Bis(4,4′-methyl­enedianilinium) naphthalene-1,5-disulfonate dihydrate

Wei, L.-H.

doi:10.1107/S160053680800723X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 4| April 2008| Page o734

doi:10.1107/S160053680800723X

Open

access

Bis(4,4′-methylenedianilinium) naphthalene-1,5-disulfonate dihydrate

Lin-Heng Wei ^a ^*

^aCollege of Environment and Planning, Henan University, Kaifeng 475001, People's Republic of China
^*Correspondence e-mail: linhengw@henu.edu.cn

(Received 10 February 2008; accepted 17 March 2008; online 20 March 2008)

The asymmetric unit of the title salt, C₁₃H₁₆N₂²⁺·C₁₀H₆O₆S₂²⁻·2H₂O, consists of one dication located on a general position, half each of two centrosymmetric dianions, and two uncoordinated water molecules in general positions. In the dication, the dihedral angle between the benzene rings is 74.67 (6)°. The cations and anions interact through N—H⋯O hydrogen bonds. The NH₃⁺ functional groups are also involved in N—H⋯O hydrogen bonds with the water molecules, forming an infinite three-dimensional framework in the crystal structure.

Related literature

For related literature, see: Wang & Wei (2007 ).

Experimental

Crystal data

C₁₃H₁₆N₂²⁺·C₁₀H₆O₆S₂²⁻·2H₂O
M_r = 522.58
Triclinic, $[P \overline 1]$
a = 7.9652 (6) Å
b = 10.9135 (8) Å
c = 13.8158 (10) Å
α = 87.429 (1)°
β = 85.820 (1)°
γ = 83.262 (1)°
V = 1188.72 (15) Å³
Z = 2
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 296 (2) K
0.13 × 0.10 × 0.08 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.966, T_max = 0.978
12513 measured reflections
4644 independent reflections
3999 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.117
S = 1.08
4644 reflections
334 parameters
30 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O1ⁱ	0.89	1.91	2.770 (2)	162
N1A—H1A1⋯O5ⁱⁱ	0.89	2.03	2.897 (3)	163
N1—H1C⋯O1Wⁱ	0.89	2.07	2.948 (3)	167
N1A—H1A2⋯O2Wⁱⁱⁱ	0.89	1.86	2.739 (3)	171
N1A—H1A3⋯O1Wⁱⁱⁱ	0.89	1.95	2.807 (3)	161
O1W—H1WA⋯O4ⁱ	0.860 (10)	1.801 (10)	2.645 (2)	166 (2)
O1W—H1WB⋯O6^iv	0.854 (10)	1.957 (11)	2.807 (2)	174 (3)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x, y+1, z; (iii) -x, -y+2, -z+1; (iv) x, y, z+1.

Data collection: SMART (Bruker, 2003 ); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680800723X/bh2163sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680800723X/bh2163Isup2.hkl

checkCIF report

Comment top

This work continues our previous synthetic and structural studies of supramolecular interactions in aromatic molecular salts and adducts (Wang & Wei, 2007). Herein we report the structure of the title salt, (I).

The title complex, (I), consists of one crystallographically independent 4,4'-diphenylmethylendiammonium dication, two water molecules and two independent half naphthalene-1,5-disulfonate dianions. In the dication, the dihedral angle between benzene rings is 74.67 (6)°, and central C1—C7—C1A angle is 112.23 (16)° (Fig. 1). Each dianion is placed on an inversion centre. The 4,4'-diphenylmethylendiammonium dication interact with two naphthalene-1,5-disulfonate dianions through N—H···O hydrogen bonds. These units are further linked by water molecules into an infinite three-dimensional framework by hydrogen bonds (Fig. 2).

Related literature top

For related literature, see: Wang & Wei (2007).

Experimental top

A 5 ml e thanol solution of 4,4'-methylene-bis(benzenamine) (0.5 mmol, 0.10 g) was added to an aqueous solution (25 ml) of naphthalene-1,5-disulfonic acid (0.50 mmol, 0.15 g). The mixture was stirred for 10 min. at 373 K. The solution was filtered, and the filtrate was allowed to stand at room temperature. After several days, colourless crystals suitable for X-ray diffraction were obtained.

