Diphenyl-5,6,7,7a-tetra­hydro­pyrrolo[1,2-c]oxazol-3(1H)-one

The title compound, C₁₈H₁₇NO₂, synthesized from enanti­omerically pure L-proline, methyl chloroformate and a Grignard reagent, crystallizes with two mol­ecules in the asymmetric unit. A chair conformation is adopted by the two fused five-membered rings.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.008 Å
• Disorder in main residue
• R factor = 0.076
• wR factor = 0.134
• Data-to-parameter ratio = 6.9

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT035_ALERT_1_A No _chemical_absolute_configuration info given .          ?

Author Response: As this is a light atom structure (C, H, N, and O) collected with Mo radiation data were averaged and thus there is no Flack parameter to report.

Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       6.92
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C6B
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C6A
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        N1B
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        N1A
PLAT301_ALERT_3_C Main Residue  Disorder .........................      11.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8
PLAT410_ALERT_2_C Short Intra H...H Contact  H21A   ..  H26A    ..       1.97 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         14

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.01
           From the CIF: _reflns_number_total               2735
           Count of symmetry unique reflns         2738
           Completeness (_total/calc)             99.89%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3B    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C21    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3A    = .          S

   1 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.

Diphenyl-5,6,7,7a-tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one

Crystal data

C18H17NO2	F(000) = 592
Mr = 279.33	Dx = 1.269 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1848 reflections
a = 9.4120 (12) Å	θ = 2.4–24.2°
b = 9.7918 (12) Å	µ = 0.08 mm^−1
c = 15.996 (2) Å	T = 298 K
β = 97.254 (2)°	Block, colorless
V = 1462.4 (3) Å^3	0.29 × 0.18 × 0.17 mm
Z = 4

Data collection

Bruker APEX area-detector diffractometer	2735 independent reflections
