11-Methyl-12a-phenyl-9a,12a-dihydrophenanthro[9',10':5,6][1,4]dioxino[2,3-d]oxazole and 9a-(10-hydroxyphenanthren-9-yl)-11,12a-diphenyl-9a,12a-dihydrophenanthro[9',10':5,6][1,4]dioxino[2,3-d]oxazole

In the title compounds, C₂₄H₁₇NO₃, (I), and C₄₃H₂₇NO₅, (II), the dioxine ring is not planar and tends toward a boat conformation. The oxazoline ring adopts a twisted conformation in mol­ecule (I) but is essentially planar in mol­ecule (II). The configuration of the dioxine-oxazoline system is determined by the sp³ state of the two shared atoms. The phenanthrene moiety is nearly coplanar with the dioxine ring, while the phenyl ring is perpendicular to the attached oxazole ring. The triclinic unit cell of (II) contains two crystallographically independent mol­ecules related by a pseudo-inversion centre.

S1. Comment

Photoinduced cycloaddition reactions of excited-state carbonyl compounds with oxazole derivatives have been widely investigated (Secretar et al., 1983; Griesbeck et al., 2000). In relation to our interest in heterocyclic photochemistry, we have recently investigated the photoinduced reactions of phenathrenequinone with several oxazole derivatives (Zhang & Xu, 2002). The title compounds, (I) and (II), were obtained from the photoinduced reactions of phenathrenequinone with an excess of 2-methyl-4-phenyloxazole and 2,4-diphenyloxazole, respectively, in benzene. We have also undertaken X-ray crystal structure analyses of the title compounds to elucidate their steric structure, and these results are presented here. \sch

The bond lengths and angles (Table 1) in (I) (Fig. 1) are within normal ranges (Allen et al., 1987). Those within the oxazoline (C15/C16/C17/O3/N1) and dioxine (C1/C14/O2/C15/C17/O1) rings agree with the corresponding values in the structures of oxazole derivatives (Fustero et al., 1996; Usman et al., 2002) and a dioxine derivative (Cherni et al., 1998) reported earlier.

In compound (I), the oxazoline ring is out of planarity and tends towards a twisted conformation, with atoms C15 and C17 being displaced slightly, by 0.102 (4) and -0.045 (4) Å, respectively, from the N1/C16/O3 plane. The local pseudo-twofold axis passes through atom C16 and the midpoint of the C15—C17 bond. This conformation was also confirmed by the puckering parameters (Cremer & Pople, 1975) of Q₂ = 0.087 (4) Å and ϕ₂ = 48 (3)°. The methyl atom C24 deviates by -0.009 (5) Å from the oxazoline mean plane, while the C18—C23 phenyl ring attached at C17 is nearly perpendicular to the oxazole, with the corresponding dihedral angle being 87.0 (2)°. The relative configurations of the C18—C23 phenyl, the oxazoline and the dioxine rings are determined by the sp³ state of atom C17, having an average subtended bond angle of 109.5°. The dihedral angle between the dioxine and oxazoline rings is 102.3 (2)°.

The dioxine ring adopts a boat conformation, with atoms O1 and O2 displaced by 0.283 (3) and 0.395 (3) Å, respectively, from the C1/C14/C15/C17 plane. The puckering parameters of this ring are Q₂ = 0.404 (3) Å, Q₃ = -0.047 (4) Å, Q_T = 0.407 (3) Å, ϕ₂ = 13.0 (6)° and θ = 96.6 (6)°.

In the phenanthrene moiety, the dihedral angles between the benzene rings are within 6.7 (2)° of each other. The phenanthrene is nearly coplanar with respect to the dioxine, due to the Csp² character of the shared atoms, C1 and C14. The dihedral angle between the phenanthrene and the dioxine is 12.1 (1)°.

As seen in Fig. 1, both atoms C15 and C17 are the R chiral centres. Since the structure belongs to a chiral space group, only one enantiomorph is present, but the Flack parameter (Flack, 1983) is unable to determine the absolute configuration.

In the crystal structure of (II), there are two crystallographically independent molecules, A and B, in the asymmetric unit. The bond lengths and angles (Table 2) of molecules A and B (Fig. 2) agree with each other and are comparable with those in (I). Molecules A and B are related by a local inversion centre. Molecule A (Fig. 2) has atoms C15 and C17 with S and R chirality, respectively, and molecule B has the opposite, R and S, chirality. The centrosymmetric space group also implies that (II) is a racemic mixture of enantiomers with opposite chiralities.

In contrast with (I), the oxazoline ring in both molecules A and B of (II) is planar. This is due to the difference in the substituents attached to the oxazoline ring, especially the bulky substituents attached at C15 and C17 in (II). As a result, the C18—C23 phenyl ring makes a much smaller dihedral angle with the oxazoline [72.2 (2)° in molecule A and 69.6 (2)° in molecule B] compared with that in (I). Another phenyl ring (C24—C29) is nearly coplanar with the oxazoline, with corresponding dihedral angles of 6.8 (2) and 4.3 (2)° in molecules A and B, respectively, facilitating the delocalization of π-conjugation between the two ring moieties.

The dioxine ring of both molecules A and B of (II) is out of planarity towards a boat conformation, with atoms O1 and O2 displaced from the C1/C14/C15/C17 plane by 0.449 (3) and 0.462 (2) Å, respectively, in molecule A, and by 0.496 (3) and 0.501 (2) Å, respectively, in molecule B. The puckering parameters are Q₂=0.528 (3) Å, Q₃=0.528 (3) Å, ϕ₂=4.3 (4)° and θ₂=90.5 (4)° for molecule A, and Q₂=0.576 (3) Å, Q₃=0.576 (3) Å, ϕ₂=0.8 (4)° and θ₂=89.8 (4)° for molecule B.

The average bond angle subtended at atoms C15 and C17 is 109.5°. The O1—C17—C15—O2 and N1—C17—C15—O3 torsion angles are 4.7 (4) and 2.1 (3)°, respectively, in molecule A, and -2.1 (4) and -1.3 (3)°, respectively, in molecule B. These imply the eclipsed configuration of the Csp³ of atoms C15 and C17 shared between the oxazoline and dioxine rings. The dihedral angles between the two rings are 97.3 (2) and 95.5 (2)° in molecules A and B, respectively.

In both molecules A and B, the phenanthrene (C1—C14) system is nearly coplanar with the dioxine, which is similar to what is observed in compound (I). The dihedral angles between the phenanthrene (C1—C14) system and the dioxine ring are 19.8 (1) and 24.3 (2)° in molecules A and B, respectively. The relative configuration of another phenanthrene system (C30—C43) and the dioxine ring is conditioned by the sp³ state of the joining atom, O4. The C15—O4—C30 bond angles are 117.7 (3) and 117.9 (3)° in molecules A and B, and the dihedral angles between the phenanthrene (C30—C43) and the dioxine ring are 36.4 (1) and 32.5 (1)° in molecules A and B, respectively.

In both molecules A and B of (II), the H atom of the hydroxy group facilitates an intermolecular hydrogen bond with one of O atoms of the dioxine moiety. This C5—H5···O1 bond (Table 3) forms a seven-membered ring, O2/C15/O4/C30/C43/O5/H5 (Fig. 2).

S2. Experimental

The title compounds, (I) and (II), were isolated from their reaction mixtures by column chromatography on silica gel. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of solutions in acetone-petroleum ether (1:1 v/v).

S3. Refinement

In both compounds, the H atoms were geometrically fixed and were treated as riding atoms on their parent C atoms, with aromatic C—H = 0.93 Å and methylene C—H = 0.96 Å, and, for (II), O—H = 0.82 Å. For compound (I), due to the absence of any significant anomalous scatterers, the 1333 Friedel equivalents were merged before the final refinement and the absolute configuration was arbitrarily chosen. Owing to a large fraction of weak data at higher angles, the 2θ maximum was limited to 50°. For compound (II), the structure contains solvent-accessible voids of 72.0 ų. There is no significant residual peak density within the voids, which is probably an indication of a loss of solvent and a reason for the poor quality of the data.

Computing details

For both compounds, data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT and SADABS (Sheldrick, 1996); program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

Figures

	Fig. 1. The structure of (I) showing 50% probability displacement ellipsoids and the atom-numbering scheme. H atoms are drawn as small spheres of arbitrary radii.
	Fig. 2. The structure of the two independent molecules of (II) showing 50% probability displacement ellipsoids and the atom-numbering scheme. H atoms are drawn as small spheres of arbitrary radii and the dashed lines denote intramolecular interactions.

(I) 11-Methyl-12a-phenyl-9a,12a-dihydrophenanthro[9',10':5,6][1,4]dioxino [2,3-d]oxazole

Crystal data

C24H17NO3	Dx = 1.368 Mg m^−3
Mr = 367.39	Melting point: 439(1)K K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3641 reflections
a = 9.7633 (4) Å	θ = 2.4–28.3°
b = 10.9896 (4) Å	µ = 0.09 mm^−1
c = 16.6210 (7) Å	T = 213 K
V = 1783.35 (12) Å^3	Slab, colourless
Z = 4	0.34 × 0.26 × 0.16 mm
F(000) = 768

Data collection

Siemens SMART CCD area-detector diffractometer	1254 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.104
Graphite monochromator	θmax = 25.0°, θmin = 2.4°
Detector resolution: 8.33 pixels mm^-1	h = −7→11
ω scans	k = −13→12
8619 measured reflections	l = −17→19
1795 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)] = 0.052	H-atom parameters constrained
wR(F^2) = 0.122	w = 1/[σ^2(Fo^2) + (0.0605P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.96	(Δ/σ)max < 0.001
1795 reflections	Δρmax = 0.23 e Å^−3
255 parameters	Δρmin = −0.20 e Å^−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.016 (3)

Special details

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 30 s covered 0.3° in ω. The crystal-to-detector distance was 5 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible.

