4-Ethyl-anilinium 4-methyl-benzene-sulfonate.

In the crystal structure of the title molecular salt, C(8)H(12)N(+)·C(7)H(7)O(3)S(-), the 4-ethyl-anilinium cations and 4-methyl-benzene-sulfonate anions are linked into chains parallel to the b axis by inter-molecular N-H⋯O hydrogen bonds.

Related literature

For background literature concerning mol­ecular–ionic compounds, see: Czupiński et al. (2002 ▶); Katrusiak & Szafrański (2006 ▶). For related structures. see: Chen (2009 ▶); Wang (2010 ▶).

Experimental

Crystal data

C8H12N+·C7H7O3S−

M = 293.38

Monoclinic,

a = 25.016 (3) Å

b = 5.6376 (11) Å

c = 21.6387 (13) Å

β = 95.227 (10)°

V = 3039.0 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.22 mm−1

T = 291 K

0.36 × 0.28 × 0.24 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.930, T max = 0.950

14572 measured reflections

3490 independent reflections

2614 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.178

S = 1.06

3490 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.44 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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 datablocks I, global. DOI: 10.1107/S1600536810028047/rz2476sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810028047/rz2476Isup2.hkl

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

C8H12N+·C7H7O3S−	F(000) = 1248
Mr = 293.38	Dx = 1.283 Mg m−3
Monoclinic, C2/c	Melting point: 465 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 25.016 (3) Å	Cell parameters from 12307 reflections
b = 5.6376 (11) Å	θ = 3.1–27.6°
c = 21.6387 (13) Å	µ = 0.22 mm−1
β = 95.227 (10)°	T = 291 K
V = 3039.0 (7) Å3	Block, colourless
Z = 8	0.36 × 0.28 × 0.24 mm

Rigaku Mercury2 diffractometer	3490 independent reflections
Radiation source: fine-focus sealed tube	2614 reflections with I > 2σ(I)
graphite	Rint = 0.048
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.3°
CCD_Profile_fitting scans	h = −32→32
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −7→7
Tmin = 0.930, Tmax = 0.950	l = −27→28
14572 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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.178	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0988P)2 + 1.990P] where P = (Fo2 + 2Fc2)/3
3490 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.44 e Å−3

