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Acta Cryst. (2007). E63, m3160-m3161
https://doi.org/10.1107/S1600536807061193
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Retracted: (Dimethyl­glyoxime-κ2N,N′)bis­(1,10-phenanthroline-κ2N,N′)copper(II) dinitrate dihydrate

H. Zhong, X.-M. Yang, C.-J. Luo and M.-L. Li
In the cation of the title compound, [Cu(C12H8N2)2(C4H8N2O2)](NO3)2·2H2O, the Cu atom has a distorted octa­hedral coordination formed by six N atoms from one dimethyl­glyoxime and two 1,10-phenanthroline ligands. In the crystal structure, components are linked into a three-dimensional framework by O—H...O and C—H...O hydrogen bonds and π–π stacking inter­actions [centroid–centroid distance 3.592 (4) Å].
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807061193/hk2390sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807061193/hk2390Isup2.hkl
Contains datablock I

CCDC reference: 1303500

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.047
  • wR factor = 0.143
  • Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found




Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D       H3A    ..  H4B     ..       1.88 Ang.
PLAT420_ALERT_2_B D-H Without Acceptor       O2     -   H2A    ...          ?
PLAT420_ALERT_2_B D-H Without Acceptor       O3     -   H3A    ...          ?
PLAT420_ALERT_2_B D-H Without Acceptor       O4     -   H4A    ...          ?


Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         49 Perc.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N7
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N8
PLAT245_ALERT_2_C U(iso) H3A     Smaller than U(eq) O3      by ...       0.05 AngSq
PLAT414_ALERT_2_C Short Intra D-H..H-X       H2A    ..  H27A    ..       1.95 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1A    ..  N2      ..       2.84 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H28A   ..  O7      ..       2.63 Ang.
PLAT482_ALERT_4_C Small D-H..A Angle Rep for O1     ..  N2      ..      94.00 Deg.


Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         13


   0 ALERT level A = In general: serious problem
   4 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check
Comment top

The crystal structure of (dimethylglyoxime-κ2N,N')bis(1,10-phenanthroline- κ2N,N')nickel(II)dinitrate dihydrate, (II), (Zhong et al., 2007a) and (dimethylglyoxime-κ2N,N')bis(1,10-phenanthroline-κ2N,N')zinc(II)dinitrate dihydrate, (III), (Zhong et al., 2007b) have previously been reported. The crystal structure determination of the title compound, (I), has been carried out in order to elucidate the molecular conformation and to compare it with those of (II) and (III). We report herein the crystal structure of (I).

In the molecule of (I) (Fig. 1), the ligand bond lengths and angles are within normal ranges (Allen et al., 1987). The six N atoms from one dimethylglyoxime and two 1,10-phenanthroline (phen) ligands are coordinated to the Cu atom in a distorted octahedral arrangement (Table 1). The dimethylglyoxime and two phen ligands are each planar, and the phen ligands are nearly perpendicular to each other, the dihedral angle of 86.04 (3)° being the same as in (II) and (III).

In the crystal structure, the molecules are linked into a three-dimensional framework by O—H···O and C—H···O hydrogen bonds (Table 2). There are π-π stacking interactions between adjacent phen ligands with a centroid-centroid distance of 3.592 (4) Å (symmetry code: 1 - x, 2 - y, 1 - z); this compares with 3.602 (3) and 3.5997 (7) Å in (II) and (III), respectively. These π-π stacking interactions and hydrogen bonds (Table 2) lead to a supramolecular network structure (Fig. 2), as in (II) and (III).

Compounds (I), (II) and (III) are isostructural.

Related literature top

For related structures, see: Zhong et al. (2007a,b). For bond-length data, see: Allen et al. (1987).

Experimental top

Crystals of the title compound were synthesized using hydrothermal method in a 23 ml Teflon-lined Parr bomb. Copper (II) nitrate pentahydrate (295.5 mg, 1 mmol), phen (180.2 mg, 1 mmol), dimethyl glyoxime (116.2 mg, 1 mmol) and distilled water (8 g) were placed into the bomb and sealed. The bomb was then heated under autogenous pressure up to 453 K over the course of 7 d and allowed to cool at room temperature for 24 h. Upon opening the bomb, a clear colorless solution was decanted from small blue crystals. These crystals were washed with distilled water followed by ethanol, and allowed to air-dry at room temperature.

