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Phosphate esters provide a rigid and stable polymeric backbone in nucleic acids. Metal complexes with phosphate ester groups have been synthesized as structural and spectroscopic models of phosphate-containing enzymes. Dinucle­ating ligands are used extensively to synthesize model complexes since they provide the support required to stabilize such complexes. The crystal structures of two dinuclear CoII complexes, namely bis­(μ-diphenyl phosphato-κ2O:O′)bis­({2-meth­oxy-N,N-bis­[(pyridin-2-yl)meth­yl]aniline-κ4N,N′,N′′,O}cobalt(II)) bis­(per­chlorate), [Co(C12H10O4P)2(C19H19N3O)2](ClO4)2, and bis­(μ-diphenyl phosphato-κ2O:O′)bis­({N,N-bis­[(pyridin-2-yl)meth­yl]quinolin-8-amine-κ4N,N′,N′′,O}cobalt(II)) bis­(perchlorate), [Co(C12H10O4P)2(C21H18N4)2](ClO4)2, with tetra­dentate 2-meth­oxy-N,N-bis­[(pyridin-2-yl)meth­yl]aniline (L1) and N,N-bis­[(pyridin-2-yl)meth­yl]quinolin-8-amine (L2) ligands are reported. The com­plexes have similar structures, with distorted octa­hedral geometries around the metal centres. Both are centrosymmetric (Z′ = 0.5), with the CoII centres doubly bridged by diphenyl phosphate ester groups. A number of aromatic–aromatic inter­actions are present and differ between the two complexes as the anisole group in L1 is replaced by a quinoline group in L2. A detailed study of these inter­actions is presented.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617007355/ky3116sup1.cif
Contains datablocks 1a, 1b, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617007355/ky31161asup2.hkl
Contains datablock 1a

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617007355/ky31161bsup3.hkl
Contains datablock 1b

CCDC references: 1550823; 1550822

Computing details top

For both structures, data collection: APEX2 (Bruker, 2012); cell refinement: APEX2 and SAINT (Bruker, 2012); data reduction: SAINT and XPREP (Bruker, 2012); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015b).

Bis(µ-diphenyl phosphato-κ2O:O')bis({2-methoxy-N,N-bis[(pyridin-2-yl)methyl]aniline-κ4N,N',N'',O}cobalt(II)) bis(perchlorate) (1a) top
Crystal data top
[Co(C12H10O4P)2(C19H19N3O)2](ClO4)2F(000) = 1468
Mr = 1425.84Dx = 1.491 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.0638 (2) ÅCell parameters from 7252 reflections
b = 14.0258 (4) Åθ = 2.5–25.8°
c = 20.8917 (6) ŵ = 0.73 mm1
β = 101.590 (1)°T = 298 K
V = 3175.84 (14) Å3Block, pink
Z = 20.35 × 0.25 × 0.15 mm
Data collection top
Bruker AXS Kappa apex2 CCD
diffractometer
5642 reflections with I > 2σ(I)
Radiation source: Sealed tubeRint = 0.029
ω and φ scanθmax = 28.3°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 1410
Tmin = 0.841, Tmax = 1.000k = 1818
24243 measured reflectionsl = 2427
7780 independent reflections
Refinement top
Refinement on F2154 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.104 w = 1/[σ2(Fo2) + (0.0478P)2 + 0.6967P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
7780 reflectionsΔρmax = 0.47 e Å3
452 parametersΔρmin = 0.37 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C110.4541 (2)0.03930 (16)0.41722 (12)0.0549 (6)
H110.5244750.0320090.3997220.066*
C100.3712 (3)0.03433 (18)0.41481 (15)0.0700 (8)
H100.3860650.0917580.3955320.084*
C90.2670 (3)0.02456 (19)0.44031 (16)0.0751 (8)
H90.2117210.0749640.4381330.090*
C80.2443 (2)0.06058 (18)0.46932 (14)0.0635 (7)
H80.1738190.0672740.4867880.076*
C70.3263 (2)0.13564 (15)0.47238 (11)0.0437 (5)
C120.43099 (19)0.12479 (14)0.44623 (10)0.0417 (5)
C60.19018 (19)0.27250 (17)0.45940 (12)0.0516 (6)
H6A0.1580870.3209460.4846310.062*
H6B0.1266890.2245810.4466610.062*
C50.2215 (2)0.31690 (16)0.39940 (11)0.0478 (5)
C40.1387 (3)0.3190 (2)0.33943 (15)0.0711 (8)
H40.0647780.2854700.3333530.085*
C30.1692 (3)0.3720 (3)0.28942 (14)0.0835 (10)
H30.1147990.3752140.2492820.100*
C20.2779 (3)0.4195 (2)0.29836 (13)0.0745 (9)
H20.2977530.4572380.2653180.089*
C10.3579 (2)0.41067 (19)0.35721 (11)0.0593 (6)
H10.4341740.4407910.3628480.071*
