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The CuII atom in the title compound, [Cu(C7H4IO2)2(C10H8N2)(H2O)], is N,N′-chelated by a 2,2′-bipyridine ligand and is coordinated by two monodentate carboxyl­ate ions and a water mol­ecule in a distorted square-pyramidal geometry. The apical site is occupied by one of the carboxyl­ate O atoms. The water mol­ecule forms intra­molecular hydrogen bonds to the uncoordinated carboxyl O atoms. The crystal studied was a nonmerohedral twin with minor components in 0.381 (3) and 0.108 (2) proportions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810044995/xu5068sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536810044995/xu5068Isup2.hkl
Contains datablock I

CCDC reference: 802964

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.012 Å
  • R factor = 0.058
  • wR factor = 0.175
  • Data-to-parameter ratio = 18.4

checkCIF/PLATON results

No syntax errors found



Alert level A REFLT03_ALERT_3_A Reflection count > 15% excess reflns - sys abs data present? From the CIF: _diffrn_reflns_theta_max 25.13 From the CIF: _diffrn_reflns_theta_full 25.13 From the CIF: _reflns_number_total 5698 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 4374 Completeness (_total/calc) 130.27%
Author Response: The data were corrected for absorption by TWINABS, which corrects for the twin components simultaneously.
PLAT971_ALERT_2_A Large Calcd. Non-Metal Positive Residual Density       6.33 eA-3
Author Response: I think the alert is false alert.
PLAT971_ALERT_2_A Large Calcd. Non-Metal Positive Residual Density       6.06 eA-3
Author Response: I think the alert is false alert.
PLAT971_ALERT_2_A Large Calcd. Non-Metal Positive Residual Density       6.06 eA-3
Author Response: I think the alert is false alert.
PLAT971_ALERT_2_A Large Calcd. Non-Metal Positive Residual Density       6.04 eA-3
Author Response: I think the alert is false alert.
PLAT972_ALERT_2_A Large Calcd. Non-Metal Negative Residual Density     -20.83 eA-3
Author Response: I think the alert is false alert.
PLAT972_ALERT_2_A Large Calcd. Non-Metal Negative Residual Density     -20.01 eA-3
Author Response: I think the alert is false alert.
PLAT974_ALERT_2_A Large Calcd. Negative Residual Density on    Cu1     -14.31 eA-3
Author Response: I think the alert is false alert.
PLAT924_ALERT_1_A The Reported and Calculated Rho(min) Differ by .      19.14 eA-3
Author Response: I think the alert is false alert.
PLAT925_ALERT_1_A The Reported and Calculated Rho(max) Differ by .       4.62 eA-3
Author Response: I think the alert is false alert.
PLAT926_ALERT_1_A Reported and Calculated   R1 * 100.0 Differ by .     -18.39
Author Response: I think the alert is false alert.
PLAT927_ALERT_1_A Reported and Calculated  wR2 * 100.0 Differ by .     -43.99
Author Response: I think the alert is false alert.
PLAT928_ALERT_1_A Reported and Calculated    S value   Differ by .      -2.23
Author Response: I think the alert is false alert.

Alert level B PLAT972_ALERT_2_B Large Calcd. Non-Metal Negative Residual Density -3.11 eA-3
Author Response: I think the alert is false alert.
PLAT972_ALERT_2_B Large Calcd. Non-Metal Negative Residual Density      -3.07 eA-3
Author Response: I think the alert is false alert.
PLAT972_ALERT_2_B Large Calcd. Non-Metal Negative Residual Density      -2.93 eA-3
Author Response: I think the alert is false alert.
PLAT972_ALERT_2_B Large Calcd. Non-Metal Negative Residual Density      -2.77 eA-3
Author Response: I think the alert is false alert.
PLAT972_ALERT_2_B Large Calcd. Non-Metal Negative Residual Density      -2.65 eA-3
Author Response: I think the alert is false alert.
PLAT972_ALERT_2_B Large Calcd. Non-Metal Negative Residual Density      -2.59 eA-3
Author Response: I think the alert is false alert.
PLAT021_ALERT_1_B Ratio Unique / Expected Reflections too High ...       1.30

Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang .. 12 PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 1 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.598 96 PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density 2.49 eA-3
Author Response: I think the alert is false alert.
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density       2.47 eA-3
Author Response: I think the alert is false alert.
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density       2.33 eA-3
Author Response: I think the alert is false alert.
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density       2.27 eA-3
Author Response: I think the alert is false alert.
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density       2.15 eA-3
Author Response: I think the alert is false alert.
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density       1.84 eA-3
Author Response: I think the alert is false alert.
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density       1.80 eA-3
Author Response: I think the alert is false alert.
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density       1.78 eA-3
Author Response: I think the alert is false alert.
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density       1.75 eA-3
Author Response: I think the alert is false alert.
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density       1.66 eA-3
Author Response: I think the alert is false alert.
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density       1.66 eA-3
Author Response: I think the alert is false alert.
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density       1.59 eA-3
Author Response: I think the alert is false alert.
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density       1.58 eA-3
Author Response: I think the alert is false alert.
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density       1.58 eA-3
Author Response: I think the alert is false alert.
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density       1.57 eA-3
Author Response: I think the alert is false alert.
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density       1.57 eA-3
Author Response: I think the alert is false alert.
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density       1.55 eA-3
Author Response: I think the alert is false alert.
PLAT972_ALERT_2_C Large Calcd. Non-Metal Negative Residual Density      -2.36 eA-3
Author Response: I think the alert is false alert.
PLAT972_ALERT_2_C Large Calcd. Non-Metal Negative Residual Density      -2.28 eA-3
Author Response: I think the alert is false alert.
PLAT972_ALERT_2_C Large Calcd. Non-Metal Negative Residual Density      -2.19 eA-3
Author Response: I think the alert is false alert.
PLAT972_ALERT_2_C Large Calcd. Non-Metal Negative Residual Density      -2.19 eA-3
Author Response: I think the alert is false alert.
PLAT972_ALERT_2_C Large Calcd. Non-Metal Negative Residual Density      -2.18 eA-3
Author Response: I think the alert is false alert.
PLAT972_ALERT_2_C Large Calcd. Non-Metal Negative Residual Density      -2.17 eA-3
Author Response: I think the alert is false alert.
PLAT972_ALERT_2_C Large Calcd. Non-Metal Negative Residual Density      -2.17 eA-3
Author Response: I think the alert is false alert.
PLAT972_ALERT_2_C Large Calcd. Non-Metal Negative Residual Density      -2.12 eA-3
Author Response: I think the alert is false alert.
PLAT972_ALERT_2_C Large Calcd. Non-Metal Negative Residual Density      -2.03 eA-3
Author Response: I think the alert is false alert.
PLAT972_ALERT_2_C Large Calcd. Non-Metal Negative Residual Density      -2.01 eA-3
Author Response: I think the alert is false alert.
PLAT972_ALERT_2_C Large Calcd. Non-Metal Negative Residual Density      -2.00 eA-3
Author Response: I think the alert is false alert.
PLAT972_ALERT_2_C Large Calcd. Non-Metal Negative Residual Density      -1.98 eA-3
Author Response: I think the alert is false alert.
PLAT972_ALERT_2_C Large Calcd. Non-Metal Negative Residual Density      -1.97 eA-3
Author Response: I think the alert is false alert.
PLAT972_ALERT_2_C Large Calcd. Non-Metal Negative Residual Density      -1.92 eA-3
Author Response: I think the alert is false alert.
PLAT972_ALERT_2_C Large Calcd. Non-Metal Negative Residual Density      -1.89 eA-3
Author Response: I think the alert is false alert.
PLAT972_ALERT_2_C Large Calcd. Non-Metal Negative Residual Density      -1.88 eA-3
Author Response: I think the alert is false alert.
PLAT153_ALERT_1_C The su's on the Cell Axes   are Equal (x 100000)         20 Ang.

Alert level G PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large. 12.08 PLAT794_ALERT_5_G Note: Tentative Bond Valency for Cu1 ....... 2.18
13 ALERT level A = In general: serious problem 7 ALERT level B = Potentially serious problem 38 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 7 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 47 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Comment top

Copper(II) benzoate and its analogs form adducts with 2,2'-bipyridine. The copper benzoate homolog furnishes a water-coordinated adduct (Yang et al., 1994), as does copper p-toluate (Li et al., 2006; Liu et al., 2006) and copper o-toluate (He et al., 2007). The copper atom in Cu(H2O)(C10H8N2)(C7H4IO2)2 (Scheme I) is chelated by the N-heterocycle and is coordinated by two monodentate carboxylate ions and a water molecule in a square-pyramidal geometry (Fig. 1). The apical site is occupied by the O atom of the carboxylate unit. The crystal studied is a non-merohedral twin with minor components in a 0.381 (3) and 0.108 (2) proportion.

