# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Ta_a
_database_code_depnum_ccdc_archive 'CCDC 2050194'
loop_
_audit_author_name
_audit_author_address
'Yu-Yang Xie'
;Shanghai jiaotong university
China
;
_audit_update_record             
;
2020-12-14 deposited with the CCDC.	2021-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H43 F6 N2 O4'
_chemical_formula_sum            'C40 H43 F6 N2 O4'
_chemical_formula_weight         729.76

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.2944(6)
_cell_length_b                   12.0674(7)
_cell_length_c                   15.9401(8)
_cell_angle_alpha                68.586(2)
_cell_angle_beta                 89.702(3)
_cell_angle_gamma                78.260(3)
_cell_volume                     1799.73(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    7216
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      67.36

_exptl_crystal_description       CHONF
_exptl_crystal_colour            coulorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_F_000             766
_exptl_transmission_factor_min   0.5276
_exptl_transmission_factor_max   0.7531
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.908
_shelx_estimated_absorpt_T_min   0.839
_shelx_estimated_absorpt_T_max   0.915
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19333
_diffrn_reflns_av_unetI/netI     0.0679
_diffrn_reflns_av_R_equivalents  0.0676
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.986
_diffrn_reflns_theta_max         68.324
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             6484
_reflns_number_gt                4006
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6484
_refine_ls_number_parameters     473
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1297
_refine_ls_R_factor_gt           0.0924
_refine_ls_wR_factor_ref         0.2891
_refine_ls_wR_factor_gt          0.2598
_refine_ls_goodness_of_fit_ref   1.634
_refine_ls_restrained_S_all      1.634
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O1 O 0.9621(3) 0.6059(3) 0.8465(2) 0.0932(9) Uani 1 1 d . . . . .
C1 C 0.5127(5) 0.7866(5) 1.1891(3) 0.0840(12) Uani 1 1 d . . . . .
N1 N 0.5125(3) 0.7678(3) 0.8446(2) 0.0768(9) Uani 1 1 d . . . . .
F1 F 0.5487(5) 0.6863(4) 1.2535(2) 0.206(3) Uani 1 1 d . . . . .
O2 O 0.7109(3) 0.7821(3) 0.71723(18) 0.0864(8) Uani 1 1 d . . . . .
C2 C 0.5062(4) 0.7806(4) 1.0992(2) 0.0701(10) Uani 1 1 d . . . . .
N2 N 0.0187(3) 0.8113(3) 0.4912(2) 0.0730(9) Uani 1 1 d . . . . .
F2 F 0.3989(5) 0.8263(5) 1.2147(2) 0.194(2) Uani 1 1 d . . . . .
O3 O 0.2228(3) 0.8042(3) 0.61386(18) 0.0850(8) Uani 1 1 d . . . . .
C3 C 0.3970(4) 0.8478(4) 1.0387(3) 0.0806(11) Uani 1 1 d . . . . .
H3 H 0.327023 0.894337 1.056594 0.097 Uiso 1 1 calc R U . . .
F3 F 0.5816(7) 0.8527(6) 1.1990(3) 0.274(4) Uani 1 1 d . . . . .
F4 F 0.0878(4) 0.8236(4) 0.10120(19) 0.1454(14) Uani 1 1 d . . . . .
O4 O 0.4600(3) 0.6107(3) 0.5789(2) 0.0902(9) Uani 1 1 d . . . . .
C4 C 0.3899(4) 0.8471(4) 0.9527(3) 0.0842(12) Uani 1 1 d . . . . .
H4 H 0.316138 0.892453 0.912680 0.101 Uiso 1 1 calc R U . . .
F6 F -0.0227(5) 0.6931(3) 0.14292(19) 0.1611(17) Uani 1 1 d . . . . .
C6 C 0.6044(3) 0.7074(3) 0.9879(2) 0.0587(8) Uani 1 1 d . . . . .
F5 F -0.1164(4) 0.8748(4) 0.0903(2) 0.1796(19) Uani 1 1 d . . . . .
C5 C 0.4948(4) 0.7776(3) 0.9271(2) 0.0664(9) Uani 1 1 d . . . . .
C9 C 0.6192(4) 0.6634(3) 0.8534(2) 0.0641(9) Uani 1 1 d . . . . .
C8 C 0.7077(3) 0.6492(3) 0.9396(2) 0.0599(9) Uani 1 1 d . . . . .
C7 C 0.6100(4) 0.7095(3) 1.0736(2) 0.0646(9) Uani 1 1 d . . . . .
H7 H 0.683088 0.663379 1.114092 0.078 Uiso 1 1 calc R U . . .
C10 C 0.7737(4) 0.5188(4) 0.9998(3) 0.0815(11) Uani 1 1 d . . . . .
H00E H 0.842647 0.486625 0.968904 0.122 Uiso 1 1 calc R U . . .
H00F H 0.708449 0.469336 1.013572 0.122 Uiso 1 1 calc R U . . .
H00H H 0.811474 0.518471 1.054858 0.122 Uiso 1 1 calc R U . . .
C11 C 0.8174(3) 0.7256(3) 0.9180(2) 0.0654(10) Uani 1 1 d . . . . .
H11 H 0.865424 0.704500 0.976498 0.079 Uiso 1 1 calc R U . . .
C12 C 0.7757(4) 0.8651(4) 0.8805(3) 0.0812(12) Uani 1 1 d . . . . .
H00J H 0.711427 0.894421 0.828726 0.097 Uiso 1 1 calc R U . . .
H00K H 0.737785 0.894494 0.926250 0.097 Uiso 1 1 calc R U . . .
C15 C 0.9239(4) 0.7002(5) 0.8577(3) 0.0787(11) Uani 1 1 d . . . . .
C16 C 0.6892(4) 0.6855(4) 0.7648(3) 0.0688(10) Uani 1 1 d . . . . .
C018 C -0.0847(5) 0.8663(5) 0.5354(3) 0.1016(15) Uani 1 1 d . . . . .
H01G H -0.125047 0.947312 0.494887 0.152 Uiso 1 1 calc R U . . .
H01H H -0.046286 0.869766 0.588871 0.152 Uiso 1 1 calc R U . . .
H01I H -0.151085 0.818113 0.551543 0.152 Uiso 1 1 calc R U . . .
C18 C 0.6701(6) 0.4761(4) 0.8217(4) 0.1090(17) Uani 1 1 d . . . . .
H01M H 0.743178 0.426316 0.866234 0.131 Uiso 1 1 calc R U . . .
H01N H 0.630556 0.423594 0.800620 0.131 Uiso 1 1 calc R U . . .
C17 C 0.7177(4) 0.5725(4) 0.7432(3) 0.0866(12) Uani 1 1 d . . . . .
H01A H 0.812209 0.547385 0.738250 0.104 Uiso 1 1 calc R U . . .
H01B H 0.670063 0.586187 0.686736 0.104 Uiso 1 1 calc R U . . .
C19 C 0.5662(4) 0.5497(4) 0.8615(3) 0.0893(13) Uani 1 1 d . . . . .
H01C H 0.556688 0.502358 0.924201 0.107 Uiso 1 1 calc R U . . .
H01D H 0.480415 0.572948 0.827825 0.107 Uiso 1 1 calc R U . . .
C13 C 0.9061(5) 0.9054(5) 0.8531(3) 0.1057(16) Uani 1 1 d . . . . .
H01S H 0.889562 0.988093 0.808744 0.127 Uiso 1 1 calc R U . . .
H01T H 0.958205 0.901135 0.905168 0.127 Uiso 1 1 calc R U . . .
C14 C 0.9767(5) 0.8149(5) 0.8130(4) 0.1154(18) Uani 1 1 d . . . . .
H01W H 0.957059 0.846620 0.748017 0.138 Uiso 1 1 calc R U . . .
H01X H 1.072239 0.798250 0.825728 0.138 Uiso 1 1 calc R U . . .
C20 C 0.4064(4) 0.8174(5) 0.7726(3) 0.1075(17) Uani 1 1 d . . . . .
H01J H 0.436528 0.797277 0.721795 0.161 Uiso 1 1 calc R U . . .
H01K H 0.382207 0.904421 0.754705 0.161 Uiso 1 1 calc R U . . .
H01L H 0.330481 0.783261 0.793785 0.161 Uiso 1 1 calc R U . . .
C21 C 0.2147(4) 0.5952(4) 0.6995(3) 0.0887(13) Uani 1 1 d . . . . .
H21 H 0.259923 0.579463 0.754393 0.106 Uiso 1 1 calc R U . . .
