ansa-Calcocenes: trans-Ph2(CH3)2C2(η5-C5H4)2Ca(DME)

Twamley, B.; Matare, G.J.; Shapiro, P.J.; Vij, A.

doi:10.1107/S1600536801013265

ansa-Calcocenes: trans-Ph₂(CH₃)₂C₂(η⁵-C₅H₄)₂Ca(DME)

B. Twamley, G. J. Matare, P. J. Shapiro and A. Vij

The title compound, (1,2-di-η⁵-cyclopentadienyl-1,2-dimethyl-trans-1,2-diphenylethane)(1,2-dimethoxyethane)calcium, trans-Ph₂(CH₃)₂C₂(η⁵-C₅H₄)₂Ca(DME) or [Ca(C₂₆H₂₄)(C₄H₁₀O₂)], was synthesized by reductively coupling 6,6-methylphenylfulvene with activated calcium in the presence of dimethoxyethane (DME). The trans isomer was isolated by fractional crystallization. The Ca atom is four-coordinate and is η⁵-bonded to both cyclopentadienyl rings [Ca—Cp(centroid) distance = 2.381 (3) Å] and the O atoms of the coordinated solvent chelate ligand [Ca—O = 2.350 (2) and 2.404 (2) Å].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801013265/om6038sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536801013265/om6038Isup2.hkl Contains datablock I

CCDC reference: 172192

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Key indicators

Single-crystal X-ray study
T = 213 K
Mean (C-C) = 0.004 Å
R factor = 0.062
wR factor = 0.117
Data-to-parameter ratio = 15.1

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No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_601  Alert C Structure Contains Solvent Accessible VOIDS of      49.00 A   3


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

Comment top

The reductive coupling of fulvenes with active metals is a convenient method for generating ethanediyl-bridged dicyclopentadienyl-ligand frameworks for ansa-metallocene complexes (Tan et al., 1975; Schwemlein & Brintzinger, 1983; Eisch & Shi, 1998). We have examined the reductive coupling of 6-methyl-6-phenylfulvene with activated calcium and report on the structure of the unusual calcocene: trans-Ph₂(CH₃)₂C₂(η⁵-C₅H₄)₂Ca(DME), (I).

The Ca atom in (I) is in a four-coordinate environment, η⁵-bonded η⁵ to both cyclopentadienyl (Cp) ligands and η¹-bonded to each O atom of the solvent ligand. Compound (I) has a Cp(centroid)—Ca distance of 2.381 (3) Å and a Cp—Ca—Cp angle of 121.3 (2)°. The Ca—O distances are slightly asymmetric [2.404 (2) and 2.350 (2) Å]. The O—Ca—O angle [69.66 (7)°] is distorted from the ideal tetrahedral angle due to the geometrical constraint of the chelate DME ligand. The dihedral angle between the two cyclopentadienyl rings is 59.6 (1)°.

There are few structurally determined ansa-bridged calcocenes for comparison. The closely related cis and trans ansa-calcocenes Ph₂C₂H₂(η⁵C₅H₄)₂Ca(THF)₂ have an average Cp—Ca distances of 2.40 and 2.42 Å, respectively with a Cp—Ca—Cp angle of 120.4 and 119.9° (Matare et al., 1998; Kane et al., 1997). The only other structurally reported carbon-bridged ansa-calcocene consists of the diiminoethane (DIE) coordinated calcocene (CH₃)₄C₂(η⁵-C₅H₄)₂Ca(^tBu₂DIE) which is closely related to (I) with asymmetric ligand N—Ca bonding of 2.503 (6) and 2.563 (6) Å, Cp—Ca distances of 2.396 (3) and 2.391 (3) Å, and a Cp—Ca—Cp angle of 119.0° (Reickhoff et al., 1993).

Experimental top

For the preparation of trans–Ph₂(CH₃)₂C₂(η⁵-C₅H₄)₂Ca(DME), (I), calcium granules (1.33 g, 33.19 mmol; preactivated with HgCl₂) were suspended in 100 ml of dry DME under an argon atmosphere. 6,6-Methylphenylfulvene (10.00 g, 59.44 mmol) was added gradually for a period of 15 min as the reaction was stirred at room temperature. The red color of the fulvene disappeared almost instantly and the reaction mixture appeared colorless within 6 h. The mixture was filtered to remove the gray precipitate and the solvent was removed under reduced pressure. The tan solid was washed with copious amounts of hexane yielding the product, a colorless solid (8.71 g, 61%). Roughly equal amounts of both the cis and trans isomers are present. The trans isomer was selectively precipitated as a colorless powder by dissolution and cooling to 195 K in a dry ice/acetone bath. Yield 2.66 g, 25%. X-ray quality crystals of the trans isomer were obtained from a saturated DME solution at room temperature after 3 d. ¹H NMR (200 MHz, DMSO-d₆): δ 1.92 (s, 6H, CH₃), 3.24 (s, 6H, CH₃—DME), 3.43 (s, 4H, CH₂—DME), 5.44 (s, 2H, Cp), 5.63–5.69 (d, 4H, Cp), 6.20 (s, 2H, Cp), 7.06–7.34 (m, 10H, Ph); ¹³C{¹H} NMR (50.3 MHz, DMSO-d₆): δ 28.2 (CH₃), 52.8 (MeCPH), 58.9 (CH₃O-DME), 71.9 (OCH₂CH₂O), 104.1, 106.7, 107.5, 108.2, 125.5 (C₅H₄), 126.5, 128.6, 129.4, 130.3, 132.5, 150.0 (C₆H₅); C₃₀H₃₄CaO₂ (calc/found%): C 77.21/77.17, H 7.34/7.31.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 1999); program(s) used to solve structure: XS (Sheldrick, 1998); program(s) used to refine structure: XL (Sheldrick, 1998); molecular graphics: XP (Sheldrick, 1998); software used to prepare material for publication: XCIF (Sheldrick, 1998).

Figures top

Fig. 1. The molecular structure of ((I)) with 30% probability ellipsoids. H atoms have been omitted for clarity.

