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In the title compound, [Cu(C8H5O5)Cl(C12H8N2)(H2O)]·2.5H2O, the CuII atom is in a square-pyramidal geometry defined by one Cl anion, one aqua O atom, one carbox­yl O atom belonging to one 5-hydroxy­isophthalate anion, and two N atoms from a 1,10-phenanthroline mol­ecule. O—H...O hydrogen bonds involving 5-hydroxy­isophthalate anions, the aqua ligands and the uncoordinated water mol­ecules, along with weak O—H...Cl hydrogen bonds, link the mononuclear units into a three-dimensional network structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805009724/su6185sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805009724/su6185Isup2.hkl
Contains datablock I

CCDC reference: 272119

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.006 Å
  • H-atom completeness 96%
  • Disorder in solvent or counterion
  • R factor = 0.050
  • wR factor = 0.156
  • Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C 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 PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ? PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.68 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 17.00 Perc. PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1 .. O9 .. 3.14 Ang.
Alert level G FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C20 H20 Cl1 Cu1 N2 O8.5 Atom count from the _atom_site data: C20 H19 Cl1 Cu1 N2 O8.5 CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected. CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional? From the CIF: _cell_formula_units_Z 2 From the CIF: _chemical_formula_sum C20 H20 Cl Cu N2 O8.5 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 40.00 40.00 0.00 H 40.00 38.00 2.00 Cl 2.00 2.00 0.00 Cu 2.00 2.00 0.00 N 4.00 4.00 0.00 O 17.00 17.00 0.00
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 6 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

Computing details top

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

Aquachloro[5-hydroxyisophthalato(1-)](1,10-phenanthroline)copper(II) 2.5-hydrate top
Crystal data top
[Cu(C8H5O5)Cl(C12H8N2)(H2O)]·2.5H2OZ = 2
Mr = 523.37F(000) = 536
Triclinic, P1Dx = 1.590 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.8508 (10) ÅCell parameters from 2931 reflections
b = 10.7516 (12) Åθ = 2.3–24.4°
c = 12.7592 (15) ŵ = 1.17 mm1
α = 114.218 (2)°T = 298 K
