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The title compound, [Cu(C4H4NO2)2(C5H6N2)2]·2H2O, has its metal atom in a square-planar trans-[CuN4] coordination environment; the CuII atom lies on a center of symmetry. Both succinimidate and 4-amino­pyridine ligands behave as monodentate ligands, which coordinate through deprotonated imidate and pyridine (not amino) N atoms, respectively. The 4-amino­pyridine is the first ligand in such CuII complexes containing two different N atoms to take potentially different coordination modes.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806006209/ob6607sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806006209/ob6607Isup2.hkl
Contains datablock I

CCDC reference: 601224

Key indicators

  • Single-crystal X-ray study
  • T = 297 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.052
  • wR factor = 0.158
  • Data-to-parameter ratio = 16.9

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.696 0.807 Tmin(prime) and Tmax expected: 0.800 0.805 RR(prime) = 0.868 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.86 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 H2 O
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999); cell refinement: WinAFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1989); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.

trans-Bis(4-aminopyridine-κN)bis(succinimidato-κN)copper(II) dihydrate top
Crystal data top
[Cu(C4H4NO2)2(C5H6N2)2].2H2OZ = 1
Mr = 483.98F(000) = 251.0
Triclinic, P1Dx = 1.521 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.945 (2) ÅCell parameters from 20 reflections
b = 8.729 (3) Åθ = 10.1–13.7°
c = 9.161 (3) ŵ = 1.08 mm1
α = 65.04 (2)°T = 297 K
β = 86.86 (3)°Prism, brown
γ = 67.59 (2)°0.20 × 0.20 × 0.20 mm
V = 528.2 (3) Å3
Data collection top
Rigaku AFC-7R
diffractometer
1771 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anode generatorRint = 0.058
Graphite monochromatorθmax = 27.5°, θmin = 2.8°
ω–2θ scansh = 1110
Absorption correction: ψ scan
(North et al., 1968)
k = 1111
Tmin = 0.696, Tmax = 0.807l = 410
2736 measured reflections3 standard reflections every 150 reflections
2430 independent reflections intensity decay: 0.4%
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)] = 0.052Hydrogen site location: mixed
wR(F2) = 0.158H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0697P)2 + 0.5544P]
where P = (Fo2 + 2Fc2)/3
2430 reflections(Δ/σ)max < 0.001
144 parametersΔρmax = 0.58 e Å3
0 restraintsΔρmin = 0.54 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.00000.00000.00000.0327 (3)
O10.1355 (5)0.0913 (5)0.3077 (5)0.0609 (9)
O20.2430 (6)0.2366 (6)0.0641 (5)0.0742 (12)
O30.3782 (6)0.0535 (5)0.2564 (5)0.0712 (12)
H3E0.337 (2)0.005 (3)0.2640 (6)0.064*
H3F0.325 (3)0.107 (3)0.205 (3)0.064*
N10.0485 (5)0.1353 (4)0.1076 (4)0.0380 (8)
N20.1873 (5)0.2370 (5)0.1653 (4)0.0394 (8)
N30.5537 (6)0.7599 (5)0.4788 (5)0.0515 (10)
H3C0.66020.80710.45250.062*
H3D0.52180.82210.56840.062*
C10.0229 (6)0.1547 (6)0.2387 (5)0.0419 (10)
C20.0534 (7)0.2613 (7)0.2885 (6)0.0520 (12)
H2A0.11560.18880.39870.062*
H2B0.04330.37430.28140.062*
C30.1862 (7)0.3016 (7)0.1694 (7)0.0547 (12)
H3A0.15450.43290.11140.065*
H3B0.31070.24200.22390.065*
C40.1661 (6)0.2235 (6)0.0562 (6)0.0456 (10)
C50.3571 (7)0.3126 (6)0.1324 (6)0.0510 (11)
