Dichlorobis­(malonamide-κ²O,O′)copper(II)

The title complex, [CuCl₂(C₃H₆N₂O₂)₂], exists in the crystal structure as a monomer and possesses a crystallographically imposed center of symmetry. The Cu atom is coordinated by two Cl atoms [Cu—Cl = 2.7696 (3) Å] and four O atoms [Cu—O = 1.9484 (8) and 1.9769 (9) Å] from two chelating malonamide ligands in a distorted octa­hedral geometry. In the crystal structure, a three-dimensional hydrogen-bonding network is formed by inter­molecular N—H...O and N—H...Cl inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.018
• wR factor = 0.041
• Data-to-parameter ratio = 19.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu1    -   Cl1     ..       9.54 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu1    -   O2      ..       5.48 su

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   2 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Dichloro-bis(malonamide-κ²O,O')copper(II)

Crystal data

[CuCl2(C3H6N2O2)2]	F(000) = 342
Mr = 338.65	Dx = 1.929 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6056 reflections
a = 8.3177 (6) Å	θ = 2.8–31.3°
b = 7.3586 (5) Å	µ = 2.34 mm^−1
c = 10.0195 (7) Å	T = 100 K
β = 108.101 (2)°	Prism, blue
V = 582.91 (7) Å^3	0.20 × 0.15 × 0.15 mm
Z = 2

Data collection

Bruker SMART APEX2 CCD area detector diffractometer	1517 independent reflections
Radiation source: fine-focus sealed tube	1446 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
φ and ω scans	θmax = 29.0°, θmin = 3.5°
Absorption correction: multi-scan (APEX2; Bruker, 2005)	h = −11→11
Tmin = 0.594, Tmax = 0.704	k = −10→10
7665 measured reflections	l = −13→13

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.018	Hydrogen site location: mixed
wR(F^2) = 0.041	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.01P)^2 + 0.55P] where P = (Fo^2 + 2Fc^2)/3
1517 reflections	(Δ/σ)max < 0.001
79 parameters	Δρmax = 0.43 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.0000	0.0000	0.5000	0.00857 (6)
Cl1	0.11620 (3)	0.05718 (4)	0.27260 (3)	0.01116 (7)
O1	0.22468 (10)	0.06546 (12)	0.62177 (9)	0.00995 (17)
O2	0.05914 (11)	−0.26085 (12)	0.50815 (9)	0.01035 (17)
N1	0.50395 (13)	0.02996 (15)	0.72153 (11)	0.0112 (2)
H1N	0.5149	0.1426	0.7583	0.013*
H2N	0.5971	−0.0346	0.7251	0.013*
N2	0.23656 (13)	−0.49997 (14)	0.55868 (11)	0.0104 (2)
H3N	0.1496	−0.5783	0.5433	0.012*
H4N	0.3426	−0.5412	0.5984	0.012*
C1	0.35643 (15)	−0.02773 (16)	0.63814 (12)	0.0084 (2)
C2	0.35889 (14)	−0.20359 (17)	0.56200 (13)	0.0099 (2)
H2A	0.3677	−0.1750	0.4680	0.012*
H2B	0.4618	−0.2720	0.6139	0.012*
C3	0.20755 (14)	−0.32453 (17)	0.54380 (12)	0.0084 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.00529 (10)	0.00571 (10)	0.01245 (11)	0.00027 (7)	−0.00051 (7)	−0.00025 (7)
Cl1	0.00807 (12)	0.01183 (14)	0.01290 (13)	0.00103 (10)	0.00227 (9)	0.00072 (10)
O1	0.0060 (4)	0.0100 (4)	0.0124 (4)	0.0003 (3)	0.0007 (3)	−0.0007 (3)
O2	0.0067 (4)	0.0080 (4)	0.0149 (4)	0.0004 (3)	0.0013 (3)	0.0003 (3)
N1	0.0067 (4)	0.0112 (5)	0.0140 (5)	−0.0004 (4)	0.0009 (4)	−0.0015 (4)
N2	0.0082 (4)	0.0085 (5)	0.0133 (5)	0.0001 (4)	0.0017 (4)	−0.0003 (4)
C1	0.0082 (5)	0.0083 (5)	0.0087 (5)	−0.0009 (4)	0.0025 (4)	0.0018 (4)
C2	0.0074 (5)	0.0087 (5)	0.0136 (5)	0.0000 (4)	0.0031 (4)	−0.0005 (4)
C3	0.0090 (5)	0.0097 (6)	0.0066 (5)	−0.0006 (4)	0.0024 (4)	−0.0009 (4)

