#------------------------------------------------------------------------------
#$Date: 2023-12-04 11:48:06 +0200 (Mon, 04 Dec 2023) $
#$Revision: 287976 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/77/8107712.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8107712
loop_
_publ_author_name
'Liu, Zi-Yu'
'Wang, Wen-Shui'
'Jiang, Sheng'
'Zhao, Feng-Lan'
'Meng, Qing-Guo'
_publ_section_title
;
 Crystal structure of (5R,8R,9R,10R,12R,13R,14R,
 17S,17Z)-2-((3-fluoropyridin-4-yl)methylene)-12-hydroxy-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)hexadecahydro-3H-cyclopenta[a]phenanthren-3-one,
 C36H52FNO3
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1237
_journal_page_last               1239
_journal_paper_doi               10.1515/ncrs-2023-0429
_journal_volume                  238
_journal_year                    2023
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C36 H52 F N O3'
_chemical_formula_sum            'C36 H52 F N O3'
_chemical_formula_weight         565.78
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8101(5)
_cell_length_b                   13.1592(7)
_cell_length_c                   30.5721(15)
_cell_measurement_reflns_used    5126
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4470
_cell_measurement_theta_min      2.5070
_cell_volume                     3142.0(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXL-2017/1 (Sheldrick, 2017)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'CCD plate'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            14083
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         2.042
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80405
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1446 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(7)
_refine_ls_extinction_coef       0.0028(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         5656
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0488
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0382P)²+0.6285P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.1048
_reflns_Friedel_coverage         0.692
_reflns_Friedel_fraction_full    0.921
_reflns_Friedel_fraction_max     0.918
_reflns_number_gt                4598
_reflns_number_total             5656
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2023-0429_suppl_001.cif
_cod_data_source_block           zsn2-5
_cod_database_code               8107712
_shelx_shelxl_version_number     2017/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.989
_shelx_estimated_absorpt_t_max   0.992
loop_
_space_group_symop_operation_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'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2736(4) -0.3268(2) 0.60107(10) 0.0250(7) Uani 1 1 d . . . . .
C2 C 0.3357(4) -0.3750(2) 0.64263(10) 0.0273(7) Uani 1 1 d . . . . .
C3 C 0.3896(4) -0.3084(2) 0.68110(9) 0.0248(7) Uani 1 1 d . . . . .
C4 C 0.3414(4) -0.1948(2) 0.67523(9) 0.0248(7) Uani 1 1 d . . . . .
H4 H 0.434761 -0.166349 0.657657 0.030 Uiso 1 1 calc R U . . .
C5 C 0.1788(4) -0.1746(2) 0.64796(9) 0.0230(7) Uani 1 1 d . . . . .
C6 C 0.2154(4) -0.2176(2) 0.60193(9) 0.0268(7) Uani 1 1 d . . . . .
H6A H 0.112144 -0.211619 0.584477 0.032 Uiso 1 1 calc R U . . .
H6B H 0.302740 -0.175984 0.588209 0.032 Uiso 1 1 calc R U . . .
C7 C 0.3467(5) -0.1351(2) 0.71759(10) 0.0361(9) Uani 1 1 d . . . . .
H7A H 0.452246 -0.150402 0.732964 0.043 Uiso 1 1 calc R U . . .
H7B H 0.251940 -0.155955 0.736044 0.043 Uiso 1 1 calc R U . . .
C8 C 0.3359(5) -0.0217(3) 0.70952(10) 0.0382(9) Uani 1 1 d . . . . .
H8A H 0.435606 -0.000437 0.692989 0.046 Uiso 1 1 calc R U . . .
H8B H 0.338266 0.013350 0.737416 0.046 Uiso 1 1 calc R U . . .
C9 C 0.1737(4) 0.0098(2) 0.68452(9) 0.0254(7) Uani 1 1 d . . . . .
C10 C 0.1569(4) -0.0567(2) 0.64259(9) 0.0230(7) Uani 1 1 d . . . . .
H10 H 0.253618 -0.035975 0.624202 0.028 Uiso 1 1 calc R U . . .
C11 C 0.1867(4) 0.1231(2) 0.66841(9) 0.0262(7) Uani 1 1 d . . . . .
C12 C 0.0233(4) 0.1541(2) 0.64317(10) 0.0252(7) Uani 1 1 d . . . . .