Refinement top

H atoms (for H2O) were located in a difference synthesis and refined isotropically [O—H = 0.811 (18)–0.880 (18) Å and Uiso(H) = 0.460 (7)–0.585 (10) Å2]. The remaining H atoms were positioned geometrically, with O—H = 0.82 Å (for OH) and C—H = 0.93 and 0.96 Å for aromatic and methyl H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C,O), where x = 1.2 for aromatic H, and x = 1.5 for all other H atoms.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL (Siemens, 1996).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A packing diagram of (I). Hydrogen bonds are shown as dashed lines.
(Dimethylglyoxime-κ2N,N')bis(1,10-phenanthroline-κ2N,N')copper(II) dinitrate dihydrate top
Crystal data top
[Cu(C12H8N2)2(C4H8N2O2)](NO3)2·2H2OF(000) = 1444
Mr = 700.13Dx = 1.536 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6015 reflections
a = 13.8102 (12) Åθ = 2.1–25.0°
b = 11.9816 (11) ŵ = 0.79 mm−1
c = 18.4018 (14) ÅT = 273 K
β = 96.204 (2)°Prism, blue
V = 3027.1 (4) Å30.31 × 0.22 × 0.19 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		6368 independent reflections
Radiation source: fine-focus sealed tube3102 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
ϕ and ω scansθmax = 27.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −17→17
Tmin = 0.794, Tmax = 0.867k = −15→15
20447 measured reflectionsl = −22→23
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.059P)2]
where P = (Fo2 + 2Fc2)/3
6368 reflections(Δ/σ)max = 0.003
444 parametersΔρmax = 0.58 e Å−3
13 restraintsΔρmin = −0.53 e Å−3
Crystal data top
[Cu(C12H8N2)2(C4H8N2O2)](NO3)2·2H2OV = 3027.1 (4) Å3
Mr = 700.13Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.8102 (12) ŵ = 0.79 mm−1
b = 11.9816 (11) ÅT = 273 K
c = 18.4018 (14) Å0.31 × 0.22 × 0.19 mm
β = 96.204 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		6368 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3102 reflections with I > 2σ(I)
Tmin = 0.794, Tmax = 0.867Rint = 0.042
20447 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04713 restraints
wR(F2) = 0.143H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.58 e Å−3
6368 reflectionsΔρmin = −0.53 e Å−3
444 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.77578 (3)0.75557 (4)0.03822 (3)0.04339 (18)
O10.7959 (2)0.9963 (2)0.04784 (15)0.0477 (7)
H1A0.81641.00290.00790.072*
O20.8348 (2)0.6027 (2)0.14811 (16)0.0540 (8)
H2A0.82780.59850.19170.081*
O30.5555 (11)0.4274 (14)0.1403 (10)0.508 (12)
H3A0.5564 (19)0.4911 (16)0.1554 (17)0.460 (7)*
