1,1′-(p-Phenyl­enedimethyl­idene)diimidazol-3-ium bis­{2-[(2-carb­oxy­phen­yl)disulfan­yl]benzoate} dihydrate

Liu, Z.; Liu, Q.; Yuan, L.; Liu, W.

doi:10.1107/S1600536810047021

organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3230

https://doi.org/10.1107/S1600536810047021

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1,1′-(p-Phenylenedimethylidene)diimidazol-3-ium bis{2-[(2-carboxyphenyl)disulfanyl]benzoate} dihydrate

Zhengming Liu,^a Qiang Liu,^b Limin Yuan ^a and Wenlong Liu ^b ^*

^aTesting Center, Yangzhou University, Yangzhou 225002, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, People's Republic of China
^*Correspondence e-mail: liuwl@yzu.edu.cn

(Received 7 November 2010; accepted 13 November 2010; online 20 November 2010)

The title salt, C₁₄H₁₆N₄²⁺·2C₁₄H₉O₄S₂⁻·2H₂O, was obtained by the co-crystalization of 2,2′-dithiodibenzoic acid with 1,4-bis(imidazol-1-ylmethyl)benzene. It consists of 2-[(2-carboxyphenyl)disulfanyl]benzoate anions, centrosymmetric 1,1′-(p-phenylenedimethylidene)diimidazol-3-ium cations and water molecules. O—H⋯O, O—H⋯S and N—H⋯O hydrogen-bonding interactions among the components lead to the formation of a three-dimensional network.

Related literature

For background to the co-crystalization of 2,2′-dithiodibenzoic acid with bipyridine-type molecules, see: Bi et al. (2002 ); Broker & Tiekink (2007 ); Broker et al. (2008 ); Hu et al. (2004 ).

Experimental

Crystal data

C₁₄H₁₆N₄²⁺·2C₁₄H₉O₄S₂⁻·2H₂O
M_r = 887.00
Triclinic, $[P \overline 1]$
a = 4.6776 (11) Å
b = 12.201 (3) Å
c = 18.850 (4) Å
α = 107.985 (3)°
β = 90.686 (3)°
γ = 100.634 (3)°
V = 1002.9 (4) Å³
Z = 1
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 296 K
0.45 × 0.43 × 0.38 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.876, T_max = 0.894
7640 measured reflections
3708 independent reflections
2720 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.134
S = 1.08
3708 reflections
284 parameters
9 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WB⋯S1ⁱ	0.88 (2)	2.80 (3)	3.507 (3)	138 (4)
O1W—H1WB⋯O2ⁱ	0.88 (2)	2.30 (2)	3.141 (4)	159 (4)
N1—H1⋯O1ⁱⁱ	0.91 (2)	1.75 (2)	2.657 (3)	176 (3)
O4—H4A⋯O1ⁱⁱ	0.87 (2)	1.73 (3)	2.567 (3)	161 (4)
O1W—H1WA⋯O2	0.88 (2)	1.94 (2)	2.811 (3)	171 (4)
Symmetry codes: (i) x-1, y, z; (ii) x, y-1, z.

Data collection: SMART (Bruker, 2002 ); 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: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810047021/ng5063sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810047021/ng5063Isup2.hkl

checkCIF report

Comment top

The dicarboxylic acid DTBA has been shown to be effective and reliable in forming a range of co-crystals with a series of bipyridine-type molecules leading to varying supramolecular architectures(Broker & Tiekink, 2007; Broker et al., 2008). In comparison, the use of biimidazole-type molecules to co-crystal with DTBA remains largely unexplored. Herein, the formation of co-crystals of 2,2'-dithiodibenzoic acid with 1,4-bis(imidazol-1-ylmethyl)benzene is described, which were isolated from methanol. The asymmetric unit of the title compound comprises a singly deprotonated DTBA anion, half a 1,4-bis(imidazolium-1-ylmethyl)benzene dication, disposed about a centre of inversion, and a solvent water molecule of crystallization (Fig. 1). The dihedral angle between the two phenyl rings of HDTBA^-and torsion angle (C2/S1/S2/C9) are 73.54 (7)° and -84.93 (12)°, respectively. There are extensive hydrogen-bonding interactions between the carboxyl groups, protonated N atoms and water molecules of (I). As shown in Fig. 2, hydrogen-bonding interactions link water molecules to (C₁₄H₉O₄S₂)^- anions, (C₁₄H₁₆N₄)²⁺ cations and connect (C₁₄H₉O₄S₂)^-anions to (C₁₄H₁₆N₄)²⁺ cations to form an extended three-dimensional network.