Related literature top

For related copper carboxylate–2,2'-bipyridine adducts, see: He et al. (2007); Li et al. (2006); Liu et al. (2006); Yang et al. (1994).

Experimental top

Copper acetate monohydrate (2.00 g, 10 mmol) and 4-iodobenzoic acid (4.96 g, 20 mmol) were heated in aqueous ethanol (1:1, 60 ml) for 1 h. The solvent was removed to give blue copper bis(4-iodobenzoate), which was isolated in 50% yield. The powder and 2,2'-bipyridine (0.77 g, 5 mmol) were dissolved in tetrahydrofuran. Crystals were isolated after several days.

Refinement top

H atoms were placed in calculated positions (C–H 0.95, O–H 0.84 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5U(C,O).

The final difference Fourier map had a peak and a hole in the vicinity of I2.

The crystal studied is a non-merohedral twin with minor components in a 38.1 (3) and 10.8 (2)% proportion. The twinned nature of the crystal structure adversely affected the quality of the diffraction measured, and this is reflected in the somewhat larger numbers in the weighting scheme.

Structure description top

Copper(II) benzoate and its analogs form adducts with 2,2'-bipyridine. The copper benzoate homolog furnishes a water-coordinated adduct (Yang et al., 1994), as does copper p-toluate (Li et al., 2006; Liu et al., 2006) and copper o-toluate (He et al., 2007). The copper atom in Cu(H2O)(C10H8N2)(C7H4IO2)2 (Scheme I) is chelated by the N-heterocycle and is coordinated by two monodentate carboxylate ions and a water molecule in a square-pyramidal geometry (Fig. 1). The apical site is occupied by the O atom of the carboxylate unit. The crystal studied is a non-merohedral twin with minor components in a 0.381 (3) and 0.108 (2) proportion.