C140.2933 (2)0.21945 (18)0.57030 (12)0.0533 (6)
H14A0.2541540.1595240.5772450.064*
H14B0.2425420.2707540.5814730.064*
C150.4184 (2)0.22394 (16)0.61395 (11)0.0483 (5)
C160.4407 (3)0.1853 (2)0.67643 (14)0.0745 (8)
H160.3807360.1486840.6902640.089*
C170.5513 (4)0.2014 (2)0.71726 (15)0.0862 (10)
H170.5660550.1776060.7596790.103*
C180.6403 (3)0.2525 (2)0.69580 (14)0.0745 (8)
H180.7159410.2644540.7232350.089*
C190.6153 (2)0.28600 (17)0.63235 (12)0.0547 (6)
H190.6763460.3193420.6170040.066*
C200.12727 (19)0.60798 (17)0.46077 (13)0.0498 (6)
C210.0938 (3)0.5948 (2)0.39413 (16)0.0781 (9)
H210.1072690.5370080.3749170.094*
C220.0387 (3)0.6716 (3)0.35649 (17)0.0961 (11)
H220.0150220.6653500.3113940.115*
C230.0197 (3)0.7557 (3)0.38580 (18)0.0823 (9)
H230.0158600.8066940.3603280.099*
C240.0517 (2)0.7659 (2)0.45095 (16)0.0666 (7)
H240.0371700.8234420.4701460.080*
C250.1055 (2)0.69226 (18)0.48930 (13)0.0542 (6)
H250.1270150.6994780.5344060.065*
C260.2811 (2)0.52682 (18)0.65765 (12)0.0525 (6)
C270.1883 (3)0.5652 (3)0.68230 (14)0.0779 (9)
H270.1469060.6189730.6631020.094*
C280.1551 (3)0.5236 (3)0.73673 (18)0.0994 (12)
H280.0917640.5501220.7541240.119*
C290.2138 (3)0.4452 (3)0.76453 (16)0.0886 (10)
H290.1893930.4167820.8001090.106*
C300.3079 (4)0.4082 (3)0.74065 (15)0.0919 (10)
H300.3494920.3548400.7603730.110*
C310.3433 (3)0.4494 (2)0.68640 (14)0.0753 (8)
H310.4087220.4240790.6701080.090*
C130.6111 (3)0.19539 (19)0.41839 (16)0.0744 (9)
H13A0.6583630.2532320.4252170.112*
H13B0.6625150.1425250.4357620.112*
H13C0.5809640.1860560.3724340.112*
Co10.44779 (2)0.32945 (2)0.49815 (2)0.03338 (9)
N20.30141 (15)0.22768 (12)0.50031 (9)0.0408 (4)
N10.33089 (16)0.36040 (13)0.40709 (8)0.0433 (4)
N30.50598 (16)0.27211 (12)0.59210 (8)0.0406 (4)
O10.50858 (13)0.20190 (10)0.45100 (8)0.0465 (4)
O20.36102 (14)0.43145 (10)0.54328 (7)0.0458 (4)
O30.31921 (16)0.57554 (11)0.60600 (8)0.0574 (4)
O40.18284 (14)0.52997 (12)0.49748 (9)0.0621 (5)
O50.60611 (13)0.39833 (10)0.49462 (7)0.0449 (3)
P10.32259 (5)0.53220 (4)0.53636 (3)0.03897 (13)
Cl10.12621 (6)0.92882 (6)0.64285 (4)0.0721 (2)
O60.2361 (8)0.9806 (7)0.6500 (6)0.127 (4)0.510 (8)
O70.0505 (7)0.9651 (8)0.6776 (5)0.149 (4)0.510 (8)
O80.0811 (8)0.9414 (9)0.5736 (3)0.172 (4)0.510 (8)
O90.1482 (9)0.8313 (5)0.6489 (6)0.167 (4)0.510 (8)
O6'0.2495 (7)0.9388 (9)0.6643 (6)0.162 (5)0.490 (8)
O7'0.0636 (11)1.0124 (6)0.6375 (6)0.198 (5)0.490 (8)
O8'0.0965 (7)0.8659 (7)0.5949 (5)0.135 (4)0.490 (8)
O9'0.0959 (10)0.8894 (8)0.7013 (4)0.184 (4)0.490 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C110.0615 (15)0.0406 (13)0.0583 (15)0.0084 (11)0.0015 (12)0.0064 (11)
C100.084 (2)0.0349 (13)0.083 (2)0.0026 (13)0.0018 (16)0.0092 (13)
C90.078 (2)0.0389 (14)0.100 (2)0.0171 (13)0.0025 (17)0.0005 (14)
C80.0572 (15)0.0461 (14)0.086 (2)0.0107 (12)0.0116 (14)0.0048 (13)
C70.0438 (12)0.0328 (10)0.0513 (13)0.0013 (9)0.0020 (10)0.0043 (10)
C120.0447 (11)0.0318 (11)0.0448 (12)0.0015 (9)0.0001 (9)0.0006 (9)
C60.0347 (11)0.0463 (13)0.0734 (17)0.0024 (10)0.0098 (11)0.0013 (12)
C50.0454 (12)0.0451 (13)0.0497 (13)0.0138 (10)0.0017 (10)0.0091 (10)
C40.0548 (15)0.079 (2)0.0689 (19)0.0162 (14)0.0123 (13)0.0220 (16)
C30.096 (2)0.105 (3)0.0392 (15)0.036 (2)0.0097 (15)0.0065 (16)
C20.085 (2)0.097 (2)0.0419 (15)0.0308 (18)0.0121 (14)0.0106 (14)
C10.0635 (15)0.0715 (17)0.0435 (14)0.0142 (13)0.0121 (11)0.0105 (12)
C140.0537 (14)0.0536 (14)0.0590 (15)0.0044 (11)0.0264 (12)0.0054 (11)
C150.0610 (14)0.0425 (12)0.0452 (13)0.0089 (11)0.0196 (11)0.0084 (10)
C160.088 (2)0.079 (2)0.0620 (18)0.0111 (16)0.0290 (16)0.0270 (15)
C170.113 (3)0.096 (2)0.0491 (17)0.025 (2)0.0133 (18)0.0254 (16)
C180.084 (2)0.075 (2)0.0531 (16)0.0167 (16)0.0131 (15)0.0027 (14)
C190.0621 (15)0.0454 (13)0.0522 (14)0.0038 (11)0.0011 (12)0.0021 (11)
C200.0310 (11)0.0493 (13)0.0676 (16)0.0016 (9)0.0065 (10)0.0047 (12)
C210.0644 (17)0.079 (2)0.085 (2)0.0005 (15)0.0004 (16)0.0276 (17)
C220.079 (2)0.133 (3)0.0617 (19)0.003 (2)0.0189 (16)0.003 (2)
C230.0604 (18)0.092 (3)0.089 (2)0.0110 (16)0.0022 (16)0.028 (2)
