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The title mononuclear complex, [Cu(C2H3O3)2(C12H8N2)]·2H2O, is isostructural with its zinc(II) analogue. The Cu atom in the complex exists in a distorted octa­hedral coordination environment, defined by four O atoms and two N atoms. O—H...O hydrogen bonds and π–π stacking inter­actions help to consolidate the crystal packing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806032028/ww2039sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806032028/ww2039Isup2.hkl
Contains datablock I

CCDC reference: 621530

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.021
  • wR factor = 0.059
  • Data-to-parameter ratio = 16.7

checkCIF/PLATON results

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Alert level B PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Cu1 - O2 .. 10.55 su PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Cu1 - O3 .. 13.44 su
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 - N1 .. 9.96 su PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SMART; data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Bis(glycolato-κ2O,O')(1,10-phenanthroline-κ2N,N')copper(II) dihydrate top
Crystal data top
[Cu(C2H3O3)2(C12H8N2)]·2H2OF(000) = 884
Mr = 429.86Dx = 1.630 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 6833 reflections
a = 8.3000 (6) Åθ = 2.7–28.3°
b = 24.534 (2) ŵ = 1.30 mm1
c = 9.1356 (7) ÅT = 273 K
β = 109.660 (1)°Block, colourless
V = 1751.9 (2) Å30.28 × 0.23 × 0.19 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
2154 independent reflections
Radiation source: fine-focus sealed tube2025 reflections with I > 2σI
Graphite monochromatorRint = 0.017
φ and ω scansθmax = 28.3°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1110
Tmin = 0.709, Tmax = 0.786k = 3232
10361 measured reflectionsl = 1212
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)] = 0.021Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.059H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.037P)2 + 0.7037P]
where P = (Fo2 + 2Fc2)/3
2154 reflections(Δ/σ)max < 0.001
129 parametersΔρmax = 0.29 e Å3
8 restraintsΔρmin = 0.31 e Å3
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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.00000.149165 (7)0.75000.02985 (8)
O10.24297 (15)0.20472 (4)1.19149 (12)0.0565 (3)
O1W0.5282 (2)0.12926 (7)1.0717 (2)0.0909 (5)
H1WA0.43290.14301.03020.129 (12)*
H1WB0.58140.14271.15730.20 (2)*
O20.17803 (12)0.16337 (4)0.96404 (11)0.0420 (2)
O30.12844 (13)0.20649 (4)0.64681 (11)0.0440 (2)
H3B0.176 (3)0.2341 (8)0.701 (2)0.070 (6)*
N10.12915 (14)0.08162 (4)0.69242 (12)0.0375 (2)
C10.25393 (18)0.08237 (6)0.63213 (16)0.0469 (3)
H1A0.29550.11580.61280.056*
C20.3254 (2)0.03448 (7)0.59645 (18)0.0572 (4)
H2A0.41160.03650.55280.069*
C30.2684 (2)0.01473 (7)0.62592 (18)0.0579 (4)
H3A0.31690.04660.60470.069*
C40.1358 (2)0.01721 (6)0.68862 (15)0.0487 (3)