Radiation source: fine-focus sealed tube	2523 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 25.0°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −11→11
Tmin = 0.976, Tmax = 0.979	k = 0→11
7716 measured reflections	l = 0→19

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)] = 0.076	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.134	H-atom parameters constrained
S = 1.35	w = 1/[σ^2(Fo^2) + (0.0329P)^2 + 0.5185P] where P = (Fo^2 + 2Fc^2)/3
2735 reflections	(Δ/σ)max = 0.001
395 parameters	Δρmax = 0.19 e Å^−3
1 restraint	Δρmin = −0.15 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.6851 (4)	0.3867 (4)	0.3830 (2)	0.0586 (10)
O2	0.5656 (6)	0.5758 (5)	0.3419 (4)	0.0980 (17)
C1	0.7524 (5)	0.2724 (5)	0.3452 (3)	0.0450 (12)
C2	0.6226 (7)	0.4727 (6)	0.3226 (5)	0.0624 (17)
N1A	0.657 (3)	0.412 (3)	0.2315 (15)	0.045 (3)	0.405 (18)
C3A	0.764 (6)	0.315 (9)	0.247 (5)	0.045 (6)	0.405 (18)
H3AA	0.7299	0.2353	0.2136	0.054*	0.405 (18)
C4A	0.887 (4)	0.350 (3)	0.219 (2)	0.060 (3)	0.405 (18)
H4AA	0.9347	0.2719	0.1984	0.072*	0.405 (18)
H4AB	0.9511	0.3963	0.2622	0.072*	0.405 (18)
C5A	0.827 (5)	0.450 (4)	0.146 (3)	0.074 (6)	0.405 (18)
H5AA	0.8949	0.5231	0.1409	0.089*	0.405 (18)
H5AB	0.8129	0.4009	0.0927	0.089*	0.405 (18)
C6A	0.690 (4)	0.507 (5)	0.164 (3)	0.077 (5)	0.405 (18)
H6AA	0.6181	0.5035	0.1153	0.092*	0.405 (18)
H6AB	0.7011	0.6002	0.1844	0.092*	0.405 (18)
N1B	0.628 (2)	0.4298 (17)	0.2549 (9)	0.045 (3)	0.595 (18)
C3B	0.727 (4)	0.313 (6)	0.254 (3)	0.045 (6)	0.595 (18)
H3BA	0.6865	0.2391	0.2171	0.054*	0.595 (18)
C4B	0.855 (2)	0.3964 (19)	0.2138 (14)	0.060 (3)	0.595 (18)
H4BA	0.9112	0.4509	0.2566	0.072*	0.595 (18)
H4BB	0.9183	0.3337	0.1895	0.072*	0.595 (18)
C5B	0.776 (3)	0.485 (2)	0.1479 (19)	0.074 (6)	0.595 (18)
H5BA	0.7583	0.4362	0.0947	0.089*	0.595 (18)
H5BB	0.8306	0.5667	0.1396	0.089*	0.595 (18)
C6B	0.637 (3)	0.519 (3)	0.1812 (15)	0.077 (5)	0.595 (18)
H6BA	0.6365	0.6146	0.1979	0.092*	0.595 (18)
H6BB	0.5565	0.5033	0.1383	0.092*	0.595 (18)
C7	0.9058 (5)	0.2631 (5)	0.3884 (3)	0.0416 (11)
C8	0.9686 (6)	0.3670 (6)	0.4382 (3)	0.0574 (14)
H8A	0.9158	0.4449	0.4467	0.069*
C9	1.1101 (7)	0.3572 (8)	0.4761 (4)	0.0709 (18)
H9A	1.1503	0.4282	0.5099	0.085*
C10	1.1902 (6)	0.2436 (8)	0.4639 (4)	0.0739 (19)
H10A	1.2847	0.2370	0.4889	0.089*
