Bis(3-methyl-anilinium) sulfate.

In the crystal structure of the title salt, 2C(7)H(7)NH(3) (+)·SO(4) (2-), the cations inter-act with the oxyanions through strong charge-assisted N-H⋯O hydrogen bonds.

Related literature

The crystal structure of m-toluidinium nitrate (Rademeyer & Liles, 2010 ▶), and the structures of three related phosphate salts, namely bis­(m-toluidinium) dihydrogen diphosphate (Akriche & Rzaigui, 2000 ▶), tetra­kis­(m-toluidinium) cyclo­tetra­phosphate (Aloui et al., 2005 ▶), and hexa­kis­(m-toluidin­ium) cyclo­hexa­phosphate (Marouni et al., 2000 ▶), have been reported. For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the most common coordination numbers for the sulfate anion, see: Chertanova & Pascard (1996 ▶).

Experimental

Crystal data

2C7H10N+·SO4 2−

M = 312.23

Monoclinic,

a = 17.2168 (8) Å

b = 15.0298 (7) Å

c = 6.1283 (3) Å

β = 110.819 (3)°

V = 1482.25 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 293 K

0.23 × 0.22 × 0.20 mm

Data collection

Oxford Xcalibur2 diffractometer

7603 measured reflections

2404 independent reflections

1615 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.135

S = 1.04

2404 reflections

104 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.27 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811045624/bt5698sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811045624/bt5698Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811045624/bt5698Isup3.cml

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

2C7H10N+·SO42−	F(000) = 664
Mr = 312.23	Dx = 1.399 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3393 reflections
a = 17.2168 (8) Å	θ = 3.6–32.1°
b = 15.0298 (7) Å	µ = 0.24 mm−1
c = 6.1283 (3) Å	T = 293 K
β = 110.819 (3)°	Block, colourless
V = 1482.25 (12) Å3	0.23 × 0.22 × 0.20 mm
Z = 4

Oxford Xcalibur2 diffractometer	1615 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
graphite	θmax = 32.1°, θmin = 3.6°
ω–2θ scans	h = −24→24
7603 measured reflections	k = −21→20
2404 independent reflections	l = −8→8

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) = 0.135	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0795P)2] where P = (Fo2 + 2Fc2)/3
2404 reflections	(Δ/σ)max = 0.017
104 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.27 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
N1	0.11567 (8)	0.10113 (10)	−0.1357 (2)	0.0333 (3)
H1A	0.1002	0.1171	−0.0174	0.053 (6)*
H1B	0.0868	0.1321	−0.2624	0.057 (6)*
H1C	0.1061	0.0433	−0.1641	0.054 (6)*
C1	0.20457 (9)	0.11906 (9)	−0.0750 (3)	0.0280 (3)
C2	0.23035 (10)	0.16302 (11)	−0.2339 (3)	0.0361 (4)
H2	0.1928	0.1786	−0.3801	0.043 (5)*
C3	0.31438 (10)	0.18371 (12)	−0.1699 (3)	0.0417 (4)
H3	0.3332	0.2138	−0.2741	0.081 (7)*
C4	0.36970 (10)	0.15994 (11)	0.0457 (3)	0.0385 (4)
H4	0.4255	0.1750	0.0863	0.066 (7)*
C5	0.34354 (9)	0.11370 (10)	0.2051 (3)	0.0325 (3)
C6	0.25958 (9)	0.09370 (10)	0.1415 (3)	0.0305 (3)
H6	0.2404	0.0633	0.2445	0.038 (5)*
C7	0.40487 (11)	0.08698 (13)	0.4386 (3)	0.0490 (5)
H7A	0.3758	0.0615	0.5313	0.073*
H7B	0.4353	0.1384	0.5165	0.073*
H7C	0.4428	0.0439	0.4174	0.073*
S1	0.0000	0.13146 (3)	0.2500	0.02700 (17)
O1	0.07354 (8)	0.07574 (8)	0.2846 (2)	0.0472 (3)
O2	−0.01386 (7)	0.18692 (7)	0.04230 (19)	0.0432 (3)

