##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2006-10-02
_journal_date_accepted     2006-10-16
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue     11
_journal_page_first     o5132
_journal_page_last     o5133
_journal_paper_category     EO
_journal_coeditor_code     OB2085
_publ_contact_author_name     'Prof. Jun Lin'
_publ_contact_author_address
;School of Chemical Science and Engineering,
Key Laboratory of Medicinal Chemistry
for Natural Resource (Ministry of Education),
Yunnan University,
Kunming 650091,
People's Republic of China
;
_publ_contact_author_email     linjun@ynu.edu.cn
_publ_contact_author_fax     '+86 871 5033922'
_publ_contact_author_phone     '+86 871 5033215'
_publ_section_title
;\
(3'S,4R)-3-(3'-Cyclopentyl-3'-phenylpropanoyl)-5,5-dimethyl-4-\
phenyl-1,3- oxazolidin-2-one
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Lei Nie' .
;School of Chemical Science and Engineering,
Key Laboratory of Medicinal Chemistry for Natural Resources
(Ministry of Education),
Yunnan University,
Kunming 650091,
People's Republic of China
;
    'Rui Yang' .
;School of Chemical Science and Engineering,
Key Laboratory of Medicinal Chemistry for Natural Resources
(Ministry of Education),
Yunnan University,
Kunming 650091,
People's Republic of China
;
    'Jing Cheng' .
;School of Chemical Science and Engineering,
Key Laboratory of Medicinal Chemistry for Natural Resources
(Ministry of Education),
Yunnan University,
Kunming 650091,
People's Republic of China
;
    'Sheng-Jiao Yan' .
;School of Chemical Science and Engineering,
Key Laboratory of Medicinal Chemistry for Natural Resources
(Ministry of Education),
Yunnan University,
Kunming 650091,
People's Republic of China
;
    'Jun Lin' .
;
State Key Laboratory of Elemento-organic Chemistry
Nankai University
Tianjin
People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(3'S,4R)-3-(3'-Cyclopentyl-3'-phenylpropanoyl)-5,5-dimethyl-4-phenyl-1,3-
oxazolidin-2-one
;
_chemical_name_common
;
;
_chemical_formula_moiety     'C25 H29 N O3'
_chemical_formula_sum     'C25 H29 N O3'
_chemical_formula_iupac     'C25 H29 N O3'
_chemical_formula_weight     391.49
_chemical_melting_point     384
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
_symmetry_space_group_name_Hall     'P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
_cell_length_a     10.2911(2)
_cell_length_b     14.0805(3)
_cell_length_c     15.6118(3)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     2262.21(8)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5993
_cell_measurement_theta_min     1.95
_cell_measurement_theta_max     28.24
_cell_measurement_temperature     273(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.31
_exptl_crystal_size_mid     0.25
_exptl_crystal_size_min     0.19
_exptl_crystal_density_diffrn     1.149
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     840
_exptl_absorpt_coefficient_mu     0.075
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 1998)'
_exptl_absorpt_correction_T_min     0.971
_exptl_absorpt_correction_T_max     0.979
_exptl_special_details
;
Spectroscopic analysis:
¹H NMR (CDCl₃, δ, p.p.m.): 7.37--6.00 (8H, m, Ar), 5.01
(s, 1H, PhCH--), 3.49--3.44 (q, 1H), 3.23--3.13 (m, 2H), 1.61 (s, 3H),
1.67--1.64 (m, 2H), 0.97 (s, 3H), 0.82--0.79 (t, 3H); ¹³C NMR (CDCl₃,
δ, p.p.m.): 172.4, 158.0, 154.1, 141.85--106.20 (Ar), 83.3, 68.0, 40.4,
37.4, 29.8, 28.1, 24.5, 12.4; ESI-MS for C₂₅H₂₉O₃N, Calcd.
414(M+Na⁺); Found: 414(M+Na⁺).
