2,2'-Biimidazolium 5-amino-2,4,6-tri-bromo-isophthalate.

In the cation of the title salt, C(6)H(8)N(4) (2+)·C(8)H(2)Br(3)NO(4) (2-), the dihedral angle between the two five-membered rings is 2.1 (3)°. In the anion, the mean planes of the carboxyl units are twisted from the benzene ring by 84.3 (4) and 86.2 (3)°. In the crystal, the components are linked by imidazolium-carboxyl-ate N-H⋯O hydrogen bonds, generating a chain running along [10].

Related literature

For the structure of 5-amino-2,4,6-tribromidoisophthalic acid, see: Beck et al. (2009 ▶). For the structures of other 2,2′-bis­(imid­azolium) carboxyl­ates, see: Gao et al. (2009 ▶); Li & Yang (2007 ▶); Zhou et al. (2009 ▶).

Experimental

Crystal data

C6H8N4 2+·C8H2Br3NO4 2−

M = 552.00

Triclinic,

a = 9.0525 (10) Å

b = 9.2043 (10) Å

c = 11.5252 (12) Å

α = 90.262 (1)°

β = 108.332 (1)°

γ = 93.136 (1)°

V = 909.96 (17) Å3

Z = 2

Mo Kα radiation

μ = 6.68 mm−1

T = 293 K

0.35 × 0.25 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.203, T max = 0.434

8042 measured reflections

4104 independent reflections

3129 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.120

S = 1.12

4104 reflections

259 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.81 e Å−3

Δρmin = −0.56 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810041899/lh5152sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041899/lh5152Isup2.hkl

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

C6H8N42+·C8H2Br3NO42−	Z = 2
Mr = 552.00	F(000) = 532
Triclinic, P1	Dx = 2.015 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0525 (10) Å	Cell parameters from 2718 reflections
b = 9.2043 (10) Å	θ = 2.4–27.4°
c = 11.5252 (12) Å	µ = 6.68 mm−1
α = 90.262 (1)°	T = 293 K
β = 108.332 (1)°	Prism, pale yellow
γ = 93.136 (1)°	0.35 × 0.25 × 0.15 mm
V = 909.96 (17) Å3

Bruker SMART APEX diffractometer	4104 independent reflections
Radiation source: fine-focus sealed tube	3129 reflections with I > 2σ(I)
graphite	Rint = 0.025
ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.203, Tmax = 0.434	k = −11→11
8042 measured reflections	l = −14→14

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ2(Fo2) + (0.0618P)2 + 0.430P] where P = (Fo2 + 2Fc2)/3
4104 reflections	(Δ/σ)max = 0.001
259 parameters	Δρmax = 0.81 e Å−3
6 restraints	Δρmin = −0.56 e Å−3