	U11	U22	U33	U12	U13	U23
N1	0.0271 (6)	0.0429 (8)	0.0312 (7)	−0.0030 (6)	0.0119 (5)	−0.0038 (6)
C1	0.0257 (7)	0.0288 (7)	0.0318 (7)	0.0002 (6)	0.0130 (6)	−0.0036 (6)
C2	0.0374 (8)	0.0407 (9)	0.0325 (9)	0.0031 (7)	0.0154 (7)	0.0034 (7)
C3	0.0415 (9)	0.0435 (10)	0.0493 (10)	−0.0004 (7)	0.0274 (8)	0.0087 (7)
C4	0.0282 (7)	0.0360 (8)	0.0545 (10)	0.0014 (6)	0.0186 (7)	0.0015 (7)
C5	0.0271 (7)	0.0273 (7)	0.0408 (9)	0.0052 (6)	0.0093 (6)	0.0007 (6)
C6	0.0296 (7)	0.0293 (7)	0.0338 (8)	0.0000 (6)	0.0127 (6)	0.0040 (6)
C7	0.0365 (9)	0.0502 (11)	0.0515 (12)	0.0048 (8)	0.0049 (8)	0.0068 (8)
S1	0.0270 (3)	0.0297 (3)	0.0256 (3)	0.000	0.0108 (2)	0.000
O1	0.0413 (7)	0.0497 (7)	0.0526 (8)	0.0160 (6)	0.0190 (6)	−0.0040 (6)
O2	0.0554 (8)	0.0420 (7)	0.0309 (6)	−0.0104 (6)	0.0137 (5)	0.0067 (5)

N1—C1	1.4659 (17)	C4—H4	0.9299
N1—H1A	0.8899	C5—C6	1.390 (2)
N1—H1B	0.8901	C5—C7	1.500 (2)
N1—H1C	0.8899	C6—H6	0.9299
C1—C2	1.374 (2)	C7—H7A	0.9600
C1—C6	1.382 (2)	C7—H7B	0.9600
C2—C3	1.393 (2)	C7—H7C	0.9600
C2—H2	0.9300	S1—O2i	1.4684 (11)
C3—C4	1.373 (2)	S1—O2	1.4684 (11)
C3—H3	0.9300	S1—O1i	1.4692 (12)
C4—C5	1.397 (2)	S1—O1	1.4692 (12)
C1—N1—H1A	109.4	C6—C5—C4	118.22 (15)
C1—N1—H1B	109.5	C6—C5—C7	121.27 (15)
H1A—N1—H1B	109.5	C4—C5—C7	120.50 (15)
C1—N1—H1C	109.5	C1—C6—C5	119.97 (14)
H1A—N1—H1C	109.5	C1—C6—H6	120.0
H1B—N1—H1C	109.5	C5—C6—H6	120.0
C2—C1—C6	121.94 (14)	C5—C7—H7A	109.5
C2—C1—N1	118.66 (14)	C5—C7—H7B	109.5
C6—C1—N1	119.37 (13)	H7A—C7—H7B	109.5
C1—C2—C3	118.21 (15)	C5—C7—H7C	109.5
C1—C2—H2	121.0	H7A—C7—H7C	109.5
C3—C2—H2	120.8	H7B—C7—H7C	109.5
C4—C3—C2	120.56 (15)	O2i—S1—O2	110.82 (9)
C4—C3—H3	119.7	O2i—S1—O1i	108.34 (7)
C2—C3—H3	119.8	O2—S1—O1i	109.42 (7)
C3—C4—C5	121.08 (15)	O2i—S1—O1	109.42 (7)
C3—C4—H4	119.4	O2—S1—O1	108.34 (7)
C5—C4—H4	119.5	O1i—S1—O1	110.51 (11)
C6—C1—C2—C3	−1.3 (2)	C3—C4—C5—C7	179.07 (17)
N1—C1—C2—C3	176.82 (14)	C2—C1—C6—C5	0.9 (2)
C1—C2—C3—C4	0.5 (3)	N1—C1—C6—C5	−177.23 (13)
C2—C3—C4—C5	0.7 (3)	C4—C5—C6—C1	0.3 (2)
C3—C4—C5—C6	−1.2 (3)	C7—C5—C6—C1	−179.89 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.89	2.15	2.9384 (19)	147.
N1—H1A···O2	0.89	2.37	3.0913 (18)	139.
N1—H1B···O2ii	0.89	1.91	2.7997 (18)	173.
N1—H1C···O1iii	0.89	1.87	2.7531 (19)	173.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.89	2.15	2.9384 (19)	147
N1—H1A⋯O2	0.89	2.37	3.0913 (18)	139
N1—H1B⋯O2i	0.89	1.91	2.7997 (18)	173
N1—H1C⋯O1ii	0.89	1.87	2.7531 (19)	173

Symmetry codes: (i) ; (ii) .