2,3,3a,4,9,9a-Hexahydro-9-phenylbenzo[f]indene derivatives

The title compounds, 3a,9a-trans-9,9a-trans-4,4-di­methyl-9-phenyl-2,3,3a,4,9,9a-hexa­hydro­benzo­[f]­indene, C₂₁H₂₄, (I), and 3a,4-trans-3a,9a-cis-9,9a-trans-4-methoxy-9-phenyl-2,3,3a,4,9,9a-hexa­hydro­benzo­[f]­indene, C₂₀H₂₂O, (II), are products of the photoinduced electron-transfer reaction of 1,1-di­phenyl-1,n-alka­dienes. The molecular structures are in good agreement with those proposed from the reaction mechanisms. The central rings of the fused systems of both compounds take chair and boat conformations in (I) and (II), respectively. There are no remarkable short contacts shorter than the sum of the van der Waals radii in the crystals, but some weak C—H...π interactions are found.

S1. Comment

Photoinduced electron-transfer reactions are recognized as versatile methods for generating radical cation species from electron-rich olefins and aromatic compounds (Neunteufel & Arnold, 1973; Majima et al., 1981; Mattes & Farid, 1986; Hoffmann et al., 1993; Heinemann & Demuth, 1997). Recently, it was found that 1,1-diphenyl-1,n-alkadienes (n = 6 or 7) were converted into 5/6/6- or 6/6/6-fused ring systems with high stereoselectivity by photoirradiation in the presence of phenanthrene and 1,4-dicyanobenzene (Ishii et al., 1998). In order to elucidate the molecular geometries of the photoreaction products, X-ray structure analyses of the title compounds, (I) and (II), were carried out. Moreover, these two compounds are considered to be good candidates for examining weak intermolecular interactions, since they have no remarkable pairs of hydrogen-bonding donors or acceptors. \sch

The molecular structure of (I) is shown in Fig. 1, along with the numbering of the atoms and the abbreviations of the rings. There are no anomalous bond lengths and angles. Ring B takes a chair conformation. Ring D is bonded to ring B at the equatorial position and is arranged almost perpendicular to the fused ring moiety. The two H atoms on the bridge heads between rings B and C are axial and are trans to each other. Ring C takes an envelope conformation, with C9a as the apical atom. The stereochemistry of (I) is in good agreement with that proposed from the reaction mechanism (Ishii et al., 1998).

The crystal structure of (I) is shown in Fig. 2. There are no remarkable short contacts shorter than the sum of the van der Waals radii. This indicates that weak interactions play an important role in the formation of the crystal. Such weak interactions contribute over long distances exceeding the sum of the van der Waals radii (Dunitz, 1996). The fused-ring moieties are arranged almost parallel to the (010) plane and those in molecules which are related by the inversion centre are face-to-face with each other, forming a dimer. The C9—H91 bond is directed towards ring A and C6—H61 is directed towards ring D of adjacent molecules; the detailed geometries (Table 1) are indicative of C–H···π interactions between them (Desiraju & Gavezzotti, 1989).

The molecular structure of (II) is shown in Fig. 3. Only the structure of one molecule, labelled X in Fig. 4, of two crystallographically independent molecules is shown in Fig. 3. The structures of the independent molecules are almost the same, except for the conformations of the methoxy groups. There are no anomalous bond lengths and angles. Ring B adopts a boat conformation. The phenyl and methoxy groups are bonded to ring B at the equatorial positions to avoid steric repulsion between them and are cis with each other. The two H atoms on the bridge heads are bonded on the axial positions and are cis with each other. This leads to an envelope conformation of ring C and the apical atom C2X is exo to ring A. The stereochemistry of (II) is in good agreement with that proposed from the reaction mechanism (Ishii, 1999).

The crystal structure of (II) is shown in Fig. 4. As in the case of (I), there are no remarkable short contacts shorter than the sum of the van der Waals radii. Each independent molecule is arranged alternately along the b axis and the fused-ring systems of molecules X and Y, as shown in Fig. 4, are almost parallel to the (100) and (011) planes, respectively. Three of the possible independent C—H···π interactions are shown in Fig. 4, with full details of the geometry in Table 2.

S2. Experimental

The syntheses of the title compounds have been reported previously by Ishii et al. (1998). Crystals of (I) and (II) were obtained from solutions in methanol.

S3. Refinement

All H atoms of (I) were located in difference maps and were refined as riding models, in which the distances of the C—H bonds were constrained to be 0.98, 0.97, 0.96 and 0.93 Å for the H atoms of methyne, methylene, methyl and aromatic moieties, respectively. The isotropic displacement parameters of the H atoms were constrained to be U_iso(H) = 1.5U_eq(C).

All H atoms of (II) were located in difference maps and were refined isotropically.

Computing details

For both compounds, data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1993). Program(s) used to solve structure: SHELXS86 (Sheldrick, 1990) for (I); SIR97 (Altomare et al., 1998) for (II). For both compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SV (Nemoto & Ohashi, 1993); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. ORTEPII (Johnson, 1976) drawing of (I). Displacement ellipsoids are drawn at 50% probability for non-H atoms and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The crystal structure of (I). Broken lines indicate the C—H···π interactions.
	Fig. 3. ORTEPII (Johnson, 1976) drawing of (II). Displacement ellipsoids are drawn at 50% probability for non-H atoms and H atoms are shown as small spheres of arbitrary radii.
	Fig. 4. The crystal structure of (II) viewed along the c axis. Broken lines indicate the C—H···π interactions.

(I) 3a,9a-trans-9,9a-trans-4,4-dimethyl-9- phenyl-2,3,3a,4,9,9a-hexahydrobenzo[f]indene

Crystal data

C21H24	F(000) = 300
Mr = 276.40	Dx = 1.119 Mg m^−3
Triclinic, P1	Melting point = 373–374 K
a = 9.483 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.042 (2) Å	Cell parameters from 25 reflections
c = 9.394 (2) Å	θ = 14–15°
α = 104.14 (2)°	µ = 0.06 mm^−1
β = 101.45 (2)°	T = 298 K
γ = 114.03 (2)°	Block, colourless
V = 820.4 (3) Å^3	0.3 × 0.3 × 0.2 mm
Z = 2

