Bis(2,2′-bipyridine)(2-hy­droxy-2,2-diphenyl­acetato)­copper(II) nitrate dihydrate

Wang, X.-J.; Zheng, C.; Mai, S.-W.; Xu, X.; Luo, Y.-F.

doi:10.1107/S1600536810035555

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page m1245

doi:10.1107/S1600536810035555

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Bis(2,2′-bipyridine)(2-hydroxy-2,2-diphenylacetato)copper(II) nitrate dihydrate

Xiao-Jun Wang,^a Chun Zheng,^a Shao-Wei Mai,^a Xuan Xu ^a ^* and Yi-Fan Luo ^a

^aSchool of Chemistry and Environment, South China Normal University, Guangzhou 510006, People's Republic of China
^*Correspondence e-mail: xuxuan2004@yahoo.com.cn

(Received 20 August 2010; accepted 3 September 2010; online 11 September 2010)

In the title complex, [Cu(C₁₄H₁₁O₃)(C₁₀H₈N₂)₂]NO₃·2H₂O, the Cu^II atom is coordinated by four N atoms from two 2,2′-bipyridine ligands and two O atoms from one benzilate ligand in a distorted octahedral geometry. A supramolecular network is formed via intermolecular O—H⋯O and C—H⋯O hydrogen-bonding interactions. π–π stacking interactions between neighboring pyridine rings are also present, the centroid—centroid distance being 3.808 (2) Å.

Related literature

For related structures, see: Carballo et al. (2005 ); Herrmann et al. (1994 ); Qiu et al. (2007 ).

Experimental

Crystal data

[Cu(C₁₄H₁₁O₃)(C₁₀H₈N₂)₂]NO₃·2H₂O
M_r = 701.18
Monoclinic, P 2₁ /c
a = 10.612 (2) Å
b = 25.758 (6) Å
c = 12.322 (3) Å
β = 108.220 (3)°
V = 3199.3 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.74 mm⁻¹
T = 296 K
0.23 × 0.21 × 0.19 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.848, T_max = 0.872
16165 measured reflections
5750 independent reflections
3659 reflections with I > 2σ(I)
R_int = 0.057

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.138
S = 1.00
5750 reflections
434 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2W—H3W⋯O5ⁱ	0.85	2.16	2.844 (6)	138
O1W—H1W⋯O4ⁱⁱ	0.85	2.07	2.884 (7)	159
O2W—H3W⋯O1Wⁱⁱⁱ	0.85	2.59	3.041 (7)	114
O1W—H2W⋯O2Wⁱⁱⁱ	0.85	2.46	3.041 (7)	126
O1W—H2W⋯O4^iv	0.85	2.28	2.856 (6)	125
O3—H3⋯O6^v	0.82	2.48	3.210 (5)	149
O3—H3⋯O1	0.82	2.10	2.597 (4)	119
C10—H10⋯O1W	0.93	2.41	3.341 (7)	174
C8—H8⋯O3^iv	0.93	2.54	3.389 (6)	152
C4—H4⋯O5^vi	0.93	2.59	3.488 (6)	162
C12—H12⋯O5^vii	0.93	2.38	3.285 (7)	165
C14—H14⋯O1^viii	0.93	2.56	3.420 (6)	155
C17—H17⋯O1^viii	0.93	2.39	3.270 (5)	159
Symmetry codes: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) -x+1, -y+1, -z+1; (iv) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (v) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (vi) x-1, y, z; (vii) $[x-1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (viii) -x+1, -y, -z+2.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810035555/pv2323sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810035555/pv2323Isup2.hkl

checkCIF report

Comment top

Hydrogen-bonding interactions between ligands are specific and directional. In this context, 2,2'-bipyridine and benzilic acid are excellent candidates for construction of three-demensional network motifs, and can simultaneously coordinate metal ions (Carballo et al., 2005; Herrmann et al., 1994; Qiu et al., 2007). Herein, we report the crystal structure of a new coordination polymer, (I).

