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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2012 May 5;68(Pt 6):m737. doi: 10.1107/S1600536812018831

(Acetyl­acetonato-κ2 O,O′)carbon­yl[dicyclo­hex­yl(2,6-diisopropyl­phen­yl)phosphane-κP]rhodium(I)

Wade L Davis a, Sfiso D Mathobela a, Reinout Meijboom a,*
PMCID: PMC3379078  PMID: 22719299

Abstract

In the title compound, [Rh(C5H7O2){C12H17P(C6H11)2}(CO)], the RhI atom is coordinated by one carbonyl C, one P and two O atoms, forming a slighlty distorted square-planar configuration.

Related literature  

For background literature on the catalytic activity of rhodium–phosphine compounds, see Moloy & Wegman (1989 ▶); Nozaki et al. (1997 ▶); Ocando-Mavarez et al. (2003 ▶); Hayashi & Yamasaki (2003 ▶); Erasmus & Conradie (2011 ▶). For related rhodium compounds, see: Riihimaki et al. (2003 ▶); Brink et al. (2007 ▶); Davis & Meijboom (2011 ▶).graphic file with name e-68-0m737-scheme1.jpg

Experimental  

Crystal data  

  • [Rh(C5H7O2)(C24H39P)(CO)]

  • M r = 588.55

  • Monoclinic, Inline graphic

  • a = 16.750 (2) Å

  • b = 9.7334 (13) Å

  • c = 19.385 (3) Å

  • β = 111.669 (3)°

  • V = 2937.1 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.66 mm−1

  • T = 100 K

  • 0.29 × 0.23 × 0.22 mm

Data collection  

  • Bruker APEX DUO 4K-CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.553, T max = 0.746

  • 14224 measured reflections

  • 6007 independent reflections

  • 5516 reflections with I > 2σ(I)

  • R int = 0.049

Refinement  

  • R[F 2 > 2σ(F 2)] = 0.043

  • wR(F 2) = 0.105

  • S = 1.05

  • 6007 reflections

  • 322 parameters

  • 2 restraints

  • H-atom parameters constrained

  • Δρmax = 1.85 e Å−3

  • Δρmin = −1.42 e Å−3

  • Absolute structure: Flack (1983 ▶), 2437 Friedel pairs

  • Flack parameter: −0.03 (3)

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT and XPREP (Bruker, 2008 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶) and WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812018831/aa2053sup1.cif

e-68-0m737-sup1.cif (32.8KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018831/aa2053Isup2.hkl

e-68-0m737-Isup2.hkl (288.1KB, hkl)

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

Financial assistance from the South African National Research Foundation (SA NRF), the Research Fund of the University of Johannesburg, Sasol and TESP is gratefully acknowledged. H. Phaza is acknowledged for the data collection.

supplementary crystallographic information

Comment

Transition metal complexes bearing functionalized phosphines are of interest due to their potential catalytic properties (Ocando-Mavarez et al., 2003). These complexes are used with various chiral ligands in the process of highly enantioselective hydroformylation reactions (Nozaki et al., 1997). Studies illustrating the catalytic importance of rhodium(I) square-planar moieties have been conducted on rhodium mono- and di-phosphane complexes containing the symmetrical bidentate ligand, acac (acac = acetylacetonate) (Moloy & Wegman, 1989; Erasmus & Conradie, 2011) as well as rhodium-catalyzed asymmetric 1,4-addition (Hayashi & Yamasaki, 2003). This work is part of an ongoing investigation aimed at determing the steric effects induced by various phosphine ligands on a rhodium(I) metal centre.