	x	y	z	Uiso*/Ueq
Br1	0.44985 (5)	0.68067 (5)	0.04955 (4)	0.03399 (14)
Br2	0.30262 (7)	0.89508 (6)	0.45860 (5)	0.05335 (18)
Br3	0.80240 (6)	0.52283 (6)	0.52786 (5)	0.05028 (17)
O1	0.6388 (4)	0.3751 (3)	0.2311 (3)	0.0364 (7)
O2	0.8128 (4)	0.5529 (3)	0.2201 (3)	0.0424 (8)
O3	0.1481 (4)	0.8223 (4)	0.1385 (3)	0.0419 (8)
O4	0.3322 (4)	1.0034 (3)	0.1754 (4)	0.0465 (9)
N1	0.5757 (6)	0.7119 (6)	0.5998 (4)	0.0536 (12)
N2	0.7881 (4)	0.1504 (4)	0.2018 (4)	0.0326 (8)
N3	0.9353 (4)	−0.0118 (4)	0.1680 (4)	0.0356 (9)
N4	1.1546 (4)	0.2242 (4)	0.1272 (3)	0.0305 (8)
N5	1.0016 (4)	0.3864 (4)	0.1539 (3)	0.0258 (7)
C1	0.6952 (5)	0.5045 (5)	0.2451 (4)	0.0300 (9)
C2	0.6062 (5)	0.6121 (4)	0.2971 (4)	0.0265 (8)
C3	0.4913 (5)	0.6934 (4)	0.2216 (4)	0.0246 (8)
C4	0.4030 (5)	0.7833 (4)	0.2686 (4)	0.0276 (9)
C5	0.4310 (5)	0.7852 (5)	0.3941 (4)	0.0329 (10)
C6	0.5465 (5)	0.7061 (5)	0.4750 (4)	0.0343 (10)
C7	0.6352 (5)	0.6244 (4)	0.4223 (4)	0.0293 (9)
C8	0.2831 (5)	0.8777 (4)	0.1859 (4)	0.0310 (9)
C9	0.7208 (6)	0.0171 (5)	0.2144 (5)	0.0491 (13)
H9	0.6293	−0.0004	0.2337	0.059*
C10	0.8132 (6)	−0.0853 (5)	0.1932 (5)	0.0485 (13)
H10	0.7967	−0.1857	0.1954	0.058*
C11	0.9166 (5)	0.1302 (4)	0.1731 (4)	0.0260 (8)
C12	1.0206 (5)	0.2449 (4)	0.1518 (4)	0.0253 (8)
C13	1.2192 (5)	0.3590 (5)	0.1138 (4)	0.0343 (10)
H13	1.3118	0.3773	0.0960	0.041*
C14	1.1255 (5)	0.4600 (4)	0.1306 (4)	0.0307 (9)
H14	1.1414	0.5604	0.1273	0.037*
H2	0.751 (7)	0.232 (4)	0.217 (5)	0.068 (19)*
H3	1.005 (5)	−0.054 (5)	0.143 (5)	0.054 (16)*
H4	1.215 (6)	0.151 (5)	0.139 (6)	0.09 (2)*
H5	0.923 (4)	0.424 (5)	0.171 (4)	0.035 (13)*
H11	0.519 (6)	0.764 (6)	0.631 (5)	0.07 (2)*
H12	0.624 (6)	0.640 (4)	0.643 (4)	0.056 (18)*

	U11	U22	U33	U12	U13	U23
Br1	0.0363 (3)	0.0361 (3)	0.0319 (2)	0.01227 (19)	0.01250 (19)	−0.00142 (18)
