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The title compound, [Cu2(C14H8O3)2(C3H4N2)2(H2O)2]·CH4O, consists of oxo-bridged dinuclear complex molecules together with methanol solvent molecules. The dimers have twofold rotation symmetry. Cu has square-pyramidal coordination, with water in the apical site. The methanol molecule is disordered over a twofold rotation axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804027096/bt6552sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804027096/bt6552Isup2.hkl
Contains datablock I

CCDC reference: 258628

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.005 Å
  • Disorder in solvent or counterion
  • R factor = 0.034
  • wR factor = 0.086
  • Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT094_ALERT_2_B Ratio of Maximum / Minimum Residual Density .... 4.73 PLAT420_ALERT_2_B D-H Without Acceptor O1W - H1W2 ... ?
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.513 0.788 Tmin' and Tmax expected: 0.607 0.778 RR' = 0.834 Please check that your absorption correction is appropriate. STRVA01_ALERT_4_C Flack test results are ambiguous. From the CIF: _refine_ls_abs_structure_Flack 0.360 From the CIF: _refine_ls_abs_structure_Flack_su 0.010 PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero ....... 0.36 PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.82 PLAT127_ALERT_1_C Implicit Hall Symbol Inconsistent with Expl .... A2 -ba2 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for Cu1 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc. PLAT432_ALERT_2_C Short Inter X...Y Contact O2 .. C18 .. 2.95 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2 PLAT731_ALERT_1_C Bond Calc 0.85(4), Rep 0.850(10) ...... 4.00 su-Rat O1W -H1W1 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.84(3), Rep 0.850(10) ...... 3.00 su-Rat O1W -H1W2 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(4), Rep 0.850(10) ...... 4.00 su-Rat O1W -H1# 1.555 1.555
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 3785 Count of symmetry unique reflns 2023 Completeness (_total/calc) 187.10% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1762 Fraction of Friedel pairs measured 0.871 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 15 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 7 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Bis(µ-9-oxidofluorene-9-carboxylato-κ3O,O':O)bis[aqua(1H-imidazole- κN3)copper(II)] methanol solvate top
Crystal data top
[Cu2(C14H8O3)2(C3H4N2)2(H2O)2]·CH4OF(000) = 1600
Mr = 779.73Dx = 1.533 Mg m3
Orthorhombic, Aba2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: A2 -ba2Cell parameters from 14470 reflections
a = 17.228 (3) Åθ = 3.0–29.7°
b = 14.464 (3) ŵ = 1.32 mm1
c = 13.556 (3) ÅT = 295 K
