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The cobalt(II) and nickel(II) cupferronato (N-nitroso-N-phenylhydroxylaminato) mixed-ligand complexes of 2-aminopyridine (2-NH2py) [Co(PhN2O2)2(2-NH2py)2] (1), [Ni(PhN2O2)2(2-NH2py)2] (2) and 2,6-diamino-4-phenyl-1,3,5-triazine (dpt) [Co(PhN2O2)2(dpt)2]·[Co(PhN2O2)2(EtOH)2] (3) have been synthesized and characterized by X-­ray diffraction analysis. The cobalt (1) and nickel (2) complexes are isostructural. The crystal lattice of (3) contains different neutral cobalt(II) complexes [Co(PhN2O2)2(dpt)2] (3a) and [Co(PhN2O2)2(EtOH)2] (3b). Molecules of (1)–(3) contain octahedral metal centres with all-cis-(1) and -(2) and all-trans-(3) disposal of the ligands. Intramolecular N—H...O hydrogen bonding between the NH2 groups and the O atom of the cupferronato anion can be observed in (1)–(3). Intermolecular N—H...O and N—H...N interactions between symmetry-related molecules of (1) and (2) led to hexameric aggregates which connect through common edges into a two-dimensional supramolecular network of hexagonal-grid type. In complex (3) the self-complementary dpt units of the (3a) molecules are maintained by intermolecular N—H...N hydrogen bonds, generating infinite chains. These (3a) chains are crosslinked by the (3b) subunits via N—H...O and O—H...N hydrogen bonds, thus completing the parallel two-dimensional supramolecular network consisting of pseudo-hexagonal-grid sheets. In each crystal structure the two-dimensional supramolecular networks are controlled by both hydrogen bonds and π...π stacking interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768101004426/de0010sup1.cif
Contains datablocks global, coapir, niapir, codpt

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768101004426/de0010coapirsup2.hkl
Contains datablock coapir

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768101004426/de0010niapirsup3.hkl
Contains datablock niapir

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768101004426/de0010codptsup4.hkl
Contains datablock codpt

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768101004426/de0010coapir1sup5.hkl
Contains datablock coapir

CCDC references: 143826; 143827; 166495

Refinement top

C1D is disordered over two sites

Computing details top

For all compounds, data collection: CAD-4 EXPRESS; cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
(coapir) 'di(2-aminopyridine)-bis(N-nitroso-N-phenylhydroxylaminato)-cobalt(II)' top
Crystal data top
C22H22CoN8O4F(000) = 1076
Mr = 521.41Dx = 1.446 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 8.270 (1) ÅCell parameters from 25 reflections
b = 11.579 (2) Åθ = 15.0–16.5°
c = 25.019 (4) ŵ = 0.76 mm1
β = 91.42 (2)°T = 293 K
V = 2395.0 (6) Å3Prism, red
Z = 40.45 × 0.40 × 0.40 mm
Data collection top
Enraf-Nonius CAD4
diffractometer
3093 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.015
Graphite monochromatorθmax = 28.0°, θmin = 2.6°
ω–2θ scansh = 100
Absorption correction: ψ scan
MolEN, Structure Determination System. Enraf-Nonius, 1990)
k = 150
Tmin = 0.945, Tmax = 1l = 3333
6214 measured reflections3 standard reflections every 60 min
5671 independent reflections intensity decay: 2%
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.041 w = 1/[σ2(Fo2) + (0.0635P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.113(Δ/σ)max = 0.002
S = 0.96Δρmax = 0.32 e Å3
5671 reflectionsΔρmin = 0.28 e Å3
316 parameters
Crystal data top
C22H22CoN8O4V = 2395.0 (6) Å3
Mr = 521.41Z = 4
Monoclinic, P21/nMo Kα radiation
a = 8.270 (1) ŵ = 0.76 mm1
b = 11.579 (2) ÅT = 293 K
c = 25.019 (4) Å0.45 × 0.40 × 0.40 mm
β = 91.42 (2)°
Data collection top
Enraf-Nonius CAD4
diffractometer
3093 reflections with I > 2σ(I)
Absorption correction: ψ scan
MolEN, Structure Determination System. Enraf-Nonius, 1990)
Rint = 0.015
Tmin = 0.945, Tmax = 13 standard reflections every 60 min
6214 measured reflections intensity decay: 2%
5671 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.113H atoms treated by a mixture of independent and constrained refinement
S = 0.96Δρmax = 0.32 e Å3
5671 reflectionsΔρmin = 0.28 e Å3
316 parameters
Special details top

