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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806043649/cv2140sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806043649/cv2140Isup2.hkl
Contains datablock I

CCDC reference: 627479

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

Computing details top

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) top
Crystal data top
[Cu(NO3)2(C3H6N2O2)2]Z = 1
Mr = 391.76F(000) = 199
Triclinic, P1Dx = 2.016 Mg m3
a = 6.8515 (7) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.0698 (7) ÅCell parameters from 3216 reflections
c = 7.4611 (8) Åθ = 5.9–58.1°
α = 89.661 (2)°µ = 1.77 mm1
β = 69.488 (2)°T = 120 K
γ = 73.482 (2)°Prism, blue
V = 322.75 (6) Å30.25 × 0.25 × 0.15 mm
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
1683 independent reflections
Radiation source: normal-focus sealed tube1663 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
φ and ω scansθmax = 29.0°, θmin = 2.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1998)
h = 99
Tmin = 0.617, Tmax = 0.767k = 99
3545 measured reflectionsl = 1010
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)] = 0.024Hydrogen site location: mixed
wR(F2) = 0.059H-atom parameters constrained
S = 0.98 w = 1/[σ2(Fo2) + (0.028P)2 + 0.35P]
where P = (Fo2 + 2Fc2)/3
1683 reflections(Δ/σ)max < 0.001
106 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = 0.64 e Å3
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
xyzUiso*/Ueq
Cu10.00001.00000.00000.00848 (8)
O10.03601 (16)0.74677 (14)0.09604 (14)0.01006 (19)
O20.23839 (17)0.98711 (15)0.08616 (15)0.0117 (2)
O30.25675 (18)0.82833 (17)0.30433 (16)0.0166 (2)
O40.60326 (18)0.67245 (18)0.45171 (17)0.0199 (2)
O50.4290 (2)0.5973 (2)0.17164 (18)0.0260 (3)
N10.0907 (2)0.46707 (18)0.21923 (19)0.0127 (2)
H1N10.05610.39450.14300.015*
H1N20.17600.41010.28500.015*
N20.4614 (2)0.86562 (19)0.24476 (19)0.0140 (2)
H2N10.55440.92350.16450.017*
H2N20.48150.79540.34120.017*
N30.4294 (2)0.69770 (18)0.30704 (18)0.0130 (2)
C10.0589 (2)0.6576 (2)0.20339 (19)0.0086 (2)
C20.1291 (2)0.7710 (2)0.32874 (19)0.0096 (2)
H2A0.00170.86780.42280.012*
H2B0.20190.67730.40150.012*
C30.2834 (2)0.87926 (19)0.21088 (19)0.0088 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.00921 (12)0.00720 (12)0.01215 (12)0.00345 (8)0.00684 (9)0.00281 (8)
O10.0117 (4)0.0084 (4)0.0131 (5)0.0038 (3)0.0074 (4)0.0025 (3)
O20.0121 (4)0.0128 (5)0.0153 (5)0.0065 (4)0.0088 (4)0.0067 (4)