;
_diffrn_ambient_temperature     273(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEX-2 CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     20251
_diffrn_reflns_av_R_equivalents     0.0249
_diffrn_reflns_av_sigmaI/netI     0.0167
_diffrn_reflns_theta_min     1.95
_diffrn_reflns_theta_max     28.24
_diffrn_reflns_theta_full     27.50
_diffrn_measured_fraction_theta_max     0.977
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -18
_diffrn_reflns_limit_k_max     18
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     20
_diffrn_standards_number     .
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_refine_special_details
;
 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 > 2sigma(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.
;
_reflns_number_total     3070
_reflns_number_gt     2359
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0579
_refine_ls_R_factor_gt     0.0412
_refine_ls_wR_factor_gt     0.1088
_refine_ls_wR_factor_ref     0.1206
_refine_ls_goodness_of_fit_ref     1.013
_refine_ls_restrained_S_all     1.035
_refine_ls_number_reflns     3070
_refine_ls_number_parameters     275
_refine_ls_number_restraints     17
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0654P)²+0.1915P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.200
_refine_diff_density_min     -0.190
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef     0.043(6)
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 1998)'
_computing_cell_refinement     'SAINT (Bruker, 1998)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 1998)'
_computing_publication_material     'SHELXTL'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.44076(19) 0.93655(14) 0.04012(15) 0.0901(6) Uani d . 1 . .
    O O2 0.37297(16) 0.79593(12) -0.00837(12) 0.0718(5) Uani d . 1 . .
    O O3 0.06448(18) 0.92985(11) 0.14736(11) 0.0714(5) Uani d . 1 . .
    N N1 0.23632(17) 0.87519(12) 0.07545(12) 0.0546(4) Uani d . 1 . .
    C C1 0.3578(2) 0.87749(18) 0.03624(17) 0.0657(6) Uani d . 1 . .
    C C2 0.2493(2) 0.74262(18) -0.01161(15) 0.0623(6) Uani d . 1 . .
    C C3 0.1803(2) 0.77892(14) 0.06982(13) 0.0519(5) Uani d . 1 . .
    H H3A 0.0867 0.7837 0.0588 0.062 Uiso calc R 1 . .
    C C4 0.2836(3) 0.63844(19) -0.01243(19) 0.0784(7) Uani d . 1 . .
    H H4A 0.3256 0.6230 -0.0656 0.118 Uiso calc R 1 . .
    H H4B 0.2059 0.6013 -0.0066 0.118 Uiso calc R 1 . .
    H H4C 0.3413 0.6247 0.0343 0.118 Uiso calc R 1 . .
    C C5 0.1764(3) 0.7738(3) -0.09173(17) 0.0897(9) Uani d . 1 . .
    H H5A 0.2210 0.7507 -0.1416 0.135 Uiso calc R 1 . .
    H H5B 0.1725 0.8418 -0.0936 0.135 Uiso calc R 1 . .
    H H5C 0.0899 0.7484 -0.0905 0.135 Uiso calc R 1 . .
    C C6 0.2025(2) 0.72197(15) 0.15048(13) 0.0555(5) Uani d . 1 . .
    C C7 0.1146(3) 0.65228(16) 0.17310(17) 0.0698(7) Uani d . 1 . .
    H H7A 0.0411 0.6422 0.1396 0.084 Uiso calc R 1 . .
    C C8 0.1352(4) 0.59704(19) 0.2456(2) 0.0893(10) Uani d . 1 . .
    H H8A 0.0756 0.5500 0.2600 0.107 Uiso calc R 1 . .
    C C9 0.2415(5) 0.6110(2) 0.29565(19) 0.1001(11) Uani d . 1 . .
    H H9A 0.2543 0.5739 0.3442 0.120 Uiso calc R 1 . .
    C C10 0.3300(4) 0.6801(3) 0.27416(18) 0.0986(10) Uani d . 1 . .
    H H10A 0.4029 0.6895 0.3083 0.118 Uiso calc R 1 . .
