Propanaminium p-toluene-sulfonate.

In the crystal structure of the title salt, C(3)H(10)N(+)·C(7)H(7)O(3)S(-), N-H⋯O hydrogen bonds involving the ammonium groups of the cations and the sulfonate O atoms result in the formation of a three-dimensional network.

Related literature

For general background to ferroelectric metal-organic frameworks, see: Zhang et al. (2009 ▶). For related structures, see: Helvenston et al. (2006 ▶); Collier et al. (2006 ▶); Koshima et al. (2001 ▶).

Experimental

Crystal data

C3H10N+·C7H7O3S−

M = 231.31

Triclinic,

a = 5.6682 (11) Å

b = 7.3927 (15) Å

c = 13.817 (3) Å

α = 93.81 (3)°

β = 94.22 (3)°

γ = 91.27 (3)°

V = 575.9 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.27 mm−1

T = 293 K

0.30 × 0.30 × 0.20 mm

Data collection

Rigaku Mercury CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.489, T max = 1.000

6023 measured reflections

2639 independent reflections

1897 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.189

S = 1.03

2639 reflections

139 parameters

H-atom parameters constrained

Δρmax = 1.02 e Å−3

Δρmin = −0.52 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: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812019435/im2372sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812019435/im2372Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812019435/im2372Isup3.cml

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

C3H10N+·C7H7O3S−	Z = 2
Mr = 231.31	F(000) = 248
Triclinic, P1	Dx = 1.334 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.6682 (11) Å	Cell parameters from 3450 reflections
b = 7.3927 (15) Å	θ = 6.2–55.3°
c = 13.817 (3) Å	µ = 0.27 mm−1
α = 93.81 (3)°	T = 293 K
β = 94.22 (3)°	Block, colorless
γ = 91.27 (3)°	0.3 × 0.3 × 0.2 mm
V = 575.9 (2) Å3

Rigaku Mercury CCD diffractometer	2639 independent reflections
Radiation source: fine-focus sealed tube	1897 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
ω scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −7→7
Tmin = 0.489, Tmax = 1.000	k = −9→9
6023 measured reflections	l = −17→17

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.189	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0894P)2 + 0.589P] where P = (Fo2 + 2Fc2)/3
2639 reflections	(Δ/σ)max < 0.001
139 parameters	Δρmax = 1.02 e Å−3
0 restraints	Δρmin = −0.52 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	0.1911 (8)	0.6760 (6)	0.2544 (3)	0.0653 (12)
H1D	0.3047	0.7734	0.2710	0.098*
H1E	0.1634	0.6599	0.1849	0.098*
H1F	0.2509	0.5662	0.2790	0.098*
C2	−0.0444 (8)	0.7220 (7)	0.2999 (3)	0.0667 (12)
H2A	−0.1012	0.8366	0.2784	0.080*
H2B	−0.1639	0.6284	0.2796	0.080*
C3	−0.0004 (9)	0.7333 (7)	0.4042 (3)	0.0677 (12)
H3A	0.1028	0.8379	0.4235	0.081*
H3B	0.0829	0.6263	0.4229	0.081*
C4	0.6719 (8)	0.7797 (6)	1.0672 (3)	0.0566 (10)
H4A	0.8354	0.7483	1.0741	0.085*
H4B	0.5784	0.6936	1.0980	0.085*
H4C	0.6535	0.8988	1.0973	0.085*
C5	0.5912 (6)	0.7771 (4)	0.9612 (2)	0.0390 (8)
C6	0.3676 (6)	0.7134 (5)	0.9274 (2)	0.0426 (8)
H6	0.2666	0.6691	0.9709	0.051*
C7	0.2909 (6)	0.7140 (4)	0.8304 (2)	0.0379 (7)
H7	0.1392	0.6712	0.8091	0.045*
C8	0.4394 (5)	0.7782 (4)	0.7650 (2)	0.0287 (6)
C9	0.6642 (6)	0.8422 (5)	0.7971 (2)	0.0403 (8)
H9	0.7662	0.8846	0.7534	0.048*
C10	0.7356 (6)	0.8427 (5)	0.8943 (2)	0.0444 (8)
H10	0.8858	0.8886	0.9158	0.053*
N1	−0.2160 (5)	0.7484 (4)	0.45840 (19)	0.0394 (7)
H1A	−0.2958	0.8447	0.4408	0.059*
H1B	−0.1749	0.7606	0.5220	0.059*
H1C	−0.3069	0.6488	0.4450	0.059*
O1	0.0916 (4)	0.7800 (4)	0.63485 (18)	0.0593 (8)
O2	0.4559 (5)	0.9336 (3)	0.60426 (17)	0.0487 (6)
O3	0.4344 (4)	0.6090 (3)	0.59619 (16)	0.0463 (6)
S1	0.34710 (14)	0.77477 (11)	0.64010 (5)	0.0344 (3)