Related literature top

For background to the co-crystalization of 2,2'-dithiodibenzoic acid with bipyridine-type molecules, see: Bi et al. (2002); Broker & Tiekink (2007); Broker et al. (2008); Hu et al. (2004).

Experimental top

2,2'-Dithiodibenzoic acid (153 mg, 0.5 mmol) was dissolved in 15 ml me thanol, and a solution of 1,4-bis(imidazol-1-ylmethyl)benzene (191 mg, 0.8 mmol) in 20 ml me thanol was added dropwise under intense agitation. The resulting mixture was stirred under reflux conditions for 1 h and allowed to cool to room temperature, filtered. After allowing the solution to stand for five days, colourless block-like crystals of (I) were obtained in 42% yield.

Structure description top

For background to the co-crystalization of 2,2'-dithiodibenzoic acid with bipyridine-type molecules, see: Bi et al. (2002); Broker & Tiekink (2007); Broker et al. (2008); Hu et al. (2004).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT-Plus (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: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Molecular structures of the title compound, showing atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. The three-dimensional packing structure of the title compound, Hydrogen bonds are shown as dashed lines.

1,1'-(p-Phenylenedimethylidene)diimidazol-3-ium bis{2-[(2-carboxyphenyl)disulfanyl]benzoate} dihydrate top

Crystal data top

C₁₄H₁₆N₄²⁺·2C₁₄H₉O₄S₂⁻·2H₂O	Z = 1
M_r = 887.00	F(000) = 462
Triclinic, P1	D_x = 1.469 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.6776 (11) Å	Cell parameters from 1975 reflections
b = 12.201 (3) Å	θ = 2.3–24.5°
c = 18.850 (4) Å	µ = 0.30 mm⁻¹
α = 107.985 (3)°	T = 296 K
β = 90.686 (3)°	Block, colourless
γ = 100.634 (3)°	0.45 × 0.43 × 0.38 mm
V = 1002.9 (4) Å³

Data collection top

Bruker SMART APEX CCD diffractometer	3708 independent reflections
Radiation source: fine-focus sealed tube	2720 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
φ and ω scans	θ_max = 25.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −5→5
T_min = 0.876, T_max = 0.894	k = −14→14
7640 measured reflections	l = −20→22

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0676P)² + 0.1163P] where P = (F_o² + 2F_c²)/3
3708 reflections	(Δ/σ)_max < 0.001
284 parameters	Δρ_max = 0.26 e Å⁻³
9 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₄H₁₆N₄²⁺·2C₁₄H₉O₄S₂⁻·2H₂O	γ = 100.634 (3)°
M_r = 887.00	V = 1002.9 (4) Å³
Triclinic, P1	Z = 1
a = 4.6776 (11) Å	Mo Kα radiation
b = 12.201 (3) Å	µ = 0.30 mm⁻¹
c = 18.850 (4) Å	T = 296 K
α = 107.985 (3)°	0.45 × 0.43 × 0.38 mm
β = 90.686 (3)°