H12 H -0.073750 0.142944 0.662913 0.030 Uiso 1 1 calc R U . . .
C13 C -0.0052(5) 0.0868(3) 0.60347(11) 0.0388(9) Uani 1 1 d . . . . .
H13 H 0.084795 0.099753 0.581837 0.047 Uiso 1 1 calc R U . . .
C14 C -0.0025(5) -0.0254(2) 0.61640(12) 0.0357(9) Uani 1 1 d . . . . .
H14A H -0.008457 -0.066389 0.590070 0.043 Uiso 1 1 calc R U . . .
H14B H -0.103623 -0.040044 0.633713 0.043 Uiso 1 1 calc R U . . .
C15 C 0.1902(5) 0.2064(2) 0.70403(11) 0.0399(9) Uani 1 1 d . . . . .
H15A H 0.113487 0.189292 0.727874 0.048 Uiso 1 1 calc R U . . .
H15B H 0.304927 0.214836 0.715601 0.048 Uiso 1 1 calc R U . . .
C16 C 0.1307(5) 0.3032(2) 0.68082(10) 0.0351(8) Uani 1 1 d . . . . .
H16A H 0.227824 0.346907 0.674720 0.042 Uiso 1 1 calc R U . . .
H16B H 0.050710 0.340182 0.699141 0.042 Uiso 1 1 calc R U . . .
C17 C 0.0425(4) 0.2707(2) 0.63743(10) 0.0242(7) Uani 1 1 d . . . . .
H17 H 0.125563 0.281737 0.613869 0.029 Uiso 1 1 calc R U . . .
C18 C -0.1180(4) 0.3348(2) 0.62630(9) 0.0245(7) Uani 1 1 d . . . . .
C19 C -0.0723(5) 0.4475(2) 0.62659(11) 0.0324(8) Uani 1 1 d . . . . .
H19A H -0.063167 0.470455 0.656640 0.039 Uiso 1 1 calc R U . . .
H19B H 0.038606 0.456517 0.612860 0.039 Uiso 1 1 calc R U . . .
C20 C -0.2032(5) 0.5125(2) 0.60289(11) 0.0375(9) Uani 1 1 d . . . . .
H20A H -0.166269 0.582899 0.602909 0.045 Uiso 1 1 calc R U . . .
H20B H -0.312562 0.508568 0.617834 0.045 Uiso 1 1 calc R U . . .
C21 C -0.2227(5) 0.4751(2) 0.55592(11) 0.0342(8) Uani 1 1 d . . . . .
H21A H -0.310335 0.514863 0.541353 0.041 Uiso 1 1 calc R U . . .
H21B H -0.115732 0.485559 0.540416 0.041 Uiso 1 1 calc R U . . .
C22 C -0.2707(4) 0.3631(2) 0.55375(10) 0.0271(8) Uani 1 1 d . . . . .
C23 C -0.2353(5) 0.3204(3) 0.50834(10) 0.0407(9) Uani 1 1 d . . . . .
H23A H -0.116555 0.329633 0.501283 0.061 Uiso 1 1 calc R U . . .
H23B H -0.304662 0.355371 0.487232 0.061 Uiso 1 1 calc R U . . .
H23C H -0.262421 0.249241 0.507876 0.061 Uiso 1 1 calc R U . . .
C24 C 0.0209(5) -0.0033(3) 0.71602(11) 0.0426(10) Uani 1 1 d . . . . .
H24A H 0.017282 -0.072198 0.726335 0.064 Uiso 1 1 calc R U . . .
H24B H -0.083650 0.012140 0.700903 0.064 Uiso 1 1 calc R U . . .
H24C H 0.033974 0.041916 0.740428 0.064 Uiso 1 1 calc R U . . .
C25 C 0.0182(4) -0.2288(2) 0.66558(11) 0.0341(8) Uani 1 1 d . . . . .
H25A H -0.080099 -0.207812 0.649044 0.051 Uiso 1 1 calc R U . . .
H25B H 0.002056 -0.211505 0.695803 0.051 Uiso 1 1 calc R U . . .
H25C H 0.032559 -0.301023 0.662878 0.051 Uiso 1 1 calc R U . . .
C26 C 0.3226(5) -0.3560(3) 0.72356(10) 0.0385(9) Uani 1 1 d . . . . .
H26A H 0.200502 -0.348153 0.724964 0.058 Uiso 1 1 calc R U . . .
