trans-5,6a-Di­hydro-5-phenyl­isoindolo­[1,2-b]benz­[1,3]­oxazepin-11-one

The title compound, C₂₂H₁₇NO₂, is composed of an oxoisoindoline moiety fused to a phenyl-substituted benzoxazepine ring and was designed and synthesized as a potential anxiolytic drug. The isoindolinone moiety is essentially planar and the central oxazepine ring adopts a twist-boat conformation with the phenyl group equatorial. In the two independent mol­ecules, the benzene ring of the benzoxazepine fragment makes an angle of 74.4 (1) or 86.1 (1)° with the plane of the isoindoline ring.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.074
• wR factor = 0.194
• Data-to-parameter ratio = 12.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

---

S1. Comment

This work is part of our continuing study aimed at designing modulators of hormonal/neurotransmitter systems as potential drugs to treat neuronal and cardiovascular disorders. Based on the recent pharmacophore/receptor model of the benzodiazepine (BDZ) receptor subtype located in the central nervous system (Huang et al., 2000), we designed the compound (4), as potential anxiolytic agent. Synthesis of the molecule (4) was achieved by a sequential reaction (Fig. 1) and led to a 5:1 diastereomeric (racemic) mixture of cis-(4a) and trans-(4 b) isomers. In order to establish the detailed stereochemistry of the two diastereomers, viz. spatial relationship between the putative pharmacophoric elements (phenyl rings and the two O atoms) which is indispensable for future molecular-modeling studies, the crystal structure determination of (4a) and (4 b) has been undertaken. We report here on the structure of the trans-(4 b) isomer.

In trans-(4 b), two independent molecules (A and B) are identical to within 4σ as far as bond distances and angles are concerned. Thus, only one molecule (A) along with the atom-numbering scheme is shown in Fig. 2. As expected, the isoindolinone ring is essentially planar. The N1—C2 bond is much shorter than the N1—C9 and N1—C18 bonds (Table 1); such N—C bond lengths resemble those typically found in cyclic amino acids (Benedetti et al., 1983), indicating that the lone-pair electrons on N1 are involved in conjugation with the adjacent carbonyl group. A similar pattern of bond distances and angles within the isoindolinone moiety has been found in the cis isomer (Lokaj et al., 2001) as well as other compounds incorporating this molecular fragment (Barrett et al., 1995; McNab et al., 1997; Khan et al., 1998).

As mentioned above, the main purpose of this structure determination was to establish the relative three-dimensional disposition of the phenyl rings and the two O atoms which are assumed to constitute the interaction pharmacophore responsible for binding of the compound to the CNS-subtype of the BDZ receptor. Obviously, the disposition of these structural elements depends primarily on the conformation of the seven-membered oxazepine ring which is the most flexible part of the molecule. A comparison of the endocyclic torsion angles for the oxazepine ring (Table 1) reveals that the ring adopts a twist-boat conformation with an approximate twofold axis passing through C9 and the midpoint of the C12—C17 bond.

The puckering parameters according to Cremer & Pople (1975) are q₂ = 0.817 (4) Å, ϕ₂ = 175.7 (3)° and q₃ = 0.370 (4) Å, ϕ₃ = 106.8 (5)° for the sequence N1A/C9A/O10A/C11A/C12A/C17A/C18A. The corresponding parameters in molecule B are q₂ = 0.814 (4) Å, ϕ₂ = 169.2 (3)° and q₃ = 0.378 (4) Å, ϕ₃ = 108.8 (6)°. The deviation from ideal C₂ symmetry described by the asymmetry parameter ΔC₂(C9) is 0.062 (1) (molecule A) and 0.026 (1) (molecule B) (Nardelli, 1983). Although the puckering mode of the oxazepine ring in molecules A and B is the same, the endocyclic torsion angles in the two molecules differ by up to 23σ. Another difference between molecules A and B concerns the orientation of the phenyl group (at C11) as shown by the torsion angle O10—C11—C19—C24 which is 46.3 (3)° in A and 64.0 (3)° in B. This points to the flexibility of the oxazepine ring and the shallow shape of the potential well corresponding to rotation of the phenyl group about the exocyclic C11—C19 bond. In both molecules, of course, the phenyl substituent occupies a pseudo-equatorial position. The equatorial arrangement of the phenyl group has also been observed for the cis isomer (Lokaj et al., 2001) but in the latter compound the oxazepine ring exists in a distorted C9-chair conformation. This is in line with the known fact that the equatorial orientation of bulky substituents attached to a saturated (or partially unsaturated) seven-membered ring is superior to the actual conformation of the ring, obviously due to low barriers along the pseudorotation pathway. Due to the relatively severe puckering of the central seven-membered ring, the molecules as a whole are non-planar: the two planar `ends' (viz. the isoindoline and the benzene ring of the benzoxazepine moiety) are inclined at an angle of 74.4 (1) and 86.1 (1)° in molecules A and B, respectively. A similar molecular shape has been found for the cis-isomer [bent angle 67.7 (1)°]. This implies an equivalent spatial relationship between the pharmacophoric elements in the two diastereomers and hence, based on the crystal structure data, a similar pharmacological behaviour for the two isomers is predicted.

