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Acta Cryst. (2009). E65, m698-m699    [ doi:10.1107/S1600536809019163 ]

[5,10,15,20-Tetrakis(4-chlorophenyl)porphyrinato]bis(tributylphosphine)cobalt(III) perchlorate

B. Etemadi, R. Kia, M. Asadi and K. Mohammadi

Abstract top

In the molecule of the title compound, [Co(C44H24Cl4N4){(C4H9)3P}2]ClO4, the CoIII centre has a slightly distorted octahedral geometry and is coordinated by four N atoms of the tetrapyrrolic ring in the equatorial positions and two phosphine ligands in the axial positions. The dihedral angles between meso-substituted chlorophenyl rings and the basic tetrapyrrolic ring are 82.66 (9), 82.16 (7), 83.97 (11) and 76.87 (8)°. In one of the phosphine ligands, the two terminal methyl groups are disordered over two positions with refined site-occupancy ratios of 0.70 (7):0.30 (7) and 0.66 (2):0.34 (2). In the crystal structure, molecules are linked together along the a axis by intermolecular C-H...Cl interactions. The crystal structure is further stabilized by intramolecular C-H...O and C-H...N interactions and intermolecular C-H...O and C-H...[pi] interactions.

Comment top

Metalloporphyrins exist ubiquitously in nature and have found a broad spectrum of applications. Among the different applications, great efforts have been made to develop new complexes as catalysts in organic transformation reactions (Liu, et al. 2007).

The molecule of the title compound, Fig. 1, is a substituted metallo- porphyrin. In the title compound, the Co atom has a slightly distorted octahedral geometry which is coordinated by four nitrogen atoms in the equatorial position of the tetrapyrrolic ring and two other phosphine ligands in the axial positions with P1–Co1–P2, P1–Co1–N1 and N1–Co1–N3 angles of 179.18 (13), 88.48 (7), and 178.85 (10)°, respectively (Table 1). The dihedral angles between meso- substituted chlorophenyl rings and the basic tetrapyrrol ring are 82.66 (9), 82.16 (7), 83.97 (11), and 76.87 (8)°. In one of the phosphine ligands the two terminal methyl groups are disordered over two positions with a refined site-occupancies ratio of 0.70 (7)/0.3 (7) and 0.66 (2)/0.34 (2). In the crystal structure, the molecules are linked together by the intermolecular C—H···Cl interactions along the a axis (Fig. 2). The crystal structure is further stabilized by the intramolecular C—H···O and C—H···N and the intermolecular C—H···O and C—H···π interactions [Cg1, Cg2, Cg3, and Cg4 are the centroids of the N1/C2–C5, N2/C7–C10, N3/C12–C15, and N4/C17–C20 five-membered pyrrole rings] (Table 2).

Related literature top

For bond-length data, see Allen et al. (1987). For applications of metalloporphyrins in organic synthesis, see: Liu et al., (2007). For the synthesis, see: Mohammadi, (2005). Cg1, Cg2, Cg3, and Cg4 are the centroids of the N1/C2–C5, N2/C7–C10, N3/C12–C15, and N4/C17–C20 rings, respectively.

Experimental top

In a round-bottomed flask the porphyrinatocobalt(II) (1 mol) was dissolved in methanol (100 ml) and then PBu3 (2 mol) was added to the solution. After heating, the reaction mixture was oxidized by blowing air into the solution for 1 h and the reaction mixture was checked for completing by UV-vis spectrophotometry. After completing, sodium perchlorate (1.2 mol) was added and by evaporating solvent, the resulting brown product was collected. Single crystals suitable for X-ray diffraction were obtained from methanol solution.

Refinement top

All of the hydrogen atoms were positioned geometrically [C—H = 0.95–0.99 Å] and refined using a riding model approximation with Uiso (H) = 1.2 or 1.5 Ueq (C). A rotating group model was applied to the methyl groups. In one of the phosphine ligands the two terminal methyl groups are disordered over two positions with a refined site-occupancies ratio of 0.70 (7)/0.3 (7) and 0.66 (2)/0.34 (2).

The bond distances of the major and minor components were restrained to be 1.54 (1) Å.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering. Hydrogen atoms were omitted for clarity. Open bonds show the minor component.
[Figure 2] Fig. 2. The crystal packing of the major component of the title compound, viewed down the c-axis, showing linking of the molecules along the a-axis through intermolecular C—H···Cl interactions. Intermolecular interactions are drawn as dashed lines.
[5,10,15,20-Tetrakis(4- chlorophenyl)porphyrinato]bis(tributylphosphine)cobalt(III) perchlorate top
Crystal data top
[Co(C44H24Cl4N4)(C12H27P1)2]ClO4F000 = 2752
Mr = 1313.46Dx = 1.349 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1298 reflections
a = 12.4803 (5) Åθ = 3.1–29.2º
b = 21.8192 (8) ŵ = 0.57 mm−1
c = 24.0902 (10) ÅT = 120 K
β = 99.542 (3)ºBlock, brown
V = 6469.2 (4) Å30.50 × 0.20 × 0.14 mm
Z = 4
Data collection top
Stoe IPDS-II
diffractometer		17260 independent reflections
Radiation source: fine-focus sealed tube13604 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.091
Detector resolution: 0.15 pixels mm-1θmax = 29.3º
T = 120 Kθmin = 1.7º
rotation method scansh = −17→16
Absorption correction: numerical
shape of crystal determined optically		k = 0→29
Tmin = 0.869, Tmax = 0.918l = 0→32
17260 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.069H-atom parameters constrained
wR(F2) = 0.181  w = 1/[σ2(Fo2) + (0.0701P)2 + 9.0268P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.002
17260 reflectionsΔρmax = 0.74 e Å−3
773 parametersΔρmin = −0.76 e Å−3
4 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Co(C44H24Cl4N4)(C12H27P1)2]ClO4V = 6469.2 (4) Å3
Mr = 1313.46Z = 4
Monoclinic, P21/cMo Kα
a = 12.4803 (5) ŵ = 0.57 mm−1
b = 21.8192 (8) ÅT = 120 K
c = 24.0902 (10) Å0.50 × 0.20 × 0.14 mm
β = 99.542 (3)º
Data collection top
Stoe IPDS-II
diffractometer		17260 independent reflections
Absorption correction: numerical
shape of crystal determined optically		13604 reflections with I > 2σ(I)
Tmin = 0.869, Tmax = 0.918Rint = 0.091
17260 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0694 restraints
wR(F2) = 0.181H-atom parameters constrained
S = 1.08Δρmax = 0.74 e Å−3
17260 reflectionsΔρmin = −0.76 e Å−3
773 parameters
Special details top