H3B0.502 (2)0.397 (2)0.119 (2)0.511 (11)*
O40.3053 (16)0.665 (2)0.7978 (7)0.580 (18)
H4A0.272 (2)0.670 (3)0.8355 (17)0.585 (10)*
H4B0.346 (9)0.612 (11)0.811 (6)0.58 (8)*
O50.7740 (2)0.1305 (3)0.9095 (2)0.0815 (11)
O60.8929 (2)0.0157 (3)0.92842 (18)0.0651 (9)
O70.8888 (3)0.1350 (4)0.8436 (3)0.1145 (16)
O80.7391 (5)0.8777 (6)0.2887 (3)0.164 (2)
O90.6155 (6)0.8839 (6)0.3362 (4)0.191 (3)
O100.6400 (7)1.0072 (6)0.2626 (5)0.329 (9)
N10.6536 (2)0.7798 (2)0.07648 (19)0.0366 (8)
N20.7070 (2)0.8183 (2)−0.05350 (18)0.0356 (8)
N30.7386 (2)0.6061 (2)0.00380 (18)0.0395 (8)
N40.8933 (2)0.7246 (2)−0.00692 (17)0.0330 (7)
N50.8370 (2)0.7042 (3)0.12949 (18)0.0383 (8)
N60.8219 (2)0.8938 (2)0.07669 (18)0.0343 (8)
N70.8516 (3)0.0927 (3)0.8921 (2)0.0582 (10)
N80.6663 (5)0.9304 (8)0.2888 (5)0.132 (3)
C10.6306 (3)0.7623 (3)0.1435 (2)0.0485 (11)
H10.67850.73660.17900.058*
C20.5363 (3)0.7812 (4)0.1628 (3)0.0607 (13)
H20.52240.76870.21040.073*
C30.4661 (3)0.8177 (4)0.1117 (3)0.0546 (12)
H30.40330.82920.12400.066*
C40.4875 (3)0.8382 (3)0.0407 (3)0.0449 (11)
C50.4208 (3)0.8803 (4)−0.0175 (3)0.0615 (14)
H50.35660.8935−0.00900.074*
C60.4482 (3)0.9016 (4)−0.0850 (3)0.0611 (13)
H60.40230.9284−0.12160.073*
C70.5458 (3)0.8837 (3)−0.1006 (3)0.0479 (11)
C80.5806 (4)0.9062 (3)−0.1657 (3)0.0579 (13)
H80.53890.9352−0.20420.069*
C90.6759 (4)0.8867 (3)−0.1750 (3)0.0583 (13)
H90.69990.9039−0.21890.070*
C100.7368 (3)0.8403 (3)−0.1170 (2)0.0449 (11)
H100.80110.8245−0.12390.054*
C110.6125 (3)0.8403 (3)−0.0440 (2)0.0402 (10)
C120.5832 (3)0.8181 (3)0.0254 (2)0.0367 (9)
C130.6603 (3)0.5464 (4)0.0144 (3)0.0557 (12)
H130.61430.57570.04240.067*
C140.6465 (3)0.4411 (4)−0.0158 (3)0.0693 (15)
H140.59020.4017−0.00870.083*
C150.7126 (4)0.3944 (4)−0.0551 (3)0.0630 (14)
H150.70250.3232−0.07460.076*
C160.7965 (3)0.4544 (3)−0.0661 (2)0.0454 (11)
C170.8721 (3)0.4153 (4)−0.1060 (2)0.0518 (12)
H170.86560.3463−0.12910.062*
C180.9519 (3)0.4752 (4)−0.1111 (2)0.0518 (12)
H181.00050.4466−0.13710.062*
C190.9649 (3)0.5826 (3)−0.0776 (2)0.0413 (10)
C201.0478 (3)0.6513 (4)−0.0800 (2)0.0485 (11)
H201.09970.6279−0.10440.058*
C211.0503 (3)0.7505 (4)−0.0466 (2)0.0483 (10)
H211.10460.7961−0.04770.058*
C220.9718 (3)0.7865 (3)−0.0099 (2)0.0425 (10)
H220.97530.85590.01280.051*
C230.8911 (3)0.6242 (3)−0.0406 (2)0.0360 (9)
C240.8063 (3)0.5595 (3)−0.0345 (2)0.0360 (9)
C250.8806 (3)0.7818 (3)0.1719 (2)0.0404 (10)
C260.8678 (3)0.8924 (3)0.1411 (2)0.0424 (10)
C270.9330 (3)0.7564 (4)0.2448 (2)0.0625 (13)
H27A0.92570.67860.25560.094*
