Bis(4-ethoxy­anilinium) sulfate trihydrate

Fu, X.

doi:10.1107/S1600536809036290

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2520

doi:10.1107/S1600536809036290

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Bis(4-ethoxyanilinium) sulfate trihydrate

Xue-qun Fu ^a ^*

^aOrdered Matter Science Research Center, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: fuxuequn222@163.com

(Received 7 September 2009; accepted 8 September 2009; online 26 September 2009)

The structure of the title compound, 2C₈H₁₂NO⁺·SO₄²⁻·3H₂O, consists of organic layers, water molecules and SO₄²⁻ anions which lie within the organic layers. In the crystal, intermolecular N—H⋯O, N—H⋯S O—H⋯O and O—H⋯S hydrogen bonds, some of which are bifurcated, stabilize the structure.

Related literature

For background to this study, see: Hang et al. (2009 ); Li et al. (2008 ).

Experimental

Crystal data

2C₈H₁₂NO⁺·SO₄²⁻·3H₂O
M_r = 426.48
Triclinic, $[P \overline 1]$
a = 7.0455 (14) Å
b = 10.969 (2) Å
c = 13.787 (3) Å
α = 101.40 (3)°
β = 94.53 (3)°
γ = 90.18 (3)°
V = 1041.0 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.96, T_max = 0.96
10835 measured reflections
4748 independent reflections
3947 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.143
S = 1.10
4748 reflections
277 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.62 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2C⋯O1ⁱ	0.89	2.05	2.870 (2)	153
N2—H2C⋯S1ⁱ	0.89	2.77	3.649 (2)	172
N2—H2D⋯O2ⁱⁱ	0.89	2.07	2.788 (2)	137
N2—H2E⋯O7Wⁱⁱⁱ	0.89	1.94	2.819 (3)	169
N1—H1D⋯O8Wⁱⁱⁱ	0.89	2.14	2.823 (2)	133
N1—H1D⋯O9Wⁱⁱ	0.89	2.46	3.166 (3)	136
N1—H1E⋯O3ⁱⁱ	0.89	1.93	2.785 (2)	162
N1—H1F⋯O1^iv	0.89	2.03	2.849 (2)	152
O7W—H7D⋯O4^v	0.81 (4)	2.11 (4)	2.893 (3)	163 (3)
O8W—H8D⋯O4^vi	0.75 (3)	2.12 (3)	2.864 (3)	172 (3)
O9W—H9E⋯O1^vii	0.92 (4)	2.07 (4)	2.991 (3)	175 (4)
O9W—H9E⋯S1^vii	0.92 (4)	2.98 (4)	3.791 (2)	147 (3)
O7W—H7C⋯O2	0.83 (4)	2.05 (4)	2.851 (3)	164 (3)
O8W—H8C⋯O3	0.90 (4)	1.94 (4)	2.815 (3)	164 (3)
O8W—H8C⋯S1	0.90 (4)	3.02 (4)	3.852 (2)	154 (3)
O9W—H9D⋯O4	1.03 (5)	2.00 (5)	2.981 (3)	158 (4)
O9W—H9D⋯S1	1.03 (5)	2.81 (5)	3.547 (2)	129 (3)
Symmetry codes: (i) x-1, y, z-1; (ii) -x+1, -y+1, -z+1; (iii) -x+2, -y+1, -z+1; (iv) x-1, y-1, z-1; (v) -x+2, -y+1, -z+2; (vi) -x+2, -y+2, -z+2; (vii) x-1, y, z.

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: PRPKAPPA (Ferguson, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809036290/jh2104sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809036290/jh2104Isup2.hkl

checkCIF report

Comment top

This study is a part of systematic investigation of dielectric-ferroelectric materials, including organic ligands (Li et al., 2008), metal–organic coordination compounds (Hang et al., 2009) and organic–inorganic hybrid. 4-Ethoxyanilinium perchlorate has no dielectric disuniform from 80 K to 480 K, (m.p. 492–493 K).

The asymmetric unit of the title compound contains two 4-ethoxyanilinium cations, one sulfate radical anion and three water molecules (Fig 1). In the anion, the torsion angles of C1—C2—O5—C3 and C9—C10—O6—C11 are -174.8 (2)° and 179.48 (19)°, respectively. The supramolecular structure consists of infinite chains of anions with one cation and three water molecules linked to each anion via N—H···O and O—H···O hydrogen bonds.

Related literature top

For background to this study, see: Hang et al. (2009); Li et al. (2008).

