(2,2'-Bipyridine)bis-(3-carboxy-pyrazine-2-carboxyl-ato)copper(II) dihydrate.

The title six-coordinated distorted octa-hedral complex, [Cu(C(6)H(3)N(2)O(4))(2)(C(10)H(8)N(2))]·2H(2)O, consists of two 3-carboxy-pyrazine-2-carboxyl-ate anions and one 2,2'-bipyridine ligand. There is a twofold rotation axis positioned at the Cu(II) center. The N atoms of the pyrazine ring occupy the axial positions and two proton-transferred O atoms of tbe acid together with the two N atoms of the 2,2'-bipyridine ligand complete the equatorial plane. The inter-actions existing in the crystal structure are inter-molecular O-H⋯O hydrogen bonds, and C-H⋯O and C-O⋯π inter-actions (O⋯π =3.145 Å, C-O⋯π = 149.75°).

Related literature

There are several compounds made from pyrazine-2,3-dicarboxylic acid, but most of them are in a polymeric form; see, for example: Tombul et al. (2007 ▶, 2008 ▶). For related literature, see: Egli & Sarkhel (2007 ▶).

Experimental

Crystal data

[Cu(C6H3N2O4)2(C10n class="Species">H8N2)]·2H2O

M = 589.96

Monoclinic,

a = 18.3080 (8) Å

b = 9.2168 (4) Å

c = 16.3235 (7) Å

β = 122.480 (5)°

V = 2323.59 (18) Å3

Z = 4

Mo Kα radiation

μ = 1.01 mm−1

T = 100 (2) K

0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.823, T max = 0.823

14982 measured reflections

3500 independent reflections

3289 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.063

S = 1.04

3500 reflections

177 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808022885/om2248sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022885/om2248Isup2.hkl

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

[Cu(C6H3N2O4)2(C10H8N2)]·2H2O	F000 = 1204
Mr = 589.96	Dx = 1.686 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9557 reflections
a = 18.3080 (8) Å	θ = 2.6–30.5º
b = 9.2168 (4) Å	µ = 1.01 mm−1
c = 16.3235 (7) Å	T = 100 (2) K
β = 122.480 (5)º	Prism, colourless
V = 2323.59 (18) Å3	0.20 × 0.20 × 0.20 mm
Z = 4

Bruker SMART APEXII diffractometer	3500 independent reflections
Radiation source: fine-focus sealed tube	3289 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.017
T = 100(2) K	θmax = 30.5º
φ and ω scans	θmin = 2.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −26→26
Tmin = 0.823, Tmax = 0.823	k = −13→13
14982 measured reflections	l = −23→23