For related copper carboxylate–2,2'-bipyridine adducts, see: He et al. (2007); Li et al. (2006); Liu et al. (2006); Yang et al. (1994).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of Cu(H2O)(C10H8N2)(C7H4IO2)2 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
Aqua(2,2'-bipyridine-κ2N,N')bis(4-iodobenzoato- κO)copper(II) top
Crystal data top
[Cu(C7H4IO2)2(C10H8N2)(H2O)]F(000) = 1404
Mr = 731.74Dx = 1.990 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1215 reflections
a = 13.0571 (2) Åθ = 2.5–24.2°
b = 16.0724 (2) ŵ = 3.46 mm1
c = 11.9605 (2) ÅT = 100 K
β = 103.298 (1)°Cube, blue
V = 2442.72 (6) Å30.30 × 0.30 × 0.30 mm
Z = 4
Data collection top
Bruker SMART APEX
diffractometer
5698 independent reflections
Radiation source: fine-focus sealed tube4505 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.092
ω scansθmax = 25.1°, θmin = 2.0°
Absorption correction: multi-scan
(TWINABS; Bruker, 2009)
h = 1515
Tmin = 0.423, Tmax = 0.423k = 019
33957 measured reflectionsl = 014
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)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.175H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.087P)2 + 12.0788P]
where P = (Fo2 + 2Fc2)/3
5698 reflections(Δ/σ)max = 0.001
310 parametersΔρmax = 1.71 e Å3
0 restraintsΔρmin = 1.69 e Å3
Crystal data top
[Cu(C7H4IO2)2(C10H8N2)(H2O)]V = 2442.72 (6) Å3
Mr = 731.74Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.0571 (2) ŵ = 3.46 mm1
b = 16.0724 (2) ÅT = 100 K
c = 11.9605 (2) Å0.30 × 0.30 × 0.30 mm
β = 103.298 (1)°
Data collection top
Bruker SMART APEX
diffractometer
5698 independent reflections
Absorption correction: multi-scan
(TWINABS; Bruker, 2009)
4505 reflections with I > 2σ(I)
Tmin = 0.423, Tmax = 0.423Rint = 0.092
33957 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0580 restraints
wR(F2) = 0.175H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.087P)2 + 12.0788P]
where P = (Fo2 + 2Fc2)/3
5698 reflectionsΔρmax = 1.71 e Å3
310 parametersΔρmin = 1.69 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I11.52100 (5)0.77933 (4)0.96178 (5)0.0307 (2)
I20.54254 (5)1.06313 (4)0.81444 (6)0.0370 (2)
Cu10.88404 (8)0.70624 (6)0.44393 (8)0.0165 (3)
O10.7975 (5)0.7791 (3)0.5186 (5)0.0189 (13)
O20.7765 (5)0.8878 (4)0.3970 (6)0.0319 (16)
O31.0368 (4)0.7208 (3)0.5695 (5)0.0182 (12)
O41.0982 (5)0.8248 (4)0.4776 (5)0.0220 (13)
O1W0.9172 (5)0.7943 (3)0.3446 (5)0.0203 (13)
H110.87730.83520.34550.030*
H120.98010.80920.36870.030*
N10.8380 (5)0.6058 (4)0.5151 (6)0.0162 (15)
N20.9245 (5)0.6191 (4)0.3416 (5)0.0144 (14)
C10.7637 (7)0.8513 (5)0.4846 (8)0.0215 (19)
C20.7064 (7)0.8978 (5)0.5618 (7)0.0209 (18)
C30.6627 (7)0.9757 (5)0.5274 (8)0.024 (2)
H30.66560.99670.45400.029*
C40.6158 (7)1.0224 (6)0.5975 (8)0.028 (2)
H40.58841.07590.57370.034*
C50.6090 (7)0.9913 (5)0.7019 (8)0.0236 (19)
C60.6510 (7)0.9127 (5)0.7390 (8)0.026 (2)
H60.64700.89190.81220.031*
