(P,M)-1,2,3,9,10,11-Hexa­methoxy-5,7-di­hydro­dibenz­[c,e]­oxepine and (P,M)-1,11-di­methyl-5,5,7,7-tetra­phenyl-5,7-di­hydro­dibenz­[c,e]­oxepine

The title compounds, C₂₀H₂₄O₇ and C₄₀H₃₂O, respectively, are racemic oxepines, the mol­ecules of which contain a chiral axis. Both mol­ecules possess crystallographic C₂ symmetry and the seven-membered ring adopts a twisted-boat confor­mation.

S1. Comment

Molecules containing a chiral axis are becoming increasingly important in asymmetric synthesis, as chiral ligands or auxiliaries (Spring et al., 2002), as well as being potential pharmaceuticals (Bringmann et al., 2002). During our investigation of the synthesis of axially chiral amino alcohols by a simple ring-opening reaction of substituted dibenzo[c,e]oxepines (Furegati & Rippert, 2002), we obtained crystals of the title compounds, (I) and (II), respectively. As we are interested in the conformation of dibenzo-annellated seven-membered rings and the angle between the aromatic ring planes in general (Schneider et al., 2000), and, in particular, in the orientation of the phenyl substituents in the molecule of compound (II), we have determined the crystal structures of the title compounds. \sch

In both (I) and (II), the bond lengths and angles are within normal ranges. Both molecules possess crystallographic C₂ symmetry, with the twofold axis passing through the middle of the biphenyl bond (which corresponds with the C3—C4 bond in the oxepine nomenclature) and the O atom of the seven-membered ring. In compound (I), the H atoms of the methyl group at atom C9 adopt two disordered nearly equally occupied orientations, which differ by a rotation of the group by approximately 50°.

The oxepine ring in (I) and (II) adopts a twisted-boat conformation, in which one O—C bond and the opposing C—C bond that is fused to one of the phenyl rings forms the floor of the boat [for example, atoms C1, C2, O1 and C7(1 − x, y, 1/2 − z)]. The choice of O—C bond is irrelevant because of the molecular C₂ symmetry. The angles between the planes defined by this four-atom floor and the three-atom bow plane [atoms C2, C7 and O1] of the boat are 48.22 (12) and 44.03 (14)° for (I) and (II), respectively, while the angles between the floor and the four-atom stern [atoms C1, C1(1 − x, y, 1/2 − z), C2(1 − x, y, 1/2 − z) and C7(1 − x, y, 1/2 − z) for (I), similarly for (II)] of the boat are 52.66 (8) and 54.72 (1)°, respectively. In (I), the angle between the planes of the biphenyl aromatic rings is 52.92 (6), whereas in (II), the angle is almost 9° greater, at 61.47 (8)°. The latter is a rather large angle for a biphenyl with a three-atom bridge and its possible cause is discussed below.

The Cambridge Structural Database (CSD, January 2004 release; Allen, 2002) contains the details of seven structures of 5,7-dihydrodibenzo[c,e]oxepines (no dinaphth[c,e]oxepines were found). Two of these structures are transition-metal complexes and so were discarded. Out of the remaining five structures, only two had peri substituents at the biphenyl moiety (Schmid et al., 1988; Roszak et al., 1996). Both structures show a twisted-boat conformation; the angle between the four-atom floor and the three-atom bow plane is in the range 44.0–50.1°, while the angle between the floor and the four-atom stern of the boat is in the range 54.1–55.5°. The angle between the planes of the biphenyl aromatic rings in these compounds is in the range 49.2–56.6°. All of these values are very similar to those in compounds (I) and (II). In the three structures with no substituents at the peri positions of the biphenyl moiety (Nieger et al., 1998; Carey et al., 2002), the outlined angles are again in similar ranges; floor/bow: 39.5–46.2°, floor/stern: 48.1–52.5° and biphenyl ring plane angle: 46.2–50.4°. Although two of these structures have a similar 5,5,7,7-tetraphenyl substitution pattern to compound (II), the angles between the planes of the biphenyl aromatic rings are no larger than usual, unlike that in (II). Therefore, the tetraphenyl substitution pattern alone does not introduce sufficient steric constraints to cause an increase in the biphenyl plane angle, but in combination with the addition of substituents at the peri position of the biphenyl moiety, as in compound (II), there is apparently sufficient steric strain to cause a significant increase in this angle.

