metal-organic compounds
H-imidazol-3-ium) tetrabromidocobaltate(II) bromide chloroform hexasolvate
of tris(1,3-dimesityl-4,5-dihydro-1aDepartment Chemie, Universität Paderborn, Warburgerstrasse 100, 33098 Paderborn, Germany
*Correspondence e-mail: ulrich.floerke@upb.de, rene.wilhelm@upb.de
In the 21H27N2)3[CoBr4]Br·6CHCl3, the tetrabromidocobaltate(II) anion and the bromide anion are located on a crystallographic threefold rotation axis. For the [CoBr4]2− group, the axis runs through one of the Br ligands and the CoII atom. All other structure moieties lie on general sites. Various tris(1,3-dimesityl-4,5-dihydro-1H-imidazol-3-ium) structures with different counter-ions have been reported. In the title compound, the N—C—N angle is 113.7 (5)°, with short C—N bond lengths of 1.297 (7) and 1.307 (7) Å. The two mesityl planes make a dihedral angle of 34.6 (1)° and the dihedral angles between the mesityl and N–C–N planes are 82.0 (1) and 88.5 (1)°, respectively. The imidazoline ring is almost planar, with atom deviations in the range 0.003 (5)–0.017 (5) Å from the best plane; the mean deviation is 0.012 (5) Å. In the crystal, non-covalent interactions of the C—H⋯Br type occur between the Br− anion and the cation, as well as between the [CoBr4]2− anion and both the chloroform solvent molecules. These H⋯A distances are slightly shorter than the sum of van der Waals radii.
of the title compound, (CCCDC reference: 1421420
1. Related literature
For similar tris(1,3-dimesityl-4,5-dihydro-1H-imidazol-3-ium) structures, see: Arduengo et al. (1995); Hagos et al. (2008); Santoro et al. (2013); Buchalski et al. (2015). For synthesis of 2-bromo-1,3-dimesityl-4,5-dihydro-1H-imidazol-3-ium bromide, see: Wiggins et al. (2012). For the application of 1,3-dimesityl-4,5-dihydro-1H-imidazol-3-ium cation as a carbene precursor, see: Díez-González et al. (2009). For catalytic application of imidazolium based [CoCl4]2− salts, see: Bica & Gärtner (2008); Wang et al. (2015).
2. Experimental
2.1. Crystal data
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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: 1421420
10.1107/S2056989015016254/nr2061sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989015016254/nr2061Isup2.hkl
All manipulations were carried out under nitrogen atmosphere using standard Schlenk techniques. MeCN was dried with an MBRAUN MB SPS-800 solvent purification system under nitrogen. CHCl3 was dried over activated molecular sieve with 3 Å pore diameter. 2-Bromo-1,3-dimesityl-4,5-dihydro-1H-imidazol-3-ium bromide (0.080 g, 0.172 mmol, 1 eq) and Cobalt powder (0.227 g, 3.852 mmol, 22 eq, grain size < 150 µm) were filled into a sealed schlenk tube equipped with a stirring bar. MeCN (3 mL) was added and the mixture was stirred and heated at 100 °C for 40 h under
The cooled down mixture was filtrated and the solvent was then removed under vacuum. The residual brown oil was separated by decantation and was dissolved in CHCl3 (0.7 mL). Crystal growth could be observed after one day. The NMR spectra are not suitable because of the paramagnetic properties of the [CoBr4]2- anion.Hydrogen atom positions were clearly derived from difference Fourier maps and then refined at idealized positions riding on the carbon atoms with isotropic displacement parameters Uiso(H) = 1.2U(Ceq) or 1.5U(-CH3) and C–H 0.95-1.00 Å. All CH3 hydrogen atoms were allowed to rotate but not to tip. It was not possible to refine a satisfactory split model for the C100–chloroform.
The cation is a common precursor for the synthesis of 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene, which is used as a ligand in various catalytic applications (Díez-González et al., 2009). Alkyl-substituted imidazolium cations with [CoX4]2- anions (X = Cl, Br) are used as metal-containing ionic liquids (Bica & Gaertner, 2008; Wang et al., 2015).
