Bis(4-methyl-imidazolium) succinate succinic acid solvate.

In the title compound, 2C(4)H(7)N(2) (+)·C(4)H(4)O(4) (2-)·C(4)H(6)O(4), the asymmetric unit consists of two 4-methyl-imidazolium cations, one succinate dianion and one netrual succinic acid mol-ecule and within the latter components, the C-O, C=O and C O bonds are clearly evidenced from their relative distances. In the crystal structure, the individual components are linked by inter-molecular N-H⋯O, O-H⋯O and C-H⋯O hydrogen bonds into a two-dimensional network parallel to the (101) plane in which R(3) (3)(9), R(3) (3)(12) and R(4) (4)(18) hydrogen-bond motifs are present.

Related literature

For general background on co-crystals, see: Aakeröy & Salmon (2005 ▶); Aakeröy et al. (2007 ▶); Childs & Hardcastle (2007 ▶); Childs et al. (2007 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

2C4H7N2 +·C4H4O4 2−·C4H6O4

M = 400.39

Monoclinic,

a = 17.260 (5) Å

b = 14.066 (4) Å

c = 7.761 (2) Å

β = 95.008 (6)°

V = 1877.0 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 296 K

0.30 × 0.10 × 0.04 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.957, T max = 0.995

20337 measured reflections

4080 independent reflections

2197 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.153

S = 0.95

4080 reflections

273 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.25 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, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809006205/lh2776sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006205/lh2776Isup2.hkl

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

2C4H7N2+·C4H4O42−·C4H6O4	F(000) = 848
Mr = 400.39	Dx = 1.417 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2035 reflections
a = 17.260 (5) Å	θ = 2.4–21.1°
b = 14.066 (4) Å	µ = 0.12 mm−1
c = 7.761 (2) Å	T = 296 K
β = 95.008 (6)°	Plate, colorless
V = 1877.0 (9) Å3	0.30 × 0.10 × 0.04 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	4080 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	2197 reflections with I > 2σ(I)
graphite	Rint = 0.063
0.3° wide ω exposures scans	θmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −22→22
Tmin = 0.957, Tmax = 0.995	k = −17→17
20337 measured reflections	l = −8→9

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ2(Fo2) + (0.0817P)2] where P = (Fo2 + 2Fc2)/3
4080 reflections	(Δ/σ)max < 0.001
273 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.25 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
C1	0.45695 (11)	0.47579 (16)	0.7860 (3)	0.0375 (6)
C2	0.50516 (13)	0.33293 (17)	0.7523 (3)	0.0476 (6)
H2	0.5380	0.2839	0.7247	0.057*
C3	0.40700 (12)	0.41101 (16)	0.8406 (3)	0.0431 (6)
H3	0.3597	0.4241	0.8847	0.052*
C4	0.45464 (13)	0.58059 (16)	0.7747 (3)	0.0498 (7)
H4A	0.4367	0.5993	0.6590	0.075*
H4B	0.5059	0.6057	0.8036	0.075*
H4C	0.4199	0.6050	0.8540	0.075*
C5	0.96099 (11)	0.34301 (16)	0.3015 (3)	0.0342 (5)
C6	0.91078 (12)	0.40732 (16)	0.3567 (3)	0.0404 (6)
H6	0.8665	0.3936	0.4122	0.049*
C7	1.00090 (12)	0.48664 (17)	0.2388 (3)	0.0435 (6)
H7	1.0302	0.5361	0.1986	0.052*
C8	0.96426 (13)	0.23840 (16)	0.3093 (3)	0.0454 (6)
H8A	0.9213	0.2150	0.3676	0.068*
H8B	1.0122	0.2190	0.3714	0.068*
H8C	0.9614	0.2131	0.1941	0.068*
C9	0.83954 (12)	0.73296 (15)	0.4322 (3)	0.0327 (5)
C10	0.76053 (11)	0.71074 (15)	0.4945 (3)	0.0352 (5)
H10A	0.7558	0.7446	0.6020	0.042*
H10B	0.7206	0.7348	0.4101	0.042*
C11	0.74541 (12)	0.60712 (15)	0.5235 (3)	0.0377 (6)
H11A	0.7865	0.5824	0.6046	0.045*
H11B	0.7482	0.5737	0.4150	0.045*
C12	0.66724 (12)	0.58515 (15)	0.5925 (3)	0.0374 (6)
C13	0.70985 (12)	0.28540 (16)	0.5270 (3)	0.0380 (6)
C14	0.76523 (12)	0.20813 (16)	0.4875 (3)	0.0398 (6)
H14A	0.8133	0.2165	0.5604	0.048*
H14B	0.7772	0.2145	0.3682	0.048*
C15	0.73494 (12)	0.10900 (16)	0.5142 (3)	0.0449 (6)
H15A	0.7241	0.1020	0.6341	0.054*
H15B	0.6863	0.1009	0.4431	0.054*
C16	0.79014 (13)	0.03232 (16)	0.4709 (3)	0.0410 (6)
N1	0.43813 (11)	0.32252 (14)	0.8197 (3)	0.0457 (5)
H1	0.4148 (14)	0.2622 (18)	0.842 (3)	0.055*
N2	0.51776 (10)	0.42424 (13)	0.7306 (3)	0.0413 (5)
H2A	0.5629 (13)	0.4491 (16)	0.678 (3)	0.050*
N3	0.93627 (10)	0.49658 (14)	0.3170 (2)	0.0433 (5)
H3A	0.9102 (13)	0.5635 (17)	0.342 (3)	0.052*
N4	1.01708 (10)	0.39539 (13)	0.2269 (2)	0.0386 (5)
H4	1.0622 (13)	0.3685 (15)	0.177 (3)	0.046*
O1	0.88428 (9)	0.66845 (11)	0.3982 (2)	0.0565 (5)
O2	0.85672 (8)	0.82023 (10)	0.4172 (2)	0.0453 (4)
O3	0.65044 (8)	0.49741 (10)	0.6087 (2)	0.0461 (4)
O4	0.62385 (9)	0.64950 (11)	0.6310 (3)	0.0647 (6)
O5	0.73726 (9)	0.37014 (12)	0.5060 (2)	0.0542 (5)
H5	0.7020 (17)	0.419 (2)	0.544 (3)	0.081*
O6	0.64637 (10)	0.27081 (12)	0.5766 (3)	0.0671 (6)
O7	0.84928 (10)	0.04663 (12)	0.4027 (3)	0.0639 (6)
O8	0.76793 (10)	−0.05217 (12)	0.5142 (3)	0.0605 (6)
H8	0.8020 (17)	−0.105 (2)	0.473 (4)	0.091*

