1,1'-[1,4-Phenyl-enebis(methyl-ene)]bis-(2-methyl-1H-imidazol-3-ium) 2,4-dicarb-oxy-benzene-1,5-dicarboxyl-ate monohydrate.

In the dication of the title compound, C(16)H(20)N(4) (2+)·C(10)H(4)O(8) (2-)·H(2)O, 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 inter-molecular N-H⋯O and O-H⋯O hydrogen bonds.

Related literature

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

Experimental

Crystal data

C16H20N4 2+·C10H4O8 2−·H2O

M = 538.51

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.073

wR(F 2) = 0.144

S = 1.10

4571 reflections

356 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.25 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681102263X/lh5268sup1.cif

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

Supplementary material file. DOI: 10.1107/S160053681102263X/lh5268Isup3.cml

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

C16H20N42+·C10H4O82−·H2O	F(000) = 1128
Mr = 538.51	Dx = 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

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

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(Fo2) + (0.0452P)2 + 1.9004P] where P = (Fo2 + 2Fc2)/3
4571 reflections	(Δ/σ)max = 0.001
356 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.25 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
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*

	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)

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

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···O1Wiv	1.07	1.59	2.651 (4)	172
O8—H8···O3v	0.82	1.81	2.586 (3)	157

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⋯O1Wiv	1.07	1.59	2.651 (4)	172
O8—H8⋯O3v	0.82	1.81	2.586 (3)	157

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .