4-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 double chains in [101]. Weak inter-molecular C-H⋯π-ring inter-actions link these chains into layers parallel to the ac plane.

Related literature

For background literature concerning 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 ▶); Kobkeatthawin et al. (2009 ▶); Li et al. (2005 ▶); Lin, (2010 ▶); Rahmouni et al. (2010 ▶); Smith et al. (2009 ▶); Tabatabaee & Noozari, (2011 ▶); Wu et al. (2009 ▶); Zhang & Liu (2010 ▶).

Experimental

Crystal data

C6H7ClN+·n class="Chemical">C7H7O3S−

M = 299.76

Triclinic,

a = 5.7253 (5) Å

b = 7.5160 (6) Å

c = 15.7642 (13) Å

α = 95.166 (6)°

β = 96.148 (7)°

γ = 92.353 (7)°

V = 670.83 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.44 mm−1

T = 173 K

0.40 × 0.20 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T min = 0.843, T max = 0.949

5280 measured reflections

3439 independent reflections

3144 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.088

S = 1.08

3439 reflections

182 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.45 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis n class="Disease">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/S160053681104712X/bt5699sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104712X/bt5699Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681104712X/bt5699Isup3.cml

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

C6H7ClN+·C7H7O3S−	Z = 2
Mr = 299.76	F(000) = 312
Triclinic, P1	Dx = 1.484 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.7253 (5) Å	Cell parameters from 2538 reflections
b = 7.5160 (6) Å	θ = 3.6–29.9°
c = 15.7642 (13) Å	µ = 0.44 mm−1
α = 95.166 (6)°	T = 173 K
β = 96.148 (7)°	Block, colorless
γ = 92.353 (7)°	0.40 × 0.20 × 0.12 mm
V = 670.83 (10) Å3

Oxford Diffraction Xcalibur Eos Gemini diffractometer	3439 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3144 reflections with I > 2σ(I)
graphite	Rint = 0.017
Detector resolution: 16.1500 pixels mm-1	θmax = 30.0°, θmin = 3.6°
ω scans	h = −7→7
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −9→9
Tmin = 0.843, Tmax = 0.949	l = −22→21
5280 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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0406P)2 + 0.2844P] where P = (Fo2 + 2Fc2)/3
3439 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 0.42 e Å−3
6 restraints	Δρmin = −0.45 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	0.64768 (6)	0.72752 (4)	0.391167 (19)	0.01562 (9)
Cl1	−0.20941 (8)	0.85567 (6)	0.86957 (3)	0.03622 (12)
O1	0.56763 (19)	0.89688 (13)	0.42702 (6)	0.0227 (2)
O2	0.52819 (19)	0.57587 (13)	0.42253 (6)	0.0231 (2)
O3	0.90320 (18)	0.71964 (16)	0.40103 (6)	0.0281 (2)
N1	0.2327 (2)	0.74505 (16)	0.54631 (7)	0.0179 (2)
H1NC	0.329 (3)	0.8434 (17)	0.5411 (11)	0.022*
H1NB	0.123 (2)	0.730 (2)	0.4992 (10)	0.022*
H1NA	0.323 (3)	0.6460 (18)	0.5467 (11)	0.022*
C1	0.5595 (2)	0.71390 (16)	0.27970 (8)	0.0150 (2)
C2	0.7106 (2)	0.7789 (2)	0.22507 (9)	0.0219 (3)
H2A	0.8638	0.8264	0.2470	0.026*
C3	0.6356 (3)	0.7737 (2)	0.13818 (9)	0.0277 (3)
H3A	0.7385	0.8182	0.1007	0.033*
C4	0.4120 (3)	0.7044 (2)	0.10515 (9)	0.0255 (3)
C5	0.2646 (3)	0.6388 (2)	0.16103 (10)	0.0267 (3)
H5A	0.1123	0.5896	0.1391	0.032*
C6	0.3357 (2)	0.6439 (2)	0.24820 (9)	0.0223 (3)
H6A	0.2326	0.6001	0.2858	0.027*
C7	0.3278 (4)	0.7036 (3)	0.01100 (10)	0.0412 (4)
H7A	0.2057	0.6079	−0.0056	0.062*
H7B	0.4601	0.6835	−0.0227	0.062*
H7C	0.2628	0.8191	0.0002	0.062*
C8	−0.0816 (3)	0.82188 (18)	0.77464 (9)	0.0210 (3)
C9	−0.1916 (2)	0.88215 (18)	0.70096 (9)	0.0211 (3)
H9A	−0.3353	0.9407	0.7021	0.025*
C10	−0.0887 (2)	0.85572 (18)	0.62520 (9)	0.0191 (3)
H10A	−0.1614	0.8961	0.5739	0.023*
C11	0.1203 (2)	0.77012 (17)	0.62529 (8)	0.0161 (2)
C12	0.2313 (2)	0.71189 (17)	0.69946 (8)	0.0184 (3)
H12A	0.3764	0.6553	0.6985	0.022*
C13	0.1287 (3)	0.73699 (19)	0.77499 (9)	0.0218 (3)
H13A	0.2014	0.6966	0.8263	0.026*

