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The 3-carboxy­phenoxy­acetate ligand in the title compound, [Cu(C9H6O5)(C5H5N)3]·3H2O, links adjacent tripyridine­copper(II) groups into a helical chain, which runs along the c axis of the hexa­gonal unit cell. The covalently bonded O atoms occupy trans sites in the basal plane of the square-pyramidal coordination of the Cu atom. The uncoordinated water mol­ecules connect the chains into a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805038316/xu6084sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805038316/xu6084Isup2.hkl
Contains datablock I

CCDC reference: 294037

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.073
  • wR factor = 0.146
  • Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT420_ALERT_2_B D-H Without Acceptor O3W - H3W2 ... ?
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.591 0.849 Tmin(prime) and Tmax expected: 0.714 0.844 RR(prime) = 0.823 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 ............. 0.82 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.61 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O2 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O3 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C8 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 6
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 5518 Count of symmetry unique reflns 3052 Completeness (_total/calc) 180.80% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2466 Fraction of Friedel pairs measured 0.808 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 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 3 ALERT type 3 Indicator that the structure quality may be low 2 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.

catena-Poly[[[tris(pyridine-κN)copper(II)]-µ-3-carboxylatophenoxyacetato- κ2O3:O'] trihydrate] top
Crystal data top
[Cu(C9H6O5)(C5H5N)3]·3H2ODx = 1.407 Mg m3
Mr = 549.04Mo Kα radiation, λ = 0.71073 Å
Hexagonal, P65Cell parameters from 26385 reflections
Hall symbol: P 65θ = 3.3–27.5°
a = 14.408 (2) ŵ = 0.89 mm1
c = 21.630 (4) ÅT = 295 K
V = 3888.6 (8) Å3Block, blue
Z = 60.37 × 0.25 × 0.19 mm
F(000) = 1710
Data collection top
Rigaku R-AXIS RAPID IP
diffractometer
5518 independent reflections
Radiation source: fine-focus sealed tube4814 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
ω scansθmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1818