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 and local programs.(C21H27N2)3[CoBr4]Br·6CHCl3 | Dx = 1.515 Mg m−3 |
Mr = 2097.02 | Mo Kα radiation, λ = 0.71073 Å |
Trigonal, R3c:H | Cell parameters from 4234 reflections |
a = 16.0535 (14) Å | θ = 2.5–19.7° |
c = 61.790 (12) Å | µ = 2.92 mm−1 |
V = 13791 (4) Å3 | T = 130 K |
Z = 6 | Prism, pale-green |
F(000) = 6306 | 0.22 × 0.21 × 0.20 mm |
Bruker SMART APEX diffractometer | 7309 independent reflections |
Radiation source: sealed tube | 4427 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.077 |
φ and ω scans | θmax = 27.9°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | h = −21→21 |
Tmin = 0.279, Tmax = 1.0 | k = −21→19 |
41734 measured reflections | l = −81→81 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.078 | w = 1/[σ2(Fo2) + (0.0298P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.79 | (Δ/σ)max = 0.001 |
7309 reflections | Δρmax = 0.65 e Å−3 |
306 parameters | Δρmin = −0.64 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 1821 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.020 (11) |
(C21H27N2)3[CoBr4]Br·6CHCl3 | Z = 6 |
Mr = 2097.02 | Mo Kα radiation |
Trigonal, R3c:H | µ = 2.92 mm−1 |
a = 16.0535 (14) Å | T = 130 K |
c = 61.790 (12) Å | 0.22 × 0.21 × 0.20 mm |
V = 13791 (4) Å3 |
Bruker SMART APEX diffractometer | 7309 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | 4427 reflections with I > 2σ(I) |
Tmin = 0.279, Tmax = 1.0 | Rint = 0.077 |
41734 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.078 | Δρmax = 0.65 e Å−3 |
S = 0.79 | Δρmin = −0.64 e Å−3 |
7309 reflections | Absolute structure: Flack (1983), 1821 Friedel pairs |
306 parameters | Absolute structure parameter: 0.020 (11) |
1 restraint |
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 | 0.6667 | 0.3333 | 0.91225 (2) | 0.0290 (3) | |
Br1 | 0.77035 (4) | 0.49648 (5) | 0.92389 (2) | 0.04336 (19) | |
Br2 | 0.6667 | 0.3333 | 0.87362 (2) | 0.0630 (4) | |
Br3 | 0.3333 | 0.6667 | 0.91594 (3) | 0.0524 (4) | |
N1 | 0.4682 (3) | −0.0461 (3) | 0.90279 (8) | 0.0296 (12) | |
N2 | 0.4612 (3) | −0.0455 (3) | 0.93802 (8) | 0.0281 (12) | |
C1 | 0.4610 (4) | −0.0918 (4) | 0.92081 (10) | 0.0292 (14) | |
H1A | 0.4561 | −0.1533 | 0.9213 | 0.035* | |
C2 | 0.4754 (4) | 0.0476 (4) | 0.90750 (10) | 0.0338 (16) | |
H2A | 0.4225 | 0.0526 | 0.9005 | 0.041* | |
