# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_200717_fjf_044_dj_0m
_database_code_depnum_ccdc_archive 'CCDC 2087902'
loop_
_audit_author_name
_audit_author_address
'Trifluoromethylated chromanone-fused Bicycle'
;Zhejiang University of Science and Technolgoy
China
;
_audit_update_record             
;
2021-06-03 deposited with the CCDC.	2021-09-13 downloaded from the CCDC.
;
_audit_creation_date             2020-07-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H13 F3 O3'
_chemical_formula_sum            'C21 H13 F3 O3'
_chemical_formula_weight         370.31
_chemical_melting_point          ?
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.411(4)
_cell_length_b                   9.622(4)
_cell_length_c                   11.004(4)
_cell_angle_alpha                82.333(14)
_cell_angle_beta                 70.00(2)
_cell_angle_gamma                79.92(2)
_cell_volume                     821.4(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6956
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.10
_cell_measurement_theta_min      2.71
_shelx_estimated_absorpt_T_max   0.965
_shelx_estimated_absorpt_T_min   0.946
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7132
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1091 before and 0.0360 after correction.
The Ratio of minimum to maximum transmission is 0.9567.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.29
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10186
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.057
_diffrn_reflns_theta_min         2.602
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'zju Bruker D8 Venture Ims3.0'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3309
_reflns_number_total             3600
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       SAINT
_computing.data_collection       Bruker
_computing.data_reduction        SAINT
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3600
_refine_ls_number_restraints     87
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0436
_refine_ls_restrained_S_all      1.138
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0445P)²+0.4416P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1083
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 F2-C21 \\sim F2A-C21
 with sigma of 0.02
 F3-C21 \\sim F3A-C21
 with sigma of 0.02
 C21-F1 \\sim C21-F1A
 with sigma of 0.02
3. Rigid bond restraints
 C21, F1, F2, F3, F1A, F2A, F3A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
C21 \\sim F1 \\sim F2 \\sim F3 \\sim F1A \\sim F2A \\sim F3A: within 1.7A with
sigma of 0.01 and sigma for terminal atoms of 0.02
5. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C7(H7), C12(H12)
6.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
6.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.05196(13) 0.81784(10) 0.95079(9) 0.0281(2) Uani 1 1 d . . . . .
O2 O -0.04243(13) 0.94386(11) 0.80177(10) 0.0313(2) Uani 1 1 d . . . . .
O3 O 0.59886(13) 0.57816(12) 0.61355(10) 0.0336(3) Uani 1 1 d . . . . .
C1 C 0.26876(18) 0.45280(15) 0.97545(14) 0.0289(3) Uani 1 1 d . . . . .
H1 H 0.302330 0.368235 0.931909 0.035 Uiso 1 1 calc R . . . .
C2 C 0.29895(19) 0.45437(17) 1.09202(15) 0.0335(3) Uani 1 1 d . . . . .
H2 H 0.351806 0.371106 1.127483 0.040 Uiso 1 1 calc R . . . .
C3 C 0.25208(19) 0.57708(18) 1.15643(14) 0.0329(3) Uani 1 1 d . . . . .
H3 H 0.274420 0.578323 1.235241 0.039 Uiso 1 1 calc R . . . .
C4 C 0.17272(18) 0.69778(16) 1.10583(13) 0.0296(3) Uani 1 1 d . . . . .
H4 H 0.139726 0.782274 1.149464 0.036 Uiso 1 1 calc R . . . .
C5 C 0.14207(16) 0.69339(14) 0.99011(13) 0.0239(3) Uani 1 1 d . . . . .
C6 C 0.18994(16) 0.57340(14) 0.92119(12) 0.0229(3) Uani 1 1 d . . . . .
C7 C 0.16032(17) 0.57785(13) 0.79182(12) 0.0234(3) Uani 1 1 d . . . . .
H7 H 0.053654 0.538695 0.801575 0.028 Uiso 1 1 calc R . . . .
C8 C 0.15496(16) 0.73368(13) 0.73300(12) 0.0209(3) Uani 1 1 d . . . . .
C9 C 0.04663(16) 0.84038(14) 0.82772(13) 0.0227(3) Uani 1 1 d . . . . .
C10 C 0.31706(19) 0.50225(14) 0.69213(13) 0.0286(3) Uani 1 1 d . . . . .
H10A H 0.362196 0.412226 0.731566 0.034 Uiso 1 1 calc R . . . .
H10B H 0.288385 0.482094 0.616746 0.034 Uiso 1 1 calc R . . . .
C11 C 0.44505(17) 0.60671(14) 0.65214(12) 0.0244(3) Uani 1 1 d . . . . .
C12 C 0.34818(15) 0.75730(13) 0.66355(12) 0.0212(3) Uani 1 1 d . . . . .
H12 H 0.393143 0.827832 0.697701 0.025 Uiso 1 1 calc R . . . .
C13 C 0.29974(16) 0.80229(13) 0.54059(12) 0.0219(3) Uani 1 1 d . . . . .
C14 C 0.13946(17) 0.76999(14) 0.59833(12) 0.0234(3) Uani 1 1 d . . . . .
C15 C 0.41129(16) 0.84782(13) 0.41228(13) 0.0227(3) Uani 1 1 d . . . . .
C16 C 0.58476(17) 0.84762(14) 0.39375(14) 0.0268(3) Uani 1 1 d . . . . .
H16 H 0.626327 0.822369 0.464973 0.032 Uiso 1 1 calc R . . . .
C17 C 0.69644(18) 0.88417(15) 0.27166(16) 0.0327(3) Uani 1 1 d . . . . .
H17 H 0.814208 0.881731 0.259661 0.039 Uiso 1 1 calc R . . . .
C18 C 0.6370(2) 0.92403(17) 0.16768(15) 0.0371(4) Uani 1 1 d . . . . .
H18 H 0.713523 0.948506 0.084351 0.044 Uiso 1 1 calc R . . . .
C19 C 0.4645(2) 0.9280(2) 0.18607(15) 0.0411(4) Uani 1 1 d . . . . .
H19 H 0.423031 0.956913 0.115153 0.049 Uiso 1 1 calc R . . . .
C20 C 0.35201(19) 0.89013(17) 0.30706(14) 0.0329(3) Uani 1 1 d . . . . .
H20 H 0.234387 0.893013 0.318304 0.039 Uiso 1 1 calc R . . . .
C21 C -0.00644(19) 0.75778(19) 0.55469(14) 0.0347(3) Uani 1 1 d D U . . .
F1 F 0.0288(3) 0.6673(3) 0.4703(3) 0.0901(11) Uani 0.723(4) 1 d D U P A 1
F2 F -0.1446(3) 0.7410(4) 0.6534(2) 0.0742(9) Uani 0.723(4) 1 d D U P A 1
F3 F -0.0561(2) 0.8828(2) 0.4922(2) 0.0610(6) Uani 0.723(4) 1 d D U P A 1
F1A F -0.0230(7) 0.6100(5) 0.5757(8) 0.0678(17) Uani 0.277(4) 1 d D U P A 2
F2A F -0.1502(8) 0.7998(10) 0.6251(8) 0.089(2) Uani 0.277(4) 1 d D U P A 2
F3A F 0.0103(9) 0.7853(11) 0.4376(5) 0.091(3) Uani 0.277(4) 1 d D U P A 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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.4014(17) . ?
O1 C9 1.3575(17) . ?
O2 C9 1.2015(17) . ?
O3 C11 1.2085(18) . ?
C1 H1 0.9500 . ?
C1 C2 1.393(2) . ?
C1 C6 1.3997(19) . ?
C2 H2 0.9500 . ?
C2 C3 1.386(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.3903(19) . ?
C5 C6 1.3901(19) . ?
C6 C7 1.5209(18) . ?
C7 H7 1.0000 . ?
C7 C8 1.5512(18) . ?
C7 C10 1.5359(19) . ?
C8 C9 1.5097(18) . ?
C8 C12 1.5844(19) . ?
C8 C14 1.5210(18) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.516(2) . ?
C11 C12 1.5312(18) . ?
C12 H12 1.0000 . ?
C12 C13 1.5308(18) . ?
C13 C14 1.3512(19) . ?
C13 C15 1.4624(19) . ?
C14 C21 1.490(2) . ?
C15 C16 1.402(2) . ?
C15 C20 1.398(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.392(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.383(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.389(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.389(2) . ?
C20 H20 0.9500 . ?
C21 F1 1.283(2) . ?
C21 F2 1.308(3) . ?
C21 F3 1.377(2) . ?
C21 F1A 1.433(5) . ?
C21 F2A 1.224(6) . ?
C21 F3A 1.245(5) . ?

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
C9 O1 C5 120.66(10) . . ?
C2 C1 H1 119.4 . . ?
C2 C1 C6 121.29(14) . . ?
C6 C1 H1 119.4 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.19(14) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 119.93(14) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 118.92(14) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 O1 114.72(12) . . ?
C6 C5 O1 122.25(12) . . ?
C6 C5 C4 122.97(13) . . ?
C1 C6 C7 123.00(12) . . ?
C5 C6 C1 116.68(13) . . ?
C5 C6 C7 120.30(12) . . ?
C6 C7 H7 111.8 . . ?
C6 C7 C8 107.76(10) . . ?
C6 C7 C10 110.74(11) . . ?
C8 C7 H7 111.8 . . ?
C10 C7 H7 111.8 . . ?
C10 C7 C8 102.61(11) . . ?
C7 C8 C12 105.72(10) . . ?
C9 C8 C7 114.31(11) . . ?
C9 C8 C12 115.88(10) . . ?
C9 C8 C14 112.68(11) . . ?
C14 C8 C7 119.93(11) . . ?
C14 C8 C12 84.66(9) . . ?
O1 C9 C8 117.30(11) . . ?
O2 C9 O1 117.90(12) . . ?
O2 C9 C8 124.80(12) . . ?
C7 C10 H10A 111.0 . . ?
C7 C10 H10B 111.0 . . ?
H10A C10 H10B 109.0 . . ?
C11 C10 C7 103.89(11) . . ?
C11 C10 H10A 111.0 . . ?
C11 C10 H10B 111.0 . . ?
O3 C11 C10 126.40(13) . . ?
O3 C11 C12 124.62(13) . . ?
C10 C11 C12 108.95(11) . . ?
C8 C12 H12 117.9 . . ?
C11 C12 C8 103.65(10) . . ?
C11 C12 H12 117.9 . . ?
C13 C12 C8 86.37(10) . . ?
C13 C12 C11 108.14(10) . . ?
C13 C12 H12 117.9 . . ?
C14 C13 C12 92.86(11) . . ?
C14 C13 C15 139.48(12) . . ?
C15 C13 C12 127.40(12) . . ?
C13 C14 C8 95.69(11) . . ?
C13 C14 C21 135.88(13) . . ?
C21 C14 C8 128.25(12) . . ?
C16 C15 C13 118.75(12) . . ?
C20 C15 C13 122.52(12) . . ?
C20 C15 C16 118.73(13) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.42(14) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.40(14) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 120.3 . . ?
C17 C18 C19 119.49(14) . . ?
C19 C18 H18 120.3 . . ?
C18 C19 H19 119.6 . . ?
C18 C19 C20 120.71(15) . . ?
C20 C19 H19 119.6 . . ?
C15 C20 H20 119.9 . . ?
C19 C20 C15 120.22(14) . . ?
C19 C20 H20 119.9 . . ?
F1 C21 C14 113.98(15) . . ?
F1 C21 F2 113.6(2) . . ?
F1 C21 F3 103.5(2) . . ?
F2 C21 C14 111.38(17) . . ?
F2 C21 F3 102.21(19) . . ?
F3 C21 C14 111.24(14) . . ?
F1A C21 C14 104.9(2) . . ?
F2A C21 C14 117.3(4) . . ?
F2A C21 F1A 96.7(5) . . ?
F2A C21 F3A 112.4(6) . . ?
F3A C21 C14 118.2(3) . . ?
F3A C21 F1A 103.3(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mo_210430_fjf_130_dj_0m
_database_code_depnum_ccdc_archive 'CCDC 2087906'
loop_
_audit_author_name
_audit_author_address
'Trifluoromethylated bicycle'
;Zhejiang University of Science and Technolgoy
China
;
_audit_update_record             
;
2021-06-03 deposited with the CCDC.	2021-09-13 downloaded from the CCDC.
;
_audit_creation_date             2021-05-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H19 F3 O4'
_chemical_formula_sum            'C22 H19 F3 O4'
_chemical_formula_weight         404.37
_chemical_melting_point          ?
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.2823(12)
_cell_length_b                   14.0355(14)
_cell_length_c                   19.007(2)
_cell_angle_alpha                83.638(4)
_cell_angle_beta                 73.089(4)
_cell_angle_gamma                65.017(4)
_cell_volume                     2841.3(5)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    9878
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      26.84
_cell_measurement_theta_min      2.46
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1045 before and 0.0815 after correction.
The Ratio of minimum to maximum transmission is 0.9070.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1260
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0783
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            53908
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.212
_diffrn_reflns_theta_min         1.966
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8602
_reflns_number_total             12491
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.702
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     845
_refine_ls_number_reflns         12491
_refine_ls_number_restraints     195
_refine_ls_R_factor_all          0.1034
_refine_ls_R_factor_gt           0.0692
_refine_ls_restrained_S_all      1.035
_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)+(0.0807P)²+2.5780P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1750
_refine_ls_wR_factor_ref         0.2011
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C13-C17 \\sim C13-C17A
 with sigma of 0.02
 C17-C18 \\sim C17A-C18A
 with sigma of 0.02
 C17-C22 \\sim C17A-C22A
 with sigma of 0.02
 C18-C19 \\sim C18A-C19A
 with sigma of 0.02
 C19-C20 \\sim C19A-C20A
 with sigma of 0.02
 C20-C21 \\sim C20A-C21A
 with sigma of 0.02
 C21-C22 \\sim C21A-C22A
 with sigma of 0.02
 C13-C18 \\sim C13-C18A
 with sigma of 0.04
 C13-C22 \\sim C13-C22A
 with sigma of 0.04
 C17-C19 \\sim C17A-C19A
 with sigma of 0.04
 C17-C21 \\sim C17A-C21A
 with sigma of 0.04
 C18-C20 \\sim C18A-C20A
 with sigma of 0.04
 C18-C22 \\sim C18A-C22A
 with sigma of 0.04
 C19-C21 \\sim C19A-C21A
 with sigma of 0.04
 C20-C22 \\sim C20A-C22A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C13 \\sim C17 \\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim C17A
\\sim C18A \\sim C19A \\sim C20A \\sim C21A \\sim C22A: within 1.7A with sigma
of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(H13A)=Sof(C17A)=Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=
 Sof(H20A)=Sof(C21A)=Sof(H21A)=Sof(C22A)=Sof(H22A)=1-FVAR(1)
 Sof(H13)=Sof(C17)=Sof(C18)=Sof(H18)=Sof(C19)=Sof(H19)=Sof(C20)=Sof(H20)=
 Sof(C21)=Sof(H21)=Sof(C22)=Sof(H22)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C7(H7), C10(H10), C12(H12), C13(H13), C13(H13A), C29(H29), C32(H32), C34(H34),
  C35(H35), C51(H51), C54(H54), C56(H56), C57(H57)
5.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C30(H30A,H30B), C52(H52A,H52B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C18(H18), C19(H19), C20(H20), C21(H21),
 C22(H22), C18A(H18A), C19A(H19A), C20A(H20A), C21A(H21A), C22A(H22A), C24(H24),
  C25(H25), C26(H26), C27(H27), C40(H40), C41(H41), C42(H42), C43(H43),
 C44(H44), C46(H46), C47(H47), C48(H48), C49(H49), C62(H62), C63(H63), C64(H64),
  C65(H65), C66(H66)
5.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C37(H37A,H37B,H37C), C59(H59A,H59B,H59C)
5.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O5(H5A), O9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.01551(17) 0.34442(17) 0.53472(10) 0.0578(5) Uani 1 1 d . . . . .
F2 F 0.0152(2) 0.2097(2) 0.49000(14) 0.0965(9) Uani 1 1 d . . . . .
F3 F 0.0126(2) 0.21260(19) 0.60278(14) 0.0927(9) Uani 1 1 d . . . . .
O1 O -0.42348(19) 0.58144(17) 0.73401(11) 0.0454(5) Uani 1 1 d . . . . .
H1 H -0.500381 0.602055 0.754140 0.068 Uiso 1 1 calc GR . . . .
O2 O -0.32879(19) 0.64520(15) 0.55947(11) 0.0437(5) Uani 1 1 d . . . . .
O3 O -0.42813(19) 0.36115(19) 0.71505(12) 0.0517(6) Uani 1 1 d . . . . .
O4 O -0.24067(18) 0.25667(15) 0.73078(10) 0.0398(5) Uani 1 1 d . . . . .
C1 C -0.3591(3) 0.5333(2) 0.78477(16) 0.0401(7) Uani 1 1 d . . . . .
C2 C -0.4119(4) 0.5540(2) 0.85956(17) 0.0489(8) Uani 1 1 d . . . . .
H2 H -0.497101 0.600296 0.877755 0.059 Uiso 1 1 calc R . . . .
C3 C -0.3378(4) 0.5056(3) 0.90783(19) 0.0608(10) Uani 1 1 d . . . . .
H3 H -0.373183 0.518034 0.959291 0.073 Uiso 1 1 calc R . . . .
C4 C -0.2138(4) 0.4402(3) 0.8810(2) 0.0636(11) Uani 1 1 d . . . . .
H4 H -0.163087 0.409434 0.913849 0.076 Uiso 1 1 calc R . . . .
C5 C -0.1631(4) 0.4191(3) 0.8067(2) 0.0528(9) Uani 1 1 d . . . . .
H5 H -0.077724 0.372922 0.788937 0.063 Uiso 1 1 calc R . . . .
C6 C -0.2344(3) 0.4643(2) 0.75714(17) 0.0398(7) Uani 1 1 d . . . . .
C7 C -0.1780(3) 0.4382(2) 0.67560(16) 0.0374(6) Uani 1 1 d . . . . .
H7 H -0.088945 0.386908 0.667662 0.045 Uiso 1 1 calc R . . . .
C8 C -0.1820(3) 0.5349(2) 0.62728(17) 0.0395(6) Uani 1 1 d . . . . .
H8A H -0.199054 0.594863 0.657953 0.047 Uiso 1 1 calc R . . . .
H8B H -0.100995 0.518595 0.589853 0.047 Uiso 1 1 calc R . . . .
C9 C -0.2850(2) 0.5621(2) 0.59043(15) 0.0359(6) Uani 1 1 d . . . . .
C10 C -0.3243(2) 0.4726(2) 0.59667(14) 0.0349(6) Uani 1 1 d . . . . .
H10 H -0.416394 0.494076 0.615670 0.042 Uiso 1 1 calc R . . . .
C11 C -0.2476(2) 0.3888(2) 0.64335(14) 0.0327(6) Uani 1 1 d . . . . .
C12 C -0.1728(3) 0.3151(2) 0.57306(15) 0.0422(7) Uani 1 1 d . . . . .
H12 H -0.195080 0.253213 0.582304 0.051 Uiso 1 1 calc R . . . .
C13 C -0.2608(3) 0.3955(2) 0.52886(15) 0.0414(7) Uani 1 1 d D U . . .
H13 H -0.322142 0.366526 0.528218 0.050 Uiso 0.811(5) 1 calc R . P A 1
H13A H -0.322450 0.366192 0.529598 0.050 Uiso 0.189(5) 1 calc R . P A 2
C14 C -0.3185(3) 0.3371(2) 0.70045(14) 0.0331(6) Uani 1 1 d . . . . .
C15 C -0.2980(3) 0.2021(3) 0.78868(17) 0.0507(8) Uani 1 1 d . . . . .
H15A H -0.341128 0.171229 0.768685 0.076 Uiso 1 1 calc GR . . . .
H15B H -0.358176 0.252024 0.828326 0.076 Uiso 1 1 calc GR . . . .
H15C H -0.233394 0.146312 0.808072 0.076 Uiso 1 1 calc GR . . . .
C16 C -0.0339(3) 0.2726(3) 0.5496(2) 0.0613(10) Uani 1 1 d . . . . .
C17 C -0.2233(4) 0.4336(3) 0.4510(2) 0.0371(11) Uani 0.811(5) 1 d D U P A 1
C18 C -0.3228(6) 0.4952(4) 0.4226(3) 0.0529(15) Uani 0.811(5) 1 d D U P A 1
H18 H -0.405613 0.510795 0.452007 0.063 Uiso 0.811(5) 1 calc R . P A 1
C19 C -0.3038(6) 0.5341(5) 0.3523(3) 0.0562(16) Uani 0.811(5) 1 d D U P A 1
H19 H -0.373512 0.575793 0.333921 0.067 Uiso 0.811(5) 1 calc R . P A 1
C20 C -0.1852(4) 0.5133(4) 0.3086(2) 0.0466(12) Uani 0.811(5) 1 d D U P A 1
H20 H -0.172275 0.541314 0.260549 0.056 Uiso 0.811(5) 1 calc R . P A 1
C21 C -0.0859(4) 0.4512(4) 0.3357(2) 0.0524(11) Uani 0.811(5) 1 d D U P A 1
H21 H -0.003434 0.435202 0.305635 0.063 Uiso 0.811(5) 1 calc R . P A 1
C22 C -0.1037(4) 0.4114(4) 0.40632(19) 0.0469(10) Uani 0.811(5) 1 d D U P A 1
H22 H -0.033595 0.368635 0.424071 0.056 Uiso 0.811(5) 1 calc R . P A 1
C17A C -0.253(2) 0.457(2) 0.4585(10) 0.043(3) Uani 0.189(5) 1 d D U P A 2
C18A C -0.335(2) 0.468(2) 0.4183(12) 0.043(3) Uani 0.189(5) 1 d D U P A 2
H18A H -0.400133 0.445220 0.438123 0.052 Uiso 0.189(5) 1 calc R . P A 2
C19A C -0.321(3) 0.511(2) 0.3494(13) 0.046(3) Uani 0.189(5) 1 d D U P A 2
H19A H -0.379444 0.522328 0.322488 0.055 Uiso 0.189(5) 1 calc R . P A 2
C20A C -0.223(2) 0.538(2) 0.3205(11) 0.046(3) Uani 0.189(5) 1 d D U P A 2
H20A H -0.206110 0.557409 0.270363 0.055 Uiso 0.189(5) 1 calc R . P A 2
C21A C -0.1473(16) 0.5374(16) 0.3612(8) 0.051(3) Uani 0.189(5) 1 d D U P A 2
H21A H -0.084923 0.563511 0.341569 0.061 Uiso 0.189(5) 1 calc R . P A 2
C22A C -0.1640(15) 0.4979(14) 0.4320(7) 0.044(3) Uani 0.189(5) 1 d D U P A 2
H22A H -0.114671 0.498781 0.462029 0.052 Uiso 0.189(5) 1 calc R . P A 2
F4 F -0.01920(15) 0.72605(15) 0.88481(9) 0.0466(4) Uani 1 1 d . . . . .
F5 F -0.01254(18) 0.59193(16) 0.83719(10) 0.0603(5) Uani 1 1 d . . . . .
F6 F 0.00921(16) 0.58454(15) 0.94661(10) 0.0593(6) Uani 1 1 d . . . . .
O5 O -0.44073(17) 0.94927(15) 1.09227(10) 0.0355(4) Uani 1 1 d . . . . .
H5A H -0.516079 0.958714 1.105422 0.053 Uiso 1 1 calc GR . . . .
O6 O -0.32493(18) 0.99891(14) 0.91334(10) 0.0363(4) Uani 1 1 d . . . . .
O7 O -0.44849(18) 0.72574(17) 1.07500(11) 0.0444(5) Uani 1 1 d . . . . .
O8 O -0.26073(17) 0.60755(14) 1.08264(10) 0.0372(5) Uani 1 1 d . . . . .
C23 C -0.3835(3) 0.8935(2) 1.14507(14) 0.0318(6) Uani 1 1 d . . . . .
C24 C -0.4442(3) 0.9128(2) 1.21963(15) 0.0385(6) Uani 1 1 d . . . . .
H24 H -0.527549 0.964122 1.235212 0.046 Uiso 1 1 calc R . . . .
C25 C -0.3815(3) 0.8560(3) 1.27083(16) 0.0465(8) Uani 1 1 d . . . . .
H25 H -0.422374 0.868179 1.321847 0.056 Uiso 1 1 calc R . . . .
C26 C -0.2604(3) 0.7821(3) 1.24822(16) 0.0481(8) Uani 1 1 d . . . . .
H26 H -0.217460 0.744241 1.283556 0.058 Uiso 1 1 calc R . . . .
C27 C -0.2014(3) 0.7631(2) 1.17386(16) 0.0407(7) Uani 1 1 d . . . . .
H27 H -0.118237 0.711414 1.158803 0.049 Uiso 1 1 calc R . . . .
C28 C -0.2614(2) 0.8182(2) 1.12063(14) 0.0317(6) Uani 1 1 d . . . . .
C29 C -0.1973(2) 0.7948(2) 1.03912(14) 0.0305(5) Uani 1 1 d . . . . .
H29 H -0.108920 0.742903 1.032997 0.037 Uiso 1 1 calc R . . . .
C30 C -0.1983(2) 0.8932(2) 0.99364(14) 0.0324(6) Uani 1 1 d . . . . .
H30A H -0.222128 0.952818 1.026598 0.039 Uiso 1 1 calc R . . . .
H30B H -0.114453 0.878971 0.960040 0.039 Uiso 1 1 calc R . . . .
C31 C -0.2924(2) 0.9194(2) 0.95007(13) 0.0300(5) Uani 1 1 d . . . . .
C32 C -0.3409(2) 0.83535(19) 0.95730(13) 0.0271(5) Uani 1 1 d . . . . .
H32 H -0.433213 0.861622 0.978946 0.033 Uiso 1 1 calc R . . . .
C33 C -0.2647(2) 0.74813(19) 1.00270(13) 0.0272(5) Uani 1 1 d . . . . .
