3-Chloro-anilinium 4-methyl-benzene-sulfonate.

In the crystal structure of the title salt, C(6)H(7)ClN(+)·C(7)H(7)O(3)S(-), the cations and anions are linked via N-H⋯O hydrogen bonds into doubled chains in [010]. Weak inter-molecular C-H⋯π inter-actions further link these chains into layers parallel to the bc plane.

Related literature

For background to mol­ecular-ionic compounds, see: Czupinski et al. (2002 ▶); Katrusiak & Szafranski (2006 ▶). For related structures, see: Chanawanno et al. (2009 ▶); Chantrapromma et al. (2010 ▶); Collier et al. (2006 ▶); Fun et al. (2010 ▶); Li et al. (2005 ▶); Lin (2010 ▶); Tabatabaee & Noozari (2011 ▶); Wu et al. (2009 ▶). For normal bond lengths in organic compounds, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C6H7ClN+·C7H7O3S−

M = 299.76

Monoclinic,

a = 12.7848 (3) Å

b = 6.7767 (2) Å

c = 16.1702 (4) Å

β = 105.081 (2)°

V = 1352.71 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.44 mm−1

T = 298 K

0.32 × 0.26 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T min = 0.872, T max = 0.917

10965 measured reflections

3222 independent reflections

2723 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.109

S = 1.02

3222 reflections

182 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.47 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811041043/cv5151sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811041043/cv5151Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811041043/cv5151Isup3.cml

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

C6H7ClN+·C7H7O3S−	F(000) = 624
Mr = 299.76	Dx = 1.472 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4281 reflections
a = 12.7848 (3) Å	θ = 3.2–30.0°
b = 6.7767 (2) Å	µ = 0.44 mm−1
c = 16.1702 (4) Å	T = 298 K
β = 105.081 (2)°	Block, colourless
V = 1352.71 (6) Å3	0.32 × 0.26 × 0.20 mm
Z = 4

Oxford Diffraction Xcalibur Eos Gemini diffractometer	3222 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2723 reflections with I > 2σ(I)
graphite	Rint = 0.020
Detector resolution: 16.1500 pixels mm-1	θmax = 27.9°, θmin = 3.3°
ω scans	h = −16→16
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −8→8
Tmin = 0.872, Tmax = 0.917	l = −21→18
10965 measured reflections

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) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0571P)2 + 0.4988P] where P = (Fo2 + 2Fc2)/3
3222 reflections	(Δ/σ)max = 0.016
182 parameters	Δρmax = 0.38 e Å−3
6 restraints	Δρmin = −0.47 e Å−3

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 > 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
S1	0.71334 (3)	0.24308 (5)	0.57609 (2)	0.03033 (13)
Cl1	0.48393 (5)	0.72176 (8)	0.12500 (3)	0.05637 (17)
O1	0.60656 (10)	0.2751 (3)	0.58758 (10)	0.0679 (5)
O2	0.74597 (11)	0.4022 (2)	0.52892 (8)	0.0533 (4)
O3	0.72546 (12)	0.0520 (2)	0.54113 (9)	0.0589 (4)
N1	0.61726 (11)	0.7273 (2)	0.45378 (9)	0.0314 (3)
H1NC	0.6457 (12)	0.8338 (18)	0.4885 (10)	0.038*
H1NB	0.6507 (12)	0.6166 (17)	0.4825 (10)	0.038*
H1NA	0.5440 (7)	0.721 (2)	0.4477 (12)	0.038*
C1	0.80291 (12)	0.2481 (2)	0.67983 (10)	0.0277 (3)
C2	0.90883 (13)	0.3131 (2)	0.69108 (11)	0.0345 (3)
H2A	0.9330	0.3532	0.6442	0.041*
C3	0.97806 (13)	0.3175 (3)	0.77261 (12)	0.0403 (4)
H3A	1.0489	0.3612	0.7800	0.048*
C4	0.94414 (16)	0.2583 (2)	0.84357 (12)	0.0421 (4)
C5	0.83782 (16)	0.1937 (3)	0.83099 (11)	0.0430 (4)
H5A	0.8137	0.1532	0.8778	0.052*
C6	0.76757 (14)	0.1887 (2)	0.74998 (10)	0.0356 (3)
H6A	0.6967	0.1456	0.7426	0.043*
C7	1.0204 (2)	0.2665 (3)	0.93256 (15)	0.0687 (7)
H7A	1.0613	0.3869	0.9391	0.103*
H7B	1.0690	0.1560	0.9406	0.103*
H7C	0.9792	0.2618	0.9744	0.103*
C8	0.58589 (15)	0.7473 (2)	0.21912 (10)	0.0347 (4)
C9	0.56033 (13)	0.7206 (2)	0.29641 (10)	0.0312 (3)
H9A	0.4907	0.6851	0.2983	0.037*
C10	0.64148 (12)	0.7483 (2)	0.37058 (10)	0.0271 (3)
C11	0.74566 (13)	0.7990 (2)	0.36897 (11)	0.0348 (3)
H11A	0.7992	0.8178	0.4196	0.042*
C12	0.76860 (15)	0.8212 (3)	0.29072 (12)	0.0412 (4)
H12A	0.8387	0.8532	0.2888	0.049*
C13	0.68918 (16)	0.7965 (2)	0.21532 (11)	0.0414 (4)
H13A	0.7050	0.8128	0.1628	0.050*