Experimental. (program? reference?)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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)
Co10.38297 (3)0.731732 (17)0.918800 (14)0.01758 (9)
Cl1−0.04116 (9)0.89313 (5)0.59051 (4)0.0456 (2)
Cl20.95841 (7)0.62065 (5)0.72825 (4)0.0405 (2)
Cl30.83243 (8)0.62163 (5)1.25879 (4)0.0479 (2)
Cl4−0.21035 (7)0.85554 (4)1.08795 (4)0.03853 (19)
P10.45653 (6)0.82911 (3)0.94063 (3)0.02090 (14)
P20.31178 (6)0.63377 (3)0.89761 (3)0.02301 (15)
N10.4121 (2)0.74303 (11)0.84075 (9)0.0209 (4)
N20.52919 (19)0.69466 (11)0.94034 (9)0.0201 (4)
N30.35557 (19)0.72185 (11)0.99768 (9)0.0196 (4)
N40.23561 (19)0.76654 (11)0.89676 (9)0.0195 (4)
C10.2392 (2)0.79044 (13)0.79671 (11)0.0226 (5)
C20.3451 (2)0.77074 (14)0.79673 (11)0.0231 (5)
C30.3958 (3)0.77163 (16)0.74726 (12)0.0294 (6)
H30.36670.78900.71180.035*
C40.4931 (3)0.74300 (16)0.76082 (12)0.0288 (6)
H40.54480.73600.73670.035*
C50.5027 (2)0.72517 (14)0.81919 (11)0.0235 (5)
C60.5919 (2)0.69390 (13)0.84806 (11)0.0220 (5)
C70.6031 (2)0.68083 (13)0.90556 (11)0.0219 (5)
C80.6994 (2)0.65403 (14)0.93724 (11)0.0240 (5)
H80.76100.63960.92270.029*
C90.6855 (2)0.65337 (14)0.99187 (11)0.0238 (5)
H90.73610.63911.02300.029*
C100.5798 (2)0.67833 (13)0.99367 (11)0.0211 (5)
C110.5342 (2)0.68264 (13)1.04294 (11)0.0205 (5)
C120.4285 (2)0.70203 (13)1.04315 (10)0.0210 (5)
C130.3801 (3)0.70369 (16)1.09331 (12)0.0282 (6)
H130.41380.69201.13010.034*
C140.2774 (3)0.72507 (15)1.07818 (12)0.0276 (6)
H140.22510.73091.10220.033*
C150.2627 (2)0.73723 (13)1.01848 (11)0.0220 (5)
C160.1684 (2)0.76223 (13)0.98752 (11)0.0218 (5)
C170.1572 (2)0.77464 (13)0.93003 (11)0.0217 (5)
C180.0608 (2)0.80118 (14)0.89788 (12)0.0254 (6)
H18−0.00430.81130.91140.031*
C190.0805 (2)0.80901 (14)0.84491 (12)0.0252 (6)
H190.03180.82560.81410.030*
C200.1890 (2)0.78753 (13)0.84395 (11)0.0222 (5)
C210.1737 (2)0.81530 (14)0.74356 (11)0.0239 (5)
C220.1873 (3)0.87534 (16)0.72700 (14)0.0340 (7)
H220.24180.90040.74800.041*
C230.1211 (3)0.89881 (17)0.67964 (14)0.0383 (8)
H230.12970.94000.66850.046*
C240.0437 (3)0.86243 (16)0.64923 (12)0.0309 (6)
C250.0300 (3)0.80183 (16)0.66358 (13)0.0330 (7)
H25−0.02290.77670.64150.040*
C260.0961 (3)0.77879 (15)0.71129 (12)0.0295 (6)
H260.08790.73730.72190.035*
C270.6818 (2)0.67604 (14)0.81741 (11)0.0236 (5)
C280.7724 (3)0.71387 (16)0.81846 (14)0.0321 (7)
H280.77600.75150.83850.038*
C290.8572 (3)0.69741 (17)0.79075 (14)0.0333 (7)
H290.91870.72330.79170.040*
C300.8499 (3)0.64217 (16)0.76158 (12)0.0280 (6)
C310.7617 (3)0.60412 (16)0.75925 (12)0.0290 (6)
H310.75840.56670.73890.035*
C320.6768 (2)0.62110 (15)0.78725 (12)0.0262 (6)
H320.61530.59510.78580.031*
C330.6057 (2)0.66694 (14)1.09760 (11)0.0221 (5)
C340.6741 (3)0.71086 (17)1.12511 (15)0.0411 (9)
H340.67330.75101.10980.049*
C350.7442 (4)0.69763 (19)1.17488 (16)0.0474 (10)
H350.79130.72831.19330.057*
C360.7443 (3)0.63962 (16)1.19687 (12)0.0294 (6)
C370.6747 (4)0.59564 (18)1.17145 (16)0.0482 (11)
H370.67380.55601.18760.058*
C380.6054 (4)0.60970 (17)1.12173 (16)0.0495 (11)
H380.55690.57931.10410.059*
C390.0766 (2)0.78129 (14)1.01628 (11)0.0229 (5)
C40−0.0219 (3)0.74974 (15)1.00936 (14)0.0300 (6)
H40−0.02890.71220.98910.036*
C41−0.1099 (3)0.77219 (15)1.03159 (14)0.0309 (6)
H41−0.17680.75051.02630.037*
C42−0.0991 (3)0.82624 (15)1.06139 (13)0.0284 (6)
C43−0.0030 (3)0.85783 (18)1.07029 (16)0.0388 (8)
H430.00370.89461.09170.047*
C440.0850 (3)0.83526 (17)1.04756 (15)0.0350 (7)
H440.15170.85711.05350.042*
C450.4623 (3)0.84880 (14)1.01521 (12)0.0288 (6)
H45A0.38810.84401.02410.035*
H45B0.50870.81791.03770.035*
C460.5035 (3)0.91218 (14)1.03605 (13)0.0297 (6)
H46A0.47370.94351.00790.036*
H46B0.58370.91321.04000.036*
C470.4697 (3)0.92759 (17)1.09295 (15)0.0365 (7)
H47A0.49510.96951.10410.044*
H47B0.38940.92761.08830.044*
C480.5142 (4)0.8835 (2)1.14015 (14)0.0439 (9)
H48A0.59340.88111.14350.066*
H48B0.48260.84281.13170.066*
H48C0.49520.89841.17570.066*
C490.3864 (3)0.89276 (14)0.90078 (13)0.0272 (6)
H49A0.43820.92720.90170.033*
H49B0.36640.87970.86100.033*
C500.2849 (3)0.91642 (15)0.92055 (15)0.0316 (7)
H50A0.30520.93490.95840.038*
H50B0.23550.88160.92390.038*
C510.2249 (3)0.96417 (19)0.88043 (18)0.0437 (9)