C11	1.1296 (6)	0.1411 (8)	0.4149 (4)	0.0751 (19)
H11A	1.1826	0.0633	0.4063	0.090*
C12	0.9893 (6)	0.1515 (6)	0.3775 (4)	0.0640 (16)
H12A	0.9502	0.0801	0.3437	0.077*
C13	0.6679 (5)	0.1438 (5)	0.3594 (3)	0.0405 (12)
C14	0.5932 (5)	0.1341 (6)	0.4278 (3)	0.0556 (14)
H14A	0.5912	0.2086	0.4636	0.067*
C15	0.5209 (6)	0.0155 (8)	0.4445 (4)	0.0642 (17)
H15A	0.4688	0.0114	0.4900	0.077*
C16	0.5275 (6)	−0.0951 (7)	0.3929 (4)	0.0594 (16)
H16A	0.4804	−0.1753	0.4042	0.071*
C17	0.6018 (6)	−0.0896 (6)	0.3257 (4)	0.0564 (15)
H17A	0.6063	−0.1655	0.2912	0.068*
C18	0.6707 (5)	0.0300 (5)	0.3090 (3)	0.0464 (13)
H18A	0.7205	0.0338	0.2624	0.056*
O3	0.0338 (3)	0.8839 (4)	0.1176 (2)	0.0512 (9)
O4	−0.1716 (4)	0.8433 (5)	0.1706 (3)	0.0818 (14)
N2	0.0453 (5)	0.8547 (5)	0.2563 (3)	0.0556 (12)
C19	0.1842 (5)	0.9028 (5)	0.1500 (3)	0.0408 (11)
C20	−0.0435 (6)	0.8588 (6)	0.1819 (4)	0.0577 (15)
C21	0.1923 (6)	0.8404 (6)	0.2382 (3)	0.0500 (14)
H21A	0.2563	0.8950	0.2782	0.060*
C22	0.2233 (7)	0.6896 (7)	0.2530 (4)	0.0642 (16)
H22A	0.3254	0.6718	0.2641	0.077*
H22B	0.1821	0.6345	0.2056	0.077*
C23	0.1487 (7)	0.6647 (8)	0.3309 (4)	0.083 (2)
H24A	0.1210	0.5696	0.3341	0.100*
H24B	0.2117	0.6879	0.3817	0.100*
C24	0.0180 (8)	0.7556 (8)	0.3213 (4)	0.084 (2)
H23A	−0.0680	0.7032	0.3036	0.101*
H23B	0.0073	0.8013	0.3740	0.101*
C25	0.2115 (5)	1.0568 (5)	0.1486 (3)	0.0406 (12)
C26	0.2874 (6)	1.1276 (6)	0.2135 (4)	0.0639 (16)
H26A	0.3249	1.0819	0.2623	0.077*
C27	0.3083 (7)	1.2675 (7)	0.2066 (4)	0.0782 (19)
H27A	0.3590	1.3148	0.2512	0.094*
C28	0.2555 (7)	1.3364 (7)	0.1351 (5)	0.0709 (18)
H28A	0.2703	1.4299	0.1308	0.085*
C29	0.1811 (6)	1.2668 (7)	0.0704 (4)	0.0659 (16)
H29A	0.1438	1.3129	0.0217	0.079*
C30	0.1604 (6)	1.1276 (6)	0.0766 (3)	0.0569 (15)
H30A	0.1110	1.0809	0.0313	0.068*
C31	0.2734 (5)	0.8263 (5)	0.0923 (3)	0.0418 (12)
C32	0.4186 (5)	0.8545 (6)	0.0963 (3)	0.0484 (13)
H32A	0.4597	0.9209	0.1333	0.058*
C33	0.5018 (6)	0.7853 (7)	0.0460 (4)	0.0662 (17)
H33A	0.5989	0.8055	0.0494	0.079*
C34	0.4448 (7)	0.6873 (7)	−0.0090 (4)	0.0726 (19)
H34A	0.5019	0.6421	−0.0435	0.087*
C35	0.3019 (7)	0.6566 (6)	−0.0126 (4)	0.0693 (17)
H35A	0.2621	0.5892	−0.0493	0.083*
C36	0.2167 (6)	0.7252 (6)	0.0380 (3)	0.0538 (14)
H36A	0.1202	0.7029	0.0353	0.065*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.080 (3)	0.035 (2)	0.060 (2)	0.0143 (19)	0.007 (2)	−0.0042 (19)