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	0.6729 (3)	0.6238 (2)	0.17570 (14)	0.0370 (7)
O2	0.6269 (3)	0.7719 (2)	0.30598 (15)	0.0369 (8)
O3	0.4103 (3)	0.6924 (3)	0.28999 (16)	0.0454 (8)
N1	0.4359 (4)	0.6013 (3)	0.1691 (2)	0.0395 (9)
C1	0.7268 (4)	0.5947 (3)	0.2501 (2)	0.0265 (9)
C2	0.8128 (4)	0.4914 (3)	0.2546 (2)	0.0267 (9)
C3	0.8365 (4)	0.4169 (3)	0.1876 (3)	0.0360 (10)
H3	0.7943	0.4353	0.1389	0.043*
C4	0.9200 (4)	0.3181 (4)	0.1925 (3)	0.0476 (12)
H4	0.9359	0.2702	0.1474	0.057*
C5	0.9812 (5)	0.2895 (4)	0.2652 (4)	0.0546 (14)
H5	1.0363	0.2207	0.2693	0.066*
C6	0.9611 (4)	0.3618 (4)	0.3311 (3)	0.0502 (13)
H6	1.0032	0.3408	0.3794	0.060*
C7	0.8803 (4)	0.4652 (4)	0.3285 (2)	0.0317 (10)
C8	0.8631 (4)	0.5488 (4)	0.3955 (2)	0.0358 (11)
C9	0.9335 (5)	0.5347 (5)	0.4698 (3)	0.0477 (12)
H9	0.9899	0.4674	0.4773	0.057*
C10	0.9200 (5)	0.6177 (5)	0.5301 (3)	0.0589 (15)
H10	0.9675	0.6067	0.5781	0.071*
C11	0.8364 (5)	0.7180 (5)	0.5206 (3)	0.0564 (14)
H11	0.8289	0.7745	0.5620	0.068*
C12	0.7649 (5)	0.7349 (4)	0.4512 (2)	0.0417 (11)
H12	0.7077	0.8021	0.4456	0.050*
C13	0.7776 (4)	0.6506 (4)	0.3879 (2)	0.0303 (9)
C14	0.7072 (4)	0.6687 (3)	0.3130 (2)	0.0301 (10)
C15	0.5178 (4)	0.7603 (4)	0.2525 (3)	0.0346 (10)
H15	0.4834	0.8416	0.2392	0.041*
C16	0.3698 (5)	0.6071 (4)	0.2343 (3)	0.0413 (11)
C17	0.5460 (4)	0.6908 (3)	0.1740 (2)	0.0302 (9)
C18	0.5520 (4)	0.7733 (4)	0.1017 (2)	0.0288 (9)
C19	0.4348 (5)	0.8356 (4)	0.0793 (2)	0.0473 (13)
H19	0.3533	0.8224	0.1069	0.057*
C20	0.4385 (6)	0.9175 (4)	0.0158 (3)	0.0550 (14)
H20	0.3594	0.9592	0.0013	0.066*
C21	0.5564 (5)	0.9374 (4)	−0.0253 (3)	0.0487 (13)
H21	0.5585	0.9927	−0.0676	0.058*
C22	0.6723 (5)	0.8755 (5)	−0.0039 (3)	0.0553 (14)
H22	0.7528	0.8879	−0.0326	0.066*
C23	0.6715 (4)	0.7942 (4)	0.0602 (2)	0.0429 (11)
H23	0.7515	0.7541	0.0749	0.052*
C24	0.2524 (5)	0.5318 (4)	0.2599 (3)	0.0618 (15)
H24A	0.1744	0.5830	0.2692	0.093*
H24B	0.2754	0.4894	0.3086	0.093*
H24C	0.2312	0.4738	0.2185	0.093*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0383 (17)	0.0472 (16)	0.0254 (14)	0.0200 (15)	−0.0043 (14)	−0.0010 (13)
O2	0.0447 (18)	0.0379 (15)	0.0281 (15)	0.0144 (14)	−0.0037 (14)	−0.0060 (13)
O3	0.0397 (18)	0.0591 (19)	0.0374 (16)	0.0076 (16)	0.0132 (15)	−0.0066 (15)
N1	0.042 (2)	0.0354 (19)	0.041 (2)	−0.0004 (18)	0.005 (2)	−0.0009 (17)
C1	0.024 (2)	0.0299 (19)	0.025 (2)	0.0023 (18)	0.0018 (19)	0.0025 (18)
C2	0.018 (2)	0.029 (2)	0.033 (2)	−0.0047 (17)	0.0049 (19)	0.0025 (18)
C3	0.027 (2)	0.034 (2)	0.046 (3)	0.002 (2)	0.010 (2)	0.004 (2)
C4	0.035 (3)	0.038 (2)	0.070 (3)	0.007 (2)	0.009 (3)	−0.004 (2)
C5	0.031 (3)	0.038 (3)	0.095 (4)	0.014 (2)	0.006 (3)	0.009 (3)
C6	0.027 (3)	0.050 (3)	0.073 (3)	0.005 (2)	−0.003 (3)	0.023 (3)
C7	0.019 (2)	0.036 (2)	0.040 (2)	−0.0027 (18)	0.001 (2)	0.014 (2)
C8	0.023 (2)	0.048 (2)	0.036 (2)	−0.007 (2)	0.003 (2)	0.013 (2)
C9	0.031 (3)	0.069 (3)	0.043 (3)	−0.002 (3)	−0.008 (2)	0.021 (3)
C10	0.049 (3)	0.093 (4)	0.035 (3)	−0.015 (3)	−0.013 (3)	0.014 (3)
C11	0.054 (3)	0.084 (4)	0.031 (3)	−0.016 (3)	−0.005 (3)	−0.006 (3)
C12	0.039 (3)	0.054 (3)	0.032 (2)	−0.007 (2)	−0.004 (2)	−0.001 (2)
C13	0.023 (2)	0.043 (2)	0.025 (2)	−0.006 (2)	−0.0009 (18)	0.0048 (19)
C14	0.030 (2)	0.028 (2)	0.033 (2)	0.0020 (19)	−0.003 (2)	0.0040 (19)
C15	0.038 (3)	0.040 (2)	0.0255 (19)	0.010 (2)	0.001 (2)	0.001 (2)
C16	0.039 (3)	0.038 (2)	0.047 (3)	0.011 (2)	0.012 (2)	0.002 (2)
C17	0.031 (2)	0.031 (2)	0.028 (2)	0.009 (2)	−0.001 (2)	0.0002 (18)
C18	0.029 (2)	0.037 (2)	0.0200 (19)	0.003 (2)	−0.0037 (19)	−0.0032 (17)
C19	0.035 (3)	0.068 (3)	0.039 (2)	0.018 (3)	0.005 (2)	0.009 (2)
C20	0.052 (3)	0.071 (3)	0.042 (3)	0.030 (3)	0.003 (3)	0.021 (3)
C21	0.059 (3)	0.049 (3)	0.038 (3)	0.011 (3)	0.004 (3)	0.011 (2)
C22	0.043 (3)	0.076 (3)	0.047 (3)	−0.007 (3)	0.008 (3)	0.022 (3)
C23	0.024 (2)	0.066 (3)	0.039 (2)	0.005 (2)	−0.002 (2)	0.008 (2)
C24	0.054 (3)	0.052 (3)	0.079 (4)	0.000 (3)	0.027 (3)	0.005 (3)

Geometric parameters (Å, º)

O1—C1	1.381 (4)	C10—C11	1.381 (7)
O1—C17	1.441 (4)	C10—H10	0.9300
O2—C14	1.384 (4)	C11—C12	1.361 (6)
O2—C15	1.393 (5)	C11—H11	0.9300
O3—C16	1.375 (5)	C12—C13	1.407 (5)
O3—C15	1.431 (5)	C12—H12	0.9300
N1—C16	1.264 (5)	C13—C14	1.436 (5)
N1—C17	1.459 (5)	C15—C17	1.537 (6)
C1—C14	1.339 (5)	C15—H15	0.9800
C1—C2	1.414 (5)	C16—C24	1.476 (6)
C2—C3	1.401 (5)	C17—C18	1.507 (5)
C2—C7	1.423 (5)	C18—C23	1.375 (6)
C3—C4	1.360 (5)	C18—C19	1.384 (6)
C3—H3	0.9300	C19—C20	1.387 (6)
C4—C5	1.385 (7)	C19—H19	0.9300
C4—H4	0.9300	C20—C21	1.356 (6)
C5—C6	1.367 (7)	C20—H20	0.9300
C5—H5	0.9300	C21—C22	1.367 (6)
C6—C7	1.384 (6)	C21—H21	0.9300
C6—H6	0.9300	C22—C23	1.389 (6)
C7—C8	1.454 (6)	C22—H22	0.9300
C8—C13	1.402 (5)	C23—H23	0.9300
C8—C9	1.420 (6)	C24—H24A	0.9600
C9—C10	1.362 (6)	C24—H24B	0.9600
C9—H9	0.9300	C24—H24C	0.9600
C1—O1—C17	117.6 (3)	C1—C14—O2	120.9 (3)
C14—O2—C15	114.3 (3)	C1—C14—C13	121.6 (3)
C16—O3—C15	105.9 (3)	O2—C14—C13	117.3 (3)
C16—N1—C17	107.2 (3)	O2—C15—O3	109.3 (3)
C14—C1—O1	120.3 (3)	O2—C15—C17	116.8 (3)
C14—C1—C2	122.1 (3)	O3—C15—C17	104.0 (3)
O1—C1—C2	117.4 (3)	O2—C15—H15	108.8
C3—C2—C1	121.7 (4)	O3—C15—H15	108.8
C3—C2—C7	119.4 (3)	C17—C15—H15	108.8
C1—C2—C7	118.9 (3)	N1—C16—O3	117.7 (4)
C4—C3—C2	121.1 (4)	N1—C16—C24	128.0 (4)
C4—C3—H3	119.4	O3—C16—C24	114.4 (4)
C2—C3—H3	119.4	O1—C17—N1	106.9 (3)
C3—C4—C5	119.5 (4)	O1—C17—C18	106.9 (3)
C3—C4—H4	120.2	N1—C17—C18	112.9 (3)
C5—C4—H4	120.2	O1—C17—C15	113.0 (3)
C6—C5—C4	120.3 (4)	N1—C17—C15	104.5 (3)
C6—C5—H5	119.8	C18—C17—C15	112.6 (3)
C4—C5—H5	119.8	C23—C18—C19	118.9 (4)
C5—C6—C7	122.3 (4)	C23—C18—C17	122.3 (4)
C5—C6—H6	118.9	C19—C18—C17	118.7 (4)
C7—C6—H6	118.9	C18—C19—C20	120.3 (4)
C6—C7—C2	117.2 (4)	C18—C19—H19	119.9
C6—C7—C8	124.1 (4)	C20—C19—H19	119.9
C2—C7—C8	118.7 (3)	C21—C20—C19	120.6 (5)
C13—C8—C9	117.0 (4)	C21—C20—H20	119.7
C13—C8—C7	120.2 (4)	C19—C20—H20	119.7
C9—C8—C7	122.7 (4)	C20—C21—C22	119.4 (4)
C10—C9—C8	121.3 (4)	C20—C21—H21	120.3
C10—C9—H9	119.3	C22—C21—H21	120.3
C8—C9—H9	119.3	C21—C22—C23	121.0 (5)
C9—C10—C11	120.5 (4)	C21—C22—H22	119.5
C9—C10—H10	119.8	C23—C22—H22	119.5
C11—C10—H10	119.8	C18—C23—C22	119.8 (4)
C12—C11—C10	120.7 (5)	C18—C23—H23	120.1
C12—C11—H11	119.7	C22—C23—H23	120.1
C10—C11—H11	119.7	C16—C24—H24A	109.5
C11—C12—C13	119.9 (5)	C16—C24—H24B	109.5
C11—C12—H12	120.1	H24A—C24—H24B	109.5
C13—C12—H12	120.1	C16—C24—H24C	109.5
C8—C13—C12	120.7 (4)	H24A—C24—H24C	109.5
C8—C13—C14	118.3 (4)	H24B—C24—H24C	109.5
C12—C13—C14	120.9 (4)
C17—O1—C1—C14	−31.7 (5)	C8—C13—C14—C1	−3.3 (6)
C17—O1—C1—C2	154.2 (3)	C12—C13—C14—C1	174.6 (4)
C14—C1—C2—C3	−177.7 (4)	C8—C13—C14—O2	−177.9 (3)
O1—C1—C2—C3	−3.7 (5)	C12—C13—C14—O2	0.0 (5)
C14—C1—C2—C7	0.2 (5)	C14—O2—C15—O3	77.5 (4)
O1—C1—C2—C7	174.2 (3)	C14—O2—C15—C17	−40.1 (5)
C1—C2—C3—C4	179.7 (4)	C16—O3—C15—O2	−133.2 (3)
C7—C2—C3—C4	1.7 (6)	C16—O3—C15—C17	−7.8 (4)
C2—C3—C4—C5	1.0 (6)	C17—N1—C16—O3	1.9 (5)
C3—C4—C5—C6	−1.9 (7)	C17—N1—C16—C24	−177.4 (4)
C4—C5—C6—C7	0.0 (7)	C15—O3—C16—N1	4.2 (5)
C5—C6—C7—C2	2.7 (6)	C15—O3—C16—C24	−176.4 (3)
C5—C6—C7—C8	−175.9 (4)	C1—O1—C17—N1	−92.7 (4)
C3—C2—C7—C6	−3.5 (5)	C1—O1—C17—C18	146.1 (3)
C1—C2—C7—C6	178.5 (4)	C1—O1—C17—C15	21.7 (5)
C3—C2—C7—C8	175.2 (4)	C16—N1—C17—O1	113.4 (4)
C1—C2—C7—C8	−2.8 (5)	C16—N1—C17—C18	−129.4 (4)
C6—C7—C8—C13	−179.1 (4)	C16—N1—C17—C15	−6.7 (4)
C2—C7—C8—C13	2.3 (5)	O2—C15—C17—O1	13.5 (5)
C6—C7—C8—C9	2.9 (6)	O3—C15—C17—O1	−107.0 (3)
C2—C7—C8—C9	−175.7 (4)	O2—C15—C17—N1	129.3 (4)
C13—C8—C9—C10	−1.1 (6)	O3—C15—C17—N1	8.8 (4)
C7—C8—C9—C10	177.0 (4)	O2—C15—C17—C18	−107.7 (4)
C8—C9—C10—C11	0.3 (7)	O3—C15—C17—C18	131.8 (3)
C9—C10—C11—C12	0.8 (8)	O1—C17—C18—C23	−12.9 (5)
C10—C11—C12—C13	−1.0 (7)	N1—C17—C18—C23	−130.1 (4)
C9—C8—C13—C12	0.9 (6)	C15—C17—C18—C23	111.8 (4)
C7—C8—C13—C12	−177.2 (4)	O1—C17—C18—C19	170.9 (3)
C9—C8—C13—C14	178.8 (4)	N1—C17—C18—C19	53.7 (5)
C7—C8—C13—C14	0.7 (5)	C15—C17—C18—C19	−64.4 (5)
C11—C12—C13—C8	0.1 (6)	C23—C18—C19—C20	0.1 (7)
C11—C12—C13—C14	−177.7 (4)	C17—C18—C19—C20	176.4 (4)
O1—C1—C14—O2	3.5 (6)	C18—C19—C20—C21	0.3 (7)
C2—C1—C14—O2	177.3 (3)	C19—C20—C21—C22	0.3 (8)
O1—C1—C14—C13	−170.9 (3)	C20—C21—C22—C23	−1.2 (8)
C2—C1—C14—C13	2.9 (6)	C19—C18—C23—C22	−1.0 (6)
C15—O2—C14—C1	33.0 (5)	C17—C18—C23—C22	−177.1 (4)
C15—O2—C14—C13	−152.4 (3)	C21—C22—C23—C18	1.5 (7)

