The title compound, [Cu(mal)(pca)(H2O)]·H2O [mal is the malonate dianion, CH2(COO)22−, and pca is pyridine-2-carboxamide, C6H6N2O), has a five-coordinated Cu atom in a distorted square-pyramidal environment, coordinated by two O atoms of the malonate ion, an O atom and an N atom of pca, and an O atom of water. An uncoordinated water molecule stabilizes the complex by participation in a hydrogen-bonding system. The crystal structure is built from layers parallel to the (111) plane.
Supporting information
CCDC reference: 236029
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.029
- wR factor = 0.067
- Data-to-parameter ratio = 14.4
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.38
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu - O6 = 6.39 su
PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor .... 2.26
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2
H2 O
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 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
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
Data collection: CrysAlis CCD (Oxford Diffraction, 2003; cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2003; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC XP (Sheldrick, 1990); software used to prepare material for publication: PLATON (Spek, 1990).
Aqua(malonato-
κ2O,
O')(pyridine-2-carboxamide-
κ2N1,
O)copper(II) monohydrate
top
Crystal data top
[Cu(C3H2O4)(C6H6N2O)(H2O)]·H2O | Z = 2 |
Mr = 323.76 | F(000) = 330 |
Triclinic, P1 | Dx = 1.749 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.0566 (5) Å | Cell parameters from 4631 reflections |
b = 8.7694 (7) Å | θ = 2.1–29.1° |
c = 10.4093 (7) Å | µ = 1.81 mm−1 |
α = 68.540 (7)° | T = 293 K |
β = 81.355 (5)° | Prism, blue |
γ = 63.933 (7)° | 0.50 × 0.15 × 0.03 mm |
V = 614.78 (9) Å3 | |
Data collection top
Kuma KM-4-CCD diffractometer | 2828 independent reflections |
Radiation source: CX-Mo12x0.4-S Seifert Mo tube | 2131 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
ω scans | θmax = 27.5°, θmin = 3.0° |
Absorption correction: numerical (XRED; Stoe & Cie, 1999) | h = −10→10 |
Tmin = 0.729, Tmax = 0.947 | k = −11→8 |
4723 measured reflections | l = −13→13 |
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)] = 0.029 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.067 | Only H-atom displacement parameters refined |
S = 0.92 | w = 1/[σ2(Fo2) + (0.0281P)2] where P = (Fo2 + 2Fc2)/3 |
2828 reflections | (Δ/σ)max < 0.001 |
196 parameters | Δρmax = 0.88 e Å−3 |
4 restraints | Δρmin = −0.37 e Å−3 |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All e.s.d.'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 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cu | 0.50158 (4) | 0.20782 (4) | 0.05629 (3) | 0.0316 (1) | |
O1 | 0.2704 (2) | 0.4138 (2) | 0.06701 (16) | 0.0361 (5) | |
O2 | 0.5128 (2) | 0.3513 (2) | −0.13265 (16) | 0.0372 (5) | |
