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
CCDC references: 1550823; 1550822
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)2 | F(000) = 1468 |
Mr = 1425.84 | Dx = 1.491 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.0638 (2) Å | Cell parameters from 7252 reflections |
b = 14.0258 (4) Å | θ = 2.5–25.8° |
c = 20.8917 (6) Å | µ = 0.73 mm−1 |
β = 101.590 (1)° | T = 298 K |
V = 3175.84 (14) Å3 | Block, pink |
Z = 2 | 0.35 × 0.25 × 0.15 mm |
Data collection top
Bruker AXS Kappa apex2 CCD diffractometer | 5642 reflections with I > 2σ(I) |
Radiation source: Sealed tube | Rint = 0.029 |
ω and φ scan | θmax = 28.3°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | h = −14→10 |
Tmin = 0.841, Tmax = 1.000 | k = −18→18 |
24243 measured reflections | l = −24→27 |
7780 independent reflections | |
Refinement top
Refinement on F2 | 154 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H-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 reflections | Δρmax = 0.47 e Å−3 |
452 parameters | Δρmin = −0.37 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
C11 | 0.4541 (2) | 0.03930 (16) | 0.41722 (12) | 0.0549 (6) | |
H11 | 0.524475 | 0.032009 | 0.399722 | 0.066* | |
C10 | 0.3712 (3) | −0.03433 (18) | 0.41481 (15) | 0.0700 (8) | |
H10 | 0.386065 | −0.091758 | 0.395532 | 0.084* | |
C9 | 0.2670 (3) | −0.02456 (19) | 0.44031 (16) | 0.0751 (8) | |
H9 | 0.211721 | −0.074964 | 0.438133 | 0.090* | |
C8 | 0.2443 (2) | 0.06058 (18) | 0.46932 (14) | 0.0635 (7) | |
H8 | 0.173819 | 0.067274 | 0.486788 | 0.076* | |
C7 | 0.3263 (2) | 0.13564 (15) | 0.47238 (11) | 0.0437 (5) | |
C12 | 0.43099 (19) | 0.12479 (14) | 0.44623 (10) | 0.0417 (5) | |
C6 | 0.19018 (19) | 0.27250 (17) | 0.45940 (12) | 0.0516 (6) | |
H6A | 0.158087 | 0.320946 | 0.484631 | 0.062* | |
H6B | 0.126689 | 0.224581 | 0.446661 | 0.062* | |
C5 | 0.2215 (2) | 0.31690 (16) | 0.39940 (11) | 0.0478 (5) | |
C4 | 0.1387 (3) | 0.3190 (2) | 0.33943 (15) | 0.0711 (8) | |
H4 | 0.064778 | 0.285470 | 0.333353 | 0.085* | |
C3 | 0.1692 (3) | 0.3720 (3) | 0.28942 (14) | 0.0835 (10) | |
H3 | 0.114799 | 0.375214 | 0.249282 | 0.100* | |
C2 | 0.2779 (3) | 0.4195 (2) | 0.29836 (13) | 0.0745 (9) | |
H2 | 0.297753 | 0.457238 | 0.265318 | 0.089* | |
C1 | 0.3579 (2) | 0.41067 (19) | 0.35721 (11) | 0.0593 (6) | |
H1 | 0.434174 | 0.440791 | 0.362848 | 0.071* | |
C14 | 0.2933 (2) | 0.21945 (18) | 0.57030 (12) | 0.0533 (6) | |
H14A | 0.254154 | 0.159524 | 0.577245 | 0.064* | |
H14B | 0.242542 | 0.270754 | 0.581473 | 0.064* | |
C15 | 0.4184 (2) | 0.22394 (16) | 0.61395 (11) | 0.0483 (5) | |
C16 | 0.4407 (3) | 0.1853 (2) | 0.67643 (14) | 0.0745 (8) | |
H16 | 0.380736 | 0.148684 | 0.690264 | 0.089* | |
C17 | 0.5513 (4) | 0.2014 (2) | 0.71726 (15) | 0.0862 (10) | |
H17 | 0.566055 | 0.177606 | 0.759679 | 0.103* | |
C18 | 0.6403 (3) | 0.2525 (2) | 0.69580 (14) | 0.0745 (8) | |
H18 | 0.715941 | 0.264454 | 0.723235 | 0.089* | |
C19 | 0.6153 (2) | 0.28600 (17) | 0.63235 (12) | 0.0547 (6) | |
H19 | 0.676346 | 0.319342 | 0.617004 | 0.066* | |
C20 | 0.12727 (19) | 0.60798 (17) | 0.46077 (13) | 0.0498 (6) | |
C21 | 0.0938 (3) | 0.5948 (2) | 0.39413 (16) | 0.0781 (9) | |
H21 | 0.107269 | 0.537008 | 0.374917 | 0.094* | |
C22 | 0.0387 (3) | 0.6716 (3) | 0.35649 (17) | 0.0961 (11) | |
H22 | 0.015022 | 0.665350 | 0.311394 | 0.115* | |
C23 | 0.0197 (3) | 0.7557 (3) | 0.38580 (18) | 0.0823 (9) | |
H23 | −0.015860 | 0.806694 | 0.360328 | 0.099* | |
C24 | 0.0517 (2) | 0.7659 (2) | 0.45095 (16) | 0.0666 (7) | |
H24 | 0.037170 | 0.823442 | 0.470146 | 0.080* | |
C25 | 0.1055 (2) | 0.69226 (18) | 0.48930 (13) | 0.0542 (6) | |
H25 | 0.127015 | 0.699478 | 0.534406 | 0.065* | |
C26 | 0.2811 (2) | 0.52682 (18) | 0.65765 (12) | 0.0525 (6) | |
C27 | 0.1883 (3) | 0.5652 (3) | 0.68230 (14) | 0.0779 (9) | |
H27 | 0.146906 | 0.618973 | 0.663102 | 0.094* | |
C28 | 0.1551 (3) | 0.5236 (3) | 0.73673 (18) | 0.0994 (12) | |
H28 | 0.091764 | 0.550122 | 0.754124 | 0.119* | |
C29 | 0.2138 (3) | 0.4452 (3) | 0.76453 (16) | 0.0886 (10) | |
H29 | 0.189393 | 0.416782 | 0.800109 | 0.106* | |
C30 | 0.3079 (4) | 0.4082 (3) | 0.74065 (15) | 0.0919 (10) | |
H30 | 0.349492 | 0.354840 | 0.760373 | 0.110* | |
C31 | 0.3433 (3) | 0.4494 (2) | 0.68640 (14) | 0.0753 (8) | |
H31 | 0.408722 | 0.424079 | 0.670108 | 0.090* | |
C13 | 0.6111 (3) | 0.19539 (19) | 0.41839 (16) | 0.0744 (9) | |
H13A | 0.658363 | 0.253232 | 0.425217 | 0.112* | |