C240.0509 (15)0.0574 (16)0.092 (2)0.0108 (12)0.0157 (14)0.0101 (15)
C250.0447 (13)0.0598 (16)0.0593 (15)0.0063 (11)0.0133 (11)0.0024 (12)
C260.0566 (14)0.0576 (15)0.0480 (13)0.0123 (12)0.0220 (11)0.0164 (11)
C270.0576 (16)0.115 (3)0.0654 (18)0.0150 (16)0.0232 (14)0.0008 (17)
C280.066 (2)0.168 (4)0.074 (2)0.006 (2)0.0362 (17)0.000 (2)
C290.093 (2)0.125 (3)0.0545 (18)0.025 (2)0.0298 (18)0.0048 (19)
C300.136 (3)0.086 (2)0.0576 (19)0.006 (2)0.028 (2)0.0036 (16)
C310.099 (2)0.0711 (19)0.0652 (18)0.0094 (17)0.0396 (17)0.0033 (15)
C130.0705 (18)0.0567 (16)0.111 (2)0.0056 (13)0.0539 (18)0.0213 (16)
Co10.03503 (15)0.03001 (14)0.03580 (15)0.00122 (11)0.00878 (10)0.00237 (11)
N20.0376 (9)0.0369 (9)0.0486 (10)0.0005 (7)0.0107 (8)0.0023 (8)
N10.0448 (10)0.0475 (10)0.0368 (9)0.0078 (8)0.0063 (8)0.0013 (8)
N30.0483 (10)0.0319 (9)0.0405 (10)0.0038 (8)0.0062 (8)0.0031 (7)
O10.0431 (8)0.0369 (8)0.0631 (10)0.0008 (6)0.0196 (7)0.0097 (7)
O20.0595 (9)0.0352 (8)0.0478 (9)0.0072 (7)0.0226 (7)0.0008 (6)
O30.0756 (11)0.0427 (9)0.0630 (11)0.0059 (8)0.0362 (9)0.0118 (8)
O40.0400 (9)0.0513 (10)0.0932 (14)0.0022 (7)0.0091 (9)0.0111 (9)
O50.0389 (8)0.0408 (8)0.0574 (9)0.0006 (6)0.0157 (7)0.0072 (7)
P10.0356 (3)0.0335 (3)0.0507 (3)0.0029 (2)0.0154 (2)0.0004 (2)
Cl10.0614 (4)0.0847 (5)0.0731 (5)0.0003 (4)0.0204 (3)0.0265 (4)
O60.123 (7)0.133 (7)0.144 (6)0.076 (6)0.073 (5)0.066 (5)
O70.120 (5)0.183 (9)0.174 (9)0.003 (5)0.101 (6)0.077 (7)
O80.173 (7)0.267 (11)0.069 (4)0.009 (8)0.008 (4)0.006 (6)
O90.204 (9)0.109 (5)0.200 (9)0.008 (5)0.071 (7)0.029 (5)
O6'0.070 (4)0.232 (12)0.182 (9)0.005 (6)0.020 (5)0.151 (8)
O7'0.235 (10)0.119 (7)0.223 (12)0.087 (7)0.004 (8)0.005 (6)
O8'0.117 (5)0.140 (7)0.144 (8)0.026 (5)0.019 (5)0.108 (6)
O9'0.222 (9)0.205 (10)0.151 (7)0.002 (8)0.100 (7)0.047 (7)
Geometric parameters (Å, º) top
C11—C101.376 (4)C21—C221.399 (5)
C11—C121.390 (3)C21—H210.9300
C11—H110.9300C22—C231.365 (5)
C10—C91.370 (4)C22—H220.9300
C10—H100.9300C23—C241.343 (4)
C9—C81.385 (4)C23—H230.9300
C9—H90.9300C24—C251.367 (4)
C8—C71.382 (3)C24—H240.9300
C8—H80.9300C25—H250.9300
C7—C121.385 (3)C26—C271.350 (3)
C7—N21.465 (3)C26—C311.359 (4)
C12—O11.372 (2)C26—O31.411 (3)
C6—N21.489 (3)C27—C281.392 (4)
C6—C51.501 (3)C27—H270.9300
C6—H6A0.9700C28—C291.348 (5)
C6—H6B0.9700C28—H280.9300
C5—N11.336 (3)C29—C301.345 (5)
C5—C41.396 (3)C29—H290.9300
C4—C31.378 (4)C30—C311.397 (4)
C4—H40.9300C30—H300.9300
C3—C21.355 (5)C31—H310.9300
C3—H30.9300C13—O11.439 (3)
C2—C11.368 (4)C13—H13A0.9600
C2—H20.9300C13—H13B0.9600
C1—N11.341 (3)C13—H13C0.9600
C1—H10.9300Co1—O52.0147 (14)
C14—N21.487 (3)Co1—O22.0545 (14)
C14—C151.498 (3)Co1—N32.0991 (17)
C14—H14A0.9700Co1—N12.1194 (17)
C14—H14B0.9700Co1—N22.1661 (17)
C15—N31.335 (3)Co1—O12.2111 (14)
C15—C161.389 (3)O2—P11.4745 (15)
C16—C171.362 (4)O3—P11.5841 (16)
C16—H160.9300O4—P11.5958 (17)
C17—C181.364 (4)O5—P1i1.4818 (14)
C17—H170.9300Cl1—O71.317 (5)
C18—C191.381 (4)Cl1—O8'1.326 (5)
C18—H180.9300Cl1—O7'1.355 (7)
C19—N31.341 (3)Cl1—O6'1.355 (8)
C19—H190.9300Cl1—O91.390 (6)
C20—C251.367 (3)Cl1—O61.398 (7)
C20—C211.379 (4)Cl1—O9'1.440 (6)
C20—O41.405 (3)Cl1—O81.443 (6)
C10—C11—C12118.9 (2)C24—C25—H25120.3
C10—C11—H11120.5C27—C26—C31120.4 (3)
C12—C11—H11120.5C27—C26—O3117.7 (3)
C9—C10—C11121.2 (2)C31—C26—O3121.5 (2)
C9—C10—H10119.4C26—C27—C28119.3 (3)
C11—C10—H10119.4C26—C27—H27120.3
C10—C9—C8119.8 (2)C28—C27—H27120.3
C10—C9—H9120.1C29—C28—C27120.8 (3)
C8—C9—H9120.1C29—C28—H28119.6
C7—C8—C9120.1 (3)C27—C28—H28119.6
C7—C8—H8119.9C30—C29—C28119.8 (3)
C9—C8—H8119.9C30—C29—H29120.1
C8—C7—C12119.4 (2)C28—C29—H29120.1
C8—C7—N2121.0 (2)C29—C30—C31120.3 (3)
C12—C7—N2119.52 (18)C29—C30—H30119.8
O1—C12—C7116.45 (18)C31—C30—H30119.8
O1—C12—C11123.0 (2)C26—C31—C30119.3 (3)
C7—C12—C11120.6 (2)C26—C31—H31120.3
N2—C6—C5110.60 (17)C30—C31—H31120.3
N2—C6—H6A109.5O1—C13—H13A109.5
C5—C6—H6A109.5O1—C13—H13B109.5
N2—C6—H6B109.5H13A—C13—H13B109.5
C5—C6—H6B109.5O1—C13—H13C109.5
H6A—C6—H6B108.1H13A—C13—H13C109.5
N1—C5—C4120.9 (2)H13B—C13—H13C109.5