A previous analysis of related dibenz- and dinaphthazepine derivatives (Schneider et al., 2000), which have an N atom in the seven-membered ring in place of the O atom, revealed quite similar conformational properties for both the conformation of the seven-membered ring and the angle between the planes of the biphenyl (or binaphthyl) aromatic rings.

S2. Experimental

The title compounds can be synthesized almost quantitatively by boiling the corresponding biphenyl diol in toluene for 12 h in the presence of catalytic amounts of toluenesulfonic acid with the reaction vessel connected to a water extractor (Wittig & Zimmermann, 1955). Compound (I) (m.p. 422 K) was crystallized from methyl tert-butyl ether/toluene (Ratio?) and compound (II) (m.p. 576 K) was crystallized from neat toluene.

S3. Refinement

For each structure, the methyl H atoms were constrained to an ideal geometry (C—H = 0.98 Å) with U_iso(H) = 1.5U_eq(C), but were allowed to rotate freely about the parent C—O or C—C bond. All remaining H atoms were placed in geometrically idealized positions (C—H = 0.95–0.99 Å) and constrained to ride on their parent atoms with U_iso(H) = 1.2U_eq(C). For (I), a difference Fourier map showed that the H atoms of the methyl group at atom C9 adopted two disordered orientations which differ by a rotation of the group by approximately 50°. Therefore, two idealized orientations were defined for these H atoms and constrained refinement of the site occupation factors led to a value of 0.55 (2) for the major conformation. For (I) and (II), two and five low-angle reflections, respectively, had unexpectedly low intensities as a result of being partially obscured by the beam stop and were omitted.

Computing details

For both compounds, data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2004).

Figures

	Fig. 1. A view of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented by circles of arbitrary size. Only one of the disordered orientations of the C9 methyl H atoms is shown. [Symmetry code: (i) 1 − x, y, 1/2 − z.]
	Fig. 2. A view of the molecule of (II) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented by circles of arbitrary size. [Symmetry code: (i) 1 − x, y, 3/2 − z.]

(I) (P,M)-1,2,3,9,10,11-hexamethoxy-5,7-dihydrodibenz[c,e]oxepine

Crystal data

C20H24O7	F(000) = 800
Mr = 376.40	Dx = 1.401 Mg m^−3
Monoclinic, C2/c	Melting point: 422 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 15.3979 (3) Å	Cell parameters from 2731 reflections
b = 10.3781 (2) Å	θ = 2.0–30.0°
c = 11.8825 (3) Å	µ = 0.11 mm^−1
β = 109.9789 (8)°	T = 160 K
V = 1784.56 (7) Å^3	Prism, colourless
Z = 4	0.25 × 0.20 × 0.10 mm

Data collection

Nonius KappaCCD area-detector diffractometer	1974 reflections with I > 2σ(I)
Radiation source: Nonius FR590 sealed-tube generator	Rint = 0.042
Horizontally mounted graphite crystal monochromator	θmax = 30.0°, θmin = 2.4°
Detector resolution: 9 pixels mm^-1	h = 0→21
ϕ and ω scans with κ offsets	k = 0→14
25172 measured reflections	l = −16→15
2607 independent reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.130	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0666P)^2 + 0.8193P] where P = (Fo^2 + 2Fc^2)/3
2605 reflections	(Δ/σ)max = 0.001
127 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Special details