O2	0.113 (4)	0.050 (3)	0.129 (5)	0.031 (3)	0.007 (3)	0.008 (3)
C1	0.060 (3)	0.034 (3)	0.040 (3)	0.002 (3)	0.004 (2)	−0.004 (2)
C2	0.063 (4)	0.034 (3)	0.089 (5)	0.001 (3)	0.003 (4)	0.010 (4)
N1A	0.070 (9)	0.045 (6)	0.024 (9)	0.017 (5)	0.016 (5)	−0.007 (6)
C3A	0.050 (18)	0.038 (3)	0.046 (8)	−0.010 (14)	0.007 (12)	−0.001 (4)
C4A	0.075 (10)	0.052 (12)	0.054 (5)	0.028 (7)	0.018 (6)	0.030 (9)
C5A	0.13 (2)	0.034 (13)	0.067 (5)	−0.001 (10)	0.031 (12)	−0.008 (9)
C6A	0.108 (19)	0.067 (7)	0.057 (11)	0.014 (11)	0.018 (9)	0.022 (8)
N1B	0.070 (9)	0.045 (6)	0.024 (9)	0.017 (5)	0.016 (5)	−0.007 (6)
C3B	0.050 (18)	0.038 (3)	0.046 (8)	−0.010 (14)	0.007 (12)	−0.001 (4)
C4B	0.075 (10)	0.052 (12)	0.054 (5)	0.028 (7)	0.018 (6)	0.030 (9)
C5B	0.13 (2)	0.034 (13)	0.067 (5)	−0.001 (10)	0.031 (12)	−0.008 (9)
C6B	0.108 (19)	0.067 (7)	0.057 (11)	0.014 (11)	0.018 (9)	0.022 (8)
C7	0.058 (3)	0.036 (3)	0.031 (3)	−0.006 (3)	0.007 (2)	−0.002 (2)
C8	0.074 (4)	0.046 (3)	0.054 (3)	−0.010 (3)	0.014 (3)	−0.006 (3)
C9	0.070 (4)	0.075 (5)	0.065 (4)	−0.024 (4)	−0.001 (3)	−0.016 (4)
C10	0.054 (4)	0.094 (6)	0.071 (4)	−0.011 (4)	−0.003 (3)	−0.003 (4)
C11	0.053 (4)	0.076 (5)	0.094 (5)	0.000 (4)	0.002 (3)	−0.017 (4)
C12	0.058 (3)	0.055 (4)	0.076 (4)	−0.004 (3)	−0.002 (3)	−0.019 (3)
C13	0.036 (3)	0.042 (3)	0.043 (3)	0.006 (2)	0.000 (2)	0.006 (2)
C14	0.047 (3)	0.061 (4)	0.059 (4)	0.009 (3)	0.009 (3)	0.002 (3)
C15	0.042 (3)	0.096 (5)	0.057 (4)	0.003 (3)	0.013 (3)	0.023 (4)
C16	0.046 (3)	0.059 (4)	0.069 (4)	−0.012 (3)	−0.009 (3)	0.020 (3)
C17	0.056 (3)	0.044 (3)	0.065 (4)	−0.003 (3)	−0.006 (3)	0.006 (3)
C18	0.047 (3)	0.041 (3)	0.052 (3)	0.000 (2)	0.009 (2)	0.002 (3)
O3	0.0408 (19)	0.063 (2)	0.049 (2)	−0.0023 (18)	0.0037 (16)	−0.0056 (19)
O4	0.048 (2)	0.096 (4)	0.105 (4)	−0.007 (2)	0.021 (2)	−0.020 (3)
N2	0.070 (3)	0.052 (3)	0.049 (3)	−0.016 (2)	0.023 (2)	−0.009 (2)
C19	0.042 (3)	0.042 (3)	0.038 (3)	−0.003 (2)	−0.001 (2)	−0.002 (2)
C20	0.056 (4)	0.049 (4)	0.068 (4)	−0.004 (3)	0.011 (3)	−0.025 (3)
C21	0.054 (3)	0.050 (3)	0.044 (3)	−0.018 (3)	−0.002 (2)	−0.003 (3)
C22	0.069 (4)	0.059 (4)	0.064 (4)	−0.003 (3)	0.005 (3)	0.018 (3)
C23	0.103 (5)	0.075 (5)	0.067 (4)	−0.032 (4)	−0.003 (4)	0.018 (4)
C24	0.111 (5)	0.088 (5)	0.060 (4)	−0.022 (5)	0.034 (4)	0.001 (4)