C34 C -0.1921(2) 0.6764(2) 0.93123(14) 0.0306(5) Uani 1 1 d . . . . .
H34 H -0.206818 0.610669 0.940232 0.037 Uiso 1 1 calc R . . . .
C35 C -0.2894(2) 0.75699(19) 0.89125(13) 0.0289(5) Uani 1 1 d . . . . .
H35 H -0.353605 0.728535 0.897065 0.035 Uiso 1 1 calc R . . . .
C36 C -0.3374(2) 0.69486(19) 1.05732(13) 0.0279(5) Uani 1 1 d . . . . .
C37 C -0.3205(3) 0.5511(3) 1.13717(17) 0.0462(7) Uani 1 1 d . . . . .
H37A H -0.367754 0.526998 1.115333 0.069 Uiso 1 1 calc GR . . . .
H37B H -0.377305 0.597832 1.179182 0.069 Uiso 1 1 calc GR . . . .
H37C H -0.256765 0.490298 1.153789 0.069 Uiso 1 1 calc GR . . . .
C38 C -0.0551(3) 0.6464(2) 0.89998(15) 0.0401(7) Uani 1 1 d . . . . .
C39 C -0.2630(2) 0.7910(2) 0.81207(13) 0.0302(5) Uani 1 1 d . . . . .
C40 C -0.1818(3) 0.8394(2) 0.78095(15) 0.0389(6) Uani 1 1 d . . . . .
H40 H -0.136740 0.850836 0.809791 0.047 Uiso 1 1 calc R . . . .
C41 C -0.1662(3) 0.8712(3) 0.70811(16) 0.0449(7) Uani 1 1 d . . . . .
H41 H -0.110131 0.903591 0.687404 0.054 Uiso 1 1 calc R . . . .
C42 C -0.2320(3) 0.8558(2) 0.66557(15) 0.0410(7) Uani 1 1 d . . . . .
H42 H -0.221024 0.877524 0.615803 0.049 Uiso 1 1 calc R . . . .
C43 C -0.3133(3) 0.8090(2) 0.69558(15) 0.0401(7) Uani 1 1 d . . . . .
H43 H -0.358996 0.798622 0.666711 0.048 Uiso 1 1 calc R . . . .
C44 C -0.3283(3) 0.7770(2) 0.76808(14) 0.0343(6) Uani 1 1 d . . . . .
H44 H -0.384589 0.744778 0.788332 0.041 Uiso 1 1 calc R . . . .
F7 F -0.97097(17) 0.94054(18) 0.80318(10) 0.0580(5) Uani 1 1 d . . . . .
F8 F -0.98898(18) 1.09020(18) 0.75434(12) 0.0718(7) Uani 1 1 d . . . . .
F9 F -0.9515(2) 1.05414(18) 0.86062(10) 0.0688(6) Uani 1 1 d . . . . .
O9 O -0.57677(19) 0.72417(16) 0.57649(11) 0.0412(5) Uani 1 1 d . . . . .
H9 H -0.499995 0.704400 0.556292 0.062 Uiso 1 1 calc GR . . . .
O10 O -0.66769(19) 0.64938(16) 0.75193(11) 0.0428(5) Uani 1 1 d . . . . .
O11 O -0.54428(18) 0.92893(16) 0.60438(11) 0.0417(5) Uani 1 1 d . . . . .
O12 O -0.73318(17) 1.05650(15) 0.60602(10) 0.0359(4) Uani 1 1 d . . . . .
C45 C -0.6427(3) 0.7921(2) 0.53136(14) 0.0333(6) Uani 1 1 d . . . . .
C46 C -0.5950(3) 0.7870(2) 0.45538(16) 0.0425(7) Uani 1 1 d . . . . .
H46 H -0.513012 0.737484 0.433090 0.051 Uiso 1 1 calc R . . . .
C47 C -0.6689(4) 0.8556(3) 0.41226(16) 0.0505(8) Uani 1 1 d . . . . .
H47 H -0.637049 0.853013 0.360252 0.061 Uiso 1 1 calc R . . . .
C48 C -0.7883(3) 0.9273(3) 0.44477(17) 0.0491(8) Uani 1 1 d . . . . .
H48 H -0.839228 0.972802 0.415171 0.059 Uiso 1 1 calc R . . . .
C49 C -0.8332(3) 0.9326(2) 0.52012(16) 0.0399(7) Uani 1 1 d . . . . .
H49 H -0.915001 0.982717 0.542033 0.048 Uiso 1 1 calc R . . . .
C50 C -0.7616(3) 0.8664(2) 0.56511(14) 0.0331(6) Uani 1 1 d . . . . .
C51 C -0.8109(2) 0.8786(2) 0.64807(14) 0.0323(6) Uani 1 1 d . . . . .
H51 H -0.898366 0.933707 0.660746 0.039 Uiso 1 1 calc R . . . .
C52 C -0.8095(3) 0.7756(2) 0.68740(15) 0.0356(6) Uani 1 1 d . . . . .
H52A H -0.889895 0.789392 0.724847 0.043 Uiso 1 1 calc R . . . .
H52B H -0.796165 0.723192 0.651462 0.043 Uiso 1 1 calc R . . . .
C53 C -0.7043(3) 0.7354(2) 0.72331(14) 0.0344(6) Uani 1 1 d . . . . .
C54 C -0.6500(2) 0.8151(2) 0.71959(13) 0.0313(6) Uani 1 1 d . . . . .
H54 H -0.558664 0.787456 0.694349 0.038 Uiso 1 1 calc R . . . .
C55 C -0.7290(2) 0.9118(2) 0.68186(13) 0.0303(5) Uani 1 1 d . . . . .
C56 C -0.7869(3) 0.9748(2) 0.75719(14) 0.0352(6) Uani 1 1 d . . . . .
H56 H -0.763772 1.036167 0.750352 0.042 Uiso 1 1 calc R . . . .
C57 C -0.6884(3) 0.8823(2) 0.79003(14) 0.0349(6) Uani 1 1 d . . . . .
H57 H -0.618780 0.904008 0.785167 0.042 Uiso 1 1 calc R . . . .
C58 C -0.6554(2) 0.9639(2) 0.62636(13) 0.0300(5) Uani 1 1 d . . . . .
C59 C -0.6753(3) 1.1087(3) 0.54697(16) 0.0444(7) Uani 1 1 d . . . . .
H59A H -0.645939 1.068902 0.500982 0.067 Uiso 1 1 calc GR . . . .
H59B H -0.604483 1.112632 0.558365 0.067 Uiso 1 1 calc GR . . . .
H59C H -0.736423 1.179861 0.541566 0.067 Uiso 1 1 calc GR . . . .
C60 C -0.9236(3) 1.0136(3) 0.79375(17) 0.0497(8) Uani 1 1 d . . . . .