Experimental. Solvent used: MTBE / toluene Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.572 (2) Frames collected: 378 Seconds exposure per frame: 30 Degrees rotation per frame: 2.0 Crystal-Detector distance (mm): 30.0

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	Occ. (<1)
O1	0.5000	0.06297 (11)	0.2500	0.0288 (3)
O4	0.83719 (6)	0.36458 (9)	0.35522 (9)	0.0335 (2)
O5	0.75241 (6)	0.56222 (8)	0.42197 (8)	0.0289 (2)
O6	0.56093 (6)	0.55950 (8)	0.36775 (7)	0.0279 (2)
C1	0.55123 (7)	0.35803 (11)	0.26849 (10)	0.0228 (2)
C2	0.59560 (8)	0.25106 (11)	0.24121 (10)	0.0248 (3)
C3	0.69147 (8)	0.24833 (12)	0.27160 (11)	0.0265 (3)
H3	0.7207	0.1752	0.2521	0.032*
C4	0.74411 (8)	0.35240 (12)	0.33028 (11)	0.0260 (3)
C5	0.70150 (8)	0.45670 (11)	0.36557 (10)	0.0248 (3)
C6	0.60557 (8)	0.45904 (11)	0.33557 (10)	0.0234 (2)
C7	0.53814 (8)	0.13833 (12)	0.17641 (11)	0.0273 (3)
H71	0.4869	0.1710	0.1064	0.033*
H72	0.5770	0.0818	0.1460	0.033*
C8	0.88330 (9)	0.26206 (14)	0.31820 (15)	0.0398 (3)
H81	0.8834	0.1849	0.3658	0.060*
H82	0.9471	0.2876	0.3302	0.060*
H8C	0.8510	0.2434	0.2333	0.060*
C9	0.82055 (10)	0.53729 (15)	0.53774 (12)	0.0391 (3)
H91	0.8235	0.4445	0.5539	0.059*	0.55 (3)
H92	0.8035	0.5828	0.5994	0.059*	0.55 (3)
H93	0.8811	0.5676	0.5387	0.059*	0.55 (3)
H94	0.8561	0.6159	0.5679	0.059*	0.45 (3)
H95	0.8623	0.4689	0.5307	0.059*	0.45 (3)
H96	0.7896	0.5101	0.5934	0.059*	0.45 (3)
C10	0.59472 (10)	0.59818 (14)	0.49093 (11)	0.0347 (3)
H101	0.6214	0.5235	0.5414	0.052*
H102	0.5436	0.6328	0.5132	0.052*
H103	0.6422	0.6646	0.5025	0.052*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0302 (6)	0.0222 (6)	0.0338 (6)	0.000	0.0105 (5)	0.000
O4	0.0229 (4)	0.0324 (5)	0.0450 (5)	−0.0013 (4)	0.0112 (4)	−0.0036 (4)
O5	0.0279 (4)	0.0259 (4)	0.0285 (4)	−0.0048 (3)	0.0039 (3)	−0.0008 (3)
O6	0.0297 (4)	0.0262 (4)	0.0254 (4)	0.0036 (3)	0.0063 (3)	−0.0043 (3)
C1	0.0229 (6)	0.0240 (6)	0.0207 (5)	0.0001 (4)	0.0065 (4)	0.0012 (4)
C2	0.0260 (5)	0.0244 (6)	0.0228 (5)	−0.0003 (4)	0.0068 (4)	−0.0002 (4)
C3	0.0272 (6)	0.0251 (6)	0.0272 (6)	0.0019 (4)	0.0093 (5)	0.0000 (4)
C4	0.0220 (5)	0.0277 (6)	0.0275 (6)	−0.0002 (4)	0.0072 (4)	0.0030 (5)
C5	0.0261 (6)	0.0233 (5)	0.0227 (5)	−0.0029 (4)	0.0056 (4)	0.0007 (4)
C6	0.0261 (6)	0.0219 (5)	0.0211 (5)	0.0011 (4)	0.0067 (4)	0.0003 (4)
C7	0.0277 (6)	0.0254 (6)	0.0280 (6)	−0.0010 (5)	0.0084 (5)	−0.0036 (4)
C8	0.0267 (6)	0.0350 (7)	0.0579 (9)	0.0046 (5)	0.0147 (6)	0.0009 (6)
C9	0.0351 (7)	0.0416 (8)	0.0316 (7)	−0.0046 (6)	−0.0001 (6)	−0.0026 (6)
C10	0.0404 (7)	0.0352 (7)	0.0270 (6)	0.0023 (6)	0.0097 (5)	−0.0050 (5)