H26B H 0.374240 -0.322590 0.748169 0.058 Uiso 1 1 calc R U . . .
H26C H 0.351060 -0.426917 0.724130 0.058 Uiso 1 1 calc R U . . .
C27 C -0.4583(5) 0.3454(3) 0.56552(11) 0.0378(9) Uani 1 1 d . . . . .
H27A H -0.479512 0.273782 0.567913 0.057 Uiso 1 1 calc R U . . .
H27B H -0.530075 0.373634 0.543107 0.057 Uiso 1 1 calc R U . . .
H27C H -0.483262 0.377737 0.592940 0.057 Uiso 1 1 calc R U . . .
C28 C 0.3478(4) 0.1416(2) 0.64014(12) 0.0391(9) Uani 1 1 d . . . . .
H28A H 0.357358 0.212725 0.633615 0.059 Uiso 1 1 calc R U . . .
H28B H 0.338415 0.103850 0.613372 0.059 Uiso 1 1 calc R U . . .
H28C H 0.447548 0.119693 0.655865 0.059 Uiso 1 1 calc R U . . .
C29 C 0.5871(4) -0.3165(3) 0.68134(10) 0.0302(8) Uani 1 1 d . . . . .
H29A H 0.620064 -0.385251 0.687705 0.045 Uiso 1 1 calc R U . . .
H29B H 0.633022 -0.272005 0.703276 0.045 Uiso 1 1 calc R U . . .
H29C H 0.630984 -0.297406 0.653180 0.045 Uiso 1 1 calc R U . . .
C30 C 0.2775(4) -0.3863(2) 0.56560(10) 0.0289(8) Uani 1 1 d . . . . .
H30 H 0.316251 -0.452238 0.570331 0.035 Uiso 1 1 calc R U . . .
C31 C 0.2294(4) -0.3627(2) 0.52022(10) 0.0271(8) Uani 1 1 d . . . . .
C32 C 0.1819(4) -0.4402(2) 0.49228(10) 0.0277(7) Uani 1 1 d . . . . .
C33 C 0.1323(4) -0.4243(3) 0.44958(10) 0.0318(8) Uani 1 1 d . . . . .
H33 H 0.099547 -0.479751 0.432689 0.038 Uiso 1 1 calc R U . . .
C34 C 0.1780(6) -0.2557(3) 0.45767(11) 0.0436(10) Uani 1 1 d . . . . .
H34 H 0.178044 -0.190536 0.445946 0.052 Uiso 1 1 calc R U . . .
C35 C 0.2278(5) -0.2669(3) 0.50075(11) 0.0393(9) Uani 1 1 d . . . . .
H35 H 0.260412 -0.210137 0.516866 0.047 Uiso 1 1 calc R U . . .
C36 C -0.2667(5) 0.3112(3) 0.65699(10) 0.0362(9) Uani 1 1 d . . . . .
H36A H -0.351862 0.363485 0.654524 0.054 Uiso 1 1 calc R U . . .
H36B H -0.225632 0.308380 0.686570 0.054 Uiso 1 1 calc R U . . .
H36C H -0.316076 0.246914 0.649212 0.054 Uiso 1 1 calc R U . . .
F1 F 0.1806(3) -0.53701(13) 0.50769(6) 0.0389(5) Uani 1 1 d . . . . .
N1 N 0.1299(4) -0.3320(2) 0.43173(9) 0.0384(7) Uani 1 1 d . . . . .
O1 O -0.1569(3) 0.30433(14) 0.58156(6) 0.0254(5) Uani 1 1 d . . . . .
O2 O -0.1682(5) 0.10256(19) 0.58389(12) 0.0840(12) Uani 1 1 d . . . . .
H2 H -0.183301 0.163538 0.579934 0.126 Uiso 1 1 calc R U . . .
O3 O 0.3489(3) -0.46721(16) 0.64538(7) 0.0382(6) Uani 1 1 d . . . . .
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 0.0016 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C30 C1 C2 115.5(3) . .
C30 C1 C6 125.4(3) . .
C2 C1 C6 119.1(3) . .
O3 C2 C1 120.4(3) . .
O3 C2 C3 119.6(3) . .
C1 C2 C3 119.9(3) . .
C2 C3 C26 108.9(3) . .
C2 C3 C29 103.8(3) . .
C26 C3 C29 108.0(3) . .