V = 3377.9 (12) Å3Prism, blue
Z = 40.37 × 0.26 × 0.19 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
3785 independent reflections
Radiation source: fine-focus sealed tube3610 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
ω scansθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 2222
Tmin = 0.513, Tmax = 0.788k = 1818
14628 measured reflectionsl = 1717
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.086 w = 1/[σ2(Fo2) + (0.0594P)2 + 0.3152P]
where P = (Fo2 + 2Fc2)/3
S = 1.12(Δ/σ)max = 0.001
3785 reflectionsΔρmax = 1.04 e Å3
249 parametersΔρmin = 0.22 e Å3
7 restraintsAbsolute structure: Flack (1983), from 1767 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.36 (1)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cu10.58395 (1)0.52722 (2)0.50000 (3)0.0314 (1)
O10.6148 (1)0.6544 (1)0.4725 (2)0.0451 (5)
O20.5692 (1)0.7963 (1)0.4543 (2)0.0487 (5)
O30.4819 (1)0.5813 (1)0.5107 (2)0.0342 (4)
O40.4891 (4)0.5626 (4)0.8133 (5)0.081 (2)0.50
O1w0.6114 (2)0.5275 (2)0.6721 (2)0.0786 (9)
N10.6832 (1)0.4721 (1)0.4606 (2)0.0353 (4)
N20.7904 (1)0.3924 (2)0.4485 (2)0.0475 (6)
C10.5597 (1)0.7119 (2)0.4672 (2)0.0348 (5)
C20.4756 (1)0.6723 (1)0.4762 (2)0.0307 (5)
C30.4370 (2)0.6825 (2)0.3755 (2)0.0344 (5)
C40.4532 (2)0.6359 (2)0.2889 (2)0.0451 (6)
C50.4099 (2)0.6565 (3)0.2052 (3)0.0566 (8)
C60.3510 (2)0.7224 (3)0.2091 (3)0.0605 (8)
C70.3338 (2)0.7685 (2)0.2957 (3)0.0531 (7)
C80.3773 (2)0.7480 (2)0.3798 (2)0.0370 (5)
C90.3689 (1)0.7794 (2)0.4822 (2)0.0357 (6)
C100.3155 (2)0.8389 (2)0.5250 (2)0.0493 (8)
C110.3166 (2)0.8495 (2)0.6263 (3)0.0529 (8)
C120.3691 (2)0.8008 (3)0.6843 (2)0.0526 (7)
C130.4235 (2)0.7422 (2)0.6409 (2)0.0413 (6)
C140.4239 (2)0.7333 (2)0.5407 (2)0.0325 (5)
C150.7311 (1)0.4165 (2)0.5076 (3)0.0396 (5)
C160.7135 (2)0.4839 (2)0.3681 (2)0.0443 (6)
C170.7798 (2)0.4335 (2)0.3600 (2)0.0513 (7)
C180.500 (2)0.521 (2)0.916 (1)0.18 (1)0.50
H1w10.567 (2)0.527 (3)0.700 (4)0.094*
H1w20.632 (2)0.580 (2)0.679 (4)0.094*
H2n0.830 (1)0.358 (2)0.453 (3)0.057*
H40.49230.59170.28670.054*
H50.42040.62610.14630.068*
H60.32270.73550.15240.073*
H70.29430.81220.29790.064*
H100.27980.87090.48650.059*
H110.28170.88990.65610.063*
H120.36780.80740.75250.063*
H130.45880.70980.67960.050*
H150.72480.39680.57240.047*
H160.69210.52050.31870.053*
H170.81150.42840.30470.062*
H4o0.481 (7)0.619 (2)0.828 (8)0.097*0.50
H18a0.45000.50520.94270.212*0.50
H18b0.52480.56520.95780.212*0.50
H18c0.53120.46640.91100.212*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0182 (1)0.0262 (1)0.0499 (2)0.0013 (1)0.0018 (2)0.0007 (2)
O10.0205 (7)0.0321 (8)0.083 (2)0.0032 (6)0.0030 (8)0.0003 (8)
O20.0294 (7)0.0260 (8)0.091 (2)0.0056 (7)0.0032 (9)0.0047 (9)
O30.0211 (6)0.0258 (6)0.056 (1)0.0006 (5)0.0003 (8)0.0036 (8)
