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The title centrosymmetric binuclear complex, [Cu2(C2O4)(C12H8N2)2(C3H7NO)2](ClO4)2, was synthesized by the reaction of 1,10-phenanthroline, 2,5-dihydr­oxy-1,4-dithiane and Cu(ClO4)2·6H2O. In the asymmetric unit, the CuII atom is in a distorted square-pyramidal coordination geometry. The closest Cu...O distance involving the perchlorate anion is 2.745 (2) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806013547/lh2035sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806013547/lh2035Isup2.hkl
Contains datablock I

CCDC reference: 608446

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.044
  • wR factor = 0.116
  • Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for O4 PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for Cl1
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct... 1 PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.59 Ratio PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C16 - C16_a ... 1.54 Ang. PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C14 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C15
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

µ-Oxalato-bis[(N,N'-dimethylformamide)(1,10-phenanthroline)copper(II)] bis(perchlorate) top
Crystal data top
[Cu2(C2O4)(C12H8N2)2(C3H7NFO)2](ClO4)2Z = 1
Mr = 920.62F(000) = 468
Triclinic, P1Dx = 1.723 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.3567 (11) ÅCell parameters from 3634 reflections
b = 9.2013 (12) Åθ = 1.8–26.5°
c = 11.7229 (15) ŵ = 1.43 mm1
α = 84.321 (17)°T = 293 K
β = 86.979 (17)°Prism, blue
γ = 81.809 (17)°0.12 × 0.10 × 0.06 mm
V = 887.1 (2) Å3
Data collection top
Bruker SMART APEX CCD
diffractometer
3634 independent reflections
Radiation source: fine-focus sealed tube2941 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
φ and ω scansθmax = 26.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1010
Tmin = 0.847, Tmax = 0.919k = 1111
7265 measured reflectionsl = 1414
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0633P)2 + 0.0846P]
where P = (Fo2 + 2Fc2)/3
3634 reflections(Δ/σ)max < 0.001
257 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = 0.34 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 > 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
O70.0209 (3)0.7941 (4)0.3501 (2)0.0692 (9)
O50.2193 (4)0.8514 (4)0.2571 (3)0.0735 (9)