    C C11 0.3112(3) 0.7359(2) 0.20190(16) 0.0756(7) Uani d . 1 . .
    H H11A 0.3714 0.7826 0.1879 0.091 Uiso calc R 1 . .
    C C12 0.1689(2) 0.94840(15) 0.11507(13) 0.0542(5) Uani d . 1 . .
    C C13 0.2230(3) 1.04713(15) 0.11489(14) 0.0613(6) Uani d . 1 B .
    H H13A 0.3062 1.0474 0.0857 0.074 Uiso calc R 1 . .
    H H13B 0.2369 1.0679 0.1734 0.074 Uiso calc R 1 . .
    C C14 0.1294(2) 1.11633(14) 0.06963(13) 0.0530(5) Uani d . 1 . .
    H H14A 0.0448 1.1112 0.0981 0.064 Uiso calc R 1 A 1
    C C15 0.1107(2) 1.08751(15) -0.02319(13) 0.0532(5) Uani d . 1 B .
    C C16 -0.0090(3) 1.0616(2) -0.05399(16) 0.0715(7) Uani d . 1 . .
    H H16A -0.0805 1.0625 -0.0176 0.086 Uiso calc R 1 B .
    C C17 -0.0251(3) 1.0341(3) -0.13893(19) 0.0907(9) Uani d . 1 B .
    H H17A -0.1069 1.0166 -0.1587 0.109 Uiso calc R 1 . .
    C C18 0.0779(4) 1.0325(2) -0.19304(17) 0.0877(9) Uani d . 1 . .
    H H18A 0.0669 1.0141 -0.2498 0.105 Uiso calc R 1 B .
    C C19 0.1976(3) 1.0580(2) -0.16365(16) 0.0868(9) Uani d . 1 B .
    H H19A 0.2683 1.0575 -0.2007 0.104 Uiso calc R 1 . .
    C C20 0.2145(3) 1.0845(2) -0.07952(16) 0.0739(7) Uani d . 1 . .
    H H20A 0.2971 1.1007 -0.0602 0.089 Uiso calc R 1 B .
    C C21 0.1760(3) 1.21898(14) 0.07973(14) 0.0623(6) Uani d PD 0.196(11) B 1
    H H21B 0.2703 1.2188 0.0713 0.075 Uiso calc PR 0.196(11) B 1
    C C22 0.151(3) 1.2576(15) 0.1696(6) 0.0766(13) Uani d PD 0.196(11) B 1
    H H22A 0.2300 1.2823 0.1946 0.092 Uiso calc PR 0.196(11) B 1
    H H22B 0.1166 1.2082 0.2066 0.092 Uiso calc PR 0.196(11) B 1
    C C23 0.051(3) 1.3370(13) 0.1578(13) 0.110(2) Uani d PD 0.196(11) B 1
    H H23A -0.0371 1.3123 0.1627 0.132 Uiso calc PR 0.196(11) B 1
    H H23B 0.0627 1.3864 0.2004 0.132 Uiso calc PR 0.196(11) B 1
    C C24 0.075(3) 1.3752(10) 0.0682(13) 0.1048(17) Uani d PD 0.196(11) B 1
    H H24A -0.0035 1.4017 0.0439 0.126 Uiso calc PR 0.196(11) B 1
    H H24B 0.1419 1.4240 0.0691 0.126 Uiso calc PR 0.196(11) B 1
    C C25 0.120(3) 1.2897(12) 0.0173(8) 0.0820(13) Uani d PD 0.196(11) B 1
    H H25A 0.0475 1.2619 -0.0133 0.098 Uiso calc PR 0.196(11) B 1
    H H25B 0.1856 1.3084 -0.0241 0.098 Uiso calc PR 0.196(11) B 1
    C C21' 0.1760(3) 1.21898(14) 0.07973(14) 0.0623(6) Uani d PD 0.804(11) B 2