S2. Experimental

The diastereomers (4a) and (4 b) were synthesized by a three-step reaction. As the first step, to bromomethylbenzophenone (1), prepared freshly from 2-methylbenzophenone (1.96 g, 0.01 mol) and N-bromosuccinimide (1.76 g, 0.01 mol), was added phthalimide (1.5 g, 0.01 mol), potassium carbonate (1.1.g, 8 mmol) and N,N-dimethylformamide (25 ml). The mixture was stirred overnight, diluted with water, extracted with diethyl ether (3 × 20 ml) and dried (magnesium sulfate). The solvent was evaporated under reduced pressure and the solid recrystallized from ethanol to give 2-(N-phthalimidomethyl)benzophenone, (2) (77% yield, m.p. 388 K). In the second step, to a solution of (2) (0.5 g, 15 mmol) in dry methanol (20 ml) at 273–283 K was added sodium borohydride (0.69 g, 30 mmol) by portions. The mixture was stirred for 2 h and monitored by TLC (dichloromethane/acetone 5:1). After 2 h, the starting material disappeared and the excess of sodium borohydride was decomposed by addition of cold water (10 ml) and 10% hydrochloric acid to neutral pH. The precipitate was separated by filtration, washed with water, dried, concentrated under reduced pressure and recrystallized from ethanol to afford a 5:1 ratio of diastereomers (3) (79% yield). Finally, compound (4) was prepared when the diols (3) (0.5 g, 1.5 mmol) were stirred in dry dichloromethane (20 ml) with a catalytic amount of p-toluenesulfonic acid for 30 min at room temperature. The solution was washed with saturated sodium hydrogen carbonate, with water, then dried and concentrated under reduced pressure. Separation of the product by flash chromatography and recrystallization from ethanol gave the corresponding 5:1 ratio of oxazepines (4a) and (4 b) (70% yield); m.p. (4a) 496 K and (4 b) 482 K. The isomers were initially characterized by IR, ¹H and ¹³C NMR spectral analyses.

S3. Refinement

Although most of the H atoms were seen in a difference Fourier map, all were refined with fixed geometry, riding on their carrier atoms, with U_iso set to 1.2U_eq of the parent atom.

Computing details

Data collection: XSCANS (Siemens, 1991); cell refinement: XSCANS; data reduction: XSCANS; 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.

Figures

Fig. 1. A view of the title molecule, showing the labelling of the non-H atoms. Displacement ellipsoids are shown at 30% probability level. Only molecule A is shown for clarity.

trans-5,6a-Dihydro-5-phenylisoindolo[1,2-b]benz[1,3]oxazepin-11-one

Crystal data

C22H17NO2	Z = 4
Mr = 327.37	F(000) = 688
Triclinic, P1	Dx = 1.304 Mg m^−3 Dm = 1.30 (1) Mg m^−3 Dm measured by flotation in bromoform/cyclohexane
a = 10.799 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.113 (4) Å	Cell parameters from 25 reflections
c = 13.775 (4) Å	θ = 7–18°
α = 104.47 (4)°	µ = 0.08 mm^−1
β = 99.40 (3)°	T = 293 K
γ = 101.26 (5)°	Prism, colourless
V = 1667.9 (9) Å^3	0.40 × 0.30 × 0.25 mm

Data collection

Siemens P4 diffractometer	Rint = 0.050
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 1.8°
Graphite monochromator	h = −1→12
ω/2θ scans	k = −13→13
6826 measured reflections	l = −16→16
5812 independent reflections	3 standard reflections every 97 reflections
3954 reflections with I > 2σ(I)	intensity decay: 2%