β = 95.770 (2)°Prism, blue
γ = 94.022 (2)°0.33 × 0.15 × 0.13 mm
V = 1093.4 (2) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
3911 independent reflections
Radiation source: fine-focus sealed tube3445 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
φ and ω scansθmax = 25.2°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 1010
Tmin = 0.810, Tmax = 0.862k = 1212
8038 measured reflectionsl = 1515
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156H atoms treated by a mixture of independent and constrained refinement
S = 1.13 w = 1/[σ2(Fo2) + (0.0785P)2 + 1.351P]
where P = (Fo2 + 2Fc2)/3
3911 reflections(Δ/σ)max < 0.001
313 parametersΔρmax = 1.28 e Å3
8 restraintsΔρmin = 0.48 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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*/UeqOcc. (<1)
Cu10.94701 (6)0.88662 (5)0.27984 (4)0.0333 (2)
Cl10.71061 (13)0.81084 (12)0.12694 (9)0.0453 (3)
O10.8466 (3)1.0061 (3)0.4076 (2)0.0381 (9)
O20.8222 (4)1.1817 (3)0.3593 (3)0.0441 (11)
O30.5900 (4)1.5828 (3)0.6309 (3)0.0504 (11)
O40.4699 (4)1.5535 (3)0.7659 (3)0.0513 (11)
O50.5235 (4)1.0742 (3)0.7163 (3)0.0433 (11)
O61.0255 (4)1.0405 (3)0.2450 (3)0.0465 (11)
N11.0769 (4)0.7580 (3)0.1751 (3)0.0343 (10)
N20.9214 (4)0.7356 (3)0.3333 (3)0.0316 (10)
C11.1576 (5)0.7746 (5)0.0982 (4)0.0438 (16)
C21.2382 (6)0.6717 (5)0.0289 (4)0.0483 (16)
C31.2338 (5)0.5497 (5)0.0374 (4)0.0449 (16)
C41.1475 (5)0.5275 (4)0.1163 (4)0.0362 (12)
C51.1344 (5)0.4027 (4)0.1335 (4)0.0431 (14)
C61.0536 (5)0.3911 (4)0.2119 (4)0.0437 (16)
C70.9789 (5)0.5027 (4)0.2857 (4)0.0357 (12)
C80.8968 (5)0.4998 (4)0.3735 (4)0.0400 (14)
C90.8330 (5)0.6126 (5)0.4384 (4)0.0426 (14)
C100.8470 (5)0.7303 (4)0.4165 (4)0.0361 (12)
C110.9878 (4)0.6238 (4)0.2693 (3)0.0304 (11)
C121.0726 (4)0.6367 (4)0.1839 (3)0.0306 (12)
C130.7970 (5)1.1183 (4)0.4205 (3)0.0321 (11)
C140.7030 (4)1.1791 (4)0.5174 (3)0.0306 (11)
C150.6647 (4)1.3110 (4)0.5493 (3)0.0320 (12)
C160.5796 (4)1.3663 (4)0.6400 (4)0.0322 (11)
C170.5296 (4)1.2880 (4)0.6971 (4)0.0338 (12)
C180.5679 (4)1.1562 (4)0.6636 (3)0.0322 (12)
C190.6560 (5)1.1026 (4)0.5756 (3)0.0330 (12)
C200.5481 (5)1.5121 (4)0.6773 (4)0.0365 (12)
O70.6859 (4)0.8519 (4)0.6776 (5)0.0858 (19)
O80.3877 (6)0.7989 (4)0.8158 (4)0.0815 (19)
O90.3090 (15)0.0112 (8)0.0159 (7)0.097 (4)0.500
H11.160400.857000.090500.0520*
H21.295000.686800.023200.0580*
H31.287600.481200.008600.0540*
H40.458401.634600.785100.0770*
