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Acta Crystallogr Sect E Struct Rep Online. 2009 February 1; 65(Pt 2): m226.
Published online 2009 January 23. doi:  10.1107/S1600536809002293
PMCID: PMC2968403

{(+)-(1R,2R)-1,2-Diphenyl-2,2′-[ethane-1,2-diylbis(nitrilo­methyl­idyne)]­di­phenol­ato}dipyridine­cobalt(III) perchlorate sesquihydrate

Abstract

In title complex, [Co(C28H22N2O2)(C5H5N)2]ClO4·1.5H2O, the CoIII ion is in a slightly distorted octa­hedral coordination environment with the pyridine ligands in a trans arrangement. In addition to the cation and anion, the asymmetric unit also contains three half-occupancy solvent water mol­ecules and all components are connected via inter­molecular O—H(...)O hydrogen bonds.

Related literature

For background information, see: Amirnasr et al. (2001 [triangle]); Cmi et al. (1998 [triangle]); Polson et al. (1997 [triangle]); Yamada (1999 [triangle]); Henson et al. (1999 [triangle]). For the synthethis of the parent Schiff base ligand, see: Zhang et al. (1990 [triangle]). For a related structure, see: Shi et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m226-scheme1.jpg

Experimental

Crystal data

  • [Co(C28H22N2O2)(C5H5N)2]ClO4·1.5H2O
  • M r = 762.08
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m226-efi1.jpg
  • a = 10.9214 (6) Å
  • b = 18.3856 (10) Å
  • c = 18.6714 (11) Å
  • V = 3749.2 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.58 mm−1
  • T = 293 (2) K
  • 0.21 × 0.16 × 0.13 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.887, T max = 0.928
  • 20101 measured reflections
  • 7290 independent reflections
  • 4733 reflections with I > 2σ(I)
  • R int = 0.059

Refinement

  • R[F 2 > 2σ(F 2)] = 0.050
  • wR(F 2) = 0.127
  • S = 0.99
  • 7290 reflections
  • 480 parameters
  • H-atom parameters constrained
  • Δρmax = 0.51 e Å−3
  • Δρmin = −0.29 e Å−3
  • Absolute structure: Flack (1983 [triangle]), with 3227 Friedel pairs
  • Flack parameter: 0.02 (2)

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT-Plus (Bruker, 2007 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809002293/lh2754sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809002293/lh2754Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

Cobalt complexes with tetradentate Schiff base ligands have been extensively used to mimic cobalamin (B12) coenzymes (Amirnasr et al., 2001; Cmi et al., 1998; Polson et al., 1997) and dioxygen carriers and oxygen activators (Yamada, 1999; Henson et al., 1999). Here, we report the crystal structure of a CoIII complex containing the chiral tetradentate Schiff base ligand (+)-(1R,2R)-N,N'-Bis(salicylidene)-1,2-diphenyl-1,2-ethanediamine.

The molecular structure of the title cation is shown in Fig. 1. The CoIII ion is six coordinated. The four equational sites are occupied by two N atoms and two O atoms of the tetradentate Schiff base ligand and the two axial sites are occupied by the N atoms of two pyridine ligands, forming a slightly distorted octahedral coordination environment. The Co—O and Co—NSchiff base bond lengths are consistent with the corresponding bond lengths in the CoIII Schiff base complex trans-[Co(salen)(py)2][BPh4] (Shi et al., 1995) as are the Co—Npy distances.

Experimental

The free Schiff base ligand (L), it was prepared according to the method reported previously (Zhang et al., 1990). The synthesis of the title complex was carried out by mixing CoClO4.6H2O, pyridine and L with a molar ratio 1:2:1 in methanol. After the mixture was stirred for about 30 min at room temperature in air, it was filtered to remove any undissolved material. The filtrate was allowed to partially evaporate in air for several days to produce crystals suitable for X-ray diffraction with a yield about 40%.

Refinement

H atoms bonded to O atoms were located in a difference Fourier map. They were refined in a riding-model approximation with O—H = 0.85 Å and Uiso(H) = 1.2Ueq(O). H atoms bonded to C atoms were placed in calculated positions with C—H distances = 0.93 and 0.98 Å, and were refined in a riding-model approximation with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The cation of the title complex with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are not shown.