C61 C -0.7139(3) 0.8406(2) 0.86674(14) 0.0363(6) Uani 1 1 d . . . . .
C62 C -0.6487(3) 0.8478(2) 0.91311(15) 0.0346(6) Uani 1 1 d . . . . .
H62 H -0.589438 0.877686 0.895304 0.041 Uiso 1 1 calc R . . . .
C63 C -0.6682(3) 0.8124(2) 0.98499(16) 0.0406(7) Uani 1 1 d . . . . .
H63 H -0.622938 0.818425 1.015903 0.049 Uiso 1 1 calc R . . . .
C64 C -0.7533(3) 0.7685(3) 1.01122(16) 0.0512(8) Uani 1 1 d . . . . .
H64 H -0.767640 0.744955 1.060497 0.061 Uiso 1 1 calc R . . . .
C65 C -0.8179(4) 0.7589(3) 0.96571(17) 0.0581(10) Uani 1 1 d . . . . .
H65 H -0.875877 0.727781 0.983642 0.070 Uiso 1 1 calc R . . . .
C66 C -0.7983(3) 0.7944(3) 0.89396(16) 0.0518(9) Uani 1 1 d . . . . .
H66 H -0.842909 0.787142 0.863062 0.062 Uiso 1 1 calc R . . . .


_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 C16 1.348(4) . ?
F2 C16 1.343(4) . ?
F3 C16 1.340(4) . ?
O1 H1 0.8400 . ?
O1 C1 1.364(3) . ?
O2 C9 1.224(3) . ?
O3 C14 1.193(3) . ?
O4 C14 1.336(3) . ?
O4 C15 1.453(3) . ?
C1 C2 1.386(4) . ?
C1 C6 1.397(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.399(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.376(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.377(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(4) . ?
C6 C7 1.517(4) . ?
C7 H7 1.0000 . ?
C7 C8 1.544(4) . ?
C7 C11 1.577(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.512(4) . ?
C9 C10 1.506(4) . ?
C10 H10 1.0000 . ?
C10 C11 1.542(3) . ?
C10 C13 1.566(4) . ?
C11 C12 1.578(4) . ?
C11 C14 1.507(4) . ?
C12 H12 1.0000 . ?
C12 C13 1.561(4) . ?
C12 C16 1.490(5) . ?
C13 H13 1.0000 . ?
C13 H13A 1.0000 . ?
C13 C17 1.524(5) . ?
C13 C17A 1.510(14) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C17 C18 1.386(6) . ?
C17 C22 1.387(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.379(6) . ?
C19 H19 0.9500 . ?
C19 C20 1.374(7) . ?
C20 H20 0.9500 . ?
C20 C21 1.372(6) . ?
C21 H21 0.9500 . ?
C21 C22 1.389(5) . ?
C22 H22 0.9500 . ?
C17A C18A 1.376(16) . ?
C17A C22A 1.391(16) . ?
C18A H18A 0.9500 . ?
C18A C19A 1.377(16) . ?
C19A H19A 0.9500 . ?
C19A C20A 1.358(17) . ?
C20A H20A 0.9500 . ?
C20A C21A 1.368(16) . ?
C21A H21A 0.9500 . ?
C21A C22A 1.388(14) . ?
C22A H22A 0.9500 . ?
F4 C38 1.340(4) . ?
F5 C38 1.336(3) . ?
F6 C38 1.349(3) . ?
O5 H5A 0.8400 . ?
O5 C23 1.373(3) . ?
O6 C31 1.227(3) . ?
O7 C36 1.196(3) . ?
O8 C36 1.333(3) . ?
O8 C37 1.452(3) . ?
C23 C24 1.392(4) . ?
C23 C28 1.395(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.386(4) . ?
C25 H25 0.9500 . ?
C25 C26 1.377(5) . ?
C26 H26 0.9500 . ?
C26 C27 1.385(4) . ?
C27 H27 0.9500 . ?
C27 C28 1.394(4) . ?
C28 C29 1.521(4) . ?
C29 H29 1.0000 . ?
C29 C30 1.544(3) . ?
C29 C33 1.576(4) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 C31 1.512(4) . ?
C31 C32 1.508(4) . ?
C32 H32 1.0000 . ?
C32 C33 1.545(3) . ?
C32 C35 1.563(3) . ?
C33 C34 1.580(3) . ?
C33 C36 1.512(3) . ?
C34 H34 1.0000 . ?
C34 C35 1.575(3) . ?
C34 C38 1.496(4) . ?
C35 H35 1.0000 . ?
C35 C39 1.512(3) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C39 C40 1.396(4) . ?
C39 C44 1.393(4) . ?
C40 H40 0.9500 . ?
C40 C41 1.390(4) . ?
C41 H41 0.9500 . ?
C41 C42 1.386(4) . ?
C42 H42 0.9500 . ?
C42 C43 1.377(4) . ?
C43 H43 0.9500 . ?
C43 C44 1.385(4) . ?
C44 H44 0.9500 . ?
F7 C60 1.351(4) . ?
F8 C60 1.343(4) . ?
F9 C60 1.341(4) . ?
O9 H9 0.8400 . ?
O9 C45 1.368(3) . ?
O10 C53 1.222(3) . ?
O11 C58 1.194(3) . ?
O12 C58 1.344(3) . ?
O12 C59 1.447(3) . ?
C45 C46 1.389(4) . ?
C45 C50 1.396(4) . ?
C46 H46 0.9500 . ?
C46 C47 1.394(4) . ?
C47 H47 0.9500 . ?
C47 C48 1.382(5) . ?
C48 H48 0.9500 . ?
C48 C49 1.375(4) . ?
C49 H49 0.9500 . ?
C49 C50 1.392(4) . ?
C50 C51 1.516(4) . ?
C51 H51 1.0000 . ?
C51 C52 1.547(4) . ?
C51 C55 1.574(4) . ?
C52 H52A 0.9900 . ?
C52 H52B 0.9900 . ?
C52 C53 1.505(4) . ?
C53 C54 1.512(4) . ?
C54 H54 1.0000 . ?
C54 C55 1.542(3) . ?
C54 C57 1.563(4) . ?
C55 C56 1.579(4) . ?
C55 C58 1.516(4) . ?
C56 H56 1.0000 . ?
C56 C57 1.572(4) . ?
C56 C60 1.494(4) . ?
C57 H57 1.0000 . ?
C57 C61 1.506(4) . ?
C59 H59A 0.9800 . ?
C59 H59B 0.9800 . ?
C59 H59C 0.9800 . ?
C61 C62 1.389(4) . ?
C61 C66 1.394(4) . ?
C62 H62 0.9500 . ?
