2-Benzoyl-3-cyclo­hexyl-4-(p-methoxy­phenyl)-5-phenyl­pyrrolidine-3-spiro-3′-chroman-4′-one

Usha, G.; Selvanayagam, S.; Yogavel, M.; Velmurugan, D.; Amalraj, A.; Raghunathan, R.; Shanmuga Sundara Raj, S.; Fun, H.-K.

doi:10.1107/S1600536803020944

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2-Benzoyl-3-cyclohexyl-4-(p-methoxyphenyl)-5-phenylpyrrolidine-3-spiro-3′-chroman-4′-one

G. Usha, S. Selvanayagam, M. Yogavel, D. Velmurugan, A. Amalraj, R. Raghunathan, S. Shanmuga Sundara Raj and H.-K. Fun

The title compound, C₃₈H₃₇NO₄, crystallizes with two molecules in the asymmetric unit. The molecules have similar geometric parameters and represent opposite enantiomers of the title compound. In both molecules, the pyrrolidine ring adopts an envelope conformation; the pyran ring in the chromanone moiety has a half-chair conformation. The molecular packing in the crystal is stabilized by C—H

O and C—H

π interactions, in addition to van der Waals forces.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803020944/ya6175sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803020944/ya6175Isup2.hkl Contains datablock I

CCDC reference: 225861

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.047
wR factor = 0.137
Data-to-parameter ratio = 10.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.09 Ratio

Alert level C
ABSMU01_ALERT_1_C  The ratio of given/expected absorption coefficient lies
               outside the range 0.99 <> 1.01
            Calculated value of mu =     0.079
            Value of mu given      =     0.080
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.99
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.34 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.25 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.20 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O1B    -   C12B     =       5.17 su
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         12
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C38 H37 N O4

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           28.30
           From the CIF: _reflns_number_total               8348
           Count of symmetry unique reflns         8422
           Completeness (_total/calc)             99.12%
           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

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

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

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: 'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 1990)'; software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

2-Benzoyl-3-cyclohexyl-4-(p-methoxyphenyl)-5-phenylpyrrolidine-3-spiro- 3'-chroman-4'-one top

Crystal data top

C₃₈H₃₇NO₄	F(000) = 2432
M_r = 571.69	D_x = 1.226 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 24284 reflections
a = 11.8945 (3) Å	θ = 2.0–28.2°
b = 19.2698 (4) Å	µ = 0.08 mm⁻¹
c = 27.0279 (6) Å	T = 293 K
V = 6194.9 (2) Å³	Block, yellow
Z = 8	0.24 × 0.20 × 0.16 mm

Data collection top

Siemens SMART CCD area-detector diffractometer	6500 reflections with I > \2s(I)
Radiation source: fine-focus sealed tube	R_int = 0.037
Graphite monochromator	θ_max = 28.3°, θ_min = 1.8°
ω scans	h = −10→15
42360 measured reflections	k = −25→23
8348 independent reflections	l = −35→32

