1,1′-[1,4-Phenyl­enebis(methyl­ene)]bis­(2-methyl-1H-imidazol-3-ium) 2,4-dicarb­oxy­benzene-1,5-dicarboxyl­ate monohydrate

Dong, G.-Y.; Liu, T.-F.; He, C.-H.; Deng, X.-C.; Shi, X.-G.

doi:10.1107/S160053681102263X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1696

doi:10.1107/S160053681102263X

Open

access

1,1′-[1,4-Phenylenebis(methylene)]bis(2-methyl-1H-imidazol-3-ium) 2,4-dicarboxybenzene-1,5-dicarboxylate monohydrate

Gui-Ying Dong,^a ^* Tong-Fei Liu,^a Cui-Hong He,^a Xiao-Chen Deng ^b and Xiao-Ge Shi ^b

^aCollege of Chemical Engineering, Hebei United University, Tangshan 063009, People's Republic of China, and ^bQian'an College, Hebei United University, Tangshan 063009, People's Republic of China
^*Correspondence e-mail: tsdgying@126.com

(Received 7 June 2011; accepted 11 June 2011; online 18 June 2011)

In the dication of the title compound, C₁₆H₂₀N₄²⁺·C₁₀H₄O₈²⁻·H₂O, the dihedral angles formed by mean planes of the imidazolium rings and the benzene ring are 69.05 (18) and 89.1 (2)°. In the crystal, the components are linked into a three-dimensional network by intermolecular N—H⋯O and O—H⋯O hydrogen bonds.

Related literature

For the synthesis of 1,4-bis(2-methyl-1H-imidazole-3-ium)benzene, see: Hoskins et al. (1997 ). For related complexes, see: Liu Wu, Wan et al. (2011 ); Liu, Wu, Zhang & Cui (2011 ).

Experimental

Crystal data

C₁₆H₂₀N₄²⁺·C₁₀H₄O₈²⁻·H₂O
M_r = 538.51
Monoclinic, P 2₁ /c
a = 9.7139 (19) Å
b = 19.428 (4) Å
c = 13.856 (3) Å
β = 97.39 (3)°
V = 2593.3 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 295 K
0.22 × 0.18 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.968, T_max = 0.971
20668 measured reflections
4571 independent reflections
3075 reflections with I > 2σ(I)
R_int = 0.078

Refinement

R[F² > 2σ(F²)] = 0.073
wR(F²) = 0.144
S = 1.10
4571 reflections
356 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O6ⁱ	0.82	1.76	2.575 (3)	172
O1W—H1A⋯O6	0.86	1.90	2.747 (3)	168
O1W—H1B⋯O5ⁱⁱ	0.85	1.98	2.743 (3)	149
N4—H1C⋯O4ⁱⁱⁱ	0.98	1.75	2.679 (4)	158
N2—H2⋯O1W^iv	1.07	1.59	2.651 (4)	172
O8—H8⋯O3^v	0.82	1.81	2.586 (3)	157
Symmetry codes: (i) x+1, y, z; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) x-1, y, z; (v) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1999 ); data reduction: SAINT; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681102263X/lh5268sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681102263X/lh5268Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681102263X/lh5268Isup3.cml

checkCIF report

Comment top

1,4-bis(2-methylimidazole-1-methyl)benzene is a flexible bridging ligand, which can participate in the construction of coordination polymers and can provide information on the influences of 2-substituted derivatives of imidazole on the structures and properties of resulting complexes (Liu et al., 2011a,2011b). In our attempt to synthesize a zinc complex with this ligand, we unexpectedly obtained the title compound (I) and report herein its synthesis and crystal structure determination.

