Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801006304/om6017sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801006304/om6017Isup2.hkl |
CCDC reference: 165634
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.012 Å
- R factor = 0.047
- wR factor = 0.161
- Data-to-parameter ratio = 12.9
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
CRYSC_01 Alert C The word below has not been recognised as a standard identifier. deep PLAT_213 Alert C Atom C11B has ADP max/min Ratio ........... 3.80
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check
A mixture of (±)-1-hydroxy-1,2-dihydroacenaphthylene, (I) (1.700 g, 10.0 mmol) and Cr(CO)6 (1.10 g, 5.0 mmol) in 50 ml of 1:1 nBu2O/heptane was thoroughly purged with argon and then refluxed for 72 h. After cooling to 293 K, the red solution was filtered (Celite) and the solvent removed in vacuo. Thin-layer chromatographic analysis (3:1 hexane/ethyl acetate) showed the presence of seven components. Flash chromatography (SiO2 under N2) provided 0.35 g (23% isolated yield) of a mixtutre of two Cr(CO)3 complexes of the alcohol, and repeating the separation on this fraction produced a pure sample, 0.10 g, 6.5% yield, of the more polar (minor) isomer, (II) [m.p. 393 K (decomposition)]. The other (less polar and less stable) Cr(CO)3 isomer was assigned the endo configuration.
The space group, P21/a, was uniquely determined from the systematic absences. The H atoms were located from difference maps and were included at geometrically idealized positions with O—H = 0.82 and C—H = 0.93–0.98 Å, in a riding mode with isotropic displacement parameters 1.2 (C atoms) and 1.5 (O atoms) times the thermal displacement parameters of the atoms to which they were attached. Two void areas of 26 Å3 each were indicated by the program PLATON (Spek, 1990) with no electron density in the difference map in those areas. The routine SQUEEZE was attempted but it could not eliminate the voids.
Treatment of 1-hydroxy-1,2-dihydroacenaphthylene, (I), with Cr(CO)6 yields two Cr(CO)3 complexes, in addition to a number of other products (Simion, 1996). Based on 1H NMR results, and on previous results from 1-indanol complexation (Jaouen & Dabard, 1971; Top et al., 1979), it was thought that the two isomers involved exo and endo η6-coordination of Cr(CO)3 on the acenaphthylene ring nearest the OH group, and that initial complexation would occur with OH mediation to give the endo product. By means of OH ionization, and recombination via the exo face, one would obtain some of the exo isomer, (II). The structure of (II) was confirmed by a single-crystal X-ray diffraction study.
The asymmetric unit of (II) is composed of two independent conformers, A and B (Figs. 1 and 2). The two conformations are different, as is evident from a comparison of Figs. 1 and 2. This difference is mainly in the projection of the Cr(CO)3 fragment relative to the C atoms of the arene ring being complexed. In conformer A, the Cr(CO)3 unit is staggered, whereas in B, it is about midway between staggered and eclipsed. Several X-ray structures of naphthalene–Cr(CO)3 complexes have been included in the Cambridge Structural Database (Allen & Kennard, 1993). In naphthalene–Cr(CO)3 (Kunz & Nowacki, 1967), the Cr(CO)3 conformation resembles that of our B conformer.
The Cr—CCO distances lie in the range 1.822 (9)–1.847 (10) Å [mean 1.833 (9) Å], while the C≡O distances lie in the narrow range 1.141 (9)–1.153 (9) Å [mean 1.149 (4) Å]. These distances are in excellent agreement with the values reported for the corresponding distances in organometallic complexes (Orpen et al., 1994). The Cr—Caromatic distances span over a wide range [2.189 (7)–2.318 (8) Å], with Cr–centroid distances of 1.744 (10) and 1.747 (10) Å for conformers A and B, respectively. In both naphthalene–Cr(CO)3 and cyclopropanaphthalene–Cr(CO)3 complexes (Müller et al., 1989), one sees a slightly displaced Cr(CO)3 relative to the center of the arene ring. In the former, the Cr—Cbridgehead carbon bonds are 2.306 and 2.337 Å versus an average of 2.200 Å for the four outside distances. Similar distances are observed in the cyclopropanaphthalene complex. One sees the same features in our A and B conformers. Thus, in A, the two central bonds average to 2.310 Å, versus 2.197 Å for the outside bonds (2.290 Å versus 2.221 Å for B). The remaining molecular dimensions in both the conformers are normal with mean bond lengths Csp3—Csp3 = 1.553 (1), Csp3—Csp2 - 1.516 (10), C—Caromatic = 1.40 (3) and Csp3—O = 1.423 (6) Å.
In both conformers, the acenaphthylene rings are essentially planar with the maximum deviation of any atom from the mean-planes being 0.061 (7) and 0.059 (7) Å, for atoms C6A and C6B in conformers A and B, respectively. The hydroxyl O atoms lie 1.187 (7) and 1.022 (8) Å from the acenaphthylene rings and the orientation of hydroxyl H atoms is different in the two molecules. The hydroxyl groups are involved in hydrogen bonding between the conformers lying about glide planes [O4A—H4A···O4B and O4B—H4B···O4A, with O···O distances of 2.835 (8) and 2.771 (8) Å, respectively], thus resulting in chains of structures along the a axis (Fig. 3); details are given in Table 2. The effect of hydrogen bonding is manifested in differences in bond angles around C15A and C15B, e.g. the O4—C15—C14 angles in conformers A and B are 109.4 (6) and 114.0 (7)°, respectively.
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1994); program(s) used to solve structure: SAPI91 (Fan 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: TEXSAN; software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
[Cr(C12H10O)(CO)3] | Dx = 1.535 Mg m−3 |
Mr = 306.23 | Melting point: 393 K |
Monoclinic, P21/a | Mo Kα radiation, λ = 0.71069 Å |
a = 10.0838 (16) Å | Cell parameters from 25 reflections |
b = 25.963 (4) Å | θ = 10.0–15.0° |
c = 10.1696 (17) Å | µ = 0.87 mm−1 |
β = 95.641 (14)° | T = 296 K |
V = 2649.6 (7) Å3 | Prism, deep red |
Z = 8 | 0.20 × 0.20 × 0.10 mm |
F(000) = 1248 |
Rigaku AFC-6S diffractometer | 1483 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.087 |
Graphite monochromator | θmax = 25.0°, θmin = 2.0° |
ω/2θ scans | h = 0→12 |
Absorption correction: empirical (using intensity measurements) via ψ-scan (3 reflections) (North et al., 1968) | k = 0→30 |
Tmin = 0.84, Tmax = 0.92 | l = −12→12 |
4946 measured reflections | 3 standard reflections every 200 reflections |
4668 independent reflections | intensity decay: <0.22% |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.161 | H-atom parameters constrained |
S = 0.95 | w = 1/[σ2(Fo2) + (0.049P)2] where P = (Fo2 + 2Fc2)/3 |
4668 reflections | (Δ/σ)max < 0.001 |
363 parameters | Δρmax = 0.40 e Å−3 |
0 restraints | Δρmin = −0.37 e Å−3 |
[Cr(C12H10O)(CO)3] | V = 2649.6 (7) Å3 |
Mr = 306.23 | Z = 8 |
Monoclinic, P21/a | Mo Kα radiation |
a = 10.0838 (16) Å | µ = 0.87 mm−1 |
b = 25.963 (4) Å | T = 296 K |
c = 10.1696 (17) Å | 0.20 × 0.20 × 0.10 mm |
β = 95.641 (14)° |
Rigaku AFC-6S diffractometer | 1483 reflections with I > 2σ(I) |
Absorption correction: empirical (using intensity measurements) via ψ-scan (3 reflections) (North et al., 1968) | Rint = 0.087 |
Tmin = 0.84, Tmax = 0.92 | 3 standard reflections every 200 reflections |
4946 measured reflections | intensity decay: <0.22% |
4668 independent reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.161 | H-atom parameters constrained |
S = 0.95 | Δρmax = 0.40 e Å−3 |
4668 reflections | Δρmin = −0.37 e Å−3 |
363 parameters |
x | y | z | Uiso*/Ueq | ||
Cr1A | 0.12684 (11) | 0.11740 (5) | 0.94167 (12) | 0.0390 (4) | |
O1A | 0.1539 (6) | 0.2095 (2) | 1.1164 (6) | 0.076 (2) | |
O2A | 0.4141 (6) | 0.1277 (3) | 0.9023 (6) | 0.098 (3) | |
O3A | 0.2096 (6) | 0.0515 (2) | 1.1753 (6) | 0.076 (2) | |
O4A | −0.0733 (5) | 0.2387 (3) | 0.6687 (6) | 0.0657 (17) | |
H4A | −0.0121 | 0.2381 | 0.6212 | 0.098* | |
C1A | 0.1429 (8) | 0.1742 (4) | 1.0492 (8) | 0.050 (2) | |
C2A | 0.3033 (9) | 0.1233 (4) | 0.9188 (8) | 0.061 (3) | |
C3A | 0.1741 (8) | 0.0763 (3) | 1.0851 (8) | 0.049 (2) | |
C4A | −0.0891 (7) | 0.1396 (3) | 0.8773 (7) | 0.040 (2) | |
C5A | −0.0009 (7) | 0.1628 (3) | 0.7972 (7) | 0.041 (2) | |
C6A | 0.0824 (8) | 0.1327 (4) | 0.7299 (7) | 0.053 (2) | |
H6A | 0.1371 | 0.1474 | 0.6717 | 0.064* | |
C7A | 0.0824 (8) | 0.0782 (3) | 0.7519 (8) | 0.051 (2) | |
H7A | 0.1372 | 0.0571 | 0.7067 | 0.061* | |
C8A | 0.0038 (8) | 0.0568 (3) | 0.8376 (8) | 0.050 (2) | |
H8A | 0.0117 | 0.0217 | 0.8554 | 0.060* | |
C9A | −0.0900 (7) | 0.0858 (3) | 0.9010 (7) | 0.041 (2) | |
C10A | −0.1861 (8) | 0.0680 (3) | 0.9859 (8) | 0.053 (2) | |
H10A | −0.1899 | 0.0333 | 1.0078 | 0.063* | |
C11A | −0.2712 (8) | 0.1019 (4) | 1.0338 (8) | 0.058 (3) | |
H11A | −0.3360 | 0.0893 | 1.0843 | 0.070* | |
C12A | −0.2667 (8) | 0.1563 (4) | 1.0110 (8) | 0.053 (2) | |
H12A | −0.3259 | 0.1784 | 1.0472 | 0.064* | |
C13A | −0.1739 (8) | 0.1747 (3) | 0.9353 (8) | 0.046 (2) | |
C14A | −0.1373 (8) | 0.2277 (3) | 0.8915 (9) | 0.060 (2) | |
H14A | −0.1055 | 0.2485 | 0.9673 | 0.072* | |
H14B | −0.2142 | 0.2445 | 0.8455 | 0.072* | |
C15A | −0.0259 (8) | 0.2211 (3) | 0.7979 (8) | 0.050 (2) | |
H15A | 0.0549 | 0.2397 | 0.8318 | 0.060* | |
Cr1B | −0.44381 (12) | 0.09708 (5) | 0.44729 (12) | 0.0451 (4) | |
O1B | −0.5489 (7) | 0.1597 (3) | 0.2151 (7) | 0.089 (2) | |
O2B | −0.7255 (6) | 0.0714 (3) | 0.4910 (7) | 0.093 (2) | |
O3B | −0.4268 (7) | 0.0074 (3) | 0.2652 (7) | 0.091 (2) | |
O4B | −0.3279 (6) | 0.2604 (2) | 0.5543 (6) | 0.0663 (17) | |
H4B | −0.2733 | 0.2523 | 0.6160 | 0.099* | |
C1B | −0.5062 (8) | 0.1350 (4) | 0.3036 (9) | 0.058 (3) | |
C2B | −0.6170 (10) | 0.0811 (4) | 0.4735 (8) | 0.066 (3) | |
C3B | −0.4363 (8) | 0.0410 (4) | 0.3367 (9) | 0.056 (2) | |
C4B | −0.2441 (8) | 0.1370 (3) | 0.4815 (7) | 0.0366 (19) | |
C5B | −0.3450 (7) | 0.1679 (3) | 0.5285 (7) | 0.039 (2) | |
C6B | −0.4188 (8) | 0.1475 (3) | 0.6264 (8) | 0.051 (2) | |
H6B | −0.4806 | 0.1677 | 0.6649 | 0.061* | |
C7B | −0.3974 (8) | 0.0967 (4) | 0.6643 (8) | 0.050 (2) | |
H7B | −0.4464 | 0.0834 | 0.7292 | 0.060* | |
C8B | −0.3049 (8) | 0.0641 (3) | 0.6095 (8) | 0.054 (2) | |
H8B | −0.2993 | 0.0295 | 0.6331 | 0.064* | |
C9B | −0.2206 (8) | 0.0845 (3) | 0.5183 (8) | 0.046 (2) | |
C10B | −0.1167 (9) | 0.0594 (4) | 0.4567 (9) | 0.067 (3) | |
H10B | −0.0973 | 0.0249 | 0.4745 | 0.080* | |
C11B | −0.0462 (9) | 0.0863 (6) | 0.3715 (10) | 0.085 (4) | |
H11B | 0.0229 | 0.0695 | 0.3348 | 0.102* | |
C12B | −0.0719 (9) | 0.1376 (5) | 0.3366 (10) | 0.077 (3) | |
H12B | −0.0214 | 0.1544 | 0.2779 | 0.092* | |
C13B | −0.1720 (8) | 0.1625 (4) | 0.3898 (8) | 0.050 (2) | |
C14B | −0.2295 (9) | 0.2157 (4) | 0.3699 (8) | 0.068 (3) | |
H14C | −0.2646 | 0.2208 | 0.2785 | 0.081* | |
H14D | −0.1620 | 0.2416 | 0.3932 | 0.081* | |
C15B | −0.3429 (8) | 0.2192 (3) | 0.4625 (8) | 0.052 (2) | |
H15B | −0.4276 | 0.2238 | 0.4076 | 0.062* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cr1A | 0.0314 (7) | 0.0461 (8) | 0.0396 (7) | 0.0008 (7) | 0.0029 (6) | −0.0046 (7) |
O1A | 0.083 (5) | 0.064 (5) | 0.078 (5) | −0.017 (4) | −0.003 (4) | −0.025 (4) |
O2A | 0.040 (4) | 0.172 (8) | 0.084 (5) | 0.000 (5) | 0.019 (4) | −0.013 (5) |
O3A | 0.092 (5) | 0.079 (5) | 0.056 (4) | −0.003 (4) | −0.001 (4) | 0.020 (4) |
O4A | 0.054 (4) | 0.073 (4) | 0.071 (4) | 0.001 (4) | 0.006 (3) | 0.020 (4) |
C1A | 0.046 (6) | 0.057 (7) | 0.046 (6) | −0.010 (5) | −0.003 (4) | −0.004 (5) |
C2A | 0.039 (5) | 0.096 (8) | 0.048 (5) | −0.001 (6) | 0.004 (4) | −0.009 (5) |
C3A | 0.055 (6) | 0.056 (6) | 0.037 (5) | −0.015 (5) | 0.011 (5) | −0.007 (5) |
C4A | 0.036 (5) | 0.041 (5) | 0.040 (5) | −0.001 (4) | −0.005 (4) | −0.007 (4) |
C5A | 0.033 (5) | 0.050 (6) | 0.039 (5) | −0.004 (4) | 0.005 (4) | −0.003 (4) |
C6A | 0.043 (5) | 0.082 (8) | 0.037 (5) | −0.008 (5) | 0.013 (4) | 0.010 (5) |
C7A | 0.054 (6) | 0.058 (7) | 0.041 (5) | 0.001 (5) | 0.009 (4) | −0.019 (5) |
C8A | 0.056 (6) | 0.047 (6) | 0.045 (5) | −0.006 (5) | −0.006 (5) | −0.005 (5) |
C9A | 0.032 (5) | 0.051 (7) | 0.040 (5) | −0.005 (4) | 0.005 (4) | −0.008 (4) |
C10A | 0.044 (6) | 0.057 (6) | 0.054 (6) | −0.002 (5) | −0.005 (5) | 0.004 (5) |
C11A | 0.038 (5) | 0.079 (8) | 0.059 (6) | −0.012 (5) | 0.011 (4) | 0.009 (5) |
C12A | 0.029 (5) | 0.076 (7) | 0.054 (6) | −0.002 (5) | 0.004 (4) | −0.011 (5) |
C13A | 0.040 (5) | 0.043 (6) | 0.053 (6) | 0.012 (4) | −0.002 (4) | 0.001 (4) |
C14A | 0.048 (5) | 0.055 (6) | 0.079 (7) | 0.015 (5) | 0.014 (5) | 0.009 (5) |
C15A | 0.040 (5) | 0.053 (6) | 0.053 (6) | −0.006 (4) | −0.013 (4) | 0.009 (5) |
Cr1B | 0.0365 (8) | 0.0571 (9) | 0.0419 (8) | −0.0011 (7) | 0.0040 (6) | −0.0039 (7) |
O1B | 0.084 (5) | 0.115 (6) | 0.061 (4) | 0.012 (4) | −0.023 (4) | 0.006 (4) |
O2B | 0.041 (4) | 0.153 (7) | 0.085 (5) | −0.017 (4) | 0.018 (4) | 0.007 (5) |
O3B | 0.128 (6) | 0.070 (5) | 0.076 (5) | −0.017 (5) | 0.020 (4) | −0.030 (4) |
O4B | 0.070 (5) | 0.052 (4) | 0.076 (5) | 0.004 (3) | 0.004 (3) | −0.006 (4) |
C1B | 0.042 (6) | 0.083 (8) | 0.047 (6) | 0.004 (5) | −0.008 (5) | 0.003 (5) |
C2B | 0.054 (7) | 0.097 (8) | 0.047 (6) | −0.014 (6) | 0.005 (5) | −0.011 (5) |
C3B | 0.053 (6) | 0.058 (7) | 0.057 (6) | −0.009 (5) | 0.007 (5) | −0.003 (5) |
C4B | 0.035 (5) | 0.043 (5) | 0.031 (5) | −0.006 (4) | −0.001 (4) | −0.005 (4) |
C5B | 0.033 (5) | 0.041 (5) | 0.043 (5) | 0.003 (4) | 0.005 (4) | 0.008 (4) |
C6B | 0.048 (6) | 0.044 (6) | 0.062 (6) | 0.006 (5) | 0.011 (5) | 0.001 (5) |
C7B | 0.050 (6) | 0.064 (7) | 0.039 (5) | −0.010 (5) | 0.013 (4) | −0.010 (5) |
C8B | 0.060 (6) | 0.052 (6) | 0.046 (6) | −0.002 (5) | −0.010 (5) | 0.011 (5) |
C9B | 0.040 (5) | 0.048 (7) | 0.048 (5) | 0.008 (4) | −0.008 (4) | −0.006 (5) |
C10B | 0.048 (6) | 0.082 (8) | 0.069 (7) | 0.022 (6) | 0.002 (5) | −0.023 (6) |
C11B | 0.023 (5) | 0.166 (13) | 0.066 (7) | 0.037 (7) | 0.002 (5) | −0.032 (8) |
C12B | 0.042 (6) | 0.123 (10) | 0.068 (7) | 0.003 (7) | 0.011 (5) | 0.005 (7) |
C13B | 0.038 (5) | 0.064 (7) | 0.045 (5) | 0.008 (5) | −0.005 (4) | −0.001 (5) |
C14B | 0.069 (7) | 0.093 (8) | 0.043 (5) | −0.022 (6) | 0.015 (5) | 0.007 (5) |
C15B | 0.053 (6) | 0.047 (6) | 0.054 (6) | 0.001 (4) | −0.006 (5) | −0.008 (5) |
Cr1A—C2A | 1.824 (9) | Cr1B—C1B | 1.822 (9) |
Cr1A—C3A | 1.833 (9) | Cr1B—C2B | 1.840 (10) |
Cr1A—C1A | 1.834 (10) | Cr1B—C3B | 1.847 (10) |
