Bis(3-methyl-anilinium) naphthalene-1,5-disulfonate.

In the crystal of the title mol-ecular salt, 2C(7)H(10)N(+)·C(10)H(6)O(6)S(2) (2-), the naphthalene-1,5-disulfonate anion is located on an inversion center and accepts N-H⋯O hydrogen bonds from the 3-methyl-anilinium cations, forming supra-molecular layers parallel to the ac plane.

Related literature

For background to ferroelectric compounds, see: Fu et al. (2011 ▶); Ye et al. (2009 ▶); Zhang & Xiong (2012 ▶); Zhang et al. (2009 ▶, 2010 ▶). For a related structure, see: Liu (2012 ▶).

Experimental

Crystal data

2C7H10N+·C10H6O6S2 2−

M = 502.59

Monoclinic,

a = 8.3426 (17) Å

b = 19.896 (4) Å

c = 7.0670 (14) Å

β = 90.14 (3)°

V = 1173.0 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.27 mm−1

T = 293 K

0.36 × 0.32 × 0.28 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.901, T max = 0.923

10755 measured reflections

2311 independent reflections

2131 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.082

wR(F 2) = 0.190

S = 1.22

2311 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.33 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812021290/xu5533sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021290/xu5533Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812021290/xu5533Isup3.cml

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

2C7H10N+·C10H6O6S22−	F(000) = 528
Mr = 502.59	Dx = 1.423 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2066 reflections
a = 8.3426 (17) Å	θ = 3.4–25.0°
b = 19.896 (4) Å	µ = 0.27 mm−1
c = 7.0670 (14) Å	T = 293 K
β = 90.14 (3)°	Block, colourless
V = 1173.0 (4) Å3	0.36 × 0.32 × 0.28 mm
Z = 2

Rigaku Mercury2 diffractometer	2311 independent reflections
Radiation source: fine-focus sealed tube	2131 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
Detector resolution: 13.6612 pixels mm-1	θmax = 26.0°, θmin = 3.1°
ω scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −24→24
Tmin = 0.901, Tmax = 0.923	l = −8→8
10755 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)] = 0.082	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.190	H-atom parameters constrained
S = 1.22	w = 1/[σ2(Fo2) + (0.0077P)2 + 6.1071P] where P = (Fo2 + 2Fc2)/3
2311 reflections	(Δ/σ)max = 0.034
156 parameters	Δρmax = 0.50 e Å−3
0 restraints	Δρmin = −0.33 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 > 2sigma(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	0.19559 (14)	0.57953 (6)	0.74214 (17)	0.0295 (3)
O2	0.2105 (5)	0.6206 (2)	0.9102 (5)	0.0493 (11)
O3	0.1516 (5)	0.6197 (2)	0.5795 (6)	0.0518 (11)
O1	0.0920 (5)	0.5221 (2)	0.7674 (7)	0.0554 (12)
N1	1.0108 (5)	0.6117 (2)	0.2234 (6)	0.0388 (10)
H1A	1.0688	0.6144	0.3290	0.058*
H1B	1.0748	0.6160	0.1236	0.058*
H1C	0.9618	0.5720	0.2189	0.058*
C11	0.3285 (6)	0.4582 (3)	0.2293 (7)	0.0360 (12)
H11	0.2464	0.4479	0.1447	0.043*
C8	0.3919 (5)	0.5474 (2)	0.6913 (7)	0.0288 (10)
C9	0.4199 (5)	0.5100 (2)	0.5201 (6)	0.0265 (10)
C7	0.7308 (6)	0.6503 (3)	0.2401 (7)	0.0334 (11)
H7	0.6988	0.6057	0.2505	0.040*
C10	0.2950 (6)	0.4918 (2)	0.3920 (7)	0.0317 (11)
H10	0.1895	0.5031	0.4200	0.038*
C6	0.8907 (6)	0.6655 (3)	0.2215 (7)	0.0331 (11)
C2	0.6166 (6)	0.7012 (3)	0.2436 (7)	0.0374 (12)
C12	0.4886 (6)	0.4387 (3)	0.1880 (7)	0.0360 (11)
H12	0.5106	0.4160	0.0759	0.043*
C5	0.9429 (7)	0.7315 (3)	0.2022 (8)	0.0441 (13)
H5	1.0511	0.7413	0.1871	0.053*
C3	0.6696 (7)	0.7671 (3)	0.2287 (8)	0.0434 (13)
H3	0.5954	0.8019	0.2342	0.052*
C4	0.8297 (8)	0.7822 (3)	0.2060 (8)	0.0461 (14)
H4	0.8617	0.8267	0.1933	0.055*
C1	0.4405 (7)	0.6864 (4)	0.2685 (11)	0.0618 (18)
H1D	0.4111	0.6935	0.3982	0.093*
H1E	0.4196	0.6404	0.2346	0.093*
H1F	0.3787	0.7156	0.1886	0.093*

