—S1	118.50 (14)	C10—C9—Cl1	118.30 (17)
C2—C1—S1	123.64 (13)	C8—C9—Cl1	118.86 (18)
C3—C2—C1	122.36 (17)	C9—C10—C11	117.3 (2)
C3—C2—N2	116.28 (17)	C9—C10—H10	121.3
C1—C2—N2	121.35 (16)	C11—C10—H10	121.3
C2—C3—C4	118.96 (19)	C12—C11—C10	122.3 (2)
C2—C3—H3	120.5	C12—C11—Cl2	119.11 (18)
C4—C3—H3	120.5	C10—C11—Cl2	118.64 (18)
C5—C4—C3	119.99 (19)	C11—C12—C7	118.90 (19)
C5—C4—H4	120.0	C11—C12—H12	120.6
C3—C4—H4	120.0	C7—C12—H12	120.6
C4—C5—C6	120.64 (18)	C7—N1—S1	123.42 (13)
C4—C5—H5	119.7	C7—N1—H1N	114.9 (16)
C6—C5—H5	119.7	S1—N1—H1N	111.2 (16)
C1—C6—C5	120.27 (18)	O4—N2—O3	124.45 (19)
C1—C6—H6	119.9	O4—N2—C2	117.1 (2)
C5—C6—H6	119.9	O3—N2—C2	118.40 (18)
C8—C7—C12	120.52 (18)	O1—S1—O2	119.91 (9)
C8—C7—N1	121.79 (18)	O1—S1—N1	108.52 (9)
C12—C7—N1	117.63 (17)	O2—S1—N1	105.46 (8)
C9—C8—C7	118.2 (2)	O1—S1—C1	106.10 (8)
C9—C8—H8	120.9	O2—S1—C1	108.89 (8)
C7—C8—H8	120.9	N1—S1—C1	107.41 (8)
C6—C1—C2—C3	0.5 (3)	C10—C11—C12—C7	−1.5 (4)
S1—C1—C2—C3	177.01 (15)	Cl2—C11—C12—C7	178.31 (17)
C6—C1—C2—N2	179.58 (17)	C8—C7—C12—C11	1.0 (3)
S1—C1—C2—N2	−3.9 (3)	N1—C7—C12—C11	−176.4 (2)
C1—C2—C3—C4	0.5 (3)	C8—C7—N1—S1	50.4 (2)
N2—C2—C3—C4	−178.64 (19)	C12—C7—N1—S1	−132.29 (17)
C2—C3—C4—C5	−0.8 (3)	C3—C2—N2—O4	−52.3 (3)
C3—C4—C5—C6	0.2 (3)	C1—C2—N2—O4	128.6 (2)
C2—C1—C6—C5	−1.2 (3)	C3—C2—N2—O3	124.8 (2)
S1—C1—C6—C5	−177.86 (16)	C1—C2—N2—O3	−54.3 (3)
C4—C5—C6—C1	0.9 (3)	C7—N1—S1—O1	−64.96 (18)
C12—C7—C8—C9	0.2 (3)	C7—N1—S1—O2	165.37 (15)
N1—C7—C8—C9	177.49 (18)	C7—N1—S1—C1	49.34 (18)
C7—C8—C9—C10	−1.0 (3)	C6—C1—S1—O1	9.79 (17)
C7—C8—C9—Cl1	−179.14 (15)	C2—C1—S1—O1	−166.71 (16)
C8—C9—C10—C11	0.5 (4)	C6—C1—S1—O2	140.13 (15)
Cl1—C9—C10—C11	178.63 (18)	C2—C1—S1—O2	−36.37 (18)
C9—C10—C11—C12	0.8 (4)	C6—C1—S1—N1	−106.13 (16)
C9—C10—C11—Cl2	−179.01 (19)	C2—C1—S1—N1	77.38 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.85 (2)	2.23 (2)	3.052 (2)	162 (2)
N1—H1N···O3	0.85 (2)	2.44 (2)	2.940 (2)	118 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.85 (2)	2.23 (2)	3.052 (2)	162 (2)
N1—H1N⋯O3	0.85 (2)	2.44 (2)	2.940 (2)	118 (2)

Symmetry code: (i) .