C22 C 0.1493(6) 0.5099(5) 0.6754(3) 0.1085(16) Uani 1 1 d . . . . .
H01Q H 0.103443 0.464956 0.725575 0.130 Uiso 1 1 calc R U . . .
H01R H 0.214449 0.452272 0.659016 0.130 Uiso 1 1 calc R U . . .
C23 C 0.0501(5) 0.5924(4) 0.5942(3) 0.0910(13) Uani 1 1 d . . . . .
H01E H 0.033234 0.547754 0.557147 0.109 Uiso 1 1 calc R U . . .
H01F H -0.033632 0.623188 0.614569 0.109 Uiso 1 1 calc R U . . .
C24 C 0.1165(4) 0.6974(3) 0.5408(2) 0.0652(9) Uani 1 1 d . . . . .
C25 C 0.1932(4) 0.7103(4) 0.6183(2) 0.0693(10) Uani 1 1 d . . . . .
C26 C 0.2018(3) 0.6755(3) 0.4626(2) 0.0632(9) Uani 1 1 d . . . . .
C27 C 0.2570(4) 0.5417(4) 0.4757(3) 0.0842(12) Uani 1 1 d . . . . .
H00A H 0.185023 0.500245 0.482479 0.126 Uiso 1 1 calc R U . . .
H00B H 0.317606 0.503161 0.528773 0.126 Uiso 1 1 calc R U . . .
H00C H 0.303051 0.537910 0.423908 0.126 Uiso 1 1 calc R U . . .
C28 C 0.3185(3) 0.7427(3) 0.4412(2) 0.0658(10) Uani 1 1 d . . . . .
H28 H 0.362442 0.718612 0.393961 0.079 Uiso 1 1 calc R U . . .
C29 C 0.4298(4) 0.7069(4) 0.5161(3) 0.0750(11) Uani 1 1 d . . . . .
C30 C 0.4939(5) 0.8131(5) 0.4991(3) 0.1106(17) Uani 1 1 d . . . . .
H01U H 0.588856 0.789070 0.495277 0.133 Uiso 1 1 calc R U . . .
H01V H 0.479659 0.843665 0.547565 0.133 Uiso 1 1 calc R U . . .
C31 C 0.4292(5) 0.9107(5) 0.4097(3) 0.1067(16) Uani 1 1 d . . . . .
H01O H 0.480485 0.905004 0.359660 0.128 Uiso 1 1 calc R U . . .
H01P H 0.420528 0.991665 0.410842 0.128 Uiso 1 1 calc R U . . .
C32 C 0.2917(4) 0.8818(4) 0.4023(3) 0.0791(11) Uani 1 1 d . . . . .
H00L H 0.229388 0.915930 0.436900 0.095 Uiso 1 1 calc R U . . .
H00M H 0.256068 0.913984 0.339764 0.095 Uiso 1 1 calc R U . . .
C33 C -0.0045(4) 0.8164(4) 0.4048(2) 0.0679(10) Uani 1 1 d . . . . .
C34 C 0.0969(3) 0.7381(3) 0.3832(2) 0.0616(9) Uani 1 1 d . . . . .
C35 C 0.0934(4) 0.7318(3) 0.2993(2) 0.0651(9) Uani 1 1 d . . . . .
H35 H 0.161611 0.680119 0.284498 0.078 Uiso 1 1 calc R U . . .
C36 C -0.0128(4) 0.8033(3) 0.2358(2) 0.0678(10) Uani 1 1 d . . . . .
C37 C -0.1135(4) 0.8790(4) 0.2586(3) 0.0770(11) Uani 1 1 d . . . . .
H37 H -0.184942 0.925162 0.216631 0.092 Uiso 1 1 calc R U . . .
C38 C -0.1106(4) 0.8880(4) 0.3432(3) 0.0811(12) Uani 1 1 d . . . . .
H38 H -0.177992 0.940565 0.357833 0.097 Uiso 1 1 calc R U . . .
C39 C -0.0158(5) 0.7987(4) 0.1443(3) 0.0813(12) Uani 1 1 d . . . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C15 1.204(5) . ?
C1 F3 1.220(5) . ?
C1 F1 1.254(5) . ?
C1 F2 1.295(6) . ?
C1 C2 1.464(5) . ?
N1 C5 1.369(5) . ?
N1 C20 1.454(5) . ?
N1 C9 1.457(5) . ?
O2 C16 1.200(4) . ?
C2 C3 1.386(6) . ?
C2 C7 1.387(5) . ?
N2 C33 1.375(4) . ?
N2 C018 1.455(5) . ?
N2 C24 1.476(5) . ?
O3 C25 1.210(5) . ?
C3 C4 1.376(6) . ?
C3 H3 0.9300 . ?
F4 C39 1.293(5) . ?
O4 C29 1.206(5) . ?
C4 C5 1.384(5) . ?
C4 H4 0.9300 . ?
F6 C39 1.299(5) . ?
C6 C7 1.377(5) . ?
C6 C5 1.398(5) . ?
C6 C8 1.516(5) . ?
F5 C39 1.305(5) . ?
C9 C19 1.540(5) . ?
C9 C16 1.541(5) . ?
C9 C8 1.588(4) . ?
C8 C10 1.525(5) . ?
C8 C11 1.560(5) . ?
C7 H7 0.9300 . ?
C10 H00E 0.9600 . ?
C10 H00F 0.9600 . ?
C10 H00H 0.9600 . ?
C11 C15 1.512(5) . ?
C11 C12 1.533(5) . ?
C11 H11 0.9800 . ?
C12 C13 1.528(6) . ?
C12 H00J 0.9700 . ?
C12 H00K 0.9700 . ?
C15 C14 1.517(7) . ?
C16 C17 1.499(6) . ?
C018 H01G 0.9600 . ?
C018 H01H 0.9600 . ?
C018 H01I 0.9600 . ?
C18 C17 1.524(6) . ?
C18 C19 1.534(6) . ?
C18 H01M 0.9700 . ?
C18 H01N 0.9700 . ?
C17 H01A 0.9700 . ?
C17 H01B 0.9700 . ?
C19 H01C 0.9700 . ?
C19 H01D 0.9700 . ?
C13 C14 1.521(7) . ?
C13 H01S 0.9700 . ?
C13 H01T 0.9700 . ?
C14 H01W 0.9700 . ?
C14 H01X 0.9700 . ?
C20 H01J 0.9600 . ?
C20 H01K 0.9600 . ?
C20 H01L 0.9600 . ?
C21 C25 1.490(6) . ?
C21 C22 1.495(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.539(6) . ?
C22 H01Q 0.9700 . ?
C22 H01R 0.9700 . ?
C23 C24 1.535(6) . ?
C23 H01E 0.9700 . ?
C23 H01F 0.9700 . ?
C24 C25 1.541(5) . ?
C24 C26 1.590(5) . ?
C26 C34 1.524(5) . ?
C26 C27 1.535(5) . ?
C26 C28 1.552(5) . ?
C27 H00A 0.9600 . ?
C27 H00B 0.9600 . ?
C27 H00C 0.9600 . ?
C28 C32 1.527(5) . ?
C28 C29 1.536(5) . ?
C28 H28 0.9800 . ?
C29 C30 1.497(6) . ?
C30 C31 1.525(7) . ?
C30 H01U 0.9700 . ?
C30 H01V 0.9700 . ?
C31 C32 1.540(6) . ?
C31 H01O 0.9700 . ?
C31 H01P 0.9700 . ?
C32 H00L 0.9700 . ?
C32 H00M 0.9700 . ?
C33 C38 1.383(5) . ?
C33 C34 1.390(5) . ?
C34 C35 1.368(5) . ?
C35 C36 1.398(5) . ?
C35 H35 0.9300 . ?
C36 C37 1.376(5) . ?
C36 C39 1.481(5) . ?
C37 C38 1.393(5) . ?
C37 H37 0.9300 . ?
C38 H38 0.9300 . ?

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
_geom_angle_publ_flag
F3 C1 F1 106.0(5) . . ?
F3 C1 F2 103.2(5) . . ?
F1 C1 F2 99.8(5) . . ?
F3 C1 C2 115.9(4) . . ?
F1 C1 C2 115.7(4) . . ?
F2 C1 C2 114.4(4) . . ?
C5 N1 C20 122.0(3) . . ?
C5 N1 C9 110.0(3) . . ?
C20 N1 C9 122.8(3) . . ?
C3 C2 C7 119.7(3) . . ?
C3 C2 C1 120.0(4) . . ?
C7 C2 C1 120.3(4) . . ?
C33 N2 C018 121.0(3) . . ?
C33 N2 C24 108.2(3) . . ?
C018 N2 C24 122.5(3) . . ?
C4 C3 C2 121.3(4) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 118.7(4) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C7 C6 C5 119.9(3) . . ?
C7 C6 C8 130.7(3) . . ?
C5 C6 C8 109.1(3) . . ?
N1 C5 C4 128.9(3) . . ?
N1 C5 C6 110.4(3) . . ?
C4 C5 C6 120.7(3) . . ?
N1 C9 C19 112.3(3) . . ?
N1 C9 C16 110.5(3) . . ?
C19 C9 C16 100.9(3) . . ?
N1 C9 C8 102.6(2) . . ?
C19 C9 C8 114.6(3) . . ?
C16 C9 C8 116.3(3) . . ?
C6 C8 C10 111.5(3) . . ?
C6 C8 C11 106.7(3) . . ?
C10 C8 C11 107.7(3) . . ?
C6 C8 C9 100.5(3) . . ?
C10 C8 C9 115.8(3) . . ?
C11 C8 C9 114.3(3) . . ?
C6 C7 C2 119.7(3) . . ?
C6 C7 H7 120.1 . . ?
C2 C7 H7 120.1 . . ?
C8 C10 H00E 109.5 . . ?
C8 C10 H00F 109.5 . . ?
H00E C10 H00F 109.5 . . ?
C8 C10 H00H 109.5 . . ?
H00E C10 H00H 109.5 . . ?
H00F C10 H00H 109.5 . . ?
C15 C11 C12 103.3(3) . . ?
C15 C11 C8 118.6(3) . . ?
C12 C11 C8 119.2(3) . . ?
C15 C11 H11 104.7 . . ?
C12 C11 H11 104.7 . . ?
C8 C11 H11 104.7 . . ?
C13 C12 C11 103.5(4) . . ?
C13 C12 H00J 111.1 . . ?
C11 C12 H00J 111.1 . . ?
C13 C12 H00K 111.1 . . ?
C11 C12 H00K 111.1 . . ?
H00J C12 H00K 109.0 . . ?
O1 C15 C11 126.8(4) . . ?
O1 C15 C14 124.9(4) . . ?
C11 C15 C14 108.3(4) . . ?
O2 C16 C17 124.7(4) . . ?
O2 C16 C9 124.5(4) . . ?
C17 C16 C9 110.7(4) . . ?
N2 C018 H01G 109.5 . . ?
N2 C018 H01H 109.5 . . ?
H01G C018 H01H 109.5 . . ?
N2 C018 H01I 109.5 . . ?
H01G C018 H01I 109.5 . . ?
H01H C018 H01I 109.5 . . ?
C17 C18 C19 104.3(4) . . ?
C17 C18 H01M 110.9 . . ?
C19 C18 H01M 110.9 . . ?
C17 C18 H01N 110.9 . . ?
C19 C18 H01N 110.9 . . ?
H01M C18 H01N 108.9 . . ?
C16 C17 C18 105.4(3) . . ?
C16 C17 H01A 110.7 . . ?
C18 C17 H01A 110.7 . . ?
C16 C17 H01B 110.7 . . ?
C18 C17 H01B 110.7 . . ?
H01A C17 H01B 108.8 . . ?
C18 C19 C9 105.5(3) . . ?
C18 C19 H01C 110.6 . . ?
C9 C19 H01C 110.6 . . ?
C18 C19 H01D 110.6 . . ?
C9 C19 H01D 110.6 . . ?
H01C C19 H01D 108.8 . . ?
C14 C13 C12 103.7(3) . . ?
C14 C13 H01S 111.0 . . ?
C12 C13 H01S 111.0 . . ?
C14 C13 H01T 111.0 . . ?
C12 C13 H01T 111.0 . . ?
H01S C13 H01T 109.0 . . ?
C15 C14 C13 105.6(4) . . ?
C15 C14 H01W 110.6 . . ?
C13 C14 H01W 110.6 . . ?
C15 C14 H01X 110.6 . . ?
C13 C14 H01X 110.6 . . ?
H01W C14 H01X 108.8 . . ?
N1 C20 H01J 109.5 . . ?
N1 C20 H01K 109.5 . . ?
H01J C20 H01K 109.5 . . ?
N1 C20 H01L 109.5 . . ?
H01J C20 H01L 109.5 . . ?
H01K C20 H01L 109.5 . . ?
C25 C21 C22 106.5(3) . . ?
C25 C21 H21 126.8 . . ?
C22 C21 H21 126.8 . . ?
C21 C22 C23 104.9(4) . . ?
C21 C22 H01Q 110.8 . . ?
C23 C22 H01Q 110.8 . . ?
C21 C22 H01R 110.8 . . ?
C23 C22 H01R 110.8 . . ?
H01Q C22 H01R 108.8 . . ?
C24 C23 C22 105.5(3) . . ?
C24 C23 H01E 110.6 . . ?
C22 C23 H01E 110.6 . . ?
C24 C23 H01F 110.6 . . ?
C22 C23 H01F 110.6 . . ?
H01E C23 H01F 108.8 . . ?
N2 C24 C23 112.5(3) . . ?
N2 C24 C25 110.7(3) . . ?
C23 C24 C25 100.6(3) . . ?
N2 C24 C26 102.5(3) . . ?
C23 C24 C26 114.5(3) . . ?
C25 C24 C26 116.5(3) . . ?
O3 C25 C21 126.1(3) . . ?
O3 C25 C24 123.5(3) . . ?
C21 C25 C24 110.2(3) . . ?
C34 C26 C27 111.5(3) . . ?
C34 C26 C28 107.8(3) . . ?
C27 C26 C28 108.0(3) . . ?
C34 C26 C24 99.6(3) . . ?
C27 C26 C24 115.7(3) . . ?
C28 C26 C24 113.9(3) . . ?
C26 C27 H00A 109.5 . . ?
C26 C27 H00B 109.5 . . ?
H00A C27 H00B 109.5 . . ?
C26 C27 H00C 109.5 . . ?
H00A C27 H00C 109.5 . . ?
H00B C27 H00C 109.5 . . ?
C32 C28 C29 103.4(3) . . ?
C32 C28 C26 120.7(3) . . ?
C29 C28 C26 117.9(3) . . ?
C32 C28 H28 104.3 . . ?
C29 C28 H28 104.3 . . ?
C26 C28 H28 104.3 . . ?
O4 C29 C30 125.3(4) . . ?
O4 C29 C28 126.4(4) . . ?
C30 C29 C28 108.3(4) . . ?
C29 C30 C31 106.7(4) . . ?
C29 C30 H01U 110.4 . . ?
C31 C30 H01U 110.4 . . ?
C29 C30 H01V 110.4 . . ?
C31 C30 H01V 110.4 . . ?
H01U C30 H01V 108.6 . . ?
C30 C31 C32 103.5(4) . . ?
C30 C31 H01O 111.1 . . ?
C32 C31 H01O 111.1 . . ?
C30 C31 H01P 111.1 . . ?
C32 C31 H01P 111.1 . . ?
H01O C31 H01P 109.0 . . ?
C28 C32 C31 104.1(4) . . ?
C28 C32 H00L 110.9 . . ?
C31 C32 H00L 110.9 . . ?
C28 C32 H00M 110.9 . . ?
C31 C32 H00M 110.9 . . ?
H00L C32 H00M 108.9 . . ?
N2 C33 C38 127.7(4) . . ?
N2 C33 C34 111.0(3) . . ?
C38 C33 C34 121.3(3) . . ?
C35 C34 C33 120.0(3) . . ?
C35 C34 C26 130.7(3) . . ?
C33 C34 C26 109.3(3) . . ?
C34 C35 C36 119.9(3) . . ?
C34 C35 H35 120.1 . . ?
C36 C35 H35 120.1 . . ?
C37 C36 C35 119.6(3) . . ?
C37 C36 C39 120.3(3) . . ?
C35 C36 C39 120.1(4) . . ?
C36 C37 C38 121.4(3) . . ?
C36 C37 H37 119.3 . . ?
C38 C37 H37 119.3 . . ?
C33 C38 C37 118.0(4) . . ?
C33 C38 H38 121.0 . . ?
C37 C38 H38 121.0 . . ?
F4 C39 F6 104.0(4) . . ?
F4 C39 F5 104.7(4) . . ?
F6 C39 F5 104.7(4) . . ?
