Diaqua-bis-(5-methyl-pyrazine-2-carboxyl-ato-κN,O)cadmium.

In the title compound, [Cd(C(6)H(5)N(2)O(2))(2)(H(2)O)(2)], the Cd(II) ion is coordinated in a severely distorted octa-hedral geometry. The N atoms are cis to each other, while the water O atoms and ligand O atoms are mutually trans. The crystal structure is stabilized by a network of O-H⋯O, O-H⋯N and C-H⋯O hydrogen bonds and π-π stacking inter-actions [centroid-centroid distances = 3.730 (3) and 3.652 (3) Å] between the 5-methyl-pyrazine-2-carboxyl-ate ligands. The structure is isotypic with the manganese analog.

Related literature

For background to coordination chemistry, see: Blake et al. (1999 ▶); Brito et al. (2011 ▶). For the isotypic Mn compound see: Chapman et al. (2002 ▶). For similar compounds of the type [M(C6H5N2O2)2(H2O)2, where M = FeII, CoII, ZnII, NiII] see: Fan et al. (2007a ▶,b ▶, 2009 ▶); Shang et al. (2007 ▶).

Experimental

Crystal data

[Cd(C6H5N2O2)2(H2O)2]

M = 422.67

Triclinic,

a = 7.2900 (15) Å

b = 7.5320 (15) Å

c = 14.090 (3) Å

α = 87.31 (3)°

β = 81.36 (3)°

γ = 80.78 (3)°

V = 754.8 (3) Å3

Z = 2

Mo Kα radiation

μ = 1.48 mm−1

T = 293 K

0.44 × 0.40 × 0.22 mm

Data collection

Oxford Diffraction CCD area-detector diffractometer

Absorption correction: multi-scan (MULABS; Spek, 2009 ▶; Blessing, 1995 ▶) T min = 0.561, T max = 0.736

5896 measured reflections

3530 independent reflections

2778 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.159

S = 1.06

3530 reflections

226 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 2.23 e Å−3

Δρmin = −1.11 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶) and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811035045/bt5630sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035045/bt5630Isup2.hkl

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

[Cd(C6H5N2O2)2(H2O)2]	Z = 2
Mr = 422.67	F(000) = 420
Triclinic, P1	Dx = 1.860 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2900 (15) Å	Cell parameters from 5011 reflections
b = 7.5320 (15) Å	θ = 3.4–29.7°
c = 14.090 (3) Å	µ = 1.48 mm−1
α = 87.31 (3)°	T = 293 K
β = 81.36 (3)°	Block, yellow
γ = 80.78 (3)°	0.44 × 0.40 × 0.22 mm
V = 754.8 (3) Å3

Oxford Diffraction CCD area-detector diffractometer	3530 independent reflections
Radiation source: fine-focus sealed tube	2778 reflections with I > 2σ(I)
graphite	Rint = 0.061
ω scans	θmax = 29.7°, θmin = 3.4°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	h = −8→9
Tmin = 0.561, Tmax = 0.736	k = −9→5
5896 measured reflections	l = −17→17