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SMART (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

Fig. 1. The structure of (I) including the asymmetric unit (labeled atoms) and anions completed through symmetry operators: unlabeled atoms in the C10 anion are related to labeled atoms by symmetry code -x + 1, -y, -z + 1; unlabeled atoms in the C16 anion are related to labeled atoms by symmetry code -x + 1, -y, -z. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level. Hydrogen bonds are shown as dashed lines.

Fig. 2. The crystal packing of (I). Hydrogen bonds are shown as dashed lines. For clarity, H atoms not involved in hydrogen bonds are omitted.

Bis(4,4'-methylenedianilinium) naphthalene-1,5-disulfonate dihydrate top

Crystal data top

C₁₃H₁₆N₂²⁺·C₁₀H₆O₆S₂²⁻·2H₂O	Z = 2
M_r = 522.58	F(000) = 548
Triclinic, P1	D_x = 1.460 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9652 (6) Å	Cell parameters from 3560 reflections
b = 10.9135 (8) Å	θ = 2.3–28.5°
c = 13.8158 (10) Å	µ = 0.28 mm⁻¹
α = 87.429 (1)°	T = 296 K
β = 85.820 (1)°	Block, colourless
γ = 83.262 (1)°	0.13 × 0.10 × 0.08 mm
V = 1188.72 (15) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4644 independent reflections
Radiation source: fine-focus sealed tube	3999 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
ω scans	θ_max = 26.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −9→9
T_min = 0.966, T_max = 0.978	k = −13→13
12513 measured reflections	l = −17→17

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0622P)² + 0.4195P] where P = (F_o² + 2F_c²)/3
4644 reflections	(Δ/σ)_max < 0.001
334 parameters	Δρ_max = 0.30 e Å⁻³
30 restraints	Δρ_min = −0.30 e Å⁻³
0 constraints

Crystal data top

C₁₃H₁₆N₂²⁺·C₁₀H₆O₆S₂²⁻·2H₂O	γ = 83.262 (1)°
M_r = 522.58	V = 1188.72 (15) Å³
Triclinic, P1	Z = 2
a = 7.9652 (6) Å	Mo Kα radiation
b = 10.9135 (8) Å	µ = 0.28 mm⁻¹
c = 13.8158 (10) Å	T = 296 K
α = 87.429 (1)°	0.13 × 0.10 × 0.08 mm
β = 85.820 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4644 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	3999 reflections with I > 2σ(I)
T_min = 0.966, T_max = 0.978	R_int = 0.015
12513 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	30 restraints
wR(F²) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.30 e Å⁻³
4644 reflections	Δρ_min = −0.30 e Å⁻³
334 parameters