The title compound, [Rh(acac)(CO){C12H17P(C6H11)2}] (acac = acetylacetonate), crystallizes in the non-centrosymmetric monoclinic space group, C c (Z=4). The Rh(I) atom has a slightly distorted square-planar geometric coordination (see Fig. 1), illustrated by C1—Rh1—P1 and O2—Rh1—O3 angles of 94.54 (1)° and 89.37 (1)°, respectively, deviating from the ideal 90° right angle. A slightly asymmetric coordination of the acac ligand is observed, whereby the Rh1—O2 distance (2.083 (3) Å) is longer than that for Rh1—O3 (2.059 (3) Å), which may be attributed to a trans influence of the phosphane ligand. The steric demand of the phosphane ligand is indicated by the smaller O3—Rh1—P1 angle, (86.64 (9)°), compared to that of the carbonyl ligand, O2—Rh1—C1 (94.97 (1)°). All geometric parameters are similar to previous reported complexes of the general formula [Rh(acac)(CO)L]; L = tertiary phosphane ligand (Davis & Meijboom, 2011; Brink et al., 2007; Riihimaki et al., 2003).

Experimental

A solution of [Rh(acac)(CO)2] (42.2 mg, 0.16 mmol) in acetone (5 ml) was slowly added to a solution of C12H17P(C6H11)2 (64.5 mg, 0.18 mmol) in acetone (5 ml). Slow evaporation of the solvent afforded the title compound as yellow crystals. Spectroscopic analysis: 31P NMR (CDCl3, 162 MHz, p.p.m.): 47.5 [d, 1J(Rh—P)= 165.7 Hz]; IR (CH2Cl2) ν(CO): 1959.2 cm-1.

Refinement

All H atoms were placed in geometrically idealized positions (C—H = 0.95–1.00) and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C) for aromatic, methine and methylene H atoms, and Uiso(H) = 1.5Ueq(C) for methyl H atoms respectively. Methyl torsion angles were refined from electron density. Friedel Pairs = 2437.

Figures

Fig. 1.

Fig. 1.

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Molecular structure of the title compound, showing the atom numbering system. Displacement ellipsoids are drawn at the 50% probability level. For the C atoms in rings; the first digit indicates ring number and the second digit indicates the position of the atom in the ring.

Crystal data

[Rh(C5H7O2)(C24H39P)(CO)] F(000) = 1240
Mr = 588.55 Dx = 1.331 Mg m−3
Monoclinic, Cc Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc Cell parameters from 5131 reflections
a = 16.750 (2) Å θ = 2.5–27.6°
b = 9.7334 (13) Å µ = 0.66 mm−1
c = 19.385 (3) Å T = 100 K
β = 111.669 (3)° Cubic, yellow
V = 2937.1 (7) Å3 0.29 × 0.23 × 0.22 mm
Z = 4
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Data collection

Bruker APEX DUO 4K-CCD diffractometer 6007 independent reflections
Radiation source: sealed tube 5516 reflections with I > 2σ(I)
Graphite monochromator Rint = 0.049
Detector resolution: 8.4 pixels mm-1 θmax = 28.2°, θmin = 2.5°
φ and ω scans h = −21→22
Absorption correction: multi-scan (SADABS; Bruker, 2008) k = −12→12
Tmin = 0.553, Tmax = 0.746 l = −25→24
14224 measured reflections
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Refinement

Refinement on F2 Secondary atom site location: difference Fourier map
Least-squares matrix: full Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043 H-atom parameters constrained
wR(F2) = 0.105 w = 1/[σ2(Fo2) + (0.0588P)2] where P = (Fo2 + 2Fc2)/3
S = 1.05 (Δ/σ)max < 0.001
6007 reflections Δρmax = 1.85 e Å−3
322 parameters Δρmin = −1.42 e Å−3
2 restraints Absolute structure: Flack (1983), 2437 Friedel pairs
Primary atom site location: structure-invariant direct methods Flack parameter: −0.03 (3)
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Special details