C25	0.034 (3)	0.046 (3)	0.043 (3)	0.007 (2)	0.009 (2)	−0.002 (2)
C26	0.073 (4)	0.049 (4)	0.066 (4)	−0.013 (3)	−0.010 (3)	0.003 (3)
C27	0.090 (5)	0.059 (4)	0.080 (5)	−0.021 (4)	−0.008 (4)	−0.009 (4)
C28	0.081 (4)	0.046 (4)	0.089 (5)	−0.002 (3)	0.024 (4)	0.008 (4)
C29	0.072 (4)	0.054 (4)	0.073 (4)	0.019 (3)	0.013 (3)	0.018 (3)
C30	0.069 (4)	0.053 (4)	0.048 (3)	0.004 (3)	0.002 (3)	0.000 (3)
C31	0.054 (3)	0.031 (3)	0.038 (3)	−0.003 (2)	−0.002 (2)	0.011 (2)
C32	0.049 (3)	0.044 (3)	0.053 (3)	−0.001 (3)	0.009 (2)	0.005 (3)
C33	0.060 (4)	0.065 (4)	0.078 (4)	0.000 (3)	0.023 (3)	0.010 (4)
C34	0.087 (5)	0.063 (4)	0.074 (4)	0.021 (4)	0.032 (4)	0.004 (4)
C35	0.096 (5)	0.050 (4)	0.062 (4)	−0.003 (4)	0.011 (3)	−0.008 (3)
C36	0.056 (3)	0.050 (4)	0.057 (3)	−0.005 (3)	0.011 (3)	−0.003 (3)

Geometric parameters (Å, º)

O1—C2	1.359 (7)	C15—C16	1.367 (9)
O1—C1	1.456 (6)	C15—H15A	0.9300
O2—C2	1.202 (8)	C16—C17	1.355 (8)
C1—C3B	1.51 (5)	C16—H16A	0.9300
C1—C13	1.522 (7)	C17—C18	1.381 (7)
C1—C7	1.523 (7)	C17—H17A	0.9300
C1—C3A	1.64 (8)	C18—H18A	0.9300
C2—N1B	1.168 (16)	O3—C20	1.355 (6)
C2—N1A	1.643 (18)	O3—C19	1.457 (5)
N1A—C3A	1.39 (8)	O4—C20	1.206 (6)
N1A—C6A	1.49 (5)	N2—C20	1.367 (7)
C3A—C4A	1.33 (6)	N2—C21	1.456 (6)
C3A—H3AA	0.9800	N2—C24	1.468 (8)
C4A—C5A	1.58 (5)	C19—C31	1.521 (7)
C4A—H4AA	0.9700	C19—C25	1.531 (7)
C4A—H4AB	0.9700	C19—C21	1.531 (7)
C5A—C6A	1.46 (4)	C21—C22	1.518 (8)
C5A—H5AA	0.9700	C21—H21A	0.9800
C5A—H5AB	0.9700	C22—C23	1.526 (8)
C6A—H6AA	0.9700	C22—H22A	0.9700
C6A—H6AB	0.9700	C22—H22B	0.9700
N1B—C3B	1.47 (5)	C23—C24	1.511 (9)
N1B—C6B	1.48 (3)	C23—H24A	0.9700
C3B—C4B	1.65 (4)	C23—H24B	0.9700
C3B—H3BA	0.9800	C24—H23A	0.9700
C4B—C5B	1.49 (3)	C24—H23B	0.9700
C4B—H4BA	0.9700	C25—C26	1.371 (7)
C4B—H4BB	0.9700	C25—C30	1.378 (7)
C5B—C6B	1.52 (2)	C26—C27	1.390 (9)
C5B—H5BA	0.9700	C26—H26A	0.9300
C5B—H5BB	0.9700	C27—C28	1.366 (9)
C6B—H6BA	0.9700	C27—H27A	0.9300
C6B—H6BB	0.9700	C28—C29	1.358 (9)
C7—C12	1.370 (7)	C28—H28A	0.9300
C7—C8	1.378 (7)	C29—C30	1.382 (8)
C8—C9	1.394 (8)	C29—H29A	0.9300
C8—H8A	0.9300	C30—H30A	0.9300
C9—C10	1.372 (9)	C31—C36	1.380 (7)
C9—H9A	0.9300	C31—C32	1.387 (7)
C10—C11	1.355 (9)	C32—C33	1.371 (7)
C10—H10A	0.9300	C32—H32A	0.9300
C11—C12	1.383 (8)	C33—C34	1.365 (8)
C11—H11A	0.9300	C33—H33A	0.9300
C12—H12A	0.9300	C34—C35	1.372 (8)