Tmin = 0.591, Tmax = 0.849k = 1818
27636 measured reflectionsl = 2826
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)] = 0.073H-atom parameters constrained
wR(F2) = 0.146 w = 1/[σ2(Fo2) + (0.0697P)2 + 0.7075P]
where P = (Fo2 + 2Fc2)/3
S = 1.24(Δ/σ)max = 0.03
5518 reflectionsΔρmax = 0.48 e Å3
325 parametersΔρmin = 0.39 e Å3
19 restraintsAbsolute structure: Flack (1983), 2571 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.05 (2)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.49488 (4)0.00056 (4)0.50004 (5)0.0515 (2)
O10.3917 (3)0.0023 (3)0.5596 (2)0.061 (1)
O20.5016 (2)0.0021 (3)0.6330 (2)0.066 (1)
O30.3345 (2)0.0087 (3)0.8301 (2)0.074 (1)
O40.2685 (3)0.0082 (3)0.9884 (2)0.068 (1)
O50.4064 (2)0.0022 (3)0.9377 (1)0.057 (1)
O1W0.6947 (5)0.0025 (6)0.6174 (3)0.140 (2)
O2W0.8857 (6)0.0568 (5)0.6762 (3)0.153 (2)
O3w0.9723 (9)0.0003 (8)0.7682 (7)0.224 (5)
N10.4281 (3)0.1623 (3)0.5108 (2)0.056 (1)
N20.3847 (3)0.0051 (3)0.4194 (2)0.061 (1)
N30.5853 (3)0.1641 (3)0.5095 (2)0.053 (1)
C10.4879 (4)0.2089 (4)0.5137 (2)0.068 (1)
C20.4450 (5)0.3187 (5)0.5173 (3)0.080 (2)
C30.3375 (6)0.3827 (5)0.5187 (3)0.088 (2)
C40.2742 (5)0.3359 (5)0.5161 (3)0.086 (2)
C50.3231 (4)0.2256 (5)0.5123 (2)0.072 (1)
C60.2907 (5)0.0092 (6)0.4291 (3)0.088 (2)
C70.2264 (6)0.0115 (7)0.3827 (5)0.114 (3)
C80.2566 (8)0.0110 (7)0.3230 (4)0.119 (3)
C90.3535 (6)0.0069 (5)0.3111 (3)0.092 (2)
C100.4121 (5)0.0044 (4)0.3609 (2)0.070 (1)
C110.5377 (4)0.2232 (4)0.5104 (2)0.064 (1)
C120.5962 (4)0.3341 (4)0.5150 (3)0.071 (1)
C130.7045 (5)0.3843 (4)0.5193 (2)0.069 (1)
C140.7541 (4)0.3228 (5)0.5190 (2)0.070 (1)
C150.6908 (4)0.2136 (4)0.5139 (2)0.059 (1)
C160.4187 (4)0.0019 (3)0.6157 (2)0.049 (1)
C170.3398 (3)0.0076 (3)0.6637 (2)0.045 (1)
C180.2378 (3)0.0280 (3)0.6474 (2)0.052 (1)
C190.1669 (4)0.0353 (4)0.6931 (2)0.054 (1)
C200.1953 (3)0.0227 (3)0.7550 (2)0.052 (1)
C210.2973 (3)0.0039 (3)0.7704 (2)0.050 (1)
C220.3678 (3)0.0041 (4)0.7254 (2)0.050 (1)
C230.2649 (4)0.0051 (4)0.8796 (2)0.059 (1)
C240.3179 (4)0.0046 (4)0.9400 (2)0.053 (1)
H1W10.62810.03740.62480.168*
H1W20.70830.00990.58090.168*
H2W10.93570.09790.65140.183*
H2w20.83830.00300.65550.183*
H3w10.95040.01790.73570.269*
H3w20.99920.04060.75480.269*
H10.56210.16540.51340.081*
H20.48970.34810.51870.096*
H30.30670.45670.52130.106*
H40.19990.37790.51700.104*
H50.28000.19450.51060.087*
H60.26860.01060.46970.106*