O60.0214 (4)0.8946 (4)0.1608 (3)0.0807 (10)
O40.1008 (4)0.6543 (3)0.2080 (3)0.0686 (8)
H130.211 (4)0.081 (4)0.433 (3)0.049 (11)*
Cu10.22596 (4)0.41809 (4)0.35355 (3)0.03075 (15)
O30.1959 (2)0.5442 (2)0.48107 (18)0.0313 (5)
O20.0014 (3)0.3832 (2)0.39197 (18)0.0322 (5)
N20.2460 (3)0.3092 (3)0.2141 (2)0.0335 (6)
N10.4393 (3)0.4738 (3)0.2957 (2)0.0299 (6)
O10.3343 (3)0.2254 (3)0.4773 (2)0.0405 (6)
C160.0566 (4)0.5466 (3)0.5255 (3)0.0278 (7)
C120.4942 (4)0.4077 (3)0.1997 (3)0.0311 (7)
N30.3130 (3)0.0016 (3)0.5725 (2)0.0368 (6)
C110.3893 (4)0.3188 (3)0.1550 (3)0.0322 (7)
C10.5289 (4)0.5628 (4)0.3363 (3)0.0365 (8)
H10.49210.60970.40140.044*
C70.4343 (5)0.2503 (4)0.0549 (3)0.0407 (8)
C40.6417 (4)0.4252 (4)0.1437 (3)0.0389 (8)
C20.6781 (4)0.5883 (4)0.2835 (3)0.0405 (8)
H20.73790.65270.31320.049*
C130.2826 (4)0.1052 (4)0.4882 (3)0.0368 (8)
C50.6868 (5)0.3513 (5)0.0426 (3)0.0534 (10)
H50.78620.36130.00530.064*
C100.1429 (5)0.2315 (4)0.1732 (3)0.0459 (9)
H100.04470.22340.21280.055*
C30.7355 (4)0.5206 (4)0.1906 (3)0.0432 (9)
H30.83580.53580.15710.052*
C90.1781 (5)0.1614 (4)0.0723 (3)0.0544 (11)
H90.10340.10850.04530.065*
C150.4046 (5)0.0240 (4)0.6687 (3)0.0505 (10)
H15A0.41470.06330.72130.076*
H15B0.34970.10560.70690.076*
H15C0.51020.04480.64190.076*
C80.3188 (6)0.1707 (4)0.0152 (3)0.0551 (11)
H80.34140.12420.05190.066*
C60.5884 (5)0.2677 (5)0.0002 (3)0.0542 (10)
H60.62100.22060.06550.065*
C140.2375 (6)0.1320 (4)0.5807 (4)0.0647 (12)
H14A0.27400.19460.64740.097*
H14B0.26660.18290.51340.097*
H14C0.12210.10680.58680.097*
Cl10.06992 (10)0.80029 (10)0.24403 (7)0.0414 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O70.0588 (18)0.094 (2)0.0460 (17)0.0124 (16)0.0150 (14)0.0035 (16)
O50.0589 (19)0.089 (2)0.082 (2)0.0363 (17)0.0032 (16)0.0121 (19)
O60.091 (2)0.083 (2)0.067 (2)0.0171 (19)0.0300 (18)0.0226 (18)
O40.080 (2)0.0595 (18)0.069 (2)0.0146 (16)0.0115 (16)0.0231 (16)
Cu10.0300 (2)0.0344 (2)0.0292 (2)0.00795 (16)0.00636 (16)0.00890 (16)
O30.0266 (11)0.0365 (12)0.0326 (12)0.0088 (9)0.0047 (9)0.0093 (10)
O20.0313 (11)0.0343 (12)0.0339 (12)0.0109 (9)0.0066 (9)0.0126 (10)
N20.0385 (15)0.0332 (15)0.0296 (14)0.0087 (12)0.0027 (12)0.0039 (12)
N10.0318 (14)0.0288 (14)0.0283 (14)0.0031 (11)0.0026 (11)0.0024 (11)
O10.0462 (14)0.0332 (13)0.0414 (14)0.0063 (11)0.0021 (11)0.0000 (11)
C160.0306 (16)0.0251 (16)0.0281 (16)0.0062 (13)0.0022 (13)0.0013 (13)