Geometric parameters (Å, º)

O1—C7	1.4394 (14)	C5—C6	1.3963 (16)
O1—C7^i	1.4394 (14)	C7—H71	0.9900
O4—C4	1.3665 (14)	C7—H72	0.9900
O4—C8	1.4294 (17)	C8—H81	0.9800
O5—C5	1.3799 (14)	C8—H82	0.9800
O5—C9	1.4401 (15)	C8—H8C	0.9800
O6—C6	1.3730 (14)	C9—H91	0.9800
O6—C10	1.4331 (15)	C9—H92	0.9800
C1—C2	1.3984 (16)	C9—H93	0.9800
C1—C6	1.4066 (16)	C9—H94	0.9800
C1—C1^i	1.486 (2)	C9—H95	0.9800
C2—C3	1.3950 (16)	C9—H96	0.9800
C2—C7	1.5096 (16)	C10—H101	0.9800
C3—C4	1.3869 (17)	C10—H102	0.9800
C3—H3	0.9500	C10—H103	0.9800
C4—C5	1.4022 (17)
C7—O1—C7^i	114.18 (12)	O1—C7—H72	108.8
C4—O4—C8	117.31 (10)	C2—C7—H72	108.8
C5—O5—C9	115.40 (10)	H71—C7—H72	107.7
C6—O6—C10	117.10 (10)	O4—C8—H81	109.5
C2—C1—C6	118.68 (10)	O4—C8—H82	109.5
C2—C1—C1^i	119.00 (8)	H81—C8—H82	109.5
C6—C1—C1^i	122.23 (8)	O4—C8—H8C	109.5
C3—C2—C1	120.91 (11)	H81—C8—H8C	109.5
C3—C2—C7	120.02 (10)	H82—C8—H8C	109.5
C1—C2—C7	119.07 (10)	O5—C9—H91	109.5
C4—C3—C2	119.96 (11)	O5—C9—H92	109.5
C4—C3—H3	120.0	O5—C9—H93	109.5
C2—C3—H3	120.0	O5—C9—H94	109.5
O4—C4—C3	124.79 (11)	O5—C9—H95	109.5
O4—C4—C5	115.28 (10)	H94—C9—H95	109.5
C3—C4—C5	119.91 (11)	O5—C9—H96	109.5
O5—C5—C6	119.08 (10)	H94—C9—H96	109.5
O5—C5—C4	120.77 (10)	H95—C9—H96	109.5
C6—C5—C4	119.96 (11)	O6—C10—H101	109.5
O6—C6—C5	121.91 (10)	O6—C10—H102	109.5
O6—C6—C1	117.80 (10)	H101—C10—H102	109.5
C5—C6—C1	120.28 (10)	O6—C10—H103	109.5
O1—C7—C2	113.63 (9)	H101—C10—H103	109.5
O1—C7—H71	108.8	H102—C10—H103	109.5
C2—C7—H71	108.8
C6—C1—C2—C3	−4.90 (17)	C3—C4—C5—C6	−3.67 (18)
C1^i—C1—C2—C3	178.40 (12)	C10—O6—C6—C5	−50.58 (15)
C6—C1—C2—C7	175.97 (10)	C10—O6—C6—C1	130.67 (12)
C1^i—C1—C2—C7	−0.73 (18)	O5—C5—C6—O6	−4.52 (16)
C1—C2—C3—C4	0.36 (18)	C4—C5—C6—O6	−179.66 (10)
C7—C2—C3—C4	179.48 (11)	O5—C5—C6—C1	174.20 (10)
C8—O4—C4—C3	−0.19 (18)	C4—C5—C6—C1	−0.94 (17)
C8—O4—C4—C5	−178.46 (11)	C2—C1—C6—O6	−176.07 (10)
C2—C3—C4—O4	−174.24 (11)	C1^i—C1—C6—O6	0.52 (18)
C2—C3—C4—C5	3.97 (18)	C2—C1—C6—C5	5.16 (17)
C9—O5—C5—C6	120.48 (12)	C1^i—C1—C6—C5	−178.25 (12)
C9—O5—C5—C4	−64.42 (15)	C7^i—O1—C7—C2	43.58 (7)
O4—C4—C5—O5	−0.37 (16)	C3—C2—C7—O1	108.10 (12)
C3—C4—C5—O5	−178.73 (10)	C1—C2—C7—O1	−72.76 (14)
O4—C4—C5—C6	174.69 (10)