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.023	H-atom parameters constrained
wR(F2) = 0.063	w = 1/[σ2(Fo2) + (0.04P)2 + 1.2P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3500 reflections	Δρmax = 0.49 e Å−3
177 parameters	Δρmin = −0.31 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
Cu1	1.0000	0.367362 (16)	0.2500	0.01104 (5)
O1	0.91326 (4)	0.21893 (8)	0.16501 (5)	0.01386 (13)
O2	0.85176 (5)	0.08782 (9)	0.02861 (6)	0.02271 (16)
O3	0.90660 (5)	0.00760 (8)	−0.12364 (6)	0.02014 (15)
H3O	0.8658	−0.0282	−0.1804	0.024*
O4	0.81385 (5)	0.19258 (9)	−0.16881 (6)	0.02211 (16)
N1	1.02854 (5)	0.32913 (9)	0.12702 (6)	0.01404 (15)
N2	1.01283 (6)	0.27792 (10)	−0.05007 (6)	0.01888 (17)
N3	0.91587 (5)	0.53313 (8)	0.19274 (6)	0.01230 (14)
C1	0.96492 (6)	0.24626 (10)	0.05929 (7)	0.01255 (15)
C2	0.95681 (6)	0.22146 (10)	−0.02994 (7)	0.01416 (16)
C3	1.07722 (7)	0.35806 (12)	0.01940 (8)	0.01958 (19)
H3A	1.1187	0.3983	0.0079	0.023*
C4	1.08554 (7)	0.38463 (11)	0.10811 (8)	0.01748 (18)
H4A	1.1321	0.4426	0.1556	0.021*
C5	0.90413 (6)	0.17769 (10)	0.08456 (7)	0.01334 (16)
C6	0.88379 (7)	0.13731 (10)	−0.11323 (7)	0.01512 (17)
C7	0.82914 (6)	0.52122 (10)	0.13793 (7)	0.01459 (16)
H7A	0.8039	0.4274	0.1197	0.018*
C8	0.77532 (6)	0.64164 (10)	0.10722 (7)	0.01620 (18)
H8A	0.7142	0.6307	0.0692	0.019*
C9	0.81274 (6)	0.77869 (11)	0.13324 (7)	0.01659 (17)
H9A	0.7773	0.8630	0.1126	0.020*
C10	0.90229 (6)	0.79146 (10)	0.18959 (7)	0.01464 (17)
H10A	0.9289	0.8843	0.2076	0.018*
C11	0.95228 (5)	0.66600 (10)	0.21923 (6)	0.01133 (15)
O5	0.80282 (5)	0.09628 (8)	0.20844 (6)	0.01843 (14)
H5A	0.8335	0.1329	0.1897	0.022*
H5B	0.7644	0.1614	0.1957	0.022*

	U11	U22	U33	U12	U13	U23
Cu1	0.01075 (8)	0.00986 (8)	0.01153 (8)	0.000	0.00533 (6)	0.000
O1	0.0162 (3)	0.0146 (3)	0.0136 (3)	−0.0032 (2)	0.0099 (3)	−0.0027 (2)
O2	0.0255 (4)	0.0255 (4)	0.0199 (4)	−0.0116 (3)	0.0140 (3)	−0.0098 (3)
O3	0.0209 (3)	0.0171 (3)	0.0184 (3)	0.0053 (3)	0.0079 (3)	−0.0022 (3)
O4	0.0193 (3)	0.0250 (4)	0.0179 (3)	0.0082 (3)	0.0072 (3)	−0.0017 (3)
N1	0.0152 (3)	0.0137 (3)	0.0149 (4)	0.0000 (3)	0.0092 (3)	0.0009 (3)
N2	0.0181 (4)	0.0255 (4)	0.0168 (4)	0.0038 (3)	0.0118 (3)	0.0035 (3)
N3	0.0119 (3)	0.0124 (3)	0.0118 (3)	0.0001 (3)	0.0058 (3)	0.0001 (3)
C1	0.0141 (4)	0.0121 (4)	0.0132 (4)	0.0018 (3)	0.0085 (3)	0.0013 (3)
C2	0.0149 (4)	0.0154 (4)	0.0132 (4)	0.0040 (3)	0.0082 (3)	0.0019 (3)
C3	0.0171 (4)	0.0257 (5)	0.0204 (5)	0.0016 (3)	0.0131 (4)	0.0045 (4)
C4	0.0156 (4)	0.0196 (4)	0.0184 (4)	−0.0010 (3)	0.0099 (4)	0.0018 (3)
C5	0.0146 (4)	0.0134 (4)	0.0133 (4)	−0.0003 (3)	0.0083 (3)	−0.0002 (3)
C6	0.0178 (4)	0.0169 (4)	0.0133 (4)	0.0035 (3)	0.0101 (4)	0.0005 (3)
C7	0.0122 (4)	0.0142 (4)	0.0154 (4)	−0.0007 (3)	0.0060 (3)	−0.0004 (3)
C8	0.0120 (4)	0.0171 (4)	0.0162 (4)	0.0008 (3)	0.0054 (3)	−0.0010 (3)
C9	0.0138 (4)	0.0149 (4)	0.0171 (4)	0.0027 (3)	0.0057 (3)	−0.0008 (3)
C10	0.0144 (4)	0.0122 (4)	0.0153 (4)	0.0006 (3)	0.0067 (3)	−0.0010 (3)
C11	0.0114 (4)	0.0126 (4)	0.0100 (4)	0.0000 (3)	0.0057 (3)	0.0003 (3)
O5	0.0213 (3)	0.0156 (3)	0.0244 (4)	0.0041 (3)	0.0163 (3)	0.0056 (3)