In (I), the Cu^II centre is coordinated by two oxygen atoms from one benzilate ligand and four N atoms from two 2,2'-bipyridine ligands (Fig. 1), and represents a distorted octahedral geometry. The Cu—N distances range from 1.982 (3) to 2.174 (3) Å, and the Cu—O distances are 1.982 (3) and 2.744 (3) Å, respectively. However, the O—Cu—N and N—Cu—N angles fall in the range from 89.06 (1) to 158.18 (1) ° and 77.87 (1) to 175.10 (1) °, respectively. Intermolecular O—H···O and C—H···O hydrogen bonding interactions (Table 1) link each asymmetric unit to form a three-dimensional supramolecular network motif (Fig. 2) in (0 0 1) plane, which is stabilized by π-π stacking interactions between neighboring pyridyl rings (the centriod—centriod distance is 3.808 Å).

Related literature top

For related structures, see: Carballo et al. (2005); Herrmann et al. (1994); Qiu et al. (2007).

Experimental top

A mixture of CuNO₃ (0.063 g, 0.5mmol), 2,2'-bipyridine (0.078 g; 0.5 mmol), benzilic acid (0.114 g; 0.5 mmol), water (10 mL) was stirred vigorously for 60 min and the blue block crystals were obtained by evaporating mother liquor.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the asymmetric unit of (I) showing the atomic-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A view of the three-dimensional supramolecular network of the title compound, hydrogen bonds are shown as dashed linesand. The H-atoms not involved in H-bonds have been excluded for clarity.

Bis(2,2'-bipyridine)(2-hydroxy-2,2-diphenylacetato)copper(II) nitrate dihydrate top

Crystal data top

[Cu(C₁₄H₁₁O₃)(C₁₀H₈N₂)₂]NO₃·2H₂O	F(000) = 1452
M_r = 701.18	D_x = 1.456 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2592 reflections
a = 10.612 (2) Å	θ = 2.2–22.7°
b = 25.758 (6) Å	µ = 0.74 mm⁻¹
c = 12.322 (3) Å	T = 296 K
β = 108.220 (3)°	Block, blue
V = 3199.3 (13) Å³	0.23 × 0.21 × 0.19 mm
Z = 4

Data collection top

Bruker APEXII area-detector diffractometer	5750 independent reflections
Radiation source: fine-focus sealed tube	3659 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.057
ϕ and ω scans	θ_max = 25.2°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→9
T_min = 0.848, T_max = 0.872	k = −30→30
16165 measured reflections	l = −14→13

Refinement top

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.053P)² + 2.8562P] where P = (F_o² + 2F_c²)/3
5750 reflections	(Δ/σ)_max < 0.001
434 parameters	Δρ_max = 0.57 e Å⁻³
6 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

[Cu(C₁₄H₁₁O₃)(C₁₀H₈N₂)₂]NO₃·2H₂O	V = 3199.3 (13) Å³
M_r = 701.18	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.612 (2) Å	µ = 0.74 mm⁻¹
b = 25.758 (6) Å	T = 296 K
c = 12.322 (3) Å	0.23 × 0.21 × 0.19 mm
β = 108.220 (3)°