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0668P)² + 1.0304P] where P = (F_o² + 2F_c²)/3
8348 reflections	(Δ/σ)_max < 0.001
775 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
N1A	0.69144 (18)	0.99116 (11)	0.14794 (8)	0.0401 (5)
C2A	0.7928 (2)	0.97466 (14)	0.17615 (9)	0.0395 (5)
H2A	0.8178	1.0154	0.1948	0.047*
C3A	0.7509 (2)	0.91714 (13)	0.21220 (9)	0.0389 (5)
H3A	0.7606	0.8730	0.1947	0.047*
C4A	0.6214 (2)	0.92842 (13)	0.21707 (9)	0.0383 (5)
C5A	0.5950 (2)	0.99122 (13)	0.18158 (9)	0.0393 (5)
H5A	0.5262	0.9815	0.1629	0.047*
C6A	0.6995 (3)	1.04323 (15)	0.10778 (11)	0.0498 (7)
H6A	0.7442	1.0210	0.0818	0.060*
C7A	0.7601 (4)	1.1100 (2)	0.11947 (16)	0.0844 (13)
H7A1	0.8327	1.0997	0.1341	0.101*
H7A2	0.7167	1.1366	0.1432	0.101*
C8A	0.7767 (5)	1.1529 (2)	0.07165 (18)	0.0992 (16)
H8A1	0.8123	1.1968	0.0798	0.119*
H8A2	0.8260	1.1280	0.0493	0.119*
C9A	0.6649 (5)	1.1667 (2)	0.04613 (19)	0.0961 (15)
H9A1	0.6197	1.1971	0.0667	0.115*
H9A2	0.6785	1.1902	0.0150	0.115*
C10A	0.6018 (4)	1.1015 (2)	0.03669 (15)	0.0824 (12)
H10A	0.6419	1.0740	0.0124	0.099*
H10B	0.5285	1.1127	0.0231	0.099*
C11A	0.5864 (3)	1.05846 (18)	0.08427 (12)	0.0575 (8)
H11A	0.5398	1.0839	0.1074	0.069*
H11B	0.5488	1.0152	0.0764	0.069*
C12A	0.5806 (2)	1.05972 (14)	0.21067 (10)	0.0443 (6)
C13A	0.4704 (3)	1.09635 (14)	0.21133 (10)	0.0464 (6)
C14A	0.3710 (3)	1.06717 (18)	0.19436 (14)	0.0611 (8)
H14A	0.3717	1.0226	0.1812	0.073*
C15A	0.2704 (3)	1.1035 (2)	0.19676 (15)	0.0702 (10)
H15A	0.2044	1.0832	0.1853	0.084*
C16A	0.2684 (3)	1.1693 (2)	0.21599 (15)	0.0718 (10)
H16A	0.2012	1.1939	0.2173	0.086*
C17A	0.3655 (4)	1.19866 (19)	0.23321 (18)	0.0825 (12)
H17A	0.3640	1.2432	0.2464	0.099*
C18A	0.4653 (3)	1.16293 (16)	0.23123 (14)	0.0644 (9)
H18A	0.5304	1.1835	0.2434	0.077*
C19A	0.5572 (2)	0.86495 (13)	0.19690 (9)	0.0407 (5)
C20A	0.4405 (2)	0.85702 (15)	0.21468 (10)	0.0458 (6)
C21A	0.3974 (3)	0.90207 (16)	0.25034 (10)	0.0490 (7)
C22A	0.5806 (2)	0.93863 (16)	0.27049 (10)	0.0453 (6)
H22A	0.5981	0.8975	0.2897	0.054*
H22B	0.6204	0.9774	0.2852	0.054*
C23A	0.3698 (3)	0.80547 (17)	0.19469 (12)	0.0574 (8)
H23A	0.3983	0.7741	0.1717	0.069*
C24A	0.2591 (3)	0.8012 (2)	0.20887 (15)	0.0725 (10)
H24A	0.2127	0.7672	0.1955	0.087*
C25A	0.2169 (3)	0.8477 (2)	0.24307 (15)	0.0766 (11)
H25A	0.1414	0.8453	0.2519	0.092*
C26A	0.2845 (3)	0.8977 (2)	0.26441 (13)	0.0667 (9)
H26A	0.2553	0.9281	0.2879	0.080*
C27A	0.8186 (2)	0.91100 (14)	0.25931 (9)	0.0404 (5)
C28A	0.8633 (2)	0.84708 (14)	0.27223 (10)	0.0456 (6)
H28A	0.8500	0.8091	0.2518	0.055*
C29A	0.9277 (3)	0.83801 (16)	0.31491 (11)	0.0541 (7)
H29A	0.9571	0.7946	0.3226	0.065*
C30A	0.9473 (3)	0.89393 (16)	0.34554 (11)	0.0548 (7)
C31A	0.9042 (3)	0.95894 (16)	0.33304 (11)	0.0565 (8)
H31A	0.9177	0.9969	0.3535	0.068*
C32A	0.8417 (3)	0.96717 (15)	0.29055 (10)	0.0486 (6)
H32A	0.8142	1.0109	0.2825	0.058*
C33A	1.0592 (5)	0.8263 (3)	0.4003 (2)	0.128 (2)
H33A	1.0981	0.8301	0.4313	0.192*
H33B	1.1118	0.8145	0.3747	0.192*
H33C	1.0029	0.7908	0.4027	0.192*
C34A	0.8886 (2)	0.94639 (14)	0.14519 (10)	0.0437 (6)
C35A	0.9985 (3)	0.95537 (19)	0.16074 (13)	0.0593 (8)
H35A	1.0136	0.9837	0.1878	0.071*
C36A	1.0871 (3)	0.9223 (2)	0.13616 (18)	0.0801 (12)
H36A	1.1607	0.9281	0.1471	0.096*
C37A	1.0650 (4)	0.8814 (2)	0.09592 (18)	0.0828 (13)
H37A	1.1238	0.8589	0.0798	0.099*
C38A	0.9573 (4)	0.87315 (19)	0.07915 (15)	0.0735 (11)
H38A	0.9434	0.8463	0.0512	0.088*
C39A	0.8688 (3)	0.90485 (16)	0.10381 (12)	0.0551 (7)
H39A	0.7956	0.8983	0.0926	0.066*
O1A	0.66158 (18)	1.08332 (11)	0.23288 (9)	0.0604 (6)
O2A	0.46192 (17)	0.95149 (11)	0.27278 (7)	0.0526 (5)
O3A	0.59905 (18)	0.82430 (11)	0.16769 (8)	0.0554 (5)
O4A	1.0073 (3)	0.89056 (14)	0.38889 (10)	0.0876 (9)
N1B	1.30653 (19)	1.02866 (11)	0.47633 (8)	0.0411 (5)
C2B	1.2027 (2)	1.05236 (14)	0.45270 (9)	0.0410 (6)
H2B	1.1747	1.0169	0.4298	0.049*
C3B	1.2446 (2)	1.11710 (14)	0.42340 (9)	0.0406 (6)
H3B	1.2416	1.1562	0.4466	0.049*
C4B	1.3722 (2)	1.10313 (13)	0.41338 (9)	0.0403 (5)
C5B	1.3963 (2)	1.03185 (13)	0.43930 (9)	0.0412 (5)
H5B	1.4697	1.0333	0.4558	0.049*
C6B	1.3002 (3)	0.97011 (15)	0.51124 (11)	0.0492 (6)
H6B	1.2570	0.9873	0.5396	0.059*
C7B	1.2396 (3)	0.90557 (18)	0.49401 (15)	0.0676 (9)
H7B1	1.2820	0.8838	0.4675	0.081*
H7B2	1.1662	0.9181	0.4812	0.081*
C8B	1.2257 (4)	0.8541 (2)	0.53706 (17)	0.0794 (12)
H8B1	1.1782	0.8744	0.5624	0.095*
H8B2	1.1896	0.8121	0.5252	0.095*
C9B	1.3402 (4)	0.8360 (2)	0.55918 (18)	0.0821 (12)
H9B1	1.3296	0.8063	0.5877	0.098*
H9B2	1.3840	0.8106	0.5350	0.098*
C10B	1.4037 (4)	0.8999 (2)	0.57453 (15)	0.0755 (10)
H10C	1.4778	0.8866	0.5862	0.091*
