2,2'-(2,2'-Biimidazole-1,1'-di-yl)diethanoic acid.

In the title compound, C(10)H(10)N(4)O(4), the two imidazole rings adopt a trans conformation and are inclined to one another at a dihedral angle of 55.64 (4)°. In the crystal structure, mol-ecules are linked by inter-molecular O-H⋯N hydrogen bonds into chains running parallel to [010] and layers are formed from these by inter-molecular C-H⋯O hydrogen bonds. Additional C-H⋯O hydrogen bonds produce a three-dimensional network.

Related literature

For the use of 2,2′-biimidazole ligands in metal complex formation, see: Pereira et al. (2006 ▶); Ion et al. (2007 ▶). For related structures, see: Barnett et al. (1999 ▶, 2002 ▶); Zhang & Liang (2009 ▶). For preparation of the starting material, see: Barnett et al. (1996 ▶).

Experimental

Crystal data

C10H10N4O4

M = 250.22

Orthorhombic,

a = 8.4327 (17) Å

b = 15.116 (3) Å

c = 16.702 (3) Å

V = 2129.0 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.12 mm−1

T = 295 K

0.51 × 0.27 × 0.2 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.961, T max = 0.978

18907 measured reflections

2436 independent reflections

2159 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.086

S = 1.05

2436 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.21 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809010897/sj2599sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010897/sj2599Isup2.hkl

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

C10H10N4O4	F(000) = 1040
Mr = 250.22	Dx = 1.561 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 17425 reflections
a = 8.4327 (17) Å	θ = 3.1–27.5°
b = 15.116 (3) Å	µ = 0.12 mm−1
c = 16.702 (3) Å	T = 295 K
V = 2129.0 (7) Å3	Prism, colorless
Z = 8	0.51 × 0.27 × 0.2 mm

Rigaku R-AXIS RAPID diffractometer	2436 independent reflections
Radiation source: fine-focus sealed tube	2159 reflections with I > 2σ(I)
graphite	Rint = 0.026
Detector resolution: 0 pixels mm-1	θmax = 27.5°, θmin = 3.0°
ω scans	h = −10→10
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −19→19
Tmin = 0.961, Tmax = 0.978	l = −21→21
18907 measured reflections

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0416P)2 + 1.0303P] where P = (Fo2 + 2Fc2)/3
2436 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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
O1	0.09214 (10)	0.31447 (5)	0.31089 (5)	0.01700 (19)
H1	0.1441	0.2674	0.2969	0.050*
O2	0.21420 (10)	0.38341 (5)	0.20945 (5)	0.01586 (18)
O4	0.24120 (10)	0.83984 (6)	0.49664 (5)	0.01865 (19)
N3	0.11682 (11)	0.68000 (6)	0.44503 (5)	0.0121 (2)
O3	0.10682 (10)	0.91340 (5)	0.40169 (5)	0.01702 (19)
H10	0.1596	0.9575	0.4189	0.050*
C5	0.12876 (13)	0.38415 (7)	0.26763 (6)	0.0124 (2)
N1	0.11865 (11)	0.54801 (6)	0.26858 (5)	0.0123 (2)
N2	0.23979 (12)	0.67789 (6)	0.26608 (5)	0.0145 (2)
N4	0.23766 (12)	0.55062 (6)	0.44669 (6)	0.0148 (2)
C6	0.18459 (13)	0.61528 (7)	0.40021 (6)	0.0121 (2)
C8	0.12794 (14)	0.65457 (7)	0.52369 (6)	0.0147 (2)
H7	0.0916	0.6857	0.5681	0.018*
C10	0.14467 (13)	0.84266 (7)	0.44296 (6)	0.0127 (2)
C1	0.18552 (13)	0.61380 (7)	0.31285 (6)	0.0120 (2)
C4	0.04544 (14)	0.46687 (7)	0.29809 (7)	0.0146 (2)
H3	−0.0647	0.4654	0.2814	0.017*
H2	0.0477	0.4670	0.3562	0.017*
C9	0.04736 (13)	0.76275 (7)	0.41703 (7)	0.0137 (2)
H9	−0.0594	0.7682	0.4381	0.016*
H8	0.0405	0.7617	0.3591	0.016*
C3	0.13028 (14)	0.57281 (7)	0.18970 (6)	0.0148 (2)
H4	0.0941	0.5413	0.1455	0.018*
C7	0.20265 (14)	0.57488 (8)	0.52384 (7)	0.0159 (2)
H6	0.2264	0.5419	0.5693	0.019*
C2	0.20507 (14)	0.65256 (8)	0.18896 (7)	0.0154 (2)
H5	0.2291	0.6850	0.1432	0.019*