C62 C63 1.390(4) . ?
C63 H63 0.9500 . ?
C63 C64 1.375(4) . ?
C64 H64 0.9500 . ?
C64 C65 1.383(4) . ?
C65 H65 0.9500 . ?
C65 C66 1.388(4) . ?
C66 H66 0.9500 . ?

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
C1 O1 H1 109.5 . . ?
C14 O4 C15 116.1(2) . . ?
O1 C1 C2 122.4(3) . . ?
O1 C1 C6 116.3(3) . . ?
C2 C1 C6 121.3(3) . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 119.0(3) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.1(3) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.3(4) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C7 121.3(2) . . ?
C5 C6 C1 118.0(3) . . ?
C5 C6 C7 120.7(3) . . ?
C6 C7 H7 108.5 . . ?
C6 C7 C8 113.6(2) . . ?
C6 C7 C11 113.3(2) . . ?
C8 C7 H7 108.5 . . ?
C8 C7 C11 104.2(2) . . ?
C11 C7 H7 108.5 . . ?
C7 C8 H8A 110.3 . . ?
C7 C8 H8B 110.3 . . ?
H8A C8 H8B 108.5 . . ?
C9 C8 C7 107.3(2) . . ?
C9 C8 H8A 110.3 . . ?
C9 C8 H8B 110.3 . . ?
O2 C9 C8 124.1(3) . . ?
O2 C9 C10 125.3(3) . . ?
C10 C9 C8 110.5(2) . . ?
C9 C10 H10 114.0 . . ?
C9 C10 C11 105.9(2) . . ?
C9 C10 C13 115.3(2) . . ?
C11 C10 H10 114.0 . . ?
C11 C10 C13 91.0(2) . . ?
C13 C10 H10 114.0 . . ?
C7 C11 C12 118.7(2) . . ?
C10 C11 C7 108.2(2) . . ?
C10 C11 C12 89.4(2) . . ?
C14 C11 C7 113.6(2) . . ?
C14 C11 C10 115.5(2) . . ?
C14 C11 C12 109.4(2) . . ?
C11 C12 H12 106.8 . . ?
C13 C12 C11 89.9(2) . . ?
C13 C12 H12 106.8 . . ?
C16 C12 C11 119.6(3) . . ?
C16 C12 H12 106.8 . . ?
C16 C12 C13 125.0(3) . . ?
C10 C13 H13 105.5 . . ?
C10 C13 H13A 104.5 . . ?
C12 C13 C10 89.1(2) . . ?
C12 C13 H13 105.5 . . ?
C12 C13 H13A 104.5 . . ?
C17 C13 C10 121.4(3) . . ?
C17 C13 C12 127.3(3) . . ?
C17 C13 H13 105.5 . . ?
C17A C13 C10 109.9(11) . . ?
C17A C13 C12 139.7(8) . . ?
C17A C13 H13A 104.5 . . ?
O3 C14 O4 124.0(3) . . ?
O3 C14 C11 125.4(2) . . ?
O4 C14 C11 110.6(2) . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
F1 C16 C12 116.1(3) . . ?
F2 C16 F1 106.7(3) . . ?
F2 C16 C12 112.0(4) . . ?
F3 C16 F1 105.8(3) . . ?
F3 C16 F2 105.7(3) . . ?
F3 C16 C12 109.8(3) . . ?
C18 C17 C13 114.4(4) . . ?
C18 C17 C22 117.9(4) . . ?
C22 C17 C13 127.7(4) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 C17 121.2(5) . . ?
C19 C18 H18 119.4 . . ?
C18 C19 H19 119.6 . . ?
C20 C19 C18 120.7(5) . . ?
C20 C19 H19 119.6 . . ?
C19 C20 H20 120.7 . . ?
C21 C20 C19 118.7(4) . . ?
C21 C20 H20 120.7 . . ?
C20 C21 H21 119.4 . . ?
C20 C21 C22 121.2(4) . . ?
C22 C21 H21 119.4 . . ?
C17 C22 C21 120.3(4) . . ?
C17 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C18A C17A C13 118.0(14) . . ?
C18A C17A C22A 119.8(14) . . ?
C22A C17A C13 122.2(13) . . ?
C17A C18A H18A 120.0 . . ?
C17A C18A C19A 120.1(17) . . ?
C19A C18A H18A 120.0 . . ?
C18A C19A H19A 120.5 . . ?
C20A C19A C18A 119.0(18) . . ?
C20A C19A H19A 120.5 . . ?
C19A C20A H20A 118.9 . . ?
C19A C20A C21A 122.2(17) . . ?
C21A C20A H20A 118.9 . . ?
C20A C21A H21A 120.7 . . ?
C20A C21A C22A 118.5(15) . . ?
C22A C21A H21A 120.7 . . ?
C17A C22A H22A 120.2 . . ?
C21A C22A C17A 119.5(13) . . ?
C21A C22A H22A 120.2 . . ?
C23 O5 H5A 109.5 . . ?
C36 O8 C37 115.8(2) . . ?
O5 C23 C24 121.3(2) . . ?
O5 C23 C28 117.1(2) . . ?
C24 C23 C28 121.7(2) . . ?
C23 C24 H24 120.4 . . ?
C25 C24 C23 119.1(3) . . ?
C25 C24 H24 120.4 . . ?
C24 C25 H25 119.8 . . ?
C26 C25 C24 120.4(3) . . ?
C26 C25 H25 119.8 . . ?
C25 C26 H26 120.1 . . ?
C25 C26 C27 119.9(3) . . ?
C27 C26 H26 120.1 . . ?
C26 C27 H27 119.3 . . ?
C26 C27 C28 121.5(3) . . ?
C28 C27 H27 119.3 . . ?
C23 C28 C29 121.4(2) . . ?
C27 C28 C23 117.4(3) . . ?
C27 C28 C29 121.2(2) . . ?
C28 C29 H29 109.0 . . ?
C28 C29 C30 113.6(2) . . ?
C28 C29 C33 111.7(2) . . ?
C30 C29 H29 109.0 . . ?
C30 C29 C33 104.48(19) . . ?
C33 C29 H29 109.0 . . ?
C29 C30 H30A 110.3 . . ?
C29 C30 H30B 110.3 . . ?
H30A C30 H30B 108.5 . . ?
C31 C30 C29 107.3(2) . . ?
C31 C30 H30A 110.3 . . ?
C31 C30 H30B 110.3 . . ?
O6 C31 C30 124.2(2) . . ?
O6 C31 C32 124.3(2) . . ?
C32 C31 C30 111.5(2) . . ?
C31 C32 H32 113.6 . . ?
C31 C32 C33 105.0(2) . . ?
C31 C32 C35 117.8(2) . . ?