Crystal data

[Co(C28H22N2O2)(C5H5N)2]ClO4·1.5H2OF(000) = 1580
Mr = 762.08Dx = 1.350 Mg m3Dm = 1.35 Mg m3Dm measured by not measured
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 2979 reflections
a = 10.9214 (6) Åθ = 2.4–20.0°
b = 18.3856 (10) ŵ = 0.58 mm1
c = 18.6714 (11) ÅT = 293 K
V = 3749.2 (4) Å3Block, red-brown
Z = 40.21 × 0.16 × 0.13 mm

Data collection

Bruker APEXII CCD area-detector diffractometer7290 independent reflections
Radiation source: fine-focus sealed tube4733 reflections with I > 2σ(I)
graphiteRint = 0.059
[var phi] and ω scansθmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −12→13
Tmin = 0.887, Tmax = 0.928k = −20→22
20101 measured reflectionsl = −22→23

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050H-atom parameters constrained
wR(F2) = 0.127w = 1/[σ2(Fo2) + (0.0572P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max = 0.001
7290 reflectionsΔρmax = 0.51 e Å3
480 parametersΔρmin = −0.29 e Å3
0 restraintsAbsolute structure: Flack (1983), with 3227 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.02 (2)

Special details

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)

xyzUiso*/UeqOcc. (<1)
Co10.24611 (5)0.00305 (3)0.17215 (3)0.03757 (15)
Cl10.35527 (13)0.30536 (8)0.25408 (9)0.0736 (4)
O10.1518 (3)−0.08004 (15)0.19449 (15)0.0469 (8)
O20.1443 (3)0.01550 (15)0.09181 (14)0.0437 (7)
O30.3774 (4)0.24263 (19)0.2999 (3)0.0960 (14)
O40.2856 (5)0.3577 (2)0.2928 (3)0.1116 (16)
O50.4678 (4)0.3364 (2)0.2330 (3)0.0932 (14)
O60.2887 (4)0.2832 (3)0.1939 (3)0.1289 (19)
O70.5661 (8)0.6832 (4)0.9108 (4)0.088 (3)0.50
H7C0.48840.68270.91360.106*0.50
H7D0.58800.65220.87960.106*0.50
O80.3200 (8)0.6862 (5)0.9246 (4)0.103 (3)0.50
H8C0.27890.72310.93800.124*0.50
H8D0.29100.67160.88490.124*0.50
O90.1910 (8)0.7977 (6)0.9603 (5)0.123 (4)0.50
H9C0.15510.78680.92140.148*0.50
H9D0.13780.80140.99330.148*0.50
N10.3507 (3)−0.00967 (18)0.25272 (17)0.0388 (8)
N20.3455 (3)0.08553 (18)0.15341 (17)0.0367 (8)
N30.3501 (4)−0.0582 (2)0.1098 (2)0.0449 (9)
N40.1290 (3)0.06249 (19)0.22734 (19)0.0407 (9)
C10.2065 (4)−0.0821 (2)0.3196 (2)0.0408 (10)
C20.1272 (4)−0.0988 (2)0.2617 (2)0.0428 (11)
C30.0206 (5)−0.1379 (3)0.2778 (3)0.0560 (13)
H3−0.0320−0.15090.24080.067*
C4−0.0077 (5)−0.1571 (3)0.3452 (3)0.0629 (15)
H4−0.0801−0.18230.35370.076*
C50.0679 (5)−0.1406 (3)0.4024 (3)0.0601 (14)
H50.0466−0.15380.44890.072*
C60.1756 (4)−0.1041 (2)0.3888 (3)0.0490 (12)
H60.2287−0.09380.42640.059*
C70.3216 (4)−0.0458 (2)0.3094 (2)0.0412 (11)
H70.3789−0.04860.34610.049*
C80.2062 (4)0.1393 (2)0.0670 (2)0.0421 (11)
C90.1321 (4)0.0775 (3)0.0570 (2)0.0403 (10)
C100.0392 (4)0.0813 (3)0.0046 (2)0.0480 (12)