The asymmetric unit of (I) is shown in (Fig. 1). Bond distances and angles are as found in other structures (Liu Wu, Wan et al., 2011); Liu, Wu, Zhang & Cui, 2011). In the dication, the dihedral angles formed by the mean-planes of the imidazole rings and the benzene ring (C11-C16) are 69.05 (18)° (N1/N2/C18/C19/C20) and 89.1 (2)° (N3/N4/C23/C24/C25). In the crystal, the components are linked into a three-dimensional network by intermolecular N—H···O and O—H···O hydrogen bonds.

Related literature top

For the synthesis of 1,4-bis(2-methyl-1H-imidazole-3-ium)benzene, see: Hoskins et al. (1997). For related complexes, see: Liu Wu, Wan et al. (2011); Liu, Wu, Zhang & Cui (2011).

Experimental top

1,4-Bis(2-methylimidazole-1-methyl)benzene was prepared by the method of Hoskins et al. (1997). A mixture of Zn(NO₃)₂.6H₂O (298 mg,1 mmol), 1,4-bis(2-methylimidazole-1-methyl)benzene (1.0 mmol, 266.4 mg), 1,2,4,5-benzenetetracarboxylic acid (1.0 mmol, 254.2 mg) and H₂O (12 mL) was placed in a Teflon-lined stainless vessel and heated to 393 K for 4 days under autogenous pressure, and then cooled to room temperature in 24 h. block-shaped colourless crystals of (I) suitable for single-crystal X-ray diffraction analysis were obtained.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Fig. 1. The molecular structure of (I), showing displacement ellipsoids at the 30% probability levels.

1,1'-[1,4-Phenylenebis(methylene)]bis(2-methyl-1H-imidazol-3-ium) 2,4-dicarboxybenzene-1,5-dicarboxylate monohydrate top

Crystal data top

C₁₆H₂₀N₄²⁺·C₁₀H₄O₈²⁻·H₂O	F(000) = 1128
M_r = 538.51	D_x = 1.379 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2963 reflections
a = 9.7139 (19) Å	θ = 4.6–23.5°
b = 19.428 (4) Å	µ = 0.11 mm⁻¹
c = 13.856 (3) Å	T = 295 K
β = 97.39 (3)°	Block, colourless
V = 2593.3 (9) Å³	0.22 × 0.18 × 0.16 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	4571 independent reflections
Radiation source: fine–focus sealed tube	3075 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.078
ϕ and ω scans	θ_max = 25.0°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.968, T_max = 0.971	k = −23→23
20668 measured reflections	l = −16→16