H70.16230.01330.39150.136*
H80.21310.01330.29060.142*
H90.37700.00590.27090.110*
H100.47680.00200.35330.083*
H110.46340.18920.50790.077*
H120.56130.37370.51520.085*
H130.74490.45850.52240.083*
H140.82820.35470.52210.084*
H150.72390.17230.51360.071*
H180.21730.03660.60610.062*
H190.09890.04900.68190.065*
H200.14780.02660.78530.063*
H220.43580.01770.73670.059*
H23a0.19840.07250.87490.071*
H23b0.24830.05230.87940.071*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0544 (3)0.0654 (3)0.0384 (2)0.0328 (3)0.0004 (2)0.0032 (2)
O10.066 (2)0.077 (2)0.044 (2)0.039 (2)0.006 (1)0.002 (1)
O20.055 (2)0.083 (2)0.062 (2)0.036 (2)0.002 (1)0.001 (2)
O30.047 (2)0.129 (3)0.037 (2)0.037 (2)0.002 (1)0.002 (2)
O40.074 (2)0.100 (3)0.041 (2)0.050 (2)0.011 (2)0.010 (2)
O50.055 (2)0.080 (2)0.040 (2)0.036 (2)0.001 (1)0.003 (1)
O1w0.130 (4)0.255 (7)0.086 (3)0.135 (5)0.023 (3)0.036 (4)
O2w0.164 (5)0.116 (4)0.162 (5)0.058 (4)0.028 (4)0.020 (4)
O3w0.232 (7)0.226 (7)0.25 (1)0.144 (6)0.026 (6)0.009 (5)
N10.058 (2)0.067 (2)0.047 (2)0.033 (2)0.001 (2)0.005 (2)
N20.060 (2)0.070 (2)0.053 (2)0.033 (2)0.014 (2)0.008 (2)
N30.057 (2)0.067 (2)0.041 (2)0.035 (2)0.003 (2)0.002 (2)
C10.066 (3)0.071 (3)0.065 (3)0.034 (3)0.007 (2)0.005 (2)
C20.097 (4)0.087 (4)0.072 (4)0.058 (4)0.012 (3)0.008 (3)
C30.115 (5)0.067 (4)0.078 (4)0.042 (4)0.004 (3)0.001 (3)
C40.076 (4)0.070 (4)0.094 (5)0.022 (3)0.003 (3)0.002 (3)
C50.067 (3)0.081 (4)0.068 (3)0.037 (3)0.001 (2)0.008 (3)
C60.074 (4)0.121 (5)0.084 (4)0.059 (4)0.013 (3)0.011 (4)
C70.082 (4)0.141 (7)0.137 (7)0.071 (5)0.039 (5)0.018 (5)
C80.147 (7)0.137 (6)0.091 (5)0.085 (6)0.064 (5)0.032 (5)
C90.124 (5)0.110 (5)0.066 (4)0.078 (4)0.030 (4)0.015 (3)
C100.088 (4)0.064 (3)0.062 (3)0.042 (3)0.017 (3)0.006 (2)
C110.059 (3)0.080 (3)0.060 (3)0.039 (3)0.005 (2)0.001 (2)
C120.078 (3)0.075 (3)0.078 (4)0.052 (3)0.007 (3)0.002 (3)
C130.073 (3)0.061 (3)0.069 (3)0.032 (3)0.002 (2)0.003 (2)
C140.058 (3)0.079 (4)0.072 (3)0.034 (3)0.007 (2)0.002 (3)
C150.062 (3)0.062 (3)0.064 (3)0.039 (2)0.011 (2)0.003 (2)
C160.052 (3)0.048 (2)0.045 (2)0.024 (2)0.006 (2)0.002 (2)
C170.046 (2)0.041 (2)0.046 (2)0.019 (2)0.001 (2)0.001 (2)
C180.052 (2)0.056 (2)0.040 (2)0.022 (2)0.009 (2)0.000 (2)
C190.043 (2)0.071 (3)0.049 (2)0.029 (2)0.006 (2)0.001 (2)
C200.044 (2)0.058 (2)0.048 (2)0.021 (2)0.006 (2)0.009 (2)
C210.048 (2)0.058 (2)0.039 (2)0.023 (2)0.002 (2)0.005 (2)