C13—C14	1.376 (7)	C34—H34A	0.9300
C13—C18	1.377 (7)	C35—C36	1.383 (8)
C14—C15	1.389 (9)	C35—H35A	0.9300
C14—H14A	0.9300	C36—H36A	0.9300
C2—O1—C1	110.6 (5)	C18—C13—C1	122.2 (4)
O1—C1—C3B	100.1 (19)	C13—C14—C15	121.5 (6)
O1—C1—C13	108.1 (4)	C13—C14—H14A	119.3
C3B—C1—C13	110.1 (18)	C15—C14—H14A	119.3
O1—C1—C7	107.1 (4)	C16—C15—C14	119.1 (5)
C3B—C1—C7	118.8 (12)	C16—C15—H15A	120.5
C13—C1—C7	111.5 (4)	C14—C15—H15A	120.5
O1—C1—C3A	107 (3)	C17—C16—C15	120.9 (6)
C13—C1—C3A	117 (3)	C17—C16—H16A	119.6
C7—C1—C3A	106 (2)	C15—C16—H16A	119.6
N1B—C2—O2	127.8 (10)	C16—C17—C18	119.4 (6)
N1B—C2—O1	111.8 (9)	C16—C17—H17A	120.3
O2—C2—O1	120.3 (7)	C18—C17—H17A	120.3
O2—C2—N1A	132.5 (12)	C13—C18—C17	121.8 (5)
O1—C2—N1A	106.9 (11)	C13—C18—H18A	119.1
C3A—N1A—C6A	110 (3)	C17—C18—H18A	119.1
C3A—N1A—C2	108 (4)	C20—O3—C19	110.1 (4)
C6A—N1A—C2	120 (2)	C20—N2—C21	108.7 (4)
N1A—C3A—C4A	114 (6)	C20—N2—C24	119.7 (5)
N1A—C3A—C1	102 (4)	C21—N2—C24	109.5 (5)
C4A—C3A—C1	124 (5)	O3—C19—C31	107.9 (4)
N1A—C3A—H3AA	105.3	O3—C19—C25	106.1 (4)
C4A—C3A—H3AA	105.2	C31—C19—C25	111.7 (4)
C1—C3A—H3AA	105.2	O3—C19—C21	102.2 (4)
C3A—C4A—C5A	100 (5)	C31—C19—C21	113.3 (4)
C3A—C4A—H4AA	112.1	C25—C19—C21	114.6 (4)
C5A—C4A—H4AA	111.9	O4—C20—O3	122.2 (6)
C3A—C4A—H4AB	111.8	O4—C20—N2	128.0 (6)
C5A—C4A—H4AB	111.7	O3—C20—N2	109.8 (4)
H4AA—C4A—H4AB	109.5	N2—C21—C22	103.4 (4)
C6A—C5A—C4A	109 (4)	N2—C21—C19	102.0 (4)
C6A—C5A—H5AA	109.9	C22—C21—C19	121.2 (5)
C4A—C5A—H5AA	110.0	N2—C21—H21A	109.8
C6A—C5A—H5AB	109.8	C22—C21—H21A	109.8
C4A—C5A—H5AB	109.8	C19—C21—H21A	109.8
H5AA—C5A—H5AB	108.3	C21—C22—C23	100.5 (5)
C5A—C6A—N1A	100 (4)	C21—C22—H22A	111.7
C5A—C6A—H6AA	111.7	C23—C22—H22A	111.7
N1A—C6A—H6AA	111.7	C21—C22—H22B	111.7
C5A—C6A—H6AB	111.7	C23—C22—H22B	111.7
N1A—C6A—H6AB	111.7	H22A—C22—H22B	109.4
H6AA—C6A—H6AB	109.5	C24—C23—C22	106.0 (5)
C2—N1B—C3B	113 (2)	C24—C23—H24A	110.5
C2—N1B—C6B	122.6 (16)	C22—C23—H24A	110.5
C3B—N1B—C6B	110 (2)	C24—C23—H24B	110.5
N1B—C3B—C1	102 (3)	C22—C23—H24B	110.5
N1B—C3B—C4B	97 (3)	H24A—C23—H24B	108.7
C1—C3B—C4B	118 (3)	N2—C24—C23	104.4 (5)
N1B—C3B—H3BA	112.5	N2—C24—H23A	110.9
C1—C3B—H3BA	112.6	C23—C24—H23A	110.9
C4B—C3B—H3BA	112.6	N2—C24—H23B	110.9
C5B—C4B—C3B	104 (2)	C23—C24—H23B	110.9
C5B—C4B—H4BA	111.1	H23A—C24—H23B	108.9
C3B—C4B—H4BA	111.0	C26—C25—C30	118.2 (5)