Experimental top

Single crystals of 4-ethoxyanilinium sulfate are prepared by slow evaporation for five days at room temperature of an ethanol solution of 4-ethoxybenzenamine and sulfuric acid (5 mol l^-).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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: PRPKAPPA (Ferguson, 1999).

Figures top

	Fig. 1. The molecular structure of the title compound, with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level, and all H atoms have been omitted for clarity.
	Fig. 2. A view of the packing of the title compound, stacking along the a axis. Dashed lines indicate hydrogen bonds.

Bis(4-ethoxyanilinium) sulfate trihydrate top

Crystal data top

2C₈H₁₂NO⁺·SO₄²⁻·3H₂O	Z = 2
M_r = 426.48	F(000) = 456
Triclinic, P1	D_x = 1.361 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0455 (14) Å	Cell parameters from 5008 reflections
b = 10.969 (2) Å	θ = 3.0–27.6°
c = 13.787 (3) Å	µ = 0.21 mm⁻¹
α = 101.40 (3)°	T = 298 K
β = 94.53 (3)°	Prism, colourless
γ = 90.18 (3)°	0.20 × 0.20 × 0.20 mm
V = 1041.0 (4) Å³

Data collection top

Rigaku SCXmini diffractometer	4748 independent reflections
Radiation source: fine-focus sealed tube	3947 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
ω scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −14→14
T_min = 0.96, T_max = 0.96	l = −17→17
10835 measured reflections

Refinement top

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.143	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.0626P)² + 0.4014P] where P = (F_o² + 2F_c²)/3
4748 reflections	(Δ/σ)_max = 0.011
277 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.62 e Å⁻³

Crystal data top

2C₈H₁₂NO⁺·SO₄²⁻·3H₂O	γ = 90.18 (3)°
M_r = 426.48	V = 1041.0 (4) Å³
Triclinic, P1	Z = 2
a = 7.0455 (14) Å	Mo Kα radiation
b = 10.969 (2) Å	µ = 0.21 mm⁻¹
c = 13.787 (3) Å	T = 298 K
α = 101.40 (3)°	0.20 × 0.20 × 0.20 mm
β = 94.53 (3)°