	U11	U22	U33	U12	U13	U23
S1	0.01884 (16)	0.01791 (16)	0.01046 (14)	0.00399 (11)	0.00187 (11)	0.00159 (11)
Cl1	0.0423 (2)	0.0452 (2)	0.02487 (19)	0.01334 (18)	0.01570 (17)	0.00412 (16)
O1	0.0323 (5)	0.0182 (5)	0.0174 (5)	0.0038 (4)	0.0042 (4)	−0.0023 (4)
O2	0.0340 (6)	0.0194 (5)	0.0183 (5)	0.0056 (4)	0.0089 (4)	0.0066 (4)
O3	0.0191 (5)	0.0480 (7)	0.0165 (5)	0.0067 (4)	−0.0019 (4)	0.0021 (4)
N1	0.0186 (5)	0.0198 (5)	0.0155 (5)	0.0024 (4)	0.0016 (4)	0.0022 (4)
C1	0.0190 (6)	0.0143 (5)	0.0120 (5)	0.0029 (4)	0.0017 (4)	0.0012 (4)
C2	0.0200 (6)	0.0294 (7)	0.0162 (6)	−0.0022 (5)	0.0019 (5)	0.0035 (5)
C3	0.0291 (8)	0.0391 (8)	0.0164 (6)	0.0010 (6)	0.0059 (6)	0.0079 (6)
C4	0.0311 (8)	0.0308 (8)	0.0138 (6)	0.0089 (6)	−0.0019 (5)	−0.0004 (5)
C5	0.0219 (7)	0.0341 (8)	0.0215 (7)	−0.0002 (6)	−0.0046 (5)	−0.0021 (6)
C6	0.0194 (6)	0.0282 (7)	0.0193 (6)	−0.0018 (5)	0.0023 (5)	0.0030 (5)
C7	0.0472 (11)	0.0604 (12)	0.0147 (7)	0.0126 (9)	−0.0049 (7)	0.0015 (7)
C8	0.0243 (7)	0.0208 (6)	0.0184 (6)	0.0018 (5)	0.0060 (5)	0.0002 (5)
C9	0.0181 (6)	0.0201 (6)	0.0254 (7)	0.0040 (5)	0.0031 (5)	0.0013 (5)
C10	0.0191 (6)	0.0195 (6)	0.0183 (6)	0.0026 (5)	−0.0017 (5)	0.0032 (5)
C11	0.0179 (6)	0.0147 (6)	0.0155 (6)	0.0005 (4)	0.0016 (5)	0.0010 (4)
C12	0.0185 (6)	0.0182 (6)	0.0185 (6)	0.0041 (5)	−0.0005 (5)	0.0022 (5)
C13	0.0262 (7)	0.0230 (7)	0.0163 (6)	0.0042 (5)	0.0003 (5)	0.0043 (5)

