metal-organic compounds
κO)cobalt(II)
of dibromidobis(1,3-dibenzyl-1,3-diazinan-2-one-aDepartment Chemie, Universität Paderborn, Warburgerstrasse 100, 33098 Paderborn, Germany
*Correspondence e-mail: ulrich.floerke@upb.de, rene.wilhelm@upb.de
The 2(C18H20N2O)2], contains 1.5 formula units per with one molecule sitting on a general site and a second one halved by a crystallographic twofold rotation axis passing through the CoII cation. Both CoII atoms are coordinated in a distorted tetrahedral manner by two Br− ligands and two O atoms of the pyrimidinone (OPyr) groups. The Br—Co—Br coordination angles are similar [115.46 (4) and 115.20 (5)°], while the O—Co—O angles differ slightly more [102.26 (18) and 98.1 (2)°]. Similarly, the Co—Br bond lengths are almost identical [2.3721 (9), 2.3757 (10) and 2.3809 (10) Å], with a larger difference between the Co—O bond lengths [1.929 (4), 1.926 (4) and 1.955 (4) Å]. The three independent OPyr groups present envelope conformations, with three C and two N atoms lying in well defined planes with maximum deviations from the least-squares planes of 0.047, 0.031 and 0.036 Å, and the external-most C atoms protruding by 0.654 (6), 0.643 (7) and 0.656 (6) Å out of the planes. The dihedral angles between the planar fractions of the OPyr planes are 50.5 (1)° for the nonsymmetric molecule and 49.7 (1)° for the symmetric one. Non-covalent interactions are of the C—H⋯Br type and they are weak, hardly shorter than van der Waals radii, with an H⋯Br distance range of 3.00–3.04 Å. The intermolecular interactions define chains parallel to [101].
of the title complex, [CoBrKeywords: crystal structure; coordination compound; cobalt pyrimidinone complex; C—H⋯Br interactions.
CCDC reference: 1416578
1. Related literature
For cobalt complexes with urea-type ligands, see: Sone et al. (1984); Schafer & Curran (1966). For related MX2(OPyr)2 structures, see: Bobicz et al. (2002); Lundberg & Eriksson (2006).
2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: SMART (Bruker, 2002); cell SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.
Supporting information
CCDC reference: 1416578
https://doi.org/10.1107/S2056989015014577/bg2562sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015014577/bg2562Isup2.hkl
Cobalt powder (0.222 g, 3.772 mmol, 20 eq, grain size < 150 µm) and 1,3-dibenzyl-2-bromo-3,4,5,6-tetrahydropyrimidin-1-ium bromide (0.080 g, 0.187 mmol, 1 eq) were filled into a schlenk tube equipped with a stirring bar. Dimethylformamide (3 mL) was added and the mixture was stirred and heated at 120 °C for 16 h under
The cooled down mixture was filtrated and the solvent was removed under vacuum. The residue was mixed with toluene until there was a light blue solution which was filtrated and overlayed carefully with pentane. Blue needle-shaped crystals suitable for X-ray diffraction were obtained after three days.HR-ESI-MS [C36H40BrCoN4O2]+ [m/z]; calc.: 698.1667; found: 698.1673. IR(KBr) ν [cm-1] = 3437, 2924, 2387, 2285, 1595, 1548, 1454, 1436, 700.
Crystalline material was of very poor quality, so various attempts were made to collect a reasonably sufficient data set. The final one still suffered from problems to give high Rint, low ratio observed/unique reflections and a ratio data/parameters of only 8, but led to suitable
results.Hydrogen atom positions were derived from geometrical considerations and then refined at idealized positions riding on the carbon atoms with isotropic displacement parameters Uiso(H) = 1.2U(Ceq) and C–H 0.95-0.99 Å.
Although the present data set is only of mean quality (see
Section), this very rare example of a MX2(OPyr)2 structure (M = transition metal; X = halogen; OPyr = pyrimidinone ligand) can be characterized adequately. Both Co centres are coordinated in a distorted tetrahedral manner from each two Br ligands and two oxygen atoms of the pyrimidinone (OPyr) groups. The enclosed angles are Br–Co1–Br 115.46 (4)°, O–Co1–O 102.26 (19)°, Br–Co2–Br 115.20 (5)° and O–Co2–O 98.1 (2)°, as well. Co–Br bond lengths range from 2.3722 (9) to 2.3809 (10) Å, Co–O bond lengths from 1.926 (4) to 1.955 (4) Å, resp. The O–C bonds are equal with 1.253 (6) to 1.284 (6) Å and the Co–O–C angles differ strongly with 141.1 (4)° at O1 and 166.8 (4)° at O2 of molecule 1 and 152.7 (4)° at O3 of molecule 2. To date, only two other MX2(OPyr)2 structures are know: the N,N'-dimethyl nickel analogue (Bobicz et al., 2002) and the N,N'-dimethyl diiodo cadmium compound (Lundberg & Eriksson, 2006). Both show similar X–M–X angles of about 126°, but very different O–M–O angles of 105.83 (12)° (Ni) and 94.78 (16)° (Cd). Additionally, these structures show almost perpendicular orientation of their respectice OPyr planes, but for the two title compounds the resulting dihedral angles are 50.5 (1)° for molecule 1 and 49.7 (1)° for molecule 2. C3, C7 and C53 atoms have not been considered.The shortest intramolecular hydrogen bond interaction is C20—H20A···Br2 with H···Br 2.966 Å. Intermolecular interactions tightly shorter than van der Waals radii are C8–H8B···Br1(-x + 0.5, -y + 2.5, -z), C70–H70B···Br3(-x, y, -z + 0.5) and C54–H54A···Br2(x, y - 1, z), see Table. These link molecules into endless rows approximately elongated along [101], Figure 3.
Although the present data set is only of mean quality (see
Section), this very rare example of a MX2(OPyr)2 structure (M = transition metal; X = halogen; OPyr = pyrimidinone ligand) can be characterized adequately. Both Co centres are coordinated in a distorted tetrahedral manner from each two Br ligands and two oxygen atoms of the pyrimidinone (OPyr) groups. The enclosed angles are Br–Co1–Br 115.46 (4)°, O–Co1–O 102.26 (19)°, Br–Co2–Br 115.20 (5)° and O–Co2–O 98.1 (2)°, as well. Co–Br bond lengths range from 2.3722 (9) to 2.3809 (10) Å, Co–O bond lengths from 1.926 (4) to 1.955 (4) Å, resp. The O–C bonds are equal with 1.253 (6) to 1.284 (6) Å and the Co–O–C angles differ strongly with 141.1 (4)° at O1 and 166.8 (4)° at O2 of molecule 1 and 152.7 (4)° at O3 of molecule 2. To date, only two other MX2(OPyr)2 structures are know: the N,N'-dimethyl nickel analogue (Bobicz et al., 2002) and the N,N'-dimethyl diiodo cadmium compound (Lundberg & Eriksson, 2006). Both show similar X–M–X angles of about 126°, but very different O–M–O angles of 105.83 (12)° (Ni) and 94.78 (16)° (Cd). Additionally, these structures show almost perpendicular orientation of their respectice OPyr planes, but for the two title compounds the resulting dihedral angles are 50.5 (1)° for molecule 1 and 49.7 (1)° for molecule 2. C3, C7 and C53 atoms have not been considered.The shortest intramolecular hydrogen bond interaction is C20—H20A···Br2 with H···Br 2.966 Å. Intermolecular interactions tightly shorter than van der Waals radii are C8–H8B···Br1(-x + 0.5, -y + 2.5, -z), C70–H70B···Br3(-x, y, -z + 0.5) and C54–H54A···Br2(x, y - 1, z), see Table. These link molecules into endless rows approximately elongated along [101], Figure 3.