C220.037 (2)0.063 (3)0.048 (2)0.025 (2)0.003 (2)0.003 (2)
C230.046 (2)0.084 (3)0.045 (2)0.031 (2)0.003 (2)0.003 (2)
C240.057 (3)0.059 (3)0.041 (2)0.028 (2)0.004 (2)0.003 (2)
Geometric parameters (Å, º) top
Cu1—O11.952 (3)C18—C191.386 (6)
Cu1—O5i1.951 (3)C19—C201.384 (6)
Cu1—N12.057 (4)C20—C211.395 (6)
Cu1—N22.332 (4)C21—C221.369 (6)
Cu1—N32.055 (4)C23—C241.512 (7)
O1—C161.274 (5)O1w—H1w10.85
O2—C161.224 (5)O1w—H1w20.85
O3—C211.375 (5)O2w—H2w10.86
O3—C231.411 (6)O2w—H2w20.86
O4—C241.252 (5)O3w—H3w10.86
O5—C241.259 (5)O3w—H3w20.89
N1—C51.320 (7)C1—H10.93
N1—C11.331 (6)C2—H20.93
N2—C101.324 (7)C3—H30.93
N2—C61.343 (7)C4—H40.93
N3—C151.321 (6)C5—H50.93
N3—C111.334 (6)C6—H60.93
C1—C21.384 (8)C7—H70.93
C2—C31.350 (10)C8—H80.93
C3—C41.379 (9)C9—H90.93
C4—C51.382 (8)C10—H100.93
C6—C71.356 (10)C11—H110.93
C7—C81.362 (13)C12—H120.93
C8—C91.392 (12)C13—H130.93
C9—C101.359 (8)C14—H140.93
C11—C121.388 (8)C15—H150.93
C12—C131.356 (8)C18—H180.93
C13—C141.389 (8)C19—H190.93
C14—C151.372 (7)C20—H200.93
C16—C171.511 (6)C22—H220.93
C17—C221.380 (6)C23—H23a0.97
C17—C181.393 (6)C23—H23b0.97
O1—Cu1—O5i177.5 (2)C22—C21—C20120.8 (4)
O1—Cu1—N189.1 (2)O3—C21—C20123.6 (4)
O1—Cu1—N289.7 (1)C21—C22—C17121.1 (4)
O1—Cu1—N389.9 (1)C21—C22—H22119.4
O5i—Cu1—N190.8 (1)C17—C22—H22119.4
O5i—Cu1—N287.9 (2)O3—C23—C24109.5 (4)
O5i—Cu1—N390.8 (1)O4—C24—O5125.5 (4)
N1—Cu1—N297.1 (2)O4—C24—C23116.5 (4)
N1—Cu1—N3164.6 (2)O5—C24—C23117.9 (4)
N2—Cu1—N398.3 (1)N1—C1—H1118.4
C16—O1—Cu1113.7 (3)C2—C1—H1118.4
C21—O3—C23119.4 (3)C3—C2—H2120.5
C24—O5—Cu1ii134.0 (3)C1—C2—H2120.5
H1w1—O1w—H1w2109.3C2—C3—H3120.7
H2w1—O2w—H2w2108.2C4—C3—H3120.7
H3w1—O3w—H3w2106.2C5—C4—H4120.6
C5—N1—C1117.2 (5)C3—C4—H4120.6
C5—N1—Cu1120.7 (4)N1—C5—H5118.5
C1—N1—Cu1121.9 (3)C4—C5—H5118.5
C10—N2—C6116.2 (5)N2—C6—H6118.4
C10—N2—Cu1121.2 (3)C7—C6—H6118.4
C6—N2—Cu1122.6 (4)C6—C7—H7120.3
C15—N3—C11118.3 (4)C8—C7—H7120.3
C15—N3—Cu1121.7 (3)C7—C8—H8120.4
C11—N3—Cu1120.0 (3)C9—C8—H8120.4
N1—C1—C2123.2 (5)C10—C9—H9121.6
C3—C2—C1119.0 (6)C8—C9—H9121.6
C2—C3—C4118.6 (6)N2—C10—H10117.3
C5—C4—C3118.9 (6)C9—C10—H10117.3
N1—C5—C4123.0 (6)N3—C11—H11119.2
N2—C6—C7123.1 (7)C12—C11—H11119.2
C6—C7—C8119.4 (7)C13—C12—H12120.2
C7—C8—C9119.1 (6)C11—C12—H12120.2
C10—C9—C8116.8 (7)C12—C13—H13120.6
N2—C10—C9125.3 (6)C14—C13—H13120.6
N3—C11—C12121.7 (5)C15—C14—H14120.9
C13—C12—C11119.6 (5)C13—C14—H14120.9
C12—C13—C14118.8 (5)N3—C15—H15118.3
C15—C14—C13118.2 (5)C14—C15—H15118.3