H10D	1.3646	0.9222	0.6017	0.091*
C11B	1.4158 (3)	0.95120 (16)	0.53183 (11)	0.0533 (7)
H11C	1.4613	0.9307	0.5059	0.064*
H11D	1.4535	0.9928	0.5434	0.064*
C12B	1.3925 (3)	0.97044 (14)	0.40265 (10)	0.0493 (7)
C13B	1.4897 (3)	0.92064 (16)	0.40035 (12)	0.0599 (9)
C14B	1.5980 (3)	0.9382 (2)	0.41412 (15)	0.0757 (11)
H14B	1.6130	0.9824	0.4263	0.091*
C15B	1.6845 (4)	0.8902 (3)	0.4097 (2)	0.1086 (19)
H15B	1.7578	0.9024	0.4180	0.130*
C16B	1.6604 (7)	0.8242 (3)	0.3930 (2)	0.131 (3)
H16B	1.7176	0.7915	0.3913	0.157*
C17B	1.5523 (7)	0.8057 (2)	0.3785 (2)	0.123 (2)
H17B	1.5378	0.7614	0.3665	0.147*
C18B	1.4664 (5)	0.85387 (18)	0.38200 (16)	0.0852 (13)
H18B	1.3938	0.8422	0.3723	0.102*
C19B	1.4454 (2)	1.15707 (13)	0.44057 (10)	0.0428 (6)
C20B	1.5627 (2)	1.16194 (14)	0.42221 (11)	0.0455 (6)
C21B	1.5962 (3)	1.12617 (15)	0.38027 (11)	0.0476 (6)
C22B	1.4064 (2)	1.10657 (16)	0.35888 (9)	0.0465 (6)
H22C	1.3594	1.0754	0.3398	0.056*
H22D	1.3946	1.1533	0.3466	0.056*
C23B	1.6434 (3)	1.20067 (16)	0.44807 (13)	0.0561 (7)
H23B	1.6217	1.2259	0.4758	0.067*
C24B	1.7540 (3)	1.2022 (2)	0.43330 (16)	0.0698 (10)
H24B	1.8067	1.2278	0.4510	0.084*
C25B	1.7860 (3)	1.1647 (2)	0.39150 (15)	0.0724 (10)
H25B	1.8606	1.1652	0.3813	0.087*
C26B	1.7083 (3)	1.12717 (19)	0.36528 (13)	0.0632 (9)
H26B	1.7304	1.1023	0.3374	0.076*
C27B	1.1724 (2)	1.13755 (14)	0.37954 (10)	0.0419 (6)
C28B	1.1315 (3)	1.09111 (14)	0.34479 (11)	0.0491 (6)
H28B	1.1494	1.0443	0.3479	0.059*
C29B	1.0641 (3)	1.11233 (14)	0.30530 (11)	0.0484 (6)
H29B	1.0370	1.0801	0.2826	0.058*
C30B	1.0380 (2)	1.18193 (14)	0.30027 (10)	0.0458 (6)
C31B	1.0770 (3)	1.22945 (14)	0.33451 (11)	0.0508 (7)
H31B	1.0587	1.2762	0.3314	0.061*
C32B	1.1436 (3)	1.20712 (14)	0.37356 (11)	0.0486 (6)
H32B	1.1696	1.2395	0.3964	0.058*
C33B	0.9203 (4)	1.1636 (2)	0.22940 (15)	0.0794 (11)
H33D	0.8799	1.1896	0.2049	0.119*
H33E	0.8687	1.1350	0.2476	0.119*
H33F	0.9751	1.1347	0.2134	0.119*
C34B	1.1109 (2)	1.07349 (14)	0.48838 (10)	0.0439 (6)
C35B	0.9988 (3)	1.06271 (19)	0.47594 (12)	0.0601 (8)
H35B	0.9805	1.0374	0.4478	0.072*
C36B	0.9135 (3)	1.0899 (3)	0.50581 (17)	0.0833 (13)
H36B	0.8388	1.0842	0.4966	0.100*
C37B	0.9389 (4)	1.1248 (2)	0.54860 (17)	0.0781 (11)
H37B	0.8817	1.1423	0.5685	0.094*
C38B	1.0491 (4)	1.13354 (19)	0.56187 (15)	0.0742 (11)
H38B	1.0667	1.1561	0.5913	0.089*
C39B	1.1346 (3)	1.10894 (17)	0.53168 (12)	0.0578 (8)
H39B	1.2090	1.1164	0.5407	0.069*
O1B	1.3088 (2)	0.96044 (12)	0.37793 (8)	0.0629 (6)
O2B	1.52243 (18)	1.08770 (11)	0.35236 (8)	0.0535 (5)
O3B	1.41214 (19)	1.19051 (12)	0.47564 (8)	0.0594 (6)
O4B	0.97510 (19)	1.20964 (11)	0.26213 (9)	0.0608 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0377 (11)	0.0463 (11)	0.0362 (10)	0.0019 (9)	0.0020 (9)	0.0033 (9)
C2A	0.0361 (13)	0.0434 (13)	0.0392 (12)	−0.0002 (11)	0.0013 (10)	0.0010 (10)
C3A	0.0400 (13)	0.0397 (13)	0.0370 (12)	−0.0021 (11)	0.0026 (10)	−0.0011 (10)
C4A	0.0387 (13)	0.0429 (12)	0.0332 (11)	−0.0018 (11)	0.0021 (10)	−0.0014 (10)
C5A	0.0380 (13)	0.0400 (12)	0.0398 (12)	0.0006 (10)	−0.0011 (11)	−0.0027 (10)
C6A	0.0495 (16)	0.0527 (15)	0.0473 (14)	−0.0001 (13)	0.0021 (12)	0.0098 (12)
C7A	0.102 (3)	0.074 (2)	0.078 (2)	−0.033 (2)	−0.019 (2)	0.018 (2)
C8A	0.122 (4)	0.080 (3)	0.095 (3)	−0.042 (3)	−0.020 (3)	0.036 (2)
C9A	0.120 (4)	0.069 (2)	0.100 (3)	0.002 (3)	−0.004 (3)	0.038 (2)
C10A	0.076 (3)	0.100 (3)	0.071 (2)	0.004 (2)	−0.009 (2)	0.038 (2)
C11A	0.0540 (18)	0.0644 (18)	0.0541 (16)	0.0036 (15)	−0.0022 (14)	0.0150 (14)
C12A	0.0440 (14)	0.0442 (14)	0.0446 (13)	−0.0022 (12)	0.0039 (12)	−0.0053 (11)
C13A	0.0521 (16)	0.0437 (14)	0.0435 (13)	0.0016 (12)	0.0064 (12)	−0.0010 (11)
C14A	0.0474 (17)	0.0582 (17)	0.078 (2)	0.0075 (15)	0.0003 (16)	−0.0174 (16)
C15A	0.0504 (18)	0.080 (2)	0.080 (2)	0.0106 (17)	0.0036 (17)	−0.015 (2)
C16A	0.066 (2)	0.071 (2)	0.079 (2)	0.0239 (19)	0.0114 (19)	−0.0036 (19)
C17A	0.088 (3)	0.0534 (19)	0.106 (3)	0.024 (2)	0.008 (3)	−0.019 (2)
C18A	0.072 (2)	0.0465 (16)	0.075 (2)	0.0035 (16)	0.0011 (18)	−0.0139 (15)
C19A	0.0438 (14)	0.0422 (13)	0.0362 (12)	−0.0052 (11)	−0.0017 (11)	0.0039 (10)
C20A	0.0461 (15)	0.0482 (14)	0.0430 (13)	−0.0070 (12)	−0.0013 (12)	0.0034 (11)
C21A	0.0463 (15)	0.0612 (17)	0.0396 (13)	−0.0101 (14)	0.0002 (12)	0.0008 (12)
C22A	0.0401 (14)	0.0593 (16)	0.0367 (12)	−0.0067 (12)	0.0018 (11)	−0.0066 (12)
C23A	0.0539 (18)	0.0590 (17)	0.0593 (18)	−0.0157 (15)	−0.0010 (15)	−0.0030 (14)
C24A	0.059 (2)	0.086 (3)	0.073 (2)	−0.0295 (19)	0.0004 (18)	−0.005 (2)
C25A	0.0447 (18)	0.111 (3)	0.074 (2)	−0.022 (2)	0.0043 (17)	−0.003 (2)