F4 C39 C36 114.2(3) . . ?
F6 C39 C36 114.3(4) . . ?
F5 C39 C36 113.8(4) . . ?

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
_geom_torsion_publ_flag
F3 C1 C2 C3 -100.4(7) . . . . ?
F1 C1 C2 C3 134.6(5) . . . . ?
F2 C1 C2 C3 19.4(7) . . . . ?
F3 C1 C2 C7 78.5(7) . . . . ?
F1 C1 C2 C7 -46.5(6) . . . . ?
F2 C1 C2 C7 -161.7(5) . . . . ?
C7 C2 C3 C4 -1.0(6) . . . . ?
C1 C2 C3 C4 177.9(4) . . . . ?
C2 C3 C4 C5 -0.1(7) . . . . ?
C20 N1 C5 C4 -10.8(7) . . . . ?
C9 N1 C5 C4 -166.1(4) . . . . ?
C20 N1 C5 C6 171.2(4) . . . . ?
C9 N1 C5 C6 15.9(4) . . . . ?
C3 C4 C5 N1 -176.4(4) . . . . ?
C3 C4 C5 C6 1.4(6) . . . . ?
C7 C6 C5 N1 176.6(3) . . . . ?
C8 C6 C5 N1 2.5(4) . . . . ?
C7 C6 C5 C4 -1.6(6) . . . . ?
C8 C6 C5 C4 -175.7(4) . . . . ?
C5 N1 C9 C19 97.5(4) . . . . ?
C20 N1 C9 C19 -57.6(5) . . . . ?
C5 N1 C9 C16 -150.7(3) . . . . ?
C20 N1 C9 C16 54.2(5) . . . . ?
C5 N1 C9 C8 -26.1(4) . . . . ?
C20 N1 C9 C8 178.8(4) . . . . ?
C7 C6 C8 C10 46.0(5) . . . . ?
C5 C6 C8 C10 -140.7(3) . . . . ?
C7 C6 C8 C11 -71.3(5) . . . . ?
C5 C6 C8 C11 101.9(3) . . . . ?
C7 C6 C8 C9 169.2(4) . . . . ?
C5 C6 C8 C9 -17.5(3) . . . . ?
N1 C9 C8 C6 25.2(3) . . . . ?
C19 C9 C8 C6 -96.8(3) . . . . ?
C16 C9 C8 C6 146.0(3) . . . . ?
N1 C9 C8 C10 145.5(3) . . . . ?
C19 C9 C8 C10 23.5(5) . . . . ?
C16 C9 C8 C10 -93.8(4) . . . . ?
N1 C9 C8 C11 -88.5(3) . . . . ?
C19 C9 C8 C11 149.5(3) . . . . ?
C16 C9 C8 C11 32.2(4) . . . . ?
C5 C6 C7 C2 0.5(5) . . . . ?
C8 C6 C7 C2 173.1(3) . . . . ?
C3 C2 C7 C6 0.8(6) . . . . ?
C1 C2 C7 C6 -178.1(4) . . . . ?
C6 C8 C11 C15 -171.2(3) . . . . ?
C10 C8 C11 C15 68.9(4) . . . . ?
C9 C8 C11 C15 -61.2(4) . . . . ?
C6 C8 C11 C12 -44.0(4) . . . . ?
C10 C8 C11 C12 -163.8(3) . . . . ?
C9 C8 C11 C12 66.1(4) . . . . ?
C15 C11 C12 C13 -36.4(4) . . . . ?
C8 C11 C12 C13 -170.5(3) . . . . ?
C12 C11 C15 O1 -160.1(4) . . . . ?
C8 C11 C15 O1 -25.7(6) . . . . ?
C12 C11 C15 C14 20.2(4) . . . . ?
C8 C11 C15 C14 154.6(3) . . . . ?
N1 C9 C16 O2 37.7(5) . . . . ?
C19 C9 C16 O2 156.7(4) . . . . ?
C8 C9 C16 O2 -78.7(5) . . . . ?
N1 C9 C16 C17 -138.4(3) . . . . ?
C19 C9 C16 C17 -19.4(4) . . . . ?
C8 C9 C16 C17 105.2(3) . . . . ?
O2 C16 C17 C18 -178.5(4) . . . . ?
C9 C16 C17 C18 -2.4(5) . . . . ?
C19 C18 C17 C16 23.5(5) . . . . ?
C17 C18 C19 C9 -36.5(5) . . . . ?
N1 C9 C19 C18 151.4(3) . . . . ?
C16 C9 C19 C18 33.7(4) . . . . ?
C8 C9 C19 C18 -92.1(4) . . . . ?
C11 C12 C13 C14 39.1(4) . . . . ?
O1 C15 C14 C13 -175.8(4) . . . . ?
C11 C15 C14 C13 3.9(5) . . . . ?
C12 C13 C14 C15 -26.5(5) . . . . ?
C25 C21 C22 C23 -19.8(5) . . . . ?
C21 C22 C23 C24 34.2(5) . . . . ?
C33 N2 C24 C23 -93.7(4) . . . . ?
C018 N2 C24 C23 54.9(5) . . . . ?
C33 N2 C24 C25 154.6(3) . . . . ?
C018 N2 C24 C25 -56.8(5) . . . . ?
C33 N2 C24 C26 29.7(4) . . . . ?
C018 N2 C24 C26 178.3(3) . . . . ?
C22 C23 C24 N2 -151.2(4) . . . . ?
C22 C23 C24 C25 -33.4(4) . . . . ?
C22 C23 C24 C26 92.3(4) . . . . ?
C22 C21 C25 O3 174.0(4) . . . . ?
C22 C21 C25 C24 -1.4(5) . . . . ?
N2 C24 C25 O3 -34.7(5) . . . . ?
C23 C24 C25 O3 -153.8(4) . . . . ?
C26 C24 C25 O3 81.8(5) . . . . ?
N2 C24 C25 C21 140.9(3) . . . . ?
C23 C24 C25 C21 21.8(4) . . . . ?
C26 C24 C25 C21 -102.6(4) . . . . ?
N2 C24 C26 C34 -28.3(3) . . . . ?
C23 C24 C26 C34 93.8(3) . . . . ?
C25 C24 C26 C34 -149.2(3) . . . . ?
N2 C24 C26 C27 -147.8(3) . . . . ?
C23 C24 C26 C27 -25.7(4) . . . . ?
C25 C24 C26 C27 91.2(4) . . . . ?
N2 C24 C26 C28 86.2(3) . . . . ?
C23 C24 C26 C28 -151.7(3) . . . . ?
C25 C24 C26 C28 -34.8(4) . . . . ?
C34 C26 C28 C32 44.4(4) . . . . ?
C27 C26 C28 C32 164.9(3) . . . . ?
C24 C26 C28 C32 -65.1(4) . . . . ?
C34 C26 C28 C29 172.7(3) . . . . ?
C27 C26 C28 C29 -66.8(4) . . . . ?
C24 C26 C28 C29 63.2(4) . . . . ?
C32 C28 C29 O4 160.3(4) . . . . ?
C26 C28 C29 O4 24.2(6) . . . . ?
C32 C28 C29 C30 -18.7(4) . . . . ?
C26 C28 C29 C30 -154.8(4) . . . . ?
O4 C29 C30 C31 176.7(4) . . . . ?
C28 C29 C30 C31 -4.3(5) . . . . ?
C29 C30 C31 C32 25.4(6) . . . . ?
C29 C28 C32 C31 34.2(4) . . . . ?
C26 C28 C32 C31 168.7(3) . . . . ?
C30 C31 C32 C28 -37.1(5) . . . . ?
C018 N2 C33 C38 12.8(7) . . . . ?
C24 N2 C33 C38 162.0(4) . . . . ?
C018 N2 C33 C34 -167.9(4) . . . . ?
C24 N2 C33 C34 -18.7(4) . . . . ?
N2 C33 C34 C35 -178.7(3) . . . . ?
C38 C33 C34 C35 0.7(6) . . . . ?
N2 C33 C34 C26 -1.6(4) . . . . ?
C38 C33 C34 C26 177.8(4) . . . . ?
C27 C26 C34 C35 -41.7(5) . . . . ?
C28 C26 C34 C35 76.6(5) . . . . ?
C24 C26 C34 C35 -164.4(4) . . . . ?
C27 C26 C34 C33 141.6(4) . . . . ?
C28 C26 C34 C33 -100.1(3) . . . . ?
C24 C26 C34 C33 19.0(4) . . . . ?
