Diaqua-bis(5-phenyl-1H-pyrazole-3-carboxyl-ato)copper(II).

In the centrosymmetric title compound, [Cu(C(10)H(7)N(2)O(2))(2)(H(2)O)(2)], the Cu(II) ion occupies an inversion centre and exhibits a distorted octa-hedral geometry. The phenyl and pyrazole rings of the ligand are twisted by an angle of 11.36 (8)°. In the crystal structure, mol-ecules are linked into a two-dimensional network parallel to the (010) plane by O-H⋯O and N-H⋯O hydrogen bonds.

Related literature

For ligand preparation, see: Crane et al. (1999 ▶); Gharbaoui et al. (2007 ▶). For general background, see: van Herk et al. (2003 ▶); Knopp (1999 ▶).

Experimental

Crystal data

[Cu(C10H7N2O2)2(H2O)2]

M = 473.92

Monoclinic,

a = 5.0443 (6) Å

b = 32.161 (4) Å

c = 6.3234 (8) Å

β = 106.293 (1)°

V = 984.6 (2) Å3

Z = 2

Mo Kα radiation

μ = 1.16 mm−1

T = 292 (2) K

0.35 × 0.25 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.690, T max = 0.829

8611 measured reflections

2254 independent reflections

1907 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.084

S = 1.08

2254 reflections

150 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.32 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808000810/ci2551sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808000810/ci2551Isup2.hkl

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

[Cu(C10H7N2O2)2(H2O)2]	F000 = 486
Mr = 473.92	Dx = 1.599 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2772 reflections
a = 5.0443 (6) Å	θ = 2.5–26.6º
b = 32.161 (4) Å	µ = 1.16 mm−1
c = 6.3234 (8) Å	T = 292 (2) K
β = 106.293 (1)º	Block, blue
V = 984.6 (2) Å3	0.35 × 0.25 × 0.17 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	2254 independent reflections
Radiation source: fine-focus sealed tube	1907 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.027
T = 292(2) K	θmax = 27.5º
φ and ω scans	θmin = 2.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −6→6
Tmin = 0.690, Tmax = 0.829	k = −41→39
8611 measured reflections	l = −8→8

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.084	w = 1/[σ2(Fo2) + (0.0302P)2 + 0.72P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
2254 reflections	Δρmax = 0.34 e Å−3
150 parameters	Δρmin = −0.32 e Å−3
3 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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	0.5000	0.0000	0.0000	0.03166 (13)
O1	0.3462 (3)	0.01796 (5)	0.2440 (2)	0.0325 (3)
O2	0.3301 (4)	0.07235 (5)	0.4604 (3)	0.0404 (4)
O3	0.0850 (4)	0.03336 (6)	−0.2706 (3)	0.0380 (4)
N1	0.6670 (4)	0.05536 (5)	0.0513 (3)	0.0294 (4)
N2	0.8212 (4)	0.08034 (5)	−0.0348 (3)	0.0301 (4)
H2	0.8956	0.0730	−0.1359	0.036*
C1	0.4084 (4)	0.05525 (7)	0.3144 (3)	0.0288 (5)
C2	0.5895 (4)	0.07783 (7)	0.2015 (3)	0.0277 (4)
C3	0.6964 (4)	0.11779 (7)	0.2111 (4)	0.0302 (5)
H3	0.6732	0.1395	0.3017	0.036*
C4	0.8454 (4)	0.11852 (6)	0.0569 (4)	0.0282 (4)
C5	1.0091 (5)	0.15138 (7)	−0.0085 (4)	0.0328 (5)
C6	1.0740 (6)	0.18727 (8)	0.1155 (5)	0.0473 (6)
H6	1.0067	0.1911	0.2368	0.057*
C7	1.2389 (7)	0.21770 (9)	0.0605 (6)	0.0641 (9)
H7	1.2821	0.2417	0.1454	0.077*
C8	1.3376 (6)	0.21240 (9)	−0.1183 (6)	0.0642 (9)
H8	1.4482	0.2328	−0.1543	0.077*
C9	1.2744 (6)	0.17720 (10)	−0.2448 (5)	0.0565 (8)
H9	1.3419	0.1738	−0.3663	0.068*
C10	1.1097 (5)	0.14664 (8)	−0.1918 (4)	0.0438 (6)
H10	1.0662	0.1229	−0.2786	0.053*
H1W	0.138 (6)	0.0417 (9)	−0.376 (4)	0.069 (10)*
H2W	−0.041 (5)	0.0163 (8)	−0.312 (5)	0.075 (11)*