H51A0.27121.00110.88130.052*0.70 (7)
H51B0.21470.94750.84170.052*0.70 (7)
H51C0.19230.94570.84550.052*0.30 (7)
H51D0.27340.99610.87280.052*0.30 (7)
C52B0.130 (3)0.986 (3)0.908 (2)0.058 (4)0.30 (7)
H52A0.07511.00600.88020.087*0.30 (7)
H52B0.15681.01600.93810.087*0.30 (7)
H52C0.09750.95140.92500.087*0.30 (7)
C52A0.1146 (13)0.9831 (10)0.8938 (13)0.058 (4)0.70 (7)
H52D0.06560.94770.88930.087*0.70 (7)
H52E0.08411.01570.86800.087*0.70 (7)
H52F0.12320.99800.93270.087*0.70 (7)
C530.5958 (3)0.83288 (15)0.92532 (16)0.0324 (7)
H53A0.64040.80390.95110.039*
H53B0.59400.81710.88660.039*
C540.6553 (3)0.89337 (17)0.92935 (16)0.0353 (7)
H54A0.60930.92420.90660.042*
H54B0.66720.90740.96900.042*
C550.7632 (3)0.88982 (19)0.90940 (19)0.0447 (9)
H55A0.75290.86860.87260.054*0.66 (2)
H55B0.81330.86460.93640.054*0.66 (2)
H55C0.75190.88580.86920.054*0.34 (2)
H55D0.80250.85450.92550.054*0.34 (2)
C56A0.8163 (8)0.9517 (4)0.9031 (6)0.061 (2)0.66 (2)
H56A0.77130.97540.87350.092*0.66 (2)
H56B0.88850.94540.89310.092*0.66 (2)
H56C0.82340.97410.93880.092*0.66 (2)
C56B0.8325 (18)0.9471 (8)0.9283 (10)0.061 (2)0.34 (2)
H56D0.78470.98250.92950.092*0.34 (2)
H56E0.88220.95500.90170.092*0.34 (2)
H56F0.87450.94000.96590.092*0.34 (2)
C570.3621 (3)0.57427 (15)0.95002 (13)0.0296 (6)
H57A0.35640.53410.93060.036*
H57B0.44020.58210.96350.036*
C580.3052 (3)0.56885 (16)1.00171 (13)0.0328 (7)
H58A0.31360.60781.02310.039*
H58B0.22660.56160.98920.039*
C590.3534 (4)0.51626 (18)1.03979 (15)0.0449 (9)
H59A0.33890.47691.01950.054*
H59B0.43320.52151.04930.054*
C600.3047 (4)0.5144 (2)1.09388 (16)0.0535 (12)
H60A0.22550.51071.08440.080*
H60B0.32320.55231.11520.080*
H60C0.33410.47921.11670.080*
C610.1631 (2)0.63131 (14)0.89282 (12)0.0255 (6)
H61A0.14520.64340.92980.031*
H61B0.13110.66250.86510.031*
C620.1079 (3)0.56971 (16)0.87610 (14)0.0321 (7)
H62A0.14900.53650.89810.039*
H62B0.10890.56190.83570.039*
C63−0.0109 (3)0.56917 (18)0.88682 (14)0.0363 (7)
H63A−0.04860.60620.86960.044*
H63B−0.04850.53290.86820.044*
C64−0.0188 (3)0.56764 (19)0.94888 (15)0.0396 (8)
H64A0.01510.60450.96720.059*
H64B0.01870.53120.96620.059*
H64C−0.09540.56620.95330.059*
C650.3362 (3)0.59678 (15)0.83241 (13)0.0302 (6)
H65A0.41530.59770.83180.036*
H65B0.31460.55320.83370.036*
C660.2784 (3)0.62395 (16)0.77757 (13)0.0347 (7)
H66A0.20620.63910.78310.042*
H66B0.32060.65950.76750.042*
C670.2639 (4)0.5789 (2)0.72945 (16)0.0545 (12)
H67A0.21230.54650.73670.065*
H67B0.33450.55910.72740.065*
C680.2215 (4)0.6094 (2)0.67360 (15)0.0514 (11)
H68A0.27550.63860.66450.077*
H68B0.15370.63110.67620.077*
H68C0.20780.57820.64400.077*
Cl50.52807 (8)0.45849 (4)0.74529 (4)0.0444 (2)
O10.4951 (3)0.50384 (14)0.78197 (15)0.0561 (8)
O20.5615 (4)0.40497 (17)0.7797 (2)0.0828 (13)
O30.6197 (3)0.48022 (15)0.72168 (15)0.0553 (8)
O40.4411 (3)0.4444 (3)0.70195 (19)0.0988 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.01903 (18)0.01944 (17)0.01378 (15)0.00064 (13)0.00131 (12)0.00126 (12)
Cl10.0540 (6)0.0447 (5)0.0299 (4)0.0044 (4)−0.0171 (4)0.0088 (3)
Cl20.0303 (4)0.0599 (6)0.0341 (4)0.0018 (4)0.0138 (3)−0.0098 (4)
Cl30.0408 (5)0.0682 (6)0.0279 (4)−0.0050 (4)−0.0144 (3)0.0130 (4)
Cl40.0267 (4)0.0418 (5)0.0500 (5)0.0055 (3)0.0149 (3)−0.0044 (4)
P10.0204 (3)0.0207 (3)0.0209 (3)−0.0004 (3)0.0014 (2)0.0017 (2)
P20.0273 (4)0.0219 (3)0.0192 (3)−0.0002 (3)0.0019 (3)−0.0002 (2)
N10.0217 (11)0.0252 (11)0.0154 (9)0.0000 (9)0.0022 (8)0.0007 (8)
N20.0217 (11)0.0230 (11)0.0153 (9)0.0017 (9)0.0020 (8)−0.0012 (8)
N30.0218 (11)0.0228 (11)0.0137 (9)0.0017 (9)0.0011 (8)0.0003 (8)
N40.0190 (10)0.0216 (11)0.0174 (9)0.0003 (9)0.0018 (8)0.0026 (8)
C10.0256 (14)0.0241 (13)0.0180 (11)−0.0006 (11)0.0027 (10)0.0049 (10)
C20.0255 (14)0.0275 (14)0.0159 (11)−0.0001 (11)0.0021 (10)0.0052 (10)
C30.0306 (15)0.0409 (17)0.0175 (12)0.0026 (13)0.0059 (11)0.0075 (11)
C40.0290 (15)0.0388 (17)0.0197 (12)0.0040 (13)0.0078 (11)0.0041 (11)
C50.0253 (14)0.0267 (13)0.0192 (11)−0.0010 (11)0.0050 (10)0.0014 (10)
C60.0247 (13)0.0229 (13)0.0185 (11)0.0019 (11)0.0042 (10)−0.0015 (9)
C70.0229 (13)0.0215 (13)0.0212 (12)0.0016 (10)0.0035 (10)0.0003 (10)
C80.0226 (13)0.0280 (14)0.0213 (12)0.0052 (11)0.0037 (10)−0.0005 (10)