	U11	U22	U33	U12	U13	U23
S1	0.0291 (2)	0.0332 (2)	0.0253 (2)	0.00048 (14)	0.00097 (14)	−0.00304 (13)
Cl1	0.0735 (4)	0.0580 (3)	0.0257 (2)	−0.0038 (2)	−0.0086 (2)	−0.00145 (18)
O1	0.0290 (7)	0.1261 (15)	0.0437 (8)	0.0078 (7)	0.0005 (6)	−0.0142 (8)
O2	0.0579 (8)	0.0538 (8)	0.0393 (7)	−0.0066 (6)	−0.0031 (6)	0.0160 (6)
O3	0.0771 (10)	0.0408 (7)	0.0450 (8)	0.0047 (7)	−0.0089 (7)	−0.0176 (6)
N1	0.0340 (7)	0.0355 (7)	0.0231 (6)	0.0001 (5)	0.0046 (5)	−0.0005 (5)
C1	0.0287 (7)	0.0251 (7)	0.0262 (7)	0.0009 (5)	0.0019 (6)	−0.0020 (5)
C2	0.0303 (8)	0.0347 (8)	0.0374 (8)	−0.0004 (6)	0.0068 (6)	−0.0022 (7)
C3	0.0297 (8)	0.0361 (8)	0.0480 (10)	0.0004 (7)	−0.0026 (7)	−0.0085 (7)
C4	0.0492 (10)	0.0313 (8)	0.0356 (9)	0.0063 (7)	−0.0073 (8)	−0.0051 (6)
C5	0.0594 (11)	0.0369 (9)	0.0302 (8)	−0.0026 (8)	0.0074 (8)	0.0037 (7)
C6	0.0378 (8)	0.0322 (8)	0.0353 (8)	−0.0061 (7)	0.0072 (7)	0.0015 (6)
C7	0.0792 (16)	0.0634 (14)	0.0436 (13)	0.0091 (11)	−0.0198 (11)	−0.0108 (9)
C8	0.0475 (9)	0.0283 (8)	0.0236 (7)	0.0016 (7)	0.0009 (6)	−0.0006 (5)
C9	0.0342 (8)	0.0300 (8)	0.0267 (7)	0.0002 (6)	0.0031 (6)	−0.0010 (6)
C10	0.0325 (7)	0.0239 (7)	0.0236 (7)	0.0025 (5)	0.0052 (6)	0.0008 (5)
C11	0.0345 (8)	0.0342 (8)	0.0329 (8)	−0.0021 (6)	0.0035 (6)	−0.0020 (6)
C12	0.0419 (9)	0.0392 (9)	0.0467 (10)	−0.0064 (7)	0.0189 (8)	−0.0009 (8)
C13	0.0625 (11)	0.0333 (8)	0.0320 (8)	−0.0050 (8)	0.0187 (8)	0.0015 (7)