Data collection

Rigaku AFC-7R diffractometer	2621 reflections with I > 2σ(I)
Radiation source: normal-focus rotating anode	Rint = 0.019
Graphite monochromator	θmax = 27.5°, θmin = 2.2°
ω/2θ scan	h = 0→12
Absorption correction: ψ-scan (North et al., 1968)	k = −14→13
Tmin = 0.920, Tmax = 0.987	l = −12→11
4073 measured reflections	3 standard reflections every 100 reflections
3769 independent reflections	intensity decay: 0.4%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: difference Fourier map
wR(F^2) = 0.149	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0726P)^2 + 0.1178P] where P = (Fo^2 + 2Fc^2)/3
3769 reflections	(Δ/σ)max < 0.001
207 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.1897 (2)	0.3213 (2)	0.75371 (19)	0.0679
H11	0.2695	0.4207	0.8109	0.102*
H12	0.2037	0.2662	0.8161	0.102*
C2	0.0155 (3)	0.3011 (3)	0.7131 (3)	0.0944
H21	0.0134	0.3818	0.7808	0.142*
H22	−0.0574	0.2156	0.7260	0.142*
C3	−0.0388 (2)	0.2886 (2)	0.5434 (2)	0.0723
H31	−0.0719	0.3596	0.5349	0.108*
H32	−0.1301	0.1949	0.4794	0.108*
C3a	0.11184 (17)	0.31334 (15)	0.49179 (17)	0.0478
H3a1	0.1779	0.4165	0.5223	0.072*
C4	0.08534 (17)	0.24763 (16)	0.31854 (17)	0.0507
C4a	0.24778 (16)	0.26046 (14)	0.30064 (15)	0.0436
C5	0.2610 (2)	0.23392 (18)	0.15135 (17)	0.0578
H51	0.1718	0.2110	0.0674	0.087*
C6	0.4004 (2)	0.24043 (19)	0.12413 (19)	0.0624
H61	0.4049	0.2218	0.0235	0.094*
C7	0.5331 (2)	0.27476 (17)	0.24710 (19)	0.0571
H71	0.6288	0.2807	0.2304	0.086*
C8	0.52460 (17)	0.30048 (15)	0.39561 (17)	0.0469
H81	0.6154	0.3237	0.4780	0.070*
C8a	0.38271 (16)	0.29244 (13)	0.42545 (15)	0.0389
C9	0.38332 (16)	0.32361 (13)	0.59363 (14)	0.0397
H91	0.4392	0.4273	0.6457	0.060*
C9a	0.20861 (17)	0.26797 (15)	0.59627 (16)	0.0453
H9a1	0.1548	0.1638	0.5578	0.068*
C10	0.47708 (16)	0.26796 (14)	0.68466 (15)	0.0423
C11	0.4323 (2)	0.12430 (16)	0.63416 (19)	0.0581
H111	0.3460	0.0619	0.5417	0.087*
C12	0.5145 (2)	0.0727 (2)	0.7199 (2)	0.0704
H121	0.4820	−0.0240	0.6852	0.106*
C13	0.6437 (2)	0.1636 (2)	0.8558 (2)	0.0705
H131	0.6990	0.1286	0.9129	0.106*
C14	0.6903 (2)	0.3056 (2)	0.90650 (19)	0.0664
H141	0.7781	0.3676	0.9980	0.100*
C15	0.60727 (18)	0.35786 (17)	0.82202 (16)	0.0532
H151	0.6395	0.4546	0.8582	0.080*
C16	0.0280 (2)	0.3308 (3)	0.2322 (2)	0.0797
H161	−0.0712	0.3253	0.2477	0.120*
H162	0.0081	0.2902	0.1229	0.120*
H163	0.1115	0.4286	0.2726	0.120*
C17	−0.0438 (2)	0.0890 (2)	0.2465 (2)	0.0845
H171	−0.1486	0.0793	0.2488	0.127*
H172	−0.0129	0.0385	0.3053	0.127*
H173	−0.0505	0.0505	0.1406	0.127*
CgA	0.3916	0.2671	0.2740	0*
CgD	0.5609	0.2153	0.7705	0*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0785 (12)	0.0933 (13)	0.0546 (9)	0.0508 (10)	0.0387 (9)	0.0325 (9)
C2	0.0893 (15)	0.145 (2)	0.0900 (15)	0.0742 (15)	0.0592 (12)	0.0518 (14)
C3	0.0558 (10)	0.0928 (14)	0.0799 (12)	0.0422 (10)	0.0337 (9)	0.0295 (10)
C3a	0.0421 (7)	0.0508 (8)	0.0534 (8)	0.0246 (6)	0.0172 (6)	0.0185 (6)
C4	0.0390 (7)	0.0601 (9)	0.0469 (8)	0.0212 (6)	0.0098 (6)	0.0179 (7)
C4a	0.0449 (7)	0.0452 (7)	0.0415 (7)	0.0217 (6)	0.0147 (6)	0.0165 (6)
C5	0.0628 (9)	0.0685 (10)	0.0408 (7)	0.0313 (8)	0.0153 (7)	0.0197 (7)
C6	0.0778 (11)	0.0756 (11)	0.0495 (8)	0.0426 (9)	0.0338 (8)	0.0272 (8)
C7	0.0635 (9)	0.0656 (9)	0.0664 (10)	0.0393 (8)	0.0393 (8)	0.0339 (8)
C8	0.0455 (7)	0.0522 (8)	0.0535 (8)	0.0267 (6)	0.0217 (6)	0.0263 (6)
C8a	0.0421 (7)	0.0361 (6)	0.0413 (7)	0.0189 (5)	0.0154 (5)	0.0172 (5)
C9	0.0428 (7)	0.0390 (6)	0.0393 (6)	0.0209 (5)	0.0136 (5)	0.0152 (5)
C9a	0.0480 (7)	0.0495 (7)	0.0456 (7)	0.0255 (6)	0.0215 (6)	0.0203 (6)
C10	0.0449 (7)	0.0485 (7)	0.0410 (7)	0.0249 (6)	0.0180 (6)	0.0207 (6)
C11	0.0643 (9)	0.0511 (8)	0.0608 (9)	0.0304 (7)	0.0144 (7)	0.0240 (7)
C12	0.0854 (12)	0.0691 (11)	0.0849 (13)	0.0507 (10)	0.0347 (10)	0.0437 (10)
C13	0.0754 (11)	0.1065 (15)	0.0707 (11)	0.0641 (11)	0.0327 (9)	0.0551 (11)
C14	0.0609 (10)	0.0938 (13)	0.0505 (9)	0.0428 (10)	0.0131 (8)	0.0301 (9)
C15	0.0525 (8)	0.0628 (9)	0.0444 (8)	0.0289 (7)	0.0148 (6)	0.0187 (7)
C16	0.0668 (11)	0.1282 (18)	0.0726 (12)	0.0643 (12)	0.0233 (9)	0.0511 (12)
C17	0.0547 (10)	0.0749 (12)	0.0732 (12)	0.0029 (9)	0.0169 (9)	−0.0003 (9)

Geometric parameters (Å, º)