C90.0251 (14)0.0266 (14)0.0185 (11)0.0021 (11)0.0006 (10)−0.0009 (10)
C100.0233 (13)0.0215 (12)0.0172 (11)−0.0005 (10)0.0001 (10)0.0007 (9)
C110.0243 (13)0.0210 (12)0.0155 (11)−0.0002 (10)0.0015 (9)0.0000 (9)
C120.0240 (13)0.0238 (13)0.0143 (10)−0.0008 (10)0.0004 (9)0.0003 (9)
C130.0280 (15)0.0401 (17)0.0169 (11)0.0005 (13)0.0046 (10)0.0026 (11)
C140.0280 (15)0.0379 (16)0.0177 (12)0.0002 (13)0.0060 (10)0.0023 (11)
C150.0228 (13)0.0258 (13)0.0177 (11)−0.0013 (11)0.0043 (10)−0.0001 (10)
C160.0218 (13)0.0238 (13)0.0199 (11)−0.0003 (10)0.0039 (10)0.0001 (10)
C170.0208 (13)0.0231 (13)0.0214 (12)0.0005 (10)0.0039 (10)−0.0010 (10)
C180.0224 (13)0.0284 (14)0.0251 (13)0.0022 (11)0.0028 (10)0.0011 (11)
C190.0233 (13)0.0281 (14)0.0225 (12)0.0021 (11)−0.0010 (10)0.0023 (10)
C200.0223 (13)0.0235 (13)0.0199 (12)−0.0010 (11)0.0010 (10)0.0027 (10)
C210.0232 (13)0.0287 (14)0.0189 (11)0.0000 (11)0.0012 (10)0.0030 (10)
C220.0323 (17)0.0329 (16)0.0313 (15)−0.0062 (13)−0.0108 (13)0.0087 (13)
C230.044 (2)0.0342 (17)0.0319 (16)−0.0073 (15)−0.0074 (14)0.0127 (13)
C240.0325 (16)0.0359 (16)0.0216 (13)0.0035 (13)−0.0033 (11)0.0039 (12)
C250.0365 (17)0.0349 (17)0.0234 (13)−0.0029 (14)−0.0077 (12)−0.0007 (12)
C260.0367 (17)0.0284 (15)0.0212 (12)−0.0015 (13)−0.0017 (12)0.0019 (11)
C270.0233 (13)0.0293 (14)0.0180 (11)0.0034 (11)0.0025 (10)0.0012 (10)
C280.0335 (17)0.0303 (15)0.0341 (15)−0.0051 (13)0.0105 (13)−0.0052 (12)
C290.0297 (16)0.0378 (17)0.0341 (15)−0.0060 (14)0.0104 (13)−0.0022 (13)
C300.0248 (14)0.0400 (17)0.0196 (12)0.0036 (13)0.0047 (10)0.0002 (11)
C310.0311 (16)0.0340 (16)0.0218 (13)0.0021 (13)0.0038 (11)−0.0054 (11)
C320.0230 (13)0.0317 (15)0.0236 (12)−0.0025 (12)0.0026 (10)−0.0040 (11)
C330.0229 (13)0.0258 (13)0.0173 (11)−0.0001 (11)0.0022 (10)0.0012 (10)
C340.050 (2)0.0313 (17)0.0338 (16)−0.0108 (16)−0.0170 (15)0.0067 (13)
C350.057 (2)0.042 (2)0.0343 (17)−0.0149 (18)−0.0189 (17)−0.0012 (15)
C360.0253 (14)0.0437 (18)0.0176 (12)−0.0011 (13)−0.0016 (10)0.0047 (11)
C370.060 (3)0.0362 (19)0.0387 (18)−0.0113 (18)−0.0204 (18)0.0158 (15)
C380.065 (3)0.0302 (17)0.0411 (19)−0.0186 (18)−0.0265 (19)0.0135 (14)
C390.0246 (13)0.0246 (13)0.0197 (11)0.0020 (11)0.0040 (10)0.0019 (10)
C400.0298 (16)0.0277 (15)0.0335 (15)−0.0026 (12)0.0086 (12)−0.0033 (12)
C410.0262 (15)0.0308 (16)0.0375 (16)−0.0006 (12)0.0104 (12)−0.0008 (12)
C420.0235 (14)0.0330 (16)0.0292 (14)0.0061 (12)0.0061 (11)0.0025 (12)
C430.0309 (17)0.0392 (19)0.0479 (19)−0.0011 (15)0.0114 (15)−0.0167 (15)
C440.0260 (15)0.0368 (17)0.0435 (18)−0.0026 (13)0.0101 (13)−0.0143 (14)
C450.0362 (17)0.0265 (14)0.0229 (13)−0.0057 (12)0.0022 (12)−0.0014 (11)
C460.0342 (16)0.0236 (14)0.0304 (14)−0.0029 (12)0.0023 (12)−0.0040 (11)
C470.0362 (18)0.0328 (17)0.0399 (17)−0.0004 (14)0.0044 (14)−0.0115 (14)
C480.053 (2)0.052 (2)0.0261 (15)0.0001 (19)0.0047 (15)−0.0092 (15)
C490.0247 (14)0.0234 (14)0.0319 (14)−0.0005 (11)0.0001 (11)0.0040 (11)
C500.0250 (15)0.0237 (14)0.0458 (18)0.0001 (12)0.0048 (13)0.0014 (13)
C510.0355 (19)0.0356 (19)0.058 (2)0.0096 (15)0.0031 (17)0.0062 (16)
C52B0.032 (4)0.040 (4)0.099 (11)0.009 (4)0.002 (6)0.005 (6)
C52A0.032 (4)0.040 (4)0.099 (11)0.009 (4)0.002 (6)0.005 (6)
C530.0236 (14)0.0286 (15)0.0470 (18)−0.0016 (12)0.0113 (13)−0.0004 (13)
C540.0309 (16)0.0349 (17)0.0428 (18)−0.0074 (14)0.0138 (14)−0.0017 (14)
C550.0294 (18)0.050 (2)0.057 (2)−0.0026 (16)0.0138 (16)0.0101 (18)
C56A0.049 (4)0.068 (4)0.072 (7)−0.021 (3)0.024 (5)0.018 (5)
C56B0.049 (4)0.068 (4)0.072 (7)−0.021 (3)0.024 (5)0.018 (5)
C570.0327 (16)0.0251 (14)0.0306 (14)0.0037 (12)0.0038 (12)0.0040 (11)
C580.0380 (18)0.0303 (16)0.0291 (14)−0.0033 (14)0.0031 (13)0.0073 (12)
C590.064 (3)0.0305 (17)0.0356 (17)−0.0032 (17)−0.0052 (17)0.0076 (14)
C600.084 (3)0.044 (2)0.0299 (17)−0.019 (2)0.0002 (19)0.0081 (15)
C610.0258 (14)0.0265 (14)0.0246 (13)−0.0022 (11)0.0055 (11)−0.0001 (11)
C620.0349 (17)0.0308 (16)0.0300 (14)−0.0086 (13)0.0034 (13)−0.0040 (12)
C630.0335 (17)0.0388 (18)0.0343 (16)−0.0124 (15)−0.0011 (13)−0.0011 (14)
C640.0373 (19)0.042 (2)0.0402 (18)−0.0040 (16)0.0087 (15)0.0055 (15)
C650.0310 (16)0.0315 (16)0.0299 (14)−0.0006 (13)0.0100 (12)−0.0077 (12)