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)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.194	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.1139P)^2] where P = (Fo^2 + 2Fc^2)/3
5812 reflections	(Δ/σ)max = 0.001
451 parameters	Δρmax = 0.35 e Å^−3
0 restraints	Δρmin = −0.52 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1A	0.4125 (2)	0.77049 (19)	0.86013 (16)	0.0476 (5)
C2A	0.4829 (3)	0.8829 (2)	0.87622 (19)	0.0481 (6)
O2A	0.59495 (18)	0.92528 (19)	0.92572 (15)	0.0629 (5)
C3A	0.3947 (2)	0.9398 (2)	0.82209 (18)	0.0443 (6)
C4A	0.4162 (3)	1.0537 (2)	0.8147 (2)	0.0553 (7)
H4A	0.4968	1.1066	0.8426	0.066*
C5A	0.3137 (3)	1.0862 (3)	0.7642 (2)	0.0600 (8)
H5A	0.3254	1.1622	0.7585	0.072*
C6A	0.1944 (3)	1.0070 (3)	0.7220 (2)	0.0583 (7)
H6A	0.1268	1.0308	0.6887	0.070*
C7A	0.1738 (3)	0.8920 (3)	0.72880 (19)	0.0517 (7)
H7A	0.0938	0.8384	0.7002	0.062*
C8A	0.2766 (2)	0.8606 (2)	0.77959 (18)	0.0432 (6)
C9A	0.2830 (2)	0.7438 (2)	0.79769 (18)	0.0445 (6)
H9A	0.2772	0.6864	0.7318	0.053*
O10A	0.18907 (16)	0.69586 (15)	0.84703 (12)	0.0458 (4)
C11A	0.2075 (2)	0.7634 (2)	0.95392 (17)	0.0404 (6)
H11A	0.2542	0.8444	0.9627	0.049*
C12A	0.2895 (2)	0.7115 (2)	1.02437 (18)	0.0415 (6)
C13A	0.2557 (3)	0.7041 (2)	1.1161 (2)	0.0526 (7)
H13A	0.1831	0.7286	1.1320	0.063*
C14A	0.3275 (3)	0.6610 (3)	1.1846 (2)	0.0610 (8)
H14A	0.3031	0.6566	1.2455	0.073*
C15A	0.4357 (3)	0.6246 (3)	1.1614 (2)	0.0598 (8)
H15A	0.4838	0.5942	1.2059	0.072*
C16A	0.4716 (3)	0.6339 (2)	1.0719 (2)	0.0540 (7)
H16A	0.5453	0.6105	1.0573	0.065*
C17A	0.4011 (2)	0.6774 (2)	1.00205 (19)	0.0449 (6)
C18A	0.4527 (3)	0.6849 (3)	0.9070 (2)	0.0544 (7)
H18A	0.5466	0.7044	0.9256	0.065*
H18B	0.4241	0.6080	0.8564	0.065*
C19A	0.0750 (2)	0.7646 (2)	0.97555 (18)	0.0445 (6)
C20A	0.0520 (3)	0.8685 (3)	1.0286 (2)	0.0579 (7)
H20A	0.1174	0.9375	1.0484	0.070*
C21A	−0.0667 (4)	0.8718 (4)	1.0528 (3)	0.0756 (10)
H21A	−0.0800	0.9424	1.0898	0.091*
C22A	−0.1644 (3)	0.7718 (4)	1.0224 (3)	0.0800 (11)
H22A	−0.2444	0.7743	1.0384	0.096*
C23A	−0.1447 (3)	0.6667 (4)	0.9679 (3)	0.0769 (10)
H23A	−0.2117	0.5987	0.9468	0.092*
C24A	−0.0247 (3)	0.6626 (3)	0.9447 (2)	0.0590 (7)
H24A	−0.0112	0.5917	0.9085	0.071*
N1B	0.2478 (2)	0.33393 (19)	0.29496 (15)	0.0477 (5)
C2B	0.3650 (3)	0.4150 (2)	0.32510 (19)	0.0471 (6)
O2B	0.4664 (2)	0.3981 (2)	0.30305 (16)	0.0678 (6)
C3B	0.3430 (2)	0.5245 (2)	0.38960 (18)	0.0438 (6)
C4B	0.4287 (3)	0.6319 (2)	0.4387 (2)	0.0557 (7)
H4B	0.5145	0.6453	0.4327	0.067*
C5B	0.3835 (3)	0.7192 (3)	0.4974 (2)	0.0655 (8)
H5B	0.4397	0.7924	0.5320	0.079*
C6B	0.2552 (3)	0.6985 (3)	0.5047 (2)	0.0646 (8)
H6B	0.2266	0.7584	0.5444	0.078*