H2B | 0.5378 | 0.1017 | 0.9026 | 0.041* | |
C3 | 0.4669 (4) | 0.0462 (4) | 0.93224 (9) | 0.0270 (14) | |
H3A | 0.5239 | 0.1015 | 0.9389 | 0.032* | |
H3B | 0.4082 | 0.0472 | 0.9368 | 0.032* | |
C4 | 0.4725 (4) | −0.0782 (4) | 0.88091 (10) | 0.0319 (15) | |
C5 | 0.5614 (5) | −0.0511 (5) | 0.87196 (13) | 0.049 (2) | |
C6 | 0.5625 (6) | −0.0800 (5) | 0.85046 (12) | 0.055 (2) | |
H6A | 0.6222 | −0.0621 | 0.8437 | 0.065* | |
C7 | 0.4769 (7) | −0.1346 (6) | 0.83901 (12) | 0.054 (2) | |
C8 | 0.3921 (6) | −0.1592 (5) | 0.84898 (11) | 0.0464 (18) | |
H8A | 0.3340 | −0.1964 | 0.8412 | 0.056* | |
C9 | 0.3867 (5) | −0.1327 (4) | 0.86980 (11) | 0.0375 (16) | |
C10 | 0.6534 (5) | 0.0048 (6) | 0.88517 (16) | 0.087 (3) | |
H10A | 0.6525 | −0.0346 | 0.8974 | 0.130* | |
H10B | 0.6577 | 0.0641 | 0.8907 | 0.130* | |
H10C | 0.7092 | 0.0210 | 0.8760 | 0.130* | |
C11 | 0.4845 (7) | −0.1602 (6) | 0.81586 (12) | 0.080 (3) | |
H11A | 0.5414 | −0.1673 | 0.8143 | 0.120* | |
H11B | 0.4902 | −0.1090 | 0.8062 | 0.120* | |
H11C | 0.4268 | −0.2209 | 0.8120 | 0.120* | |
C12 | 0.2910 (5) | −0.1610 (5) | 0.87956 (12) | 0.0503 (19) | |
H12A | 0.2405 | −0.1947 | 0.8687 | 0.075* | |
H12B | 0.2902 | −0.1032 | 0.8844 | 0.075* | |
H12C | 0.2795 | −0.2035 | 0.8919 | 0.075* | |
C13 | 0.4495 (4) | −0.0797 (4) | 0.96013 (10) | 0.0293 (14) | |
C14 | 0.5308 (4) | −0.0439 (4) | 0.97348 (11) | 0.0356 (16) | |
C15 | 0.5164 (5) | −0.0718 (4) | 0.99472 (11) | 0.0395 (17) | |
H15A | 0.5707 | −0.0479 | 1.0040 | 0.047* | |
C16 | 0.4255 (5) | −0.1339 (4) | 1.00332 (11) | 0.0403 (17) | |
C17 | 0.3468 (5) | −0.1667 (5) | 0.98966 (12) | 0.0454 (19) | |
H17A | 0.2845 | −0.2091 | 0.9953 | 0.055* | |
C18 | 0.3559 (5) | −0.1394 (4) | 0.96770 (12) | 0.0378 (16) | |
C19 | 0.6300 (4) | 0.0195 (5) | 0.96462 (11) | 0.0487 (19) | |
H19A | 0.6332 | 0.0760 | 0.9577 | 0.073* | |
H19B | 0.6447 | −0.0163 | 0.9539 | 0.073* | |
H19C | 0.6769 | 0.0403 | 0.9764 | 0.073* | |
C20 | 0.4143 (6) | −0.1603 (5) | 1.02691 (12) | 0.059 (2) | |
H20A | 0.4242 | −0.2153 | 1.0290 | 0.089* | |
H20B | 0.3495 | −0.1774 | 1.0317 | 0.089* | |
H20C | 0.4620 | −0.1054 | 1.0354 | 0.089* | |
C21 | 0.2699 (4) | −0.1763 (5) | 0.95317 (12) | 0.0503 (19) | |
H21A | 0.2725 | −0.2195 | 0.9423 | 0.076* | |
H21B | 0.2698 | −0.1221 | 0.9459 | 0.076* | |
H21C | 0.2111 | −0.2116 | 0.9618 | 0.076* | |
