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In the title compound, [Cu(C14H9O3)2(C5H5NO)2]·2CH3OH, the Cu atom (site symmetry \overline{1}) is chelated by two 9-hydroxy­fluorene-9-carboxyl­ate ligands. Two N-bound 3-hydroxy­pyridine mol­ecules, which are disordered over two adjacent positions, complete the coordination of the distorted CuO4N2 octa­hedron. Various O—H...O hydrogen bonds link the metal-bearing unit and the methanol solvent mol­ecules into a linear chain structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805031156/hb6278sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805031156/hb6278Isup2.hkl
Contains datablock I

CCDC reference: 274774

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.002 Å
  • Disorder in main residue
  • R factor = 0.033
  • wR factor = 0.101
  • Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.684 0.889 Tmin(prime) and Tmax expected: 0.771 0.886 RR(prime) = 0.884 Please check that your absorption correction is appropriate. PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.88 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.71 Ratio PLAT301_ALERT_3_C Main Residue Disorder ......................... 20.00 Perc. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 1 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: difference Fourier, with Cu at 1/2, 1/2, 1/2; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Bis(9-hydroxyfluorene-9-carboxylato-κ2O,O')bis(3-hydroxypyridine- κN)copper(II) methanol disolvate top
Crystal data top
[Cu(C14H9O3)2(C5H5NO)2]·2CH4OF(000) = 798
Mr = 768.25Dx = 1.422 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 14783 reflections
a = 14.877 (3) Åθ = 3.0–27.5°
b = 7.872 (2) ŵ = 0.67 mm1
c = 16.527 (3) ÅT = 295 K
β = 112.04 (3)°Block, blue
V = 1794.2 (6) Å30.38 × 0.26 × 0.18 mm
Z = 2
Data collection top
Rigaku RAXIS-RAPID IP
diffractometer
4101 independent reflections
Radiation source: fine-focus sealed tube3706 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
ω scansθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1919
Tmin = 0.684, Tmax = 0.889k = 1010
16937 measured reflectionsl = 2121
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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0675P)2 + 0.3683P]
where P = (Fo2 + 2Fc2)/3
4101 reflections(Δ/σ)max = 0.001
298 parametersΔρmax = 0.39 e Å3