C660.047 (2)0.0336 (17)0.0233 (13)−0.0010 (15)0.0062 (13)−0.0064 (12)
C670.070 (3)0.059 (3)0.0304 (17)0.017 (2)−0.0035 (18)−0.0141 (17)
C680.055 (3)0.070 (3)0.0281 (16)0.015 (2)0.0021 (16)−0.0107 (17)
Cl50.0376 (5)0.0345 (4)0.0592 (5)0.0042 (4)0.0022 (4)−0.0150 (4)
O10.0504 (18)0.0419 (16)0.078 (2)0.0039 (14)0.0177 (16)−0.0198 (15)
O20.083 (3)0.047 (2)0.124 (4)0.023 (2)0.033 (3)0.017 (2)
O30.0460 (17)0.0484 (17)0.073 (2)0.0070 (14)0.0150 (15)−0.0066 (15)
O40.055 (2)0.151 (5)0.084 (3)−0.011 (3)−0.009 (2)−0.059 (3)
Geometric parameters (Å, °) top
Co1—N41.979 (2)C42—C431.369 (5)
Co1—N21.985 (2)C43—C441.395 (5)
Co1—N11.989 (2)C43—H430.9500
Co1—N31.997 (2)C44—H440.9500
Co1—P22.3385 (9)C45—C461.531 (4)
Co1—P12.3395 (8)C45—H45A0.9900
Cl1—C241.753 (3)C45—H45B0.9900
Cl2—C301.750 (3)C46—C471.536 (5)
Cl3—C361.745 (3)C46—H46A0.9900
Cl4—C421.744 (3)C46—H46B0.9900
P1—C491.827 (3)C47—C481.521 (5)
P1—C451.837 (3)C47—H47A0.9900
P1—C531.837 (3)C47—H47B0.9900
P2—C651.836 (3)C48—H48A0.9800
P2—C611.841 (3)C48—H48B0.9800
P2—C571.847 (3)C48—H48C0.9800
N1—C51.376 (4)C49—C501.516 (5)
N1—C21.377 (3)C49—H49A0.9900
N2—C71.378 (4)C49—H49B0.9900
N2—C101.381 (3)C50—C511.530 (5)
N3—C121.373 (3)C50—H50A0.9900
N3—C151.378 (4)C50—H50B0.9900
N4—C171.375 (4)C51—C52A1.521 (7)
N4—C201.386 (3)C51—C52B1.537 (10)
C1—C201.389 (4)C51—H51A0.9900
C1—C21.389 (4)C51—H51B0.9900
C1—C211.502 (4)C51—H51C0.9599
C2—C31.440 (4)C51—H51D0.9601
C3—C41.356 (5)C52B—H52A0.9800
C3—H30.9500C52B—H52B0.9800
C4—C51.445 (4)C52B—H52C0.9800
C4—H40.9500C52A—H52D0.9800
C5—C61.391 (4)C52A—H52E0.9800
C6—C71.398 (4)C52A—H52F0.9800
C6—C271.493 (4)C53—C541.510 (5)
C7—C81.438 (4)C53—H53A0.9900
C8—C91.356 (4)C53—H53B0.9900
C8—H80.9500C54—C551.505 (5)
C9—C101.434 (4)C54—H54A0.9900
C9—H90.9500C54—H54B0.9900
C10—C111.402 (4)C55—C56A1.522 (7)
C11—C121.387 (4)C55—C56B1.544 (9)
C11—C331.503 (4)C55—H55A0.9900
C12—C131.438 (4)C55—H55B0.9900
C13—C141.357 (4)C55—H55C0.9601
C13—H130.9500C55—H55D0.9599
C14—C151.444 (4)C56A—H56A0.9800
C14—H140.9500C56A—H56B0.9800
C15—C161.396 (4)C56A—H56C0.9800
C16—C171.395 (4)C56B—H56D0.9800
C16—C391.493 (4)C56B—H56E0.9800
C17—C181.441 (4)C56B—H56F0.9800
C18—C191.350 (4)C57—C581.537 (5)
C18—H180.9500C57—H57A0.9900
C19—C201.437 (4)C57—H57B0.9900
C19—H190.9500C58—C591.529 (5)
C21—C221.388 (4)C58—H58A0.9900
C21—C261.389 (4)C58—H58B0.9900
C22—C231.391 (4)C59—C601.527 (6)
C22—H220.9500C59—H59A0.9900
C23—C241.366 (5)C59—H59B0.9900
C23—H230.9500C60—H60A0.9800
C24—C251.385 (5)C60—H60B0.9800
C25—C261.393 (4)C60—H60C0.9800
C25—H250.9500C61—C621.533 (4)
C26—H260.9500C61—H61A0.9900
C27—C281.396 (4)C61—H61B0.9900
C27—C321.398 (4)C62—C631.546 (5)
C28—C291.389 (5)C62—H62A0.9900
C28—H280.9500C62—H62B0.9900
C29—C301.390 (5)C63—C641.515 (5)
C29—H290.9500C63—H63A0.9900
C30—C311.372 (5)C63—H63B0.9900
C31—C321.397 (4)C64—H64A0.9800
C31—H310.9500C64—H64B0.9800
C32—H320.9500C64—H64C0.9800
C33—C341.378 (4)C65—C661.517 (5)
C33—C381.378 (4)C65—H65A0.9900
C34—C351.393 (5)C65—H65B0.9900
C34—H340.9500C66—C671.508 (5)
C35—C361.372 (5)C66—H66A0.9900
C35—H350.9500C66—H66B0.9900
C36—C371.368 (5)C67—C681.516 (6)
C37—C381.391 (5)C67—H67A0.9900
C37—H370.9500C67—H67B0.9900
C38—H380.9500C68—H68A0.9800
C39—C441.393 (4)C68—H68B0.9800
C39—C401.395 (4)C68—H68C0.9800
C40—C411.388 (4)Cl5—O41.410 (4)
C40—H400.9500Cl5—O11.432 (3)
C41—C421.375 (5)Cl5—O31.440 (3)
C41—H410.9500Cl5—O21.453 (4)
N4—Co1—N2178.50 (10)P1—C45—H45B107.5
N4—Co1—N190.36 (10)H45A—C45—H45B107.0
N2—Co1—N189.63 (10)C45—C46—C47111.3 (3)
N4—Co1—N389.92 (9)C45—C46—H46A109.4
N2—Co1—N390.13 (9)C47—C46—H46A109.4
N1—Co1—N3178.85 (10)C45—C46—H46B109.4
N4—Co1—P289.41 (7)C47—C46—H46B109.4
N2—Co1—P289.09 (7)H46A—C46—H46B108.0
N1—Co1—P291.68 (7)C48—C47—C46114.1 (3)
N3—Co1—P289.44 (7)C48—C47—H47A108.7
N4—Co1—P191.40 (7)C46—C47—H47A108.7
N2—Co1—P190.10 (7)C48—C47—H47B108.7
N1—Co1—P188.48 (7)C46—C47—H47B108.7
N3—Co1—P190.39 (7)H47A—C47—H47B107.6
P2—Co1—P1179.18 (3)C47—C48—H48A109.5
C49—P1—C45105.88 (15)C47—C48—H48B109.5
C49—P1—C53104.33 (15)H48A—C48—H48B109.5
C45—P1—C53107.52 (16)C47—C48—H48C109.5
C49—P1—Co1115.86 (11)H48A—C48—H48C109.5
C45—P1—Co1112.48 (10)H48B—C48—H48C109.5
C53—P1—Co1110.16 (11)C50—C49—P1116.5 (2)
C65—P2—C61104.00 (15)C50—C49—H49A108.2
