Crystal structure of 1H,1′H-[2,2′-biimid­azol]-3-ium hydrogen tartrate hemi­hydrate

Gao, X.-L.; Bian, L.-F.; Guo, S.-W.

doi:10.1107/S160053681402371X

organic compounds

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ISSN: 2056-9890

Volume 70| Part 11| November 2014| Pages o1221-o1222

doi:10.1107/S160053681402371X

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Crystal structure of 1H,1′H-[2,2′-biimidazol]-3-ium hydrogen tartrate hemihydrate

Xiao-Li Gao,^a ^* Li-Fang Bian ^a and Shao-Wei Guo ^a

^aDepartment of Chemistry, Taiyuan Normal College, Taiyuan, Shanxi 030031, People's Republic of China
^*Correspondence e-mail: xiaoli.gao@sohu.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 14 October 2014; accepted 28 October 2014; online 31 October 2014)

In the crystal of the title hydrated salt, C₆H₇N₄⁺·C₄H₅O₆⁻·0.5H₂O, the biimidazole monocation, 1H,1′H-[2,2′-biimidazol]-3-ium, is hydrogen bonded, via N—H⋯O, O—H⋯O and O—H⋯N hydrogen bonds, to the hydrogen tartrate anion and the water molecule, which is located on a twofold rotation axis, forming sheets parallel to (001). The sheets are linked via C—H⋯O hydrogen bonds, forming a three-dimensional structure. There are also C=O⋯π interactions present [O⋯π distances are 3.00 (9) and 3.21 (7) Å], involving the carbonyl O atoms and the imidazolium ring, which may help to consolidate the structure. In the cation, the dihedral angle between the rings is 11.6 (2)°.

Keywords: crystal structure; biimidazole; imidazolium; tartrate; hydrogen bonding.

CCDC reference: 1031345

1. Related literature

For background to the use of 2,2′-biimidazoles in crystal engineering, see: Shankar et al. (2013 ); Gulbransen & Fitchett (2012 ); Tadokoro & Nakasuji (2000 ). For similar structures, see: Liu & Zhu (2010 ); Gao et al. (2009 ); Li & Yang (2006 ); Mori & Miyoshi (2004 ).

2. Experimental

2.1. Crystal data

C₄H₅O₆⁻·C₆H₇N₄⁺·0.5H₂O
M_r = 293.25
Monoclinic, C 2
a = 19.3211 (13) Å
b = 4.8198 (2) Å
c = 16.1795 (10) Å
β = 122.694 (7)°
V = 1267.99 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 296 K
0.35 × 0.30 × 0.23 mm

2.2. Data collection

Bruker SMART diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ) T_min = 0.956, T_max = 0.971
4238 measured reflections
2292 independent reflections
2100 reflections with I > 2σ(I)
R_int = 0.030

2.3. Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.099
S = 1.11
2292 reflections
202 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2ⁱ	0.92 (3)	1.78 (3)	2.683 (3)	169 (3)
N3—H3A⋯O5ⁱⁱ	0.94 (3)	1.81 (3)	2.729 (3)	167 (3)
N4—H4A⋯O1ⁱ	0.91 (3)	1.73 (3)	2.630 (3)	167 (3)
O3—H3⋯O7	0.83	2.05	2.871 (2)	168
O4—H4⋯O3ⁱⁱⁱ	0.91 (4)	1.86 (4)	2.761 (3)	175 (3)
O6—H6A⋯N1^iv	0.82	1.79	2.598 (3)	168
O7—H7A⋯O1	0.93	2.19	2.802 (2)	123
C2—H2⋯O2^v	0.93	2.35	3.215 (3)	154
C5—H5⋯O4^vi	0.93	2.55	3.415 (3)	155
C6—H6⋯O5^vii	0.93	2.37	3.205 (3)	149
Symmetry codes: (i) x, y-1, z; (ii) $[x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (iii) x, y+1, z; (iv) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (v) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+1]$ ; (vi) -x+1, y-1, -z+2; (vii) -x+1, y, -z+2.