Cu1—O1	1.9880 (7)	C2—C6	1.5117 (14)
Cu1—N3	2.0085 (8)	C3—C4	1.3940 (15)
Cu1—N1	2.3565 (8)	C3—H3A	0.9500
O1—C5	1.2890 (11)	C4—H4A	0.9500
O2—C5	1.2243 (12)	C7—C8	1.3869 (13)
O3—C6	1.3072 (12)	C7—H7A	0.9500
O3—H3O	0.8844	C8—C9	1.3903 (13)
O4—C6	1.2142 (12)	C8—H8A	0.9500
N1—C1	1.3340 (12)	C9—C10	1.3886 (13)
N1—C4	1.3386 (12)	C9—H9A	0.9500
N2—C3	1.3362 (15)	C10—C11	1.3904 (13)
N2—C2	1.3388 (12)	C10—H10A	0.9500
N3—C7	1.3446 (11)	C11—C11i	1.4754 (17)
N3—C11	1.3496 (12)	O5—H5A	0.8419
C1—C2	1.4012 (13)	O5—H5B	0.8612
C1—C5	1.5169 (12)
O1—Cu1—O1i	93.03 (4)	C4—C3—H3A	118.9
O1—Cu1—N3i	166.86 (3)	N1—C4—C3	120.57 (10)
O1—Cu1—N3	94.19 (3)	N1—C4—H4A	119.7
O1i—Cu1—N3	166.86 (3)	C3—C4—H4A	119.7
N3i—Cu1—N3	80.95 (4)	O2—C5—O1	125.49 (9)
O1—Cu1—N1i	91.84 (3)	O2—C5—C1	118.30 (8)
N3—Cu1—N1i	92.57 (3)	O1—C5—C1	116.20 (8)
O1—Cu1—N1	76.24 (3)	O4—C6—O3	124.67 (10)
N3—Cu1—N1	100.53 (3)	O4—C6—C2	121.68 (9)
N1i—Cu1—N1	162.80 (4)	O3—C6—C2	113.34 (8)
C5—O1—Cu1	122.13 (6)	N3—C7—C8	122.08 (9)
C6—O3—H3O	109.2	N3—C7—H7A	119.0
C1—N1—C4	118.00 (9)	C8—C7—H7A	119.0
C1—N1—Cu1	107.29 (6)	C7—C8—C9	118.61 (9)
C4—N1—Cu1	134.12 (7)	C7—C8—H8A	120.7
C3—N2—C2	116.72 (9)	C9—C8—H8A	120.7
C7—N3—C11	119.40 (8)	C10—C9—C8	119.48 (9)
C7—N3—Cu1	125.73 (6)	C10—C9—H9A	120.3
C11—N3—Cu1	114.69 (6)	C8—C9—H9A	120.3
N1—C1—C2	120.85 (8)	C9—C10—C11	118.84 (9)
N1—C1—C5	117.05 (8)	C9—C10—H10A	120.6
C2—C1—C5	122.07 (8)	C11—C10—H10A	120.6
N2—C2—C1	121.62 (9)	N3—C11—C10	121.57 (8)
N2—C2—C6	113.75 (8)	N3—C11—C11i	114.75 (5)
C1—C2—C6	124.57 (8)	C10—C11—C11i	123.67 (5)
N2—C3—C4	122.22 (9)	H5A—O5—H5B	104.5
N2—C3—H3A	118.9
O1i—Cu1—O1—C5	−96.65 (7)	C3—N2—C2—C6	177.66 (9)
N3i—Cu1—O1—C5	26.65 (17)	N1—C1—C2—N2	0.90 (14)
N3—Cu1—O1—C5	94.33 (7)	C5—C1—C2—N2	−177.34 (9)
N1i—Cu1—O1—C5	−172.96 (7)	N1—C1—C2—C6	−175.91 (9)
N1—Cu1—O1—C5	−5.49 (7)	C5—C1—C2—C6	5.84 (14)