Data collection top

Bruker SMART APEX CCD diffractometer	3708 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	2720 reflections with I > 2σ(I)
T_min = 0.876, T_max = 0.894	R_int = 0.030
7640 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	9 restraints
wR(F²) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.26 e Å⁻³
3708 reflections	Δρ_min = −0.24 e Å⁻³
284 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
C1	0.9224 (5)	0.7640 (2)	0.21093 (14)	0.0356 (6)
C2	0.9027 (5)	0.6438 (2)	0.19945 (14)	0.0352 (6)
C3	1.0412 (6)	0.5796 (2)	0.14067 (15)	0.0443 (7)
H3	1.0227	0.4990	0.1313	0.053*
C4	1.2053 (6)	0.6331 (2)	0.09606 (16)	0.0500 (7)
H4	1.2968	0.5885	0.0571	0.060*
C5	1.2351 (6)	0.7522 (3)	0.10862 (17)	0.0483 (7)
H5	1.3507	0.7889	0.0794	0.058*
C6	1.0910 (6)	0.8157 (2)	0.16511 (16)	0.0437 (7)
H6	1.1066	0.8958	0.1729	0.052*
C7	0.7699 (6)	0.8391 (2)	0.27118 (16)	0.0405 (6)
C8	0.5723 (5)	0.1938 (2)	0.13953 (14)	0.0375 (6)
C9	0.5950 (5)	0.3156 (2)	0.15799 (14)	0.0357 (6)
C10	0.4493 (6)	0.3591 (2)	0.11132 (15)	0.0433 (7)
H10	0.4668	0.4399	0.1224	0.052*
C11	0.2789 (6)	0.2841 (3)	0.04877 (17)	0.0496 (7)
H11	0.1817	0.3148	0.0184	0.060*
C12	0.2513 (6)	0.1640 (3)	0.03089 (17)	0.0530 (8)
H12	0.1350	0.1135	−0.0110	0.064*
C13	0.3991 (6)	0.1202 (2)	0.07623 (16)	0.0461 (7)
H13	0.3825	0.0393	0.0642	0.055*
C14	0.7222 (6)	0.1414 (2)	0.18676 (16)	0.0445 (7)
S1	0.69255 (16)	0.57314 (5)	0.25775 (4)	0.0440 (2)
S2	0.81448 (17)	0.41403 (6)	0.23901 (4)	0.0461 (2)
O1	0.7530 (4)	0.94073 (15)	0.26811 (11)	0.0504 (5)
O2	0.6751 (5)	0.80190 (17)	0.32150 (12)	0.0636 (6)
O3	0.8747 (5)	0.19838 (17)	0.24241 (13)	0.0676 (7)
O4	0.6690 (6)	0.02564 (17)	0.16259 (13)	0.0670 (7)
H4A	0.737 (8)	0.003 (3)	0.1976 (19)	0.100*
C15	0.3094 (6)	0.1496 (3)	0.35488 (17)	0.0514 (7)
H15	0.3404	0.1817	0.3162	0.062*
C16	0.3162 (9)	0.0374 (3)	0.4231 (2)	0.0735 (10)
H16	0.3513	−0.0234	0.4398	0.088*
C17	0.1658 (8)	0.1195 (3)	0.4573 (2)	0.0731 (11)
H17	0.0816	0.1277	0.5026	0.088*
C18	0.0401 (6)	0.2974 (2)	0.43199 (18)	0.0513 (7)
H18A	−0.1118	0.2936	0.4662	0.062*
H18B	−0.0463	0.3040	0.3868	0.062*
C19	0.2748 (5)	0.4039 (2)	0.46723 (14)	0.0406 (6)
C20	0.4029 (7)	0.4741 (3)	0.42709 (17)	0.0623 (9)
H20	0.3376	0.4576	0.3774	0.075*
C21	0.3731 (7)	0.4311 (3)	0.54080 (16)	0.0656 (9)
H21	0.2879	0.3853	0.5692	0.079*
N1	0.4076 (5)	0.0579 (2)	0.36030 (15)	0.0512 (6)
H1	0.519 (5)	0.016 (2)	0.3270 (14)	0.056 (9)*
N2	0.1594 (5)	0.18873 (19)	0.41342 (13)	0.0466 (6)
O1W	0.2006 (6)	0.7532 (2)	0.40459 (14)	0.0758 (7)
H1WA	0.351 (5)	0.761 (4)	0.378 (2)	0.114*
H1WB	0.049 (5)	0.747 (4)	0.374 (2)	0.114*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0361 (14)	0.0302 (13)	0.0407 (15)	0.0070 (11)	−0.0009 (11)	0.0114 (11)
C2	0.0401 (14)	0.0307 (13)	0.0356 (14)	0.0101 (11)	0.0003 (11)	0.0098 (11)
C3	0.0482 (16)	0.0360 (14)	0.0505 (17)	0.0155 (12)	0.0083 (13)	0.0120 (13)
C4	0.0498 (17)	0.0509 (17)	0.0504 (18)	0.0191 (14)	0.0140 (14)	0.0121 (14)
C5	0.0459 (16)	0.0509 (17)	0.0537 (18)	0.0078 (13)	0.0100 (14)	0.0252 (14)
C6	0.0470 (16)	0.0321 (14)	0.0559 (18)	0.0072 (12)	0.0038 (14)	0.0201 (13)
C7	0.0451 (16)	0.0284 (13)	0.0477 (16)	0.0093 (11)	0.0017 (13)	0.0105 (12)
C8	0.0435 (15)	0.0298 (13)	0.0393 (15)	0.0086 (11)	0.0084 (12)	0.0103 (12)
C9	0.0403 (14)	0.0293 (13)	0.0380 (14)	0.0082 (11)	0.0092 (11)	0.0103 (11)
C10	0.0503 (16)	0.0351 (14)	0.0475 (16)	0.0142 (12)	0.0005 (13)	0.0141 (13)
C11	0.0501 (17)	0.0482 (17)	0.0500 (18)	0.0097 (14)	−0.0029 (14)	0.0148 (14)
C12	0.0528 (18)	0.0459 (17)	0.0484 (18)	−0.0006 (14)	−0.0066 (14)	0.0043 (14)
C13	0.0561 (17)	0.0312 (14)	0.0462 (17)	0.0035 (13)	0.0066 (14)	0.0083 (13)
C14	0.0612 (18)	0.0312 (14)	0.0445 (17)	0.0142 (13)	0.0093 (14)	0.0137 (13)
S1	0.0631 (5)	0.0266 (3)	0.0436 (4)	0.0107 (3)	0.0119 (3)	0.0114 (3)
S2	0.0665 (5)	0.0276 (3)	0.0438 (4)	0.0100 (3)	−0.0065 (3)	0.0108 (3)
O1	0.0689 (13)	0.0263 (9)	0.0578 (12)	0.0160 (9)	0.0077 (10)	0.0122 (9)
O2	0.0914 (16)	0.0426 (12)	0.0683 (15)	0.0263 (11)	0.0380 (13)	0.0250 (11)
O3	0.1023 (18)	0.0354 (11)	0.0633 (15)	0.0134 (11)	−0.0240 (13)	0.0143 (11)
O4	0.1058 (19)	0.0289 (10)	0.0678 (15)	0.0140 (11)	−0.0092 (13)	0.0178 (10)
C15	0.0584 (19)	0.0508 (18)	0.0452 (17)	0.0190 (15)	0.0045 (15)	0.0108 (14)
C16	0.104 (3)	0.0493 (19)	0.079 (3)	0.0279 (19)	0.024 (2)	0.0288 (19)
C17	0.106 (3)	0.0486 (19)	0.074 (2)	0.0176 (19)	0.040 (2)	0.0295 (18)
C18	0.0451 (16)	0.0388 (15)	0.0627 (19)	0.0098 (13)	0.0029 (14)	0.0049 (14)
C19	0.0419 (15)	0.0333 (14)	0.0432 (16)	0.0086 (11)	0.0046 (12)	0.0067 (12)
C20	0.076 (2)	0.057 (2)	0.0456 (18)	−0.0079 (17)	−0.0084 (16)	0.0171 (16)
C21	0.085 (2)	0.0540 (19)	0.0502 (19)	−0.0174 (17)	−0.0008 (17)	0.0245 (16)
N1	0.0537 (15)	0.0364 (13)	0.0564 (16)	0.0104 (11)	0.0033 (13)	0.0034 (12)
N2	0.0457 (13)	0.0360 (13)	0.0523 (15)	0.0053 (10)	0.0051 (11)	0.0070 (11)
O1W	0.0771 (17)	0.0846 (18)	0.0666 (17)	0.0079 (15)	0.0150 (13)	0.0294 (14)