    H H21A 0.2594 1.2263 0.0501 0.075 Uiso calc PR 0.804(11) B 2
    C C22' 0.1923(6) 1.2500(4) 0.1744(2) 0.0766(13) Uani d PD 0.804(11) B 2
    H H22C 0.1481 1.2059 0.2122 0.092 Uiso calc PR 0.804(11) B 2
    H H22D 0.2836 1.2518 0.1898 0.092 Uiso calc PR 0.804(11) B 2
    C C23' 0.1331(9) 1.3477(3) 0.1814(3) 0.110(2) Uani d PD 0.804(11) B 2
    H H23C 0.0542 1.3452 0.2154 0.132 Uiso calc PR 0.804(11) B 2
    H H23D 0.1935 1.3908 0.2090 0.132 Uiso calc PR 0.804(11) B 2
    C C24' 0.1033(6) 1.3812(3) 0.0940(4) 0.1048(17) Uani d PD 0.804(11) B 2
    H H24C 0.1763 1.4160 0.0704 0.126 Uiso calc PR 0.804(11) B 2
    H H24D 0.0277 1.4224 0.0944 0.126 Uiso calc PR 0.804(11) B 2
    C C25' 0.0769(5) 1.2923(3) 0.0422(4) 0.0820(13) Uani d PD 0.804(11) B 2
    H H25C 0.0925 1.3032 -0.0183 0.098 Uiso calc PR 0.804(11) B 2
    H H25D -0.0119 1.2708 0.0500 0.098 Uiso calc PR 0.804(11) B 2
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C1 . 1.193(3) ?
    O2 C1 . 1.352(3) ?
    O2 C2 . 1.478(3) ?
    O3 C12 . 1.215(3) ?
    N1 C12 . 1.388(3) ?
    N1 C1 . 1.393(3) ?
    N1 C3 . 1.476(3) ?
    C2 C4 . 1.509(4) ?
    C2 C5 . 1.523(4) ?
    C2 C3 . 1.544(3) ?
    C3 C6 . 1.510(3) ?
    C3 H3A . 0.9800 ?
    C4 H4A . 0.9600 ?
    C4 H4B . 0.9600 ?
    C4 H4C . 0.9600 ?
    C5 H5A . 0.9600 ?
    C5 H5B . 0.9600 ?
    C5 H5C . 0.9600 ?
    C6 C7 . 1.380(3) ?
    C6 C11 . 1.391(4) ?
    C7 C8 . 1.390(4) ?
    C7 H7A . 0.9300 ?
    C8 C9 . 1.358(5) ?
    C8 H8A . 0.9300 ?
    C9 C10 . 1.375(5) ?
    C9 H9A . 0.9300 ?
    C10 C11 . 1.388(4) ?
    C10 H10A . 0.9300 ?
    C11 H11A . 0.9300 ?
    C12 C13 . 1.497(3) ?
    C13 C14 . 1.541(3) ?
    C13 H13A . 0.9700 ?
    C13 H13B . 0.9700 ?
    C14 C15 . 1.517(3) ?
    C14 C21 . 1.531(3) ?
    C14 H14A . 0.9800 ?
    C15 C16 . 1.372(3) ?
    C15 C20 . 1.384(3) ?
    C16 C17 . 1.392(4) ?
    C16 H16A . 0.9300 ?
    C17 C18 . 1.355(4) ?
    C17 H17A . 0.9300 ?
    C18 C19 . 1.362(5) ?
    C18 H18A . 0.9300 ?
    C19 C20 . 1.377(4) ?
    C19 H19A . 0.9300 ?
    C20 H20A . 0.9300 ?
    C21 C25 . 1.507(8) ?
    C21 C22 . 1.527(9) ?
    C21 H21B . 0.9800 ?
    C22 C23 . 1.531(9) ?
    C22 H22A . 0.9700 ?
    C22 H22B . 0.9700 ?
    C23 C24 . 1.521(10) ?