Data collection top

Rigaku SCXmini diffractometer	4748 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	3947 reflections with I > 2σ(I)
T_min = 0.96, T_max = 0.96	R_int = 0.041
10835 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.143	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.30 e Å⁻³
4748 reflections	Δρ_min = −0.62 e Å⁻³
277 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C10	0.0896 (3)	0.6806 (2)	0.58350 (17)	0.0449 (5)
H10A	−0.0396	0.6635	0.5538	0.054*
H10B	0.1251	0.7648	0.5791	0.054*
C13	0.1606 (3)	0.6525 (2)	0.27781 (16)	0.0376 (5)
H13A	0.0981	0.7046	0.2406	0.045*
C14	0.2775 (3)	0.56205 (18)	0.23343 (15)	0.0298 (4)
C11	0.2290 (3)	0.5885 (2)	0.43338 (15)	0.0338 (4)
C16	0.3460 (3)	0.4968 (2)	0.38719 (16)	0.0405 (5)
H16A	0.4083	0.4440	0.4238	0.049*
C12	0.1355 (3)	0.6664 (2)	0.37864 (17)	0.0394 (5)
H12A	0.0564	0.7276	0.4089	0.047*
C15	0.3701 (3)	0.4838 (2)	0.28761 (16)	0.0383 (5)
H15A	0.4487	0.4224	0.2570	0.046*
N2	0.2998 (2)	0.54499 (16)	0.12718 (12)	0.0323 (4)
H2C	0.2325	0.6016	0.1020	0.049*
H2D	0.2583	0.4692	0.0971	0.049*
H2E	0.4222	0.5538	0.1177	0.049*
O6	0.2170 (2)	0.59385 (16)	0.53274 (11)	0.0454 (4)
C7	0.4295 (3)	0.1249 (2)	0.29676 (16)	0.0383 (5)
H7A	0.5285	0.1591	0.2695	0.046*
C8	0.4180 (3)	0.1505 (2)	0.39883 (16)	0.0402 (5)
H8A	0.5088	0.2020	0.4400	0.048*
C6	0.2953 (3)	0.04922 (18)	0.23606 (14)	0.0284 (4)
C3	0.2702 (3)	0.09881 (19)	0.43898 (15)	0.0329 (4)
C5	0.1461 (3)	−0.0017 (2)	0.27536 (15)	0.0348 (5)
H5A	0.0550	−0.0525	0.2338	0.042*
C4	0.1337 (3)	0.0235 (2)	0.37657 (16)	0.0365 (5)
H4A	0.0333	−0.0101	0.4033	0.044*
N1	0.3073 (2)	0.02291 (16)	0.12851 (12)	0.0316 (4)
H1D	0.4093	0.0617	0.1140	0.047*
H1E	0.2031	0.0497	0.0991	0.047*
H1F	0.3168	−0.0587	0.1070	0.047*
O4	0.8618 (2)	0.76777 (14)	1.06802 (12)	0.0419 (4)
O3	0.9964 (2)	0.84402 (14)	0.93687 (12)	0.0411 (4)
O1	1.2016 (2)	0.76811 (14)	1.05715 (11)	0.0376 (3)
C9	0.1020 (4)	0.6671 (3)	0.69069 (18)	0.0547 (7)
H9A	0.0183	0.7250	0.7268	0.082*
H9B	0.2304	0.6839	0.7192	0.082*
H9C	0.0651	0.5839	0.6942	0.082*
C2	0.3919 (3)	0.1835 (2)	0.60656 (16)	0.0435 (5)
H2A	0.4021	0.2688	0.5976	0.052*
H2B	0.5136	0.1442	0.5956	0.052*
S1	1.01303 (6)	0.75062 (4)	0.99930 (3)	0.02523 (14)
O2	1.0005 (2)	0.62454 (13)	0.93962 (12)	0.0415 (4)
O5	0.2452 (2)	0.11746 (16)	0.53811 (11)	0.0425 (4)
C1	0.3390 (4)	0.1809 (3)	0.70955 (17)	0.0509 (6)
H1A	0.4344	0.2252	0.7572	0.076*
H1B	0.3307	0.0962	0.7178	0.076*
H1C	0.2181	0.2195	0.7195	0.076*
O7W	1.3057 (3)	0.4580 (2)	0.89486 (15)	0.0507 (5)
O8W	1.2987 (2)	0.98944 (19)	0.89593 (15)	0.0476 (4)
O9W	0.5193 (3)	0.7333 (2)	0.92324 (17)	0.0644 (5)
H7D	1.249 (5)	0.393 (3)	0.893 (2)	0.072 (10)*
H8D	1.255 (4)	1.052 (3)	0.899 (2)	0.050 (9)*
H7C	1.227 (5)	0.514 (3)	0.900 (2)	0.067 (10)*
H9E	0.427 (6)	0.747 (4)	0.968 (3)	0.104 (14)*
H8C	1.209 (5)	0.932 (3)	0.899 (2)	0.077 (10)*
H9D	0.614 (7)	0.757 (4)	0.985 (3)	0.132 (17)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C10	0.0433 (13)	0.0460 (13)	0.0452 (13)	0.0036 (10)	0.0118 (10)	0.0049 (10)
C13	0.0376 (11)	0.0343 (11)	0.0436 (12)	0.0107 (9)	0.0059 (9)	0.0127 (9)
C14	0.0276 (9)	0.0277 (10)	0.0337 (10)	−0.0022 (7)	0.0035 (8)	0.0046 (8)
C11	0.0329 (10)	0.0346 (11)	0.0332 (10)	0.0009 (8)	0.0020 (8)	0.0052 (8)
C16	0.0423 (12)	0.0400 (12)	0.0384 (11)	0.0140 (9)	−0.0019 (9)	0.0074 (9)
C12	0.0380 (11)	0.0363 (11)	0.0446 (12)	0.0119 (9)	0.0102 (9)	0.0065 (9)
C15	0.0364 (11)	0.0360 (11)	0.0406 (11)	0.0127 (9)	0.0018 (9)	0.0033 (9)
N2	0.0330 (9)	0.0299 (9)	0.0346 (9)	0.0019 (7)	0.0048 (7)	0.0068 (7)
O6	0.0510 (10)	0.0508 (10)	0.0346 (8)	0.0146 (8)	0.0059 (7)	0.0073 (7)
C7	0.0361 (11)	0.0389 (12)	0.0402 (11)	−0.0116 (9)	0.0133 (9)	0.0047 (9)
C8	0.0392 (11)	0.0429 (12)	0.0354 (11)	−0.0152 (9)	0.0078 (9)	−0.0019 (9)
C6	0.0299 (9)	0.0252 (9)	0.0310 (10)	0.0029 (7)	0.0069 (7)	0.0059 (7)
C3	0.0324 (10)	0.0327 (10)	0.0335 (10)	−0.0011 (8)	0.0081 (8)	0.0045 (8)
C5	0.0317 (10)	0.0363 (11)	0.0362 (11)	−0.0081 (8)	0.0022 (8)	0.0071 (8)
C4	0.0309 (10)	0.0431 (12)	0.0375 (11)	−0.0099 (9)	0.0080 (8)	0.0107 (9)
N1	0.0322 (9)	0.0316 (9)	0.0319 (9)	−0.0001 (7)	0.0067 (7)	0.0068 (7)
O4	0.0408 (9)	0.0383 (9)	0.0515 (9)	0.0061 (7)	0.0238 (7)	0.0126 (7)
O3	0.0387 (8)	0.0403 (9)	0.0517 (9)	0.0021 (6)	0.0062 (7)	0.0261 (7)
O1	0.0327 (8)	0.0346 (8)	0.0450 (9)	−0.0015 (6)	−0.0045 (6)	0.0098 (6)
C9	0.0543 (15)	0.0663 (17)	0.0406 (13)	−0.0081 (13)	0.0121 (11)	0.0005 (12)
C2	0.0406 (12)	0.0485 (13)	0.0379 (12)	−0.0098 (10)	0.0048 (9)	−0.0006 (10)
S1	0.0243 (2)	0.0203 (2)	0.0323 (3)	0.00085 (16)	0.00592 (18)	0.00655 (17)
O2	0.0384 (8)	0.0265 (8)	0.0552 (10)	−0.0019 (6)	0.0070 (7)	−0.0040 (7)
O5	0.0378 (8)	0.0560 (10)	0.0318 (8)	−0.0121 (7)	0.0067 (6)	0.0029 (7)
C1	0.0497 (14)	0.0651 (17)	0.0361 (12)	−0.0007 (12)	0.0038 (10)	0.0052 (11)
O7W	0.0384 (9)	0.0393 (10)	0.0775 (13)	0.0026 (8)	0.0194 (9)	0.0133 (9)
O8W	0.0383 (9)	0.0386 (10)	0.0700 (12)	0.0061 (8)	0.0199 (8)	0.0146 (9)
O9W	0.0516 (11)	0.0690 (14)	0.0738 (14)	0.0023 (10)	0.0175 (11)	0.0121 (11)