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0751P)2] where P = (Fo2 + 2Fc2)/3
3530 reflections	(Δ/σ)max = 0.002
226 parameters	Δρmax = 2.23 e Å−3
0 restraints	Δρmin = −1.11 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Cd1	0.61134 (5)	0.67712 (5)	0.73978 (3)	0.03763 (19)
O1	0.6127 (6)	0.3946 (6)	0.6951 (3)	0.0472 (11)
O2	0.2944 (6)	0.7316 (6)	0.7793 (3)	0.0475 (10)
O3	0.6360 (9)	0.9759 (7)	0.7328 (5)	0.0593 (14)
H3A	0.625 (7)	1.019 (8)	0.781 (4)	0.020 (15)*
H3B	0.607 (14)	1.024 (13)	0.690 (7)	0.09 (4)*
O4	0.9122 (7)	0.6009 (8)	0.7706 (4)	0.0581 (13)
H4A	0.995 (10)	0.560 (10)	0.726 (6)	0.06 (2)*
H4B	0.943 (13)	0.705 (14)	0.793 (7)	0.10 (3)*
O5	0.6558 (8)	0.2045 (6)	0.5758 (3)	0.0561 (12)
O6	0.0540 (6)	0.8123 (8)	0.8930 (4)	0.0607 (13)
N1	0.6959 (7)	0.6675 (6)	0.5708 (3)	0.0354 (10)
N2	0.8477 (7)	0.5928 (7)	0.3815 (4)	0.0421 (12)
N3	0.5370 (6)	0.6945 (6)	0.9084 (3)	0.0346 (10)
N4	0.4226 (7)	0.8321 (7)	1.0909 (4)	0.0411 (12)
C1	0.7138 (7)	0.5011 (7)	0.5376 (4)	0.0344 (12)
C2	0.7863 (8)	0.4661 (8)	0.4434 (4)	0.0398 (13)
H2	0.7933	0.3503	0.4215	0.048*
C3	0.8288 (8)	0.7586 (8)	0.4138 (4)	0.0418 (13)
C4	0.7530 (9)	0.7945 (8)	0.5084 (4)	0.0417 (13)
H4	0.7412	0.9115	0.5295	0.050*
C5	0.8947 (11)	0.9043 (10)	0.3470 (5)	0.0591 (18)
H5A	0.9502	0.9833	0.3817	0.089*
H5B	0.7898	0.9714	0.3207	0.089*
H5C	0.9862	0.8512	0.2958	0.089*
C6	0.6543 (8)	0.3540 (8)	0.6091 (5)	0.0400 (13)
C7	0.6558 (8)	0.6841 (8)	0.9727 (4)	0.0405 (13)
H7	0.7798	0.6306	0.9555	0.049*
C8	0.6001 (8)	0.7502 (8)	1.0637 (4)	0.0392 (13)
C9	0.3029 (8)	0.8382 (8)	1.0262 (4)	0.0425 (14)
H9	0.1785	0.8906	1.0433	0.051*
C10	0.3579 (7)	0.7703 (8)	0.9364 (4)	0.0365 (12)
C11	0.2241 (8)	0.7717 (8)	0.8637 (5)	0.0424 (14)
C12	0.7340 (10)	0.7352 (10)	1.1345 (5)	0.0532 (17)
H12A	0.7154	0.8453	1.1688	0.080*
H12B	0.8603	0.7131	1.1015	0.080*
H12C	0.7127	0.6375	1.1789	0.080*