C26A	0.0447 (17)	0.098 (3)	0.0577 (18)	−0.0078 (18)	0.0111 (15)	−0.0060 (19)
C27A	0.0381 (13)	0.0452 (13)	0.0377 (12)	−0.0039 (11)	0.0003 (10)	−0.0003 (10)
C28A	0.0455 (15)	0.0445 (13)	0.0467 (14)	−0.0007 (12)	−0.0012 (12)	−0.0020 (11)
C29A	0.0552 (17)	0.0505 (15)	0.0566 (16)	0.0059 (14)	−0.0099 (14)	0.0026 (13)
C30A	0.0527 (17)	0.0607 (17)	0.0509 (15)	−0.0045 (14)	−0.0153 (14)	0.0045 (14)
C31A	0.068 (2)	0.0510 (15)	0.0504 (15)	−0.0132 (15)	−0.0120 (15)	−0.0071 (13)
C32A	0.0578 (17)	0.0395 (13)	0.0484 (14)	−0.0020 (12)	−0.0071 (13)	0.0001 (11)
C33A	0.169 (6)	0.090 (3)	0.125 (4)	0.014 (3)	−0.101 (4)	0.008 (3)
C34A	0.0417 (14)	0.0460 (14)	0.0434 (13)	0.0004 (12)	0.0087 (11)	0.0077 (11)
C35A	0.0417 (16)	0.075 (2)	0.0608 (18)	−0.0027 (15)	0.0030 (14)	0.0071 (16)
C36A	0.0390 (17)	0.095 (3)	0.106 (3)	0.0087 (18)	0.0188 (19)	0.030 (3)
C37A	0.075 (3)	0.072 (2)	0.102 (3)	0.016 (2)	0.051 (2)	0.015 (2)
C38A	0.086 (3)	0.0608 (19)	0.074 (2)	0.0000 (19)	0.039 (2)	−0.0066 (17)
C39A	0.0575 (18)	0.0524 (16)	0.0553 (16)	−0.0015 (14)	0.0131 (14)	−0.0018 (13)
O1A	0.0511 (12)	0.0581 (12)	0.0721 (14)	−0.0056 (10)	−0.0037 (11)	−0.0215 (11)
O2A	0.0447 (11)	0.0684 (13)	0.0448 (10)	−0.0054 (10)	0.0084 (9)	−0.0113 (9)
O3A	0.0545 (12)	0.0530 (11)	0.0586 (12)	−0.0043 (10)	0.0015 (10)	−0.0169 (10)
O4A	0.110 (2)	0.0744 (16)	0.0781 (17)	−0.0002 (16)	−0.0525 (17)	−0.0017 (13)
N1B	0.0407 (11)	0.0430 (11)	0.0396 (11)	0.0020 (10)	0.0048 (9)	0.0043 (9)
C2B	0.0397 (13)	0.0442 (13)	0.0390 (12)	0.0012 (11)	0.0007 (11)	0.0015 (11)
C3B	0.0432 (14)	0.0395 (13)	0.0390 (12)	0.0005 (11)	0.0031 (11)	−0.0038 (10)
C4B	0.0445 (14)	0.0388 (12)	0.0375 (12)	−0.0005 (11)	0.0027 (11)	−0.0008 (10)
C5B	0.0399 (13)	0.0416 (12)	0.0422 (13)	0.0022 (11)	0.0031 (11)	−0.0006 (10)
C6B	0.0483 (16)	0.0486 (15)	0.0507 (15)	−0.0010 (13)	0.0046 (13)	0.0097 (12)
C7B	0.066 (2)	0.0563 (18)	0.080 (2)	−0.0134 (17)	−0.0106 (18)	0.0125 (17)
C8B	0.077 (2)	0.061 (2)	0.100 (3)	−0.0229 (19)	−0.012 (2)	0.028 (2)
C9B	0.086 (3)	0.055 (2)	0.105 (3)	−0.0069 (19)	−0.013 (2)	0.030 (2)
C10B	0.079 (2)	0.076 (2)	0.071 (2)	−0.001 (2)	−0.007 (2)	0.0282 (19)
C11B	0.0545 (17)	0.0523 (16)	0.0531 (16)	−0.0014 (14)	−0.0039 (14)	0.0102 (13)
C12B	0.0582 (18)	0.0449 (14)	0.0449 (14)	0.0018 (13)	0.0168 (14)	−0.0011 (12)
C13B	0.078 (2)	0.0494 (16)	0.0525 (17)	0.0167 (16)	0.0263 (16)	0.0097 (13)
C14B	0.071 (2)	0.084 (2)	0.072 (2)	0.029 (2)	0.021 (2)	0.0170 (19)
C15B	0.088 (3)	0.132 (4)	0.106 (3)	0.062 (3)	0.038 (3)	0.042 (3)
C16B	0.161 (6)	0.100 (4)	0.132 (5)	0.082 (4)	0.065 (5)	0.047 (4)
C17B	0.193 (7)	0.055 (2)	0.120 (4)	0.041 (4)	0.071 (5)	0.016 (2)
C18B	0.123 (4)	0.0505 (18)	0.082 (2)	0.015 (2)	0.042 (3)	0.0035 (17)
C19B	0.0500 (15)	0.0390 (12)	0.0394 (13)	−0.0016 (12)	0.0004 (12)	0.0007 (10)
C20B	0.0447 (14)	0.0416 (13)	0.0502 (14)	−0.0037 (12)	0.0015 (12)	0.0080 (12)
C21B	0.0459 (15)	0.0467 (14)	0.0503 (14)	−0.0036 (12)	0.0059 (13)	0.0066 (12)
C22B	0.0481 (15)	0.0543 (15)	0.0372 (13)	0.0017 (13)	0.0049 (12)	0.0011 (11)
C23B	0.0562 (18)	0.0485 (15)	0.0636 (18)	−0.0069 (14)	−0.0018 (15)	0.0032 (14)
C24B	0.055 (2)	0.066 (2)	0.088 (3)	−0.0140 (17)	−0.0058 (19)	0.0114 (19)
C25B	0.0469 (19)	0.082 (2)	0.088 (3)	−0.0049 (18)	0.0104 (18)	0.014 (2)
C26B	0.0528 (19)	0.069 (2)	0.067 (2)	−0.0014 (16)	0.0147 (16)	0.0083 (17)
C27B	0.0423 (14)	0.0422 (13)	0.0411 (13)	0.0027 (11)	0.0021 (11)	0.0012 (11)
C28B	0.0574 (17)	0.0376 (13)	0.0523 (15)	0.0021 (13)	−0.0062 (14)	0.0003 (11)
C29B	0.0536 (16)	0.0440 (13)	0.0475 (14)	−0.0044 (13)	−0.0058 (13)	−0.0008 (11)
C30B	0.0415 (14)	0.0484 (14)	0.0476 (14)	−0.0017 (12)	0.0001 (12)	0.0081 (12)
C31B	0.0563 (17)	0.0409 (13)	0.0552 (16)	0.0043 (13)	−0.0010 (14)	0.0056 (12)
C32B	0.0546 (17)	0.0426 (13)	0.0486 (15)	0.0005 (13)	−0.0031 (13)	−0.0023 (12)
C33B	0.081 (3)	0.072 (2)	0.086 (3)	−0.008 (2)	−0.041 (2)	0.007 (2)
C34B	0.0413 (14)	0.0459 (14)	0.0445 (13)	0.0005 (12)	0.0032 (12)	0.0069 (11)
C35B	0.0438 (16)	0.083 (2)	0.0537 (17)	−0.0022 (16)	−0.0021 (13)	0.0080 (16)
C36B	0.0428 (18)	0.121 (3)	0.086 (3)	0.009 (2)	0.0101 (18)	0.031 (3)
C37B	0.067 (2)	0.079 (2)	0.089 (3)	0.014 (2)	0.034 (2)	0.007 (2)
C38B	0.082 (3)	0.064 (2)	0.077 (2)	−0.0068 (19)	0.032 (2)	−0.0167 (18)
C39B	0.0539 (18)	0.0593 (18)	0.0603 (17)	−0.0066 (15)	0.0119 (15)	−0.0123 (15)
O1B	0.0643 (14)	0.0648 (13)	0.0597 (12)	−0.0014 (12)	0.0001 (12)	−0.0213 (11)
O2B	0.0506 (11)	0.0616 (12)	0.0482 (11)	0.0004 (10)	0.0100 (9)	−0.0051 (9)
O3B	0.0608 (13)	0.0628 (13)	0.0546 (12)	−0.0050 (11)	0.0037 (10)	−0.0177 (10)
O4B	0.0610 (13)	0.0547 (11)	0.0668 (13)	−0.0026 (11)	−0.0219 (11)	0.0105 (10)