H5A0.39190.24580.03550.061*
C60.4815 (6)0.4820 (6)0.2333 (6)0.0505 (11)
H6A0.59780.52720.20410.061*
C70.4368 (6)0.5885 (5)0.3795 (5)0.0380 (9)
C80.2613 (6)0.5063 (6)0.4159 (5)0.0407 (9)
H8A0.22440.56810.51380.050*
C90.1447 (6)0.3364 (6)0.3084 (5)0.0431 (10)
H9A0.02850.28610.33560.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0345 (4)0.0288 (4)0.0359 (4)0.0112 (3)0.0048 (3)0.0162 (3)
O10.059 (2)0.065 (2)0.070 (2)0.0301 (19)0.0245 (19)0.036 (2)
O20.086 (3)0.096 (3)0.075 (3)0.056 (3)0.040 (2)0.055 (2)
O30.079 (3)0.070 (3)0.079 (3)0.038 (2)0.034 (2)0.041 (2)
N10.0394 (19)0.0321 (16)0.047 (2)0.0136 (15)0.0048 (15)0.0214 (15)
N20.0421 (19)0.0348 (17)0.0405 (19)0.0141 (15)0.0023 (15)0.0163 (15)
N30.049 (2)0.0365 (19)0.050 (2)0.0081 (17)0.0075 (18)0.0096 (17)
C10.042 (2)0.036 (2)0.046 (2)0.0103 (18)0.0059 (19)0.0211 (19)
C20.062 (3)0.049 (3)0.054 (3)0.018 (2)0.004 (2)0.033 (2)
C30.054 (3)0.053 (3)0.070 (3)0.024 (2)0.004 (2)0.036 (3)
C40.046 (2)0.046 (2)0.052 (3)0.019 (2)0.009 (2)0.027 (2)
C50.050 (3)0.044 (2)0.045 (3)0.018 (2)0.010 (2)0.007 (2)
C60.038 (2)0.042 (2)0.052 (3)0.0065 (19)0.010 (2)0.012 (2)
C70.042 (2)0.034 (2)0.039 (2)0.0159 (17)0.0020 (17)0.0162 (17)
C80.047 (2)0.038 (2)0.038 (2)0.0156 (19)0.0102 (18)0.0181 (18)
C90.041 (2)0.043 (2)0.043 (2)0.0105 (19)0.0080 (19)0.0228 (19)
Geometric parameters (Å, º) top
Cu1—N11.971 (3)C2—C31.503 (7)
Cu1—N22.011 (4)C2—H2A0.9700
O1—C11.235 (6)C2—H2B0.9700
O2—C41.214 (6)C3—C41.505 (6)
O3—H3E0.73 (3)C3—H3A0.9700
O3—H3F0.79 (3)C3—H3B0.9700
N1—C11.349 (6)C5—C61.360 (6)
N1—C41.371 (6)C5—H5A0.9300
N2—C51.339 (6)C6—C71.390 (6)
N2—C91.342 (6)C6—H6A0.9300
N3—C71.346 (5)C7—C81.399 (6)
N3—H3C0.8600C8—C91.359 (6)
N3—H3D0.8600C8—H8A0.9300
C1—C21.503 (6)C9—H9A0.9300
N1—Cu1—N289.93 (14)C4—C3—H3A111.0
H3E—O3—H3F113 (2)C2—C3—H3B111.0
C1—N1—C4110.2 (4)C4—C3—H3B111.0
C1—N1—Cu1127.0 (3)H3A—C3—H3B109.0
C4—N1—Cu1122.8 (3)O2—C4—N1124.6 (4)
C5—N2—C9116.2 (4)O2—C4—C3124.8 (4)
C5—N2—Cu1121.5 (3)N1—C4—C3110.6 (4)
C9—N2—Cu1122.0 (3)N2—C5—C6123.5 (4)
C7—N3—H3C120.0N2—C5—H5A118.2
C7—N3—H3D120.0C6—C5—H5A118.2
H3C—N3—H3D120.0C5—C6—C7120.8 (4)
O1—C1—N1123.6 (4)C5—C6—H6A119.6
O1—C1—C2125.4 (4)C7—C6—H6A119.6
N1—C1—C2111.1 (4)N3—C7—C6122.3 (4)
C3—C2—C1104.2 (4)N3—C7—C8122.2 (4)
C3—C2—H2A110.9C6—C7—C8115.5 (4)
C1—C2—H2A110.9C9—C8—C7120.1 (4)
C3—C2—H2B110.9C9—C8—H8A119.9
C1—C2—H2B110.9C7—C8—H8A119.9
H2A—C2—H2B108.9N2—C9—C8123.9 (4)
C2—C3—C4103.7 (4)N2—C9—H9A118.1
C2—C3—H3A111.0C8—C9—H9A118.1
N2—Cu1—N1—C197.4 (4)Cu1—N1—C4—C3175.6 (3)
N2—Cu1—N1—C483.2 (3)C2—C3—C4—O2175.7 (5)
N1—Cu1—N2—C579.7 (4)C2—C3—C4—N14.3 (5)
N1—Cu1—N2—C994.1 (3)C9—N2—C5—C61.6 (7)
C4—N1—C1—O1178.7 (4)Cu1—N2—C5—C6172.5 (4)
Cu1—N1—C1—O11.9 (6)N2—C5—C6—C70.3 (8)
C4—N1—C1—C21.7 (5)C5—C6—C7—N3177.0 (4)
Cu1—N1—C1—C2177.7 (3)C5—C6—C7—C82.4 (7)
O1—C1—C2—C3178.6 (5)N3—C7—C8—C9176.8 (4)
N1—C1—C2—C31.1 (5)C6—C7—C8—C92.5 (6)
C1—C2—C3—C43.1 (5)C5—N2—C9—C81.5 (6)
C1—N1—C4—O2176.2 (5)Cu1—N2—C9—C8172.7 (3)
Cu1—N1—C4—O24.4 (7)C7—C8—C9—N20.7 (7)
C1—N1—C4—C33.8 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3E···O10.73 (3)2.13 (2)2.827 (5)161 (2)
O3—H3F···O2i0.79 (3)1.99 (2)2.770 (7)168 (2)
N3—H3C···O1ii0.862.203.016 (5)158
N3—H3D···O3iii0.862.082.917 (6)164
Symmetry codes: (i) x, y, z; (ii) x+1, y1, z; (iii) x, y1, z+1.
 

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