N1—C5—C6116.39 (19)O5—Co1—O299.94 (6)
C4—C5—C6122.6 (2)O5—Co1—N396.45 (7)
C3—C4—C5118.4 (3)O2—Co1—N385.50 (6)
C3—C4—H4120.8O5—Co1—N1104.31 (7)
C5—C4—H4120.8O2—Co1—N190.70 (6)
C2—C3—C4120.4 (3)N3—Co1—N1159.24 (7)
C2—C3—H3119.8O5—Co1—N2167.42 (6)
C4—C3—H3119.8O2—Co1—N291.67 (6)
C3—C2—C1118.3 (3)N3—Co1—N279.52 (7)
C3—C2—H2120.8N1—Co1—N280.20 (7)
C1—C2—H2120.8O5—Co1—O191.56 (6)
N1—C1—C2122.8 (3)O2—Co1—O1168.47 (6)
N1—C1—H1118.6N3—Co1—O192.46 (6)
C2—C1—H1118.6N1—Co1—O187.21 (6)
N2—C14—C15111.41 (17)N2—Co1—O176.81 (6)
N2—C14—H14A109.3C7—N2—C14112.11 (17)
C15—C14—H14A109.3C7—N2—C6110.06 (17)
N2—C14—H14B109.3C14—N2—C6113.03 (17)
C15—C14—H14B109.3C7—N2—Co1111.79 (12)
H14A—C14—H14B108.0C14—N2—Co1105.33 (13)
N3—C15—C16121.0 (2)C6—N2—Co1104.17 (12)
N3—C15—C14117.28 (19)C5—N1—C1119.0 (2)
C16—C15—C14121.6 (2)C5—N1—Co1112.90 (15)
C17—C16—C15119.5 (3)C1—N1—Co1127.91 (16)
C17—C16—H16120.3C15—N3—C19119.0 (2)
C15—C16—H16120.3C15—N3—Co1113.97 (15)
C16—C17—C18119.8 (3)C19—N3—Co1126.81 (16)
C16—C17—H17120.1C12—O1—C13117.18 (17)
C18—C17—H17120.1C12—O1—Co1115.36 (12)
C17—C18—C19118.4 (3)C13—O1—Co1126.99 (14)
C17—C18—H18120.8P1—O2—Co1140.76 (9)
C19—C18—H18120.8C26—O3—P1125.61 (14)
N3—C19—C18122.3 (3)C20—O4—P1122.38 (14)
N3—C19—H19118.9P1i—O5—Co1150.98 (10)
C18—C19—H19118.9O2—P1—O5i120.31 (8)
C25—C20—C21121.4 (2)O2—P1—O3109.70 (9)
C25—C20—O4122.1 (2)O5i—P1—O3105.17 (9)
C21—C20—O4116.5 (2)O2—P1—O4105.19 (9)
C20—C21—C22117.6 (3)O5i—P1—O4109.70 (9)
C20—C21—H21121.2O3—P1—O4106.01 (10)
C22—C21—H21121.2O8'—Cl1—O7'117.9 (6)
C23—C22—C21120.2 (3)O8'—Cl1—O6'113.5 (5)
C23—C22—H22119.9O7'—Cl1—O6'113.7 (6)
C21—C22—H22119.9O7—Cl1—O9116.7 (5)
C24—C23—C22120.9 (3)O7—Cl1—O6112.1 (5)
C24—C23—H23119.6O9—Cl1—O6111.6 (5)
C22—C23—H23119.6O8'—Cl1—O9'108.7 (5)
C23—C24—C25120.6 (3)O7'—Cl1—O9'101.6 (6)
C23—C24—H24119.7O6'—Cl1—O9'98.6 (6)
C25—C24—H24119.7O7—Cl1—O8112.1 (6)
C20—C25—C24119.4 (3)O9—Cl1—O8103.3 (5)
C20—C25—H25120.3O6—Cl1—O899.3 (5)
C12—C11—C10—C90.1 (4)C8—C7—N2—C1461.7 (3)
C11—C10—C9—C80.2 (4)C12—C7—N2—C14120.9 (2)
C10—C9—C8—C70.2 (4)C8—C7—N2—C665.0 (3)
C9—C8—C7—C120.0 (4)C12—C7—N2—C6112.4 (2)
C9—C8—C7—N2177.3 (2)C8—C7—N2—Co1179.76 (19)
C8—C7—C12—O1179.9 (2)C12—C7—N2—Co12.9 (2)
N2—C7—C12—O12.7 (3)C15—C14—N2—C784.5 (2)
C8—C7—C12—C110.1 (3)C15—C14—N2—C6150.37 (19)
N2—C7—C12—C11177.5 (2)C15—C14—N2—Co137.3 (2)
C10—C11—C12—O1179.8 (2)C5—C6—N2—C778.1 (2)
C10—C11—C12—C70.1 (3)C5—C6—N2—C14155.68 (19)
N2—C6—C5—N138.4 (3)C5—C6—N2—Co141.9 (2)
N2—C6—C5—C4145.8 (2)C4—C5—N1—C13.5 (3)
N1—C5—C4—C34.0 (4)C6—C5—N1—C1172.4 (2)
C6—C5—C4—C3171.6 (2)C4—C5—N1—Co1171.74 (18)
C5—C4—C3—C21.0 (4)C6—C5—N1—Co112.4 (2)
C4—C3—C2—C12.3 (4)C2—C1—N1—C50.0 (4)
C3—C2—C1—N12.9 (4)C2—C1—N1—Co1174.42 (19)
N2—C14—C15—N327.5 (3)C16—C15—N3—C192.5 (3)
N2—C14—C15—C16156.7 (2)C14—C15—N3—C19173.3 (2)
N3—C15—C16—C173.8 (4)C16—C15—N3—Co1177.11 (19)
C14—C15—C16—C17171.8 (3)C14—C15—N3—Co11.3 (2)
C15—C16—C17—C182.2 (5)C18—C19—N3—C150.3 (3)
C16—C17—C18—C190.5 (5)C18—C19—N3—Co1173.56 (19)
C17—C18—C19—N31.8 (4)C7—C12—O1—C13173.9 (2)
C25—C20—C21—C221.2 (4)C11—C12—O1—C136.4 (3)
O4—C20—C21—C22179.7 (3)C7—C12—O1—Co11.2 (2)
C20—C21—C22—C230.1 (5)C11—C12—O1—Co1179.11 (17)
C21—C22—C23—C240.9 (5)C27—C26—O3—P1123.1 (2)
C22—C23—C24—C250.8 (5)C31—C26—O3—P163.6 (3)
C21—C20—C25—C241.4 (4)C25—C20—O4—P166.4 (3)
O4—C20—C25—C24179.6 (2)C21—C20—O4—P1114.5 (2)
C23—C24—C25—C200.4 (4)Co1—O2—P1—O5i30.1 (2)
C31—C26—C27—C281.3 (5)Co1—O2—P1—O3152.23 (14)
O3—C26—C27—C28174.7 (3)Co1—O2—P1—O494.14 (17)
C26—C27—C28—C290.6 (5)C26—O3—P1—O237.1 (2)
C27—C28—C29—C301.9 (6)C26—O3—P1—O5i167.80 (19)
C28—C29—C30—C311.3 (6)C26—O3—P1—O476.0 (2)
C27—C26—C31—C301.8 (5)C20—O4—P1—O2156.18 (18)
O3—C26—C31—C30175.0 (3)C20—O4—P1—O5i25.4 (2)
C29—C30—C31—C260.5 (5)C20—O4—P1—O387.6 (2)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O6ii0.932.523.349 (11)148
C2—H2···O6ii0.932.533.395 (11)155
C31—H31···O20.932.603.046 (3)110
C13—H13A···O3i0.962.513.367 (3)148
C13—H13A···O50.962.633.268 (3)124
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+3/2, z1/2.