H13B | 0.662515 | 0.142525 | 0.435762 | 0.112* | |
H13C | 0.580964 | 0.186056 | 0.372434 | 0.112* | |
Co1 | 0.44779 (2) | 0.32945 (2) | 0.49815 (2) | 0.03338 (9) | |
N2 | 0.30141 (15) | 0.22768 (12) | 0.50031 (9) | 0.0408 (4) | |
N1 | 0.33089 (16) | 0.36040 (13) | 0.40709 (8) | 0.0433 (4) | |
N3 | 0.50598 (16) | 0.27211 (12) | 0.59210 (8) | 0.0406 (4) | |
O1 | 0.50858 (13) | 0.20190 (10) | 0.45100 (8) | 0.0465 (4) | |
O2 | 0.36102 (14) | 0.43145 (10) | 0.54328 (7) | 0.0458 (4) | |
O3 | 0.31921 (16) | 0.57554 (11) | 0.60600 (8) | 0.0574 (4) | |
O4 | 0.18284 (14) | 0.52997 (12) | 0.49748 (9) | 0.0621 (5) | |
O5 | 0.60611 (13) | 0.39833 (10) | 0.49462 (7) | 0.0449 (3) | |
P1 | 0.32259 (5) | 0.53220 (4) | 0.53636 (3) | 0.03897 (13) | |
Cl1 | 0.12621 (6) | 0.92882 (6) | 0.64285 (4) | 0.0721 (2) | |
O6 | 0.2361 (8) | 0.9806 (7) | 0.6500 (6) | 0.127 (4) | 0.510 (8) |
O7 | 0.0505 (7) | 0.9651 (8) | 0.6776 (5) | 0.149 (4) | 0.510 (8) |
O8 | 0.0811 (8) | 0.9414 (9) | 0.5736 (3) | 0.172 (4) | 0.510 (8) |
O9 | 0.1482 (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 | U11 | U22 | U33 | U12 | U13 | U23 |
C11 | 0.0615 (15) | 0.0406 (13) | 0.0583 (15) | 0.0084 (11) | 0.0015 (12) | −0.0064 (11) |
C10 | 0.084 (2) | 0.0349 (13) | 0.083 (2) | 0.0026 (13) | −0.0018 (16) | −0.0092 (13) |
C9 | 0.078 (2) | 0.0389 (14) | 0.100 (2) | −0.0171 (13) | −0.0025 (17) | 0.0005 (14) |
C8 | 0.0572 (15) | 0.0461 (14) | 0.086 (2) | −0.0107 (12) | 0.0116 (14) | 0.0048 (13) |
C7 | 0.0438 (12) | 0.0328 (10) | 0.0513 (13) | −0.0013 (9) | 0.0020 (10) | 0.0043 (10) |
C12 | 0.0447 (11) | 0.0318 (11) | 0.0448 (12) | 0.0015 (9) | 0.0001 (9) | 0.0006 (9) |
C6 | 0.0347 (11) | 0.0463 (13) | 0.0734 (17) | 0.0024 (10) | 0.0098 (11) | −0.0013 (12) |
C5 | 0.0454 (12) | 0.0451 (13) | 0.0497 (13) | 0.0138 (10) | 0.0017 (10) | −0.0091 (10) |
C4 | 0.0548 (15) | 0.079 (2) | 0.0689 (19) | 0.0162 (14) | −0.0123 (13) | −0.0220 (16) |
C3 | 0.096 (2) | 0.105 (3) | 0.0392 (15) | 0.036 (2) | −0.0097 (15) | −0.0065 (16) |
C2 | 0.085 (2) | 0.097 (2) | 0.0419 (15) | 0.0308 (18) | 0.0121 (14) | 0.0106 (14) |
C1 | 0.0635 (15) | 0.0715 (17) | 0.0435 (14) | 0.0142 (13) | 0.0121 (11) | 0.0105 (12) |
C14 | 0.0537 (14) | 0.0536 (14) | 0.0590 (15) | −0.0044 (11) | 0.0264 (12) | 0.0054 (11) |
C15 | 0.0610 (14) | 0.0425 (12) | 0.0452 (13) | 0.0089 (11) | 0.0196 (11) | 0.0084 (10) |
C16 | 0.088 (2) | 0.079 (2) | 0.0620 (18) | 0.0111 (16) | 0.0290 (16) | 0.0270 (15) |
C17 | 0.113 (3) | 0.096 (2) | 0.0491 (17) | 0.025 (2) | 0.0133 (18) | 0.0254 (16) |
C18 | 0.084 (2) | 0.075 (2) | 0.0531 (16) | 0.0167 (16) | −0.0131 (15) | 0.0027 (14) |
C19 | 0.0621 (15) | 0.0454 (13) | 0.0522 (14) | 0.0038 (11) | 0.0011 (12) | 0.0021 (11) |
C20 | 0.0310 (11) | 0.0493 (13) | 0.0676 (16) | 0.0016 (9) | 0.0065 (10) | 0.0047 (12) |
C21 | 0.0644 (17) | 0.079 (2) | 0.085 (2) | −0.0005 (15) | −0.0004 (16) | −0.0276 (17) |
C22 | 0.079 (2) | 0.133 (3) | 0.0617 (19) | 0.003 (2) | −0.0189 (16) | −0.003 (2) |
C23 | 0.0604 (18) | 0.092 (3) | 0.089 (2) | 0.0110 (16) | 0.0022 (16) | 0.028 (2) |
C24 | 0.0509 (15) | 0.0574 (16) | 0.092 (2) | 0.0108 (12) | 0.0157 (14) | 0.0101 (15) |
C25 | 0.0447 (13) | 0.0598 (16) | 0.0593 (15) | 0.0063 (11) | 0.0133 (11) | −0.0024 (12) |
C26 | 0.0566 (14) | 0.0576 (15) | 0.0480 (13) | −0.0123 (12) | 0.0220 (11) | −0.0164 (11) |
C27 | 0.0576 (16) | 0.115 (3) | 0.0654 (18) | 0.0150 (16) | 0.0232 (14) | −0.0008 (17) |
C28 | 0.066 (2) | 0.168 (4) | 0.074 (2) | 0.006 (2) | 0.0362 (17) | 0.000 (2) |
C29 | 0.093 (2) | 0.125 (3) | 0.0545 (18) | −0.025 (2) | 0.0298 (18) | −0.0048 (19) |
C30 | 0.136 (3) | 0.086 (2) | 0.0576 (19) | 0.006 (2) | 0.028 (2) | 0.0036 (16) |
C31 | 0.099 (2) | 0.0711 (19) | 0.0652 (18) | 0.0094 (17) | 0.0396 (17) | −0.0033 (15) |
C13 | 0.0705 (18) | 0.0567 (16) | 0.111 (2) | −0.0056 (13) | 0.0539 (18) | −0.0213 (16) |
Co1 | 0.03503 (15) | 0.03001 (14) | 0.03580 (15) | 0.00122 (11) | 0.00878 (10) | 0.00237 (11) |
N2 | 0.0376 (9) | 0.0369 (9) | 0.0486 (10) | 0.0005 (7) | 0.0107 (8) | 0.0023 (8) |
N1 | 0.0448 (10) | 0.0475 (10) | 0.0368 (9) | 0.0078 (8) | 0.0063 (8) | 0.0013 (8) |
N3 | 0.0483 (10) | 0.0319 (9) | 0.0405 (10) | 0.0038 (8) | 0.0062 (8) | 0.0031 (7) |
O1 | 0.0431 (8) | 0.0369 (8) | 0.0631 (10) | −0.0008 (6) | 0.0196 (7) | −0.0097 (7) |
O2 | 0.0595 (9) | 0.0352 (8) | 0.0478 (9) | 0.0072 (7) | 0.0226 (7) | 0.0008 (6) |
O3 | 0.0756 (11) | 0.0427 (9) | 0.0630 (11) | −0.0059 (8) | 0.0362 (9) | −0.0118 (8) |
