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In the title mononuclear copper(II) complex, [Cu(C12H17N3O3)2](NO3)2, the CuII ion, lying on an inversion centre, is four-coordinated in a square-planar geometry by two phenolate O atoms and two imine N atoms from two Schiff base ligands. In the crystal structure, mol­ecules are linked through inter­molecular N—H...O hydrogen bonds, forming a network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807001353/at2206sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807001353/at2206Isup2.hkl
Contains datablock I

CCDC reference: 636123

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.048
  • wR factor = 0.123
  • Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.71 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.30 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N4
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Bis{4-nitro-2-[2-(isopropylamino)ethyliminomethyl]phenolato}copper(II) dinitrate top
Crystal data top
[Cu(C12H17N3O3)2](NO3)2F(000) = 718
Mr = 690.13Dx = 1.523 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2520 reflections
a = 7.710 (1) Åθ = 2.4–24.9°
b = 21.608 (2) ŵ = 0.80 mm1
c = 9.075 (1) ÅT = 298 K
β = 95.434 (2)°Block, blue
V = 1505.1 (3) Å30.18 × 0.12 × 0.06 mm
Z = 2
Data collection top
Bruker SMART CCD area-detector
diffractometer
3394 independent reflections
Radiation source: fine-focus sealed tube2630 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
ω scansθmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 99
Tmin = 0.869, Tmax = 0.954k = 2727
11622 measured reflectionsl = 1111
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0565P)2 + 0.6314P]
where P = (Fo2 + 2Fc2)/3
3394 reflections(Δ/σ)max < 0.001
207 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = 0.26 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
Cu11.00001.00000.50000.03829 (16)
O10.9944 (3)1.06093 (9)0.3494 (2)0.0565 (6)
O20.7860 (3)1.09947 (14)0.3200 (3)0.0824 (8)
O30.6231 (4)1.02057 (12)0.2817 (3)0.0881 (9)
O40.1580 (4)0.25815 (12)0.4210 (3)0.0854 (8)
O50.1065 (4)0.25720 (12)0.1863 (3)0.0917 (9)
O60.0009 (3)0.32855 (11)0.3104 (3)0.0739 (7)
N10.8464 (3)0.94340 (9)0.3698 (2)0.0349 (5)
N20.5724 (3)0.82970 (9)0.5556 (2)0.0396 (5)
H2A0.66000.80490.59210.048*
H2B0.52300.81220.47200.048*
N30.7305 (4)1.06067 (13)0.2390 (3)0.0595 (7)
N40.0882 (3)0.28118 (11)0.3062 (3)0.0525 (6)
C10.8225 (3)1.01080 (11)0.1529 (3)0.0373 (6)
C20.9265 (4)1.06014 (12)0.2137 (3)0.0410 (6)
C30.9583 (4)1.11024 (13)0.1198 (3)0.0503 (7)
H31.02441.14350.15800.060*
C40.8944 (4)1.11087 (13)0.0254 (3)0.0504 (7)
H40.91821.14390.08590.060*
C50.7934 (4)1.06165 (13)0.0821 (3)0.0457 (7)
C60.7552 (4)1.01276 (12)0.0047 (3)0.0432 (6)
H60.68460.98080.03500.052*
C70.7897 (3)0.95576 (11)0.2360 (3)0.0386 (6)
H70.71940.92590.18670.046*
C80.7961 (3)0.88219 (11)0.4234 (3)0.0385 (6)
H8A0.89430.86320.48120.046*
H8B0.76100.85540.34010.046*
C90.6465 (4)0.89043 (11)0.5180 (3)0.0421 (6)
H9A0.68720.91210.60830.051*
H9B0.55640.91540.46500.051*
C100.4388 (4)0.83287 (14)0.6661 (3)0.0526 (7)
H100.34630.86160.62940.063*
C110.5199 (5)0.85551 (18)0.8123 (4)0.0748 (10)
H11A0.61270.82820.84790.112*
H11B0.43350.85650.88190.112*
H11C0.56540.89640.80100.112*
C120.3611 (6)0.7688 (2)0.6795 (5)0.1011 (16)
H12A0.30710.75600.58470.152*
H12B0.27540.76990.74960.152*
H12C0.45150.74010.71250.152*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0404 (3)0.0332 (2)0.0394 (3)0.00963 (19)0.00617 (18)0.00462 (18)
O10.0723 (15)0.0435 (11)0.0485 (11)0.0237 (10)0.0214 (10)0.0129 (9)
