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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804002727/hb6017sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804002727/hb6017Isup2.hkl
Contains datablock I

CCDC reference: 236029

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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

Computing details top

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)]·H2OZ = 2
Mr = 323.76F(000) = 330
Triclinic, P1Dx = 1.749 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.0566 (5) ÅCell parameters from 4631 reflections
b = 8.7694 (7) Åθ = 2.1–29.1°
c = 10.4093 (7) ŵ = 1.81 mm1
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 tube2131 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
ω scansθmax = 27.5°, θmin = 3.0°
Absorption correction: numerical
(XRED; Stoe & Cie, 1999)
h = 1010
Tmin = 0.729, Tmax = 0.947k = 118
4723 measured reflectionsl = 1313
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)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.067Only 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 parametersΔρmax = 0.88 e Å3
4 restraintsΔρmin = 0.37 e Å3
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
xyzUiso*/Ueq
Cu0.50158 (4)0.20782 (4)0.05629 (3)0.0316 (1)
O10.2704 (2)0.4138 (2)0.06701 (16)0.0361 (5)
O20.5128 (2)0.3513 (2)0.13265 (16)0.0372 (5)
O30.6386 (2)0.4237 (2)0.33273 (16)0.0495 (6)
O40.6975 (2)0.01048 (19)0.03874 (16)0.0358 (5)
O50.9420 (2)0.1694 (2)0.05578 (16)0.0338 (5)
O60.6904 (2)0.2665 (2)0.16217 (18)0.0357 (6)
N10.4164 (2)0.0891 (2)0.24070 (18)0.0258 (5)
N20.0098 (2)0.5024 (2)0.1857 (2)0.0326 (6)
C10.1736 (3)0.3826 (3)0.1707 (2)0.0257 (6)
C20.2541 (3)0.1986 (3)0.2797 (2)0.0249 (6)
C30.1755 (3)0.1432 (3)0.4048 (2)0.0327 (7)
C40.2693 (3)0.0315 (3)0.4942 (2)0.0370 (8)
C50.4347 (3)0.1429 (3)0.4550 (2)0.0339 (7)
C60.5051 (3)0.0787 (3)0.3265 (2)0.0299 (7)
C70.6454 (3)0.3180 (3)0.2145 (2)0.0279 (7)
C80.8205 (3)0.1451 (3)0.1693 (2)0.0322 (7)
C90.8180 (3)0.0229 (3)0.0549 (2)0.0245 (6)
O70.7553 (2)0.4586 (3)0.59919 (18)0.0507 (7)
H10.035000.607000.123000.045 (8)*
H20.053100.476600.258300.033 (7)*
H30.062600.220500.429000.030 (6)*
H40.220100.072500.579800.031 (6)*
H50.498900.260000.513800.033 (6)*
H60.616800.154500.299700.030 (6)*
H610.7966 (14)0.247 (4)0.136 (3)0.057 (9)*
H620.643 (3)0.3751 (8)0.149 (3)0.053 (9)*
H810.909200.174600.141600.049 (8)*
H820.869800.111200.250600.049 (8)*
H710.745 (4)0.426 (4)0.5150 (3)0.055 (9)*
H720.654 (2)0.495 (5)0.634 (3)0.097 (14)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu0.0303 (2)0.0211 (2)0.0278 (2)0.0038 (1)0.0064 (1)0.0026 (1)
O10.0332 (9)0.0220 (8)0.0306 (9)0.0039 (7)0.0077 (7)0.0031 (7)
O20.0372 (9)0.0219 (8)0.0291 (9)0.0000 (7)0.0049 (7)0.0004 (7)
O30.0541 (11)0.0323 (10)0.0259 (9)0.0010 (8)0.0056 (8)0.0059 (8)
O40.0368 (9)0.0199 (8)0.0322 (9)0.0035 (7)0.0084 (7)0.0025 (7)