Experimental. this compound is isostructural with the analogous Ni(II) complex

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
Co10.66666 (4)0.41944 (3)0.872180 (12)0.05022 (12)
O1A0.4982 (2)0.35131 (16)0.81839 (7)0.0627 (5)
O2A0.4501 (2)0.50908 (16)0.88450 (7)0.0646 (5)
N1A0.3784 (2)0.42418 (17)0.81123 (8)0.0507 (5)
N2A0.3473 (3)0.50499 (19)0.84483 (8)0.0607 (5)
C1A0.2742 (3)0.4112 (2)0.76493 (9)0.0529 (6)
C2A0.1309 (3)0.4716 (3)0.76034 (12)0.0727 (8)
H2A0.10060.52250.78700.095*
C3A0.0341 (4)0.4552 (3)0.71583 (15)0.0924 (11)
H3A0.06380.49440.71280.120*
C4A0.0781 (4)0.3827 (4)0.67607 (14)0.0926 (11)
H4A0.01220.37400.64570.120*
C5A0.2211 (4)0.3221 (4)0.68109 (12)0.0924 (11)
H5A0.25060.27080.65440.120*
C6A0.3197 (3)0.3373 (3)0.72513 (11)0.0717 (8)
H6A0.41730.29770.72820.093*
O1B0.8002 (2)0.54463 (14)0.91259 (6)0.0579 (4)
O2B0.7268 (3)0.5372 (2)0.81340 (7)0.0773 (6)
N1B0.8244 (3)0.63231 (19)0.88088 (8)0.0555 (5)
N2B0.7912 (3)0.6303 (2)0.83034 (10)0.0724 (6)
C1B0.8944 (3)0.7368 (2)0.90277 (11)0.0569 (6)
C2B0.8649 (4)0.8405 (3)0.87728 (14)0.0790 (9)
H2B0.79780.84390.84690.103*
C3B0.9361 (5)0.9380 (3)0.89754 (19)0.0992 (12)
H3B0.91591.00900.88130.129*
C4B1.0381 (5)0.9317 (3)0.9420 (2)0.1010 (12)
H4B1.09010.99780.95470.131*
C5B1.0624 (4)0.8303 (3)0.96702 (15)0.0909 (10)
H5B1.12970.82720.99730.118*
C6B0.9885 (4)0.7299 (3)0.94818 (13)0.0740 (8)
H6B1.00280.66010.96600.096*
N1C0.6148 (2)0.30970 (17)0.93901 (7)0.0497 (5)
N2C0.6729 (3)0.43834 (18)1.00703 (8)0.0613 (6)
H2C10.72550.48010.98500.074*
H2C20.66590.45951.03980.074*
C1C0.6021 (3)0.3408 (2)0.99038 (9)0.0503 (6)
C2C0.5168 (4)0.2710 (2)1.02627 (11)0.0659 (7)
H2C0.50420.29521.06140.086*
C3C0.4538 (4)0.1699 (3)1.01003 (12)0.0725 (8)
H3C0.39520.12471.03340.094*
C4C0.4768 (4)0.1332 (2)0.95787 (13)0.0723 (8)
H4C0.43970.06140.94630.094*
C5C0.5549 (3)0.2053 (2)0.92439 (12)0.0637 (7)
H5C0.56810.18150.88930.083*
N1D0.8671 (2)0.30835 (19)0.85570 (8)0.0575 (5)
N2D0.7621 (4)0.2262 (3)0.77968 (11)0.1106 (11)
H2D10.67370.26370.78410.133*
H2D20.77110.18090.75270.133*
C1D0.8847 (4)0.2381 (2)0.81455 (11)0.0658 (7)
C2D1.0316 (4)0.1760 (3)0.80775 (15)0.0828 (10)
H2D1.04410.12770.77850.108*
C3D1.1514 (4)0.1886 (3)0.84437 (18)0.0861 (10)
H3D1.24800.14880.84050.112*
C4D1.1322 (4)0.2594 (3)0.88706 (15)0.0838 (9)
H4D1.21450.26800.91280.109*
C5D0.9913 (4)0.3169 (3)0.89134 (12)0.0700 (7)
H5D0.97920.36540.92060.091*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.0553 (2)0.0607 (2)0.03462 (16)0.00110 (17)0.00042 (12)0.00401 (15)
O1A0.0603 (11)0.0723 (12)0.0549 (10)0.0137 (10)0.0087 (8)0.0146 (9)
O2A0.0703 (11)0.0751 (12)0.0481 (10)0.0145 (10)0.0075 (9)0.0136 (9)
N1A0.0515 (11)0.0563 (12)0.0441 (11)0.0002 (10)0.0009 (8)0.0026 (10)
N2A0.0658 (14)0.0675 (14)0.0486 (12)0.0072 (11)0.0022 (10)0.0033 (11)
C1A0.0507 (14)0.0620 (15)0.0458 (13)0.0149 (12)0.0003 (10)0.0049 (12)
C2A0.0573 (17)0.089 (2)0.0710 (19)0.0004 (16)0.0067 (14)0.0036 (16)
C3A0.0582 (19)0.125 (3)0.093 (3)0.0050 (19)0.0167 (17)0.000 (2)
C4A0.067 (2)0.144 (3)0.065 (2)0.016 (2)0.0161 (16)0.000 (2)
C5A0.078 (2)0.142 (3)0.0576 (19)0.008 (2)0.0056 (16)0.023 (2)
C6A0.0611 (16)0.101 (2)0.0527 (16)0.0007 (16)0.0017 (13)0.0125 (16)
O1B0.0753 (11)0.0562 (10)0.0421 (9)0.0107 (9)0.0036 (8)0.0095 (7)
O2B0.0961 (15)0.0901 (14)0.0455 (11)0.0072 (13)0.0019 (10)0.0072 (10)
N1B0.0582 (12)0.0605 (12)0.0477 (12)0.0001 (10)0.0025 (9)0.0131 (10)
N2B0.0796 (16)0.0843 (17)0.0532 (14)0.0015 (14)0.0014 (12)0.0165 (13)
C1B0.0529 (14)0.0550 (15)0.0632 (17)0.0002 (12)0.0091 (12)0.0098 (12)
C2B0.080 (2)0.070 (2)0.088 (2)0.0002 (16)0.0179 (17)0.0262 (17)
C3B0.110 (3)0.065 (2)0.124 (3)0.007 (2)0.027 (3)0.026 (2)
C4B0.097 (3)0.069 (2)0.138 (4)0.024 (2)0.026 (3)0.006 (2)
C5B0.080 (2)0.088 (3)0.104 (3)0.0048 (19)0.0131 (19)0.017 (2)
C6B0.078 (2)0.0630 (18)0.080 (2)0.0045 (15)0.0087 (16)0.0003 (15)
N1C0.0546 (11)0.0516 (11)0.0432 (11)0.0077 (10)0.0040 (9)0.0008 (9)
N2C0.0823 (15)0.0644 (14)0.0375 (11)0.0049 (12)0.0076 (10)0.0009 (9)
C1C0.0518 (13)0.0537 (15)0.0458 (13)0.0177 (12)0.0065 (10)0.0067 (11)
C2C0.0763 (18)0.0622 (17)0.0600 (17)0.0148 (15)0.0184 (14)0.0127 (13)
C3C0.076 (2)0.071 (2)0.071 (2)0.0120 (16)0.0181 (15)0.0180 (16)
C4C0.0746 (19)0.0521 (16)0.090 (2)0.0007 (15)0.0000 (17)0.0120 (15)
C5C0.0654 (17)0.0604 (17)0.0652 (17)0.0091 (14)0.0010 (13)0.0031 (13)
N1D0.0571 (12)0.0664 (14)0.0494 (13)0.0023 (10)0.0073 (10)0.0040 (10)
N2D0.090 (2)0.159 (3)0.083 (2)0.007 (2)0.0104 (16)0.069 (2)