Cr1A—C7A | 2.189 (7) | Cr1B—C7B | 2.210 (8) |
Cr1A—C6A | 2.192 (8) | Cr1B—C5B | 2.211 (8) |
Cr1A—C5A | 2.198 (8) | Cr1B—C8B | 2.227 (8) |
Cr1A—C8A | 2.209 (8) | Cr1B—C6B | 2.237 (8) |
Cr1A—C4A | 2.285 (8) | Cr1B—C4B | 2.261 (7) |
Cr1A—C9A | 2.334 (8) | Cr1B—C9B | 2.318 (8) |
O1A—C1A | 1.141 (9) | O1B—C1B | 1.152 (9) |
O2A—C2A | 1.152 (9) | O2B—C2B | 1.153 (9) |
O3A—C3A | 1.149 (9) | O3B—C3B | 1.145 (9) |
O4A—C15A | 1.429 (8) | O4B—C15B | 1.417 (8) |
O4A—H4A | 0.8200 | O4B—H4B | 0.8200 |
C4A—C5A | 1.399 (10) | C4B—C13B | 1.403 (11) |
C4A—C9A | 1.418 (10) | C4B—C5B | 1.415 (10) |
C4A—C13A | 1.419 (10) | C4B—C9B | 1.427 (10) |
C5A—C6A | 1.377 (10) | C5B—C6B | 1.403 (10) |
C5A—C15A | 1.536 (11) | C5B—C15B | 1.494 (10) |
C6A—C7A | 1.434 (11) | C6B—C7B | 1.385 (10) |
C6A—H6A | 0.9300 | C6B—H6B | 0.9300 |
C7A—C8A | 1.353 (10) | C7B—C8B | 1.414 (11) |
C7A—H7A | 0.9300 | C7B—H7B | 0.9300 |
C8A—C9A | 1.413 (10) | C8B—C9B | 1.420 (11) |
C8A—H8A | 0.9300 | C8B—H8B | 0.9300 |
C9A—C10A | 1.436 (10) | C9B—C10B | 1.429 (11) |
C10A—C11A | 1.354 (11) | C10B—C11B | 1.366 (13) |
C10A—H10A | 0.9300 | C10B—H10B | 0.9300 |
C11A—C12A | 1.433 (11) | C11B—C12B | 1.396 (14) |
C11A—H11A | 0.9300 | C11B—H11B | 0.9300 |
C12A—C13A | 1.355 (11) | C12B—C13B | 1.355 (12) |
C12A—H12A | 0.9300 | C12B—H12B | 0.9300 |
C13A—C14A | 1.502 (10) | C13B—C14B | 1.506 (11) |
C14A—C15A | 1.552 (10) | C14B—C15B | 1.554 (10) |
C14A—H14A | 0.9700 | C14B—H14C | 0.9700 |
C14A—H14B | 0.9700 | C14B—H14D | 0.9700 |
C15A—H15A | 0.9800 | C15B—H15B | 0.9800 |
C2A—Cr1A—C3A | 88.2 (4) | C1B—Cr1B—C2B | 88.9 (4) |
C2A—Cr1A—C1A | 88.8 (4) | C1B—Cr1B—C3B | 88.3 (4) |
C3A—Cr1A—C1A | 89.6 (4) | C2B—Cr1B—C3B | 90.3 (4) |
C2A—Cr1A—C7A | 92.6 (4) | C1B—Cr1B—C7B | 145.6 (4) |
C3A—Cr1A—C7A | 116.4 (3) | C2B—Cr1B—C7B | 88.0 (3) |
C1A—Cr1A—C7A | 154.0 (4) | C3B—Cr1B—C7B | 126.0 (4) |
C2A—Cr1A—C6A | 88.2 (3) | C1B—Cr1B—C5B | 87.5 (3) |
C3A—Cr1A—C6A | 154.1 (4) | C2B—Cr1B—C5B | 122.2 (3) |
C1A—Cr1A—C6A | 116.0 (4) | C3B—Cr1B—C5B | 147.1 (3) |
C7A—Cr1A—C6A | 38.2 (3) | C7B—Cr1B—C5B | 65.6 (3) |
C2A—Cr1A—C5A | 112.7 (4) | C1B—Cr1B—C8B | 160.7 (4) |
C3A—Cr1A—C5A | 159.0 (3) | C2B—Cr1B—C8B | 110.0 (4) |
C1A—Cr1A—C5A | 88.8 (3) | C3B—Cr1B—C8B | 95.0 (4) |
C7A—Cr1A—C5A | 66.7 (3) | C7B—Cr1B—C8B | 37.1 (3) |
C6A—Cr1A—C5A | 36.5 (3) | C5B—Cr1B—C8B | 79.4 (3) |
C2A—Cr1A—C8A | 120.5 (4) | C1B—Cr1B—C6B | 109.8 (4) |
C3A—Cr1A—C8A | 93.2 (3) | C2B—Cr1B—C6B | 92.7 (3) |
C1A—Cr1A—C8A | 150.6 (3) | C3B—Cr1B—C6B | 161.7 (4) |
C7A—Cr1A—C8A | 35.8 (3) | C7B—Cr1B—C6B | 36.3 (3) |
C6A—Cr1A—C8A | 66.9 (3) | C5B—Cr1B—C6B | 36.8 (3) |
C5A—Cr1A—C8A | 78.3 (3) | C8B—Cr1B—C6B | 67.0 (3) |
C2A—Cr1A—C4A | 149.0 (4) | C1B—Cr1B—C4B | 96.2 (3) |
C3A—Cr1A—C4A | 122.8 (3) | C2B—Cr1B—C4B | 157.7 (3) |
C1A—Cr1A—C4A | 89.7 (3) | C3B—Cr1B—C4B | 111.5 (3) |
C7A—Cr1A—C4A | 76.0 (3) | C7B—Cr1B—C4B | 75.5 (3) |
C6A—Cr1A—C4A | 64.9 (3) | C5B—Cr1B—C4B | 36.9 (3) |
C5A—Cr1A—C4A | 36.3 (3) | C8B—Cr1B—C4B | 64.9 (3) |
C8A—Cr1A—C4A | 64.4 (3) | C6B—Cr1B—C4B | 65.1 (3) |
C2A—Cr1A—C9A | 156.3 (3) | C1B—Cr1B—C9B | 125.0 (3) |
C3A—Cr1A—C9A | 95.9 (3) | C2B—Cr1B—C9B | 146.0 (4) |
C1A—Cr1A—C9A | 114.5 (3) | C3B—Cr1B—C9B | 89.0 (3) |
C7A—Cr1A—C9A | 64.7 (3) | C7B—Cr1B—C9B | 65.4 (3) |
C6A—Cr1A—C9A | 78.0 (3) | C5B—Cr1B—C9B | 67.2 (3) |
C5A—Cr1A—C9A | 66.0 (3) | C8B—Cr1B—C9B | 36.3 (3) |
C8A—Cr1A—C9A | 36.1 (3) | C6B—Cr1B—C9B | 78.5 (3) |
C4A—Cr1A—C9A | 35.7 (3) | C4B—Cr1B—C9B | 36.3 (3) |
C15A—O4A—H4A | 109.5 | C15B—O4B—H4B | 109.5 |
O1A—C1A—Cr1A | 179.5 (8) | O1B—C1B—Cr1B | 177.8 (8) |
O2A—C2A—Cr1A | 178.5 (9) | O2B—C2B—Cr1B | 179.2 (9) |
O3A—C3A—Cr1A | 176.8 (8) | O3B—C3B—Cr1B | 176.6 (8) |
C5A—C4A—C9A | 122.5 (8) | C13B—C4B—C5B | 113.2 (7) |
C5A—C4A—C13A | 114.2 (8) | C13B—C4B—C9B | 122.7 (8) |
C9A—C4A—C13A | 123.3 (8) | C5B—C4B—C9B | 124.0 (7) |
C5A—C4A—Cr1A | 68.5 (4) | C13B—C4B—Cr1B | 128.7 (5) |
C9A—C4A—Cr1A | 74.0 (5) | C5B—C4B—Cr1B | 69.7 (4) |
C13A—C4A—Cr1A | 129.8 (5) | C9B—C4B—Cr1B | 74.0 (4) |
C6A—C5A—C4A | 119.9 (8) | C6B—C5B—C4B | 118.4 (7) |
C6A—C5A—C15A | 132.1 (7) | C6B—C5B—C15B | 133.4 (8) |
C4A—C5A—C15A | 107.9 (7) | C4B—C5B—C15B | 108.2 (7) |
C6A—C5A—Cr1A | 71.5 (5) | C6B—C5B—Cr1B | 72.6 (5) |
C4A—C5A—Cr1A | 75.2 (5) | C4B—C5B—Cr1B | 73.5 (5) |
C15A—C5A—Cr1A | 127.7 (5) | C15B—C5B—Cr1B | 126.9 (5) |
C5A—C6A—C7A | 118.2 (7) | C7B—C6B—C5B | 118.5 (8) |
C5A—C6A—Cr1A | 72.0 (5) | C7B—C6B—Cr1B | 70.8 (5) |
C7A—C6A—Cr1A | 70.8 (4) | C5B—C6B—Cr1B | 70.6 (5) |