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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.144	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0452P)² + 1.9004P] where P = (F_o² + 2F_c²)/3
4571 reflections	(Δ/σ)_max = 0.001
356 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₆H₂₀N₄²⁺·C₁₀H₄O₈²⁻·H₂O	V = 2593.3 (9) Å³
M_r = 538.51	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.7139 (19) Å	µ = 0.11 mm⁻¹
b = 19.428 (4) Å	T = 295 K
c = 13.856 (3) Å	0.22 × 0.18 × 0.16 mm
β = 97.39 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4571 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3075 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.971	R_int = 0.078
20668 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.073	0 restraints
wR(F²) = 0.144	H-atom parameters constrained
S = 1.10	Δρ_max = 0.30 e Å⁻³
4571 reflections	Δρ_min = −0.25 e Å⁻³
356 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
O1	1.3527 (2)	0.26814 (12)	0.7753 (2)	0.0460 (7)
H1	1.4361	0.2598	0.7806	0.069*
C1	1.1278 (3)	0.21981 (14)	0.7695 (2)	0.0211 (7)
O6	0.6182 (2)	0.25426 (12)	0.78948 (16)	0.0389 (6)
N2	0.0283 (3)	0.27283 (15)	1.00182 (19)	0.0370 (7)
C6	1.0713 (3)	0.28578 (15)	0.7517 (2)	0.0241 (7)
H6	1.1309	0.3232	0.7512	0.029*
C5	0.9277 (3)	0.29696 (14)	0.7346 (2)	0.0215 (7)
C2	1.0382 (3)	0.16286 (15)	0.7718 (2)	0.0228 (7)
O3	1.0942 (3)	0.04591 (11)	0.73740 (17)	0.0466 (7)
C10	0.8718 (3)	0.36897 (15)	0.7201 (2)	0.0280 (7)
O7	0.7529 (2)	0.38125 (12)	0.6872 (2)	0.0552 (8)
C4	0.8365 (3)	0.23966 (15)	0.7314 (2)	0.0211 (7)
C9	0.6773 (3)	0.24479 (15)	0.7138 (2)	0.0280 (7)
C3	0.8944 (3)	0.17407 (15)	0.7510 (2)	0.0251 (7)
H3	0.8351	0.1364	0.7501	0.030*
N3	0.4318 (3)	0.51795 (13)	0.63373 (19)	0.0311 (7)
O5	0.6155 (2)	0.23446 (14)	0.62994 (17)	0.0487 (7)
N1	0.2118 (3)	0.33609 (14)	1.03805 (19)	0.0341 (7)
C7	1.2841 (3)	0.21099 (16)	0.7850 (2)	0.0269 (7)
O4	1.1014 (3)	0.07904 (12)	0.89343 (18)	0.0526 (7)
C18	0.0723 (4)	0.33800 (18)	1.0185 (2)	0.0359 (8)
O2	1.3390 (2)	0.15570 (12)	0.8038 (2)	0.0622 (9)
C8	1.0850 (3)	0.08958 (16)	0.8028 (3)	0.0291 (8)
C14	0.4739 (3)	0.47375 (16)	0.8037 (2)	0.0303 (8)
O8	0.9640 (3)	0.41682 (12)	0.7470 (3)	0.0736 (10)
H8	0.9268	0.4547	0.7415	0.110*
C23	0.3679 (4)	0.47019 (17)	0.5734 (2)	0.0355 (8)
C25	0.3698 (4)	0.58156 (17)	0.6113 (3)	0.0398 (9)
H25	0.3942	0.6232	0.6419	0.048*
C17	0.3073 (4)	0.39578 (18)	1.0599 (3)	0.0445 (9)
H17A	0.3840	0.3821	1.1079	0.053*
H17B	0.2579	0.4327	1.0877	0.053*
C11	0.3644 (4)	0.42225 (17)	0.9695 (2)	0.0369 (9)
N4	0.2683 (3)	0.50177 (15)	0.5137 (2)	0.0436 (8)
C22	0.5378 (3)	0.50329 (17)	0.7177 (2)	0.0357 (8)
H22A	0.5868	0.5454	0.7377	0.043*
H22B	0.6047	0.4708	0.6981	0.043*
C19	0.1416 (4)	0.22940 (18)	1.0100 (3)	0.0411 (9)
H19	0.1395	0.1819	1.0015	0.049*
C20	0.2568 (4)	0.26881 (18)	1.0327 (2)	0.0388 (9)
H20	0.3482	0.2535	1.0427	0.047*
C13	0.5502 (4)	0.4301 (2)	0.8693 (3)	0.0532 (11)
H13	0.6392	0.4174	0.8586	0.064*
C24	0.2675 (4)	0.57139 (19)	0.5368 (3)	0.0476 (10)
H24	0.2079	0.6047	0.5068	0.057*
C16	0.2873 (5)	0.4638 (2)	0.9035 (3)	0.0718 (14)
H16	0.1973	0.4755	0.9134	0.086*
C12	0.4964 (4)	0.4048 (2)	0.9512 (3)	0.0556 (11)
H12	0.5504	0.3758	0.9940	0.067*
C15	0.3412 (4)	0.4890 (2)	0.8213 (3)	0.0677 (14)
H15	0.2857	0.5167	0.7775	0.081*
O1W	0.7588 (2)	0.24523 (16)	0.97416 (18)	0.0651 (9)