Data collection top

Bruker APEXII area-detector diffractometer	5750 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3659 reflections with I > 2σ(I)
T_min = 0.848, T_max = 0.872	R_int = 0.057
16165 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	6 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 1.00	Δρ_max = 0.57 e Å⁻³
5750 reflections	Δρ_min = −0.51 e Å⁻³
434 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cu1	0.41218 (5)	0.128914 (18)	0.88185 (4)	0.03907 (17)
O1	0.6773 (3)	0.12292 (11)	1.0021 (2)	0.0493 (7)
O2	0.5624 (3)	0.15418 (10)	0.8330 (2)	0.0416 (7)
O3	0.9044 (3)	0.15772 (12)	0.9953 (2)	0.0487 (7)
H3	0.8800	0.1396	1.0397	0.073*
O4	0.9802 (5)	0.43639 (17)	0.8832 (4)	0.1032 (14)
O5	1.1068 (4)	0.38476 (16)	0.8257 (4)	0.0910 (13)
O6	0.9367 (4)	0.42004 (17)	0.7058 (4)	0.0890 (12)
O1W	0.1694 (5)	0.02577 (18)	0.5874 (4)	0.1147 (15)
H2W	0.1658	0.0353	0.5204	0.172*
H1W	0.1207	−0.0011	0.5773	0.172*
O2W	0.6493 (5)	0.92807 (19)	0.5360 (4)	0.1224 (16)
H4W	0.6297	0.9527	0.4877	0.184*
H3W	0.7332	0.9259	0.5527	0.184*
N1	0.4082 (3)	0.19785 (13)	0.9567 (3)	0.0407 (8)
N2	0.2541 (3)	0.16914 (13)	0.7536 (3)	0.0422 (8)
N3	0.3174 (3)	0.08879 (13)	0.9731 (3)	0.0432 (8)
N4	0.4228 (3)	0.05833 (12)	0.8213 (3)	0.0414 (8)
N5	1.0072 (5)	0.41464 (17)	0.8048 (4)	0.0656 (11)
C1	0.4840 (4)	0.20910 (18)	1.0623 (4)	0.0509 (11)
H1	0.5372	0.1831	1.1055	0.061*
C2	0.4873 (5)	0.2571 (2)	1.1103 (4)	0.0637 (14)
H2	0.5397	0.2634	1.1851	0.076*
C3	0.4119 (5)	0.2954 (2)	1.0458 (5)	0.0705 (16)
H3A	0.4146	0.3287	1.0753	0.085*
C4	0.3318 (5)	0.28473 (18)	0.9368 (5)	0.0644 (14)
H4	0.2789	0.3107	0.8928	0.077*
C5	0.3301 (4)	0.23523 (16)	0.8930 (4)	0.0442 (10)
C6	0.2447 (4)	0.21925 (16)	0.7790 (3)	0.0415 (10)
C7	0.1595 (5)	0.25249 (19)	0.7035 (4)	0.0591 (13)
H7	0.1552	0.2873	0.7221	0.071*
C8	0.0810 (5)	0.2338 (2)	0.6007 (4)	0.0714 (15)
H8	0.0226	0.2557	0.5488	0.086*
C9	0.0892 (5)	0.1829 (2)	0.5753 (4)	0.0701 (15)
H9	0.0365	0.1695	0.5059	0.084*
C10	0.1764 (5)	0.15173 (18)	0.6536 (4)	0.0547 (12)
H10	0.1814	0.1168	0.6360	0.066*
C11	0.2639 (5)	0.10780 (19)	1.0494 (4)	0.0549 (12)
H11	0.2707	0.1433	1.0639	0.066*
C12	0.1999 (5)	0.0782 (2)	1.1073 (4)	0.0670 (14)
H12	0.1633	0.0928	1.1596	0.080*
C13	0.1914 (6)	0.0260 (2)	1.0854 (5)	0.0752 (16)
H13	0.1497	0.0044	1.1242	0.090*
C14	0.2437 (5)	0.0054 (2)	1.0070 (4)	0.0623 (13)
H14	0.2363	−0.0300	0.9911	0.075*