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

	x	y	z	U_iso*/U_eq
S1	0.40383 (6)	0.31683 (4)	0.49763 (3)	0.04147 (14)
S2	0.37003 (7)	0.28607 (4)	0.09053 (4)	0.04796 (16)
N1	0.4334 (2)	0.52270 (16)	0.28512 (13)	0.0515 (4)
H1A	0.4107	0.4478	0.3063	0.077*
H1B	0.4850	0.5571	0.3302	0.077*
H1C	0.5006	0.5166	0.2308	0.077*
N1A	−0.0574 (3)	1.33594 (17)	0.21344 (16)	0.0635 (5)
H1A1	0.0516	1.3376	0.1947	0.095*
H1A2	−0.0772	1.3627	0.2736	0.095*
H1A3	−0.1207	1.3845	0.1734	0.095*
O1	0.4100 (2)	0.32750 (13)	0.60152 (11)	0.0566 (4)
O2	0.5575 (2)	0.34399 (13)	0.44339 (12)	0.0595 (4)
O3	0.2547 (2)	0.38716 (13)	0.46064 (14)	0.0666 (5)
O4	0.5241 (2)	0.33961 (14)	0.05942 (14)	0.0723 (5)
O5	0.3092 (2)	0.31235 (14)	0.18981 (12)	0.0669 (5)
O6	0.2382 (2)	0.31961 (13)	0.02363 (12)	0.0615 (4)
O1W	0.2991 (2)	0.49532 (17)	0.87440 (13)	0.0664 (4)
H1WA	0.358 (3)	0.541 (2)	0.9040 (17)	0.079 (5)*
H1WB	0.273 (4)	0.4416 (19)	0.9181 (15)	0.085 (5)*
O2W	0.0816 (3)	0.5858 (2)	0.59992 (18)	0.0880 (6)
H2WA	0.171 (2)	0.538 (2)	0.610 (2)	0.088 (5)*
H2WB	0.014 (3)	0.542 (2)	0.578 (3)	0.111 (5)*
C1	−0.0257 (2)	0.74496 (17)	0.22988 (14)	0.0439 (4)
C2	0.0752 (3)	0.68758 (19)	0.15493 (14)	0.0485 (5)
H2	0.0409	0.6979	0.0919	0.058*
C3	0.2255 (3)	0.61548 (18)	0.17187 (14)	0.0457 (4)
H3	0.2924	0.5783	0.1209	0.055*
C4	0.2745 (2)	0.59965 (16)	0.26548 (14)	0.0404 (4)
C5	0.1767 (3)	0.65344 (17)	0.34204 (14)	0.0450 (4)
H5	0.2110	0.6411	0.4050	0.054*
C6	0.0275 (3)	0.72579 (18)	0.32417 (14)	0.0466 (4)
H6	−0.0388	0.7624	0.3756	0.056*
C7	−0.1870 (3)	0.8271 (2)	0.21082 (17)	0.0532 (5)
H7A	−0.2744	0.8101	0.2606	0.064*
H7B	−0.2248	0.8081	0.1486	0.064*
C8	0.3828 (2)	0.15788 (15)	0.48048 (12)	0.0361 (4)
C9	0.2418 (2)	0.13005 (17)	0.43965 (14)	0.0434 (4)
H9	0.1597	0.1931	0.4217	0.052*
C10	0.2200 (3)	0.00641 (18)	0.42456 (15)	0.0459 (4)
H10	0.1227	−0.0117	0.3974	0.055*
C11	0.6604 (2)	0.08693 (16)	0.55070 (13)	0.0410 (4)
H11	0.6764	0.1680	0.5620	0.049*
C12	0.5117 (2)	0.06267 (15)	0.50798 (11)	0.0330 (4)
C13	0.4159 (2)	0.12309 (16)	0.08655 (13)	0.0387 (4)
C14	0.4905 (2)	0.06601 (15)	0.00027 (13)	0.0342 (4)
C15	0.5455 (2)	0.13320 (16)	−0.08410 (14)	0.0424 (4)
H15	0.5351	0.2190	−0.0839	0.051*
C16	0.6129 (3)	0.07474 (18)	−0.16519 (15)	0.0521 (5)
H16	0.6467	0.1208	−0.2199	0.062*
C17	0.3680 (3)	0.05438 (18)	0.16698 (14)	0.0503 (5)
H17	0.3225	0.0935	0.2230	0.060*
C1A	−0.1634 (2)	0.96266 (19)	0.21010 (14)	0.0461 (4)
C2A	−0.2043 (3)	1.0326 (2)	0.29072 (17)	0.0642 (6)
H2A	−0.2545	0.9966	0.3461	0.077*
C3A	−0.1734 (3)	1.1542 (2)	0.29229 (18)	0.0649 (6)
H3A	−0.2018	1.1990	0.3480	0.078*
C4A	−0.1006 (3)	1.20806 (19)	0.21109 (16)	0.0508 (5)
C5A	−0.0614 (4)	1.1428 (2)	0.12952 (18)	0.0773 (8)
H5A	−0.0133	1.1800	0.0740	0.093*