C2 C3 C4 113.4(2) . .
C26 C3 C4 114.1(3) . .
C29 C3 C4 108.0(3) . .
C7 C4 C5 113.3(3) . .
C7 C4 C3 113.2(2) . .
C5 C4 C3 115.4(3) . .
C7 C4 H4 104.5 . .
C5 C4 H4 104.5 . .
C3 C4 H4 104.5 . .
C25 C5 C4 113.7(2) . .
C25 C5 C6 107.5(3) . .
C4 C5 C6 106.1(2) . .
C25 C5 C10 114.0(3) . .
C4 C5 C10 108.4(2) . .
C6 C5 C10 106.7(2) . .
C1 C6 C5 114.9(2) . .
C1 C6 H6A 108.5 . .
C5 C6 H6A 108.5 . .
C1 C6 H6B 108.5 . .
C5 C6 H6B 108.5 . .
H6A C6 H6B 107.5 . .
C4 C7 C8 111.7(3) . .
C4 C7 H7A 109.3 . .
C8 C7 H7A 109.3 . .
C4 C7 H7B 109.3 . .
C8 C7 H7B 109.3 . .
H7A C7 H7B 107.9 . .
C7 C8 C9 113.1(3) . .
C7 C8 H8A 108.9 . .
C9 C8 H8A 108.9 . .
C7 C8 H8B 108.9 . .
C9 C8 H8B 108.9 . .
H8A C8 H8B 107.8 . .
C8 C9 C24 107.3(3) . .
C8 C9 C10 109.1(3) . .
C24 C9 C10 112.7(3) . .
C8 C9 C11 111.0(3) . .
C24 C9 C11 110.6(3) . .
C10 C9 C11 106.3(2) . .
C14 C10 C9 110.3(3) . .
C14 C10 C5 114.0(2) . .
C9 C10 C5 117.4(2) . .
C14 C10 H10 104.5 . .
C9 C10 H10 104.5 . .
C5 C10 H10 104.5 . .
C28 C11 C15 105.6(3) . .
C28 C11 C12 110.6(2) . .
C15 C11 C12 100.3(3) . .
C28 C11 C9 112.2(3) . .
C15 C11 C9 116.9(2) . .
C12 C11 C9 110.6(3) . .
C13 C12 C11 111.5(3) . .
C13 C12 C17 120.0(3) . .
C11 C12 C17 103.7(2) . .
C13 C12 H12 107.0 . .
C11 C12 H12 107.0 . .
C17 C12 H12 107.0 . .
O2 C13 C12 112.5(3) . .
O2 C13 C14 105.2(3) . .
C12 C13 C14 110.7(3) . .
O2 C13 H13 109.4 . .
C12 C13 H13 109.4 . .
C14 C13 H13 109.4 . .
C13 C14 C10 113.9(3) . .
C13 C14 H14A 108.8 . .
C10 C14 H14A 108.8 . .
C13 C14 H14B 108.8 . .
C10 C14 H14B 108.8 . .
H14A C14 H14B 107.7 . .
C16 C15 C11 105.0(2) . .
C16 C15 H15A 110.8 . .
C11 C15 H15A 110.8 . .
C16 C15 H15B 110.8 . .
C11 C15 H15B 110.8 . .
H15A C15 H15B 108.8 . .
C15 C16 C17 107.5(3) . .
C15 C16 H16A 110.2 . .
C17 C16 H16A 110.2 . .
C15 C16 H16B 110.2 . .
C17 C16 H16B 110.2 . .
H16A C16 H16B 108.5 . .
C18 C17 C12 119.0(3) . .
C18 C17 C16 113.3(2) . .
C12 C17 C16 102.6(2) . .
C18 C17 H17 107.1 . .
C12 C17 H17 107.1 . .
C16 C17 H17 107.1 . .
O1 C18 C19 108.8(2) . .
O1 C18 C36 111.2(2) . .
C19 C18 C36 111.9(3) . .
O1 C18 C17 103.0(2) . .
C19 C18 C17 109.8(3) . .
C36 C18 C17 111.7(2) . .
C20 C19 C18 112.8(3) . .
C20 C19 H19A 109.0 . .
C18 C19 H19A 109.0 . .
C20 C19 H19B 109.0 . .
C18 C19 H19B 109.0 . .
H19A C19 H19B 107.8 . .