Geometric parameters (Å, º) top

C1—C6	1.391 (3)	C14—O3	1.200 (3)
C1—C2	1.400 (3)	C14—O4	1.317 (3)
C1—C7	1.502 (4)	S1—S2	2.0515 (10)
C2—C3	1.389 (3)	O4—H4A	0.87 (2)
C2—S1	1.793 (3)	C15—N1	1.316 (4)
C3—C4	1.376 (4)	C15—N2	1.325 (4)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.378 (4)	C16—C17	1.337 (5)
C4—H4	0.9300	C16—N1	1.342 (4)
C5—C6	1.375 (4)	C16—H16	0.9300
C5—H5	0.9300	C17—N2	1.356 (4)
C6—H6	0.9300	C17—H17	0.9300
C7—O2	1.226 (3)	C18—N2	1.478 (3)
C7—O1	1.276 (3)	C18—C19	1.503 (4)
C8—C13	1.391 (4)	C18—H18A	0.9700
C8—C9	1.400 (3)	C18—H18B	0.9700
C8—C14	1.482 (4)	C19—C20	1.374 (3)
C9—C10	1.389 (4)	C19—C21	1.374 (3)
C9—S2	1.790 (3)	C20—C21ⁱ	1.381 (3)
C10—C11	1.380 (4)	C20—H20	0.9300
C10—H10	0.9300	C21—C20ⁱ	1.381 (3)
C11—C12	1.379 (4)	C21—H21	0.9300
C11—H11	0.9300	N1—H1	0.911 (17)
C12—C13	1.378 (4)	O1W—H1WA	0.876 (18)
C12—H12	0.9300	O1W—H1WB	0.883 (18)
C13—H13	0.9300

