Aqua-(2,2'-bipyrimidine-κN,N')(succin-ato-κO,O)copper(II) dihydrate.

In the crystal structure of the title compound, [Cu(C(4)H(4)O(4))(C(8)H(6)N(4))(H(2)O)]·2H(2)O, the Cu(II) atom is chelated by a 2,2'-bipyrimidine (bpm) ligand and a succinate anion in the basal plane; a water mol-ecule in the apical position completes the slightly distorted square-pyramidal coordination geometry. Another carboxyl-ate O atom from an adjacent complex is located in the opposite apical direction, with a Cu⋯O distance of 2.706 (3) Å, and is not considered as a bridging atom. Extensive O-H⋯O and O-H⋯N hydrogen bonding is present in the crystal structure.

Related literature

For general background, see: McCann et al. (1997 ▶); Ray et al. (2004 ▶); Zhang et al. (2004 ▶).

Experimental

Crystal data

[Cu(C4H4O4)(C8H6N4)(H2O)]·2H2O

M = 391.83

Monoclinic,

a = 10.6905 (8) Å

b = 18.9321 (14) Å

c = 7.6105 (6) Å

β = 92.2290 (10)°

V = 1539.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 1.46 mm−1

T = 293 K

0.30 × 0.20 × 0.09 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.700, T max = 0.877

7725 measured reflections

2735 independent reflections

2085 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.123

S = 1.06

2735 reflections

235 parameters

10 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.46 e Å−3

Δρmin = −0.66 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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/S1600536809013518/xu2509sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809013518/xu2509Isup2.hkl

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

[Cu(C4H4O4)(C8H6N4)(H2O)]·2H2O	F(000) = 804
Mr = 391.83	Dx = 1.691 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3225 reflections
a = 10.6905 (8) Å	θ = 1.9–25.1°
b = 18.9321 (14) Å	µ = 1.46 mm−1
c = 7.6105 (6) Å	T = 293 K
β = 92.229 (1)°	Prism, blue
V = 1539.2 (2) Å3	0.30 × 0.20 × 0.09 mm
Z = 4

Bruker SMART CCD diffractometer	2735 independent reflections
Radiation source: fine-focus sealed tube	2085 reflections with I > 2σ(I)
graphite	Rint = 0.036
φ and ω scans	θmax = 25.1°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.700, Tmax = 0.877	k = −22→22
7725 measured reflections	l = −9→4

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0588P)2 + 1.4777P] where P = (Fo2 + 2Fc2)/3
2735 reflections	(Δ/σ)max = 0.001
235 parameters	Δρmax = 0.46 e Å−3
10 restraints	Δρmin = −0.65 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
Cu1	0.83883 (5)	0.98092 (2)	0.42287 (7)	0.0376 (2)
O1	0.7210 (3)	0.94912 (16)	0.1622 (4)	0.0477 (8)
H1A	0.673 (4)	0.9136 (17)	0.160 (6)	0.072*
H1B	0.774 (4)	0.945 (2)	0.082 (5)	0.072*
O1W	0.6018 (4)	0.82533 (18)	0.2132 (6)	0.0724 (11)
H1WA	0.5230 (12)	0.819 (3)	0.212 (9)	0.109*
H1WB	0.637 (4)	0.790 (2)	0.170 (9)	0.109*
O2	0.7834 (3)	1.07626 (14)	0.4543 (4)	0.0459 (7)
O2W	0.6560 (4)	0.3145 (2)	0.2485 (6)	0.0810 (12)
H2WB	0.674 (7)	0.2726 (15)	0.280 (8)	0.121*
H2WA	0.676 (7)	0.321 (3)	0.143 (4)	0.121*
O3	0.7344 (3)	1.18623 (16)	0.3913 (5)	0.0606 (9)
O4	1.1035 (3)	1.06421 (15)	0.1176 (4)	0.0490 (8)
O5	0.9903 (3)	1.00736 (14)	0.3069 (4)	0.0395 (7)
N1	0.8883 (3)	0.87826 (17)	0.4388 (4)	0.0362 (8)
N2	0.7034 (3)	0.94476 (18)	0.5757 (4)	0.0382 (8)
N3	0.8133 (3)	0.76731 (17)	0.5315 (5)	0.0468 (9)
N4	0.6295 (3)	0.8392 (2)	0.7042 (5)	0.0494 (10)
C1	0.9872 (4)	0.8470 (2)	0.3680 (6)	0.0435 (10)
H1C	1.0466	0.8745	0.3135	0.052*
C2	1.0017 (4)	0.7748 (2)	0.3750 (6)	0.0499 (11)
H2	1.0700	0.7525	0.3272	0.060*
C3	0.9102 (4)	0.7374 (2)	0.4561 (6)	0.0491 (11)
H3	0.9164	0.6884	0.4584	0.059*
C4	0.8069 (4)	0.8370 (2)	0.5194 (5)	0.0368 (9)
C5	0.7056 (4)	0.8751 (2)	0.6045 (5)	0.0376 (9)
C6	0.5436 (4)	0.8772 (3)	0.7835 (7)	0.0573 (13)
H6	0.4886	0.8539	0.8557	0.069*
C7	0.5319 (4)	0.9492 (3)	0.7641 (6)	0.0546 (12)
H7	0.4704	0.9746	0.8201	0.066*
C8	0.6163 (4)	0.9822 (2)	0.6570 (6)	0.0459 (11)
H8	0.6124	1.0309	0.6414	0.055*
C9	0.7701 (4)	1.1270 (2)	0.3460 (6)	0.0413 (10)
C10	0.7927 (4)	1.1167 (2)	0.1584 (6)	0.0442 (11)
H10A	0.7179	1.0939	0.1097	0.053*
H10B	0.7932	1.1638	0.1082	0.053*
C11	0.8904 (4)	1.0823 (2)	0.0863 (6)	0.0409 (10)
H11A	0.9243	1.1155	0.0036	0.049*
H11B	0.8523	1.0448	0.0156	0.049*
C12	1.0022 (4)	1.0491 (2)	0.1772 (5)	0.0370 (9)

