2-Chloro-6-(2,3-di-chloro-benzene-sulfonamido)-benzoic acid.

In the title compound, C13H8Cl3NO4S, the aromatic rings are oriented at a dihedral angle of 68.94 (1)° and the mol-ecule adopts a V-shape. An intra-molecular N-H⋯O inter-action generates a six-membered S(6) ring motif. In the crystal, pairs of O-H⋯O hydrogen bonds involving the carb-oxy group link the mol-ecules into inversion dimers with an R 2 (2)(8) motif. N-H⋯O and non-classical C-H⋯O inter-actions connect the mol-ecules, forming sheets propagating in (100).

Related literature

For the synthesis, see: Arshad et al. (2012 ▶) For related structures, see: Arshad et al. (2009 ▶, 2011 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H8Cl3NO4S

M = 380.61

Monoclinic,

a = 9.0164 (3) Å

b = 18.6017 (5) Å

c = 9.8574 (3) Å

β = 111.653 (3)°

V = 1536.62 (8) Å3

Z = 4

Cu Kα radiation

μ = 6.83 mm−1

T = 296 K

0.38 × 0.20 × 0.18 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas, CCD) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.467, T max = 1.000

11742 measured reflections

3018 independent reflections

2597 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.104

S = 1.04

3018 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −0.60 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: WinGX (Farrugia, 2012 ▶) and X-SEED (Barbour, 2001 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813011574/hg5312sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813011574/hg5312Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813011574/hg5312Isup3.cml

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

C13H8Cl3NO4S	F(000) = 768
Mr = 380.61	Dx = 1.645 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 5339 reflections
a = 9.0164 (3) Å	θ = 4.8–73.0°
b = 18.6017 (5) Å	µ = 6.83 mm−1
c = 9.8574 (3) Å	T = 296 K
β = 111.653 (3)°	Prismatic, colorless
V = 1536.62 (8) Å3	0.38 × 0.20 × 0.18 mm
Z = 4

Agilent SuperNova (Dual, Cu at zero, Atlas, CCD) diffractometer	3018 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2597 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.025
ω scans	θmax = 73.1°, θmin = 5.4°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	h = −10→11
Tmin = 0.467, Tmax = 1.000	k = −22→22
11742 measured reflections	l = −12→11

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)] = 0.038	H-atom parameters constrained
wR(F2) = 0.104	w = 1/[σ2(Fo2) + (0.0471P)2 + 1.0131P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3018 reflections	Δρmax = 0.55 e Å−3
201 parameters	Δρmin = −0.60 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0022 (2)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Cl1	0.21203 (15)	0.41272 (5)	0.58195 (14)	0.1161 (5)
Cl2	0.17428 (9)	0.55156 (5)	0.74492 (8)	0.0718 (3)
Cl3	0.94473 (9)	0.58369 (5)	1.01517 (11)	0.0797 (3)
S1	0.24536 (6)	0.70690 (3)	0.62789 (6)	0.03763 (17)
O1	0.1045 (2)	0.71147 (11)	0.6596 (2)	0.0562 (5)
O2	0.2792 (2)	0.76184 (9)	0.54279 (18)	0.0482 (4)
O3	0.5137 (2)	0.59728 (8)	1.02304 (19)	0.0460 (4)
H3	0.4816	0.5600	1.0473	0.055*
O4	0.6012 (2)	0.52066 (9)	0.8971 (2)	0.0572 (5)
N1	0.3928 (2)	0.70318 (10)	0.78616 (19)	0.0357 (4)
H1	0.3706	0.7032	0.8638	0.043*
C1	0.2524 (3)	0.62421 (13)	0.5405 (2)	0.0417 (5)
C2	0.2255 (3)	0.55805 (14)	0.5932 (3)	0.0510 (6)
C3	0.2403 (4)	0.49629 (16)	0.5195 (4)	0.0693 (9)
C4	0.2779 (4)	0.5009 (2)	0.3962 (4)	0.0843 (11)
H4	0.2867	0.4592	0.3476	0.101*
C5	0.3022 (5)	0.5663 (2)	0.3450 (4)	0.0804 (10)
H5	0.3269	0.5691	0.2615	0.096*
C6	0.2903 (4)	0.62797 (17)	0.4168 (3)	0.0583 (7)
H6	0.3078	0.6724	0.3823	0.070*
C7	0.5563 (2)	0.69989 (11)	0.8019 (2)	0.0327 (4)
C8	0.6539 (2)	0.64427 (11)	0.8821 (2)	0.0329 (4)
C9	0.8156 (3)	0.64584 (13)	0.9024 (3)	0.0418 (5)
C10	0.8775 (3)	0.69735 (14)	0.8382 (3)	0.0485 (6)
H10	0.9852	0.6970	0.8518	0.058*
C11	0.7777 (3)	0.74919 (15)	0.7535 (3)	0.0536 (7)
H11	0.8175	0.7829	0.7061	0.064*
C12	0.6188 (3)	0.75223 (13)	0.7376 (3)	0.0467 (6)
H12	0.5540	0.7892	0.6840	0.056*
C13	0.5870 (3)	0.58240 (11)	0.9374 (2)	0.0348 (4)