	U11	U22	U33	U12	U13	U23
C1	0.0270 (11)	0.0344 (13)	0.0528 (14)	0.0012 (9)	0.0138 (10)	−0.0009 (11)
C2	0.0344 (13)	0.0358 (15)	0.0763 (18)	−0.0018 (11)	0.0253 (12)	−0.0020 (13)
C3	0.0284 (12)	0.0410 (15)	0.0625 (16)	−0.0039 (11)	0.0202 (11)	0.0011 (12)
C4	0.0381 (14)	0.0369 (15)	0.0772 (18)	−0.0010 (11)	0.0215 (13)	0.0039 (13)
C5	0.0255 (10)	0.0325 (13)	0.0465 (14)	−0.0003 (9)	0.0148 (10)	−0.0016 (10)
C6	0.0282 (12)	0.0356 (14)	0.0606 (16)	0.0007 (10)	0.0217 (11)	−0.0004 (11)
C7	0.0356 (13)	0.0347 (15)	0.0629 (16)	−0.0005 (10)	0.0199 (11)	−0.0009 (12)
C8	0.0384 (13)	0.0350 (14)	0.0663 (17)	0.0041 (10)	0.0233 (12)	0.0009 (12)
C9	0.0264 (11)	0.0247 (12)	0.0488 (14)	−0.0004 (9)	0.0130 (10)	−0.0008 (10)
C10	0.0279 (11)	0.0303 (13)	0.0497 (14)	−0.0003 (9)	0.0167 (10)	0.0027 (10)
C11	0.0284 (11)	0.0291 (13)	0.0583 (15)	−0.0022 (9)	0.0186 (11)	0.0014 (11)
C12	0.0307 (12)	0.0264 (13)	0.0573 (16)	0.0006 (10)	0.0162 (11)	−0.0019 (11)
C13	0.0300 (11)	0.0330 (14)	0.0532 (15)	0.0001 (10)	0.0164 (10)	0.0005 (11)
C14	0.0293 (12)	0.0372 (14)	0.0553 (15)	0.0034 (10)	0.0167 (11)	−0.0011 (11)
C15	0.0314 (12)	0.0370 (15)	0.0693 (17)	0.0051 (10)	0.0222 (12)	−0.0016 (12)
C16	0.0322 (12)	0.0341 (14)	0.0594 (15)	0.0004 (10)	0.0184 (11)	−0.0030 (11)
N1	0.0371 (11)	0.0327 (12)	0.0697 (14)	−0.0074 (9)	0.0195 (10)	0.0020 (10)
N2	0.0298 (10)	0.0333 (12)	0.0639 (13)	−0.0044 (8)	0.0223 (9)	0.0000 (10)
N3	0.0353 (10)	0.0325 (12)	0.0645 (14)	0.0056 (9)	0.0183 (9)	−0.0042 (10)
N4	0.0280 (10)	0.0344 (12)	0.0561 (13)	0.0016 (8)	0.0200 (9)	−0.0018 (9)
O1	0.0422 (10)	0.0304 (10)	0.1026 (14)	0.0040 (7)	0.0383 (9)	−0.0027 (9)
O2	0.0326 (9)	0.0257 (9)	0.0821 (12)	−0.0009 (7)	0.0309 (8)	0.0033 (8)
O3	0.0342 (8)	0.0266 (9)	0.0819 (12)	−0.0027 (7)	0.0300 (8)	0.0026 (8)
O4	0.0474 (10)	0.0309 (10)	0.1235 (16)	0.0039 (8)	0.0513 (11)	−0.0015 (10)
O5	0.0409 (9)	0.0291 (10)	0.0980 (15)	0.0005 (7)	0.0368 (10)	−0.0032 (9)
O6	0.0406 (10)	0.0420 (11)	0.1255 (16)	0.0021 (8)	0.0465 (11)	0.0062 (10)
O7	0.0452 (10)	0.0430 (11)	0.1108 (15)	0.0044 (8)	0.0480 (10)	0.0016 (10)
O8	0.0464 (10)	0.0310 (11)	0.1109 (16)	0.0043 (8)	0.0453 (10)	0.0041 (10)

