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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): m1351.
Published online 2009 October 13. doi:  10.1107/S160053680904046X
PMCID: PMC2971102

Bis[4′-(4-cyano­phen­yl)-2,2′:6′,2′′-terpyridine]cobalt(II) dichloride

Abstract

The title complex, [Co(C22H14N4)2]Cl2, has been synthesized by a solvothermal reaction of the 4′-(4-cyano­phen­yl)-2,2′:6′,2′′-terpyridine ligand with CoCl2·6H2O. The cobalt(II) ion is six-coordinated by two tridentate ligands in a distorted octa­hedral geometry. The benzene rings form dihedral angles of 30.02 (7) and 30.26 (7)° with the mean planes of the terpyridine ring systems. The chloride anions are statistically disordered over two positions with refined site occupancies of 0.601 (2) and 0.399 (2).

Related literature

For the synthesis of functionalized terpyridines, see: Heller & Schubert (2003 [triangle]). For the structure of related cobalt complexes, see: Yu et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-m1351-scheme1.jpg

Experimental

Crystal data

  • [Co(C22H14N4)2]Cl2
  • M r = 798.57
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1351-efi1.jpg
  • a = 13.258 (3) Å
  • b = 12.349 (3) Å
  • c = 25.394 (7) Å
  • β = 101.585 (13)°
  • V = 4072.9 (18) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.59 mm−1
  • T = 291 K
  • 0.30 × 0.26 × 0.24 mm

Data collection

  • Rigaku SCXmini diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 [triangle]) T min = 0.84, T max = 0.87
  • 18347 measured reflections
  • 7941 independent reflections
  • 7439 reflections with I > 2σ(I)
  • R int = 0.030

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.103
  • S = 1.04
  • 7941 reflections
  • 515 parameters
  • 2 restraints
  • H-atom parameters constrained
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.32 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 3940 Friedel pairs
  • Flack parameter: 0.079 (12)

Data collection: CrystalClear (Rigaku, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680904046X/rz2368sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680904046X/rz2368Isup2.hkl

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

supplementary crystallographic information

Comment

Polypyridine ligands have played an important role in many areas. In particular, the chelating ligand terpyridine and its derivatives have been studied extensively as outstanding complexing agents for a wide range of metal ions (Heller & Schubert, 2003). In this paper, we report the crystal structure of the title compound obtained by a solvothermal reaction of CoCl2.6H2O and the tridentate 4'-(4-cyanophenyl)-2,2': 6',2''-terpyridine ligand.

An ORTEP drawing of the title compound is shown in Fig. 1. Both Cl- anions are disordered over two positions with refined site occupancies of 0.601 (2) and 0.399 (2). The cobalt(II) ion is six-coordinated by two mer-arranged tridentate N3-terpyridine ligands in a distorted octahedral geometry. As observed in the related complexes bis[4'-(4-cyanophenyl)-2,2':6',2''-terpyridine]cobalt(II) bis(tetrafluoridoborate) nitromethane solvate and bis[4'-(4-cyanophenyl)-2,2':6',2''-terpyridine]cobalt(III) tris(tetrafluoridoborate) nitromethane solvate (Yu et al., 2008), the Co–N1 and Co–N4 bond distances of the central pyridine rings [2.000 (3) and 1.980 (3) Å, respectively] are significantly shorter than those involving the side pyridine rings [Co–N2 = 2.105 (3) Å; Co–N3 = 2.089 (3) Å; Co–N5 = 2.119 (3) Å; Co–N6 = 2.093 (3) Å], resulting in a pronounced distortion of the octahedral coordination geometry at the metal centre. The terpyridine ring systems are only approximately planar (maximum deviation of 0.170 (4) Å for atom C34) and form dihedral angles of 30.02 (7) and 30.26 (7)° with the attached benzene rings.

Experimental

A mixture of 4'-(4-cyanophenyl)-2,2':6',2''-terpyridine (33.4 mg, 0.1 mmol), CoCl2.6H2O (12 mg, 0.05 mmol) in a 10% water-ethanol solution (2 ml) were sealed in a glass tube was kept at 125 °C. Red crystals suitable for X-ray analysis were obtained after 5 days.

Refinement

All H atoms were positioned geometrically and treated as riding, with C—H = 0.93 Å and Uiso(H) = 1.2 Ueq(C).

Figures

Fig. 1.
A view of the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen atoms are omitted for the clarity.