For related literature [on what subject?], see: Sone et al. (1984); Schafer & Curran (1966). For related MX2(OPyr)2 structures, see: Bobicz et al. (2002); Lundberg & Eriksson, 2006.
Cobalt powder (0.222 g, 3.772 mmol, 20 eq, grain size < 150 µm) and 1,3-dibenzyl-2-bromo-3,4,5,6-tetrahydropyrimidin-1-ium bromide (0.080 g, 0.187 mmol, 1 eq) were filled into a schlenk tube equipped with a stirring bar. Dimethylformamide (3 mL) was added and the mixture was stirred and heated at 120 °C for 16 h under
The cooled down mixture was filtrated and the solvent was removed under vacuum. The residue was mixed with toluene until there was a light blue solution which was filtrated and overlayed carefully with pentane. Blue needle-shaped crystals suitable for X-ray diffraction were obtained after three days.HR-ESI-MS [C36H40BrCoN4O2]+ [m/z]; calc.: 698.1667; found: 698.1673. IR(KBr) ν [cm-1] = 3437, 2924, 2387, 2285, 1595, 1548, 1454, 1436, 700.
detailsCrystalline material was of very poor quality, so various attempts were made to collect a reasonably sufficient data set. The final one still suffered from problems to give high Rint, low ratio observed/unique reflections and a ratio data/parameters of only 8, but led to suitable
results.Hydrogen atom positions were derived from geometrical considerations and then refined at idealized positions riding on the carbon atoms with isotropic displacement parameters Uiso(H) = 1.2U(Ceq) and C–H 0.95-0.99 Å.
Data collection: SMART (Bruker, 2002); cell
SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and local programs.Fig. 1. Molecular structure of molecule 1 of the title compound with anisotropic displacement ellipsoids drawn at the 50% probability level. | |
Fig. 2. Molecular structure of molecule 2 of the title compound with anisotropic displacement ellipsoids drawn at the 50% probability level. | |
Fig. 3. Crystal packing approximately viewed along b axis with intermolecular hydrogen bonds as dotted lines. H-atoms not involved are omitted. |
[CoBr2(C18H20N2O)2] | F(000) = 4764 |
Mr = 779.47 | Dx = 1.496 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 24.182 (7) Å | Cell parameters from 2887 reflections |
b = 10.744 (3) Å | θ = 3.0–20.9° |
c = 40.003 (11) Å | µ = 2.84 mm−1 |
β = 92.687 (9)° | T = 130 K |
V = 10382 (5) Å3 | Prism, blue |
Z = 12 | 0.47 × 0.16 × 0.11 mm |
Bruker SMART APEX diffractometer | 12393 independent reflections |
Radiation source: sealed tube | 4968 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.143 |
φ and ω scans | θmax = 27.9°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | h = −31→31 |
Tmin = 0.448, Tmax = 0.907 | k = −14→13 |
47347 measured reflections | l = −52→52 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.053 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 0.74 | w = 1/[σ2(Fo2) + (0.0282P)2] where P = (Fo2 + 2Fc2)/3 |
12393 reflections | (Δ/σ)max = 0.001 |
609 parameters | Δρmax = 0.74 e Å−3 |
0 restraints | Δρmin = −0.93 e Å−3 |
[CoBr2(C18H20N2O)2] | V = 10382 (5) Å3 |
Mr = 779.47 | Z = 12 |
Monoclinic, C2/c | Mo Kα radiation |
a = 24.182 (7) Å | µ = 2.84 mm−1 |
b = 10.744 (3) Å | T = 130 K |
c = 40.003 (11) Å | 0.47 × 0.16 × 0.11 mm |
β = 92.687 (9)° |
Bruker SMART APEX diffractometer | 12393 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | 4968 reflections with I > 2σ(I) |
Tmin = 0.448, Tmax = 0.907 | Rint = 0.143 |
47347 measured reflections |
R[F2 > 2σ(F2)] = 0.053 | 0 restraints |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 0.74 | Δρmax = 0.74 e Å−3 |
12393 reflections | Δρmin = −0.93 e Å−3 |
609 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
Co1 | 0.16145 (3) | 1.20093 (7) | 0.07902 (2) | 0.02788 (19) | |
Br1 | 0.23444 (2) | 1.30819 (5) | 0.10883 (2) | 0.03701 (16) | |
Br2 | 0.08817 (2) | 1.32827 (5) | 0.05696 (2) | 0.03692 (16) | |
O1 | 0.13393 (14) | 1.0661 (3) | 0.10652 (10) | 0.0376 (10) | |
O2 | 0.19345 (15) | 1.1117 (4) | 0.04292 (10) | 0.0537 (12) | |
N1 | 0.15492 (18) | 1.0075 (4) | 0.16022 (11) | 0.0347 (12) | |
N2 | 0.06457 (19) | 1.0539 (4) | 0.14287 (12) | 0.0380 (12) | |
N3 | 0.16914 (18) | 1.0201 (4) | −0.00641 (11) | 0.0369 (12) | |
