3,3'-(p-Phenyl-enedimethyl-ene)di-1H-imidazol-1-ium bis-(4-nitro-benzoate)-4-nitro-benzoic acid (1/2).

The asymmetric unit of the title compound, C(14)H(16)N(4) (2+)·2C(7)H(4)NO(4) (-)·2C(7)H(5)NO(4), comprises one-half of the 3,3'-(p-phenyl-enedimethyl-ene)di-1H-imidazol-1-ium dication, which lies on an inversion centre, one 4-nitro-benzoate anion and one 4-nitro-benzoic acid mol-ecule. In the crystal, the components are linked into a two-dimensional network parallel to (110) by O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds.

Related literature

For the synthesis of 1,4-bis­(imidazol-1-ylmeth­yl)benzene, see: Hoskins et al. (1997 ▶). For a related structure, see: Chen et al. (2010 ▶).

Experimental

Crystal data

C14H16N4 2+·2C7H4NO4−·2C7H5NO4

M = 906.77

Triclinic,

a = 7.2659 (15) Å

b = 12.689 (3) Å

c = 13.028 (3) Å

α = 112.94 (3)°

β = 102.49 (3)°

γ = 101.94 (3)°

V = 1021.8 (6) Å3

Z = 1

Mo Kα radiation

μ = 0.12 mm−1

T = 295 K

0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.968, T max = 0.971

8835 measured reflections

3590 independent reflections

2019 reflections with I > 2σ(I)

R int = 0.066

Refinement

R[F 2 > 2σ(F 2)] = 0.081

wR(F 2) = 0.191

S = 1.19

3590 reflections

298 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.24 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 datablocks I, global. DOI: 10.1107/S160053681001929X/ci5093sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001929X/ci5093Isup2.hkl

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

C14H16N42+·2C7H4NO4−·2C7H5NO4	Z = 1
Mr = 906.77	F(000) = 470
Triclinic, P1	Dx = 1.474 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2659 (15) Å	Cell parameters from 3889 reflections
b = 12.689 (3) Å	θ = 4.6–22.7°
c = 13.028 (3) Å	µ = 0.12 mm−1
α = 112.94 (3)°	T = 295 K
β = 102.49 (3)°	Prism, colourless
γ = 101.94 (3)°	0.20 × 0.20 × 0.20 mm
V = 1021.8 (6) Å3

Bruker SMART CCD area-detector diffractometer	3590 independent reflections
Radiation source: fine–focus sealed tube	2019 reflections with I > 2σ(I)
graphite	Rint = 0.066
φ and ω scans	θmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.968, Tmax = 0.971	k = −15→15
8835 measured reflections	l = −15→15