(II) 9a-(10-hydroxyphenanthren-9-yl)-11,12a-diphenyl- 9a,12a-dihydrophenanthro[9',10':5,6][1,4]dioxino[2,3-d]oxazole

Crystal data

C43H27NO5	Z = 4
Mr = 637.66	F(000) = 1328
Triclinic, P1	Dx = 1.334 Mg m^−3
Hall symbol: -P 1	Melting point: 456(1)K K
a = 12.4812 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.3317 (1) Å	Cell parameters from 5405 reflections
c = 18.5727 (3) Å	θ = 2.8–28.4°
α = 102.607 (1)°	µ = 0.09 mm^−1
β = 99.511 (1)°	T = 213 K
γ = 94.529 (1)°	Slab, yellow
V = 3174.64 (9) Å^3	0.5 × 0.4 × 0.1 mm

Data collection

Siemens SMART CCD area-detector diffractometer	4506 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.088
Graphite monochromator	θmax = 28.4°, θmin = 2.8°
Detector resolution: 8.33 pixels mm^-1	h = −10→16
ω scans	k = −19→19
19415 measured reflections	l = −24→21
14575 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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.194	H-atom parameters constrained
S = 0.75	w = 1/[σ^2(Fo^2) + (0.03P)^2] where P = (Fo^2 + 2Fc^2)/3
14575 reflections	(Δ/σ)max < 0.001
883 parameters	Δρmax = 0.41 e Å^−3
0 restraints	Δρmin = −0.41 e Å^−3

Special details

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 5 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible.