	U11	U22	U33	U12	U13	U23
Cu1	0.0386 (2)	0.0297 (2)	0.0341 (2)	−0.00911 (17)	0.02227 (17)	−0.00583 (17)
O1	0.0365 (9)	0.0338 (8)	0.0339 (8)	−0.0071 (7)	0.0207 (7)	−0.0019 (7)
O2	0.0523 (11)	0.0407 (9)	0.0388 (9)	−0.0031 (8)	0.0301 (8)	−0.0036 (7)
O3	0.0416 (10)	0.0443 (10)	0.0361 (9)	−0.0093 (8)	0.0239 (8)	−0.0051 (8)
N1	0.0332 (10)	0.0304 (10)	0.0301 (9)	−0.0060 (7)	0.0177 (8)	−0.0028 (7)
N2	0.0334 (10)	0.0325 (10)	0.0311 (10)	−0.0064 (8)	0.0203 (8)	−0.0029 (8)
C1	0.0276 (11)	0.0349 (12)	0.0264 (11)	0.0006 (9)	0.0115 (9)	0.0032 (9)
C2	0.0286 (11)	0.0311 (11)	0.0260 (10)	0.0004 (8)	0.0119 (9)	−0.0003 (8)
C3	0.0315 (11)	0.0298 (11)	0.0320 (12)	0.0002 (9)	0.0133 (9)	−0.0033 (9)
C4	0.0282 (10)	0.0277 (11)	0.0296 (11)	0.0005 (8)	0.0094 (9)	0.0016 (9)
C5	0.0285 (11)	0.0303 (11)	0.0402 (12)	0.0008 (9)	0.0108 (9)	0.0071 (10)
C6	0.0478 (15)	0.0366 (14)	0.0641 (18)	−0.0063 (11)	0.0264 (13)	−0.0051 (12)
C7	0.0610 (19)	0.0357 (15)	0.104 (3)	−0.0135 (13)	0.0363 (19)	−0.0046 (15)
C8	0.0521 (18)	0.0476 (17)	0.101 (3)	−0.0060 (14)	0.0345 (18)	0.0248 (17)
C9	0.0530 (17)	0.0655 (19)	0.0588 (18)	−0.0018 (14)	0.0287 (14)	0.0232 (15)
C10	0.0481 (15)	0.0462 (15)	0.0411 (14)	−0.0060 (11)	0.0189 (12)	0.0055 (11)