Experimental. The intensity data was collected on a Bruker Apex DUO 4 K CCD diffractometer using an exposure time of 2 s/frame. A total of 1125 frames were collected with a frame width of 0.5° covering up to θ = 28.18° with 99.1% completeness accomplished.
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.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
Rh1 1.04568 (3) 0.50680 (3) 0.55184 (3) 0.01467 (8)
P1 0.96331 (6) 0.64795 (10) 0.45914 (6) 0.0128 (2)
O1 0.9055 (2) 0.4101 (4) 0.5979 (2) 0.0355 (9)
O3 1.14853 (18) 0.5725 (3) 0.52656 (17) 0.0212 (6)
O2 1.12596 (19) 0.3671 (3) 0.62714 (18) 0.0223 (7)
C1 0.9568 (3) 0.4502 (5) 0.5774 (2) 0.0230 (9)
C31 0.9846 (2) 0.5943 (4) 0.3744 (2) 0.0151 (8)
H2 0.9303 0.6115 0.3309 0.018*
C36 1.0561 (3) 0.6742 (4) 0.3596 (2) 0.0187 (8)
H3A 1.0459 0.7742 0.3609 0.022*
H3B 1.1125 0.6528 0.3987 0.022*
C35 1.0568 (3) 0.6340 (5) 0.2839 (2) 0.0212 (9)
H4A 1.1039 0.6833 0.2753 0.025*
H4B 1.0019 0.6625 0.2449 0.025*
C34 1.0688 (3) 0.4798 (5) 0.2781 (3) 0.0271 (10)
H5A 1.1272 0.4535 0.312 0.033*
H5B 1.0636 0.457 0.2268 0.033*
C33 1.0022 (3) 0.3972 (5) 0.2977 (3) 0.0225 (9)
H6A 0.9442 0.4137 0.2598 0.027*
H6B 1.0149 0.2979 0.2977 0.027*
C32 1.0034 (3) 0.4391 (4) 0.3742 (2) 0.0177 (8)
H7A 1.0603 0.4184 0.4126 0.021*
H7B 0.9595 0.3862 0.3859 0.021*
C11 0.9794 (2) 0.8374 (4) 0.4696 (2) 0.0151 (8)
C12 1.0292 (2) 0.8964 (4) 0.5403 (2) 0.0157 (8)
C7 1.0743 (3) 0.8194 (4) 0.6126 (2) 0.0208 (9)
H10 1.0627 0.7193 0.6019 0.025*
C9 1.1720 (3) 0.8394 (5) 0.6400 (3) 0.0383 (13)
H11A 1.1927 0.8107 0.6011 0.057*
H11B 1.1998 0.7837 0.6845 0.057*
H11C 1.1859 0.9365 0.6518 0.057*
C8 1.0383 (4) 0.8585 (5) 0.6715 (3) 0.0405 (13)
H12A 1.0432 0.958 0.6796 0.061*
H12B 1.0708 0.811 0.718 0.061*
H12C 0.9778 0.8315 0.6548 0.061*
C13 1.0382 (4) 1.0397 (4) 0.5487 (4) 0.0209 (9)
H13 1.0712 1.0772 0.5959 0.025*
C14 0.9997 (3) 1.1268 (5) 0.4895 (3) 0.0245 (10)
H14 1.0064 1.2234 0.4961 0.029*
C15 0.9518 (3) 1.0737 (5) 0.4209 (3) 0.0218 (9)
H15 0.9255 1.1344 0.3805 0.026*
C16 0.9410 (2) 0.9319 (4) 0.4096 (2) 0.0161 (8)