Crystal data

[Co(C22H14N4)2]Cl2F(000) = 1636
Mr = 798.57Dx = 1.302 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 2346 reflections
a = 13.258 (3) Åθ = 2.1–27.4°
b = 12.349 (3) ŵ = 0.59 mm1
c = 25.394 (7) ÅT = 291 K
β = 101.585 (13)°Block, red
V = 4072.9 (18) Å30.30 × 0.26 × 0.24 mm
Z = 4

Data collection

Rigaku SCXmini diffractometer7941 independent reflections
Radiation source: sealed tube7439 reflections with I > 2σ(I)
graphiteRint = 0.030
Detector resolution: 13.6612 pixels mm-1θmax = 26.0°, θmin = 3.0°
ω scansh = −16→16
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)k = −15→15
Tmin = 0.84, Tmax = 0.87l = −31→31
18347 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.103w = 1/[σ2(Fo2) + (0.06P)2 + 1.99P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
7941 reflectionsΔρmax = 0.19 e Å3
515 parametersΔρmin = −0.32 e Å3
2 restraintsAbsolute structure: Flack (1983), 3940 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.079 (12)

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)
C10.4556 (2)0.7500 (3)0.66226 (14)0.0433 (7)
H1A0.44300.77130.69550.052*
C20.4258 (3)0.6489 (3)0.64410 (15)0.0504 (8)
H2A0.39670.60130.66530.060*
C30.4396 (3)0.6178 (3)0.59307 (15)0.0533 (9)
H3A0.41790.54980.57970.064*
C40.4871 (3)0.6904 (3)0.56123 (15)0.0525 (8)
H4A0.49860.67110.52750.063*
C50.5151 (2)0.7915 (2)0.58384 (13)0.0390 (6)
C60.5656 (2)0.8774 (2)0.55783 (12)0.0394 (6)
C70.5987 (3)0.8635 (3)0.50908 (15)0.0517 (8)
H7A0.58540.79880.49020.062*
C80.6519 (2)0.9472 (3)0.48857 (12)0.0400 (7)
C90.6644 (3)1.0457 (2)0.51690 (14)0.0439 (7)
H9A0.69531.10390.50300.053*
C100.6306 (2)1.0582 (3)0.56667 (13)0.0404 (7)
C110.6467 (2)1.1512 (2)0.59883 (13)0.0391 (6)
C120.6815 (3)1.2479 (3)0.58696 (15)0.0555 (9)
H12A0.70201.25840.55440.067*
C130.6872 (3)1.3370 (3)0.62514 (15)0.0522 (8)
H13A0.71021.40490.61690.063*
C140.6589 (3)1.3198 (3)0.67199 (15)0.0543 (9)
H14A0.65941.37640.69620.065*
C150.6290 (3)1.2182 (3)0.68424 (16)0.0514 (8)
H15A0.61481.20750.71830.062*
C160.6931 (3)0.9314 (3)0.43904 (13)0.0423 (7)
C170.7813 (3)0.9872 (3)0.43298 (14)0.0543 (9)
H17A0.80971.03910.45810.065*
C180.8274 (3)0.9655 (3)0.38933 (17)0.0597 (9)
H18A0.88701.00200.38570.072*
C190.7838 (3)0.8889 (3)0.35105 (14)0.0554 (9)
C200.6954 (3)0.8334 (4)0.35633 (15)0.0593 (10)
H20A0.66670.78240.33070.071*
C210.6496 (3)0.8545 (3)0.40035 (16)0.0553 (9)
H21A0.59020.81760.40400.066*
C220.8327 (3)0.8633 (3)0.30799 (15)0.0565 (9)
C310.3510 (2)1.0851 (3)0.62015 (14)0.0471 (8)
H31A0.36871.08610.58650.057*
C320.2585 (2)1.1288 (3)0.62426 (14)0.0478 (8)
H32A0.21711.16250.59490.057*
C330.2299 (3)1.1225 (3)0.66953 (14)0.0488 (8)
H33A0.16551.14920.67220.059*
C340.2927 (2)1.0764 (3)0.71530 (14)0.0450 (7)
H34A0.27321.07340.74840.054*
C350.3859 (3)1.0358 (2)0.70731 (14)0.0418 (7)
C360.4629 (2)0.9833 (2)0.75215 (13)0.0388 (7)