(I) top

Crystal data top

[Ca(C₂₆H₂₄)(C₄H₁₀O₂)]	F(000) = 2000
M_r = 466.65	D_x = 1.195 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 27.726 (3) Å	Cell parameters from 8192 reflections
b = 12.412 (2) Å	θ = 1.8–25.0°
c = 16.087 (3) Å	µ = 0.27 mm⁻¹
β = 110.46 (2)°	T = 213 K
V = 5186.7 (14) Å³	Block, colorless
Z = 8	0.25 × 0.20 × 0.15 mm

Data collection top

Siemens SMART 1K diffractometer	4564 independent reflections
Radiation source: normal-focus sealed tube	4294 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 8.3 pixels mm^-1	θ_max = 25.0°, θ_min = 1.8°
ω scans	h = −32→32
Absorption correction: empirical (using intensity measurements) (XPREP; Sheldrick, 1998)	k = −7→14
T_min = 0.937, T_max = 0.961	l = −19→19
14054 measured reflections

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H-atom parameters constrained
S = 1.29	w = 1/[σ²(F_o²) + (0.0165P)² + 8.9225P] where P = (F_o² + 2F_c²)/3
4564 reflections	(Δ/σ)_max = 0.001
302 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

[Ca(C₂₆H₂₄)(C₄H₁₀O₂)]	V = 5186.7 (14) Å³
M_r = 466.65	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 27.726 (3) Å	µ = 0.27 mm⁻¹
b = 12.412 (2) Å	T = 213 K
c = 16.087 (3) Å	0.25 × 0.20 × 0.15 mm
β = 110.46 (2)°