Geometric parameters (Å, º) top

C10—O6	1.430 (3)	C3—C4	1.390 (3)
C10—C9	1.510 (3)	C5—C4	1.378 (3)
C10—H10A	0.9700	C5—H5A	0.9300
C10—H10B	0.9700	C4—H4A	0.9300
C13—C14	1.372 (3)	N1—H1D	0.8900
C13—C12	1.394 (3)	N1—H1E	0.8900
C13—H13A	0.9300	N1—H1F	0.8900
C14—C15	1.378 (3)	O4—S1	1.4693 (15)
C14—N2	1.461 (3)	O3—S1	1.4621 (15)
C11—O6	1.369 (3)	O1—S1	1.4861 (15)
C11—C12	1.383 (3)	C9—H9A	0.9600
C11—C16	1.389 (3)	C9—H9B	0.9600
C16—C15	1.376 (3)	C9—H9C	0.9600
C16—H16A	0.9300	C2—O5	1.434 (3)
C12—H12A	0.9300	C2—C1	1.502 (3)
C15—H15A	0.9300	C2—H2A	0.9700
N2—H2C	0.8900	C2—H2B	0.9700
N2—H2D	0.8900	S1—O2	1.4613 (15)
N2—H2E	0.8900	C1—H1A	0.9600
C7—C6	1.371 (3)	C1—H1B	0.9600
C7—C8	1.389 (3)	C1—H1C	0.9600
C7—H7A	0.9300	O7W—H7D	0.81 (4)
C8—C3	1.386 (3)	O7W—H7C	0.83 (4)
C8—H8A	0.9300	O8W—H8D	0.75 (3)
C6—C5	1.384 (3)	O8W—H8C	0.90 (4)
C6—N1	1.463 (2)	O9W—H9E	0.92 (4)
C3—O5	1.367 (2)	O9W—H9D	1.03 (5)