C70.6977 (7)0.8665 (5)0.6682 (7)0.0219 (19)
H70.72450.81280.69160.026*
C81.1036 (7)0.7747 (5)0.5605 (7)0.0195 (18)
C91.2009 (7)0.7822 (5)0.6583 (7)0.0171 (17)
C101.2850 (7)0.8289 (5)0.6483 (7)0.0217 (19)
H101.28080.86120.58090.026*
C111.3773 (7)0.8306 (5)0.7346 (7)0.0222 (19)
H11A1.43650.86230.72630.027*
C121.3794 (7)0.7842 (5)0.8332 (7)0.0216 (19)
C131.2941 (7)0.7393 (5)0.8471 (8)0.0235 (19)
H131.29690.70960.91640.028*
C141.2052 (7)0.7373 (5)0.7612 (7)0.0204 (18)
H141.14600.70590.77030.024*
C150.7940 (7)0.6048 (5)0.6056 (7)0.0218 (19)
H150.78040.65660.63780.026*
C160.7670 (8)0.5324 (5)0.6550 (8)0.025 (2)
H160.73640.53390.71980.030*
C170.7866 (7)0.4578 (6)0.6057 (8)0.026 (2)
H170.76870.40680.63650.031*
C180.8320 (7)0.4570 (5)0.5122 (8)0.0230 (19)
H180.84560.40590.47820.028*
C190.8573 (6)0.5329 (5)0.4690 (7)0.0152 (17)
C200.9038 (6)0.5399 (5)0.3673 (7)0.0166 (17)
C210.9213 (7)0.4734 (5)0.3003 (8)0.026 (2)
H210.90650.41810.32000.031*
C220.9603 (8)0.4886 (6)0.2050 (7)0.026 (2)
H220.97340.44390.15820.031*
C230.9802 (7)0.5701 (5)0.1779 (8)0.024 (2)
H231.00540.58210.11120.029*
C240.9627 (6)0.6336 (5)0.2493 (7)0.0195 (18)
H240.97840.68920.23200.023*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.0258 (3)0.0370 (4)0.0256 (4)0.0053 (3)0.0018 (2)0.0007 (2)
I20.0303 (4)0.0424 (4)0.0393 (4)0.0066 (3)0.0099 (3)0.0150 (3)
Cu10.0216 (6)0.0126 (5)0.0153 (5)0.0010 (4)0.0045 (4)0.0007 (4)
O10.026 (3)0.016 (3)0.015 (3)0.000 (2)0.007 (3)0.004 (2)
O20.039 (4)0.029 (4)0.032 (4)0.010 (3)0.017 (3)0.017 (3)
O30.017 (3)0.020 (3)0.015 (3)0.002 (2)0.000 (2)0.000 (2)
O40.025 (3)0.021 (3)0.019 (3)0.007 (3)0.003 (3)0.008 (2)
O1W0.025 (3)0.017 (3)0.018 (3)0.000 (2)0.002 (3)0.001 (2)
N10.020 (4)0.010 (3)0.017 (4)0.003 (3)0.000 (3)0.001 (3)
N20.016 (3)0.017 (4)0.008 (3)0.003 (3)0.000 (3)0.001 (3)
C10.016 (4)0.020 (5)0.028 (5)0.004 (3)0.005 (4)0.007 (4)
C20.017 (4)0.020 (4)0.025 (5)0.001 (3)0.002 (4)0.000 (3)
C30.025 (5)0.023 (5)0.026 (5)0.000 (4)0.008 (4)0.004 (3)
C40.022 (5)0.026 (5)0.036 (6)0.001 (4)0.006 (4)0.003 (4)
C50.015 (4)0.026 (5)0.027 (5)0.003 (4)0.001 (4)0.011 (4)
C60.021 (5)0.022 (5)0.036 (6)0.001 (4)0.009 (4)0.001 (4)
C70.017 (4)0.017 (4)0.027 (5)0.001 (3)0.007 (4)0.002 (3)
C80.023 (5)0.015 (4)0.022 (5)0.003 (4)0.008 (4)0.004 (3)
C90.020 (4)0.019 (4)0.014 (4)0.004 (3)0.005 (3)0.002 (3)
C100.030 (5)0.024 (5)0.013 (4)0.002 (4)0.009 (4)0.000 (3)
C110.019 (4)0.032 (5)0.017 (4)0.005 (4)0.007 (4)0.006 (3)
C120.029 (5)0.022 (4)0.015 (4)0.009 (4)0.007 (4)0.008 (3)
C130.026 (5)0.019 (4)0.025 (5)0.005 (4)0.004 (4)0.001 (3)
C140.025 (5)0.012 (4)0.024 (5)0.004 (3)0.006 (4)0.002 (3)
C150.024 (5)0.017 (4)0.024 (5)0.000 (4)0.004 (4)0.001 (3)
C160.034 (5)0.023 (5)0.019 (5)0.004 (4)0.008 (4)0.002 (3)
C170.028 (5)0.027 (5)0.023 (5)0.006 (4)0.008 (4)0.006 (4)
C180.019 (5)0.013 (4)0.037 (5)0.003 (3)0.006 (4)0.003 (4)
C190.010 (4)0.019 (4)0.015 (4)0.004 (3)0.002 (3)0.004 (3)
C200.016 (4)0.014 (4)0.019 (5)0.001 (3)0.000 (3)0.000 (3)