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
O1A	0.95668 (19)	0.72877 (17)	0.44058 (12)	0.0329 (7)
O2A	0.83467 (19)	0.65480 (16)	0.30442 (13)	0.0301 (6)
O3A	0.80239 (18)	0.81080 (16)	0.30895 (12)	0.0285 (6)
O4A	0.68672 (18)	0.70544 (16)	0.34642 (12)	0.0290 (6)
O5A	0.6574 (2)	0.52331 (17)	0.24329 (14)	0.0403 (7)
H5AA	0.7203	0.5464	0.2632	0.060*
N1A	0.8966 (2)	0.8765 (2)	0.42768 (16)	0.0295 (7)
C1A	1.0083 (3)	0.7044 (2)	0.3789 (2)	0.0266 (9)
C2A	1.1241 (3)	0.7166 (2)	0.3916 (2)	0.0275 (9)
C3A	1.1890 (3)	0.7631 (3)	0.4609 (2)	0.0435 (11)
H3A	1.1553	0.7867	0.5011	0.052*
C4A	1.2991 (3)	0.7747 (3)	0.4711 (2)	0.0492 (12)
H4A	1.3406	0.8049	0.5180	0.059*
C5A	1.3508 (3)	0.7408 (3)	0.4102 (2)	0.0498 (12)
H5A	1.4267	0.7486	0.4169	0.060*
C6A	1.2898 (3)	0.6966 (3)	0.3415 (2)	0.0394 (10)
H6A	1.3252	0.6746	0.3019	0.047*
C7A	1.1753 (3)	0.6836 (3)	0.3291 (2)	0.0300 (9)
C8A	1.1087 (3)	0.6385 (2)	0.2556 (2)	0.0267 (9)
C9A	1.1532 (3)	0.6043 (3)	0.1918 (2)	0.0357 (10)
H9A	1.2288	0.6106	0.1957	0.043*
C10A	1.0884 (4)	0.5618 (3)	0.1242 (2)	0.0457 (11)
H10A	1.1200	0.5385	0.0829	0.055*
C11A	0.9751 (4)	0.5533 (3)	0.1166 (2)	0.0488 (12)
H11A	0.9313	0.5242	0.0703	0.059*
C12A	0.9280 (3)	0.5873 (3)	0.1770 (2)	0.0381 (10)
H12A	0.8523	0.5814	0.1717	0.046*
C13A	0.9940 (3)	0.6311 (2)	0.2467 (2)	0.0254 (9)
C14A	0.9485 (3)	0.6651 (2)	0.3116 (2)	0.0257 (9)
C15A	0.7943 (3)	0.7342 (3)	0.34517 (19)	0.0267 (9)
C16A	0.8626 (3)	0.8884 (3)	0.3621 (2)	0.0270 (9)
C17A	0.8612 (3)	0.7768 (3)	0.42701 (19)	0.0254 (9)
C18A	0.7977 (3)	0.7694 (3)	0.48884 (19)	0.0324 (9)
C19A	0.7346 (3)	0.8411 (3)	0.5115 (2)	0.0544 (13)
H19A	0.7335	0.8940	0.4901	0.065*
C20A	0.6723 (4)	0.8343 (4)	0.5664 (2)	0.0618 (14)
H20A	0.6272	0.8811	0.5803	0.074*
C21A	0.6785 (4)	0.7576 (4)	0.5998 (2)	0.0620 (15)
H21A	0.6382	0.7535	0.6371	0.074*
C22A	0.7423 (4)	0.6879 (4)	0.5791 (2)	0.0547 (13)
H22A	0.7466	0.6370	0.6028	0.066*
C23A	0.8014 (3)	0.6927 (3)	0.5221 (2)	0.0402 (11)
H23A	0.8433	0.6439	0.5067	0.048*
C24A	0.8781 (3)	0.9775 (2)	0.3386 (2)	0.0255 (8)
C25A	0.9307 (3)	1.0600 (3)	0.3909 (2)	0.0366 (10)
H25A	0.9546	1.0575	0.4405	0.044*
C26A	0.9473 (3)	1.1438 (3)	0.3699 (2)	0.0427 (11)
H26A	0.9785	1.1995	0.4057	0.051*
C27A	0.9181 (3)	1.1471 (3)	0.2952 (2)	0.0423 (11)
H27A	0.9323	1.2044	0.2808	0.051*
C28A	0.8685 (3)	1.0665 (3)	0.2427 (2)	0.0388 (10)
H28A	0.8485	1.0693	0.1928	0.047*
C29A	0.8475 (3)	0.9803 (3)	0.2634 (2)	0.0353 (10)
H29A	0.8137	0.9253	0.2277	0.042*
C30A	0.6108 (3)	0.6830 (3)	0.2771 (2)	0.0299 (9)
C31A	0.5394 (3)	0.7534 (3)	0.2645 (2)	0.0360 (10)
C32A	0.5493 (3)	0.8432 (3)	0.3151 (3)	0.0490 (12)
H32A	0.6053	0.8585	0.3571	0.059*
C33A	0.4765 (4)	0.9099 (3)	0.3035 (3)	0.0667 (15)
H33A	0.4848	0.9703	0.3363	0.080*
C34A	0.3911 (4)	0.8838 (4)	0.2415 (3)	0.0668 (15)
H34A	0.3401	0.9264	0.2343	0.080*
C35A	0.3808 (4)	0.7972 (3)	0.1914 (3)	0.0571 (13)
H35A	0.3238	0.7830	0.1501	0.069*
C36A	0.4535 (3)	0.7287 (3)	0.2001 (2)	0.0409 (11)
C37A	0.4443 (3)	0.6363 (3)	0.1484 (2)	0.0368 (10)
C38A	0.3638 (3)	0.6090 (4)	0.0819 (3)	0.0579 (13)
H38A	0.3175	0.6529	0.0689	0.069*
C39A	0.3539 (4)	0.5186 (4)	0.0368 (3)	0.0667 (15)
H39A	0.2991	0.5012	−0.0058	0.080*
C40A	0.4233 (4)	0.4524 (4)	0.0530 (2)	0.0625 (14)
H40A	0.4154	0.3910	0.0217	0.075*
C41A	0.5039 (3)	0.4789 (3)	0.1159 (2)	0.0476 (12)
H41A	0.5522	0.4354	0.1264	0.057*
C42A	0.5148 (3)	0.5694 (3)	0.1642 (2)	0.0359 (10)
C43A	0.5973 (3)	0.5947 (3)	0.2309 (2)	0.0295 (9)
O1B	0.03184 (19)	0.23942 (18)	0.03253 (13)	0.0356 (7)
O2B	0.14754 (19)	0.33973 (16)	0.16290 (13)	0.0294 (6)
O3B	0.18429 (18)	0.19302 (16)	0.18320 (12)	0.0251 (6)
O4B	0.29917 (18)	0.28248 (16)	0.13242 (12)	0.0257 (6)
O5B	0.3283 (2)	0.46375 (16)	0.23738 (14)	0.0373 (7)
H5BA	0.2666	0.4411	0.2144	0.056*
C1B	−0.0237 (3)	0.2728 (3)	0.0906 (2)	0.0288 (9)
C2B	−0.1398 (3)	0.2520 (3)	0.0784 (2)	0.0349 (10)
C3B	−0.2018 (3)	0.1934 (3)	0.0117 (2)	0.0453 (11)
H3B	−0.1671	0.1658	−0.0269	0.054*
C4B	−0.3111 (4)	0.1770 (3)	0.0031 (3)	0.0606 (14)
H4B	−0.3512	0.1396	−0.0421	0.073*
C5B	−0.3657 (4)	0.2149 (4)	0.0603 (3)	0.0604 (14)
H5B	−0.4414	0.2022	0.0534	0.072*
C6B	−0.3074 (3)	0.2710 (3)	0.1272 (3)	0.0520 (13)
H6B	−0.3442	0.2962	0.1653	0.062*
C7B	−0.1933 (3)	0.2906 (3)	0.1388 (2)	0.0358 (10)
C8B	−0.1287 (3)	0.3461 (3)	0.2095 (2)	0.0326 (10)
C9B	−0.1744 (3)	0.3820 (3)	0.2734 (2)	0.0407 (11)
H9B	−0.2499	0.3719	0.2696	0.049*
C10B	−0.1121 (4)	0.4306 (3)	0.3398 (3)	0.0474 (12)
H10B	−0.1455	0.4537	0.3802	0.057*
C11B	0.0010 (4)	0.4463 (3)	0.3486 (2)	0.0463 (12)
H11B	0.0434	0.4792	0.3944	0.056*
C12B	0.0493 (3)	0.4121 (2)	0.2876 (2)	0.0349 (10)
H12B	0.1249	0.4224	0.2925	0.042*
C13B	−0.0144 (3)	0.3620 (2)	0.2187 (2)	0.0274 (9)
C14B	0.0332 (3)	0.3240 (3)	0.1560 (2)	0.0308 (9)
C15B	0.1920 (3)	0.2560 (3)	0.13468 (19)	0.0267 (9)
C16B	0.1259 (3)	0.1081 (2)	0.1400 (2)	0.0254 (9)
N1B	0.0918 (2)	0.1028 (2)	0.07032 (16)	0.0294 (8)
C17B	0.1267 (3)	0.1953 (3)	0.05625 (19)	0.0253 (9)
C18B	0.1932 (3)	0.1841 (3)	−0.00588 (19)	0.0317 (10)
C19B	0.2105 (3)	0.2593 (3)	−0.0407 (2)	0.0443 (11)
H19B	0.1759	0.3144	−0.0294	0.053*
C20B	0.2808 (4)	0.2510 (4)	−0.0928 (2)	0.0563 (13)
H20B	0.2919	0.3002	−0.1171	0.068*
C21B	0.3327 (4)	0.1709 (4)	−0.1078 (2)	0.0637 (15)
H21B	0.3815	0.1669	−0.1409	0.076*
C22B	0.3140 (4)	0.0967 (4)	−0.0750 (2)	0.0586 (14)
H22B	0.3487	0.0418	−0.0868	0.070*
C23B	0.2428 (3)	0.1022 (3)	−0.0237 (2)	0.0448 (12)
H23B	0.2293	0.0509	−0.0019	0.054*
C24B	0.1142 (3)	0.0312 (2)	0.1781 (2)	0.0249 (8)
C25B	0.0610 (3)	−0.0587 (3)	0.1377 (2)	0.0381 (10)
H25B	0.0333	−0.0687	0.0866	0.046*
C26B	0.0494 (3)	−0.1329 (3)	0.1732 (3)	0.0455 (11)
H26B	0.0157	−0.1933	0.1459	0.055*
C27B	0.0878 (3)	−0.1170 (3)	0.2495 (2)	0.0430 (11)
H27B	0.0799	−0.1669	0.2736	0.052*
C28B	0.1376 (3)	−0.0282 (3)	0.2897 (2)	0.0392 (10)
H28B	0.1626	−0.0182	0.3411	0.047*
C29B	0.1510 (3)	0.0462 (3)	0.2554 (2)	0.0298 (9)
H29B	0.1844	0.1064	0.2834	0.036*
C30B	0.3761 (3)	0.3040 (3)	0.20081 (19)	0.0275 (9)
C31B	0.4442 (3)	0.2315 (3)	0.2123 (2)	0.0296 (9)
C32B	0.4302 (3)	0.1409 (3)	0.1626 (2)	0.0382 (10)
H32B	0.3742	0.1267	0.1207	0.046*
C33B	0.4970 (3)	0.0730 (3)	0.1745 (3)	0.0478 (12)
H33B	0.4859	0.0126	0.1414	0.057*
C34B	0.5824 (4)	0.0944 (3)	0.2365 (3)	0.0561 (13)
H34B	0.6287	0.0483	0.2444	0.067*
C35B	0.5988 (3)	0.1822 (3)	0.2858 (2)	0.0442 (11)
H35B	0.6565	0.1949	0.3267	0.053*
C36B	0.5306 (3)	0.2540 (3)	0.2764 (2)	0.0312 (9)
C37B	0.5431 (3)	0.3465 (3)	0.3286 (2)	0.0304 (9)
C38B	0.6230 (3)	0.3734 (3)	0.3948 (2)	0.0460 (11)
H38B	0.6704	0.3296	0.4062	0.055*
C39B	0.6327 (4)	0.4615 (4)	0.4424 (2)	0.0575 (13)
H39B	0.6870	0.4772	0.4853	0.069*
C40B	0.5622 (4)	0.5290 (3)	0.4277 (2)	0.0544 (13)
H40B	0.5698	0.5896	0.4600	0.065*
C41B	0.4816 (3)	0.5040 (3)	0.3649 (2)	0.0393 (10)
H41B	0.4324	0.5474	0.3557	0.047*
C42B	0.4720 (3)	0.4150 (3)	0.31441 (19)	0.0293 (9)