C1—C3	1.348 (3)	C10—C11	1.501 (3)
C1—N2	1.375 (3)	C10—H10A	0.9700
C1—C4	1.477 (3)	C10—H10B	0.9700
C2—N2	1.316 (3)	C11—C12	1.526 (3)
C2—N1	1.319 (3)	C11—H11A	0.9700
C2—H2	0.9300	C11—H11B	0.9700
C3—N1	1.371 (3)	C12—O4	1.228 (3)
C3—H3	0.9300	C12—O3	1.276 (2)
C4—H4A	0.9600	C13—O6	1.210 (2)
C4—H4B	0.9600	C13—O5	1.298 (3)
C4—H4C	0.9600	C13—C14	1.497 (3)
C5—C6	1.348 (3)	C14—C15	1.510 (3)
C5—N4	1.383 (3)	C14—H14A	0.9700
C5—C8	1.474 (3)	C14—H14B	0.9700
C6—N3	1.374 (3)	C15—C16	1.497 (3)
C6—H6	0.9300	C15—H15A	0.9700
C7—N4	1.319 (3)	C15—H15B	0.9700
C7—N3	1.323 (3)	C16—O7	1.207 (2)
C7—H7	0.9300	C16—O8	1.302 (3)
C8—H8A	0.9600	N1—H1	0.96 (2)
C8—H8B	0.9600	N2—H2A	0.97 (2)
C8—H8C	0.9600	N3—H3A	1.07 (2)
C9—O1	1.235 (2)	N4—H4	0.98 (2)
C9—O2	1.271 (2)	O5—H5	0.98 (3)
C9—C10	1.519 (3)	O8—H8	1.02 (3)
C3—C1—N2	105.6 (2)	C10—C11—H11A	108.6
C3—C1—C4	132.7 (2)	C12—C11—H11A	108.6
N2—C1—C4	121.66 (19)	C10—C11—H11B	108.6
N2—C2—N1	108.6 (2)	C12—C11—H11B	108.6
N2—C2—H2	125.7	H11A—C11—H11B	107.5
N1—C2—H2	125.7	O4—C12—O3	122.69 (19)
C1—C3—N1	107.98 (19)	O4—C12—C11	120.84 (19)
C1—C3—H3	126.0	O3—C12—C11	116.47 (18)
N1—C3—H3	126.0	O6—C13—O5	123.1 (2)
C1—C4—H4A	109.5	O6—C13—C14	123.7 (2)
C1—C4—H4B	109.5	O5—C13—C14	113.25 (18)
H4A—C4—H4B	109.5	C13—C14—C15	114.05 (17)
C1—C4—H4C	109.5	C13—C14—H14A	108.7
H4A—C4—H4C	109.5	C15—C14—H14A	108.7
H4B—C4—H4C	109.5	C13—C14—H14B	108.7
C6—C5—N4	105.58 (19)	C15—C14—H14B	108.7
C6—C5—C8	132.85 (19)	H14A—C14—H14B	107.6
N4—C5—C8	121.57 (18)	C16—C15—C14	113.57 (18)
C5—C6—N3	108.32 (18)	C16—C15—H15A	108.9
C5—C6—H6	125.8	C14—C15—H15A	108.9
N3—C6—H6	125.8	C16—C15—H15B	108.9
N4—C7—N3	109.1 (2)	C14—C15—H15B	108.9
N4—C7—H7	125.4	H15A—C15—H15B	107.7
N3—C7—H7	125.4	O7—C16—O8	123.0 (2)
C5—C8—H8A	109.5	O7—C16—C15	123.9 (2)
C5—C8—H8B	109.5	O8—C16—C15	113.10 (19)
H8A—C8—H8B	109.5	C2—N1—C3	108.21 (19)
C5—C8—H8C	109.5	C2—N1—H1	124.3 (15)
H8A—C8—H8C	109.5	C3—N1—H1	127.4 (15)
H8B—C8—H8C	109.5	C2—N2—C1	109.59 (18)
O1—C9—O2	122.35 (18)	C2—N2—H2A	123.4 (13)
O1—C9—C10	120.83 (19)	C1—N2—H2A	126.9 (13)