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)] = 0.081	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.191	H-atom parameters constrained
S = 1.19	w = 1/[σ2(Fo2) + (0.0648P)2 + 0.2399P] where P = (Fo2 + 2Fc2)/3
3590 reflections	(Δ/σ)max = 0.001
298 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O7	0.1748 (5)	0.3773 (3)	0.6201 (3)	0.0628 (9)
O8	0.2413 (5)	0.4626 (3)	0.5069 (3)	0.0636 (9)
N4	0.2722 (5)	0.3310 (3)	0.2960 (3)	0.0468 (9)
H4A	0.2596	0.3328	0.3607	0.056*
N3	0.3203 (4)	0.3884 (3)	0.1672 (3)	0.0341 (8)
C11	0.2099 (5)	0.5846 (3)	0.6892 (3)	0.0346 (10)
C12	0.1960 (6)	0.5971 (4)	0.7973 (3)	0.0378 (10)
H12	0.1787	0.5305	0.8124	0.045*
C20	0.0546 (6)	0.4031 (4)	−0.0614 (3)	0.0417 (11)
H20	0.0910	0.3371	−0.1031	0.050*
C10	0.2349 (6)	0.6835 (4)	0.6673 (4)	0.0454 (11)
H10	0.2447	0.6753	0.5947	0.054*
C21	−0.1173 (6)	0.4176 (4)	−0.1146 (4)	0.0417 (11)
H21	−0.1952	0.3621	−0.1918	0.050*
C13	0.2074 (6)	0.7074 (4)	0.8830 (4)	0.0426 (11)
H13	0.1981	0.7160	0.9558	0.051*
C17	0.2842 (6)	0.2657 (4)	0.1182 (4)	0.0397 (10)
H17	0.2808	0.2161	0.0427	0.048*
C8	0.2328 (6)	0.8040 (4)	0.8581 (4)	0.0423 (11)
C14	0.2070 (6)	0.4663 (4)	0.5962 (4)	0.0417 (11)
C19	0.1743 (6)	0.4850 (4)	0.0531 (3)	0.0359 (10)
C9	0.2457 (6)	0.7939 (4)	0.7505 (4)	0.0510 (12)
H9	0.2612	0.8603	0.7351	0.061*
N2	0.2409 (6)	0.9230 (4)	0.9474 (4)	0.0642 (12)
C15	0.3111 (6)	0.4252 (4)	0.2754 (4)	0.0405 (10)
H15	0.3291	0.5044	0.3279	0.049*
O6	0.2194 (6)	0.9302 (3)	1.0400 (3)	0.0946 (14)
C16	0.2548 (6)	0.2308 (4)	0.1995 (4)	0.0445 (11)
H16	0.2277	0.1525	0.1913	0.053*
O5	0.2639 (7)	1.0065 (3)	0.9231 (4)	0.1088 (16)
C18	0.3622 (6)	0.4672 (4)	0.1113 (4)	0.0472 (11)
H18A	0.4226	0.4318	0.0525	0.057*
H18B	0.4567	0.5452	0.1706	0.057*
C4	0.4933 (6)	0.8837 (3)	0.5529 (3)	0.0360 (10)
O3	0.4409 (5)	0.7026 (3)	0.3853 (3)	0.0731 (11)
O2	0.4178 (6)	1.2399 (3)	0.8522 (3)	0.0791 (11)
O4	0.7429 (5)	0.7925 (3)	0.5183 (3)	0.0700 (10)
C1	0.3648 (7)	1.0618 (4)	0.6869 (4)	0.0423 (11)
N1	0.2961 (7)	1.1562 (4)	0.7606 (4)	0.0616 (11)
C5	0.6275 (6)	0.9830 (3)	0.6549 (3)	0.0417 (11)
H5	0.7610	0.9887	0.6779	0.050*
C3	0.2940 (6)	0.8758 (4)	0.5190 (3)	0.0432 (11)
H3	0.2041	0.8099	0.4503	0.052*
C2	0.2281 (7)	0.9650 (4)	0.5863 (4)	0.0473 (11)
H2	0.0947	0.9596	0.5642	0.057*
C6	0.5638 (7)	1.0733 (4)	0.7224 (4)	0.0451 (11)
H6	0.6533	1.1403	0.7903	0.054*
C7	0.5608 (8)	0.7845 (4)	0.4785 (4)	0.0470 (11)
O1	0.1202 (7)	1.1467 (4)	0.7276 (4)	0.1083 (15)
H2A	0.2107	0.3206	0.5773	0.162*