93 restraintsΔρmin = 0.42 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cu10.50000.50000.50000.0306 (1)
O10.5232 (1)0.7003 (1)0.4387 (1)0.0356 (2)
O20.6256 (1)0.8724 (1)0.4115 (1)0.0454 (3)
O30.6524 (1)0.4568 (1)0.4995 (1)0.0331 (2)
O50.7311 (1)0.1504 (2)0.5008 (1)0.0563 (3)
N10.4370 (1)0.3747 (2)0.3853 (1)0.0358 (3)
C10.6049 (1)0.7332 (2)0.4354 (1)0.0305 (3)
C20.6820 (1)0.5906 (2)0.4573 (1)0.0289 (3)
C30.6948 (1)0.5356 (2)0.3738 (1)0.0320 (3)
C40.6266 (1)0.4689 (2)0.2986 (1)0.0423 (4)
C50.6560 (2)0.4254 (2)0.2307 (1)0.0520 (4)
C60.7512 (2)0.4480 (3)0.2382 (1)0.0546 (5)
C70.8188 (2)0.5162 (2)0.3124 (1)0.0469 (4)
C80.7904 (1)0.5623 (2)0.3807 (1)0.0356 (3)
C90.8447 (1)0.6384 (2)0.4659 (1)0.0359 (3)
C100.9411 (1)0.6894 (2)0.5039 (1)0.0485 (4)
C110.9744 (1)0.7551 (3)0.5874 (1)0.0547 (5)
C120.9138 (1)0.7688 (2)0.6334 (1)0.0518 (4)
C130.8168 (1)0.7196 (2)0.5955 (1)0.0420 (4)
C140.7832 (1)0.6558 (2)0.5120 (1)0.0320 (3)
O40.4598 (5)0.0181 (5)0.2856 (2)0.090 (2)0.66 (1)
C150.4668 (3)0.2205 (5)0.3747 (4)0.037 (1)0.66 (1)
C160.4288 (4)0.1357 (5)0.2957 (3)0.048 (1)0.66 (1)
C170.3585 (5)0.217 (1)0.2257 (4)0.053 (2)0.66 (1)
C180.3283 (7)0.376 (1)0.2379 (7)0.050 (2)0.66 (1)
C190.3689 (4)0.454 (1)0.3180 (5)0.040 (1)0.66 (1)
C200.8202 (2)0.1491 (3)0.4902 (2)0.0653 (6)
O4'0.4092 (6)0.0694 (9)0.3085 (5)0.065 (2)0.34 (1)
C15'0.4467 (5)0.202 (1)0.3852 (6)0.032 (1)0.34 (1)
C16'0.4024 (5)0.100 (1)0.3116 (5)0.041 (2)0.34 (1)
C17'0.3445 (8)0.182 (2)0.2351 (8)0.043 (2)0.34 (1)
C18'0.334 (1)0.356 (2)0.235 (1)0.049 (4)0.34 (1)
C19'0.3813 (7)0.449 (2)0.3101 (8)0.038 (3)0.34 (1)
H3o0.65300.36700.47460.040*
H5o0.69570.07670.46990.068*
H40.56270.45350.29350.051*
H50.61110.38030.17950.062*
H60.76940.41650.19230.066*
H70.88250.53150.31710.056*
H100.98230.67940.47360.058*
H111.03850.79070.61320.066*
H120.93790.81120.69010.062*
H130.77590.72970.62610.050*
H4o0.50230.06460.32670.109*0.66 (1)
H150.51460.16790.42160.045*0.66 (1)
H170.33230.16370.17160.064*0.66 (1)
H180.28040.43120.19200.060*0.66 (1)
H190.34910.56330.32560.048*0.66 (1)
H20a0.86130.23650.52570.098*
H20b0.80970.16930.43010.098*
H20c0.85080.04060.50770.098*
H4'o0.44260.12220.35220.078*0.34 (1)
H15'0.48480.14910.43710.038*0.34 (1)
H17'0.31290.11950.18460.051*0.34 (1)
H18'0.29600.41180.18370.059*0.34 (1)
H19'0.37400.56630.30860.046*0.34 (1)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0291 (2)0.0303 (2)0.0365 (2)0.0027 (1)0.0169 (1)0.0035 (1)