	U11	U22	U33	U12	U13	U23
Cd1	0.0420 (3)	0.0324 (3)	0.0377 (3)	−0.00852 (18)	0.00199 (18)	−0.00820 (19)
O1	0.069 (3)	0.033 (2)	0.041 (2)	−0.019 (2)	0.003 (2)	−0.0051 (19)
O2	0.042 (2)	0.058 (3)	0.042 (2)	−0.005 (2)	−0.0048 (18)	−0.010 (2)
O3	0.102 (4)	0.035 (3)	0.041 (3)	−0.021 (3)	−0.001 (3)	−0.011 (3)
O4	0.037 (3)	0.070 (4)	0.066 (3)	−0.003 (2)	−0.001 (2)	−0.032 (3)
O5	0.092 (4)	0.027 (2)	0.050 (3)	−0.017 (2)	−0.003 (2)	−0.008 (2)
O6	0.031 (2)	0.086 (4)	0.066 (3)	−0.009 (2)	−0.002 (2)	−0.015 (3)
N1	0.048 (3)	0.023 (2)	0.036 (3)	−0.0080 (19)	−0.004 (2)	−0.005 (2)
N2	0.048 (3)	0.035 (3)	0.042 (3)	−0.003 (2)	−0.002 (2)	−0.007 (2)
N3	0.034 (2)	0.033 (3)	0.036 (3)	−0.0069 (19)	0.0004 (19)	−0.005 (2)
N4	0.049 (3)	0.036 (3)	0.038 (3)	−0.008 (2)	−0.002 (2)	−0.004 (2)
C1	0.037 (3)	0.023 (3)	0.043 (3)	−0.003 (2)	−0.005 (2)	−0.008 (2)
C2	0.042 (3)	0.030 (3)	0.047 (4)	−0.004 (2)	−0.004 (2)	−0.011 (3)
C3	0.049 (3)	0.036 (3)	0.040 (3)	−0.007 (3)	−0.008 (3)	0.000 (3)
C4	0.057 (4)	0.023 (3)	0.044 (3)	−0.005 (2)	0.000 (3)	−0.007 (2)
C5	0.076 (5)	0.053 (4)	0.050 (4)	−0.017 (4)	−0.006 (3)	0.002 (3)
C6	0.043 (3)	0.030 (3)	0.047 (4)	−0.006 (2)	−0.006 (3)	−0.006 (3)
C7	0.032 (3)	0.044 (4)	0.044 (3)	−0.007 (2)	−0.001 (2)	0.002 (3)
C8	0.041 (3)	0.036 (3)	0.042 (3)	−0.014 (2)	−0.003 (2)	0.003 (3)
C9	0.036 (3)	0.041 (3)	0.047 (4)	−0.005 (2)	0.005 (2)	−0.012 (3)
C10	0.033 (3)	0.032 (3)	0.043 (3)	−0.010 (2)	0.005 (2)	−0.003 (2)
C11	0.038 (3)	0.035 (3)	0.055 (4)	−0.009 (2)	−0.004 (3)	−0.008 (3)
C12	0.060 (4)	0.055 (4)	0.050 (4)	−0.017 (3)	−0.016 (3)	−0.004 (3)