N4 | 0.26004 (18) | 1.0732 (4) | 0.00709 (11) | 0.0334 (12) | |
C1 | 0.1179 (2) | 1.0447 (5) | 0.13583 (15) | 0.0309 (14) | |
C2 | 0.1386 (2) | 0.9630 (5) | 0.19308 (14) | 0.0425 (16) | |
H2A | 0.1439 | 1.0304 | 0.2098 | 0.051* | |
H2B | 0.1624 | 0.8921 | 0.2003 | 0.051* | |
C3 | 0.0799 (2) | 0.9234 (6) | 0.19150 (14) | 0.0467 (17) | |
H3A | 0.0677 | 0.9070 | 0.2144 | 0.056* | |
H3B | 0.0757 | 0.8457 | 0.1783 | 0.056* | |
C4 | 0.0448 (2) | 1.0237 (6) | 0.17544 (14) | 0.0488 (17) | |
H4A | 0.0059 | 0.9953 | 0.1731 | 0.059* | |
H4B | 0.0461 | 1.0989 | 0.1898 | 0.059* | |
C5 | 0.2076 (2) | 1.0702 (5) | 0.01531 (14) | 0.0337 (14) | |
C6 | 0.1846 (3) | 0.9579 (6) | −0.03707 (14) | 0.0571 (19) | |
H6A | 0.1809 | 1.0169 | −0.0560 | 0.069* | |
H6B | 0.1592 | 0.8872 | −0.0419 | 0.069* | |
C7 | 0.2421 (3) | 0.9118 (7) | −0.03374 (16) | 0.064 (2) | |
H7A | 0.2445 | 0.8432 | −0.0172 | 0.077* | |
H7B | 0.2533 | 0.8788 | −0.0555 | 0.077* | |
C8 | 0.2801 (2) | 1.0131 (6) | −0.02279 (14) | 0.0522 (18) | |
H8A | 0.3176 | 0.9788 | −0.0178 | 0.063* | |
H8B | 0.2826 | 1.0751 | −0.0410 | 0.063* | |
C10 | 0.2137 (2) | 0.9993 (5) | 0.15410 (13) | 0.0321 (14) | |
H10A | 0.2350 | 1.0424 | 0.1724 | 0.038* | |
H10B | 0.2208 | 1.0429 | 0.1329 | 0.038* | |
C11 | 0.2335 (2) | 0.8685 (5) | 0.15192 (13) | 0.0290 (13) | |
C12 | 0.2787 (2) | 0.8255 (5) | 0.17192 (13) | 0.0360 (15) | |
H12A | 0.2973 | 0.8803 | 0.1873 | 0.043* | |
C13 | 0.2961 (2) | 0.7043 (6) | 0.16929 (15) | 0.0448 (16) | |
H13A | 0.3275 | 0.6768 | 0.1824 | 0.054* | |
C14 | 0.2690 (2) | 0.6231 (5) | 0.14821 (15) | 0.0449 (16) | |
H14A | 0.2807 | 0.5388 | 0.1474 | 0.054* | |
C15 | 0.2245 (2) | 0.6628 (5) | 0.12787 (14) | 0.0422 (16) | |
H15A | 0.2063 | 0.6067 | 0.1126 | 0.051* | |
C16 | 0.2069 (2) | 0.7846 (5) | 0.12998 (13) | 0.0348 (14) | |
H16A | 0.1762 | 0.8118 | 0.1162 | 0.042* | |
C20 | 0.0230 (2) | 1.1003 (5) | 0.11813 (16) | 0.0505 (18) | |
H20A | 0.0415 | 1.1267 | 0.0977 | 0.061* | |
H20B | 0.0042 | 1.1738 | 0.1273 | 0.061* | |
C21 | −0.0201 (2) | 0.9995 (6) | 0.10897 (14) | 0.0357 (15) | |
C22 | −0.0051 (2) | 0.8939 (6) | 0.09253 (15) | 0.0432 (16) | |
H22A | 0.0317 | 0.8838 | 0.0858 | 0.052* | |
C23 | −0.0440 (3) | 0.8025 (6) | 0.08585 (15) | 0.0513 (17) | |
H23A | −0.0335 | 0.7276 | 0.0752 | 0.062* | |
C24 | −0.0969 (3) | 0.8183 (6) | 0.09425 (14) | 0.0461 (17) | |
H24A | −0.1236 | 0.7555 | 0.0890 | 0.055* | |
C25 | −0.1123 (2) | 0.9238 (6) | 0.11028 (14) | 0.0423 (16) | |
H25A | −0.1497 | 0.9344 | 0.1161 | 0.051* | |
C26 | −0.0737 (2) | 1.0156 (5) | 0.11811 (13) | 0.0351 (14) | |
H26A | −0.0841 | 1.0886 | 0.1296 | 0.042* | |
C30 | 0.1112 (2) | 1.0188 (5) | 0.00070 (14) | 0.0366 (15) | |
H30A | 0.0892 | 1.0439 | −0.0197 | 0.044* | |
H30B | 0.1046 | 1.0809 | 0.0184 | 0.044* | |
C31 | 0.0917 (2) | 0.8945 (5) | 0.01186 (13) | 0.0341 (14) | |
C32 | 0.0416 (2) | 0.8423 (5) | 0.00001 (14) | 0.0392 (16) | |
H32A | 0.0189 | 0.8875 | −0.0157 | 0.047* | |
C33 | 0.0242 (2) | 0.7273 (5) | 0.01045 (14) | 0.0414 (16) | |
H33A | −0.0099 | 0.6939 | 0.0018 | 0.050* | |
C34 | 0.0563 (2) | 0.6608 (5) | 0.03349 (15) | 0.0455 (16) | |
H34A | 0.0445 | 0.5815 | 0.0408 | 0.055* | |
C35 | 0.1050 (2) | 0.7093 (5) | 0.04562 (15) | 0.0428 (16) | |
H35A | 0.1271 | 0.6628 | 0.0614 | 0.051* | |
C36 | 0.1231 (2) | 0.8233 (5) | 0.03577 (14) | 0.0385 (15) | |
H36A | 0.1570 | 0.8552 | 0.0451 | 0.046* | |
C40 | 0.3025 (2) | 1.1271 (5) | 0.03009 (14) | 0.0391 (15) | |
H40A | 0.2844 | 1.1793 | 0.0468 | 0.047* | |
H40B | 0.3271 | 1.1813 | 0.0174 | 0.047* | |
C41 | 0.3368 (2) | 1.0275 (5) | 0.04802 (14) | 0.0305 (14) | |
C42 | 0.3118 (2) | 0.9505 (5) | 0.07092 (14) | 0.0413 (16) | |
H42A | 0.2741 | 0.9625 | 0.0759 | 0.050* | |
C43 | 0.3427 (3) | 0.8560 (5) | 0.08636 (14) | 0.0443 (16) | |
H43A | 0.3259 | 0.8022 | 0.1018 | 0.053* | |
C44 | 0.3967 (3) | 0.8397 (5) | 0.07969 (15) | 0.0451 (17) | |
H44A | 0.4173 | 0.7744 | 0.0903 | 0.054* | |
C45 | 0.4220 (2) | 0.9173 (6) | 0.05755 (15) | 0.0428 (16) | |
H45A | 0.4599 | 0.9067 | 0.0531 | 0.051* | |
C46 | 0.3910 (2) | 1.0110 (5) | 0.04198 (13) | 0.0345 (14) | |
H46A | 0.4081 | 1.0648 | 0.0267 | 0.041* | |