	U11	U22	U33	U12	U13	U23
Cu1	0.0438 (3)	0.0255 (3)	0.0444 (3)	0.0014 (2)	0.0122 (2)	0.0028 (2)
O1	0.0475 (18)	0.0452 (17)	0.0511 (19)	−0.0081 (14)	0.0088 (15)	−0.0032 (15)
O1W	0.071 (2)	0.0425 (19)	0.104 (3)	−0.0055 (18)	0.012 (2)	−0.008 (2)
O2	0.0617 (19)	0.0287 (14)	0.0479 (18)	0.0054 (14)	0.0112 (15)	0.0025 (13)
O2W	0.100 (3)	0.063 (2)	0.081 (3)	0.028 (2)	0.022 (3)	0.024 (2)
O3	0.083 (2)	0.0362 (17)	0.063 (2)	0.0214 (17)	0.0051 (19)	−0.0003 (16)
O4	0.0475 (18)	0.0434 (17)	0.057 (2)	−0.0044 (14)	0.0187 (16)	0.0048 (15)
O5	0.0417 (16)	0.0332 (14)	0.0439 (17)	−0.0001 (12)	0.0055 (13)	0.0063 (13)
N1	0.0393 (18)	0.0300 (17)	0.0395 (19)	0.0004 (15)	0.0026 (16)	−0.0003 (15)
N2	0.0403 (18)	0.0358 (18)	0.039 (2)	0.0019 (15)	0.0066 (16)	0.0009 (15)
N3	0.055 (2)	0.0281 (18)	0.057 (2)	−0.0029 (16)	0.001 (2)	0.0058 (17)
N4	0.042 (2)	0.049 (2)	0.058 (2)	−0.0074 (17)	0.0105 (19)	0.0130 (19)
C1	0.046 (2)	0.041 (2)	0.044 (2)	−0.001 (2)	0.008 (2)	−0.002 (2)
C2	0.052 (3)	0.041 (2)	0.057 (3)	0.010 (2)	0.005 (2)	−0.003 (2)
C3	0.062 (3)	0.030 (2)	0.056 (3)	0.006 (2)	0.003 (2)	−0.001 (2)
C4	0.038 (2)	0.033 (2)	0.039 (2)	−0.0051 (17)	0.0001 (19)	0.0064 (18)
C5	0.038 (2)	0.037 (2)	0.038 (2)	−0.0028 (18)	−0.0011 (19)	0.0060 (18)
C6	0.045 (3)	0.069 (3)	0.059 (3)	−0.003 (2)	0.011 (2)	0.014 (3)
C7	0.045 (3)	0.068 (3)	0.051 (3)	0.005 (2)	0.012 (2)	0.002 (3)
C8	0.050 (3)	0.042 (2)	0.046 (3)	0.010 (2)	0.005 (2)	0.002 (2)
C9	0.038 (2)	0.032 (2)	0.054 (3)	0.0007 (18)	0.006 (2)	0.001 (2)
C10	0.044 (2)	0.033 (2)	0.056 (3)	−0.0061 (19)	0.001 (2)	0.010 (2)
C11	0.050 (2)	0.031 (2)	0.042 (2)	−0.0139 (19)	0.003 (2)	0.0073 (19)
C12	0.048 (2)	0.0251 (19)	0.039 (2)	−0.0006 (18)	0.008 (2)	−0.0044 (18)