C43B	0.3883 (3)	0.3912 (3)	0.2479 (2)	0.0271 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0317 (16)	0.0513 (17)	0.0242 (15)	0.0163 (13)	0.0144 (11)	0.0159 (13)
O2A	0.0243 (15)	0.0343 (15)	0.0332 (15)	0.0041 (12)	0.0133 (11)	0.0050 (12)
O3A	0.0302 (15)	0.0318 (15)	0.0255 (15)	0.0011 (12)	0.0087 (11)	0.0091 (12)
O4A	0.0229 (15)	0.0391 (16)	0.0273 (15)	−0.0021 (12)	0.0152 (11)	0.0067 (12)
O5A	0.0270 (16)	0.0408 (16)	0.0537 (19)	0.0034 (13)	0.0096 (13)	0.0109 (14)
N1A	0.0309 (19)	0.0389 (19)	0.0208 (18)	0.0041 (15)	0.0110 (13)	0.0071 (15)
C1A	0.027 (2)	0.032 (2)	0.026 (2)	0.0108 (18)	0.0163 (17)	0.0091 (18)
C2A	0.026 (2)	0.034 (2)	0.029 (2)	0.0078 (18)	0.0092 (17)	0.0159 (18)
C3A	0.042 (3)	0.064 (3)	0.029 (2)	0.019 (2)	0.008 (2)	0.016 (2)
C4A	0.035 (3)	0.071 (3)	0.042 (3)	0.003 (2)	0.004 (2)	0.018 (2)
C5A	0.035 (3)	0.076 (3)	0.042 (3)	0.012 (2)	0.006 (2)	0.019 (2)
C6A	0.030 (2)	0.057 (3)	0.038 (3)	0.009 (2)	0.0134 (19)	0.018 (2)
C7A	0.029 (2)	0.038 (2)	0.034 (2)	0.0162 (19)	0.0128 (18)	0.0203 (19)
C8A	0.028 (2)	0.025 (2)	0.032 (2)	0.0042 (18)	0.0122 (17)	0.0112 (17)
C9A	0.033 (2)	0.046 (3)	0.040 (3)	0.018 (2)	0.023 (2)	0.017 (2)
C10A	0.048 (3)	0.058 (3)	0.032 (3)	0.010 (2)	0.020 (2)	0.002 (2)
C11A	0.045 (3)	0.067 (3)	0.030 (3)	0.011 (2)	0.009 (2)	−0.001 (2)
C12A	0.036 (3)	0.043 (3)	0.038 (3)	0.013 (2)	0.016 (2)	0.005 (2)
C13A	0.026 (2)	0.026 (2)	0.029 (2)	0.0038 (17)	0.0129 (17)	0.0094 (17)
C14A	0.021 (2)	0.027 (2)	0.030 (2)	0.0043 (17)	0.0111 (17)	0.0038 (18)
C15A	0.026 (2)	0.033 (2)	0.027 (2)	0.0062 (18)	0.0169 (16)	0.0093 (18)
C16A	0.0149 (19)	0.034 (2)	0.032 (2)	0.0004 (17)	0.0120 (16)	0.0023 (19)
C17A	0.022 (2)	0.034 (2)	0.025 (2)	0.0035 (18)	0.0145 (16)	0.0089 (17)
C18A	0.034 (2)	0.043 (2)	0.019 (2)	−0.001 (2)	0.0109 (17)	0.0028 (19)
C19A	0.052 (3)	0.082 (4)	0.038 (3)	0.022 (3)	0.028 (2)	0.013 (2)
C20A	0.049 (3)	0.092 (4)	0.044 (3)	0.007 (3)	0.029 (2)	0.000 (3)
C21A	0.046 (3)	0.101 (4)	0.030 (3)	−0.026 (3)	0.018 (2)	−0.001 (3)
C22A	0.054 (3)	0.076 (4)	0.030 (3)	−0.033 (3)	0.012 (2)	0.016 (2)
C23A	0.041 (3)	0.056 (3)	0.024 (2)	−0.007 (2)	0.0102 (18)	0.012 (2)
C24A	0.020 (2)	0.026 (2)	0.031 (2)	0.0008 (17)	0.0074 (16)	0.0056 (17)
C25A	0.043 (3)	0.038 (2)	0.031 (2)	0.006 (2)	0.0106 (19)	0.008 (2)
C26A	0.048 (3)	0.034 (3)	0.043 (3)	−0.005 (2)	0.014 (2)	0.002 (2)
C27A	0.039 (3)	0.042 (3)	0.053 (3)	0.006 (2)	0.016 (2)	0.021 (2)
C28A	0.031 (2)	0.053 (3)	0.037 (3)	0.003 (2)	0.0054 (19)	0.021 (2)
C29A	0.033 (2)	0.043 (3)	0.030 (2)	0.005 (2)	0.0051 (18)	0.010 (2)
C30A	0.024 (2)	0.045 (3)	0.028 (2)	0.0056 (19)	0.0135 (17)	0.0163 (19)
C31A	0.028 (2)	0.044 (3)	0.046 (3)	0.008 (2)	0.024 (2)	0.017 (2)
C32A	0.043 (3)	0.047 (3)	0.068 (3)	0.013 (2)	0.031 (2)	0.019 (2)
C33A	0.061 (4)	0.051 (3)	0.102 (4)	0.021 (3)	0.042 (3)	0.021 (3)
C34A	0.053 (4)	0.075 (4)	0.097 (5)	0.035 (3)	0.037 (3)	0.046 (3)
C35A	0.034 (3)	0.073 (3)	0.083 (4)	0.010 (3)	0.028 (2)	0.045 (3)
C36A	0.019 (2)	0.065 (3)	0.053 (3)	0.007 (2)	0.016 (2)	0.036 (2)
C37A	0.022 (2)	0.058 (3)	0.036 (3)	−0.003 (2)	0.0125 (18)	0.020 (2)
C38A	0.040 (3)	0.095 (4)	0.048 (3)	0.012 (3)	0.014 (2)	0.031 (3)
C39A	0.040 (3)	0.108 (5)	0.052 (3)	−0.011 (3)	0.010 (2)	0.023 (3)
C40A	0.046 (3)	0.089 (4)	0.045 (3)	−0.013 (3)	0.017 (2)	0.001 (3)
C41A	0.033 (3)	0.064 (3)	0.039 (3)	−0.013 (2)	0.010 (2)	0.002 (2)
C42A	0.023 (2)	0.052 (3)	0.034 (2)	−0.004 (2)	0.0113 (18)	0.013 (2)
C43A	0.022 (2)	0.038 (2)	0.032 (2)	0.0031 (19)	0.0127 (17)	0.0101 (19)
O1B	0.0273 (16)	0.0573 (18)	0.0264 (15)	0.0148 (14)	0.0080 (12)	0.0130 (13)
O2B	0.0221 (15)	0.0296 (15)	0.0386 (16)	0.0055 (12)	0.0141 (11)	0.0056 (12)
O3B	0.0247 (14)	0.0286 (14)	0.0236 (14)	−0.0013 (12)	0.0088 (10)	0.0082 (11)
O4B	0.0143 (13)	0.0395 (15)	0.0246 (14)	−0.0017 (12)	0.0084 (10)	0.0086 (12)
O5B	0.0298 (16)	0.0333 (15)	0.0466 (17)	0.0048 (13)	0.0063 (12)	0.0052 (13)
C1B	0.019 (2)	0.041 (2)	0.032 (2)	0.0085 (19)	0.0093 (17)	0.0161 (19)
C2B	0.033 (3)	0.042 (3)	0.038 (3)	0.010 (2)	0.0089 (19)	0.021 (2)
C3B	0.034 (3)	0.063 (3)	0.041 (3)	0.003 (2)	0.005 (2)	0.019 (2)
C4B	0.037 (3)	0.091 (4)	0.050 (3)	−0.001 (3)	−0.004 (2)	0.020 (3)
C5B	0.030 (3)	0.109 (4)	0.050 (3)	0.002 (3)	0.008 (2)	0.038 (3)
C6B	0.030 (3)	0.085 (4)	0.056 (3)	0.013 (3)	0.020 (2)	0.036 (3)
C7B	0.030 (2)	0.042 (2)	0.049 (3)	0.012 (2)	0.017 (2)	0.029 (2)
C8B	0.029 (2)	0.035 (2)	0.045 (3)	0.0116 (19)	0.0207 (19)	0.020 (2)
C9B	0.036 (3)	0.044 (3)	0.056 (3)	0.016 (2)	0.023 (2)	0.027 (2)
C10B	0.052 (3)	0.049 (3)	0.055 (3)	0.021 (2)	0.032 (2)	0.020 (2)
C11B	0.058 (3)	0.047 (3)	0.040 (3)	0.019 (2)	0.021 (2)	0.008 (2)
C12B	0.038 (3)	0.032 (2)	0.045 (3)	0.010 (2)	0.022 (2)	0.017 (2)
C13B	0.031 (2)	0.021 (2)	0.036 (2)	0.0054 (18)	0.0140 (18)	0.0116 (18)
C14B	0.023 (2)	0.031 (2)	0.047 (3)	0.0094 (19)	0.0151 (19)	0.019 (2)
C15B	0.026 (2)	0.031 (2)	0.031 (2)	0.0082 (18)	0.0163 (17)	0.0143 (18)
C16B	0.019 (2)	0.024 (2)	0.030 (2)	−0.0040 (17)	0.0124 (16)	−0.0030 (18)
N1B	0.0275 (18)	0.038 (2)	0.0204 (18)	0.0002 (15)	0.0082 (13)	0.0006 (15)
C17B	0.023 (2)	0.034 (2)	0.020 (2)	0.0042 (18)	0.0093 (15)	0.0051 (17)
C18B	0.025 (2)	0.051 (3)	0.018 (2)	0.003 (2)	0.0058 (16)	0.0041 (19)
C19B	0.043 (3)	0.063 (3)	0.028 (2)	−0.001 (2)	0.0116 (19)	0.010 (2)
C20B	0.058 (3)	0.078 (4)	0.029 (3)	−0.025 (3)	0.009 (2)	0.014 (3)
C21B	0.051 (3)	0.105 (5)	0.026 (3)	−0.012 (3)	0.016 (2)	0.000 (3)
C22B	0.048 (3)	0.089 (4)	0.036 (3)	0.014 (3)	0.022 (2)	−0.004 (3)
C23B	0.041 (3)	0.064 (3)	0.028 (2)	0.014 (2)	0.0142 (19)	0.000 (2)
C24B	0.021 (2)	0.023 (2)	0.031 (2)	0.0006 (17)	0.0094 (16)	0.0046 (17)
C25B	0.035 (2)	0.037 (2)	0.041 (3)	−0.002 (2)	0.0117 (19)	0.005 (2)
C26B	0.047 (3)	0.031 (2)	0.060 (3)	−0.004 (2)	0.020 (2)	0.007 (2)
C27B	0.038 (3)	0.038 (3)	0.063 (3)	0.009 (2)	0.017 (2)	0.025 (2)
C28B	0.039 (3)	0.041 (3)	0.046 (3)	0.005 (2)	0.015 (2)	0.022 (2)
C29B	0.032 (2)	0.024 (2)	0.033 (2)	0.0016 (18)	0.0093 (17)	0.0035 (18)
C30B	0.026 (2)	0.036 (2)	0.023 (2)	0.0013 (19)	0.0101 (16)	0.0094 (18)
C31B	0.022 (2)	0.038 (2)	0.033 (2)	0.0039 (19)	0.0148 (17)	0.0096 (19)
C32B	0.026 (2)	0.040 (2)	0.050 (3)	0.005 (2)	0.0147 (19)	0.008 (2)
C33B	0.037 (3)	0.044 (3)	0.064 (3)	0.013 (2)	0.018 (2)	0.008 (2)
C34B	0.045 (3)	0.050 (3)	0.084 (4)	0.022 (2)	0.023 (3)	0.025 (3)
C35B	0.025 (2)	0.054 (3)	0.061 (3)	0.004 (2)	0.010 (2)	0.028 (2)
C36B	0.020 (2)	0.042 (2)	0.039 (2)	0.0016 (19)	0.0173 (18)	0.017 (2)
C37B	0.020 (2)	0.047 (3)	0.029 (2)	−0.0018 (19)	0.0128 (17)	0.0161 (19)
C38B	0.033 (3)	0.071 (3)	0.033 (3)	−0.001 (2)	0.003 (2)	0.014 (2)
C39B	0.047 (3)	0.088 (4)	0.027 (3)	−0.008 (3)	−0.001 (2)	0.005 (3)
C40B	0.044 (3)	0.072 (3)	0.038 (3)	0.003 (3)	0.009 (2)	−0.006 (2)
C41B	0.032 (2)	0.049 (3)	0.030 (2)	−0.002 (2)	0.0079 (18)	−0.004 (2)
C42B	0.023 (2)	0.040 (2)	0.027 (2)	−0.0025 (19)	0.0138 (17)	0.0066 (19)
C43B	0.025 (2)	0.029 (2)	0.030 (2)	0.0031 (18)	0.0160 (17)	0.0069 (18)