C26	0.4009 (4)	0.39518 (18)	0.5750 (3)	0.0522 (11)
H26A	0.3520	0.3725	0.6219	0.078*
H26B	0.4990	0.3889	0.5923	0.078*
H26C	0.3731	0.3759	0.5117	0.078*
C21	−0.0224 (4)	0.3989 (2)	1.0153 (3)	0.0587 (11)
H21A	−0.0020	0.4250	1.0742	0.088*
H21B	−0.1170	0.3835	1.0089	0.088*
H21C	−0.0089	0.4274	0.9606	0.088*
H1C	0.2174	0.4787	0.4575	0.088*
H2	−0.0820	0.2658	0.9924	0.088*
H1A	0.7048	0.2485	0.9205	0.088*
H1B	0.6895	0.2529	1.0044	0.088*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0160 (11)	0.0409 (15)	0.0811 (19)	0.0003 (11)	0.0055 (13)	0.0144 (13)
C1	0.0194 (16)	0.0217 (16)	0.0228 (17)	0.0016 (13)	0.0051 (13)	−0.0015 (13)
O6	0.0169 (11)	0.0709 (17)	0.0295 (13)	0.0036 (11)	0.0052 (10)	0.0011 (12)
N2	0.0357 (17)	0.0423 (18)	0.0331 (17)	0.0002 (14)	0.0045 (14)	−0.0022 (13)
C6	0.0203 (16)	0.0203 (16)	0.0315 (18)	−0.0035 (13)	0.0025 (14)	0.0007 (13)
C5	0.0186 (16)	0.0220 (16)	0.0241 (17)	0.0036 (13)	0.0037 (13)	0.0022 (13)
C2	0.0222 (16)	0.0205 (16)	0.0258 (17)	0.0003 (13)	0.0034 (13)	−0.0019 (13)
O3	0.0692 (18)	0.0224 (13)	0.0476 (16)	0.0054 (12)	0.0056 (13)	−0.0041 (12)
C10	0.0247 (18)	0.0238 (18)	0.035 (2)	0.0001 (15)	0.0030 (15)	0.0039 (14)
O7	0.0304 (15)	0.0345 (15)	0.097 (2)	0.0101 (11)	−0.0081 (14)	0.0086 (14)
C4	0.0175 (15)	0.0250 (17)	0.0206 (16)	0.0013 (13)	0.0016 (13)	0.0034 (13)
C9	0.0210 (17)	0.0278 (18)	0.035 (2)	0.0005 (14)	0.0019 (16)	0.0033 (15)
C3	0.0207 (16)	0.0234 (17)	0.0312 (18)	−0.0071 (13)	0.0029 (14)	0.0013 (14)
N3	0.0331 (15)	0.0300 (16)	0.0306 (16)	−0.0048 (13)	0.0059 (13)	−0.0040 (13)
O5	0.0243 (13)	0.086 (2)	0.0335 (15)	−0.0021 (13)	−0.0040 (11)	−0.0098 (13)
N1	0.0387 (17)	0.0352 (17)	0.0283 (16)	−0.0049 (14)	0.0037 (13)	0.0000 (13)
C7	0.0249 (17)	0.0249 (18)	0.0303 (19)	0.0020 (15)	0.0015 (15)	−0.0041 (14)
O4	0.0766 (19)	0.0400 (15)	0.0376 (16)	0.0118 (13)	−0.0067 (14)	0.0096 (12)
C18	0.041 (2)	0.040 (2)	0.0267 (19)	0.0029 (17)	0.0053 (16)	−0.0015 (16)
O2	0.0251 (13)	0.0291 (14)	0.130 (3)	0.0091 (11)	−0.0012 (15)	0.0043 (15)
C8	0.0228 (17)	0.0228 (18)	0.041 (2)	−0.0009 (14)	0.0020 (16)	0.0040 (16)
C14	0.0293 (18)	0.0299 (18)	0.0314 (19)	−0.0041 (15)	0.0023 (15)	−0.0035 (15)
O8	0.0444 (16)	0.0205 (14)	0.146 (3)	0.0020 (12)	−0.0264 (18)	0.0019 (17)
C23	0.040 (2)	0.032 (2)	0.034 (2)	−0.0040 (16)	0.0042 (17)	−0.0010 (16)
C25	0.049 (2)	0.0268 (19)	0.043 (2)	−0.0006 (17)	0.0027 (19)	−0.0008 (17)
C17	0.052 (2)	0.043 (2)	0.038 (2)	−0.0125 (19)	0.0045 (18)	−0.0023 (17)
C11	0.040 (2)	0.033 (2)	0.038 (2)	−0.0066 (17)	0.0048 (17)	−0.0026 (16)
N4	0.0488 (19)	0.0444 (19)	0.0342 (18)	−0.0055 (15)	−0.0076 (15)	−0.0051 (14)
C22	0.0316 (19)	0.036 (2)	0.038 (2)	−0.0015 (15)	−0.0029 (16)	−0.0011 (16)
C19	0.048 (2)	0.034 (2)	0.042 (2)	−0.0005 (18)	0.0113 (18)	−0.0044 (17)
C20	0.040 (2)	0.041 (2)	0.037 (2)	0.0061 (17)	0.0092 (17)	0.0013 (17)
C13	0.043 (2)	0.061 (3)	0.059 (3)	0.016 (2)	0.015 (2)	0.015 (2)
C24	0.055 (3)	0.040 (2)	0.044 (2)	0.0078 (19)	−0.006 (2)	0.0033 (18)
C16	0.055 (3)	0.093 (4)	0.073 (3)	0.030 (3)	0.034 (2)	0.032 (3)
C12	0.050 (3)	0.061 (3)	0.057 (3)	0.014 (2)	0.010 (2)	0.021 (2)
C15	0.055 (3)	0.084 (3)	0.068 (3)	0.030 (2)	0.022 (2)	0.045 (3)
O1W	0.0330 (14)	0.123 (3)	0.0385 (16)	−0.0012 (15)	0.0002 (12)	−0.0064 (16)
C26	0.059 (3)	0.036 (2)	0.059 (3)	−0.0044 (18)	0.000 (2)	−0.0091 (19)
C21	0.059 (3)	0.054 (3)	0.063 (3)	0.014 (2)	0.007 (2)	−0.004 (2)