Geometric parameters (Å, º) top

N1A—C2A	1.461 (3)	N1B—C2B	1.464 (3)
N1A—C5A	1.464 (3)	N1B—C5B	1.465 (3)
N1A—C6A	1.481 (3)	N1B—C6B	1.473 (3)
C2A—C34A	1.515 (4)	C2B—C34B	1.513 (4)
C2A—C3A	1.557 (4)	C2B—C3B	1.559 (4)
C2A—H2A	0.9800	C2B—H2B	0.9800
C3A—C27A	1.511 (4)	C3B—C27B	1.516 (4)
C3A—C4A	1.562 (4)	C3B—C4B	1.564 (4)
C3A—H3A	0.9800	C3B—H3B	0.9800
C4A—C5A	1.576 (4)	C4B—C5B	1.568 (4)
C4A—C22A	1.536 (3)	C4B—C22B	1.530 (3)
C4A—C19A	1.541 (4)	C4B—C19B	1.543 (4)
C5A—C12A	1.546 (4)	C5B—C12B	1.544 (4)
C5A—H5A	0.9800	C5B—H5B	0.9800
C6A—C7A	1.508 (5)	C6B—C7B	1.511 (4)
C6A—C11A	1.516 (4)	C6B—C11B	1.528 (4)
C6A—H6A	0.9800	C6B—H6B	0.9800
C7A—C8A	1.548 (5)	C7B—C8B	1.538 (5)
C7A—H7A1	0.9700	C7B—H7B1	0.9700
C7A—H7A2	0.9700	C7B—H7B2	0.9700
C8A—C9A	1.522 (7)	C8B—C9B	1.527 (6)
C8A—H8A1	0.9700	C8B—H8B1	0.9700
C8A—H8A2	0.9700	C8B—H8B2	0.9700
C9A—C10A	1.486 (6)	C9B—C10B	1.502 (6)
C9A—H9A1	0.9700	C9B—H9B1	0.9700
C9A—H9A2	0.9700	C9B—H9B2	0.9700
C10A—C11A	1.541 (5)	C10B—C11B	1.527 (4)
C10A—H10A	0.9700	C10B—H10C	0.9700
C10A—H10B	0.9700	C10B—H10D	0.9700
C11A—H11A	0.9700	C11B—H11C	0.9700
C11A—H11B	0.9700	C11B—H11D	0.9700
C12A—O1A	1.223 (3)	C12B—O1B	1.214 (4)
C12A—C13A	1.488 (4)	C12B—C13B	1.504 (4)
C13A—C14A	1.388 (4)	C13B—C14B	1.383 (6)
C13A—C18A	1.393 (4)	C13B—C18B	1.407 (5)
C14A—C15A	1.387 (5)	C14B—C15B	1.389 (5)
C14A—H14A	0.9300	C14B—H14B	0.9300
C15A—C16A	1.371 (6)	C15B—C16B	1.379 (10)
C15A—H15A	0.9300	C15B—H15B	0.9300
C16A—C17A	1.368 (6)	C16B—C17B	1.391 (10)
C16A—H16A	0.9300	C16B—H16B	0.9300
C17A—C18A	1.373 (5)	C17B—C18B	1.383 (7)
C17A—H17A	0.9300	C17B—H17B	0.9300
C18A—H18A	0.9300	C18B—H18B	0.9300
C19A—O3A	1.219 (3)	C19B—O3B	1.212 (3)
C19A—C20A	1.477 (4)	C19B—C20B	1.484 (4)
C20A—C21A	1.395 (4)	C20B—C21B	1.385 (4)
C20A—C23A	1.409 (4)	C20B—C23B	1.403 (4)
C21A—O2A	1.365 (3)	C21B—O2B	1.374 (4)
C21A—C26A	1.398 (4)	C21B—C26B	1.393 (4)
C22A—O2A	1.435 (3)	C22B—O2B	1.438 (4)
C22A—H22A	0.9700	C22B—H22C	0.9700
C22A—H22B	0.9700	C22B—H22D	0.9700
C23A—C24A	1.375 (5)	C23B—C24B	1.375 (5)
C23A—H23A	0.9300	C23B—H23B	0.9300
C24A—C25A	1.381 (6)	C24B—C25B	1.393 (6)
C24A—H24A	0.9300	C24B—H24B	0.9300
C25A—C26A	1.382 (5)	C25B—C26B	1.371 (5)
C25A—H25A	0.9300	C25B—H25B	0.9300
C26A—H26A	0.9300	C26B—H26B	0.9300
C27A—C28A	1.386 (4)	C27B—C28B	1.386 (4)
C27A—C32A	1.400 (4)	C27B—C32B	1.393 (4)
C28A—C29A	1.396 (4)	C28B—C29B	1.396 (4)
C28A—H28A	0.9300	C28B—H28B	0.9300
C29A—C30A	1.379 (4)	C29B—C30B	1.383 (4)
C29A—H29A	0.9300	C29B—H29B	0.9300
C30A—O4A	1.373 (4)	C30B—O4B	1.381 (3)
C30A—C31A	1.395 (4)	C30B—C31B	1.382 (4)
C31A—C32A	1.377 (4)	C31B—C32B	1.388 (4)
C31A—H31A	0.9300	C31B—H31B	0.9300
C32A—H32A	0.9300	C32B—H32B	0.9300
C33A—O4A	1.418 (5)	C33B—O4B	1.413 (4)
C33A—H33A	0.9600	C33B—H33D	0.9600
C33A—H33B	0.9600	C33B—H33E	0.9600
C33A—H33C	0.9600	C33B—H33F	0.9600
C34A—C35A	1.384 (4)	C34B—C39B	1.384 (4)
C34A—C39A	1.396 (4)	C34B—C35B	1.391 (4)
C35A—C36A	1.399 (5)	C35B—C36B	1.398 (5)
C35A—H35A	0.9300	C35B—H35B	0.9300
C36A—C37A	1.369 (6)	C36B—C37B	1.372 (6)
C36A—H36A	0.9300	C36B—H36B	0.9300
C37A—C38A	1.369 (6)	C37B—C38B	1.369 (6)
C37A—H37A	0.9300	C37B—H37B	0.9300
C38A—C39A	1.388 (5)	C38B—C39B	1.387 (5)
C38A—H38A	0.9300	C38B—H38B	0.9300
C39A—H39A	0.9300	C39B—H39B	0.9300