C1—C9a	1.527 (2)	C8—C8a	1.4005 (19)
C1—C2	1.528 (3)	C8—H81	0.9300
C1—H11	0.9700	C8a—C9	1.5308 (18)
C1—H12	0.9700	C9—C10	1.5163 (17)
C2—C3	1.528 (3)	C9—C9a	1.5224 (18)
C2—H21	0.9700	C9—H91	0.9800
C2—H22	0.9700	C9a—H9a1	0.9800
C3—C3a	1.540 (2)	C10—C15	1.385 (2)
C3—H31	0.9700	C10—C11	1.388 (2)
C3—H32	0.9700	C11—C12	1.384 (2)
C3a—C4	1.533 (2)	C11—H111	0.9300
C3a—C9a	1.5209 (19)	C12—C13	1.375 (3)
C3a—H3a1	0.9800	C12—H121	0.9300
C4—C4a	1.5355 (19)	C13—C14	1.367 (3)
C4—C17	1.539 (2)	C13—H131	0.9300
C4—C16	1.547 (2)	C14—C15	1.389 (2)
C4a—C5	1.4027 (19)	C14—H141	0.9300
C4a—C8a	1.4038 (19)	C15—H151	0.9300
C5—C6	1.373 (2)	C16—H161	0.9600
C5—H51	0.9300	C16—H162	0.9600
C6—C7	1.372 (2)	C16—H163	0.9600
C6—H61	0.9300	C17—H171	0.9600
C7—C8	1.380 (2)	C17—H172	0.9600
C7—H71	0.9300	C17—H173	0.9600
C9a—C1—C2	104.58 (14)	C8—C8a—C4a	118.61 (12)
C9a—C1—H11	110.8	C8—C8a—C9	118.58 (11)
C2—C1—H11	110.8	C4a—C8a—C9	122.78 (12)
C9a—C1—H12	110.8	C10—C9—C9a	111.80 (11)
C2—C1—H12	110.8	C10—C9—C8a	113.00 (10)
H11—C1—H12	108.9	C9a—C9—C8a	110.24 (11)
C1—C2—C3	107.15 (15)	C10—C9—H91	107.2
C1—C2—H21	110.3	C9a—C9—H91	107.2
C3—C2—H21	110.3	C8a—C9—H91	107.2
C1—C2—H22	110.3	C3a—C9a—C9	110.95 (11)
C3—C2—H22	110.3	C3a—C9a—C1	103.48 (12)
H21—C2—H22	108.5	C9—C9a—C1	116.29 (13)
C2—C3—C3a	105.52 (14)	C3a—C9a—H9a1	108.6
C2—C3—H31	110.6	C9—C9a—H9a1	108.6
C3a—C3—H31	110.6	C1—C9a—H9a1	108.6
C2—C3—H32	110.6	C15—C10—C11	118.00 (13)
C3a—C3—H32	110.6	C15—C10—C9	121.25 (13)
H31—C3—H32	108.8	C11—C10—C9	120.74 (13)
C9a—C3a—C4	113.35 (11)	C12—C11—C10	120.76 (16)
C9a—C3a—C3	104.16 (13)	C12—C11—H111	119.6
C4—C3a—C3	118.91 (13)	C10—C11—H111	119.6
C9a—C3a—H3a1	106.6	C13—C12—C11	120.48 (17)
C4—C3a—H3a1	106.6	C13—C12—H121	119.8
C3—C3a—H3a1	106.6	C11—C12—H121	119.8
C3a—C4—C4a	109.07 (11)	C14—C13—C12	119.48 (15)
C3a—C4—C17	112.22 (13)	C14—C13—H131	120.3
C4a—C4—C17	108.11 (14)	C12—C13—H131	120.3
C3a—C4—C16	107.89 (13)	C13—C14—C15	120.35 (16)
C4a—C4—C16	110.20 (13)	C13—C14—H141	119.8
C17—C4—C16	109.36 (15)	C15—C14—H141	119.8
C5—C4a—C8a	117.87 (13)	C10—C15—C14	120.93 (16)
C5—C4a—C4	118.68 (13)	C10—C15—H151	119.5
C8a—C4a—C4	123.40 (12)	C14—C15—H151	119.5
C6—C5—C4a	122.64 (15)	C4—C16—H161	109.5
C6—C5—H51	118.7	C4—C16—H162	109.5
C4a—C5—H51	118.7	H161—C16—H162	109.5
C7—C6—C5	119.20 (14)	C4—C16—H163	109.5
C7—C6—H61	120.4	H161—C16—H163	109.5
C5—C6—H61	120.4	H162—C16—H163	109.5
C6—C7—C8	119.97 (14)	C4—C17—H171	109.5
C6—C7—H71	120.0	C4—C17—H172	109.5
C8—C7—H71	120.0	H171—C17—H172	109.5
C7—C8—C8a	121.69 (14)	C4—C17—H173	109.5
C7—C8—H81	119.2	H171—C17—H173	109.5
C8a—C8—H81	119.2	H172—C17—H173	109.5
C9a—C1—C2—C3	−19.5 (2)	C8—C8a—C9—C10	−37.39 (16)
C1—C2—C3—C3a	−4.2 (2)	C4a—C8a—C9—C10	144.64 (12)
C2—C3—C3a—C9a	26.40 (19)	C8—C8a—C9—C9a	−163.31 (11)
C2—C3—C3a—C4	153.73 (16)	C4a—C8a—C9—C9a	18.72 (16)
C9a—C3a—C4—C4a	−45.62 (16)	C4—C3a—C9a—C9	65.33 (15)
C3—C3a—C4—C4a	−168.49 (14)	C3—C3a—C9a—C9	−163.98 (12)
C9a—C3a—C4—C17	74.14 (17)	C4—C3a—C9a—C1	−169.25 (13)
C3—C3a—C4—C17	−48.7 (2)	C3—C3a—C9a—C1	−38.57 (16)
C9a—C3a—C4—C16	−165.32 (13)	C10—C9—C9a—C3a	−174.55 (11)
C3—C3a—C4—C16	71.81 (18)	C8a—C9—C9a—C3a	−47.97 (14)
C3a—C4—C4a—C5	−167.22 (13)	C10—C9—C9a—C1	67.56 (16)
C17—C4—C4a—C5	70.50 (18)	C8a—C9—C9a—C1	−165.85 (12)
C16—C4—C4a—C5	−48.96 (19)	C2—C1—C9a—C3a	35.91 (18)
C3a—C4—C4a—C8a	15.20 (18)	C2—C1—C9a—C9	157.82 (15)
C17—C4—C4a—C8a	−107.08 (17)	C9a—C9—C10—C15	−112.21 (14)
C16—C4—C4a—C8a	133.46 (15)	C8a—C9—C10—C15	122.72 (14)
C8a—C4a—C5—C6	−1.1 (2)	C9a—C9—C10—C11	66.37 (17)
C4—C4a—C5—C6	−178.82 (15)	C8a—C9—C10—C11	−58.71 (17)
C4a—C5—C6—C7	−0.3 (3)	C15—C10—C11—C12	0.7 (2)
C5—C6—C7—C8	0.8 (2)	C9—C10—C11—C12	−177.90 (14)
C6—C7—C8—C8a	0.1 (2)	C10—C11—C12—C13	−0.9 (3)
C7—C8—C8a—C4a	−1.5 (2)	C11—C12—C13—C14	0.3 (3)
C7—C8—C8a—C9	−179.52 (12)	C12—C13—C14—C15	0.4 (3)
C5—C4a—C8a—C8	1.92 (19)	C11—C10—C15—C14	0.0 (2)
C4—C4a—C8a—C8	179.52 (12)	C9—C10—C15—C14	178.61 (13)
C5—C4a—C8a—C9	179.89 (12)	C13—C14—C15—C10	−0.6 (3)
C4—C4a—C8a—C9	−2.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H91···C4a^i	0.98	3.34	4.198 (2)	147
C9—H91···C5^i	0.98	3.38	4.317 (3)	161
C9—H91···C6^i	0.98	3.27	4.240 (3)	169
C9—H91···C7^i	0.98	3.08	3.995 (2)	156
C9—H91···C8^i	0.98	3.01	3.848 (2)	144
C9—H91···C8a^i	0.98	3.17	3.975 (2)	140
C9—H91···CgA^i	0.98	2.90	3.86	166
C6—H61···C10^ii	0.93	3.50	4.392 (2)	162
C6—H61···C11^ii	0.93	3.64	4.572 (3)	175
C6—H61···C12^ii	0.93	3.49	4.341 (3)	153
C6—H61···C13^ii	0.93	3.18	3.905 (3)	136
C6—H61···C14^ii	0.93	3.00	3.687 (3)	131
C6—H61···C15^ii	0.93	3.16	3.939 (2)	142
C6—H61···CgD^ii	0.93	3.04	3.91	157

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y, z−1.

(II) 3a,4-trans-3a,9a-cis-9,9a-trans-4-methoxy-9- phenyl-2,3,3a,4,9,9a-hexahydrobenzo[f]indene

Crystal data

C20H22O	Z = 4
Mr = 278.38	F(000) = 600
Triclinic, P1	Dx = 1.234 Mg m^−3
a = 9.0001 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 19.287 (2) Å	Cell parameters from 25 reflections
c = 8.9918 (8) Å	θ = 14–15°
α = 96.654 (8)°	µ = 0.07 mm^−1
β = 101.494 (7)°	T = 100 K
γ = 97.908 (8)°	Block, colourless
V = 1498.4 (2) Å^3	0.30 × 0.19 × 0.12 mm