Geometric parameters (Å, º) top

O1—C7	1.311 (4)	C14—C22	1.524 (5)
O1—H1	0.8200	O8—H8	0.8200
C1—C6	1.404 (4)	C23—N4	1.338 (4)
C1—C2	1.411 (4)	C23—C26	1.492 (5)
C1—C7	1.516 (4)	C25—C24	1.352 (5)
O6—C9	1.272 (4)	C25—H25	0.9300
N2—C18	1.347 (4)	C17—C11	1.523 (5)
N2—C19	1.380 (4)	C17—H17A	0.9700
N2—H2	1.0718	C17—H17B	0.9700
C6—C5	1.402 (4)	C11—C16	1.369 (5)
C6—H6	0.9300	C11—C12	1.381 (5)
C5—C4	1.420 (4)	N4—C24	1.390 (4)
C5—C10	1.505 (4)	N4—H1C	0.9761
C2—C3	1.406 (4)	C22—H22A	0.9700
C2—C8	1.539 (4)	C22—H22B	0.9700
O3—C8	1.253 (4)	C19—C20	1.359 (5)
C10—O7	1.210 (4)	C19—H19	0.9300
C10—O8	1.312 (4)	C20—H20	0.9300
C4—C3	1.405 (4)	C13—C12	1.398 (5)
C4—C9	1.538 (4)	C13—H13	0.9300
C9—O5	1.253 (4)	C24—H24	0.9300
C3—H3	0.9300	C16—C15	1.402 (5)
N3—C23	1.346 (4)	C16—H16	0.9300
N3—C25	1.392 (4)	C12—H12	0.9300
N3—C22	1.479 (4)	C15—H15	0.9300
N1—C18	1.349 (4)	O1W—H1A	0.8558
N1—C20	1.383 (4)	O1W—H1B	0.8509
N1—C17	1.492 (4)	C26—H26A	0.9600
C7—O2	1.212 (4)	C26—H26B	0.9600
O4—C8	1.262 (4)	C26—H26C	0.9600
C18—C21	1.496 (5)	C21—H21A	0.9600
C14—C15	1.374 (5)	C21—H21B	0.9600
C14—C13	1.386 (5)	C21—H21C	0.9600