C1D0.0734 (18)0.0716 (18)0.0533 (16)0.0072 (15)0.0222 (14)0.0103 (13)
C2D0.089 (2)0.0636 (18)0.098 (2)0.0018 (17)0.051 (2)0.0080 (17)
C3D0.0608 (19)0.073 (2)0.125 (3)0.0054 (16)0.027 (2)0.019 (2)
C4D0.0611 (18)0.087 (2)0.103 (3)0.0153 (17)0.0020 (17)0.010 (2)
C5D0.0647 (17)0.0790 (19)0.0659 (18)0.0073 (15)0.0051 (14)0.0002 (15)
Geometric parameters (Å, º) top
Co1—O1A2.0690 (17)C1B—C6B1.363 (4)
Co1—O1B2.0708 (17)C1B—C2B1.378 (4)
Co1—O2B2.075 (2)C2B—C3B1.365 (5)
Co1—O2A2.0992 (18)C3B—C4B1.382 (5)
Co1—N1D2.146 (2)C4B—C5B1.342 (5)
Co1—N1C2.152 (2)C5B—C6B1.390 (4)
O1A—N1A1.310 (2)N1C—C1C1.341 (3)
O2A—N2A1.292 (3)N1C—C5C1.353 (3)
N1A—N2A1.288 (3)N2C—C1C1.333 (3)
N1A—C1A1.435 (3)C1C—C2C1.411 (3)
C1A—C6A1.372 (4)C2C—C3C1.340 (4)
C1A—C2A1.378 (4)C3C—C4C1.390 (4)
C2A—C3A1.369 (4)C4C—C5C1.358 (4)
C3A—C4A1.358 (5)N1D—C1D1.323 (3)
C4A—C5A1.378 (5)N1D—C5D1.347 (3)
C5A—C6A1.366 (4)N2D—C1D1.328 (4)
O1B—N1B1.307 (2)C1D—C2D1.425 (4)
O2B—N2B1.271 (3)C2D—C3D1.341 (5)
N1B—N2B1.287 (3)C3D—C4D1.358 (5)
N1B—C1B1.443 (3)C4D—C5D1.349 (4)
O1A—Co1—O1B157.94 (7)N2B—N1B—C1B117.5 (2)
O1A—Co1—O2B87.63 (8)O1B—N1B—C1B119.1 (2)
O1B—Co1—O2B75.63 (8)O2B—N2B—N1B114.8 (2)
O1A—Co1—O2A73.80 (7)C6B—C1B—C2B121.8 (3)
O1B—Co1—O2A91.65 (7)C6B—C1B—N1B118.9 (2)
O2B—Co1—O2A89.96 (8)C2B—C1B—N1B119.3 (3)
O1A—Co1—N1D99.04 (8)C3B—C2B—C1B118.6 (3)
O1B—Co1—N1D96.21 (8)C2B—C3B—C4B120.3 (3)
O2B—Co1—N1D93.32 (9)C5B—C4B—C3B120.2 (3)
O2A—Co1—N1D172.01 (8)C4B—C5B—C6B120.9 (4)
O1A—Co1—N1C97.84 (8)C1B—C6B—C5B118.1 (3)
O1B—Co1—N1C98.52 (7)C1C—N1C—C5C117.6 (2)
O2B—Co1—N1C174.11 (8)C1C—N1C—Co1127.42 (16)
O2A—Co1—N1C89.46 (7)C5C—N1C—Co1113.33 (17)
N1D—Co1—N1C88.01 (8)N2C—C1C—N1C118.9 (2)
N1A—O1A—Co1109.75 (13)N2C—C1C—C2C120.6 (2)
N2A—O2A—Co1114.62 (14)N1C—C1C—C2C120.5 (3)
N2A—N1A—O1A122.8 (2)C3C—C2C—C1C120.3 (3)
N2A—N1A—C1A118.5 (2)C2C—C3C—C4C119.4 (3)
O1A—N1A—C1A118.70 (19)C5C—C4C—C3C118.0 (3)
N1A—N2A—O2A112.9 (2)N1C—C5C—C4C124.0 (3)
C6A—C1A—C2A120.4 (2)C1D—N1D—C5D117.6 (2)
C6A—C1A—N1A118.7 (2)C1D—N1D—Co1128.21 (19)
C2A—C1A—N1A120.8 (2)C5D—N1D—Co1114.11 (18)
C3A—C2A—C1A118.8 (3)N1D—C1D—N2D118.6 (3)
C4A—C3A—C2A121.3 (3)N1D—C1D—C2D120.9 (3)
C3A—C4A—C5A119.5 (3)N2D—C1D—C2D120.6 (3)
C6A—C5A—C4A120.1 (3)C3D—C2D—C1D118.8 (3)
C5A—C6A—C1A119.8 (3)C2D—C3D—C4D120.3 (3)
N1B—O1B—Co1109.59 (14)C5D—C4D—C3D118.6 (3)
N2B—O2B—Co1115.27 (16)N1D—C5D—C4D123.9 (3)
N2B—N1B—O1B123.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2C—H2C1···O1B0.862.072.886 (3)159
N2D—H2D1···O1A0.861.982.812 (3)161
N2C—H2C2···O2Ai0.862.172.984 (3)157
N2D—H2D2···O2Bii0.862.353.198 (3)171
N2D—H2D2···N2Bii0.862.212.990 (3)152
Symmetry codes: (i) x+1, y+1, z+2; (ii) x+3/2, y1/2, z+3/2.
(niapir) 'di(2-aminopyridine)-bis(N-nitroso-N-phenylhydroxylaminato)-nickel(II)' top
Crystal data top
C22H22N8NiO4F(000) = 1080
Mr = 521.19Dx = 1.452 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 8.321 (1) ÅCell parameters from 25 reflections
b = 11.535 (2) Åθ = 14.3–18.4°
c = 24.852 (2) ŵ = 0.86 mm1
β = 91.55 (1)°T = 293 K
V = 2384.5 (5) Å3Prism, green
Z = 40.65 × 0.40 × 0.30 mm
Data collection top
Enraf-Nonius CAd4
diffractometer
3620 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.017
Graphite monochromatorθmax = 30.0°, θmin = 2.4°
ω–2θ scansh = 011
Absorption correction: ψ scan
MolEN, Structure Determination System. Enraf-Nonius, 1990)
k = 016
Tmin = 0.876, Tmax = 1l = 3434
7525 measured reflections3 standard reflections every 60 min
6888 independent reflections intensity decay: 4%
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.036 w = 1/[σ2(Fo2) + (0.0484P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.095(Δ/σ)max = 0.001
S = 0.93Δρmax = 0.33 e Å3
6888 reflectionsΔρmin = 0.27 e Å3
316 parameters
Crystal data top
C22H22N8NiO4V = 2384.5 (5) Å3
Mr = 521.19Z = 4
Monoclinic, P21/nMo Kα radiation
a = 8.321 (1) ŵ = 0.86 mm1
b = 11.535 (2) ÅT = 293 K
c = 24.852 (2) Å0.65 × 0.40 × 0.30 mm
β = 91.55 (1)°
Data collection top
Enraf-Nonius CAd4
diffractometer
3620 reflections with I > 2σ(I)
Absorption correction: ψ scan
MolEN, Structure Determination System. Enraf-Nonius, 1990)
Rint = 0.017
Tmin = 0.876, Tmax = 13 standard reflections every 60 min
7525 measured reflections intensity decay: 4%
6888 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.095H atoms treated by a mixture of independent and constrained refinement
S = 0.93Δρmax = 0.33 e Å3
6888 reflectionsΔρmin = 0.27 e Å3
316 parameters
Special details top