Data collection

Rigaku AFC-7R diffractometer	6799 reflections with I > 2σ(I)
Radiation source: normal-focus rotating anode	Rint = 0.016
Graphite monochromator	θmax = 30.0°, θmin = 2.4°
ω/2θ scan	h = −8→12
Absorption correction: ψ-scan North et al., 1968	k = −27→26
Tmin = 0.965, Tmax = 0.991	l = −12→12
12299 measured reflections	3 standard reflections every 100 reflections
8747 independent reflections	intensity decay: 0.7%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: difference Fourier map
wR(F^2) = 0.121	All H-atom parameters refined
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0585P)^2 + 0.3481P] where P = (Fo^2 + 2Fc^2)/3
8747 reflections	(Δ/σ)max < 0.001
555 parameters	Δρmax = 0.43 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1X	0.17475 (13)	0.07985 (6)	0.89731 (12)	0.0177
H11X	0.2807 (16)	0.0761 (7)	0.9538 (16)	0.015 (3)*
H12X	0.0987 (17)	0.0504 (8)	0.9395 (17)	0.024 (4)*
C2X	0.15187 (14)	0.15727 (6)	0.90588 (13)	0.0196
H21X	0.1950 (18)	0.1850 (8)	1.0097 (18)	0.028 (4)*
H22X	0.0413 (17)	0.1608 (7)	0.8808 (16)	0.020 (3)*
C3X	0.22946 (14)	0.18390 (6)	0.78181 (13)	0.0193
H31X	0.1994 (17)	0.2301 (8)	0.7501 (17)	0.024 (4)*
H32X	0.3442 (17)	0.1909 (7)	0.8174 (16)	0.020 (3)*
C3aX	0.18343 (12)	0.12211 (5)	0.64901 (11)	0.01424
H3a1X	0.0816 (16)	0.1261 (7)	0.5830 (15)	0.015 (3)*
C4X	0.29768 (12)	0.12076 (5)	0.54401 (12)	0.01476
H41X	0.4020 (16)	0.1307 (7)	0.6086 (15)	0.014 (3)*
C4aX	0.27782 (12)	0.04863 (5)	0.44914 (12)	0.01446
C5X	0.26173 (12)	0.03805 (6)	0.29039 (12)	0.0170
H51X	0.2577 (17)	0.0791 (8)	0.2372 (17)	0.021 (3)*
C6X	0.25213 (13)	−0.02969 (6)	0.21175 (12)	0.0188
H61X	0.2380 (16)	−0.0368 (8)	0.0998 (17)	0.020 (3)*
C7X	0.26092 (13)	−0.08684 (6)	0.29251 (12)	0.0188
H71X	0.2566 (18)	−0.1342 (8)	0.2366 (17)	0.025 (4)*
C8X	0.27185 (12)	−0.07690 (6)	0.45070 (12)	0.01623
H81X	0.2769 (17)	−0.1180 (8)	0.5054 (17)	0.024 (4)*
C8aX	0.27786 (11)	−0.00968 (5)	0.52969 (11)	0.01377
C9X	0.28187 (12)	0.00529 (5)	0.70043 (11)	0.01334
H91X	0.3874 (17)	0.0333 (7)	0.7522 (16)	0.019 (3)*
C9aX	0.16330 (12)	0.05382 (5)	0.72561 (11)	0.01406
H9a1X	0.0599 (17)	0.0264 (7)	0.6788 (17)	0.020 (3)*
C10X	0.25862 (12)	−0.06166 (5)	0.77241 (11)	0.01416
C11X	0.38367 (12)	−0.08411 (6)	0.86041 (12)	0.01648
H111X	0.4874 (18)	−0.0551 (8)	0.8767 (17)	0.025 (4)*
C12X	0.36443 (14)	−0.14673 (6)	0.92318 (13)	0.0208
H121X	0.4562 (19)	−0.1619 (8)	0.9858 (18)	0.030 (4)*
C13X	0.22016 (14)	−0.18770 (6)	0.89813 (13)	0.0215
H131X	0.2092 (18)	−0.2317 (8)	0.9406 (18)	0.027 (4)*
C14X	0.09434 (13)	−0.16591 (6)	0.81039 (13)	0.0204
H141X	−0.0069 (18)	−0.1935 (8)	0.7924 (17)	0.026 (4)*
C15X	0.11375 (13)	−0.10325 (6)	0.74822 (12)	0.0177
H151X	0.0255 (17)	−0.0886 (8)	0.6892 (17)	0.022 (4)*
O1X	0.28090 (10)	0.17657 (4)	0.45421 (9)	0.01998
C16X	0.42121 (16)	0.20589 (7)	0.41787 (16)	0.0275
H161X	0.5030 (19)	0.2249 (8)	0.5145 (19)	0.031 (4)*
H162X	0.3966 (19)	0.2451 (9)	0.3624 (19)	0.033 (4)*
H163X	0.460 (2)	0.1708 (9)	0.352 (2)	0.038 (5)*
CgAX	0.2671	−0.0194	0.3707	0*
CgDX	0.2392	−0.1249	0.8355	0*
C1Y	0.09569 (13)	0.45094 (6)	0.26877 (15)	0.0223
H11Y	0.0479 (18)	0.4724 (8)	0.1756 (18)	0.028 (4)*
H12Y	0.0476 (19)	0.4665 (9)	0.3552 (19)	0.033 (4)*
C2Y	0.06822 (13)	0.37070 (6)	0.22366 (15)	0.0230
H21Y	−0.0401 (19)	0.3507 (8)	0.1614 (18)	0.030 (4)*
H22Y	0.0823 (18)	0.3470 (8)	0.3193 (18)	0.027 (4)*
C3Y	0.19496 (14)	0.35885 (7)	0.13737 (15)	0.0259
H31Y	0.210 (2)	0.3089 (9)	0.1257 (19)	0.036 (4)*
H32Y	0.170 (2)	0.3739 (9)	0.032 (2)	0.037 (4)*
C3aY	0.33807 (12)	0.40931 (6)	0.23547 (12)	0.0172
H3a1Y	0.3876 (18)	0.3864 (8)	0.3233 (17)	0.026 (4)*
C4Y	0.46475 (12)	0.43085 (6)	0.14870 (12)	0.01668
H41Y	0.4119 (16)	0.4373 (7)	0.0397 (16)	0.018 (3)*
C4aY	0.56725 (12)	0.49936 (5)	0.22675 (12)	0.01587
C5Y	0.72681 (12)	0.50830 (6)	0.24910 (13)	0.0185
H51Y	0.7749 (19)	0.4678 (9)	0.2162 (18)	0.030 (4)*
C6Y	0.81655 (13)	0.57324 (6)	0.31727 (13)	0.0202
H61Y	0.9270 (19)	0.5792 (8)	0.3311 (18)	0.030 (4)*
C7Y	0.74637 (13)	0.62956 (6)	0.36203 (13)	0.0198
H71Y	0.8084 (18)	0.6766 (8)	0.4092 (18)	0.026 (4)*
C8Y	0.58678 (12)	0.62097 (6)	0.33945 (12)	0.0171
H81Y	0.5373 (16)	0.6608 (7)	0.3674 (16)	0.017 (3)*