C7—O1—H1	109.5	N1—C17—C11	112.2 (3)
C6—C1—C2	119.5 (3)	N1—C17—H17A	109.2
C6—C1—C7	119.4 (3)	C11—C17—H17A	109.2
C2—C1—C7	121.2 (3)	N1—C17—H17B	109.2
C18—N2—C19	109.2 (3)	C11—C17—H17B	109.2
C18—N2—H2	115.5	H17A—C17—H17B	107.9
C19—N2—H2	134.9	C16—C11—C12	117.6 (3)
C5—C6—C1	122.0 (3)	C16—C11—C17	121.5 (3)
C5—C6—H6	119.0	C12—C11—C17	120.9 (3)
C1—C6—H6	119.0	C23—N4—C24	109.2 (3)
C6—C5—C4	119.2 (3)	C23—N4—H1C	122.3
C6—C5—C10	120.1 (3)	C24—N4—H1C	127.8
C4—C5—C10	120.8 (2)	N3—C22—C14	112.0 (3)
C3—C2—C1	118.2 (3)	N3—C22—H22A	109.2
C3—C2—C8	116.8 (2)	C14—C22—H22A	109.2
C1—C2—C8	124.8 (3)	N3—C22—H22B	109.2
O7—C10—O8	123.5 (3)	C14—C22—H22B	109.2
O7—C10—C5	123.0 (3)	H22A—C22—H22B	107.9
O8—C10—C5	113.5 (3)	C20—C19—N2	107.4 (3)
C3—C4—C5	118.2 (3)	C20—C19—H19	126.3
C3—C4—C9	117.3 (3)	N2—C19—H19	126.3
C5—C4—C9	124.4 (2)	C19—C20—N1	106.8 (3)
O5—C9—O6	125.1 (3)	C19—C20—H20	126.6
O5—C9—C4	119.2 (3)	N1—C20—H20	126.6
O6—C9—C4	115.4 (3)	C14—C13—C12	121.6 (3)
C4—C3—C2	122.9 (3)	C14—C13—H13	119.2
C4—C3—H3	118.6	C12—C13—H13	119.2
C2—C3—H3	118.6	C25—C24—N4	107.0 (3)
C23—N3—C25	108.8 (3)	C25—C24—H24	126.5
C23—N3—C22	125.1 (3)	N4—C24—H24	126.5
C25—N3—C22	125.7 (3)	C11—C16—C15	121.3 (4)
C18—N1—C20	109.4 (3)	C11—C16—H16	119.4
C18—N1—C17	127.0 (3)	C15—C16—H16	119.4
C20—N1—C17	123.6 (3)	C11—C12—C13	121.0 (4)
O2—C7—O1	123.9 (3)	C11—C12—H12	119.5
O2—C7—C1	122.4 (3)	C13—C12—H12	119.5
O1—C7—C1	113.8 (3)	C14—C15—C16	121.7 (4)
N2—C18—N1	107.3 (3)	C14—C15—H15	119.1
N2—C18—C21	124.0 (3)	C16—C15—H15	119.1
N1—C18—C21	128.8 (3)	H1A—O1W—H1B	88.8
O3—C8—O4	126.8 (3)	C23—C26—H26A	109.5
O3—C8—C2	118.0 (3)	C23—C26—H26B	109.5
O4—C8—C2	115.0 (3)	H26A—C26—H26B	109.5
C15—C14—C13	116.7 (3)	C23—C26—H26C	109.5
C15—C14—C22	122.9 (3)	H26A—C26—H26C	109.5
C13—C14—C22	120.4 (3)	H26B—C26—H26C	109.5
C10—O8—H8	109.5	C18—C21—H21A	109.5
N4—C23—N3	107.9 (3)	C18—C21—H21B	109.5
N4—C23—C26	126.4 (3)	H21A—C21—H21B	109.5
N3—C23—C26	125.7 (3)	C18—C21—H21C	109.5
C24—C25—N3	107.1 (3)	H21A—C21—H21C	109.5
C24—C25—H25	126.4	H21B—C21—H21C	109.5
N3—C25—H25	126.4