C210.031 (5)0.017 (5)0.029 (5)0.005 (4)0.006 (4)0.002 (3)
C220.035 (5)0.023 (5)0.020 (5)0.002 (4)0.007 (4)0.006 (4)
C230.023 (5)0.028 (5)0.020 (5)0.002 (4)0.002 (4)0.004 (4)
C240.019 (4)0.025 (5)0.017 (5)0.002 (4)0.009 (4)0.001 (3)
Geometric parameters (Å, º) top
I1—C122.117 (9)C8—C91.521 (12)
I2—C52.106 (8)C9—C101.358 (12)
Cu1—N11.982 (7)C9—C141.416 (11)
Cu1—N22.009 (6)C10—C111.395 (12)
Cu1—O11.977 (5)C10—H100.9500
Cu1—O32.216 (6)C11—C121.390 (12)
Cu1—O1W1.959 (5)C11—H11A0.9500
O1—C11.275 (10)C12—C131.369 (13)
O2—C11.246 (10)C13—C141.363 (12)
O3—C81.251 (10)C13—H130.9500
O4—C81.268 (10)C14—H140.9500
O1W—H110.8400C15—C161.387 (12)
O1W—H120.8400C15—H150.9500
N1—C151.338 (11)C16—C171.386 (12)
N1—C191.344 (10)C16—H160.9500
N2—C241.332 (10)C17—C181.380 (12)
N2—C201.351 (10)C17—H170.9500
C1—C21.513 (12)C18—C191.394 (11)
C2—C71.396 (12)C18—H180.9500
C2—C31.397 (12)C19—C201.484 (12)
C3—C41.369 (12)C20—C211.386 (12)
C3—H30.9500C21—C221.373 (12)
C4—C51.367 (13)C21—H210.9500
C4—H40.9500C22—C231.389 (13)
C5—C61.409 (12)C22—H220.9500
C6—C71.370 (12)C23—C241.383 (12)
C6—H60.9500C23—H230.9500
C7—H70.9500C24—H240.9500
O1W—Cu1—O194.3 (2)C14—C9—C8119.1 (7)
O1W—Cu1—N1168.6 (3)C9—C10—C11121.6 (8)
O1—Cu1—N191.6 (3)C9—C10—H10119.2
O1W—Cu1—N290.5 (3)C11—C10—H10119.2
O1—Cu1—N2161.0 (3)C12—C11—C10117.5 (8)
N1—Cu1—N280.9 (3)C12—C11—H11A121.3
O1W—Cu1—O392.6 (2)C10—C11—H11A121.3
O1—Cu1—O398.7 (2)C13—C12—C11121.9 (8)
N1—Cu1—O396.3 (2)C13—C12—I1119.4 (6)
N2—Cu1—O399.5 (2)C11—C12—I1118.6 (7)
C1—O1—Cu1126.0 (5)C14—C13—C12119.8 (8)
C8—O3—Cu1123.5 (5)C14—C13—H13120.1
Cu1—O1W—H11109.5C12—C13—H13120.1
Cu1—O1W—H12109.5C13—C14—C9120.0 (8)
H11—O1W—H12109.5C13—C14—H14120.0
C15—N1—C19118.6 (7)C9—C14—H14120.0
C15—N1—Cu1125.9 (5)N1—C15—C16123.6 (8)
C19—N1—Cu1115.5 (5)N1—C15—H15118.2
C24—N2—C20119.1 (7)C16—C15—H15118.2
C24—N2—Cu1125.7 (6)C17—C16—C15117.1 (8)
C20—N2—Cu1115.1 (5)C17—C16—H16121.5
O2—C1—O1126.4 (8)C15—C16—H16121.5
O2—C1—C2117.5 (7)C18—C17—C16120.6 (8)
O1—C1—C2116.1 (7)C18—C17—H17119.7
C7—C2—C3118.5 (8)C16—C17—H17119.7
C7—C2—C1122.2 (8)C17—C18—C19118.3 (8)
C3—C2—C1119.3 (7)C17—C18—H18120.9
C4—C3—C2121.4 (8)C19—C18—H18120.9
C4—C3—H3119.3N1—C19—C18121.9 (7)
C2—C3—H3119.3N1—C19—C20114.9 (7)
C5—C4—C3119.4 (9)C18—C19—C20123.2 (7)
C5—C4—H4120.3N2—C20—C21121.8 (7)
C3—C4—H4120.3N2—C20—C19113.5 (7)
C4—C5—C6120.9 (8)C21—C20—C19124.6 (7)
C4—C5—I2120.5 (7)C22—C21—C20119.0 (8)
C6—C5—I2118.6 (6)C22—C21—H21120.5
C7—C6—C5119.2 (8)C20—C21—H21120.5
C7—C6—H6120.4C21—C22—C23119.1 (8)
C5—C6—H6120.4C21—C22—H22120.4
C6—C7—C2120.6 (8)C23—C22—H22120.4
C6—C7—H7119.7C24—C23—C22119.1 (8)
C2—C7—H7119.7C24—C23—H23120.5
O3—C8—O4126.4 (8)C22—C23—H23120.5
O3—C8—C9117.7 (7)N2—C24—C23121.9 (8)
O4—C8—C9115.9 (7)N2—C24—H24119.0
C10—C9—C14119.1 (8)C23—C24—H24119.0
C10—C9—C8121.7 (7)
O1W—Cu1—O1—C113.0 (7)Cu1—O3—C8—C9174.9 (5)
N1—Cu1—O1—C1157.2 (7)O3—C8—C9—C10169.1 (8)
N2—Cu1—O1—C191.2 (10)O4—C8—C9—C1011.3 (11)