Experimental. this compound is isostructural with the analogous Co(II) complex

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
Ni10.66627 (3)0.41821 (2)0.872731 (9)0.04894 (9)
O1A0.49723 (16)0.34994 (12)0.82018 (5)0.0579 (3)
O2A0.45975 (17)0.51374 (12)0.88548 (5)0.0624 (4)
N1A0.38060 (19)0.42625 (14)0.81286 (6)0.0509 (4)
N2A0.3562 (2)0.51052 (15)0.84567 (6)0.0591 (4)
C1A0.2762 (2)0.41478 (17)0.76617 (7)0.0526 (4)
C2A0.1348 (3)0.4765 (2)0.76241 (9)0.0704 (6)
H2A0.10620.52680.78980.091*
C3A0.0365 (3)0.4625 (3)0.71747 (12)0.0898 (8)
H3A0.05940.50370.71440.117*
C4A0.0791 (3)0.3879 (3)0.67689 (10)0.0904 (9)
H4A0.01210.37900.64660.118*
C5A0.2194 (3)0.3271 (3)0.68117 (10)0.0866 (8)
H5A0.24840.27730.65370.113*
C6A0.3187 (3)0.3394 (2)0.72632 (9)0.0686 (6)
H6A0.41350.29690.72960.089*
O1B0.80078 (16)0.54060 (11)0.91317 (5)0.0550 (3)
O2B0.7211 (2)0.53312 (14)0.81327 (5)0.0700 (4)
N1B0.8227 (2)0.62988 (14)0.88091 (6)0.0524 (4)
N2B0.7871 (2)0.62687 (18)0.82984 (7)0.0664 (5)
C1B0.8934 (2)0.73362 (17)0.90198 (8)0.0548 (5)
C2B0.8625 (3)0.8378 (2)0.87642 (10)0.0744 (6)
H2B0.79450.84100.84620.097*
C3B0.9344 (4)0.9369 (2)0.89653 (13)0.0914 (9)
H3B0.91391.00800.88010.119*
C4B1.0365 (4)0.9308 (2)0.94109 (15)0.0952 (9)
H4B1.08800.99740.95370.124*
C5B1.0627 (3)0.8277 (3)0.96690 (12)0.0877 (8)
H5B1.12920.82480.99760.114*
C6B0.9904 (3)0.7276 (2)0.94745 (10)0.0709 (6)
H6B1.00720.65720.96490.092*
N1C0.60937 (18)0.30755 (13)0.93652 (6)0.0497 (4)
N2C0.6679 (2)0.43514 (14)1.00605 (6)0.0605 (4)
H2C10.72080.47690.98400.073*
H2C20.66120.45601.03910.073*
C1C0.5960 (2)0.33741 (16)0.98887 (7)0.0504 (4)
C2C0.5112 (3)0.2669 (2)1.02438 (9)0.0667 (6)
H2C0.49780.29031.05980.087*
C3C0.4494 (3)0.1652 (2)1.00705 (10)0.0715 (6)
H3C0.39100.11911.03020.093*
C4C0.4732 (3)0.12964 (19)0.95435 (10)0.0696 (6)
H4C0.43700.05770.94220.090*
C5C0.5508 (3)0.20283 (18)0.92121 (9)0.0606 (5)
H5C0.56460.17970.88580.079*
N1D0.86621 (19)0.31411 (14)0.85667 (6)0.0537 (4)
N2D0.7608 (3)0.2348 (2)0.77907 (8)0.1065 (9)
H2D10.67370.27310.78400.128*
H2D20.76850.19050.75140.128*
C1D0.8838 (3)0.24414 (18)0.81426 (8)0.0618 (5)
C2D1.0278 (3)0.1816 (2)0.80765 (11)0.0778 (7)
H2D1.03950.13370.77790.101*
C3D1.1490 (3)0.1918 (2)0.84487 (12)0.0803 (7)
H3D1.24420.15090.84090.104*
C4D1.1303 (3)0.2626 (2)0.88831 (11)0.0809 (7)
H4D1.21210.27060.91430.105*
C5D0.9903 (3)0.3207 (2)0.89263 (9)0.0665 (6)
H5D0.97870.36860.92240.086*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.05824 (15)0.05740 (15)0.03106 (11)0.00112 (12)0.00096 (9)0.00355 (11)
O1A0.0621 (8)0.0640 (8)0.0471 (7)0.0111 (7)0.0075 (6)0.0089 (6)
O2A0.0748 (9)0.0689 (9)0.0432 (7)0.0124 (7)0.0047 (7)0.0099 (7)
N1A0.0550 (9)0.0569 (9)0.0407 (8)0.0004 (8)0.0010 (7)0.0006 (7)
N2A0.0695 (11)0.0638 (11)0.0439 (9)0.0082 (9)0.0010 (8)0.0013 (8)
C1A0.0521 (11)0.0631 (12)0.0425 (9)0.0123 (10)0.0013 (8)0.0078 (9)
C2A0.0633 (14)0.0800 (15)0.0672 (14)0.0025 (12)0.0071 (11)0.0014 (12)
C3A0.0606 (15)0.120 (2)0.088 (2)0.0018 (15)0.0183 (13)0.0050 (17)
C4A0.0687 (16)0.142 (3)0.0600 (15)0.0201 (17)0.0173 (12)0.0046 (16)
C5A0.0777 (17)0.127 (2)0.0545 (14)0.0123 (16)0.0060 (12)0.0177 (14)
C6A0.0636 (13)0.0926 (17)0.0492 (12)0.0007 (12)0.0032 (10)0.0093 (11)
O1B0.0749 (9)0.0529 (7)0.0369 (6)0.0073 (7)0.0042 (6)0.0068 (6)
O2B0.0919 (11)0.0817 (10)0.0362 (7)0.0063 (9)0.0034 (7)0.0053 (7)
N1B0.0606 (10)0.0549 (9)0.0419 (8)0.0002 (8)0.0033 (7)0.0089 (7)
N2B0.0793 (12)0.0761 (12)0.0439 (10)0.0004 (10)0.0014 (9)0.0138 (9)
C1B0.0528 (11)0.0550 (12)0.0572 (12)0.0022 (9)0.0102 (9)0.0065 (9)
C2B0.0817 (16)0.0646 (14)0.0775 (16)0.0009 (12)0.0129 (13)0.0216 (12)
C3B0.108 (2)0.0680 (17)0.099 (2)0.0078 (15)0.0261 (18)0.0192 (15)
C4B0.099 (2)0.0709 (18)0.117 (3)0.0250 (16)0.0278 (19)0.0092 (17)
C5B0.0817 (17)0.0842 (19)0.096 (2)0.0043 (15)0.0113 (15)0.0188 (16)
C6B0.0770 (15)0.0607 (13)0.0742 (15)0.0053 (12)0.0112 (12)0.0005 (11)
N1C0.0565 (9)0.0524 (9)0.0404 (8)0.0065 (7)0.0030 (7)0.0003 (7)
N2C0.0812 (12)0.0655 (11)0.0351 (8)0.0017 (9)0.0055 (8)0.0029 (7)
C1C0.0590 (11)0.0533 (11)0.0390 (9)0.0169 (9)0.0037 (8)0.0058 (8)
C2C0.0800 (15)0.0671 (14)0.0537 (12)0.0156 (12)0.0165 (11)0.0150 (10)
C3C0.0773 (15)0.0633 (14)0.0746 (16)0.0091 (12)0.0159 (12)0.0198 (12)
C4C0.0769 (15)0.0495 (12)0.0823 (17)0.0019 (11)0.0007 (13)0.0077 (11)
C5C0.0679 (13)0.0563 (12)0.0573 (12)0.0062 (10)0.0004 (10)0.0009 (10)
N1D0.0575 (10)0.0618 (10)0.0420 (9)0.0019 (8)0.0064 (7)0.0033 (7)