C370.4442 (2)0.9479 (3)0.80124 (13)0.0422 (7)
H37A0.38110.96250.81040.051*
C380.5186 (2)0.8908 (3)0.83676 (13)0.0423 (7)
C390.6133 (2)0.8692 (3)0.82105 (11)0.0370 (6)
H39A0.66550.83180.84380.044*
C400.6266 (2)0.9048 (3)0.77123 (12)0.0383 (6)
C410.7216 (2)0.8845 (3)0.74866 (12)0.0393 (6)
C420.8132 (2)0.8443 (3)0.77910 (14)0.0468 (7)
H42A0.81950.82520.81500.056*
C430.8944 (2)0.8347 (3)0.75235 (13)0.0455 (7)
H43A0.95770.81090.77160.055*
C440.8859 (3)0.8579 (3)0.70063 (14)0.0457 (7)
H44A0.94080.84660.68350.055*
C450.7900 (2)0.9006 (3)0.67171 (14)0.0458 (7)
H45A0.78410.92000.63580.055*
C460.4954 (3)0.8463 (3)0.88779 (13)0.0443 (7)
C470.4241 (3)0.8945 (3)0.91366 (13)0.0470 (7)
H47A0.39220.95840.89980.056*
C480.3989 (3)0.8503 (3)0.95938 (14)0.0566 (10)
H48A0.35240.88450.97680.068*
C490.4469 (3)0.7497 (3)0.97918 (14)0.0494 (8)
C500.5180 (3)0.7026 (3)0.95501 (16)0.0543 (8)
H50A0.54980.63860.96870.065*
C510.5438 (3)0.7506 (3)0.90896 (14)0.0451 (7)
H51A0.59310.71850.89270.054*
C520.4167 (3)0.7051 (3)1.02482 (13)0.0497 (8)
Cl10.72405 (11)0.45349 (12)0.35812 (5)0.0485 (4)0.601 (2)
Cl20.56620 (11)0.38709 (12)0.92594 (5)0.0514 (4)0.601 (2)
Cl1'0.81405 (18)0.33040 (19)0.38569 (9)0.0536 (6)0.399 (2)
Cl2'0.64297 (16)0.43338 (17)0.98097 (9)0.0480 (5)0.399 (2)
Co10.56329 (2)0.97563 (3)0.660571 (17)0.03465 (10)
N10.5537 (2)0.9571 (2)0.73767 (12)0.0383 (6)
N20.70937 (18)0.9132 (2)0.69502 (10)0.0395 (6)
N30.4179 (2)1.0409 (2)0.66062 (11)0.0436 (6)
N40.5838 (3)0.9701 (2)0.58551 (13)0.0459 (7)
N50.50297 (19)0.8216 (2)0.63437 (11)0.0374 (5)
N60.6186 (2)1.1312 (2)0.65007 (11)0.0432 (6)
N70.3920 (2)0.6612 (3)1.06197 (12)0.0552 (7)
N80.8747 (3)0.8401 (3)0.27126 (13)0.0613 (8)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0369 (15)0.0384 (16)0.0550 (18)−0.0097 (12)0.0103 (13)0.0049 (14)
C20.0429 (18)0.0469 (19)0.064 (2)−0.0191 (15)0.0168 (15)0.0096 (16)
C30.0385 (17)0.059 (2)0.060 (2)−0.0194 (15)0.0027 (15)−0.0081 (17)
C40.052 (2)0.0401 (18)0.061 (2)−0.0016 (14)0.0011 (16)−0.0100 (15)
C50.0376 (15)0.0299 (14)0.0463 (16)0.0047 (12)0.0003 (12)−0.0015 (12)
C60.0455 (17)0.0322 (15)0.0377 (15)−0.0036 (12)0.0013 (12)0.0028 (12)
C70.063 (2)0.0440 (18)0.0527 (19)−0.0052 (16)0.0228 (17)−0.0014 (15)
C80.0460 (17)0.0369 (15)0.0314 (14)0.0031 (13)−0.0054 (12)0.0138 (12)
C90.0508 (18)0.0262 (14)0.0557 (19)0.0024 (12)0.0129 (15)0.0108 (13)
C100.0301 (14)0.0406 (16)0.0472 (16)−0.0022 (12)0.0000 (12)0.0068 (13)
C110.0328 (14)0.0344 (15)0.0482 (16)0.0037 (12)0.0035 (12)0.0125 (13)
C120.067 (2)0.0419 (19)0.055 (2)−0.0191 (17)0.0046 (17)0.0135 (15)
C130.0383 (17)0.0499 (19)0.067 (2)−0.0189 (15)0.0076 (15)−0.0020 (17)
C140.056 (2)0.0464 (19)0.060 (2)−0.0027 (16)0.0096 (17)−0.0196 (16)
C150.0401 (17)0.0428 (19)0.071 (2)0.0005 (14)0.0094 (15)−0.0177 (16)
C160.0464 (16)0.0396 (16)0.0386 (15)0.0070 (13)0.0030 (13)0.0065 (13)