C2A—N1A—C5A	108.84 (19)	C2B—N1B—C5B	107.69 (19)
C2A—N1A—C6A	118.4 (2)	C2B—N1B—C6B	118.4 (2)
C5A—N1A—C6A	120.4 (2)	C5B—N1B—C6B	120.5 (2)
N1A—C2A—C34A	114.2 (2)	N1B—C2B—C34B	114.5 (2)
N1A—C2A—C3A	102.6 (2)	N1B—C2B—C3B	101.6 (2)
C34A—C2A—C3A	109.3 (2)	C34B—C2B—C3B	109.8 (2)
N1A—C2A—H2A	110.2	N1B—C2B—H2B	110.2
C34A—C2A—H2A	110.2	C34B—C2B—H2B	110.2
C3A—C2A—H2A	110.2	C3B—C2B—H2B	110.2
C27A—C3A—C2A	114.4 (2)	C27B—C3B—C2B	115.1 (2)
C27A—C3A—C4A	117.7 (2)	C27B—C3B—C4B	117.3 (2)
C2A—C3A—C4A	105.6 (2)	C2B—C3B—C4B	105.1 (2)
C27A—C3A—H3A	106.1	C27B—C3B—H3B	106.2
C2A—C3A—H3A	106.1	C2B—C3B—H3B	106.2
C4A—C3A—H3A	106.1	C4B—C3B—H3B	106.2
C22A—C4A—C19A	106.1 (2)	C22B—C4B—C19B	106.2 (2)
C22A—C4A—C3A	114.1 (2)	C22B—C4B—C3B	114.7 (2)
C19A—C4A—C3A	110.4 (2)	C19B—C4B—C3B	110.4 (2)
C22A—C4A—C5A	114.3 (2)	C22B—C4B—C5B	114.8 (2)
C19A—C4A—C5A	107.17 (19)	C19B—C4B—C5B	105.9 (2)
C3A—C4A—C5A	104.6 (2)	C3B—C4B—C5B	104.5 (2)
N1A—C5A—C12A	113.8 (2)	N1B—C5B—C12B	112.6 (2)
N1A—C5A—C4A	102.8 (2)	N1B—C5B—C4B	102.0 (2)
C12A—C5A—C4A	111.6 (2)	C12B—C5B—C4B	112.3 (2)
N1A—C5A—H5A	109.5	N1B—C5B—H5B	109.9
C12A—C5A—H5A	109.5	C12B—C5B—H5B	109.9
C4A—C5A—H5A	109.5	C4B—C5B—H5B	109.9
N1A—C6A—C7A	117.1 (3)	N1B—C6B—C7B	117.2 (3)
N1A—C6A—C11A	112.4 (2)	N1B—C6B—C11B	111.7 (2)
C7A—C6A—C11A	110.3 (3)	C7B—C6B—C11B	110.2 (3)
N1A—C6A—H6A	105.4	N1B—C6B—H6B	105.6
C7A—C6A—H6A	105.4	C7B—C6B—H6B	105.6
C11A—C6A—H6A	105.4	C11B—C6B—H6B	105.6
C6A—C7A—C8A	110.0 (3)	C6B—C7B—C8B	110.4 (3)
C6A—C7A—H7A1	109.7	C6B—C7B—H7B1	109.6
C8A—C7A—H7A1	109.7	C8B—C7B—H7B1	109.6
C6A—C7A—H7A2	109.7	C6B—C7B—H7B2	109.6
C8A—C7A—H7A2	109.7	C8B—C7B—H7B2	109.6
H7A1—C7A—H7A2	108.2	H7B1—C7B—H7B2	108.1
C9A—C8A—C7A	111.1 (4)	C9B—C8B—C7B	110.3 (3)
C9A—C8A—H8A1	109.4	C9B—C8B—H8B1	109.6
C7A—C8A—H8A1	109.4	C7B—C8B—H8B1	109.6
C9A—C8A—H8A2	109.4	C9B—C8B—H8B2	109.6
C7A—C8A—H8A2	109.4	C7B—C8B—H8B2	109.6
H8A1—C8A—H8A2	108.0	H8B1—C8B—H8B2	108.1
C10A—C9A—C8A	111.9 (4)	C10B—C9B—C8B	111.7 (3)
C10A—C9A—H9A1	109.2	C10B—C9B—H9B1	109.3
C8A—C9A—H9A1	109.2	C8B—C9B—H9B1	109.3
C10A—C9A—H9A2	109.2	C10B—C9B—H9B2	109.3
C8A—C9A—H9A2	109.2	C8B—C9B—H9B2	109.3
H9A1—C9A—H9A2	107.9	H9B1—C9B—H9B2	107.9
C9A—C10A—C11A	111.8 (4)	C9B—C10B—C11B	111.7 (3)
C9A—C10A—H10A	109.3	C9B—C10B—H10C	109.3
C11A—C10A—H10A	109.3	C11B—C10B—H10C	109.3
C9A—C10A—H10B	109.3	C9B—C10B—H10D	109.3
C11A—C10A—H10B	109.3	C11B—C10B—H10D	109.3
H10A—C10A—H10B	107.9	H10C—C10B—H10D	107.9
C6A—C11A—C10A	110.4 (3)	C10B—C11B—C6B	110.2 (3)
C6A—C11A—H11A	109.6	C10B—C11B—H11C	109.6
C10A—C11A—H11A	109.6	C6B—C11B—H11C	109.6
C6A—C11A—H11B	109.6	C10B—C11B—H11D	109.6
C10A—C11A—H11B	109.6	C6B—C11B—H11D	109.6
H11A—C11A—H11B	108.1	H11C—C11B—H11D	108.1
O1A—C12A—C13A	120.8 (2)	O1B—C12B—C13B	120.4 (3)
O1A—C12A—C5A	118.7 (2)	O1B—C12B—C5B	119.9 (3)
C13A—C12A—C5A	120.6 (2)	C13B—C12B—C5B	119.5 (3)
C14A—C13A—C18A	117.6 (3)	C14B—C13B—C18B	120.2 (4)
C14A—C13A—C12A	123.7 (2)	C14B—C13B—C12B	123.3 (3)
C18A—C13A—C12A	118.7 (3)	C18B—C13B—C12B	116.5 (4)
C15A—C14A—C13A	121.0 (3)	C13B—C14B—C15B	120.3 (5)
C15A—C14A—H14A	119.5	C13B—C14B—H14B	119.9
C13A—C14A—H14A	119.5	C15B—C14B—H14B	119.9
C16A—C15A—C14A	120.0 (4)	C16B—C15B—C14B	119.2 (6)
C16A—C15A—H15A	120.0	C16B—C15B—H15B	120.4
C14A—C15A—H15A	120.0	C14B—C15B—H15B	120.4
C17A—C16A—C15A	119.7 (3)	C15B—C16B—C17B	121.4 (5)
C17A—C16A—H16A	120.1	C15B—C16B—H16B	119.3
C15A—C16A—H16A	120.1	C17B—C16B—H16B	119.3
C16A—C17A—C18A	120.6 (3)	C18B—C17B—C16B	119.5 (5)
C16A—C17A—H17A	119.7	C18B—C17B—H17B	120.3