Symmetry code: (i) −x+1, y, −z+1/2.

(II) (P,M)-1,11-dimethyl-5,5,7,7-tetraphenyl-5,7-dihydrodibenz[c,e]oxepine

Crystal data

C40H32O	Dx = 1.235 Mg m^−3
Mr = 528.66	Melting point: 576 K
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 2853 reflections
a = 16.6918 (4) Å	θ = 2.0–25.0°
b = 9.6863 (3) Å	µ = 0.07 mm^−1
c = 17.5921 (5) Å	T = 160 K
V = 2844.32 (14) Å^3	Prism, colourless
Z = 4	0.22 × 0.15 × 0.12 mm
F(000) = 1120

Data collection

Nonius KappaCCD area-detector diffractometer	1920 reflections with I > 2σ(I)
Radiation source: Nonius FR590 sealed tube generator	Rint = 0.063
Horizontally mounted graphite crystal monochromator	θmax = 25.0°, θmin = 3.4°
Detector resolution: 9 pixels mm^-1	h = 0→19
ϕ and ω scans with κ offsets	k = 0→11
25719 measured reflections	l = −20→0
2507 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H-atom parameters constrained
wR(F^2) = 0.129	w = 1/[σ^2(Fo^2) + (0.0767P)^2 + 0.6145P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
2502 reflections	Δρmax = 0.25 e Å^−3
188 parameters	Δρmin = −0.22 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.011 (2)

Special details

Experimental. Solvent used: toluene Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 1.164 (2) Frames collected: 391 Seconds exposure per frame: 63 Degrees rotation per frame: 0.7 Crystal-Detector distance (mm): 30.0