O40.074 (4)0.059 (3)0.109 (5)0.014 (3)0.001 (3)0.024 (3)
O1w0.064 (2)0.116 (3)0.056 (2)0.006 (2)0.011 (2)0.003 (2)
N10.023 (1)0.030 (1)0.054 (1)0.0002 (7)0.000 (1)0.0032 (8)
N20.025 (1)0.045 (1)0.073 (2)0.010 (1)0.001 (1)0.000 (1)
C10.024 (1)0.028 (1)0.052 (1)0.002 (1)0.000 (1)0.001 (1)
C20.021 (1)0.024 (1)0.047 (2)0.001 (1)0.002 (1)0.000 (1)
C30.027 (1)0.030 (1)0.046 (1)0.005 (1)0.000 (1)0.003 (1)
C40.040 (1)0.046 (1)0.050 (2)0.003 (1)0.010 (1)0.003 (1)
C50.058 (2)0.068 (2)0.044 (2)0.009 (2)0.003 (1)0.000 (2)
C60.058 (2)0.074 (2)0.049 (2)0.002 (2)0.009 (2)0.012 (2)
C70.046 (2)0.058 (2)0.055 (2)0.009 (2)0.009 (1)0.012 (1)
C80.031 (1)0.033 (1)0.047 (1)0.000 (1)0.003 (1)0.006 (1)
C90.028 (1)0.0290 (9)0.050 (2)0.002 (1)0.000 (1)0.003 (1)
C100.035 (1)0.042 (1)0.071 (2)0.013 (1)0.003 (1)0.001 (1)
C110.039 (1)0.049 (2)0.071 (2)0.011 (1)0.012 (1)0.013 (1)
C120.047 (2)0.061 (2)0.050 (2)0.001 (1)0.007 (1)0.013 (1)
C130.032 (1)0.042 (1)0.050 (2)0.001 (1)0.005 (1)0.003 (1)
C140.021 (1)0.027 (1)0.050 (1)0.000 (1)0.001 (1)0.004 (1)
C150.028 (1)0.039 (1)0.052 (1)0.004 (1)0.003 (1)0.003 (2)
C160.037 (1)0.044 (1)0.053 (2)0.000 (1)0.004 (1)0.007 (1)
C170.038 (1)0.057 (2)0.059 (2)0.002 (1)0.013 (1)0.001 (1)
C180.097 (8)0.18 (2)0.25 (2)0.04 (2)0.00 (2)0.14 (2)
Geometric parameters (Å, º) top
Cu1—O31.929 (1)C9—C141.403 (3)
Cu1—O3i1.943 (2)C10—C111.381 (5)
Cu1—O11.951 (2)C11—C121.389 (5)
Cu1—N11.961 (2)C12—C131.394 (4)
Cu1—O1w2.380 (3)C13—C141.366 (4)
Cu1—Cu1i2.9977 (7)C16—C171.359 (4)
O1—C11.264 (3)O4—C181.524 (9)
O2—C11.243 (3)O4—H4o0.85 (1)
O3—C21.401 (3)O1w—H1w10.85 (1)
N1—C151.316 (3)O1w—H1w20.85 (1)
N1—C161.369 (4)N2—H2n0.85 (1)
N2—C151.344 (4)C4—H40.9300
N2—C171.352 (4)C5—H50.9300
C1—C21.562 (3)C6—H60.9300
C2—C31.526 (3)C7—H70.9300
C2—C141.529 (3)C11—H110.9300
C3—C41.382 (4)C12—H120.9300
C3—C81.400 (4)C13—H130.9300
C4—C51.390 (5)C15—H150.9300
C5—C61.394 (5)C16—H160.9300
C6—C71.383 (5)C18—H18a0.9600
C7—C81.395 (4)C18—H18b0.9600
C8—C91.468 (4)C18—H18c0.9600
C9—C101.387 (4)
O1—Cu1—O383.1 (1)C11—C12—C13120.5 (3)
O1—Cu1—O3i159.3 (1)C14—C13—C12118.7 (3)
O1—Cu1—O1w97.6 (1)C13—C14—C9120.9 (2)
O1—Cu1—N195.4 (1)C13—C14—C2128.8 (2)
O3—Cu1—O3i77.9 (1)C9—C14—C2110.2 (2)
O3—Cu1—O1w96.1 (1)N1—C15—N2110.3 (3)
O3—Cu1—N1168.5 (1)C17—C16—N1109.1 (3)
O3i—Cu1—O1w92.5 (1)N2—C17—C16106.1 (3)
O3i—Cu1—N1101.6 (1)Cu1—O1w—H1w1105 (4)
O1w—Cu1—N195.4 (1)Cu1—O1w—H1w2102 (4)
C1—O1—Cu1115.3 (2)H1w1—O1w—H1w2109 (2)
C2—O3—Cu1115.3 (1)C15—N2—H2n136 (2)
C2—O3—Cu1i133.6 (1)C17—N2—H2n116 (2)
Cu1—O3—Cu1i101.5 (1)C3—C4—H4120.6
C15—N1—C16106.3 (2)C5—C4—H4120.6
C15—N1—Cu1131.6 (2)C4—C5—H5119.8
C16—N1—Cu1122.1 (2)C6—C5—H5119.8
C15—N2—C17108.2 (2)C7—C6—H6119.4
O2—C1—O1123.7 (2)C5—C6—H6119.4
O2—C1—C2119.5 (2)C6—C7—H7120.7
O1—C1—C2116.7 (2)C8—C7—H7120.7