Bis(µ-diphenyl phosphato-κ2O:O')bis({N,N-bis[(pyridin-2-yl)methyl]quinolin-8-amine-κ4N,N',N'',O}cobalt(II)) bis(perchlorate) (1b) top
Crystal data top
[Co(C12H10O4P)2(C21H18N4)2](ClO4)2F(000) = 1508
Mr = 1467.88Dx = 1.478 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.0021 (2) ÅCell parameters from 7902 reflections
b = 12.8075 (3) Åθ = 2.4–23.9°
c = 19.8373 (4) ŵ = 0.71 mm1
β = 93.008 (1)°T = 296 K
V = 3298.84 (11) Å3Square, pink
Z = 20.25 × 0.20 × 0.16 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer
4391 reflections with I > 2σ(I)
Radiation source: Sealed tubeRint = 0.023
ω and φ scanθmax = 24.2°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 1414
Tmin = 0.654, Tmax = 0.745k = 1414
19894 measured reflectionsl = 2222
5273 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.109 w = 1/[σ2(Fo2) + (0.0453P)2 + 3.339P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.002
5273 reflectionsΔρmax = 0.42 e Å3
433 parametersΔρmin = 0.50 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.6627 (3)1.0353 (4)0.0386 (2)0.0693 (11)
H10.6833700.9658110.0395380.083*
C20.5752 (4)1.0661 (5)0.0767 (3)0.0977 (17)
H20.5381181.0176880.1031340.117*
C30.5440 (4)1.1672 (5)0.0750 (3)0.1006 (17)
H30.4852681.1884280.1000700.121*
C40.5992 (3)1.2373 (4)0.0363 (2)0.0742 (12)
H40.5788041.3067810.0346970.089*
C50.6862 (3)1.2036 (3)0.00064 (17)0.0492 (9)
C60.7520 (3)1.2755 (3)0.04257 (17)0.0523 (9)
H6A0.8056111.3037310.0156660.063*
H6B0.7106291.3333500.0574760.063*
C70.8948 (3)1.2719 (3)0.12945 (19)0.0527 (9)
H7A0.8771081.3297470.1582360.063*
H7B0.9327381.2995790.0926170.063*
C80.9608 (2)1.1958 (3)0.16922 (17)0.0472 (8)
C91.0244 (3)1.2248 (4)0.2250 (2)0.0678 (12)
H91.0245671.2932010.2407550.081*
C101.0861 (3)1.1513 (5)0.2562 (2)0.0766 (13)
H101.1287051.1693390.2935170.092*
C111.0853 (3)1.0518 (4)0.2328 (2)0.0704 (12)
H111.1273831.0010910.2533700.084*
C121.0210 (3)1.0279 (3)0.17814 (18)0.0597 (10)
H121.0198330.9594120.1624870.072*
C130.7246 (3)0.9234 (3)0.15816 (18)0.0504 (9)
H130.7551010.8682690.1361030.061*
C140.6579 (3)0.9006 (3)0.20973 (19)0.0573 (10)
H140.6467330.8317390.2223490.069*
C150.6103 (3)0.9794 (3)0.24076 (19)0.0562 (10)
H150.5649000.9651230.2742820.067*
C160.6294 (2)1.0828 (3)0.22229 (16)0.0443 (8)
C170.5859 (3)1.1710 (3)0.25351 (19)0.0613 (10)
H170.5381421.1607720.2861640.074*
C180.6125 (3)1.2700 (3)0.2368 (2)0.0661 (11)
H180.5836841.3266040.2583250.079*
C190.6835 (3)1.2867 (3)0.18697 (19)0.0565 (9)
H190.7016451.3546340.1759850.068*
C200.7263 (2)1.2047 (2)0.15434 (15)0.0389 (7)
C210.7003 (2)1.1005 (2)0.17176 (15)0.0377 (7)
C221.0283 (3)0.6881 (3)0.09565 (16)0.0440 (8)
C231.1241 (3)0.7142 (3)0.12233 (19)0.0636 (10)
H231.1405570.7834120.1321620.076*
C241.1959 (4)0.6361 (4)0.1344 (2)0.0830 (14)
H241.2613830.6529730.1522290.100*
C251.1715 (4)0.5339 (4)0.1203 (3)0.0835 (14)
H251.2200490.4814860.1288160.100*
C261.0766 (4)0.5100 (3)0.0941 (3)0.0820 (13)
H261.0601170.4408200.0841850.098*
C271.0030 (3)0.5874 (3)0.0815 (2)0.0620 (10)
H270.9374980.5703140.0637500.074*
C280.7975 (2)0.7505 (3)0.05410 (17)0.0432 (8)
C290.7412 (3)0.6885 (3)0.0144 (2)0.0671 (11)
H290.7701470.6607090.0255580.080*
C300.6399 (3)0.6677 (4)0.0346 (3)0.0913 (16)
H300.6004920.6248830.0082220.110*
C310.5970 (3)0.7093 (4)0.0928 (3)0.0867 (15)
H310.5289870.6942880.1060310.104*
C320.6535 (3)0.7726 (4)0.1313 (2)0.0776 (13)
H320.6238410.8018400.1706120.093*