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
O1	0.5000	1.10879 (14)	0.7500	0.0293 (4)
C1	0.49553 (10)	0.80328 (15)	0.70779 (9)	0.0304 (4)
C2	0.45619 (9)	0.91417 (15)	0.67192 (9)	0.0289 (4)
C3	0.44774 (10)	0.91548 (17)	0.59321 (9)	0.0329 (4)
H3	0.4202	0.9894	0.5692	0.039*
C4	0.47945 (10)	0.80920 (17)	0.54972 (10)	0.0383 (4)
H4	0.4727	0.8094	0.4961	0.046*
C5	0.52073 (11)	0.70320 (17)	0.58452 (10)	0.0390 (5)
H5	0.5434	0.6321	0.5542	0.047*
C6	0.52992 (10)	0.69820 (16)	0.66328 (10)	0.0351 (4)
C7	0.43018 (9)	1.03781 (15)	0.72078 (9)	0.0289 (4)
C8	0.58112 (12)	0.58504 (17)	0.69659 (12)	0.0448 (5)
H81	0.5519	0.4974	0.6946	0.067*
H82	0.5939	0.6073	0.7496	0.067*
H83	0.6308	0.5769	0.6673	0.067*
C9	0.38753 (10)	1.15068 (16)	0.67370 (9)	0.0299 (4)
C10	0.42623 (11)	1.27278 (17)	0.65410 (10)	0.0355 (4)
H10	0.4792	1.2893	0.6716	0.043*
C11	0.38812 (12)	1.37113 (18)	0.60903 (10)	0.0415 (5)
H11	0.4151	1.4545	0.5966	0.050*
C12	0.31191 (12)	1.34882 (19)	0.58236 (10)	0.0430 (5)
H12	0.2867	1.4151	0.5506	0.052*
C13	0.27211 (11)	1.22854 (19)	0.60230 (10)	0.0424 (5)
H13	0.2191	1.2128	0.5846	0.051*
C14	0.30926 (11)	1.13119 (18)	0.64795 (10)	0.0377 (4)
H14	0.2810	1.0499	0.6619	0.045*
C15	0.37339 (9)	0.99495 (16)	0.78546 (9)	0.0307 (4)
C16	0.37386 (10)	1.06295 (18)	0.85510 (10)	0.0354 (4)
H16	0.4113	1.1351	0.8638	0.042*
C17	0.32038 (10)	1.0265 (2)	0.91179 (10)	0.0429 (5)
H17	0.3217	1.0731	0.9593	0.051*
C18	0.26491 (11)	0.9225 (2)	0.89964 (11)	0.0474 (5)
H18	0.2284	0.8973	0.9387	0.057*
C19	0.26295 (11)	0.8556 (2)	0.83041 (11)	0.0440 (5)
H19	0.2245	0.7852	0.8215	0.053*
C20	0.31694 (10)	0.89097 (17)	0.77387 (11)	0.0364 (4)
H20	0.3155	0.8437	0.7266	0.044*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0298 (8)	0.0261 (8)	0.0318 (9)	0.000	−0.0052 (7)	0.000
C1	0.0328 (9)	0.0278 (8)	0.0305 (9)	−0.0044 (7)	0.0022 (7)	−0.0021 (7)
C2	0.0298 (8)	0.0280 (8)	0.0289 (9)	−0.0053 (7)	0.0014 (7)	−0.0010 (6)
C3	0.0355 (9)	0.0333 (9)	0.0298 (9)	−0.0038 (7)	−0.0012 (7)	0.0004 (7)
C4	0.0470 (10)	0.0406 (10)	0.0272 (9)	−0.0047 (8)	0.0011 (8)	−0.0045 (8)
C5	0.0490 (11)	0.0339 (9)	0.0342 (10)	−0.0023 (8)	0.0074 (8)	−0.0078 (7)
C6	0.0406 (10)	0.0286 (9)	0.0362 (10)	−0.0037 (7)	0.0029 (7)	−0.0043 (7)
C7	0.0302 (8)	0.0287 (8)	0.0278 (9)	−0.0010 (7)	−0.0035 (6)	−0.0012 (7)
C8	0.0569 (12)	0.0319 (9)	0.0456 (11)	0.0088 (8)	0.0033 (9)	−0.0035 (8)
C9	0.0360 (9)	0.0302 (9)	0.0236 (8)	0.0036 (7)	−0.0017 (7)	−0.0022 (6)
C10	0.0387 (9)	0.0334 (9)	0.0343 (10)	0.0013 (7)	−0.0036 (7)	0.0006 (7)
C11	0.0546 (12)	0.0331 (9)	0.0370 (11)	0.0049 (8)	−0.0032 (8)	0.0040 (8)
C12	0.0565 (12)	0.0414 (10)	0.0312 (10)	0.0147 (9)	−0.0068 (9)	0.0005 (8)
C13	0.0406 (10)	0.0492 (11)	0.0375 (11)	0.0095 (8)	−0.0102 (8)	−0.0042 (8)
C14	0.0383 (10)	0.0379 (9)	0.0370 (10)	0.0005 (8)	−0.0054 (8)	−0.0019 (8)
C15	0.0303 (8)	0.0315 (8)	0.0301 (9)	0.0036 (7)	−0.0012 (7)	0.0034 (7)
C16	0.0343 (9)	0.0390 (9)	0.0329 (9)	0.0036 (7)	−0.0030 (7)	−0.0009 (7)
C17	0.0383 (10)	0.0596 (12)	0.0307 (10)	0.0067 (9)	0.0028 (7)	0.0009 (9)
C18	0.0385 (10)	0.0647 (12)	0.0392 (11)	0.0034 (9)	0.0086 (8)	0.0117 (9)
C19	0.0361 (10)	0.0474 (11)	0.0486 (12)	−0.0039 (8)	0.0032 (8)	0.0091 (9)
C20	0.0361 (9)	0.0364 (9)	0.0366 (10)	−0.0017 (7)	−0.0003 (7)	0.0007 (8)

