trans-Bis(4-amino­pyridine-κN)bis­(succinimidato-κN)copper(II) dihydrate

The title compound, [Cu(C₄H₄NO₂)₂(C₅H₆N₂)₂]·2H₂O, has its metal atom in a square-planar trans-[CuN₄] coordination environment; the Cu^II 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 Cu^II complexes containing two different N atoms to take potentially different coordination modes.

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

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Computing details

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

Crystal data

[Cu(C4H4NO2)2(C5H6N2)2].2H2O	Z = 1
Mr = 483.98	F(000) = 251.0
Triclinic, P1	Dx = 1.521 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.945 (2) Å	Cell parameters from 20 reflections
b = 8.729 (3) Å	θ = 10.1–13.7°
c = 9.161 (3) Å	µ = 1.08 mm^−1
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) Å^3

Data collection

Rigaku AFC-7R diffractometer	1771 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anode generator	Rint = 0.058
Graphite monochromator	θmax = 27.5°, θmin = 2.8°
ω–2θ scans	h = −11→10
Absorption correction: ψ scan (North et al., 1968)	k = −11→11
Tmin = 0.696, Tmax = 0.807	l = −4→10
2736 measured reflections	3 standard reflections every 150 reflections
2430 independent reflections	intensity decay: 0.4%

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)] = 0.052	Hydrogen site location: mixed
wR(F^2) = 0.158	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0697P)^2 + 0.5544P] where P = (Fo^2 + 2Fc^2)/3
2430 reflections	(Δ/σ)max < 0.001
144 parameters	Δρmax = 0.58 e Å^−3
0 restraints	Δρmin = −0.54 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.0000	0.0000	0.0000	0.0327 (3)
O1	0.1355 (5)	−0.0913 (5)	−0.3077 (5)	0.0609 (9)
O2	−0.2430 (6)	−0.2366 (6)	0.0641 (5)	0.0742 (12)
O3	0.3782 (6)	0.0535 (5)	−0.2564 (5)	0.0712 (12)
H3E	0.337 (2)	−0.005 (3)	−0.2640 (6)	0.064*
H3F	0.325 (3)	0.107 (3)	−0.205 (3)	0.064*
N1	−0.0485 (5)	−0.1353 (4)	−0.1076 (4)	0.0380 (8)
N2	0.1873 (5)	−0.2370 (5)	0.1653 (4)	0.0394 (8)
N3	0.5537 (6)	−0.7599 (5)	0.4788 (5)	0.0515 (10)
H3C	0.6602	−0.8071	0.4525	0.062*
H3D	0.5218	−0.8221	0.5684	0.062*
C1	0.0229 (6)	−0.1547 (6)	−0.2387 (5)	0.0419 (10)
C2	−0.0534 (7)	−0.2613 (7)	−0.2885 (6)	0.0520 (12)
H2A	−0.1156	−0.1888	−0.3987	0.062*
H2B	0.0433	−0.3743	−0.2814	0.062*
C3	−0.1862 (7)	−0.3016 (7)	−0.1694 (7)	0.0547 (12)
H3A	−0.1545	−0.4329	−0.1114	0.065*
H3B	−0.3107	−0.2420	−0.2239	0.065*
C4	−0.1661 (6)	−0.2235 (6)	−0.0562 (6)	0.0456 (10)
C5	0.3571 (7)	−0.3126 (6)	0.1324 (6)	0.0510 (11)
H5A	0.3919	−0.2458	0.0355	0.061*
C6	0.4815 (6)	−0.4820 (6)	0.2333 (6)	0.0505 (11)
H6A	0.5978	−0.5272	0.2041	0.061*
C7	0.4368 (6)	−0.5885 (5)	0.3795 (5)	0.0380 (9)
C8	0.2613 (6)	−0.5063 (6)	0.4159 (5)	0.0407 (9)
H8A	0.2244	−0.5681	0.5138	0.050*
C9	0.1447 (6)	−0.3364 (6)	0.3084 (5)	0.0431 (10)
H9A	0.0285	−0.2861	0.3356	0.052*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0345 (4)	0.0288 (4)	0.0359 (4)	−0.0112 (3)	0.0048 (3)	−0.0162 (3)
O1	0.059 (2)	0.065 (2)	0.070 (2)	−0.0301 (19)	0.0245 (19)	−0.036 (2)
O2	0.086 (3)	0.096 (3)	0.075 (3)	−0.056 (3)	0.040 (2)	−0.055 (2)
O3	0.079 (3)	0.070 (3)	0.079 (3)	−0.038 (2)	0.034 (2)	−0.041 (2)
N1	0.0394 (19)	0.0321 (16)	0.047 (2)	−0.0136 (15)	0.0048 (15)	−0.0214 (15)
N2	0.0421 (19)	0.0348 (17)	0.0405 (19)	−0.0141 (15)	0.0023 (15)	−0.0163 (15)
N3	0.049 (2)	0.0365 (19)	0.050 (2)	−0.0081 (17)	0.0075 (18)	−0.0096 (17)
C1	0.042 (2)	0.036 (2)	0.046 (2)	−0.0103 (18)	0.0059 (19)	−0.0211 (19)
C2	0.062 (3)	0.049 (3)	0.054 (3)	−0.018 (2)	0.004 (2)	−0.033 (2)
C3	0.054 (3)	0.053 (3)	0.070 (3)	−0.024 (2)	0.004 (2)	−0.036 (3)
C4	0.046 (2)	0.046 (2)	0.052 (3)	−0.019 (2)	0.009 (2)	−0.027 (2)
C5	0.050 (3)	0.044 (2)	0.045 (3)	−0.018 (2)	0.010 (2)	−0.007 (2)
C6	0.038 (2)	0.042 (2)	0.052 (3)	−0.0065 (19)	0.010 (2)	−0.012 (2)
C7	0.042 (2)	0.034 (2)	0.039 (2)	−0.0159 (17)	0.0020 (17)	−0.0162 (17)
C8	0.047 (2)	0.038 (2)	0.038 (2)	−0.0156 (19)	0.0102 (18)	−0.0181 (18)
C9	0.041 (2)	0.043 (2)	0.043 (2)	−0.0105 (19)	0.0080 (19)	−0.0228 (19)