C8aY	0.49613 (12)	0.55611 (5)	0.27217 (12)	0.01517
C9Y	0.32202 (12)	0.54230 (5)	0.24341 (12)	0.01526
H91Y	0.2791 (17)	0.5327 (8)	0.1258 (17)	0.022 (3)*
C9aY	0.27206 (12)	0.47359 (5)	0.30533 (12)	0.01601
H9a1Y	0.3120 (16)	0.4811 (7)	0.4184 (16)	0.016 (3)*
C10Y	0.25510 (12)	0.60448 (5)	0.30606 (13)	0.0169
C11Y	0.18400 (13)	0.64635 (6)	0.20634 (15)	0.0225
H111Y	0.1765 (18)	0.6335 (8)	0.0975 (18)	0.027 (4)*
C12Y	0.12451 (15)	0.70474 (7)	0.26193 (18)	0.0291
H121Y	0.074 (2)	0.7316 (9)	0.191 (2)	0.038 (5)*
C13Y	0.13645 (15)	0.72235 (6)	0.41807 (18)	0.0306
H131Y	0.094 (2)	0.7634 (9)	0.460 (2)	0.038 (5)*
C14Y	0.20719 (14)	0.68123 (7)	0.51869 (16)	0.0265
H141Y	0.2187 (19)	0.6938 (9)	0.628 (2)	0.034 (4)*
C15Y	0.26564 (13)	0.62262 (6)	0.46337 (14)	0.0209
H151Y	0.3185 (17)	0.5949 (8)	0.5361 (17)	0.022 (4)*
O1Y	0.56203 (10)	0.37890 (4)	0.13506 (10)	0.02288
C16Y	0.49376 (15)	0.31733 (6)	0.02903 (15)	0.0246
H161Y	0.4362 (19)	0.2808 (8)	0.0787 (18)	0.030 (4)*
H162Y	0.4204 (18)	0.3285 (8)	−0.0609 (18)	0.027 (4)*
H163Y	0.580 (2)	0.2982 (9)	−0.003 (2)	0.042 (5)*
CgAY	0.6566	0.5646	0.2945	0*
CgDY	0.1955	0.6636	0.3618	0*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1X	0.0227 (5)	0.0176 (5)	0.0138 (4)	0.0042 (4)	0.0056 (4)	0.0024 (4)
C2X	0.0252 (6)	0.0177 (5)	0.0169 (5)	0.0049 (4)	0.0072 (4)	0.0004 (4)
C3X	0.0257 (6)	0.0148 (5)	0.0172 (5)	0.0029 (4)	0.0057 (4)	0.0005 (4)
C3aX	0.0160 (5)	0.0141 (4)	0.0131 (4)	0.0034 (3)	0.0034 (4)	0.0025 (3)
C4X	0.0159 (5)	0.0140 (4)	0.0151 (4)	0.0027 (4)	0.0038 (4)	0.0040 (3)
C4aX	0.0133 (4)	0.0155 (4)	0.0149 (4)	0.0023 (3)	0.0038 (3)	0.0026 (3)
C5X	0.0179 (5)	0.0190 (5)	0.0152 (5)	0.0026 (4)	0.0054 (4)	0.0046 (4)
C6X	0.0210 (5)	0.0220 (5)	0.0137 (4)	0.0027 (4)	0.0060 (4)	0.0012 (4)
C7X	0.0208 (5)	0.0179 (5)	0.0175 (5)	0.0027 (4)	0.0058 (4)	−0.0004 (4)
C8X	0.0178 (5)	0.0156 (5)	0.0161 (5)	0.0034 (4)	0.0049 (4)	0.0026 (4)
C8aX	0.0126 (4)	0.0160 (4)	0.0131 (4)	0.0027 (3)	0.0034 (3)	0.0020 (3)
C9X	0.0138 (4)	0.0135 (4)	0.0126 (4)	0.0020 (3)	0.0025 (3)	0.0024 (3)
C9aX	0.0146 (4)	0.0145 (4)	0.0131 (4)	0.0026 (3)	0.0029 (3)	0.0020 (3)
C10X	0.0168 (5)	0.0142 (4)	0.0121 (4)	0.0035 (4)	0.0040 (3)	0.0019 (3)
C11X	0.0163 (5)	0.0168 (5)	0.0166 (5)	0.0039 (4)	0.0035 (4)	0.0024 (4)
C12X	0.0243 (5)	0.0189 (5)	0.0205 (5)	0.0078 (4)	0.0034 (4)	0.0056 (4)
C13X	0.0292 (6)	0.0161 (5)	0.0211 (5)	0.0041 (4)	0.0080 (4)	0.0059 (4)
C14X	0.0210 (5)	0.0181 (5)	0.0221 (5)	−0.0001 (4)	0.0070 (4)	0.0029 (4)
C15X	0.0170 (5)	0.0182 (5)	0.0178 (5)	0.0023 (4)	0.0030 (4)	0.0036 (4)
O1X	0.0253 (4)	0.0167 (4)	0.0218 (4)	0.0053 (3)	0.0097 (3)	0.0089 (3)
C16X	0.0349 (7)	0.0193 (5)	0.0323 (6)	0.0001 (5)	0.0189 (5)	0.0056 (5)
C1Y	0.0150 (5)	0.0207 (5)	0.0312 (6)	0.0017 (4)	0.0056 (4)	0.0047 (4)
C2Y	0.0166 (5)	0.0216 (5)	0.0280 (6)	−0.0030 (4)	0.0037 (4)	0.0018 (4)
C3Y	0.0212 (5)	0.0216 (6)	0.0311 (6)	−0.0038 (4)	0.0067 (5)	−0.0050 (5)
C3aY	0.0159 (5)	0.0152 (4)	0.0197 (5)	0.0017 (4)	0.0028 (4)	0.0026 (4)
C4Y	0.0163 (5)	0.0155 (5)	0.0182 (5)	0.0045 (4)	0.0029 (4)	0.0018 (4)
C4aY	0.0148 (5)	0.0165 (5)	0.0164 (4)	0.0024 (4)	0.0027 (4)	0.0040 (4)
C5Y	0.0152 (5)	0.0200 (5)	0.0216 (5)	0.0043 (4)	0.0052 (4)	0.0044 (4)
C6Y	0.0140 (5)	0.0219 (5)	0.0252 (5)	0.0015 (4)	0.0046 (4)	0.0067 (4)
C7Y	0.0171 (5)	0.0184 (5)	0.0229 (5)	−0.0005 (4)	0.0031 (4)	0.0053 (4)
C8Y	0.0174 (5)	0.0157 (5)	0.0187 (5)	0.0020 (4)	0.0045 (4)	0.0040 (4)
C8aY	0.0131 (4)	0.0174 (5)	0.0154 (4)	0.0026 (4)	0.0028 (4)	0.0047 (4)
C9Y	0.0134 (4)	0.0149 (4)	0.0176 (5)	0.0035 (3)	0.0024 (4)	0.0033 (4)
C9aY	0.0146 (5)	0.0152 (4)	0.0183 (5)	0.0020 (4)	0.0039 (4)	0.0029 (4)
C10Y	0.0122 (4)	0.0149 (4)	0.0240 (5)	0.0018 (3)	0.0048 (4)	0.0030 (4)
C11Y	0.0198 (5)	0.0201 (5)	0.0300 (6)	0.0054 (4)	0.0070 (4)	0.0083 (4)
C12Y	0.0219 (6)	0.0188 (5)	0.0503 (8)	0.0074 (4)	0.0100 (5)	0.0122 (5)
C13Y	0.0206 (6)	0.0157 (5)	0.0569 (9)	0.0025 (4)	0.0155 (6)	−0.0009 (5)
C14Y	0.0217 (6)	0.0223 (5)	0.0342 (7)	−0.0011 (4)	0.0119 (5)	−0.0058 (5)
C15Y	0.0173 (5)	0.0202 (5)	0.0248 (5)	0.0024 (4)	0.0059 (4)	0.0008 (4)
O1Y	0.0196 (4)	0.0183 (4)	0.0294 (4)	0.0067 (3)	0.0029 (3)	−0.0024 (3)
C16Y	0.0294 (6)	0.0188 (5)	0.0262 (6)	0.0059 (5)	0.0088 (5)	−0.0013 (4)