C5B—C4B—H4BB	111.0	C26—C25—C19	124.0 (5)
C3B—C4B—H4BB	110.9	C30—C25—C19	117.8 (5)
H4BA—C4B—H4BB	109.0	C25—C26—C27	120.2 (6)
C4B—C5B—C6B	105 (2)	C25—C26—H26A	119.9
C4B—C5B—H5BA	110.8	C27—C26—H26A	119.9
C6B—C5B—H5BA	110.8	C28—C27—C26	120.9 (6)
C4B—C5B—H5BB	110.7	C28—C27—H27A	119.6
C6B—C5B—H5BB	110.8	C26—C27—H27A	119.6
H5BA—C5B—H5BB	108.9	C29—C28—C27	119.2 (6)
N1B—C6B—C5B	107 (2)	C29—C28—H28A	120.4
N1B—C6B—H6BA	110.4	C27—C28—H28A	120.4
C5B—C6B—H6BA	110.4	C28—C29—C30	120.3 (6)
N1B—C6B—H6BB	110.4	C28—C29—H29A	119.8
C5B—C6B—H6BB	110.4	C30—C29—H29A	119.8
H6BA—C6B—H6BB	108.6	C25—C30—C29	121.2 (6)
C12—C7—C8	116.8 (5)	C25—C30—H30A	119.4
C12—C7—C1	121.0 (5)	C29—C30—H30A	119.4
C8—C7—C1	122.1 (5)	C36—C31—C32	118.2 (5)
C7—C8—C9	121.2 (6)	C36—C31—C19	122.4 (4)
C7—C8—H8A	119.4	C32—C31—C19	119.3 (4)
C9—C8—H8A	119.4	C33—C32—C31	120.4 (5)
C10—C9—C8	120.3 (6)	C33—C32—H32A	119.8
C10—C9—H9A	119.8	C31—C32—H32A	119.8
C8—C9—H9A	119.8	C34—C33—C32	121.3 (6)
C11—C10—C9	119.0 (6)	C34—C33—H33A	119.4
C11—C10—H10A	120.5	C32—C33—H33A	119.4
C9—C10—H10A	120.5	C33—C34—C35	119.0 (6)
C10—C11—C12	120.4 (6)	C33—C34—H34A	120.5
C10—C11—H11A	119.8	C35—C34—H34A	120.5
C12—C11—H11A	119.8	C34—C35—C36	120.4 (6)
C7—C12—C11	122.3 (6)	C34—C35—H35A	119.8
C7—C12—H12A	118.8	C36—C35—H35A	119.8
C11—C12—H12A	118.8	C31—C36—C35	120.7 (5)
C14—C13—C18	117.3 (5)	C31—C36—H36A	119.7
C14—C13—C1	120.3 (5)	C35—C36—H36A	119.7
C2—O1—C1—C3B	3.9 (15)	C3A—C1—C13—C14	−148 (3)
C2—O1—C1—C13	−111.2 (5)	O1—C1—C13—C18	157.2 (4)
C2—O1—C1—C7	128.5 (5)	C3B—C1—C13—C18	48.8 (17)
C2—O1—C1—C3A	15 (2)	C7—C1—C13—C18	−85.2 (6)
C1—O1—C2—N1B	5.4 (12)	C3A—C1—C13—C18	37 (3)
C1—O1—C2—O2	−177.5 (6)	C18—C13—C14—C15	−1.4 (7)
C1—O1—C2—N1A	−2.3 (13)	C1—C13—C14—C15	−176.8 (4)
O2—C2—N1A—C3A	160 (3)	C13—C14—C15—C16	1.8 (8)
O1—C2—N1A—C3A	−14 (4)	C14—C15—C16—C17	−0.8 (8)
O2—C2—N1A—C6A	33 (4)	C15—C16—C17—C18	−0.4 (8)
O1—C2—N1A—C6A	−141 (3)	C14—C13—C18—C17	0.1 (7)
C6A—N1A—C3A—C4A	18 (7)	C1—C13—C18—C17	175.4 (5)
C2—N1A—C3A—C4A	−114 (5)	C16—C17—C18—C13	0.9 (8)
C6A—N1A—C3A—C1	154 (3)	C20—O3—C19—C31	137.3 (4)
C2—N1A—C3A—C1	22 (5)	C20—O3—C19—C25	−102.8 (5)
O1—C1—C3A—N1A	−24 (5)	C20—O3—C19—C21	17.6 (5)
C13—C1—C3A—N1A	98 (4)	C19—O3—C20—O4	178.0 (5)
C7—C1—C3A—N1A	−138 (3)	C19—O3—C20—N2	−2.1 (6)
O1—C1—C3A—C4A	106 (6)	C21—N2—C20—O4	164.2 (6)