O6—C10—C9	107.7 (2)	C8—C3—C4	119.69 (19)
O6—C10—H10A	110.2	C4—C5—C6	119.50 (19)
C9—C10—H10A	110.2	C4—C5—H5A	120.2
O6—C10—H10B	110.2	C6—C5—H5A	120.2
C9—C10—H10B	110.2	C5—C4—C3	120.39 (19)
H10A—C10—H10B	108.5	C5—C4—H4A	119.8
C14—C13—C12	120.0 (2)	C3—C4—H4A	119.8
C14—C13—H13A	120.0	C6—N1—H1D	109.5
C12—C13—H13A	120.0	C6—N1—H1E	109.5
C13—C14—C15	120.56 (19)	H1D—N1—H1E	109.5
C13—C14—N2	120.11 (18)	C6—N1—H1F	109.5
C15—C14—N2	119.29 (18)	H1D—N1—H1F	109.5
O6—C11—C12	124.93 (19)	H1E—N1—H1F	109.5
O6—C11—C16	115.39 (19)	C10—C9—H9A	109.5
C12—C11—C16	119.7 (2)	C10—C9—H9B	109.5
C15—C16—C11	120.4 (2)	H9A—C9—H9B	109.5
C15—C16—H16A	119.8	C10—C9—H9C	109.5
C11—C16—H16A	119.8	H9A—C9—H9C	109.5
C11—C12—C13	119.60 (19)	H9B—C9—H9C	109.5
C11—C12—H12A	120.2	O5—C2—C1	107.52 (19)
C13—C12—H12A	120.2	O5—C2—H2A	110.2
C16—C15—C14	119.79 (19)	C1—C2—H2A	110.2
C16—C15—H15A	120.1	O5—C2—H2B	110.2
C14—C15—H15A	120.1	C1—C2—H2B	110.2
C14—N2—H2C	109.5	H2A—C2—H2B	108.5
C14—N2—H2D	109.5	O2—S1—O3	111.43 (10)
H2C—N2—H2D	109.5	O2—S1—O4	109.70 (10)
C14—N2—H2E	109.5	O3—S1—O4	109.51 (9)
H2C—N2—H2E	109.5	O2—S1—O1	108.58 (9)
H2D—N2—H2E	109.5	O3—S1—O1	108.27 (9)
C11—O6—C10	118.27 (18)	O4—S1—O1	109.31 (10)
C6—C7—C8	120.18 (19)	C3—O5—C2	118.10 (16)
C6—C7—H7A	119.9	C2—C1—H1A	109.5
C8—C7—H7A	119.9	C2—C1—H1B	109.5
C3—C8—C7	119.60 (19)	H1A—C1—H1B	109.5
C3—C8—H8A	120.2	C2—C1—H1C	109.5
C7—C8—H8A	120.2	H1A—C1—H1C	109.5
C7—C6—C5	120.63 (19)	H1B—C1—H1C	109.5
C7—C6—N1	120.03 (17)	H7D—O7W—H7C	108 (3)
C5—C6—N1	119.33 (18)	H8D—O8W—H8C	111 (3)
O5—C3—C8	124.56 (19)	H9E—O9W—H9D	85 (3)
O5—C3—C4	115.74 (18)

C12—C13—C14—C15	0.4 (3)	C6—C7—C8—C3	0.2 (4)
C12—C13—C14—N2	178.24 (19)	C8—C7—C6—C5	0.5 (3)
O6—C11—C16—C15	−179.3 (2)	C8—C7—C6—N1	179.7 (2)
C12—C11—C16—C15	0.4 (3)	C7—C8—C3—O5	179.9 (2)
O6—C11—C12—C13	179.3 (2)	C7—C8—C3—C4	−1.0 (4)
C16—C11—C12—C13	−0.4 (3)	C7—C6—C5—C4	−0.4 (3)
C14—C13—C12—C11	0.0 (3)	N1—C6—C5—C4	−179.62 (19)
C11—C16—C15—C14	−0.1 (3)	C6—C5—C4—C3	−0.4 (3)
C13—C14—C15—C16	−0.3 (3)	O5—C3—C4—C5	−179.7 (2)
N2—C14—C15—C16	−178.2 (2)	C8—C3—C4—C5	1.1 (3)
C12—C11—O6—C10	4.3 (3)	C8—C3—O5—C2	−7.2 (3)
C16—C11—O6—C10	−176.0 (2)	C4—C3—O5—C2	173.6 (2)
C9—C10—O6—C11	179.48 (19)	C1—C2—O5—C3	−174.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2C···O1ⁱ	0.89	2.05	2.870 (2)	153
N2—H2C···S1ⁱ	0.89	2.77	3.649 (2)	172
N2—H2D···O2ⁱⁱ	0.89	2.07	2.788 (2)	137
N2—H2E···O7Wⁱⁱⁱ	0.89	1.94	2.819 (3)	169
N1—H1D···O8Wⁱⁱⁱ	0.89	2.14	2.823 (2)	133
N1—H1D···O9Wⁱⁱ	0.89	2.46	3.166 (3)	136
N1—H1E···O3ⁱⁱ	0.89	1.93	2.785 (2)	162
N1—H1F···O1^iv	0.89	2.03	2.849 (2)	152
O7W—H7D···O4^v	0.81 (4)	2.11 (4)	2.893 (3)	163 (3)
O8W—H8D···O4^vi	0.75 (3)	2.12 (3)	2.864 (3)	172 (3)
O9W—H9E···O1^vii	0.92 (4)	2.07 (4)	2.991 (3)	175 (4)
O9W—H9E···S1^vii	0.92 (4)	2.98 (4)	3.791 (2)	147 (3)
O7W—H7C···O2	0.83 (4)	2.05 (4)	2.851 (3)	164 (3)
O8W—H8C···O3	0.90 (4)	1.94 (4)	2.815 (3)	164 (3)
O8W—H8C···S1	0.90 (4)	3.02 (4)	3.852 (2)	154 (3)
O9W—H9D···O4	1.03 (5)	2.00 (5)	2.981 (3)	158 (4)
O9W—H9D···S1	1.03 (5)	2.81 (5)	3.547 (2)	129 (3)