C6—C1—C2	118.7 (2)	C8—C13—H13	119.2
C6—C1—C7	118.9 (2)	O3—C14—O4	122.8 (3)
C2—C1—C7	122.4 (2)	O3—C14—C8	123.6 (2)
C3—C2—C1	118.8 (2)	O4—C14—C8	113.6 (3)
C3—C2—S1	120.61 (19)	C2—S1—S2	106.04 (8)
C1—C2—S1	120.52 (19)	C9—S2—S1	105.87 (8)
C4—C3—C2	121.1 (2)	C14—O4—H4A	107 (3)
C4—C3—H3	119.5	N1—C15—N2	109.0 (3)
C2—C3—H3	119.5	N1—C15—H15	125.5
C3—C4—C5	120.5 (3)	N2—C15—H15	125.5
C3—C4—H4	119.7	C17—C16—N1	108.1 (3)
C5—C4—H4	119.7	C17—C16—H16	125.9
C6—C5—C4	118.8 (3)	N1—C16—H16	125.9
C6—C5—H5	120.6	C16—C17—N2	107.0 (3)
C4—C5—H5	120.6	C16—C17—H17	126.5
C5—C6—C1	122.0 (2)	N2—C17—H17	126.5
C5—C6—H6	119.0	N2—C18—C19	111.0 (2)
C1—C6—H6	119.0	N2—C18—H18A	109.4
O2—C7—O1	123.3 (2)	C19—C18—H18A	109.4
O2—C7—C1	119.2 (2)	N2—C18—H18B	109.4
O1—C7—C1	117.5 (2)	C19—C18—H18B	109.4
C13—C8—C9	119.1 (2)	H18A—C18—H18B	108.0
C13—C8—C14	119.2 (2)	C20—C19—C21	118.3 (2)
C9—C8—C14	121.7 (2)	C20—C19—C18	121.7 (2)
C10—C9—C8	118.8 (2)	C21—C19—C18	120.0 (2)
C10—C9—S2	120.34 (19)	C19—C20—C21ⁱ	121.2 (3)
C8—C9—S2	120.83 (19)	C19—C20—H20	119.4
C11—C10—C9	120.9 (3)	C21ⁱ—C20—H20	119.4
C11—C10—H10	119.6	C19—C21—C20ⁱ	120.5 (3)
C9—C10—H10	119.6	C19—C21—H21	119.7
C12—C11—C10	120.7 (3)	C20ⁱ—C21—H21	119.7
C12—C11—H11	119.7	C15—N1—C16	108.1 (3)
C10—C11—H11	119.7	C15—N1—H1	125.3 (19)
C13—C12—C11	118.8 (3)	C16—N1—H1	126.6 (19)
C13—C12—H12	120.6	C15—N2—C17	107.8 (3)
C11—C12—H12	120.6	C15—N2—C18	125.6 (3)
C12—C13—C8	121.7 (3)	C17—N2—C18	126.2 (3)
C12—C13—H13	119.2	H1WA—O1W—H1WB	104 (3)