S1—O2	1.4565 (10)	C5—C6	1.387 (2)
S1—O1	1.4572 (10)	C5—H5A	0.9500
S1—O3	1.4587 (11)	C6—H6A	0.9500
S1—C1	1.7682 (13)	C7—H7A	0.9800
Cl1—C8	1.7381 (14)	C7—H7B	0.9800
N1—C11	1.4626 (17)	C7—H7C	0.9800
N1—H1NC	0.920 (12)	C8—C9	1.383 (2)
N1—H1NB	0.916 (12)	C8—C13	1.385 (2)
N1—H1NA	0.925 (12)	C9—C10	1.3894 (19)
C1—C6	1.3880 (19)	C9—H9A	0.9500
C1—C2	1.3892 (18)	C10—C11	1.3817 (18)
C2—C3	1.3875 (19)	C10—H10A	0.9500
C2—H2A	0.9500	C11—C12	1.3850 (18)
C3—C4	1.391 (2)	C12—C13	1.3845 (19)
C3—H3A	0.9500	C12—H12A	0.9500
C4—C5	1.391 (2)	C13—H13A	0.9500
C4—C7	1.510 (2)
O2—S1—O1	111.46 (6)	C5—C6—C1	119.09 (13)
O2—S1—O3	113.20 (7)	C5—C6—H6A	120.5
O1—S1—O3	113.02 (7)	C1—C6—H6A	120.5
O2—S1—C1	106.02 (6)	C4—C7—H7A	109.5
O1—S1—C1	106.15 (6)	C4—C7—H7B	109.5
O3—S1—C1	106.33 (6)	H7A—C7—H7B	109.5
C11—N1—H1NC	110.2 (11)	C4—C7—H7C	109.5
C11—N1—H1NB	111.0 (11)	H7A—C7—H7C	109.5
H1NC—N1—H1NB	108.1 (13)	H7B—C7—H7C	109.5
C11—N1—H1NA	110.6 (11)	C9—C8—C13	121.80 (13)
H1NC—N1—H1NA	108.1 (13)	C9—C8—Cl1	119.03 (11)
H1NB—N1—H1NA	108.8 (13)	C13—C8—Cl1	119.16 (11)
C6—C1—C2	120.72 (12)	C8—C9—C10	118.97 (13)
C6—C1—S1	119.31 (10)	C8—C9—H9A	120.5
C2—C1—S1	119.93 (10)	C10—C9—H9A	120.5
C3—C2—C1	119.31 (13)	C11—C10—C9	119.32 (12)
C3—C2—H2A	120.3	C11—C10—H10A	120.3
C1—C2—H2A	120.3	C9—C10—H10A	120.3
C2—C3—C4	121.00 (14)	C10—C11—C12	121.49 (12)
C2—C3—H3A	119.5	C10—C11—N1	119.76 (12)
C4—C3—H3A	119.5	C12—C11—N1	118.71 (12)
C5—C4—C3	118.61 (13)	C13—C12—C11	119.38 (12)
C5—C4—C7	120.37 (15)	C13—C12—H12A	120.3
C3—C4—C7	121.01 (15)	C11—C12—H12A	120.3
C6—C5—C4	121.26 (14)	C12—C13—C8	119.02 (13)
C6—C5—H5A	119.4	C12—C13—H13A	120.5
C4—C5—H5A	119.4	C8—C13—H13A	120.5
O2—S1—C1—C6	32.26 (12)	C4—C5—C6—C1	−0.8 (2)
O1—S1—C1—C6	−86.39 (12)	C2—C1—C6—C5	0.3 (2)
O3—S1—C1—C6	153.01 (11)	S1—C1—C6—C5	177.95 (11)
O2—S1—C1—C2	−150.07 (11)	C13—C8—C9—C10	0.4 (2)
O1—S1—C1—C2	91.28 (12)	Cl1—C8—C9—C10	179.74 (11)
O3—S1—C1—C2	−29.32 (13)	C8—C9—C10—C11	0.0 (2)
C6—C1—C2—C3	0.1 (2)	C9—C10—C11—C12	−0.8 (2)
S1—C1—C2—C3	−177.49 (11)	C9—C10—C11—N1	−178.68 (12)
C1—C2—C3—C4	−0.1 (2)	C10—C11—C12—C13	1.2 (2)
C2—C3—C4—C5	−0.4 (2)	N1—C11—C12—C13	179.09 (12)
C2—C3—C4—C7	178.22 (15)	C11—C12—C13—C8	−0.8 (2)
C3—C4—C5—C6	0.9 (2)	C9—C8—C13—C12	0.0 (2)
C7—C4—C5—C6	−177.77 (15)	Cl1—C8—C13—C12	−179.35 (11)

Cg2 is the centroid of the C8–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1NC···O1i	0.92 (1)	2.02 (1)	2.8579 (16)	151.(2)
N1—H1NC···O1	0.92 (1)	2.42 (2)	3.0814 (16)	129.(1)
N1—H1NB···O3ii	0.92 (1)	1.88 (1)	2.7940 (15)	175.(2)
N1—H1NA···O2iii	0.93 (1)	1.98 (1)	2.8764 (15)	163.(2)
C2—H2A···Cg2i	0.95	2.91	3.5340 (16)	124

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1NC⋯O1i	0.92 (1)	2.02 (1)	2.8579 (16)	151 (2)
N1—H1NC⋯O1	0.92 (1)	2.42 (2)	3.0814 (16)	129 (1)
N1—H1NB⋯O3ii	0.92 (1)	1.88 (1)	2.7940 (15)	175 (2)
N1—H1NA⋯O2iii	0.93 (1)	1.98 (1)	2.8764 (15)	163 (2)
C2—H2A⋯Cg2i	0.95	2.91	3.5340 (16)	124

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