C15	0.3082 (4)	0.03765 (16)	0.9512 (4)	0.0434 (10)
C16	0.3693 (4)	0.02037 (16)	0.8674 (3)	0.0417 (10)
C17	0.3744 (5)	−0.03074 (17)	0.8344 (4)	0.0560 (12)
H17	0.3370	−0.0569	0.8664	0.067*
C18	0.4351 (5)	−0.04255 (18)	0.7543 (4)	0.0639 (14)
H18	0.4390	−0.0768	0.7316	0.077*
C19	0.4897 (5)	−0.00371 (18)	0.7080 (4)	0.0626 (13)
H19	0.5320	−0.0109	0.6541	0.075*
C20	0.4803 (5)	0.04618 (17)	0.7434 (4)	0.0518 (12)
H20	0.5161	0.0728	0.7112	0.062*
C21	0.6700 (4)	0.14445 (14)	0.9122 (4)	0.0387 (10)
C22	0.8000 (4)	0.16241 (15)	0.8909 (3)	0.0376 (9)
C23	0.7908 (4)	0.21966 (15)	0.8583 (3)	0.0393 (10)
C24	0.7320 (5)	0.25356 (16)	0.9140 (4)	0.0506 (11)
H24	0.6962	0.2409	0.9687	0.061*
C25	0.7252 (5)	0.30584 (18)	0.8902 (5)	0.0645 (14)
H25	0.6849	0.3282	0.9286	0.077*
C26	0.7776 (5)	0.32494 (18)	0.8103 (4)	0.0606 (13)
H26	0.7723	0.3602	0.7932	0.073*
C27	0.8376 (5)	0.29183 (19)	0.7558 (4)	0.0610 (13)
H27	0.8742	0.3048	0.7020	0.073*
C28	0.8451 (4)	0.23917 (17)	0.7792 (4)	0.0511 (11)
H28	0.8868	0.2171	0.7415	0.061*
C29	0.8237 (4)	0.12686 (15)	0.7997 (3)	0.0392 (9)
C30	0.7340 (5)	0.12378 (17)	0.6913 (4)	0.0546 (12)
H30	0.6588	0.1447	0.6715	0.066*
C31	0.7548 (6)	0.0900 (2)	0.6122 (4)	0.0709 (15)
H31	0.6929	0.0877	0.5397	0.085*
C32	0.8672 (7)	0.0595 (2)	0.6401 (6)	0.0791 (17)
H32	0.8820	0.0370	0.5864	0.095*
C33	0.9555 (6)	0.0627 (2)	0.7457 (6)	0.0794 (17)
H33	1.0314	0.0422	0.7646	0.095*
C34	0.9351 (5)	0.09591 (18)	0.8255 (4)	0.0592 (13)
H34	0.9971	0.0975	0.8980	0.071*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0364 (3)	0.0342 (3)	0.0450 (3)	−0.0020 (2)	0.0105 (2)	0.0002 (2)
O1	0.0513 (19)	0.0515 (18)	0.0466 (18)	0.0013 (15)	0.0173 (15)	0.0154 (14)
O2	0.0374 (17)	0.0392 (16)	0.0461 (17)	−0.0033 (13)	0.0101 (14)	0.0019 (13)
O3	0.0391 (17)	0.056 (2)	0.0426 (17)	−0.0052 (14)	0.0012 (14)	0.0060 (14)
O4	0.122 (4)	0.099 (3)	0.101 (3)	−0.014 (3)	0.052 (3)	−0.037 (3)
O5	0.083 (3)	0.087 (3)	0.106 (3)	0.021 (2)	0.035 (3)	0.023 (2)
O6	0.072 (3)	0.113 (3)	0.075 (3)	−0.002 (2)	0.013 (2)	0.013 (2)
O1W	0.105 (4)	0.113 (4)	0.120 (4)	−0.008 (3)	0.025 (3)	−0.028 (3)
O2W	0.091 (3)	0.142 (4)	0.126 (4)	0.007 (3)	0.022 (3)	0.002 (3)
N1	0.0338 (19)	0.045 (2)	0.043 (2)	−0.0035 (16)	0.0108 (17)	−0.0041 (16)
N2	0.036 (2)	0.040 (2)	0.046 (2)	0.0015 (16)	0.0063 (17)	−0.0025 (16)
N3	0.037 (2)	0.043 (2)	0.049 (2)	0.0013 (16)	0.0127 (17)	0.0030 (16)