C65—P2—C57100.97 (15)P1—C49—H49A108.2
C61—P2—C57104.32 (15)C50—C49—H49B108.2
C65—P2—Co1118.53 (11)P1—C49—H49B108.2
C61—P2—Co1112.51 (10)H49A—C49—H49B107.3
C57—P2—Co1114.80 (11)C49—C50—C51112.3 (3)
C5—N1—C2105.4 (2)C49—C50—H50A109.1
C5—N1—Co1127.74 (19)C51—C50—H50A109.1
C2—N1—Co1126.86 (19)C49—C50—H50B109.1
C7—N2—C10105.1 (2)C51—C50—H50B109.1
C7—N2—Co1127.51 (18)H50A—C50—H50B107.9
C10—N2—Co1127.38 (19)C52A—C51—C50114.6 (11)
C12—N3—C15105.8 (2)C50—C51—C52B106 (2)
C12—N3—Co1126.70 (19)C52A—C51—H51A108.6
C15—N3—Co1127.35 (18)C50—C51—H51A108.6
C17—N4—C20105.2 (2)C52B—C51—H51A102.9
C17—N4—Co1127.75 (18)C52A—C51—H51B108.6
C20—N4—Co1127.07 (19)C50—C51—H51B108.6
C20—C1—C2123.0 (3)C52B—C51—H51B122.8
C20—C1—C21117.3 (3)H51A—C51—H51B107.6
C2—C1—C21119.7 (2)C52A—C51—H51C91.8
N1—C2—C1126.3 (2)C50—C51—H51C111.1
N1—C2—C3110.4 (3)C52B—C51—H51C105.8
C1—C2—C3123.0 (3)H51A—C51—H51C121.4
C4—C3—C2107.1 (3)C52A—C51—H51D117.7
C4—C3—H3126.5C50—C51—H51D110.9
C2—C3—H3126.5C52B—C51—H51D114.2
C3—C4—C5106.5 (3)H51B—C51—H51D94.2
C3—C4—H4126.7H51C—C51—H51D109.1
C5—C4—H4126.7C51—C52B—H52A109.5
N1—C5—C6126.2 (2)C51—C52B—H52B109.5
N1—C5—C4110.5 (3)H52A—C52B—H52B109.5
C6—C5—C4123.3 (3)C51—C52B—H52C109.5
C5—C6—C7122.4 (3)H52A—C52B—H52C109.5
C5—C6—C27119.1 (2)C51—C52A—H52D109.5
C7—C6—C27118.5 (3)C51—C52A—H52E109.5
N2—C7—C6126.2 (3)C51—C52A—H52F109.5
N2—C7—C8110.6 (2)C54—C53—P1119.9 (2)
C6—C7—C8123.1 (3)C54—C53—H53A107.4
C9—C8—C7106.8 (3)P1—C53—H53A107.4
C9—C8—H8126.6C54—C53—H53B107.4
C7—C8—H8126.6P1—C53—H53B107.4
C8—C9—C10107.0 (2)H53A—C53—H53B106.9
C8—C9—H9126.5C55—C54—C53113.0 (3)
C10—C9—H9126.5C55—C54—H54A109.0
N2—C10—C11125.7 (3)C53—C54—H54A109.0
N2—C10—C9110.5 (2)C55—C54—H54B109.0
C11—C10—C9123.7 (2)C53—C54—H54B109.0
C12—C11—C10122.9 (2)H54A—C54—H54B107.8
C12—C11—C33119.6 (2)C54—C55—C56A114.4 (5)
C10—C11—C33117.5 (3)C54—C55—C56B110.5 (9)
N3—C12—C11126.8 (2)C54—C55—H55A108.7
N3—C12—C13110.3 (3)C56A—C55—H55A108.7
C11—C12—C13122.9 (2)C56B—C55—H55A128.8
C14—C13—C12107.0 (2)C54—C55—H55B108.7
C14—C13—H13126.5C56A—C55—H55B108.7
C12—C13—H13126.5C56B—C55—H55B89.7
C13—C14—C15106.8 (3)H55A—C55—H55B107.6
C13—C14—H14126.6C54—C55—H55C109.7
C15—C14—H14126.6C56A—C55—H55C88.6
N3—C15—C16125.9 (2)C56B—C55—H55C110.8
N3—C15—C14110.0 (2)H55B—C55—H55C125.6
C16—C15—C14124.1 (3)C54—C55—H55D109.6
C17—C16—C15122.9 (3)C56A—C55—H55D123.4
C17—C16—C39116.6 (3)C56B—C55—H55D107.9
C15—C16—C39120.3 (2)H55A—C55—H55D88.2
N4—C17—C16126.2 (3)H55C—C55—H55D108.2
N4—C17—C18110.5 (2)C55—C56A—H56A109.5
C16—C17—C18123.3 (3)C55—C56A—H56B109.5
C19—C18—C17107.0 (3)C55—C56A—H56C109.5
C19—C18—H18126.5C55—C56B—H56D109.5
C17—C18—H18126.5C55—C56B—H56E109.5
C18—C19—C20107.1 (3)H56D—C56B—H56E109.5
C18—C19—H19126.5C55—C56B—H56F109.5
C20—C19—H19126.5H56D—C56B—H56F109.5
N4—C20—C1126.1 (3)H56E—C56B—H56F109.5
N4—C20—C19110.3 (2)C58—C57—P2117.2 (2)
C1—C20—C19123.6 (3)C58—C57—H57A108.0
C22—C21—C26119.2 (3)P2—C57—H57A108.0
C22—C21—C1120.7 (3)C58—C57—H57B108.0
C26—C21—C1120.1 (3)P2—C57—H57B108.0
C21—C22—C23119.9 (3)H57A—C57—H57B107.2
C21—C22—H22120.0C59—C58—C57110.8 (3)
C23—C22—H22120.0C59—C58—H58A109.5
C24—C23—C22119.8 (3)C57—C58—H58A109.5
C24—C23—H23120.1C59—C58—H58B109.5
C22—C23—H23120.1C57—C58—H58B109.5
C23—C24—C25121.8 (3)H58A—C58—H58B108.1
C23—C24—Cl1119.3 (3)C60—C59—C58111.0 (4)
C25—C24—Cl1118.9 (3)C60—C59—H59A109.4
C24—C25—C26118.0 (3)C58—C59—H59A109.4
C24—C25—H25121.0C60—C59—H59B109.4
C26—C25—H25121.0C58—C59—H59B109.4
C21—C26—C25121.2 (3)H59A—C59—H59B108.0
C21—C26—H26119.4C59—C60—H60A109.5
C25—C26—H26119.4C59—C60—H60B109.5
C28—C27—C32118.9 (3)H60A—C60—H60B109.5
C28—C27—C6120.6 (3)C59—C60—H60C109.5
C32—C27—C6120.5 (3)H60A—C60—H60C109.5
C29—C28—C27121.2 (3)H60B—C60—H60C109.5
C29—C28—H28119.4C62—C61—P2116.5 (2)
C27—C28—H28119.4C62—C61—H61A108.2
C28—C29—C30118.4 (3)P2—C61—H61A108.2
C28—C29—H29120.8C62—C61—H61B108.2
C30—C29—H29120.8P2—C61—H61B108.2
C31—C30—C29122.0 (3)H61A—C61—H61B107.3
C31—C30—Cl2119.7 (3)C61—C62—C63111.4 (3)
C29—C30—Cl2118.3 (3)C61—C62—H62A109.4
C30—C31—C32119.1 (3)C63—C62—H62A109.4
C30—C31—H31120.4C61—C62—H62B109.4
C32—C31—H31120.4C63—C62—H62B109.4
C31—C32—C27120.4 (3)H62A—C62—H62B108.0
C31—C32—H32119.8C64—C63—C62112.7 (3)