O4 | 0.0400 (9) | 0.0513 (10) | 0.0932 (14) | −0.0022 (7) | 0.0091 (9) | 0.0111 (9) |
O5 | 0.0389 (8) | 0.0408 (8) | 0.0574 (9) | −0.0006 (6) | 0.0157 (7) | 0.0072 (7) |
P1 | 0.0356 (3) | 0.0335 (3) | 0.0507 (3) | 0.0029 (2) | 0.0154 (2) | 0.0004 (2) |
Cl1 | 0.0614 (4) | 0.0847 (5) | 0.0731 (5) | 0.0003 (4) | 0.0204 (3) | −0.0265 (4) |
O6 | 0.123 (7) | 0.133 (7) | 0.144 (6) | −0.076 (6) | 0.073 (5) | −0.066 (5) |
O7 | 0.120 (5) | 0.183 (9) | 0.174 (9) | 0.003 (5) | 0.101 (6) | −0.077 (7) |
O8 | 0.173 (7) | 0.267 (11) | 0.069 (4) | −0.009 (8) | 0.008 (4) | −0.006 (6) |
O9 | 0.204 (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—C10 | 1.376 (4) | C21—C22 | 1.399 (5) |
C11—C12 | 1.390 (3) | C21—H21 | 0.9300 |
C11—H11 | 0.9300 | C22—C23 | 1.365 (5) |
C10—C9 | 1.370 (4) | C22—H22 | 0.9300 |
C10—H10 | 0.9300 | C23—C24 | 1.343 (4) |
C9—C8 | 1.385 (4) | C23—H23 | 0.9300 |
C9—H9 | 0.9300 | C24—C25 | 1.367 (4) |
C8—C7 | 1.382 (3) | C24—H24 | 0.9300 |
C8—H8 | 0.9300 | C25—H25 | 0.9300 |
C7—C12 | 1.385 (3) | C26—C27 | 1.350 (3) |
C7—N2 | 1.465 (3) | C26—C31 | 1.359 (4) |
C12—O1 | 1.372 (2) | C26—O3 | 1.411 (3) |
C6—N2 | 1.489 (3) | C27—C28 | 1.392 (4) |
C6—C5 | 1.501 (3) | C27—H27 | 0.9300 |
C6—H6A | 0.9700 | C28—C29 | 1.348 (5) |
C6—H6B | 0.9700 | C28—H28 | 0.9300 |
C5—N1 | 1.336 (3) | C29—C30 | 1.345 (5) |
C5—C4 | 1.396 (3) | C29—H29 | 0.9300 |
C4—C3 | 1.378 (4) | C30—C31 | 1.397 (4) |
C4—H4 | 0.9300 | C30—H30 | 0.9300 |
C3—C2 | 1.355 (5) | C31—H31 | 0.9300 |
C3—H3 | 0.9300 | C13—O1 | 1.439 (3) |
C2—C1 | 1.368 (4) | C13—H13A | 0.9600 |
C2—H2 | 0.9300 | C13—H13B | 0.9600 |
C1—N1 | 1.341 (3) | C13—H13C | 0.9600 |
C1—H1 | 0.9300 | Co1—O5 | 2.0147 (14) |
C14—N2 | 1.487 (3) | Co1—O2 | 2.0545 (14) |
C14—C15 | 1.498 (3) | Co1—N3 | 2.0991 (17) |
C14—H14A | 0.9700 | Co1—N1 | 2.1194 (17) |
C14—H14B | 0.9700 | Co1—N2 | 2.1661 (17) |
C15—N3 | 1.335 (3) | Co1—O1 | 2.2111 (14) |
C15—C16 | 1.389 (3) | O2—P1 | 1.4745 (15) |
C16—C17 | 1.362 (4) | O3—P1 | 1.5841 (16) |
C16—H16 | 0.9300 | O4—P1 | 1.5958 (17) |
C17—C18 | 1.364 (4) | O5—P1i | 1.4818 (14) |
C17—H17 | 0.9300 | Cl1—O7 | 1.317 (5) |
C18—C19 | 1.381 (4) | Cl1—O8' | 1.326 (5) |
C18—H18 | 0.9300 | Cl1—O7' | 1.355 (7) |
C19—N3 | 1.341 (3) | Cl1—O6' | 1.355 (8) |
C19—H19 | 0.9300 | Cl1—O9 | 1.390 (6) |
C20—C25 | 1.367 (3) | Cl1—O6 | 1.398 (7) |
C20—C21 | 1.379 (4) | Cl1—O9' | 1.440 (6) |
C20—O4 | 1.405 (3) | Cl1—O8 | 1.443 (6) |
| | | |
C10—C11—C12 | 118.9 (2) | C24—C25—H25 | 120.3 |
C10—C11—H11 | 120.5 | C27—C26—C31 | 120.4 (3) |
C12—C11—H11 | 120.5 | C27—C26—O3 | 117.7 (3) |
C9—C10—C11 | 121.2 (2) | C31—C26—O3 | 121.5 (2) |
C9—C10—H10 | 119.4 | C26—C27—C28 | 119.3 (3) |
C11—C10—H10 | 119.4 | C26—C27—H27 | 120.3 |
C10—C9—C8 | 119.8 (2) | C28—C27—H27 | 120.3 |
C10—C9—H9 | 120.1 | C29—C28—C27 | 120.8 (3) |
C8—C9—H9 | 120.1 | C29—C28—H28 | 119.6 |
C7—C8—C9 | 120.1 (3) | C27—C28—H28 | 119.6 |
C7—C8—H8 | 119.9 | C30—C29—C28 | 119.8 (3) |
C9—C8—H8 | 119.9 | C30—C29—H29 | 120.1 |
C8—C7—C12 | 119.4 (2) | C28—C29—H29 | 120.1 |
C8—C7—N2 | 121.0 (2) | C29—C30—C31 | 120.3 (3) |
C12—C7—N2 | 119.52 (18) | C29—C30—H30 | 119.8 |
O1—C12—C7 | 116.45 (18) | C31—C30—H30 | 119.8 |
O1—C12—C11 | 123.0 (2) | C26—C31—C30 | 119.3 (3) |
C7—C12—C11 | 120.6 (2) | C26—C31—H31 | 120.3 |
N2—C6—C5 | 110.60 (17) | C30—C31—H31 | 120.3 |
N2—C6—H6A | 109.5 | O1—C13—H13A | 109.5 |
C5—C6—H6A | 109.5 | O1—C13—H13B | 109.5 |
N2—C6—H6B | 109.5 | H13A—C13—H13B | 109.5 |
C5—C6—H6B | 109.5 | O1—C13—H13C | 109.5 |
H6A—C6—H6B | 108.1 | H13A—C13—H13C | 109.5 |
N1—C5—C4 | 120.9 (2) | H13B—C13—H13C | 109.5 |
N1—C5—C6 | 116.39 (19) | O5—Co1—O2 | 99.94 (6) |
C4—C5—C6 | 122.6 (2) | O5—Co1—N3 | 96.45 (7) |
C3—C4—C5 | 118.4 (3) | O2—Co1—N3 | 85.50 (6) |
C3—C4—H4 | 120.8 | O5—Co1—N1 | 104.31 (7) |
C5—C4—H4 | 120.8 | O2—Co1—N1 | 90.70 (6) |
C2—C3—C4 | 120.4 (3) | N3—Co1—N1 | 159.24 (7) |
C2—C3—H3 | 119.8 | O5—Co1—N2 | 167.42 (6) |
C4—C3—H3 | 119.8 | O2—Co1—N2 | 91.67 (6) |
C3—C2—C1 | 118.3 (3) | N3—Co1—N2 | 79.52 (7) |
C3—C2—H2 | 120.8 | N1—Co1—N2 | 80.20 (7) |
C1—C2—H2 | 120.8 | O5—Co1—O1 | 91.56 (6) |
N1—C1—C2 | 122.8 (3) | O2—Co1—O1 | 168.47 (6) |
N1—C1—H1 | 118.6 | N3—Co1—O1 | 92.46 (6) |
C2—C1—H1 | 118.6 | N1—Co1—O1 | 87.21 (6) |
N2—C14—C15 | 111.41 (17) | N2—Co1—O1 | 76.81 (6) |
N2—C14—H14A | 109.3 | C7—N2—C14 | 112.11 (17) |
C15—C14—H14A | 109.3 | C7—N2—C6 | 110.06 (17) |