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT (Bruker, 2000); 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: pubCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1031345

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S160053681402371X/su5001sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681402371X/su5001Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681402371X/su5001Isup3.cml

checkCIF report

Synthesis and crystallization top

Diimidazole (1.0 mmol) and tartaric acid (1.0 mmol) were dissolved in water (15 ml) by adding 1.2 ml of 2M HCl while stirring. The solution was left to stand at room temperature and colourless crystals of the title compound were obtained after several weeks.

Refinement top

The NH H atoms and the water molecule H atom were located in a difference Fourier map and refined with U_iso(H) = 1.2U_eq(N,O). The O and C bound H atoms were placed in geometrically idealized positions with C—H = 0.93Å and O—H = 0.84 Å and constrained to refine with U_iso(H) = 1.2U_eq(O,C).

Comment top

Supramolecular assemblies built by means of hydrogen bonding interactions have provided numerous materials with very attractive properties (Gulbransen & Fitchett, 2012; Shankar et al., 2013). 2,2'-Biimidazole, H₂biim, is not only a proton donor, but also a proton acceptor, so that it possesses five possible forms, viz. diprotonated (dication, H₄biim²⁺), monoprotonated (monocation, H₃biim⁺), dideprotonated (dianion, biim^2-), monodeprotonated (monoanion, Hbiim^-) (Tadokoro & Nakasuji, 2000; Mori & Miyoshi, 2004). Therefore, H₂biim appears as an interesting molecular building block for the design of new multidimensional supramolecular arrangements, owing to its capacity to act as a donor or acceptor in the formation of hydrogen bonds (Li & Yang, 2006; Gao et al., 2009; Liu & Zhu, 2010).

The fundamental asymmetric unit of compound (I), contains two monoprotonated biimidazolium cations, two tatrate anions and one water molecular, in which the two imidazole rings of biimidazole are little tortile with the dihedral number is 11.5°. Strong N—H···O and O—H···N hydrogen bonds link neighbour tatrate and biimidazolium moities, then O—H···O hydrogen bonds between water molecular and tatrates link them to form two different zigzag layers as shown in Fig. 1. Two groups of these parallel layers on a twofold rotation axis and invension centre forming a zigzag conformation, then further assemble to tapes via weak C=O···π (centroid of imidazolium ring) interaction arranged alternatively in three-dimensional structure as described in Table 1 and shown in Fig. 2.

Related literature top

For background to the use of 2,2'-biimidazoles in crystal engineering, see: Shankar et al. (2013); Gulbransen & Fitchett (2012); Tadokoro & Nakasuji (2000). For similar structures, see: Liu & Zhu (2010); Gao et al. (2009); Li & Yang (2006); Mori & Miyoshi (2004).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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: pubCIF (Westrip, 2010).

Figures top

Molecular structure and atom labelling of the title compound, with displacement ellipsoids drawn at the 30% probability level. Dashed line indicates hydrogen bonds [see Table 1 for details; symmetry codes: (i) x, y + 1, z; (ii) x + 3/2, y + 3/2, z + 2; (iii) x + 3/2, y + 1/2, z + 2].

Partial crystal packing of the title compound, with the hydrogen bonds (dashed lines) and C═O···π interactions (dashed solid lines) between neighbouring tapes. Cg1 is the centroid of the C4/C5/C6/N3/N4 imidazole ring. [Symmetry codes: (i) x + 3/2, y + 1/2, z + 2; (ii) - x, y, - z; (iii) x, y + 1, z; (iv) x + 3/2, y - 3/2, z + 2; (v) - x - 1, y, - z.]