C27—C32—H32119.8C64—C63—H63A109.0
C34—C33—C38118.2 (3)C62—C63—H63A109.0
C34—C33—C11119.6 (3)C64—C63—H63B109.0
C38—C33—C11122.2 (3)C62—C63—H63B109.0
C33—C34—C35121.4 (3)H63A—C63—H63B107.8
C33—C34—H34119.3C63—C64—H64A109.5
C35—C34—H34119.3C63—C64—H64B109.5
C36—C35—C34118.9 (3)H64A—C64—H64B109.5
C36—C35—H35120.5C63—C64—H64C109.5
C34—C35—H35120.5H64A—C64—H64C109.5
C37—C36—C35121.0 (3)H64B—C64—H64C109.5
C37—C36—Cl3119.2 (3)C66—C65—P2116.8 (2)
C35—C36—Cl3119.8 (3)C66—C65—H65A108.1
C36—C37—C38119.2 (3)P2—C65—H65A108.1
C36—C37—H37120.4C66—C65—H65B108.1
C38—C37—H37120.4P2—C65—H65B108.1
C33—C38—C37121.2 (3)H65A—C65—H65B107.3
C33—C38—H38119.4C67—C66—C65113.2 (3)
C37—C38—H38119.4C67—C66—H66A108.9
C44—C39—C40117.8 (3)C65—C66—H66A108.9
C44—C39—C16119.5 (3)C67—C66—H66B108.9
C40—C39—C16122.4 (3)C65—C66—H66B108.9
C41—C40—C39121.2 (3)H66A—C66—H66B107.7
C41—C40—H40119.4C66—C67—C68112.1 (4)
C39—C40—H40119.4C66—C67—H67A109.2
C42—C41—C40119.2 (3)C68—C67—H67A109.2
C42—C41—H41120.4C66—C67—H67B109.2
C40—C41—H41120.4C68—C67—H67B109.2
C43—C42—C41121.4 (3)H67A—C67—H67B107.9
C43—C42—Cl4119.2 (3)C67—C68—H68A109.5
C41—C42—Cl4119.4 (3)C67—C68—H68B109.5
C42—C43—C44119.1 (3)H68A—C68—H68B109.5
C42—C43—H43120.4C67—C68—H68C109.5
C44—C43—H43120.4H68A—C68—H68C109.5
C39—C44—C43121.2 (3)H68B—C68—H68C109.5
C39—C44—H44119.4O4—Cl5—O1110.1 (2)
C43—C44—H44119.4O4—Cl5—O3110.1 (3)
C46—C45—P1119.2 (2)O1—Cl5—O3110.2 (2)
C46—C45—H45A107.5O4—Cl5—O2111.1 (3)
P1—C45—H45A107.5O1—Cl5—O2106.7 (2)
C46—C45—H45B107.5O3—Cl5—O2108.6 (2)
N4—Co1—P1—C49−29.06 (14)C13—C14—C15—C16−177.3 (3)
N2—Co1—P1—C49150.88 (14)N3—C15—C16—C170.2 (5)
N1—Co1—P1—C4961.26 (14)C14—C15—C16—C17178.7 (3)
N3—Co1—P1—C49−118.99 (14)N3—C15—C16—C39−175.2 (3)
N4—Co1—P1—C4592.92 (14)C14—C15—C16—C393.2 (5)
N2—Co1—P1—C45−87.14 (14)C20—N4—C17—C16−177.3 (3)
N1—Co1—P1—C45−176.77 (14)Co1—N4—C17—C163.2 (4)
N3—Co1—P1—C452.99 (14)C20—N4—C17—C18−0.2 (3)
N4—Co1—P1—C53−147.15 (14)Co1—N4—C17—C18−179.7 (2)
N2—Co1—P1—C5332.79 (14)C15—C16—C17—N4−2.4 (5)
N1—Co1—P1—C53−56.83 (14)C39—C16—C17—N4173.2 (3)
N3—Co1—P1—C53122.92 (14)C15—C16—C17—C18−179.2 (3)
N4—Co1—P2—C65104.68 (14)C39—C16—C17—C18−3.5 (4)
N2—Co1—P2—C65−75.26 (14)N4—C17—C18—C190.2 (3)
N1—Co1—P2—C6514.34 (15)C16—C17—C18—C19177.4 (3)
N3—Co1—P2—C65−165.40 (15)C17—C18—C19—C20−0.1 (3)
N4—Co1—P2—C61−16.89 (12)C17—N4—C20—C1177.6 (3)
N2—Co1—P2—C61163.18 (12)Co1—N4—C20—C1−2.9 (4)
N1—Co1—P2—C61−107.22 (12)C17—N4—C20—C190.2 (3)
N3—Co1—P2—C6173.04 (12)Co1—N4—C20—C19179.7 (2)
N4—Co1—P2—C57−135.99 (13)C2—C1—C20—N41.4 (5)
N2—Co1—P2—C5744.07 (13)C21—C1—C20—N4−179.6 (3)
N1—Co1—P2—C57133.67 (14)C2—C1—C20—C19178.5 (3)
N3—Co1—P2—C57−46.07 (14)C21—C1—C20—C19−2.4 (4)
N4—Co1—N1—C5−175.6 (3)C18—C19—C20—N4−0.1 (3)
N2—Co1—N1—C52.9 (3)C18—C19—C20—C1−177.6 (3)
P2—Co1—N1—C5−86.2 (2)C20—C1—C21—C22100.4 (4)
P1—Co1—N1—C593.0 (2)C2—C1—C21—C22−80.6 (4)
N4—Co1—N1—C24.6 (2)C20—C1—C21—C26−77.6 (4)
N2—Co1—N1—C2−176.9 (2)C2—C1—C21—C26101.5 (4)
P2—Co1—N1—C294.0 (2)C26—C21—C22—C232.1 (5)
P1—Co1—N1—C2−86.8 (2)C1—C21—C22—C23−175.8 (3)
N1—Co1—N2—C7−5.7 (2)C21—C22—C23—C24−0.7 (6)
N3—Co1—N2—C7175.5 (2)C22—C23—C24—C25−1.2 (6)
P2—Co1—N2—C786.0 (2)C22—C23—C24—Cl1178.6 (3)
P1—Co1—N2—C7−94.1 (2)C23—C24—C25—C261.6 (6)
N1—Co1—N2—C10172.9 (2)Cl1—C24—C25—C26−178.2 (3)
N3—Co1—N2—C10−6.0 (2)C22—C21—C26—C25−1.7 (5)
P2—Co1—N2—C10−95.5 (2)C1—C21—C26—C25176.3 (3)
P1—Co1—N2—C1084.4 (2)C24—C25—C26—C21−0.1 (5)
N4—Co1—N3—C12−175.6 (2)C5—C6—C27—C2893.9 (4)
N2—Co1—N3—C125.9 (2)C7—C6—C27—C28−83.4 (4)
P2—Co1—N3—C1295.0 (2)C5—C6—C27—C32−86.2 (4)
P1—Co1—N3—C12−84.2 (2)C7—C6—C27—C3296.5 (3)
N4—Co1—N3—C15−0.3 (2)C32—C27—C28—C29−0.8 (5)
N2—Co1—N3—C15−178.8 (2)C6—C27—C28—C29179.1 (3)
P2—Co1—N3—C15−89.7 (2)C27—C28—C29—C300.2 (5)
P1—Co1—N3—C1591.1 (2)C28—C29—C30—C310.4 (5)
N1—Co1—N4—C17179.5 (2)C28—C29—C30—Cl2−178.4 (3)
N3—Co1—N4—C17−1.6 (2)C29—C30—C31—C32−0.4 (5)
P2—Co1—N4—C1787.8 (2)Cl2—C30—C31—C32178.4 (2)
P1—Co1—N4—C17−92.0 (2)C30—C31—C32—C27−0.2 (5)
N1—Co1—N4—C200.1 (2)C28—C27—C32—C310.8 (4)
N3—Co1—N4—C20179.0 (2)C6—C27—C32—C31−179.1 (3)
P2—Co1—N4—C20−91.5 (2)C12—C11—C33—C34−94.3 (4)
P1—Co1—N4—C2088.6 (2)C10—C11—C33—C3484.1 (4)
C5—N1—C2—C1172.8 (3)C12—C11—C33—C3885.5 (4)
Co1—N1—C2—C1−7.3 (4)C10—C11—C33—C38−96.1 (4)