C170.069 (2)0.056 (2)0.0392 (16)−0.0119 (17)0.0138 (16)0.0093 (15)
C180.057 (2)0.063 (2)0.064 (2)0.0085 (17)0.0223 (18)−0.0002 (18)
C190.067 (2)0.058 (2)0.0415 (17)0.0193 (18)0.0111 (16)0.0131 (16)
C200.071 (3)0.067 (2)0.0409 (18)0.013 (2)0.0142 (17)0.0030 (17)
C210.061 (2)0.048 (2)0.059 (2)−0.0084 (17)0.0161 (17)−0.0154 (17)
C220.065 (2)0.056 (2)0.051 (2)0.0216 (18)0.0165 (16)0.0117 (16)
C310.0339 (15)0.0512 (19)0.0505 (18)0.0025 (13)−0.0056 (13)0.0189 (15)
C320.0386 (17)0.0442 (18)0.0546 (19)−0.0034 (13)−0.0052 (14)0.0128 (15)
C330.0424 (18)0.0469 (19)0.058 (2)0.0129 (15)0.0113 (15)−0.0011 (15)
C340.0399 (16)0.0527 (19)0.0448 (16)0.0029 (14)0.0145 (13)0.0049 (14)
C350.0438 (16)0.0326 (14)0.0489 (17)0.0072 (12)0.0091 (13)−0.0060 (13)
C360.0355 (15)0.0325 (15)0.0509 (18)0.0096 (12)0.0148 (13)−0.0055 (13)
C370.0339 (15)0.0481 (18)0.0450 (17)0.0086 (13)0.0091 (12)−0.0081 (14)
C380.0371 (15)0.0505 (18)0.0397 (16)0.0101 (13)0.0089 (12)−0.0016 (14)
C390.0318 (14)0.0410 (15)0.0368 (14)0.0037 (11)0.0032 (11)−0.0065 (12)
C400.0330 (14)0.0396 (16)0.0428 (15)−0.0076 (12)0.0087 (12)0.0002 (12)
C410.0309 (14)0.0403 (15)0.0461 (16)−0.0013 (12)0.0067 (12)0.0028 (13)
C420.0381 (16)0.0544 (19)0.0459 (17)0.0134 (14)0.0035 (13)0.0014 (15)
C430.0256 (13)0.0537 (19)0.0503 (17)0.0067 (13)−0.0089 (12)0.0118 (15)
C440.0343 (16)0.0488 (18)0.0574 (19)−0.0001 (13)0.0177 (14)0.0167 (15)
C450.0374 (16)0.0502 (18)0.0485 (17)−0.0050 (14)0.0057 (13)0.0018 (15)
C460.0474 (17)0.0502 (19)0.0372 (16)0.0021 (14)0.0128 (13)−0.0030 (14)
C470.054 (2)0.0486 (19)0.0398 (16)0.0064 (15)0.0113 (14)−0.0024 (14)
C480.071 (2)0.064 (2)0.0406 (17)0.0236 (19)0.0238 (16)0.0010 (16)
C490.0485 (18)0.0510 (19)0.0516 (18)−0.0031 (15)0.0174 (15)0.0040 (15)
C500.0500 (19)0.051 (2)0.066 (2)0.0079 (16)0.0214 (16)0.0120 (17)
C510.053 (2)0.0357 (17)0.0490 (17)−0.0016 (14)0.0170 (14)−0.0021 (13)
C520.057 (2)0.0485 (19)0.0454 (18)−0.0119 (15)0.0151 (15)−0.0010 (15)
Cl10.0543 (8)0.0529 (8)0.0400 (6)0.0026 (6)0.0133 (5)−0.0035 (5)
Cl20.0559 (8)0.0544 (8)0.0461 (7)0.0087 (6)0.0155 (6)−0.0008 (6)
Cl1'0.0564 (13)0.0522 (12)0.0563 (12)−0.0047 (9)0.0214 (9)0.0021 (10)
Cl2'0.0534 (11)0.0402 (10)0.0516 (11)0.0032 (8)0.0135 (9)−0.0007 (9)
Co10.03243 (18)0.03119 (17)0.04075 (19)−0.00312 (17)0.00836 (13)0.00386 (18)
N10.0307 (13)0.0365 (13)0.0492 (16)−0.0026 (10)0.0118 (11)0.0048 (12)
N20.0317 (12)0.0365 (13)0.0499 (14)−0.0017 (10)0.0074 (10)−0.0021 (11)
N30.0432 (14)0.0421 (14)0.0432 (14)0.0090 (11)0.0033 (11)0.0115 (11)
N40.061 (2)0.0309 (14)0.0445 (16)−0.0045 (12)0.0073 (14)0.0030 (12)
N50.0311 (12)0.0323 (12)0.0497 (14)−0.0009 (9)0.0105 (10)0.0081 (11)
N60.0590 (16)0.0298 (12)0.0426 (14)−0.0034 (11)0.0147 (12)−0.0024 (11)
N70.0517 (17)0.0637 (19)0.0507 (16)0.0008 (14)0.0114 (13)0.0039 (15)
N80.071 (2)0.061 (2)0.0559 (18)0.0210 (17)0.0214 (16)−0.0034 (15)