C18A—C17A—H17A	119.7	C16B—C17B—H17B	120.3
C17A—C18A—C13A	121.0 (4)	C17B—C18B—C13B	119.5 (5)
C17A—C18A—H18A	119.5	C17B—C18B—H18B	120.3
C13A—C18A—H18A	119.5	C13B—C18B—H18B	120.3
O3A—C19A—C20A	121.9 (2)	O3B—C19B—C20B	122.3 (3)
O3A—C19A—C4A	122.5 (2)	O3B—C19B—C4B	123.1 (3)
C20A—C19A—C4A	115.6 (2)	C20B—C19B—C4B	114.5 (2)
C21A—C20A—C23A	119.0 (3)	C21B—C20B—C23B	118.4 (3)
C21A—C20A—C19A	120.4 (3)	C21B—C20B—C19B	120.8 (3)
C23A—C20A—C19A	120.6 (3)	C23B—C20B—C19B	120.7 (3)
O2A—C21A—C20A	122.3 (3)	O2B—C21B—C20B	122.3 (3)
O2A—C21A—C26A	117.5 (3)	O2B—C21B—C26B	117.3 (3)
C20A—C21A—C26A	120.2 (3)	C20B—C21B—C26B	120.4 (3)
O2A—C22A—C4A	111.9 (2)	O2B—C22B—C4B	111.3 (2)
O2A—C22A—H22A	109.2	O2B—C22B—H22C	109.4
C4A—C22A—H22A	109.2	C4B—C22B—H22C	109.4
O2A—C22A—H22B	109.2	O2B—C22B—H22D	109.4
C4A—C22A—H22B	109.2	C4B—C22B—H22D	109.4
H22A—C22A—H22B	107.9	H22C—C22B—H22D	108.0
C24A—C23A—C20A	120.5 (3)	C24B—C23B—C20B	121.4 (3)
C24A—C23A—H23A	119.8	C24B—C23B—H23B	119.3
C20A—C23A—H23A	119.8	C20B—C23B—H23B	119.3
C23A—C24A—C25A	119.7 (3)	C23B—C24B—C25B	119.1 (3)
C23A—C24A—H24A	120.1	C23B—C24B—H24B	120.5
C25A—C24A—H24A	120.1	C25B—C24B—H24B	120.5
C24A—C25A—C26A	121.3 (3)	C26B—C25B—C24B	120.6 (3)
C24A—C25A—H25A	119.3	C26B—C25B—H25B	119.7
C26A—C25A—H25A	119.3	C24B—C25B—H25B	119.7
C25A—C26A—C21A	119.2 (4)	C25B—C26B—C21B	120.1 (3)
C25A—C26A—H26A	120.4	C25B—C26B—H26B	119.9
C21A—C26A—H26A	120.4	C21B—C26B—H26B	119.9
C28A—C27A—C32A	117.4 (2)	C28B—C27B—C32B	117.1 (3)
C28A—C27A—C3A	119.1 (2)	C28B—C27B—C3B	124.1 (2)
C32A—C27A—C3A	123.5 (2)	C32B—C27B—C3B	118.7 (2)
C27A—C28A—C29A	122.0 (3)	C27B—C28B—C29B	122.1 (3)
C27A—C28A—H28A	119.0	C27B—C28B—H28B	119.0
C29A—C28A—H28A	119.0	C29B—C28B—H28B	119.0
C30A—C29A—C28A	119.4 (3)	C30B—C29B—C28B	119.2 (3)
C30A—C29A—H29A	120.3	C30B—C29B—H29B	120.4
C28A—C29A—H29A	120.3	C28B—C29B—H29B	120.4
O4A—C30A—C29A	124.3 (3)	O4B—C30B—C31B	115.2 (2)
O4A—C30A—C31A	116.1 (3)	O4B—C30B—C29B	124.7 (3)
C29A—C30A—C31A	119.6 (3)	C31B—C30B—C29B	120.1 (3)
C32A—C31A—C30A	120.3 (3)	C30B—C31B—C32B	119.7 (3)
C32A—C31A—H31A	119.9	C30B—C31B—H31B	120.2
C30A—C31A—H31A	119.9	C32B—C31B—H31B	120.2
C31A—C32A—C27A	121.3 (3)	C31B—C32B—C27B	121.8 (3)
C31A—C32A—H32A	119.3	C31B—C32B—H32B	119.1
C27A—C32A—H32A	119.3	C27B—C32B—H32B	119.1
O4A—C33A—H33A	109.5	O4B—C33B—H33D	109.5
O4A—C33A—H33B	109.5	O4B—C33B—H33E	109.5
H33A—C33A—H33B	109.5	H33D—C33B—H33E	109.5
O4A—C33A—H33C	109.5	O4B—C33B—H33F	109.5
H33A—C33A—H33C	109.5	H33D—C33B—H33F	109.5
H33B—C33A—H33C	109.5	H33E—C33B—H33F	109.5
C35A—C34A—C39A	118.3 (3)	C39B—C34B—C35B	118.2 (3)
C35A—C34A—C2A	119.9 (3)	C39B—C34B—C2B	121.7 (3)
C39A—C34A—C2A	121.5 (3)	C35B—C34B—C2B	119.9 (3)
C34A—C35A—C36A	120.7 (3)	C34B—C35B—C36B	120.0 (3)
C34A—C35A—H35A	119.7	C34B—C35B—H35B	120.0
C36A—C35A—H35A	119.7	C36B—C35B—H35B	120.0
C37A—C36A—C35A	119.7 (4)	C37B—C36B—C35B	120.7 (4)
C37A—C36A—H36A	120.2	C37B—C36B—H36B	119.6
C35A—C36A—H36A	120.2	C35B—C36B—H36B	119.6
C38A—C37A—C36A	120.6 (3)	C38B—C37B—C36B	119.5 (3)
C38A—C37A—H37A	119.7	C38B—C37B—H37B	120.3
C36A—C37A—H37A	119.7	C36B—C37B—H37B	120.3
C37A—C38A—C39A	120.0 (4)	C37B—C38B—C39B	120.4 (4)
C37A—C38A—H38A	120.0	C37B—C38B—H38B	119.8
C39A—C38A—H38A	120.0	C39B—C38B—H38B	119.8
C38A—C39A—C34A	120.6 (3)	C34B—C39B—C38B	121.1 (3)
C38A—C39A—H39A	119.7	C34B—C39B—H39B	119.4
C34A—C39A—H39A	119.7	C38B—C39B—H39B	119.4
C21A—O2A—C22A	114.4 (2)	C21B—O2B—C22B	114.2 (2)
C30A—O4A—C33A	117.0 (3)	C30B—O4B—C33B	118.3 (2)