N2D0.0875 (15)0.157 (2)0.0750 (14)0.0033 (15)0.0055 (12)0.0682 (15)
C1D0.0679 (13)0.0660 (13)0.0525 (12)0.0087 (11)0.0185 (10)0.0109 (10)
C2D0.0862 (17)0.0613 (14)0.0880 (18)0.0034 (13)0.0426 (15)0.0095 (13)
C3D0.0685 (16)0.0656 (15)0.108 (2)0.0099 (12)0.0251 (15)0.0127 (15)
C4D0.0657 (15)0.0867 (18)0.0903 (18)0.0129 (13)0.0005 (13)0.0078 (15)
C5D0.0663 (14)0.0762 (15)0.0567 (13)0.0089 (12)0.0018 (10)0.0011 (11)
Geometric parameters (Å, º) top
Ni1—O2B2.0458 (15)C1B—C6B1.372 (3)
Ni1—O1B2.0481 (13)C1B—C2B1.380 (3)
Ni1—O1A2.0506 (13)C2B—C3B1.378 (4)
Ni1—O2A2.0730 (14)C3B—C4B1.380 (4)
Ni1—N1D2.0988 (16)C4B—C5B1.366 (4)
Ni1—N1C2.0994 (15)C5B—C6B1.384 (3)
O1A—N1A1.3192 (19)N1C—C5C1.353 (3)
O2A—N2A1.295 (2)N1C—C1C1.353 (2)
N1A—N2A1.288 (2)N2C—C1C1.341 (2)
N1A—C1A1.436 (2)C1C—C2C1.404 (3)
C1A—C6A1.372 (3)C2C—C3C1.346 (3)
C1A—C2A1.376 (3)C3C—C4C1.392 (3)
C2A—C3A1.376 (3)C4C—C5C1.355 (3)
C3A—C4A1.379 (4)N1D—C1D1.339 (2)
C4A—C5A1.364 (4)N1D—C5D1.350 (3)
C5A—C6A1.383 (3)N2D—C1D1.332 (3)
O1B—N1B1.3207 (19)C1D—C2D1.412 (3)
O2B—N2B1.276 (2)C2D—C3D1.355 (4)
N1B—N2B1.296 (2)C3D—C4D1.366 (4)
N1B—C1B1.427 (3)C4D—C5D1.351 (3)
O2B—Ni1—O1B77.19 (6)N2B—N1B—C1B117.57 (16)
O2B—Ni1—O1A87.21 (6)O1B—N1B—C1B119.58 (15)
O1B—Ni1—O1A159.00 (5)O2B—N2B—N1B115.07 (16)
O2B—Ni1—O2A88.17 (6)C6B—C1B—C2B121.4 (2)
O1B—Ni1—O2A90.16 (6)C6B—C1B—N1B119.14 (18)
O1A—Ni1—O2A75.19 (5)C2B—C1B—N1B119.5 (2)
O2B—Ni1—N1D92.28 (6)C3B—C2B—C1B118.8 (2)
O1B—Ni1—N1D93.57 (6)C2B—C3B—C4B120.0 (2)
O1A—Ni1—N1D101.12 (6)C5B—C4B—C3B120.6 (2)
O2A—Ni1—N1D176.25 (6)C4B—C5B—C6B120.0 (3)
O2B—Ni1—N1C177.04 (6)C1B—C6B—C5B119.1 (2)
O1B—Ni1—N1C100.37 (5)C5C—N1C—C1C117.33 (17)
O1A—Ni1—N1C94.74 (6)C5C—N1C—Ni1114.66 (13)
O2A—Ni1—N1C90.17 (6)C1C—N1C—Ni1126.68 (13)
N1D—Ni1—N1C89.53 (6)N2C—C1C—N1C118.19 (17)
N1A—O1A—Ni1108.72 (10)N2C—C1C—C2C120.97 (18)
N2A—O2A—Ni1113.91 (11)N1C—C1C—C2C120.83 (19)
N2A—N1A—O1A122.98 (15)C3C—C2C—C1C119.8 (2)
N2A—N1A—C1A118.58 (16)C2C—C3C—C4C119.7 (2)
O1A—N1A—C1A118.44 (15)C5C—C4C—C3C118.1 (2)
N1A—N2A—O2A113.07 (15)N1C—C5C—C4C124.0 (2)
C6A—C1A—C2A121.03 (19)C1D—N1D—C5D117.23 (18)
C6A—C1A—N1A118.66 (18)C1D—N1D—Ni1126.77 (14)
C2A—C1A—N1A120.29 (19)C5D—N1D—Ni1115.99 (13)
C3A—C2A—C1A118.9 (2)N2D—C1D—N1D117.8 (2)
C2A—C3A—C4A120.5 (2)N2D—C1D—C2D121.5 (2)
C5A—C4A—C3A120.0 (2)N1D—C1D—C2D120.7 (2)
C4A—C5A—C6A120.1 (2)C3D—C2D—C1D119.6 (2)
C1A—C6A—C5A119.4 (2)C2D—C3D—C4D119.6 (2)
N1B—O1B—Ni1108.80 (10)C5D—C4D—C3D118.4 (2)
N2B—O2B—Ni1114.72 (11)N1D—C5D—C4D124.4 (2)
N2B—N1B—O1B122.82 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2C—H2C1···O1B0.862.042.858 (2)160
N2D—H2D1···O1A0.861.962.782 (3)161
N2C—H2C2···O2Ai0.862.182.983 (2)156
N2D—H2D2···O2Bii0.862.433.274 (2)168
N2D—H2D2···N2Bii0.862.192.996 (2)157
Symmetry codes: (i) x+1, y+1, z+2; (ii) x+3/2, y1/2, z+3/2.
(codpt) 'Di-(2,6-diamino-4-phenyl-1,3,5-triazine)-bis(N-nitroso-N– phenylhydroxylaminato)-cobalt(II) di-ethanol-bis(N-nitroso-N– phenylhydroxylaminato)-cobalt(II)' top
Crystal data top
C23H25CoN9O5Z = 2
Mr = 566.45F(000) = 586
Triclinic, P1Dx = 1.479 Mg m3
a = 10.225 (1) ÅMo Kα radiation, λ = 0.71070 Å
b = 10.214 (2) ÅCell parameters from 25 reflections
c = 14.163 (1) Åθ = 14.0–14.9°
α = 73.340 (9)°µ = 0.73 mm1
β = 68.180 (8)°T = 293 K
γ = 70.450 (13)°Prism, dark-orange
V = 1271.6 (3) Å30.50 × 0.25 × 0.25 mm
Data collection top
Enraf-Nonius CAD4
diffractometer
7753 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.013
Graphite monochromatorθmax = 35.0°, θmin = 2.2°
ω–2θ scansh = 1616
Absorption correction: ψ scan
MolEN, Structure Determination System. Enraf-Nonius, 1990)
k = 1616
Tmin = 0.889, Tmax = 1l = 2222
23705 measured reflections3 standard reflections every 60 min
11074 independent reflections intensity decay: 4%
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.036 w = 1/[σ2(Fo2) + (0.0683P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.106(Δ/σ)max < 0.001
S = 0.98Δρmax = 0.64 e Å3
11074 reflectionsΔρmin = 0.46 e Å3
360 parameters
Crystal data top
C23H25CoN9O5γ = 70.450 (13)°
Mr = 566.45V = 1271.6 (3) Å3
Triclinic, P1Z = 2
a = 10.225 (1) ÅMo Kα radiation
b = 10.214 (2) ŵ = 0.73 mm1
c = 14.163 (1) ÅT = 293 K
α = 73.340 (9)°0.50 × 0.25 × 0.25 mm
β = 68.180 (8)°
Data collection top
Enraf-Nonius CAD4
diffractometer
7753 reflections with I > 2σ(I)
Absorption correction: ψ scan
MolEN, Structure Determination System. Enraf-Nonius, 1990)
Rint = 0.013
Tmin = 0.889, Tmax = 13 standard reflections every 60 min