Geometric parameters (Å, º)

O1A—C1A	1.398 (4)	O1B—C1B	1.395 (4)
O1A—C17A	1.437 (4)	O1B—C17B	1.436 (4)
O2A—C14A	1.397 (4)	O2B—C15B	1.396 (4)
O2A—C15A	1.401 (4)	O2B—C14B	1.407 (4)
O3A—C16A	1.385 (4)	O3B—C16B	1.377 (4)
O3A—C15A	1.412 (4)	O3B—C15B	1.417 (4)
O4A—C15A	1.378 (4)	O4B—C15B	1.371 (4)
O4A—C30A	1.424 (4)	O4B—C30B	1.418 (4)
O5A—C43A	1.352 (4)	O5B—C43B	1.358 (4)
O5A—H5AA	0.8200	O5B—H5BA	0.8200
N1A—C16A	1.273 (4)	C1B—C14B	1.328 (5)
N1A—C17A	1.459 (4)	C1B—C2B	1.426 (5)
C1A—C14A	1.325 (4)	C2B—C3B	1.403 (5)
C1A—C2A	1.416 (5)	C2B—C7B	1.430 (5)
C2A—C3A	1.397 (5)	C3B—C4B	1.342 (5)
C2A—C7A	1.426 (5)	C3B—H3B	0.9300
C3A—C4A	1.347 (5)	C4B—C5B	1.390 (6)
C3A—H3A	0.9300	C4B—H4B	0.9300
C4A—C5A	1.408 (5)	C5B—C6B	1.376 (5)
C4A—H4A	0.9300	C5B—H5B	0.9300
C5A—C6A	1.363 (5)	C6B—C7B	1.400 (5)
C5A—H5A	0.9300	C6B—H6B	0.9300
C6A—C7A	1.400 (5)	C7B—C8B	1.449 (5)
C6A—H6A	0.9300	C8B—C13B	1.402 (5)
C7A—C8A	1.458 (5)	C8B—C9B	1.415 (5)
C8A—C9A	1.400 (5)	C9B—C10B	1.355 (5)
C8A—C13A	1.407 (5)	C9B—H9B	0.9300
C9A—C10A	1.362 (5)	C10B—C11B	1.388 (5)
C9A—H9A	0.9300	C10B—H10B	0.9300
C10A—C11A	1.390 (5)	C11B—C12B	1.384 (5)
C10A—H10A	0.9300	C11B—H11B	0.9300
C11A—C12A	1.365 (5)	C12B—C13B	1.399 (5)
C11A—H11A	0.9300	C12B—H12B	0.9300
C12A—C13A	1.399 (5)	C13B—C14B	1.417 (5)
C12A—H12A	0.9300	C15B—C17B	1.577 (5)
C13A—C14A	1.425 (5)	N1B—C16B	1.278 (4)
C15A—C17A	1.574 (5)	C16B—C24B	1.444 (5)
C16A—C24A	1.447 (5)	N1B—C17B	1.453 (4)
C17A—C18A	1.516 (5)	C17B—C18B	1.518 (5)
C18A—C23A	1.374 (5)	C18B—C23B	1.372 (5)
C18A—C19A	1.379 (5)	C18B—C19B	1.392 (5)
C19A—C20A	1.396 (6)	C19B—C20B	1.403 (5)
C19A—H19A	0.9300	C19B—H19B	0.9300
C20A—C21A	1.377 (6)	C20B—C21B	1.361 (6)
C20A—H20A	0.9300	C20B—H20B	0.9300
C21A—C22A	1.356 (6)	C21B—C22B	1.359 (6)
C21A—H21A	0.9300	C21B—H21B	0.9300
C22A—C23A	1.397 (5)	C22B—C23B	1.402 (5)
C22A—H22A	0.9300	C22B—H22B	0.9300
C23A—H23A	0.9300	C23B—H23B	0.9300
C24A—C25A	1.392 (5)	C24B—C25B	1.394 (5)
C24A—C29A	1.397 (5)	C24B—C29B	1.396 (4)
C25A—C26A	1.352 (5)	C25B—C26B	1.378 (5)
C25A—H25A	0.9300	C25B—H25B	0.9300
C26A—C27A	1.388 (5)	C26B—C27B	1.381 (5)
C26A—H26A	0.9300	C26B—H26B	0.9300
C27A—C28A	1.364 (5)	C27B—C28B	1.367 (5)
C27A—H27A	0.9300	C27B—H27B	0.9300
C28A—C29A	1.390 (5)	C28B—C29B	1.369 (5)
C28A—H28A	0.9300	C28B—H28B	0.9300
C29A—H29A	0.9300	C29B—H29B	0.9300
C30A—C43A	1.345 (5)	C30B—C43B	1.340 (4)
C30A—C31A	1.430 (5)	C30B—C31B	1.423 (5)
C31A—C32A	1.401 (5)	C31B—C32B	1.399 (5)
C31A—C36A	1.427 (5)	C31B—C36B	1.427 (5)
C32A—C33A	1.396 (5)	C32B—C33B	1.361 (5)
C32A—H32A	0.9300	C32B—H32B	0.9300
C33A—C34A	1.395 (6)	C33B—C34B	1.395 (5)
C33A—H33A	0.9300	C33B—H33B	0.9300
C34A—C35A	1.361 (6)	C34B—C35B	1.362 (5)
C34A—H34A	0.9300	C34B—H34B	0.9300
C35A—C36A	1.405 (5)	C35B—C36B	1.409 (5)
C35A—H35A	0.9300	C35B—H35B	0.9300
C36A—C37A	1.440 (5)	C36B—C37B	1.441 (5)
C37A—C42A	1.397 (5)	C37B—C38B	1.408 (5)
C37A—C38A	1.416 (5)	C37B—C42B	1.411 (5)
C38A—C39A	1.364 (6)	C38B—C39B	1.358 (5)
C38A—H38A	0.9300	C38B—H38B	0.9300
C39A—C40A	1.382 (6)	C39B—C40B	1.398 (6)
C39A—H39A	0.9300	C39B—H39B	0.9300
C40A—C41A	1.371 (5)	C40B—C41B	1.369 (5)
C40A—H40A	0.9300	C40B—H40B	0.9300
C41A—C42A	1.389 (5)	C41B—C42B	1.392 (5)
C41A—H41A	0.9300	C41B—H41B	0.9300
C42A—C43A	1.432 (5)	C42B—C43B	1.438 (5)
C1A—O1A—C17A	114.5 (3)	C1B—O1B—C17B	113.1 (3)
C14A—O2A—C15A	113.9 (3)	C15B—O2B—C14B	112.5 (3)
C16A—O3A—C15A	106.4 (3)	C16B—O3B—C15B	106.8 (3)
C15A—O4A—C30A	117.7 (3)	C15B—O4B—C30B	117.9 (3)
C43A—O5A—H5AA	109.5	C43B—O5B—H5BA	109.5
C16A—N1A—C17A	107.2 (3)	C14B—C1B—O1B	118.9 (3)
C14A—C1A—O1A	119.4 (3)	C14B—C1B—C2B	121.5 (3)
C14A—C1A—C2A	122.0 (3)	O1B—C1B—C2B	119.6 (3)
O1A—C1A—C2A	118.4 (3)	C3B—C2B—C1B	123.0 (4)
C3A—C2A—C1A	123.1 (3)	C3B—C2B—C7B	119.5 (4)
C3A—C2A—C7A	119.3 (3)	C1B—C2B—C7B	117.5 (4)
C1A—C2A—C7A	117.5 (3)	C4B—C3B—C2B	120.4 (4)
C4A—C3A—C2A	121.8 (4)	C4B—C3B—H3B	119.8
C4A—C3A—H3A	119.1	C2B—C3B—H3B	119.8
C2A—C3A—H3A	119.1	C3B—C4B—C5B	121.5 (4)
C3A—C4A—C5A	119.5 (4)	C3B—C4B—H4B	119.3
C3A—C4A—H4A	120.3	C5B—C4B—H4B	119.3
C5A—C4A—H4A	120.3	C6B—C5B—C4B	119.8 (4)
C6A—C5A—C4A	120.2 (4)	C6B—C5B—H5B	120.1
C6A—C5A—H5A	119.9	C4B—C5B—H5B	120.1
C4A—C5A—H5A	119.9	C5B—C6B—C7B	120.9 (4)
C5A—C6A—C7A	121.7 (4)	C5B—C6B—H6B	119.5
C5A—C6A—H6A	119.2	C7B—C6B—H6B	119.5
C7A—C6A—H6A	119.2	C6B—C7B—C2B	117.9 (4)
C6A—C7A—C2A	117.5 (3)	C6B—C7B—C8B	122.5 (4)
C6A—C7A—C8A	122.5 (3)	C2B—C7B—C8B	119.6 (4)
C2A—C7A—C8A	120.0 (3)	C13B—C8B—C9B	116.5 (4)
C9A—C8A—C13A	117.5 (3)	C13B—C8B—C7B	120.3 (3)
C9A—C8A—C7A	123.2 (3)	C9B—C8B—C7B	123.2 (4)
C13A—C8A—C7A	119.4 (3)	C10B—C9B—C8B	122.2 (4)
C10A—C9A—C8A	121.5 (4)	C10B—C9B—H9B	118.9
C10A—C9A—H9A	119.2	C8B—C9B—H9B	118.9
C8A—C9A—H9A	119.2	C9B—C10B—C11B	121.1 (4)
C9A—C10A—C11A	120.3 (4)	C9B—C10B—H10B	119.5
C9A—C10A—H10A	119.8	C11B—C10B—H10B	119.5
C11A—C10A—H10A	119.8	C12B—C11B—C10B	118.6 (4)
C12A—C11A—C10A	120.2 (4)	C12B—C11B—H11B	120.7
C12A—C11A—H11A	119.9	C10B—C11B—H11B	120.7
C10A—C11A—H11A	119.9	C11B—C12B—C13B	120.8 (4)
C11A—C12A—C13A	119.9 (4)	C11B—C12B—H12B	119.6
C11A—C12A—H12A	120.0	C13B—C12B—H12B	119.6
C13A—C12A—H12A	120.0	C12B—C13B—C8B	120.8 (3)
C12A—C13A—C8A	120.5 (3)	C12B—C13B—C14B	121.8 (4)
C12A—C13A—C14A	121.8 (3)	C8B—C13B—C14B	117.3 (3)
C8A—C13A—C14A	117.5 (3)	C1B—C14B—O2B	117.3 (3)
C1A—C14A—O2A	118.2 (3)	C1B—C14B—C13B	123.8 (4)
C1A—C14A—C13A	123.5 (3)	O2B—C14B—C13B	118.8 (3)
O2A—C14A—C13A	118.3 (3)	O4B—C15B—O2B	107.4 (3)
O4A—C15A—O2A	106.9 (3)	O4B—C15B—O3B	110.9 (3)
O4A—C15A—O3A	111.1 (3)	O2B—C15B—O3B	108.6 (3)
O2A—C15A—O3A	108.9 (3)	O4B—C15B—C17B	112.1 (3)
O4A—C15A—C17A	111.0 (3)	O2B—C15B—C17B	114.1 (3)
O2A—C15A—C17A	114.6 (3)	O3B—C15B—C17B	103.7 (3)
O3A—C15A—C17A	104.4 (3)	N1B—C16B—O3B	118.0 (3)
N1A—C16A—O3A	118.0 (3)	N1B—C16B—C24B	126.1 (3)
N1A—C16A—C24A	125.5 (3)	O3B—C16B—C24B	115.8 (3)
O3A—C16A—C24A	116.5 (3)	C16B—N1B—C17B	107.0 (3)
O1A—C17A—N1A	108.4 (3)	O1B—C17B—N1B	109.1 (3)
O1A—C17A—C18A	106.8 (3)	O1B—C17B—C18B	107.5 (3)