H10−0.00840.0406−0.00500.058*
C110.0183 (4)0.1454 (3)−0.0326 (2)0.0538 (13)
H11−0.04430.1472−0.06630.065*
C120.0887 (5)0.2064 (3)−0.0203 (3)0.0511 (13)
H120.07260.2492−0.04510.061*
C130.1821 (4)0.2038 (3)0.0282 (2)0.0472 (12)
H130.23030.24480.03580.057*
C140.3136 (4)0.1386 (3)0.1134 (2)0.0408 (11)
H140.36260.17990.11390.049*
C150.4731 (4)0.0235 (2)0.2419 (2)0.0394 (10)
H150.5198−0.00890.21040.047*
C160.4541 (4)0.0942 (2)0.2025 (2)0.0377 (10)
H160.43190.13090.23840.045*
C170.5483 (4)0.0344 (2)0.3105 (2)0.0432 (11)
C180.6548 (4)−0.0041 (3)0.3210 (3)0.0573 (11)
H180.6797−0.03810.28710.069*
C190.7252 (5)0.0073 (4)0.3816 (3)0.0746 (15)
H190.7963−0.01960.38860.089*
C200.6908 (6)0.0581 (4)0.4313 (4)0.0787 (19)
H200.73920.06620.47150.094*
C210.5833 (6)0.0977 (3)0.4217 (3)0.0755 (17)
H210.55930.13210.45530.091*
C220.5124 (5)0.0850 (3)0.3614 (3)0.0587 (14)
H220.44000.11070.35500.070*
C230.5701 (4)0.1209 (2)0.1656 (2)0.0417 (10)
C240.6226 (5)0.0834 (3)0.1097 (3)0.0610 (14)
H240.58480.04190.09180.073*
C250.7327 (5)0.1077 (3)0.0797 (3)0.0687 (15)
H250.76780.08260.04170.082*
C260.7883 (5)0.1682 (3)0.1062 (3)0.0606 (15)
H260.86160.18400.08620.073*
C270.7379 (5)0.2061 (2)0.1619 (3)0.0544 (12)
H270.77700.24720.17980.065*
C280.6272 (4)0.1827 (2)0.1917 (2)0.0439 (11)
H280.59190.20870.22900.053*
C290.3837 (5)−0.1252 (3)0.1278 (3)0.0616 (15)
H290.3636−0.14190.17330.074*
C300.4459 (7)−0.1706 (3)0.0833 (4)0.088 (2)
H300.4667−0.21740.09780.105*
C310.4777 (6)−0.1458 (4)0.0160 (4)0.087 (2)
H310.5205−0.1756−0.01550.104*
C320.4457 (6)−0.0779 (4)−0.0031 (3)0.0739 (17)
H320.4680−0.0599−0.04780.089*
C330.3795 (5)−0.0349 (3)0.0439 (3)0.0547 (13)
H330.35480.01120.02940.066*
C340.1608 (4)0.1158 (2)0.2719 (2)0.0487 (12)
H340.24360.12560.27850.058*
C350.0761 (5)0.1572 (3)0.3087 (3)0.0648 (15)
H350.10150.19440.33910.078*
C36−0.0459 (5)0.1425 (3)0.2998 (3)0.0732 (16)
H36−0.10490.16860.32490.088*
C37−0.0793 (5)0.0884 (3)0.2533 (3)0.0661 (15)
H37−0.16180.07820.24600.079*
C380.0086 (4)0.0492 (3)0.2173 (3)0.0496 (12)
H38−0.01540.01290.18550.060*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Co10.0380 (3)0.0441 (3)0.0307 (2)−0.0055 (3)−0.0038 (3)0.0024 (3)
Cl10.0614 (9)0.0627 (8)0.0966 (11)0.0083 (7)−0.0118 (9)−0.0187 (8)
O10.0477 (18)0.0533 (18)0.0398 (19)−0.0136 (16)−0.0067 (15)0.0072 (14)
O20.0463 (17)0.0517 (19)0.0331 (16)−0.0078 (15)−0.0100 (13)0.0051 (14)
O30.101 (3)0.055 (2)0.132 (4)0.005 (2)−0.002 (3)−0.001 (2)
O40.127 (4)0.087 (3)0.121 (4)0.035 (3)0.032 (3)−0.011 (3)
O50.057 (2)0.098 (3)0.124 (4)−0.008 (2)−0.002 (3)0.012 (3)
O60.103 (4)0.153 (4)0.131 (4)0.010 (3)−0.049 (3)−0.046 (4)
O70.098 (6)0.118 (7)0.047 (5)0.066 (5)−0.001 (4)−0.044 (5)
