Bis(2-methyl-imidazolium) chloranilate.

The asymmetric unit of the title structure, 2C(4)H(7)N(2) (+)·C(6)Cl(2)O(4) (2-), consists of one 2-methyl-imidazolium cation and one-half of a chloranilate anion, the formula unit being generated by crystallographic inversion symmetry. N-H⋯O hydrogen bonds link the ions into a two-dimensional framework parallel to the (102) plane. No π-π stacking or C-H⋯π inter-actions are observed in the crystal structure.

Related literature

For related literature, see: Bernstein et al. (1995 ▶); Ishida & Kashino (2001 ▶); Ishida (2004a ▶,b ▶); Meng & Qian (2006 ▶); Min et al. (2006 ▶); Wang & Wei (2005 ▶).

Experimental

Crystal data

2C4H7N2 +·C6Cl2O4 2−

M = 373.20

Monoclinic,

a = 8.5092 (10) Å

b = 7.6658 (9) Å

c = 12.7204 (16) Å

β = 91.204 (2)°

V = 829.57 (17) Å3

Z = 2

Mo Kα radiation

μ = 0.42 mm−1

T = 296 (2) K

0.12 × 0.05 × 0.02 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.942, T max = 0.992

9164 measured reflections

1880 independent reflections

1150 reflections with I > 2σ(I)

R int = 0.067

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.132

S = 1.01

1880 reflections

116 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807048374/lh2514sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807048374/lh2514Isup2.hkl

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

2C4H7N2+·C6Cl2O42–	F000 = 384
Mr = 373.20	Dx = 1.494 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 863 reflections
a = 8.5092 (10) Å	θ = 2.4–19.5º
b = 7.6658 (9) Å	µ = 0.42 mm−1
c = 12.7204 (16) Å	T = 296 (2) K
β = 91.204 (2)º	Plate, red
V = 829.57 (17) Å3	0.12 × 0.05 × 0.02 mm
Z = 2

Bruker SMART APEX CCD area-detector diffractometer	1150 reflections with I > 2σ(I)
Radiation source: fine focus sealed Siemens Mo tube	Rint = 0.067
Monochromator: graphite	θmax = 27.5º
0.3° wide ω exposures scans	θmin = 2.4º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.942, Tmax = 0.992	k = −9→9
9164 measured reflections	l = −16→16
1880 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.132	w = 1/[σ2(Fo2) + (0.0635P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
1880 reflections	Δρmax = 0.28 e Å−3
116 parameters	Δρmin = −0.23 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
C1	0.9935 (3)	0.3795 (3)	0.1722 (2)	0.0386 (7)
C2	0.8754 (4)	0.2917 (4)	0.0266 (2)	0.0472 (7)
H2	0.8591	0.2450	−0.0403	0.057*
C3	0.7656 (3)	0.3549 (4)	0.0898 (2)	0.0457 (7)
H3	0.6582	0.3609	0.0751	0.055*
C4	1.1147 (4)	0.4178 (5)	0.2537 (2)	0.0614 (9)
H4A	1.1663	0.3116	0.2745	0.092*
H4B	1.0661	0.4695	0.3136	0.092*
H4C	1.1905	0.4974	0.2260	0.092*
C5	0.5122 (3)	0.3827 (3)	0.41260 (19)	0.0346 (6)
C6	0.6258 (3)	0.5121 (3)	0.42497 (17)	0.0310 (6)
C7	0.6127 (3)	0.6382 (3)	0.51780 (19)	0.0336 (6)
Cl1	0.52835 (9)	0.23376 (10)	0.31053 (5)	0.0543 (3)
N1	0.8402 (3)	0.4086 (3)	0.17996 (17)	0.0404 (6)
H1A	0.794 (3)	0.452 (3)	0.246 (2)	0.049*
N2	1.0162 (3)	0.3091 (3)	0.07907 (18)	0.0419 (6)
H2A	1.105 (4)	0.275 (4)	0.066 (2)	0.050*
O1	0.7415 (2)	0.5352 (2)	0.36643 (13)	0.0413 (5)
O2	0.7146 (2)	0.7533 (3)	0.52727 (15)	0.0512 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0307 (16)	0.0390 (16)	0.0466 (16)	−0.0006 (13)	0.0121 (12)	−0.0012 (12)
C2	0.0474 (19)	0.0524 (18)	0.0419 (15)	−0.0007 (15)	0.0054 (14)	−0.0076 (14)
C3	0.0331 (16)	0.0542 (18)	0.0500 (17)	0.0010 (14)	0.0045 (14)	−0.0066 (14)
C4	0.0455 (19)	0.074 (2)	0.065 (2)	0.0006 (17)	−0.0009 (16)	−0.0138 (17)
C5	0.0292 (14)	0.0381 (15)	0.0370 (13)	−0.0020 (12)	0.0105 (11)	−0.0084 (11)
C6	0.0245 (14)	0.0386 (15)	0.0299 (12)	0.0022 (11)	0.0042 (11)	0.0018 (11)
C7	0.0285 (14)	0.0361 (15)	0.0363 (13)	−0.0010 (12)	0.0059 (11)	0.0007 (11)
Cl1	0.0482 (5)	0.0624 (5)	0.0532 (5)	−0.0135 (4)	0.0227 (4)	−0.0260 (4)
N1	0.0347 (14)	0.0444 (14)	0.0428 (13)	0.0027 (11)	0.0158 (11)	−0.0063 (11)
N2	0.0347 (14)	0.0450 (15)	0.0468 (13)	0.0075 (11)	0.0177 (12)	−0.0038 (11)
O1	0.0315 (11)	0.0521 (12)	0.0409 (10)	−0.0071 (9)	0.0177 (8)	−0.0033 (9)
O2	0.0441 (12)	0.0547 (13)	0.0557 (12)	−0.0212 (10)	0.0237 (10)	−0.0174 (10)