C330.7557 (3)0.7937 (3)0.11216 (18)0.0607 (10)
H330.7950440.8367000.1384830.073*
Cl10.65199 (8)0.56711 (8)0.15434 (6)0.0669 (3)
Co10.84769 (3)1.06875 (3)0.06506 (2)0.03324 (14)
N10.7177 (2)1.1036 (2)0.00074 (14)0.0461 (7)
N20.79944 (19)1.22094 (19)0.10202 (13)0.0386 (6)
N30.9599 (2)1.0980 (2)0.14607 (13)0.0443 (7)
N40.74576 (19)1.0191 (2)0.13985 (13)0.0397 (6)
O10.94517 (15)1.13453 (16)0.00421 (10)0.0407 (5)
O20.87291 (16)0.92070 (16)0.03622 (12)0.0460 (6)
O30.95296 (17)0.76609 (18)0.08654 (11)0.0493 (6)
O40.90328 (16)0.76707 (17)0.03819 (11)0.0454 (5)
O50.6551 (3)0.6763 (2)0.1479 (2)0.1269 (15)
O60.6495 (3)0.5389 (3)0.22227 (19)0.1047 (11)
O70.7437 (2)0.5270 (3)0.12750 (18)0.0903 (10)
O80.5650 (3)0.5283 (4)0.1202 (2)0.1341 (16)
P10.94875 (6)0.83950 (6)0.02126 (4)0.0353 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.065 (3)0.070 (3)0.071 (3)0.002 (2)0.013 (2)0.009 (2)
C20.080 (3)0.103 (4)0.105 (4)0.000 (3)0.044 (3)0.018 (3)
C30.072 (3)0.115 (5)0.110 (4)0.017 (3)0.034 (3)0.014 (4)
C40.061 (3)0.076 (3)0.085 (3)0.019 (2)0.002 (2)0.016 (3)
C50.0446 (19)0.053 (2)0.051 (2)0.0137 (17)0.0130 (16)0.0105 (17)
C60.068 (2)0.0379 (19)0.052 (2)0.0162 (17)0.0154 (18)0.0070 (16)
C70.050 (2)0.041 (2)0.069 (2)0.0062 (16)0.0214 (18)0.0201 (18)
C80.0417 (18)0.057 (2)0.0445 (19)0.0095 (17)0.0168 (15)0.0138 (17)
C90.061 (2)0.088 (3)0.056 (2)0.012 (2)0.013 (2)0.029 (2)
C100.060 (3)0.124 (4)0.045 (2)0.011 (3)0.0028 (19)0.006 (3)
C110.067 (3)0.093 (4)0.050 (2)0.004 (2)0.007 (2)0.014 (2)
C120.059 (2)0.070 (3)0.049 (2)0.001 (2)0.0057 (18)0.0110 (19)
C130.058 (2)0.039 (2)0.055 (2)0.0050 (17)0.0112 (17)0.0036 (16)
C140.069 (2)0.046 (2)0.058 (2)0.0192 (19)0.0158 (19)0.0033 (18)
C150.053 (2)0.064 (3)0.052 (2)0.0194 (19)0.0172 (17)0.0025 (19)
C160.0349 (17)0.059 (2)0.0389 (18)0.0046 (16)0.0053 (14)0.0063 (16)
C170.046 (2)0.080 (3)0.060 (2)0.001 (2)0.0151 (18)0.003 (2)
C180.059 (2)0.069 (3)0.072 (3)0.018 (2)0.018 (2)0.009 (2)
C190.059 (2)0.048 (2)0.063 (2)0.0105 (18)0.0140 (19)0.0007 (18)
C200.0373 (16)0.0377 (18)0.0426 (18)0.0061 (14)0.0092 (14)0.0032 (14)
C210.0299 (15)0.0453 (19)0.0378 (17)0.0010 (14)0.0012 (13)0.0042 (14)
C220.051 (2)0.046 (2)0.0352 (17)0.0035 (16)0.0087 (15)0.0069 (15)
C230.078 (3)0.056 (2)0.055 (2)0.006 (2)0.011 (2)0.0066 (19)
C240.068 (3)0.099 (4)0.078 (3)0.005 (3)0.028 (2)0.017 (3)
C250.078 (3)0.073 (3)0.099 (4)0.023 (3)0.010 (3)0.018 (3)
C260.085 (3)0.048 (2)0.112 (4)0.012 (2)0.004 (3)0.004 (2)
C270.055 (2)0.046 (2)0.085 (3)0.0010 (18)0.002 (2)0.004 (2)
C280.0378 (17)0.0425 (19)0.050 (2)0.0005 (15)0.0125 (15)0.0117 (15)
C290.046 (2)0.077 (3)0.080 (3)0.001 (2)0.0123 (19)0.024 (2)
C300.050 (3)0.103 (4)0.123 (4)0.014 (2)0.020 (3)0.024 (3)
C310.045 (2)0.116 (4)0.098 (4)0.009 (3)0.000 (2)0.022 (3)
C320.065 (3)0.113 (4)0.054 (2)0.008 (3)0.008 (2)0.013 (3)
C330.062 (2)0.078 (3)0.043 (2)0.005 (2)0.0080 (18)0.002 (2)
Cl10.0620 (6)0.0511 (6)0.0887 (8)0.0012 (5)0.0133 (5)0.0065 (5)
Co10.0331 (2)0.0307 (2)0.0363 (2)0.00442 (17)0.00581 (17)0.00351 (18)
N10.0395 (15)0.0517 (18)0.0469 (16)0.0043 (13)0.0004 (12)0.0041 (14)
N20.0407 (14)0.0315 (14)0.0446 (15)0.0027 (11)0.0119 (12)0.0015 (12)
N30.0418 (15)0.0546 (18)0.0369 (15)0.0026 (13)0.0064 (12)0.0009 (13)
N40.0397 (14)0.0382 (15)0.0417 (15)0.0002 (12)0.0074 (12)0.0036 (12)
O10.0405 (12)0.0396 (12)0.0426 (12)0.0007 (10)0.0091 (9)0.0025 (10)
O20.0472 (13)0.0308 (11)0.0613 (14)0.0028 (10)0.0152 (11)0.0069 (10)