O3 | 0.6386 (2) | 0.4237 (2) | −0.33273 (16) | 0.0495 (6) | |
O4 | 0.6975 (2) | −0.01048 (19) | 0.03874 (16) | 0.0358 (5) | |
O5 | 0.9420 (2) | −0.1694 (2) | −0.05578 (16) | 0.0338 (5) | |
O6 | 0.6904 (2) | 0.2665 (2) | 0.16217 (18) | 0.0357 (6) | |
N1 | 0.4164 (2) | 0.0891 (2) | 0.24070 (18) | 0.0258 (5) | |
N2 | 0.0098 (2) | 0.5024 (2) | 0.1857 (2) | 0.0326 (6) | |
C1 | 0.1736 (3) | 0.3826 (3) | 0.1707 (2) | 0.0257 (6) | |
C2 | 0.2541 (3) | 0.1986 (3) | 0.2797 (2) | 0.0249 (6) | |
C3 | 0.1755 (3) | 0.1432 (3) | 0.4048 (2) | 0.0327 (7) | |
C4 | 0.2693 (3) | −0.0315 (3) | 0.4942 (2) | 0.0370 (8) | |
C5 | 0.4347 (3) | −0.1429 (3) | 0.4550 (2) | 0.0339 (7) | |
C6 | 0.5051 (3) | −0.0787 (3) | 0.3265 (2) | 0.0299 (7) | |
C7 | 0.6454 (3) | 0.3180 (3) | −0.2145 (2) | 0.0279 (7) | |
C8 | 0.8205 (3) | 0.1451 (3) | −0.1693 (2) | 0.0322 (7) | |
C9 | 0.8180 (3) | −0.0229 (3) | −0.0549 (2) | 0.0245 (6) | |
O7 | 0.7553 (2) | 0.4586 (3) | −0.59919 (18) | 0.0507 (7) | |
H1 | −0.03500 | 0.60700 | 0.12300 | 0.045 (8)* | |
H2 | −0.05310 | 0.47660 | 0.25830 | 0.033 (7)* | |
H3 | 0.06260 | 0.22050 | 0.42900 | 0.030 (6)* | |
H4 | 0.22010 | −0.07250 | 0.57980 | 0.031 (6)* | |
H5 | 0.49890 | −0.26000 | 0.51380 | 0.033 (6)* | |
H6 | 0.61680 | −0.15450 | 0.29970 | 0.030 (6)* | |
H61 | 0.7966 (14) | 0.247 (4) | 0.136 (3) | 0.057 (9)* | |
H62 | 0.643 (3) | 0.3751 (8) | 0.149 (3) | 0.053 (9)* | |
H81 | 0.90920 | 0.17460 | −0.14160 | 0.049 (8)* | |
H82 | 0.86980 | 0.11120 | −0.25060 | 0.049 (8)* | |
H71 | 0.745 (4) | 0.426 (4) | −0.5150 (3) | 0.055 (9)* | |
H72 | 0.654 (2) | 0.495 (5) | −0.634 (3) | 0.097 (14)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu | 0.0303 (2) | 0.0211 (2) | 0.0278 (2) | −0.0038 (1) | 0.0064 (1) | −0.0026 (1) |
O1 | 0.0332 (9) | 0.0220 (8) | 0.0306 (9) | −0.0039 (7) | 0.0077 (7) | 0.0031 (7) |
O2 | 0.0372 (9) | 0.0219 (8) | 0.0291 (9) | 0.0000 (7) | 0.0049 (7) | −0.0004 (7) |
O3 | 0.0541 (11) | 0.0323 (10) | 0.0259 (9) | −0.0010 (8) | 0.0056 (8) | 0.0059 (8) |
O4 | 0.0368 (9) | 0.0199 (8) | 0.0322 (9) | −0.0035 (7) | 0.0084 (7) | −0.0025 (7) |
O5 | 0.0313 (8) | 0.0209 (8) | 0.0372 (9) | −0.0026 (6) | 0.0025 (7) | −0.0080 (7) |
O6 | 0.0367 (10) | 0.0255 (9) | 0.0402 (10) | −0.0122 (8) | 0.0054 (8) | −0.0088 (8) |
N1 | 0.0273 (9) | 0.0188 (9) | 0.0258 (10) | −0.0076 (7) | −0.0008 (7) | −0.0037 (8) |
N2 | 0.0304 (10) | 0.0207 (10) | 0.0296 (10) | −0.0033 (8) | 0.0049 (8) | −0.0010 (8) |
C1 | 0.0262 (11) | 0.0210 (11) | 0.0248 (11) | −0.0086 (9) | 0.0014 (9) | −0.0043 (9) |
C2 | 0.0245 (11) | 0.0196 (11) | 0.0277 (11) | −0.0082 (9) | −0.0020 (9) | −0.0052 (9) |
C3 | 0.0336 (12) | 0.0284 (12) | 0.0275 (12) | −0.0101 (10) | 0.0046 (10) | −0.0053 (10) |
C4 | 0.0465 (14) | 0.0341 (14) | 0.0250 (12) | −0.0200 (11) | 0.0049 (10) | −0.0019 (10) |
C5 | 0.0412 (13) | 0.0199 (11) | 0.0329 (13) | −0.0115 (10) | −0.0078 (10) | 0.0010 (10) |