C1—N2	1.319 (3)	C4—H4C	0.9600
C1—N1	1.329 (3)	C5—C6	1.392 (3)
C1—C4	1.477 (4)	C5—C7i	1.406 (3)
C2—C3	1.337 (4)	C5—Cl1	1.737 (2)
C2—N2	1.366 (4)	C6—O1	1.259 (3)
C2—H2	0.9300	C6—C7	1.532 (3)
C3—N1	1.363 (3)	C7—O2	1.242 (3)
C3—Cl1	3.613 (3)	C7—C5i	1.406 (3)
C3—H3	0.9300	N1—H1A	0.99 (3)
C4—H4A	0.9600	N2—H2A	0.82 (3)
C4—H4B	0.9600
N2—C1—N1	107.3 (2)	H4B—C4—H4C	109.5
N2—C1—C4	126.8 (3)	C6—C5—C7i	122.8 (2)
N1—C1—C4	125.9 (3)	C6—C5—Cl1	119.15 (18)
C3—C2—N2	106.7 (3)	C7i—C5—Cl1	117.96 (19)
C3—C2—H2	126.7	O1—C6—C5	125.7 (2)
N2—C2—H2	126.7	O1—C6—C7	115.9 (2)
C2—C3—N1	107.3 (3)	C5—C6—C7	118.4 (2)
C2—C3—Cl1	141.6 (2)	O2—C7—C5i	123.7 (2)
N1—C3—Cl1	71.46 (15)	O2—C7—C6	117.5 (2)
C2—C3—H3	126.4	C5i—C7—C6	118.8 (2)
N1—C3—H3	126.4	C5—Cl1—C3	117.80 (10)
Cl1—C3—H3	66.9	C1—N1—C3	109.1 (2)
C1—C4—H4A	109.5	C1—N1—H1A	121.6 (15)
C1—C4—H4B	109.5	C3—N1—H1A	129.0 (15)
H4A—C4—H4B	109.5	C1—N2—C2	109.6 (2)
C1—C4—H4C	109.5	C1—N2—H2A	118 (2)
H4A—C4—H4C	109.5	C2—N2—H2A	132 (2)
N2—C2—C3—N1	−0.4 (3)	C7i—C5—Cl1—C3	161.62 (18)
N2—C2—C3—Cl1	−82.1 (4)	C2—C3—Cl1—C5	135.2 (3)
C7i—C5—C6—O1	178.7 (2)	N1—C3—Cl1—C5	40.6 (2)
Cl1—C5—C6—O1	1.6 (4)	N2—C1—N1—C3	0.2 (3)
C7i—C5—C6—C7	−0.7 (4)	C4—C1—N1—C3	−179.3 (3)
Cl1—C5—C6—C7	−177.85 (17)	C2—C3—N1—C1	0.2 (3)
O1—C6—C7—O2	0.9 (3)	Cl1—C3—N1—C1	139.7 (2)
C5—C6—C7—O2	−179.6 (2)	N1—C1—N2—C2	−0.4 (3)
O1—C6—C7—C5i	−178.8 (2)	C4—C1—N2—C2	179.1 (3)
C5—C6—C7—C5i	0.7 (4)	C3—C2—N2—C1	0.5 (3)
C6—C5—Cl1—C3	−21.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.99 (3)	1.73 (3)	2.713 (3)	172 (2)
N2—H2A···O2ii	0.82 (3)	1.96 (3)	2.719 (3)	152 (3)
N2—H2A···O1ii	0.82 (3)	2.40 (3)	3.014 (3)	132 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.99 (3)	1.73 (3)	2.713 (3)	172 (2)
N2—H2A⋯O2i	0.82 (3)	1.96 (3)	2.719 (3)	152 (3)
N2—H2A⋯O1i	0.82 (3)	2.40 (3)	3.014 (3)	132 (3)

Symmetry code: (i) .