    C23 H23A . 0.9700 ?
    C23 H23B . 0.9700 ?
    C24 C25 . 1.514(9) ?
    C24 H24A . 0.9700 ?
    C24 H24B . 0.9700 ?
    C25 H25A . 0.9700 ?
    C25 H25B . 0.9700 ?
    C22' C23' . 1.509(6) ?
    C22' H22C . 0.9700 ?
    C22' H22D . 0.9700 ?
    C23' C24' . 1.475(7) ?
    C23' H23C . 0.9700 ?
    C23' H23D . 0.9700 ?
    C24' C25' . 1.515(6) ?
    C24' H24C . 0.9700 ?
    C24' H24D . 0.9700 ?
    C25' H25C . 0.9700 ?
    C25' H25D . 0.9700 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C1 O2 C2 . . 110.48(17) ?
    C12 N1 C1 . . 128.9(2) ?
    C12 N1 C3 . . 120.87(17) ?
    C1 N1 C3 . . 110.26(18) ?
    O1 C1 O2 . . 122.4(2) ?
    O1 C1 N1 . . 129.5(2) ?
    O2 C1 N1 . . 108.1(2) ?
    O2 C2 C4 . . 107.0(2) ?
    O2 C2 C5 . . 107.8(2) ?
    C4 C2 C5 . . 112.8(2) ?
    O2 C2 C3 . . 101.54(17) ?
    C4 C2 C3 . . 115.9(2) ?
    C5 C2 C3 . . 110.7(2) ?
    N1 C3 C6 . . 112.27(18) ?
    N1 C3 C2 . . 99.97(17) ?
    C6 C3 C2 . . 116.19(17) ?
    N1 C3 H3A . . 109.3 ?
    C6 C3 H3A . . 109.3 ?
    C2 C3 H3A . . 109.3 ?
    C2 C4 H4A . . 109.5 ?
    C2 C4 H4B . . 109.5 ?
    H4A C4 H4B . . 109.5 ?
    C2 C4 H4C . . 109.5 ?
    H4A C4 H4C . . 109.5 ?
    H4B C4 H4C . . 109.5 ?
    C2 C5 H5A . . 109.5 ?
    C2 C5 H5B . . 109.5 ?
    H5A C5 H5B . . 109.5 ?
    C2 C5 H5C . . 109.5 ?
    H5A C5 H5C . . 109.5 ?
    H5B C5 H5C . . 109.5 ?
    C7 C6 C11 . . 118.7(2) ?
    C7 C6 C3 . . 119.4(2) ?
    C11 C6 C3 . . 121.9(2) ?
    C6 C7 C8 . . 120.4(3) ?
    C6 C7 H7A . . 119.8 ?
    C8 C7 H7A . . 119.8 ?
    C9 C8 C7 . . 120.7(3) ?
    C9 C8 H8A . . 119.6 ?
    C7 C8 H8A . . 119.6 ?
    C8 C9 C10 . . 119.7(3) ?
    C8 C9 H9A . . 120.2 ?
    C10 C9 H9A . . 120.2 ?
    C9 C10 C11 . . 120.5(3) ?
    C9 C10 H10A . . 119.8 ?
    C11 C10 H10A . . 119.8 ?
    C10 C11 C6 . . 120.1(3) ?
    C10 C11 H11A . . 120.0 ?
    C6 C11 H11A . . 120.0 ?
    O3 C12 N1 . . 117.9(2) ?
    O3 C12 C13 . . 121.9(2) ?
    N1 C12 C13 . . 120.2(2) ?
    C12 C13 C14 . . 110.8(2) ?
    C12 C13 H13A . . 109.5 ?
    C14 C13 H13A . . 109.5 ?
    C12 C13 H13B . . 109.5 ?
    C14 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 108.1 ?
    C15 C14 C21 . . 112.99(17) ?
    C15 C14 C13 . . 110.38(18) ?
    C21 C14 C13 . . 110.76(19) ?