N4	0.040 (2)	0.040 (2)	0.043 (2)	−0.0030 (16)	0.0110 (17)	0.0023 (16)
N5	0.069 (3)	0.060 (3)	0.072 (3)	−0.016 (2)	0.028 (3)	0.000 (2)
C1	0.042 (3)	0.057 (3)	0.051 (3)	−0.003 (2)	0.010 (2)	−0.008 (2)
C2	0.050 (3)	0.075 (4)	0.066 (3)	−0.008 (3)	0.017 (3)	−0.027 (3)
C3	0.061 (3)	0.058 (3)	0.091 (4)	−0.004 (3)	0.021 (3)	−0.039 (3)
C4	0.058 (3)	0.047 (3)	0.084 (4)	0.008 (2)	0.016 (3)	−0.007 (3)
C5	0.035 (2)	0.042 (2)	0.055 (3)	0.001 (2)	0.014 (2)	−0.006 (2)
C6	0.034 (2)	0.046 (3)	0.044 (3)	0.0041 (19)	0.011 (2)	0.000 (2)
C7	0.051 (3)	0.056 (3)	0.065 (3)	0.016 (2)	0.011 (3)	0.012 (2)
C8	0.054 (3)	0.087 (4)	0.060 (4)	0.023 (3)	−0.002 (3)	0.014 (3)
C9	0.053 (3)	0.090 (4)	0.051 (3)	0.006 (3)	−0.007 (3)	−0.005 (3)
C10	0.050 (3)	0.051 (3)	0.054 (3)	0.001 (2)	0.003 (2)	−0.006 (2)
C11	0.050 (3)	0.059 (3)	0.061 (3)	0.000 (2)	0.026 (3)	0.000 (2)
C12	0.061 (3)	0.081 (4)	0.069 (3)	−0.001 (3)	0.034 (3)	0.005 (3)
C13	0.083 (4)	0.078 (4)	0.076 (4)	−0.013 (3)	0.041 (3)	0.018 (3)
C14	0.067 (3)	0.056 (3)	0.066 (3)	−0.006 (3)	0.023 (3)	0.011 (2)
C15	0.035 (2)	0.043 (3)	0.046 (3)	−0.0045 (19)	0.003 (2)	0.009 (2)
C16	0.036 (2)	0.040 (2)	0.043 (3)	−0.0039 (18)	0.003 (2)	0.0070 (19)
C17	0.064 (3)	0.037 (3)	0.065 (3)	−0.009 (2)	0.018 (3)	0.004 (2)
C18	0.075 (4)	0.040 (3)	0.072 (4)	−0.001 (3)	0.018 (3)	−0.007 (2)
C19	0.071 (4)	0.049 (3)	0.073 (3)	0.000 (3)	0.030 (3)	−0.010 (2)
C20	0.054 (3)	0.049 (3)	0.054 (3)	−0.009 (2)	0.018 (2)	−0.003 (2)
C21	0.041 (3)	0.030 (2)	0.044 (3)	0.0003 (18)	0.012 (2)	−0.0027 (18)
C22	0.033 (2)	0.041 (2)	0.037 (2)	−0.0013 (18)	0.0094 (19)	0.0019 (18)
C23	0.035 (2)	0.035 (2)	0.044 (2)	−0.0055 (18)	0.008 (2)	−0.0010 (18)
C24	0.060 (3)	0.040 (3)	0.057 (3)	−0.007 (2)	0.025 (2)	−0.003 (2)
C25	0.070 (4)	0.045 (3)	0.080 (4)	−0.001 (3)	0.025 (3)	−0.008 (3)
C26	0.055 (3)	0.041 (3)	0.075 (4)	−0.006 (2)	0.006 (3)	0.007 (3)
C27	0.061 (3)	0.053 (3)	0.067 (3)	−0.013 (3)	0.018 (3)	0.017 (3)
C28	0.051 (3)	0.050 (3)	0.056 (3)	−0.005 (2)	0.022 (2)	0.003 (2)
C29	0.039 (2)	0.036 (2)	0.047 (2)	−0.0025 (19)	0.019 (2)	0.0019 (19)
C30	0.067 (3)	0.050 (3)	0.047 (3)	0.003 (2)	0.018 (2)	−0.003 (2)
C31	0.095 (5)	0.065 (3)	0.054 (3)	−0.010 (3)	0.025 (3)	−0.009 (3)
C32	0.107 (5)	0.058 (3)	0.091 (5)	0.005 (3)	0.058 (4)	−0.012 (3)
C33	0.073 (4)	0.074 (4)	0.099 (5)	0.016 (3)	0.040 (4)	−0.001 (3)
C34	0.048 (3)	0.063 (3)	0.069 (3)	0.010 (2)	0.022 (3)	0.002 (3)