O50.0313 (8)0.0209 (8)0.0372 (9)0.0026 (6)0.0025 (7)0.0080 (7)
O60.0367 (10)0.0255 (9)0.0402 (10)0.0122 (8)0.0054 (8)0.0088 (8)
N10.0273 (9)0.0188 (9)0.0258 (10)0.0076 (7)0.0008 (7)0.0037 (8)
N20.0304 (10)0.0207 (10)0.0296 (10)0.0033 (8)0.0049 (8)0.0010 (8)
C10.0262 (11)0.0210 (11)0.0248 (11)0.0086 (9)0.0014 (9)0.0043 (9)
C20.0245 (11)0.0196 (11)0.0277 (11)0.0082 (9)0.0020 (9)0.0052 (9)
C30.0336 (12)0.0284 (12)0.0275 (12)0.0101 (10)0.0046 (10)0.0053 (10)
C40.0465 (14)0.0341 (14)0.0250 (12)0.0200 (11)0.0049 (10)0.0019 (10)
C50.0412 (13)0.0199 (11)0.0329 (13)0.0115 (10)0.0078 (10)0.0010 (10)
C60.0310 (12)0.0178 (11)0.0335 (13)0.0057 (9)0.0044 (10)0.0043 (9)
C70.0333 (12)0.0210 (11)0.0243 (11)0.0076 (9)0.0015 (9)0.0062 (9)
C80.0308 (12)0.0254 (12)0.0293 (12)0.0088 (10)0.0000 (10)0.0009 (10)
C90.0236 (10)0.0218 (11)0.0249 (11)0.0069 (9)0.0054 (8)0.0053 (9)
O70.0367 (11)0.0613 (13)0.0356 (11)0.0117 (9)0.0100 (9)0.0111 (10)
Geometric parameters (Å, º) top
Cu—O11.9679 (17)N2—C11.307 (3)
Cu—O21.9223 (16)N2—H20.86
Cu—O41.9244 (17)N2—H10.86
Cu—O62.3239 (18)C1—C21.508 (3)
Cu—N12.0023 (18)C2—C31.376 (3)
O1—C11.252 (3)C3—C41.391 (3)
O2—C71.260 (3)C4—C51.371 (4)
O3—C71.232 (3)C5—C61.389 (3)
O4—C91.267 (3)C7—C81.519 (4)
O5—C91.236 (3)C8—C91.525 (3)
O6—H610.82 (2)C3—H30.93
O6—H620.82 (2)C4—H40.93
O7—H710.82 (1)C5—H50.93
O7—H720.82 (3)C6—H60.93
N1—C61.334 (3)C8—H820.97
N1—C21.349 (3)C8—H810.97
O1—Cu—O286.50 (7)N1—C2—C3122.4 (2)
O1—Cu—O4169.20 (8)C1—C2—C3125.7 (2)
O1—Cu—O696.63 (7)C2—C3—C4118.3 (2)
O1—Cu—N181.30 (7)C3—C4—C5119.5 (2)
O2—Cu—O494.43 (7)C4—C5—C6119.2 (2)
O2—Cu—O6100.56 (7)N1—C6—C5121.6 (2)
O2—Cu—N1164.35 (8)O2—C7—O3121.6 (2)
O4—Cu—O693.78 (7)O2—C7—C8120.57 (18)
O4—Cu—N195.75 (7)O3—C7—C8117.8 (2)
O6—Cu—N190.60 (7)C7—C8—C9121.3 (2)
Cu—O1—C1115.76 (15)O4—C9—O5122.2 (2)
Cu—O2—C7127.51 (15)O5—C9—C8116.8 (2)
Cu—O4—C9126.76 (15)O4—C9—C8120.9 (2)
H61—O6—H62103 (3)C4—C3—H3120.84
Cu—O6—H61120 (2)C2—C3—H3120.88
Cu—O6—H62107.5 (18)C3—C4—H4120.26
H71—O7—H72108 (3)C5—C4—H4120.27
Cu—N1—C2113.72 (14)C4—C5—H5120.36
C2—N1—C6119.08 (19)C6—C5—H5120.45
Cu—N1—C6127.15 (15)C5—C6—H6119.18
H1—N2—H2120.01N1—C6—H6119.22
C1—N2—H1120.00C7—C8—H81107.06
C1—N2—H2119.99C7—C8—H82106.99
O1—C1—C2117.0 (2)C9—C8—H82106.98
O1—C1—N2122.4 (2)H81—C8—H82106.71
N2—C1—C2120.6 (2)C9—C8—H81107.03
N1—C2—C1111.96 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H1···O5i0.862.112.939 (2)161
N2—H2···O7ii0.861.992.837 (3)168
O6—H61···O5iii0.822.062.865 (3)170
O6—H62···O2iv0.822.122.930 (2)171
O7—H71···O30.821.962.742 (2)160
O7—H72···O3v0.822.182.983 (3)164
C3—H3···O7ii0.932.413.293 (3)159
C5—H5···O3vi0.932.463.389 (3)174
C8—H81···O5iii0.972.513.357 (3)146
Symmetry codes: (i) x1, y+1, z; (ii) x1, y, z+1; (iii) x+2, y, z; (iv) x+1, y+1, z; (v) x+1, y+1, z1; (vi) x, y1, z+1.
 

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