C13—C1—C3A—C4A	−133 (6)	C24—N2—C20—O4	37.5 (9)
C7—C1—C3A—C4A	−8 (7)	C21—N2—C20—O3	−15.7 (6)
N1A—C3A—C4A—C5A	−26 (7)	C24—N2—C20—O3	−142.4 (5)
C1—C3A—C4A—C5A	−151 (6)	C20—N2—C21—C22	−100.9 (5)
C3A—C4A—C5A—C6A	25 (6)	C24—N2—C21—C22	31.5 (6)
C4A—C5A—C6A—N1A	−15 (5)	C20—N2—C21—C19	25.5 (5)
C3A—N1A—C6A—C5A	0 (6)	C24—N2—C21—C19	157.9 (5)
C2—N1A—C6A—C5A	126 (3)	O3—C19—C21—N2	−25.1 (5)
O2—C2—N1B—C3B	170.2 (18)	C31—C19—C21—N2	−140.9 (4)
O1—C2—N1B—C3B	−13 (2)	C25—C19—C21—N2	89.2 (5)
O2—C2—N1B—C6B	34 (2)	O3—C19—C21—C22	88.8 (6)
O1—C2—N1B—C6B	−149.0 (16)	C31—C19—C21—C22	−27.1 (7)
C2—N1B—C3B—C1	15 (3)	C25—C19—C21—C22	−157.0 (5)
C6B—N1B—C3B—C1	156 (2)	N2—C21—C22—C23	−39.6 (5)
C2—N1B—C3B—C4B	−106 (2)	C19—C21—C22—C23	−152.7 (5)
C6B—N1B—C3B—C4B	35 (3)	C21—C22—C23—C24	34.6 (6)
O1—C1—C3B—N1B	−10 (2)	C20—N2—C24—C23	117.1 (6)
C13—C1—C3B—N1B	104 (2)	C21—N2—C24—C23	−9.3 (6)
C7—C1—C3B—N1B	−125.8 (16)	C22—C23—C24—N2	−16.5 (7)
O1—C1—C3B—C4B	95 (3)	O3—C19—C25—C26	135.5 (5)
C13—C1—C3B—C4B	−151 (3)	C31—C19—C25—C26	−107.1 (6)
C7—C1—C3B—C4B	−21 (4)	C21—C19—C25—C26	23.6 (7)
C3A—C1—C3B—C4B	−27 (19)	O3—C19—C25—C30	−46.6 (6)
N1B—C3B—C4B—C5B	−41 (3)	C31—C19—C25—C30	70.8 (5)
C1—C3B—C4B—C5B	−149 (3)	C21—C19—C25—C30	−158.5 (5)
C3B—C4B—C5B—C6B	32 (3)	C30—C25—C26—C27	1.4 (9)
C2—N1B—C6B—C5B	119 (2)	C19—C25—C26—C27	179.3 (6)
C3B—N1B—C6B—C5B	−18 (3)	C25—C26—C27—C28	−0.7 (10)
C4B—C5B—C6B—N1B	−11 (3)	C26—C27—C28—C29	0.3 (10)
O1—C1—C7—C12	168.2 (5)	C27—C28—C29—C30	−0.6 (10)
C3B—C1—C7—C12	−80 (2)	C26—C25—C30—C29	−1.8 (8)
C13—C1—C7—C12	50.1 (6)	C19—C25—C30—C29	−179.8 (5)
C3A—C1—C7—C12	−78 (3)	C28—C29—C30—C25	1.4 (9)
O1—C1—C7—C8	−13.5 (6)	O3—C19—C31—C36	−18.4 (6)
C3B—C1—C7—C8	99 (2)	C25—C19—C31—C36	−134.7 (5)
C13—C1—C7—C8	−131.7 (5)	C21—C19—C31—C36	93.9 (5)
C3A—C1—C7—C8	100 (3)	O3—C19—C31—C32	164.2 (4)
C12—C7—C8—C9	−0.7 (8)	C25—C19—C31—C32	47.9 (6)
C1—C7—C8—C9	−178.9 (5)	C21—C19—C31—C32	−83.5 (5)
C7—C8—C9—C10	0.5 (9)	C36—C31—C32—C33	1.4 (7)
C8—C9—C10—C11	−0.3 (10)	C19—C31—C32—C33	178.9 (5)
C9—C10—C11—C12	0.3 (10)	C31—C32—C33—C34	0.0 (9)
C8—C7—C12—C11	0.7 (9)	C32—C33—C34—C35	−1.1 (9)
C1—C7—C12—C11	179.0 (5)	C33—C34—C35—C36	0.8 (9)
C10—C11—C12—C7	−0.5 (10)	C32—C31—C36—C35	−1.6 (8)
O1—C1—C13—C14	−27.5 (6)	C19—C31—C36—C35	−179.1 (5)
C3B—C1—C13—C14	−135.9 (17)	C34—C35—C36—C31	0.6 (9)
C7—C1—C13—C14	90.0 (5)