C50.06880 (17)0.03268 (5)0.71916 (13)0.0379 (3)
C60.0646 (2)0.06698 (6)0.72126 (19)0.0610 (4)
H6A0.10870.10000.70230.073*
C70.14454 (17)0.19558 (5)1.05722 (14)0.0379 (3)
C80.0274 (2)0.22343 (6)0.49500 (16)0.0495 (3)
H8C0.08700.21490.42290.059*
H8B0.01120.26260.49420.059*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.03295 (11)0.02764 (11)0.02641 (11)0.0000.00664 (8)0.000
O10.0694 (7)0.0464 (5)0.0377 (5)0.0010 (5)0.0032 (5)0.0082 (4)
O1W0.0626 (8)0.0910 (10)0.1147 (13)0.0181 (8)0.0238 (9)0.0198 (10)
O20.0384 (5)0.0460 (5)0.0361 (5)0.0036 (4)0.0052 (4)0.0054 (4)
O30.0493 (5)0.0409 (5)0.0367 (5)0.0123 (4)0.0078 (4)0.0015 (4)
N10.0413 (5)0.0374 (5)0.0316 (5)0.0045 (4)0.0091 (4)0.0008 (4)
C10.0458 (7)0.0536 (8)0.0415 (7)0.0073 (6)0.0149 (6)0.0015 (6)
C20.0502 (8)0.0751 (11)0.0458 (8)0.0197 (8)0.0154 (7)0.0042 (7)
C30.0623 (9)0.0564 (9)0.0460 (8)0.0244 (7)0.0065 (7)0.0089 (6)
C40.0598 (8)0.0389 (7)0.0336 (6)0.0115 (6)0.0021 (6)0.0044 (5)
C50.0468 (7)0.0327 (6)0.0263 (5)0.0043 (5)0.0020 (5)0.0012 (4)
C60.0799 (11)0.0324 (7)0.0515 (9)0.0081 (6)0.0035 (8)0.0048 (6)
C70.0475 (7)0.0294 (5)0.0324 (6)0.0042 (5)0.0077 (5)0.0017 (4)
C80.0628 (9)0.0477 (8)0.0345 (6)0.0147 (6)0.0116 (6)0.0024 (5)
Geometric parameters (Å, º) top
Cu1—O2i2.0456 (9)C1—H1A0.9300
Cu1—O22.0456 (9)C2—C31.356 (3)
Cu1—N12.1334 (11)C2—H2A0.9300
Cu1—N1i2.1335 (11)C3—C41.403 (2)
Cu1—O32.1632 (10)C3—H3A0.9300
Cu1—O3i2.1632 (10)C4—C51.4106 (18)
O1—C71.2442 (15)C4—C61.431 (2)
O1W—H1WA0.8256C5—C5i1.434 (3)
O1W—H1WB0.8266C6—C6i1.343 (4)
O2—C71.2591 (16)C6—H6A0.9300
O3—C81.4200 (17)C7—C8i1.5078 (19)
O3—H3B0.86 (2)C8—C7i1.5078 (19)
N1—C11.3267 (17)C8—H8C0.9700
N1—C51.3544 (16)C8—H8B0.9700
C1—C21.403 (2)
O2i—Cu1—O2160.38 (6)C2—C1—H1A118.8
O2i—Cu1—N199.09 (4)C3—C2—C1119.75 (15)
O2—Cu1—N196.13 (4)C3—C2—H2A120.1
O2i—Cu1—N1i96.13 (4)C1—C2—H2A120.1
O2—Cu1—N1i99.09 (4)C2—C3—C4119.59 (14)
N1—Cu1—N1i78.07 (6)C2—C3—H3A120.2
O2i—Cu1—O377.06 (4)C4—C3—H3A120.2
O2—Cu1—O390.14 (4)C3—C4—C5117.30 (14)
N1—Cu1—O392.03 (4)C3—C4—C6123.92 (14)
N1i—Cu1—O3167.07 (4)C5—C4—C6118.77 (15)
O2i—Cu1—O3i90.14 (4)N1—C5—C4122.64 (13)
O2—Cu1—O3i77.06 (4)N1—C5—C5i117.57 (7)
N1—Cu1—O3i167.07 (4)C4—C5—C5i119.79 (9)
N1i—Cu1—O3i92.03 (4)C6i—C6—C4121.43 (9)
O3—Cu1—O3i98.90 (6)C6i—C6—H6A119.3
H1WA—O1W—H1WB113.3C4—C6—H6A119.3
C7—O2—Cu1120.03 (8)O1—C7—O2123.95 (13)
C8—O3—Cu1113.60 (8)O1—C7—C8i117.91 (12)
C8—O3—H3B110.1 (14)O2—C7—C8i118.11 (11)
Cu1—O3—H3B117.4 (13)O3—C8—C7i111.19 (11)
C1—N1—C5118.35 (12)O3—C8—H8C109.4
C1—N1—Cu1128.23 (10)C7i—C8—H8C109.4
C5—N1—Cu1113.40 (8)O3—C8—H8B109.4
N1—C1—C2122.34 (15)C7i—C8—H8B109.4
N1—C1—H1A118.8H8C—C8—H8B108.0
Symmetry code: (i) x, y, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1WA···O20.832.062.8622 (19)165
O1W—H1WB···O1ii0.832.232.992 (2)153
O3—H3B···O1iii0.86 (2)1.79 (2)2.6469 (14)174 (2)
Symmetry codes: (ii) x+1, y, z+5/2; (iii) x+1/2, y+1/2, z+2.
 

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