Co2 | 0.0000 | 0.23548 (9) | 0.2500 | 0.0269 (3) | |
Br3 | −0.07599 (2) | 0.11717 (5) | 0.22782 (2) | 0.03648 (16) | |
O3 | 0.02697 (15) | 0.3531 (3) | 0.21818 (10) | 0.0448 (11) | |
N5 | −0.00272 (18) | 0.4274 (4) | 0.16733 (11) | 0.0351 (12) | |
N6 | 0.09039 (18) | 0.3875 (4) | 0.17940 (11) | 0.0329 (11) | |
C51 | 0.0384 (2) | 0.3867 (5) | 0.18848 (15) | 0.0334 (14) | |
C52 | 0.0093 (2) | 0.4792 (5) | 0.13441 (13) | 0.0432 (16) | |
H52A | −0.0188 | 0.5428 | 0.1279 | 0.052* | |
H52B | 0.0074 | 0.4123 | 0.1174 | 0.052* | |
C53 | 0.0653 (3) | 0.5366 (6) | 0.13563 (15) | 0.0517 (18) | |
H53A | 0.0660 | 0.6099 | 0.1506 | 0.062* | |
H53B | 0.0744 | 0.5649 | 0.1130 | 0.062* | |
C54 | 0.1071 (3) | 0.4437 (7) | 0.14817 (14) | 0.059 (2) | |
H54A | 0.1111 | 0.3779 | 0.1311 | 0.070* | |
H54B | 0.1434 | 0.4850 | 0.1519 | 0.070* | |
C60 | −0.0591 (2) | 0.4325 (5) | 0.17713 (14) | 0.0381 (15) | |
H60A | −0.0623 | 0.3837 | 0.1979 | 0.046* | |
H60B | −0.0832 | 0.3930 | 0.1595 | 0.046* | |
C61 | −0.0791 (2) | 0.5618 (5) | 0.18288 (13) | 0.0314 (14) | |
C62 | −0.0484 (2) | 0.6419 (6) | 0.20404 (14) | 0.0431 (16) | |
H62A | −0.0155 | 0.6130 | 0.2153 | 0.052* | |
C63 | −0.0655 (2) | 0.7610 (6) | 0.20863 (15) | 0.0474 (17) | |
H63A | −0.0442 | 0.8144 | 0.2232 | 0.057* | |
C64 | −0.1130 (2) | 0.8054 (5) | 0.19258 (15) | 0.0442 (16) | |
H64A | −0.1242 | 0.8892 | 0.1957 | 0.053* | |
C65 | −0.1443 (2) | 0.7279 (6) | 0.17192 (15) | 0.0430 (16) | |
H65A | −0.1775 | 0.7573 | 0.1610 | 0.052* | |
C66 | −0.1271 (2) | 0.6078 (5) | 0.16719 (13) | 0.0365 (15) | |
H66A | −0.1488 | 0.5547 | 0.1528 | 0.044* | |
C70 | 0.1342 (2) | 0.3297 (5) | 0.20009 (16) | 0.0470 (17) | |
H70A | 0.1550 | 0.2713 | 0.1862 | 0.056* | |
H70B | 0.1175 | 0.2808 | 0.2180 | 0.056* | |
C71 | 0.1742 (2) | 0.4233 (5) | 0.21587 (13) | 0.0327 (14) | |
C72 | 0.1546 (3) | 0.5266 (6) | 0.23188 (14) | 0.0469 (17) | |
H72A | 0.1158 | 0.5395 | 0.2327 | 0.056* | |
C73 | 0.1910 (3) | 0.6120 (6) | 0.24678 (15) | 0.0546 (19) | |
H73A | 0.1773 | 0.6842 | 0.2573 | 0.066* | |
C74 | 0.2466 (3) | 0.5917 (6) | 0.24624 (14) | 0.0495 (18) | |
H74A | 0.2715 | 0.6502 | 0.2565 | 0.059* | |
C75 | 0.2672 (2) | 0.4868 (6) | 0.23089 (14) | 0.0433 (16) | |
H75A | 0.3059 | 0.4722 | 0.2309 | 0.052* | |
C76 | 0.2305 (2) | 0.4038 (5) | 0.21561 (13) | 0.0357 (14) | |
H76A | 0.2442 | 0.3323 | 0.2048 | 0.043* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Co1 | 0.0283 (4) | 0.0333 (5) | 0.0216 (4) | −0.0008 (4) | −0.0037 (3) | 0.0007 (4) |
Br1 | 0.0366 (4) | 0.0414 (4) | 0.0319 (3) | −0.0063 (3) | −0.0102 (3) | −0.0002 (3) |
Br2 | 0.0362 (4) | 0.0448 (4) | 0.0290 (3) | 0.0082 (3) | −0.0059 (3) | 0.0052 (3) |
O1 | 0.034 (2) | 0.042 (3) | 0.036 (2) | −0.0061 (18) | −0.0001 (19) | 0.006 (2) |
O2 | 0.036 (3) | 0.080 (3) | 0.046 (3) | 0.010 (2) | 0.000 (2) | −0.031 (3) |
N1 | 0.033 (3) | 0.049 (3) | 0.021 (3) | −0.002 (2) | −0.002 (2) | 0.002 (2) |
N2 | 0.030 (3) | 0.044 (3) | 0.039 (3) | −0.005 (2) | 0.000 (2) | −0.003 (2) |
N3 | 0.025 (3) | 0.057 (3) | 0.029 (3) | −0.002 (2) | −0.004 (2) | −0.002 (3) |
N4 | 0.032 (3) | 0.045 (3) | 0.023 (3) | −0.002 (2) | 0.001 (2) | 0.000 (2) |
C1 | 0.027 (3) | 0.031 (3) | 0.034 (4) | 0.001 (3) | 0.000 (3) | −0.003 (3) |
C2 | 0.054 (4) | 0.046 (4) | 0.027 (4) | 0.004 (3) | 0.004 (3) | −0.002 (3) |
C3 | 0.067 (5) | 0.057 (5) | 0.016 (3) | −0.018 (4) | 0.011 (3) | −0.006 (3) |
C4 | 0.043 (4) | 0.073 (5) | 0.031 (4) | −0.004 (3) | 0.011 (3) | −0.020 (4) |
C5 | 0.040 (4) | 0.033 (4) | 0.028 (4) | 0.005 (3) | 0.000 (3) | 0.001 (3) |
C6 | 0.061 (5) | 0.088 (6) | 0.022 (4) | 0.001 (4) | −0.002 (3) | −0.013 (4) |
C7 | 0.078 (6) | 0.090 (6) | 0.026 (4) | 0.009 (5) | 0.017 (4) | −0.015 (4) |
C8 | 0.040 (4) | 0.088 (5) | 0.028 (4) | 0.004 (4) | 0.002 (3) | 0.010 (4) |
C10 | 0.026 (3) | 0.040 (4) | 0.030 (3) | −0.004 (3) | −0.005 (3) | 0.004 (3) |
C11 | 0.036 (3) | 0.027 (3) | 0.023 (3) | 0.001 (3) | −0.004 (3) | 0.005 (3) |
C12 | 0.040 (4) | 0.041 (4) | 0.027 (3) | −0.002 (3) | −0.005 (3) | 0.010 (3) |
C13 | 0.045 (4) | 0.049 (4) | 0.039 (4) | 0.013 (3) | −0.005 (3) | 0.013 (3) |
C14 | 0.059 (4) | 0.031 (4) | 0.045 (4) | 0.009 (3) | 0.006 (3) | 0.005 (3) |