    C15 C14 H14A . . 107.5 ?
    C21 C14 H14A . . 107.5 ?
    C13 C14 H14A . . 107.5 ?
    C16 C15 C20 . . 117.5(2) ?
    C16 C15 C14 . . 121.3(2) ?
    C20 C15 C14 . . 121.1(2) ?
    C15 C16 C17 . . 121.0(3) ?
    C15 C16 H16A . . 119.5 ?
    C17 C16 H16A . . 119.5 ?
    C18 C17 C16 . . 120.4(3) ?
    C18 C17 H17A . . 119.8 ?
    C16 C17 H17A . . 119.8 ?
    C17 C18 C19 . . 119.5(2) ?
    C17 C18 H18A . . 120.2 ?
    C19 C18 H18A . . 120.2 ?
    C18 C19 C20 . . 120.5(3) ?
    C18 C19 H19A . . 119.8 ?
    C20 C19 H19A . . 119.8 ?
    C19 C20 C15 . . 121.1(3) ?
    C19 C20 H20A . . 119.4 ?
    C15 C20 H20A . . 119.4 ?
    C25 C21 C22 . . 107.0(5) ?
    C25 C21 C14 . . 116.0(9) ?
    C22 C21 C14 . . 112.2(11) ?
    C25 C21 H21B . . 107.1 ?
    C22 C21 H21B . . 107.1 ?
    C14 C21 H21B . . 107.1 ?
    C21 C22 C23 . . 105.4(6) ?
    C21 C22 H22A . . 110.7 ?
    C23 C22 H22A . . 110.7 ?
    C21 C22 H22B . . 110.7 ?
    C23 C22 H22B . . 110.7 ?
    H22A C22 H22B . . 108.8 ?
    C24 C23 C22 . . 104.8(7) ?
    C24 C23 H23A . . 110.8 ?
    C22 C23 H23A . . 110.8 ?
    C24 C23 H23B . . 110.8 ?
    C22 C23 H23B . . 110.8 ?
    H23A C23 H23B . . 108.9 ?
    C25 C24 C23 . . 104.6(7) ?
    C25 C24 H24A . . 110.8 ?
    C23 C24 H24A . . 110.8 ?
    C25 C24 H24B . . 110.8 ?
    C23 C24 H24B . . 110.8 ?
    H24A C24 H24B . . 108.9 ?
    C21 C25 C24 . . 107.6(6) ?
    C21 C25 H25A . . 110.2 ?
    C24 C25 H25A . . 110.2 ?
    C21 C25 H25B . . 110.2 ?
    C24 C25 H25B . . 110.2 ?
    H25A C25 H25B . . 108.5 ?
    C23' C22' H22C . . 110.5 ?
    C23' C22' H22D . . 110.5 ?
    H22C C22' H22D . . 108.6 ?
    C24' C23' C22' . . 108.0(3) ?
    C24' C23' H23C . . 110.1 ?
    C22' C23' H23C . . 110.1 ?
    C24' C23' H23D . . 110.1 ?
    C22' C23' H23D . . 110.1 ?
    H23C C23' H23D . . 108.4 ?
    C23' C24' C25' . . 105.5(3) ?
    C23' C24' H24C . . 110.6 ?
    C25' C24' H24C . . 110.6 ?
    C23' C24' H24D . . 110.6 ?
    C25' C24' H24D . . 110.6 ?
    H24C C24' H24D . . 108.8 ?
    C24' C25' H25C . . 111.1 ?
    C24' C25' H25D . . 111.1 ?
    H25C C25' H25D . . 109.1 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C2 O2 C1 O1 . . . . -172.3(2) ?
    C2 O2 C1 N1 . . . . 9.6(3) ?
    C12 N1 C1 O1 . . . . 14.4(4) ?
    C3 N1 C1 O1 . . . . -166.1(3) ?
    C12 N1 C1 O2 . . . . -167.7(2) ?