23705 measured reflections intensity decay: 4%
11074 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.106H atoms treated by a mixture of independent and constrained refinement
S = 0.98Δρmax = 0.64 e Å3
11074 reflectionsΔρmin = 0.46 e Å3
360 parameters
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*/UeqOcc. (<1)
Co10.50001.00000.50000.02564 (5)
N1A0.38326 (10)1.19585 (10)0.63098 (7)0.03233 (17)
N2A0.31499 (11)1.10040 (11)0.68729 (7)0.03554 (19)
O1A0.47578 (9)1.18812 (8)0.53713 (6)0.03358 (15)
O2A0.34867 (9)0.99251 (8)0.64424 (6)0.03227 (15)
C1A0.35251 (13)1.31944 (13)0.67309 (9)0.0379 (2)
C2A0.3185 (2)1.3104 (2)0.77839 (11)0.0611 (4)
H2A0.31551.22390.82320.079*
C3A0.2889 (2)1.4311 (2)0.81652 (13)0.0721 (5)
H3A0.26711.42540.88720.094*
C4A0.29137 (19)1.5593 (2)0.75083 (14)0.0652 (5)
H4A0.26941.64030.77720.085*
C5A0.3264 (2)1.56773 (17)0.64575 (15)0.0619 (4)
H5A0.32931.65440.60130.081*
C6A0.35757 (17)1.44727 (14)0.60573 (11)0.0489 (3)
H6A0.38141.45270.53490.064*
N1B0.67461 (9)0.89881 (9)0.57653 (6)0.02890 (16)
N3B0.72022 (10)0.78253 (10)0.73848 (7)0.03336 (18)
N5B0.86067 (10)0.93883 (10)0.62033 (7)0.03169 (17)
N2B0.57089 (12)0.71853 (11)0.68169 (8)0.0415 (2)
H2B10.52850.72810.63690.054*
H2B20.55760.65560.73720.054*
N6B0.82505 (10)1.03854 (11)0.46191 (7)0.03482 (19)
H6B10.78031.05270.41770.045*
H6B20.89541.07680.44640.045*
C7B0.88620 (12)0.84949 (12)0.79025 (8)0.0335 (2)
C8B0.89527 (14)0.73386 (14)0.87116 (10)0.0424 (3)
H8B0.85680.65990.87780.055*
C9B0.96179 (16)0.72961 (17)0.94150 (11)0.0510 (3)
H9B0.96830.65220.99510.066*
C101.01847 (18)0.83884 (18)0.93289 (11)0.0540 (3)
H10B1.06240.83510.98090.070*
C11B1.01017 (18)0.95429 (18)0.85288 (11)0.0536 (3)
H11B1.04911.02760.84680.070*
C12B0.94341 (15)0.96033 (14)0.78153 (9)0.0422 (3)
H12B0.93701.03810.72810.055*
C2B0.65685 (11)0.80099 (11)0.66506 (8)0.02988 (18)
C4B0.81714 (11)0.85785 (11)0.71232 (8)0.02985 (18)
C6B0.78537 (10)0.95738 (11)0.55442 (7)0.02777 (17)
Co20.50000.50001.00000.03589 (6)
N1C0.73154 (11)0.41686 (10)0.82994 (7)0.03597 (19)
O1C0.58834 (10)0.46681 (10)0.85274 (6)0.03897 (17)
N2C0.80358 (12)0.39799 (13)0.89313 (8)0.0444 (2)
O2C0.72266 (11)0.43358 (12)0.98057 (7)0.0495 (2)
C1C0.80906 (14)0.37803 (13)0.73042 (9)0.0409 (2)
C2C0.73077 (19)0.34609 (16)0.68257 (11)0.0532 (3)
H2C0.63260.34870.71460.069*
C3C0.8028 (2)0.31005 (19)0.58538 (14)0.0712 (5)
H3C0.75320.28590.55230.093*
C4C0.9474 (3)0.3099 (2)0.53759 (14)0.0816 (7)
H4C0.99370.29010.47110.106*
C5C1.0221 (2)0.3385 (2)0.58727 (14)0.0788 (6)
H5C1.12080.33370.55550.102*
C6C0.95473 (18)0.37501 (19)0.68483 (12)0.0588 (4)
H6C1.00600.39660.71800.077*
O1D0.52678 (15)0.70957 (11)0.94015 (9)0.0613 (3)
H1D0.589 (3)0.730 (3)0.885 (2)0.092*
C1DX0.4549 (5)0.8301 (3)0.9885 (3)0.0890 (15)0.738 (9)
H1D10.55510.83230.97190.107*0.738 (9)
H1D20.41260.77601.05520.107*0.738 (9)
C1DY0.4112 (9)0.8499 (8)0.9295 (9)0.077 (3)0.262 (9)
H1D30.43820.92300.87060.092*0.262 (9)
H1D40.31110.84550.94870.092*0.262 (9)
C2D0.3686 (5)0.9315 (5)0.9409 (6)0.231 (3)
H2D10.41871.00250.89810.347*
H2D20.28260.97320.99140.347*
H2D30.34150.89280.89870.347*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.02650 (9)0.02858 (9)0.02481 (8)0.01247 (6)0.00845 (6)0.00209 (6)
N1A0.0341 (4)0.0376 (4)0.0291 (4)0.0147 (3)0.0081 (3)0.0074 (3)
N2A0.0365 (4)0.0439 (5)0.0297 (4)0.0196 (4)0.0054 (3)0.0073 (3)
O1A0.0386 (4)0.0358 (4)0.0280 (3)0.0174 (3)0.0044 (3)0.0066 (3)
O2A0.0347 (4)0.0368 (4)0.0287 (3)0.0169 (3)0.0085 (3)0.0035 (3)
C1A0.0369 (5)0.0443 (6)0.0386 (5)0.0163 (4)0.0069 (4)0.0161 (4)
C2A0.0849 (11)0.0698 (10)0.0393 (6)0.0420 (9)0.0052 (7)0.0181 (6)
C3A0.0843 (12)0.0939 (13)0.0514 (8)0.0485 (11)0.0075 (8)0.0405 (9)
C4A0.0575 (9)0.0700 (10)0.0797 (11)0.0288 (8)0.0021 (8)0.0471 (9)
C5A0.0719 (10)0.0453 (7)0.0795 (11)0.0175 (7)0.0250 (9)0.0222 (7)
C6A0.0621 (8)0.0423 (6)0.0494 (7)0.0177 (6)0.0181 (6)0.0123 (5)
N1B0.0276 (4)0.0329 (4)0.0299 (4)0.0158 (3)0.0125 (3)0.0031 (3)
N3B0.0346 (4)0.0389 (4)0.0307 (4)0.0190 (3)0.0147 (3)0.0051 (3)
N5B0.0304 (4)0.0424 (4)0.0280 (4)0.0188 (3)0.0118 (3)0.0001 (3)
N2B0.0467 (5)0.0401 (5)0.0476 (5)0.0276 (4)0.0268 (4)0.0137 (4)
N6B0.0340 (4)0.0479 (5)0.0285 (4)0.0248 (4)0.0124 (3)0.0049 (3)
C7B0.0328 (5)0.0427 (5)0.0288 (4)0.0151 (4)0.0129 (4)0.0013 (4)
C8B0.0463 (6)0.0467 (6)0.0400 (6)0.0199 (5)0.0221 (5)0.0047 (5)
C9B0.0534 (7)0.0623 (8)0.0408 (6)0.0173 (6)0.0271 (6)0.0053 (6)
C100.0583 (8)0.0743 (10)0.0433 (6)0.0226 (7)0.0288 (6)0.0068 (6)