C7B	0.1681 (3)	0.5902 (3)	0.4544 (2)	0.0580 (7)
H7B	0.0817	0.5771	0.4589	0.070*
C8B	0.2149 (2)	0.5027 (2)	0.39726 (18)	0.0446 (6)
C9B	0.1469 (2)	0.3770 (2)	0.33863 (19)	0.0467 (6)
H9B	0.0764	0.3752	0.2832	0.056*
O10B	0.09768 (15)	0.30679 (15)	0.39956 (12)	0.0456 (4)
C11B	0.1990 (2)	0.2913 (2)	0.47483 (17)	0.0401 (6)
H11B	0.2733	0.3591	0.4912	0.048*
C12B	0.2441 (2)	0.1802 (2)	0.43206 (18)	0.0419 (6)
C13B	0.2789 (3)	0.1161 (2)	0.4984 (2)	0.0504 (7)
H13B	0.2700	0.1398	0.5660	0.061*
C14B	0.3266 (3)	0.0176 (2)	0.4663 (2)	0.0598 (8)
H14B	0.3495	−0.0236	0.5122	0.072*
C15B	0.3396 (3)	−0.0183 (3)	0.3669 (2)	0.0633 (8)
H15B	0.3704	−0.0846	0.3446	0.076*
C16B	0.3068 (3)	0.0444 (2)	0.2996 (2)	0.0564 (7)
H16B	0.3162	0.0196	0.2323	0.068*
C17B	0.2598 (2)	0.1444 (2)	0.33045 (19)	0.0466 (6)
C18B	0.2291 (3)	0.2079 (2)	0.2506 (2)	0.0555 (7)
H18C	0.2840	0.1950	0.2018	0.067*
H18D	0.1399	0.1742	0.2130	0.067*
C19B	0.1475 (2)	0.2957 (2)	0.57105 (18)	0.0414 (6)
C20B	0.2052 (3)	0.3872 (2)	0.6604 (2)	0.0563 (7)
H20B	0.2766	0.4447	0.6610	0.068*
C21B	0.1577 (3)	0.3935 (3)	0.7483 (2)	0.0746 (9)
H21B	0.1975	0.4552	0.8075	0.090*
C22B	0.0530 (3)	0.3102 (3)	0.7492 (2)	0.0714 (9)
H22B	0.0217	0.3150	0.8087	0.086*
C23B	−0.0065 (3)	0.2182 (3)	0.6606 (3)	0.0666 (9)
H23B	−0.0779	0.1612	0.6606	0.080*
C24B	0.0410 (3)	0.2115 (3)	0.5719 (2)	0.0532 (7)
H24B	0.0009	0.1499	0.5127	0.064*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0445 (12)	0.0524 (13)	0.0485 (12)	0.0145 (10)	0.0138 (10)	0.0150 (10)
C2A	0.0429 (15)	0.0601 (17)	0.0411 (13)	0.0112 (13)	0.0158 (12)	0.0111 (12)
O2A	0.0425 (11)	0.0802 (14)	0.0621 (12)	0.0105 (10)	0.0080 (9)	0.0198 (11)
C3A	0.0461 (15)	0.0509 (15)	0.0352 (12)	0.0095 (12)	0.0130 (11)	0.0106 (11)
C4A	0.0601 (17)	0.0513 (16)	0.0481 (15)	0.0022 (13)	0.0111 (13)	0.0127 (12)
C5A	0.078 (2)	0.0478 (16)	0.0567 (17)	0.0161 (15)	0.0155 (15)	0.0193 (13)
C6A	0.0641 (19)	0.0640 (19)	0.0500 (15)	0.0218 (16)	0.0076 (14)	0.0211 (14)
C7A	0.0475 (15)	0.0624 (18)	0.0410 (14)	0.0081 (13)	0.0048 (12)	0.0152 (12)
C8A	0.0460 (14)	0.0472 (14)	0.0348 (12)	0.0084 (12)	0.0104 (11)	0.0105 (10)
C9A	0.0455 (14)	0.0465 (14)	0.0391 (12)	0.0094 (11)	0.0123 (11)	0.0081 (11)
O10A	0.0471 (10)	0.0464 (10)	0.0372 (9)	0.0031 (8)	0.0090 (8)	0.0069 (7)
C11A	0.0408 (13)	0.0414 (13)	0.0362 (12)	0.0082 (11)	0.0066 (10)	0.0087 (10)
C12A	0.0417 (14)	0.0404 (13)	0.0406 (13)	0.0086 (11)	0.0093 (11)	0.0096 (10)
C13A	0.0532 (16)	0.0591 (17)	0.0501 (15)	0.0172 (13)	0.0132 (13)	0.0206 (13)
C14A	0.070 (2)	0.072 (2)	0.0512 (16)	0.0218 (16)	0.0157 (14)	0.0309 (14)
C15A	0.0669 (19)	0.0556 (17)	0.0614 (18)	0.0220 (15)	0.0061 (15)	0.0253 (14)
