The title complex, [Cu(NO
3)
2(C
3H
6N
2O
2)
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 NO
3 groups in a distorted octahedral geometry. The crystal packing is stabilized by intermolecular N—H
O hydrogen bonds.
Supporting information
CCDC reference: 627479
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (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
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 = 391.76 | 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) Å3 | 0.25 × 0.25 × 0.15 mm |
Data collection top
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 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)] = 0.024 | Hydrogen site location: mixed |
wR(F2) = 0.059 | H-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 parameters | Δρmax = 0.41 e Å−3 |
0 restraints | Δρmin = −0.64 e Å−3 |
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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
Cu1—O2 | 1.9339 (10) | N1—C1 | 1.3135 (18) |
Cu1—O2i | 1.9339 (10) | N1—H1N1 | 0.9000 |
Cu1—O1 | 1.9727 (10) | N1—H1N2 | 0.9000 |
Cu1—O1i | 1.9727 (10) | N2—C3 | 1.3078 (18) |
Cu1—O3i | 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—O2i | 180.0 | H1N1—N1—H1N2 | 121.8 |
O2—Cu1—O1 | 93.86 (4) | C3—N2—H2N1 | 115.8 |
O2i—Cu1—O1 | 86.14 (4) | C3—N2—H2N2 | 117.4 |
O2—Cu1—O1i | 86.14 (4) | H2N1—N2—H2N2 | 126.8 |
O2i—Cu1—O1i | 93.86 (4) | O5—N3—O4 | 120.12 (13) |
O1—Cu1—O1i | 180.0 | O5—N3—O3 | 121.09 (13) |
O2—Cu1—O3i | 90.10 (4) | O4—N3—O3 | 118.78 (13) |
O2i—Cu1—O3i | 89.90 (4) | O1—C1—N1 | 122.06 (12) |
O1—Cu1—O3i | 89.49 (4) | O1—C1—C2 | 120.46 (12) |
O1i—Cu1—O3i | 90.51 (4) | N1—C1—C2 | 117.38 (12) |
O2—Cu1—O3 | 89.90 (4) | C3—C2—C1 | 111.66 (11) |
O2i—Cu1—O3 | 90.10 (4) | C3—C2—H2A | 109.3 |
O1—Cu1—O3 | 90.51 (4) | C1—C2—H2A | 109.3 |
O1i—Cu1—O3 | 89.49 (4) | C3—C2—H2B | 109.3 |
O3i—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) | O1i—Cu1—O3—N3 | 120.32 (11) |
O2i—Cu1—O1—C1 | −169.61 (11) | Cu1—O3—N3—O5 | 32.30 (18) |
O3i—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) |
O1i—Cu1—O2—C3 | 161.58 (11) | O1—C1—C2—C3 | −58.31 (16) |
O3i—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) |
O2i—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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N1···O1ii | 0.90 | 2.11 | 2.990 (2) | 164 |
N2—H2N1···O2iii | 0.90 | 2.13 | 3.007 (2) | 163 |
N1—H1N2···O4iv | 0.90 | 2.23 | 3.120 (2) | 169 |
N2—H2N2···O4v | 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. |