C11B0.0639 (9)0.0682 (9)0.0484 (7)0.0323 (7)0.0269 (7)0.0086 (6)
C12B0.0517 (7)0.0507 (6)0.0350 (5)0.0254 (5)0.0191 (5)0.0015 (5)
C2B0.0288 (4)0.0307 (4)0.0317 (4)0.0137 (3)0.0127 (3)0.0037 (3)
C4B0.0288 (4)0.0355 (5)0.0281 (4)0.0133 (4)0.0111 (3)0.0010 (3)
C6B0.0255 (4)0.0330 (4)0.0271 (4)0.0135 (3)0.0091 (3)0.0005 (3)
Co20.03992 (11)0.03612 (11)0.02803 (9)0.01189 (8)0.00715 (8)0.00244 (7)
N1C0.0382 (5)0.0366 (4)0.0315 (4)0.0093 (4)0.0108 (4)0.0041 (3)
O1C0.0376 (4)0.0448 (4)0.0328 (4)0.0101 (3)0.0110 (3)0.0049 (3)
N2C0.0438 (5)0.0508 (6)0.0398 (5)0.0102 (4)0.0158 (4)0.0085 (4)
O2C0.0476 (5)0.0653 (6)0.0384 (4)0.0115 (4)0.0165 (4)0.0129 (4)
C1C0.0466 (6)0.0368 (5)0.0337 (5)0.0030 (5)0.0119 (5)0.0078 (4)
C2C0.0659 (9)0.0484 (7)0.0477 (7)0.0042 (6)0.0242 (7)0.0157 (6)
C3C0.0976 (14)0.0601 (9)0.0555 (9)0.0102 (9)0.0368 (9)0.0280 (7)
C4C0.0965 (15)0.0744 (12)0.0469 (8)0.0231 (10)0.0195 (9)0.0282 (8)
C5C0.0633 (11)0.0896 (14)0.0513 (9)0.0054 (9)0.0005 (8)0.0193 (9)
C6C0.0485 (8)0.0703 (10)0.0477 (7)0.0064 (7)0.0083 (6)0.0152 (7)
O1D0.0760 (8)0.0387 (5)0.0507 (6)0.0212 (5)0.0046 (5)0.0055 (4)
C1DX0.140 (3)0.0393 (12)0.0669 (19)0.0177 (15)0.014 (2)0.0084 (12)
C1DY0.071 (5)0.043 (3)0.080 (7)0.013 (3)0.011 (4)0.007 (3)
C2D0.138 (4)0.105 (3)0.451 (10)0.046 (3)0.118 (5)0.107 (5)
Geometric parameters (Å, º) top
Co1—O1A2.0479 (8)C7B—C12B1.3959 (16)
Co1—O1Ai2.0479 (8)C7B—C4B1.4863 (13)
Co1—O2Ai2.0526 (8)C8B—C9B1.3843 (17)
Co1—O2A2.0526 (8)C9B—C101.378 (2)
Co1—N1B2.2342 (8)C10—C11B1.386 (2)
Co1—N1Bi2.2342 (8)C11B—C12B1.3928 (16)
N1A—N2A1.2921 (12)Co2—O1Cii2.0200 (9)
N1A—O1A1.3203 (11)Co2—O1C2.0200 (9)
N1A—C1A1.4404 (15)Co2—O2C2.0801 (10)
N2A—O2A1.2962 (13)Co2—O2Cii2.0801 (10)
C1A—C2A1.3821 (18)Co2—O1Dii2.1342 (11)
C1A—C6A1.3827 (19)Co2—O1D2.1342 (11)
C2A—C3A1.384 (2)N1C—N2C1.2949 (14)
C3A—C4A1.374 (3)N1C—O1C1.3235 (14)
C4A—C5A1.379 (3)N1C—C1C1.4324 (15)
C5A—C6A1.393 (2)N2C—O2C1.2827 (15)
N1B—C6B1.3495 (12)C1C—C6C1.379 (2)
N1B—C2B1.3554 (12)C1C—C2C1.383 (2)
N3B—C4B1.3360 (13)C2C—C3C1.389 (2)
N3B—C2B1.3577 (13)C3C—C4C1.378 (3)
N5B—C4B1.3330 (13)C4C—C5C1.353 (3)
N5B—C6B1.3548 (12)C5C—C6C1.392 (2)
N2B—C2B1.3287 (13)O1D—C1DY1.533 (7)
N6B—C6B1.3325 (12)C1DX—C1DY1.028 (11)
C7B—C8B1.3951 (16)C1DX—C2D1.317 (7)
O1A—Co1—O1Ai180.000 (1)N2B—C2B—N1B118.01 (9)
O1A—Co1—O2Ai102.99 (3)N2B—C2B—N3B117.74 (9)
O1Ai—Co1—O2Ai77.01 (3)N1B—C2B—N3B124.24 (9)
O1A—Co1—O2A77.01 (3)N5B—C4B—N3B125.43 (9)
O1Ai—Co1—O2A102.99 (3)N5B—C4B—C7B116.28 (9)
O2Ai—Co1—O2A180.0N3B—C4B—C7B118.27 (9)
O1A—Co1—N1B89.18 (3)N6B—C6B—N1B118.69 (8)
O1Ai—Co1—N1B90.82 (3)N6B—C6B—N5B117.06 (8)
O2Ai—Co1—N1B91.54 (3)N1B—C6B—N5B124.25 (8)
O2A—Co1—N1B88.46 (3)O1Cii—Co2—O1C180.000 (1)
O1A—Co1—N1Bi90.82 (3)O1Cii—Co2—O2C103.38 (4)
O1Ai—Co1—N1Bi89.18 (4)O1C—Co2—O2C76.62 (4)
O2Ai—Co1—N1Bi88.46 (3)O1Cii—Co2—O2Cii76.62 (4)
O2A—Co1—N1Bi91.54 (3)O1C—Co2—O2Cii103.38 (4)
N1B—Co1—N1Bi180.0O2C—Co2—O2Cii180.0
N2A—N1A—O1A124.04 (9)O1Cii—Co2—O1Dii87.19 (4)
N2A—N1A—C1A117.30 (9)O1C—Co2—O1Dii92.81 (4)
O1A—N1A—C1A118.64 (8)O2C—Co2—O1Dii92.89 (5)
N1A—N2A—O2A113.63 (9)O2Cii—Co2—O1Dii87.11 (5)
N1A—O1A—Co1109.60 (6)O1Cii—Co2—O1D92.81 (4)
N2A—O2A—Co1115.67 (6)O1C—Co2—O1D87.19 (4)
C2A—C1A—C6A120.85 (12)O2C—Co2—O1D87.11 (5)
C2A—C1A—N1A120.72 (12)O2Cii—Co2—O1D92.89 (5)
C6A—C1A—N1A118.43 (10)O1Dii—Co2—O1D180.0
C1A—C2A—C3A119.35 (16)N2C—N1C—O1C123.79 (10)
C4A—C3A—C2A120.55 (15)N2C—N1C—C1C118.89 (10)
C3A—C4A—C5A119.91 (14)O1C—N1C—C1C117.29 (9)
C4A—C5A—C6A120.43 (16)N1C—O1C—Co2110.63 (7)
C1A—C6A—C5A118.90 (14)O2C—N2C—N1C113.43 (10)
C6B—N1B—C2B114.46 (8)N2C—O2C—Co2115.37 (7)
C6B—N1B—Co1121.09 (6)C6C—C1C—C2C122.18 (13)
C2B—N1B—Co1122.12 (6)C6C—C1C—N1C120.83 (12)
C4B—N3B—C2B114.74 (8)C2C—C1C—N1C116.98 (12)
C4B—N5B—C6B115.30 (8)C1C—C2C—C3C118.14 (17)
C8B—C7B—C12B119.60 (10)C4C—C3C—C2C120.45 (18)
C8B—C7B—C4B121.60 (10)C5C—C4C—C3C120.07 (16)
C12B—C7B—C4B118.80 (9)C4C—C5C—C6C121.54 (19)
C9B—C8B—C7B119.75 (12)C1C—C6C—C5C117.55 (17)
C10—C9B—C8B120.71 (12)C1DY—O1D—Co2129.3 (4)
C9B—C10—C11B120.11 (12)C1DY—C1DX—C2D39.2 (5)
C10—C11B—C12B119.92 (13)C1DX—C1DY—O1D64.0 (5)
C11B—C12B—C7B119.92 (12)
Symmetry codes: (i) x+1, y+2, z+1; (ii) x+1, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2B—H2B1···O1Ai0.862.383.1372 (13)147
N6B—H6B1···O2Ai0.862.052.8550 (12)155
N6B—H6B2···N5Biii0.862.283.0491 (13)149
N2B—H2B2···O1C0.862.162.9923 (13)163
O1D—H1D···N3B0.83 (3)2.04 (3)2.8622 (15)171 (2)
Symmetry codes: (i) x+1, y+2, z+1; (iii) x+2, y+2, z+1.