O2—C9—C10	116.82 (18)	C7—N3—C6	107.79 (19)
C11—C10—C9	114.85 (17)	C7—N3—H3A	124.3 (12)
C11—C10—H10A	108.6	C6—N3—H3A	127.9 (12)
C9—C10—H10A	108.6	C7—N4—C5	109.20 (18)
C11—C10—H10B	108.6	C7—N4—H4	126.0 (13)
C9—C10—H10B	108.6	C5—N4—H4	124.8 (13)
H10A—C10—H10B	107.5	C13—O5—H5	111.4 (16)
C10—C11—C12	114.83 (17)	C16—O8—H8	113.4 (16)
N2—C1—C3—N1	0.7 (3)	C14—C15—C16—O7	−8.0 (4)
C4—C1—C3—N1	179.0 (3)	C14—C15—C16—O8	172.0 (2)
N4—C5—C6—N3	−0.3 (3)	N2—C2—N1—C3	0.3 (3)
C8—C5—C6—N3	179.4 (2)	C1—C3—N1—C2	−0.6 (3)
O1—C9—C10—C11	4.6 (3)	N1—C2—N2—C1	0.1 (3)
O2—C9—C10—C11	−175.4 (2)	C3—C1—N2—C2	−0.5 (3)
C9—C10—C11—C12	177.83 (19)	C4—C1—N2—C2	−179.0 (2)
C10—C11—C12—O4	−4.7 (3)	N4—C7—N3—C6	0.2 (3)
C10—C11—C12—O3	175.8 (2)	C5—C6—N3—C7	0.0 (3)
O6—C13—C14—C15	0.2 (4)	N3—C7—N4—C5	−0.4 (3)
O5—C13—C14—C15	179.0 (2)	C6—C5—N4—C7	0.4 (3)
C13—C14—C15—C16	178.83 (19)	C8—C5—N4—C7	−179.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4i	0.96 (2)	1.74 (2)	2.699 (3)	176 (2)
N2—H2A···O3	0.97 (2)	1.78 (2)	2.752 (2)	173.0 (19)
N3—H3A···O1	1.07 (2)	1.61 (2)	2.673 (2)	170.6 (19)
N4—H4···O2ii	0.98 (2)	1.77 (2)	2.745 (2)	178.8 (19)
O5—H5···O3	0.98 (3)	1.53 (3)	2.509 (2)	177 (3)
O8—H8···O2iii	1.02 (3)	1.50 (3)	2.518 (2)	176 (3)
C2—H2···O6	0.93	2.29	3.024 (3)	136
C3—H3···O8iv	0.93	2.43	3.354 (3)	176
C6—H6···O5	0.93	2.43	3.346 (3)	169
C7—H7···O7v	0.93	2.29	3.017 (3)	134

Table 1

Selected bond lengths (Å)

C9—O1	1.235 (2)
C9—O2	1.271 (2)
C12—O4	1.228 (3)
C12—O3	1.276 (2)
C13—O6	1.210 (2)
C13—O5	1.298 (3)
C16—O7	1.207 (2)
C16—O8	1.302 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4i	0.96 (2)	1.74 (2)	2.699 (3)	176 (2)
N2—H2A⋯O3	0.97 (2)	1.78 (2)	2.752 (2)	173.0 (19)
N3—H3A⋯O1	1.07 (2)	1.61 (2)	2.673 (2)	170.6 (19)
N4—H4⋯O2ii	0.98 (2)	1.77 (2)	2.745 (2)	178.8 (19)
O5—H5⋯O3	0.98 (3)	1.53 (3)	2.509 (2)	177 (3)
O8—H8⋯O2iii	1.02 (3)	1.50 (3)	2.518 (2)	176 (3)
C2—H2⋯O6	0.93	2.29	3.024 (3)	136
C3—H3⋯O8iv	0.93	2.43	3.354 (3)	176
C6—H6⋯O5	0.93	2.43	3.346 (3)	169
C7—H7⋯O7v	0.93	2.29	3.017 (3)	134

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