Geometric parameters (Å, º)

Cu1—O1^i	1.9484 (8)	N1—H1N	0.9000
Cu1—O1	1.9484 (8)	N1—H2N	0.9000
Cu1—O2	1.9769 (9)	N2—C3	1.3133 (16)
Cu1—O2^i	1.9769 (9)	N2—H3N	0.9000
Cu1—Cl1	2.7696 (3)	N2—H4N	0.9000
Cu1—Cl1^i	2.7696 (3)	C1—C2	1.5056 (17)
O1—C1	1.2595 (14)	C2—C3	1.5058 (16)
O2—C3	1.2637 (14)	C2—H2A	0.9900
N1—C1	1.3217 (15)	C2—H2B	0.9900
O1^i—Cu1—O1	180.0	C3—N2—H4N	120.1
O1^i—Cu1—O2	87.92 (4)	H3N—N2—H4N	119.0
O1—Cu1—O2	92.08 (4)	O1—C1—N1	120.45 (11)
O1^i—Cu1—O2^i	92.08 (4)	O1—C1—C2	123.38 (10)
O1—Cu1—O2^i	87.92 (4)	N1—C1—C2	116.12 (10)
O2—Cu1—O2^i	180.00 (5)	C3—C2—C1	115.27 (10)
O1—Cu1—Cl1	88.03 (3)	C3—C2—H2A	108.5
O2—Cu1—Cl1	92.04 (3)	C1—C2—H2A	108.5
C1—O1—Cu1	124.99 (8)	C3—C2—H2B	108.5
C3—O2—Cu1	125.48 (8)	C1—C2—H2B	108.5
C1—N1—H1N	120.7	H2A—C2—H2B	107.5
C1—N1—H2N	118.3	O2—C3—N2	121.70 (11)
H1N—N1—H2N	119.6	O2—C3—C2	121.43 (11)
C3—N2—H3N	120.0	N2—C3—C2	116.75 (11)
O2—Cu1—O1—C1	23.63 (10)	O1—C1—C2—C3	−38.65 (16)
O2^i—Cu1—O1—C1	−156.37 (10)	N1—C1—C2—C3	143.83 (11)
O1^i—Cu1—O2—C3	160.90 (10)	Cu1—O2—C3—N2	173.77 (9)
O1—Cu1—O2—C3	−19.10 (10)	Cu1—O2—C3—C2	−10.30 (16)
Cu1—O1—C1—N1	178.83 (8)	C1—C2—C3—O2	43.03 (16)
Cu1—O1—C1—C2	1.42 (16)	C1—C2—C3—N2	−140.85 (11)

Symmetry code: (i) −x, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···Cl1^ii	0.90	2.35	3.1728 (11)	151
N1—H2N···Cl1^iii	0.90	2.38	3.2064 (11)	152
N2—H3N···O2^iv	0.90	2.03	2.9278 (14)	174
N2—H4N···Cl1^v	0.90	2.40	3.2461 (11)	156

Symmetry codes: (ii) x+1/2, −y+1/2, z+1/2; (iii) −x+1, −y, −z+1; (iv) −x, −y−1, −z+1; (v) x+1/2, −y−1/2, z+1/2.