Data collection top

Siemens SMART 1K diffractometer	4564 independent reflections
Absorption correction: empirical (using intensity measurements) (XPREP; Sheldrick, 1998)	4294 reflections with I > 2σ(I)
T_min = 0.937, T_max = 0.961	R_int = 0.028
14054 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.29	Δρ_max = 0.25 e Å⁻³
4564 reflections	Δρ_min = −0.24 e Å⁻³
302 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
C1	0.38450 (12)	0.2368 (2)	0.29348 (17)	0.0460 (7)
H1	0.4192	0.2207	0.3254	0.055*
C2	0.35100 (14)	0.2918 (3)	0.32724 (19)	0.0561 (8)
H2	0.3595	0.3190	0.3851	0.067*
C3	0.30308 (13)	0.2990 (2)	0.2601 (2)	0.0517 (8)
H3	0.2735	0.3316	0.2646	0.062*
C4	0.30698 (10)	0.2488 (2)	0.18423 (18)	0.0400 (6)
H4	0.2801	0.2425	0.1292	0.048*
C5	0.35753 (9)	0.2092 (2)	0.20347 (16)	0.0335 (6)
C6	0.43328 (11)	0.3845 (2)	0.13082 (19)	0.0426 (7)
H6	0.4629	0.3476	0.1664	0.051*
C7	0.42732 (15)	0.4974 (3)	0.1259 (2)	0.0585 (9)
H7	0.4521	0.5482	0.1574	0.070*
C8	0.37849 (15)	0.5204 (2)	0.0667 (2)	0.0573 (9)
H8	0.3644	0.5896	0.0512	0.069*
C9	0.35378 (12)	0.4225 (2)	0.03404 (18)	0.0430 (7)
H9	0.3202	0.4155	−0.0074	0.052*
C10	0.38750 (9)	0.3356 (2)	0.07341 (16)	0.0313 (5)
C11	0.38072 (9)	0.14745 (19)	0.14325 (15)	0.0296 (5)
C12	0.37407 (9)	0.21585 (19)	0.05301 (15)	0.0272 (5)
C13	0.25200 (13)	0.5674 (3)	0.1584 (3)	0.0754 (11)
H13A	0.2369	0.5340	0.1980	0.113*
H13B	0.2434	0.5255	0.1043	0.113*
H13C	0.2386	0.6399	0.1442	0.113*
C14	0.32294 (16)	0.6384 (3)	0.2767 (2)	0.0800 (12)
H14A	0.3118	0.6074	0.3231	0.096*
H14B	0.3072	0.7098	0.2617	0.096*
C15	0.37921 (17)	0.6483 (3)	0.3093 (3)	0.0881 (14)
H15A	0.3899	0.6878	0.2659	0.106*
H15B	0.3908	0.6888	0.3651	0.106*
C16	0.44406 (13)	0.5315 (3)	0.4031 (2)	0.0662 (10)
H16A	0.4714	0.5807	0.4038	0.099*
H16B	0.4567	0.4580	0.4080	0.099*
H16C	0.4329	0.5473	0.4526	0.099*
C17	0.30937 (11)	0.0062 (2)	0.12679 (19)	0.0466 (7)
H17	0.2911	0.0581	0.1464	0.056*
C18	0.28880 (13)	−0.0970 (3)	0.1054 (2)	0.0595 (9)
H18	0.2567	−0.1131	0.1102	0.071*
C19	0.31457 (15)	−0.1750 (3)	0.0778 (2)	0.0660 (10)
H19	0.3008	−0.2447	0.0644	0.079*
C20	0.36100 (15)	−0.1497 (3)	0.0698 (3)	0.0708 (10)
H20	0.3790	−0.2022	0.0501	0.085*
C21	0.38141 (12)	−0.0472 (2)	0.0907 (2)	0.0551 (8)
H21	0.4133	−0.0318	0.0851	0.066*
C22	0.35646 (10)	0.0337 (2)	0.11957 (16)	0.0341 (6)
C23	0.43838 (9)	0.1298 (2)	0.19634 (18)	0.0410 (6)
H23A	0.4546	0.1986	0.2173	0.061*
H23B	0.4547	0.0963	0.1585	0.061*
H23C	0.4421	0.0833	0.2467	0.061*
C24	0.38594 (11)	0.0974 (2)	−0.0698 (2)	0.0473 (7)
H24	0.3517	0.0747	−0.0835	0.057*
C25	0.41374 (13)	0.0588 (3)	−0.1206 (2)	0.0631 (9)
H25	0.3981	0.0111	−0.1678	0.076*
C26	0.46386 (13)	0.0900 (3)	−0.1021 (2)	0.0626 (9)
H26	0.4827	0.0651	−0.1368	0.075*
C27	0.48622 (11)	0.1584 (3)	−0.0317 (2)	0.0523 (8)
H27	0.5208	0.1790	−0.0175	0.063*
C28	0.45824 (10)	0.1973 (2)	0.01840 (17)	0.0386 (6)
H28	0.4743	0.2445	0.0657	0.046*
C29	0.40698 (9)	0.16856 (19)	0.00069 (16)	0.0311 (5)
C30	0.31725 (9)	0.2097 (2)	−0.00820 (16)	0.0345 (6)
H30A	0.2963	0.2517	0.0172	0.052*
H30B	0.3059	0.1353	−0.0142	0.052*
H30C	0.3137	0.2384	−0.0661	0.052*
Ca1	0.36396 (2)	0.42404 (4)	0.20534 (4)	0.03889 (16)
O1	0.30689 (8)	0.57156 (16)	0.20084 (13)	0.0509 (5)
O2	0.40246 (9)	0.54348 (18)	0.32334 (14)	0.0689 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0578 (18)	0.0461 (17)	0.0294 (14)	−0.0095 (14)	0.0093 (13)	0.0055 (12)
C2	0.088 (2)	0.0542 (19)	0.0355 (16)	−0.0110 (18)	0.0339 (17)	−0.0049 (14)
C3	0.064 (2)	0.0519 (18)	0.0577 (19)	−0.0058 (16)	0.0441 (17)	−0.0044 (15)
C4	0.0394 (15)	0.0455 (16)	0.0398 (15)	−0.0049 (13)	0.0197 (12)	−0.0029 (12)
C5	0.0354 (14)	0.0347 (14)	0.0296 (13)	−0.0051 (11)	0.0105 (11)	0.0027 (11)
C6	0.0429 (16)	0.0427 (16)	0.0489 (17)	−0.0114 (13)	0.0246 (13)	−0.0107 (13)
C7	0.082 (2)	0.0428 (17)	0.068 (2)	−0.0265 (17)	0.049 (2)	−0.0194 (16)
C8	0.103 (3)	0.0299 (16)	0.061 (2)	0.0027 (17)	0.056 (2)	0.0014 (14)
C9	0.0620 (18)	0.0368 (15)	0.0372 (15)	0.0086 (14)	0.0263 (14)	0.0032 (12)
C10	0.0377 (14)	0.0316 (13)	0.0300 (13)	−0.0005 (11)	0.0186 (11)	0.0001 (11)
C11	0.0257 (12)	0.0316 (13)	0.0288 (12)	0.0008 (10)	0.0060 (10)	0.0041 (10)
C12	0.0259 (12)	0.0296 (13)	0.0254 (12)	−0.0008 (10)	0.0081 (10)	0.0003 (10)
C13	0.058 (2)	0.076 (3)	0.086 (3)	0.0066 (19)	0.018 (2)	−0.008 (2)
C14	0.099 (3)	0.078 (3)	0.050 (2)	0.034 (2)	0.009 (2)	−0.0222 (19)
C15	0.106 (3)	0.051 (2)	0.072 (3)	0.011 (2)	−0.013 (2)	−0.0288 (19)
C16	0.052 (2)	0.079 (3)	0.059 (2)	0.0045 (18)	0.0091 (17)	−0.0122 (19)
C17	0.0524 (18)	0.0419 (16)	0.0509 (17)	−0.0106 (14)	0.0250 (14)	−0.0041 (13)
C18	0.065 (2)	0.054 (2)	0.068 (2)	−0.0228 (17)	0.0345 (18)	−0.0031 (17)
C19	0.089 (3)	0.0372 (18)	0.076 (2)	−0.0178 (18)	0.034 (2)	−0.0021 (17)
C20	0.082 (3)	0.0341 (17)	0.108 (3)	−0.0004 (17)	0.049 (2)	−0.0055 (18)
C21	0.0536 (19)	0.0357 (16)	0.084 (2)	0.0021 (14)	0.0341 (18)	0.0023 (16)
C22	0.0356 (14)	0.0339 (14)	0.0310 (13)	−0.0007 (11)	0.0094 (11)	0.0070 (11)
C23	0.0315 (14)	0.0472 (16)	0.0386 (15)	0.0022 (12)	0.0052 (12)	0.0119 (13)
C24	0.0459 (16)	0.0424 (16)	0.0564 (18)	−0.0027 (13)	0.0213 (14)	−0.0162 (14)
C25	0.066 (2)	0.060 (2)	0.067 (2)	0.0040 (17)	0.0278 (18)	−0.0266 (18)
C26	0.066 (2)	0.066 (2)	0.069 (2)	0.0134 (18)	0.0395 (18)	−0.0143 (18)
C27	0.0391 (16)	0.060 (2)	0.065 (2)	0.0082 (14)	0.0263 (15)	−0.0004 (17)
C28	0.0349 (14)	0.0414 (15)	0.0402 (14)	0.0057 (12)	0.0140 (12)	0.0003 (12)
C29	0.0338 (13)	0.0284 (13)	0.0311 (13)	0.0056 (11)	0.0114 (11)	0.0043 (10)
C30	0.0277 (13)	0.0438 (15)	0.0300 (13)	0.0023 (11)	0.0078 (10)	0.0037 (11)
Ca1	0.0529 (3)	0.0342 (3)	0.0356 (3)	−0.0035 (3)	0.0231 (3)	−0.0064 (2)
O1	0.0579 (13)	0.0513 (12)	0.0438 (11)	0.0047 (10)	0.0181 (10)	−0.0120 (10)
O2	0.0838 (17)	0.0530 (14)	0.0474 (13)	0.0130 (12)	−0.0056 (12)	−0.0184 (11)