C100 | 0.8893 (6) | 0.1327 (6) | 0.92865 (13) | 0.070 (3) | |
H10 | 0.8362 | 0.1455 | 0.9248 | 0.084* | |
Cl11 | 0.91290 (19) | 0.1546 (2) | 0.95548 (4) | 0.0938 (8) | |
Cl12 | 0.8521 (2) | 0.0149 (2) | 0.92250 (7) | 0.1562 (18) | |
Cl13 | 0.9911 (3) | 0.2121 (2) | 0.91398 (5) | 0.1293 (12) | |
C200 | 0.0704 (6) | 0.8507 (6) | 0.01629 (18) | 0.091 (3) | |
H20 | 0.0749 | 0.9066 | 0.0245 | 0.109* | |
Cl21 | 0.1365 (2) | 0.8900 (2) | −0.00698 (6) | 0.1410 (14) | |
Cl22 | 0.11836 (19) | 0.7912 (2) | 0.03238 (5) | 0.1032 (9) | |
Cl23 | −0.05036 (16) | 0.76626 (15) | 0.01124 (4) | 0.0790 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Co1 | 0.0214 (5) | 0.0214 (5) | 0.0440 (10) | 0.0107 (2) | 0.000 | 0.000 |
Br1 | 0.0253 (3) | 0.0267 (3) | 0.0769 (5) | 0.0121 (3) | −0.0062 (4) | −0.0129 (3) |
Br2 | 0.0687 (6) | 0.0687 (6) | 0.0515 (9) | 0.0344 (3) | 0.000 | 0.000 |
Br3 | 0.0263 (4) | 0.0263 (4) | 0.1045 (11) | 0.01314 (19) | 0.000 | 0.000 |
N1 | 0.030 (3) | 0.027 (3) | 0.033 (3) | 0.015 (2) | −0.001 (2) | −0.004 (2) |
N2 | 0.032 (3) | 0.026 (3) | 0.028 (3) | 0.016 (2) | 0.003 (2) | 0.000 (2) |
C1 | 0.023 (3) | 0.024 (3) | 0.034 (4) | 0.007 (3) | 0.002 (3) | 0.002 (3) |
C2 | 0.032 (4) | 0.025 (3) | 0.046 (5) | 0.015 (3) | −0.004 (3) | −0.004 (3) |
C3 | 0.031 (3) | 0.027 (3) | 0.027 (4) | 0.017 (3) | −0.001 (3) | −0.005 (3) |
C4 | 0.041 (4) | 0.024 (3) | 0.031 (4) | 0.016 (3) | 0.004 (3) | 0.004 (3) |
C5 | 0.051 (5) | 0.034 (4) | 0.065 (6) | 0.023 (4) | 0.013 (4) | −0.001 (4) |
C6 | 0.072 (6) | 0.049 (5) | 0.056 (6) | 0.041 (4) | 0.036 (5) | 0.017 (4) |
C7 | 0.092 (6) | 0.056 (5) | 0.037 (5) | 0.055 (5) | −0.005 (5) | −0.002 (4) |
C8 | 0.062 (5) | 0.056 (5) | 0.029 (4) | 0.034 (4) | −0.001 (4) | −0.007 (4) |
C9 | 0.052 (4) | 0.032 (4) | 0.031 (4) | 0.023 (3) | −0.005 (3) | −0.003 (3) |
C10 | 0.029 (4) | 0.098 (7) | 0.125 (9) | 0.026 (5) | 0.007 (5) | −0.044 (6) |
C11 | 0.149 (9) | 0.094 (7) | 0.044 (6) | 0.095 (7) | 0.010 (5) | 0.005 (5) |
C12 | 0.043 (4) | 0.047 (4) | 0.050 (5) | 0.014 (4) | −0.009 (4) | −0.015 (4) |
C13 | 0.037 (4) | 0.020 (3) | 0.032 (4) | 0.015 (3) | 0.004 (3) | 0.002 (3) |
C14 | 0.039 (4) | 0.027 (3) | 0.039 (5) | 0.015 (3) | 0.001 (3) | 0.010 (3) |
C15 | 0.047 (4) | 0.040 (4) | 0.035 (5) | 0.024 (4) | 0.000 (3) | 0.007 (3) |
C16 | 0.060 (5) | 0.034 (4) | 0.034 (4) | 0.030 (4) | 0.005 (4) | 0.004 (3) |