	U11	U22	U33	U12	U13	U23
C1	0.073 (3)	0.068 (3)	0.058 (3)	0.010 (2)	0.025 (2)	0.006 (2)
C2	0.072 (3)	0.070 (3)	0.057 (3)	0.004 (2)	−0.004 (2)	0.005 (2)
C3	0.079 (3)	0.065 (3)	0.059 (3)	−0.004 (2)	0.013 (2)	−0.003 (2)
C4	0.076 (3)	0.059 (2)	0.0333 (18)	0.015 (2)	−0.0078 (18)	0.0034 (17)
C5	0.050 (2)	0.0366 (17)	0.0294 (15)	0.0122 (15)	−0.0036 (14)	0.0001 (13)
C6	0.051 (2)	0.0438 (19)	0.0345 (16)	−0.0011 (16)	0.0067 (15)	0.0081 (14)
C7	0.0376 (17)	0.0409 (18)	0.0349 (16)	−0.0059 (14)	0.0036 (13)	0.0010 (13)
C8	0.0336 (15)	0.0271 (14)	0.0251 (13)	0.0081 (12)	0.0012 (11)	−0.0021 (11)
C9	0.0331 (17)	0.052 (2)	0.0361 (16)	−0.0024 (14)	0.0050 (14)	0.0024 (15)
C10	0.0329 (17)	0.058 (2)	0.0406 (18)	0.0017 (15)	−0.0019 (14)	−0.0033 (16)
N1	0.0468 (16)	0.0387 (15)	0.0326 (14)	0.0032 (12)	0.0017 (12)	0.0022 (12)
O1	0.0358 (14)	0.103 (2)	0.0379 (13)	0.0121 (14)	−0.0045 (11)	−0.0013 (14)
O2	0.0657 (17)	0.0429 (14)	0.0392 (13)	0.0082 (12)	0.0040 (12)	0.0136 (11)
O3	0.0599 (16)	0.0423 (13)	0.0356 (12)	0.0057 (11)	0.0045 (11)	−0.0088 (10)
S1	0.0370 (5)	0.0403 (5)	0.0255 (4)	0.0057 (3)	0.0007 (3)	0.0003 (3)

C1—C2	1.552 (6)	C6—C7	1.378 (4)
C1—H1D	0.9600	C6—H6	0.9300
C1—H1E	0.9600	C7—C8	1.379 (4)
C1—H1F	0.9600	C7—H7	0.9300
C2—C3	1.442 (6)	C8—C9	1.381 (4)
C2—H2A	0.9700	C8—S1	1.764 (3)
C2—H2B	0.9700	C9—C10	1.374 (5)
C3—N1	1.482 (5)	C9—H9	0.9300
C3—H3A	0.9700	C10—H10	0.9300
C3—H3B	0.9700	N1—H1A	0.8900
C4—C5	1.500 (4)	N1—H1B	0.8900
C4—H4A	0.9600	N1—H1C	0.8900
C4—H4B	0.9600	O1—S1	1.446 (3)
C4—H4C	0.9600	O2—S1	1.447 (3)
C5—C6	1.380 (5)	O3—S1	1.445 (2)
C5—C10	1.383 (5)
C2—C1—H1D	109.5	C7—C6—C5	121.3 (3)
C2—C1—H1E	109.5	C7—C6—H6	119.3
H1D—C1—H1E	109.5	C5—C6—H6	119.3
C2—C1—H1F	109.5	C6—C7—C8	120.0 (3)
H1D—C1—H1F	109.5	C6—C7—H7	120.0
H1E—C1—H1F	109.5	C8—C7—H7	120.0
C3—C2—C1	108.1 (4)	C7—C8—C9	119.8 (3)
C3—C2—H2A	110.1	C7—C8—S1	120.6 (2)
C1—C2—H2A	110.1	C9—C8—S1	119.6 (2)
C3—C2—H2B	110.1	C10—C9—C8	119.3 (3)
C1—C2—H2B	110.1	C10—C9—H9	120.4
H2A—C2—H2B	108.4	C8—C9—H9	120.4
C2—C3—N1	114.5 (4)	C9—C10—C5	122.1 (3)
C2—C3—H3A	108.6	C9—C10—H10	118.9
N1—C3—H3A	108.6	C5—C10—H10	118.9
C2—C3—H3B	108.6	C3—N1—H1A	109.5
N1—C3—H3B	108.6	C3—N1—H1B	109.5
H3A—C3—H3B	107.6	H1A—N1—H1B	109.5
C5—C4—H4A	109.5	C3—N1—H1C	109.5
C5—C4—H4B	109.5	H1A—N1—H1C	109.5
H4A—C4—H4B	109.5	H1B—N1—H1C	109.5
C5—C4—H4C	109.5	O3—S1—O1	113.29 (17)
H4A—C4—H4C	109.5	O3—S1—O2	111.81 (15)
H4B—C4—H4C	109.5	O1—S1—O2	112.99 (17)
C6—C5—C10	117.6 (3)	O3—S1—C8	106.01 (14)
C6—C5—C4	121.1 (3)	O1—S1—C8	105.90 (15)
C10—C5—C4	121.3 (3)	O2—S1—C8	106.13 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.89	2.00	2.892 (4)	176
N1—H1C···O3ii	0.89	2.05	2.921 (4)	165
N1—H1B···O1	0.89	2.09	2.884 (4)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.89	2.00	2.892 (4)	176
N1—H1C⋯O3ii	0.89	2.05	2.921 (4)	165
N1—H1B⋯O1	0.89	2.09	2.884 (4)	149

Symmetry codes: (i) ; (ii) .