C6A	−0.0929 (4)	1.0208 (2)	0.12897 (17)	0.0735 (7)
H6A	−0.0660	0.9770	0.0726	0.088*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0483 (3)	0.0258 (2)	0.0497 (3)	−0.00183 (18)	−0.0032 (2)	−0.00024 (18)
S2	0.0611 (3)	0.0264 (2)	0.0561 (3)	−0.0029 (2)	−0.0017 (2)	−0.00822 (19)
N1	0.0616 (11)	0.0389 (9)	0.0524 (10)	0.0040 (8)	−0.0110 (8)	0.0015 (7)
N1A	0.0630 (12)	0.0455 (10)	0.0768 (13)	0.0069 (9)	0.0045 (10)	0.0060 (9)
O1	0.0774 (10)	0.0408 (8)	0.0526 (9)	−0.0095 (7)	−0.0006 (7)	−0.0113 (6)
O2	0.0672 (10)	0.0366 (7)	0.0731 (10)	−0.0118 (7)	0.0141 (8)	0.0023 (7)
O3	0.0683 (10)	0.0322 (7)	0.0996 (13)	0.0047 (7)	−0.0284 (9)	0.0023 (7)
O4	0.0768 (11)	0.0421 (8)	0.1011 (14)	−0.0221 (8)	0.0043 (10)	−0.0137 (8)
O5	0.0972 (13)	0.0412 (8)	0.0606 (10)	0.0018 (8)	0.0009 (9)	−0.0181 (7)
O6	0.0727 (10)	0.0348 (7)	0.0754 (11)	0.0048 (7)	−0.0159 (8)	0.0043 (7)
O1W	0.0779 (11)	0.0591 (10)	0.0653 (10)	−0.0166 (8)	−0.0188 (9)	0.0083 (8)
O2W	0.0815 (14)	0.0805 (14)	0.1024 (16)	−0.0080 (11)	0.0011 (12)	−0.0227 (12)
C1	0.0446 (10)	0.0385 (10)	0.0500 (11)	−0.0097 (8)	−0.0055 (8)	0.0018 (8)
C2	0.0612 (12)	0.0451 (11)	0.0396 (10)	−0.0037 (9)	−0.0107 (9)	0.0003 (8)
C3	0.0595 (12)	0.0370 (10)	0.0398 (10)	−0.0013 (8)	−0.0025 (9)	−0.0042 (8)
C4	0.0503 (11)	0.0273 (8)	0.0441 (10)	−0.0058 (7)	−0.0062 (8)	0.0004 (7)
C5	0.0588 (12)	0.0392 (10)	0.0382 (10)	−0.0089 (9)	−0.0079 (8)	0.0021 (8)
C6	0.0523 (11)	0.0438 (10)	0.0432 (10)	−0.0066 (9)	0.0027 (8)	−0.0036 (8)
C7	0.0434 (11)	0.0549 (12)	0.0615 (13)	−0.0049 (9)	−0.0071 (9)	0.0006 (10)
C8	0.0441 (10)	0.0274 (8)	0.0360 (9)	−0.0027 (7)	−0.0007 (7)	0.0002 (7)
C9	0.0471 (10)	0.0346 (9)	0.0478 (10)	0.0008 (8)	−0.0091 (8)	0.0008 (8)
C10	0.0455 (11)	0.0415 (10)	0.0527 (11)	−0.0062 (8)	−0.0142 (9)	−0.0031 (8)
C11	0.0474 (10)	0.0323 (9)	0.0446 (10)	−0.0075 (7)	−0.0060 (8)	−0.0039 (7)
C12	0.0404 (9)	0.0287 (8)	0.0293 (8)	−0.0037 (7)	0.0013 (7)	−0.0004 (6)
C13	0.0451 (10)	0.0274 (8)	0.0432 (10)	−0.0016 (7)	−0.0041 (8)	−0.0038 (7)
C14	0.0343 (9)	0.0268 (8)	0.0416 (9)	−0.0028 (6)	−0.0057 (7)	−0.0012 (7)
C15	0.0490 (11)	0.0273 (8)	0.0497 (11)	−0.0032 (7)	0.0008 (8)	0.0021 (7)
C16	0.0668 (13)	0.0393 (10)	0.0462 (11)	−0.0011 (9)	0.0083 (10)	0.0084 (8)
C17	0.0665 (13)	0.0398 (10)	0.0414 (10)	0.0027 (9)	0.0042 (9)	−0.0033 (8)
C1A	0.0366 (10)	0.0529 (11)	0.0465 (11)	0.0030 (8)	−0.0043 (8)	0.0057 (9)
C2A	0.0727 (15)	0.0602 (14)	0.0555 (13)	−0.0088 (12)	0.0233 (11)	0.0015 (10)
C3A	0.0736 (16)	0.0576 (14)	0.0583 (14)	0.0000 (12)	0.0213 (12)	−0.0067 (11)
C4A	0.0478 (11)	0.0427 (11)	0.0570 (12)	0.0091 (9)	0.0008 (9)	0.0079 (9)
C5A	0.120 (2)	0.0620 (15)	0.0465 (13)	−0.0132 (15)	0.0164 (14)	0.0118 (11)
C6A	0.111 (2)	0.0629 (15)	0.0436 (12)	−0.0113 (14)	0.0155 (13)	−0.0026 (11)