C16A	0.0563 (17)	0.0479 (16)	0.0603 (17)	0.0190 (13)	0.0113 (14)	0.0167 (13)
C17A	0.0477 (15)	0.0397 (14)	0.0461 (14)	0.0114 (11)	0.0098 (11)	0.0106 (11)
C18A	0.0571 (17)	0.0609 (17)	0.0562 (16)	0.0281 (14)	0.0210 (13)	0.0207 (13)
C19A	0.0399 (14)	0.0548 (15)	0.0410 (13)	0.0139 (12)	0.0090 (11)	0.0162 (11)
C20A	0.0629 (18)	0.0626 (18)	0.0575 (16)	0.0255 (15)	0.0206 (14)	0.0216 (14)
C21A	0.077 (2)	0.100 (3)	0.073 (2)	0.049 (2)	0.0340 (19)	0.034 (2)
C22A	0.055 (2)	0.133 (4)	0.063 (2)	0.037 (2)	0.0208 (16)	0.033 (2)
C23A	0.0430 (17)	0.112 (3)	0.0627 (19)	−0.0047 (18)	0.0076 (15)	0.024 (2)
C24A	0.0476 (16)	0.0690 (19)	0.0534 (16)	0.0043 (14)	0.0114 (13)	0.0132 (14)
N1B	0.0524 (13)	0.0511 (13)	0.0410 (11)	0.0141 (11)	0.0129 (10)	0.0134 (10)
C2B	0.0505 (16)	0.0584 (16)	0.0413 (13)	0.0185 (13)	0.0162 (12)	0.0228 (12)
O2B	0.0618 (13)	0.0812 (15)	0.0732 (13)	0.0277 (11)	0.0345 (11)	0.0248 (11)
C3B	0.0424 (14)	0.0529 (15)	0.0415 (13)	0.0150 (12)	0.0087 (11)	0.0214 (11)
C4B	0.0496 (16)	0.0535 (17)	0.0624 (17)	0.0097 (13)	0.0040 (13)	0.0220 (14)
C5B	0.075 (2)	0.0474 (17)	0.0640 (18)	0.0113 (15)	−0.0013 (16)	0.0120 (14)
C6B	0.083 (2)	0.0538 (18)	0.0629 (18)	0.0317 (17)	0.0182 (16)	0.0143 (14)
C7B	0.0596 (18)	0.0606 (18)	0.0671 (18)	0.0281 (15)	0.0209 (14)	0.0274 (15)
C8B	0.0485 (15)	0.0490 (15)	0.0425 (13)	0.0167 (12)	0.0085 (11)	0.0220 (11)
C9B	0.0436 (14)	0.0569 (16)	0.0434 (13)	0.0133 (12)	0.0064 (11)	0.0225 (12)
O10B	0.0370 (9)	0.0532 (10)	0.0463 (9)	0.0081 (8)	0.0039 (7)	0.0198 (8)
C11B	0.0361 (13)	0.0432 (14)	0.0401 (12)	0.0096 (11)	0.0042 (10)	0.0134 (10)
C12B	0.0400 (13)	0.0400 (13)	0.0440 (13)	0.0087 (11)	0.0088 (11)	0.0104 (11)
C13B	0.0558 (16)	0.0490 (15)	0.0512 (15)	0.0174 (13)	0.0143 (13)	0.0179 (12)
C14B	0.0657 (19)	0.0502 (16)	0.073 (2)	0.0222 (14)	0.0204 (15)	0.0252 (14)
C15B	0.0665 (19)	0.0448 (16)	0.080 (2)	0.0183 (14)	0.0232 (16)	0.0129 (15)
C16B	0.0616 (18)	0.0466 (16)	0.0553 (16)	0.0097 (13)	0.0190 (14)	0.0034 (13)
C17B	0.0457 (15)	0.0428 (14)	0.0457 (14)	0.0061 (11)	0.0099 (11)	0.0067 (11)
C18B	0.0703 (19)	0.0522 (16)	0.0420 (14)	0.0154 (14)	0.0141 (13)	0.0088 (12)
C19B	0.0418 (14)	0.0432 (14)	0.0443 (13)	0.0166 (11)	0.0101 (11)	0.0169 (11)
C20B	0.0594 (18)	0.0548 (17)	0.0510 (16)	0.0103 (14)	0.0175 (14)	0.0085 (13)
C21B	0.081 (2)	0.082 (2)	0.0552 (18)	0.0174 (19)	0.0242 (17)	0.0077 (16)
C22B	0.077 (2)	0.098 (3)	0.0569 (18)	0.036 (2)	0.0357 (17)	0.0291 (18)
C23B	0.0505 (17)	0.086 (2)	0.079 (2)	0.0190 (16)	0.0273 (16)	0.0420 (19)
C24B	0.0457 (15)	0.0601 (17)	0.0538 (16)	0.0090 (13)	0.0134 (13)	0.0180 (13)