C15 | 0.056 (4) | 0.042 (4) | 0.029 (4) | −0.006 (3) | 0.002 (3) | 0.000 (3) |
C16 | 0.038 (4) | 0.039 (4) | 0.028 (3) | 0.003 (3) | 0.000 (3) | 0.002 (3) |
C20 | 0.029 (4) | 0.047 (4) | 0.075 (5) | 0.003 (3) | −0.008 (3) | 0.013 (4) |
C21 | 0.028 (3) | 0.044 (4) | 0.035 (4) | 0.002 (3) | −0.004 (3) | 0.017 (3) |
C22 | 0.034 (4) | 0.053 (4) | 0.043 (4) | 0.003 (3) | 0.005 (3) | 0.003 (4) |
C23 | 0.057 (5) | 0.060 (5) | 0.037 (4) | 0.001 (4) | 0.006 (3) | −0.010 (3) |
C24 | 0.054 (4) | 0.056 (4) | 0.028 (3) | −0.015 (4) | −0.008 (3) | −0.007 (3) |
C25 | 0.037 (4) | 0.060 (4) | 0.030 (4) | −0.009 (3) | −0.002 (3) | 0.009 (3) |
C26 | 0.032 (4) | 0.046 (4) | 0.028 (3) | 0.002 (3) | 0.002 (3) | 0.006 (3) |
C30 | 0.032 (4) | 0.043 (4) | 0.034 (4) | −0.001 (3) | −0.008 (3) | 0.004 (3) |
C31 | 0.037 (4) | 0.035 (4) | 0.029 (3) | −0.001 (3) | −0.004 (3) | −0.010 (3) |
C32 | 0.040 (4) | 0.047 (4) | 0.030 (3) | 0.000 (3) | −0.006 (3) | −0.002 (3) |
C33 | 0.043 (4) | 0.044 (4) | 0.037 (4) | −0.009 (3) | −0.004 (3) | −0.009 (3) |
C34 | 0.050 (4) | 0.043 (4) | 0.044 (4) | 0.001 (3) | 0.006 (3) | 0.000 (3) |
C35 | 0.042 (4) | 0.043 (4) | 0.044 (4) | 0.009 (3) | 0.004 (3) | 0.009 (3) |
C36 | 0.032 (3) | 0.048 (4) | 0.034 (4) | 0.004 (3) | −0.004 (3) | 0.001 (3) |
C40 | 0.036 (4) | 0.036 (4) | 0.045 (4) | −0.006 (3) | −0.005 (3) | 0.003 (3) |
C41 | 0.029 (3) | 0.035 (4) | 0.027 (3) | −0.003 (3) | −0.005 (3) | −0.005 (3) |
C42 | 0.039 (4) | 0.058 (4) | 0.028 (4) | −0.004 (3) | 0.002 (3) | −0.003 (3) |
C43 | 0.052 (4) | 0.053 (4) | 0.028 (4) | −0.007 (3) | −0.005 (3) | 0.007 (3) |
C44 | 0.058 (5) | 0.039 (4) | 0.037 (4) | 0.011 (3) | −0.013 (3) | 0.000 (3) |
C45 | 0.030 (4) | 0.061 (5) | 0.037 (4) | 0.006 (3) | −0.005 (3) | −0.004 (3) |
C46 | 0.039 (4) | 0.045 (4) | 0.020 (3) | 0.000 (3) | 0.005 (3) | 0.001 (3) |
Co2 | 0.0271 (6) | 0.0337 (7) | 0.0194 (6) | 0.000 | −0.0047 (5) | 0.000 |
Br3 | 0.0356 (3) | 0.0454 (4) | 0.0276 (3) | −0.0082 (3) | −0.0079 (3) | −0.0022 (3) |
O3 | 0.041 (2) | 0.050 (3) | 0.043 (3) | −0.0133 (19) | −0.005 (2) | 0.012 (2) |
N5 | 0.035 (3) | 0.041 (3) | 0.029 (3) | 0.002 (2) | −0.002 (2) | 0.006 (2) |
N6 | 0.027 (3) | 0.045 (3) | 0.026 (3) | −0.002 (2) | −0.001 (2) | −0.005 (2) |
C51 | 0.032 (4) | 0.035 (4) | 0.033 (4) | −0.004 (3) | 0.002 (3) | 0.002 (3) |
C52 | 0.056 (4) | 0.050 (4) | 0.022 (3) | 0.002 (3) | −0.002 (3) | 0.001 (3) |
C53 | 0.076 (5) | 0.058 (5) | 0.022 (3) | −0.025 (4) | 0.008 (3) | 0.005 (3) |
C54 | 0.046 (4) | 0.110 (6) | 0.021 (4) | −0.017 (4) | 0.004 (3) | −0.007 (4) |
C60 | 0.025 (3) | 0.049 (4) | 0.039 (4) | −0.002 (3) | −0.006 (3) | 0.004 (3) |
C61 | 0.028 (3) | 0.035 (4) | 0.030 (3) | 0.002 (3) | −0.006 (3) | 0.008 (3) |
C62 | 0.032 (4) | 0.063 (5) | 0.034 (4) | −0.002 (3) | −0.001 (3) | −0.005 (3) |
C63 | 0.048 (4) | 0.056 (5) | 0.038 (4) | −0.008 (4) | 0.007 (3) | −0.012 (4) |
C64 | 0.050 (4) | 0.032 (4) | 0.052 (4) | 0.005 (3) | 0.015 (3) | 0.001 (3) |
C65 | 0.044 (4) | 0.047 (4) | 0.037 (4) | 0.011 (3) | −0.003 (3) | 0.000 (3) |
C66 | 0.038 (4) | 0.043 (4) | 0.029 (3) | −0.008 (3) | −0.006 (3) | 0.003 (3) |
C70 | 0.029 (4) | 0.037 (4) | 0.074 (5) | 0.007 (3) | 0.000 (3) | 0.002 (3) |
C71 | 0.036 (4) | 0.038 (4) | 0.024 (3) | 0.003 (3) | −0.001 (3) | −0.002 (3) |
C72 | 0.041 (4) | 0.062 (5) | 0.037 (4) | 0.004 (3) | −0.004 (3) | −0.005 (3) |
C73 | 0.054 (5) | 0.071 (5) | 0.038 (4) | 0.018 (4) | −0.011 (3) | −0.023 (4) |
C74 | 0.052 (4) | 0.066 (5) | 0.028 (4) | −0.004 (4) | −0.012 (3) | −0.006 (4) |
C75 | 0.039 (4) | 0.057 (4) | 0.034 (4) | 0.001 (3) | −0.003 (3) | 0.005 (3) |
C76 | 0.037 (4) | 0.042 (4) | 0.029 (3) | 0.001 (3) | 0.004 (3) | 0.002 (3) |
Co1—O2 | 1.926 (4) | C33—C34 | 1.377 (7) |
Co1—O1 | 1.955 (4) | C33—H33A | 0.9500 |
Co1—Br2 | 2.3757 (10) | C34—C35 | 1.357 (7) |
Co1—Br1 | 2.3809 (10) | C34—H34A | 0.9500 |
O1—C1 | 1.273 (6) | C35—C36 | 1.364 (7) |
O2—C5 | 1.253 (6) | C35—H35A | 0.9500 |
N1—C1 | 1.354 (6) | C36—H36A | 0.9500 |
N1—C10 | 1.455 (6) | C40—C41 | 1.515 (7) |
N1—C2 | 1.470 (6) | C40—H40A | 0.9900 |
N2—C1 | 1.336 (6) | C40—H40B | 0.9900 |
N2—C4 | 1.445 (7) | C41—C46 | 1.355 (7) |
N2—C20 | 1.464 (6) | C41—C42 | 1.393 (7) |