1H,1'H-[2,2'-Biimidazol]-3-ium 3-carboxy-2,3-dihydroxypropanoate hemihydrate top

Crystal data top

C₄H₅O₆⁻·C₆H₇N₄⁺·0.5H₂O	F(000) = 612
M_r = 293.25	D_x = 1.536 Mg m⁻³
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 2195 reflections
a = 19.3211 (13) Å	θ = 3.5–25.0°
b = 4.8198 (2) Å	µ = 0.13 mm⁻¹
c = 16.1795 (10) Å	T = 296 K
β = 122.694 (7)°	Plate, colourless
V = 1267.99 (13) Å³	0.35 × 0.30 × 0.23 mm
Z = 4

Data collection top

Bruker SMART diffractometer	2292 independent reflections
Radiation source: fine-focus sealed tube	2100 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
Detector resolution: 16.0733 pixels mm^-1	θ_max = 25.5°, θ_min = 3.6°
phi and ω scans	h = −23→10
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	k = −5→5
T_min = 0.956, T_max = 0.971	l = −18→19
4238 measured reflections

Refinement top

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ²(F_o²) + (0.0364P)² + 0.5619P] where P = (F_o² + 2F_c²)/3
2292 reflections	(Δ/σ)_max < 0.001
202 parameters	Δρ_max = 0.16 e Å⁻³
1 restraint	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₄H₅O₆⁻·C₆H₇N₄⁺·0.5H₂O	V = 1267.99 (13) Å³
M_r = 293.25	Z = 4
Monoclinic, C2	Mo Kα radiation
a = 19.3211 (13) Å	µ = 0.13 mm⁻¹
b = 4.8198 (2) Å	T = 296 K
c = 16.1795 (10) Å	0.35 × 0.30 × 0.23 mm
β = 122.694 (7)°

Data collection top

Bruker SMART diffractometer	2292 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	2100 reflections with I > 2σ(I)
T_min = 0.956, T_max = 0.971	R_int = 0.030
4238 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	1 restraint
wR(F²) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	Δρ_max = 0.16 e Å⁻³
2292 reflections	Δρ_min = −0.27 e Å⁻³
202 parameters

Special details top

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.

