Bis(malonamide-κ²O,O′)bis­(nitrato-κO)copper(II)

The title complex, [Cu(NO₃)₂(C₃H₆N₂O₂)₂], exists in the crystal structure as a monomer and possesses a crystallographically imposed center of symmetry. The Cu atom is coordinated by six O atoms [Cu—O = 1.9339 (10)–2.3964 (11) Å] from two chelating malonamide ligands and two terminal NO₃ groups in a distorted octa­hedral geometry. The crystal packing is stabilized by inter­molecular N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.024
• wR factor = 0.059
• Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.57 Ratio
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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
   1 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; 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.

Bis(malonamide-κ2O,O')-bis(nitrato-κO)copper(II)

Crystal data

[Cu(NO3)2(C3H6N2O2)2]	Z = 1
Mr = 391.76	F(000) = 199
Triclinic, P1	Dx = 2.016 Mg m^−3
a = 6.8515 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.0698 (7) Å	Cell parameters from 3216 reflections
c = 7.4611 (8) Å	θ = 5.9–58.1°
α = 89.661 (2)°	µ = 1.77 mm^−1
β = 69.488 (2)°	T = 120 K
γ = 73.482 (2)°	Prism, blue
V = 322.75 (6) Å^3	0.25 × 0.25 × 0.15 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer	1683 independent reflections
Radiation source: normal-focus sealed tube	1663 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
φ and ω scans	θmax = 29.0°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −9→9
Tmin = 0.617, Tmax = 0.767	k = −9→9
3545 measured reflections	l = −10→10

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)] = 0.024	Hydrogen site location: mixed
wR(F^2) = 0.059	H-atom parameters constrained
S = 0.98	w = 1/[σ^2(Fo^2) + (0.028P)^2 + 0.35P] where P = (Fo^2 + 2Fc^2)/3
1683 reflections	(Δ/σ)max < 0.001
106 parameters	Δρmax = 0.41 e Å^−3
0 restraints	Δρmin = −0.64 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	1.0000	0.0000	0.00848 (8)
O1	−0.03601 (16)	0.74677 (14)	0.09604 (14)	0.01006 (19)
O2	0.23839 (17)	0.98711 (15)	0.08616 (15)	0.0117 (2)
O3	0.25675 (18)	0.82833 (17)	−0.30433 (16)	0.0166 (2)
O4	0.60326 (18)	0.67245 (18)	−0.45171 (17)	0.0199 (2)
O5	0.4290 (2)	0.5973 (2)	−0.17164 (18)	0.0260 (3)
N1	0.0907 (2)	0.46707 (18)	0.21923 (19)	0.0127 (2)
H1N1	0.0561	0.3945	0.1430	0.015*
H1N2	0.1760	0.4101	0.2850	0.015*
N2	0.4614 (2)	0.86562 (19)	0.24476 (19)	0.0140 (2)
H2N1	0.5544	0.9235	0.1645	0.017*
H2N2	0.4815	0.7954	0.3412	0.017*
N3	0.4294 (2)	0.69770 (18)	−0.30704 (18)	0.0130 (2)
C1	0.0589 (2)	0.6576 (2)	0.20339 (19)	0.0086 (2)
C2	0.1291 (2)	0.7710 (2)	0.32874 (19)	0.0096 (2)
H2A	−0.0017	0.8678	0.4228	0.012*
H2B	0.2019	0.6773	0.4015	0.012*
C3	0.2834 (2)	0.87926 (19)	0.21088 (19)	0.0088 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.00921 (12)	0.00720 (12)	0.01215 (12)	−0.00345 (8)	−0.00684 (9)	0.00281 (8)
O1	0.0117 (4)	0.0084 (4)	0.0131 (5)	−0.0038 (3)	−0.0074 (4)	0.0025 (3)
O2	0.0121 (4)	0.0128 (5)	0.0153 (5)	−0.0065 (4)	−0.0088 (4)	0.0067 (4)
O3	0.0141 (5)	0.0171 (5)	0.0143 (5)	0.0041 (4)	−0.0067 (4)	−0.0007 (4)
O4	0.0131 (5)	0.0228 (6)	0.0169 (5)	−0.0003 (4)	−0.0014 (4)	0.0049 (4)
O5	0.0220 (6)	0.0261 (6)	0.0178 (6)	0.0055 (5)	−0.0030 (5)	0.0089 (5)
N1	0.0172 (6)	0.0083 (5)	0.0169 (6)	−0.0048 (4)	−0.0105 (5)	0.0024 (4)
N2	0.0132 (6)	0.0172 (6)	0.0168 (6)	−0.0074 (5)	−0.0096 (5)	0.0072 (5)
N3	0.0127 (5)	0.0106 (5)	0.0132 (5)	0.0007 (4)	−0.0050 (4)	−0.0012 (4)
C1	0.0081 (5)	0.0086 (6)	0.0093 (6)	−0.0030 (4)	−0.0030 (4)	0.0005 (4)
C2	0.0112 (6)	0.0097 (6)	0.0097 (6)	−0.0047 (5)	−0.0048 (5)	0.0012 (5)
C3	0.0097 (6)	0.0068 (5)	0.0100 (6)	−0.0020 (4)	−0.0042 (5)	−0.0004 (4)