C17 0.8849 (3) 0.8926 (4) 0.3296 (2) 0.0203 (9)
H17 0.885 0.7902 0.3256 0.024*
C19 0.9197 (3) 0.9524 (5) 0.2727 (3) 0.0269 (10)
H18A 0.9139 1.0527 0.2715 0.04*
H18B 0.887 0.9148 0.2234 0.04*
H18C 0.9805 0.9278 0.287 0.04*
C18 0.7919 (3) 0.9396 (5) 0.3118 (3) 0.0273 (10)
H19A 0.7689 0.8945 0.3457 0.041*
H19B 0.7568 0.9148 0.2605 0.041*
H19C 0.7906 1.0394 0.3178 0.041*
C21 0.8441 (2) 0.6307 (4) 0.4276 (2) 0.0165 (8)
H20 0.8194 0.6898 0.3824 0.02*
C22 0.8091 (3) 0.6873 (4) 0.4847 (3) 0.0220 (9)
H21A 0.8251 0.7853 0.4943 0.026*
H21B 0.8353 0.6365 0.532 0.026*
C23 0.7110 (3) 0.6732 (5) 0.4567 (3) 0.0290 (11)
H22A 0.6905 0.7054 0.4956 0.035*
H22B 0.6848 0.7323 0.4125 0.035*
C24 0.6826 (3) 0.5260 (5) 0.4366 (3) 0.0307 (11)
H23A 0.6191 0.521 0.4179 0.037*
H23B 0.7056 0.4676 0.4814 0.037*
C25 0.7146 (3) 0.4728 (5) 0.3773 (3) 0.0282 (11)
H24A 0.6876 0.5266 0.3311 0.034*
H24B 0.6972 0.3756 0.3661 0.034*
C26 0.8128 (3) 0.4839 (4) 0.4030 (3) 0.0216 (9)
H25A 0.8397 0.42 0.4449 0.026*
H25B 0.831 0.4564 0.3619 0.026*
C2 1.2259 (3) 0.5256 (5) 0.5547 (3) 0.0224 (9)
C5 1.2883 (3) 0.5932 (6) 0.5257 (3) 0.0346 (12)
H27A 1.2702 0.576 0.4723 0.052*
H27B 1.3458 0.5551 0.5513 0.052*
H27C 1.2893 0.6924 0.5346 0.052*
C3 1.2540 (3) 0.4204 (5) 0.6063 (2) 0.0245 (10)
H28 1.3128 0.3949 0.6212 0.029*
C4 1.2047 (3) 0.3483 (4) 0.6385 (2) 0.0238 (9)
C6 1.2468 (3) 0.2315 (5) 0.6923 (3) 0.0353 (12)
H30A 1.2111 0.2084 0.7209 0.053*
H30B 1.3038 0.2604 0.7262 0.053*
H30C 1.2523 0.1507 0.6642 0.053*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
Rh1 0.01337 (12) 0.01245 (13) 0.01730 (13) −0.00060 (14) 0.00463 (9) 0.00048 (14)
P1 0.0102 (4) 0.0110 (4) 0.0173 (5) −0.0018 (4) 0.0051 (4) −0.0003 (4)
O1 0.0222 (16) 0.046 (2) 0.0360 (19) −0.0074 (16) 0.0083 (15) 0.0175 (16)
O3 0.0128 (14) 0.0242 (16) 0.0269 (16) 0.0011 (12) 0.0076 (12) 0.0011 (13)
O2 0.0182 (15) 0.0164 (14) 0.0269 (17) 0.0012 (12) 0.0020 (13) 0.0057 (12)
C1 0.026 (2) 0.021 (2) 0.019 (2) −0.0007 (19) 0.0043 (18) 0.0068 (17)
C31 0.0133 (17) 0.0171 (18) 0.0155 (19) 0.0034 (15) 0.0060 (15) −0.0016 (14)