C33 C34 C35 C36 -0.7(5) . . . . ?
C26 C34 C35 C36 -177.1(3) . . . . ?
C34 C35 C36 C37 -0.3(5) . . . . ?
C34 C35 C36 C39 178.8(4) . . . . ?
C35 C36 C37 C38 1.3(6) . . . . ?
C39 C36 C37 C38 -177.8(4) . . . . ?
N2 C33 C38 C37 179.5(4) . . . . ?
C34 C33 C38 C37 0.3(6) . . . . ?
C36 C37 C38 C33 -1.3(6) . . . . ?
C37 C36 C39 F4 122.8(5) . . . . ?
C35 C36 C39 F4 -56.2(6) . . . . ?
C37 C36 C39 F6 -117.5(5) . . . . ?
C35 C36 C39 F6 63.4(5) . . . . ?
C37 C36 C39 F5 2.8(6) . . . . ?
C35 C36 C39 F5 -176.3(4) . . . . ?

_refine_diff_density_max         0.592
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.053

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ba_a
_database_code_depnum_ccdc_archive 'CCDC 2050195'
loop_
_audit_author_name
_audit_author_address
'Yu-Yang Xie'
;Shanghai jiaotong university
China
;
_audit_update_record             
;
2020-12-14 deposited with the CCDC.	2021-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 F3 N O2'
_chemical_formula_sum            'C20 H22 F3 N O2'
_chemical_formula_weight         365.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.432
_cell_length_b                   10.4321(5)
_cell_length_c                   32.8983(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3580.2(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9922
_cell_measurement_theta_min      5.02
_cell_measurement_theta_max      68.11

_exptl_crystal_description       block
_exptl_crystal_colour            coulorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_F_000             1536
_exptl_transmission_factor_min   0.6447
_exptl_transmission_factor_max   0.7531
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.913
_shelx_estimated_absorpt_T_min   0.853
_shelx_estimated_absorpt_T_max   0.875
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26856
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         2.686
_diffrn_reflns_theta_max         68.348
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3276
_reflns_number_gt                2739
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1157P)²+1.9015P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3276
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0663
_refine_ls_wR_factor_ref         0.2081
_refine_ls_wR_factor_gt          0.1961
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
F1 F 0.6889(3) 0.4832(5) 0.52743(8) 0.191(2) Uani 1 1 d . . . . .
F2 F 0.7685(4) 0.3123(3) 0.51707(11) 0.198(2) Uani 1 1 d . . . . .
F3 F 0.8553(3) 0.4717(4) 0.49465(7) 0.1497(13) Uani 1 1 d . . . . .
O1 O 0.31139(16) 0.57824(18) 0.31427(6) 0.0628(5) Uani 1 1 d . . . . .
O2 O 0.5045(2) 0.7982(2) 0.30911(6) 0.0764(6) Uani 1 1 d . . . . .
N1 N 0.4609(2) 0.39370(19) 0.35563(6) 0.0524(5) Uani 1 1 d . . . . .
C1 C 0.7439(3) 0.4209(4) 0.49958(9) 0.0754(9) Uani 1 1 d . . . . .
C2 C 0.6689(3) 0.4071(3) 0.46172(8) 0.0583(6) Uani 1 1 d . . . . .
C3 C 0.5866(3) 0.3043(3) 0.45673(8) 0.0631(7) Uani 1 1 d . . . . .
H3 H 0.579821 0.243223 0.477203 0.076 Uiso 1 1 calc R U . . .
C4 C 0.5140(3) 0.2909(2) 0.42173(8) 0.0585(7) Uani 1 1 d . . . . .
H4 H 0.460299 0.220678 0.418197 0.070 Uiso 1 1 calc R U . . .
C5 C 0.5236(2) 0.3850(2) 0.39208(7) 0.0476(5) Uani 1 1 d . . . . .
C6 C 0.6041(2) 0.4910(2) 0.39730(7) 0.0448(5) Uani 1 1 d . . . . .
C7 C 0.6780(2) 0.5020(2) 0.43163(7) 0.0527(6) Uani 1 1 d . . . . .
H7 H 0.733103 0.571310 0.434903 0.063 Uiso 1 1 calc R U . . .
C8 C 0.5885(2) 0.5832(2) 0.36161(6) 0.0420(5) Uani 1 1 d . . . . .
C9 C 0.5220(2) 0.4900(2) 0.32928(7) 0.0425(5) Uani 1 1 d . . . . .
C10 C 0.3892(3) 0.2866(3) 0.33890(10) 0.0677(8) Uani 1 1 d . . . . .
H10A H 0.338870 0.315541 0.316262 0.102 Uiso 1 1 calc R U . . .
H10B H 0.333637 0.252025 0.359416 0.102 Uiso 1 1 calc R U . . .
H10C H 0.447745 0.221409 0.329968 0.102 Uiso 1 1 calc R U . . .
C11 C 0.6132(2) 0.4324(3) 0.29732(8) 0.0599(7) Uani 1 1 d . . . . .
H11A H 0.700565 0.430607 0.307438 0.072 Uiso 1 1 calc R U . . .
H11B H 0.587586 0.345710 0.290376 0.072 Uiso 1 1 calc R U . . .
C12 C 0.6024(3) 0.5206(3) 0.26039(9) 0.0737(8) Uani 1 1 d . . . . .
H12A H 0.654768 0.596674 0.263834 0.088 Uiso 1 1 calc R U . . .
H12B H 0.628577 0.476679 0.235770 0.088 Uiso 1 1 calc R U . . .
C13 C 0.4618(3) 0.5547(3) 0.25891(8) 0.0698(8) Uani 1 1 d . . . . .
H13A H 0.449832 0.639601 0.247468 0.084 Uiso 1 1 calc R U . . .
H13B H 0.414855 0.493362 0.242511 0.084 Uiso 1 1 calc R U . . .
C14 C 0.4169(2) 0.5509(2) 0.30209(7) 0.0492(6) Uani 1 1 d . . . . .
C15 C 0.7179(2) 0.6397(3) 0.34863(8) 0.0571(6) Uani 1 1 d . . . . .
H15A H 0.707596 0.686056 0.323635 0.086 Uiso 1 1 calc R U . . .
H15B H 0.778673 0.571661 0.344775 0.086 Uiso 1 1 calc R U . . .
H15C H 0.748497 0.696802 0.369362 0.086 Uiso 1 1 calc R U . . .
C16 C 0.4955(2) 0.6916(2) 0.37487(7) 0.0470(6) Uani 1 1 d . . . . .
H16 H 0.410122 0.653034 0.377111 0.056 Uiso 1 1 calc R U . . .
C17 C 0.4839(2) 0.8038(2) 0.34516(8) 0.0563(6) Uani 1 1 d . . . . .
C18 C 0.4482(4) 0.9229(3) 0.36813(11) 0.0769(9) Uani 1 1 d . . . . .
H18A H 0.367532 0.957359 0.358313 0.092 Uiso 1 1 calc R U . . .
H18B H 0.514010 0.987960 0.365268 0.092 Uiso 1 1 calc R U . . .
C19 C 0.4362(4) 0.8804(3) 0.41228(10) 0.0818(9) Uani 1 1 d . . . . .
H19A H 0.348009 0.859587 0.418887 0.098 Uiso 1 1 calc R U . . .
H19B H 0.465923 0.946973 0.430568 0.098 Uiso 1 1 calc R U . . .
C20 C 0.5215(3) 0.7613(3) 0.41519(9) 0.0682(8) Uani 1 1 d . . . . .
H20A H 0.497709 0.708524 0.438252 0.082 Uiso 1 1 calc R U . . .
H20B H 0.611189 0.784856 0.417601 0.082 Uiso 1 1 calc R U . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.261(4) . ?
F2 C1 1.297(4) . ?
F3 C1 1.287(4) . ?
O1 C14 1.205(3) . ?
O2 C17 1.207(3) . ?
N1 C5 1.369(3) . ?
N1 C10 1.453(3) . ?
N1 C9 1.472(3) . ?
C1 C2 1.478(4) . ?
C2 C3 1.384(4) . ?
C2 C7 1.404(4) . ?
C3 C4 1.385(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.399(3) . ?
C6 C7 1.372(3) . ?
C6 C8 1.527(3) . ?
C7 H7 0.9300 . ?
C8 C15 1.534(3) . ?
C8 C16 1.553(3) . ?
C8 C9 1.599(3) . ?
C9 C11 1.541(3) . ?
C9 C14 1.551(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.529(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.510(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.496(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.530(3) . ?
