exo-(±)-Tri­carbonyl(η6-1-hydroxy-1,2-di­hydro­ace­naphthyl­ene)­chromium(0)

Parvez, M.; Simion, D.V.; Sorensen, T.S.

doi:10.1107/S1600536801006304

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exo-(±)-Tricarbonyl(η⁶-1-hydroxy-1,2-dihydroacenaphthylene)chromium(0)

M. Parvez, D. V. Simion and T. S. Sorensen

The crystal structure of the title compound, [Cr(C₁₂H₁₀O)(CO)₃], contains two conformers in an asymmetric unit. The projection of the Cr(CO)₃ unit on the arene ring is staggered in one conformer, whereas it is about midway between staggered and eclipsed in the other. In both conformers, the Cr(CO)₃ unit is slightly displaced relative to the center of the arene ring. The hydroxyl groups are involved in hydrogen bonding between the conformers lying about glide planes, with O

O distances of 2.835 (8) and 2.771 (8) Å, resulting in chains along the a axis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801006304/om6017sup1.cif Contains datablocks Global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536801006304/om6017Isup2.hkl Contains datablock I

CCDC reference: 165634

checkCIF report

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

Comment top

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—C_CO 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—C_aromatic 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—C_bridgehead 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—C_aromatic = 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.

Experimental top

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.

Structure description top

Computing details top

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).

Figures top

	Fig. 1. ORTEPII (Johnson, 1976) drawing of conformer A of (II). Displacement ellipsoids have been plotted at 30% probability level.
	Fig. 2. ORTEPII (Johnson, 1976) drawing of conformer B of (II). Displacement ellipsoids have been plotted at 30% probability level.
	Fig. 3. The unit-cell packing in (II) showing the hydrogen bonds.

exo-(±)-Tricarbonyl(η⁶-1-hydroxy-1,2-dihydroacenaphthylene)chromium(0) top

Crystal data top

[Cr(C₁₂H₁₀O)(CO)₃]	D_x = 1.535 Mg m⁻³
M_r = 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

Data collection top

Rigaku AFC-6S diffractometer	1483 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.087
Graphite monochromator	θ_max = 25.0°, θ_min = 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
T_min = 0.84, T_max = 0.92	l = −12→12
4946 measured reflections	3 standard reflections every 200 reflections
4668 independent reflections	intensity decay: <0.22%

Refinement top

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(F_o²) + (0.049P)²] where P = (F_o² + 2F_c²)/3
4668 reflections	(Δ/σ)_max < 0.001
363 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

[Cr(C₁₂H₁₀O)(CO)₃]	V = 2649.6 (7) Å³
M_r = 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)°

Data collection top

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)	R_int = 0.087
T_min = 0.84, T_max = 0.92	3 standard reflections every 200 reflections
4946 measured reflections	intensity decay: <0.22%
4668 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.161	H-atom parameters constrained
S = 0.95	Δρ_max = 0.40 e Å⁻³
4668 reflections	Δρ_min = −0.37 e Å⁻³
363 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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]
M_r	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)
T_min, T_max	0.84, 0.92
No. of measured, independent and observed [I > 2σ(I)] reflections	4946, 4668, 1483
R_int	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
Δρ_max, Δρ_min (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.

Selected geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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.

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