N2—C14—H14B | 109.3 | C14—N2—C6 | 113.03 (17) |
C15—C14—H14B | 109.3 | C7—N2—Co1 | 111.79 (12) |
H14A—C14—H14B | 108.0 | C14—N2—Co1 | 105.33 (13) |
N3—C15—C16 | 121.0 (2) | C6—N2—Co1 | 104.17 (12) |
N3—C15—C14 | 117.28 (19) | C5—N1—C1 | 119.0 (2) |
C16—C15—C14 | 121.6 (2) | C5—N1—Co1 | 112.90 (15) |
C17—C16—C15 | 119.5 (3) | C1—N1—Co1 | 127.91 (16) |
C17—C16—H16 | 120.3 | C15—N3—C19 | 119.0 (2) |
C15—C16—H16 | 120.3 | C15—N3—Co1 | 113.97 (15) |
C16—C17—C18 | 119.8 (3) | C19—N3—Co1 | 126.81 (16) |
C16—C17—H17 | 120.1 | C12—O1—C13 | 117.18 (17) |
C18—C17—H17 | 120.1 | C12—O1—Co1 | 115.36 (12) |
C17—C18—C19 | 118.4 (3) | C13—O1—Co1 | 126.99 (14) |
C17—C18—H18 | 120.8 | P1—O2—Co1 | 140.76 (9) |
C19—C18—H18 | 120.8 | C26—O3—P1 | 125.61 (14) |
N3—C19—C18 | 122.3 (3) | C20—O4—P1 | 122.38 (14) |
N3—C19—H19 | 118.9 | P1i—O5—Co1 | 150.98 (10) |
C18—C19—H19 | 118.9 | O2—P1—O5i | 120.31 (8) |
C25—C20—C21 | 121.4 (2) | O2—P1—O3 | 109.70 (9) |
C25—C20—O4 | 122.1 (2) | O5i—P1—O3 | 105.17 (9) |
C21—C20—O4 | 116.5 (2) | O2—P1—O4 | 105.19 (9) |
C20—C21—C22 | 117.6 (3) | O5i—P1—O4 | 109.70 (9) |
C20—C21—H21 | 121.2 | O3—P1—O4 | 106.01 (10) |
C22—C21—H21 | 121.2 | O8'—Cl1—O7' | 117.9 (6) |
C23—C22—C21 | 120.2 (3) | O8'—Cl1—O6' | 113.5 (5) |
C23—C22—H22 | 119.9 | O7'—Cl1—O6' | 113.7 (6) |
C21—C22—H22 | 119.9 | O7—Cl1—O9 | 116.7 (5) |
C24—C23—C22 | 120.9 (3) | O7—Cl1—O6 | 112.1 (5) |
C24—C23—H23 | 119.6 | O9—Cl1—O6 | 111.6 (5) |
C22—C23—H23 | 119.6 | O8'—Cl1—O9' | 108.7 (5) |
C23—C24—C25 | 120.6 (3) | O7'—Cl1—O9' | 101.6 (6) |
C23—C24—H24 | 119.7 | O6'—Cl1—O9' | 98.6 (6) |
C25—C24—H24 | 119.7 | O7—Cl1—O8 | 112.1 (6) |
C20—C25—C24 | 119.4 (3) | O9—Cl1—O8 | 103.3 (5) |
C20—C25—H25 | 120.3 | O6—Cl1—O8 | 99.3 (5) |
| | | |
C12—C11—C10—C9 | 0.1 (4) | C8—C7—N2—C14 | 61.7 (3) |
C11—C10—C9—C8 | −0.2 (4) | C12—C7—N2—C14 | −120.9 (2) |
C10—C9—C8—C7 | 0.2 (4) | C8—C7—N2—C6 | −65.0 (3) |
C9—C8—C7—C12 | 0.0 (4) | C12—C7—N2—C6 | 112.4 (2) |
C9—C8—C7—N2 | 177.3 (2) | C8—C7—N2—Co1 | 179.76 (19) |
C8—C7—C12—O1 | −179.9 (2) | C12—C7—N2—Co1 | −2.9 (2) |
N2—C7—C12—O1 | 2.7 (3) | C15—C14—N2—C7 | 84.5 (2) |
C8—C7—C12—C11 | −0.1 (3) | C15—C14—N2—C6 | −150.37 (19) |
N2—C7—C12—C11 | −177.5 (2) | C15—C14—N2—Co1 | −37.3 (2) |
C10—C11—C12—O1 | 179.8 (2) | C5—C6—N2—C7 | −78.1 (2) |
C10—C11—C12—C7 | 0.1 (3) | C5—C6—N2—C14 | 155.68 (19) |
N2—C6—C5—N1 | −38.4 (3) | C5—C6—N2—Co1 | 41.9 (2) |
N2—C6—C5—C4 | 145.8 (2) | C4—C5—N1—C1 | 3.5 (3) |
N1—C5—C4—C3 | −4.0 (4) | C6—C5—N1—C1 | −172.4 (2) |
C6—C5—C4—C3 | 171.6 (2) | C4—C5—N1—Co1 | −171.74 (18) |
C5—C4—C3—C2 | 1.0 (4) | C6—C5—N1—Co1 | 12.4 (2) |
C4—C3—C2—C1 | 2.3 (4) | C2—C1—N1—C5 | 0.0 (4) |
C3—C2—C1—N1 | −2.9 (4) | C2—C1—N1—Co1 | 174.42 (19) |
N2—C14—C15—N3 | 27.5 (3) | C16—C15—N3—C19 | −2.5 (3) |
N2—C14—C15—C16 | −156.7 (2) | C14—C15—N3—C19 | 173.3 (2) |
N3—C15—C16—C17 | 3.8 (4) | C16—C15—N3—Co1 | −177.11 (19) |
C14—C15—C16—C17 | −171.8 (3) | C14—C15—N3—Co1 | −1.3 (2) |
C15—C16—C17—C18 | −2.2 (5) | C18—C19—N3—C15 | −0.3 (3) |
C16—C17—C18—C19 | −0.5 (5) | C18—C19—N3—Co1 | 173.56 (19) |
C17—C18—C19—N3 | 1.8 (4) | C7—C12—O1—C13 | −173.9 (2) |
C25—C20—C21—C22 | 1.2 (4) | C11—C12—O1—C13 | 6.4 (3) |
O4—C20—C21—C22 | −179.7 (3) | C7—C12—O1—Co1 | −1.2 (2) |
C20—C21—C22—C23 | −0.1 (5) | C11—C12—O1—Co1 | 179.11 (17) |
C21—C22—C23—C24 | −0.9 (5) | C27—C26—O3—P1 | −123.1 (2) |
C22—C23—C24—C25 | 0.8 (5) | C31—C26—O3—P1 | 63.6 (3) |
C21—C20—C25—C24 | −1.4 (4) | C25—C20—O4—P1 | −66.4 (3) |
O4—C20—C25—C24 | 179.6 (2) | C21—C20—O4—P1 | 114.5 (2) |
C23—C24—C25—C20 | 0.4 (4) | Co1—O2—P1—O5i | −30.1 (2) |
C31—C26—C27—C28 | −1.3 (5) | Co1—O2—P1—O3 | −152.23 (14) |
O3—C26—C27—C28 | −174.7 (3) | Co1—O2—P1—O4 | 94.14 (17) |
C26—C27—C28—C29 | −0.6 (5) | C26—O3—P1—O2 | −37.1 (2) |
C27—C28—C29—C30 | 1.9 (6) | C26—O3—P1—O5i | −167.80 (19) |
C28—C29—C30—C31 | −1.3 (6) | C26—O3—P1—O4 | 76.0 (2) |
C27—C26—C31—C30 | 1.8 (5) | C20—O4—P1—O2 | −156.18 (18) |
O3—C26—C31—C30 | 175.0 (3) | C20—O4—P1—O5i | −25.4 (2) |
C29—C30—C31—C26 | −0.5 (5) | C20—O4—P1—O3 | 87.6 (2) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O6ii | 0.93 | 2.52 | 3.349 (11) | 148 |
C2—H2···O6′ii | 0.93 | 2.53 | 3.395 (11) | 155 |
C31—H31···O2 | 0.93 | 2.60 | 3.046 (3) | 110 |
C13—H13A···O3i | 0.96 | 2.51 | 3.367 (3) | 148 |
C13—H13A···O5 | 0.96 | 2.63 | 3.268 (3) | 124 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+3/2, z−1/2. |
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)2 | F(000) = 1508 |