H50.465901.112600.762800.0650*
H5A1.183400.329300.088800.0510*
H61.045100.308500.219400.0530*
H6A0.981701.107700.278400.0700*
H6B1.116801.087800.278300.0700*
H80.886200.421200.387100.0480*
H90.780000.612000.497500.0510*
H100.802600.806700.461700.0430*
H150.695801.362600.510200.0390*
H170.471201.324200.756900.0410*
H190.683901.014800.555400.0390*
H7A0.656 (5)0.775 (3)0.675 (5)0.0540*
H7B0.621 (4)0.905 (4)0.682 (5)0.0540*
H8A0.339 (5)0.794 (5)0.756 (2)0.0540*
H8B0.372 (6)0.849 (5)0.8802 (19)0.0540*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0409 (3)0.0250 (3)0.0390 (3)0.0099 (2)0.0165 (2)0.0151 (2)
Cl10.0472 (6)0.0468 (6)0.0403 (6)0.0129 (5)0.0144 (5)0.0138 (5)
O10.0536 (18)0.0276 (15)0.0397 (16)0.0145 (13)0.0190 (14)0.0166 (13)
O20.059 (2)0.0340 (16)0.0525 (19)0.0175 (14)0.0257 (16)0.0255 (15)
O30.075 (2)0.0291 (16)0.054 (2)0.0148 (15)0.0217 (17)0.0203 (15)
O40.069 (2)0.0313 (17)0.059 (2)0.0224 (16)0.0286 (17)0.0174 (16)
O50.0533 (19)0.0332 (16)0.055 (2)0.0164 (14)0.0281 (15)0.0238 (15)
O60.0532 (19)0.0305 (16)0.065 (2)0.0114 (14)0.0282 (16)0.0239 (15)
N10.0366 (18)0.0308 (18)0.0358 (18)0.0076 (14)0.0096 (15)0.0128 (15)
N20.0358 (18)0.0268 (17)0.0347 (18)0.0076 (14)0.0096 (15)0.0137 (14)
C10.053 (3)0.040 (2)0.044 (3)0.007 (2)0.016 (2)0.021 (2)
C20.053 (3)0.053 (3)0.040 (2)0.011 (2)0.020 (2)0.017 (2)
C30.047 (3)0.043 (3)0.040 (2)0.016 (2)0.016 (2)0.009 (2)
C40.035 (2)0.034 (2)0.033 (2)0.0075 (17)0.0054 (17)0.0070 (18)
C50.048 (3)0.031 (2)0.044 (2)0.0157 (19)0.010 (2)0.0070 (19)
C60.055 (3)0.026 (2)0.049 (3)0.0108 (19)0.006 (2)0.014 (2)
C70.037 (2)0.026 (2)0.040 (2)0.0049 (17)0.0016 (18)0.0106 (17)
C80.051 (3)0.030 (2)0.044 (2)0.0029 (19)0.006 (2)0.021 (2)
C90.050 (3)0.040 (2)0.044 (2)0.006 (2)0.015 (2)0.022 (2)
C100.042 (2)0.032 (2)0.037 (2)0.0102 (18)0.0128 (18)0.0146 (18)
C110.032 (2)0.0250 (19)0.031 (2)0.0048 (16)0.0020 (16)0.0090 (16)
C120.032 (2)0.028 (2)0.031 (2)0.0035 (16)0.0031 (16)0.0120 (17)
C130.037 (2)0.0226 (19)0.035 (2)0.0061 (16)0.0084 (17)0.0092 (17)
C140.033 (2)0.0233 (19)0.033 (2)0.0043 (16)0.0039 (16)0.0095 (16)
C150.037 (2)0.026 (2)0.034 (2)0.0038 (16)0.0059 (17)0.0133 (17)
C160.034 (2)0.0229 (19)0.038 (2)0.0052 (16)0.0050 (17)0.0108 (17)
C170.033 (2)0.029 (2)0.037 (2)0.0070 (17)0.0109 (17)0.0098 (18)
C180.034 (2)0.028 (2)0.037 (2)0.0045 (16)0.0088 (17)0.0150 (18)
C190.036 (2)0.025 (2)0.038 (2)0.0067 (16)0.0078 (17)0.0123 (17)