C120.0336 (17)0.0292 (16)0.0287 (16)0.0014 (13)0.0010 (13)0.0015 (13)
N30.0395 (16)0.0300 (15)0.0401 (16)0.0030 (12)0.0017 (13)0.0035 (12)
C110.0396 (18)0.0322 (17)0.0239 (16)0.0039 (14)0.0019 (13)0.0010 (13)
C10.0368 (18)0.0377 (19)0.0358 (19)0.0066 (15)0.0007 (14)0.0061 (15)
C70.057 (2)0.0362 (19)0.0283 (17)0.0062 (16)0.0056 (15)0.0030 (15)
C40.0335 (18)0.046 (2)0.0348 (18)0.0016 (15)0.0041 (14)0.0001 (15)
C20.0364 (19)0.040 (2)0.047 (2)0.0134 (15)0.0070 (16)0.0005 (16)
C130.0350 (18)0.036 (2)0.039 (2)0.0026 (15)0.0021 (15)0.0065 (15)
C50.045 (2)0.072 (3)0.040 (2)0.002 (2)0.0128 (17)0.008 (2)
C100.054 (2)0.050 (2)0.038 (2)0.0205 (18)0.0009 (17)0.0064 (17)
C30.0299 (18)0.054 (2)0.044 (2)0.0071 (16)0.0019 (15)0.0046 (17)
C90.080 (3)0.054 (2)0.037 (2)0.033 (2)0.001 (2)0.0088 (18)
C150.058 (2)0.044 (2)0.045 (2)0.0073 (18)0.0031 (18)0.0036 (18)
C80.088 (3)0.050 (2)0.032 (2)0.020 (2)0.006 (2)0.0140 (18)
C60.065 (3)0.060 (3)0.037 (2)0.004 (2)0.0163 (19)0.0132 (19)
C140.076 (3)0.043 (2)0.077 (3)0.022 (2)0.000 (2)0.004 (2)
Cl10.0414 (5)0.0474 (5)0.0356 (5)0.0097 (4)0.0024 (4)0.0023 (4)
Geometric parameters (Å, º) top
O7—Cl11.422 (3)C1—C21.402 (4)
O5—Cl11.416 (3)C1—H10.9300
O6—Cl11.418 (3)C7—C81.414 (5)
O4—Cl11.433 (3)C7—C61.431 (5)
Cu1—O31.966 (2)C4—C31.422 (5)
Cu1—O21.970 (2)C4—C51.431 (5)
Cu1—N21.988 (3)C2—C31.341 (5)
Cu1—N11.991 (3)C2—H20.9300
Cu1—O12.289 (2)C13—H130.96 (4)
O3—C161.248 (4)C5—C61.347 (5)
O2—C16i1.254 (4)C5—H50.9300
N2—C101.330 (4)C10—C91.401 (5)
N2—C111.362 (4)C10—H100.9300
N1—C11.323 (4)C3—H30.9300
N1—C121.359 (4)C9—C81.331 (6)
O1—C131.236 (4)C9—H90.9300
C16—O2i1.254 (4)C15—H15A0.9600
C16—C16i1.543 (6)C15—H15B0.9600
C12—C41.388 (4)C15—H15C0.9600
C12—C111.431 (4)C8—H80.9300
N3—C131.311 (4)C6—H60.9300
N3—C151.443 (5)C14—H14A0.9600
N3—C141.453 (4)C14—H14B0.9600
C11—C71.396 (4)C14—H14C0.9600
O3—Cu1—O285.20 (9)C3—C2—H2119.7
O3—Cu1—N2173.88 (10)C1—C2—H2119.7
O2—Cu1—N294.33 (10)O1—C13—N3125.8 (3)
O3—Cu1—N196.51 (10)O1—C13—H13121 (2)
O2—Cu1—N1171.53 (10)N3—C13—H13113 (2)
N2—Cu1—N183.08 (11)C6—C5—C4121.5 (3)
O3—Cu1—O189.32 (9)C6—C5—H5119.3
O2—Cu1—O193.71 (9)C4—C5—H5119.3
N2—Cu1—O196.79 (10)N2—C10—C9121.9 (3)
N1—Cu1—O194.61 (9)N2—C10—H10119.1
C16—O3—Cu1110.73 (19)C9—C10—H10119.1
C16i—O2—Cu1110.83 (18)C2—C3—C4119.5 (3)
C10—N2—C11118.0 (3)C2—C3—H3120.2
C10—N2—Cu1129.9 (2)C4—C3—H3120.2
C11—N2—Cu1112.2 (2)C8—C9—C10119.8 (4)