Symmetry codes: (i) x−1, y, z−1; (ii) −x+1, −y+1, −z+1; (iii) −x+2, −y+1, −z+1; (iv) x−1, y−1, z−1; (v) −x+2, −y+1, −z+2; (vi) −x+2, −y+2, −z+2; (vii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	2C₈H₁₂NO⁺·SO₄²⁻·3H₂O
M_r	426.48
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.0455 (14), 10.969 (2), 13.787 (3)
α, β, γ (°)	101.40 (3), 94.53 (3), 90.18 (3)
V (Å³)	1041.0 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.96, 0.96
No. of measured, independent and observed [I > 2σ(I)] reflections	10835, 4748, 3947
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.143, 1.10
No. of reflections	4748
No. of parameters	277
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.62

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PRPKAPPA (Ferguson, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2C···O1ⁱ	0.89	2.05	2.870 (2)	153.2
N2—H2C···S1ⁱ	0.89	2.77	3.649 (2)	171.6
N2—H2D···O2ⁱⁱ	0.89	2.07	2.788 (2)	137.4
N2—H2E···O7Wⁱⁱⁱ	0.89	1.94	2.819 (3)	168.8
N1—H1D···O8Wⁱⁱⁱ	0.89	2.14	2.823 (2)	132.8
N1—H1D···O9Wⁱⁱ	0.89	2.46	3.166 (3)	136.3
N1—H1E···O3ⁱⁱ	0.89	1.93	2.785 (2)	161.8
N1—H1F···O1^iv	0.89	2.03	2.849 (2)	152.2
O7W—H7D···O4^v	0.81 (4)	2.11 (4)	2.893 (3)	163 (3)
O8W—H8D···O4^vi	0.75 (3)	2.12 (3)	2.864 (3)	172 (3)
O9W—H9E···O1^vii	0.92 (4)	2.07 (4)	2.991 (3)	175 (4)
O9W—H9E···S1^vii	0.92 (4)	2.98 (4)	3.791 (2)	147 (3)
O7W—H7C···O2	0.83 (4)	2.05 (4)	2.851 (3)	164 (3)
O8W—H8C···O3	0.90 (4)	1.94 (4)	2.815 (3)	164 (3)
O8W—H8C···S1	0.90 (4)	3.02 (4)	3.852 (2)	154 (3)
O9W—H9D···O4	1.03 (5)	2.00 (5)	2.981 (3)	158 (4)
O9W—H9D···S1	1.03 (5)	2.81 (5)	3.547 (2)	129 (3)

Symmetry codes: (i) x−1, y, z−1; (ii) −x+1, −y+1, −z+1; (iii) −x+2, −y+1, −z+1; (iv) x−1, y−1, z−1; (v) −x+2, −y+1, −z+2; (vi) −x+2, −y+2, −z+2; (vii) x−1, y, z.

Acknowledgements

The author is grateful to the starter fund of Southeast University for financial support to buy the X-ray diffractometer.

References

Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada. Google Scholar
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