Geometric parameters (Å, º) top

C1—C2	1.406 (4)	C14—C15	1.467 (5)
C1—C5	1.420 (4)	C14—H14A	0.9800
C1—Ca1	2.678 (3)	C14—H14B	0.9800
C1—H1	0.9400	C15—O2	1.434 (4)
C2—C3	1.392 (4)	C15—H15A	0.9800
C2—Ca1	2.676 (3)	C15—H15B	0.9800
C2—H2	0.9400	C16—O2	1.401 (4)
C3—C4	1.409 (4)	C16—H16A	0.9700
C3—Ca1	2.660 (3)	C16—H16B	0.9700
C3—H3	0.9400	C16—H16C	0.9700
C4—C5	1.414 (4)	C17—C22	1.393 (4)
C4—Ca1	2.639 (3)	C17—C18	1.395 (4)
C4—H4	0.9400	C17—H17	0.9400
C5—C11	1.541 (3)	C18—C19	1.367 (5)
C5—Ca1	2.672 (3)	C18—H18	0.9400
C6—C7	1.409 (4)	C19—C20	1.374 (5)
C6—C10	1.419 (4)	C19—H19	0.9400
C6—Ca1	2.642 (3)	C20—C21	1.386 (4)
C6—H6	0.9400	C20—H20	0.9400
C7—C8	1.386 (5)	C21—C22	1.388 (4)
C7—Ca1	2.667 (3)	C21—H21	0.9400
C7—H7	0.9400	C23—H23A	0.9700
C8—C9	1.404 (4)	C23—H23B	0.9700
C8—Ca1	2.682 (3)	C23—H23C	0.9700
C8—H8	0.9400	C24—C25	1.391 (4)
C9—C10	1.423 (4)	C24—C29	1.394 (4)
C9—Ca1	2.670 (3)	C24—H24	0.9400
C9—H9	0.9400	C25—C26	1.371 (5)
C10—C12	1.540 (3)	C25—H25	0.9400
C10—Ca1	2.665 (2)	C26—C27	1.377 (4)
C11—C23	1.542 (3)	C26—H26	0.9400
C11—C22	1.553 (3)	C27—C28	1.386 (4)
C11—C12	1.636 (3)	C27—H27	0.9400
C12—C30	1.540 (3)	C28—C29	1.395 (3)
C12—C29	1.556 (3)	C28—H28	0.9400
C13—O1	1.435 (4)	C30—H30A	0.9700
C13—H13A	0.9700	C30—H30B	0.9700
C13—H13B	0.9700	C30—H30C	0.9700
C13—H13C	0.9700	Ca1—O2	2.350 (2)
C14—O1	1.413 (4)	Ca1—O1	2.404 (2)

C2—C1—C5	109.1 (3)	C18—C19—H19	120.6
C2—C1—Ca1	74.68 (17)	C20—C19—H19	120.6
C5—C1—Ca1	74.37 (15)	C19—C20—C21	120.3 (3)
C2—C1—H1	125.4	C19—C20—H20	119.9
C5—C1—H1	125.4	C21—C20—H20	119.9
Ca1—C1—H1	117.4	C20—C21—C22	122.4 (3)
C3—C2—C1	108.2 (3)	C20—C21—H21	118.8
C3—C2—Ca1	74.23 (17)	C22—C21—H21	118.8
C1—C2—Ca1	74.88 (16)	C21—C22—C17	116.2 (3)
C3—C2—H2	125.9	C21—C22—C11	121.1 (2)
C1—C2—H2	125.9	C17—C22—C11	122.7 (2)
Ca1—C2—H2	117.0	C11—C23—H23A	109.5
C2—C3—C4	107.6 (3)	C11—C23—H23B	109.5
C2—C3—Ca1	75.53 (17)	H23A—C23—H23B	109.5
C4—C3—Ca1	73.80 (15)	C11—C23—H23C	109.5
C2—C3—H3	126.2	H23A—C23—H23C	109.5
C4—C3—H3	126.2	H23B—C23—H23C	109.5
Ca1—C3—H3	116.6	C25—C24—C29	122.4 (3)
C3—C4—C5	109.6 (3)	C25—C24—H24	118.8
C3—C4—Ca1	75.37 (16)	C29—C24—H24	118.8
C5—C4—Ca1	75.85 (15)	C26—C25—C24	120.1 (3)
C3—C4—H4	125.2	C26—C25—H25	119.9
C5—C4—H4	125.2	C24—C25—H25	119.9
Ca1—C4—H4	115.5	C25—C26—C27	119.0 (3)
C4—C5—C1	105.5 (2)	C25—C26—H26	120.5
C4—C5—C11	129.4 (2)	C27—C26—H26	120.5
C1—C5—C11	125.1 (2)	C26—C27—C28	120.7 (3)
C4—C5—Ca1	73.29 (15)	C26—C27—H27	119.7
C1—C5—Ca1	74.86 (16)	C28—C27—H27	119.7
C11—C5—Ca1	117.55 (15)	C27—C28—C29	122.0 (3)
C7—C6—C10	109.2 (3)	C27—C28—H28	119.0
C7—C6—Ca1	75.59 (17)	C29—C28—H28	119.0
C10—C6—Ca1	75.39 (14)	C24—C29—C28	115.8 (2)
C7—C6—H6	125.4	C24—C29—C12	121.4 (2)
C10—C6—H6	125.4	C28—C29—C12	122.8 (2)
Ca1—C6—H6	115.6	C12—C30—H30A	109.5