C1—N1—C12118.4 (3)C8—C9—H9120.1
C1—N1—Cu1129.7 (2)C10—C9—H9120.1
C12—N1—Cu1111.9 (2)N3—C15—H15A109.5
C13—O1—Cu1122.3 (2)N3—C15—H15B109.5
O3—C16—O2i126.8 (3)H15A—C15—H15B109.5
O3—C16—C16i117.0 (3)N3—C15—H15C109.5
O2i—C16—C16i116.2 (3)H15A—C15—H15C109.5
N1—C12—C4123.5 (3)H15B—C15—H15C109.5
N1—C12—C11116.5 (3)C9—C8—C7121.0 (3)
C4—C12—C11119.9 (3)C9—C8—H8119.5
C13—N3—C15121.3 (3)C7—C8—H8119.5
C13—N3—C14121.3 (3)C5—C6—C7120.9 (3)
C15—N3—C14116.9 (3)C5—C6—H6119.6
N2—C11—C7123.5 (3)C7—C6—H6119.6
N2—C11—C12116.1 (3)N3—C14—H14A109.5
C7—C11—C12120.3 (3)N3—C14—H14B109.5
N1—C1—C2121.5 (3)H14A—C14—H14B109.5
N1—C1—H1119.3N3—C14—H14C109.5
C2—C1—H1119.3H14A—C14—H14C109.5
C11—C7—C8115.8 (3)H14B—C14—H14C109.5
C11—C7—C6118.6 (3)O5—Cl1—O6110.2 (2)
C8—C7—C6125.6 (3)O5—Cl1—O7110.7 (2)
C12—C4—C3116.4 (3)O6—Cl1—O7109.4 (2)
C12—C4—C5118.8 (3)O5—Cl1—O4109.1 (2)
C3—C4—C5124.7 (3)O6—Cl1—O4109.4 (2)
C3—C2—C1120.6 (3)O7—Cl1—O4108.0 (2)
O2—Cu1—O3—C160.6 (2)N1—C12—C11—N20.5 (4)
N1—Cu1—O3—C16171.0 (2)C4—C12—C11—N2179.0 (3)
O1—Cu1—O3—C1694.4 (2)N1—C12—C11—C7178.2 (3)
O3—Cu1—O2—C16i0.5 (2)C4—C12—C11—C70.3 (5)
N2—Cu1—O2—C16i173.4 (2)C12—N1—C1—C20.7 (5)
O1—Cu1—O2—C16i89.5 (2)Cu1—N1—C1—C2179.7 (2)
O2—Cu1—N2—C105.3 (3)N2—C11—C7—C81.4 (5)
N1—Cu1—N2—C10177.2 (3)C12—C11—C7—C8177.2 (3)
O1—Cu1—N2—C1089.0 (3)N2—C11—C7—C6179.8 (3)
O2—Cu1—N2—C11175.0 (2)C12—C11—C7—C61.6 (5)
N1—Cu1—N2—C113.1 (2)N1—C12—C4—C31.2 (5)
O1—Cu1—N2—C1190.7 (2)C11—C12—C4—C3177.2 (3)
O3—Cu1—N1—C12.4 (3)N1—C12—C4—C5179.4 (3)
N2—Cu1—N1—C1176.2 (3)C11—C12—C4—C51.0 (5)
O1—Cu1—N1—C187.5 (3)N1—C1—C2—C31.0 (5)
O3—Cu1—N1—C12177.2 (2)Cu1—O1—C13—N3164.6 (2)
N2—Cu1—N1—C123.4 (2)C15—N3—C13—O14.7 (5)
O1—Cu1—N1—C1292.9 (2)C14—N3—C13—O1176.0 (4)
O3—Cu1—O1—C13126.3 (3)C12—C4—C5—C61.0 (6)
O2—Cu1—O1—C1341.1 (3)C3—C4—C5—C6177.0 (4)
N2—Cu1—O1—C1353.7 (3)C11—N2—C10—C90.3 (5)
N1—Cu1—O1—C13137.2 (3)Cu1—N2—C10—C9180.0 (3)
Cu1—O3—C16—O2i179.7 (3)C1—C2—C3—C41.7 (5)
Cu1—O3—C16—C16i0.7 (4)C12—C4—C3—C20.6 (5)
C1—N1—C12—C41.9 (5)C5—C4—C3—C2177.5 (3)
Cu1—N1—C12—C4178.5 (3)N2—C10—C9—C80.6 (6)
C1—N1—C12—C11176.6 (3)C10—C9—C8—C70.2 (6)
Cu1—N1—C12—C113.0 (3)C11—C7—C8—C91.1 (6)
C10—N2—C11—C70.7 (5)C6—C7—C8—C9179.8 (4)
Cu1—N2—C11—C7179.0 (3)C4—C5—C6—C70.2 (6)
C10—N2—C11—C12177.9 (3)C11—C7—C6—C51.6 (6)
Cu1—N2—C11—C122.4 (3)C8—C7—C6—C5177.1 (4)
Symmetry code: (i) x, y+1, z+1.
 

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