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	0.18002 (12)	0.6568 (8)	0.1475 (2)	0.0771 (11)
H1A	0.1636	0.7869	0.1243	0.116*
H1B	0.1634	0.6386	0.1855	0.116*
H1C	0.1754	0.5138	0.1235	0.116*
C2	0.23944 (10)	0.7059 (5)	0.16208 (13)	0.0448 (7)
C3	0.26270 (11)	0.9123 (6)	0.14269 (15)	0.0549 (8)
H3A	0.2414	1.0231	0.1201	0.066*
C4	0.31647 (11)	0.9576 (5)	0.15593 (14)	0.0471 (7)
H4A	0.3311	1.0985	0.1428	0.056*
C5	0.34871 (9)	0.7941 (4)	0.18873 (10)	0.0304 (5)
C6	0.32643 (10)	0.5882 (5)	0.20886 (13)	0.0416 (6)
H6A	0.3478	0.4769	0.2312	0.050*
C7	0.27173 (11)	0.5477 (5)	0.19556 (13)	0.0473 (7)
H7A	0.2568	0.4094	0.2098	0.057*
C8	0.32058 (15)	0.5450 (11)	0.52795 (18)	0.1058 (18)
H8A	0.3026	0.5895	0.5635	0.159*
H8B	0.3130	0.3819	0.5180	0.159*
H8C	0.3082	0.6432	0.4933	0.159*
C9	0.37861 (13)	0.5763 (7)	0.54173 (14)	0.0620 (9)
H9A	0.3908	0.4785	0.5771	0.074*
H9B	0.3859	0.7404	0.5530	0.074*
C10	0.41024 (10)	0.5113 (5)	0.48754 (12)	0.0414 (6)
C11	0.41036 (12)	0.6573 (5)	0.43615 (13)	0.0473 (7)
H11A	0.3919	0.8006	0.4358	0.057*
C12	0.43700 (11)	0.5966 (5)	0.38534 (12)	0.0420 (6)
H12A	0.4365	0.6969	0.3512	0.050*
C13	0.46425 (9)	0.3857 (4)	0.38629 (11)	0.0317 (5)
C14	0.46589 (10)	0.2380 (5)	0.43700 (12)	0.0417 (6)
H14A	0.4851	0.0967	0.4375	0.050*
C15	0.43868 (11)	0.3020 (5)	0.48717 (13)	0.0467 (7)
H15A	0.4396	0.2019	0.5214	0.056*
N1	0.49149 (8)	0.3138 (4)	0.33224 (9)	0.0373 (5)
H1D	0.4874	0.4261	0.3033	0.056*
H1E	0.4774	0.1786	0.3171	0.056*
H1F	0.5263	0.2931	0.3435	0.056*
O1	0.44138 (7)	0.6248 (4)	0.22484 (10)	0.0543 (6)
O2	0.42345 (8)	1.0277 (4)	0.25272 (9)	0.0534 (5)
O3	0.43719 (8)	0.9314 (4)	0.14712 (9)	0.0575 (6)
S1	0.41818 (2)	0.84917 (11)	0.20463 (3)	0.0335 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0355 (16)	0.105 (3)	0.089 (3)	−0.0119 (18)	−0.0011 (16)	−0.011 (2)
C2	0.0313 (13)	0.0591 (18)	0.0439 (14)	−0.0054 (12)	0.0019 (11)	−0.0108 (13)
C3	0.0425 (15)	0.0547 (18)	0.0650 (19)	0.0104 (13)	−0.0090 (14)	0.0114 (16)
C4	0.0420 (14)	0.0369 (14)	0.0616 (18)	−0.0030 (12)	0.0007 (12)	0.0127 (13)
C5	0.0289 (11)	0.0313 (12)	0.0311 (11)	−0.0021 (9)	0.0031 (9)	−0.0010 (9)
C6	0.0387 (13)	0.0366 (14)	0.0486 (15)	−0.0047 (11)	−0.0004 (11)	0.0118 (12)
C7	0.0450 (15)	0.0435 (16)	0.0543 (16)	−0.0164 (13)	0.0093 (12)	0.0019 (13)
C8	0.068 (2)	0.188 (5)	0.067 (2)	−0.008 (3)	0.032 (2)	−0.023 (3)
C9	0.069 (2)	0.076 (2)	0.0434 (16)	0.0024 (18)	0.0176 (15)	−0.0095 (17)
C10	0.0435 (14)	0.0475 (15)	0.0338 (13)	−0.0005 (12)	0.0067 (11)	−0.0056 (12)
C11	0.0578 (17)	0.0398 (15)	0.0454 (15)	0.0134 (13)	0.0117 (13)	−0.0001 (12)
C12	0.0542 (16)	0.0352 (14)	0.0373 (14)	0.0034 (12)	0.0084 (11)	0.0060 (11)
C13	0.0303 (11)	0.0342 (13)	0.0308 (12)	−0.0043 (10)	0.0037 (9)	−0.0019 (10)
C14	0.0441 (14)	0.0363 (14)	0.0449 (15)	0.0076 (12)	0.0045 (12)	0.0071 (12)
C15	0.0531 (16)	0.0511 (17)	0.0360 (14)	0.0065 (13)	0.0055 (12)	0.0122 (12)
N1	0.0373 (11)	0.0397 (12)	0.0355 (11)	−0.0024 (9)	0.0067 (8)	−0.0065 (9)
O1	0.0368 (10)	0.0510 (12)	0.0746 (15)	0.0090 (9)	0.0017 (9)	0.0067 (11)
O2	0.0467 (11)	0.0567 (13)	0.0561 (12)	−0.0120 (9)	0.0005 (9)	−0.0235 (10)
O3	0.0493 (12)	0.0805 (16)	0.0439 (11)	−0.0235 (11)	0.0106 (9)	0.0028 (11)
S1	0.0288 (3)	0.0368 (4)	0.0350 (3)	−0.0045 (2)	0.0031 (2)	−0.0028 (3)