O80.116 (7)0.148 (8)0.046 (5)0.011 (6)−0.024 (5)0.004 (5)
O90.088 (7)0.195 (11)0.087 (7)−0.027 (7)−0.009 (5)−0.009 (7)
N10.0372 (18)0.0435 (19)0.0358 (19)−0.0038 (18)−0.0029 (15)−0.0018 (18)
N20.0333 (19)0.044 (2)0.032 (2)−0.0011 (17)−0.0010 (16)−0.0020 (16)
N30.049 (2)0.049 (2)0.036 (2)0.000 (2)−0.0080 (19)−0.0043 (17)
N40.039 (2)0.049 (2)0.034 (2)−0.0047 (18)0.0004 (17)0.0069 (17)
C10.039 (2)0.045 (2)0.038 (3)0.001 (2)−0.005 (2)0.004 (2)
C20.043 (3)0.044 (2)0.041 (3)−0.003 (2)−0.005 (2)0.008 (2)
C30.048 (3)0.061 (3)0.058 (3)−0.014 (3)−0.009 (3)0.017 (3)
C40.046 (3)0.079 (4)0.064 (4)−0.019 (3)−0.002 (3)0.025 (3)
C50.047 (3)0.076 (4)0.058 (4)−0.001 (3)0.006 (3)0.013 (3)
C60.046 (3)0.056 (3)0.044 (3)0.000 (2)−0.003 (2)0.009 (2)
C70.042 (3)0.048 (3)0.034 (3)0.001 (2)−0.007 (2)0.004 (2)
C80.043 (3)0.051 (3)0.032 (3)0.000 (2)0.0064 (19)0.002 (2)
C90.040 (3)0.054 (3)0.027 (2)0.001 (2)0.0042 (19)−0.002 (2)
C100.040 (3)0.070 (3)0.034 (3)0.003 (3)0.000 (2)0.002 (2)
C110.042 (3)0.083 (4)0.037 (3)0.013 (3)−0.001 (2)0.011 (3)
C120.050 (3)0.062 (3)0.042 (3)0.011 (3)0.005 (2)0.017 (2)
C130.051 (3)0.054 (3)0.037 (3)0.004 (2)0.005 (2)0.009 (2)
C140.041 (3)0.046 (3)0.036 (3)−0.007 (2)0.002 (2)0.000 (2)
C150.032 (2)0.047 (3)0.039 (3)−0.0034 (19)−0.0050 (19)−0.001 (2)
C160.035 (2)0.043 (2)0.035 (2)−0.005 (2)−0.0020 (19)−0.002 (2)
C170.038 (2)0.049 (3)0.043 (3)−0.006 (2)−0.008 (2)0.007 (2)
C180.044 (3)0.066 (3)0.062 (3)−0.006 (3)−0.007 (2)0.006 (3)
C190.054 (3)0.094 (4)0.076 (4)−0.005 (4)−0.020 (3)0.013 (4)
C200.069 (4)0.096 (5)0.071 (4)−0.025 (4)−0.028 (3)0.023 (4)
C210.087 (4)0.078 (4)0.061 (4)−0.008 (3)−0.021 (4)−0.003 (3)
C220.063 (3)0.068 (3)0.045 (3)0.004 (3)−0.016 (3)−0.002 (3)
C230.035 (2)0.050 (3)0.040 (3)0.001 (2)0.001 (2)0.002 (2)
C240.056 (3)0.070 (3)0.057 (3)−0.011 (3)0.012 (3)−0.013 (3)
C250.052 (3)0.087 (4)0.067 (3)−0.006 (3)0.022 (3)−0.012 (3)
C260.040 (3)0.075 (4)0.066 (4)−0.006 (3)0.011 (2)0.014 (3)
C270.048 (3)0.052 (3)0.064 (3)−0.005 (3)0.005 (3)0.011 (2)
C280.040 (3)0.044 (2)0.047 (3)−0.001 (2)0.001 (2)0.004 (2)
C290.073 (4)0.060 (3)0.051 (3)0.010 (3)−0.010 (3)−0.006 (3)
C300.111 (5)0.077 (4)0.075 (5)0.037 (4)−0.014 (4)−0.014 (4)
C310.093 (5)0.093 (5)0.075 (5)0.033 (4)−0.002 (4)−0.028 (4)
C320.088 (5)0.082 (4)0.051 (3)0.010 (4)0.005 (3)−0.010 (3)
C330.061 (3)0.058 (3)0.045 (3)−0.003 (3)0.002 (3)−0.012 (2)
C340.040 (3)0.060 (3)0.047 (3)−0.002 (2)0.006 (2)−0.002 (2)
C350.066 (4)0.069 (3)0.059 (4)0.010 (3)0.009 (3)−0.013 (3)
C360.055 (4)0.088 (4)0.076 (4)0.016 (3)0.016 (3)0.003 (4)
C370.041 (3)0.093 (4)0.064 (4)0.007 (3)0.008 (3)0.013 (3)
C380.041 (3)0.061 (3)0.047 (3)−0.003 (2)−0.002 (2)0.009 (2)