C5—N1—C2—C3−1.5 (3)C38—C33—C34—C352.4 (6)
Co1—N1—C2—C3178.4 (2)C11—C33—C34—C35−177.8 (4)
C20—C1—C2—N14.0 (5)C33—C34—C35—C36−0.4 (7)
C21—C1—C2—N1−175.1 (3)C34—C35—C36—C37−1.8 (7)
C20—C1—C2—C3177.6 (3)C34—C35—C36—Cl3179.3 (3)
C21—C1—C2—C3−1.4 (5)C35—C36—C37—C381.9 (7)
N1—C2—C3—C41.5 (4)Cl3—C36—C37—C38−179.2 (4)
C1—C2—C3—C4−173.1 (3)C34—C33—C38—C37−2.3 (7)
C2—C3—C4—C5−0.7 (4)C11—C33—C38—C37178.0 (4)
C2—N1—C5—C6−178.5 (3)C36—C37—C38—C330.2 (7)
Co1—N1—C5—C61.6 (4)C17—C16—C39—C44−100.2 (4)
C2—N1—C5—C41.0 (3)C15—C16—C39—C4475.5 (4)
Co1—N1—C5—C4−178.8 (2)C17—C16—C39—C4074.3 (4)
C3—C4—C5—N1−0.2 (4)C15—C16—C39—C40−110.0 (3)
C3—C4—C5—C6179.4 (3)C44—C39—C40—C411.7 (5)
N1—C5—C6—C7−5.1 (5)C16—C39—C40—C41−172.9 (3)
C4—C5—C6—C7175.4 (3)C39—C40—C41—C42−0.6 (5)
N1—C5—C6—C27177.8 (3)C40—C41—C42—C43−1.0 (5)
C4—C5—C6—C27−1.7 (4)C40—C41—C42—Cl4178.5 (3)
C10—N2—C7—C6−174.5 (3)C41—C42—C43—C441.4 (6)
Co1—N2—C7—C64.3 (4)Cl4—C42—C43—C44−178.1 (3)
C10—N2—C7—C81.6 (3)C40—C39—C44—C43−1.3 (5)
Co1—N2—C7—C8−179.6 (2)C16—C39—C44—C43173.4 (3)
C5—C6—C7—N22.0 (5)C42—C43—C44—C39−0.2 (6)
C27—C6—C7—N2179.1 (3)C49—P1—C45—C46−49.8 (3)
C5—C6—C7—C8−173.6 (3)C53—P1—C45—C4661.3 (3)
C27—C6—C7—C83.5 (4)Co1—P1—C45—C46−177.2 (2)
N2—C7—C8—C9−1.9 (3)P1—C45—C46—C47162.2 (3)
C6—C7—C8—C9174.3 (3)C45—C46—C47—C4860.9 (4)
C7—C8—C9—C101.3 (3)C45—P1—C49—C50−44.9 (3)
C7—N2—C10—C11−178.2 (3)C53—P1—C49—C50−158.2 (2)
Co1—N2—C10—C113.0 (4)Co1—P1—C49—C5080.6 (2)
C7—N2—C10—C9−0.8 (3)P1—C49—C50—C51−173.1 (3)
Co1—N2—C10—C9−179.6 (2)C49—C50—C51—C52A172.0 (13)
C8—C9—C10—N2−0.4 (3)C49—C50—C51—C52B−176 (2)
C8—C9—C10—C11177.1 (3)C49—P1—C53—C5447.7 (3)
N2—C10—C11—C122.8 (5)C45—P1—C53—C54−64.5 (3)
C9—C10—C11—C12−174.3 (3)Co1—P1—C53—C54172.6 (3)
N2—C10—C11—C33−175.5 (3)P1—C53—C54—C55−173.7 (3)
C9—C10—C11—C337.4 (4)C53—C54—C55—C56A169.8 (7)
C15—N3—C12—C11−178.9 (3)C53—C54—C55—C56B−165.5 (11)
Co1—N3—C12—C11−2.8 (4)C65—P2—C57—C58−147.6 (3)
C15—N3—C12—C131.2 (3)C61—P2—C57—C58−39.9 (3)
Co1—N3—C12—C13177.4 (2)Co1—P2—C57—C5883.7 (3)
C10—C11—C12—N3−2.9 (5)P2—C57—C58—C59178.0 (2)
C33—C11—C12—N3175.4 (3)C57—C58—C59—C60174.7 (3)
C10—C11—C12—C13177.0 (3)C65—P2—C61—C6247.5 (3)
C33—C11—C12—C13−4.8 (4)C57—P2—C61—C62−58.0 (3)
N3—C12—C13—C14−0.4 (4)Co1—P2—C61—C62176.98 (19)
C11—C12—C13—C14179.7 (3)P2—C61—C62—C63166.8 (2)
C12—C13—C14—C15−0.6 (4)C61—C62—C63—C64−70.9 (4)
C12—N3—C15—C16177.0 (3)C61—P2—C65—C6656.3 (3)
Co1—N3—C15—C160.9 (4)C57—P2—C65—C66164.2 (3)
C12—N3—C15—C14−1.6 (3)Co1—P2—C65—C66−69.5 (3)
Co1—N3—C15—C14−177.7 (2)P2—C65—C66—C67−156.2 (3)
C13—C14—C15—N31.4 (4)C65—C66—C67—C68−171.5 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C22—H22···O3i0.952.483.403 (5)165
C31—H31···O30.952.553.277 (5)134
C32—H32···O10.952.493.407 (5)163
C34—H34···Cl4ii0.952.803.643 (4)148
C50—H50B···N40.992.593.359 (4)134
C67—H67B···O10.992.523.376 (6)145
C66—H66B···Cg10.992.433.335 (4)151
C53—H53A···Cg20.992.893.574 (4)127
C58—H58A···Cg30.992.483.431 (4)161
C50—H50B···Cg40.992.473.353 (4)149
C61—H61B···Cg40.992.773.428 (3)125
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x+1, y, z.
Table 1
Selected geometric parameters (Å, °) top
Co1—N41.979 (2)Co1—N31.997 (2)
Co1—N21.985 (2)Co1—P22.3385 (9)
Co1—N11.989 (2)Co1—P12.3395 (8)
N4—Co1—N2178.50 (10)N1—Co1—P291.68 (7)
N4—Co1—N190.36 (10)N3—Co1—P289.44 (7)
N2—Co1—N189.63 (10)N4—Co1—P191.40 (7)
N4—Co1—N389.92 (9)N2—Co1—P190.10 (7)
N2—Co1—N390.13 (9)N1—Co1—P188.48 (7)
N1—Co1—N3178.85 (10)N3—Co1—P190.39 (7)
N4—Co1—P289.41 (7)P2—Co1—P1179.18 (3)
N2—Co1—P289.09 (7)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C22—H22···O3i0.952.483.403 (5)165
C31—H31···O30.952.553.277 (5)134
C32—H32···O10.952.493.407 (5)163
C34—H34···Cl4ii0.952.803.643 (4)148
C50—H50B···N40.992.593.359 (4)134
C67—H67B···O10.992.523.376 (6)145
C66—H66B···Cg10.992.433.335 (4)151
C53—H53A···Cg20.992.893.574 (4)127
C58—H58A···Cg30.992.483.431 (4)161
C50—H50B···Cg40.992.473.353 (4)149
C61—H61B···Cg40.992.773.428 (3)125
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x+1, y, z.
Acknowledgements top

We thank Shiraz and Persian Gulf Universities for the financial support.

references
References top

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