	U11	U22	U33	U12	U13	U23
Cl1	0.1280 (9)	0.0446 (5)	0.1266 (9)	−0.0192 (5)	−0.0106 (7)	0.0082 (5)
Cl2	0.0734 (5)	0.0782 (5)	0.0597 (4)	−0.0271 (4)	0.0197 (3)	0.0177 (4)
Cl3	0.0502 (4)	0.0720 (5)	0.1115 (7)	0.0207 (3)	0.0236 (4)	0.0361 (5)
S1	0.0363 (3)	0.0420 (3)	0.0365 (3)	0.0046 (2)	0.0158 (2)	0.0039 (2)
O1	0.0388 (9)	0.0760 (13)	0.0587 (11)	0.0094 (8)	0.0238 (8)	0.0034 (9)
O2	0.0531 (9)	0.0456 (10)	0.0438 (9)	0.0048 (7)	0.0153 (7)	0.0123 (7)
O3	0.0692 (11)	0.0324 (8)	0.0514 (10)	−0.0026 (8)	0.0397 (9)	0.0004 (7)
O4	0.0914 (14)	0.0287 (8)	0.0748 (13)	−0.0047 (8)	0.0580 (11)	−0.0055 (8)
N1	0.0380 (9)	0.0422 (10)	0.0303 (9)	0.0018 (7)	0.0167 (7)	0.0005 (7)
C1	0.0419 (11)	0.0449 (13)	0.0356 (11)	−0.0006 (10)	0.0111 (9)	−0.0023 (9)
C2	0.0446 (13)	0.0496 (15)	0.0468 (14)	−0.0081 (11)	0.0027 (11)	0.0017 (11)
C3	0.0639 (17)	0.0444 (16)	0.072 (2)	−0.0044 (13)	−0.0075 (15)	−0.0037 (14)
C4	0.095 (2)	0.070 (2)	0.070 (2)	0.0129 (19)	0.0098 (19)	−0.0296 (18)
C5	0.108 (3)	0.078 (2)	0.0594 (19)	0.012 (2)	0.0362 (19)	−0.0156 (17)
C6	0.0753 (18)	0.0590 (17)	0.0460 (14)	0.0016 (14)	0.0285 (13)	−0.0020 (12)
C7	0.0369 (10)	0.0302 (10)	0.0325 (10)	−0.0020 (8)	0.0148 (8)	−0.0012 (8)
C8	0.0405 (10)	0.0270 (10)	0.0336 (10)	−0.0026 (8)	0.0166 (8)	−0.0021 (8)
C9	0.0396 (11)	0.0391 (12)	0.0474 (13)	0.0024 (9)	0.0168 (10)	0.0002 (10)
C10	0.0369 (11)	0.0556 (15)	0.0568 (15)	−0.0089 (10)	0.0218 (11)	−0.0030 (12)
C11	0.0518 (14)	0.0530 (16)	0.0602 (16)	−0.0145 (11)	0.0257 (12)	0.0121 (12)
C12	0.0468 (13)	0.0401 (13)	0.0515 (14)	−0.0042 (10)	0.0161 (11)	0.0126 (10)
C13	0.0418 (11)	0.0297 (10)	0.0357 (11)	0.0013 (8)	0.0174 (9)	0.0012 (8)