C17 | 0.052 (5) | 0.036 (4) | 0.045 (5) | 0.021 (4) | 0.028 (4) | 0.011 (4) |
C18 | 0.041 (4) | 0.027 (4) | 0.046 (5) | 0.017 (3) | 0.005 (3) | −0.005 (3) |
C19 | 0.034 (4) | 0.050 (4) | 0.050 (5) | 0.012 (4) | −0.001 (3) | 0.007 (4) |
C20 | 0.073 (6) | 0.052 (5) | 0.052 (5) | 0.030 (4) | 0.019 (4) | 0.021 (4) |
C21 | 0.035 (4) | 0.050 (4) | 0.058 (5) | 0.015 (4) | 0.011 (4) | 0.000 (4) |
C100 | 0.076 (6) | 0.086 (6) | 0.074 (7) | 0.061 (6) | −0.032 (5) | −0.030 (5) |
Cl11 | 0.106 (2) | 0.119 (2) | 0.0673 (17) | 0.0651 (18) | −0.0027 (14) | 0.0048 (15) |
Cl12 | 0.159 (3) | 0.107 (2) | 0.248 (5) | 0.101 (2) | −0.115 (3) | −0.096 (3) |
Cl13 | 0.192 (3) | 0.165 (3) | 0.115 (2) | 0.153 (3) | 0.073 (2) | 0.067 (2) |
C200 | 0.061 (6) | 0.049 (5) | 0.147 (10) | 0.016 (5) | 0.028 (6) | −0.021 (6) |
Cl21 | 0.128 (3) | 0.114 (2) | 0.181 (4) | 0.060 (2) | 0.098 (3) | 0.067 (2) |
Cl22 | 0.096 (2) | 0.0933 (19) | 0.107 (2) | 0.0379 (16) | −0.0029 (17) | −0.0331 (17) |
Cl23 | 0.0694 (15) | 0.0597 (14) | 0.0825 (17) | 0.0131 (12) | 0.0122 (13) | −0.0093 (12) |
Co1—Br2 | 2.387 (2) | C11—H11C | 0.9800 |
Co1—Br1 | 2.4057 (8) | C12—H12A | 0.9800 |
Co1—Br1i | 2.4057 (8) | C12—H12B | 0.9800 |
Co1—Br1ii | 2.4057 (8) | C12—H12C | 0.9800 |
N1—C1 | 1.307 (7) | C13—C18 | 1.397 (8) |
N1—C4 | 1.460 (7) | C13—C14 | 1.402 (8) |
N1—C2 | 1.479 (7) | C14—C15 | 1.368 (8) |
N2—C1 | 1.297 (7) | C14—C19 | 1.500 (8) |
N2—C13 | 1.449 (7) | C15—C16 | 1.397 (9) |
N2—C3 | 1.472 (7) | C15—H15A | 0.9500 |
C1—H1A | 0.9500 | C16—C17 | 1.386 (10) |
C2—C3 | 1.534 (8) | C16—C20 | 1.504 (9) |
C2—H2A | 0.9900 | C17—C18 | 1.411 (9) |
C2—H2B | 0.9900 | C17—H17A | 0.9500 |
C3—H3A | 0.9900 | C18—C21 | 1.499 (9) |
C3—H3B | 0.9900 | C19—H19A | 0.9800 |
C4—C5 | 1.383 (9) | C19—H19B | 0.9800 |
C4—C9 | 1.389 (8) | C19—H19C | 0.9800 |
C5—C6 | 1.410 (10) | C20—H20A | 0.9800 |
C5—C10 | 1.525 (10) | C20—H20B | 0.9800 |
C6—C7 | 1.397 (10) | C20—H20C | 0.9800 |
C6—H6A | 0.9500 | C21—H21A | 0.9800 |
C7—C8 | 1.360 (10) | C21—H21B | 0.9800 |
C7—C11 | 1.510 (10) | C21—H21C | 0.9800 |
C8—C9 | 1.371 (9) | C100—Cl11 | 1.698 (8) |
C8—H8A | 0.9500 | C100—Cl12 | 1.716 (8) |
C9—C12 | 1.494 (9) | C100—Cl13 | 1.741 (9) |
C10—H10A | 0.9800 | C100—H10 | 1.0000 |
C10—H10B | 0.9800 | C200—Cl21 | 1.709 (10) |
C10—H10C | 0.9800 | C200—Cl23 | 1.751 (9) |
C11—H11A | 0.9800 | C200—Cl22 | 1.797 (11) |