O30.0548 (14)0.0476 (14)0.0474 (13)0.0084 (11)0.0198 (11)0.0109 (11)
O40.0385 (12)0.0478 (13)0.0508 (13)0.0003 (10)0.0109 (10)0.0146 (11)
O50.167 (4)0.0462 (19)0.171 (4)0.017 (2)0.036 (3)0.002 (2)
O60.103 (3)0.114 (3)0.099 (3)0.017 (2)0.027 (2)0.017 (2)
O70.082 (2)0.080 (2)0.113 (3)0.0142 (17)0.0446 (19)0.0039 (19)
O80.086 (3)0.171 (4)0.144 (4)0.043 (3)0.008 (2)0.024 (3)
P10.0391 (4)0.0291 (4)0.0387 (4)0.0020 (3)0.0118 (3)0.0011 (3)
Geometric parameters (Å, º) top
C1—N11.336 (5)C19—H190.9300
C1—C21.389 (6)C20—C211.424 (4)
C1—H10.9300C20—N21.459 (4)
C2—C31.358 (7)C21—N41.370 (4)
C2—H20.9300C22—C271.358 (5)
C3—C41.361 (7)C22—C231.370 (5)
C3—H30.9300C22—O31.403 (4)
C4—C51.383 (5)C23—C241.380 (6)
C4—H40.9300C23—H230.9300
C5—N11.346 (4)C24—C251.373 (7)
C5—C61.482 (5)C24—H240.9300
C6—N21.478 (4)C25—C261.350 (6)
C6—H6A0.9700C25—H250.9300
C6—H6B0.9700C26—C271.391 (6)
C7—N21.479 (4)C26—H260.9300
C7—C81.497 (5)C27—H270.9300
C7—H7A0.9700C28—C291.359 (5)
C7—H7B0.9700C28—C331.365 (5)
C8—N31.334 (4)C28—O41.411 (4)
C8—C91.396 (5)C29—C301.382 (6)
C9—C101.364 (6)C29—H290.9300
C9—H90.9300C30—C311.363 (7)
C10—C111.356 (6)C30—H300.9300
C10—H100.9300C31—C321.357 (7)
C11—C121.368 (5)C31—H310.9300
C11—H110.9300C32—C331.389 (6)
C12—N31.338 (5)C32—H320.9300
C12—H120.9300C33—H330.9300
C13—N41.311 (4)Cl1—O81.380 (4)
C13—C141.406 (5)Cl1—O61.397 (4)
C13—H130.9300Cl1—O51.405 (3)
C14—C151.350 (5)Cl1—O71.426 (3)
C14—H140.9300Co1—O22.012 (2)
C15—C161.399 (5)Co1—O12.095 (2)
C15—H150.9300Co1—N12.128 (3)
C16—C211.415 (4)Co1—N42.137 (2)
C16—C171.420 (5)Co1—N32.146 (3)
C17—C181.361 (6)Co1—N22.186 (2)
C17—H170.9300O1—P1i1.475 (2)
C18—C191.403 (5)O2—P11.474 (2)
C18—H180.9300O3—P11.599 (2)
C19—C201.367 (5)O4—P11.590 (2)
N1—C1—C2121.3 (4)C25—C24—H24119.7
N1—C1—H1119.4C23—C24—H24119.7
C2—C1—H1119.4C26—C25—C24119.4 (4)
C3—C2—C1119.6 (5)C26—C25—H25120.3
C3—C2—H2120.2C24—C25—H25120.3
C1—C2—H2120.2C25—C26—C27121.0 (4)
C2—C3—C4119.6 (4)C25—C26—H26119.5
C2—C3—H3120.2C27—C26—H26119.5
C4—C3—H3120.2C22—C27—C26118.9 (4)
C3—C4—C5119.0 (4)C22—C27—H27120.5
C3—C4—H4120.5C26—C27—H27120.5
C5—C4—H4120.5C29—C28—C33121.6 (3)
N1—C5—C4121.8 (4)C29—C28—O4120.4 (3)
N1—C5—C6115.8 (3)C33—C28—O4117.9 (3)
C4—C5—C6122.3 (4)C28—C29—C30118.6 (4)
N2—C6—C5111.0 (3)C28—C29—H29120.7
N2—C6—H6A109.4C30—C29—H29120.7
C5—C6—H6A109.4C31—C30—C29120.7 (4)
N2—C6—H6B109.4C31—C30—H30119.6
C5—C6—H6B109.4C29—C30—H30119.6
H6A—C6—H6B108.0C32—C31—C30120.1 (4)
N2—C7—C8110.7 (3)C32—C31—H31119.9
N2—C7—H7A109.5C30—C31—H31119.9
C8—C7—H7A109.5C31—C32—C33120.0 (4)
N2—C7—H7B109.5C31—C32—H32120.0
C8—C7—H7B109.5C33—C32—H32120.0
H7A—C7—H7B108.1C28—C33—C32119.0 (4)
N3—C8—C9121.1 (4)C28—C33—H33120.5
N3—C8—C7115.8 (3)C32—C33—H33120.5
C9—C8—C7123.0 (3)O8—Cl1—O6108.7 (3)
C10—C9—C8119.0 (4)O8—Cl1—O5110.0 (3)
C10—C9—H9120.5O6—Cl1—O5110.3 (3)
C8—C9—H9120.5O8—Cl1—O7111.5 (3)
C11—C10—C9119.9 (4)O6—Cl1—O7109.2 (2)
C11—C10—H10120.0O5—Cl1—O7107.2 (2)
C9—C10—H10120.0O2—Co1—O194.55 (9)
C10—C11—C12118.4 (4)O2—Co1—N199.17 (10)
C10—C11—H11120.8O1—Co1—N190.10 (9)
C12—C11—H11120.8O2—Co1—N491.90 (9)
N3—C12—C11123.3 (4)O1—Co1—N4173.54 (9)
N3—C12—H12118.3N1—Co1—N489.24 (10)
C11—C12—H12118.3O2—Co1—N3105.24 (10)
N4—C13—C14122.8 (3)O1—Co1—N390.59 (9)
N4—C13—H13118.6N1—Co1—N3155.45 (11)
C14—C13—H13118.6N4—Co1—N387.36 (10)
C15—C14—C13119.4 (3)O2—Co1—N2171.65 (9)
C15—C14—H14120.3O1—Co1—N293.18 (9)
C13—C14—H14120.3N1—Co1—N277.64 (10)
C14—C15—C16119.7 (3)N4—Co1—N280.40 (9)