Geometric parameters (Å, º) top

Cu1—O2	1.982 (3)	C11—H11	0.9300
Cu1—N4	1.982 (3)	C12—C13	1.369 (7)
Cu1—N1	2.007 (3)	C12—H12	0.9300
Cu1—N3	2.013 (3)	C13—C14	1.362 (7)
Cu1—N2	2.174 (3)	C13—H13	0.9300
O1—C21	1.220 (5)	C14—C15	1.388 (6)
O2—C21	1.274 (5)	C14—H14	0.9300
O3—C22	1.417 (4)	C15—C16	1.450 (6)
O3—H3	0.8200	C16—C17	1.384 (6)
O4—N5	1.225 (5)	C17—C18	1.370 (6)
O5—N5	1.267 (5)	C17—H17	0.9300
O6—N5	1.223 (5)	C18—C19	1.367 (7)
O1W—H2W	0.8499	C18—H18	0.9300
O1W—H1W	0.8501	C19—C20	1.371 (6)
O2W—H4W	0.8499	C19—H19	0.9300
O2W—H3W	0.8499	C20—H20	0.9300
N1—C1	1.330 (5)	C21—C22	1.553 (6)
N1—C5	1.350 (5)	C22—C23	1.523 (5)
N2—C10	1.328 (5)	C22—C29	1.530 (5)
N2—C6	1.339 (5)	C23—C28	1.374 (6)
N3—C11	1.334 (5)	C23—C24	1.375 (6)
N3—C15	1.342 (5)	C24—C25	1.375 (6)
N4—C20	1.326 (5)	C24—H24	0.9300
N4—C16	1.343 (5)	C25—C26	1.365 (7)
C1—C2	1.366 (6)	C25—H25	0.9300
C1—H1	0.9300	C26—C27	1.360 (7)
C2—C3	1.359 (7)	C26—H26	0.9300
C2—H2	0.9300	C27—C28	1.384 (6)
C3—C4	1.374 (7)	C27—H27	0.9300
C3—H3A	0.9300	C28—H28	0.9300
C4—C5	1.383 (6)	C29—C34	1.378 (6)
C4—H4	0.9300	C29—C30	1.379 (6)
C5—C6	1.473 (6)	C30—C31	1.375 (6)
C6—C7	1.375 (6)	C30—H30	0.9300
C7—C8	1.368 (7)	C31—C32	1.379 (8)
C7—H7	0.9300	C31—H31	0.9300
C8—C9	1.356 (7)	C32—C33	1.347 (8)
C8—H8	0.9300	C32—H32	0.9300
C9—C10	1.369 (6)	C33—C34	1.371 (7)
C9—H9	0.9300	C33—H33	0.9300
C10—H10	0.9300	C34—H34	0.9300
C11—C12	1.362 (6)