Cl1—C3	1.725 (3)	C4—C5	1.366 (5)
Cl2—C2	1.725 (3)	C4—H4	0.9300
Cl3—C9	1.724 (2)	C5—C6	1.373 (4)
S1—O1	1.4179 (17)	C5—H5	0.9300
S1—O2	1.4247 (17)	C6—H6	0.9300
S1—N1	1.6357 (18)	C7—C12	1.389 (3)
S1—C1	1.776 (2)	C7—C8	1.399 (3)
O3—C13	1.279 (3)	C8—C9	1.397 (3)
O3—H3	0.8200	C8—C13	1.493 (3)
O4—C13	1.238 (3)	C9—C10	1.375 (3)
N1—C7	1.426 (3)	C10—C11	1.372 (4)
N1—H1	0.8600	C10—H10	0.9300
C1—C6	1.384 (3)	C11—C12	1.383 (3)
C1—C2	1.391 (3)	C11—H11	0.9300
C2—C3	1.391 (4)	C12—H12	0.9300
C3—C4	1.380 (5)
O1—S1—O2	119.37 (11)	C5—C6—C1	120.3 (3)
O1—S1—N1	105.73 (10)	C5—C6—H6	119.9
O2—S1—N1	108.47 (10)	C1—C6—H6	119.9
O1—S1—C1	110.74 (12)	C12—C7—C8	120.0 (2)
O2—S1—C1	106.38 (11)	C12—C7—N1	119.82 (19)
N1—S1—C1	105.32 (10)	C8—C7—N1	120.19 (18)
C13—O3—H3	109.5	C9—C8—C7	118.12 (19)
C7—N1—S1	123.33 (14)	C9—C8—C13	120.35 (19)
C7—N1—H1	118.3	C7—C8—C13	121.44 (18)
S1—N1—H1	118.3	C10—C9—C8	121.9 (2)
C6—C1—C2	120.5 (2)	C10—C9—Cl3	118.17 (18)
C6—C1—S1	116.6 (2)	C8—C9—Cl3	119.94 (18)
C2—C1—S1	122.88 (19)	C11—C10—C9	118.9 (2)
C1—C2—C3	118.2 (3)	C11—C10—H10	120.5
C1—C2—Cl2	121.7 (2)	C9—C10—H10	120.5
C3—C2—Cl2	120.2 (2)	C10—C11—C12	121.2 (2)
C4—C3—C2	120.7 (3)	C10—C11—H11	119.4
C4—C3—Cl1	119.1 (3)	C12—C11—H11	119.4
C2—C3—Cl1	120.2 (3)	C11—C12—C7	119.8 (2)
C5—C4—C3	120.4 (3)	C11—C12—H12	120.1
C5—C4—H4	119.8	C7—C12—H12	120.1
C3—C4—H4	119.8	O4—C13—O3	123.6 (2)
C4—C5—C6	120.0 (3)	O4—C13—C8	119.58 (19)
C4—C5—H5	120.0	O3—C13—C8	116.82 (18)
C6—C5—H5	120.0
O1—S1—N1—C7	−178.47 (17)	S1—C1—C6—C5	178.3 (3)
O2—S1—N1—C7	−49.3 (2)	S1—N1—C7—C12	55.1 (3)
C1—S1—N1—C7	64.24 (19)	S1—N1—C7—C8	−125.01 (19)
O1—S1—C1—C6	132.5 (2)	C12—C7—C8—C9	3.9 (3)
O2—S1—C1—C6	1.4 (2)	N1—C7—C8—C9	−175.94 (19)
N1—S1—C1—C6	−113.6 (2)	C12—C7—C8—C13	−172.5 (2)
O1—S1—C1—C2	−49.0 (2)	N1—C7—C8—C13	7.6 (3)
O2—S1—C1—C2	179.83 (19)	C7—C8—C9—C10	−4.4 (3)
N1—S1—C1—C2	64.8 (2)	C13—C8—C9—C10	172.1 (2)
C6—C1—C2—C3	1.0 (4)	C7—C8—C9—Cl3	173.60 (17)
S1—C1—C2—C3	−177.45 (19)	C13—C8—C9—Cl3	−9.9 (3)
C6—C1—C2—Cl2	−178.7 (2)	C8—C9—C10—C11	1.0 (4)
S1—C1—C2—Cl2	2.9 (3)	Cl3—C9—C10—C11	−177.0 (2)
C1—C2—C3—C4	−1.1 (4)	C9—C10—C11—C12	3.0 (4)
Cl2—C2—C3—C4	178.6 (2)	C10—C11—C12—C7	−3.4 (4)
C1—C2—C3—Cl1	178.77 (19)	C8—C7—C12—C11	−0.2 (4)
Cl2—C2—C3—Cl1	−1.5 (3)	N1—C7—C12—C11	179.7 (2)
C2—C3—C4—C5	0.4 (5)	C9—C8—C13—O4	−56.9 (3)
Cl1—C3—C4—C5	−179.4 (3)	C7—C8—C13—O4	119.5 (2)
C3—C4—C5—C6	0.4 (6)	C9—C8—C13—O3	124.7 (2)
C4—C5—C6—C1	−0.5 (5)	C7—C8—C13—O3	−58.9 (3)
C2—C1—C6—C5	−0.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3	0.86	2.55	2.940 (2)	108
C12—H12···O3i	0.93	2.59	3.425 (3)	150
O3—H3···O4ii	0.82	1.85	2.666 (2)	176
N1—H1···O2iii	0.86	2.30	3.128 (2)	162
C5—H5···O4iv	0.93	2.53	3.256 (4)	135
C10—H10···O1v	0.93	2.51	3.165 (3)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3	0.86	2.55	2.940 (2)	108
C12—H12⋯O3i	0.93	2.59	3.425 (3)	150
O3—H3⋯O4ii	0.82	1.85	2.666 (2)	176
N1—H1⋯O2iii	0.86	2.30	3.128 (2)	162
C5—H5⋯O4iv	0.93	2.53	3.256 (4)	135
C10—H10⋯O1v	0.93	2.51	3.165 (3)	127

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .