In the title compound, [Cu(Cl
2CHCO
2)
2(C
6H
6N
2O)
2(H
2O)], both the Cu
II atom and the O atom of the coordinated water molecule lie on a crystallographic twofold rotation axis. The Cu
II 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
CCDC reference: 640260
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (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
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 m−3 |
Mr = 581.68 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P42/n | Cell parameters from 5828 reflections |
Hall symbol: -P 4bc | θ = 3.4–35.0° |
a = 14.145 (3) Å | µ = 1.50 mm−1 |
c = 11.165 (3) Å | T = 294 K |
V = 2233.9 (9) Å3 | Needle, blue |
Z = 4 | 0.84 × 0.17 × 0.15 mm |
F(000) = 1172 | |
Data collection top
Kuma KM-4 CCD diffractometer | 4847 independent reflections |
Radiation source: large-focus sealed tube | 2650 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
ω scans | θmax = 35.0°, θmin = 3.4° |
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2003) | h = −21→18 |
Tmin = 0.426, Tmax = 0.799 | k = −22→22 |
22722 measured reflections | l = −12→18 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.077 | H 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 parameters | Δρmax = 0.46 e Å−3 |
2 restraints | Δρmin = −0.31 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Cu | 0.7500 | 0.2500 | 0.42261 (2) | 0.02337 (7) | |
Cl1 | 1.08185 (3) | 0.25658 (4) | 0.35906 (5) | 0.05667 (14) | |
Cl2 | 1.11889 (3) | 0.30776 (3) | 0.60607 (5) | 0.05210 (13) | |
N1 | 0.80469 (8) | 0.12079 (8) | 0.42602 (10) | 0.0251 (2) | |
O1 | 0.87848 (7) | 0.30854 (7) | 0.43491 (9) | 0.0302 (2) | |
O2 | 0.92327 (8) | 0.23875 (8) | 0.60474 (10) | 0.0382 (3) | |
O1W | 0.7500 | 0.2500 | 0.22185 (14) | 0.0408 (4) | |
O3 | 0.98843 (9) | 0.05744 (9) | 0.15707 (11) | 0.0472 (3) | |
C1 | 0.87198 (10) | 0.10043 (10) | 0.34600 (12) | 0.0271 (3) | |
H1 | 0.8900 | 0.1472 | 0.2921 | 0.032* | |
C2 | 0.91601 (10) | 0.01363 (10) | 0.33934 (13) | 0.0284 (3) | |
C3 | 0.88986 (13) | −0.05471 (11) | 0.42197 (15) | 0.0410 (4) | |
H3 | 0.9197 | −0.1133 | 0.4225 | 0.049* | |
C4 | 0.81941 (12) | −0.03496 (11) | 0.50308 (16) | 0.0430 (4) | |
H4 | 0.8000 | −0.0808 | 0.5576 | 0.052* | |
C5 | 0.77787 (11) | 0.05279 (11) | 0.50317 (13) | 0.0335 (4) | |
H5 | 0.7300 | 0.0655 | 0.5579 | 0.040* | |
C6 | 0.98538 (11) | −0.00055 (11) | 0.23910 (13) | 0.0338 (4) | |
C7 | 0.93890 (10) | 0.28495 (9) | 0.51436 (13) | 0.0264 (3) | |
C8 | 1.03918 (10) | 0.32035 (11) | 0.48552 (14) | 0.0340 (3) | |
H8 | 1.0355 | 0.3875 | 0.4643 | 0.041* | |
N2 | 1.03989 (10) | −0.07704 (10) | 0.24351 (12) | 0.0474 (4) | |
H2A | 1.0798 | −0.0880 | 0.1871 | 0.057* | |
H2B | 1.0352 | −0.1156 | 0.3028 | 0.057* | |
H1W | 0.7546 (16) | 0.2966 (9) | 0.1786 (16) | 0.071* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu | 0.02416 (13) | 0.01961 (12) | 0.02633 (12) | 0.00345 (10) | 0.000 | 0.000 |
Cl1 | 0.0463 (3) | 0.0710 (3) | 0.0527 (3) | 0.0109 (2) | 0.0176 (2) | 0.0039 (2) |
Cl2 | 0.0358 (2) | 0.0508 (3) | 0.0697 (3) | 0.0003 (2) | −0.0167 (2) | 0.0008 (2) |
N1 | 0.0259 (6) | 0.0221 (6) | 0.0274 (6) | 0.0033 (4) | 0.0032 (5) | 0.0018 (5) |
O1 | 0.0255 (5) | 0.0267 (5) | 0.0383 (6) | 0.0004 (4) | −0.0028 (4) | 0.0088 (5) |
O2 | 0.0339 (6) | 0.0453 (7) | 0.0354 (6) | −0.0002 (5) | 0.0029 (5) | 0.0142 (5) |
O1W | 0.0715 (12) | 0.0266 (8) | 0.0244 (8) | 0.0098 (9) | 0.000 | 0.000 |
O3 | 0.0505 (7) | 0.0451 (7) | 0.0460 (7) | 0.0173 (6) | 0.0215 (6) | 0.0161 (6) |
C1 | 0.0295 (7) | 0.0240 (7) | 0.0277 (7) | 0.0021 (6) | 0.0025 (6) | 0.0051 (6) |
C2 | 0.0295 (7) | 0.0260 (7) | 0.0297 (8) | 0.0048 (6) | 0.0025 (6) | 0.0022 (6) |
C3 | 0.0517 (10) | 0.0251 (7) | 0.0461 (10) | 0.0132 (7) | 0.0147 (8) | 0.0077 (7) |
C4 | 0.0536 (11) | 0.0297 (9) | 0.0457 (9) | 0.0069 (7) | 0.0176 (8) | 0.0135 (7) |
C5 | 0.0367 (9) | 0.0313 (8) | 0.0326 (8) | 0.0050 (6) | 0.0111 (7) | 0.0054 (7) |
C6 | 0.0320 (9) | 0.0330 (8) | 0.0366 (9) | 0.0081 (7) | 0.0067 (7) | 0.0026 (7) |
C7 | 0.0247 (7) | 0.0213 (7) | 0.0333 (8) | 0.0022 (5) | 0.0010 (6) | 0.0006 (6) |
C8 | 0.0261 (8) | 0.0312 (8) | 0.0448 (9) | 0.0007 (6) | 0.0009 (7) | 0.0082 (7) |
N2 | 0.0502 (9) | 0.0451 (8) | 0.0470 (9) | 0.0267 (7) | 0.0212 (7) | 0.0135 (7) |
Geometric parameters (Å, º) top
Cu—N1i | 1.9850 (12) | C2—C3 | 1.386 (2) |
Cu—N1 | 1.9850 (12) | C2—C6 | 1.502 (2) |
Cu—O1 | 2.0018 (11) | C3—C4 | 1.375 (2) |
Cu—O1i | 2.0019 (11) | C3—H3 | 0.930 |
Cu—O1W | 2.2415 (17) | C4—C5 | 1.373 (2) |
Cl1—C8 | 1.7809 (17) | C4—H4 | 0.930 |
Cl2—C8 | 1.7649 (17) | C5—H5 | 0.930 |
N1—C1 | 1.3369 (18) | C6—N2 | 1.3295 (19) |
N1—C5 | 1.3457 (18) | C7—C8 | 1.538 (2) |
O1—C7 | 1.2762 (17) | C8—H8 | 0.980 |
O2—C7 | 1.2224 (17) | N2—H2A | 0.860 |
O3—C6 | 1.2302 (18) | N2—H2B | 0.860 |
C1—C2 | 1.379 (2) | O1W—H1W | 0.82 (1) |
C1—H1 | 0.930 | | |
| | | |
N1i—Cu—N1 | 177.80 (7) | C2—C3—H3 | 120.3 |
N1i—Cu—O1 | 88.38 (4) | C5—C4—C3 | 119.61 (15) |
N1—Cu—O1 | 91.47 (4) | C5—C4—H4 | 120.2 |
N1i—Cu—O1i | 91.47 (4) | C3—C4—H4 | 120.2 |
N1—Cu—O1i | 88.38 (4) | N1—C5—C4 | 121.66 (13) |
O1—Cu—O1i | 172.13 (6) | N1—C5—H5 | 119.2 |
N1i—Cu—O1W | 91.10 (3) | C4—C5—H5 | 119.2 |
N1—Cu—O1W | 91.10 (3) | O3—C6—N2 | 123.36 (14) |
O1—Cu—O1W | 93.93 (3) | O3—C6—C2 | 119.25 (13) |
O1i—Cu—O1W | 93.93 (3) | N2—C6—C2 | 117.38 (13) |
C1—N1—C5 | 118.33 (12) | O2—C7—O1 | 126.33 (13) |
C1—N1—Cu | 117.58 (9) | O2—C7—C8 | 120.91 (13) |
C5—N1—Cu | 124.09 (10) | O1—C7—C8 | 112.76 (12) |
C7—O1—Cu | 123.20 (9) | C7—C8—Cl2 | 113.37 (11) |
Cu—O1W—H1W | 126.1 (15) | C7—C8—Cl1 | 108.28 (10) |
N1—C1—C2 | 123.33 (13) | Cl2—C8—Cl1 | 109.69 (8) |
N1—C1—H1 | 118.3 | C7—C8—H8 | 108.5 |
C2—C1—H1 | 118.3 | Cl2—C8—H8 | 108.5 |
C1—C2—C3 | 117.68 (13) | Cl1—C8—H8 | 108.5 |
C1—C2—C6 | 117.01 (13) | C6—N2—H2A | 120.0 |
C3—C2—C6 | 125.24 (13) | C6—N2—H2B | 120.0 |
C4—C3—C2 | 119.33 (14) | H2A—N2—H2B | 120.0 |
C4—C3—H3 | 120.3 | | |
| | | |
O1—Cu—N1—C1 | −53.80 (11) | C2—C3—C4—C5 | −1.8 (3) |
O1i—Cu—N1—C1 | 134.07 (11) | C1—N1—C5—C4 | 1.6 (2) |
O1W—Cu—N1—C1 | 40.16 (10) | Cu—N1—C5—C4 | −178.74 (12) |
O1—Cu—N1—C5 | 126.57 (12) | C3—C4—C5—N1 | −0.4 (3) |
O1i—Cu—N1—C5 | −45.56 (12) | C1—C2—C6—O3 | −12.2 (2) |
O1W—Cu—N1—C5 | −139.46 (12) | C3—C2—C6—O3 | 164.79 (17) |
N1i—Cu—O1—C7 | 127.04 (11) | C1—C2—C6—N2 | 168.72 (15) |
N1—Cu—O1—C7 | −50.76 (11) | C3—C2—C6—N2 | −14.3 (2) |
O1W—Cu—O1—C7 | −141.97 (11) | Cu—O1—C7—O2 | −14.3 (2) |
C5—N1—C1—C2 | −0.7 (2) | Cu—O1—C7—C8 | 165.07 (9) |
Cu—N1—C1—C2 | 179.62 (11) | O2—C7—C8—Cl2 | −11.56 (18) |
N1—C1—C2—C3 | −1.4 (2) | O1—C7—C8—Cl2 | 168.99 (10) |
N1—C1—C2—C6 | 175.85 (14) | O2—C7—C8—Cl1 | 110.40 (14) |
C1—C2—C3—C4 | 2.6 (3) | O1—C7—C8—Cl1 | −69.05 (14) |
C6—C2—C3—C4 | −174.40 (17) | | |
Symmetry code: (i) −x+3/2, −y+1/2, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1ii | 0.86 | 2.14 | 2.994 (2) | 172 |
N2—H2B···O2iii | 0.86 | 2.11 | 2.894 (2) | 152 |
O1W—H1W···O2iv | 0.82 (1) | 1.98 (1) | 2.782 (1) | 168 (1) |
C8—H8···O3v | 0.98 | 2.24 | 3.149 (2) | 154 |
Symmetry codes: (ii) −y+3/2, x−1, −z+1/2; (iii) −x+2, −y, −z+1; (iv) −y+1, x−1/2, z−1/2; (v) y+1, −x+3/2, −z+1/2. |