N3—C5 | 1.354 (6) | C42—C43 | 1.388 (7) |
N3—C30 | 1.442 (6) | C42—H42A | 0.9500 |
N3—C6 | 1.460 (7) | C43—C44 | 1.357 (8) |
N4—C5 | 1.325 (6) | C43—H43A | 0.9500 |
N4—C8 | 1.462 (7) | C44—C45 | 1.379 (8) |
N4—C40 | 1.465 (6) | C44—H44A | 0.9500 |
C2—C3 | 1.480 (7) | C45—C46 | 1.384 (7) |
C2—H2A | 0.9900 | C45—H45A | 0.9500 |
C2—H2B | 0.9900 | C46—H46A | 0.9500 |
C3—C4 | 1.497 (8) | Co2—O3i | 1.929 (4) |
C3—H3A | 0.9900 | Co2—O3 | 1.929 (4) |
C3—H3B | 0.9900 | Co2—Br3 | 2.3721 (9) |
C4—H4A | 0.9900 | Co2—Br3i | 2.3722 (9) |
C4—H4B | 0.9900 | O3—C51 | 1.284 (6) |
C6—C7 | 1.478 (8) | N5—C51 | 1.347 (6) |
C6—H6A | 0.9900 | N5—C60 | 1.436 (6) |
C6—H6B | 0.9900 | N5—C52 | 1.471 (6) |
C7—C8 | 1.477 (8) | N6—C51 | 1.326 (6) |
C7—H7A | 0.9900 | N6—C70 | 1.454 (6) |
C7—H7B | 0.9900 | N6—C54 | 1.461 (7) |
C8—H8A | 0.9900 | C52—C53 | 1.488 (7) |
C8—H8B | 0.9900 | C52—H52A | 0.9900 |
C10—C11 | 1.489 (7) | C52—H52B | 0.9900 |
C10—H10A | 0.9900 | C53—C54 | 1.490 (8) |
C10—H10B | 0.9900 | C53—H53A | 0.9900 |
C11—C16 | 1.394 (7) | C53—H53B | 0.9900 |
C11—C12 | 1.402 (6) | C54—H54A | 0.9900 |
C12—C13 | 1.375 (7) | C54—H54B | 0.9900 |
C12—H12A | 0.9500 | C60—C61 | 1.492 (7) |
C13—C14 | 1.360 (7) | C60—H60A | 0.9900 |
C13—H13A | 0.9500 | C60—H60B | 0.9900 |
C14—C15 | 1.386 (7) | C61—C66 | 1.385 (6) |
C14—H14A | 0.9500 | C61—C62 | 1.396 (7) |
C15—C16 | 1.381 (7) | C62—C63 | 1.360 (7) |
C15—H15A | 0.9500 | C62—H62A | 0.9500 |
C16—H16A | 0.9500 | C63—C64 | 1.375 (7) |
C20—C21 | 1.535 (7) | C63—H63A | 0.9500 |
C20—H20A | 0.9900 | C64—C65 | 1.375 (7) |
C20—H20B | 0.9900 | C64—H64A | 0.9500 |
C21—C22 | 1.368 (7) | C65—C66 | 1.371 (7) |
C21—C26 | 1.376 (7) | C65—H65A | 0.9500 |
C22—C23 | 1.378 (8) | C66—H66A | 0.9500 |
C22—H22A | 0.9500 | C70—C71 | 1.512 (7) |
C23—C24 | 1.349 (8) | C70—H70A | 0.9900 |
C23—H23A | 0.9500 | C70—H70B | 0.9900 |
C24—C25 | 1.363 (7) | C71—C72 | 1.377 (7) |
C24—H24A | 0.9500 | C71—C76 | 1.378 (7) |
C25—C26 | 1.384 (7) | C72—C73 | 1.387 (8) |
C25—H25A | 0.9500 | C72—H72A | 0.9500 |
C26—H26A | 0.9500 | C73—C74 | 1.362 (7) |
C30—C31 | 1.492 (7) | C73—H73A | 0.9500 |
C30—H30A | 0.9900 | C74—C75 | 1.388 (7) |
C30—H30B | 0.9900 | C74—H74A | 0.9500 |
C31—C32 | 1.398 (7) | C75—C76 | 1.380 (7) |
C31—C36 | 1.417 (7) | C75—H75A | 0.9500 |
C32—C33 | 1.377 (7) | C76—H76A | 0.9500 |
C32—H32A | 0.9500 | ||
O2—Co1—O1 | 102.26 (18) | C33—C32—H32A | 119.0 |
O2—Co1—Br2 | 109.10 (12) | C31—C32—H32A | 119.0 |
O1—Co1—Br2 | 111.60 (11) | C34—C33—C32 | 119.8 (6) |
O2—Co1—Br1 | 107.58 (12) | C34—C33—H33A | 120.1 |
O1—Co1—Br1 | 109.93 (11) | C32—C33—H33A | 120.1 |
Br2—Co1—Br1 | 115.46 (4) | C35—C34—C33 | 119.6 (6) |
C1—O1—Co1 | 141.1 (4) | C35—C34—H34A | 120.2 |
C5—O2—Co1 | 166.8 (4) | C33—C34—H34A | 120.2 |
C1—N1—C10 | 121.0 (5) | C34—C35—C36 | 121.7 (6) |
C1—N1—C2 | 122.9 (5) | C34—C35—H35A | 119.1 |
C10—N1—C2 | 115.9 (4) | C36—C35—H35A | 119.1 |
C1—N2—C4 | 122.4 (5) | C35—C36—C31 | 120.8 (5) |
C1—N2—C20 | 121.4 (5) | C35—C36—H36A | 119.6 |
C4—N2—C20 | 116.1 (5) | C31—C36—H36A | 119.6 |
C5—N3—C30 | 121.4 (5) | N4—C40—C41 | 111.7 (4) |
C5—N3—C6 | 121.7 (5) | N4—C40—H40A | 109.3 |
C30—N3—C6 | 116.7 (5) | C41—C40—H40A | 109.3 |
C5—N4—C8 | 123.4 (5) | N4—C40—H40B | 109.3 |
C5—N4—C40 | 120.3 (5) | C41—C40—H40B | 109.3 |
C8—N4—C40 | 116.0 (5) | H40A—C40—H40B | 107.9 |
O1—C1—N2 | 121.3 (5) | C46—C41—C42 | 119.5 (5) |
O1—C1—N1 | 119.8 (5) | C46—C41—C40 | 121.4 (5) |
N2—C1—N1 | 118.8 (5) | C42—C41—C40 | 119.1 (5) |
N1—C2—C3 | 110.7 (5) | C43—C42—C41 | 119.0 (6) |
N1—C2—H2A | 109.5 | C43—C42—H42A | 120.5 |
C3—C2—H2A | 109.5 | C41—C42—H42A | 120.5 |
N1—C2—H2B | 109.5 | C44—C43—C42 | 120.7 (6) |
C3—C2—H2B | 109.5 | C44—C43—H43A | 119.7 |
H2A—C2—H2B | 108.1 | C42—C43—H43A | 119.7 |
C2—C3—C4 | 109.5 (5) | C43—C44—C45 | 120.5 (6) |
C2—C3—H3A | 109.8 | C43—C44—H44A | 119.8 |
C4—C3—H3A | 109.8 | C45—C44—H44A | 119.8 |
C2—C3—H3B | 109.8 | C44—C45—C46 | 118.8 (6) |
C4—C3—H3B | 109.8 | C44—C45—H45A | 120.6 |
H3A—C3—H3B | 108.2 | C46—C45—H45A | 120.6 |
N2—C4—C3 | 110.1 (5) | C41—C46—C45 | 121.4 (6) |
N2—C4—H4A | 109.6 | C41—C46—H46A | 119.3 |
C3—C4—H4A | 109.6 | C45—C46—H46A | 119.3 |
N2—C4—H4B | 109.6 | O3i—Co2—O3 | 98.1 (2) |