N1A—C17A—C18A	112.2 (3)	N1B—C17B—C18B	111.6 (3)
O1A—C17A—C15A	110.9 (3)	O1B—C17B—C15B	110.4 (3)
N1A—C17A—C15A	104.0 (3)	N1B—C17B—C15B	104.4 (3)
C18A—C17A—C15A	114.4 (3)	C18B—C17B—C15B	113.8 (3)
C23A—C18A—C19A	119.7 (4)	C23B—C18B—C19B	120.2 (4)
C23A—C18A—C17A	121.3 (3)	C23B—C18B—C17B	119.5 (4)
C19A—C18A—C17A	118.9 (4)	C19B—C18B—C17B	120.2 (3)
C18A—C19A—C20A	120.1 (5)	C18B—C19B—C20B	119.2 (4)
C18A—C19A—H19A	119.9	C18B—C19B—H19B	120.4
C20A—C19A—H19A	119.9	C20B—C19B—H19B	120.4
C21A—C20A—C19A	119.2 (5)	C21B—C20B—C19B	120.0 (5)
C21A—C20A—H20A	120.4	C21B—C20B—H20B	120.0
C19A—C20A—H20A	120.4	C19B—C20B—H20B	120.0
C22A—C21A—C20A	121.1 (4)	C22B—C21B—C20B	120.8 (4)
C22A—C21A—H21A	119.5	C22B—C21B—H21B	119.6
C20A—C21A—H21A	119.5	C20B—C21B—H21B	119.6
C21A—C22A—C23A	119.8 (5)	C21B—C22B—C23B	120.5 (5)
C21A—C22A—H22A	120.1	C21B—C22B—H22B	119.7
C23A—C22A—H22A	120.1	C23B—C22B—H22B	119.7
C18A—C23A—C22A	120.1 (4)	C18B—C23B—C22B	119.3 (5)
C18A—C23A—H23A	120.0	C18B—C23B—H23B	120.4
C22A—C23A—H23A	120.0	C22B—C23B—H23B	120.4
C25A—C24A—C29A	119.6 (4)	C25B—C24B—C29B	119.1 (4)
C25A—C24A—C16A	119.4 (3)	C25B—C24B—C16B	119.6 (3)
C29A—C24A—C16A	120.8 (3)	C29B—C24B—C16B	121.3 (3)
C26A—C25A—C24A	120.4 (4)	C26B—C25B—C24B	120.2 (4)
C26A—C25A—H25A	119.8	C26B—C25B—H25B	119.9
C24A—C25A—H25A	119.8	C24B—C25B—H25B	119.9
C25A—C26A—C27A	120.3 (4)	C25B—C26B—C27B	119.8 (4)
C25A—C26A—H26A	119.8	C25B—C26B—H26B	120.1
C27A—C26A—H26A	119.8	C27B—C26B—H26B	120.1
C28A—C27A—C26A	120.2 (4)	C28B—C27B—C26B	120.2 (4)
C28A—C27A—H27A	119.9	C28B—C27B—H27B	119.9
C26A—C27A—H27A	119.9	C26B—C27B—H27B	119.9
C27A—C28A—C29A	120.5 (4)	C27B—C28B—C29B	121.0 (4)
C27A—C28A—H28A	119.7	C27B—C28B—H28B	119.5
C29A—C28A—H28A	119.7	C29B—C28B—H28B	119.5
C28A—C29A—C24A	118.9 (4)	C28B—C29B—C24B	119.6 (3)
C28A—C29A—H29A	120.6	C28B—C29B—H29B	120.2
C24A—C29A—H29A	120.6	C24B—C29B—H29B	120.2
C43A—C30A—O4A	121.0 (3)	C43B—C30B—O4B	120.6 (3)
C43A—C30A—C31A	121.7 (4)	C43B—C30B—C31B	123.1 (3)
O4A—C30A—C31A	116.7 (3)	O4B—C30B—C31B	116.0 (3)
C32A—C31A—C36A	120.0 (4)	C32B—C31B—C30B	122.3 (3)
C32A—C31A—C30A	121.6 (4)	C32B—C31B—C36B	119.7 (3)
C36A—C31A—C30A	118.3 (4)	C30B—C31B—C36B	117.9 (3)
C33A—C32A—C31A	121.0 (4)	C33B—C32B—C31B	121.2 (4)
C33A—C32A—H32A	119.5	C33B—C32B—H32B	119.4
C31A—C32A—H32A	119.5	C31B—C32B—H32B	119.4
C34A—C33A—C32A	118.3 (5)	C32B—C33B—C34B	119.6 (4)
C34A—C33A—H33A	120.8	C32B—C33B—H33B	120.2
C32A—C33A—H33A	120.8	C34B—C33B—H33B	120.2
C35A—C34A—C33A	121.4 (5)	C35B—C34B—C33B	120.7 (4)
C35A—C34A—H34A	119.3	C35B—C34B—H34B	119.6
C33A—C34A—H34A	119.3	C33B—C34B—H34B	119.6
C34A—C35A—C36A	122.1 (5)	C34B—C35B—C36B	121.6 (4)
C34A—C35A—H35A	119.0	C34B—C35B—H35B	119.2
C36A—C35A—H35A	119.0	C36B—C35B—H35B	119.2
C35A—C36A—C31A	117.1 (4)	C35B—C36B—C31B	117.1 (4)
C35A—C36A—C37A	123.5 (4)	C35B—C36B—C37B	123.2 (4)
C31A—C36A—C37A	119.5 (4)	C31B—C36B—C37B	119.6 (3)
C42A—C37A—C38A	117.9 (4)	C38B—C37B—C42B	116.9 (4)
C42A—C37A—C36A	119.8 (4)	C38B—C37B—C36B	123.5 (4)
C38A—C37A—C36A	122.3 (4)	C42B—C37B—C36B	119.6 (3)
C39A—C38A—C37A	120.3 (4)	C39B—C38B—C37B	121.8 (4)
C39A—C38A—H38A	119.8	C39B—C38B—H38B	119.1
C37A—C38A—H38A	119.8	C37B—C38B—H38B	119.1
C38A—C39A—C40A	121.6 (5)	C38B—C39B—C40B	120.9 (4)
C38A—C39A—H39A	119.2	C38B—C39B—H39B	119.6
C40A—C39A—H39A	119.2	C40B—C39B—H39B	119.6
C41A—C40A—C39A	118.8 (5)	C41B—C40B—C39B	118.7 (4)
C41A—C40A—H40A	120.6	C41B—C40B—H40B	120.7
C39A—C40A—H40A	120.6	C39B—C40B—H40B	120.7
C40A—C41A—C42A	121.3 (4)	C40B—C41B—C42B	121.3 (4)
C40A—C41A—H41A	119.3	C40B—C41B—H41B	119.4
C42A—C41A—H41A	119.3	C42B—C41B—H41B	119.4
C41A—C42A—C37A	120.1 (4)	C41B—C42B—C37B	120.4 (3)
C41A—C42A—C43A	120.6 (4)	C41B—C42B—C43B	120.3 (3)
C37A—C42A—C43A	119.3 (4)	C37B—C42B—C43B	119.3 (3)
C30A—C43A—O5A	124.0 (3)	C30B—C43B—O5B	125.0 (3)
C30A—C43A—C42A	121.2 (4)	C30B—C43B—C42B	120.3 (3)
O5A—C43A—C42A	114.8 (3)	O5B—C43B—C42B	114.7 (3)
C17A—O1A—C1A—C14A	−44.6 (4)	C17B—O1B—C1B—C14B	47.0 (4)
C17A—O1A—C1A—C2A	139.6 (3)	C17B—O1B—C1B—C2B	−133.4 (3)
C14A—C1A—C2A—C3A	175.9 (4)	C14B—C1B—C2B—C3B	−176.1 (4)
O1A—C1A—C2A—C3A	−8.4 (5)	O1B—C1B—C2B—C3B	4.3 (5)
C14A—C1A—C2A—C7A	−0.9 (5)	C14B—C1B—C2B—C7B	1.7 (5)
O1A—C1A—C2A—C7A	174.7 (3)	O1B—C1B—C2B—C7B	−177.9 (3)
C1A—C2A—C3A—C4A	−179.2 (4)	C1B—C2B—C3B—C4B	−179.4 (4)
C7A—C2A—C3A—C4A	−2.4 (6)	C7B—C2B—C3B—C4B	2.8 (6)
C2A—C3A—C4A—C5A	1.2 (6)	C2B—C3B—C4B—C5B	−1.8 (7)
C3A—C4A—C5A—C6A	0.0 (7)	C3B—C4B—C5B—C6B	0.5 (7)
C4A—C5A—C6A—C7A	0.1 (6)	C4B—C5B—C6B—C7B	−0.1 (7)
C5A—C6A—C7A—C2A	−1.2 (6)	C5B—C6B—C7B—C2B	1.1 (6)
C5A—C6A—C7A—C8A	178.5 (4)	C5B—C6B—C7B—C8B	−177.4 (4)
C3A—C2A—C7A—C6A	2.3 (5)	C3B—C2B—C7B—C6B	−2.4 (5)
C1A—C2A—C7A—C6A	179.3 (3)	C1B—C2B—C7B—C6B	179.7 (4)
C3A—C2A—C7A—C8A	−177.4 (3)	C3B—C2B—C7B—C8B	176.1 (3)
C1A—C2A—C7A—C8A	−0.4 (5)	C1B—C2B—C7B—C8B	−1.8 (5)
C6A—C7A—C8A—C9A	0.4 (6)	C6B—C7B—C8B—C13B	178.7 (4)
C2A—C7A—C8A—C9A	−179.9 (3)	C2B—C7B—C8B—C13B	0.2 (5)
C6A—C7A—C8A—C13A	−177.6 (3)	C6B—C7B—C8B—C9B	2.3 (6)
C2A—C7A—C8A—C13A	2.1 (5)	C2B—C7B—C8B—C9B	−176.2 (3)
C13A—C8A—C9A—C10A	−2.5 (5)	C13B—C8B—C9B—C10B	0.9 (5)
C7A—C8A—C9A—C10A	179.4 (3)	C7B—C8B—C9B—C10B	177.4 (3)
C8A—C9A—C10A—C11A	1.3 (6)	C8B—C9B—C10B—C11B	−0.9 (6)
C9A—C10A—C11A—C12A	0.0 (6)	C9B—C10B—C11B—C12B	0.6 (6)
C10A—C11A—C12A—C13A	0.1 (6)	C10B—C11B—C12B—C13B	−0.4 (6)
C11A—C12A—C13A—C8A	−1.4 (6)	C11B—C12B—C13B—C8B	0.5 (5)
C11A—C12A—C13A—C14A	−178.1 (4)	C11B—C12B—C13B—C14B	−178.3 (4)
C9A—C8A—C13A—C12A	2.5 (5)	C9B—C8B—C13B—C12B	−0.8 (5)
C7A—C8A—C13A—C12A	−179.3 (3)	C7B—C8B—C13B—C12B	−177.3 (3)
C9A—C8A—C13A—C14A	179.4 (3)	C9B—C8B—C13B—C14B	178.1 (3)
C7A—C8A—C13A—C14A	−2.4 (5)	C7B—C8B—C13B—C14B	1.5 (5)
O1A—C1A—C14A—O2A	3.7 (5)	O1B—C1B—C14B—O2B	−1.2 (5)
C2A—C1A—C14A—O2A	179.3 (3)	C2B—C1B—C14B—O2B	179.2 (3)
O1A—C1A—C14A—C13A	−175.0 (3)	O1B—C1B—C14B—C13B	179.6 (3)
C2A—C1A—C14A—C13A	0.6 (6)	C2B—C1B—C14B—C13B	0.0 (6)
C15A—O2A—C14A—C1A	41.1 (4)	C15B—O2B—C14B—C1B	−45.8 (4)
C15A—O2A—C14A—C13A	−140.1 (3)	C15B—O2B—C14B—C13B	133.4 (3)