Mr = 1467.88 | Dx = 1.478 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 13.0021 (2) Å | Cell parameters from 7902 reflections |
b = 12.8075 (3) Å | θ = 2.4–23.9° |
c = 19.8373 (4) Å | µ = 0.71 mm−1 |
β = 93.008 (1)° | T = 296 K |
V = 3298.84 (11) Å3 | Square, pink |
Z = 2 | 0.25 × 0.20 × 0.16 mm |
Data collection top
Bruker Kappa APEXII CCD diffractometer | 4391 reflections with I > 2σ(I) |
Radiation source: Sealed tube | Rint = 0.023 |
ω and φ scan | θmax = 24.2°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | h = −14→14 |
Tmin = 0.654, Tmax = 0.745 | k = −14→14 |
19894 measured reflections | l = −22→22 |
5273 independent reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H-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 reflections | Δρmax = 0.42 e Å−3 |
433 parameters | Δρmin = −0.50 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C1 | 0.6627 (3) | 1.0353 (4) | −0.0386 (2) | 0.0693 (11) | |
H1 | 0.683370 | 0.965811 | −0.039538 | 0.083* | |
C2 | 0.5752 (4) | 1.0661 (5) | −0.0767 (3) | 0.0977 (17) | |
H2 | 0.538118 | 1.017688 | −0.103134 | 0.117* | |
C3 | 0.5440 (4) | 1.1672 (5) | −0.0750 (3) | 0.1006 (17) | |
H3 | 0.485268 | 1.188428 | −0.100070 | 0.121* | |
C4 | 0.5992 (3) | 1.2373 (4) | −0.0363 (2) | 0.0742 (12) | |
H4 | 0.578804 | 1.306781 | −0.034697 | 0.089* | |
C5 | 0.6862 (3) | 1.2036 (3) | 0.00064 (17) | 0.0492 (9) | |
C6 | 0.7520 (3) | 1.2755 (3) | 0.04257 (17) | 0.0523 (9) | |
H6A | 0.805611 | 1.303731 | 0.015666 | 0.063* | |
H6B | 0.710629 | 1.333350 | 0.057476 | 0.063* | |
C7 | 0.8948 (3) | 1.2719 (3) | 0.12945 (19) | 0.0527 (9) | |
H7A | 0.877108 | 1.329747 | 0.158236 | 0.063* | |
H7B | 0.932738 | 1.299579 | 0.092617 | 0.063* | |
C8 | 0.9608 (2) | 1.1958 (3) | 0.16922 (17) | 0.0472 (8) | |
C9 | 1.0244 (3) | 1.2248 (4) | 0.2250 (2) | 0.0678 (12) | |
H9 | 1.024567 | 1.293201 | 0.240755 | 0.081* | |
C10 | 1.0861 (3) | 1.1513 (5) | 0.2562 (2) | 0.0766 (13) | |
H10 | 1.128705 | 1.169339 | 0.293517 | 0.092* | |
C11 | 1.0853 (3) | 1.0518 (4) | 0.2328 (2) | 0.0704 (12) | |
H11 | 1.127383 | 1.001091 | 0.253370 | 0.084* | |
C12 | 1.0210 (3) | 1.0279 (3) | 0.17814 (18) | 0.0597 (10) | |
H12 | 1.019833 | 0.959412 | 0.162487 | 0.072* | |
C13 | 0.7246 (3) | 0.9234 (3) | 0.15816 (18) | 0.0504 (9) | |
H13 | 0.755101 | 0.868269 | 0.136103 | 0.061* | |
C14 | 0.6579 (3) | 0.9006 (3) | 0.20973 (19) | 0.0573 (10) | |
H14 | 0.646733 | 0.831739 | 0.222349 | 0.069* | |
C15 | 0.6103 (3) | 0.9794 (3) | 0.24076 (19) | 0.0562 (10) | |
H15 | 0.564900 | 0.965123 | 0.274282 | 0.067* | |
C16 | 0.6294 (2) | 1.0828 (3) | 0.22229 (16) | 0.0443 (8) | |
C17 | 0.5859 (3) | 1.1710 (3) | 0.25351 (19) | 0.0613 (10) | |
H17 | 0.538142 | 1.160772 | 0.286164 | 0.074* | |
C18 | 0.6125 (3) | 1.2700 (3) | 0.2368 (2) | 0.0661 (11) | |
H18 | 0.583684 | 1.326604 | 0.258325 | 0.079* | |
C19 | 0.6835 (3) | 1.2867 (3) | 0.18697 (19) | 0.0565 (9) | |
H19 | 0.701645 | 1.354634 | 0.175985 | 0.068* | |
C20 | 0.7263 (2) | 1.2047 (2) | 0.15434 (15) | 0.0389 (7) | |
C21 | 0.7003 (2) | 1.1005 (2) | 0.17176 (15) | 0.0377 (7) | |
C22 | 1.0283 (3) | 0.6881 (3) | 0.09565 (16) | 0.0440 (8) | |
C23 | 1.1241 (3) | 0.7142 (3) | 0.12233 (19) | 0.0636 (10) | |
H23 | 1.140557 | 0.783412 | 0.132162 | 0.076* | |
C24 | 1.1959 (4) | 0.6361 (4) | 0.1344 (2) | 0.0830 (14) | |
H24 | 1.261383 | 0.652973 | 0.152229 | 0.100* | |
C25 | 1.1715 (4) | 0.5339 (4) | 0.1203 (3) | 0.0835 (14) | |
H25 | 1.220049 | 0.481486 | 0.128816 | 0.100* | |
C26 | 1.0766 (4) | 0.5100 (3) | 0.0941 (3) | 0.0820 (13) | |
H26 | 1.060117 | 0.440820 | 0.084185 | 0.098* | |
C27 | 1.0030 (3) | 0.5874 (3) | 0.0815 (2) | 0.0620 (10) | |
H27 | 0.937498 | 0.570314 | 0.063750 | 0.074* | |
C28 | 0.7975 (2) | 0.7505 (3) | −0.05410 (17) | 0.0432 (8) | |
C29 | 0.7412 (3) | 0.6885 (3) | −0.0144 (2) | 0.0671 (11) | |
H29 | 0.770147 | 0.660709 | 0.025558 | 0.080* | |
C30 | 0.6399 (3) | 0.6677 (4) | −0.0346 (3) | 0.0913 (16) | |
H30 | 0.600492 | 0.624883 | −0.008222 | 0.110* | |
C31 | 0.5970 (3) | 0.7093 (4) | −0.0928 (3) | 0.0867 (15) | |
H31 | 0.528987 | 0.694288 | −0.106031 | 0.104* | |
C32 | 0.6535 (3) | 0.7726 (4) | −0.1313 (2) | 0.0776 (13) | |
H32 | 0.623841 | 0.801840 | −0.170612 | 0.093* | |
C33 | 0.7557 (3) | 0.7937 (3) | −0.11216 (18) | 0.0607 (10) | |
H33 | 0.795044 | 0.836700 | −0.138483 | 0.073* | |
Cl1 | 0.65199 (8) | 0.56711 (8) | 0.15434 (6) | 0.0669 (3) | |