Br2	0.0560 (4)	0.0543 (4)	0.0623 (4)	0.0200 (3)	0.0340 (3)	−0.0138 (3)
Br3	0.0441 (3)	0.0611 (4)	0.0420 (3)	0.0224 (3)	0.0049 (2)	0.0071 (2)
O1	0.0342 (17)	0.0232 (15)	0.060 (2)	0.0058 (13)	0.0254 (15)	−0.0047 (14)
O2	0.0372 (19)	0.0282 (17)	0.075 (2)	0.0075 (14)	0.0350 (18)	0.0010 (16)
O3	0.0223 (16)	0.0374 (19)	0.063 (2)	0.0091 (14)	0.0084 (15)	−0.0072 (16)
O4	0.0372 (19)	0.0170 (16)	0.088 (3)	0.0121 (14)	0.0217 (18)	0.0094 (16)
N1	0.067 (3)	0.062 (3)	0.036 (2)	0.020 (3)	0.019 (2)	−0.005 (2)
N2	0.0230 (18)	0.0250 (19)	0.055 (2)	0.0067 (15)	0.0198 (17)	−0.0002 (17)
N3	0.028 (2)	0.0250 (19)	0.059 (2)	0.0073 (16)	0.0192 (18)	−0.0025 (17)
N4	0.0188 (17)	0.034 (2)	0.042 (2)	0.0098 (15)	0.0134 (15)	0.0030 (16)
N5	0.0170 (16)	0.0258 (18)	0.0388 (19)	0.0093 (14)	0.0134 (14)	0.0022 (15)
C1	0.034 (2)	0.030 (2)	0.030 (2)	0.0114 (19)	0.0135 (18)	0.0013 (17)
C2	0.027 (2)	0.0187 (19)	0.036 (2)	0.0059 (16)	0.0125 (17)	−0.0015 (16)
C3	0.028 (2)	0.020 (2)	0.0280 (19)	0.0052 (16)	0.0116 (17)	−0.0030 (15)
C4	0.024 (2)	0.021 (2)	0.041 (2)	0.0066 (16)	0.0145 (18)	−0.0016 (17)
C5	0.031 (2)	0.030 (2)	0.044 (2)	0.0102 (19)	0.019 (2)	−0.0103 (19)
C6	0.034 (2)	0.036 (2)	0.036 (2)	0.005 (2)	0.015 (2)	−0.0061 (19)
C7	0.025 (2)	0.024 (2)	0.039 (2)	0.0078 (17)	0.0091 (18)	0.0007 (17)
C8	0.031 (2)	0.020 (2)	0.048 (3)	0.0161 (18)	0.018 (2)	−0.0008 (18)
C9	0.041 (3)	0.034 (3)	0.084 (4)	−0.002 (2)	0.035 (3)	−0.002 (3)
C10	0.042 (3)	0.023 (2)	0.088 (4)	0.002 (2)	0.031 (3)	0.003 (2)
C11	0.029 (2)	0.0151 (19)	0.034 (2)	0.0067 (16)	0.0089 (17)	−0.0003 (16)
C12	0.030 (2)	0.0144 (18)	0.033 (2)	0.0075 (16)	0.0107 (17)	0.0003 (15)
C13	0.036 (2)	0.027 (2)	0.045 (3)	0.0033 (19)	0.019 (2)	0.0031 (19)
C14	0.035 (2)	0.0154 (19)	0.042 (2)	0.0045 (17)	0.0125 (19)	0.0054 (17)