C200.040 (2)0.027 (2)0.038 (2)0.0083 (17)0.0063 (18)0.0083 (18)
O70.055 (2)0.038 (2)0.171 (5)0.0106 (18)0.024 (3)0.048 (3)
O80.122 (4)0.058 (3)0.061 (3)0.045 (3)0.009 (3)0.017 (2)
O90.214 (11)0.044 (4)0.049 (5)0.031 (6)0.044 (6)0.027 (4)
Geometric parameters (Å, º) top
Cu1—Cl12.5463 (12)C5—C61.327 (6)
Cu1—O11.957 (3)C6—C71.440 (7)
Cu1—O61.980 (4)C7—C81.405 (6)
Cu1—N12.009 (4)C7—C111.399 (7)
Cu1—N22.010 (4)C8—C91.357 (7)
O1—C131.265 (6)C9—C101.404 (7)
O2—C131.255 (6)C11—C121.430 (5)
O3—C201.200 (6)C13—C141.506 (5)
O4—C201.320 (6)C14—C191.384 (6)
O5—C181.369 (6)C14—C151.383 (6)
O4—H40.8200C15—C161.391 (5)
O5—H50.8200C16—C201.496 (7)
O6—H6A0.8200C16—C171.397 (7)
O6—H6B0.8900C17—C181.380 (6)
O7—H7A0.84 (4)C18—C191.382 (5)
O7—H7B0.83 (4)C1—H10.9300
O8—H8B0.81 (3)C2—H20.9300
O8—H8A0.82 (3)C3—H30.9300
N1—C11.331 (6)C5—H5A0.9300
N1—C121.352 (6)C6—H60.9300
N2—C101.322 (6)C8—H80.9300
N2—C111.359 (5)C9—H90.9300
C1—C21.396 (7)C10—H100.9300
C2—C31.358 (8)C15—H150.9300
C3—C41.407 (7)C17—H170.9300
C4—C51.445 (7)C19—H190.9300
C4—C121.398 (6)
Cl1—Cu1—O195.62 (8)N1—C12—C4123.7 (4)
Cl1—Cu1—O694.93 (11)C4—C12—C11119.8 (4)
Cl1—Cu1—N194.68 (10)O1—C13—C14116.8 (4)
Cl1—Cu1—N298.51 (11)O2—C13—C14118.6 (4)
O1—Cu1—O692.98 (14)O1—C13—O2124.5 (4)
O1—Cu1—N1167.95 (13)C13—C14—C19119.6 (4)
O1—Cu1—N290.42 (14)C15—C14—C19119.9 (3)
O6—Cu1—N192.33 (15)C13—C14—C15120.5 (4)
O6—Cu1—N2165.74 (15)C14—C15—C16119.8 (4)
N1—Cu1—N281.89 (14)C15—C16—C17120.3 (4)
Cu1—O1—C13127.8 (3)C17—C16—C20121.1 (4)
C20—O4—H4109.00C15—C16—C20118.6 (4)
C18—O5—H5109.00C16—C17—C18119.2 (4)
Cu1—O6—H6B121.00C17—C18—C19120.6 (4)
H6A—O6—H6B92.00O5—C18—C19117.2 (4)
Cu1—O6—H6A109.00O5—C18—C17122.2 (3)
H7A—O7—H7B117 (4)C14—C19—C18120.3 (4)
H8A—O8—H8B124 (5)O4—C20—C16112.8 (4)
Cu1—N1—C12112.6 (3)O3—C20—C16123.0 (4)
C1—N1—C12118.2 (4)O3—C20—O4124.2 (4)
Cu1—N1—C1129.2 (3)C2—C1—H1119.00
C10—N2—C11118.3 (4)N1—C1—H1119.00
Cu1—N2—C11112.4 (3)C3—C2—H2120.00
Cu1—N2—C10129.3 (3)C1—C2—H2120.00
N1—C1—C2121.8 (5)C2—C3—H3120.00
C1—C2—C3120.2 (5)C4—C3—H3120.00
C2—C3—C4119.7 (5)C4—C5—H5A119.00
C3—C4—C5124.8 (4)C6—C5—H5A120.00
C5—C4—C12118.6 (4)C5—C6—H6119.00
C3—C4—C12116.5 (4)C7—C6—H6119.00
C4—C5—C6121.1 (4)C9—C8—H8120.00
C5—C6—C7121.9 (4)C7—C8—H8120.00
C6—C7—C8125.1 (4)C8—C9—H9120.00
C6—C7—C11118.0 (4)C10—C9—H9120.00
C8—C7—C11117.0 (4)N2—C10—H10119.00
C7—C8—C9119.5 (5)C9—C10—H10119.00
C8—C9—C10120.1 (4)C16—C15—H15120.00
N2—C10—C9121.9 (4)C14—C15—H15120.00