C8—C7—C6	108.1 (3)	C12—C30—H30B	109.5
C8—C7—Ca1	75.58 (18)	H30A—C30—H30B	109.5
C6—C7—Ca1	73.63 (16)	C12—C30—H30C	109.5
C8—C7—H7	125.9	H30A—C30—H30C	109.5
C6—C7—H7	125.9	H30B—C30—H30C	109.5
Ca1—C7—H7	116.9	O2—Ca1—O1	69.66 (8)
C7—C8—C9	108.1 (3)	O2—Ca1—C4	134.92 (9)
C7—C8—Ca1	74.39 (18)	O1—Ca1—C4	105.41 (8)
C9—C8—Ca1	74.33 (16)	O2—Ca1—C6	106.64 (9)
C7—C8—H8	126.0	O1—Ca1—C6	134.67 (8)
C9—C8—H8	126.0	C4—Ca1—C6	106.63 (8)
Ca1—C8—H8	117.3	O2—Ca1—C3	105.19 (10)
C8—C9—C10	109.3 (3)	O1—Ca1—C3	88.11 (9)
C8—C9—Ca1	75.26 (16)	C6—Ca1—C3	133.53 (9)
C10—C9—Ca1	74.34 (14)	O2—Ca1—C10	137.25 (9)
C8—C9—H9	125.3	O1—Ca1—C10	129.15 (8)
C10—C9—H9	125.3	C4—Ca1—C10	81.97 (8)
Ca1—C9—H9	117.0	C3—Ca1—C10	112.59 (8)
C6—C10—C9	105.3 (2)	O2—Ca1—C7	88.98 (10)
C6—C10—C12	130.3 (2)	O1—Ca1—C7	105.21 (9)
C9—C10—C12	124.4 (2)	C4—Ca1—C7	133.19 (9)
C6—C10—Ca1	73.61 (14)	C3—Ca1—C7	163.40 (9)
C9—C10—Ca1	74.73 (14)	C10—Ca1—C7	51.22 (8)
C12—C10—Ca1	117.33 (15)	O2—Ca1—C9	133.81 (9)
C5—C11—C23	107.6 (2)	O1—Ca1—C9	98.24 (8)
C5—C11—C22	111.5 (2)	C4—Ca1—C9	91.08 (9)
C23—C11—C22	106.4 (2)	C6—Ca1—C9	50.33 (9)
C5—C11—C12	110.95 (19)	C3—Ca1—C9	119.18 (10)
C23—C11—C12	109.80 (19)	C7—Ca1—C9	50.05 (10)
C22—C11—C12	110.45 (18)	O2—Ca1—C5	130.41 (8)
C10—C12—C30	107.5 (2)	O1—Ca1—C5	135.98 (8)
C10—C12—C29	109.60 (19)	C6—Ca1—C5	82.30 (8)
C30—C12—C29	107.33 (19)	C3—Ca1—C5	51.25 (8)
C10—C12—C11	111.60 (18)	C10—Ca1—C5	67.29 (7)
C30—C12—C11	108.34 (18)	C7—Ca1—C5	112.81 (9)
C29—C12—C11	112.25 (18)	C9—Ca1—C5	89.93 (8)
O1—C13—H13A	109.5	O2—Ca1—C2	86.24 (9)
O1—C13—H13B	109.5	O1—Ca1—C2	103.51 (9)
H13A—C13—H13B	109.5	C4—Ca1—C2	50.30 (9)
O1—C13—H13C	109.5	C6—Ca1—C2	121.59 (10)
H13A—C13—H13C	109.5	C10—Ca1—C2	117.64 (9)
H13B—C13—H13C	109.5	C7—Ca1—C2	147.12 (12)
O1—C14—C15	109.4 (3)	C9—Ca1—C2	139.39 (9)
O1—C14—H14A	109.8	C5—Ca1—C2	51.00 (8)
C15—C14—H14A	109.8	O2—Ca1—C1	99.63 (8)
O1—C14—H14B	109.8	O1—Ca1—C1	133.85 (9)
C15—C14—H14B	109.8	C4—Ca1—C1	50.19 (9)
H14A—C14—H14B	108.2	C6—Ca1—C1	91.45 (9)
O2—C15—C14	110.1 (3)	C3—Ca1—C1	50.24 (10)
O2—C15—H15A	109.6	C10—Ca1—C1	89.89 (8)
C14—C15—H15A	109.6	C7—Ca1—C1	119.73 (11)
O2—C15—H15B	109.6	C9—Ca1—C1	117.80 (8)
C14—C15—H15B	109.6	O2—Ca1—C8	103.43 (10)
H15A—C15—H15B	108.1	O1—Ca1—C8	85.63 (9)
O2—C16—H16A	109.5	C4—Ca1—C8	121.18 (10)
O2—C16—H16B	109.5	C6—Ca1—C8	50.29 (10)
H16A—C16—H16B	109.5	C3—Ca1—C8	146.40 (11)
O2—C16—H16C	109.5	C10—Ca1—C8	51.09 (8)
H16A—C16—H16C	109.5	C5—Ca1—C8	117.68 (8)
H16B—C16—H16C	109.5	C2—Ca1—C8	168.66 (9)
C22—C17—C18	121.3 (3)	C1—Ca1—C8	139.58 (9)
C22—C17—H17	119.4	C14—O1—C13	113.2 (3)
C18—C17—H17	119.4	C14—O1—Ca1	114.58 (19)
C19—C18—C17	121.0 (3)	C13—O1—Ca1	124.36 (19)
C19—C18—H18	119.5	C16—O2—C15	115.0 (3)
C17—C18—H18	119.5	C16—O2—Ca1	131.9 (2)
C18—C19—C20	118.8 (3)	C15—O2—Ca1	113.09 (18)

