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In the title compound, [Cu(Cl2CHCO2)2(C6H6N2O)2(H2O)], both the CuII atom and the O atom of the coordinated water mol­ecule lie on a crystallographic twofold rotation axis. The CuII atom is coordinated by O atoms from two monodentate chloro­acetate anions, pyridine N atoms from two monodentate nicotinamide ligands and by the water mol­ecule, forming a tetra­gonal–pyramidal coordination polyhedron. The complexes are linked by O—H...O, N—H...O and C—H...O hydrogen bonds into a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807006423/bi2155sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807006423/bi2155Isup2.hkl
Contains datablock I

CCDC reference: 640260

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.035
  • wR factor = 0.077
  • Data-to-parameter ratio = 32.5

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT063_ALERT_3_B Crystal Probably too Large for Beam Size ....... 0.84 mm
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: enCIFer (Allen et al., 2004).

Aquabis(dichloroacetato-κO)bis(nicotinamide-κN)copper(II) top
Crystal data top
[Cu(C2HCl2O2)2(C6H6N2O)2(H2O)]Dx = 1.729 Mg m3
Mr = 581.68Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P42/nCell parameters from 5828 reflections
Hall symbol: -P 4bcθ = 3.4–35.0°
a = 14.145 (3) ŵ = 1.50 mm1
c = 11.165 (3) ÅT = 294 K
V = 2233.9 (9) Å3Needle, blue
Z = 40.84 × 0.17 × 0.15 mm
F(000) = 1172
Data collection top
Kuma KM-4 CCD
diffractometer
4847 independent reflections
Radiation source: large-focus sealed tube2650 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
ω scansθmax = 35.0°, θmin = 3.4°
Absorption correction: analytical
(CrysAlis RED; Oxford Diffraction, 2003)
h = 2118
Tmin = 0.426, Tmax = 0.799k = 2222
22722 measured reflectionsl = 1218
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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.031P)2]
where P = (Fo2 + 2Fc2)/3
4847 reflections(Δ/σ)max = 0.001
149 parametersΔρmax = 0.46 e Å3
2 restraintsΔρmin = 0.31 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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*/Ueq
Cu0.75000.25000.42261 (2)0.02337 (7)
Cl11.08185 (3)0.25658 (4)0.35906 (5)0.05667 (14)
Cl21.11889 (3)0.30776 (3)0.60607 (5)0.05210 (13)
N10.80469 (8)0.12079 (8)0.42602 (10)0.0251 (2)
O10.87848 (7)0.30854 (7)0.43491 (9)0.0302 (2)
O20.92327 (8)0.23875 (8)0.60474 (10)0.0382 (3)
O1W0.75000.25000.22185 (14)0.0408 (4)
O30.98843 (9)0.05744 (9)0.15707 (11)0.0472 (3)
C10.87198 (10)0.10043 (10)0.34600 (12)0.0271 (3)
H10.89000.14720.29210.032*
C20.91601 (10)0.01363 (10)0.33934 (13)0.0284 (3)
C30.88986 (13)0.05471 (11)0.42197 (15)0.0410 (4)
H30.91970.11330.42250.049*
C40.81941 (12)0.03496 (11)0.50308 (16)0.0430 (4)
H40.80000.08080.55760.052*
C50.77787 (11)0.05279 (11)0.50317 (13)0.0335 (4)
H50.73000.06550.55790.040*
C60.98538 (11)0.00055 (11)0.23910 (13)0.0338 (4)
C70.93890 (10)0.28495 (9)0.51436 (13)0.0264 (3)
C81.03918 (10)0.32035 (11)0.48552 (14)0.0340 (3)
H81.03550.38750.46430.041*
N21.03989 (10)0.07704 (10)0.24351 (12)0.0474 (4)
H2A1.07980.08800.18710.057*
H2B1.03520.11560.30280.057*
H1W0.7546 (16)0.2966 (9)0.1786 (16)0.071*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu0.02416 (13)0.01961 (12)0.02633 (12)0.00345 (10)0.0000.000