	U11	U22	U33	U12	U13	U23
O1	0.0212 (4)	0.0099 (4)	0.0199 (4)	0.0007 (3)	0.0056 (3)	0.0007 (3)
O2	0.0179 (4)	0.0146 (4)	0.0151 (4)	0.0005 (3)	0.0031 (3)	−0.0006 (3)
O4	0.0233 (4)	0.0155 (4)	0.0172 (4)	−0.0035 (3)	−0.0063 (3)	0.0016 (3)
N3	0.0147 (4)	0.0096 (4)	0.0120 (4)	0.0001 (4)	−0.0002 (3)	−0.0005 (3)
O3	0.0196 (4)	0.0103 (4)	0.0212 (4)	−0.0015 (3)	−0.0053 (3)	0.0019 (3)
C5	0.0118 (5)	0.0114 (5)	0.0140 (5)	−0.0021 (4)	−0.0025 (4)	−0.0014 (4)
N1	0.0143 (4)	0.0092 (4)	0.0134 (4)	−0.0002 (4)	0.0011 (3)	−0.0010 (3)
N2	0.0187 (5)	0.0116 (4)	0.0131 (5)	−0.0011 (4)	0.0000 (4)	0.0015 (3)
N4	0.0184 (5)	0.0121 (4)	0.0138 (4)	0.0022 (4)	0.0008 (4)	0.0017 (3)
C6	0.0141 (5)	0.0092 (5)	0.0132 (5)	−0.0008 (4)	0.0002 (4)	0.0000 (4)
C8	0.0178 (5)	0.0154 (5)	0.0108 (5)	−0.0012 (4)	0.0012 (4)	0.0001 (4)
C10	0.0140 (5)	0.0118 (5)	0.0124 (5)	0.0008 (4)	0.0023 (4)	−0.0009 (4)
C1	0.0137 (5)	0.0087 (5)	0.0135 (5)	0.0009 (4)	0.0001 (4)	−0.0004 (4)
C4	0.0151 (5)	0.0102 (5)	0.0184 (5)	−0.0023 (4)	0.0034 (4)	−0.0010 (4)
C9	0.0152 (5)	0.0098 (5)	0.0160 (5)	0.0017 (4)	−0.0016 (4)	0.0000 (4)
C3	0.0168 (5)	0.0154 (5)	0.0122 (5)	0.0020 (4)	−0.0005 (4)	−0.0020 (4)
C7	0.0198 (5)	0.0162 (5)	0.0118 (5)	−0.0003 (4)	0.0007 (4)	0.0024 (4)
C2	0.0191 (5)	0.0153 (5)	0.0119 (5)	0.0007 (4)	0.0002 (4)	0.0012 (4)

O1—C5	1.3140 (13)	N4—C6	1.3260 (14)
O1—H1	0.8677	N4—C7	1.3718 (14)
O2—C5	1.2098 (14)	C6—C1	1.4592 (15)
O4—C10	1.2117 (14)	C8—C7	1.3594 (17)
N3—C6	1.3579 (14)	C8—H7	0.9300
N3—C8	1.3720 (14)	C10—C9	1.5230 (15)
N3—C9	1.4583 (13)	C4—H3	0.9700
O3—C10	1.3116 (13)	C4—H2	0.9700
O3—H10	0.8513	C9—H9	0.9700
C5—C4	1.5217 (15)	C9—H8	0.9700
N1—C1	1.3614 (14)	C3—C2	1.3605 (17)
N1—C3	1.3733 (14)	C3—H4	0.9300
N1—C4	1.4589 (14)	C7—H6	0.9300
N2—C1	1.3259 (14)	C2—H5	0.9300
N2—C2	1.3752 (14)
C5—O1—H1	113.0	N2—C1—C6	125.43 (10)
C6—N3—C8	107.30 (9)	N1—C1—C6	123.50 (10)
C6—N3—C9	127.61 (9)	N1—C4—C5	112.49 (9)
C8—N3—C9	125.08 (9)	N1—C4—H3	109.1
C10—O3—H10	109.5	C5—C4—H3	109.1
O2—C5—O1	125.04 (10)	N1—C4—H2	109.1
O2—C5—C4	123.44 (10)	C5—C4—H2	109.1
O1—C5—C4	111.49 (9)	H3—C4—H2	107.8
C1—N1—C3	106.98 (9)	N3—C9—C10	111.88 (9)
C1—N1—C4	127.30 (9)	N3—C9—H9	109.2
C3—N1—C4	125.72 (9)	C10—C9—H9	109.2
C1—N2—C2	105.96 (9)	N3—C9—H8	109.2
C6—N4—C7	106.27 (9)	C10—C9—H8	109.2
N4—C6—N3	110.50 (10)	H9—C9—H8	107.9
N4—C6—C1	124.91 (10)	C2—C3—N1	106.48 (9)
N3—C6—C1	124.37 (10)	C2—C3—H4	126.8
C7—C8—N3	106.36 (9)	N1—C3—H4	126.8
C7—C8—H7	126.8	C8—C7—N4	109.57 (10)
N3—C8—H7	126.8	C8—C7—H6	125.2
O4—C10—O3	125.52 (10)	N4—C7—H6	125.2
O4—C10—C9	122.99 (10)	C3—C2—N2	109.69 (10)
O3—C10—C9	111.47 (9)	C3—C2—H5	125.2
N2—C1—N1	110.89 (9)	N2—C2—H5	125.2

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2i	0.87	1.75	2.6137 (13)	176
O3—H10···N4ii	0.85	1.72	2.5666 (13)	176
C4—H2···N4	0.97	2.54	3.2234 (17)	127
C4—H3···O2iii	0.97	2.24	3.0675 (16)	142
C2—H5···O4iv	0.93	2.48	3.2286 (16)	138
C8—H7···O1v	0.93	2.55	3.3610 (15)	146
C9—H8···N2	0.97	2.62	3.2611 (16)	124
C9—H9···O4vi	0.97	2.59	3.3391 (15)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2i	0.87	1.75	2.6137 (13)	176
O3—H10⋯N4ii	0.85	1.72	2.5666 (13)	176
C4—H2⋯N4	0.97	2.54	3.2234 (17)	127
C4—H3⋯O2iii	0.97	2.24	3.0675 (16)	142
C2—H5⋯O4iv	0.93	2.48	3.2286 (16)	138
C8—H7⋯O1v	0.93	2.55	3.3610 (15)	146
C9—H8⋯N2	0.97	2.62	3.2611 (16)	124
C9—H9⋯O4vi	0.97	2.59	3.3391 (15)	135

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