H27B0.90630.80050.28140.094*
H27C1.00080.77360.24460.094*
C280.9050 (3)0.9928 (4)0.1832 (3)0.0655 (14)
H28A0.96910.97770.20690.098*
H28B0.86221.01040.21930.098*
H28C0.90781.05480.15050.098*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0398 (3)0.0422 (3)0.0474 (3)0.0021 (2)0.0012 (2)−0.0023 (3)
O10.0571 (18)0.0342 (15)0.051 (2)0.0071 (13)0.0022 (15)−0.0008 (14)
O20.0619 (19)0.0469 (19)0.052 (2)0.0035 (14)0.0016 (16)0.0154 (15)
O30.43 (2)0.68 (3)0.48 (2)0.07 (2)0.37 (2)0.14 (2)
O40.47 (3)0.92 (5)0.33 (2)0.09 (3)−0.065 (17)−0.35 (2)
O50.059 (2)0.082 (3)0.105 (3)0.0161 (19)0.017 (2)0.008 (2)
O60.064 (2)0.0503 (19)0.080 (3)0.0093 (16)0.0021 (18)0.0147 (18)
O70.107 (3)0.120 (4)0.125 (4)0.032 (3)0.055 (3)0.059 (3)
O80.158 (5)0.171 (6)0.158 (6)−0.022 (5)−0.004 (5)−0.018 (4)
O90.243 (9)0.178 (6)0.150 (7)−0.005 (6)0.007 (6)−0.012 (5)
O100.433 (15)0.123 (5)0.356 (13)−0.061 (6)−0.305 (11)0.106 (6)
N10.0351 (18)0.0340 (18)0.040 (2)0.0010 (13)−0.0003 (15)0.0014 (15)
N20.038 (2)0.0291 (18)0.039 (2)0.0021 (14)−0.0014 (15)−0.0052 (15)
N30.0348 (18)0.0357 (18)0.047 (2)0.0007 (15)0.0007 (16)0.0009 (16)
N40.0282 (17)0.0293 (18)0.040 (2)0.0027 (13)−0.0033 (14)−0.0009 (14)
N50.0318 (18)0.0396 (19)0.044 (2)0.0048 (15)0.0046 (15)0.0028 (17)
N60.0318 (17)0.0326 (18)0.038 (2)0.0025 (14)0.0020 (15)−0.0013 (15)
N70.052 (3)0.056 (3)0.068 (3)−0.008 (2)0.010 (2)0.009 (2)
N80.089 (5)0.176 (9)0.123 (7)−0.005 (5)−0.021 (5)−0.079 (7)
C10.038 (2)0.057 (3)0.050 (3)0.009 (2)0.0039 (19)0.004 (2)
C20.057 (3)0.069 (3)0.059 (3)0.000 (2)0.021 (3)−0.001 (3)
C30.033 (2)0.054 (3)0.078 (4)0.000 (2)0.013 (2)−0.016 (3)
C40.035 (2)0.033 (2)0.066 (3)0.0021 (18)−0.002 (2)−0.006 (2)
C50.033 (2)0.051 (3)0.098 (5)0.007 (2)−0.005 (3)−0.007 (3)
C60.052 (3)0.048 (3)0.077 (4)0.010 (2)−0.020 (3)−0.004 (3)
C70.050 (3)0.036 (2)0.053 (3)0.003 (2)−0.015 (2)−0.005 (2)
C80.072 (3)0.046 (3)0.051 (4)0.008 (2)−0.018 (3)0.001 (2)
C90.091 (4)0.042 (3)0.039 (3)−0.002 (2)−0.007 (3)0.000 (2)
C100.056 (3)0.040 (2)0.038 (3)0.001 (2)0.003 (2)−0.006 (2)
C110.043 (3)0.026 (2)0.048 (3)0.0012 (17)−0.010 (2)−0.0047 (19)
C120.035 (2)0.028 (2)0.046 (3)−0.0028 (17)0.0000 (19)−0.0025 (19)
C130.042 (3)0.042 (3)0.084 (4)−0.003 (2)0.009 (2)−0.007 (2)
C140.053 (3)0.045 (3)0.109 (5)−0.017 (2)0.004 (3)−0.008 (3)
C150.066 (3)0.035 (2)0.085 (4)−0.006 (2)−0.005 (3)−0.011 (2)
C160.051 (3)0.034 (2)0.048 (3)0.006 (2)−0.010 (2)−0.001 (2)
C170.070 (3)0.039 (3)0.044 (3)0.011 (2)−0.005 (2)−0.005 (2)
C180.069 (3)0.050 (3)0.035 (3)0.029 (2)0.003 (2)−0.005 (2)