Geometric parameters (Å, º)

N1A—C2A	1.368 (4)	N1B—C2B	1.370 (4)
N1A—C9A	1.447 (3)	N1B—C9B	1.449 (3)
N1A—C18A	1.449 (3)	N1B—C18B	1.456 (3)
C2A—O2A	1.227 (3)	C2B—O2B	1.224 (3)
C2A—C3A	1.490 (4)	C2B—C3B	1.486 (4)
C3A—C8A	1.373 (4)	C3B—C4B	1.375 (4)
C3A—C4A	1.386 (4)	C3B—C8B	1.382 (4)
C4A—C5A	1.385 (4)	C4B—C5B	1.383 (4)
C4A—H4A	0.9300	C4B—H4B	0.9300
C5A—C6A	1.383 (4)	C5B—C6B	1.384 (4)
C5A—H5A	0.9300	C5B—H5B	0.9300
C6A—C7A	1.397 (4)	C6B—C7B	1.392 (4)
C6A—H6A	0.9300	C6B—H6B	0.9300
C7A—C8A	1.383 (4)	C7B—C8B	1.386 (4)
C7A—H7A	0.9300	C7B—H7B	0.9300
C8A—C9A	1.510 (4)	C8B—C9B	1.506 (4)
C9A—O10A	1.421 (3)	C9B—O10B	1.427 (3)
C9A—H9A	0.9800	C9B—H9B	0.9800
O10A—C11A	1.455 (3)	O10B—C11B	1.454 (3)
C11A—C19A	1.510 (3)	C11B—C19B	1.512 (3)
C11A—C12A	1.537 (3)	C11B—C12B	1.533 (3)
C11A—H11A	0.9800	C11B—H11B	0.9800
C12A—C13A	1.390 (3)	C12B—C13B	1.391 (4)
C12A—C17A	1.403 (3)	C12B—C17B	1.407 (3)
C13A—C14A	1.389 (4)	C13B—C14B	1.391 (4)
C13A—H13A	0.9300	C13B—H13B	0.9300
C14A—C15A	1.384 (4)	C14B—C15B	1.369 (4)
C14A—H14A	0.9300	C14B—H14B	0.9300
C15A—C16A	1.376 (4)	C15B—C16B	1.381 (4)
C15A—H15A	0.9300	C15B—H15B	0.9300
C16A—C17A	1.397 (4)	C16B—C17B	1.399 (4)
C16A—H16A	0.9300	C16B—H16B	0.9300
C17A—C18A	1.520 (4)	C17B—C18B	1.522 (4)
C18A—H18A	0.9700	C18B—H18C	0.9700
C18A—H18B	0.9700	C18B—H18D	0.9700
C19A—C20A	1.379 (4)	C19B—C24B	1.384 (4)
C19A—C24A	1.391 (4)	C19B—C20B	1.388 (4)
C20A—C21A	1.381 (4)	C20B—C21B	1.381 (4)
C20A—H20A	0.9300	C20B—H20B	0.9300
C21A—C22A	1.363 (5)	C21B—C22B	1.364 (5)
C21A—H21A	0.9300	C21B—H21B	0.9300
C22A—C23A	1.382 (5)	C22B—C23B	1.388 (5)
C22A—H22A	0.9300	C22B—H22B	0.9300
C23A—C24A	1.392 (4)	C23B—C24B	1.390 (4)
C23A—H23A	0.9300	C23B—H23B	0.9300
C24A—H24A	0.9300	C24B—H24B	0.9300
C2A—N1A—C9A	114.1 (2)	C2B—N1B—C9B	113.4 (2)
C2A—N1A—C18A	125.8 (2)	C2B—N1B—C18B	125.0 (2)
C9A—N1A—C18A	119.9 (2)	C9B—N1B—C18B	119.2 (2)
O2A—C2A—N1A	125.9 (3)	O2B—C2B—N1B	125.9 (3)
O2A—C2A—C3A	128.7 (3)	O2B—C2B—C3B	128.0 (3)
N1A—C2A—C3A	105.5 (2)	N1B—C2B—C3B	106.1 (2)
C8A—C3A—C4A	121.5 (2)	C4B—C3B—C8B	121.9 (3)
C8A—C3A—C2A	108.8 (2)	C4B—C3B—C2B	129.7 (2)
C4A—C3A—C2A	129.7 (2)	C8B—C3B—C2B	108.3 (2)
C5A—C4A—C3A	117.7 (3)	C3B—C4B—C5B	118.1 (3)
C5A—C4A—H4A	121.1	C3B—C4B—H4B	121.0
C3A—C4A—H4A	121.1	C5B—C4B—H4B	121.0
C6A—C5A—C4A	120.9 (3)	C4B—C5B—C6B	120.4 (3)
C6A—C5A—H5A	119.5	C4B—C5B—H5B	119.8
C4A—C5A—H5A	119.5	C6B—C5B—H5B	119.8
C5A—C6A—C7A	121.0 (3)	C5B—C6B—C7B	121.7 (3)
C5A—C6A—H6A	119.5	C5B—C6B—H6B	119.2
C7A—C6A—H6A	119.5	C7B—C6B—H6B	119.2
C8A—C7A—C6A	117.6 (3)	C8B—C7B—C6B	117.4 (3)
C8A—C7A—H7A	121.2	C8B—C7B—H7B	121.3
C6A—C7A—H7A	121.2	C6B—C7B—H7B	121.3
C3A—C8A—C7A	121.2 (3)	C3B—C8B—C7B	120.5 (3)
C3A—C8A—C9A	109.6 (2)	C3B—C8B—C9B	109.7 (2)
C7A—C8A—C9A	129.2 (2)	C7B—C8B—C9B	129.8 (3)
O10A—C9A—N1A	111.18 (19)	O10B—C9B—N1B	110.8 (2)
O10A—C9A—C8A	116.6 (2)	O10B—C9B—C8B	115.0 (2)
N1A—C9A—C8A	101.9 (2)	N1B—C9B—C8B	102.3 (2)
O10A—C9A—H9A	108.9	O10B—C9B—H9B	109.5