C16 C20 1.537(3) . ?
C16 H16 0.9800 . ?
C17 C18 1.501(4) . ?
C18 C19 1.524(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.531(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?

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
_geom_angle_publ_flag
C5 N1 C10 121.8(2) . . ?
C5 N1 C9 110.73(18) . . ?
C10 N1 C9 121.6(2) . . ?
F1 C1 F3 106.9(4) . . ?
F1 C1 F2 102.6(4) . . ?
F3 C1 F2 103.7(4) . . ?
F1 C1 C2 114.9(3) . . ?
F3 C1 C2 114.3(2) . . ?
F2 C1 C2 113.2(3) . . ?
C3 C2 C7 120.3(2) . . ?
C3 C2 C1 120.3(3) . . ?
C7 C2 C1 119.3(3) . . ?
C2 C3 C4 121.1(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 118.3(2) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
N1 C5 C4 128.9(2) . . ?
N1 C5 C6 110.0(2) . . ?
C4 C5 C6 121.1(2) . . ?
C7 C6 C5 120.3(2) . . ?
C7 C6 C8 129.8(2) . . ?
C5 C6 C8 109.82(19) . . ?
C6 C7 C2 118.9(2) . . ?
C6 C7 H7 120.5 . . ?
C2 C7 H7 120.5 . . ?
C6 C8 C15 111.25(18) . . ?
C6 C8 C16 108.02(17) . . ?
C15 C8 C16 110.37(19) . . ?
C6 C8 C9 100.08(16) . . ?
C15 C8 C9 115.52(18) . . ?
C16 C8 C9 110.99(17) . . ?
N1 C9 C11 113.79(19) . . ?
N1 C9 C14 108.27(18) . . ?
C11 C9 C14 101.72(18) . . ?
N1 C9 C8 102.19(16) . . ?
C11 C9 C8 114.99(18) . . ?
C14 C9 C8 116.17(17) . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C9 105.2(2) . . ?
C12 C11 H11A 110.7 . . ?
C9 C11 H11A 110.7 . . ?
C12 C11 H11B 110.7 . . ?
C9 C11 H11B 110.7 . . ?
H11A C11 H11B 108.8 . . ?
C13 C12 C11 103.9(2) . . ?
C13 C12 H12A 111.0 . . ?
C11 C12 H12A 111.0 . . ?
C13 C12 H12B 111.0 . . ?
C11 C12 H12B 111.0 . . ?
H12A C12 H12B 109.0 . . ?
C14 C13 C12 105.5(2) . . ?
C14 C13 H13A 110.6 . . ?
C12 C13 H13A 110.6 . . ?
C14 C13 H13B 110.6 . . ?
C12 C13 H13B 110.6 . . ?
H13A C13 H13B 108.8 . . ?
O1 C14 C13 126.5(2) . . ?
O1 C14 C9 123.4(2) . . ?
C13 C14 C9 109.7(2) . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C20 101.7(2) . . ?
C17 C16 C8 115.3(2) . . ?
C20 C16 C8 118.5(2) . . ?
C17 C16 H16 106.9 . . ?
C20 C16 H16 106.9 . . ?
C8 C16 H16 106.9 . . ?
O2 C17 C18 125.4(2) . . ?
O2 C17 C16 125.2(2) . . ?
C18 C17 C16 109.4(2) . . ?
C17 C18 C19 105.0(2) . . ?
C17 C18 H18A 110.7 . . ?
C19 C18 H18A 110.7 . . ?
C17 C18 H18B 110.7 . . ?
C19 C18 H18B 110.7 . . ?
H18A C18 H18B 108.8 . . ?
C18 C19 C20 104.4(3) . . ?
C18 C19 H19A 110.9 . . ?
C20 C19 H19A 110.9 . . ?
C18 C19 H19B 110.9 . . ?
C20 C19 H19B 110.9 . . ?
H19A C19 H19B 108.9 . . ?
C19 C20 C16 103.1(2) . . ?
C19 C20 H20A 111.1 . . ?
C16 C20 H20A 111.1 . . ?
C19 C20 H20B 111.1 . . ?
C16 C20 H20B 111.1 . . ?
H20A C20 H20B 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C2 C3 -89.3(4) . . . . ?
F3 C1 C2 C3 146.5(3) . . . . ?
F2 C1 C2 C3 28.1(5) . . . . ?
F1 C1 C2 C7 88.1(4) . . . . ?
F3 C1 C2 C7 -36.1(5) . . . . ?
F2 C1 C2 C7 -154.5(4) . . . . ?
C7 C2 C3 C4 1.6(4) . . . . ?
C1 C2 C3 C4 179.0(3) . . . . ?
C2 C3 C4 C5 -1.5(4) . . . . ?
C10 N1 C5 C4 -12.4(4) . . . . ?
C9 N1 C5 C4 -165.9(2) . . . . ?
C10 N1 C5 C6 168.6(2) . . . . ?
C9 N1 C5 C6 15.2(3) . . . . ?
C3 C4 C5 N1 -179.0(2) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
N1 C5 C6 C7 -179.3(2) . . . . ?
C4 C5 C6 C7 1.7(4) . . . . ?
N1 C5 C6 C8 3.1(3) . . . . ?
C4 C5 C6 C8 -175.9(2) . . . . ?
C5 C6 C7 C2 -1.5(4) . . . . ?
C8 C6 C7 C2 175.5(2) . . . . ?
C3 C2 C7 C6 -0.1(4) . . . . ?
C1 C2 C7 C6 -177.4(3) . . . . ?
C7 C6 C8 C15 42.3(3) . . . . ?
C5 C6 C8 C15 -140.4(2) . . . . ?
C7 C6 C8 C16 -79.0(3) . . . . ?
C5 C6 C8 C16 98.3(2) . . . . ?
C7 C6 C8 C9 164.9(2) . . . . ?
C5 C6 C8 C9 -17.8(2) . . . . ?
C5 N1 C9 C11 99.0(2) . . . . ?
C10 N1 C9 C11 -54.5(3) . . . . ?
C5 N1 C9 C14 -148.72(19) . . . . ?
C10 N1 C9 C14 57.8(3) . . . . ?
C5 N1 C9 C8 -25.6(2) . . . . ?
C10 N1 C9 C8 -179.1(2) . . . . ?
C6 C8 C9 N1 24.8(2) . . . . ?
C15 C8 C9 N1 144.32(19) . . . . ?
C16 C8 C9 N1 -89.1(2) . . . . ?
C6 C8 C9 C11 -99.0(2) . . . . ?
C15 C8 C9 C11 20.5(3) . . . . ?
C16 C8 C9 C11 147.1(2) . . . . ?
C6 C8 C9 C14 142.40(19) . . . . ?
C15 C8 C9 C14 -98.1(2) . . . . ?
C16 C8 C9 C14 28.5(2) . . . . ?
N1 C9 C11 C12 147.1(2) . . . . ?
C14 C9 C11 C12 30.9(2) . . . . ?
C8 C9 C11 C12 -95.5(2) . . . . ?
C9 C11 C12 C13 -38.5(3) . . . . ?
C11 C12 C13 C14 29.9(3) . . . . ?
C12 C13 C14 O1 176.3(3) . . . . ?
C12 C13 C14 C9 -10.6(3) . . . . ?
N1 C9 C14 O1 40.6(3) . . . . ?
C11 C9 C14 O1 160.7(2) . . . . ?
C8 C9 C14 O1 -73.6(3) . . . . ?
N1 C9 C14 C13 -132.8(2) . . . . ?
C11 C9 C14 C13 -12.6(3) . . . . ?
C8 C9 C14 C13 113.0(2) . . . . ?
C6 C8 C16 C17 171.25(19) . . . . ?
C15 C8 C16 C17 49.4(3) . . . . ?
C9 C8 C16 C17 -80.0(2) . . . . ?
C6 C8 C16 C20 50.5(3) . . . . ?
C15 C8 C16 C20 -71.4(3) . . . . ?
C9 C8 C16 C20 159.2(2) . . . . ?
C20 C16 C17 O2 154.6(3) . . . . ?
C8 C16 C17 O2 25.0(4) . . . . ?
C20 C16 C17 C18 -23.1(3) . . . . ?
C8 C16 C17 C18 -152.7(2) . . . . ?
O2 C17 C18 C19 -178.6(3) . . . . ?
C16 C17 C18 C19 -0.9(3) . . . . ?
C17 C18 C19 C20 24.9(3) . . . . ?