Cd1—O1	2.245 (4)	N4—C9	1.347 (8)
Cd1—O2	2.269 (4)	N4—C8	1.349 (8)
Cd1—O4	2.278 (5)	C1—C2	1.374 (8)
Cd1—O3	2.283 (5)	C1—C6	1.532 (8)
Cd1—N3	2.361 (5)	C2—H2	0.9300
Cd1—N1	2.370 (5)	C3—C4	1.385 (8)
O1—C6	1.244 (7)	C3—C5	1.502 (9)
O2—C11	1.253 (8)	C4—H4	0.9300
O3—H3A	0.75 (6)	C5—H5A	0.9600
O3—H3B	0.73 (9)	C5—H5B	0.9600
O4—H4A	0.83 (8)	C5—H5C	0.9600
O4—H4B	0.93 (11)	C7—C8	1.376 (8)
O5—C6	1.238 (7)	C7—H7	0.9300
O6—C11	1.240 (7)	C8—C12	1.486 (8)
N1—C1	1.339 (7)	C9—C10	1.366 (8)
N1—C4	1.342 (7)	C9—H9	0.9300
N2—C3	1.329 (8)	C10—C11	1.516 (8)
N2—C2	1.346 (8)	C12—H12A	0.9600
N3—C7	1.335 (7)	C12—H12B	0.9600
N3—C10	1.347 (7)	C12—H12C	0.9600
O1—Cd1—O2	93.45 (17)	N2—C3—C4	120.1 (6)
O1—Cd1—O4	90.14 (19)	N2—C3—C5	119.0 (6)
O2—Cd1—O4	154.86 (19)	C4—C3—C5	120.9 (6)
O1—Cd1—O3	161.4 (2)	N1—C4—C3	122.7 (5)
O2—Cd1—O3	92.9 (2)	N1—C4—H4	118.6
O4—Cd1—O3	91.5 (2)	C3—C4—H4	118.6
O1—Cd1—N3	109.65 (16)	C3—C5—H5A	109.5
O2—Cd1—N3	71.25 (16)	C3—C5—H5B	109.5
O4—Cd1—N3	84.11 (18)	H5A—C5—H5B	109.5
O3—Cd1—N3	89.0 (2)	C3—C5—H5C	109.5
O1—Cd1—N1	72.18 (16)	H5A—C5—H5C	109.5
O2—Cd1—N1	110.48 (16)	H5B—C5—H5C	109.5
O4—Cd1—N1	94.30 (19)	O5—C6—O1	126.1 (6)
O3—Cd1—N1	89.2 (2)	O5—C6—C1	116.6 (6)
N3—Cd1—N1	177.55 (14)	O1—C6—C1	117.2 (5)
C6—O1—Cd1	120.4 (4)	N3—C7—C8	122.0 (5)
C11—O2—Cd1	119.5 (4)	N3—C7—H7	119.0
Cd1—O3—H3A	114 (4)	C8—C7—H7	119.0
Cd1—O3—H3B	115 (8)	N4—C8—C7	120.9 (5)
H3A—O3—H3B	124 (10)	N4—C8—C12	118.0 (6)
Cd1—O4—H4A	119 (5)	C7—C8—C12	121.1 (6)
Cd1—O4—H4B	105 (6)	N4—C9—C10	122.3 (5)
H4A—O4—H4B	109 (8)	N4—C9—H9	118.8
C1—N1—C4	116.9 (5)	C10—C9—H9	118.8
C1—N1—Cd1	112.5 (4)	N3—C10—C9	120.8 (5)
C4—N1—Cd1	129.8 (4)	N3—C10—C11	116.2 (5)
C3—N2—C2	117.3 (5)	C9—C10—C11	123.0 (5)
C7—N3—C10	117.3 (5)	O6—C11—O2	125.5 (6)
C7—N3—Cd1	127.7 (4)	O6—C11—C10	117.1 (6)
C10—N3—Cd1	112.4 (4)	O2—C11—C10	117.4 (5)
C9—N4—C8	116.6 (5)	C8—C12—H12A	109.5
N1—C1—C2	120.3 (5)	C8—C12—H12B	109.5
N1—C1—C6	117.3 (5)	H12A—C12—H12B	109.5
C2—C1—C6	122.4 (5)	C8—C12—H12C	109.5
N2—C2—C1	122.7 (6)	H12A—C12—H12C	109.5
N2—C2—H2	118.7	H12B—C12—H12C	109.5
C1—C2—H2	118.7
O2—Cd1—O1—C6	110.9 (5)	C6—C1—C2—N2	−176.5 (5)
O4—Cd1—O1—C6	−94.0 (5)	C2—N2—C3—C4	1.6 (8)
O3—Cd1—O1—C6	1.2 (9)	C2—N2—C3—C5	−179.7 (5)
N3—Cd1—O1—C6	−177.8 (4)	C1—N1—C4—C3	−0.5 (8)
N1—Cd1—O1—C6	0.5 (4)	Cd1—N1—C4—C3	168.3 (4)
O1—Cd1—O2—C11	119.9 (5)	N2—C3—C4—N1	0.0 (9)
O4—Cd1—O2—C11	22.2 (7)	C5—C3—C4—N1	−178.7 (6)
O3—Cd1—O2—C11	−77.7 (5)	Cd1—O1—C6—O5	−178.3 (5)
N3—Cd1—O2—C11	10.3 (5)	Cd1—O1—C6—C1	3.2 (7)
N1—Cd1—O2—C11	−167.9 (4)	N1—C1—C6—O5	173.8 (5)
O1—Cd1—N1—C1	−4.4 (3)	C2—C1—C6—O5	−7.4 (8)
O2—Cd1—N1—C1	−91.4 (4)	N1—C1—C6—O1	−7.5 (8)
O4—Cd1—N1—C1	84.3 (4)	C2—C1—C6—O1	171.2 (5)
O3—Cd1—N1—C1	175.8 (4)	C10—N3—C7—C8	−1.1 (8)
O1—Cd1—N1—C4	−173.7 (5)	Cd1—N3—C7—C8	159.3 (4)
O2—Cd1—N1—C4	99.3 (5)	C9—N4—C8—C7	2.7 (8)
O4—Cd1—N1—C4	−84.9 (5)	C9—N4—C8—C12	−177.8 (5)
O3—Cd1—N1—C4	6.5 (5)	N3—C7—C8—N4	−1.3 (9)
O1—Cd1—N3—C7	96.2 (5)	N3—C7—C8—C12	179.2 (5)
O2—Cd1—N3—C7	−176.9 (5)	C8—N4—C9—C10	−1.8 (9)
O4—Cd1—N3—C7	8.2 (5)	C7—N3—C10—C9	1.9 (8)
O3—Cd1—N3—C7	−83.5 (5)	Cd1—N3—C10—C9	−161.4 (5)
O1—Cd1—N3—C10	−102.6 (4)	C7—N3—C10—C11	−177.0 (5)
O2—Cd1—N3—C10	−15.7 (4)	Cd1—N3—C10—C11	19.7 (6)
O4—Cd1—N3—C10	169.4 (4)	N4—C9—C10—N3	−0.5 (9)
O3—Cd1—N3—C10	77.7 (4)	N4—C9—C10—C11	178.4 (5)
C4—N1—C1—C2	−0.5 (8)	Cd1—O2—C11—O6	176.5 (5)
Cd1—N1—C1—C2	−171.3 (4)	Cd1—O2—C11—C10	−3.6 (7)
C4—N1—C1—C6	178.3 (5)	N3—C10—C11—O6	168.1 (5)
Cd1—N1—C1—C6	7.5 (6)	C9—C10—C11—O6	−10.8 (9)
C3—N2—C2—C1	−2.7 (8)	N3—C10—C11—O2	−11.8 (8)
N1—C1—C2—N2	2.2 (9)	C9—C10—C11—O2	169.3 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···N4i	0.75 (6)	2.12 (6)	2.875 (9)	173 (6)
O3—H3B···O5ii	0.73 (10)	2.08 (10)	2.740 (8)	150 (10)
O4—H4A···N2iii	0.84 (8)	2.04 (8)	2.852 (8)	164 (8)
O4—H4B···O6iv	0.93 (11)	1.99 (10)	2.811 (8)	146 (8)
C4—H4···O5ii	0.93	2.29	3.211 (7)	169