Geometric parameters (Å, º)

C1X—C2X	1.5304 (15)	C1Y—C2Y	1.5265 (17)
C1X—C9aX	1.5456 (14)	C1Y—C9aY	1.5448 (15)
C1X—H11X	1.004 (14)	C1Y—H11Y	1.022 (16)
C1X—H12X	0.990 (15)	C1Y—H12Y	0.998 (17)
C2X—C3X	1.5299 (16)	C2Y—C3Y	1.5293 (17)
C2X—H21X	0.996 (16)	C2Y—H21Y	1.021 (16)
C2X—H22X	0.989 (15)	C2Y—H22Y	1.014 (16)
C3X—C3aX	1.5346 (14)	C3Y—C3aY	1.5451 (16)
C3X—H31X	1.022 (15)	C3Y—H31Y	0.987 (17)
C3X—H32X	1.003 (15)	C3Y—H32Y	1.010 (17)
C3aX—C4X	1.5290 (14)	C3aY—C4Y	1.5428 (15)
C3aX—C9aX	1.5609 (14)	C3aY—C9aY	1.5670 (15)
C3aX—H3a1X	1.006 (14)	C3aY—H3a1Y	1.007 (15)
C4X—O1X	1.4251 (12)	C4Y—O1Y	1.4287 (13)
C4X—C4aX	1.5136 (14)	C4Y—C4aY	1.5105 (15)
C4X—H41X	0.981 (14)	C4Y—H41Y	1.029 (14)
C4aX—C5X	1.3936 (14)	C4aY—C5Y	1.3932 (15)
C4aX—C8aX	1.4065 (14)	C4aY—C8aY	1.4028 (14)
C5X—C6X	1.3945 (15)	C5Y—C6Y	1.3942 (16)
C5X—H51X	0.972 (15)	C5Y—H51Y	0.989 (16)
C6X—C7X	1.3910 (15)	C6Y—C7Y	1.3891 (16)
C6X—H61X	0.980 (14)	C6Y—H61Y	0.966 (16)
C7X—C8X	1.3949 (14)	C7Y—C8Y	1.3936 (15)
C7X—H71X	0.982 (15)	C7Y—H71Y	0.996 (16)
C8X—C8aX	1.3931 (14)	C8Y—C8aY	1.3942 (15)
C8X—H81X	0.981 (15)	C8Y—H81Y	0.972 (14)
C8aX—C9X	1.5211 (14)	C8aY—C9Y	1.5169 (14)
C9X—C10X	1.5177 (14)	C9Y—C10Y	1.5152 (14)
C9X—C9aX	1.5455 (14)	C9Y—C9aY	1.5413 (15)
C9X—H91X	1.017 (15)	C9Y—H91Y	1.036 (15)
C9aX—H9a1X	0.990 (15)	C9aY—H9a1Y	0.995 (14)
C10X—C11X	1.3925 (14)	C10Y—C11Y	1.3954 (16)
C10X—C15X	1.3963 (15)	C10Y—C15Y	1.3982 (16)
C11X—C12X	1.3951 (15)	C11Y—C12Y	1.3954 (17)
C11X—H111X	0.994 (16)	C11Y—H111Y	0.968 (16)
C12X—C13X	1.3860 (17)	C12Y—C13Y	1.385 (2)
C12X—H121X	1.003 (16)	C12Y—H121Y	0.953 (18)
C13X—C14X	1.3904 (17)	C13Y—C14Y	1.389 (2)
C13X—H131X	0.971 (16)	C13Y—H131Y	0.992 (18)
C14X—C15X	1.3932 (15)	C14Y—C15Y	1.3927 (16)
C14X—H141X	0.963 (16)	C14Y—H141Y	0.966 (17)
C15X—H151X	0.960 (15)	C15Y—H151Y	0.984 (15)
O1X—C16X	1.4254 (15)	O1Y—C16Y	1.4142 (14)
C16X—H161X	1.014 (17)	C16Y—H161Y	1.014 (16)
C16X—H162X	0.979 (17)	C16Y—H162Y	1.002 (16)
C16X—H163X	0.992 (18)	C16Y—H163Y	0.984 (18)
C2X—C1X—C9aX	105.46 (8)	C2Y—C1Y—C9aY	105.37 (9)
C2X—C1X—H11X	110.8 (8)	C2Y—C1Y—H11Y	107.9 (9)
C9aX—C1X—H11X	107.3 (8)	C9aY—C1Y—H11Y	109.3 (9)
C2X—C1X—H12X	112.8 (9)	C2Y—C1Y—H12Y	113.1 (9)
C9aX—C1X—H12X	111.8 (9)	C9aY—C1Y—H12Y	113.2 (10)
H11X—C1X—H12X	108.6 (11)	H11Y—C1Y—H12Y	107.8 (13)
C3X—C2X—C1X	103.34 (9)	C1Y—C2Y—C3Y	103.01 (9)
C3X—C2X—H21X	113.4 (9)	C1Y—C2Y—H21Y	113.4 (9)
C1X—C2X—H21X	112.9 (9)	C3Y—C2Y—H21Y	113.9 (9)
C3X—C2X—H22X	109.8 (8)	C1Y—C2Y—H22Y	109.8 (9)
C1X—C2X—H22X	110.9 (8)	C3Y—C2Y—H22Y	110.3 (9)
H21X—C2X—H22X	106.6 (12)	H21Y—C2Y—H22Y	106.4 (13)
C2X—C3X—C3aX	103.94 (9)	C2Y—C3Y—C3aY	103.70 (9)
C2X—C3X—H31X	113.8 (9)	C2Y—C3Y—H31Y	112.0 (10)
C3aX—C3X—H31X	112.8 (8)	C3aY—C3Y—H31Y	112.8 (10)
C2X—C3X—H32X	110.2 (8)	C2Y—C3Y—H32Y	110.5 (10)
C3aX—C3X—H32X	107.4 (8)	C3aY—C3Y—H32Y	108.7 (10)
H31X—C3X—H32X	108.4 (12)	H31Y—C3Y—H32Y	109.1 (14)
C4X—C3aX—C3X	113.41 (9)	C4Y—C3aY—C3Y	114.90 (9)
C4X—C3aX—C9aX	113.04 (8)	C4Y—C3aY—C9aY	113.56 (8)
C3X—C3aX—C9aX	105.60 (8)	C3Y—C3aY—C9aY	104.37 (9)
C4X—C3aX—H3a1X	106.7 (8)	C4Y—C3aY—H3a1Y	106.3 (9)
C3X—C3aX—H3a1X	109.4 (8)	C3Y—C3aY—H3a1Y	110.1 (9)
C9aX—C3aX—H3a1X	108.6 (8)	C9aY—C3aY—H3a1Y	107.5 (9)
O1X—C4X—C4aX	113.56 (8)	O1Y—C4Y—C4aY	107.09 (8)
O1X—C4X—C3aX	108.15 (8)	O1Y—C4Y—C3aY	113.08 (9)
C4aX—C4X—C3aX	111.29 (8)	C4aY—C4Y—C3aY	111.73 (9)
O1X—C4X—H41X	107.7 (8)	O1Y—C4Y—H41Y	107.9 (8)
C4aX—C4X—H41X	107.8 (8)	C4aY—C4Y—H41Y	109.0 (8)
C3aX—C4X—H41X	108.2 (8)	C3aY—C4Y—H41Y	107.9 (8)
C5X—C4aX—C8aX	119.82 (9)	C5Y—C4aY—C8aY	119.91 (10)
C5X—C4aX—C4X	123.66 (9)	C5Y—C4aY—C4Y	122.41 (10)
C8aX—C4aX—C4X	116.52 (9)	C8aY—C4aY—C4Y	117.63 (9)
C4aX—C5X—C6X	120.36 (10)	C4aY—C5Y—C6Y	120.41 (10)
C4aX—C5X—H51X	118.0 (9)	C4aY—C5Y—H51Y	118.8 (10)
C6X—C5X—H51X	121.6 (9)	C6Y—C5Y—H51Y	120.8 (10)
C7X—C6X—C5X	119.80 (10)	C7Y—C6Y—C5Y	119.79 (10)
C7X—C6X—H61X	120.4 (8)	C7Y—C6Y—H61Y	120.3 (10)
C5X—C6X—H61X	119.8 (8)	C5Y—C6Y—H61Y	119.9 (9)
C6X—C7X—C8X	120.04 (10)	C6Y—C7Y—C8Y	120.03 (10)
C6X—C7X—H71X	119.3 (9)	C6Y—C7Y—H71Y	120.9 (9)
C8X—C7X—H71X	120.6 (9)	C8Y—C7Y—H71Y	119.0 (9)