C5A—C6A—H6A | 120.9 | C7B—C6B—H6B | 120.7 |
C7A—C6A—H6A | 120.9 | C5B—C6B—H6B | 120.7 |
Cr1A—C6A—H6A | 128.5 | Cr1B—C6B—H6B | 130.2 |
C8A—C7A—C6A | 121.0 (8) | C6B—C7B—C8B | 123.5 (8) |
C8A—C7A—Cr1A | 72.9 (5) | C6B—C7B—Cr1B | 72.9 (5) |
C6A—C7A—Cr1A | 71.0 (4) | C8B—C7B—Cr1B | 72.1 (4) |
C8A—C7A—H7A | 119.5 | C6B—C7B—H7B | 118.3 |
C6A—C7A—H7A | 119.5 | C8B—C7B—H7B | 118.3 |
Cr1A—C7A—H7A | 129.0 | Cr1B—C7B—H7B | 129.4 |
C7A—C8A—C9A | 122.4 (8) | C7B—C8B—C9B | 119.6 (8) |
C7A—C8A—Cr1A | 71.3 (5) | C7B—C8B—Cr1B | 70.8 (5) |
C9A—C8A—Cr1A | 76.8 (5) | C9B—C8B—Cr1B | 75.3 (5) |
C7A—C8A—H8A | 118.8 | C7B—C8B—H8B | 120.2 |
C9A—C8A—H8A | 118.8 | C9B—C8B—H8B | 120.2 |
Cr1A—C8A—H8A | 124.8 | Cr1B—C8B—H8B | 125.4 |
C4A—C9A—C8A | 115.6 (7) | C8B—C9B—C10B | 128.9 (9) |
C4A—C9A—C10A | 115.8 (8) | C8B—C9B—C4B | 115.6 (8) |
C8A—C9A—C10A | 128.6 (8) | C10B—C9B—C4B | 115.5 (8) |
C4A—C9A—Cr1A | 70.2 (4) | C8B—C9B—Cr1B | 68.3 (4) |
C8A—C9A—Cr1A | 67.1 (4) | C10B—C9B—Cr1B | 131.2 (6) |
C10A—C9A—Cr1A | 133.0 (5) | C4B—C9B—Cr1B | 69.7 (4) |
C11A—C10A—C9A | 119.7 (8) | C11B—C10B—C9B | 119.7 (9) |
C11A—C10A—H10A | 120.1 | C11B—C10B—H10B | 120.2 |
C9A—C10A—H10A | 120.1 | C9B—C10B—H10B | 120.2 |
C10A—C11A—C12A | 123.5 (8) | C10B—C11B—C12B | 123.6 (9) |
C10A—C11A—H11A | 118.3 | C10B—C11B—H11B | 118.2 |
C12A—C11A—H11A | 118.3 | C12B—C11B—H11B | 118.2 |
C13A—C12A—C11A | 118.3 (8) | C13B—C12B—C11B | 118.7 (10) |
C13A—C12A—H12A | 120.8 | C13B—C12B—H12B | 120.6 |
C11A—C12A—H12A | 120.8 | C11B—C12B—H12B | 120.6 |
C12A—C13A—C4A | 119.2 (8) | C12B—C13B—C4B | 119.7 (9) |
C12A—C13A—C14A | 134.0 (8) | C12B—C13B—C14B | 132.6 (9) |
C4A—C13A—C14A | 106.8 (7) | C4B—C13B—C14B | 107.7 (7) |
C13A—C14A—C15A | 107.2 (7) | C13B—C14B—C15B | 105.6 (7) |
C13A—C14A—H14A | 110.3 | C13B—C14B—H14C | 110.6 |
C15A—C14A—H14A | 110.3 | C15B—C14B—H14C | 110.6 |
C13A—C14A—H14B | 110.3 | C13B—C14B—H14D | 110.6 |
C15A—C14A—H14B | 110.3 | C15B—C14B—H14D | 110.6 |
H14A—C14A—H14B | 108.5 | H14C—C14B—H14D | 108.7 |
O4A—C15A—C5A | 110.6 (7) | O4B—C15B—C5B | 112.4 (7) |
O4A—C15A—C14A | 109.4 (6) | O4B—C15B—C14B | 114.0 (7) |
C5A—C15A—C14A | 103.9 (6) | C5B—C15B—C14B | 105.3 (7) |
O4A—C15A—H15A | 110.9 | O4B—C15B—H15B | 108.3 |
C5A—C15A—H15A | 110.9 | C5B—C15B—H15B | 108.3 |
C14A—C15A—H15A | 110.9 | C14B—C15B—H15B | 108.3 |
C2A—Cr1A—C4A—C5A | 1.4 (9) | C1B—Cr1B—C4B—C13B | −26.5 (8) |
C3A—Cr1A—C4A—C5A | 177.8 (5) | C2B—Cr1B—C4B—C13B | −128.7 (10) |
C1A—Cr1A—C4A—C5A | 88.5 (5) | C3B—Cr1B—C4B—C13B | 64.1 (9) |
C7A—Cr1A—C4A—C5A | −69.6 (5) | C7B—Cr1B—C4B—C13B | −172.5 (9) |
C6A—Cr1A—C4A—C5A | −30.6 (5) | C5B—Cr1B—C4B—C13B | −104.0 (9) |
C8A—Cr1A—C4A—C5A | −105.8 (5) | C8B—Cr1B—C4B—C13B | 149.5 (9) |
C9A—Cr1A—C4A—C5A | −135.6 (7) | C6B—Cr1B—C4B—C13B | −135.4 (9) |
C2A—Cr1A—C4A—C9A | 137.0 (7) | C9B—Cr1B—C4B—C13B | 119.5 (10) |
C3A—Cr1A—C4A—C9A | −46.7 (6) | C1B—Cr1B—C4B—C5B | 77.5 (5) |
C1A—Cr1A—C4A—C9A | −136.0 (5) | C2B—Cr1B—C4B—C5B | −24.7 (12) |
C7A—Cr1A—C4A—C9A | 66.0 (5) | C3B—Cr1B—C4B—C5B | 168.1 (5) |
C6A—Cr1A—C4A—C9A | 105.0 (5) | C7B—Cr1B—C4B—C5B | −68.5 (5) |
C5A—Cr1A—C4A—C9A | 135.6 (7) | C8B—Cr1B—C4B—C5B | −106.5 (5) |
C8A—Cr1A—C4A—C9A | 29.8 (4) | C6B—Cr1B—C4B—C5B | −31.5 (4) |
C2A—Cr1A—C4A—C13A | −102.7 (10) | C9B—Cr1B—C4B—C5B | −136.6 (7) |
C3A—Cr1A—C4A—C13A | 73.6 (9) | C1B—Cr1B—C4B—C9B | −145.9 (5) |
C1A—Cr1A—C4A—C13A | −15.7 (8) | C2B—Cr1B—C4B—C9B | 111.8 (10) |
C7A—Cr1A—C4A—C13A | −173.7 (9) | C3B—Cr1B—C4B—C9B | −55.4 (6) |
C6A—Cr1A—C4A—C13A | −134.8 (9) | C7B—Cr1B—C4B—C9B | 68.0 (5) |
C5A—Cr1A—C4A—C13A | −104.1 (10) | C5B—Cr1B—C4B—C9B | 136.6 (7) |
C8A—Cr1A—C4A—C13A | 150.1 (9) | C8B—Cr1B—C4B—C9B | 30.1 (5) |
C9A—Cr1A—C4A—C13A | 120.3 (10) | C6B—Cr1B—C4B—C9B | 105.1 (5) |
C9A—C4A—C5A—C6A | 5.0 (12) | C13B—C4B—C5B—C6B | −176.4 (7) |
C13A—C4A—C5A—C6A | −176.8 (7) | C9B—C4B—C5B—C6B | 6.1 (11) |
Cr1A—C4A—C5A—C6A | 58.0 (7) | Cr1B—C4B—C5B—C6B | 59.0 (6) |
C9A—C4A—C5A—C15A | −178.3 (7) | C13B—C4B—C5B—C15B | 0.4 (9) |
C13A—C4A—C5A—C15A | −0.2 (9) | C9B—C4B—C5B—C15B | −177.0 (7) |
Cr1A—C4A—C5A—C15A | −125.4 (6) | Cr1B—C4B—C5B—C15B | −124.1 (6) |
C9A—C4A—C5A—Cr1A | −52.9 (7) | C13B—C4B—C5B—Cr1B | 124.6 (6) |
C13A—C4A—C5A—Cr1A | 125.2 (6) | C9B—C4B—C5B—Cr1B | −52.9 (7) |
C2A—Cr1A—C5A—C6A | 51.6 (6) | C1B—Cr1B—C5B—C6B | 128.6 (5) |
C3A—Cr1A—C5A—C6A | −134.5 (9) | C2B—Cr1B—C5B—C6B | 41.4 (6) |
C1A—Cr1A—C5A—C6A | 139.7 (5) | C3B—Cr1B—C5B—C6B | −148.4 (6) |
C7A—Cr1A—C5A—C6A | −31.1 (5) | C7B—Cr1B—C5B—C6B | −29.3 (5) |