Geometric parameters (Å, º)

O1—C7^i	1.4475 (17)	C10—C11	1.393 (2)
O1—C7	1.4475 (17)	C10—H10	0.9500
C1—C6	1.407 (2)	C11—C12	1.373 (3)
C1—C2	1.408 (2)	C11—H11	0.9500
C1—C1^i	1.493 (3)	C12—C13	1.386 (3)
C2—C3	1.392 (2)	C12—H12	0.9500
C2—C7	1.537 (2)	C13—C14	1.385 (3)
C3—C4	1.388 (2)	C13—H13	0.9500
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.380 (2)	C15—C16	1.391 (2)
C4—H4	0.9500	C15—C20	1.394 (2)
C5—C6	1.395 (3)	C16—C17	1.384 (3)
C5—H5	0.9500	C16—H16	0.9500
C6—C8	1.508 (2)	C17—C18	1.385 (3)
C7—C15	1.538 (2)	C17—H17	0.9500
C7—C9	1.545 (2)	C18—C19	1.380 (3)
C8—H81	0.9800	C18—H18	0.9500
C8—H82	0.9800	C19—C20	1.385 (3)
C8—H83	0.9800	C19—H19	0.9500
C9—C10	1.391 (2)	C20—H20	0.9500
C9—C14	1.396 (2)
C7^i—O1—C7	123.28 (15)	C9—C10—C11	120.69 (17)
C6—C1—C2	119.52 (16)	C9—C10—H10	119.7
C6—C1—C1^i	120.87 (13)	C11—C10—H10	119.7
C2—C1—C1^i	119.50 (12)	C12—C11—C10	120.66 (18)
C3—C2—C1	120.00 (15)	C12—C11—H11	119.7
C3—C2—C7	121.38 (14)	C10—C11—H11	119.7
C1—C2—C7	118.39 (14)	C11—C12—C13	119.32 (17)
C4—C3—C2	120.21 (16)	C11—C12—H12	120.3
C4—C3—H3	119.9	C13—C12—H12	120.3
C2—C3—H3	119.9	C14—C13—C12	120.29 (17)
C5—C4—C3	119.86 (16)	C14—C13—H13	119.9
C5—C4—H4	120.1	C12—C13—H13	119.9
C3—C4—H4	120.1	C13—C14—C9	121.01 (17)
C4—C5—C6	121.43 (16)	C13—C14—H14	119.5
C4—C5—H5	119.3	C9—C14—H14	119.5
C6—C5—H5	119.3	C16—C15—C20	118.33 (16)
C5—C6—C1	118.88 (15)	C16—C15—C7	121.35 (15)
C5—C6—C8	118.26 (15)	C20—C15—C7	120.23 (15)
C1—C6—C8	122.73 (16)	C17—C16—C15	120.67 (17)
O1—C7—C2	109.95 (12)	C17—C16—H16	119.7
O1—C7—C15	111.21 (12)	C15—C16—H16	119.7
C2—C7—C15	112.18 (12)	C16—C17—C18	120.37 (18)
O1—C7—C9	103.01 (12)	C16—C17—H17	119.8
C2—C7—C9	112.44 (13)	C18—C17—H17	119.8
