2-Ethyl-6-methyl-anilinium 4-methyl-benzene-sulfonate.

The title compound, C(9)H(14)N(+)·C(7)H(7)SO(3) (-), contains a 2-ethyl-6-methyl-anilinium cation and a 4-methyl-benzene-sulfonic anion. The cations are anchored between the anions through N-H⋯O hydrogen bonds. Electrostatic and van der Waals inter-actions, as well as hydrogen bonds, maintain the structural cohesion.

Related literature

For related structures, see: Benali-Cherif et al. (2007 ▶); Benslimane et al. (2007 ▶); Elmali et al. (2001 ▶); Fábry et al. (2001 ▶, 2002 ▶); Khemiri et al. (2008 ▶); Muthamizhchelvan et al. (2005 ▶); Smirani et al. (2008 ▶); Smirani & Rzaigui (2009 ▶).

Experimental

Crystal data

C9H14N+·n class="Chemical">C7H7O3S−

M = 307.40

Monoclinic,

a = 15.2514 (9) Å

b = 6.1889 (4) Å

c = 16.9242 (10) Å

β = 102.850 (1)°

V = 1557.46 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 173 (2) K

0.45 × 0.34 × 0.27 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.904, T max = 0.944

7882 measured reflections

3354 independent reflections

2555 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.109

S = 1.08

3354 reflections

194 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.34 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2003 ▶); data reduction: SAIn class="Chemical">NT-Plus; 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/S160053680900230X/pv2133sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680900230X/pv2133Isup2.hkl

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

C9H14N+·C7H7O3S−	F(000) = 656
Mr = 307.40	Dx = 1.311 Mg m−3
Monoclinic, P21/n	Melting point: 428 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 15.2514 (9) Å	Cell parameters from 3656 reflections
b = 6.1889 (4) Å	θ = 2.5–27.0°
c = 16.9242 (10) Å	µ = 0.22 mm−1
β = 102.850 (1)°	T = 173 K
V = 1557.46 (16) Å3	Block, colourless
Z = 4	0.45 × 0.34 × 0.27 mm

Bruker SMART 1000 CCD diffractometer	3354 independent reflections
Radiation source: fine-focus sealed tube	2555 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω scans	θmax = 27.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −16→19
Tmin = 0.904, Tmax = 0.944	k = −7→7
7882 measured reflections	l = −21→15

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0601P)2 + 0.2665P] where P = (Fo2 + 2Fc2)/3
3354 reflections	(Δ/σ)max = 0.003
194 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.34 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
S1	0.90482 (3)	0.20760 (7)	0.10019 (2)	0.02108 (14)
C1	0.78421 (10)	0.5823 (3)	0.90053 (9)	0.0194 (3)
C2	0.80908 (11)	0.4025 (3)	0.86141 (10)	0.0221 (4)
C3	0.74104 (12)	0.2913 (3)	0.80842 (10)	0.0268 (4)
H3	0.7557	0.1687	0.7802	0.032*
C4	0.65245 (12)	0.3572 (3)	0.79640 (11)	0.0299 (4)
H4	0.6068	0.2791	0.7603	0.036*
C5	0.62989 (12)	0.5364 (3)	0.83675 (11)	0.0275 (4)
H5	0.5687	0.5799	0.8279	0.033*
C6	0.69564 (11)	0.6543 (3)	0.89020 (10)	0.0214 (4)
C7	0.90521 (12)	0.3284 (3)	0.87383 (11)	0.0290 (4)
H7A	0.9409	0.4405	0.8547	0.044*
H7B	0.9077	0.1949	0.8433	0.044*
H7C	0.9297	0.3017	0.9316	0.044*
C8	0.67261 (11)	0.8507 (3)	0.93471 (11)	0.0267 (4)
H8A	0.7064	0.9759	0.9204	0.032*
H8B	0.6937	0.8256	0.9936	0.032*
C9	0.57363 (13)	0.9096 (4)	0.91767 (15)	0.0467 (6)
H9A	0.5525	0.9429	0.8600	0.070*
H9B	0.5653	1.0361	0.9500	0.070*
H9C	0.5392	0.7876	0.9320	0.070*
C10	0.88515 (10)	0.1172 (3)	0.19401 (10)	0.0206 (3)
C11	0.90431 (11)	0.2524 (3)	0.26121 (10)	0.0246 (4)
H11	0.9258	0.3948	0.2564	0.029*
C12	0.89200 (12)	0.1787 (3)	0.33539 (11)	0.0281 (4)
H12	0.9053	0.2716	0.3812	0.034*
C13	0.86041 (11)	−0.0297 (3)	0.34369 (11)	0.0266 (4)
C14	0.84062 (12)	−0.1613 (3)	0.27551 (12)	0.0302 (4)
H14	0.8180	−0.3028	0.2799	0.036*
C15	0.85323 (12)	−0.0899 (3)	0.20085 (11)	0.0283 (4)
H15	0.8401	−0.1825	0.1550	0.034*
C16	0.84628 (14)	−0.1093 (4)	0.42440 (12)	0.0380 (5)
H16A	0.8966	−0.0624	0.4677	0.057*
H16B	0.8430	−0.2675	0.4238	0.057*
H16C	0.7900	−0.0497	0.4340	0.057*
N1	0.85616 (9)	0.6956 (2)	0.95856 (8)	0.0200 (3)
H1A	0.8349	0.8242	0.9725	0.030*
H1B	0.9036	0.7195	0.9352	0.030*
H1C	0.8743	0.6129	1.0037	0.030*
O1	0.88551 (8)	0.43864 (19)	0.09615 (7)	0.0257 (3)
O2	0.84407 (8)	0.0861 (2)	0.03804 (7)	0.0307 (3)
O3	0.99931 (8)	0.1642 (2)	0.10318 (8)	0.0311 (3)