N1A—C9A—H9A	108.9	N1B—C9B—H9B	109.5
C8A—C9A—H9A	108.9	C8B—C9B—H9B	109.5
C9A—O10A—C11A	112.93 (18)	C9B—O10B—C11B	112.97 (18)
O10A—C11A—C19A	107.54 (19)	O10B—C11B—C19B	106.65 (19)
O10A—C11A—C12A	109.91 (19)	O10B—C11B—C12B	111.68 (19)
C19A—C11A—C12A	113.9 (2)	C19B—C11B—C12B	115.0 (2)
O10A—C11A—H11A	108.5	O10B—C11B—H11B	107.7
C19A—C11A—H11A	108.5	C19B—C11B—H11B	107.7
C12A—C11A—H11A	108.5	C12B—C11B—H11B	107.7
C13A—C12A—C17A	118.9 (2)	C13B—C12B—C17B	118.5 (2)
C13A—C12A—C11A	118.6 (2)	C13B—C12B—C11B	118.5 (2)
C17A—C12A—C11A	122.3 (2)	C17B—C12B—C11B	122.9 (2)
C14A—C13A—C12A	121.7 (3)	C14B—C13B—C12B	121.7 (3)
C14A—C13A—H13A	119.2	C14B—C13B—H13B	119.1
C12A—C13A—H13A	119.2	C12B—C13B—H13B	119.1
C15A—C14A—C13A	119.4 (3)	C15B—C14B—C13B	119.7 (3)
C15A—C14A—H14A	120.3	C15B—C14B—H14B	120.2
C13A—C14A—H14A	120.3	C13B—C14B—H14B	120.2
C16A—C15A—C14A	119.4 (3)	C14B—C15B—C16B	119.8 (3)
C16A—C15A—H15A	120.3	C14B—C15B—H15B	120.1
C14A—C15A—H15A	120.3	C16B—C15B—H15B	120.1
C15A—C16A—C17A	122.2 (3)	C15B—C16B—C17B	121.6 (3)
C15A—C16A—H16A	118.9	C15B—C16B—H16B	119.2
C17A—C16A—H16A	118.9	C17B—C16B—H16B	119.2
C16A—C17A—C12A	118.4 (2)	C16B—C17B—C12B	118.8 (2)
C16A—C17A—C18A	116.8 (2)	C16B—C17B—C18B	117.1 (2)
C12A—C17A—C18A	124.8 (2)	C12B—C17B—C18B	124.1 (2)
N1A—C18A—C17A	114.5 (2)	N1B—C18B—C17B	113.3 (2)
N1A—C18A—H18A	108.6	N1B—C18B—H18C	108.9
C17A—C18A—H18A	108.6	C17B—C18B—H18C	108.9
N1A—C18A—H18B	108.6	N1B—C18B—H18D	108.9
C17A—C18A—H18B	108.6	C17B—C18B—H18D	108.9
H18A—C18A—H18B	107.6	H18C—C18B—H18D	107.7
C20A—C19A—C24A	118.7 (3)	C24B—C19B—C20B	118.6 (2)
C20A—C19A—C11A	119.7 (2)	C24B—C19B—C11B	121.4 (2)
C24A—C19A—C11A	121.6 (2)	C20B—C19B—C11B	120.0 (2)
C19A—C20A—C21A	121.1 (3)	C21B—C20B—C19B	120.6 (3)
C19A—C20A—H20A	119.5	C21B—C20B—H20B	119.7
C21A—C20A—H20A	119.5	C19B—C20B—H20B	119.7
C22A—C21A—C20A	120.1 (3)	C22B—C21B—C20B	120.8 (3)
C22A—C21A—H21A	119.9	C22B—C21B—H21B	119.6
C20A—C21A—H21A	119.9	C20B—C21B—H21B	119.6
C21A—C22A—C23A	120.1 (3)	C21B—C22B—C23B	119.5 (3)
C21A—C22A—H22A	120.0	C21B—C22B—H22B	120.2
C23A—C22A—H22A	120.0	C23B—C22B—H22B	120.2
C22A—C23A—C24A	120.0 (3)	C22B—C23B—C24B	119.9 (3)
C22A—C23A—H23A	120.0	C22B—C23B—H23B	120.0
C24A—C23A—H23A	120.0	C24B—C23B—H23B	120.0
C19A—C24A—C23A	119.9 (3)	C19B—C24B—C23B	120.6 (3)
C19A—C24A—H24A	120.0	C19B—C24B—H24B	119.7
C23A—C24A—H24A	120.0	C23B—C24B—H24B	119.7
C9A—N1A—C2A—O2A	−179.3 (2)	C9B—N1B—C2B—O2B	176.1 (2)
C18A—N1A—C2A—O2A	6.6 (4)	C18B—N1B—C2B—O2B	13.9 (4)
C9A—N1A—C2A—C3A	1.0 (3)	C9B—N1B—C2B—C3B	−3.3 (3)
C18A—N1A—C2A—C3A	−173.1 (2)	C18B—N1B—C2B—C3B	−165.4 (2)
O2A—C2A—C3A—C8A	−178.0 (3)	O2B—C2B—C3B—C4B	0.6 (4)
N1A—C2A—C3A—C8A	1.7 (3)	N1B—C2B—C3B—C4B	180.0 (2)
O2A—C2A—C3A—C4A	−0.5 (4)	O2B—C2B—C3B—C8B	−177.7 (3)
N1A—C2A—C3A—C4A	179.2 (3)	N1B—C2B—C3B—C8B	1.6 (3)
C8A—C3A—C4A—C5A	1.1 (4)	C8B—C3B—C4B—C5B	0.2 (4)
C2A—C3A—C4A—C5A	−176.2 (2)	C2B—C3B—C4B—C5B	−177.9 (2)
C3A—C4A—C5A—C6A	−0.5 (4)	C3B—C4B—C5B—C6B	−0.7 (4)