The line _refine_ls_abs_structure_Flack -1.5 (15) has been removed. According to the comment in an absolute configuration has been assigned, obtained using x by least-squares refinement. There is too high standard uncertainty on x and no information available that the assigned value is confirmed by the diffraction measurements.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.12363 (19)	0.3256 (7)	0.54798 (19)	0.0501 (8)
H1	0.0811	0.4221	0.4950	0.060*
C2	0.17427 (17)	0.1439 (8)	0.54276 (19)	0.0465 (8)
H2	0.1729	0.0925	0.4865	0.056*
C3	0.20830 (14)	0.1770 (6)	0.69462 (16)	0.0287 (6)
C4	0.25343 (14)	0.1445 (5)	0.80032 (16)	0.0266 (5)
C5	0.33858 (17)	−0.0022 (6)	0.95007 (19)	0.0385 (7)
H5	0.3788	−0.1057	1.0029	0.046*
C6	0.29783 (17)	0.2162 (6)	0.95549 (18)	0.0380 (7)
H6	0.3044	0.2923	1.0121	0.046*
N1	0.14434 (14)	0.3465 (5)	0.64335 (15)	0.0400 (6)
N2	0.22801 (13)	0.0497 (5)	0.63601 (15)	0.0357 (5)
N3	0.24455 (13)	0.3045 (5)	0.86056 (14)	0.0307 (5)
N4	0.31045 (13)	−0.0455 (5)	0.85300 (15)	0.0307 (5)
H2A	0.2689 (17)	−0.079 (6)	0.6544 (19)	0.037*
H3A	0.2032 (17)	0.440 (6)	0.8388 (18)	0.037*
H4A	0.3337 (16)	−0.172 (7)	0.8333 (19)	0.037*
C7	0.38284 (14)	0.5315 (5)	0.74083 (18)	0.0295 (6)
C8	0.44290 (15)	0.3252 (6)	0.74053 (18)	0.0308 (6)
C9	0.51381 (14)	0.4868 (5)	0.74572 (17)	0.0288 (6)
H9	0.4916	0.6076	0.6881	0.035*
C10	0.57380 (15)	0.2829 (6)	0.74598 (17)	0.0299 (6)
O1	0.37823 (11)	0.5416 (4)	0.81509 (13)	0.0379 (5)
O2	0.34295 (11)	0.6789 (4)	0.66602 (12)	0.0436 (5)
O3	0.47460 (11)	0.1317 (4)	0.81901 (13)	0.0382 (5)
H3	0.4744	0.1836	0.8679	0.046*
O4	0.55700 (11)	0.6495 (4)	0.83171 (14)	0.0402 (5)
O5	0.64334 (10)	0.2498 (4)	0.81780 (12)	0.0353 (5)
O6	0.54328 (11)	0.1477 (5)	0.66429 (13)	0.0475 (5)
H6A	0.5803	0.0673	0.6635	0.057*
H4	0.5313 (19)	0.807 (8)	0.832 (2)	0.057*
H8	0.4108 (19)	0.231 (7)	0.676 (2)	0.057*
O7	0.5000	0.3371 (9)	1.0000	0.0714 (10)
H7A	0.4667	0.4934	0.9729	0.086*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0480 (17)	0.063 (2)	0.0286 (13)	0.0215 (17)	0.0139 (13)	0.0062 (15)
C2	0.0506 (17)	0.0589 (19)	0.0278 (13)	0.0134 (17)	0.0196 (12)	0.0000 (14)
C3	0.0276 (12)	0.0321 (13)	0.0280 (12)	0.0028 (12)	0.0161 (10)	0.0002 (12)
C4	0.0262 (12)	0.0257 (12)	0.0282 (11)	0.0020 (11)	0.0149 (10)	0.0017 (11)
C5	0.0380 (14)	0.0426 (16)	0.0297 (13)	0.0072 (13)	0.0149 (11)	0.0046 (12)
C6	0.0405 (15)	0.0437 (17)	0.0273 (12)	0.0023 (13)	0.0168 (12)	−0.0015 (12)
N1	0.0373 (12)	0.0501 (14)	0.0286 (11)	0.0179 (12)	0.0152 (10)	0.0038 (11)
N2	0.0348 (12)	0.0400 (13)	0.0305 (11)	0.0110 (11)	0.0165 (10)	−0.0011 (10)
N3	0.0327 (11)	0.0322 (12)	0.0293 (11)	0.0050 (10)	0.0180 (9)	0.0005 (9)
N4	0.0318 (11)	0.0310 (12)	0.0295 (11)	0.0067 (10)	0.0167 (9)	0.0033 (9)
C7	0.0245 (12)	0.0283 (13)	0.0354 (13)	−0.0009 (11)	0.0160 (10)	−0.0059 (11)
C8	0.0300 (13)	0.0297 (14)	0.0312 (12)	0.0041 (11)	0.0155 (11)	−0.0018 (11)
C9	0.0299 (12)	0.0254 (13)	0.0286 (12)	0.0069 (11)	0.0141 (10)	0.0028 (11)
C10	0.0322 (13)	0.0296 (13)	0.0318 (13)	−0.0007 (11)	0.0198 (12)	−0.0003 (11)
O1	0.0442 (11)	0.0357 (10)	0.0423 (10)	0.0090 (9)	0.0290 (9)	0.0043 (8)
O2	0.0412 (11)	0.0545 (13)	0.0332 (9)	0.0233 (11)	0.0190 (8)	0.0074 (10)
O3	0.0501 (11)	0.0284 (10)	0.0445 (10)	0.0103 (9)	0.0311 (9)	0.0066 (9)
O4	0.0355 (10)	0.0283 (9)	0.0462 (10)	0.0036 (9)	0.0151 (8)	−0.0117 (9)
O5	0.0268 (9)	0.0365 (10)	0.0347 (9)	0.0052 (8)	0.0114 (8)	−0.0045 (8)
O6	0.0349 (10)	0.0641 (14)	0.0352 (9)	0.0139 (10)	0.0135 (8)	−0.0140 (10)
O7	0.064 (2)	0.078 (3)	0.061 (2)	0.000	0.0266 (18)	0.000