C5—C1—C2—C3	0.3 (3)	C6—C10—Ca1—C8	75.47 (19)
Ca1—C1—C2—C3	67.3 (2)	C9—C10—Ca1—C8	−35.98 (17)
C5—C1—C2—Ca1	−67.00 (19)	C12—C10—Ca1—C8	−157.2 (2)
C1—C2—C3—C4	−0.4 (3)	C8—C7—Ca1—O2	−119.68 (18)
Ca1—C2—C3—C4	67.4 (2)	C6—C7—Ca1—O2	126.1 (2)
C1—C2—C3—Ca1	−67.8 (2)	C8—C7—Ca1—O1	−51.09 (18)
C2—C3—C4—C5	0.2 (3)	C6—C7—Ca1—O1	−165.29 (18)
Ca1—C3—C4—C5	68.84 (19)	C8—C7—Ca1—C4	78.2 (2)
C2—C3—C4—Ca1	−68.6 (2)	C6—C7—Ca1—C4	−36.0 (3)
C3—C4—C5—C1	0.0 (3)	C8—C7—Ca1—C6	114.2 (3)
Ca1—C4—C5—C1	68.50 (18)	C8—C7—Ca1—C3	91.3 (4)
C3—C4—C5—C11	179.2 (2)	C6—C7—Ca1—C3	−22.9 (5)
Ca1—C4—C5—C11	−112.2 (3)	C8—C7—Ca1—C10	77.30 (19)
C3—C4—C5—Ca1	−68.5 (2)	C6—C7—Ca1—C10	−36.90 (17)
C2—C1—C5—C4	−0.2 (3)	C8—C7—Ca1—C9	36.96 (17)
Ca1—C1—C5—C4	−67.40 (18)	C6—C7—Ca1—C9	−77.23 (19)
C2—C1—C5—C11	−179.5 (2)	C8—C7—Ca1—C5	106.23 (18)
Ca1—C1—C5—C11	113.3 (2)	C6—C7—Ca1—C5	−8.0 (2)
C2—C1—C5—Ca1	67.2 (2)	C8—C7—Ca1—C2	158.86 (19)
C10—C6—C7—C8	0.2 (3)	C6—C7—Ca1—C2	44.7 (3)
Ca1—C6—C7—C8	−68.3 (2)	C8—C7—Ca1—C1	139.80 (17)
C10—C6—C7—Ca1	68.58 (18)	C6—C7—Ca1—C1	25.6 (2)
C6—C7—C8—C9	−0.2 (3)	C6—C7—Ca1—C8	−114.2 (3)
Ca1—C7—C8—C9	−67.3 (2)	C8—C9—Ca1—O2	−3.1 (2)
C6—C7—C8—Ca1	67.0 (2)	C10—C9—Ca1—O2	112.26 (17)
C7—C8—C9—C10	0.2 (3)	C8—C9—Ca1—O1	66.5 (2)
Ca1—C8—C9—C10	−67.17 (18)	C10—C9—Ca1—O1	−178.09 (15)
C7—C8—C9—Ca1	67.3 (2)	C8—C9—Ca1—C4	172.2 (2)
C7—C6—C10—C9	−0.1 (3)	C10—C9—Ca1—C4	−72.35 (16)
Ca1—C6—C10—C9	68.58 (17)	C8—C9—Ca1—C6	−76.9 (2)
C7—C6—C10—C12	179.1 (2)	C10—C9—Ca1—C6	38.52 (15)
Ca1—C6—C10—C12	−112.2 (2)	C8—C9—Ca1—C3	158.94 (19)
C7—C6—C10—Ca1	−68.7 (2)	C10—C9—Ca1—C3	−85.64 (18)
C8—C9—C10—C6	0.0 (3)	C8—C9—Ca1—C10	−115.4 (3)
Ca1—C9—C10—C6	−67.78 (17)	C8—C9—Ca1—C7	−36.47 (19)
C8—C9—C10—C12	−179.3 (2)	C10—C9—Ca1—C7	78.94 (18)
Ca1—C9—C10—C12	112.9 (2)	C8—C9—Ca1—C5	−156.9 (2)
C8—C9—C10—Ca1	67.77 (19)	C10—C9—Ca1—C5	−41.51 (16)
C4—C5—C11—C23	176.7 (3)	C8—C9—Ca1—C2	−171.4 (2)
C1—C5—C11—C23	−4.2 (3)	C10—C9—Ca1—C2	−56.0 (2)
Ca1—C5—C11—C23	86.2 (2)	C8—C9—Ca1—C1	−143.31 (19)
C4—C5—C11—C22	−67.0 (3)	C10—C9—Ca1—C1	−27.90 (19)
C1—C5—C11—C22	112.2 (3)	C10—C9—Ca1—C8	115.4 (3)
Ca1—C5—C11—C22	−157.49 (15)	C4—C5—Ca1—O2	112.54 (17)
C4—C5—C11—C12	56.6 (3)	C1—C5—Ca1—O2	0.8 (2)
C1—C5—C11—C12	−124.3 (3)	C11—C5—Ca1—O2	−121.23 (17)
Ca1—C5—C11—C12	−33.9 (2)	C4—C5—Ca1—O1	9.6 (2)
C6—C10—C12—C30	175.2 (2)	C1—C5—Ca1—O1	−102.17 (18)
C9—C10—C12—C30	−5.7 (3)	C11—C5—Ca1—O1	135.83 (16)
Ca1—C10—C12—C30	83.9 (2)	C1—C5—Ca1—C4	−111.8 (2)
C6—C10—C12—C29	−68.5 (3)	C11—C5—Ca1—C4	126.2 (2)
C9—C10—C12—C29	110.6 (3)	C4—C5—Ca1—C6	−142.14 (16)
Ca1—C10—C12—C29	−159.70 (15)	C1—C5—Ca1—C6	106.09 (17)
C6—C10—C12—C11	56.5 (3)	C11—C5—Ca1—C6	−15.91 (17)
C9—C10—C12—C11	−124.4 (2)	C4—C5—Ca1—C3	36.55 (16)
Ca1—C10—C12—C11	−34.7 (2)	C1—C5—Ca1—C3	−75.22 (18)
C5—C11—C12—C10	44.2 (3)	C11—C5—Ca1—C3	162.8 (2)
C23—C11—C12—C10	−74.6 (2)	C4—C5—Ca1—C10	−113.90 (16)
C22—C11—C12—C10	168.33 (19)	C1—C5—Ca1—C10	134.33 (18)
C5—C11—C12—C30	−74.0 (2)	C11—C5—Ca1—C10	12.33 (16)
C23—C11—C12—C30	167.2 (2)	C4—C5—Ca1—C7	−138.03 (16)
C22—C11—C12—C30	50.2 (2)	C1—C5—Ca1—C7	110.20 (18)
C5—C11—C12—C29	167.67 (19)	C11—C5—Ca1—C7	−11.8 (2)
C23—C11—C12—C29	48.9 (3)	C4—C5—Ca1—C9	−92.23 (16)
C22—C11—C12—C29	−68.2 (2)	C1—C5—Ca1—C9	156.00 (17)
O1—C14—C15—O2	−53.9 (5)	C11—C5—Ca1—C9	34.00 (18)
C22—C17—C18—C19	0.8 (5)	C4—C5—Ca1—C2	75.69 (17)