Geometric parameters (Å, °)

C1—N51.362 (4)C32—C331.283 (5)
C1—C21.363 (5)C32—H32A0.9300
C1—H1A0.9300C33—C341.407 (5)
C2—C31.398 (5)C33—H33A0.9300
C2—H2A0.9300C34—C351.385 (4)
C3—C41.435 (5)C34—H34A0.9300
C3—H3A0.9300C35—N31.338 (4)
C4—C51.393 (5)C35—C361.514 (4)
C4—H4A0.9300C36—N11.367 (4)
C5—N51.376 (4)C36—C371.390 (5)
C5—C61.480 (4)C37—C381.388 (4)
C6—N41.340 (4)C37—H37A0.9300
C6—C71.404 (5)C38—C391.416 (4)
C7—C81.409 (5)C38—C461.496 (5)
C7—H7A0.9300C39—C401.384 (4)
C8—C91.406 (5)C39—H39A0.9300
C8—C161.482 (5)C40—N11.322 (4)
C9—C101.432 (5)C40—C411.506 (4)
C9—H9A0.9300C41—N21.385 (4)
C10—N41.385 (4)C41—C421.393 (4)
C10—C111.401 (5)C42—C431.389 (5)
C11—C121.336 (4)C42—H42A0.9300
C11—N61.445 (4)C43—C441.327 (5)
C12—C131.459 (5)C43—H43A0.9300
C12—H12A0.9300C44—C451.435 (5)
C13—C141.334 (5)C44—H44A0.9300
C13—H13A0.9300C45—N21.331 (4)
C14—C151.370 (5)C45—H45A0.9300
C14—H14A0.9300C46—C471.389 (5)
C15—N61.371 (4)C46—C511.400 (5)
C15—H15A0.9300C47—C481.383 (5)
C16—C171.392 (5)C47—H47A0.9300
C16—C211.404 (5)C48—C491.439 (5)
C17—C181.395 (5)C48—H48A0.9300
C17—H17A0.9300C49—C501.355 (5)
C18—C191.396 (6)C49—C521.412 (5)
C18—H18A0.9300C50—C511.413 (5)
C19—C201.387 (6)C50—H50A0.9300
C19—C221.414 (5)C51—H51A0.9300
C20—C211.400 (5)C52—N71.190 (4)
C20—H20A0.9300Co1—N41.980 (3)
C21—H21A0.9300Co1—N12.000 (3)
C22—N81.213 (5)Co1—N32.089 (3)
C31—N31.332 (4)Co1—N62.093 (3)
C31—C321.363 (5)Co1—N22.105 (3)
C31—H31A0.9300Co1—N52.119 (3)
N5—C1—C2123.5 (3)C37—C36—C35126.5 (3)
N5—C1—H1A118.3C38—C37—C36120.8 (3)
C2—C1—H1A118.3C38—C37—H37A119.6
C1—C2—C3118.8 (3)C36—C37—H37A119.6
C1—C2—H2A120.6C37—C38—C39117.8 (3)
C3—C2—H2A120.6C37—C38—C46120.4 (3)
C2—C3—C4120.3 (3)C39—C38—C46121.5 (3)
C2—C3—H3A119.8C40—C39—C38118.8 (3)
C4—C3—H3A119.8C40—C39—H39A120.6
C5—C4—C3116.0 (3)C38—C39—H39A120.6
C5—C4—H4A122.0N1—C40—C39122.3 (3)
C3—C4—H4A122.0N1—C40—C41113.2 (3)
N5—C5—C4123.8 (3)C39—C40—C41124.5 (3)
N5—C5—C6111.7 (3)N2—C41—C42123.6 (3)
C4—C5—C6124.4 (3)N2—C41—C40113.0 (3)
N4—C6—C7120.8 (3)C42—C41—C40123.4 (3)
N4—C6—C5115.4 (3)C43—C42—C41115.7 (3)
C7—C6—C5123.7 (3)C43—C42—H42A122.1
C6—C7—C8120.3 (3)C41—C42—H42A122.1
C6—C7—H7A119.9C44—C43—C42123.1 (3)
C8—C7—H7A119.9C44—C43—H43A118.5
C9—C8—C7117.5 (3)C42—C43—H43A118.5