C36 0.0183 (19) 0.0192 (19) 0.020 (2) −0.0018 (16) 0.0091 (16) 0.0009 (16)
C35 0.016 (2) 0.029 (2) 0.023 (2) −0.0042 (18) 0.0127 (17) −0.0004 (18)
C34 0.022 (2) 0.036 (3) 0.029 (2) 0.0006 (19) 0.016 (2) −0.0075 (19)
C33 0.021 (2) 0.022 (2) 0.027 (2) −0.0014 (18) 0.0114 (18) −0.0071 (17)
C32 0.0127 (17) 0.0171 (19) 0.026 (2) 0.0004 (15) 0.0096 (16) −0.0027 (17)
C11 0.0090 (18) 0.017 (2) 0.021 (2) −0.0017 (15) 0.0078 (16) −0.0016 (16)
C12 0.013 (2) 0.0143 (17) 0.019 (2) −0.0025 (14) 0.0056 (17) −0.0003 (15)
C7 0.028 (2) 0.014 (2) 0.016 (2) 0.0003 (18) 0.0030 (17) 0.0014 (16)
C9 0.028 (2) 0.028 (3) 0.042 (3) −0.005 (2) −0.008 (2) 0.000 (2)
C8 0.075 (4) 0.029 (3) 0.024 (2) −0.007 (3) 0.025 (3) −0.002 (2)
C13 0.020 (2) 0.0188 (17) 0.028 (2) −0.004 (2) 0.0135 (19) −0.007 (3)
C14 0.030 (2) 0.0125 (19) 0.036 (3) 0.0042 (18) 0.018 (2) 0.0016 (17)
C15 0.019 (2) 0.017 (2) 0.030 (2) 0.0021 (17) 0.0097 (18) 0.0032 (17)
C16 0.0118 (17) 0.0167 (19) 0.021 (2) −0.0008 (15) 0.0073 (16) 0.0013 (16)
C17 0.0180 (19) 0.018 (2) 0.022 (2) 0.0019 (16) 0.0035 (16) 0.0009 (16)
C19 0.025 (2) 0.033 (2) 0.022 (2) 0.0050 (19) 0.0070 (19) 0.0047 (19)
C18 0.017 (2) 0.029 (2) 0.030 (2) 0.0018 (18) 0.0011 (18) 0.001 (2)
C21 0.0100 (17) 0.020 (2) 0.0190 (19) −0.0015 (15) 0.0050 (15) 0.0000 (15)
C22 0.0152 (18) 0.021 (2) 0.031 (2) −0.0007 (16) 0.0100 (17) −0.0059 (17)
C23 0.0135 (19) 0.033 (3) 0.043 (3) −0.0033 (18) 0.0138 (19) −0.010 (2)
C24 0.019 (2) 0.040 (3) 0.039 (3) −0.0161 (19) 0.019 (2) −0.017 (2)
C25 0.015 (2) 0.038 (3) 0.033 (3) −0.0107 (18) 0.011 (2) −0.013 (2)
C26 0.017 (2) 0.027 (2) 0.021 (2) −0.0037 (17) 0.0073 (17) −0.0056 (16)
C2 0.0127 (19) 0.026 (2) 0.026 (2) −0.0012 (16) 0.0035 (17) −0.0091 (17)
C5 0.015 (2) 0.051 (3) 0.039 (3) 0.001 (2) 0.011 (2) −0.002 (2)
C3 0.0144 (19) 0.026 (2) 0.028 (2) 0.0031 (17) 0.0012 (17) −0.0081 (18)
C4 0.027 (2) 0.018 (2) 0.019 (2) 0.0032 (17) 0.0005 (17) −0.0056 (16)
C6 0.027 (2) 0.020 (2) 0.042 (3) 0.0058 (19) −0.007 (2) 0.001 (2)
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Geometric parameters (Å, º)