Cl10.0463 (3)0.0710 (3)0.0527 (3)0.0109 (2)0.0176 (2)0.0039 (2)
Cl20.0358 (2)0.0508 (3)0.0697 (3)0.0003 (2)0.0167 (2)0.0008 (2)
N10.0259 (6)0.0221 (6)0.0274 (6)0.0033 (4)0.0032 (5)0.0018 (5)
O10.0255 (5)0.0267 (5)0.0383 (6)0.0004 (4)0.0028 (4)0.0088 (5)
O20.0339 (6)0.0453 (7)0.0354 (6)0.0002 (5)0.0029 (5)0.0142 (5)
O1W0.0715 (12)0.0266 (8)0.0244 (8)0.0098 (9)0.0000.000
O30.0505 (7)0.0451 (7)0.0460 (7)0.0173 (6)0.0215 (6)0.0161 (6)
C10.0295 (7)0.0240 (7)0.0277 (7)0.0021 (6)0.0025 (6)0.0051 (6)
C20.0295 (7)0.0260 (7)0.0297 (8)0.0048 (6)0.0025 (6)0.0022 (6)
C30.0517 (10)0.0251 (7)0.0461 (10)0.0132 (7)0.0147 (8)0.0077 (7)
C40.0536 (11)0.0297 (9)0.0457 (9)0.0069 (7)0.0176 (8)0.0135 (7)
C50.0367 (9)0.0313 (8)0.0326 (8)0.0050 (6)0.0111 (7)0.0054 (7)
C60.0320 (9)0.0330 (8)0.0366 (9)0.0081 (7)0.0067 (7)0.0026 (7)
C70.0247 (7)0.0213 (7)0.0333 (8)0.0022 (5)0.0010 (6)0.0006 (6)
C80.0261 (8)0.0312 (8)0.0448 (9)0.0007 (6)0.0009 (7)0.0082 (7)
N20.0502 (9)0.0451 (8)0.0470 (9)0.0267 (7)0.0212 (7)0.0135 (7)
Geometric parameters (Å, º) top
Cu—N1i1.9850 (12)C2—C31.386 (2)
Cu—N11.9850 (12)C2—C61.502 (2)
Cu—O12.0018 (11)C3—C41.375 (2)
Cu—O1i2.0019 (11)C3—H30.930
Cu—O1W2.2415 (17)C4—C51.373 (2)
Cl1—C81.7809 (17)C4—H40.930
Cl2—C81.7649 (17)C5—H50.930
N1—C11.3369 (18)C6—N21.3295 (19)
N1—C51.3457 (18)C7—C81.538 (2)
O1—C71.2762 (17)C8—H80.980
O2—C71.2224 (17)N2—H2A0.860
O3—C61.2302 (18)N2—H2B0.860
C1—C21.379 (2)O1W—H1W0.82 (1)
C1—H10.930
N1i—Cu—N1177.80 (7)C2—C3—H3120.3
N1i—Cu—O188.38 (4)C5—C4—C3119.61 (15)
N1—Cu—O191.47 (4)C5—C4—H4120.2
N1i—Cu—O1i91.47 (4)C3—C4—H4120.2
N1—Cu—O1i88.38 (4)N1—C5—C4121.66 (13)
O1—Cu—O1i172.13 (6)N1—C5—H5119.2
N1i—Cu—O1W91.10 (3)C4—C5—H5119.2
N1—Cu—O1W91.10 (3)O3—C6—N2123.36 (14)
O1—Cu—O1W93.93 (3)O3—C6—C2119.25 (13)
O1i—Cu—O1W93.93 (3)N2—C6—C2117.38 (13)
C1—N1—C5118.33 (12)O2—C7—O1126.33 (13)
C1—N1—Cu117.58 (9)O2—C7—C8120.91 (13)
C5—N1—Cu124.09 (10)O1—C7—C8112.76 (12)
C7—O1—Cu123.20 (9)C7—C8—Cl2113.37 (11)
Cu—O1W—H1W126.1 (15)C7—C8—Cl1108.28 (10)
N1—C1—C2123.33 (13)Cl2—C8—Cl1109.69 (8)
N1—C1—H1118.3C7—C8—H8108.5
C2—C1—H1118.3Cl2—C8—H8108.5
C1—C2—C3117.68 (13)Cl1—C8—H8108.5
C1—C2—C6117.01 (13)C6—N2—H2A120.0
C3—C2—C6125.24 (13)C6—N2—H2B120.0
C4—C3—C2119.33 (14)H2A—N2—H2B120.0
C4—C3—H3120.3
O1—Cu—N1—C153.80 (11)C2—C3—C4—C51.8 (3)
O1i—Cu—N1—C1134.07 (11)C1—N1—C5—C41.6 (2)
O1W—Cu—N1—C140.16 (10)Cu—N1—C5—C4178.74 (12)
O1—Cu—N1—C5126.57 (12)C3—C4—C5—N10.4 (3)
O1i—Cu—N1—C545.56 (12)C1—C2—C6—O312.2 (2)
O1W—Cu—N1—C5139.46 (12)C3—C2—C6—O3164.79 (17)
N1i—Cu—O1—C7127.04 (11)C1—C2—C6—N2168.72 (15)
N1—Cu—O1—C750.76 (11)C3—C2—C6—N214.3 (2)
O1W—Cu—O1—C7141.97 (11)Cu—O1—C7—O214.3 (2)
C5—N1—C1—C20.7 (2)Cu—O1—C7—C8165.07 (9)
Cu—N1—C1—C2179.62 (11)O2—C7—C8—Cl211.56 (18)
N1—C1—C2—C31.4 (2)O1—C7—C8—Cl2168.99 (10)
N1—C1—C2—C6175.85 (14)O2—C7—C8—Cl1110.40 (14)
C1—C2—C3—C42.6 (3)O1—C7—C8—Cl169.05 (14)
C6—C2—C3—C4174.40 (17)
Symmetry code: (i) x+3/2, y+1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O1ii0.862.142.994 (2)172
N2—H2B···O2iii0.862.112.894 (2)152
O1W—H1W···O2iv0.82 (1)1.98 (1)2.782 (1)168 (1)
C8—H8···O3v0.982.243.149 (2)154
Symmetry codes: (ii) y+3/2, x1, z+1/2; (iii) x+2, y, z+1; (iv) y+1, x1/2, z1/2; (v) y+1, x+3/2, z+1/2.
 

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