Ring 1	Ring 2	α	d	Δ
N1/C1/C2/N2/C3/C4	(N1/C1/C2/N2/C3/C4)i	0	3.730 (3)	1.237
N3/C7/C8/N4/C9/C10	(N3/C7/C8/N4/C9/C10)ii	0	3.652 (3)	1.307

Cd1—O1	2.245 (4)
Cd1—O2	2.269 (4)
Cd1—O4	2.278 (5)
Cd1—O3	2.283 (5)
Cd1—N3	2.361 (5)
Cd1—N1	2.370 (5)

O2—Cd1—O4	154.86 (19)
O1—Cd1—O3	161.4 (2)
O2—Cd1—N3	71.25 (16)
O3—Cd1—N3	89.0 (2)
O1—Cd1—N1	72.18 (16)
N3—Cd1—N1	177.55 (14)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯N4i	0.75 (6)	2.12 (6)	2.875 (9)	173 (6)
O3—H3B⋯O5ii	0.73 (10)	2.08 (10)	2.740 (8)	150 (10)
O4—H4A⋯N2iii	0.84 (8)	2.04 (8)	2.852 (8)	164 (8)
O4—H4B⋯O6iv	0.93 (11)	1.99 (10)	2.811 (8)	146 (8)
C4—H4⋯O5ii	0.93	2.29	3.211 (7)	169

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