	U11	U22	U33	U12	U13	U23
S1	0.0236 (5)	0.0366 (6)	0.0282 (6)	0.0052 (5)	0.0023 (4)	−0.0040 (5)
O2	0.050 (2)	0.064 (3)	0.034 (2)	0.007 (2)	0.0046 (17)	−0.0176 (19)
O3	0.063 (3)	0.055 (3)	0.037 (2)	0.026 (2)	0.0026 (19)	0.0006 (19)
O1	0.033 (2)	0.051 (3)	0.082 (3)	−0.0064 (18)	0.012 (2)	0.000 (2)
N1	0.042 (2)	0.038 (2)	0.037 (2)	0.0038 (19)	0.0001 (19)	−0.0004 (19)
C11	0.026 (2)	0.042 (3)	0.039 (3)	−0.001 (2)	−0.006 (2)	−0.012 (2)
C8	0.026 (2)	0.031 (2)	0.030 (2)	0.0020 (19)	0.0028 (19)	−0.0006 (19)
C9	0.027 (2)	0.026 (2)	0.027 (2)	0.0007 (18)	0.0021 (18)	0.0014 (18)
C7	0.040 (3)	0.032 (3)	0.028 (2)	−0.004 (2)	0.002 (2)	−0.004 (2)
C10	0.026 (2)	0.037 (3)	0.033 (3)	0.003 (2)	−0.0034 (19)	−0.002 (2)
C6	0.037 (3)	0.034 (3)	0.027 (2)	0.003 (2)	0.002 (2)	0.002 (2)
C2	0.038 (3)	0.045 (3)	0.029 (3)	−0.002 (2)	0.001 (2)	−0.003 (2)
C12	0.038 (3)	0.037 (3)	0.033 (3)	0.004 (2)	0.001 (2)	−0.006 (2)
C5	0.042 (3)	0.048 (3)	0.042 (3)	−0.011 (3)	0.004 (2)	0.001 (3)
C3	0.051 (3)	0.035 (3)	0.044 (3)	0.007 (2)	−0.003 (3)	−0.001 (2)
C4	0.061 (4)	0.033 (3)	0.045 (3)	−0.006 (3)	0.001 (3)	0.006 (2)
C1	0.037 (3)	0.066 (4)	0.083 (5)	−0.002 (3)	0.007 (3)	−0.002 (4)

S1—O1	1.444 (4)	C7—C2	1.392 (7)
S1—O2	1.446 (4)	C7—H7	0.9300
S1—O3	1.446 (4)	C10—H10	0.9300
S1—C8	1.795 (5)	C6—C5	1.391 (7)
N1—C6	1.467 (6)	C2—C3	1.387 (8)
N1—H1A	0.8900	C2—C1	1.509 (8)
N1—H1B	0.8900	C12—C8i	1.339 (7)
N1—H1C	0.8900	C12—H12	0.9300
C11—C10	1.360 (7)	C5—C4	1.381 (8)
C11—C12	1.422 (7)	C5—H5	0.9300
C11—H11	0.9300	C3—C4	1.379 (8)
C8—C12i	1.339 (7)	C3—H3	0.9300
C8—C9	1.440 (6)	C4—H4	0.9300
C9—C10	1.425 (6)	C1—H1D	0.9600
C9—C9i	1.424 (9)	C1—H1E	0.9600
C7—C6	1.374 (7)	C1—H1F	0.9600
O1—S1—O2	113.3 (3)	C9—C10—H10	119.7
O1—S1—O3	112.6 (3)	C7—C6—C5	121.4 (5)
O2—S1—O3	111.3 (2)	C7—C6—N1	120.2 (5)
O1—S1—C8	106.8 (2)	C5—C6—N1	118.5 (5)
O2—S1—C8	106.8 (2)	C3—C2—C7	117.9 (5)
O3—S1—C8	105.5 (2)	C3—C2—C1	120.3 (5)
C6—N1—H1A	109.5	C7—C2—C1	121.7 (5)
C6—N1—H1B	109.5	C8i—C12—C11	120.7 (5)
H1A—N1—H1B	109.5	C8i—C12—H12	119.6
C6—N1—H1C	109.5	C11—C12—H12	119.6
H1A—N1—H1C	109.5	C4—C5—C6	118.3 (5)
H1B—N1—H1C	109.5	C4—C5—H5	120.9
C10—C11—C12	120.2 (5)	C6—C5—H5	120.9
C10—C11—H11	119.9	C4—C3—C2	121.6 (5)
C12—C11—H11	119.9	C4—C3—H3	119.2
C12i—C8—C9	121.3 (4)	C2—C3—H3	119.2
C12i—C8—S1	118.5 (4)	C3—C4—C5	120.4 (5)
C9—C8—S1	120.1 (3)	C3—C4—H4	119.8
C10—C9—C9i	119.2 (5)	C5—C4—H4	119.8
C10—C9—C8	123.0 (4)	C2—C1—H1D	109.5
C9i—C9—C8	117.8 (5)	C2—C1—H1E	109.5
C6—C7—C2	120.5 (5)	H1D—C1—H1E	109.5
C6—C7—H7	119.8	C2—C1—H1F	109.5
C2—C7—H7	119.8	H1D—C1—H1F	109.5
C11—C10—C9	120.7 (4)	H1E—C1—H1F	109.5
C11—C10—H10	119.7

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3ii	0.89	1.90	2.779 (6)	168
N1—H1B···O2iii	0.89	1.89	2.779 (6)	177
N1—H1C···O1i	0.89	1.93	2.797 (6)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3i	0.89	1.90	2.779 (6)	168
N1—H1B⋯O2ii	0.89	1.89	2.779 (6)	177
N1—H1C⋯O1iii	0.89	1.93	2.797 (6)	165

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