N3—C15—C14123.4 (4)C19—C18—H18120.2
O2—C16—O1125.4 (4)C17—C18—H18120.2
O2—C16—C17118.9 (4)C20—C19—H19119.3
O1—C16—C17115.8 (4)C18—C19—H19119.3
C22—C17—C18118.9 (4)C19—C20—H20121.0
C22—C17—C16119.4 (4)C21—C20—H20121.0
C18—C17—C16121.6 (4)O3—C23—H23a109.8
C19—C18—C17119.7 (4)C24—C23—H23a109.8
C20—C19—C18121.4 (4)O3—C23—H23b109.8
C19—C20—C21118.0 (4)C24—C23—H23b109.8
C22—C21—O3115.6 (4)H23a—C23—H23b108.2
N3—Cu1—O1—C1682.7 (3)N2—C6—C7—C80.9 (12)
N1—Cu1—O1—C1682.0 (3)C6—C7—C8—C90.7 (13)
N2—Cu1—O1—C16179.0 (3)C7—C8—C9—C100.4 (11)
O5i—Cu1—N1—C5133.8 (4)C6—N2—C10—C90.3 (8)
O1—Cu1—N1—C543.8 (4)Cu1—N2—C10—C9179.6 (5)
N3—Cu1—N1—C5130.1 (5)C8—C9—C10—N20.3 (10)
N2—Cu1—N1—C545.8 (4)C15—N3—C11—C120.9 (7)
O5i—Cu1—N1—C143.2 (4)Cu1—N3—C11—C12178.2 (4)
O1—Cu1—N1—C1139.3 (4)N3—C11—C12—C130.6 (8)
N3—Cu1—N1—C152.9 (7)C11—C12—C13—C140.0 (8)
N2—Cu1—N1—C1131.1 (4)C12—C13—C14—C150.4 (8)
O5i—Cu1—N2—C100.8 (4)C11—N3—C15—C140.5 (7)
O1—Cu1—N2—C10179.5 (4)Cu1—N3—C15—C14178.6 (4)
N3—Cu1—N2—C1089.7 (4)C13—C14—C15—N30.2 (8)
N1—Cu1—N2—C1091.4 (4)Cu1—O1—C16—O21.4 (5)
O5i—Cu1—N2—C6179.2 (5)Cu1—O1—C16—C17178.1 (2)
O1—Cu1—N2—C60.4 (4)O2—C16—C17—C227.4 (6)
N3—Cu1—N2—C690.3 (4)O1—C16—C17—C22173.0 (4)
N1—Cu1—N2—C688.6 (4)O2—C16—C17—C18170.5 (4)
O5i—Cu1—N3—C1545.3 (3)O1—C16—C17—C189.1 (6)
O1—Cu1—N3—C15137.1 (3)C22—C17—C18—C190.4 (6)
N1—Cu1—N3—C1550.8 (7)C16—C17—C18—C19178.4 (4)
N2—Cu1—N3—C15133.2 (3)C17—C18—C19—C200.1 (7)
O5i—Cu1—N3—C11133.8 (3)C18—C19—C20—C211.0 (7)
O1—Cu1—N3—C1143.8 (4)C23—O3—C21—C22176.0 (5)
N1—Cu1—N3—C11130.1 (5)C23—O3—C21—C204.6 (7)
N2—Cu1—N3—C1145.8 (4)C19—C20—C21—C221.4 (6)
C5—N1—C1—C21.0 (8)C19—C20—C21—O3179.2 (4)
Cu1—N1—C1—C2176.0 (4)O3—C21—C22—C17179.6 (4)
N1—C1—C2—C30.9 (9)C20—C21—C22—C170.9 (7)
C1—C2—C3—C40.4 (9)C18—C17—C22—C210.0 (6)
C2—C3—C4—C50.0 (10)C16—C17—C22—C21178.0 (4)
C1—N1—C5—C40.6 (8)C21—O3—C23—C24171.1 (4)
Cu1—N1—C5—C4176.5 (5)Cu1ii—O5—C24—O41.1 (7)
C3—C4—C5—N10.1 (9)Cu1ii—O5—C24—C23180.0 (3)
C10—N2—C6—C70.6 (9)O3—C23—C24—O4174.9 (4)
Cu1—N2—C6—C7179.3 (6)O3—C23—C24—O56.1 (6)
Symmetry codes: (i) x+1, y, z1/2; (ii) x+1, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1w—H1w1···O20.852.172.800 (6)131
O1w—H1w2···O4i0.852.032.835 (6)158
O2w—H2w1···O4iii0.862.252.789 (7)121
O2w—H2w2···O1w0.862.222.766 (8)121
O3w—H3w1···O2w0.861.832.69 (1)170
Symmetry codes: (i) x+1, y, z1/2; (iii) y+1, xy, z1/3.
 

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