	U11	U22	U33	U12	U13	U23
O7	0.086 (3)	0.0432 (19)	0.072 (2)	0.0297 (18)	0.0469 (19)	0.0238 (18)
O8	0.086 (3)	0.065 (2)	0.0381 (19)	0.0274 (19)	0.0290 (18)	0.0162 (17)
N4	0.048 (2)	0.062 (3)	0.035 (2)	0.0202 (19)	0.0143 (17)	0.025 (2)
N3	0.035 (2)	0.038 (2)	0.032 (2)	0.0177 (16)	0.0105 (15)	0.0157 (17)
C11	0.028 (2)	0.039 (2)	0.032 (2)	0.0081 (18)	0.0080 (18)	0.013 (2)
C12	0.039 (3)	0.042 (3)	0.041 (3)	0.016 (2)	0.019 (2)	0.023 (2)
C20	0.049 (3)	0.041 (3)	0.043 (3)	0.023 (2)	0.018 (2)	0.021 (2)
C10	0.058 (3)	0.047 (3)	0.034 (3)	0.017 (2)	0.017 (2)	0.019 (2)
C21	0.049 (3)	0.038 (3)	0.032 (2)	0.013 (2)	0.008 (2)	0.013 (2)
C13	0.041 (3)	0.053 (3)	0.034 (2)	0.017 (2)	0.016 (2)	0.016 (2)
C17	0.045 (3)	0.034 (2)	0.037 (3)	0.020 (2)	0.012 (2)	0.011 (2)
C8	0.038 (3)	0.036 (2)	0.041 (3)	0.013 (2)	0.009 (2)	0.007 (2)
C14	0.029 (2)	0.045 (3)	0.042 (3)	0.009 (2)	0.008 (2)	0.013 (2)
C19	0.036 (3)	0.040 (2)	0.037 (3)	0.008 (2)	0.011 (2)	0.025 (2)
C9	0.064 (3)	0.043 (3)	0.053 (3)	0.019 (2)	0.020 (2)	0.026 (3)
N2	0.065 (3)	0.050 (3)	0.059 (3)	0.022 (2)	0.013 (2)	0.008 (3)
C15	0.033 (3)	0.040 (3)	0.035 (3)	0.015 (2)	0.0044 (19)	0.006 (2)
O6	0.138 (4)	0.083 (3)	0.046 (2)	0.055 (3)	0.026 (2)	0.006 (2)
C16	0.046 (3)	0.034 (3)	0.050 (3)	0.014 (2)	0.010 (2)	0.018 (2)
O5	0.177 (5)	0.046 (2)	0.115 (4)	0.046 (3)	0.072 (3)	0.029 (2)
C18	0.041 (3)	0.054 (3)	0.053 (3)	0.015 (2)	0.014 (2)	0.032 (2)
C4	0.053 (3)	0.025 (2)	0.032 (2)	0.012 (2)	0.015 (2)	0.0134 (19)
O3	0.082 (3)	0.047 (2)	0.051 (2)	0.0251 (18)	−0.0019 (19)	−0.0063 (17)
O2	0.091 (3)	0.054 (2)	0.066 (2)	0.023 (2)	0.032 (2)	−0.001 (2)
O4	0.057 (2)	0.047 (2)	0.076 (2)	0.0193 (17)	0.0156 (19)	0.0005 (18)
C1	0.056 (3)	0.036 (2)	0.046 (3)	0.021 (2)	0.025 (2)	0.021 (2)
N1	0.067 (3)	0.049 (3)	0.065 (3)	0.023 (2)	0.035 (3)	0.015 (2)
C5	0.044 (3)	0.033 (2)	0.042 (3)	0.010 (2)	0.010 (2)	0.014 (2)
C3	0.050 (3)	0.036 (3)	0.033 (2)	0.009 (2)	0.004 (2)	0.013 (2)
C2	0.047 (3)	0.044 (3)	0.043 (3)	0.013 (2)	0.011 (2)	0.016 (2)
C6	0.059 (3)	0.033 (2)	0.034 (2)	0.012 (2)	0.014 (2)	0.009 (2)
C7	0.066 (4)	0.028 (2)	0.042 (3)	0.012 (2)	0.015 (3)	0.014 (2)
O1	0.072 (3)	0.086 (3)	0.129 (4)	0.040 (2)	0.037 (3)	0.003 (3)