Cu1—O1	2.386 (3)	N4—C5	1.323 (5)
Cu1—O2	1.918 (3)	N4—C6	1.330 (6)
Cu1—O5	1.940 (3)	C1—C2	1.376 (6)
Cu1—N1	2.017 (3)	C1—H1C	0.9300
Cu1—N2	2.012 (3)	C2—C3	1.374 (6)
O1—H1A	0.85 (4)	C2—H2	0.9300
O1—H1B	0.85 (4)	C3—H3	0.9300
O1W—H1WA	0.85 (4)	C4—C5	1.472 (6)
O1W—H1WB	0.84 (4)	C6—C7	1.377 (7)
O2—C9	1.270 (5)	C6—H6	0.9300
O2W—H2WB	0.85 (4)	C7—C8	1.388 (6)
O2W—H2WA	0.85 (4)	C7—H7	0.9300
O3—C9	1.239 (5)	C8—H8	0.9300
O4—C12	1.224 (5)	C9—C10	1.469 (6)
O5—C12	1.275 (5)	C10—C11	1.365 (5)
N1—C4	1.336 (5)	C10—H10A	0.9700
N1—C1	1.343 (5)	C10—H10B	0.9700
N2—C5	1.336 (5)	C11—C12	1.495 (6)
N2—C8	1.341 (5)	C11—H11A	0.9700
N3—C4	1.324 (5)	C11—H11B	0.9700
N3—C3	1.330 (5)
O2—Cu1—O5	94.68 (12)	N3—C4—N1	125.6 (4)
O2—Cu1—N2	90.87 (13)	N3—C4—C5	119.7 (3)
O5—Cu1—N2	169.41 (13)	N1—C4—C5	114.7 (3)
O2—Cu1—N1	168.87 (13)	N4—C5—N2	126.5 (4)
O5—Cu1—N1	93.13 (13)	N4—C5—C4	118.6 (4)
N2—Cu1—N1	80.22 (13)	N2—C5—C4	114.9 (3)
O2—Cu1—O1	100.69 (12)	N4—C6—C7	123.2 (4)
O5—Cu1—O1	96.32 (12)	N4—C6—H6	118.4
N2—Cu1—O1	91.50 (12)	C7—C6—H6	118.4
N1—Cu1—O1	86.30 (12)	C6—C7—C8	116.8 (4)
Cu1—O1—H1A	121 (4)	C6—C7—H7	121.6
Cu1—O1—H1B	106 (3)	C8—C7—H7	121.6
H1A—O1—H1B	109 (4)	N2—C8—C7	120.8 (4)
H1WA—O1W—H1WB	110 (5)	N2—C8—H8	119.6
C9—O2—Cu1	131.1 (3)	C7—C8—H8	119.6
H2WB—O2W—H2WA	110 (6)	O3—C9—O2	122.1 (4)
C12—O5—Cu1	128.5 (3)	O3—C9—C10	117.0 (4)
C4—N1—C1	117.6 (3)	O2—C9—C10	120.9 (4)
C4—N1—Cu1	114.7 (3)	C11—C10—C9	127.7 (4)
C1—N1—Cu1	127.5 (3)	C11—C10—H10A	105.4
C5—N2—C8	117.0 (4)	C9—C10—H10A	105.4
C5—N2—Cu1	115.0 (3)	C11—C10—H10B	105.4
C8—N2—Cu1	128.0 (3)	C9—C10—H10B	105.4
C4—N3—C3	115.7 (4)	H10A—C10—H10B	106.0
C5—N4—C6	115.7 (4)	C10—C11—C12	128.7 (4)
N1—C1—C2	120.7 (4)	C10—C11—H11A	105.1
N1—C1—H1C	119.6	C12—C11—H11A	105.1
C2—C1—H1C	119.6	C10—C11—H11B	105.1
C3—C2—C1	116.7 (4)	C12—C11—H11B	105.1
C3—C2—H2	121.7	H11A—C11—H11B	105.9
C1—C2—H2	121.7	O4—C12—O5	123.2 (4)
N3—C3—C2	123.6 (4)	O4—C12—C11	115.7 (4)
N3—C3—H3	118.2	O5—C12—C11	121.1 (4)
C2—C3—H3	118.2
O5—Cu1—O2—C9	51.3 (4)	C3—N3—C4—C5	−177.7 (4)
N2—Cu1—O2—C9	−137.8 (4)	C1—N1—C4—N3	−2.0 (6)
N1—Cu1—O2—C9	−174.3 (6)	Cu1—N1—C4—N3	173.5 (4)
O1—Cu1—O2—C9	−46.1 (4)	C1—N1—C4—C5	176.0 (4)