Co1 | 0.84769 (3) | 1.06875 (3) | 0.06506 (2) | 0.03324 (14) | |
N1 | 0.7177 (2) | 1.1036 (2) | −0.00074 (14) | 0.0461 (7) | |
N2 | 0.79944 (19) | 1.22094 (19) | 0.10202 (13) | 0.0386 (6) | |
N3 | 0.9599 (2) | 1.0980 (2) | 0.14607 (13) | 0.0443 (7) | |
N4 | 0.74576 (19) | 1.0191 (2) | 0.13985 (13) | 0.0397 (6) | |
O1 | 0.94517 (15) | 1.13453 (16) | −0.00421 (10) | 0.0407 (5) | |
O2 | 0.87291 (16) | 0.92070 (16) | 0.03622 (12) | 0.0460 (6) | |
O3 | 0.95296 (17) | 0.76609 (18) | 0.08654 (11) | 0.0493 (6) | |
O4 | 0.90328 (16) | 0.76707 (17) | −0.03819 (11) | 0.0454 (5) | |
O5 | 0.6551 (3) | 0.6763 (2) | 0.1479 (2) | 0.1269 (15) | |
O6 | 0.6495 (3) | 0.5389 (3) | 0.22227 (19) | 0.1047 (11) | |
O7 | 0.7437 (2) | 0.5270 (3) | 0.12750 (18) | 0.0903 (10) | |
O8 | 0.5650 (3) | 0.5283 (4) | 0.1202 (2) | 0.1341 (16) | |
P1 | 0.94875 (6) | 0.83950 (6) | 0.02126 (4) | 0.0353 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.065 (3) | 0.070 (3) | 0.071 (3) | 0.002 (2) | −0.013 (2) | −0.009 (2) |
C2 | 0.080 (3) | 0.103 (4) | 0.105 (4) | 0.000 (3) | −0.044 (3) | −0.018 (3) |
C3 | 0.072 (3) | 0.115 (5) | 0.110 (4) | 0.017 (3) | −0.034 (3) | 0.014 (4) |
C4 | 0.061 (3) | 0.076 (3) | 0.085 (3) | 0.019 (2) | −0.002 (2) | 0.016 (3) |
C5 | 0.0446 (19) | 0.053 (2) | 0.051 (2) | 0.0137 (17) | 0.0130 (16) | 0.0105 (17) |
C6 | 0.068 (2) | 0.0379 (19) | 0.052 (2) | 0.0162 (17) | 0.0154 (18) | 0.0070 (16) |
C7 | 0.050 (2) | 0.041 (2) | 0.069 (2) | −0.0062 (16) | 0.0214 (18) | −0.0201 (18) |
C8 | 0.0417 (18) | 0.057 (2) | 0.0445 (19) | −0.0095 (17) | 0.0168 (15) | −0.0138 (17) |
C9 | 0.061 (2) | 0.088 (3) | 0.056 (2) | −0.012 (2) | 0.013 (2) | −0.029 (2) |
C10 | 0.060 (3) | 0.124 (4) | 0.045 (2) | −0.011 (3) | −0.0028 (19) | −0.006 (3) |
C11 | 0.067 (3) | 0.093 (4) | 0.050 (2) | −0.004 (2) | −0.007 (2) | 0.014 (2) |
C12 | 0.059 (2) | 0.070 (3) | 0.049 (2) | 0.001 (2) | −0.0057 (18) | 0.0110 (19) |
C13 | 0.058 (2) | 0.039 (2) | 0.055 (2) | −0.0050 (17) | 0.0112 (17) | −0.0036 (16) |
C14 | 0.069 (2) | 0.046 (2) | 0.058 (2) | −0.0192 (19) | 0.0158 (19) | 0.0033 (18) |
C15 | 0.053 (2) | 0.064 (3) | 0.052 (2) | −0.0194 (19) | 0.0172 (17) | −0.0025 (19) |
C16 | 0.0349 (17) | 0.059 (2) | 0.0389 (18) | −0.0046 (16) | 0.0053 (14) | −0.0063 (16) |
C17 | 0.046 (2) | 0.080 (3) | 0.060 (2) | 0.001 (2) | 0.0151 (18) | −0.003 (2) |
C18 | 0.059 (2) | 0.069 (3) | 0.072 (3) | 0.018 (2) | 0.018 (2) | −0.009 (2) |
C19 | 0.059 (2) | 0.048 (2) | 0.063 (2) | 0.0105 (18) | 0.0140 (19) | 0.0007 (18) |
C20 | 0.0373 (16) | 0.0377 (18) | 0.0426 (18) | 0.0061 (14) | 0.0092 (14) | −0.0032 (14) |
C21 | 0.0299 (15) | 0.0453 (19) | 0.0378 (17) | 0.0010 (14) | 0.0012 (13) | −0.0042 (14) |
C22 | 0.051 (2) | 0.046 (2) | 0.0352 (17) | 0.0035 (16) | 0.0087 (15) | 0.0069 (15) |
C23 | 0.078 (3) | 0.056 (2) | 0.055 (2) | −0.006 (2) | −0.011 (2) | 0.0066 (19) |
C24 | 0.068 (3) | 0.099 (4) | 0.078 (3) | 0.005 (3) | −0.028 (2) | 0.017 (3) |
C25 | 0.078 (3) | 0.073 (3) | 0.099 (4) | 0.023 (3) | −0.010 (3) | 0.018 (3) |
C26 | 0.085 (3) | 0.048 (2) | 0.112 (4) | 0.012 (2) | −0.004 (3) | 0.004 (2) |
C27 | 0.055 (2) | 0.046 (2) | 0.085 (3) | −0.0010 (18) | −0.002 (2) | 0.004 (2) |
C28 | 0.0378 (17) | 0.0425 (19) | 0.050 (2) | −0.0005 (15) | 0.0125 (15) | −0.0117 (15) |
C29 | 0.046 (2) | 0.077 (3) | 0.080 (3) | 0.001 (2) | 0.0123 (19) | 0.024 (2) |
C30 | 0.050 (3) | 0.103 (4) | 0.123 (4) | −0.014 (2) | 0.020 (3) | 0.024 (3) |
C31 | 0.045 (2) | 0.116 (4) | 0.098 (4) | −0.009 (3) | 0.000 (2) | −0.022 (3) |
C32 | 0.065 (3) | 0.113 (4) | 0.054 (2) | 0.008 (3) | −0.008 (2) | −0.013 (3) |
C33 | 0.062 (2) | 0.078 (3) | 0.043 (2) | −0.005 (2) | 0.0080 (18) | −0.002 (2) |
Cl1 | 0.0620 (6) | 0.0511 (6) | 0.0887 (8) | 0.0012 (5) | 0.0133 (5) | −0.0065 (5) |
Co1 | 0.0331 (2) | 0.0307 (2) | 0.0363 (2) | 0.00442 (17) | 0.00581 (17) | −0.00351 (18) |
N1 | 0.0395 (15) | 0.0517 (18) | 0.0469 (16) | 0.0043 (13) | 0.0004 (12) | −0.0041 (14) |
N2 | 0.0407 (14) | 0.0315 (14) | 0.0446 (15) | 0.0027 (11) | 0.0119 (12) | −0.0015 (12) |
N3 | 0.0418 (15) | 0.0546 (18) | 0.0369 (15) | −0.0026 (13) | 0.0064 (12) | −0.0009 (13) |
N4 | 0.0397 (14) | 0.0382 (15) | 0.0417 (15) | −0.0002 (12) | 0.0074 (12) | −0.0036 (12) |
O1 | 0.0405 (12) | 0.0396 (12) | 0.0426 (12) | −0.0007 (10) | 0.0091 (9) | 0.0025 (10) |
O2 | 0.0472 (13) | 0.0308 (11) | 0.0613 (14) | 0.0028 (10) | 0.0152 (11) | −0.0069 (10) |