C15—C7—C9	107.68 (13)	C19—C18—C17	119.57 (17)
C6—C8—H81	109.5	C19—C18—H18	120.2
C6—C8—H82	109.5	C17—C18—H18	120.2
H81—C8—H82	109.5	C18—C19—C20	120.17 (18)
C6—C8—H83	109.5	C18—C19—H19	119.9
H81—C8—H83	109.5	C20—C19—H19	119.9
H82—C8—H83	109.5	C19—C20—C15	120.88 (17)
C10—C9—C14	117.99 (15)	C19—C20—H20	119.6
C10—C9—C7	121.36 (14)	C15—C20—H20	119.6
C14—C9—C7	120.63 (14)
C6—C1—C2—C3	3.5 (2)	O1—C7—C9—C14	−167.51 (14)
C1^i—C1—C2—C3	179.79 (16)	C2—C7—C9—C14	74.17 (19)
C6—C1—C2—C7	−171.09 (14)	C15—C7—C9—C14	−49.91 (19)
C1^i—C1—C2—C7	5.2 (2)	C14—C9—C10—C11	−1.1 (3)
C1—C2—C3—C4	−1.4 (2)	C7—C9—C10—C11	177.38 (15)
C7—C2—C3—C4	173.06 (15)	C9—C10—C11—C12	−0.7 (3)
C2—C3—C4—C5	−1.2 (2)	C10—C11—C12—C13	1.6 (3)
C3—C4—C5—C6	1.6 (3)	C11—C12—C13—C14	−0.8 (3)
C4—C5—C6—C1	0.6 (3)	C12—C13—C14—C9	−1.1 (3)
C4—C5—C6—C8	−175.43 (16)	C10—C9—C14—C13	2.0 (3)
C2—C1—C6—C5	−3.1 (2)	C7—C9—C14—C13	−176.50 (16)
C1^i—C1—C6—C5	−179.34 (17)	O1—C7—C15—C16	23.4 (2)
C2—C1—C6—C8	172.74 (16)	C2—C7—C15—C16	147.06 (15)
C1^i—C1—C6—C8	−3.5 (3)	C9—C7—C15—C16	−88.71 (17)
C7^i—O1—C7—C2	−41.74 (9)	O1—C7—C15—C20	−160.03 (14)
C7^i—O1—C7—C15	83.13 (11)	C2—C7—C15—C20	−36.4 (2)
C7^i—O1—C7—C9	−161.78 (12)	C9—C7—C15—C20	87.81 (17)
C3—C2—C7—O1	−108.36 (16)	C20—C15—C16—C17	1.0 (2)
C1—C2—C7—O1	66.14 (17)	C7—C15—C16—C17	177.62 (15)
C3—C2—C7—C15	127.33 (15)	C15—C16—C17—C18	−0.7 (3)
C1—C2—C7—C15	−58.17 (18)	C16—C17—C18—C19	−0.3 (3)
C3—C2—C7—C9	5.8 (2)	C17—C18—C19—C20	1.0 (3)
C1—C2—C7—C9	−179.72 (14)	C18—C19—C20—C15	−0.6 (3)
O1—C7—C9—C10	14.09 (19)	C16—C15—C20—C19	−0.4 (3)
C2—C7—C9—C10	−104.23 (17)	C7—C15—C20—C19	−176.99 (15)
C15—C7—C9—C10	131.69 (16)

Symmetry code: (i) −x+1, y, −z+3/2.