C18 C19 C20 C16 -39.6(3) . . . . ?
C17 C16 C20 C19 37.9(3) . . . . ?
C8 C16 C20 C19 165.4(2) . . . . ?

_refine_diff_density_max         0.875
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.050

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ta
_database_code_depnum_ccdc_archive 'CCDC 1992544'
loop_
_audit_author_name
_audit_author_address
'Yu-Yang Xie'
;Shanghai jiaotong university
China
;
_audit_update_record             
;
2020-12-14 deposited with the CCDC.	2021-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H23 N O2'
_chemical_formula_sum            'C19 H23 N O2'
_chemical_formula_weight         297.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.2267(7)
_cell_length_b                   21.6420(17)
_cell_length_c                   8.7088(7)
_cell_angle_alpha                90
_cell_angle_beta                 112.336(2)
_cell_angle_gamma                90
_cell_volume                     1608.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9858
_cell_measurement_theta_min      5.18
_cell_measurement_theta_max      68.14

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   0.6880
_exptl_transmission_factor_max   0.7531
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.623
_shelx_estimated_absorpt_T_min   0.886
_shelx_estimated_absorpt_T_max   0.886
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker d8 venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24900
_diffrn_reflns_av_unetI/netI     0.0134
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         5.182
_diffrn_reflns_theta_max         68.269
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             2913
_reflns_number_gt                2713
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0820P)²+0.3662P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2913
_refine_ls_number_parameters     205
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1478
_refine_ls_wR_factor_gt          0.1450
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O1 O 0.46637(17) 0.68909(7) 0.81312(19) 0.0867(5) Uani 1 1 d . . . . .
O2 O 0.61895(14) 0.55541(7) 0.76886(16) 0.0758(4) Uani 1 1 d . . . . .
N3 N 0.14543(16) 0.67082(6) 0.58767(19) 0.0585(4) Uani 1 1 d . . . . .
C1 C -0.1337(2) 0.63790(14) 0.1575(3) 0.0957(7) Uani 1 1 d . U . . .
H1 H -0.222028 0.652946 0.071793 0.115 Uiso 1 1 calc R U . . .
C2 C -0.0756(2) 0.67008(10) 0.3073(3) 0.0788(6) Uani 1 1 d . U . . .
H4 H -0.124319 0.705764 0.323276 0.095 Uiso 1 1 calc R U . . .
C3 C 0.05839(17) 0.64665(7) 0.4326(2) 0.0528(4) Uani 1 1 d . . . . .
C4 C 0.27055(15) 0.57800(6) 0.56102(16) 0.0402(3) Uani 1 1 d . . . . .
C5 C 0.41655(17) 0.65944(7) 0.4387(2) 0.0534(4) Uani 1 1 d . . . . .
H11 H 0.386465 0.692497 0.495757 0.064 Uiso 1 1 calc R U . . .
H15 H 0.346167 0.659340 0.322874 0.064 Uiso 1 1 calc R U . . .
C6 C 0.58749(19) 0.66668(9) 0.4558(2) 0.0648(5) Uani 1 1 d . . . . .
H14 H 0.606970 0.643710 0.369930 0.078 Uiso 1 1 calc R U . . .
H2 H 0.613096 0.709795 0.448982 0.078 Uiso 1 1 calc R U . . .
C7 C -0.0651(3) 0.58511(14) 0.1324(2) 0.0926(7) Uani 1 1 d . U . . .
H22 H -0.106097 0.565072 0.030395 0.111 Uiso 1 1 calc R U . . .
H23 H 0.418(2) 0.5663(8) 0.438(2) 0.054(4) Uiso 1 1 d . . . . .
C8 C 0.0654(2) 0.56127(10) 0.2583(2) 0.0651(5) Uani 1 1 d . . . . .
H3 H 0.112139 0.525062 0.242361 0.078 Uiso 1 1 calc R U . . .
C9 C 0.23989(16) 0.62118(7) 0.69304(17) 0.0466(4) Uani 1 1 d . . . . .
C10 C 0.3894(2) 0.64679(10) 0.8301(2) 0.0659(5) Uani 1 1 d . . . . .
C11 C 0.4181(3) 0.61325(16) 0.9896(3) 0.1107(10) Uani 1 1 d . . . . .
H10 H 0.413766 0.641727 1.073721 0.133 Uiso 1 1 calc R U . . .
H5 H 0.520480 0.593760 1.029585 0.133 Uiso 1 1 calc R U . . .
C12 C 0.2910(3) 0.56516(15) 0.9523(3) 0.1003(8) Uani 1 1 d . . . . .
H8 H 0.255953 0.561463 1.043768 0.120 Uiso 1 1 calc R U . . .
H9 H 0.328156 0.525189 0.932485 0.120 Uiso 1 1 calc R U . . .
C13 C 0.1593(2) 0.58851(9) 0.7970(2) 0.0637(5) Uani 1 1 d . . . . .
H6 H 0.092971 0.617210 0.825904 0.076 Uiso 1 1 calc R U . . .
H7 H 0.095414 0.554375 0.735324 0.076 Uiso 1 1 calc R U . . .
C14 C 0.68177(19) 0.64046(8) 0.6262(2) 0.0617(4) Uani 1 1 d . . . . .
H12 H 0.777939 0.621755 0.628024 0.074 Uiso 1 1 calc R U . . .
H13 H 0.707996 0.672653 0.709888 0.074 Uiso 1 1 calc R U . . .
C15 C 0.57730(17) 0.59256(7) 0.65722(18) 0.0491(4) Uani 1 1 d . . . . .
C16 C 0.2816(2) 0.50862(7) 0.6018(2) 0.0597(4) Uani 1 1 d . . . . .
H16 H 0.190242 0.495972 0.621105 0.090 Uiso 1 1 calc R U . . .
H17 H 0.373438 0.500920 0.699563 0.090 Uiso 1 1 calc R U . . .
H18 H 0.288132 0.485658 0.510372 0.090 Uiso 1 1 calc R U . . .
C18 C 0.12505(16) 0.59222(7) 0.40837(17) 0.0462(3) Uani 1 1 d . . . . .
C17 C 0.0860(3) 0.72108(9) 0.6565(3) 0.0899(7) Uani 1 1 d . . . . .
H21 H 0.073563 0.757209 0.588688 0.135 Uiso 1 1 calc R U . . .
H19 H 0.158607 0.729746 0.767153 0.135 Uiso 1 1 calc R U . . .
H20 H -0.013435 0.709653 0.659341 0.135 Uiso 1 1 calc R U . . .
C19 C 0.41462(15) 0.59699(6) 0.51999(16) 0.0410(3) Uani 1 1 d . . . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C10 1.202(2) . ?
O2 C15 1.2063(19) . ?
N3 C3 1.385(2) . ?
N3 C17 1.447(2) . ?
N3 C9 1.466(2) . ?
C1 C7 1.363(4) . ?
C1 C2 1.394(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.397(2) . ?
C2 H4 0.9300 . ?
C3 C18 1.382(2) . ?
C4 C18 1.5192(18) . ?
C4 C16 1.5374(19) . ?
C4 C19 1.5571(18) . ?
C4 C9 1.5882(18) . ?
C5 C19 1.529(2) . ?
C5 C6 1.535(2) . ?
C5 H11 0.9700 . ?
C5 H15 0.9700 . ?
C6 C14 1.516(3) . ?
C6 H14 0.9700 . ?
C6 H2 0.9700 . ?
C7 C8 1.384(3) . ?
C7 H22 0.9300 . ?
C8 C18 1.383(2) . ?
C8 H3 0.9300 . ?
C9 C13 1.544(2) . ?
C9 C10 1.544(2) . ?
C10 C11 1.498(3) . ?
C11 C12 1.508(4) . ?
C11 H10 0.9700 . ?
C11 H5 0.9700 . ?
C12 C13 1.521(3) . ?
C12 H8 0.9700 . ?
C12 H9 0.9700 . ?
C13 H6 0.9700 . ?
C13 H7 0.9700 . ?
C14 C15 1.508(2) . ?
C14 H12 0.9700 . ?
C14 H13 0.9700 . ?
C15 C19 1.5255(19) . ?
C16 H16 0.9600 . ?
C16 H17 0.9600 . ?
C16 H18 0.9600 . ?
C17 H21 0.9600 . ?
C17 H19 0.9600 . ?
C17 H20 0.9600 . ?
C19 H23 0.983(17) . ?

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
_geom_angle_publ_flag
C3 N3 C17 121.16(16) . . ?