C6 | 0.0310 (12) | 0.0178 (11) | 0.0335 (13) | −0.0057 (9) | −0.0044 (10) | −0.0043 (9) |
C7 | 0.0333 (12) | 0.0210 (11) | 0.0243 (11) | −0.0076 (9) | −0.0015 (9) | −0.0062 (9) |
C8 | 0.0308 (12) | 0.0254 (12) | 0.0293 (12) | −0.0088 (10) | 0.0000 (10) | −0.0009 (10) |
C9 | 0.0236 (10) | 0.0218 (11) | 0.0249 (11) | −0.0069 (9) | −0.0054 (8) | −0.0053 (9) |
O7 | 0.0367 (11) | 0.0613 (13) | 0.0356 (11) | −0.0117 (9) | 0.0100 (9) | −0.0111 (10) |
Geometric parameters (Å, º) top
Cu—O1 | 1.9679 (17) | N2—C1 | 1.307 (3) |
Cu—O2 | 1.9223 (16) | N2—H2 | 0.86 |
Cu—O4 | 1.9244 (17) | N2—H1 | 0.86 |
Cu—O6 | 2.3239 (18) | C1—C2 | 1.508 (3) |
Cu—N1 | 2.0023 (18) | C2—C3 | 1.376 (3) |
O1—C1 | 1.252 (3) | C3—C4 | 1.391 (3) |
O2—C7 | 1.260 (3) | C4—C5 | 1.371 (4) |
O3—C7 | 1.232 (3) | C5—C6 | 1.389 (3) |
O4—C9 | 1.267 (3) | C7—C8 | 1.519 (4) |
O5—C9 | 1.236 (3) | C8—C9 | 1.525 (3) |
O6—H61 | 0.82 (2) | C3—H3 | 0.93 |
O6—H62 | 0.82 (2) | C4—H4 | 0.93 |
O7—H71 | 0.82 (1) | C5—H5 | 0.93 |
O7—H72 | 0.82 (3) | C6—H6 | 0.93 |
N1—C6 | 1.334 (3) | C8—H82 | 0.97 |
N1—C2 | 1.349 (3) | C8—H81 | 0.97 |
| | | |
O1—Cu—O2 | 86.50 (7) | N1—C2—C3 | 122.4 (2) |
O1—Cu—O4 | 169.20 (8) | C1—C2—C3 | 125.7 (2) |
O1—Cu—O6 | 96.63 (7) | C2—C3—C4 | 118.3 (2) |
O1—Cu—N1 | 81.30 (7) | C3—C4—C5 | 119.5 (2) |
O2—Cu—O4 | 94.43 (7) | C4—C5—C6 | 119.2 (2) |
O2—Cu—O6 | 100.56 (7) | N1—C6—C5 | 121.6 (2) |
O2—Cu—N1 | 164.35 (8) | O2—C7—O3 | 121.6 (2) |
O4—Cu—O6 | 93.78 (7) | O2—C7—C8 | 120.57 (18) |
O4—Cu—N1 | 95.75 (7) | O3—C7—C8 | 117.8 (2) |
O6—Cu—N1 | 90.60 (7) | C7—C8—C9 | 121.3 (2) |
Cu—O1—C1 | 115.76 (15) | O4—C9—O5 | 122.2 (2) |
Cu—O2—C7 | 127.51 (15) | O5—C9—C8 | 116.8 (2) |
Cu—O4—C9 | 126.76 (15) | O4—C9—C8 | 120.9 (2) |
H61—O6—H62 | 103 (3) | C4—C3—H3 | 120.84 |
Cu—O6—H61 | 120 (2) | C2—C3—H3 | 120.88 |
Cu—O6—H62 | 107.5 (18) | C3—C4—H4 | 120.26 |
H71—O7—H72 | 108 (3) | C5—C4—H4 | 120.27 |
Cu—N1—C2 | 113.72 (14) | C4—C5—H5 | 120.36 |
C2—N1—C6 | 119.08 (19) | C6—C5—H5 | 120.45 |
Cu—N1—C6 | 127.15 (15) | C5—C6—H6 | 119.18 |
H1—N2—H2 | 120.01 | N1—C6—H6 | 119.22 |
C1—N2—H1 | 120.00 | C7—C8—H81 | 107.06 |
C1—N2—H2 | 119.99 | C7—C8—H82 | 106.99 |
O1—C1—C2 | 117.0 (2) | C9—C8—H82 | 106.98 |
O1—C1—N2 | 122.4 (2) | H81—C8—H82 | 106.71 |
N2—C1—C2 | 120.6 (2) | C9—C8—H81 | 107.03 |
N1—C2—C1 | 111.96 (18) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H1···O5i | 0.86 | 2.11 | 2.939 (2) | 161 |
N2—H2···O7ii | 0.86 | 1.99 | 2.837 (3) | 168 |
O6—H61···O5iii | 0.82 | 2.06 | 2.865 (3) | 170 |
O6—H62···O2iv | 0.82 | 2.12 | 2.930 (2) | 171 |
O7—H71···O3 | 0.82 | 1.96 | 2.742 (2) | 160 |
O7—H72···O3v | 0.82 | 2.18 | 2.983 (3) | 164 |
C3—H3···O7ii | 0.93 | 2.41 | 3.293 (3) | 159 |
C5—H5···O3vi | 0.93 | 2.46 | 3.389 (3) | 174 |
C8—H81···O5iii | 0.97 | 2.51 | 3.357 (3) | 146 |
Symmetry codes: (i) x−1, y+1, z; (ii) x−1, y, z+1; (iii) −x+2, −y, −z; (iv) −x+1, −y+1, −z; (v) −x+1, −y+1, −z−1; (vi) x, y−1, z+1. |