C8A—Cr1A—C5A—C6A | −66.8 (5) | C8B—Cr1B—C5B—C6B | −65.6 (5) |
C4A—Cr1A—C5A—C6A | −129.2 (7) | C4B—Cr1B—C5B—C6B | −127.8 (7) |
C9A—Cr1A—C5A—C6A | −102.7 (5) | C9B—Cr1B—C5B—C6B | −101.6 (5) |
C2A—Cr1A—C5A—C4A | −179.2 (5) | C1B—Cr1B—C5B—C4B | −103.7 (5) |
C3A—Cr1A—C5A—C4A | −5.3 (11) | C2B—Cr1B—C5B—C4B | 169.2 (5) |
C1A—Cr1A—C5A—C4A | −91.0 (5) | C3B—Cr1B—C5B—C4B | −20.7 (8) |
C7A—Cr1A—C5A—C4A | 98.1 (5) | C7B—Cr1B—C5B—C4B | 98.5 (5) |
C6A—Cr1A—C5A—C4A | 129.2 (7) | C8B—Cr1B—C5B—C4B | 62.1 (5) |
C8A—Cr1A—C5A—C4A | 62.4 (5) | C6B—Cr1B—C5B—C4B | 127.8 (7) |
C9A—Cr1A—C5A—C4A | 26.6 (4) | C9B—Cr1B—C5B—C4B | 26.2 (4) |
C2A—Cr1A—C5A—C15A | −77.8 (7) | C1B—Cr1B—C5B—C15B | −3.1 (7) |
C3A—Cr1A—C5A—C15A | 96.1 (11) | C2B—Cr1B—C5B—C15B | −90.2 (8) |
C1A—Cr1A—C5A—C15A | 10.4 (7) | C3B—Cr1B—C5B—C15B | 79.9 (9) |
C7A—Cr1A—C5A—C15A | −160.5 (8) | C7B—Cr1B—C5B—C15B | −160.9 (8) |
C6A—Cr1A—C5A—C15A | −129.3 (9) | C8B—Cr1B—C5B—C15B | 162.7 (7) |
C8A—Cr1A—C5A—C15A | 163.8 (7) | C6B—Cr1B—C5B—C15B | −131.6 (9) |
C4A—Cr1A—C5A—C15A | 101.4 (8) | C4B—Cr1B—C5B—C15B | 100.6 (8) |
C9A—Cr1A—C5A—C15A | 128.0 (7) | C9B—Cr1B—C5B—C15B | 126.8 (7) |
C4A—C5A—C6A—C7A | −4.4 (11) | C4B—C5B—C6B—C7B | −5.4 (11) |
C15A—C5A—C6A—C7A | 179.8 (8) | C15B—C5B—C6B—C7B | 178.7 (8) |
Cr1A—C5A—C6A—C7A | 55.4 (7) | Cr1B—C5B—C6B—C7B | 54.0 (7) |
C4A—C5A—C6A—Cr1A | −59.8 (7) | C4B—C5B—C6B—Cr1B | −59.5 (6) |
C15A—C5A—C6A—Cr1A | 124.5 (9) | C15B—C5B—C6B—Cr1B | 124.7 (9) |
C2A—Cr1A—C6A—C5A | −133.7 (6) | C1B—Cr1B—C6B—C7B | 172.7 (5) |
C3A—Cr1A—C6A—C5A | 144.2 (8) | C2B—Cr1B—C6B—C7B | 82.9 (6) |
C1A—Cr1A—C6A—C5A | −45.9 (6) | C3B—Cr1B—C6B—C7B | −16.4 (13) |
C7A—Cr1A—C6A—C5A | 129.8 (7) | C5B—Cr1B—C6B—C7B | −131.1 (7) |
C8A—Cr1A—C6A—C5A | 101.8 (5) | C8B—Cr1B—C6B—C7B | −27.7 (5) |
C4A—Cr1A—C6A—C5A | 30.4 (4) | C4B—Cr1B—C6B—C7B | −99.6 (5) |
C9A—Cr1A—C6A—C5A | 65.7 (5) | C9B—Cr1B—C6B—C7B | −63.9 (5) |
C2A—Cr1A—C6A—C7A | 96.5 (6) | C1B—Cr1B—C6B—C5B | −56.1 (6) |
C3A—Cr1A—C6A—C7A | 14.4 (10) | C2B—Cr1B—C6B—C5B | −145.9 (5) |
C1A—Cr1A—C6A—C7A | −175.8 (5) | C3B—Cr1B—C6B—C5B | 114.7 (11) |
C5A—Cr1A—C6A—C7A | −129.8 (7) | C7B—Cr1B—C6B—C5B | 131.1 (7) |
C8A—Cr1A—C6A—C7A | −28.0 (5) | C8B—Cr1B—C6B—C5B | 103.4 (5) |
C4A—Cr1A—C6A—C7A | −99.4 (5) | C4B—Cr1B—C6B—C5B | 31.5 (4) |
C9A—Cr1A—C6A—C7A | −64.2 (5) | C9B—Cr1B—C6B—C5B | 67.2 (5) |
C5A—C6A—C7A—C8A | −0.7 (12) | C5B—C6B—C7B—C8B | 0.0 (12) |
Cr1A—C6A—C7A—C8A | 55.3 (7) | Cr1B—C6B—C7B—C8B | 53.9 (7) |
C5A—C6A—C7A—Cr1A | −56.0 (7) | C5B—C6B—C7B—Cr1B | −53.9 (7) |
C2A—Cr1A—C7A—C8A | 143.8 (6) | C1B—Cr1B—C7B—C6B | −12.2 (9) |
C3A—Cr1A—C7A—C8A | 54.5 (6) | C2B—Cr1B—C7B—C6B | −97.3 (6) |
C1A—Cr1A—C7A—C8A | −123.8 (8) | C3B—Cr1B—C7B—C6B | 173.7 (5) |
C6A—Cr1A—C7A—C8A | −132.5 (8) | C5B—Cr1B—C7B—C6B | 29.7 (5) |
C5A—Cr1A—C7A—C8A | −102.6 (6) | C8B—Cr1B—C7B—C6B | 134.9 (8) |
C4A—Cr1A—C7A—C8A | −65.4 (5) | C4B—Cr1B—C7B—C6B | 67.5 (5) |
C9A—Cr1A—C7A—C8A | −29.3 (5) | C9B—Cr1B—C7B—C6B | 104.6 (5) |
C2A—Cr1A—C7A—C6A | −83.8 (5) | C1B—Cr1B—C7B—C8B | −147.0 (6) |
C3A—Cr1A—C7A—C6A | −173.0 (5) | C2B—Cr1B—C7B—C8B | 127.8 (6) |
C1A—Cr1A—C7A—C6A | 8.7 (10) | C3B—Cr1B—C7B—C8B | 38.8 (7) |
C5A—Cr1A—C7A—C6A | 29.9 (4) | C5B—Cr1B—C7B—C8B | −105.2 (5) |
C8A—Cr1A—C7A—C6A | 132.5 (8) | C6B—Cr1B—C7B—C8B | −134.9 (8) |
C4A—Cr1A—C7A—C6A | 67.0 (5) | C4B—Cr1B—C7B—C8B | −67.4 (5) |
C9A—Cr1A—C7A—C6A | 103.2 (5) | C9B—Cr1B—C7B—C8B | −30.3 (5) |
C6A—C7A—C8A—C9A | 5.5 (12) | C6B—C7B—C8B—C9B | 5.2 (12) |
Cr1A—C7A—C8A—C9A | 59.9 (7) | Cr1B—C7B—C8B—C9B | 59.5 (7) |
C6A—C7A—C8A—Cr1A | −54.4 (7) | C6B—C7B—C8B—Cr1B | −54.3 (7) |
C2A—Cr1A—C8A—C7A | −43.3 (7) | C1B—Cr1B—C8B—C7B | 111.4 (11) |
C3A—Cr1A—C8A—C7A | −133.1 (6) | C2B—Cr1B—C8B—C7B | −57.2 (6) |
C1A—Cr1A—C8A—C7A | 132.0 (7) | C3B—Cr1B—C8B—C7B | −149.4 (5) |
C6A—Cr1A—C8A—C7A | 29.7 (5) | C5B—Cr1B—C8B—C7B | 63.4 (5) |
C5A—Cr1A—C8A—C7A | 66.3 (5) | C6B—Cr1B—C8B—C7B | 27.1 (5) |
C4A—Cr1A—C8A—C7A | 101.9 (6) | C4B—Cr1B—C8B—C7B | 99.2 (5) |
C9A—Cr1A—C8A—C7A | 131.4 (8) | C9B—Cr1B—C8B—C7B | 129.3 (7) |
C2A—Cr1A—C8A—C9A | −174.6 (5) | C1B—Cr1B—C8B—C9B | −17.8 (13) |
C3A—Cr1A—C8A—C9A | 95.5 (5) | C2B—Cr1B—C8B—C9B | 173.6 (5) |
C1A—Cr1A—C8A—C9A | 0.6 (9) | C3B—Cr1B—C8B—C9B | 81.4 (5) |
C7A—Cr1A—C8A—C9A | −131.4 (8) | C7B—Cr1B—C8B—C9B | −129.3 (7) |
C6A—Cr1A—C8A—C9A | −101.6 (5) | C5B—Cr1B—C8B—C9B | −65.8 (5) |
C5A—Cr1A—C8A—C9A | −65.1 (5) | C6B—Cr1B—C8B—C9B | −102.2 (5) |
C4A—Cr1A—C8A—C9A | −29.5 (4) | C4B—Cr1B—C8B—C9B | −30.0 (4) |