C11—H11B | 0.9800 | C200—H20 | 1.0000 |
Br2—Co1—Br1 | 107.39 (4) | H11B—C11—H11C | 109.5 |
Br2—Co1—Br1i | 107.39 (4) | C9—C12—H12A | 109.5 |
Br1—Co1—Br1i | 111.47 (4) | C9—C12—H12B | 109.5 |
Br2—Co1—Br1ii | 107.39 (4) | H12A—C12—H12B | 109.5 |
Br1—Co1—Br1ii | 111.47 (4) | C9—C12—H12C | 109.5 |
Br1i—Co1—Br1ii | 111.47 (4) | H12A—C12—H12C | 109.5 |
C1—N1—C4 | 126.6 (5) | H12B—C12—H12C | 109.5 |
C1—N1—C2 | 110.1 (5) | C18—C13—C14 | 123.0 (6) |
C4—N1—C2 | 123.2 (5) | C18—C13—N2 | 117.9 (5) |
C1—N2—C13 | 126.4 (5) | C14—C13—N2 | 118.8 (5) |
C1—N2—C3 | 110.8 (5) | C15—C14—C13 | 117.4 (6) |
C13—N2—C3 | 122.6 (5) | C15—C14—C19 | 121.4 (6) |
N2—C1—N1 | 113.7 (5) | C13—C14—C19 | 121.2 (6) |
N2—C1—H1A | 123.1 | C14—C15—C16 | 123.0 (6) |
N1—C1—H1A | 123.1 | C14—C15—H15A | 118.5 |
N1—C2—C3 | 102.7 (5) | C16—C15—H15A | 118.5 |
N1—C2—H2A | 111.2 | C17—C16—C15 | 117.9 (6) |
C3—C2—H2A | 111.2 | C17—C16—C20 | 121.7 (6) |
N1—C2—H2B | 111.2 | C15—C16—C20 | 120.3 (7) |
C3—C2—H2B | 111.2 | C16—C17—C18 | 122.3 (6) |
H2A—C2—H2B | 109.1 | C16—C17—H17A | 118.9 |
N2—C3—C2 | 102.5 (4) | C18—C17—H17A | 118.9 |
N2—C3—H3A | 111.3 | C13—C18—C17 | 116.4 (6) |
C2—C3—H3A | 111.3 | C13—C18—C21 | 122.2 (6) |
N2—C3—H3B | 111.3 | C17—C18—C21 | 121.4 (6) |
C2—C3—H3B | 111.3 | C14—C19—H19A | 109.5 |
H3A—C3—H3B | 109.2 | C14—C19—H19B | 109.5 |
C5—C4—C9 | 122.9 (6) | H19A—C19—H19B | 109.5 |
C5—C4—N1 | 118.9 (6) | C14—C19—H19C | 109.5 |
C9—C4—N1 | 118.2 (5) | H19A—C19—H19C | 109.5 |
C4—C5—C6 | 117.0 (7) | H19B—C19—H19C | 109.5 |
C4—C5—C10 | 121.0 (7) | C16—C20—H20A | 109.5 |
C6—C5—C10 | 122.0 (7) | C16—C20—H20B | 109.5 |
C7—C6—C5 | 120.9 (7) | H20A—C20—H20B | 109.5 |
C7—C6—H6A | 119.5 | C16—C20—H20C | 109.5 |
C5—C6—H6A | 119.5 | H20A—C20—H20C | 109.5 |
C8—C7—C6 | 118.7 (7) | H20B—C20—H20C | 109.5 |
C8—C7—C11 | 123.7 (8) | C18—C21—H21A | 109.5 |
C6—C7—C11 | 117.5 (8) | C18—C21—H21B | 109.5 |
C7—C8—C9 | 123.0 (7) | H21A—C21—H21B | 109.5 |
C7—C8—H8A | 118.5 | C18—C21—H21C | 109.5 |
C9—C8—H8A | 118.5 | H21A—C21—H21C | 109.5 |
C8—C9—C4 | 117.6 (6) | H21B—C21—H21C | 109.5 |
C8—C9—C12 | 119.9 (6) | Cl11—C100—Cl12 | 111.3 (5) |
C4—C9—C12 | 122.5 (6) | Cl11—C100—Cl13 | 109.0 (5) |
C5—C10—H10A | 109.5 | Cl12—C100—Cl13 | 112.0 (5) |
C5—C10—H10B | 109.5 | Cl11—C100—H10 | 108.1 |
H10A—C10—H10B | 109.5 | Cl12—C100—H10 | 108.1 |
C5—C10—H10C | 109.5 | Cl13—C100—H10 | 108.1 |