O3 | 0.0548 (14) | 0.0476 (14) | 0.0474 (13) | 0.0084 (11) | 0.0198 (11) | 0.0109 (11) |
O4 | 0.0385 (12) | 0.0478 (13) | 0.0508 (13) | −0.0003 (10) | 0.0109 (10) | −0.0146 (11) |
O5 | 0.167 (4) | 0.0462 (19) | 0.171 (4) | 0.017 (2) | 0.036 (3) | −0.002 (2) |
O6 | 0.103 (3) | 0.114 (3) | 0.099 (3) | 0.017 (2) | 0.027 (2) | 0.017 (2) |
O7 | 0.082 (2) | 0.080 (2) | 0.113 (3) | 0.0142 (17) | 0.0446 (19) | 0.0039 (19) |
O8 | 0.086 (3) | 0.171 (4) | 0.144 (4) | −0.043 (3) | −0.008 (2) | −0.024 (3) |
P1 | 0.0391 (4) | 0.0291 (4) | 0.0387 (4) | 0.0020 (3) | 0.0118 (3) | −0.0011 (3) |
Geometric parameters (Å, º) top
C1—N1 | 1.336 (5) | C19—H19 | 0.9300 |
C1—C2 | 1.389 (6) | C20—C21 | 1.424 (4) |
C1—H1 | 0.9300 | C20—N2 | 1.459 (4) |
C2—C3 | 1.358 (7) | C21—N4 | 1.370 (4) |
C2—H2 | 0.9300 | C22—C27 | 1.358 (5) |
C3—C4 | 1.361 (7) | C22—C23 | 1.370 (5) |
C3—H3 | 0.9300 | C22—O3 | 1.403 (4) |
C4—C5 | 1.383 (5) | C23—C24 | 1.380 (6) |
C4—H4 | 0.9300 | C23—H23 | 0.9300 |
C5—N1 | 1.346 (4) | C24—C25 | 1.373 (7) |
C5—C6 | 1.482 (5) | C24—H24 | 0.9300 |
C6—N2 | 1.478 (4) | C25—C26 | 1.350 (6) |
C6—H6A | 0.9700 | C25—H25 | 0.9300 |
C6—H6B | 0.9700 | C26—C27 | 1.391 (6) |
C7—N2 | 1.479 (4) | C26—H26 | 0.9300 |
C7—C8 | 1.497 (5) | C27—H27 | 0.9300 |
C7—H7A | 0.9700 | C28—C29 | 1.359 (5) |
C7—H7B | 0.9700 | C28—C33 | 1.365 (5) |
C8—N3 | 1.334 (4) | C28—O4 | 1.411 (4) |
C8—C9 | 1.396 (5) | C29—C30 | 1.382 (6) |
C9—C10 | 1.364 (6) | C29—H29 | 0.9300 |
C9—H9 | 0.9300 | C30—C31 | 1.363 (7) |
C10—C11 | 1.356 (6) | C30—H30 | 0.9300 |
C10—H10 | 0.9300 | C31—C32 | 1.357 (7) |
C11—C12 | 1.368 (5) | C31—H31 | 0.9300 |
C11—H11 | 0.9300 | C32—C33 | 1.389 (6) |
C12—N3 | 1.338 (5) | C32—H32 | 0.9300 |
C12—H12 | 0.9300 | C33—H33 | 0.9300 |
C13—N4 | 1.311 (4) | Cl1—O8 | 1.380 (4) |
C13—C14 | 1.406 (5) | Cl1—O6 | 1.397 (4) |
C13—H13 | 0.9300 | Cl1—O5 | 1.405 (3) |
C14—C15 | 1.350 (5) | Cl1—O7 | 1.426 (3) |
C14—H14 | 0.9300 | Co1—O2 | 2.012 (2) |
C15—C16 | 1.399 (5) | Co1—O1 | 2.095 (2) |
C15—H15 | 0.9300 | Co1—N1 | 2.128 (3) |
C16—C21 | 1.415 (4) | Co1—N4 | 2.137 (2) |
C16—C17 | 1.420 (5) | Co1—N3 | 2.146 (3) |
C17—C18 | 1.361 (6) | Co1—N2 | 2.186 (2) |
C17—H17 | 0.9300 | O1—P1i | 1.475 (2) |
C18—C19 | 1.403 (5) | O2—P1 | 1.474 (2) |
C18—H18 | 0.9300 | O3—P1 | 1.599 (2) |
C19—C20 | 1.367 (5) | O4—P1 | 1.590 (2) |
| | | |
N1—C1—C2 | 121.3 (4) | C25—C24—H24 | 119.7 |
N1—C1—H1 | 119.4 | C23—C24—H24 | 119.7 |
C2—C1—H1 | 119.4 | C26—C25—C24 | 119.4 (4) |
C3—C2—C1 | 119.6 (5) | C26—C25—H25 | 120.3 |
C3—C2—H2 | 120.2 | C24—C25—H25 | 120.3 |
C1—C2—H2 | 120.2 | C25—C26—C27 | 121.0 (4) |
C2—C3—C4 | 119.6 (4) | C25—C26—H26 | 119.5 |
C2—C3—H3 | 120.2 | C27—C26—H26 | 119.5 |
C4—C3—H3 | 120.2 | C22—C27—C26 | 118.9 (4) |
C3—C4—C5 | 119.0 (4) | C22—C27—H27 | 120.5 |
C3—C4—H4 | 120.5 | C26—C27—H27 | 120.5 |
C5—C4—H4 | 120.5 | C29—C28—C33 | 121.6 (3) |
N1—C5—C4 | 121.8 (4) | C29—C28—O4 | 120.4 (3) |
N1—C5—C6 | 115.8 (3) | C33—C28—O4 | 117.9 (3) |
C4—C5—C6 | 122.3 (4) | C28—C29—C30 | 118.6 (4) |
N2—C6—C5 | 111.0 (3) | C28—C29—H29 | 120.7 |
N2—C6—H6A | 109.4 | C30—C29—H29 | 120.7 |
C5—C6—H6A | 109.4 | C31—C30—C29 | 120.7 (4) |
N2—C6—H6B | 109.4 | C31—C30—H30 | 119.6 |
C5—C6—H6B | 109.4 | C29—C30—H30 | 119.6 |
H6A—C6—H6B | 108.0 | C32—C31—C30 | 120.1 (4) |
N2—C7—C8 | 110.7 (3) | C32—C31—H31 | 119.9 |
N2—C7—H7A | 109.5 | C30—C31—H31 | 119.9 |
C8—C7—H7A | 109.5 | C31—C32—C33 | 120.0 (4) |
N2—C7—H7B | 109.5 | C31—C32—H32 | 120.0 |
C8—C7—H7B | 109.5 | C33—C32—H32 | 120.0 |
H7A—C7—H7B | 108.1 | C28—C33—C32 | 119.0 (4) |
N3—C8—C9 | 121.1 (4) | C28—C33—H33 | 120.5 |
N3—C8—C7 | 115.8 (3) | C32—C33—H33 | 120.5 |
C9—C8—C7 | 123.0 (3) | O8—Cl1—O6 | 108.7 (3) |
C10—C9—C8 | 119.0 (4) | O8—Cl1—O5 | 110.0 (3) |
C10—C9—H9 | 120.5 | O6—Cl1—O5 | 110.3 (3) |
C8—C9—H9 | 120.5 | O8—Cl1—O7 | 111.5 (3) |
C11—C10—C9 | 119.9 (4) | O6—Cl1—O7 | 109.2 (2) |
C11—C10—H10 | 120.0 | O5—Cl1—O7 | 107.2 (2) |
C9—C10—H10 | 120.0 | O2—Co1—O1 | 94.55 (9) |
C10—C11—C12 | 118.4 (4) | O2—Co1—N1 | 99.17 (10) |
C10—C11—H11 | 120.8 | O1—Co1—N1 | 90.10 (9) |
C12—C11—H11 | 120.8 | O2—Co1—N4 | 91.90 (9) |
N3—C12—C11 | 123.3 (4) | O1—Co1—N4 | 173.54 (9) |
N3—C12—H12 | 118.3 | N1—Co1—N4 | 89.24 (10) |
C11—C12—H12 | 118.3 | O2—Co1—N3 | 105.24 (10) |
N4—C13—C14 | 122.8 (3) | O1—Co1—N3 | 90.59 (9) |
N4—C13—H13 | 118.6 | N1—Co1—N3 | 155.45 (11) |
C14—C13—H13 | 118.6 | N4—Co1—N3 | 87.36 (10) |
C15—C14—C13 | 119.4 (3) | O2—Co1—N2 | 171.65 (9) |