C190.046 (3)0.045 (2)0.032 (3)0.013 (2)−0.0020 (19)0.002 (2)
C200.042 (3)0.065 (3)0.040 (3)0.011 (2)0.008 (2)0.002 (2)
C210.036 (2)0.057 (3)0.052 (3)−0.003 (2)0.0042 (19)0.004 (3)
C220.042 (3)0.037 (2)0.047 (3)0.0025 (18)−0.001 (2)−0.0027 (19)
C230.037 (2)0.038 (2)0.032 (2)0.0078 (18)−0.0040 (18)0.0026 (19)
C240.041 (2)0.031 (2)0.034 (3)0.0058 (18)−0.0033 (18)−0.0009 (18)
C250.036 (2)0.051 (3)0.034 (3)0.0035 (19)0.0040 (18)0.003 (2)
C260.038 (2)0.042 (2)0.047 (3)−0.0004 (19)0.007 (2)−0.013 (2)
C270.058 (3)0.078 (3)0.048 (3)−0.003 (3)−0.011 (2)0.006 (3)
C280.072 (3)0.057 (3)0.065 (4)−0.006 (2)−0.007 (3)−0.022 (3)
Geometric parameters (Å, º) top
Cu1—N11.919 (3)C8—C91.365 (6)
Cu1—N21.992 (3)C8—H80.9300
Cu1—N31.950 (3)C9—C101.401 (6)
Cu1—N41.937 (3)C9—H90.9300
Cu1—N51.899 (3)C10—H100.9300
Cu1—N61.885 (3)C11—C121.406 (5)
O1—N61.370 (4)C13—C141.382 (6)
O1—H1A0.8200C13—H130.9300
O2—N51.265 (4)C14—C151.346 (6)
O2—H2A0.8200C14—H140.9300
O5—N71.236 (4)C15—C161.398 (6)
O6—N71.242 (4)C15—H150.9300
O7—N71.190 (5)C16—C241.386 (5)
O8—N81.188 (7)C16—C171.419 (6)
O9—N81.303 (9)C17—C181.326 (6)
O10—N81.083 (9)C17—H170.9300
N1—C11.322 (5)C18—C191.430 (5)
N1—C121.358 (5)C18—H180.9300
N2—C101.307 (5)C19—C231.379 (5)
N2—C111.360 (5)C19—C201.415 (5)
N3—C131.328 (5)C20—C211.336 (5)
N3—C241.352 (5)C20—H200.9300
N4—C221.320 (5)C21—C221.405 (5)
N4—C231.353 (4)C21—H210.9300
N5—C251.317 (5)C22—H220.9300
N6—C261.283 (5)C23—C241.419 (5)
C1—C21.405 (5)C25—C261.445 (5)
C1—H10.9300C25—C271.485 (5)
C2—C31.347 (6)C26—C281.492 (5)
C2—H20.9300C27—H27A0.9600
C3—C41.393 (6)C27—H27B0.9600
C3—H30.9300C27—H27C0.9600
C4—C121.401 (5)C28—H28A0.9600
C4—C51.426 (6)C28—H28B0.9600
C5—C61.362 (6)C28—H28C0.9600
C5—H50.9300O3—H3A0.811 (18)
C6—C71.425 (6)O3—H3B0.880 (18)
C6—H60.9300O4—H4B0.87 (13)
C7—C81.365 (6)O4—H4A0.876 (19)
C7—C111.413 (5)
N1—Cu1—N284.03 (14)C10—C9—H9120.6
N1—Cu1—N392.68 (13)N2—C10—C9122.6 (4)
N1—Cu1—N4175.34 (13)N2—C10—H10118.7
N1—Cu1—N592.83 (13)C9—C10—H10118.7
N1—Cu1—N690.22 (12)N2—C11—C12117.0 (3)
N2—Cu1—N389.24 (12)N2—C11—C7122.3 (4)
N2—Cu1—N493.09 (13)C12—C11—C7120.7 (4)
N2—Cu1—N5175.75 (13)N1—C12—C4122.6 (4)
N2—Cu1—N695.58 (13)N1—C12—C11116.0 (3)
N3—Cu1—N483.61 (13)C4—C12—C11121.4 (4)
N3—Cu1—N593.78 (14)N3—C13—C14120.8 (4)
N3—Cu1—N6174.62 (13)N3—C13—H13119.6
N4—Cu1—N590.22 (12)C14—C13—H13119.6
N4—Cu1—N693.71 (12)C15—C14—C13121.5 (4)
N5—Cu1—N681.54 (14)C15—C14—H14119.2
N6—O1—H1A109.5C13—C14—H14119.2
N5—O2—H2A109.5C14—C15—C16119.0 (4)
C1—N1—C12118.2 (3)C14—C15—H15120.5