C19 C20 C21 109.5(3) . .
C19 C20 H20A 109.8 . .
C21 C20 H20A 109.8 . .
C19 C20 H20B 109.8 . .
C21 C20 H20B 109.8 . .
H20A C20 H20B 108.2 . .
C22 C21 C20 112.2(3) . .
C22 C21 H21A 109.2 . .
C20 C21 H21A 109.2 . .
C22 C21 H21B 109.2 . .
C20 C21 H21B 109.2 . .
H21A C21 H21B 107.9 . .
O1 C22 C21 109.8(3) . .
O1 C22 C23 103.1(2) . .
C21 C22 C23 110.6(3) . .
O1 C22 C27 111.6(3) . .
C21 C22 C27 112.0(3) . .
C23 C22 C27 109.4(3) . .
C22 C23 H23A 109.5 . .
C22 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
C22 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
C9 C24 H24A 109.5 . .
C9 C24 H24B 109.5 . .
H24A C24 H24B 109.5 . .
C9 C24 H24C 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
C5 C25 H25A 109.5 . .
C5 C25 H25B 109.5 . .
H25A C25 H25B 109.5 . .
C5 C25 H25C 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
C3 C26 H26A 109.5 . .
C3 C26 H26B 109.5 . .
H26A C26 H26B 109.5 . .
C3 C26 H26C 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
C22 C27 H27A 109.5 . .
C22 C27 H27B 109.5 . .
H27A C27 H27B 109.5 . .
C22 C27 H27C 109.5 . .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
C11 C28 H28A 109.5 . .
C11 C28 H28B 109.5 . .
H28A C28 H28B 109.5 . .
C11 C28 H28C 109.5 . .
H28A C28 H28C 109.5 . .
H28B C28 H28C 109.5 . .
C3 C29 H29A 109.5 . .
C3 C29 H29B 109.5 . .
H29A C29 H29B 109.5 . .
C3 C29 H29C 109.5 . .
H29A C29 H29C 109.5 . .
H29B C29 H29C 109.5 . .
C1 C30 C31 129.4(3) . .
C1 C30 H30 115.3 . .
C31 C30 H30 115.3 . .
C32 C31 C35 113.7(3) . .
C32 C31 C30 119.7(3) . .
C35 C31 C30 126.6(3) . .
F1 C32 C33 118.0(3) . .
F1 C32 C31 118.7(3) . .
C33 C32 C31 123.3(3) . .
N1 C33 C32 122.1(3) . .
N1 C33 H33 119.0 . .
C32 C33 H33 119.0 . .
N1 C34 C35 124.6(3) . .
N1 C34 H34 117.7 . .
C35 C34 H34 117.7 . .
C34 C35 C31 120.4(3) . .
C34 C35 H35 119.8 . .
C31 C35 H35 119.8 . .
C18 C36 H36A 109.5 . .
C18 C36 H36B 109.5 . .
H36A C36 H36B 109.5 . .
C18 C36 H36C 109.5 . .
H36A C36 H36C 109.5 . .
H36B C36 H36C 109.5 . .
C33 N1 C34 116.0(3) . .
C22 O1 C18 122.0(2) . .
C13 O2 H2 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C30 1.338(4) .
C1 C2 1.501(4) .
C1 C6 1.508(4) .
C2 O3 1.221(4) .
C2 C3 1.526(4) .
C3 C26 1.533(4) .
C3 C29 1.546(4) .
C3 C4 1.552(4) .
C4 C7 1.515(4) .
C4 C5 1.542(4) .
C4 H4 0.9800 .
C5 C25 1.540(4) .
C5 C6 1.543(4) .
C5 C10 1.570(4) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 C8 1.515(5) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 C9 1.537(5) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 C24 1.543(5) .
C9 C10 1.557(4) .
C9 C11 1.573(4) .
C10 C14 1.537(4) .
C10 H10 0.9800 .
C11 C28 1.545(5) .
C11 C15 1.545(4) .
C11 C12 1.546(4) .
C12 C13 1.519(4) .
C12 C17 1.552(4) .
C12 H12 0.9800 .
C13 O2 1.422(4) .
C13 C14 1.528(4) .
C13 H13 0.9800 .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C15 C16 1.530(5) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 C17 1.555(4) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C17 C18 1.549(4) .
C17 H17 0.9800 .
C18 O1 1.458(3) .