Geometric parameters (Å, º)

Cu1—O2	1.9339 (10)	N1—C1	1.3135 (18)
Cu1—O2^i	1.9339 (10)	N1—H1N1	0.9000
Cu1—O1	1.9727 (10)	N1—H1N2	0.9000
Cu1—O1^i	1.9727 (10)	N2—C3	1.3078 (18)
Cu1—O3^i	2.3964 (11)	N2—H2N1	0.9001
Cu1—O3	2.3964 (11)	N2—H2N2	0.9000
O1—C1	1.2600 (17)	C1—C2	1.5137 (18)
O2—C3	1.2653 (17)	C2—C3	1.5093 (19)
O3—N3	1.2705 (16)	C2—H2A	0.9900
O4—N3	1.2636 (17)	C2—H2B	0.9900
O5—N3	1.2308 (18)
O2—Cu1—O2^i	180.0	H1N1—N1—H1N2	121.8
O2—Cu1—O1	93.86 (4)	C3—N2—H2N1	115.8
O2^i—Cu1—O1	86.14 (4)	C3—N2—H2N2	117.4
O2—Cu1—O1^i	86.14 (4)	H2N1—N2—H2N2	126.8
O2^i—Cu1—O1^i	93.86 (4)	O5—N3—O4	120.12 (13)
O1—Cu1—O1^i	180.0	O5—N3—O3	121.09 (13)
O2—Cu1—O3^i	90.10 (4)	O4—N3—O3	118.78 (13)
O2^i—Cu1—O3^i	89.90 (4)	O1—C1—N1	122.06 (12)
O1—Cu1—O3^i	89.49 (4)	O1—C1—C2	120.46 (12)
O1^i—Cu1—O3^i	90.51 (4)	N1—C1—C2	117.38 (12)
O2—Cu1—O3	89.90 (4)	C3—C2—C1	111.66 (11)
O2^i—Cu1—O3	90.10 (4)	C3—C2—H2A	109.3
O1—Cu1—O3	90.51 (4)	C1—C2—H2A	109.3
O1^i—Cu1—O3	89.49 (4)	C3—C2—H2B	109.3
O3^i—Cu1—O3	180.0	C1—C2—H2B	109.3
C1—O1—Cu1	122.57 (9)	H2A—C2—H2B	107.9
C3—O2—Cu1	125.11 (9)	O2—C3—N2	120.31 (13)
N3—O3—Cu1	118.15 (9)	O2—C3—C2	120.90 (12)
C1—N1—H1N1	119.5	N2—C3—C2	118.75 (12)
C1—N1—H1N2	117.0
O2—Cu1—O1—C1	10.39 (11)	O1^i—Cu1—O3—N3	120.32 (11)
O2^i—Cu1—O1—C1	−169.61 (11)	Cu1—O3—N3—O5	32.30 (18)
O3^i—Cu1—O1—C1	−79.68 (11)	Cu1—O3—N3—O4	−147.44 (11)
O3—Cu1—O1—C1	100.32 (11)	Cu1—O1—C1—N1	−158.62 (11)
O1—Cu1—O2—C3	−18.42 (11)	Cu1—O1—C1—C2	25.00 (16)
O1^i—Cu1—O2—C3	161.58 (11)	O1—C1—C2—C3	−58.31 (16)
O3^i—Cu1—O2—C3	71.08 (11)	N1—C1—C2—C3	125.15 (13)
O3—Cu1—O2—C3	−108.92 (11)	Cu1—O2—C3—N2	172.87 (10)
O2—Cu1—O3—N3	34.18 (11)	Cu1—O2—C3—C2	−9.65 (18)
O2^i—Cu1—O3—N3	−145.82 (11)	C1—C2—C3—O2	49.38 (17)
O1—Cu1—O3—N3	−59.68 (11)	C1—C2—C3—N2	−133.10 (13)

Symmetry code: (i) −x, −y+2, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1^ii	0.90	2.11	2.990 (2)	164
N2—H2N1···O2^iii	0.90	2.13	3.007 (2)	163
N1—H1N2···O4^iv	0.90	2.23	3.120 (2)	169
N2—H2N2···O4^v	0.90	2.08	2.948 (2)	163

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