C6—C1—C2—C3	−2.9 (4)	C14—C8—C13—C12	179.1 (3)
C7—C1—C2—C3	177.6 (2)	C13—C8—C14—O3	−179.7 (3)
C6—C1—C2—S1	179.13 (19)	C9—C8—C14—O3	−1.2 (4)
C7—C1—C2—S1	−0.4 (3)	C13—C8—C14—O4	−0.7 (4)
C1—C2—C3—C4	2.6 (4)	C9—C8—C14—O4	177.8 (2)
S1—C2—C3—C4	−179.4 (2)	C3—C2—S1—S2	16.6 (2)
C2—C3—C4—C5	−0.2 (4)	C1—C2—S1—S2	−165.39 (19)
C3—C4—C5—C6	−1.9 (4)	C10—C9—S2—S1	16.4 (2)
C4—C5—C6—C1	1.6 (4)	C8—C9—S2—S1	−165.10 (18)
C2—C1—C6—C5	0.8 (4)	C2—S1—S2—C9	−84.96 (12)
C7—C1—C6—C5	−179.6 (3)	N1—C16—C17—N2	1.7 (4)
C6—C1—C7—O2	−164.2 (3)	N2—C18—C19—C20	100.9 (3)
C2—C1—C7—O2	15.3 (4)	N2—C18—C19—C21	−77.0 (3)
C6—C1—C7—O1	13.9 (4)	C21—C19—C20—C21ⁱ	0.8 (5)
C2—C1—C7—O1	−166.5 (2)	C18—C19—C20—C21ⁱ	−177.2 (3)
C13—C8—C9—C10	−1.6 (4)	C20—C19—C21—C20ⁱ	−0.8 (5)
C14—C8—C9—C10	179.9 (2)	C18—C19—C21—C20ⁱ	177.2 (3)
C13—C8—C9—S2	179.85 (19)	N2—C15—N1—C16	0.6 (4)
C14—C8—C9—S2	1.4 (3)	C17—C16—N1—C15	−1.5 (4)
C8—C9—C10—C11	1.6 (4)	N1—C15—N2—C17	0.5 (4)
S2—C9—C10—C11	−179.8 (2)	N1—C15—N2—C18	173.2 (2)
C9—C10—C11—C12	−0.5 (4)	C16—C17—N2—C15	−1.4 (4)
C10—C11—C12—C13	−0.6 (4)	C16—C17—N2—C18	−174.1 (3)
C11—C12—C13—C8	0.6 (4)	C19—C18—N2—C15	−78.1 (3)
C9—C8—C13—C12	0.5 (4)	C19—C18—N2—C17	93.3 (4)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WB···S1ⁱⁱ	0.88 (2)	2.80 (3)	3.507 (3)	138 (4)
O1W—H1WB···O2ⁱⁱ	0.88 (2)	2.30 (2)	3.141 (4)	159 (4)
N1—H1···O1ⁱⁱⁱ	0.91 (2)	1.75 (2)	2.657 (3)	176 (3)
O4—H4A···O1ⁱⁱⁱ	0.87 (2)	1.73 (3)	2.567 (3)	161 (4)
O1W—H1WA···O2	0.88 (2)	1.94 (2)	2.811 (3)	171 (4)

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₆N₄²⁺·2C₁₄H₉O₄S₂⁻·2H₂O
M_r	887.00
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	4.6776 (11), 12.201 (3), 18.850 (4)
α, β, γ (°)	107.985 (3), 90.686 (3), 100.634 (3)
V (Å³)	1002.9 (4)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.45 × 0.43 × 0.38

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.876, 0.894
No. of measured, independent and observed [I > 2σ(I)] reflections	7640, 3708, 2720
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.134, 1.08
No. of reflections	3708
No. of parameters	284
No. of restraints	9
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.24

Computer programs: SMART (Bruker, 2002), SAINT-Plus (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WB···S1ⁱ	0.883 (18)	2.80 (3)	3.507 (3)	138 (4)
O1W—H1WB···O2ⁱ	0.883 (18)	2.30 (2)	3.141 (4)	159 (4)
N1—H1···O1ⁱⁱ	0.911 (17)	1.748 (18)	2.657 (3)	176 (3)
O4—H4A···O1ⁱⁱ	0.87 (2)	1.73 (3)	2.567 (3)	161 (4)
O1W—H1WA···O2	0.876 (18)	1.94 (2)	2.811 (3)	171 (4)

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

Acknowledgements

This work was supported by the Foundation of the Key Laboratory of Environmental Materials and Environmental Engineering of Jiangsu Province.

References

Bi, W., Sun, D., Cao, R. & Hong, M. (2002). Acta Cryst. E58, o837–o839. Web of Science CSD CrossRef IUCr Journals Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Broker, G. A., Bettens, R. P. A. & Tiekink, E. R. T. (2008). CrystEngComm, 10, 879–887. Web of Science CSD CrossRef CAS Google Scholar
Broker, G. A. & Tiekink, E. R. T. (2007). CrystEngComm, 9, 1096–1109. Web of Science CSD CrossRef CAS Google Scholar
Bruker (2002). SMART for WNT/2000. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2003). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hu, R.-F., Wen, Y.-H., Zhang, J., Li, Z.-J. & Yao, Y.-G. (2004). Acta Cryst. E60, o2029–o2031. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2004). 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
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1,1′-(p-Phenyl­enedi­methyl­­idene)diimidazol-3-ium bis­­{2-[(2-carb­­oxy­phen­yl)disulfan­yl]benzoate} dihydrate

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Experimental

Crystal data

Data collection

Refinement

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References

organic compounds

1,1′-(p-Phenylenedimethylidene)diimidazol-3-ium bis{2-[(2-carboxyphenyl)disulfanyl]benzoate} dihydrate