C3—C4—H4B | 109.6 | O3i—Co2—Br3 | 108.54 (11) |
H4A—C4—H4B | 108.2 | O3—Co2—Br3 | 112.60 (11) |
O2—C5—N4 | 120.9 (5) | O3i—Co2—Br3i | 112.60 (11) |
O2—C5—N3 | 120.0 (5) | O3—Co2—Br3i | 108.54 (11) |
N4—C5—N3 | 119.1 (5) | Br3—Co2—Br3i | 115.20 (5) |
N3—C6—C7 | 110.8 (5) | C51—O3—Co2 | 152.7 (4) |
N3—C6—H6A | 109.5 | C51—N5—C60 | 121.4 (5) |
C7—C6—H6A | 109.5 | C51—N5—C52 | 121.0 (5) |
N3—C6—H6B | 109.5 | C60—N5—C52 | 117.3 (4) |
C7—C6—H6B | 109.5 | C51—N6—C70 | 121.2 (5) |
H6A—C6—H6B | 108.1 | C51—N6—C54 | 122.7 (5) |
C8—C7—C6 | 110.5 (6) | C70—N6—C54 | 116.1 (5) |
C8—C7—H7A | 109.5 | O3—C51—N6 | 120.2 (5) |
C6—C7—H7A | 109.5 | O3—C51—N5 | 119.2 (5) |
C8—C7—H7B | 109.5 | N6—C51—N5 | 120.5 (5) |
C6—C7—H7B | 109.5 | N5—C52—C53 | 110.2 (4) |
H7A—C7—H7B | 108.1 | N5—C52—H52A | 109.6 |
N4—C8—C7 | 110.0 (5) | C53—C52—H52A | 109.6 |
N4—C8—H8A | 109.7 | N5—C52—H52B | 109.6 |
C7—C8—H8A | 109.7 | C53—C52—H52B | 109.6 |
N4—C8—H8B | 109.7 | H52A—C52—H52B | 108.1 |
C7—C8—H8B | 109.7 | C52—C53—C54 | 109.6 (5) |
H8A—C8—H8B | 108.2 | C52—C53—H53A | 109.8 |
N1—C10—C11 | 112.8 (4) | C54—C53—H53A | 109.8 |
N1—C10—H10A | 109.0 | C52—C53—H53B | 109.8 |
C11—C10—H10A | 109.0 | C54—C53—H53B | 109.8 |
N1—C10—H10B | 109.0 | H53A—C53—H53B | 108.2 |
C11—C10—H10B | 109.0 | N6—C54—C53 | 110.8 (5) |
H10A—C10—H10B | 107.8 | N6—C54—H54A | 109.5 |
C16—C11—C12 | 118.1 (5) | C53—C54—H54A | 109.5 |
C16—C11—C10 | 120.4 (5) | N6—C54—H54B | 109.5 |
C12—C11—C10 | 121.5 (5) | C53—C54—H54B | 109.5 |
C13—C12—C11 | 120.1 (5) | H54A—C54—H54B | 108.1 |
C13—C12—H12A | 119.9 | N5—C60—C61 | 113.4 (5) |
C11—C12—H12A | 119.9 | N5—C60—H60A | 108.9 |
C14—C13—C12 | 121.0 (6) | C61—C60—H60A | 108.9 |
C14—C13—H13A | 119.5 | N5—C60—H60B | 108.9 |
C12—C13—H13A | 119.5 | C61—C60—H60B | 108.9 |
C13—C14—C15 | 120.3 (6) | H60A—C60—H60B | 107.7 |
C13—C14—H14A | 119.8 | C66—C61—C62 | 117.7 (5) |
C15—C14—H14A | 119.8 | C66—C61—C60 | 122.3 (5) |
C16—C15—C14 | 119.3 (5) | C62—C61—C60 | 120.0 (5) |
C16—C15—H15A | 120.4 | C63—C62—C61 | 120.4 (6) |
C14—C15—H15A | 120.4 | C63—C62—H62A | 119.8 |
C15—C16—C11 | 121.1 (5) | C61—C62—H62A | 119.8 |
C15—C16—H16A | 119.4 | C62—C63—C64 | 121.0 (6) |
C11—C16—H16A | 119.4 | C62—C63—H63A | 119.5 |
N2—C20—C21 | 111.0 (5) | C64—C63—H63A | 119.5 |
N2—C20—H20A | 109.4 | C65—C64—C63 | 119.7 (6) |
C21—C20—H20A | 109.4 | C65—C64—H64A | 120.2 |
N2—C20—H20B | 109.4 | C63—C64—H64A | 120.2 |
C21—C20—H20B | 109.4 | C66—C65—C64 | 119.5 (6) |
H20A—C20—H20B | 108.0 | C66—C65—H65A | 120.3 |
C22—C21—C26 | 120.3 (6) | C64—C65—H65A | 120.3 |
C22—C21—C20 | 120.6 (5) | C65—C66—C61 | 121.7 (5) |
C26—C21—C20 | 119.1 (6) | C65—C66—H66A | 119.1 |
C21—C22—C23 | 119.4 (6) | C61—C66—H66A | 119.1 |
C21—C22—H22A | 120.3 | N6—C70—C71 | 112.8 (5) |
C23—C22—H22A | 120.3 | N6—C70—H70A | 109.0 |
C24—C23—C22 | 120.6 (6) | C71—C70—H70A | 109.0 |
C24—C23—H23A | 119.7 | N6—C70—H70B | 109.0 |
C22—C23—H23A | 119.7 | C71—C70—H70B | 109.0 |
C23—C24—C25 | 120.3 (6) | H70A—C70—H70B | 107.8 |
C23—C24—H24A | 119.8 | C72—C71—C76 | 119.1 (5) |
C25—C24—H24A | 119.8 | C72—C71—C70 | 120.3 (5) |
C24—C25—C26 | 120.2 (6) | C76—C71—C70 | 120.5 (5) |
C24—C25—H25A | 119.9 | C71—C72—C73 | 120.5 (6) |
C26—C25—H25A | 119.9 | C71—C72—H72A | 119.7 |
C21—C26—C25 | 119.1 (6) | C73—C72—H72A | 119.7 |
C21—C26—H26A | 120.5 | C74—C73—C72 | 119.6 (6) |
C25—C26—H26A | 120.5 | C74—C73—H73A | 120.2 |
N3—C30—C31 | 113.0 (5) | C72—C73—H73A | 120.2 |
N3—C30—H30A | 109.0 | C73—C74—C75 | 120.8 (6) |
C31—C30—H30A | 109.0 | C73—C74—H74A | 119.6 |
N3—C30—H30B | 109.0 | C75—C74—H74A | 119.6 |
C31—C30—H30B | 109.0 | C76—C75—C74 | 118.9 (6) |
H30A—C30—H30B | 107.8 | C76—C75—H75A | 120.5 |
C32—C31—C36 | 116.1 (5) | C74—C75—H75A | 120.5 |
C32—C31—C30 | 122.6 (5) | C71—C76—C75 | 120.9 (6) |
C36—C31—C30 | 121.3 (5) | C71—C76—H76A | 119.5 |
C33—C32—C31 | 122.0 (5) | C75—C76—H76A | 119.5 |
Co1—O1—C1—N2 | 91.8 (7) | C36—C31—C32—C33 | −1.2 (8) |
Co1—O1—C1—N1 | −90.7 (7) | C30—C31—C32—C33 | 179.8 (5) |
C4—N2—C1—O1 | 176.6 (5) | C31—C32—C33—C34 | 0.6 (9) |
C20—N2—C1—O1 | −5.9 (8) | C32—C33—C34—C35 | −0.1 (9) |
C4—N2—C1—N1 | −1.0 (8) | C33—C34—C35—C36 | 0.4 (9) |