Geometric parameters (Å, º) top

C1—C2	1.350 (4)	N4—H4A	0.91 (3)
C1—N1	1.373 (3)	C7—O2	1.247 (3)
C1—H1	0.9300	C7—O1	1.253 (3)
C2—N2	1.367 (3)	C7—C8	1.530 (4)
C2—H2	0.9300	C8—O3	1.421 (3)
C3—N1	1.333 (3)	C8—C9	1.538 (4)
C3—N2	1.346 (3)	C8—H8	0.99 (3)
C3—C4	1.449 (3)	C9—O4	1.412 (3)
C4—N3	1.325 (3)	C9—C10	1.518 (3)
C4—N4	1.328 (3)	C9—H9	0.9800
C5—C6	1.346 (4)	C10—O5	1.222 (3)
C5—N4	1.372 (3)	C10—O6	1.295 (3)
C5—H5	0.9300	O3—H3	0.8309
C6—N3	1.375 (3)	O4—H4	0.91 (4)
C6—H6	0.9300	O6—H6A	0.8200
N2—H2A	0.92 (3)	O7—H7A	0.9324
N3—H3A	0.94 (3)

C2—C1—N1	109.7 (2)	C4—N4—C5	107.9 (2)
C2—C1—H1	125.2	C4—N4—H4A	129.2 (17)
N1—C1—H1	125.2	C5—N4—H4A	122.4 (17)
C1—C2—N2	106.9 (2)	O2—C7—O1	125.6 (2)
C1—C2—H2	126.6	O2—C7—C8	116.0 (2)
N2—C2—H2	126.6	O1—C7—C8	118.4 (2)
N1—C3—N2	111.2 (2)	O3—C8—C7	112.7 (2)
N1—C3—C4	124.5 (2)	O3—C8—C9	110.02 (19)
N2—C3—C4	124.3 (2)	C7—C8—C9	109.0 (2)
N3—C4—N4	108.8 (2)	O3—C8—H8	111 (2)
N3—C4—C3	124.8 (2)	C7—C8—H8	105.0 (19)
N4—C4—C3	126.4 (2)	C9—C8—H8	108.7 (18)
C6—C5—N4	108.0 (2)	O4—C9—C10	108.24 (19)
C6—C5—H5	126.0	O4—C9—C8	111.7 (2)
N4—C5—H5	126.0	C10—C9—C8	109.19 (19)
C5—C6—N3	106.3 (2)	O4—C9—H9	109.2
C5—C6—H6	126.8	C10—C9—H9	109.2
N3—C6—H6	126.8	C8—C9—H9	109.2
C3—N1—C1	105.3 (2)	O5—C10—O6	124.4 (2)
C3—N2—C2	106.9 (2)	O5—C10—C9	122.2 (2)
C3—N2—H2A	126.9 (17)	O6—C10—C9	113.4 (2)
C2—N2—H2A	126.1 (17)	C8—O3—H3	115.5
C4—N3—C6	109.0 (2)	C9—O4—H4	116 (2)
C4—N3—H3A	123.3 (16)	C10—O6—H6A	109.5
C6—N3—H3A	127.3 (16)