C12A—C13A—C14A—C1A	178.0 (3)	C12B—C13B—C14B—C1B	177.2 (3)
C8A—C13A—C14A—C1A	1.2 (5)	C8B—C13B—C14B—C1B	−1.7 (5)
C12A—C13A—C14A—O2A	−0.7 (5)	C12B—C13B—C14B—O2B	−2.0 (5)
C8A—C13A—C14A—O2A	−177.5 (3)	C8B—C13B—C14B—O2B	179.2 (3)
C30A—O4A—C15A—O2A	−66.4 (4)	C30B—O4B—C15B—O2B	77.3 (3)
C30A—O4A—C15A—O3A	52.3 (4)	C30B—O4B—C15B—O3B	−41.2 (4)
C30A—O4A—C15A—C17A	168.0 (3)	C30B—O4B—C15B—C17B	−156.7 (3)
C14A—O2A—C15A—O4A	−166.8 (3)	C14B—O2B—C15B—O4B	169.9 (3)
C14A—O2A—C15A—O3A	73.1 (3)	C14B—O2B—C15B—O3B	−70.1 (3)
C14A—O2A—C15A—C17A	−43.3 (4)	C14B—O2B—C15B—C17B	45.0 (4)
C16A—O3A—C15A—O4A	118.2 (3)	C16B—O3B—C15B—O4B	−119.5 (3)
C16A—O3A—C15A—O2A	−124.3 (3)	C16B—O3B—C15B—O2B	122.8 (3)
C16A—O3A—C15A—C17A	−1.5 (3)	C16B—O3B—C15B—C17B	1.1 (3)
C17A—N1A—C16A—O3A	1.1 (4)	C15B—O3B—C16B—N1B	−0.5 (4)
C17A—N1A—C16A—C24A	178.8 (3)	C15B—O3B—C16B—C24B	176.4 (3)
C15A—O3A—C16A—N1A	0.4 (4)	O3B—C16B—N1B—C17B	−0.5 (4)
C15A—O3A—C16A—C24A	−177.6 (3)	C24B—C16B—N1B—C17B	−177.0 (3)
C1A—O1A—C17A—N1A	−76.2 (3)	C1B—O1B—C17B—N1B	71.9 (3)
C1A—O1A—C17A—C18A	162.7 (3)	C1B—O1B—C17B—C18B	−166.9 (3)
C1A—O1A—C17A—C15A	37.4 (4)	C1B—O1B—C17B—C15B	−42.3 (4)
C16A—N1A—C17A—O1A	116.2 (3)	C16B—N1B—C17B—O1B	−116.9 (3)
C16A—N1A—C17A—C18A	−126.1 (3)	C16B—N1B—C17B—C18B	124.5 (3)
C16A—N1A—C17A—C15A	−1.9 (3)	C16B—N1B—C17B—C15B	1.1 (3)
O4A—C15A—C17A—O1A	125.9 (3)	O4B—C15B—C17B—O1B	−124.4 (3)
O2A—C15A—C17A—O1A	4.7 (4)	O2B—C15B—C17B—O1B	−2.1 (4)
O3A—C15A—C17A—O1A	−114.3 (3)	O3B—C15B—C17B—O1B	115.8 (3)
O4A—C15A—C17A—N1A	−117.7 (3)	O4B—C15B—C17B—N1B	118.4 (3)
O2A—C15A—C17A—N1A	121.0 (3)	O2B—C15B—C17B—N1B	−119.3 (3)
O3A—C15A—C17A—N1A	2.1 (3)	O3B—C15B—C17B—N1B	−1.3 (3)
O4A—C15A—C17A—C18A	5.1 (4)	O4B—C15B—C17B—C18B	−3.5 (4)
O2A—C15A—C17A—C18A	−116.2 (3)	O2B—C15B—C17B—C18B	118.8 (3)
O3A—C15A—C17A—C18A	124.8 (3)	O3B—C15B—C17B—C18B	−123.3 (3)
O1A—C17A—C18A—C23A	−29.8 (5)	O1B—C17B—C18B—C23B	−140.7 (3)
N1A—C17A—C18A—C23A	−148.5 (3)	N1B—C17B—C18B—C23B	−21.1 (5)
C15A—C17A—C18A—C23A	93.3 (4)	C15B—C17B—C18B—C23B	96.8 (4)
O1A—C17A—C18A—C19A	150.6 (3)	O1B—C17B—C18B—C19B	44.1 (4)
N1A—C17A—C18A—C19A	32.0 (5)	N1B—C17B—C18B—C19B	163.7 (3)
C15A—C17A—C18A—C19A	−86.3 (4)	C15B—C17B—C18B—C19B	−78.4 (4)
C23A—C18A—C19A—C20A	−1.8 (6)	C23B—C18B—C19B—C20B	−1.2 (6)
C17A—C18A—C19A—C20A	177.8 (4)	C17B—C18B—C19B—C20B	173.9 (3)
C18A—C19A—C20A—C21A	2.7 (7)	C18B—C19B—C20B—C21B	−1.2 (6)
C19A—C20A—C21A—C22A	−1.3 (7)	C19B—C20B—C21B—C22B	2.6 (7)
C20A—C21A—C22A—C23A	−1.2 (7)	C20B—C21B—C22B—C23B	−1.6 (7)
C19A—C18A—C23A—C22A	−0.6 (6)	C19B—C18B—C23B—C22B	2.3 (6)
C17A—C18A—C23A—C22A	179.8 (3)	C17B—C18B—C23B—C22B	−172.9 (3)
C21A—C22A—C23A—C18A	2.1 (6)	C21B—C22B—C23B—C18B	−0.9 (6)
N1A—C16A—C24A—C25A	−2.6 (5)	N1B—C16B—C24B—C25B	−0.2 (5)
O3A—C16A—C24A—C25A	175.2 (3)	O3B—C16B—C24B—C25B	−176.8 (3)
N1A—C16A—C24A—C29A	173.2 (3)	N1B—C16B—C24B—C29B	−177.5 (3)
O3A—C16A—C24A—C29A	−9.0 (5)	O3B—C16B—C24B—C29B	6.0 (5)
C29A—C24A—C25A—C26A	3.3 (5)	C29B—C24B—C25B—C26B	−2.8 (5)
C16A—C24A—C25A—C26A	179.2 (3)	C16B—C24B—C25B—C26B	179.9 (3)
C24A—C25A—C26A—C27A	−3.9 (6)	C24B—C25B—C26B—C27B	1.8 (6)
C25A—C26A—C27A—C28A	2.5 (6)	C25B—C26B—C27B—C28B	−0.2 (6)
C26A—C27A—C28A—C29A	−0.5 (6)	C26B—C27B—C28B—C29B	−0.5 (6)
C27A—C28A—C29A—C24A	0.0 (5)	C27B—C28B—C29B—C24B	−0.5 (5)
C25A—C24A—C29A—C28A	−1.4 (5)	C25B—C24B—C29B—C28B	2.1 (5)
C16A—C24A—C29A—C28A	−177.1 (3)	C16B—C24B—C29B—C28B	179.4 (3)
C15A—O4A—C30A—C43A	85.3 (4)	C15B—O4B—C30B—C43B	−82.2 (4)
C15A—O4A—C30A—C31A	−103.7 (4)	C15B—O4B—C30B—C31B	103.0 (4)
C43A—C30A—C31A—C32A	176.0 (4)	C43B—C30B—C31B—C32B	179.9 (4)
O4A—C30A—C31A—C32A	5.0 (5)	O4B—C30B—C31B—C32B	−5.4 (5)
C43A—C30A—C31A—C36A	−1.5 (6)	C43B—C30B—C31B—C36B	−1.3 (6)
O4A—C30A—C31A—C36A	−172.5 (3)	O4B—C30B—C31B—C36B	173.4 (3)
C36A—C31A—C32A—C33A	−0.3 (6)	C30B—C31B—C32B—C33B	179.4 (4)
C30A—C31A—C32A—C33A	−177.7 (4)	C36B—C31B—C32B—C33B	0.6 (6)
C31A—C32A—C33A—C34A	2.2 (7)	C31B—C32B—C33B—C34B	−1.2 (7)
C32A—C33A—C34A—C35A	−2.8 (7)	C32B—C33B—C34B—C35B	0.8 (7)
C33A—C34A—C35A—C36A	1.6 (7)	C33B—C34B—C35B—C36B	0.3 (7)
C34A—C35A—C36A—C31A	0.3 (6)	C34B—C35B—C36B—C31B	−0.9 (6)
C34A—C35A—C36A—C37A	179.5 (4)	C34B—C35B—C36B—C37B	177.9 (4)
C32A—C31A—C36A—C35A	−1.0 (6)	C32B—C31B—C36B—C35B	0.4 (5)
C30A—C31A—C36A—C35A	176.5 (4)	C30B—C31B—C36B—C35B	−178.4 (3)
C32A—C31A—C36A—C37A	179.9 (4)	C32B—C31B—C36B—C37B	−178.4 (3)
C30A—C31A—C36A—C37A	−2.6 (5)	C30B—C31B—C36B—C37B	2.8 (5)
C35A—C36A—C37A—C42A	−174.9 (4)	C35B—C36B—C37B—C38B	−1.5 (6)
C31A—C36A—C37A—C42A	4.2 (6)	C31B—C36B—C37B—C38B	177.3 (4)
C35A—C36A—C37A—C38A	3.5 (6)	C35B—C36B—C37B—C42B	179.2 (4)
C31A—C36A—C37A—C38A	−177.4 (4)	C31B—C36B—C37B—C42B	−2.1 (5)
C42A—C37A—C38A—C39A	2.4 (6)	C42B—C37B—C38B—C39B	−1.0 (6)
C36A—C37A—C38A—C39A	−176.1 (4)	C36B—C37B—C38B—C39B	179.6 (4)
C37A—C38A—C39A—C40A	−2.0 (7)	C37B—C38B—C39B—C40B	0.8 (7)
C38A—C39A—C40A—C41A	−0.1 (7)	C38B—C39B—C40B—C41B	1.0 (7)
C39A—C40A—C41A—C42A	1.8 (7)	C39B—C40B—C41B—C42B	−2.7 (7)
C40A—C41A—C42A—C37A	−1.4 (6)	C40B—C41B—C42B—C37B	2.5 (6)
C40A—C41A—C42A—C43A	178.1 (4)	C40B—C41B—C42B—C43B	−178.6 (4)
C38A—C37A—C42A—C41A	−0.7 (6)	C38B—C37B—C42B—C41B	−0.6 (5)
C36A—C37A—C42A—C41A	177.8 (4)	C36B—C37B—C42B—C41B	178.8 (3)
C38A—C37A—C42A—C43A	179.8 (4)	C38B—C37B—C42B—C43B	−179.5 (3)
C36A—C37A—C42A—C43A	−1.7 (6)	C36B—C37B—C42B—C43B	−0.1 (5)
O4A—C30A—C43A—O5A	−4.2 (6)	O4B—C30B—C43B—O5B	2.6 (6)
C31A—C30A—C43A—O5A	−174.9 (3)	C31B—C30B—C43B—O5B	177.0 (3)
O4A—C30A—C43A—C42A	174.7 (3)	O4B—C30B—C43B—C42B	−175.3 (3)
C31A—C30A—C43A—C42A	4.1 (6)	C31B—C30B—C43B—C42B	−0.9 (6)
C41A—C42A—C43A—C30A	178.1 (4)	C41B—C42B—C43B—C30B	−177.3 (4)
C37A—C42A—C43A—C30A	−2.5 (6)	C37B—C42B—C43B—C30B	1.6 (5)
C41A—C42A—C43A—O5A	−2.9 (5)	C41B—C42B—C43B—O5B	4.5 (5)
C37A—C42A—C43A—O5A	176.6 (3)	C37B—C42B—C43B—O5B	−176.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5A—H5AA···O2A	0.82	1.95	2.704 (3)	152
O5B—H5BA···O2B	0.82	1.95	2.725 (3)	156