Geometric parameters (Å, º) top

S1—O2	1.4417 (16)	C7—H7A	0.9700
S1—O3	1.4495 (15)	C7—H7B	0.9700
S1—O1	1.4501 (15)	C8—C9	1.364 (3)
S1—C8	1.7900 (17)	C8—C12	1.432 (2)
S2—O4	1.4496 (17)	C9—C10	1.407 (3)
S2—O5	1.4507 (17)	C9—H9	0.9300
S2—O6	1.4531 (17)	C10—C11ⁱ	1.360 (3)
S2—C13	1.7759 (17)	C10—H10	0.9300
N1—C4	1.470 (2)	C11—C10ⁱ	1.360 (3)
N1—H1A	0.8900	C11—C12	1.418 (3)
N1—H1B	0.8900	C11—H11	0.9300
N1—H1C	0.8900	C12—C12ⁱ	1.431 (3)
N1A—C4A	1.478 (3)	C13—C17	1.369 (3)
N1A—H1A1	0.8900	C13—C14	1.428 (2)
N1A—H1A2	0.8900	C14—C15	1.419 (3)
N1A—H1A3	0.8900	C14—C14ⁱⁱ	1.431 (3)
O1W—H1WA	0.860 (10)	C15—C16	1.359 (3)
O1W—H1WB	0.854 (10)	C15—H15	0.9300
O2W—H2WA	0.847 (10)	C16—C17ⁱⁱ	1.401 (3)
O2W—H2WB	0.840 (10)	C16—H16	0.9300
C1—C2	1.389 (3)	C17—C16ⁱⁱ	1.401 (3)
C1—C6	1.399 (3)	C17—H17	0.9300
C1—C7	1.510 (3)	C1A—C2A	1.376 (3)
C2—C3	1.382 (3)	C1A—C6A	1.379 (3)
C2—H2	0.9300	C2A—C3A	1.379 (3)
C3—C4	1.375 (3)	C2A—H2A	0.9300
C3—H3	0.9300	C3A—C4A	1.366 (3)
C4—C5	1.378 (3)	C3A—H3A	0.9300
C5—C6	1.379 (3)	C4A—C5A	1.358 (3)
C5—H5	0.9300	C5A—C6A	1.384 (4)
C6—H6	0.9300	C5A—H5A	0.9300
C7—C1A	1.512 (3)	C6A—H6A	0.9300

O2—S1—O3	112.14 (10)	H7A—C7—H7B	107.9
O2—S1—O1	113.15 (10)	C9—C8—C12	120.94 (16)
O3—S1—O1	112.19 (10)	C9—C8—S1	118.27 (14)
O2—S1—C8	106.96 (8)	C12—C8—S1	120.78 (13)
O3—S1—C8	106.27 (9)	C8—C9—C10	120.28 (17)
O1—S1—C8	105.51 (8)	C8—C9—H9	119.9
O4—S2—O5	113.54 (11)	C10—C9—H9	119.9
O4—S2—O6	111.67 (11)	C11ⁱ—C10—C9	120.71 (18)
O5—S2—O6	111.49 (11)	C11ⁱ—C10—H10	119.6
O4—S2—C13	107.67 (9)	C9—C10—H10	119.6
O5—S2—C13	106.25 (9)	C10ⁱ—C11—C12	121.09 (17)
O6—S2—C13	105.67 (9)	C10ⁱ—C11—H11	119.5
C4—N1—H1A	109.5	C12—C11—H11	119.5
C4—N1—H1B	109.5	C11—C12—C12ⁱ	118.75 (19)
H1A—N1—H1B	109.5	C11—C12—C8	123.03 (15)
C4—N1—H1C	109.5	C12ⁱ—C12—C8	118.22 (19)
H1A—N1—H1C	109.5	C17—C13—C14	121.41 (16)
H1B—N1—H1C	109.5	C17—C13—S2	117.57 (14)
C4A—N1A—H1A1	109.5	C14—C13—S2	120.91 (13)
C4A—N1A—H1A2	109.5	C15—C14—C13	123.46 (15)
H1A1—N1A—H1A2	109.5	C15—C14—C14ⁱⁱ	118.9 (2)
C4A—N1A—H1A3	109.5	C13—C14—C14ⁱⁱ	117.66 (19)
H1A1—N1A—H1A3	109.5	C16—C15—C14	121.31 (17)
H1A2—N1A—H1A3	109.5	C16—C15—H15	119.3
H1WA—O1W—H1WB	103.5 (14)	C14—C15—H15	119.3
H2WA—O2W—H2WB	106.2 (15)	C15—C16—C17ⁱⁱ	120.51 (18)
C2—C1—C6	117.94 (19)	C15—C16—H16	119.7
C2—C1—C7	121.48 (18)	C17ⁱⁱ—C16—H16	119.7
C6—C1—C7	120.57 (19)	C13—C17—C16ⁱⁱ	120.20 (18)
C3—C2—C1	121.54 (18)	C13—C17—H17	119.9
C3—C2—H2	119.2	C16ⁱⁱ—C17—H17	119.9
C1—C2—H2	119.2	C2A—C1A—C6A	116.8 (2)
C4—C3—C2	118.83 (19)	C2A—C1A—C7	122.09 (19)
C4—C3—H3	120.6	C6A—C1A—C7	121.1 (2)
C2—C3—H3	120.6	C1A—C2A—C3A	122.3 (2)
C3—C4—C5	121.45 (18)	C1A—C2A—H2A	118.8
C3—C4—N1	119.68 (18)	C3A—C2A—H2A	118.8
C5—C4—N1	118.87 (17)	C4A—C3A—C2A	119.3 (2)
C4—C5—C6	119.20 (18)	C4A—C3A—H3A	120.4
C4—C5—H5	120.4	C2A—C3A—H3A	120.4
C6—C5—H5	120.4	C5A—C4A—C3A	120.2 (2)
C5—C6—C1	121.03 (19)	C5A—C4A—N1A	119.9 (2)
C5—C6—H6	119.5	C3A—C4A—N1A	119.9 (2)
C1—C6—H6	119.5	C4A—C5A—C6A	120.0 (2)
C1—C7—C1A	112.23 (16)	C4A—C5A—H5A	120.0
C1—C7—H7A	109.2	C6A—C5A—H5A	120.0
C1A—C7—H7A	109.2	C1A—C6A—C5A	121.5 (2)
C1—C7—H7B	109.2	C1A—C6A—H6A	119.3
C1A—C7—H7B	109.2	C5A—C6A—H6A	119.3