	U11	U22	U33	U12	U13	U23
S1	0.0223 (2)	0.0194 (2)	0.0217 (2)	0.00109 (16)	0.00531 (16)	−0.00141 (17)
C1	0.0208 (8)	0.0203 (8)	0.0165 (8)	−0.0022 (6)	0.0031 (6)	0.0025 (6)
C2	0.0273 (9)	0.0191 (8)	0.0200 (8)	0.0006 (7)	0.0055 (7)	0.0029 (7)
C3	0.0354 (10)	0.0221 (9)	0.0236 (9)	−0.0033 (7)	0.0078 (7)	−0.0031 (7)
C4	0.0294 (10)	0.0329 (10)	0.0253 (9)	−0.0110 (8)	0.0019 (7)	−0.0032 (8)
C5	0.0217 (9)	0.0322 (10)	0.0276 (9)	−0.0028 (7)	0.0037 (7)	0.0022 (8)
C6	0.0226 (8)	0.0227 (9)	0.0191 (8)	−0.0006 (7)	0.0051 (6)	0.0040 (7)
C7	0.0310 (10)	0.0255 (10)	0.0307 (10)	0.0039 (7)	0.0072 (8)	−0.0050 (8)
C8	0.0208 (9)	0.0275 (9)	0.0313 (10)	0.0002 (7)	0.0047 (7)	−0.0035 (8)
C9	0.0288 (11)	0.0464 (13)	0.0616 (15)	0.0094 (10)	0.0029 (10)	−0.0170 (11)
C10	0.0187 (8)	0.0204 (8)	0.0232 (8)	0.0015 (6)	0.0055 (6)	−0.0007 (7)
C11	0.0241 (9)	0.0231 (9)	0.0267 (9)	−0.0039 (7)	0.0062 (7)	−0.0028 (7)
C12	0.0276 (9)	0.0316 (10)	0.0252 (9)	−0.0024 (8)	0.0060 (7)	−0.0048 (8)
C13	0.0203 (9)	0.0315 (10)	0.0294 (9)	0.0036 (7)	0.0086 (7)	0.0040 (8)
C14	0.0331 (10)	0.0208 (9)	0.0390 (11)	−0.0013 (7)	0.0132 (8)	0.0027 (8)
C15	0.0328 (10)	0.0224 (9)	0.0312 (10)	−0.0029 (7)	0.0102 (8)	−0.0051 (8)
C16	0.0379 (11)	0.0462 (12)	0.0331 (11)	0.0019 (9)	0.0148 (9)	0.0071 (9)
N1	0.0186 (7)	0.0212 (7)	0.0197 (7)	0.0017 (6)	0.0031 (5)	−0.0007 (6)
O1	0.0323 (7)	0.0203 (6)	0.0238 (6)	0.0022 (5)	0.0050 (5)	0.0008 (5)
O2	0.0375 (7)	0.0285 (7)	0.0248 (7)	−0.0043 (6)	0.0044 (5)	−0.0072 (5)
O3	0.0250 (7)	0.0335 (8)	0.0374 (7)	0.0061 (5)	0.0125 (5)	0.0071 (6)