C9—C8—C16121.5 (3)C43—C44—C45118.5 (3)
C7—C8—C16121.0 (3)C43—C44—H44A120.8
C8—C9—C10121.3 (3)C45—C44—H44A120.8
C8—C9—H9A119.4N2—C45—C44121.6 (3)
C10—C9—H9A119.4N2—C45—H45A119.2
N4—C10—C11118.0 (3)C44—C45—H45A119.2
N4—C10—C9117.5 (3)C47—C46—C51118.9 (3)
C11—C10—C9124.4 (3)C47—C46—C38122.1 (3)
C12—C11—C10128.4 (3)C51—C46—C38119.0 (3)
C12—C11—N6121.3 (3)C48—C47—C46122.0 (3)
C10—C11—N6110.4 (3)C48—C47—H47A119.0
C11—C12—C13119.9 (3)C46—C47—H47A119.0
C11—C12—H12A120.0C47—C48—C49118.0 (3)
C13—C12—H12A120.0C47—C48—H48A121.0
C14—C13—C12119.1 (3)C49—C48—H48A121.0
C14—C13—H13A120.5C50—C49—C52122.8 (4)
C12—C13—H13A120.5C50—C49—C48120.7 (3)
C13—C14—C15119.6 (3)C52—C49—C48116.5 (3)
C13—C14—H14A120.2C49—C50—C51120.1 (3)
C15—C14—H14A120.2C49—C50—H50A120.0
C14—C15—N6124.8 (4)C51—C50—H50A120.0
C14—C15—H15A117.6C46—C51—C50120.2 (3)
N6—C15—H15A117.6C46—C51—H51A119.9
C17—C16—C21119.6 (3)C50—C51—H51A119.9
C17—C16—C8119.3 (3)N7—C52—C49175.9 (4)
C21—C16—C8120.9 (3)N4—Co1—N1170.50 (11)
C16—C17—C18120.3 (4)N4—Co1—N3108.59 (12)
C16—C17—H17A119.8N1—Co1—N378.69 (11)
C18—C17—H17A119.8N4—Co1—N677.85 (11)
C17—C18—C19119.8 (4)N1—Co1—N6108.82 (11)
C17—C18—H18A120.1N3—Co1—N689.60 (11)
C19—C18—H18A120.1N4—Co1—N295.44 (12)
C20—C19—C18120.5 (4)N1—Co1—N277.59 (11)
C20—C19—C22119.5 (4)N3—Co1—N2155.92 (10)
C18—C19—C22120.0 (4)N6—Co1—N294.15 (11)
C19—C20—C21119.7 (4)N4—Co1—N577.46 (11)
C19—C20—H20A120.1N1—Co1—N596.34 (10)
C21—C20—H20A120.1N3—Co1—N593.23 (11)
C20—C21—C16120.1 (4)N6—Co1—N5154.74 (10)
C20—C21—H21A120.0N2—Co1—N593.40 (10)
C16—C21—H21A120.0C40—N1—C36120.8 (3)
N8—C22—C19179.2 (4)C40—N1—Co1120.4 (2)
N3—C31—C32125.0 (3)C36—N1—Co1117.9 (2)
N3—C31—H31A117.5C45—N2—C41117.5 (3)
C32—C31—H31A117.5C45—N2—Co1127.7 (2)
C33—C32—C31118.5 (3)C41—N2—Co1114.74 (19)
C33—C32—H32A120.8C31—N3—C35114.9 (3)
C31—C32—H32A120.8C31—N3—Co1129.0 (2)
C32—C33—C34122.1 (3)C35—N3—Co1116.1 (2)
C32—C33—H33A118.9C6—N4—C10122.4 (3)
C34—C33—H33A118.9C6—N4—Co1119.3 (2)
C35—C34—C33115.0 (3)C10—N4—Co1117.6 (2)
C35—C34—H34A122.5C1—N5—C5117.5 (3)
C33—C34—H34A122.5C1—N5—Co1127.1 (2)
N3—C35—C34124.3 (3)C5—N5—Co1115.35 (19)
N3—C35—C36113.6 (3)C15—N6—C11115.1 (3)
C34—C35—C36122.1 (3)C15—N6—Co1129.2 (2)
N1—C36—C37119.5 (3)C11—N6—Co1115.61 (19)