H10A—C10—H10C | 109.5 | Cl21—C200—Cl23 | 112.2 (6) |
H10B—C10—H10C | 109.5 | Cl21—C200—Cl22 | 108.1 (5) |
C7—C11—H11A | 109.5 | Cl23—C200—Cl22 | 106.8 (5) |
C7—C11—H11B | 109.5 | Cl21—C200—H20 | 109.9 |
H11A—C11—H11B | 109.5 | Cl23—C200—H20 | 109.9 |
C7—C11—H11C | 109.5 | Cl22—C200—H20 | 109.9 |
H11A—C11—H11C | 109.5 | ||
C13—N2—C1—N1 | 176.7 (5) | C5—C4—C9—C8 | −0.7 (9) |
C3—N2—C1—N1 | 1.7 (7) | N1—C4—C9—C8 | 177.6 (5) |
C4—N1—C1—N2 | 178.3 (5) | C5—C4—C9—C12 | −179.5 (6) |
C2—N1—C1—N2 | 0.4 (7) | N1—C4—C9—C12 | −1.2 (9) |
C1—N1—C2—C3 | −2.2 (6) | C1—N2—C13—C18 | −82.7 (7) |
C4—N1—C2—C3 | 179.9 (5) | C3—N2—C13—C18 | 91.8 (7) |
C1—N2—C3—C2 | −2.9 (6) | C1—N2—C13—C14 | 103.6 (7) |
C13—N2—C3—C2 | −178.1 (5) | C3—N2—C13—C14 | −81.9 (7) |
N1—C2—C3—N2 | 2.8 (5) | C18—C13—C14—C15 | 1.8 (9) |
C1—N1—C4—C5 | −91.4 (7) | N2—C13—C14—C15 | 175.0 (5) |
C2—N1—C4—C5 | 86.2 (7) | C18—C13—C14—C19 | 179.6 (6) |
C1—N1—C4—C9 | 90.3 (7) | N2—C13—C14—C19 | −7.1 (9) |
C2—N1—C4—C9 | −92.1 (7) | C13—C14—C15—C16 | 0.5 (9) |
C9—C4—C5—C6 | 1.1 (9) | C19—C14—C15—C16 | −177.3 (6) |
N1—C4—C5—C6 | −177.2 (5) | C14—C15—C16—C17 | −1.3 (10) |
C9—C4—C5—C10 | −177.1 (7) | C14—C15—C16—C20 | −178.8 (6) |
N1—C4—C5—C10 | 4.6 (10) | C15—C16—C17—C18 | −0.1 (9) |
C4—C5—C6—C7 | −0.8 (10) | C20—C16—C17—C18 | 177.3 (6) |
C10—C5—C6—C7 | 177.3 (7) | C14—C13—C18—C17 | −3.0 (9) |
C5—C6—C7—C8 | 0.3 (10) | N2—C13—C18—C17 | −176.4 (5) |
C5—C6—C7—C11 | 178.3 (6) | C14—C13—C18—C21 | 179.7 (6) |
C6—C7—C8—C9 | 0.1 (11) | N2—C13—C18—C21 | 6.3 (9) |
C11—C7—C8—C9 | −177.8 (6) | C16—C17—C18—C13 | 2.2 (9) |
C7—C8—C9—C4 | 0.1 (10) | C16—C17—C18—C21 | 179.5 (6) |
C7—C8—C9—C12 | 178.9 (6) |
Symmetry codes: (i) −x+y+1, −x+1, z; (ii) −y+1, x−y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···Br3iii | 0.95 | 2.58 | 3.373 (4) | 141 |
C100—H10···Br1i | 1.00 | 2.71 | 3.668 (5) | 161 |
C200—H20···Br2iv | 1.00 | 2.54 | 3.454 (6) | 152 |
Symmetry codes: (i) −x+y+1, −x+1, z; (iii) x, y−1, z; (iv) −y+1/3, −x+5/3, z−5/6. |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···Br3ii | 0.95 | 2.58 | 3.373 (4) | 141.3 |
C100—H10···Br1i | 1.00 | 2.71 | 3.668 (5) | 160.7 |
C200—H20···Br2iii | 1.00 | 2.54 | 3.454 (6) | 151.7 |
Symmetry codes: (i) −x+y+1, −x+1, z; (ii) x, y−1, z; (iii) −y+1/3, −x+5/3, z−5/6. |
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