    C3 N1 C1 O2 . . . . 11.8(3) ?
    C1 O2 C2 C4 . . . . -147.4(2) ?
    C1 O2 C2 C5 . . . . 90.9(2) ?
    C1 O2 C2 C3 . . . . -25.5(2) ?
    C12 N1 C3 C6 . . . . -83.1(2) ?
    C1 N1 C3 C6 . . . . 97.4(2) ?
    C12 N1 C3 C2 . . . . 153.16(19) ?
    C1 N1 C3 C2 . . . . -26.4(2) ?
    O2 C2 C3 N1 . . . . 29.5(2) ?
    C4 C2 C3 N1 . . . . 145.1(2) ?
    C5 C2 C3 N1 . . . . -84.7(2) ?
    O2 C2 C3 C6 . . . . -91.5(2) ?
    C4 C2 C3 C6 . . . . 24.1(3) ?
    C5 C2 C3 C6 . . . . 154.2(2) ?
    N1 C3 C6 C7 . . . . 151.4(2) ?
    C2 C3 C6 C7 . . . . -94.4(2) ?
    N1 C3 C6 C11 . . . . -30.3(3) ?
    C2 C3 C6 C11 . . . . 83.9(3) ?
    C11 C6 C7 C8 . . . . -0.3(3) ?
    C3 C6 C7 C8 . . . . 178.0(2) ?
    C6 C7 C8 C9 . . . . 0.4(4) ?
    C7 C8 C9 C10 . . . . -0.3(5) ?
    C8 C9 C10 C11 . . . . 0.2(5) ?
    C9 C10 C11 C6 . . . . -0.2(5) ?
    C7 C6 C11 C10 . . . . 0.2(4) ?
    C3 C6 C11 C10 . . . . -178.1(2) ?
    C1 N1 C12 O3 . . . . -178.1(2) ?
    C3 N1 C12 O3 . . . . 2.4(3) ?
    C1 N1 C12 C13 . . . . 3.7(3) ?
    C3 N1 C12 C13 . . . . -175.75(19) ?
    O3 C12 C13 C14 . . . . -58.5(3) ?
    N1 C12 C13 C14 . . . . 119.6(2) ?
    C12 C13 C14 C15 . . . . -61.5(2) ?
    C12 C13 C14 C21 . . . . 172.56(18) ?
    C21 C14 C15 C16 . . . . -117.6(3) ?
    C13 C14 C15 C16 . . . . 117.7(3) ?
    C21 C14 C15 C20 . . . . 63.7(3) ?
    C13 C14 C15 C20 . . . . -60.9(3) ?
    C20 C15 C16 C17 . . . . -0.4(4) ?
    C14 C15 C16 C17 . . . . -179.1(3) ?
    C15 C16 C17 C18 . . . . -0.1(5) ?
    C16 C17 C18 C19 . . . . 0.1(5) ?
    C17 C18 C19 C20 . . . . 0.5(5) ?
    C18 C19 C20 C15 . . . . -1.1(5) ?
    C16 C15 C20 C19 . . . . 1.0(4) ?
    C14 C15 C20 C19 . . . . 179.7(3) ?
    C15 C14 C21 C25 . . . . 37.1(10) ?
    C13 C14 C21 C25 . . . . 161.5(9) ?
    C15 C14 C21 C22 . . . . 160.5(9) ?
    C13 C14 C21 C22 . . . . -75.1(10) ?
    C25 C21 C22 C23 . . . . 14(2) ?
    C14 C21 C22 C23 . . . . -114.2(16) ?
    C21 C22 C23 C24 . . . . -29(2) ?
    C22 C23 C24 C25 . . . . 33(2) ?
    C22 C21 C25 C24 . . . . 6(2) ?
    C14 C21 C25 C24 . . . . 132.3(17) ?
    C23 C24 C25 C21 . . . . -24(2) ?
    C22' C23' C24' C25' . . . . 29.0(6) ?