O10.031 (1)0.033 (1)0.046 (1)0.004 (1)0.019 (1)0.003 (1)
O20.047 (1)0.029 (1)0.065 (1)0.003 (1)0.027 (1)0.010 (1)
O30.036 (1)0.025 (1)0.046 (1)0.001 (1)0.023 (1)0.003 (1)
O50.054 (1)0.033 (1)0.090 (1)0.001 (1)0.036 (1)0.007 (1)
N10.031 (1)0.039 (1)0.039 (1)0.002 (1)0.015 (1)0.004 (1)
C10.033 (1)0.027 (1)0.034 (1)0.002 (1)0.014 (1)0.001 (1)
C20.029 (1)0.026 (1)0.036 (1)0.000 (1)0.017 (1)0.001 (1)
C30.036 (1)0.026 (1)0.039 (1)0.004 (1)0.020 (1)0.002 (1)
C40.045 (1)0.039 (1)0.043 (1)0.001 (1)0.017 (1)0.004 (1)
C50.071 (1)0.045 (1)0.043 (1)0.004 (1)0.024 (1)0.006 (1)
C60.083 (1)0.043 (1)0.054 (1)0.009 (1)0.045 (1)0.002 (1)
C70.058 (1)0.037 (1)0.064 (1)0.006 (1)0.043 (1)0.004 (1)
C80.040 (1)0.027 (1)0.048 (1)0.005 (1)0.026 (1)0.005 (1)
C90.032 (1)0.029 (1)0.052 (1)0.003 (1)0.021 (1)0.005 (1)
C100.032 (1)0.041 (1)0.077 (1)0.000 (1)0.025 (1)0.002 (1)
C110.031 (1)0.048 (1)0.076 (1)0.003 (1)0.008 (1)0.003 (1)
C120.047 (1)0.046 (1)0.050 (1)0.006 (1)0.004 (1)0.000 (1)
C130.042 (1)0.041 (1)0.043 (1)0.004 (1)0.016 (1)0.001 (1)
C140.030 (1)0.028 (1)0.040 (1)0.000 (1)0.015 (1)0.004 (1)
O40.128 (4)0.053 (2)0.055 (2)0.032 (2)0.007 (2)0.020 (1)
C150.033 (2)0.042 (2)0.037 (2)0.005 (1)0.013 (1)0.003 (1)
C160.064 (2)0.034 (2)0.039 (2)0.003 (2)0.009 (1)0.004 (1)
C170.062 (3)0.048 (3)0.035 (2)0.005 (2)0.001 (2)0.001 (2)
C180.048 (3)0.047 (3)0.049 (4)0.008 (2)0.010 (2)0.007 (2)
C190.039 (2)0.042 (2)0.041 (2)0.005 (2)0.018 (2)0.004 (2)
C200.060 (1)0.048 (1)0.101 (2)0.0057 (9)0.044 (1)0.005 (1)
O4'0.075 (4)0.044 (3)0.052 (3)0.020 (3)0.005 (2)0.014 (2)
C15'0.020 (3)0.048 (3)0.030 (3)0.005 (2)0.012 (2)0.008 (2)
C16'0.042 (3)0.041 (3)0.037 (3)0.006 (2)0.011 (2)0.002 (2)
C17'0.044 (3)0.035 (5)0.043 (4)0.004 (3)0.010 (3)0.009 (3)
C18'0.051 (7)0.053 (7)0.030 (5)0.001 (4)0.000 (4)0.002 (4)
C19'0.037 (4)0.036 (4)0.048 (5)0.002 (3)0.025 (3)0.002 (3)
Geometric parameters (Å, º) top
Cu1—O11.973 (1)C16—C171.389 (6)
Cu1—O1i1.973 (1)C17—C181.373 (6)
Cu1—N12.028 (1)C18—C191.377 (6)
Cu1—N1i2.028 (1)O4'—C16'1.340 (6)
Cu1—O32.295 (1)C15'—C16'1.399 (8)
Cu1—O3i2.295 (1)C16'—C17'1.392 (9)
O1—C11.265 (2)C17'—C18'1.382 (9)
O2—C11.242 (2)C18'—C19'1.386 (9)
O3—C21.422 (2)O3—H3o0.82
O5—C201.402 (2)O5—H5o0.82
N1—C151.326 (4)C4—H40.93
N1—C19'1.341 (9)C5—H50.93
N1—C191.346 (5)C6—H60.93
N1—C15'1.368 (8)C7—H70.93
C1—C21.548 (2)C10—H100.93
C2—C141.525 (2)C11—H110.93
C2—C31.525 (2)C12—H120.93
C3—C41.379 (2)C13—H130.93
C3—C81.398 (2)O4—H4o0.82