C20—N2—C1—N1 | 176.5 (5) | C34—C35—C36—C31 | −1.1 (9) |
C10—N1—C1—O1 | 4.1 (8) | C32—C31—C36—C35 | 1.4 (8) |
C2—N1—C1—O1 | −170.5 (5) | C30—C31—C36—C35 | −179.6 (5) |
C10—N1—C1—N2 | −178.3 (5) | C5—N4—C40—C41 | 103.5 (6) |
C2—N1—C1—N2 | 7.1 (8) | C8—N4—C40—C41 | −70.2 (6) |
C1—N1—C2—C3 | 19.8 (7) | N4—C40—C41—C46 | 112.1 (6) |
C10—N1—C2—C3 | −155.0 (5) | N4—C40—C41—C42 | −67.2 (7) |
N1—C2—C3—C4 | −50.2 (6) | C46—C41—C42—C43 | −1.8 (8) |
C1—N2—C4—C3 | −30.9 (7) | C40—C41—C42—C43 | 177.5 (5) |
C20—N2—C4—C3 | 151.4 (5) | C41—C42—C43—C44 | 1.0 (9) |
C2—C3—C4—N2 | 55.8 (6) | C42—C43—C44—C45 | 0.4 (9) |
Co1—O2—C5—N4 | 119.6 (17) | C43—C44—C45—C46 | −0.8 (9) |
Co1—O2—C5—N3 | −61 (2) | C42—C41—C46—C45 | 1.4 (8) |
C8—N4—C5—O2 | 172.3 (5) | C40—C41—C46—C45 | −177.9 (5) |
C40—N4—C5—O2 | −0.9 (8) | C44—C45—C46—C41 | −0.1 (9) |
C8—N4—C5—N3 | −6.9 (8) | Co2—O3—C51—N6 | −103.5 (8) |
C40—N4—C5—N3 | 179.9 (5) | Co2—O3—C51—N5 | 80.1 (10) |
C30—N3—C5—O2 | 3.2 (8) | C70—N6—C51—O3 | 11.5 (8) |
C6—N3—C5—O2 | −172.8 (5) | C54—N6—C51—O3 | −169.6 (5) |
C30—N3—C5—N4 | −177.6 (5) | C70—N6—C51—N5 | −172.1 (5) |
C6—N3—C5—N4 | 6.4 (8) | C54—N6—C51—N5 | 6.8 (8) |
C5—N3—C6—C7 | 23.9 (8) | C60—N5—C51—O3 | −0.8 (8) |
C30—N3—C6—C7 | −152.3 (5) | C52—N5—C51—O3 | 173.4 (5) |
N3—C6—C7—C8 | −52.7 (7) | C60—N5—C51—N6 | −177.2 (5) |
C5—N4—C8—C7 | −23.0 (8) | C52—N5—C51—N6 | −3.0 (8) |
C40—N4—C8—C7 | 150.5 (5) | C51—N5—C52—C53 | −28.5 (7) |
C6—C7—C8—N4 | 52.0 (7) | C60—N5—C52—C53 | 146.0 (5) |
C1—N1—C10—C11 | −107.8 (5) | N5—C52—C53—C54 | 54.6 (6) |
C2—N1—C10—C11 | 67.1 (6) | C51—N6—C54—C53 | 21.5 (8) |
N1—C10—C11—C16 | 53.2 (7) | C70—N6—C54—C53 | −159.5 (5) |
N1—C10—C11—C12 | −126.0 (5) | C52—C53—C54—N6 | −51.4 (7) |
C16—C11—C12—C13 | 0.9 (8) | C51—N5—C60—C61 | 107.4 (6) |
C10—C11—C12—C13 | −179.9 (5) | C52—N5—C60—C61 | −67.1 (6) |
C11—C12—C13—C14 | −2.1 (9) | N5—C60—C61—C66 | 126.7 (5) |
C12—C13—C14—C15 | 2.7 (9) | N5—C60—C61—C62 | −51.7 (7) |
C13—C14—C15—C16 | −1.9 (9) | C66—C61—C62—C63 | −0.5 (9) |
C14—C15—C16—C11 | 0.7 (9) | C60—C61—C62—C63 | 178.0 (5) |
C12—C11—C16—C15 | −0.1 (8) | C61—C62—C63—C64 | −0.1 (9) |
C10—C11—C16—C15 | −179.4 (5) | C62—C63—C64—C65 | 0.9 (9) |
C1—N2—C20—C21 | 117.0 (6) | C63—C64—C65—C66 | −1.1 (9) |
C4—N2—C20—C21 | −65.3 (7) | C64—C65—C66—C61 | 0.4 (9) |
N2—C20—C21—C22 | −66.0 (7) | C62—C61—C66—C65 | 0.4 (8) |
N2—C20—C21—C26 | 112.7 (6) | C60—C61—C66—C65 | −178.1 (5) |
C26—C21—C22—C23 | −1.5 (9) | C51—N6—C70—C71 | −111.2 (6) |
C20—C21—C22—C23 | 177.2 (5) | C54—N6—C70—C71 | 69.9 (7) |
C21—C22—C23—C24 | 2.5 (9) | N6—C70—C71—C72 | 47.9 (8) |
C22—C23—C24—C25 | −1.7 (9) | N6—C70—C71—C76 | −134.7 (5) |
C23—C24—C25—C26 | −0.1 (9) | C76—C71—C72—C73 | 1.8 (9) |
C22—C21—C26—C25 | −0.3 (8) | C70—C71—C72—C73 | 179.2 (6) |
C20—C21—C26—C25 | −179.0 (5) | C71—C72—C73—C74 | −1.6 (9) |
C24—C25—C26—C21 | 1.1 (8) | C72—C73—C74—C75 | 0.1 (10) |
C5—N3—C30—C31 | −103.0 (6) | C73—C74—C75—C76 | 1.1 (9) |
C6—N3—C30—C31 | 73.2 (6) | C72—C71—C76—C75 | −0.5 (8) |
N3—C30—C31—C32 | −136.3 (5) | C70—C71—C76—C75 | −177.9 (5) |
N3—C30—C31—C36 | 44.8 (7) | C74—C75—C76—C71 | −0.9 (9) |
Symmetry code: (i) −x, y, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8B···Br1ii | 0.99 | 3.00 | 3.943 (6) | 159 |
C70—H70B···Br3i | 0.99 | 3.00 | 3.987 (6) | 175 |
C54—H54A···Br2iii | 0.99 | 3.04 | 3.860 (6) | 141 |
Symmetry codes: (i) −x, y, −z+1/2; (ii) −x+1/2, −y+5/2, −z; (iii) x, y−1, z. |
Co1—O2 | 1.926 (4) | Co1—Br1 | 2.3809 (10) |
Co1—O1 | 1.955 (4) | Co2—O3 | 1.929 (4) |
Co1—Br2 | 2.3757 (10) | Co2—Br3 | 2.3721 (9) |
O2—Co1—O1 | 102.26 (18) | Br2—Co1—Br1 | 115.46 (4) |
O2—Co1—Br2 | 109.10 (12) | O3i—Co2—O3 | 98.1 (2) |
O1—Co1—Br2 | 111.60 (11) | O3—Co2—Br3 | 112.60 (11) |
O2—Co1—Br1 | 107.58 (12) | O3—Co2—Br3i | 108.54 (11) |
O1—Co1—Br1 | 109.93 (11) | Br3—Co2—Br3i | 115.20 (5) |
Symmetry code: (i) −x, y, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8B···Br1ii | 0.99 | 3.00 | 3.943 (6) | 159.2 |
C70—H70B···Br3i | 0.99 | 3.00 | 3.987 (6) | 174.6 |
C54—H54A···Br2iii | 0.99 | 3.04 | 3.860 (6) | 141.1 |
Symmetry codes: (i) −x, y, −z+1/2; (ii) −x+1/2, −y+5/2, −z; (iii) x, y−1, z. |
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