C3 N3 C9 108.68(12) . . ?
C17 N3 C9 121.37(16) . . ?
C7 C1 C2 122.14(18) . . ?
C7 C1 H1 118.9 . . ?
C2 C1 H1 118.9 . . ?
C1 C2 C3 117.4(2) . . ?
C1 C2 H4 121.3 . . ?
C3 C2 H4 121.3 . . ?
C18 C3 N3 110.12(13) . . ?
C18 C3 C2 120.23(17) . . ?
N3 C3 C2 129.63(17) . . ?
C18 C4 C16 111.05(12) . . ?
C18 C4 C19 107.05(10) . . ?
C16 C4 C19 108.87(12) . . ?
C18 C4 C9 99.96(11) . . ?
C16 C4 C9 114.94(12) . . ?
C19 C4 C9 114.41(11) . . ?
C19 C5 C6 103.74(12) . . ?
C19 C5 H11 111.0 . . ?
C6 C5 H11 111.0 . . ?
C19 C5 H15 111.0 . . ?
C6 C5 H15 111.0 . . ?
H11 C5 H15 109.0 . . ?
C14 C6 C5 104.07(13) . . ?
C14 C6 H14 110.9 . . ?
C5 C6 H14 110.9 . . ?
C14 C6 H2 110.9 . . ?
C5 C6 H2 110.9 . . ?
H14 C6 H2 109.0 . . ?
C1 C7 C8 120.2(2) . . ?
C1 C7 H22 119.9 . . ?
C8 C7 H22 119.9 . . ?
C18 C8 C7 118.8(2) . . ?
C18 C8 H3 120.6 . . ?
C7 C8 H3 120.6 . . ?
N3 C9 C13 113.48(13) . . ?
N3 C9 C10 111.41(13) . . ?
C13 C9 C10 101.47(12) . . ?
N3 C9 C4 101.84(11) . . ?
C13 C9 C4 114.39(12) . . ?
C10 C9 C4 114.73(11) . . ?
O1 C10 C11 125.34(18) . . ?
O1 C10 C9 125.05(18) . . ?
C11 C10 C9 109.52(17) . . ?
C10 C11 C12 106.59(17) . . ?
C10 C11 H10 110.4 . . ?
C12 C11 H10 110.4 . . ?
C10 C11 H5 110.4 . . ?
C12 C11 H5 110.4 . . ?
H10 C11 H5 108.6 . . ?
C11 C12 C13 104.8(2) . . ?
C11 C12 H8 110.8 . . ?
C13 C12 H8 110.8 . . ?
C11 C12 H9 110.8 . . ?
C13 C12 H9 110.8 . . ?
H8 C12 H9 108.9 . . ?
C12 C13 C9 105.88(14) . . ?
C12 C13 H6 110.6 . . ?
C9 C13 H6 110.6 . . ?
C12 C13 H7 110.6 . . ?
C9 C13 H7 110.6 . . ?
H6 C13 H7 108.7 . . ?
C15 C14 C6 105.33(13) . . ?
C15 C14 H12 110.7 . . ?
C6 C14 H12 110.7 . . ?
C15 C14 H13 110.7 . . ?
C6 C14 H13 110.7 . . ?
H12 C14 H13 108.8 . . ?
O2 C15 C14 124.95(14) . . ?
O2 C15 C19 126.20(14) . . ?
C14 C15 C19 108.78(12) . . ?
C4 C16 H16 109.5 . . ?
C4 C16 H17 109.5 . . ?
H16 C16 H17 109.5 . . ?
C4 C16 H18 109.5 . . ?
H16 C16 H18 109.5 . . ?
H17 C16 H18 109.5 . . ?
C3 C18 C8 121.12(15) . . ?
C3 C18 C4 109.62(12) . . ?
C8 C18 C4 129.10(15) . . ?
N3 C17 H21 109.5 . . ?
N3 C17 H19 109.5 . . ?
H21 C17 H19 109.5 . . ?
N3 C17 H20 109.5 . . ?
H21 C17 H20 109.5 . . ?
H19 C17 H20 109.5 . . ?
C15 C19 C5 103.73(12) . . ?
C15 C19 C4 118.37(11) . . ?
C5 C19 C4 120.06(11) . . ?
C15 C19 H23 103.3(10) . . ?
C5 C19 H23 104.7(9) . . ?
C4 C19 H23 104.7(10) . . ?

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
_geom_torsion_publ_flag
C7 C1 C2 C3 0.8(3) . . . . ?
C17 N3 C3 C18 -168.41(15) . . . . ?
C9 N3 C3 C18 -20.56(16) . . . . ?
C17 N3 C3 C2 13.2(3) . . . . ?
C9 N3 C3 C2 161.05(15) . . . . ?
C1 C2 C3 C18 -2.6(2) . . . . ?
C1 C2 C3 N3 175.66(16) . . . . ?
C19 C5 C6 C14 -38.41(17) . . . . ?
C2 C1 C7 C8 0.8(3) . . . . ?
C1 C7 C8 C18 -0.6(3) . . . . ?
C3 N3 C9 C13 -92.71(15) . . . . ?
C17 N3 C9 C13 55.05(19) . . . . ?
C3 N3 C9 C10 153.51(12) . . . . ?
C17 N3 C9 C10 -58.73(19) . . . . ?
C3 N3 C9 C4 30.73(14) . . . . ?
C17 N3 C9 C4 178.49(14) . . . . ?
C18 C4 C9 N3 -28.22(13) . . . . ?
C16 C4 C9 N3 -147.16(12) . . . . ?
C19 C4 C9 N3 85.78(13) . . . . ?
C18 C4 C9 C13 94.60(14) . . . . ?
C16 C4 C9 C13 -24.34(18) . . . . ?
C19 C4 C9 C13 -151.40(13) . . . . ?
C18 C4 C9 C10 -148.70(13) . . . . ?
C16 C4 C9 C10 92.36(16) . . . . ?
C19 C4 C9 C10 -34.70(18) . . . . ?
N3 C9 C10 O1 -37.3(2) . . . . ?
C13 C9 C10 O1 -158.35(18) . . . . ?
C4 C9 C10 O1 77.8(2) . . . . ?
N3 C9 C10 C11 139.48(18) . . . . ?
C13 C9 C10 C11 18.4(2) . . . . ?
C4 C9 C10 C11 -105.48(18) . . . . ?
O1 C10 C11 C12 178.7(2) . . . . ?
C9 C10 C11 C12 2.0(3) . . . . ?
C10 C11 C12 C13 -22.1(3) . . . . ?
C11 C12 C13 C9 34.3(2) . . . . ?
N3 C9 C13 C12 -151.54(17) . . . . ?
C10 C9 C13 C12 -31.9(2) . . . . ?
C4 C9 C13 C12 92.20(19) . . . . ?
C5 C6 C14 C15 28.76(18) . . . . ?
C6 C14 C15 O2 168.68(16) . . . . ?
C6 C14 C15 C19 -8.48(18) . . . . ?
N3 C3 C18 C8 -175.72(13) . . . . ?
C2 C3 C18 C8 2.8(2) . . . . ?
N3 C3 C18 C4 0.11(16) . . . . ?
C2 C3 C18 C4 178.67(13) . . . . ?
C7 C8 C18 C3 -1.2(2) . . . . ?
C7 C8 C18 C4 -176.15(15) . . . . ?
C16 C4 C18 C3 139.76(13) . . . . ?
C19 C4 C18 C3 -101.52(13) . . . . ?
C9 C4 C18 C3 18.00(14) . . . . ?
C16 C4 C18 C8 -44.8(2) . . . . ?
C19 C4 C18 C8 73.89(18) . . . . ?
C9 C4 C18 C8 -166.60(14) . . . . ?
O2 C15 C19 C5 167.71(16) . . . . ?
C14 C15 C19 C5 -15.17(15) . . . . ?
O2 C15 C19 C4 31.8(2) . . . . ?
C14 C15 C19 C4 -151.06(13) . . . . ?
C6 C5 C19 C15 32.60(16) . . . . ?
C6 C5 C19 C4 167.55(13) . . . . ?
C18 C4 C19 C15 175.15(12) . . . . ?
C16 C4 C19 C15 -64.72(16) . . . . ?
C9 C4 C19 C15 65.40(16) . . . . ?
C18 C4 C19 C5 46.53(16) . . . . ?
C16 C4 C19 C5 166.65(13) . . . . ?
C9 C4 C19 C5 -63.22(16) . . . . ?

_refine_diff_density_max         0.219
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.031