N1—C36—C35113.4 (3)
N5—C1—C2—C3−3.2 (5)N3—Co1—N1—C40174.6 (3)
C1—C2—C3—C41.8 (5)N6—Co1—N1—C40−99.8 (2)
C2—C3—C4—C5−1.5 (5)N2—Co1—N1—C40−9.6 (2)
C3—C4—C5—N52.6 (5)N5—Co1—N1—C4082.5 (2)
C3—C4—C5—C6179.5 (3)N3—Co1—N1—C365.4 (2)
N5—C5—C6—N4−4.4 (4)N6—Co1—N1—C3691.1 (2)
C4—C5—C6—N4178.3 (3)N2—Co1—N1—C36−178.7 (2)
N5—C5—C6—C7172.0 (3)N5—Co1—N1—C36−86.6 (2)
C4—C5—C6—C7−5.3 (5)C44—C45—N2—C410.7 (5)
N4—C6—C7—C80.1 (5)C44—C45—N2—Co1179.2 (2)
C5—C6—C7—C8−176.1 (3)C42—C41—N2—C450.4 (5)
C6—C7—C8—C9−3.8 (5)C40—C41—N2—C45178.5 (3)
C6—C7—C8—C16176.1 (3)C42—C41—N2—Co1−178.3 (3)
C7—C8—C9—C104.1 (5)C40—C41—N2—Co1−0.2 (3)
C16—C8—C9—C10−175.7 (3)N4—Co1—N2—C4512.7 (3)
C8—C9—C10—N4−0.9 (5)N1—Co1—N2—C45−173.9 (3)
C8—C9—C10—C11175.5 (3)N3—Co1—N2—C45−163.8 (3)
N4—C10—C11—C12−173.4 (3)N6—Co1—N2—C45−65.5 (3)
C9—C10—C11—C1210.2 (5)N5—Co1—N2—C4590.4 (3)
N4—C10—C11—N65.8 (4)N4—Co1—N2—C41−168.8 (2)
C9—C10—C11—N6−170.5 (3)N1—Co1—N2—C414.7 (2)
C10—C11—C12—C13176.4 (3)N3—Co1—N2—C4114.7 (4)
N6—C11—C12—C13−2.7 (5)N6—Co1—N2—C41113.1 (2)
C11—C12—C13—C141.0 (6)N5—Co1—N2—C41−91.1 (2)
C12—C13—C14—C152.6 (6)C32—C31—N3—C353.7 (5)
C13—C14—C15—N6−4.8 (6)C32—C31—N3—Co1−177.9 (3)
C9—C8—C16—C1730.1 (5)C34—C35—N3—C31−2.5 (5)
C7—C8—C16—C17−149.8 (3)C36—C35—N3—C31178.9 (3)
C9—C8—C16—C21−155.2 (3)C34—C35—N3—Co1178.9 (3)
C7—C8—C16—C2124.9 (5)C36—C35—N3—Co10.3 (3)
C21—C16—C17—C18−1.2 (5)N4—Co1—N3—C31−7.7 (3)
C8—C16—C17—C18173.6 (3)N1—Co1—N3—C31178.7 (3)
C16—C17—C18—C191.2 (6)N6—Co1—N3—C3169.4 (3)
C17—C18—C19—C20−0.6 (6)N2—Co1—N3—C31168.7 (3)
C17—C18—C19—C22−177.3 (4)N5—Co1—N3—C31−85.5 (3)
C18—C19—C20—C210.1 (6)N4—Co1—N3—C35170.7 (2)
C22—C19—C20—C21176.8 (4)N1—Co1—N3—C35−3.0 (2)
C19—C20—C21—C16−0.1 (6)N6—Co1—N3—C35−112.2 (2)
C17—C16—C21—C200.7 (5)N2—Co1—N3—C35−12.9 (4)
C8—C16—C21—C20−174.0 (3)N5—Co1—N3—C3592.9 (2)
N3—C31—C32—C33−4.0 (6)C7—C6—N4—C103.4 (5)
C31—C32—C33—C342.9 (6)C5—C6—N4—C10179.9 (3)
C32—C33—C34—C35−1.8 (5)C7—C6—N4—Co1−167.0 (3)
C33—C34—C35—N31.7 (5)C5—C6—N4—Co19.5 (4)
C33—C34—C35—C36−179.9 (3)C11—C10—N4—C6−179.6 (3)
N3—C35—C36—N14.0 (4)C9—C10—N4—C6−3.0 (5)
C34—C35—C36—N1−174.6 (3)C11—C10—N4—Co1−9.1 (4)
N3—C35—C36—C37−166.5 (3)C9—C10—N4—Co1167.5 (2)
C34—C35—C36—C3714.9 (5)N3—Co1—N4—C6−97.3 (3)