Rh1—C1 1.820 (5) C14—C15 1.374 (7)
Rh1—O3 2.059 (3) C14—H14 0.95
Rh1—O2 2.083 (3) C15—C16 1.399 (6)
Rh1—P1 2.2780 (12) C15—H15 0.95
P1—C11 1.864 (4) C16—C17 1.536 (6)
P1—C21 1.868 (4) C17—C18 1.536 (6)
P1—C31 1.879 (4) C17—C19 1.539 (7)
O1—C1 1.141 (6) C17—H17 1
O3—C2 1.289 (5) C19—H18A 0.98
O2—C4 1.268 (5) C19—H18B 0.98
C31—C36 1.542 (6) C19—H18C 0.98
C31—C32 1.543 (6) C18—H19A 0.98
C31—H2 1 C18—H19B 0.98
C36—C35 1.523 (6) C18—H19C 0.98
C36—H3A 0.99 C21—C22 1.534 (6)
C36—H3B 0.99 C21—C26 1.536 (6)
C35—C34 1.525 (6) C21—H20 1
C35—H4A 0.99 C22—C23 1.534 (5)
C35—H4B 0.99 C22—H21A 0.99
C34—C33 1.533 (7) C22—H21B 0.99
C34—H5A 0.99 C23—C24 1.514 (6)
C34—H5B 0.99 C23—H22A 0.99
C33—C32 1.531 (6) C23—H22B 0.99
C33—H6A 0.99 C24—C25 1.527 (7)
C33—H6B 0.99 C24—H23A 0.99
C32—H7A 0.99 C24—H23B 0.99
C32—H7B 0.99 C25—C26 1.537 (6)
C11—C12 1.435 (5) C25—H24A 0.99
C11—C16 1.435 (6) C25—H24B 0.99
C12—C13 1.405 (5) C26—H25A 0.99
C12—C7 1.522 (6) C26—H25B 0.99
C7—C8 1.523 (7) C2—C3 1.387 (7)
C7—C9 1.535 (7) C2—C5 1.508 (7)
C7—H10 1 C5—H27A 0.98
C9—H11A 0.98 C5—H27B 0.98
C9—H11B 0.98 C5—H27C 0.98
C9—H11C 0.98 C3—C4 1.396 (7)
C8—H12A 0.98 C3—H28 0.95
C8—H12B 0.98 C4—C6 1.527 (6)
C8—H12C 0.98 C6—H30A 0.98
C13—C14 1.380 (8) C6—H30B 0.98
C13—H13 0.95 C6—H30C 0.98
C1—Rh1—O3 178.09 (18) C14—C15—C16 121.2 (4)
C1—Rh1—O2 89.60 (17) C14—C15—H15 119.4
O3—Rh1—O2 89.37 (12) C16—C15—H15 119.4
C1—Rh1—P1 94.54 (14) C15—C16—C11 120.8 (4)
O3—Rh1—P1 86.64 (9) C15—C16—C17 113.5 (3)
O2—Rh1—P1 173.12 (11) C11—C16—C17 125.6 (4)
C11—P1—C21 102.61 (18) C16—C17—C18 110.1 (4)
C11—P1—C31 107.71 (19) C16—C17—C19 112.2 (4)
C21—P1—C31 102.32 (18) C18—C17—C19 110.4 (4)
C11—P1—Rh1 119.33 (13) C16—C17—H17 108
C21—P1—Rh1 117.86 (14) C18—C17—H17 108
C31—P1—Rh1 105.47 (13) C19—C17—H17 108
C2—O3—Rh1 126.0 (3) C17—C19—H18A 109.5
C4—O2—Rh1 125.3 (3) C17—C19—H18B 109.5
O1—C1—Rh1 174.9 (4) H18A—C19—H18B 109.5
C36—C31—C32 108.7 (3) C17—C19—H18C 109.5
C36—C31—P1 115.7 (3) H18A—C19—H18C 109.5
C32—C31—P1 112.3 (3) H18B—C19—H18C 109.5
C36—C31—H2 106.5 C17—C18—H19A 109.5
C32—C31—H2 106.5 C17—C18—H19B 109.5
P1—C31—H2 106.5 H19A—C18—H19B 109.5
C35—C36—C31 109.4 (3) C17—C18—H19C 109.5
C35—C36—H3A 109.8 H19A—C18—H19C 109.5
C31—C36—H3A 109.8 H19B—C18—H19C 109.5
C35—C36—H3B 109.8 C22—C21—C26 112.4 (3)
C31—C36—H3B 109.8 C22—C21—P1 112.2 (3)
H3A—C36—H3B 108.2 C26—C21—P1 112.7 (3)
C36—C35—C34 111.9 (4) C22—C21—H20 106.3