C17—C18—C19—C20	−1.0 (6)	C1—C5—Ca1—C2	−36.08 (17)
C18—C19—C20—C21	0.8 (6)	C11—C5—Ca1—C2	−158.1 (2)
C19—C20—C21—C22	−0.4 (6)	C4—C5—Ca1—C1	111.8 (2)
C20—C21—C22—C17	0.2 (5)	C11—C5—Ca1—C1	−122.0 (3)
C20—C21—C22—C11	179.4 (3)	C4—C5—Ca1—C8	−105.17 (17)
C18—C17—C22—C21	−0.4 (4)	C1—C5—Ca1—C8	143.05 (18)
C18—C17—C22—C11	−179.6 (3)	C11—C5—Ca1—C8	21.1 (2)
C5—C11—C22—C21	−159.6 (2)	C3—C2—Ca1—O2	129.36 (19)
C23—C11—C22—C21	−42.6 (3)	C1—C2—Ca1—O2	−116.28 (19)
C12—C11—C22—C21	76.5 (3)	C3—C2—Ca1—O1	61.33 (19)
C5—C11—C22—C17	19.6 (3)	C1—C2—Ca1—O1	175.69 (17)
C23—C11—C22—C17	136.6 (3)	C3—C2—Ca1—C4	−37.63 (17)
C12—C11—C22—C17	−104.3 (3)	C1—C2—Ca1—C4	76.73 (18)
C29—C24—C25—C26	0.3 (5)	C3—C2—Ca1—C6	−123.39 (18)
C24—C25—C26—C27	1.1 (5)	C1—C2—Ca1—C6	−9.0 (2)
C25—C26—C27—C28	−1.5 (5)	C1—C2—Ca1—C3	114.4 (3)
C26—C27—C28—C29	0.6 (5)	C3—C2—Ca1—C10	−87.86 (19)
C25—C24—C29—C28	−1.2 (4)	C1—C2—Ca1—C10	26.5 (2)
C25—C24—C29—C12	176.4 (3)	C3—C2—Ca1—C7	−148.37 (19)
C27—C28—C29—C24	0.7 (4)	C1—C2—Ca1—C7	−34.0 (3)
C27—C28—C29—C12	−176.8 (2)	C3—C2—Ca1—C9	−59.1 (2)
C10—C12—C29—C24	−139.5 (2)	C1—C2—Ca1—C9	55.2 (3)
C30—C12—C29—C24	−23.0 (3)	C3—C2—Ca1—C5	−77.87 (19)
C11—C12—C29—C24	95.9 (3)	C1—C2—Ca1—C5	36.49 (16)
C10—C12—C29—C28	37.8 (3)	C3—C2—Ca1—C1	−114.4 (3)
C30—C12—C29—C28	154.3 (2)	C3—C2—Ca1—C8	−81.8 (6)
C11—C12—C29—C28	−86.8 (3)	C1—C2—Ca1—C8	32.6 (7)
C3—C4—Ca1—O2	18.4 (2)	C2—C1—Ca1—O2	65.16 (19)
C5—C4—Ca1—O2	−96.65 (17)	C5—C1—Ca1—O2	−179.41 (16)
C3—C4—Ca1—O1	−58.08 (19)	C2—C1—Ca1—O1	−5.8 (2)
C5—C4—Ca1—O1	−173.10 (14)	C5—C1—Ca1—O1	109.61 (17)
C3—C4—Ca1—C6	154.42 (18)	C2—C1—Ca1—C4	−77.1 (2)
C5—C4—Ca1—C6	39.40 (17)	C5—C1—Ca1—C4	38.32 (15)
C5—C4—Ca1—C3	−115.0 (2)	C2—C1—Ca1—C6	172.31 (19)
C3—C4—Ca1—C10	173.42 (19)	C5—C1—Ca1—C6	−72.26 (17)
C5—C4—Ca1—C10	58.40 (15)	C2—C1—Ca1—C3	−36.64 (18)
C3—C4—Ca1—C7	172.73 (19)	C5—C1—Ca1—C3	78.79 (18)
C5—C4—Ca1—C7	57.7 (2)	C2—C1—Ca1—C10	−156.72 (19)
C3—C4—Ca1—C9	−156.93 (19)	C5—C1—Ca1—C10	−41.29 (16)
C5—C4—Ca1—C9	88.05 (15)	C2—C1—Ca1—C7	159.53 (18)
C3—C4—Ca1—C5	115.0 (2)	C5—C1—Ca1—C7	−85.04 (18)
C3—C4—Ca1—C2	36.86 (18)	C2—C1—Ca1—C9	−142.80 (18)
C5—C4—Ca1—C2	−78.15 (17)	C5—C1—Ca1—C9	−27.4 (2)
C3—C4—Ca1—C1	76.8 (2)	C2—C1—Ca1—C5	−115.4 (3)
C5—C4—Ca1—C1	−38.21 (15)	C5—C1—Ca1—C2	115.4 (3)
C3—C4—Ca1—C8	−152.35 (19)	C2—C1—Ca1—C8	−170.6 (2)
C5—C4—Ca1—C8	92.64 (17)	C5—C1—Ca1—C8	−55.2 (2)
C7—C6—Ca1—O2	−57.4 (2)	C7—C8—Ca1—O2	63.27 (19)
C10—C6—Ca1—O2	−172.12 (15)	C9—C8—Ca1—O2	177.66 (18)
C7—C6—Ca1—O1	20.2 (2)	C7—C8—Ca1—O1	131.14 (18)
C10—C6—Ca1—O1	−94.53 (17)	C9—C8—Ca1—O1	−114.47 (19)
C7—C6—Ca1—C4	153.4 (2)	C7—C8—Ca1—C4	−123.47 (18)
C10—C6—Ca1—C4	38.73 (17)	C9—C8—Ca1—C4	−9.1 (2)
C7—C6—Ca1—C3	171.2 (2)	C7—C8—Ca1—C6	−37.35 (17)
C10—C6—Ca1—C3	56.5 (2)	C9—C8—Ca1—C6	77.04 (19)
C7—C6—Ca1—C10	114.7 (3)	C7—C8—Ca1—C3	−148.9 (2)
C10—C6—Ca1—C7	−114.7 (3)	C9—C8—Ca1—C3	−34.5 (3)
C7—C6—Ca1—C9	76.2 (2)	C7—C8—Ca1—C10	−77.76 (19)
C10—C6—Ca1—C9	−38.43 (15)	C9—C8—Ca1—C10	36.64 (16)
C7—C6—Ca1—C5	172.6 (2)	C9—C8—Ca1—C7	114.4 (3)
C10—C6—Ca1—C5	57.92 (16)	C7—C8—Ca1—C9	−114.4 (3)
C7—C6—Ca1—C2	−153.4 (2)	C7—C8—Ca1—C5	−88.12 (19)
C10—C6—Ca1—C2	91.94 (18)	C9—C8—Ca1—C5	26.3 (2)
C7—C6—Ca1—C1	−157.9 (2)	C7—C8—Ca1—C2	−84.7 (6)
C10—C6—Ca1—C1	87.37 (16)	C9—C8—Ca1—C2	29.7 (7)
C7—C6—Ca1—C8	36.39 (19)	C7—C8—Ca1—C1	−59.8 (2)
C10—C6—Ca1—C8	−78.28 (18)	C9—C8—Ca1—C1	54.6 (3)