O7—C14	1.274 (5)	C8—N2	1.484 (5)
O7—H2A	0.85	C19—C21i	1.387 (5)
O8—C14	1.227 (5)	C19—C18	1.519 (5)
N4—C15	1.313 (5)	C9—H9	0.93
N4—C16	1.354 (5)	N2—O5	1.210 (5)
N4—H4A	0.86	N2—O6	1.220 (5)
N3—C15	1.324 (5)	C15—H15	0.93
N3—C17	1.373 (5)	C16—H16	0.93
N3—C18	1.469 (5)	C18—H18A	0.97
C11—C10	1.378 (5)	C18—H18B	0.97
C11—C12	1.383 (5)	C4—C5	1.389 (5)
C11—C14	1.510 (5)	C4—C3	1.389 (5)
C12—C13	1.380 (5)	C4—C7	1.509 (6)
C12—H12	0.93	O3—C7	1.224 (5)
C20—C21	1.376 (5)	O2—N1	1.225 (5)
C20—C19	1.385 (5)	O4—C7	1.279 (5)
C20—H20	0.93	C1—C2	1.374 (6)
C10—C9	1.370 (6)	C1—C6	1.377 (6)
C10—H10	0.93	C1—N1	1.472 (5)
C21—C19i	1.387 (5)	N1—O1	1.221 (5)
C21—H21	0.93	C5—C6	1.382 (5)
C13—C8	1.373 (5)	C5—H5	0.93
C13—H13	0.93	C3—C2	1.382 (5)
C17—C16	1.336 (5)	C3—H3	0.93
C17—H17	0.93	C2—H2	0.93
C8—C9	1.382 (6)	C6—H6	0.93
C14—O7—H2A	111.6	O5—N2—O6	123.9 (4)
C15—N4—C16	109.4 (3)	O5—N2—C8	118.0 (5)
C15—N4—H4A	125.3	O6—N2—C8	118.1 (5)
C16—N4—H4A	125.3	N4—C15—N3	108.4 (4)
C15—N3—C17	108.0 (3)	N4—C15—H15	125.8
C15—N3—C18	125.0 (3)	N3—C15—H15	125.8
C17—N3—C18	127.0 (3)	C17—C16—N4	107.0 (4)
C10—C11—C12	119.4 (4)	C17—C16—H16	126.5
C10—C11—C14	119.0 (4)	N4—C16—H16	126.5
C12—C11—C14	121.6 (4)	N3—C18—C19	111.7 (3)
C13—C12—C11	120.7 (4)	N3—C18—H18A	109.3
C13—C12—H12	119.7	C19—C18—H18A	109.3
C11—C12—H12	119.7	N3—C18—H18B	109.3
C21—C20—C19	121.1 (4)	C19—C18—H18B	109.3
C21—C20—H20	119.4	H18A—C18—H18B	107.9
C19—C20—H20	119.4	C5—C4—C3	119.5 (4)
C9—C10—C11	121.2 (4)	C5—C4—C7	121.0 (4)
C9—C10—H10	119.4	C3—C4—C7	119.6 (4)
C11—C10—H10	119.4	C2—C1—C6	122.6 (4)
C20—C21—C19i	120.0 (4)	C2—C1—N1	118.9 (4)
C20—C21—H21	120.0	C6—C1—N1	118.5 (4)
C19i—C21—H21	120.0	O1—N1—O2	123.3 (4)
C8—C13—C12	118.3 (4)	O1—N1—C1	118.3 (4)
C8—C13—H13	120.8	O2—N1—C1	118.4 (5)
C12—C13—H13	120.8	C6—C5—C4	120.4 (4)
C16—C17—N3	107.1 (4)	C6—C5—H5	119.8
C16—C17—H17	126.4	C4—C5—H5	119.8
N3—C17—H17	126.4	C2—C3—C4	120.7 (4)
C13—C8—C9	122.2 (4)	C2—C3—H3	119.7
C13—C8—N2	119.5 (4)	C4—C3—H3	119.7
C9—C8—N2	118.2 (4)	C1—C2—C3	118.4 (4)
O8—C14—O7	124.9 (4)	C1—C2—H2	120.8
O8—C14—C11	119.4 (4)	C3—C2—H2	120.8
O7—C14—C11	115.7 (4)	C1—C6—C5	118.5 (4)
C20—C19—C21i	118.8 (4)	C1—C6—H6	120.7
C20—C19—C18	120.6 (4)	C5—C6—H6	120.7
C21i—C19—C18	120.5 (4)	O3—C7—O4	124.3 (4)
C10—C9—C8	118.2 (4)	O3—C7—C4	119.0 (5)
C10—C9—H9	120.9	O4—C7—C4	116.7 (4)
C8—C9—H9	120.9

D—H···A	D—H	H···A	D···A	D—H···A
O7—H2A···O3ii	0.85	2.57	3.167 (5)	128
O7—H2A···O4ii	0.85	1.65	2.494 (5)	173
N4—H4A···O8	0.86	2.03	2.690 (5)	133
C15—H15···O3	0.93	2.23	3.073 (7)	150
C17—H17···O5iii	0.93	2.46	3.228 (7)	140
C21—H21···O3i	0.93	2.46	3.321 (6)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H2A⋯O3i	0.85	2.57	3.167 (5)	128
O7—H2A⋯O4i	0.85	1.65	2.494 (5)	173
N4—H4A⋯O8	0.86	2.03	2.690 (5)	133
C15—H15⋯O3	0.93	2.23	3.073 (7)	150
C17—H17⋯O5ii	0.93	2.46	3.228 (7)	140
C21—H21⋯O3iii	0.93	2.46	3.321 (6)	154

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