C36—C35—H4A 109.2 C26—C21—H20 106.3
C34—C35—H4A 109.2 P1—C21—H20 106.3
C36—C35—H4B 109.2 C21—C22—C23 110.9 (3)
C34—C35—H4B 109.2 C21—C22—H21A 109.5
H4A—C35—H4B 107.9 C23—C22—H21A 109.5
C35—C34—C33 111.7 (4) C21—C22—H21B 109.5
C35—C34—H5A 109.3 C23—C22—H21B 109.5
C33—C34—H5A 109.3 H21A—C22—H21B 108.1
C35—C34—H5B 109.3 C24—C23—C22 111.7 (4)
C33—C34—H5B 109.3 C24—C23—H22A 109.3
H5A—C34—H5B 107.9 C22—C23—H22A 109.3
C32—C33—C34 110.5 (4) C24—C23—H22B 109.3
C32—C33—H6A 109.5 C22—C23—H22B 109.3
C34—C33—H6A 109.5 H22A—C23—H22B 107.9
C32—C33—H6B 109.5 C23—C24—C25 110.5 (4)
C34—C33—H6B 109.5 C23—C24—H23A 109.6
H6A—C33—H6B 108.1 C25—C24—H23A 109.6
C33—C32—C31 109.5 (3) C23—C24—H23B 109.6
C33—C32—H7A 109.8 C25—C24—H23B 109.6
C31—C32—H7A 109.8 H23A—C24—H23B 108.1
C33—C32—H7B 109.8 C24—C25—C26 111.3 (4)
C31—C32—H7B 109.8 C24—C25—H24A 109.4
H7A—C32—H7B 108.2 C26—C25—H24A 109.4
C12—C11—C16 116.4 (4) C24—C25—H24B 109.4
C12—C11—P1 120.7 (3) C26—C25—H24B 109.4
C16—C11—P1 122.9 (3) H24A—C25—H24B 108
C13—C12—C11 120.5 (4) C21—C26—C25 111.6 (4)
C13—C12—C7 112.8 (4) C21—C26—H25A 109.3
C11—C12—C7 126.7 (4) C25—C26—H25A 109.3
C12—C7—C8 111.6 (4) C21—C26—H25B 109.3
C12—C7—C9 111.1 (4) C25—C26—H25B 109.3
C8—C7—C9 112.1 (4) H25A—C26—H25B 108
C12—C7—H10 107.3 O3—C2—C3 126.0 (5)
C8—C7—H10 107.3 O3—C2—C5 114.5 (4)
C9—C7—H10 107.3 C3—C2—C5 119.5 (4)
C7—C9—H11A 109.5 C2—C5—H27A 109.5
C7—C9—H11B 109.5 C2—C5—H27B 109.5
H11A—C9—H11B 109.5 H27A—C5—H27B 109.5
C7—C9—H11C 109.5 C2—C5—H27C 109.5
H11A—C9—H11C 109.5 H27A—C5—H27C 109.5
H11B—C9—H11C 109.5 H27B—C5—H27C 109.5
C7—C8—H12A 109.5 C2—C3—C4 126.5 (4)
C7—C8—H12B 109.5 C2—C3—H28 116.8
H12A—C8—H12B 109.5 C4—C3—H28 116.8
C7—C8—H12C 109.5 O2—C4—C3 126.8 (4)
H12A—C8—H12C 109.5 O2—C4—C6 114.5 (4)
H12B—C8—H12C 109.5 C3—C4—C6 118.7 (4)
C14—C13—C12 121.1 (5) C4—C6—H30A 109.5
C14—C13—H13 119.4 C4—C6—H30B 109.5
C12—C13—H13 119.4 H30A—C6—H30B 109.5
C15—C14—C13 119.9 (4) C4—C6—H30C 109.5
C15—C14—H14 120 H30A—C6—H30C 109.5
C13—C14—H14 120 H30B—C6—H30C 109.5
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AA2053).

References

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812018831/aa2053sup1.cif

e-68-0m737-sup1.cif (32.8KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018831/aa2053Isup2.hkl

e-68-0m737-Isup2.hkl (288.1KB, hkl)

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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