C4—C51.392 (2)C15—H150.93
C5—C61.386 (3)C17—H170.93
C6—C71.371 (3)C18—H180.93
C7—C81.395 (2)C19—H190.93
C8—C91.462 (2)C20—H20a0.96
C9—C101.391 (2)C20—H20b0.96
C9—C141.400 (2)C20—H20c0.96
C10—C111.380 (3)O4'—H4'o0.82
C11—C121.385 (3)C15'—H15'0.93
C12—C131.394 (2)C17'—H17'0.93
C13—C141.375 (2)C18'—H18'0.93
O4—C161.328 (4)C19'—H19'0.93
C15—C161.384 (5)
O1—Cu1—O1i180C15—C16—C17118.5 (5)
O3—Cu1—O3i180C18—C17—C16118.9 (8)
N1i—Cu1—N1180C19—C18—C17120 (1)
O1i—Cu1—O3i75.74 (4)N1—C19—C18121 (1)
O1i—Cu1—O3104.26 (4)N1—C15'—C16'123.8 (8)
O1i—Cu1—N1i90.99 (5)O4'—C16'—C17'117.1 (8)
O1i—Cu1—N189.01 (5)O4'—C16'—C15'125.9 (6)
O3i—Cu1—N1i92.00 (5)C17'—C16'—C15'117.0 (9)
O3i—Cu1—N188.00 (5)C18'—C17'—C16'120 (1)
O1—Cu1—O375.74 (4)C17'—C18'—C19'120 (2)
O1—Cu1—O3i104.26 (4)C2—O3—H3o109.1
O1—Cu1—N190.99 (5)Cu1—O3—H3o109.1
O1—Cu1—N1i89.01 (5)C20—O5—H5o109.5
O3—Cu1—N192.00 (5)C3—C4—H4120.9
O3—Cu1—N1i88.00 (5)C5—C4—H4120.9
C1—O1—Cu1122.82 (9)C6—C5—H5119.5
C2—O3—Cu1112.37 (8)C4—C5—H5119.5
C15—N1—C19120.1 (6)C7—C6—H6119.6
C19'—N1—C15'117 (1)C5—C6—H6119.6
C15—N1—Cu1120.6 (3)C6—C7—H7120.6
C19'—N1—Cu1124.2 (9)C8—C7—H7120.6
C19—N1—Cu1119.1 (5)C11—C10—H10120.6
C15'—N1—Cu1118.2 (4)C9—C10—H10120.6
O2—C1—O1123.5 (1)C10—C11—H11119.5
O2—C1—C2117.7 (1)C12—C11—H11119.5
O1—C1—C2118.8 (1)C11—C12—H12119.7
O3—C2—C14112.2 (1)C13—C12—H12119.7
O3—C2—C3113.6 (1)C14—C13—H13120.7
C14—C2—C3101.6 (1)C12—C13—H13120.7
O3—C2—C1108.2 (1)C16—O4—H4o120.0
C14—C2—C1112.0 (1)N1—C15—H15119.1
C3—C2—C1109.1 (1)C16—C15—H15119.1
C4—C3—C8120.9 (2)C18—C17—H17120.5
C4—C3—C2128.6 (1)C16—C17—H17120.5
C8—C3—C2110.6 (1)C19—C18—H18120.0
C3—C4—C5118.2 (2)C17—C18—H18120.0
C6—C5—C4121.1 (2)N1—C19—H19119.7
C7—C6—C5120.8 (2)C18—C19—H19119.7
C6—C7—C8118.9 (2)O5—C20—H20a109.5
C7—C8—C3120.1 (2)O5—C20—H20b109.5
C7—C8—C9131.3 (2)H20a—C20—H20b109.5
C3—C8—C9108.6 (1)O5—C20—H20C109.5
C10—C9—C14120.0 (2)H20a—C20—H20c109.5
C10—C9—C8131.1 (2)H20b—C20—H20c109.5
C14—C9—C8109.0 (1)C16'—O4'—H4'o120.0
C11—C10—C9118.9 (2)N1—C15'—H15'118.1
C10—C11—C12121.0 (2)C16'—C15'—H15'118.1
C11—C12—C13120.6 (2)C18'—C17'—H17'120.2
C14—C13—C12118.6 (2)C16'—C17'—H17'120.2
C13—C14—C9121.0 (1)C17'—C18'—H18'120.0
C13—C14—C2128.7 (1)C19'—C18'—H18'120.0
C9—C14—C2110.3 (1)N1—C19'—C18'122.2 (17)
N1—C15—C16121.9 (4)N1—C19'—H19'118.9
O4—C16—C15121.3 (4)C18'—C19'—H19'118.9
O4—C16—C17120.2 (5)
N1i—Cu1—O1—C178.7 (1)C2—C3—C8—C91.3 (2)
N1—Cu1—O1—C1101.3 (1)C7—C8—C9—C100.9 (3)