S1—O2	1.4482 (12)	C8—H8B	0.9900
S1—O3	1.4557 (13)	C9—H9A	0.9800
S1—O1	1.4584 (12)	C9—H9B	0.9800
S1—C10	1.7709 (17)	C9—H9C	0.9800
C1—C2	1.390 (2)	C10—C15	1.385 (2)
C1—C6	1.396 (2)	C10—C11	1.390 (2)
C1—N1	1.477 (2)	C11—C12	1.387 (2)
C2—C3	1.393 (2)	C11—H11	0.9500
C2—C7	1.505 (2)	C12—C13	1.395 (2)
C3—C4	1.382 (3)	C12—H12	0.9500
C3—H3	0.9500	C13—C14	1.389 (3)
C4—C5	1.386 (3)	C13—C16	1.512 (2)
C4—H4	0.9500	C14—C15	1.392 (3)
C5—C6	1.397 (2)	C14—H14	0.9500
C5—H5	0.9500	C15—H15	0.9500
C6—C8	1.512 (2)	C16—H16A	0.9800
C7—H7A	0.9800	C16—H16B	0.9800
C7—H7B	0.9800	C16—H16C	0.9800
C7—H7C	0.9800	N1—H1A	0.9100
C8—C9	1.517 (2)	N1—H1B	0.9100
C8—H8A	0.9900	N1—H1C	0.9100
O2—S1—O3	113.45 (8)	C8—C9—H9A	109.5
O2—S1—O1	112.66 (7)	C8—C9—H9B	109.5
O3—S1—O1	111.75 (7)	H9A—C9—H9B	109.5
O2—S1—C10	106.17 (8)	C8—C9—H9C	109.5
O3—S1—C10	105.92 (7)	H9A—C9—H9C	109.5
O1—S1—C10	106.21 (7)	H9B—C9—H9C	109.5
C2—C1—C6	123.69 (15)	C15—C10—C11	120.17 (16)
C2—C1—N1	117.11 (14)	C15—C10—S1	120.01 (13)
C6—C1—N1	119.15 (14)	C11—C10—S1	119.79 (13)
C1—C2—C3	117.31 (15)	C12—C11—C10	119.79 (16)
C1—C2—C7	122.52 (15)	C12—C11—H11	120.1
C3—C2—C7	120.16 (16)	C10—C11—H11	120.1
C4—C3—C2	120.86 (16)	C11—C12—C13	120.95 (17)
C4—C3—H3	119.6	C11—C12—H12	119.5
C2—C3—H3	119.6	C13—C12—H12	119.5
C3—C4—C5	120.35 (16)	C14—C13—C12	118.31 (16)
C3—C4—H4	119.8	C14—C13—C16	120.74 (17)
C5—C4—H4	119.8	C12—C13—C16	120.94 (17)
C4—C5—C6	121.05 (16)	C13—C14—C15	121.31 (17)
C4—C5—H5	119.5	C13—C14—H14	119.3
C6—C5—H5	119.5	C15—C14—H14	119.3
C1—C6—C5	116.73 (15)	C10—C15—C14	119.45 (17)
C1—C6—C8	121.31 (15)	C10—C15—H15	120.3
C5—C6—C8	121.96 (15)	C14—C15—H15	120.3
C2—C7—H7A	109.5	C13—C16—H16A	109.5
C2—C7—H7B	109.5	C13—C16—H16B	109.5
H7A—C7—H7B	109.5	H16A—C16—H16B	109.5
C2—C7—H7C	109.5	C13—C16—H16C	109.5
H7A—C7—H7C	109.5	H16A—C16—H16C	109.5
H7B—C7—H7C	109.5	H16B—C16—H16C	109.5
C6—C8—C9	115.46 (15)	C1—N1—H1A	109.5
C6—C8—H8A	108.4	C1—N1—H1B	109.5
C9—C8—H8A	108.4	H1A—N1—H1B	109.5
C6—C8—H8B	108.4	C1—N1—H1C	109.5
C9—C8—H8B	108.4	H1A—N1—H1C	109.5
H8A—C8—H8B	107.5	H1B—N1—H1C	109.5
C6—C1—C2—C3	0.8 (2)	O2—S1—C10—C15	27.27 (16)
N1—C1—C2—C3	178.16 (14)	O3—S1—C10—C15	−93.63 (15)
C6—C1—C2—C7	−179.91 (16)	O1—S1—C10—C15	147.40 (13)
N1—C1—C2—C7	−2.5 (2)	O2—S1—C10—C11	−154.60 (13)
C1—C2—C3—C4	−0.7 (3)	O3—S1—C10—C11	84.50 (14)
C7—C2—C3—C4	179.95 (16)	O1—S1—C10—C11	−34.46 (15)
C2—C3—C4—C5	0.4 (3)	C15—C10—C11—C12	0.5 (3)
C3—C4—C5—C6	0.0 (3)	S1—C10—C11—C12	−177.65 (13)
C2—C1—C6—C5	−0.5 (2)	C10—C11—C12—C13	−0.1 (3)
N1—C1—C6—C5	−177.76 (14)	C11—C12—C13—C14	−0.7 (3)
C2—C1—C6—C8	179.76 (16)	C11—C12—C13—C16	−179.50 (16)
N1—C1—C6—C8	2.5 (2)	C12—C13—C14—C15	1.1 (3)
C4—C5—C6—C1	0.0 (2)	C16—C13—C14—C15	179.94 (17)
C4—C5—C6—C8	179.83 (17)	C11—C10—C15—C14	−0.1 (3)
C1—C6—C8—C9	−179.87 (17)	S1—C10—C15—C14	178.07 (13)
C5—C6—C8—C9	0.4 (3)	C13—C14—C15—C10	−0.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O1i	0.91	1.88	2.7727 (18)	168
N1—H1B···O3ii	0.91	1.89	2.7800 (19)	166
N1—H1A···O2iii	0.91	1.95	2.7917 (18)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1C⋯O1i	0.91	1.88	2.7727 (18)	168
N1—H1B⋯O3ii	0.91	1.89	2.7800 (19)	166
N1—H1A⋯O2iii	0.91	1.95	2.7917 (18)	153

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