O2—Cu1—N4	92.34 (13)	C12—C13—H13	119.8
O2—Cu1—N1	89.06 (12)	C13—C14—C15	119.5 (5)
N4—Cu1—N1	175.10 (14)	C13—C14—H14	120.3
O2—Cu1—N3	158.18 (12)	C15—C14—H14	120.3
N4—Cu1—N3	80.61 (14)	N3—C15—C14	120.2 (4)
N1—Cu1—N3	96.40 (14)	N3—C15—C16	115.1 (4)
O2—Cu1—N2	97.69 (12)	C14—C15—C16	124.7 (4)
N4—Cu1—N2	106.57 (13)	N4—C16—C17	120.5 (4)
N1—Cu1—N2	77.87 (13)	N4—C16—C15	114.9 (4)
N3—Cu1—N2	104.11 (13)	C17—C16—C15	124.7 (4)
C21—O2—Cu1	108.4 (3)	C18—C17—C16	119.6 (4)
C22—O3—H3	109.5	C18—C17—H17	120.2
H2W—O1W—H1W	104.6	C16—C17—H17	120.2
H4W—O2W—H3W	103.2	C19—C18—C17	119.6 (4)
C1—N1—C5	119.1 (4)	C19—C18—H18	120.2
C1—N1—Cu1	123.3 (3)	C17—C18—H18	120.2
C5—N1—Cu1	117.5 (3)	C18—C19—C20	118.1 (5)
C10—N2—C6	118.1 (4)	C18—C19—H19	120.9
C10—N2—Cu1	128.9 (3)	C20—C19—H19	120.9
C6—N2—Cu1	112.8 (3)	N4—C20—C19	123.2 (4)
C11—N3—C15	118.8 (4)	N4—C20—H20	118.4
C11—N3—Cu1	127.0 (3)	C19—C20—H20	118.4
C15—N3—Cu1	114.1 (3)	O1—C21—O2	125.0 (4)
C20—N4—C16	119.1 (4)	O1—C21—C22	118.8 (4)
C20—N4—Cu1	125.6 (3)	O2—C21—C22	116.3 (3)
C16—N4—Cu1	115.3 (3)	O3—C22—C23	106.8 (3)
O6—N5—O4	120.8 (5)	O3—C22—C29	110.7 (3)
O6—N5—O5	118.8 (5)	C23—C22—C29	113.4 (3)
O4—N5—O5	120.3 (5)	O3—C22—C21	107.8 (3)
N1—C1—C2	123.2 (5)	C23—C22—C21	110.2 (3)
N1—C1—H1	118.4	C29—C22—C21	107.7 (3)
C2—C1—H1	118.4	C28—C23—C24	118.6 (4)
C3—C2—C1	118.2 (5)	C28—C23—C22	122.3 (4)
C3—C2—H2	120.9	C24—C23—C22	119.0 (4)
C1—C2—H2	120.9	C23—C24—C25	121.2 (4)
C2—C3—C4	119.8 (5)	C23—C24—H24	119.4
C2—C3—H3A	120.1	C25—C24—H24	119.4
C4—C3—H3A	120.1	C26—C25—C24	120.0 (5)
C3—C4—C5	119.6 (5)	C26—C25—H25	120.0
C3—C4—H4	120.2	C24—C25—H25	120.0
C5—C4—H4	120.2	C27—C26—C25	119.3 (5)
N1—C5—C4	120.0 (4)	C27—C26—H26	120.4
N1—C5—C6	116.0 (4)	C25—C26—H26	120.4
C4—C5—C6	124.0 (4)	C26—C27—C28	121.2 (5)
N2—C6—C7	121.6 (4)	C26—C27—H27	119.4
N2—C6—C5	115.0 (3)	C28—C27—H27	119.4
C7—C6—C5	123.4 (4)	C23—C28—C27	119.8 (4)
C8—C7—C6	119.2 (5)	C23—C28—H28	120.1
C8—C7—H7	120.4	C27—C28—H28	120.1
C6—C7—H7	120.4	C34—C29—C30	118.2 (4)
C9—C8—C7	119.3 (5)	C34—C29—C22	120.2 (4)
C9—C8—H8	120.3	C30—C29—C22	121.6 (4)
C7—C8—H8	120.3	C31—C30—C29	120.5 (5)
C8—C9—C10	118.8 (5)	C31—C30—H30	119.7
C8—C9—H9	120.6	C29—C30—H30	119.7
C10—C9—H9	120.6	C30—C31—C32	120.1 (5)
N2—C10—C9	122.9 (4)	C30—C31—H31	119.9
N2—C10—H10	118.6	C32—C31—H31	119.9
C9—C10—H10	118.6	C33—C32—C31	119.5 (5)
N3—C11—C12	123.7 (5)	C33—C32—H32	120.3
N3—C11—H11	118.2	C31—C32—H32	120.3
C12—C11—H11	118.2	C32—C33—C34	120.9 (5)
C11—C12—C13	117.4 (5)	C32—C33—H33	119.6
C11—C12—H12	121.3	C34—C33—H33	119.6
C13—C12—H12	121.3	C33—C34—C29	120.8 (5)
C14—C13—C12	120.4 (5)	C33—C34—H34	119.6
C14—C13—H13	119.8	C29—C34—H34	119.6