C4A—C5A—C6A—C7A	−0.3 (4)	C4B—C5B—C6B—C7B	0.2 (5)
C5A—C6A—C7A—C8A	0.4 (4)	C5B—C6B—C7B—C8B	0.9 (4)
C4A—C3A—C8A—C7A	−0.9 (4)	C4B—C3B—C8B—C7B	0.9 (4)
C2A—C3A—C8A—C7A	176.8 (2)	C2B—C3B—C8B—C7B	179.4 (2)
C4A—C3A—C8A—C9A	178.7 (2)	C4B—C3B—C8B—C9B	−178.0 (2)
C2A—C3A—C8A—C9A	−3.6 (3)	C2B—C3B—C8B—C9B	0.5 (3)
C6A—C7A—C8A—C3A	0.2 (4)	C6B—C7B—C8B—C3B	−1.4 (4)
C6A—C7A—C8A—C9A	−179.4 (2)	C6B—C7B—C8B—C9B	177.2 (2)
C2A—N1A—C9A—O10A	−127.8 (2)	C2B—N1B—C9B—O10B	−119.5 (2)
C18A—N1A—C9A—O10A	46.6 (3)	C18B—N1B—C9B—O10B	43.7 (3)
C2A—N1A—C9A—C8A	−3.0 (3)	C2B—N1B—C9B—C8B	3.5 (3)
C18A—N1A—C9A—C8A	171.5 (2)	C18B—N1B—C9B—C8B	166.8 (2)
C3A—C8A—C9A—O10A	125.1 (2)	C3B—C8B—C9B—O10B	117.9 (2)
C7A—C8A—C9A—O10A	−55.3 (3)	C7B—C8B—C9B—O10B	−60.8 (3)
C3A—C8A—C9A—N1A	3.9 (3)	C3B—C8B—C9B—N1B	−2.3 (2)
C7A—C8A—C9A—N1A	−176.5 (2)	C7B—C8B—C9B—N1B	179.0 (2)
N1A—C9A—O10A—C11A	47.9 (3)	N1B—C9B—O10B—C11B	51.1 (3)
C8A—C9A—O10A—C11A	−68.3 (3)	C8B—C9B—O10B—C11B	−64.3 (3)
C9A—O10A—C11A—C19A	141.9 (2)	C9B—O10B—C11B—C19B	141.8 (2)
C9A—O10A—C11A—C12A	−93.7 (2)	C9B—O10B—C11B—C12B	−91.7 (2)
O10A—C11A—C12A—C13A	−139.5 (2)	O10B—C11B—C12B—C13B	−144.5 (2)
C19A—C11A—C12A—C13A	−18.7 (3)	C19B—C11B—C12B—C13B	−22.8 (3)
O10A—C11A—C12A—C17A	44.1 (3)	O10B—C11B—C12B—C17B	39.8 (3)
C19A—C11A—C12A—C17A	164.9 (2)	C19B—C11B—C12B—C17B	161.5 (2)
C17A—C12A—C13A—C14A	−1.8 (4)	C17B—C12B—C13B—C14B	−1.0 (4)
C11A—C12A—C13A—C14A	−178.3 (2)	C11B—C12B—C13B—C14B	−176.9 (2)
C12A—C13A—C14A—C15A	0.2 (4)	C12B—C13B—C14B—C15B	−0.2 (4)
C13A—C14A—C15A—C16A	1.2 (4)	C13B—C14B—C15B—C16B	0.8 (5)
C14A—C15A—C16A—C17A	−1.0 (4)	C14B—C15B—C16B—C17B	−0.2 (5)
C15A—C16A—C17A—C12A	−0.6 (4)	C15B—C16B—C17B—C12B	−1.0 (4)
C15A—C16A—C17A—C18A	179.0 (2)	C15B—C16B—C17B—C18B	178.9 (3)
C13A—C12A—C17A—C16A	1.9 (4)	C13B—C12B—C17B—C16B	1.5 (4)
C11A—C12A—C17A—C16A	178.3 (2)	C11B—C12B—C17B—C16B	177.3 (2)
C13A—C12A—C17A—C18A	−177.6 (2)	C13B—C12B—C17B—C18B	−178.4 (2)
C11A—C12A—C17A—C18A	−1.2 (4)	C11B—C12B—C17B—C18B	−2.6 (4)
C2A—N1A—C18A—C17A	96.5 (3)	C2B—N1B—C18B—C17B	79.7 (3)
C9A—N1A—C18A—C17A	−77.2 (3)	C9B—N1B—C18B—C17B	−81.5 (3)
C16A—C17A—C18A—N1A	−156.1 (2)	C16B—C17B—C18B—N1B	−149.4 (2)
C12A—C17A—C18A—N1A	23.5 (4)	C12B—C17B—C18B—N1B	30.5 (4)
O10A—C11A—C19A—C20A	−134.8 (2)	O10B—C11B—C19B—C24B	64.0 (3)
C12A—C11A—C19A—C20A	103.2 (3)	C12B—C11B—C19B—C24B	−60.4 (3)
O10A—C11A—C19A—C24A	46.3 (3)	O10B—C11B—C19B—C20B	−114.4 (2)
C12A—C11A—C19A—C24A	−75.8 (3)	C12B—C11B—C19B—C20B	121.1 (3)
C24A—C19A—C20A—C21A	1.3 (4)	C24B—C19B—C20B—C21B	0.3 (4)
C11A—C19A—C20A—C21A	−177.7 (3)	C11B—C19B—C20B—C21B	178.8 (3)
C19A—C20A—C21A—C22A	−1.3 (5)	C19B—C20B—C21B—C22B	−0.1 (5)
C20A—C21A—C22A—C23A	0.4 (5)	C20B—C21B—C22B—C23B	−0.1 (5)
C21A—C22A—C23A—C24A	0.5 (5)	C21B—C22B—C23B—C24B	0.1 (5)
C22A—C23A—C24A—C19A	−0.6 (5)	C20B—C19B—C24B—C23B	−0.3 (4)
C20A—C19A—C24A—C23A	−0.3 (4)	C11B—C19B—C24B—C23B	−178.8 (2)
C11A—C19A—C24A—C23A	178.6 (2)	C22B—C23B—C24B—C19B	0.1 (4)