C18 C19 1.524(4) .
C18 C36 1.525(4) .
C19 C20 1.517(5) .
C19 H19A 0.9700 .
C19 H19B 0.9700 .
C20 C21 1.526(5) .
C20 H20A 0.9700 .
C20 H20B 0.9700 .
C21 C22 1.522(4) .
C21 H21A 0.9700 .
C21 H21B 0.9700 .
C22 O1 1.453(4) .
C22 C23 1.523(4) .
C22 C27 1.527(5) .
C23 H23A 0.9600 .
C23 H23B 0.9600 .
C23 H23C 0.9600 .
C24 H24A 0.9600 .
C24 H24B 0.9600 .
C24 H24C 0.9600 .
C25 H25A 0.9600 .
C25 H25B 0.9600 .
C25 H25C 0.9600 .
C26 H26A 0.9600 .
C26 H26B 0.9600 .
C26 H26C 0.9600 .
C27 H27A 0.9600 .
C27 H27B 0.9600 .
C27 H27C 0.9600 .
C28 H28A 0.9600 .
C28 H28B 0.9600 .
C28 H28C 0.9600 .
C29 H29A 0.9600 .
C29 H29B 0.9600 .
C29 H29C 0.9600 .
C30 C31 1.471(4) .
C30 H30 0.9300 .
C31 C32 1.381(4) .
C31 C35 1.394(4) .
C32 F1 1.359(3) .
C32 C33 1.378(4) .
C33 N1 1.332(4) .
C33 H33 0.9300 .
C34 N1 1.333(4) .
C34 C35 1.381(5) .
C34 H34 0.9300 .
C35 H35 0.9300 .
C36 H36A 0.9600 .
C36 H36B 0.9600 .
C36 H36C 0.9600 .
O2 H2 0.8200 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O1 0.82 1.86 2.658(3) 162.3 . yes
C33 H33 O2 0.93 2.48 2.996(4) 115.0 4_546 yes
C21 H21B F1 0.97 2.54 3.482(4) 163.9 1_565 yes
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C30 C1 C2 O3 -16.5(5) . . . .
C6 C1 C2 O3 164.4(3) . . . .
C30 C1 C2 C3 161.0(3) . . . .
C6 C1 C2 C3 -18.1(4) . . . .
O3 C2 C3 C26 -43.6(4) . . . .
C1 C2 C3 C26 138.8(3) . . . .
O3 C2 C3 C29 71.2(4) . . . .
C1 C2 C3 C29 -106.3(3) . . . .
O3 C2 C3 C4 -171.8(3) . . . .
C1 C2 C3 C4 10.7(4) . . . .
C2 C3 C4 C7 163.2(3) . . . .
C26 C3 C4 C7 37.7(4) . . . .
C29 C3 C4 C7 -82.3(3) . . . .
C2 C3 C4 C5 30.5(4) . . . .
C26 C3 C4 C5 -95.0(3) . . . .
C29 C3 C4 C5 145.0(3) . . . .
C7 C4 C5 C25 -76.6(4) . . . .
C3 C4 C5 C25 56.1(3) . . . .
C7 C4 C5 C6 165.6(3) . . . .
C3 C4 C5 C6 -61.7(3) . . . .
C7 C4 C5 C10 51.3(3) . . . .
C3 C4 C5 C10 -176.0(2) . . . .
C30 C1 C6 C5 164.9(3) . . . .
C2 C1 C6 C5 -16.1(4) . . . .
C25 C5 C6 C1 -68.6(3) . . . .
C4 C5 C6 C1 53.4(3) . . . .
C10 C5 C6 C1 168.9(3) . . . .
C5 C4 C7 C8 -58.2(4) . . . .
C3 C4 C7 C8 168.1(3) . . . .
C4 C7 C8 C9 58.0(4) . . . .
C7 C8 C9 C24 71.0(3) . . . .
C7 C8 C9 C10 -51.3(4) . . . .
C7 C8 C9 C11 -168.1(3) . . . .
C8 C9 C10 C14 -178.9(3) . . . .
C24 C9 C10 C14 62.1(3) . . . .
C11 C9 C10 C14 -59.2(3) . . . .
C8 C9 C10 C5 48.2(4) . . . .
C24 C9 C10 C5 -70.8(4) . . . .
C11 C9 C10 C5 167.9(3) . . . .