C5A—C4A—C9A—C8A | −0.4 (11) | C7B—C8B—C9B—C10B | 176.6 (8) |
C13A—C4A—C9A—C8A | −178.4 (7) | Cr1B—C8B—C9B—C10B | −126.2 (8) |
Cr1A—C4A—C9A—C8A | −50.9 (6) | C7B—C8B—C9B—C4B | −4.5 (11) |
C5A—C4A—C9A—C10A | 179.7 (7) | Cr1B—C8B—C9B—C4B | 52.8 (6) |
C13A—C4A—C9A—C10A | 1.8 (11) | C7B—C8B—C9B—Cr1B | −57.2 (6) |
Cr1A—C4A—C9A—C10A | 129.2 (6) | C13B—C4B—C9B—C8B | −178.3 (7) |
C5A—C4A—C9A—Cr1A | 50.5 (7) | C5B—C4B—C9B—C8B | −1.1 (11) |
C13A—C4A—C9A—Cr1A | −127.4 (7) | Cr1B—C4B—C9B—C8B | −52.1 (6) |
C7A—C8A—C9A—C4A | −4.9 (11) | C13B—C4B—C9B—C10B | 0.8 (11) |
Cr1A—C8A—C9A—C4A | 52.5 (6) | C5B—C4B—C9B—C10B | 178.0 (7) |
C7A—C8A—C9A—C10A | 175.0 (8) | Cr1B—C4B—C9B—C10B | 127.0 (7) |
Cr1A—C8A—C9A—C10A | −127.6 (8) | C13B—C4B—C9B—Cr1B | −126.2 (7) |
C7A—C8A—C9A—Cr1A | −57.4 (7) | C5B—C4B—C9B—Cr1B | 51.0 (6) |
C2A—Cr1A—C9A—C4A | −118.9 (9) | C1B—Cr1B—C9B—C8B | 172.9 (5) |
C3A—Cr1A—C9A—C4A | 142.1 (5) | C2B—Cr1B—C9B—C8B | −10.9 (8) |
C1A—Cr1A—C9A—C4A | 49.8 (5) | C3B—Cr1B—C9B—C8B | −99.9 (5) |
C7A—Cr1A—C9A—C4A | −101.4 (5) | C7B—Cr1B—C9B—C8B | 30.9 (5) |
C6A—Cr1A—C9A—C4A | −63.4 (5) | C5B—Cr1B—C9B—C8B | 103.5 (5) |
C5A—Cr1A—C9A—C4A | −27.0 (4) | C6B—Cr1B—C9B—C8B | 66.7 (5) |
C8A—Cr1A—C9A—C4A | −130.5 (7) | C4B—Cr1B—C9B—C8B | 130.0 (7) |
C2A—Cr1A—C9A—C8A | 11.6 (11) | C1B—Cr1B—C9B—C10B | −63.7 (10) |
C3A—Cr1A—C9A—C8A | −87.5 (5) | C2B—Cr1B—C9B—C10B | 112.5 (10) |
C1A—Cr1A—C9A—C8A | −179.7 (5) | C3B—Cr1B—C9B—C10B | 23.5 (9) |
C7A—Cr1A—C9A—C8A | 29.1 (5) | C7B—Cr1B—C9B—C10B | 154.3 (10) |
C6A—Cr1A—C9A—C8A | 67.1 (5) | C5B—Cr1B—C9B—C10B | −133.1 (10) |
C5A—Cr1A—C9A—C8A | 103.5 (5) | C8B—Cr1B—C9B—C10B | 123.4 (11) |
C4A—Cr1A—C9A—C8A | 130.5 (7) | C6B—Cr1B—C9B—C10B | −169.9 (10) |
C2A—Cr1A—C9A—C10A | 133.8 (10) | C4B—Cr1B—C9B—C10B | −106.6 (11) |
C3A—Cr1A—C9A—C10A | 34.7 (9) | C1B—Cr1B—C9B—C4B | 42.9 (6) |
C1A—Cr1A—C9A—C10A | −57.5 (9) | C2B—Cr1B—C9B—C4B | −140.9 (6) |
C7A—Cr1A—C9A—C10A | 151.2 (10) | C3B—Cr1B—C9B—C4B | 130.0 (5) |
C6A—Cr1A—C9A—C10A | −170.8 (9) | C7B—Cr1B—C9B—C4B | −99.1 (5) |
C5A—Cr1A—C9A—C10A | −134.3 (9) | C5B—Cr1B—C9B—C4B | −26.6 (4) |
C8A—Cr1A—C9A—C10A | 122.2 (11) | C8B—Cr1B—C9B—C4B | −130.0 (7) |
C4A—Cr1A—C9A—C10A | −107.3 (10) | C6B—Cr1B—C9B—C4B | −63.3 (5) |
C4A—C9A—C10A—C11A | 2.1 (11) | C8B—C9B—C10B—C11B | −179.6 (8) |
C8A—C9A—C10A—C11A | −177.7 (8) | C4B—C9B—C10B—C11B | 1.5 (12) |
Cr1A—C9A—C10A—C11A | 88.6 (10) | Cr1B—C9B—C10B—C11B | 86.0 (11) |
C9A—C10A—C11A—C12A | −3.7 (13) | C9B—C10B—C11B—C12B | −2.0 (15) |
C10A—C11A—C12A—C13A | 1.3 (13) | C10B—C11B—C12B—C13B | 0.2 (15) |
C11A—C12A—C13A—C4A | 2.6 (12) | C11B—C12B—C13B—C4B | 2.1 (13) |
C11A—C12A—C13A—C14A | −179.0 (8) | C11B—C12B—C13B—C14B | −176.9 (9) |
C5A—C4A—C13A—C12A | 177.7 (7) | C5B—C4B—C13B—C12B | 179.9 (8) |
C9A—C4A—C13A—C12A | −4.2 (12) | C9B—C4B—C13B—C12B | −2.7 (12) |
Cr1A—C4A—C13A—C12A | −101.0 (9) | Cr1B—C4B—C13B—C12B | −98.2 (9) |
C5A—C4A—C13A—C14A | −1.1 (9) | C5B—C4B—C13B—C14B | −0.9 (9) |
C9A—C4A—C13A—C14A | 177.0 (7) | C9B—C4B—C13B—C14B | 176.6 (7) |
Cr1A—C4A—C13A—C14A | 80.3 (9) | Cr1B—C4B—C13B—C14B | 81.0 (9) |
C12A—C13A—C14A—C15A | −176.6 (9) | C12B—C13B—C14B—C15B | −179.9 (9) |
C4A—C13A—C14A—C15A | 1.9 (9) | C4B—C13B—C14B—C15B | 1.0 (8) |
C6A—C5A—C15A—O4A | 60.1 (11) | C6B—C5B—C15B—O4B | 51.7 (12) |
C4A—C5A—C15A—O4A | −116.0 (7) | C4B—C5B—C15B—O4B | −124.5 (7) |
Cr1A—C5A—C15A—O4A | 159.1 (5) | Cr1B—C5B—C15B—O4B | 152.9 (5) |
C6A—C5A—C15A—C14A | 177.4 (8) | C6B—C5B—C15B—C14B | 176.4 (8) |
C4A—C5A—C15A—C14A | 1.3 (8) | C4B—C5B—C15B—C14B | 0.2 (8) |
Cr1A—C5A—C15A—C14A | −83.6 (7) | Cr1B—C5B—C15B—C14B | −82.4 (7) |
C13A—C14A—C15A—O4A | 116.2 (7) | C13B—C14B—C15B—O4B | 123.0 (7) |
C13A—C14A—C15A—C5A | −1.9 (8) | C13B—C14B—C15B—C5B | −0.7 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4A—H4A···O4Bi | 0.82 | 2.04 | 2.835 (8) | 163 |
O4B—H4B···O4A | 0.82 | 2.07 | 2.771 (8) | 144 |
Symmetry code: (i) x+1/2, −y+1/2, z. |
Experimental details
Crystal data | |
Chemical formula | [Cr(C12H10O)(CO)3] |
Mr | 306.23 |
Crystal system, space group | Monoclinic, P21/a |
Temperature (K) | 296 |
a, b, c (Å) | 10.0838 (16), 25.963 (4), 10.1696 (17) |
β (°) | 95.641 (14) |
V (Å3) | 2649.6 (7) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.87 |
Crystal size (mm) | 0.20 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Rigaku AFC-6S |
Absorption correction | Empirical (using intensity measurements) via ψ-scan (3 reflections) (North et al., 1968) |