C5A—N1A—C2A—C34A	158.0 (2)	C5B—N1B—C2B—C34B	−162.0 (2)
C6A—N1A—C2A—C34A	−59.6 (3)	C6B—N1B—C2B—C34B	57.0 (3)
C5A—N1A—C2A—C3A	39.9 (2)	C5B—N1B—C2B—C3B	−43.7 (2)
C6A—N1A—C2A—C3A	−177.7 (2)	C6B—N1B—C2B—C3B	175.3 (2)
N1A—C2A—C3A—C27A	−155.1 (2)	N1B—C2B—C3B—C27B	156.8 (2)
C34A—C2A—C3A—C27A	83.3 (3)	C34B—C2B—C3B—C27B	−81.6 (3)
N1A—C2A—C3A—C4A	−24.0 (2)	N1B—C2B—C3B—C4B	26.2 (2)
C34A—C2A—C3A—C4A	−145.6 (2)	C34B—C2B—C3B—C4B	147.8 (2)
C27A—C3A—C4A—C22A	5.4 (3)	C27B—C3B—C4B—C22B	−4.5 (3)
C2A—C3A—C4A—C22A	−123.7 (2)	C2B—C3B—C4B—C22B	124.8 (2)
C27A—C3A—C4A—C19A	−114.0 (2)	C27B—C3B—C4B—C19B	115.4 (2)
C2A—C3A—C4A—C19A	116.9 (2)	C2B—C3B—C4B—C19B	−115.3 (2)
C27A—C3A—C4A—C5A	131.0 (2)	C27B—C3B—C4B—C5B	−131.1 (2)
C2A—C3A—C4A—C5A	1.9 (3)	C2B—C3B—C4B—C5B	−1.8 (2)
C2A—N1A—C5A—C12A	82.1 (3)	C2B—N1B—C5B—C12B	−78.0 (3)
C6A—N1A—C5A—C12A	−59.4 (3)	C6B—N1B—C5B—C12B	62.1 (3)
C2A—N1A—C5A—C4A	−38.7 (2)	C2B—N1B—C5B—C4B	42.6 (3)
C6A—N1A—C5A—C4A	179.8 (2)	C6B—N1B—C5B—C4B	−177.4 (2)
C22A—C4A—C5A—N1A	146.4 (2)	C22B—C4B—C5B—N1B	−149.7 (2)
C19A—C4A—C5A—N1A	−96.3 (2)	C19B—C4B—C5B—N1B	93.5 (2)
C3A—C4A—C5A—N1A	20.9 (2)	C3B—C4B—C5B—N1B	−23.2 (2)
C22A—C4A—C5A—C12A	24.1 (3)	C22B—C4B—C5B—C12B	−28.9 (3)
C19A—C4A—C5A—C12A	141.4 (2)	C19B—C4B—C5B—C12B	−145.7 (2)
C3A—C4A—C5A—C12A	−101.4 (2)	C3B—C4B—C5B—C12B	97.6 (2)
C2A—N1A—C6A—C7A	−46.9 (4)	C2B—N1B—C6B—C7B	50.5 (4)
C5A—N1A—C6A—C7A	91.0 (4)	C5B—N1B—C6B—C7B	−85.5 (3)
C2A—N1A—C6A—C11A	−176.1 (2)	C2B—N1B—C6B—C11B	179.0 (2)
C5A—N1A—C6A—C11A	−38.1 (3)	C5B—N1B—C6B—C11B	43.1 (3)
N1A—C6A—C7A—C8A	171.2 (4)	N1B—C6B—C7B—C8B	−171.8 (3)
C11A—C6A—C7A—C8A	−58.6 (5)	C11B—C6B—C7B—C8B	58.9 (4)
C6A—C7A—C8A—C9A	56.2 (6)	C6B—C7B—C8B—C9B	−56.9 (5)
C7A—C8A—C9A—C10A	−54.1 (6)	C7B—C8B—C9B—C10B	54.8 (5)
C8A—C9A—C10A—C11A	54.0 (6)	C8B—C9B—C10B—C11B	−54.9 (5)
N1A—C6A—C11A—C10A	−169.1 (3)	C9B—C10B—C11B—C6B	56.2 (4)
C7A—C6A—C11A—C10A	58.3 (4)	N1B—C6B—C11B—C10B	169.6 (3)
C9A—C10A—C11A—C6A	−56.0 (5)	C7B—C6B—C11B—C10B	−58.2 (4)
N1A—C5A—C12A—O1A	−50.9 (3)	N1B—C5B—C12B—O1B	58.3 (3)
C4A—C5A—C12A—O1A	64.8 (3)	C4B—C5B—C12B—O1B	−56.2 (3)
N1A—C5A—C12A—C13A	128.7 (3)	N1B—C5B—C12B—C13B	−117.6 (3)
C4A—C5A—C12A—C13A	−115.6 (3)	C4B—C5B—C12B—C13B	127.9 (3)
O1A—C12A—C13A—C14A	−168.6 (3)	O1B—C12B—C13B—C14B	158.9 (3)
C5A—C12A—C13A—C14A	11.8 (4)	C5B—C12B—C13B—C14B	−25.2 (4)
O1A—C12A—C13A—C18A	9.6 (4)	O1B—C12B—C13B—C18B	−19.6 (4)
C5A—C12A—C13A—C18A	−170.0 (3)	C5B—C12B—C13B—C18B	156.3 (3)
C18A—C13A—C14A—C15A	0.7 (5)	C18B—C13B—C14B—C15B	0.3 (6)
C12A—C13A—C14A—C15A	178.8 (3)	C12B—C13B—C14B—C15B	−178.2 (3)
C13A—C14A—C15A—C16A	0.1 (6)	C13B—C14B—C15B—C16B	−2.0 (7)
C14A—C15A—C16A—C17A	−0.6 (6)	C14B—C15B—C16B—C17B	2.7 (8)
C15A—C16A—C17A—C18A	0.3 (7)	C15B—C16B—C17B—C18B	−1.6 (9)
C16A—C17A—C18A—C13A	0.6 (7)	C16B—C17B—C18B—C13B	−0.2 (7)
C14A—C13A—C18A—C17A	−1.0 (5)	C14B—C13B—C18B—C17B	0.8 (6)
C12A—C13A—C18A—C17A	−179.3 (4)	C12B—C13B—C18B—C17B	179.4 (4)
C22A—C4A—C19A—O3A	−145.9 (3)	C22B—C4B—C19B—O3B	145.7 (3)
C3A—C4A—C19A—O3A	−21.8 (3)	C3B—C4B—C19B—O3B	20.7 (4)
C5A—C4A—C19A—O3A	91.6 (3)	C5B—C4B—C19B—O3B	−91.9 (3)
C22A—C4A—C19A—C20A	35.0 (3)	C22B—C4B—C19B—C20B	−37.8 (3)
C3A—C4A—C19A—C20A	159.1 (2)	C3B—C4B—C19B—C20B	−162.7 (2)
C5A—C4A—C19A—C20A	−87.5 (3)	C5B—C4B—C19B—C20B	84.7 (3)
O3A—C19A—C20A—C21A	176.2 (3)	O3B—C19B—C20B—C21B	−176.1 (3)
C4A—C19A—C20A—C21A	−4.7 (4)	C4B—C19B—C20B—C21B	7.3 (4)
O3A—C19A—C20A—C23A	−6.1 (4)	O3B—C19B—C20B—C23B	6.5 (4)
C4A—C19A—C20A—C23A	173.0 (3)	C4B—C19B—C20B—C23B	−170.1 (2)
C23A—C20A—C21A—O2A	177.4 (3)	C23B—C20B—C21B—O2B	−179.1 (3)
C19A—C20A—C21A—O2A	−4.8 (4)	C19B—C20B—C21B—O2B	3.4 (4)
C23A—C20A—C21A—C26A	−2.6 (4)	C23B—C20B—C21B—C26B	2.0 (4)
C19A—C20A—C21A—C26A	175.2 (3)	C19B—C20B—C21B—C26B	−175.5 (3)
C19A—C4A—C22A—O2A	−60.5 (3)	C19B—C4B—C22B—O2B	62.4 (3)
C3A—C4A—C22A—O2A	177.7 (2)	C3B—C4B—C22B—O2B	−175.3 (2)
C5A—C4A—C22A—O2A	57.4 (3)	C5B—C4B—C22B—O2B	−54.2 (3)
C21A—C20A—C23A—C24A	2.2 (5)	C21B—C20B—C23B—C24B	−1.6 (5)
C19A—C20A—C23A—C24A	−175.6 (3)	C19B—C20B—C23B—C24B	175.8 (3)
C20A—C23A—C24A—C25A	−0.2 (6)	C20B—C23B—C24B—C25B	0.5 (5)
C23A—C24A—C25A—C26A	−1.6 (6)	C23B—C24B—C25B—C26B	0.3 (6)
C24A—C25A—C26A—C21A	1.2 (6)	C24B—C25B—C26B—C21B	0.1 (6)
O2A—C21A—C26A—C25A	−179.1 (3)	O2B—C21B—C26B—C25B	179.8 (3)
C20A—C21A—C26A—C25A	0.9 (5)	C20B—C21B—C26B—C25B	−1.2 (5)
C2A—C3A—C27A—C28A	−125.9 (3)	C2B—C3B—C27B—C28B	−45.8 (4)
C4A—C3A—C27A—C28A	109.2 (3)	C4B—C3B—C27B—C28B	78.6 (4)
C2A—C3A—C27A—C32A	52.4 (3)	C2B—C3B—C27B—C32B	133.4 (3)
C4A—C3A—C27A—C32A	−72.5 (3)	C4B—C3B—C27B—C32B	−102.1 (3)
C32A—C27A—C28A—C29A	0.8 (4)	C32B—C27B—C28B—C29B	0.0 (5)
C3A—C27A—C28A—C29A	179.2 (3)	C3B—C27B—C28B—C29B	179.2 (3)
C27A—C28A—C29A—C30A	0.4 (5)	C27B—C28B—C29B—C30B	0.6 (5)
C28A—C29A—C30A—O4A	178.6 (3)	C28B—C29B—C30B—O4B	178.0 (3)
C28A—C29A—C30A—C31A	−1.1 (5)	C28B—C29B—C30B—C31B	−1.0 (5)
O4A—C30A—C31A—C32A	−179.2 (3)	O4B—C30B—C31B—C32B	−178.3 (3)
C29A—C30A—C31A—C32A	0.5 (5)	C29B—C30B—C31B—C32B	0.8 (5)
C30A—C31A—C32A—C27A	0.8 (5)	C30B—C31B—C32B—C27B	−0.2 (5)
C28A—C27A—C32A—C31A	−1.4 (4)	C28B—C27B—C32B—C31B	−0.2 (5)
C3A—C27A—C32A—C31A	−179.7 (3)	C3B—C27B—C32B—C31B	−179.5 (3)
N1A—C2A—C34A—C35A	153.2 (3)	N1B—C2B—C34B—C39B	38.7 (4)
C3A—C2A—C34A—C35A	−92.6 (3)	C3B—C2B—C34B—C39B	−74.9 (3)
N1A—C2A—C34A—C39A	−33.7 (4)	N1B—C2B—C34B—C35B	−147.0 (3)
C3A—C2A—C34A—C39A	80.5 (3)	C3B—C2B—C34B—C35B	99.5 (3)
C39A—C34A—C35A—C36A	−1.4 (5)	C39B—C34B—C35B—C36B	2.6 (5)
C2A—C34A—C35A—C36A	171.9 (3)	C2B—C34B—C35B—C36B	−172.0 (3)
C34A—C35A—C36A—C37A	0.9 (6)	C34B—C35B—C36B—C37B	−2.8 (6)
C35A—C36A—C37A—C38A	0.8 (6)	C35B—C36B—C37B—C38B	0.6 (7)
C36A—C37A—C38A—C39A	−1.8 (6)	C36B—C37B—C38B—C39B	1.7 (6)
C37A—C38A—C39A—C34A	1.3 (5)	C35B—C34B—C39B—C38B	−0.4 (5)
C35A—C34A—C39A—C38A	0.3 (5)	C2B—C34B—C39B—C38B	174.1 (3)
C2A—C34A—C39A—C38A	−172.8 (3)	C37B—C38B—C39B—C34B	−1.8 (6)
C20A—C21A—O2A—C22A	−20.7 (4)	C20B—C21B—O2B—C22B	20.9 (4)
C26A—C21A—O2A—C22A	159.3 (3)	C26B—C21B—O2B—C22B	−160.1 (3)
C4A—C22A—O2A—C21A	55.1 (3)	C4B—C22B—O2B—C21B	−55.4 (3)
C29A—C30A—O4A—C33A	5.1 (6)	C31B—C30B—O4B—C33B	−171.9 (3)
C31A—C30A—O4A—C33A	−175.3 (4)	C29B—C30B—O4B—C33B	9.0 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3A—H3A···O3A	0.98	2.26	2.813 (3)	115
C3B—H3B···O3B	0.98	2.27	2.822 (3)	114
C2A—H2A···O1A	0.98	2.49	3.028 (3)	114
C2B—H2B···O1B	0.98	2.39	2.969 (3)	118
C22A—H22B···O1A	0.97	2.53	3.120 (4)	119
C22B—H22C···O1B	0.97	2.52	3.089 (4)	118
C26A—H26A···O1Bⁱ	0.93	2.59	3.310 (4)	134

Symmetry code: (i) x−1, y, z.

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