N2—C11—C12116.2 (4)C16—C17—H17120.00
N2—C11—C7123.3 (4)C18—C17—H17120.00
C7—C11—C12120.6 (4)C18—C19—H19120.00
N1—C12—C11116.6 (4)C14—C19—H19120.00
Cl1—Cu1—O1—C1368.5 (3)C3—C4—C12—C11177.5 (4)
O6—Cu1—O1—C1326.8 (3)C5—C4—C12—C111.2 (6)
N2—Cu1—O1—C13167.1 (3)C4—C5—C6—C71.8 (7)
Cl1—Cu1—N1—C184.2 (4)C5—C6—C7—C112.8 (7)
Cl1—Cu1—N1—C1292.8 (3)C5—C6—C7—C8177.3 (5)
O6—Cu1—N1—C111.0 (4)C6—C7—C8—C9179.2 (4)
O6—Cu1—N1—C12172.1 (3)C6—C7—C11—N2179.7 (4)
N2—Cu1—N1—C1177.9 (4)C6—C7—C11—C121.8 (6)
N2—Cu1—N1—C125.2 (3)C11—C7—C8—C91.0 (6)
Cl1—Cu1—N2—C1089.4 (4)C8—C7—C11—C12178.3 (4)
Cl1—Cu1—N2—C1188.1 (3)C8—C7—C11—N20.2 (6)
O1—Cu1—N2—C106.3 (4)C7—C8—C9—C101.0 (7)
O1—Cu1—N2—C11176.1 (3)C8—C9—C10—N20.1 (7)
N1—Cu1—N2—C10177.0 (4)N2—C11—C12—C4178.5 (4)
N1—Cu1—N2—C115.4 (3)C7—C11—C12—N1179.1 (4)
Cu1—O1—C13—O29.8 (6)N2—C11—C12—N10.5 (5)
Cu1—O1—C13—C14171.0 (2)C7—C11—C12—C40.1 (6)
Cu1—N1—C1—C2177.7 (3)O2—C13—C14—C19171.2 (4)
C1—N1—C12—C40.4 (6)O2—C13—C14—C159.5 (6)
C1—N1—C12—C11178.6 (4)O1—C13—C14—C15169.8 (3)
Cu1—N1—C12—C114.1 (4)O1—C13—C14—C199.6 (5)
C12—N1—C1—C20.9 (6)C13—C14—C15—C16179.1 (3)
Cu1—N1—C12—C4177.0 (3)C15—C14—C19—C181.5 (6)
C11—N2—C10—C91.2 (6)C19—C14—C15—C160.2 (5)
C10—N2—C11—C71.2 (6)C13—C14—C19—C18179.1 (3)
Cu1—N2—C11—C7176.6 (3)C14—C15—C16—C171.5 (6)
Cu1—N2—C11—C124.8 (4)C14—C15—C16—C20176.3 (4)
Cu1—N2—C10—C9176.3 (3)C20—C16—C17—C18176.7 (4)
C10—N2—C11—C12177.3 (4)C15—C16—C17—C181.1 (6)
N1—C1—C2—C31.1 (7)C17—C16—C20—O3179.5 (4)
C1—C2—C3—C40.1 (7)C15—C16—C20—O31.7 (7)
C2—C3—C4—C5179.8 (5)C15—C16—C20—O4178.3 (4)
C2—C3—C4—C121.2 (7)C17—C16—C20—O40.5 (6)
C12—C4—C5—C60.2 (7)C16—C17—C18—C190.7 (6)
C3—C4—C5—C6178.3 (5)C16—C17—C18—O5179.6 (4)
C5—C4—C12—N1179.9 (4)C17—C18—C19—C142.0 (6)
C3—C4—C12—N11.4 (6)O5—C18—C19—C14179.0 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O8i0.821.822.623 (6)167
O5—H5···Cl1ii0.822.182.998 (4)172
O6—H6A···O20.821.862.601 (5)149
O6—H6B···O7iii0.891.772.642 (5)167
O7—H7A···O3iv0.84 (4)1.93 (4)2.754 (6)167 (6)
O7—H7B···O50.83 (4)1.97 (5)2.771 (6)162 (4)
O8—H8A···O2ii0.82 (3)2.05 (4)2.844 (6)163 (4)
O8—H8B···O9v0.81 (3)2.05 (4)2.831 (10)162 (5)
C1—H1···O9vi0.932.573.371 (11)144
C8—H8···O2iv0.932.473.364 (6)162
C10—H10···O10.932.523.014 (6)113
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+2, z+1; (iii) x+2, y+2, z+1; (iv) x, y1, z; (v) x, y+1, z+1; (vi) x+1, y+1, z.
 

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