C1—C2	1.517 (4)	C9—H9A	0.9700
C1—H1A	0.9600	C9—H9B	0.9700
C1—H1B	0.9600	C10—C15	1.378 (4)
C1—H1C	0.9600	C10—C11	1.384 (4)
C2—C7	1.366 (4)	C11—C12	1.379 (4)
C2—C3	1.383 (4)	C11—H11A	0.9300
C3—C4	1.374 (4)	C12—C13	1.370 (3)
C3—H3A	0.9300	C12—H12A	0.9300
C4—C5	1.378 (3)	C13—C14	1.375 (3)
C4—H4A	0.9300	C13—N1	1.463 (3)
C5—C6	1.375 (3)	C14—C15	1.381 (4)
C5—S1	1.768 (2)	C14—H14A	0.9300
C6—C7	1.391 (4)	C15—H15A	0.9300
C6—H6A	0.9300	N1—H1D	0.8900
C7—H7A	0.9300	N1—H1E	0.8900
C8—C9	1.466 (5)	N1—H1F	0.8900
C8—H8A	0.9600	O1—S1	1.443 (2)
C8—H8B	0.9600	O2—S1	1.4451 (19)
C8—H8C	0.9600	O3—S1	1.448 (2)
C9—C10	1.518 (4)
C2—C1—H1A	109.5	C8—C9—H9B	109.0
C2—C1—H1B	109.5	C10—C9—H9B	109.0
H1A—C1—H1B	109.5	H9A—C9—H9B	107.8
C2—C1—H1C	109.5	C15—C10—C11	117.7 (2)
H1A—C1—H1C	109.5	C15—C10—C9	121.1 (3)
H1B—C1—H1C	109.5	C11—C10—C9	121.1 (3)
C7—C2—C3	117.7 (2)	C12—C11—C10	122.0 (2)
C7—C2—C1	120.8 (3)	C12—C11—H11A	119.0
C3—C2—C1	121.5 (3)	C10—C11—H11A	119.0
C4—C3—C2	121.6 (3)	C13—C12—C11	118.6 (2)
C4—C3—H3A	119.2	C13—C12—H12A	120.7
C2—C3—H3A	119.2	C11—C12—H12A	120.7
C3—C4—C5	119.9 (3)	C12—C13—C14	121.1 (2)
C3—C4—H4A	120.0	C12—C13—N1	119.7 (2)
C5—C4—H4A	120.0	C14—C13—N1	119.2 (2)
C6—C5—C4	119.5 (2)	C13—C14—C15	119.2 (2)
C6—C5—S1	120.41 (19)	C13—C14—H14A	120.4
C4—C5—S1	120.08 (19)	C15—C14—H14A	120.4
C5—C6—C7	119.5 (2)	C10—C15—C14	121.3 (2)
C5—C6—H6A	120.2	C10—C15—H15A	119.3
C7—C6—H6A	120.2	C14—C15—H15A	119.3
C2—C7—C6	121.7 (3)	C13—N1—H1D	109.5
C2—C7—H7A	119.2	C13—N1—H1E	109.5
C6—C7—H7A	119.2	H1D—N1—H1E	109.5
C9—C8—H8A	109.5	C13—N1—H1F	109.5
C9—C8—H8B	109.5	H1D—N1—H1F	109.5
H8A—C8—H8B	109.5	H1E—N1—H1F	109.5
C9—C8—H8C	109.5	O1—S1—O2	112.62 (13)
H8A—C8—H8C	109.5	O1—S1—O3	112.74 (14)
H8B—C8—H8C	109.5	O2—S1—O3	112.34 (13)
C8—C9—C10	113.0 (3)	O1—S1—C5	105.43 (11)
C8—C9—H9A	109.0	O2—S1—C5	106.63 (11)
C10—C9—H9A	109.0	O3—S1—C5	106.43 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···O1i	0.89	2.24	2.792 (3)	120
N1—H1D···O1	0.89	2.26	3.085 (3)	154
N1—H1E···O2ii	0.89	2.04	2.815 (3)	146
N1—H1F···O3iii	0.89	2.24	2.808 (3)	122

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1D⋯O1i	0.89	2.24	2.792 (3)	120
N1—H1D⋯O1	0.89	2.26	3.085 (3)	154
N1—H1E⋯O2ii	0.89	2.04	2.815 (3)	146
N1—H1F⋯O3iii	0.89	2.24	2.808 (3)	122

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