O2—Cu1—O5—C12	−50.4 (3)	Cu1—N1—C4—C5	−8.5 (4)
N2—Cu1—O5—C12	−171.8 (6)	C6—N4—C5—N2	−0.5 (7)
N1—Cu1—O5—C12	137.5 (3)	C6—N4—C5—C4	177.1 (4)
O1—Cu1—O5—C12	50.9 (3)	C8—N2—C5—N4	0.7 (6)
O2—Cu1—N1—C4	43.9 (8)	Cu1—N2—C5—N4	177.8 (3)
O5—Cu1—N1—C4	178.4 (3)	C8—N2—C5—C4	−177.1 (4)
N2—Cu1—N1—C4	6.7 (3)	Cu1—N2—C5—C4	0.0 (5)
O1—Cu1—N1—C4	−85.5 (3)	N3—C4—C5—N4	5.8 (6)
O2—Cu1—N1—C1	−141.1 (6)	N1—C4—C5—N4	−172.3 (4)
O5—Cu1—N1—C1	−6.6 (4)	N3—C4—C5—N2	−176.3 (4)
N2—Cu1—N1—C1	−178.3 (4)	N1—C4—C5—N2	5.6 (5)
O1—Cu1—N1—C1	89.5 (4)	C5—N4—C6—C7	0.5 (7)
O2—Cu1—N2—C5	−176.8 (3)	N4—C6—C7—C8	−0.6 (8)
O5—Cu1—N2—C5	−55.1 (8)	C5—N2—C8—C7	−0.8 (6)
N1—Cu1—N2—C5	−3.5 (3)	Cu1—N2—C8—C7	−177.4 (3)
O1—Cu1—N2—C5	82.5 (3)	C6—C7—C8—N2	0.8 (7)
O2—Cu1—N2—C8	0.0 (4)	Cu1—O2—C9—O3	−178.8 (3)
O5—Cu1—N2—C8	121.6 (7)	Cu1—O2—C9—C10	3.2 (6)
N1—Cu1—N2—C8	173.2 (4)	O3—C9—C10—C11	137.1 (5)
O1—Cu1—N2—C8	−100.8 (4)	O2—C9—C10—C11	−44.9 (7)
C4—N1—C1—C2	1.6 (6)	C9—C10—C11—C12	−3.2 (7)
Cu1—N1—C1—C2	−173.3 (3)	Cu1—O5—C12—O4	177.3 (3)
N1—C1—C2—C3	0.5 (7)	Cu1—O5—C12—C11	−3.5 (5)
C4—N3—C3—C2	2.2 (7)	C10—C11—C12—O4	−131.7 (4)
C1—C2—C3—N3	−2.5 (7)	C10—C11—C12—O5	49.0 (6)
C3—N3—C4—N1	0.2 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O1W	0.85 (4)	1.89 (4)	2.703 (5)	162 (4)
O1—H1B···O4i	0.85 (4)	2.05 (4)	2.903 (4)	178 (4)
O1W—H1WA···O2Wii	0.85 (4)	1.95 (2)	2.790 (6)	169 (5)
O1W—H1WB···N3iii	0.84 (4)	2.45 (5)	3.216 (5)	152 (4)
O1W—H1WB···N4iii	0.84 (4)	2.46 (4)	3.130 (5)	137 (5)
O2W—H2WA···O3iii	0.85 (4)	2.04 (4)	2.876 (6)	167 (5)
O2W—H2WB···O3iv	0.85 (4)	1.94 (4)	2.777 (5)	168 (4)

Table 1

Selected bond lengths (Å)

Cu1—O1	2.386 (3)
Cu1—O2	1.918 (3)
Cu1—O5	1.940 (3)
Cu1—N1	2.017 (3)
Cu1—N2	2.012 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O1W	0.85 (4)	1.89 (4)	2.703 (5)	162 (4)
O1—H1B⋯O4i	0.85 (4)	2.05 (4)	2.903 (4)	178 (4)
O1W—H1WA⋯O2Wii	0.85 (4)	1.950 (17)	2.790 (6)	169 (5)
O1W—H1WB⋯N3iii	0.84 (4)	2.45 (5)	3.216 (5)	152 (4)
O1W—H1WB⋯N4iii	0.84 (4)	2.46 (4)	3.130 (5)	137 (5)
O2W—H2WA⋯O3iii	0.85 (4)	2.04 (4)	2.876 (6)	167 (5)
O2W—H2WB⋯O3iv	0.85 (4)	1.94 (4)	2.777 (5)	168 (4)

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