C25 C5 C10 C14 -51.5(4) . . . .
C4 C5 C10 C14 -179.3(3) . . . .
C6 C5 C10 C14 66.9(3) . . . .
C25 C5 C10 C9 79.6(3) . . . .
C4 C5 C10 C9 -48.1(4) . . . .
C6 C5 C10 C9 -162.0(3) . . . .
C8 C9 C11 C28 55.9(3) . . . .
C24 C9 C11 C28 174.8(3) . . . .
C10 C9 C11 C28 -62.6(3) . . . .
C8 C9 C11 C15 -66.2(4) . . . .
C24 C9 C11 C15 52.7(4) . . . .
C10 C9 C11 C15 175.3(3) . . . .
C8 C9 C11 C12 179.8(2) . . . .
C24 C9 C11 C12 -61.3(3) . . . .
C10 C9 C11 C12 61.4(3) . . . .
C28 C11 C12 C13 65.3(3) . . . .
C15 C11 C12 C13 176.3(3) . . . .
C9 C11 C12 C13 -59.6(3) . . . .
C28 C11 C12 C17 -65.2(3) . . . .
C15 C11 C12 C17 45.8(3) . . . .
C9 C11 C12 C17 169.9(2) . . . .
C11 C12 C13 O2 170.3(3) . . . .
C17 C12 C13 O2 -68.2(4) . . . .
C11 C12 C13 C14 52.9(4) . . . .
C17 C12 C13 C14 174.4(3) . . . .
O2 C13 C14 C10 -174.1(3) . . . .
C12 C13 C14 C10 -52.3(4) . . . .
C9 C10 C14 C13 56.9(4) . . . .
C5 C10 C14 C13 -168.6(3) . . . .
C28 C11 C15 C16 76.8(4) . . . .
C12 C11 C15 C16 -38.1(4) . . . .
C9 C11 C15 C16 -157.7(3) . . . .
C11 C15 C16 C17 16.8(4) . . . .
C13 C12 C17 C18 73.2(4) . . . .
C11 C12 C17 C18 -161.6(2) . . . .
C13 C12 C17 C16 -160.8(3) . . . .
C11 C12 C17 C16 -35.6(3) . . . .
C15 C16 C17 C18 141.1(3) . . . .
C15 C16 C17 C12 11.5(4) . . . .
C12 C17 C18 O1 -69.7(3) . . . .
C16 C17 C18 O1 169.6(2) . . . .
C12 C17 C18 C19 174.6(3) . . . .
C16 C17 C18 C19 53.8(3) . . . .
C12 C17 C18 C36 49.8(4) . . . .
C16 C17 C18 C36 -71.0(3) . . . .
O1 C18 C19 C20 50.2(4) . . . .
C36 C18 C19 C20 -73.1(3) . . . .
C17 C18 C19 C20 162.3(3) . . . .
C18 C19 C20 C21 -57.1(4) . . . .
C19 C20 C21 C22 56.2(4) . . . .
C20 C21 C22 O1 -49.3(4) . . . .
C20 C21 C22 C23 -162.4(3) . . . .
C20 C21 C22 C27 75.3(4) . . . .
C2 C1 C30 C31 -178.8(3) . . . .
C6 C1 C30 C31 0.3(6) . . . .
C1 C30 C31 C32 -156.0(3) . . . .
C1 C30 C31 C35 25.0(6) . . . .
C35 C31 C32 F1 179.3(3) . . . .
C30 C31 C32 F1 0.1(5) . . . .
C35 C31 C32 C33 -2.0(5) . . . .
C30 C31 C32 C33 178.8(3) . . . .
F1 C32 C33 N1 -179.9(3) . . . .
C31 C32 C33 N1 1.4(5) . . . .
N1 C34 C35 C31 -0.4(6) . . . .
C32 C31 C35 C34 1.4(5) . . . .
C30 C31 C35 C34 -179.4(4) . . . .
C32 C33 N1 C34 -0.1(5) . . . .
C35 C34 N1 C33 -0.4(6) . . . .
C21 C22 O1 C18 47.5(4) . . . .
C23 C22 O1 C18 165.4(3) . . . .
C27 C22 O1 C18 -77.2(3) . . . .
C19 C18 O1 C22 -47.5(4) . . . .
C36 C18 O1 C22 76.1(3) . . . .
C17 C18 O1 C22 -164.0(2) . . . .