C1—N1—Cu1128.8 (3)C16—C15—H15120.5
C12—N1—Cu1112.9 (3)C24—C16—C15116.8 (4)
C10—N2—C11118.4 (3)C24—C16—C17118.2 (4)
C10—N2—Cu1131.7 (3)C15—C16—C17125.0 (4)
C11—N2—Cu1109.9 (3)C18—C17—C16121.4 (4)
C13—N3—C24118.3 (3)C18—C17—H17119.3
C13—N3—Cu1129.6 (3)C16—C17—H17119.3
C24—N3—Cu1112.1 (2)C17—C18—C19121.5 (4)
C22—N4—C23117.3 (3)C17—C18—H18119.2
C22—N4—Cu1129.9 (3)C19—C18—H18119.2
C23—N4—Cu1112.9 (2)C23—C19—C20116.7 (4)
O2—N5—C25122.7 (3)C23—C19—C18118.2 (4)
O2—N5—Cu1122.0 (3)C20—C19—C18125.1 (4)
C25—N5—Cu1115.3 (3)C21—C20—C19119.0 (4)
C26—N6—O1116.9 (3)C21—C20—H20120.5
C26—N6—Cu1116.6 (3)C19—C20—H20120.5
O1—N6—Cu1125.4 (2)C20—C21—C22120.7 (4)
O7—N7—O5119.6 (4)C20—C21—H21119.6
O7—N7—O6120.6 (4)C22—C21—H21119.6
O5—N7—O6119.6 (4)N4—C22—C21121.8 (4)
O10—N8—O8133.9 (12)N4—C22—H22119.1
O10—N8—O9118.9 (10)C21—C22—H22119.1
O8—N8—O9106.9 (10)N4—C23—C19124.5 (4)
N1—C1—C2122.2 (4)N4—C23—C24115.3 (3)
N1—C1—H1118.9C19—C23—C24120.1 (4)
C2—C1—H1118.9N3—C24—C16123.5 (4)
C3—C2—C1119.5 (4)N3—C24—C23116.0 (3)
C3—C2—H2120.2C16—C24—C23120.4 (4)
C1—C2—H2120.2N5—C25—C26112.7 (4)
C2—C3—C4120.1 (4)N5—C25—C27122.5 (4)
C2—C3—H3120.0C26—C25—C27124.7 (4)
C4—C3—H3120.0N6—C26—C25113.7 (3)
C3—C4—C12117.3 (4)N6—C26—C28125.3 (4)
C3—C4—C5125.5 (4)C25—C26—C28121.0 (4)
C12—C4—C5117.2 (4)C25—C27—H27A109.5
C6—C5—C4122.0 (4)C25—C27—H27B109.5
C6—C5—H5119.0H27A—C27—H27B109.5
C4—C5—H5119.0C25—C27—H27C109.5
C5—C6—C7121.2 (4)H27A—C27—H27C109.5
C5—C6—H6119.4H27B—C27—H27C109.5
C7—C6—H6119.4C26—C28—H28A109.5
C8—C7—C11117.2 (4)C26—C28—H28B109.5
C8—C7—C6125.3 (4)H28A—C28—H28B109.5
C11—C7—C6117.6 (5)C26—C28—H28C109.5
C9—C8—C7120.7 (4)H28A—C28—H28C109.5
C9—C8—H8119.6H28B—C28—H28C109.5
C7—C8—H8119.6H3A—O3—H3B122 (3)
C8—C9—C10118.7 (4)H4B—O4—H4A102 (8)
C8—C9—H9120.6H4A—O4—H4B102 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C27—H27A···O20.962.402.806 (5)105
C27—H27B···O80.962.503.225 (10)132
C28—H28C···O10.962.412.769 (5)102
O1—H1A···N20.822.843.006 (4)94
C1—H1···N50.932.492.972 (5)112
C13—H13···N10.932.573.027 (5)111
C22—H22···N60.932.573.033 (5)111
O1—H1A···O5i0.822.392.999 (4)131
O1—H1A···O6i0.821.902.704 (4)167
C3—H3···O5ii0.932.513.354 (5)152
C5—H5···O1iii0.932.523.331 (5)145
C18—H18···O2iv0.932.383.233 (5)152
C22—H22···O6v0.932.533.279 (5)137
C15—H15···O5vi0.932.543.357 (6)147
C27—H27C···O7v0.962.593.356 (6)137
C28—H28A···O7v0.962.633.316 (6)128
Symmetry codes: (i) x, y+1, z−1; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+2, −z; (iv) −x+2, −y+1, −z; (v) −x+2, −y+1, −z+1; (vi) x, y, z−1.