Tmin, Tmax | 0.84, 0.92 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4946, 4668, 1483 |
Rint | 0.087 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.161, 0.95 |
No. of reflections | 4668 |
No. of parameters | 363 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.40, −0.37 |
Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1994), SAPI91 (Fan 1991), SHELXL97 (Sheldrick, 1997), TEXSAN.
Cr1A—C2A | 1.824 (9) | Cr1A—C4A | 2.285 (8) |
Cr1A—C3A | 1.833 (9) | Cr1A—C9A | 2.334 (8) |
Cr1A—C1A | 1.834 (10) | O1A—C1A | 1.141 (9) |
Cr1A—C7A | 2.189 (7) | O2A—C2A | 1.152 (9) |
Cr1A—C6A | 2.192 (8) | O3A—C3A | 1.149 (9) |
Cr1A—C5A | 2.198 (8) | O4A—C15A | 1.429 (8) |
Cr1A—C8A | 2.209 (8) | ||
C2A—Cr1A—C3A | 88.2 (4) | C3A—Cr1A—C1A | 89.6 (4) |
C2A—Cr1A—C1A | 88.8 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4A—H4A···O4Bi | 0.82 | 2.04 | 2.835 (8) | 163 |
O4B—H4B···O4A | 0.82 | 2.07 | 2.771 (8) | 144 |
Symmetry code: (i) x+1/2, −y+1/2, z. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
Treatment of 1-hydroxy-1,2-dihydroacenaphthylene, (I), with Cr(CO)6 yields two Cr(CO)3 complexes, in addition to a number of other products (Simion, 1996). Based on 1H NMR results, and on previous results from 1-indanol complexation (Jaouen & Dabard, 1971; Top et al., 1979), it was thought that the two isomers involved exo and endo η6-coordination of Cr(CO)3 on the acenaphthylene ring nearest the OH group, and that initial complexation would occur with OH mediation to give the endo product. By means of OH ionization, and recombination via the exo face, one would obtain some of the exo isomer, (II). The structure of (II) was confirmed by a single-crystal X-ray diffraction study.
The asymmetric unit of (II) is composed of two independent conformers, A and B (Figs. 1 and 2). The two conformations are different, as is evident from a comparison of Figs. 1 and 2. This difference is mainly in the projection of the Cr(CO)3 fragment relative to the C atoms of the arene ring being complexed. In conformer A, the Cr(CO)3 unit is staggered, whereas in B, it is about midway between staggered and eclipsed. Several X-ray structures of naphthalene–Cr(CO)3 complexes have been included in the Cambridge Structural Database (Allen & Kennard, 1993). In naphthalene–Cr(CO)3 (Kunz & Nowacki, 1967), the Cr(CO)3 conformation resembles that of our B conformer.
The Cr—CCO distances lie in the range 1.822 (9)–1.847 (10) Å [mean 1.833 (9) Å], while the C≡O distances lie in the narrow range 1.141 (9)–1.153 (9) Å [mean 1.149 (4) Å]. These distances are in excellent agreement with the values reported for the corresponding distances in organometallic complexes (Orpen et al., 1994). The Cr—Caromatic distances span over a wide range [2.189 (7)–2.318 (8) Å], with Cr–centroid distances of 1.744 (10) and 1.747 (10) Å for conformers A and B, respectively. In both naphthalene–Cr(CO)3 and cyclopropanaphthalene–Cr(CO)3 complexes (Müller et al., 1989), one sees a slightly displaced Cr(CO)3 relative to the center of the arene ring. In the former, the Cr—Cbridgehead carbon bonds are 2.306 and 2.337 Å versus an average of 2.200 Å for the four outside distances. Similar distances are observed in the cyclopropanaphthalene complex. One sees the same features in our A and B conformers. Thus, in A, the two central bonds average to 2.310 Å, versus 2.197 Å for the outside bonds (2.290 Å versus 2.221 Å for B). The remaining molecular dimensions in both the conformers are normal with mean bond lengths Csp3—Csp3 = 1.553 (1), Csp3—Csp2 - 1.516 (10), C—Caromatic = 1.40 (3) and Csp3—O = 1.423 (6) Å.
In both conformers, the acenaphthylene rings are essentially planar with the maximum deviation of any atom from the mean-planes being 0.061 (7) and 0.059 (7) Å, for atoms C6A and C6B in conformers A and B, respectively. The hydroxyl O atoms lie 1.187 (7) and 1.022 (8) Å from the acenaphthylene rings and the orientation of hydroxyl H atoms is different in the two molecules. The hydroxyl groups are involved in hydrogen bonding between the conformers lying about glide planes [O4A—H4A···O4B and O4B—H4B···O4A, with O···O distances of 2.835 (8) and 2.771 (8) Å, respectively], thus resulting in chains of structures along the a axis (Fig. 3); details are given in Table 2. The effect of hydrogen bonding is manifested in differences in bond angles around C15A and C15B, e.g. the O4—C15—C14 angles in conformers A and B are 109.4 (6) and 114.0 (7)°, respectively.