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O6ⁱ	0.82	1.76	2.575 (3)	172
O1W—H1A···O6	0.86	1.90	2.747 (3)	168
O1W—H1B···O5ⁱⁱ	0.85	1.98	2.743 (3)	149
N4—H1C···O4ⁱⁱⁱ	0.98	1.75	2.679 (4)	158
N2—H2···O1W^iv	1.07	1.59	2.651 (4)	172
O8—H8···O3^v	0.82	1.81	2.586 (3)	157

Symmetry codes: (i) x+1, y, z; (ii) x, −y+1/2, z+1/2; (iii) x−1, −y+1/2, z−1/2; (iv) x−1, y, z; (v) −x+2, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₂₀N₄²⁺·C₁₀H₄O₈²⁻·H₂O
M_r	538.51
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	9.7139 (19), 19.428 (4), 13.856 (3)
β (°)	97.39 (3)
V (Å³)	2593.3 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.22 × 0.18 × 0.16

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.968, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	20668, 4571, 3075
R_int	0.078
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.073, 0.144, 1.10
No. of reflections	4571
No. of parameters	356
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.25

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O6ⁱ	0.82	1.76	2.575 (3)	172
O1W—H1A···O6	0.86	1.90	2.747 (3)	168
O1W—H1B···O5ⁱⁱ	0.85	1.98	2.743 (3)	149
N4—H1C···O4ⁱⁱⁱ	0.98	1.75	2.679 (4)	158
N2—H2···O1W^iv	1.07	1.59	2.651 (4)	172
O8—H8···O3^v	0.82	1.81	2.586 (3)	157

Symmetry codes: (i) x+1, y, z; (ii) x, −y+1/2, z+1/2; (iii) x−1, −y+1/2, z−1/2; (iv) x−1, y, z; (v) −x+2, y+1/2, −z+3/2.

Acknowledgements

The authors thank Hebei United University for supporting this work.

References

Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hoskins, B. F., Robson, R. & Slizys, D. A. (1997). J. Am. Chem. Soc. 119, 2952–2953. CSD CrossRef CAS Web of Science Google Scholar
Liu, T.-F., Wu, W.-F., Wan, C.-Q., He, C.-H., Jiao, C.-H. & Cui, G.-H. (2011). J. Coord. Chem. 64, 975–986. CrossRef CAS Google Scholar
Liu, T.-F., Wu, W.-F., Zhang, W.-G. & Cui, G.-H. (2011). Z. Anorg. Allg. Chem. 637, 148–153. CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). 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

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 67| Part 7| July 2011| Page o1696

doi:10.1107/S160053681102263X

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

1,1′-[1,4-Phenyl­enebis(methyl­ene)]bis­­(2-methyl-1H-imidazol-3-ium) 2,4-dicarb­­oxy­benzene-1,5-di­carboxyl­ate monohydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1,1′-[1,4-Phenylenebis(methylene)]bis(2-methyl-1H-imidazol-3-ium) 2,4-dicarboxybenzene-1,5-dicarboxylate monohydrate