O3—C2—C3115.0 (2)C11—C10—H10120.8
O3—C2—C14113.4 (2)C9—C10—H10120.8
C3—C2—C14101.6 (2)C10—C11—H11119.5
O3—C2—C1107.4 (2)C12—C11—H11119.5
C3—C2—C1107.4 (2)C11—C12—H12119.7
C14—C2—C1112.0 (2)C13—C12—H12119.7
C4—C3—C8120.9 (3)C14—C13—H13120.6
C4—C3—C2128.6 (2)C12—C13—H13120.6
C8—C3—C2110.4 (2)N1—C15—H15124.9
C3—C4—C5118.7 (3)N2—C15—H15124.9
C4—C5—C6120.5 (3)C17—C16—H16125.4
C7—C6—C5121.1 (3)N1—C16—H16125.4
C6—C7—C8118.5 (3)N2—C17—H17127.0
C7—C8—C3120.3 (3)C16—C17—H17127.0
C7—C8—C9130.9 (3)C18—O4—H4O101 (8)
C3—C8—C9108.7 (2)O4—C18—H18a109.5
C10—C9—C14120.4 (3)O4—C18—H18b109.5
C10—C9—C8130.7 (2)H18a—C18—H18b109.5
C14—C9—C8108.7 (2)O4—C18—H18c109.5
C11—C10—C9118.4 (3)H18a—C18—H18c109.5
C10—C11—C12121.0 (3)H18b—C18—H18c109.5
O3—Cu1—O1—C14.2 (2)C14—C2—C3—C85.9 (2)
O3i—Cu1—O1—C119.0 (4)C1—C2—C3—C8111.7 (2)
N1—Cu1—O1—C1164.3 (2)C8—C3—C4—C51.1 (4)
O1w—Cu1—O1—C199.5 (2)C2—C3—C4—C5179.9 (3)
Cu1i—Cu1—O1—C18.2 (2)C3—C4—C5—C60.5 (5)
O3i—Cu1—O3—C2159.6 (1)C4—C5—C6—C70.2 (5)
O1—Cu1—O3—C212.25 (18)C5—C6—C7—C80.3 (5)
N1—Cu1—O3—C271.0 (4)C6—C7—C8—C30.3 (5)
O1w—Cu1—O3—C2109.2 (2)C6—C7—C8—C9174.5 (3)
Cu1i—Cu1—O3—C2150.9 (2)C4—C3—C8—C71.0 (4)
O3i—Cu1—O3—Cu1i8.7 (1)C2—C3—C8—C7180.0 (2)
O1—Cu1—O3—Cu1i163.1 (1)C4—C3—C8—C9174.9 (2)
N1—Cu1—O3—Cu1i79.9 (3)C2—C3—C8—C94.1 (3)
O1w—Cu1—O3—Cu1i100.0 (1)C7—C8—C9—C100.3 (5)
O3—Cu1—N1—C15152.3 (3)C3—C8—C9—C10175.6 (3)
O3i—Cu1—N1—C1566.1 (2)C7—C8—C9—C14175.6 (3)
O1—Cu1—N1—C15125.7 (2)C3—C8—C9—C140.3 (3)
O1w—Cu1—N1—C1527.6 (2)C14—C9—C10—C111.7 (4)
Cu1i—Cu1—N1—C1585.2 (3)C8—C9—C10—C11173.8 (3)
O3—Cu1—N1—C1623.9 (5)C9—C10—C11—C121.0 (5)
O3i—Cu1—N1—C16110.1 (2)C10—C11—C12—C132.0 (5)
O1—Cu1—N1—C1658.1 (2)C11—C12—C13—C140.3 (5)
O1w—Cu1—N1—C16156.2 (2)C12—C13—C14—C92.3 (4)
Cu1i—Cu1—N1—C1691.0 (2)C12—C13—C14—C2178.3 (3)
Cu1—O1—C1—O2176.9 (2)C10—C9—C14—C133.4 (4)
Cu1—O1—C1—C23.9 (3)C8—C9—C14—C13173.0 (2)
Cu1—O3—C2—C3103.38 (19)C10—C9—C14—C2179.9 (2)
Cu1i—O3—C2—C335.4 (3)C8—C9—C14—C23.6 (3)
Cu1—O3—C2—C14140.33 (16)O3—C2—C14—C1346.6 (3)
Cu1i—O3—C2—C1480.9 (3)C3—C2—C14—C13170.6 (3)
Cu1—O3—C2—C116.1 (2)C1—C2—C14—C1375.1 (3)
Cu1i—O3—C2—C1154.91 (18)O3—C2—C14—C9129.7 (2)
O2—C1—C2—O3167.7 (3)C3—C2—C14—C95.7 (2)
O1—C1—C2—O313.0 (3)C1—C2—C14—C9108.6 (2)
O2—C1—C2—C368.1 (3)C16—N1—C15—N20.2 (3)
O1—C1—C2—C3111.2 (3)Cu1—N1—C15—N2176.5 (2)
O2—C1—C2—C1442.6 (3)C17—N2—C15—N10.5 (3)
O1—C1—C2—C14138.1 (2)C15—N1—C16—C170.8 (3)
O3—C2—C3—C450.1 (3)Cu1—N1—C16—C17176.3 (2)
C14—C2—C3—C4173.0 (2)C15—N2—C17—C160.9 (3)
C1—C2—C3—C469.4 (3)N1—C16—C17—N21.1 (3)
O3—C2—C3—C8128.8 (2)
Symmetry code: (i) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1w—H1w1···O40.85 (1)2.11 (3)2.892 (7)153 (5)
N2—H2n···O2ii0.85 (1)1.95 (1)2.792 (3)170 (3)
Symmetry code: (ii) x+3/2, y1/2, z.
 

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