O1—Cu1—N1—C1	8.79 (6)	C2—N2—C3—C4	−1.13 (15)
O1i—Cu1—N1—C1	101.46 (6)	C1—N1—C4—C3	1.09 (14)
N3i—Cu1—N1—C1	−164.26 (6)	Cu1—N1—C4—C3	−168.92 (7)
N3—Cu1—N1—C1	−82.99 (6)	N2—C3—C4—N1	0.34 (16)
N1i—Cu1—N1—C1	55.98 (14)	Cu1—O1—C5—O2	−179.47 (8)
O1—Cu1—N1—C4	179.57 (10)	Cu1—O1—C5—C1	1.41 (11)
O1i—Cu1—N1—C4	−87.76 (10)	N1—C1—C5—O2	−171.48 (9)
N3i—Cu1—N1—C4	6.52 (10)	C2—C1—C5—O2	6.83 (14)
N3—Cu1—N1—C4	87.79 (10)	N1—C1—C5—O1	7.71 (12)
N1i—Cu1—N1—C4	−133.24 (9)	C2—C1—C5—O1	−173.98 (9)
O1—Cu1—N3—C7	15.90 (8)	N2—C2—C6—O4	−96.00 (11)
O1i—Cu1—N3—C7	−107.29 (14)	C1—C2—C6—O4	81.03 (13)
N3i—Cu1—N3—C7	−176.39 (10)	N2—C2—C6—O3	77.89 (11)
N1i—Cu1—N3—C7	−76.14 (8)	C1—C2—C6—O3	−105.07 (11)
N1—Cu1—N3—C7	92.66 (8)	C11—N3—C7—C8	0.14 (14)
O1—Cu1—N3—C11	−169.01 (6)	Cu1—N3—C7—C8	175.02 (7)
O1i—Cu1—N3—C11	67.81 (15)	N3—C7—C8—C9	0.79 (15)
N3i—Cu1—N3—C11	−1.30 (5)	C7—C8—C9—C10	−0.57 (15)
N1i—Cu1—N3—C11	98.96 (6)	C8—C9—C10—C11	−0.53 (15)
N1—Cu1—N3—C11	−92.25 (7)	C7—N3—C11—C10	−1.31 (13)
C4—N1—C1—C2	−1.68 (14)	Cu1—N3—C11—C10	−176.74 (7)
Cu1—N1—C1—C2	170.83 (7)	C7—N3—C11—C11i	178.90 (9)
C4—N1—C1—C5	176.65 (8)	Cu1—N3—C11—C11i	3.47 (12)
Cu1—N1—C1—C5	−10.84 (9)	C9—C10—C11—N3	1.50 (14)
C3—N2—C2—C1	0.53 (14)	C9—C10—C11—C11i	−178.73 (10)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O5ii	0.88	1.66	2.5390 (12)	170
O5—H5A···O1	0.84	1.89	2.7218 (13)	173
O5—H5B···O4iii	0.86	1.84	2.6989 (13)	177
C7—H7A···O2iii	0.95	2.57	3.1144 (14)	117
C8—H8A···O2iii	0.95	2.45	3.0433 (13)	121
C9—H9A···O5iv	0.95	2.55	3.2168 (13)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O5i	0.88	1.66	2.5390 (12)	170
O5—H5A⋯O1	0.84	1.89	2.7218 (13)	173
O5—H5B⋯O4ii	0.86	1.84	2.6989 (13)	177
C7—H7A⋯O2ii	0.95	2.57	3.1144 (14)	117
C8—H8A⋯O2ii	0.95	2.45	3.0433 (13)	121
C9—H9A⋯O5iii	0.95	2.55	3.2168 (13)	127

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