C2—C3—Ca1—O2	−53.07 (19)	C15—C14—O1—C13	−173.2 (3)
C4—C3—Ca1—O2	−166.63 (17)	C15—C14—O1—Ca1	36.2 (4)
C2—C3—Ca1—O1	−121.40 (18)	O2—Ca1—O1—C14	−9.7 (2)
C4—C3—Ca1—O1	125.04 (18)	C4—Ca1—O1—C14	123.0 (3)
C2—C3—Ca1—C4	113.6 (3)	C6—Ca1—O1—C14	−103.3 (3)
C2—C3—Ca1—C6	78.8 (2)	C3—Ca1—O1—C14	97.3 (3)
C4—C3—Ca1—C6	−34.8 (2)	C10—Ca1—O1—C14	−144.8 (2)
C2—C3—Ca1—C10	106.50 (18)	C7—Ca1—O1—C14	−92.8 (3)
C4—C3—Ca1—C10	−7.1 (2)	C9—Ca1—O1—C14	−143.5 (3)
C2—C3—Ca1—C7	94.7 (4)	C5—Ca1—O1—C14	118.0 (3)
C4—C3—Ca1—C7	−18.8 (5)	C2—Ca1—O1—C14	71.0 (3)
C2—C3—Ca1—C9	140.22 (18)	C1—Ca1—O1—C14	74.0 (3)
C4—C3—Ca1—C9	26.7 (2)	C8—Ca1—O1—C14	−115.8 (3)
C2—C3—Ca1—C5	76.97 (19)	O2—Ca1—O1—C13	−156.5 (3)
C4—C3—Ca1—C5	−36.59 (16)	C4—Ca1—O1—C13	−23.8 (3)
C4—C3—Ca1—C2	−113.6 (3)	C6—Ca1—O1—C13	109.9 (3)
C2—C3—Ca1—C1	36.91 (17)	C3—Ca1—O1—C13	−49.6 (3)
C4—C3—Ca1—C1	−76.65 (19)	C10—Ca1—O1—C13	68.4 (3)
C2—C3—Ca1—C8	159.41 (19)	C7—Ca1—O1—C13	120.4 (3)
C4—C3—Ca1—C8	45.8 (3)	C9—Ca1—O1—C13	69.7 (3)
C6—C10—Ca1—O2	11.2 (2)	C5—Ca1—O1—C13	−28.8 (3)
C9—C10—Ca1—O2	−100.30 (19)	C2—Ca1—O1—C13	−75.8 (3)
C12—C10—Ca1—O2	138.52 (16)	C1—Ca1—O1—C13	−72.8 (3)
C6—C10—Ca1—O1	113.89 (17)	C8—Ca1—O1—C13	97.4 (3)
C9—C10—Ca1—O1	2.4 (2)	C14—C15—O2—C16	−135.3 (3)
C12—C10—Ca1—O1	−118.75 (17)	C14—C15—O2—Ca1	45.8 (4)
C6—C10—Ca1—C4	−142.74 (17)	O1—Ca1—O2—C16	162.0 (3)
C9—C10—Ca1—C4	105.81 (17)	C4—Ca1—O2—C16	70.3 (3)
C12—C10—Ca1—C4	−15.37 (17)	C6—Ca1—O2—C16	−65.8 (3)
C9—C10—Ca1—C6	−111.5 (2)	C3—Ca1—O2—C16	79.9 (3)
C12—C10—Ca1—C6	127.4 (3)	C10—Ca1—O2—C16	−71.8 (3)
C6—C10—Ca1—C3	−139.09 (17)	C7—Ca1—O2—C16	−91.3 (3)
C9—C10—Ca1—C3	109.46 (17)	C9—Ca1—O2—C16	−116.3 (3)
C12—C10—Ca1—C3	−11.7 (2)	C5—Ca1—O2—C16	28.3 (3)
C6—C10—Ca1—C7	36.62 (18)	C2—Ca1—O2—C16	56.1 (3)
C9—C10—Ca1—C7	−74.84 (19)	C1—Ca1—O2—C16	28.7 (3)
C12—C10—Ca1—C7	164.0 (2)	C8—Ca1—O2—C16	−117.9 (3)
C6—C10—Ca1—C9	111.5 (2)	O1—Ca1—O2—C15	−19.3 (3)
C12—C10—Ca1—C9	−121.2 (3)	C4—Ca1—O2—C15	−111.1 (3)
C6—C10—Ca1—C5	−114.47 (17)	C6—Ca1—O2—C15	112.9 (3)
C9—C10—Ca1—C5	134.08 (18)	C3—Ca1—O2—C15	−101.4 (3)
C12—C10—Ca1—C5	12.90 (16)	C10—Ca1—O2—C15	106.9 (3)
C6—C10—Ca1—C2	−106.07 (18)	C7—Ca1—O2—C15	87.3 (3)
C9—C10—Ca1—C2	142.48 (17)	C9—Ca1—O2—C15	62.4 (3)
C12—C10—Ca1—C2	21.3 (2)	C5—Ca1—O2—C15	−153.1 (3)
C6—C10—Ca1—C1	−93.00 (17)	C2—Ca1—O2—C15	−125.2 (3)
C9—C10—Ca1—C1	155.55 (17)	C1—Ca1—O2—C15	−152.7 (3)
C12—C10—Ca1—C1	34.37 (18)	C8—Ca1—O2—C15	60.8 (3)

Experimental details

Crystal data
Chemical formula	[Ca(C₂₆H₂₄)(C₄H₁₀O₂)]
M_r	466.65
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	213
a, b, c (Å)	27.726 (3), 12.412 (2), 16.087 (3)
β (°)	110.46 (2)
V (Å³)	5186.7 (14)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Siemens SMART 1K diffractometer
Absorption correction	Empirical (using intensity measurements) (XPREP; Sheldrick, 1998)
T_min, T_max	0.937, 0.961
No. of measured, independent and observed [I > 2σ(I)] reflections	14054, 4564, 4294
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.117, 1.29
No. of reflections	4564
No. of parameters	302
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.24

Computer programs: SMART (Bruker, 1997), SMART, SAINT-Plus (Bruker, 1999), XS (Sheldrick, 1998), XL (Sheldrick, 1998), XP (Sheldrick, 1998), XCIF (Sheldrick, 1998).

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