O30.0141 (5)0.0171 (5)0.0143 (5)0.0041 (4)0.0067 (4)0.0007 (4)
O40.0131 (5)0.0228 (6)0.0169 (5)0.0003 (4)0.0014 (4)0.0049 (4)
O50.0220 (6)0.0261 (6)0.0178 (6)0.0055 (5)0.0030 (5)0.0089 (5)
N10.0172 (6)0.0083 (5)0.0169 (6)0.0048 (4)0.0105 (5)0.0024 (4)
N20.0132 (6)0.0172 (6)0.0168 (6)0.0074 (5)0.0096 (5)0.0072 (5)
N30.0127 (5)0.0106 (5)0.0132 (5)0.0007 (4)0.0050 (4)0.0012 (4)
C10.0081 (5)0.0086 (6)0.0093 (6)0.0030 (4)0.0030 (4)0.0005 (4)
C20.0112 (6)0.0097 (6)0.0097 (6)0.0047 (5)0.0048 (5)0.0012 (5)
C30.0097 (6)0.0068 (5)0.0100 (6)0.0020 (4)0.0042 (5)0.0004 (4)
Geometric parameters (Å, º) top
Cu1—O21.9339 (10)N1—C11.3135 (18)
Cu1—O2i1.9339 (10)N1—H1N10.9000
Cu1—O11.9727 (10)N1—H1N20.9000
Cu1—O1i1.9727 (10)N2—C31.3078 (18)
Cu1—O3i2.3964 (11)N2—H2N10.9001
Cu1—O32.3964 (11)N2—H2N20.9000
O1—C11.2600 (17)C1—C21.5137 (18)
O2—C31.2653 (17)C2—C31.5093 (19)
O3—N31.2705 (16)C2—H2A0.9900
O4—N31.2636 (17)C2—H2B0.9900
O5—N31.2308 (18)
O2—Cu1—O2i180.0H1N1—N1—H1N2121.8
O2—Cu1—O193.86 (4)C3—N2—H2N1115.8
O2i—Cu1—O186.14 (4)C3—N2—H2N2117.4
O2—Cu1—O1i86.14 (4)H2N1—N2—H2N2126.8
O2i—Cu1—O1i93.86 (4)O5—N3—O4120.12 (13)
O1—Cu1—O1i180.0O5—N3—O3121.09 (13)
O2—Cu1—O3i90.10 (4)O4—N3—O3118.78 (13)
O2i—Cu1—O3i89.90 (4)O1—C1—N1122.06 (12)
O1—Cu1—O3i89.49 (4)O1—C1—C2120.46 (12)
O1i—Cu1—O3i90.51 (4)N1—C1—C2117.38 (12)
O2—Cu1—O389.90 (4)C3—C2—C1111.66 (11)
O2i—Cu1—O390.10 (4)C3—C2—H2A109.3
O1—Cu1—O390.51 (4)C1—C2—H2A109.3
O1i—Cu1—O389.49 (4)C3—C2—H2B109.3
O3i—Cu1—O3180.0C1—C2—H2B109.3
C1—O1—Cu1122.57 (9)H2A—C2—H2B107.9
C3—O2—Cu1125.11 (9)O2—C3—N2120.31 (13)
N3—O3—Cu1118.15 (9)O2—C3—C2120.90 (12)
C1—N1—H1N1119.5N2—C3—C2118.75 (12)
C1—N1—H1N2117.0
O2—Cu1—O1—C110.39 (11)O1i—Cu1—O3—N3120.32 (11)
O2i—Cu1—O1—C1169.61 (11)Cu1—O3—N3—O532.30 (18)
O3i—Cu1—O1—C179.68 (11)Cu1—O3—N3—O4147.44 (11)
O3—Cu1—O1—C1100.32 (11)Cu1—O1—C1—N1158.62 (11)
O1—Cu1—O2—C318.42 (11)Cu1—O1—C1—C225.00 (16)
O1i—Cu1—O2—C3161.58 (11)O1—C1—C2—C358.31 (16)
O3i—Cu1—O2—C371.08 (11)N1—C1—C2—C3125.15 (13)
O3—Cu1—O2—C3108.92 (11)Cu1—O2—C3—N2172.87 (10)
O2—Cu1—O3—N334.18 (11)Cu1—O2—C3—C29.65 (18)
O2i—Cu1—O3—N3145.82 (11)C1—C2—C3—O249.38 (17)
O1—Cu1—O3—N359.68 (11)C1—C2—C3—N2133.10 (13)
Symmetry code: (i) x, y+2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N1···O1ii0.902.112.990 (2)164
N2—H2N1···O2iii0.902.133.007 (2)163
N1—H1N2···O4iv0.902.233.120 (2)169
N2—H2N2···O4v0.902.082.948 (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.
 

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