O3—Cu1—O1—C1106.2 (7)O3—C8—C9—C149.0 (11)
O1W—Cu1—O3—C82.8 (6)O4—C8—C9—C14170.5 (7)
O1—Cu1—O3—C891.9 (6)C14—C9—C10—C113.1 (12)
N1—Cu1—O3—C8175.6 (6)C8—C9—C10—C11175.0 (7)
N2—Cu1—O3—C893.8 (6)C9—C10—C11—C121.6 (12)
O1W—Cu1—N1—C15138.5 (12)C10—C11—C12—C131.0 (12)
O1—Cu1—N1—C1517.7 (7)C10—C11—C12—I1176.3 (6)
N2—Cu1—N1—C15179.8 (7)C11—C12—C13—C142.0 (12)
O3—Cu1—N1—C1581.2 (7)I1—C12—C13—C14175.3 (6)
O1W—Cu1—N1—C1944.0 (17)C12—C13—C14—C90.5 (12)
O1—Cu1—N1—C19164.8 (6)C10—C9—C14—C132.1 (12)
N2—Cu1—N1—C192.3 (6)C8—C9—C14—C13176.1 (7)
O3—Cu1—N1—C1996.3 (6)C19—N1—C15—C160.1 (13)
O1W—Cu1—N2—C242.9 (7)Cu1—N1—C15—C16177.3 (7)
O1—Cu1—N2—C24107.7 (9)N1—C15—C16—C170.6 (14)
N1—Cu1—N2—C24175.3 (7)C15—C16—C17—C180.6 (14)
O3—Cu1—N2—C2489.8 (7)C16—C17—C18—C190.0 (14)
O1W—Cu1—N2—C20172.7 (6)C15—N1—C19—C180.5 (12)
O1—Cu1—N2—C2068.0 (10)Cu1—N1—C19—C18178.2 (6)
N1—Cu1—N2—C200.3 (6)C15—N1—C19—C20178.5 (7)
O3—Cu1—N2—C2094.6 (6)Cu1—N1—C19—C203.8 (9)
Cu1—O1—C1—O22.1 (13)C17—C18—C19—N10.6 (13)
Cu1—O1—C1—C2175.2 (5)C17—C18—C19—C20178.4 (8)
O2—C1—C2—C7172.9 (8)C24—N2—C20—C210.1 (12)
O1—C1—C2—C74.7 (12)Cu1—N2—C20—C21176.0 (7)
O2—C1—C2—C35.4 (13)C24—N2—C20—C19177.5 (7)
O1—C1—C2—C3177.0 (8)Cu1—N2—C20—C191.5 (9)
C7—C2—C3—C42.5 (13)N1—C19—C20—N23.5 (11)
C1—C2—C3—C4175.9 (9)C18—C19—C20—N2178.6 (8)
C2—C3—C4—C51.8 (14)N1—C19—C20—C21174.0 (8)
C3—C4—C5—C61.1 (14)C18—C19—C20—C214.0 (14)
C3—C4—C5—I2177.7 (7)N2—C20—C21—C220.3 (14)
C4—C5—C6—C71.1 (13)C19—C20—C21—C22176.9 (8)
I2—C5—C6—C7177.8 (7)C20—C21—C22—C230.6 (14)
C5—C6—C7—C21.7 (13)C21—C22—C23—C241.6 (14)
C3—C2—C7—C62.4 (13)C20—N2—C24—C231.1 (13)
C1—C2—C7—C6175.9 (8)Cu1—N2—C24—C23174.4 (6)
Cu1—O3—C8—O44.6 (12)C22—C23—C24—N21.9 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1w—H11···O20.841.792.560 (9)152
O1w—H12···O40.841.792.575 (8)154

Experimental details

Crystal data
Chemical formula[Cu(C7H4IO2)2(C10H8N2)(H2O)]
Mr731.74
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)13.0571 (2), 16.0724 (2), 11.9605 (2)
β (°) 103.298 (1)
V3)2442.72 (6)
Z4
Radiation typeMo Kα
µ (mm1)3.46
Crystal size (mm)0.30 × 0.30 × 0.30
Data collection
DiffractometerBruker SMART APEX
Absorption correctionMulti-scan
(TWINABS; Bruker, 2009)
Tmin, Tmax0.423, 0.423
No. of measured, independent and
observed [I > 2σ(I)] reflections
33957, 5698, 4505
Rint0.092
(sin θ/λ)max1)0.598
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.175, 1.08
No. of reflections5698
No. of parameters310
H-atom treatmentH-atom parameters constrained
w = 1/[σ2(Fo2) + (0.087P)2 + 12.0788P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)1.71, 1.69

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Selected bond lengths (Å) top
Cu1—N11.982 (7)Cu1—O32.216 (6)
Cu1—N22.009 (6)Cu1—O1W1.959 (5)
Cu1—O11.977 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1w—H11···O20.841.792.560 (9)151.9
O1w—H12···O40.841.792.575 (8)153.9
 

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