C8aX—C8X—C7X	120.51 (10)	C7Y—C8Y—C8aY	120.60 (10)
C8aX—C8X—H81X	120.7 (9)	C7Y—C8Y—H81Y	120.1 (8)
C7X—C8X—H81X	118.8 (9)	C8aY—C8Y—H81Y	119.3 (8)
C8X—C8aX—C4aX	119.32 (9)	C8Y—C8aY—C4aY	119.27 (9)
C8X—C8aX—C9X	123.90 (9)	C8Y—C8aY—C9Y	123.96 (9)
C4aX—C8aX—C9X	116.77 (9)	C4aY—C8aY—C9Y	116.77 (9)
C10X—C9X—C8aX	112.83 (8)	C10Y—C9Y—C8aY	113.42 (9)
C10X—C9X—C9aX	112.31 (8)	C10Y—C9Y—C9aY	113.05 (9)
C8aX—C9X—C9aX	109.06 (8)	C8aY—C9Y—C9aY	108.44 (8)
C10X—C9X—H91X	108.3 (8)	C10Y—C9Y—H91Y	107.1 (8)
C8aX—C9X—H91X	107.3 (8)	C8aY—C9Y—H91Y	108.0 (8)
C9aX—C9X—H91X	106.8 (8)	C9aY—C9Y—H91Y	106.5 (8)
C9X—C9aX—C1X	112.47 (8)	C9Y—C9aY—C1Y	112.67 (9)
C9X—C9aX—C3aX	112.91 (8)	C9Y—C9aY—C3aY	112.37 (8)
C1X—C9aX—C3aX	105.67 (8)	C1Y—C9aY—C3aY	106.04 (9)
C9X—C9aX—H9a1X	107.4 (8)	C9Y—C9aY—H9a1Y	108.5 (8)
C1X—C9aX—H9a1X	110.1 (8)	C1Y—C9aY—H9a1Y	109.5 (8)
C3aX—C9aX—H9a1X	108.3 (8)	C3aY—C9aY—H9a1Y	107.7 (8)
C11X—C10X—C15X	118.53 (9)	C11Y—C10Y—C15Y	118.30 (10)
C11X—C10X—C9X	120.17 (9)	C11Y—C10Y—C9Y	120.01 (10)
C15X—C10X—C9X	121.27 (9)	C15Y—C10Y—C9Y	121.67 (10)
C10X—C11X—C12X	120.68 (10)	C12Y—C11Y—C10Y	120.93 (12)
C10X—C11X—H111X	118.9 (9)	C12Y—C11Y—H111Y	121.0 (9)
C12X—C11X—H111X	120.5 (9)	C10Y—C11Y—H111Y	118.1 (9)
C13X—C12X—C11X	120.31 (10)	C13Y—C12Y—C11Y	120.18 (12)
C13X—C12X—H121X	120.4 (9)	C13Y—C12Y—H121Y	120.6 (10)
C11X—C12X—H121X	119.3 (9)	C11Y—C12Y—H121Y	119.2 (10)
C12X—C13X—C14X	119.59 (10)	C12Y—C13Y—C14Y	119.51 (11)
C12X—C13X—H131X	119.2 (9)	C12Y—C13Y—H131Y	121.3 (10)
C14X—C13X—H131X	121.2 (9)	C14Y—C13Y—H131Y	119.2 (10)
C13X—C14X—C15X	119.99 (10)	C13Y—C14Y—C15Y	120.41 (12)
C13X—C14X—H141X	120.7 (9)	C13Y—C14Y—H141Y	120.1 (10)
C15X—C14X—H141X	119.3 (9)	C15Y—C14Y—H141Y	119.4 (10)
C14X—C15X—C10X	120.89 (10)	C14Y—C15Y—C10Y	120.67 (11)
C14X—C15X—H151X	119.0 (9)	C14Y—C15Y—H151Y	119.6 (9)
C10X—C15X—H151X	120.1 (9)	C10Y—C15Y—H151Y	119.7 (9)
C4X—O1X—C16X	113.00 (9)	C16Y—O1Y—C4Y	114.91 (9)
O1X—C16X—H161X	111.0 (9)	O1Y—C16Y—H161Y	111.5 (9)
O1X—C16X—H162X	105.3 (10)	O1Y—C16Y—H162Y	111.5 (9)
H161X—C16X—H162X	109.3 (13)	H161Y—C16Y—H162Y	108.4 (13)
O1X—C16X—H163X	111.8 (10)	O1Y—C16Y—H163Y	105.0 (10)
H161X—C16X—H163X	109.5 (14)	H161Y—C16Y—H163Y	109.0 (13)
H162X—C16X—H163X	109.8 (14)	H162Y—C16Y—H163Y	111.5 (14)
C9aX—C1X—C2X—C3X	−35.19 (11)	C9aY—C1Y—C2Y—C3Y	−35.95 (12)
C1X—C2X—C3X—C3aX	40.33 (11)	C1Y—C2Y—C3Y—C3aY	42.38 (12)
C2X—C3X—C3aX—C4X	−154.26 (9)	C2Y—C3Y—C3aY—C4Y	−157.19 (10)
C2X—C3X—C3aX—C9aX	−29.95 (11)	C2Y—C3Y—C3aY—C9aY	−32.17 (12)
C3X—C3aX—C4X—O1X	−73.07 (11)	C3Y—C3aY—C4Y—O1Y	−81.70 (12)
C9aX—C3aX—C4X—O1X	166.76 (8)	C9aY—C3aY—C4Y—O1Y	158.24 (9)
C3X—C3aX—C4X—C4aX	161.53 (9)	C3Y—C3aY—C4Y—C4aY	157.39 (10)
C9aX—C3aX—C4X—C4aX	41.36 (11)	C9aY—C3aY—C4Y—C4aY	37.33 (12)
O1X—C4X—C4aX—C5X	6.77 (14)	O1Y—C4Y—C4aY—C5Y	11.04 (14)
C3aX—C4X—C4aX—C5X	129.09 (10)	C3aY—C4Y—C4aY—C5Y	135.38 (10)
O1X—C4X—C4aX—C8aX	−173.95 (9)	O1Y—C4Y—C4aY—C8aY	−171.39 (9)
C3aX—C4X—C4aX—C8aX	−51.62 (12)	C3aY—C4Y—C4aY—C8aY	−47.05 (13)
C8aX—C4aX—C5X—C6X	−2.70 (16)	C8aY—C4aY—C5Y—C6Y	0.39 (16)
C4X—C4aX—C5X—C6X	176.56 (10)	C4Y—C4aY—C5Y—C6Y	177.91 (10)
C4aX—C5X—C6X—C7X	−0.94 (16)	C4aY—C5Y—C6Y—C7Y	−0.53 (17)
C5X—C6X—C7X—C8X	3.08 (17)	C5Y—C6Y—C7Y—C8Y	0.31 (17)
C6X—C7X—C8X—C8aX	−1.58 (16)	C6Y—C7Y—C8Y—C8aY	0.06 (17)
C7X—C8X—C8aX—C4aX	−2.05 (15)	C7Y—C8Y—C8aY—C4aY	−0.20 (16)
C7X—C8X—C8aX—C9X	176.87 (10)	C7Y—C8Y—C8aY—C9Y	−179.97 (10)
C5X—C4aX—C8aX—C8X	4.17 (15)	C5Y—C4aY—C8aY—C8Y	−0.03 (15)
C4X—C4aX—C8aX—C8X	−175.14 (9)	C4Y—C4aY—C8aY—C8Y	−177.66 (9)
C5X—C4aX—C8aX—C9X	−174.82 (9)	C5Y—C4aY—C8aY—C9Y	179.76 (9)
C4X—C4aX—C8aX—C9X	5.86 (13)	C4Y—C4aY—C8aY—C9Y	2.12 (14)
C8X—C8aX—C9X—C10X	−7.17 (14)	C8Y—C8aY—C9Y—C10Y	−4.42 (14)
C4aX—C8aX—C9X—C10X	171.77 (9)	C4aY—C8aY—C9Y—C10Y	175.81 (9)
C8X—C8aX—C9X—C9aX	−132.71 (10)	C8Y—C8aY—C9Y—C9aY	−130.87 (10)
C4aX—C8aX—C9X—C9aX	46.23 (12)	C4aY—C8aY—C9Y—C9aY	49.35 (12)
C10X—C9X—C9aX—C1X	61.82 (11)	C10Y—C9Y—C9aY—C1Y	58.49 (12)
C8aX—C9X—C9aX—C1X	−172.34 (8)	C8aY—C9Y—C9aY—C1Y	−174.85 (9)
C10X—C9X—C9aX—C3aX	−178.70 (8)	C10Y—C9Y—C9aY—C3aY	178.21 (9)
C8aX—C9X—C9aX—C3aX	−52.86 (11)	C8aY—C9Y—C9aY—C3aY	−55.13 (11)