N1—C1—C2—N2	−0.3 (4)	N3—C4—N4—C5	−0.2 (3)
N1—C3—C4—N3	−9.7 (4)	C3—C4—N4—C5	179.2 (3)
N2—C3—C4—N3	166.9 (3)	C6—C5—N4—C4	0.1 (3)
N1—C3—C4—N4	170.9 (3)	O2—C7—C8—O3	−169.2 (2)
N2—C3—C4—N4	−12.4 (4)	O1—C7—C8—O3	11.6 (3)
N4—C5—C6—N3	0.1 (3)	O2—C7—C8—C9	68.4 (3)
N2—C3—N1—C1	−0.6 (3)	O1—C7—C8—C9	−110.8 (3)
C4—C3—N1—C1	176.5 (3)	O3—C8—C9—O4	−64.0 (2)
C2—C1—N1—C3	0.5 (4)	C7—C8—C9—O4	60.0 (2)
N1—C3—N2—C2	0.4 (3)	O3—C8—C9—C10	55.7 (3)
C4—C3—N2—C2	−176.7 (3)	C7—C8—C9—C10	179.7 (2)
C1—C2—N2—C3	0.0 (4)	O4—C9—C10—O5	9.8 (3)
N4—C4—N3—C6	0.3 (3)	C8—C9—C10—O5	−112.0 (3)
C3—C4—N3—C6	−179.1 (3)	O4—C9—C10—O6	−171.4 (2)
C5—C6—N3—C4	−0.3 (3)	C8—C9—C10—O6	66.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.92 (3)	1.78 (3)	2.683 (3)	169 (3)
N3—H3A···O5ⁱⁱ	0.94 (3)	1.81 (3)	2.729 (3)	167 (3)
N4—H4A···O1ⁱ	0.91 (3)	1.73 (3)	2.630 (3)	167 (3)
O3—H3···O7	0.83	2.05	2.871 (2)	168
O4—H4···O3ⁱⁱⁱ	0.91 (4)	1.86 (4)	2.761 (3)	175 (3)
O6—H6A···N1^iv	0.82	1.79	2.598 (3)	168
O7—H7A···O1	0.93	2.19	2.802 (2)	123
C2—H2···O2^v	0.93	2.35	3.215 (3)	154
C5—H5···O4^vi	0.93	2.55	3.415 (3)	155
C6—H6···O5^vii	0.93	2.37	3.205 (3)	149

Symmetry codes: (i) x, y−1, z; (ii) x−1/2, y+1/2, z; (iii) x, y+1, z; (iv) x+1/2, y−1/2, z; (v) −x+1/2, y−1/2, −z+1; (vi) −x+1, y−1, −z+2; (vii) −x+1, y, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.92 (3)	1.78 (3)	2.683 (3)	169 (3)
N3—H3A···O5ⁱⁱ	0.94 (3)	1.81 (3)	2.729 (3)	167 (3)
N4—H4A···O1ⁱ	0.91 (3)	1.73 (3)	2.630 (3)	167 (3)
O3—H3···O7	0.83	2.05	2.871 (2)	168
O4—H4···O3ⁱⁱⁱ	0.91 (4)	1.86 (4)	2.761 (3)	175 (3)
O6—H6A···N1^iv	0.82	1.79	2.598 (3)	168
O7—H7A···O1	0.93	2.19	2.802 (2)	123
C2—H2···O2^v	0.93	2.35	3.215 (3)	154
C5—H5···O4^vi	0.93	2.55	3.415 (3)	155
C6—H6···O5^vii	0.93	2.37	3.205 (3)	149

Symmetry codes: (i) x, y−1, z; (ii) x−1/2, y+1/2, z; (iii) x, y+1, z; (iv) x+1/2, y−1/2, z; (v) −x+1/2, y−1/2, −z+1; (vi) −x+1, y−1, −z+2; (vii) −x+1, y, −z+2.

Acknowledgements

We are grateful to the National Natural Science Foundation of China (grant No. 51174275) for financial support.

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Volume 70| Part 11| November 2014| Pages o1221-o1222

doi:10.1107/S160053681402371X

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of 1H,1′H-[2,2′-biimid­azol]-3-ium hydrogen tartrate hemi­hydrate

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 1H,1′H-[2,2′-biimidazol]-3-ium hydrogen tartrate hemihydrate