S1—O3	1.4374 (13)	C5—C6	1.382 (2)
S1—O2	1.4437 (13)	C5—H5A	0.9300
S1—O1	1.4413 (14)	C6—H6A	0.9300
S1—C1	1.7682 (15)	C7—H7A	0.9600
Cl1—C8	1.7359 (17)	C7—H7B	0.9600
N1—C10	1.464 (2)	C7—H7C	0.9600
N1—H1NC	0.928 (9)	C8—C9	1.383 (2)
N1—H1NB	0.927 (8)	C8—C13	1.379 (3)
N1—H1NA	0.916 (9)	C9—C10	1.379 (2)
C1—C6	1.386 (2)	C9—H9A	0.9300
C1—C2	1.390 (2)	C10—C11	1.382 (2)
C2—C3	1.384 (2)	C11—C12	1.379 (2)
C2—H2A	0.9300	C11—H11A	0.9300
C3—C4	1.387 (3)	C12—C13	1.379 (3)
C3—H3A	0.9300	C12—H12A	0.9300
C4—C5	1.392 (3)	C13—H13A	0.9300
C4—C7	1.515 (3)
O3—S1—O2	112.92 (9)	C1—C6—C5	119.92 (16)
O3—S1—O1	112.90 (10)	C1—C6—H6A	120.0
O2—S1—O1	111.66 (10)	C5—C6—H6A	120.0
O3—S1—C1	106.32 (7)	C4—C7—H7A	109.5
O2—S1—C1	106.38 (7)	C4—C7—H7B	109.5
O1—S1—C1	106.03 (8)	H7A—C7—H7B	109.5
C10—N1—H1NC	109.7 (11)	C4—C7—H7C	109.5
C10—N1—H1NB	111.1 (11)	H7A—C7—H7C	109.5
H1NC—N1—H1NB	105.6 (14)	H7B—C7—H7C	109.5
C10—N1—H1NA	111.2 (12)	C9—C8—C13	121.74 (16)
H1NC—N1—H1NA	109.0 (13)	C9—C8—Cl1	118.62 (14)
H1NB—N1—H1NA	110.1 (13)	C13—C8—Cl1	119.64 (13)
C6—C1—C2	119.93 (14)	C10—C9—C8	117.81 (15)
C6—C1—S1	120.17 (12)	C10—C9—H9A	121.1
C2—C1—S1	119.91 (12)	C8—C9—H9A	121.1
C3—C2—C1	119.43 (16)	C9—C10—C11	121.86 (14)
C3—C2—H2A	120.3	C9—C10—N1	119.65 (14)
C1—C2—H2A	120.3	C11—C10—N1	118.47 (13)
C2—C3—C4	121.43 (16)	C12—C11—C10	118.70 (15)
C2—C3—H3A	119.3	C12—C11—H11A	120.7
C4—C3—H3A	119.3	C10—C11—H11A	120.7
C3—C4—C5	118.27 (16)	C13—C12—C11	120.97 (16)
C3—C4—C7	120.85 (19)	C13—C12—H12A	119.5
C5—C4—C7	120.9 (2)	C11—C12—H12A	119.5
C6—C5—C4	121.02 (17)	C12—C13—C8	118.91 (16)
C6—C5—H5A	119.5	C12—C13—H13A	120.5
C4—C5—H5A	119.5	C8—C13—H13A	120.5
O3—S1—C1—C6	−90.75 (15)	C2—C1—C6—C5	−0.2 (2)
O2—S1—C1—C6	148.65 (13)	S1—C1—C6—C5	−179.74 (13)
O1—S1—C1—C6	29.65 (16)	C4—C5—C6—C1	0.2 (3)
O3—S1—C1—C2	89.72 (14)	C13—C8—C9—C10	1.2 (2)
O2—S1—C1—C2	−30.89 (15)	Cl1—C8—C9—C10	−177.74 (11)
O1—S1—C1—C2	−149.88 (14)	C8—C9—C10—C11	−0.7 (2)
C6—C1—C2—C3	0.1 (2)	C8—C9—C10—N1	178.21 (13)
S1—C1—C2—C3	179.61 (12)	C9—C10—C11—C12	−0.4 (2)
C1—C2—C3—C4	0.1 (3)	N1—C10—C11—C12	−179.27 (15)
C2—C3—C4—C5	−0.1 (3)	C10—C11—C12—C13	1.0 (3)
C2—C3—C4—C7	−179.20 (16)	C11—C12—C13—C8	−0.6 (3)
C3—C4—C5—C6	−0.1 (3)	C9—C8—C13—C12	−0.5 (2)
C7—C4—C5—C6	179.06 (17)	Cl1—C8—C13—C12	178.34 (13)

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1NA···O1i	0.92 (1)	1.86 (1)	2.7640 (19)	168.(2)
N1—H1NC···O3ii	0.93 (1)	1.87 (1)	2.7806 (18)	166.(2)
N1—H1NB···O2	0.93 (1)	1.92 (1)	2.8282 (19)	167.(2)
C12—H12A···Cg1iii	0.93	2.76	3.267 (2)	115

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1NA⋯O1i	0.92 (1)	1.86 (1)	2.7640 (19)	168 (2)
N1—H1NC⋯O3ii	0.93 (1)	1.87 (1)	2.7806 (18)	166 (2)
N1—H1NB⋯O2	0.93 (1)	1.92 (1)	2.8282 (19)	167 (2)
C12—H12A⋯Cg1iii	0.93	2.76	3.267 (2)	115

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