C2X—C1X—C9aX—C9X	140.17 (9)	C2Y—C1Y—C9aY—C9Y	139.17 (10)
C2X—C1X—C9aX—C3aX	16.56 (11)	C2Y—C1Y—C9aY—C3aY	15.86 (12)
C4X—C3aX—C9aX—C9X	9.47 (12)	C4Y—C3aY—C9aY—C9Y	12.41 (12)
C3X—C3aX—C9aX—C9X	−115.07 (9)	C3Y—C3aY—C9aY—C9Y	−113.46 (10)
C4X—C3aX—C9aX—C1X	132.81 (9)	C4Y—C3aY—C9aY—C1Y	135.91 (9)
C3X—C3aX—C9aX—C1X	8.27 (11)	C3Y—C3aY—C9aY—C1Y	10.05 (11)
C8aX—C9X—C10X—C11X	102.86 (11)	C8aY—C9Y—C10Y—C11Y	104.92 (11)
C9aX—C9X—C10X—C11X	−133.38 (10)	C9aY—C9Y—C10Y—C11Y	−131.11 (11)
C8aX—C9X—C10X—C15X	−74.96 (12)	C8aY—C9Y—C10Y—C15Y	−73.50 (13)
C9aX—C9X—C10X—C15X	48.80 (12)	C9aY—C9Y—C10Y—C15Y	50.48 (13)
C15X—C10X—C11X—C12X	−0.11 (15)	C15Y—C10Y—C11Y—C12Y	−0.17 (17)
C9X—C10X—C11X—C12X	−177.99 (9)	C9Y—C10Y—C11Y—C12Y	−178.64 (11)
C10X—C11X—C12X—C13X	0.27 (16)	C10Y—C11Y—C12Y—C13Y	0.53 (18)
C11X—C12X—C13X—C14X	−0.22 (17)	C11Y—C12Y—C13Y—C14Y	−0.40 (19)
C12X—C13X—C14X—C15X	0.03 (17)	C12Y—C13Y—C14Y—C15Y	−0.08 (18)
C13X—C14X—C15X—C10X	0.13 (17)	C13Y—C14Y—C15Y—C10Y	0.43 (18)
C11X—C10X—C15X—C14X	−0.09 (15)	C11Y—C10Y—C15Y—C14Y	−0.30 (16)
C9X—C10X—C15X—C14X	177.77 (10)	C9Y—C10Y—C15Y—C14Y	178.13 (10)
C4aX—C4X—O1X—C16X	−87.95 (11)	C4aY—C4Y—O1Y—C16Y	−163.39 (9)
C3aX—C4X—O1X—C16X	148.01 (9)	C3aY—C4Y—O1Y—C16Y	73.10 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9aX—H9a1X···C4aX^i	0.990 (15)	3.109 (15)	4.0952 (15)	174.3 (11)
C9aX—H9a1X···C5X^i	0.990 (15)	3.067 (15)	3.9559 (15)	150.0 (11)
C9aX—H9a1X···C6X^i	0.990 (15)	3.161 (15)	3.8645 (15)	129.2 (10)
C9aX—H9a1X···C7X^i	0.990 (15)	3.304 (15)	3.9312 (16)	122.9 (10)
C9aX—H9a1X···C8X^i	0.990 (15)	3.301 (15)	4.0272 (15)	131.6 (10)
C9aX—H9a1X···C8aX^i	0.990 (15)	3.190 (15)	4.0919 (15)	152.1 (11)
C9aX—H9a1X···CgAX^i	0.990 (15)	2.87	3.74	147.8
C6X—H61X···C10X^ii	0.980 (14)	2.974 (15)	3.9404 (15)	168.9 (11)
C6X—H61X···C11X^ii	0.980 (14)	2.861 (14)	3.6807 (15)	141.7 (11)
C6X—H61X···C12X^ii	0.980 (14)	2.986 (14)	3.6285 (16)	124.2 (10)
C6X—H61X···C13X^ii	0.980 (14)	3.212 (14)	3.8428 (16)	123.6 (10)
C6X—H61X···C14X^ii	0.980 (14)	3.304 (14)	4.0838 (16)	137.8 (10)
C6X—H61X···C15X^ii	0.980 (14)	3.185 (15)	4.1244 (16)	161.1 (11)
C6X—H61X···CgDX^ii	0.980 (14)	2.76	3.63	148.3
C9aY—H9a1Y···C4aY^iii	0.995 (14)	3.120 (14)	4.1140 (15)	178.5 (11)
C9aY—H9a1Y···C5Y^iii	0.995 (14)	3.066 (14)	3.9790 (16)	153.2 (10)
C9aY—H9a1Y···C6Y^iii	0.995 (14)	3.070 (14)	3.8155 (16)	132.7 (10)
C9aY—H9a1Y···C7Y^iii	0.995 (14)	3.132 (14)	3.7971 (16)	125.5 (9)
C9aY—H9a1Y···C8Y^iii	0.995 (14)	3.185 (14)	3.9387 (15)	133.8 (10)
C9aY—H9a1Y···C8aY^iii	0.995 (14)	3.183 (14)	4.0974 (15)	153.6 (10)
C9aY—H9a1Y···CgAY^iii	0.995 (14)	2.80	3.71	151.9
C4Y—H41Y···C4aY^iv	1.029 (14)	2.840 (14)	3.7503 (15)	147.6 (10)
C4Y—H41Y···C5Y^iv	1.029 (14)	3.018 (14)	4.0270 (16)	166.8 (10)
C4Y—H41Y···C6Y^iv	1.029 (14)	3.417 (14)	4.4286 (16)	167.7 (10)
C4Y—H41Y···C7Y^iv	1.029 (14)	3.620 (14)	4.5532 (16)	151.7 (10)
C4Y—H41Y···C8Y^iv	1.029 (14)	3.467 (14)	4.3041 (16)	139.7 (10)
C4Y—H41Y···C8aY^iv	1.029 (14)	3.090 (14)	3.9033 (15)	136.7 (10)
C4Y—H41Y···CgAY^iv	1.029 (14)	2.94	3.93	161.8
C6Y—H61Y···C10Y^v	0.966 (16)	2.983 (17)	3.9331 (16)	167.9 (12)
C6Y—H61Y···C11Y^v	0.966 (16)	2.972 (16)	3.7786 (17)	141.8 (12)
C6Y—H61Y···C12Y^v	0.966 (16)	3.002 (16)	3.6428 (17)	125.0 (11)
C6Y—H61Y···C13Y^v	0.966 (16)	3.044 (16)	3.6687 (17)	123.7 (11)
C6Y—H61Y···C14Y^v	0.966 (16)	3.040 (16)	3.8147 (17)	138.1 (12)
C6Y—H61Y···C15Y^v	0.966 (16)	3.004 (17)	3.9375 (16)	162.8 (12)
C6Y—H61Y···CgDY^v	0.966 (16)	2.67	3.53	150.0
C16X—H161X···C10Y^iii	1.014 (17)	3.684 (16)	4.4842 (18)	137.5 (11)
C16X—H161X···C11Y^iii	1.014 (17)	3.770 (17)	4.729 (2)	158.6 (11)
C16X—H161X···C12Y^iii	1.014 (17)	3.543 (17)	4.494 (2)	157.1 (12)
C16X—H161X···C13Y^iii	1.014 (17)	3.177 (17)	3.951 (2)	134.1 (11)
C16X—H161X···C14Y^iii	1.014 (17)	3.050 (16)	3.6331 (18)	117.6 (11)
C16X—H161X···C15Y^iii	1.014 (17)	3.322 (16)	3.9295 (18)	120.1 (11)
C16X—H161X···CgDY^iii	1.014 (17)	3.14	3.99	141.8

Symmetry codes: (i) −x, −y, −z+1; (ii) x, y, z−1; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y+1, −z; (v) x+1, y, z.