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O1ⁱⁱⁱ	0.89	1.91	2.770 (2)	162
N1A—H1A1···O5^iv	0.89	2.03	2.897 (3)	163
N1—H1C···O1Wⁱⁱⁱ	0.89	2.07	2.948 (3)	167
N1A—H1A2···O2W^v	0.89	1.86	2.739 (3)	171
N1A—H1A3···O1W^v	0.89	1.95	2.807 (3)	161
O1W—H1WA···O4ⁱⁱⁱ	0.86 (1)	1.80 (1)	2.645 (2)	166 (2)
O1W—H1WB···O6^vi	0.85 (1)	1.96 (1)	2.807 (2)	174 (3)
N1—H1A···O2	0.89	2.46	3.007 (2)	120
N1—H1A···O5	0.89	2.47	2.996 (2)	118
N1—H1A···O3	0.89	2.49	3.125 (3)	129
O2W—H2WA···O2ⁱⁱⁱ	0.85 (1)	2.68 (3)	3.072 (3)	110 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₆N₂²⁺·C₁₀H₆O₆S₂²⁻·2H₂O
M_r	522.58
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.9652 (6), 10.9135 (8), 13.8158 (10)
α, β, γ (°)	87.429 (1), 85.820 (1), 83.262 (1)
V (Å³)	1188.72 (15)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.13 × 0.10 × 0.08

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.966, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	12513, 4644, 3999
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.117, 1.08
No. of reflections	4644
No. of parameters	334
No. of restraints	30
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.30

Computer programs: SMART (Bruker, 2003), SAINT-Plus (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O1ⁱ	0.89	1.91	2.770 (2)	162.4
N1A—H1A1···O5ⁱⁱ	0.89	2.03	2.897 (3)	162.9
N1—H1C···O1Wⁱ	0.89	2.07	2.948 (3)	166.8
N1A—H1A2···O2Wⁱⁱⁱ	0.89	1.86	2.739 (3)	170.9
N1A—H1A3···O1Wⁱⁱⁱ	0.89	1.95	2.807 (3)	161.4
O1W—H1WA···O4ⁱ	0.860 (10)	1.801 (10)	2.645 (2)	166 (2)
O1W—H1WB···O6^iv	0.854 (10)	1.957 (11)	2.807 (2)	174 (3)

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

References

Bruker (2003). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, Z.-L. & Wei, L.-H. (2007). Acta Cryst. E63, o1448–o1449. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 4| April 2008| Page o734

doi:10.1107/S160053680800723X

Open

access