Br1—C3	1.901 (4)	N5—C12	1.325 (5)
Br2—C5	1.895 (4)	N5—C14	1.377 (5)
Br3—C7	1.911 (4)	N5—H5	0.882 (10)
O1—C1	1.259 (5)	C1—C2	1.541 (5)
O2—C1	1.248 (5)	C2—C7	1.386 (6)
O3—C8	1.250 (5)	C2—C3	1.386 (5)
O4—C8	1.237 (5)	C3—C4	1.399 (5)
N1—C6	1.378 (6)	C4—C5	1.388 (6)
N1—H11	0.877 (10)	C4—C8	1.517 (6)
N1—H12	0.879 (10)	C5—C6	1.403 (6)
N2—C11	1.327 (5)	C6—C7	1.396 (6)
N2—C9	1.369 (6)	C9—C10	1.364 (7)
N2—H2	0.880 (10)	C9—H9	0.9300
N3—C11	1.330 (5)	C10—H10	0.9300
N3—C10	1.373 (6)	C11—C12	1.449 (6)
N3—H3	0.879 (10)	C13—C14	1.346 (6)
N4—C12	1.352 (5)	C13—H13	0.9300
N4—C13	1.373 (6)	C14—H14	0.9300
N4—H4	0.880 (10)
C6—N1—H11	120 (4)	C6—C5—Br2	118.5 (3)
C6—N1—H12	118 (4)	N1—C6—C7	121.3 (4)
H11—N1—H12	119 (6)	N1—C6—C5	122.5 (4)
C11—N2—C9	108.4 (4)	C7—C6—C5	116.1 (4)
C11—N2—H2	129 (4)	C2—C7—C6	123.0 (4)
C9—N2—H2	122 (4)	C2—C7—Br3	118.6 (3)
C11—N3—C10	108.3 (4)	C6—C7—Br3	118.4 (3)
C11—N3—H3	127 (4)	O4—C8—O3	127.7 (4)
C10—N3—H3	124 (4)	O4—C8—C4	114.7 (4)
C12—N4—C13	107.4 (4)	O3—C8—C4	117.7 (4)
C12—N4—H4	132 (4)	C10—C9—N2	107.2 (4)
C13—N4—H4	117 (4)	C10—C9—H9	126.4
C12—N5—C14	108.8 (3)	N2—C9—H9	126.4
C12—N5—H5	124 (3)	C9—C10—N3	106.9 (4)
C14—N5—H5	127 (3)	C9—C10—H10	126.6
O2—C1—O1	126.7 (4)	N3—C10—H10	126.6
O2—C1—C2	117.9 (4)	N2—C11—N3	109.2 (4)
O1—C1—C2	115.4 (4)	N2—C11—C12	125.3 (4)
C7—C2—C3	118.2 (4)	N3—C11—C12	125.5 (4)
C7—C2—C1	119.9 (4)	N5—C12—N4	108.7 (3)
C3—C2—C1	121.8 (4)	N5—C12—C11	126.1 (4)
C2—C3—C4	121.7 (4)	N4—C12—C11	125.2 (4)
C2—C3—Br1	119.4 (3)	C14—C13—N4	108.2 (4)
C4—C3—Br1	118.9 (3)	C14—C13—H13	125.9
C5—C4—C3	117.6 (4)	N4—C13—H13	125.9
C5—C4—C8	121.0 (3)	C13—C14—N5	106.9 (4)
C3—C4—C8	121.3 (4)	C13—C14—H14	126.5
C4—C5—C6	123.2 (4)	N5—C14—H14	126.5
C4—C5—Br2	118.3 (3)
O2—C1—C2—C7	−96.8 (5)	C5—C6—C7—C2	−4.4 (6)
O1—C1—C2—C7	83.9 (5)	N1—C6—C7—Br3	−1.2 (6)
O2—C1—C2—C3	86.3 (5)	C5—C6—C7—Br3	176.5 (3)
O1—C1—C2—C3	−93.0 (5)	C5—C4—C8—O4	85.3 (5)
C7—C2—C3—C4	−1.5 (6)	C3—C4—C8—O4	−93.6 (5)
C1—C2—C3—C4	175.4 (4)	C5—C4—C8—O3	−93.5 (5)
C7—C2—C3—Br1	179.4 (3)	C3—C4—C8—O3	87.6 (5)
C1—C2—C3—Br1	−3.7 (5)	C11—N2—C9—C10	0.4 (6)
C2—C3—C4—C5	−2.0 (6)	N2—C9—C10—N3	0.0 (7)
Br1—C3—C4—C5	177.1 (3)	C11—N3—C10—C9	−0.4 (6)
C2—C3—C4—C8	176.9 (4)	C9—N2—C11—N3	−0.7 (5)
Br1—C3—C4—C8	−4.1 (5)	C9—N2—C11—C12	179.9 (4)
C3—C4—C5—C6	2.5 (6)	C10—N3—C11—N2	0.7 (5)
C8—C4—C5—C6	−176.4 (4)	C10—N3—C11—C12	−179.9 (4)
C3—C4—C5—Br2	−175.5 (3)	C14—N5—C12—N4	−0.2 (5)
C8—C4—C5—Br2	5.6 (6)	C14—N5—C12—C11	179.4 (4)
C4—C5—C6—N1	178.2 (5)	C13—N4—C12—N5	0.0 (5)
Br2—C5—C6—N1	−3.8 (6)	C13—N4—C12—C11	−179.7 (4)
C4—C5—C6—C7	0.6 (7)	N2—C11—C12—N5	−2.3 (7)
Br2—C5—C6—C7	178.6 (3)	N3—C11—C12—N5	178.4 (4)
C3—C2—C7—C6	4.9 (6)	N2—C11—C12—N4	177.3 (4)
C1—C2—C7—C6	−172.0 (4)	N3—C11—C12—N4	−2.0 (7)
C3—C2—C7—Br3	−176.0 (3)	C12—N4—C13—C14	0.2 (5)
C1—C2—C7—Br3	7.0 (5)	N4—C13—C14—N5	−0.4 (5)
N1—C6—C7—C2	177.9 (4)	C12—N5—C14—C13	0.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.88 (1)	1.74 (2)	2.608 (4)	168 (6)
N3—H3···O3i	0.88 (1)	1.78 (2)	2.624 (5)	160 (5)
N4—H4···O4i	0.88 (1)	1.74 (1)	2.614 (5)	175 (7)
N5—H5···O2	0.88 (1)	1.79 (2)	2.636 (4)	160 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.88 (1)	1.74 (2)	2.608 (4)	168 (6)
N3—H3⋯O3i	0.88 (1)	1.78 (2)	2.624 (5)	160 (5)
N4—H4⋯O4i	0.88 (1)	1.74 (1)	2.614 (5)	175 (7)
N5—H5⋯O2	0.88 (1)	1.79 (2)	2.636 (4)	160 (4)

Symmetry code: (i) .