Experimental details

(coapir)(niapir)(codpt)
Crystal data
Chemical formulaC22H22CoN8O4C22H22N8NiO4C23H25CoN9O5
Mr521.41521.19566.45
Crystal system, space groupMonoclinic, P21/nMonoclinic, P21/nTriclinic, P1
Temperature (K)293293293
a, b, c (Å)8.270 (1), 11.579 (2), 25.019 (4)8.321 (1), 11.535 (2), 24.852 (2)10.225 (1), 10.214 (2), 14.163 (1)
α, β, γ (°)90, 91.42 (2), 9090, 91.55 (1), 9073.340 (9), 68.180 (8), 70.450 (13)
V3)2395.0 (6)2384.5 (5)1271.6 (3)
Z442
Radiation typeMo KαMo KαMo Kα
µ (mm1)0.760.860.73
Crystal size (mm)0.45 × 0.40 × 0.400.65 × 0.40 × 0.300.50 × 0.25 × 0.25
Data collection
DiffractometerEnraf-Nonius CAD4
diffractometer
Enraf-Nonius CAd4
diffractometer
Enraf-Nonius CAD4
diffractometer
Absorption correctionψ scan
MolEN, Structure Determination System. Enraf-Nonius, 1990)
ψ scan
MolEN, Structure Determination System. Enraf-Nonius, 1990)
ψ scan
MolEN, Structure Determination System. Enraf-Nonius, 1990)
Tmin, Tmax0.945, 10.876, 10.889, 1
No. of measured, independent and
observed [I > 2σ(I)] reflections
6214, 5671, 3093 7525, 6888, 3620 23705, 11074, 7753
Rint0.0150.0170.013
(sin θ/λ)max1)0.6600.7030.806
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.113, 0.96 0.036, 0.095, 0.93 0.036, 0.106, 0.98
No. of reflections5671688811074
No. of parameters316316360
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.32, 0.280.33, 0.270.64, 0.46

Computer programs: CAD-4 EXPRESS, XCAD4 (Harms & Wocadlo, 1996), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 1999).

Hydrogen-bond geometry (Å, º) for (coapir) top
D—H···AD—HH···AD···AD—H···A
N2C—H2C1···O1B0.862.072.886 (3)158.8
N2D—H2D1···O1A0.861.982.812 (3)161.4
N2C—H2C2···O2Ai0.862.172.984 (3)157.0
N2D—H2D2···O2Bii0.862.353.198 (3)171.3
N2D—H2D2···N2Bii0.862.212.990 (3)151.5
Symmetry codes: (i) x+1, y+1, z+2; (ii) x+3/2, y1/2, z+3/2.
Hydrogen-bond geometry (Å, º) for (niapir) top
D—H···AD—HH···AD···AD—H···A
N2C—H2C1···O1B0.862.042.858 (2)159.8
N2D—H2D1···O1A0.861.962.782 (3)160.8
N2C—H2C2···O2Ai0.862.182.983 (2)155.6
N2D—H2D2···O2Bii0.862.433.274 (2)167.9
N2D—H2D2···N2Bii0.862.192.996 (2)156.8
Symmetry codes: (i) x+1, y+1, z+2; (ii) x+3/2, y1/2, z+3/2.
Hydrogen-bond geometry (Å, º) for (codpt) top
D—H···AD—HH···AD···AD—H···A
N2B—H2B1···O1Ai0.862.383.1372 (13)147.4
N6B—H6B1···O2Ai0.862.052.8550 (12)154.6
N6B—H6B2···N5Bii0.862.283.0491 (13)148.6
N2B—H2B2···O1C0.862.162.9923 (13)163.2
O1D—H1D···N3B0.83 (3)2.04 (3)2.8622 (15)171 (2)
Symmetry codes: (i) x+1, y+2, z+1; (ii) x+2, y+2, z+1.
 

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