Experimental details

Crystal data
Chemical formula[Cu(C12H8N2)2(C4H8N2O2)](NO3)2·2H2O
Mr700.13
Crystal system, space groupMonoclinic, P21/c
Temperature (K)273
a, b, c (Å)13.8102 (12), 11.9816 (11), 18.4018 (14)
β (°) 96.204 (2)
V (Å3)3027.1 (4)
Z4
Radiation typeMo Kα
µ (mm−1)0.79
Crystal size (mm)0.31 × 0.22 × 0.19
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.794, 0.867
No. of measured, independent and
observed [I > 2σ(I)] reflections		20447, 6368, 3102
Rint0.042
(sin θ/λ)max (Å−1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.143, 1.01
No. of reflections6368
No. of parameters444
No. of restraints13
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.58, −0.53

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996).

Selected geometric parameters (Å, º) top
Cu1—N11.919 (3)Cu1—N41.937 (3)
Cu1—N21.992 (3)Cu1—N51.899 (3)
Cu1—N31.950 (3)Cu1—N61.885 (3)
N1—Cu1—N284.03 (14)N2—Cu1—N695.58 (13)
N1—Cu1—N392.68 (13)N3—Cu1—N483.61 (13)
N1—Cu1—N4175.34 (13)N3—Cu1—N593.78 (14)
N1—Cu1—N592.83 (13)N3—Cu1—N6174.62 (13)
N1—Cu1—N690.22 (12)N4—Cu1—N590.22 (12)
N2—Cu1—N389.24 (12)N4—Cu1—N693.71 (12)
N2—Cu1—N493.09 (13)N5—Cu1—N681.54 (14)
N2—Cu1—N5175.75 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C27—H27A···O20.962.402.806 (5)105
C27—H27B···O80.962.503.225 (10)132
C28—H28C···O10.962.412.769 (5)102
O1—H1A···N20.822.843.006 (4)94
C1—H1···N50.932.492.972 (5)112
C13—H13···N10.932.573.027 (5)111
C22—H22···N60.932.573.033 (5)111
O1—H1A···O5i0.822.392.999 (4)131
O1—H1A···O6i0.821.902.704 (4)167
C3—H3···O5ii0.932.513.354 (5)152
C5—H5···O1iii0.932.523.331 (5)145
C18—H18···O2iv0.932.383.233 (5)152
C22—H22···O6v0.932.533.279 (5)137
C15—H15···O5vi0.932.543.357 (6)147
C27—H27C···O7v0.962.593.356 (6)137
C28—H28A···O7v0.962.633.316 (6)128
Symmetry codes: (i) x, y+1, z−1; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+2, −z; (iv) −x+2, −y+1, −z; (v) −x+2, −y+1, −z+1; (vi) x, y, z−1.
 

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