O3i—Cu1—O1—C1170.5 (1)C3—C8—C9—C10179.7 (2)
O3—Cu1—O1—C19.5 (1)C7—C8—C9—C14178.5 (2)
O1—Cu1—O3—C20.0 (1)C3—C8—C9—C141.0 (2)
O1i—Cu1—O3—C2180.0 (1)C14—C9—C10—C110.7 (2)
N1i—Cu1—O3—C289.5 (1)C8—C9—C10—C11178.6 (2)
N1—Cu1—O3—C290.5 (1)C9—C10—C11—C120.7 (3)
O1—Cu1—N1—C15127.4 (2)C10—C11—C12—C131.4 (3)
O1i—Cu1—N1—C1552.6 (2)C11—C12—C13—C140.6 (3)
O3i—Cu1—N1—C15128.4 (2)C12—C13—C14—C90.7 (2)
O3—Cu1—N1—C1551.6 (2)C12—C13—C14—C2178.7 (2)
O1—Cu1—N1—C19'36.2 (5)C10—C9—C14—C131.4 (2)
O1i—Cu1—N1—C19'143.8 (5)C8—C9—C14—C13178.0 (1)
O3i—Cu1—N1—C19'68.0 (5)C10—C9—C14—C2179.7 (1)
O3—Cu1—N1—C19'112.0 (5)C8—C9—C14—C20.3 (2)
O1—Cu1—N1—C1948.1 (3)O3—C2—C14—C1356.9 (2)
O1i—Cu1—N1—C19131.9 (3)C3—C2—C14—C13178.6 (2)
O3i—Cu1—N1—C1956.1 (3)C1—C2—C14—C1365.0 (2)
O3—Cu1—N1—C19123.9 (3)O3—C2—C14—C9121.2 (1)
O1—Cu1—N1—C15'148.0 (3)C3—C2—C14—C90.5 (2)
O1i—Cu1—N1—C15'32.0 (3)C1—C2—C14—C9116.9 (1)
O3i—Cu1—N1—C15'107.7 (3)C19'—N1—C15—C1611.2 (6)
O3—Cu1—N1—C15'72.3 (3)C19—N1—C15—C161.0 (3)
Cu1—O1—C1—O2166.3 (1)C15'—N1—C15—C1696 (2)
Cu1—O1—C1—C217.1 (2)Cu1—N1—C15—C16176.5 (2)
Cu1—O3—C2—C14130.9 (1)N1—C15—C16—O4179.5 (2)
Cu1—O3—C2—C3114.6 (1)N1—C15—C16—C170.9 (4)
Cu1—O3—C2—C16.8 (1)O4—C16—C17—C18179.6 (4)
O2—C1—C2—O3168.3 (1)C15—C16—C17—C181.0 (6)
O1—C1—C2—O314.9 (2)C16—C17—C18—C191.2 (7)
O2—C1—C2—C1444.1 (2)C15—N1—C19—C181.1 (5)
O1—C1—C2—C14139.1 (1)C19'—N1—C19—C1857 (6)
O2—C1—C2—C367.6 (2)C15'—N1—C19—C1819.9 (5)
O1—C1—C2—C3109.2 (1)Cu1—N1—C19—C18176.7 (3)
O3—C2—C3—C460.9 (2)C17—C18—C19—N11.2 (7)
C14—C2—C3—C4178.5 (2)C15—N1—C15'—C16'81 (2)
C1—C2—C3—C460.0 (2)C19'—N1—C15'—C16'0.4 (4)
O3—C2—C3—C8119.6 (1)C19—N1—C15'—C16'12.8 (6)
C14—C2—C3—C81.1 (2)Cu1—N1—C15'—C16'176.4 (3)
C1—C2—C3—C8119.5 (1)N1—C15'—C16'—O4'179.5 (3)
C8—C3—C4—C51.5 (2)N1—C15'—C16'—C17'0.9 (5)
C2—C3—C4—C5179.0 (2)O4'—C16'—C17'—C18'179.5 (5)
C3—C4—C5—C60.1 (3)C15'—C16'—C17'—C18'0.8 (7)
C4—C5—C6—C70.9 (3)C16'—C17'—C18'—C19'0.2 (8)
C5—C6—C7—C80.2 (3)C15—N1—C19'—C18'19.9 (6)
C6—C7—C8—C31.3 (2)C19—N1—C19'—C18'109 (6)
C6—C7—C8—C9179.2 (2)C15'—N1—C19'—C18'0.3 (6)
C4—C3—C8—C72.2 (2)Cu1—N1—C19'—C18'175.5 (5)
C2—C3—C8—C7178.2 (1)C17'—C18'—C19'—N10.4 (9)
C4—C3—C8—C9178.3 (1)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3o···O50.822.022.677 (2)137
O5—H5o···O2ii0.821.962.773 (2)170
O4—H4o···O2ii0.821.912.702 (4)162
O4—H4o···O1ii0.822.042.838 (6)166
Symmetry code: (ii) x, y1, z.
 

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