O20.0758 (17)0.125 (2)0.0481 (13)0.0210 (16)0.0153 (12)0.0313 (14)
O30.143 (3)0.0625 (15)0.0515 (14)0.0137 (17)0.0290 (15)0.0055 (12)
O40.105 (2)0.0807 (17)0.0663 (15)0.0351 (16)0.0118 (14)0.0210 (13)
O50.129 (3)0.0749 (17)0.0721 (17)0.0082 (17)0.0159 (17)0.0148 (14)
O60.0619 (15)0.0629 (14)0.0944 (18)0.0184 (12)0.0058 (13)0.0155 (13)
N10.0325 (11)0.0310 (10)0.0403 (11)0.0059 (8)0.0006 (9)0.0022 (8)
N20.0428 (13)0.0339 (11)0.0420 (12)0.0046 (9)0.0039 (10)0.0009 (9)
N30.0722 (19)0.0645 (17)0.0409 (14)0.0301 (15)0.0012 (13)0.0020 (13)
N40.0532 (16)0.0464 (14)0.0566 (15)0.0058 (12)0.0015 (12)0.0025 (12)
C10.0352 (14)0.0342 (13)0.0417 (13)0.0018 (10)0.0000 (11)0.0013 (10)
C20.0393 (15)0.0387 (14)0.0441 (14)0.0033 (11)0.0015 (11)0.0053 (11)
C30.0516 (17)0.0425 (15)0.0553 (17)0.0061 (13)0.0031 (14)0.0098 (12)
C40.0495 (18)0.0476 (16)0.0544 (17)0.0069 (13)0.0067 (14)0.0186 (13)
C50.0464 (16)0.0522 (16)0.0387 (14)0.0168 (13)0.0047 (12)0.0035 (12)
C60.0455 (16)0.0390 (14)0.0440 (15)0.0069 (11)0.0022 (12)0.0040 (11)
C70.0346 (14)0.0354 (13)0.0450 (14)0.0042 (10)0.0011 (11)0.0047 (10)
C80.0404 (14)0.0303 (12)0.0441 (14)0.0075 (10)0.0006 (11)0.0008 (10)
C90.0461 (16)0.0295 (12)0.0512 (15)0.0036 (11)0.0067 (12)0.0013 (11)
C100.0489 (17)0.0531 (17)0.0579 (18)0.0046 (14)0.0160 (14)0.0025 (13)
C110.088 (3)0.081 (2)0.058 (2)0.016 (2)0.0251 (19)0.0086 (18)
C120.118 (4)0.092 (3)0.102 (3)0.059 (3)0.056 (3)0.013 (2)
Geometric parameters (Å, º) top
Cu1—O11.895 (2)C3—C41.362 (4)
Cu1—O1i1.895 (2)C3—H30.9300
Cu1—N1i2.007 (2)C4—C51.388 (4)
Cu1—N12.007 (2)C4—H40.9300
O1—C21.292 (3)C5—C61.366 (4)
O2—N31.219 (3)C6—H60.9300
O3—N31.235 (4)C7—H70.9300
O4—N41.232 (3)C8—C91.512 (3)
O5—N41.226 (3)C8—H8A0.9700
O6—N41.228 (3)C8—H8B0.9700
N1—C71.279 (3)C9—H9A0.9700
N1—C81.474 (3)C9—H9B0.9700
N2—C91.484 (3)C10—C111.494 (5)
N2—C101.505 (4)C10—C121.517 (4)
N2—H2A0.9000C10—H100.9800
N2—H2B0.9000C11—H11A0.9600
N3—C51.461 (4)C11—H11B0.9600
C1—C61.396 (4)C11—H11C0.9600
C1—C21.414 (4)C12—H12A0.9600
C1—C71.443 (3)C12—H12B0.9600
C2—C31.413 (4)C12—H12C0.9600
O1—Cu1—O1i180.0C5—C6—C1119.9 (3)
O1—Cu1—N1i88.45 (8)C5—C6—H6120.1
O1i—Cu1—N1i91.55 (8)C1—C6—H6120.1
O1—Cu1—N191.55 (8)N1—C7—C1127.4 (2)
O1i—Cu1—N188.45 (8)N1—C7—H7116.3
N1i—Cu1—N1180.0C1—C7—H7116.3
C2—O1—Cu1131.12 (17)N1—C8—C9108.7 (2)
C7—N1—C8115.1 (2)N1—C8—H8A109.9
C7—N1—Cu1124.12 (17)C9—C8—H8A109.9
C8—N1—Cu1120.78 (16)N1—C8—H8B109.9
C9—N2—C10114.6 (2)C9—C8—H8B109.9
C9—N2—H2A108.6H8A—C8—H8B108.3
C10—N2—H2A108.6N2—C9—C8111.0 (2)
C9—N2—H2B108.6N2—C9—H9A109.4
C10—N2—H2B108.6C8—C9—H9A109.4
H2A—N2—H2B107.6N2—C9—H9B109.4
O2—N3—O3123.8 (3)C8—C9—H9B109.4
O2—N3—C5118.4 (3)H9A—C9—H9B108.0
O3—N3—C5117.8 (3)C11—C10—N2110.6 (3)
O5—N4—O6119.3 (3)C11—C10—C12111.3 (3)
O5—N4—O4120.2 (3)N2—C10—C12108.2 (3)
O6—N4—O4120.5 (3)C11—C10—H10108.9
C6—C1—C2119.9 (2)N2—C10—H10108.9
C6—C1—C7117.5 (2)C12—C10—H10108.9
C2—C1—C7122.6 (2)C10—C11—H11A109.5
O1—C2—C3119.1 (2)C10—C11—H11B109.5
O1—C2—C1123.1 (2)H11A—C11—H11B109.5
C3—C2—C1117.8 (2)C10—C11—H11C109.5
C4—C3—C2121.5 (3)H11A—C11—H11C109.5
C4—C3—H3119.2H11B—C11—H11C109.5
C2—C3—H3119.2C10—C12—H12A109.5
C3—C4—C5119.3 (3)C10—C12—H12B109.5
C3—C4—H4120.3H12A—C12—H12B109.5
C5—C4—H4120.3C10—C12—H12C109.5
C6—C5—C4121.5 (3)H12A—C12—H12C109.5
C6—C5—N3118.8 (3)H12B—C12—H12C109.5
C4—C5—N3119.7 (3)
Symmetry code: (i) x+2, y+2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···O5ii0.902.052.933 (4)167
N2—H2A···O4iii0.901.972.808 (3)155
Symmetry codes: (ii) x+1/2, y+1/2, z+1/2; (iii) x+1, y+1, z+1.
 

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