Cu1—N1	1.9572 (17)	C3—C4	1.388 (3)
Cu1—N1i	1.9573 (17)	C3—H3	0.93
Cu1—O1i	1.9968 (14)	C4—C5	1.470 (3)
Cu1—O1	1.9968 (14)	C5—C6	1.382 (3)
Cu1—O3	2.5400 (19)	C5—C10	1.398 (3)
O1—C1	1.287 (3)	C6—C7	1.390 (4)
O2—C1	1.231 (3)	C6—H6	0.93
O3—H1W	0.827 (10)	C7—C8	1.368 (5)
O3—H2W	0.825 (10)	C7—H7	0.93
N1—C2	1.336 (3)	C8—C9	1.371 (5)
N1—N2	1.336 (2)	C8—H8	0.93
N2—C4	1.349 (3)	C9—C10	1.387 (3)
N2—H2	0.86	C9—H9	0.93
C1—C2	1.496 (3)	C10—H10	0.93
C2—C3	1.388 (3)
N1—Cu1—N1i	180	C3—C2—C1	135.23 (19)
N1—Cu1—O1i	98.56 (6)	C4—C3—C2	105.36 (19)
N1i—Cu1—O1i	81.44 (6)	C4—C3—H3	127.3
N1—Cu1—O1	81.44 (6)	C2—C3—H3	127.3
N1i—Cu1—O1	98.56 (6)	N2—C4—C3	106.56 (18)
O1i—Cu1—O1	180	N2—C4—C5	121.60 (19)
N1—Cu1—O3	87.85 (7)	C3—C4—C5	131.8 (2)
N1i—Cu1—O3	92.15 (7)	C6—C5—C10	118.6 (2)
O1i—Cu1—O3	91.56 (6)	C6—C5—C4	120.2 (2)
O1—Cu1—O3	88.44 (6)	C10—C5—C4	121.2 (2)
C1—O1—Cu1	115.29 (13)	C5—C6—C7	120.6 (3)
Cu1—O3—H1W	107 (2)	C5—C6—H6	119.7
Cu1—O3—H2W	110 (2)	C7—C6—H6	119.7
H1W—O3—H2W	111 (2)	C8—C7—C6	120.1 (3)
C2—N1—N2	106.51 (17)	C8—C7—H7	120.0
C2—N1—Cu1	114.33 (14)	C6—C7—H7	120.0
N2—N1—Cu1	138.77 (14)	C7—C8—C9	120.4 (3)
N1—N2—C4	111.41 (17)	C7—C8—H8	119.8
N1—N2—H2	124.3	C9—C8—H8	119.8
C4—N2—H2	124.3	C8—C9—C10	120.1 (3)
O2—C1—O1	125.27 (19)	C8—C9—H9	120.0
O2—C1—C2	120.58 (19)	C10—C9—H9	120.0
O1—C1—C2	114.14 (18)	C9—C10—C5	120.3 (3)
N1—C2—C3	110.16 (18)	C9—C10—H10	119.9
N1—C2—C1	114.60 (18)	C5—C10—H10	119.9
N1—Cu1—O1—C1	2.75 (15)	O1—C1—C2—C3	176.1 (2)
N1i—Cu1—O1—C1	−177.25 (15)	N1—C2—C3—C4	0.0 (2)
O3—Cu1—O1—C1	−85.31 (15)	C1—C2—C3—C4	−178.6 (2)
O1i—Cu1—N1—C2	175.94 (15)	N1—N2—C4—C3	−0.1 (2)
O1—Cu1—N1—C2	−4.06 (15)	N1—N2—C4—C5	179.06 (19)
O3—Cu1—N1—C2	84.69 (16)	C2—C3—C4—N2	0.1 (2)
O1i—Cu1—N1—N2	4.4 (2)	C2—C3—C4—C5	−179.0 (2)
O1—Cu1—N1—N2	−175.6 (2)	N2—C4—C5—C6	−167.6 (2)
O3—Cu1—N1—N2	−86.8 (2)	C3—C4—C5—C6	11.3 (4)
C2—N1—N2—C4	0.1 (2)	N2—C4—C5—C10	10.3 (3)
Cu1—N1—N2—C4	172.02 (17)	C3—C4—C5—C10	−170.8 (2)
Cu1—O1—C1—O2	178.61 (18)	C10—C5—C6—C7	−0.8 (4)
Cu1—O1—C1—C2	−1.0 (2)	C4—C5—C6—C7	177.2 (3)
N2—N1—C2—C3	0.0 (2)	C5—C6—C7—C8	0.3 (5)
Cu1—N1—C2—C3	−174.22 (15)	C6—C7—C8—C9	0.2 (5)
N2—N1—C2—C1	178.84 (17)	C7—C8—C9—C10	−0.1 (5)
Cu1—N1—C2—C1	4.7 (2)	C8—C9—C10—C5	−0.5 (4)
O2—C1—C2—N1	178.0 (2)	C6—C5—C10—C9	0.9 (4)
O1—C1—C2—N1	−2.4 (3)	C4—C5—C10—C9	−177.1 (2)
O2—C1—C2—C3	−3.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1W···O2ii	0.83 (3)	1.88 (3)	2.679 (3)	161 (3)
N2—H2···O3iii	0.86	1.93	2.719 (3)	152
O3—H2W···O1iv	0.83 (3)	2.04 (3)	2.773 (3)	149 (3)

Cu1—N1	1.9572 (17)
Cu1—O1	1.9968 (14)
Cu1—O3	2.5400 (19)

N1—Cu1—N1i	180
N1—Cu1—O1i	98.56 (6)
N1—Cu1—O1	81.44 (6)
O1i—Cu1—O1	180
N1—Cu1—O3	87.85 (7)
N1i—Cu1—O3	92.15 (7)
O1i—Cu1—O3	91.56 (6)
O1—Cu1—O3	88.44 (6)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1W⋯O2ii	0.83 (3)	1.88 (3)	2.679 (3)	161 (3)
N2—H2⋯O3iii	0.86	1.93	2.719 (3)	152
O3—H2W⋯O1iv	0.83 (3)	2.04 (3)	2.773 (3)	149 (3)

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