Geometric parameters (Å, °)

Co1—O21.881 (3)C13—H130.9300
Co1—O11.889 (3)C14—H140.9300
Co1—N21.897 (3)C15—C161.509 (6)
Co1—N11.904 (3)C15—C171.534 (6)
Co1—N41.973 (4)C15—H150.9800
Co1—N31.978 (4)C16—C231.524 (6)
Cl1—O61.400 (5)C16—H160.9800
Cl1—O51.412 (4)C17—C181.376 (6)
Cl1—O41.424 (4)C17—C221.387 (6)
Cl1—O31.456 (4)C18—C191.383 (7)
O1—C21.329 (5)C18—H180.9300
O2—C91.318 (5)C19—C201.369 (8)
O7—H7C0.8501C19—H190.9300
O7—H7D0.8499C20—C211.393 (8)
O8—H8C0.8500C20—H200.9300
O8—H8D0.8500C21—C221.386 (7)
O9—H9C0.8500C21—H210.9300
O9—H9D0.8500C22—H220.9300
N1—C71.290 (5)C23—C241.374 (6)
N1—C151.482 (5)C23—C281.385 (6)
N2—C141.277 (5)C24—C251.400 (7)
N2—C161.508 (5)C24—H240.9300
N3—C291.328 (6)C25—C261.359 (7)
N3—C331.342 (6)C25—H250.9300
N4—C341.332 (5)C26—C271.366 (7)
N4—C381.351 (5)C26—H260.9300
C1—C61.395 (6)C27—C281.398 (6)
C1—C21.418 (6)C27—H270.9300
C1—C71.436 (6)C28—H280.9300
C2—C31.401 (6)C29—C301.361 (8)
C3—C41.343 (7)C29—H290.9300
C3—H30.9300C30—C311.380 (9)
C4—C51.383 (7)C30—H300.9300
C4—H40.9300C31—C321.345 (9)
C5—C61.378 (7)C31—H310.9300
C5—H50.9300C32—C331.385 (7)
C6—H60.9300C32—H320.9300
C7—H70.9300C33—H330.9300
C8—C91.408 (6)C34—C351.381 (6)
C8—C131.414 (6)C34—H340.9300
C8—C141.459 (6)C35—C361.370 (8)
C9—C101.412 (6)C35—H350.9300
C10—C111.386 (7)C36—C371.369 (8)
C10—H100.9300C36—H360.9300
C11—C121.379 (7)C37—C381.376 (7)
C11—H110.9300C37—H370.9300
C12—C131.365 (7)C38—H380.9300
C12—H120.9300
O2—Co1—O187.26 (12)C8—C14—H14117.5
O2—Co1—N295.39 (13)N1—C15—C16107.3 (3)
O1—Co1—N2177.35 (14)N1—C15—C17115.0 (3)
O2—Co1—N1179.34 (15)C16—C15—C17111.6 (3)
O1—Co1—N193.06 (13)N1—C15—H15107.6
N2—Co1—N184.29 (15)C16—C15—H15107.6
O2—Co1—N488.04 (14)C17—C15—H15107.6
O1—Co1—N488.81 (14)N2—C16—C15108.3 (3)
N2—Co1—N491.41 (14)N2—C16—C23114.4 (3)
N1—Co1—N492.55 (14)C15—C16—C23112.6 (4)
O2—Co1—N386.52 (14)N2—C16—H16107.1
O1—Co1—N388.97 (15)C15—C16—H16107.1
N2—Co1—N391.06 (15)C23—C16—H16107.1
N1—Co1—N392.90 (15)C18—C17—C22119.0 (4)
N4—Co1—N3174.22 (16)C18—C17—C15120.3 (4)
O6—Cl1—O5110.2 (3)C22—C17—C15120.6 (4)
O6—Cl1—O4109.1 (3)C17—C18—C19120.6 (5)
O5—Cl1—O4109.5 (3)C17—C18—H18119.7
O6—Cl1—O3109.1 (3)C19—C18—H18119.7
O5—Cl1—O3109.8 (3)C20—C19—C18120.3 (6)
O4—Cl1—O3109.0 (3)C20—C19—H19119.8
C2—O1—Co1121.9 (3)C18—C19—H19119.8
C9—O2—Co1123.9 (3)C19—C20—C21120.0 (6)
H7C—O7—H7D108.5C19—C20—H20120.0