Geometric parameters (Å, º)

Cu1—N1	1.971 (3)	C2—C3	1.503 (7)
Cu1—N2	2.011 (4)	C2—H2A	0.9700
O1—C1	1.235 (6)	C2—H2B	0.9700
O2—C4	1.214 (6)	C3—C4	1.505 (6)
O3—H3E	0.73 (3)	C3—H3A	0.9700
O3—H3F	0.79 (3)	C3—H3B	0.9700
N1—C1	1.349 (6)	C5—C6	1.360 (6)
N1—C4	1.371 (6)	C5—H5A	0.9300
N2—C5	1.339 (6)	C6—C7	1.390 (6)
N2—C9	1.342 (6)	C6—H6A	0.9300
N3—C7	1.346 (5)	C7—C8	1.399 (6)
N3—H3C	0.8600	C8—C9	1.359 (6)
N3—H3D	0.8600	C8—H8A	0.9300
C1—C2	1.503 (6)	C9—H9A	0.9300
N1—Cu1—N2	89.93 (14)	C4—C3—H3A	111.0
H3E—O3—H3F	113 (2)	C2—C3—H3B	111.0
C1—N1—C4	110.2 (4)	C4—C3—H3B	111.0
C1—N1—Cu1	127.0 (3)	H3A—C3—H3B	109.0
C4—N1—Cu1	122.8 (3)	O2—C4—N1	124.6 (4)
C5—N2—C9	116.2 (4)	O2—C4—C3	124.8 (4)
C5—N2—Cu1	121.5 (3)	N1—C4—C3	110.6 (4)
C9—N2—Cu1	122.0 (3)	N2—C5—C6	123.5 (4)
C7—N3—H3C	120.0	N2—C5—H5A	118.2
C7—N3—H3D	120.0	C6—C5—H5A	118.2
H3C—N3—H3D	120.0	C5—C6—C7	120.8 (4)
O1—C1—N1	123.6 (4)	C5—C6—H6A	119.6
O1—C1—C2	125.4 (4)	C7—C6—H6A	119.6
N1—C1—C2	111.1 (4)	N3—C7—C6	122.3 (4)
C3—C2—C1	104.2 (4)	N3—C7—C8	122.2 (4)
C3—C2—H2A	110.9	C6—C7—C8	115.5 (4)
C1—C2—H2A	110.9	C9—C8—C7	120.1 (4)
C3—C2—H2B	110.9	C9—C8—H8A	119.9
C1—C2—H2B	110.9	C7—C8—H8A	119.9
H2A—C2—H2B	108.9	N2—C9—C8	123.9 (4)
C2—C3—C4	103.7 (4)	N2—C9—H9A	118.1
C2—C3—H3A	111.0	C8—C9—H9A	118.1
N2—Cu1—N1—C1	−97.4 (4)	Cu1—N1—C4—C3	175.6 (3)
N2—Cu1—N1—C4	83.2 (3)	C2—C3—C4—O2	−175.7 (5)
N1—Cu1—N2—C5	79.7 (4)	C2—C3—C4—N1	4.3 (5)
N1—Cu1—N2—C9	−94.1 (3)	C9—N2—C5—C6	1.6 (7)
C4—N1—C1—O1	−178.7 (4)	Cu1—N2—C5—C6	−172.5 (4)
Cu1—N1—C1—O1	1.9 (6)	N2—C5—C6—C7	0.3 (8)
C4—N1—C1—C2	1.7 (5)	C5—C6—C7—N3	177.0 (4)
Cu1—N1—C1—C2	−177.7 (3)	C5—C6—C7—C8	−2.4 (7)
O1—C1—C2—C3	−178.6 (5)	N3—C7—C8—C9	−176.8 (4)
N1—C1—C2—C3	1.1 (5)	C6—C7—C8—C9	2.5 (6)
C1—C2—C3—C4	−3.1 (5)	C5—N2—C9—C8	−1.5 (6)
C1—N1—C4—O2	176.2 (5)	Cu1—N2—C9—C8	172.7 (3)
Cu1—N1—C4—O2	−4.4 (7)	C7—C8—C9—N2	−0.7 (7)
C1—N1—C4—C3	−3.8 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3E···O1	0.73 (3)	2.13 (2)	2.827 (5)	161 (2)
O3—H3F···O2^i	0.79 (3)	1.99 (2)	2.770 (7)	168 (2)
N3—H3C···O1^ii	0.86	2.20	3.016 (5)	158
N3—H3D···O3^iii	0.86	2.08	2.917 (6)	164

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