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2W—H3W···O5ⁱ	0.85	2.16	2.844 (6)	138
O1W—H1W···O4ⁱⁱ	0.85	2.07	2.884 (7)	159
O2W—H3W···O1Wⁱⁱⁱ	0.85	2.59	3.041 (7)	114
O1W—H2W···O2Wⁱⁱⁱ	0.85	2.46	3.041 (7)	126
O1W—H2W···O4^iv	0.85	2.28	2.856 (6)	125
O3—H3···O6^v	0.82	2.48	3.210 (5)	149
O3—H3···O1	0.82	2.10	2.597 (4)	119
C20—H20···O2	0.93	2.53	3.019 (5)	113
C30—H30···O2	0.93	2.52	2.994 (5)	112
C34—H34···O3	0.93	2.35	2.728 (6)	104
C10—H10···O1W	0.93	2.41	3.341 (7)	174
C8—H8···O3^iv	0.93	2.54	3.389 (6)	152
C4—H4···O5^vi	0.93	2.59	3.488 (6)	162
C12—H12···O5^vii	0.93	2.38	3.285 (7)	165
C14—H14···O1^viii	0.93	2.56	3.420 (6)	155
C17—H17···O1^viii	0.93	2.39	3.270 (5)	159

Symmetry codes: (i) −x+2, y+1/2, −z+3/2; (ii) −x+1, y−1/2, −z+3/2; (iii) −x+1, −y+1, −z+1; (iv) x−1, −y+1/2, z−1/2; (v) x, −y+1/2, z+1/2; (vi) x−1, y, z; (vii) x−1, −y+1/2, z+1/2; (viii) −x+1, −y, −z+2.

Experimental details

Crystal data
Chemical formula	[Cu(C₁₄H₁₁O₃)(C₁₀H₈N₂)₂]NO₃·2H₂O
M_r	701.18
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	10.612 (2), 25.758 (6), 12.322 (3)
β (°)	108.220 (3)
V (Å³)	3199.3 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.74
Crystal size (mm)	0.23 × 0.21 × 0.19

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.848, 0.872
No. of measured, independent and observed [I > 2σ(I)] reflections	16165, 5750, 3659
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.138, 1.00
No. of reflections	5750
No. of parameters	434
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.51

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2W—H3W···O5ⁱ	0.85	2.16	2.844 (6)	137.5
O1W—H1W···O4ⁱⁱ	0.85	2.07	2.884 (7)	159.0
O2W—H3W···O1Wⁱⁱⁱ	0.85	2.59	3.041 (7)	114.3
O1W—H2W···O2Wⁱⁱⁱ	0.85	2.46	3.041 (7)	125.8
O1W—H2W···O4^iv	0.85	2.28	2.856 (6)	125.4
O3—H3···O6^v	0.82	2.48	3.210 (5)	149.1
O3—H3···O1	0.82	2.10	2.597 (4)	119.0
C10—H10···O1W	0.93	2.41	3.341 (7)	173.9
C8—H8···O3^iv	0.93	2.54	3.389 (6)	151.6
C4—H4···O5^vi	0.93	2.59	3.488 (6)	162.1
C12—H12···O5^vii	0.93	2.38	3.285 (7)	165.4
C14—H14···O1^viii	0.93	2.56	3.420 (6)	154.8
C17—H17···O1^viii	0.93	2.39	3.270 (5)	158.5

Acknowledgements

The authors acknowledge the Natural Science Foundation of Guangdong Province (No. 9151063101000037) for support of this work.

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Carballo, R., Covelo, B., Vazquez-Lopez, E. M., Garcia-Martinez, E., Castineiras, A. & Niclos, J. (2005). Z. Anorg. Allg. Chem. 631, 785–792. Web of Science CSD CrossRef CAS Google Scholar
Herrmann, W. A., Roesky, P. W., Scherer, W. & Kleine, M. (1994). Organometallics, 13, 4536–4542. CSD CrossRef CAS Web of Science Google Scholar
Qiu, Y. C., Wang, K. N., Liu, Y., Deng, H., Sun, F. & Cai, Y. P. (2007). Inorg. Chim. Acta, 360, 1819–1824. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 66| Part 10| October 2010| Page m1245

doi:10.1107/S1600536810035555

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Bis(2,2′-bi­pyridine)(2-hy­dr­oxy-2,2-di­phenyl­acetato)­copper(II) nitrate dihydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis(2,2′-bipyridine)(2-hydroxy-2,2-diphenylacetato)copper(II) nitrate dihydrate