H8C—O8—H8D108.3C21—C20—H20120.0
H9C—O9—H9D108.8C22—C21—C20119.2 (6)
C7—N1—C15123.1 (3)C22—C21—H21120.4
C7—N1—Co1124.3 (3)C20—C21—H21120.4
C15—N1—Co1112.5 (3)C21—C22—C17120.8 (5)
C14—N2—C16119.3 (4)C21—C22—H22119.6
C14—N2—Co1124.2 (3)C17—C22—H22119.6
C16—N2—Co1115.0 (2)C24—C23—C28119.3 (4)
C29—N3—C33117.5 (4)C24—C23—C16122.0 (4)
C29—N3—Co1122.5 (3)C28—C23—C16118.6 (4)
C33—N3—Co1119.7 (3)C23—C24—C25120.1 (5)
C34—N4—C38118.3 (4)C23—C24—H24119.9
C34—N4—Co1124.4 (3)C25—C24—H24119.9
C38—N4—Co1117.3 (3)C26—C25—C24119.9 (5)
C6—C1—C2119.7 (4)C26—C25—H25120.0
C6—C1—C7117.9 (4)C24—C25—H25120.0
C2—C1—C7122.3 (4)C25—C26—C27120.9 (5)
O1—C2—C3120.3 (4)C25—C26—H26119.5
O1—C2—C1122.7 (4)C27—C26—H26119.5
C3—C2—C1117.0 (4)C26—C27—C28119.6 (5)
C4—C3—C2121.9 (5)C26—C27—H27120.2
C4—C3—H3119.1C28—C27—H27120.2
C2—C3—H3119.1C23—C28—C27120.1 (4)
C3—C4—C5121.9 (5)C23—C28—H28119.9
C3—C4—H4119.1C27—C28—H28119.9
C5—C4—H4119.1N3—C29—C30123.5 (6)
C6—C5—C4118.3 (5)N3—C29—H29118.2
C6—C5—H5120.9C30—C29—H29118.2
C4—C5—H5120.9C29—C30—C31118.6 (6)
C5—C6—C1121.2 (4)C29—C30—H30120.7
C5—C6—H6119.4C31—C30—H30120.7
C1—C6—H6119.4C32—C31—C30119.0 (6)
N1—C7—C1124.4 (4)C32—C31—H31120.5
N1—C7—H7117.8C30—C31—H31120.5
C1—C7—H7117.8C31—C32—C33119.8 (6)
C9—C8—C13120.2 (4)C31—C32—H32120.1
C9—C8—C14122.2 (4)C33—C32—H32120.1
C13—C8—C14117.5 (4)N3—C33—C32121.6 (5)
O2—C9—C8125.1 (4)N3—C33—H33119.2
O2—C9—C10117.2 (4)C32—C33—H33119.2
C8—C9—C10117.7 (4)N4—C34—C35122.8 (5)
C11—C10—C9120.6 (5)N4—C34—H34118.6
C11—C10—H10119.7C35—C34—H34118.6
C9—C10—H10119.7C36—C35—C34118.8 (5)
C12—C11—C10121.0 (5)C36—C35—H35120.6
C12—C11—H11119.5C34—C35—H35120.6
C10—C11—H11119.5C37—C36—C35118.7 (5)
C13—C12—C11119.9 (5)C37—C36—H36120.7
C13—C12—H12120.0C35—C36—H36120.7
C11—C12—H12120.0C36—C37—C38120.3 (5)
C12—C13—C8120.5 (5)C36—C37—H37119.9
C12—C13—H13119.8C38—C37—H37119.9
C8—C13—H13119.8N4—C38—C37121.1 (5)
N2—C14—C8125.0 (4)N4—C38—H38119.4
N2—C14—H14117.5C37—C38—H38119.4

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O7—H7C···O80.851.852.701 (12)176
O7—H7D···O1i0.852.042.888 (8)176
O8—H8C···O90.851.732.575 (14)177
O8—H8D···O4ii0.851.992.835 (10)176
O9—H9C···O3ii0.852.363.175 (11)161

Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) −x+1/2, −y+1, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2754).

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