C14—C15—H15120.1N3—Co1—N277.82 (10)
C16—C15—H15120.1C1—N1—C5118.7 (3)
C15—C16—C21118.0 (3)C1—N1—Co1126.3 (3)
C15—C16—C17123.9 (3)C5—N1—Co1114.8 (2)
C21—C16—C17118.1 (3)C20—N2—C6112.0 (2)
C18—C17—C16121.5 (3)C20—N2—C7111.5 (2)
C18—C17—H17119.2C6—N2—C7113.0 (3)
C16—C17—H17119.2C20—N2—Co1108.73 (18)
C17—C18—C19119.9 (4)C6—N2—Co1105.63 (19)
C17—C18—H18120.0C7—N2—Co1105.51 (18)
C19—C18—H18120.0C8—N3—C12118.1 (3)
C20—C19—C18121.0 (4)C8—N3—Co1114.6 (2)
C20—C19—H19119.5C12—N3—Co1127.1 (3)
C18—C19—H19119.5C13—N4—C21118.8 (3)
C19—C20—C21119.8 (3)C13—N4—Co1128.1 (2)
C19—C20—N2121.6 (3)C21—N4—Co1113.1 (2)
C21—C20—N2118.6 (3)P1i—O1—Co1147.81 (14)
N4—C21—C16121.2 (3)P1—O2—Co1147.43 (14)
N4—C21—C20119.2 (3)C22—O3—P1121.11 (19)
C16—C21—C20119.6 (3)C28—O4—P1125.02 (18)
C27—C22—C23121.1 (3)O2—P1—O1i122.04 (13)
C27—C22—O3119.3 (3)O2—P1—O4109.53 (13)
C23—C22—O3119.4 (3)O1i—P1—O4106.09 (12)
C22—C23—C24118.9 (4)O2—P1—O3104.28 (12)
C22—C23—H23120.5O1i—P1—O3109.00 (12)
C24—C23—H23120.5O4—P1—O3104.67 (13)
C25—C24—C23120.6 (4)
N1—C1—C2—C30.7 (8)O4—C28—C33—C32175.6 (3)
C1—C2—C3—C40.4 (9)C31—C32—C33—C280.4 (7)
C2—C3—C4—C50.1 (8)C2—C1—N1—C50.7 (6)
C3—C4—C5—N10.1 (6)C2—C1—N1—Co1176.0 (4)
C3—C4—C5—C6178.4 (4)C4—C5—N1—C10.4 (5)
N1—C5—C6—N232.9 (4)C6—C5—N1—C1178.8 (3)
C4—C5—C6—N2148.7 (3)C4—C5—N1—Co1176.2 (3)
N2—C7—C8—N335.3 (4)C6—C5—N1—Co15.4 (4)
N2—C7—C8—C9148.1 (3)C19—C20—N2—C664.1 (4)
N3—C8—C9—C100.1 (5)C21—C20—N2—C6116.5 (3)
C7—C8—C9—C10176.6 (3)C19—C20—N2—C763.7 (4)
C8—C9—C10—C110.1 (6)C21—C20—N2—C7115.7 (3)
C9—C10—C11—C120.5 (6)C19—C20—N2—Co1179.6 (3)
C10—C11—C12—N30.9 (6)C21—C20—N2—Co10.2 (3)
N4—C13—C14—C152.2 (6)C5—C6—N2—C2076.5 (3)
C13—C14—C15—C161.3 (6)C5—C6—N2—C7156.5 (3)
C14—C15—C16—C211.0 (5)C5—C6—N2—Co141.7 (3)
C14—C15—C16—C17177.7 (4)C8—C7—N2—C2075.4 (3)
C15—C16—C17—C18175.5 (4)C8—C7—N2—C6157.4 (3)
C21—C16—C17—C181.3 (5)C8—C7—N2—Co142.4 (3)
C16—C17—C18—C190.8 (6)C9—C8—N3—C120.4 (5)
C17—C18—C19—C200.4 (6)C7—C8—N3—C12177.2 (3)
C18—C19—C20—C211.2 (5)C9—C8—N3—Co1175.3 (2)
C18—C19—C20—N2179.4 (3)C7—C8—N3—Co18.0 (3)
C15—C16—C21—N42.6 (5)C11—C12—N3—C80.8 (5)
C17—C16—C21—N4179.6 (3)C11—C12—N3—Co1175.0 (3)
C15—C16—C21—C20176.4 (3)C14—C13—N4—C210.6 (5)
C17—C16—C21—C200.6 (5)C14—C13—N4—Co1178.1 (3)
C19—C20—C21—N4178.4 (3)C16—C21—N4—C131.8 (4)
N2—C20—C21—N41.1 (4)C20—C21—N4—C13177.2 (3)
C19—C20—C21—C160.6 (5)C16—C21—N4—Co1179.2 (2)
N2—C20—C21—C16179.9 (3)C20—C21—N4—Co11.8 (3)
C27—C22—C23—C240.5 (6)C27—C22—O3—P1100.9 (3)
O3—C22—C23—C24176.6 (3)C23—C22—O3—P182.9 (4)
C22—C23—C24—C250.4 (7)C29—C28—O4—P174.4 (4)
C23—C24—C25—C260.4 (8)C33—C28—O4—P1109.1 (3)
C24—C25—C26—C270.5 (8)Co1—O2—P1—O1i21.0 (3)
C23—C22—C27—C260.5 (6)Co1—O2—P1—O4145.7 (3)
O3—C22—C27—C26176.7 (4)Co1—O2—P1—O3102.8 (3)
C25—C26—C27—C220.5 (7)C28—O4—P1—O225.7 (3)
C33—C28—C29—C301.3 (6)C28—O4—P1—O1i159.2 (2)
O4—C28—C29—C30175.0 (4)C28—O4—P1—O385.6 (3)
C28—C29—C30—C310.7 (8)C22—O3—P1—O2170.4 (2)
C29—C30—C31—C320.5 (8)C22—O3—P1—O1i38.6 (3)
C30—C31—C32—C331.1 (8)C22—O3—P1—O474.6 (3)
C29—C28—C33—C320.8 (6)
Symmetry code: (i) x+2, y+2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7B···O4i0.972.583.305 (4)131
C13—H13···O20.932.653.172 (4)116
C14—H14···O50.932.483.123 (5)126
C19—H19···Cl1ii0.932.823.668 (4)151
C19—H19···O6ii0.932.633.339 (5)133
C19—H19···O7ii0.932.483.402 (5)171
Symmetry codes: (i) x+2, y+2, z; (ii) x, y+1, z.
 

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