C15—C14—H14 | 120.3 | O1—Co1—N2 | 93.18 (9) |
C13—C14—H14 | 120.3 | N1—Co1—N2 | 77.64 (10) |
C14—C15—C16 | 119.7 (3) | N4—Co1—N2 | 80.40 (9) |
C14—C15—H15 | 120.1 | N3—Co1—N2 | 77.82 (10) |
C16—C15—H15 | 120.1 | C1—N1—C5 | 118.7 (3) |
C15—C16—C21 | 118.0 (3) | C1—N1—Co1 | 126.3 (3) |
C15—C16—C17 | 123.9 (3) | C5—N1—Co1 | 114.8 (2) |
C21—C16—C17 | 118.1 (3) | C20—N2—C6 | 112.0 (2) |
C18—C17—C16 | 121.5 (3) | C20—N2—C7 | 111.5 (2) |
C18—C17—H17 | 119.2 | C6—N2—C7 | 113.0 (3) |
C16—C17—H17 | 119.2 | C20—N2—Co1 | 108.73 (18) |
C17—C18—C19 | 119.9 (4) | C6—N2—Co1 | 105.63 (19) |
C17—C18—H18 | 120.0 | C7—N2—Co1 | 105.51 (18) |
C19—C18—H18 | 120.0 | C8—N3—C12 | 118.1 (3) |
C20—C19—C18 | 121.0 (4) | C8—N3—Co1 | 114.6 (2) |
C20—C19—H19 | 119.5 | C12—N3—Co1 | 127.1 (3) |
C18—C19—H19 | 119.5 | C13—N4—C21 | 118.8 (3) |
C19—C20—C21 | 119.8 (3) | C13—N4—Co1 | 128.1 (2) |
C19—C20—N2 | 121.6 (3) | C21—N4—Co1 | 113.1 (2) |
C21—C20—N2 | 118.6 (3) | P1i—O1—Co1 | 147.81 (14) |
N4—C21—C16 | 121.2 (3) | P1—O2—Co1 | 147.43 (14) |
N4—C21—C20 | 119.2 (3) | C22—O3—P1 | 121.11 (19) |
C16—C21—C20 | 119.6 (3) | C28—O4—P1 | 125.02 (18) |
C27—C22—C23 | 121.1 (3) | O2—P1—O1i | 122.04 (13) |
C27—C22—O3 | 119.3 (3) | O2—P1—O4 | 109.53 (13) |
C23—C22—O3 | 119.4 (3) | O1i—P1—O4 | 106.09 (12) |
C22—C23—C24 | 118.9 (4) | O2—P1—O3 | 104.28 (12) |
C22—C23—H23 | 120.5 | O1i—P1—O3 | 109.00 (12) |
C24—C23—H23 | 120.5 | O4—P1—O3 | 104.67 (13) |
C25—C24—C23 | 120.6 (4) | | |
| | | |
N1—C1—C2—C3 | −0.7 (8) | O4—C28—C33—C32 | 175.6 (3) |
C1—C2—C3—C4 | 0.4 (9) | C31—C32—C33—C28 | −0.4 (7) |
C2—C3—C4—C5 | −0.1 (8) | C2—C1—N1—C5 | 0.7 (6) |
C3—C4—C5—N1 | 0.1 (6) | C2—C1—N1—Co1 | 176.0 (4) |
C3—C4—C5—C6 | 178.4 (4) | C4—C5—N1—C1 | −0.4 (5) |
N1—C5—C6—N2 | −32.9 (4) | C6—C5—N1—C1 | −178.8 (3) |
C4—C5—C6—N2 | 148.7 (3) | C4—C5—N1—Co1 | −176.2 (3) |
N2—C7—C8—N3 | 35.3 (4) | C6—C5—N1—Co1 | 5.4 (4) |
N2—C7—C8—C9 | −148.1 (3) | C19—C20—N2—C6 | −64.1 (4) |
N3—C8—C9—C10 | −0.1 (5) | C21—C20—N2—C6 | 116.5 (3) |
C7—C8—C9—C10 | −176.6 (3) | C19—C20—N2—C7 | 63.7 (4) |
C8—C9—C10—C11 | 0.1 (6) | C21—C20—N2—C7 | −115.7 (3) |
C9—C10—C11—C12 | −0.5 (6) | C19—C20—N2—Co1 | 179.6 (3) |
C10—C11—C12—N3 | 0.9 (6) | C21—C20—N2—Co1 | 0.2 (3) |
N4—C13—C14—C15 | 2.2 (6) | C5—C6—N2—C20 | −76.5 (3) |
C13—C14—C15—C16 | −1.3 (6) | C5—C6—N2—C7 | 156.5 (3) |
C14—C15—C16—C21 | −1.0 (5) | C5—C6—N2—Co1 | 41.7 (3) |
C14—C15—C16—C17 | −177.7 (4) | C8—C7—N2—C20 | 75.4 (3) |
C15—C16—C17—C18 | 175.5 (4) | C8—C7—N2—C6 | −157.4 (3) |
C21—C16—C17—C18 | −1.3 (5) | C8—C7—N2—Co1 | −42.4 (3) |
C16—C17—C18—C19 | 0.8 (6) | C9—C8—N3—C12 | 0.4 (5) |
C17—C18—C19—C20 | 0.4 (6) | C7—C8—N3—C12 | 177.2 (3) |
C18—C19—C20—C21 | −1.2 (5) | C9—C8—N3—Co1 | 175.3 (2) |
C18—C19—C20—N2 | 179.4 (3) | C7—C8—N3—Co1 | −8.0 (3) |
C15—C16—C21—N4 | 2.6 (5) | C11—C12—N3—C8 | −0.8 (5) |
C17—C16—C21—N4 | 179.6 (3) | C11—C12—N3—Co1 | −175.0 (3) |
C15—C16—C21—C20 | −176.4 (3) | C14—C13—N4—C21 | −0.6 (5) |
C17—C16—C21—C20 | 0.6 (5) | C14—C13—N4—Co1 | 178.1 (3) |
C19—C20—C21—N4 | −178.4 (3) | C16—C21—N4—C13 | −1.8 (4) |
N2—C20—C21—N4 | 1.1 (4) | C20—C21—N4—C13 | 177.2 (3) |
C19—C20—C21—C16 | 0.6 (5) | C16—C21—N4—Co1 | 179.2 (2) |
N2—C20—C21—C16 | −179.9 (3) | C20—C21—N4—Co1 | −1.8 (3) |
C27—C22—C23—C24 | 0.5 (6) | C27—C22—O3—P1 | −100.9 (3) |
O3—C22—C23—C24 | 176.6 (3) | C23—C22—O3—P1 | 82.9 (4) |
C22—C23—C24—C25 | −0.4 (7) | C29—C28—O4—P1 | −74.4 (4) |
C23—C24—C25—C26 | 0.4 (8) | C33—C28—O4—P1 | 109.1 (3) |
C24—C25—C26—C27 | −0.5 (8) | Co1—O2—P1—O1i | −21.0 (3) |
C23—C22—C27—C26 | −0.5 (6) | Co1—O2—P1—O4 | −145.7 (3) |
O3—C22—C27—C26 | −176.7 (4) | Co1—O2—P1—O3 | 102.8 (3) |
C25—C26—C27—C22 | 0.5 (7) | C28—O4—P1—O2 | −25.7 (3) |
C33—C28—C29—C30 | 1.3 (6) | C28—O4—P1—O1i | −159.2 (2) |
O4—C28—C29—C30 | −175.0 (4) | C28—O4—P1—O3 | 85.6 (3) |
C28—C29—C30—C31 | −0.7 (8) | C22—O3—P1—O2 | −170.4 (2) |
C29—C30—C31—C32 | −0.5 (8) | C22—O3—P1—O1i | −38.6 (3) |
C30—C31—C32—C33 | 1.1 (8) | C22—O3—P1—O4 | 74.6 (3) |
C29—C28—C33—C32 | −0.8 (6) | | |
Symmetry code: (i) −x+2, −y+2, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7B···O4i | 0.97 | 2.58 | 3.305 (4) | 131 |
C13—H13···O2 | 0.93 | 2.65 | 3.172 (4) | 116 |
C14—H14···O5 | 0.93 | 2.48 | 3.123 (5) | 126 |
C19—H19···Cl1ii | 0.93 | 2.82 | 3.668 (4) | 151 |
C19—H19···O6ii | 0.93 | 2.63 | 3.339 (5) | 133 |
C19—H19···O7ii | 0.93 | 2.48 | 3.402 (5) | 171 |
Symmetry codes: (i) −x+2, −y+2, −z; (ii) x, y+1, z. |