N1—C36—C37—C383.2 (5)N6—Co1—N4—C6177.3 (3)
C35—C36—C37—C38173.3 (3)N2—Co1—N4—C684.2 (3)
C36—C37—C38—C39−0.6 (5)N5—Co1—N4—C6−8.1 (3)
C36—C37—C38—C46−175.7 (3)N3—Co1—N4—C1091.9 (3)
C37—C38—C39—C40−0.6 (5)N6—Co1—N4—C106.4 (2)
C46—C38—C39—C40174.4 (3)N2—Co1—N4—C10−86.6 (3)
C38—C39—C40—N1−0.7 (5)N5—Co1—N4—C10−178.9 (3)
C38—C39—C40—C41−178.0 (3)C2—C1—N5—C54.1 (5)
N1—C40—C41—N2−7.2 (4)C2—C1—N5—Co1−174.9 (3)
C39—C40—C41—N2170.3 (3)C4—C5—N5—C1−3.8 (4)
N1—C40—C41—C42170.9 (3)C6—C5—N5—C1178.9 (3)
C39—C40—C41—C42−11.6 (5)C4—C5—N5—Co1175.3 (2)
N2—C41—C42—C430.4 (5)C6—C5—N5—Co1−2.0 (3)
C40—C41—C42—C43−177.5 (3)N4—Co1—N5—C1−175.7 (3)
C41—C42—C43—C44−2.5 (5)N1—Co1—N5—C111.6 (3)
C42—C43—C44—C453.6 (5)N3—Co1—N5—C1−67.4 (3)
C43—C44—C45—N2−2.7 (5)N6—Co1—N5—C1−163.4 (3)
C37—C38—C46—C47−28.6 (5)N2—Co1—N5—C189.4 (3)
C39—C38—C46—C47156.4 (3)N4—Co1—N5—C55.2 (2)
C37—C38—C46—C51148.7 (3)N1—Co1—N5—C5−167.5 (2)
C39—C38—C46—C51−26.3 (5)N3—Co1—N5—C5113.6 (2)
C51—C46—C47—C48−0.5 (5)N6—Co1—N5—C517.6 (4)
C38—C46—C47—C48176.8 (4)N2—Co1—N5—C5−89.6 (2)
C46—C47—C48—C49−1.8 (6)C14—C15—N6—C113.0 (5)
C47—C48—C49—C502.9 (6)C14—C15—N6—Co1−174.7 (3)
C47—C48—C49—C52−177.9 (4)C12—C11—N6—C150.8 (4)
C52—C49—C50—C51179.1 (3)C10—C11—N6—C15−178.4 (3)
C48—C49—C50—C51−1.7 (6)C12—C11—N6—Co1178.9 (3)
C47—C46—C51—C501.8 (5)C10—C11—N6—Co1−0.4 (3)
C38—C46—C51—C50−175.6 (3)N4—Co1—N6—C15174.5 (3)
C49—C50—C51—C46−0.7 (6)N1—Co1—N6—C15−12.5 (3)
C39—C40—N1—C363.4 (5)N3—Co1—N6—C1565.4 (3)
C41—C40—N1—C36−179.1 (3)N2—Co1—N6—C15−90.8 (3)
C39—C40—N1—Co1−165.5 (2)N5—Co1—N6—C15162.1 (3)
C41—C40—N1—Co112.1 (4)N4—Co1—N6—C11−3.2 (2)
C37—C36—N1—C40−4.6 (5)N1—Co1—N6—C11169.8 (2)
C35—C36—N1—C40−175.9 (3)N3—Co1—N6—C11−112.3 (2)
C37—C36—N1—Co1164.5 (2)N2—Co1—N6—C1191.5 (2)
C35—C36—N1—Co1−6.8 (3)N5—Co1—N6—C11−15.6 (4)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2368).

References

  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Heller, M. & Schubert, U. S. (2003). Eur. J. Org. Chem. pp. 947–961.
  • Rigaku (2005). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Yu, Z., Nabei, A., Izumi, T., Okubo, T. & Kuroda-Sowa, T. (2008). Acta Cryst. C64, m209–m212. [PubMed]

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