C33 C32 H32 113.6 . . ?
C33 C32 C35 90.58(18) . . ?
C35 C32 H32 113.6 . . ?
C29 C33 C34 121.3(2) . . ?
C32 C33 C29 108.3(2) . . ?
C32 C33 C34 89.48(17) . . ?
C36 C33 C29 113.0(2) . . ?
C36 C33 C32 115.0(2) . . ?
C36 C33 C34 107.9(2) . . ?
C33 C34 H34 108.5 . . ?
C35 C34 C33 88.89(18) . . ?
C35 C34 H34 108.5 . . ?
C38 C34 C33 119.6(2) . . ?
C38 C34 H34 108.5 . . ?
C38 C34 C35 121.3(2) . . ?
C32 C35 C34 89.02(18) . . ?
C32 C35 H35 105.3 . . ?
C34 C35 H35 105.3 . . ?
C39 C35 C32 122.5(2) . . ?
C39 C35 C34 127.0(2) . . ?
C39 C35 H35 105.3 . . ?
O7 C36 O8 124.2(2) . . ?
O7 C36 C33 124.9(2) . . ?
O8 C36 C33 110.9(2) . . ?
O8 C37 H37A 109.5 . . ?
O8 C37 H37B 109.5 . . ?
O8 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
F4 C38 F6 105.5(2) . . ?
F4 C38 C34 116.1(2) . . ?
F5 C38 F4 106.1(2) . . ?
F5 C38 F6 107.0(2) . . ?
F5 C38 C34 110.6(3) . . ?
F6 C38 C34 111.0(2) . . ?
C40 C39 C35 124.5(2) . . ?
C44 C39 C35 117.7(2) . . ?
C44 C39 C40 117.8(2) . . ?
C39 C40 H40 119.7 . . ?
C41 C40 C39 120.6(3) . . ?
C41 C40 H40 119.7 . . ?
C40 C41 H41 119.8 . . ?
C42 C41 C40 120.3(3) . . ?
C42 C41 H41 119.8 . . ?
C41 C42 H42 120.1 . . ?
C43 C42 C41 119.9(3) . . ?
C43 C42 H42 120.1 . . ?
C42 C43 H43 120.2 . . ?
C42 C43 C44 119.7(3) . . ?
C44 C43 H43 120.2 . . ?
C39 C44 H44 119.1 . . ?
C43 C44 C39 121.8(3) . . ?
C43 C44 H44 119.1 . . ?
C45 O9 H9 109.5 . . ?
C58 O12 C59 115.6(2) . . ?
O9 C45 C46 121.9(3) . . ?
O9 C45 C50 116.9(2) . . ?
C46 C45 C50 121.2(3) . . ?
C45 C46 H46 120.4 . . ?
C45 C46 C47 119.2(3) . . ?
C47 C46 H46 120.4 . . ?
C46 C47 H47 119.8 . . ?
C48 C47 C46 120.3(3) . . ?
C48 C47 H47 119.8 . . ?
C47 C48 H48 120.1 . . ?
C49 C48 C47 119.7(3) . . ?
C49 C48 H48 120.1 . . ?
C48 C49 H49 119.2 . . ?
C48 C49 C50 121.6(3) . . ?
C50 C49 H49 119.2 . . ?
C45 C50 C51 121.7(2) . . ?
C49 C50 C45 117.9(3) . . ?
C49 C50 C51 120.3(3) . . ?
C50 C51 H51 108.9 . . ?
C50 C51 C52 113.3(2) . . ?
C50 C51 C55 111.6(2) . . ?
C52 C51 H51 108.9 . . ?
C52 C51 C55 105.0(2) . . ?
C55 C51 H51 108.9 . . ?
C51 C52 H52A 110.3 . . ?
C51 C52 H52B 110.3 . . ?
H52A C52 H52B 108.5 . . ?
C53 C52 C51 107.1(2) . . ?
C53 C52 H52A 110.3 . . ?
C53 C52 H52B 110.3 . . ?
O10 C53 C52 124.3(3) . . ?
O10 C53 C54 124.4(2) . . ?
C52 C53 C54 111.3(2) . . ?
C53 C54 H54 113.3 . . ?
C53 C54 C55 105.6(2) . . ?
C53 C54 C57 118.2(2) . . ?
C55 C54 H54 113.3 . . ?
C55 C54 C57 90.7(2) . . ?
C57 C54 H54 113.3 . . ?
C51 C55 C56 120.9(2) . . ?
C54 C55 C51 107.9(2) . . ?
C54 C55 C56 89.58(19) . . ?
C58 C55 C51 112.7(2) . . ?
C58 C55 C54 114.9(2) . . ?
C58 C55 C56 109.1(2) . . ?
C55 C56 H56 108.1 . . ?
C57 C56 C55 89.04(19) . . ?
C57 C56 H56 108.1 . . ?
C60 C56 C55 120.3(2) . . ?
C60 C56 H56 108.1 . . ?
C60 C56 C57 121.6(2) . . ?
C54 C57 C56 89.08(19) . . ?
C54 C57 H57 105.7 . . ?
C56 C57 H57 105.7 . . ?
C61 C57 C54 123.0(2) . . ?
C61 C57 C56 125.4(2) . . ?
C61 C57 H57 105.7 . . ?
O11 C58 O12 124.6(2) . . ?
O11 C58 C55 125.3(2) . . ?
O12 C58 C55 110.2(2) . . ?
O12 C59 H59A 109.5 . . ?
O12 C59 H59B 109.5 . . ?
O12 C59 H59C 109.5 . . ?
H59A C59 H59B 109.5 . . ?
H59A C59 H59C 109.5 . . ?
H59B C59 H59C 109.5 . . ?
F7 C60 C56 115.3(3) . . ?
F8 C60 F7 105.8(3) . . ?
F8 C60 C56 110.7(2) . . ?
F9 C60 F7 106.5(2) . . ?
F9 C60 F8 107.2(3) . . ?
F9 C60 C56 111.0(3) . . ?
C62 C61 C57 118.0(3) . . ?
C62 C61 C66 117.9(3) . . ?
C66 C61 C57 124.1(2) . . ?
C61 C62 H62 119.3 . . ?
C61 C62 C63 121.4(3) . . ?
C63 C62 H62 119.3 . . ?
C62 C63 H63 120.1 . . ?
C64 C63 C62 119.8(3) . . ?
C64 C63 H63 120.1 . . ?
C63 C64 H64 120.1 . . ?
C63 C64 C65 119.9(3) . . ?
C65 C64 H64 120.1 . . ?
C64 C65 H65 119.9 . . ?
C64 C65 C66 120.3(3) . . ?
C66 C65 H65 119.9 . . ?
C61 C66 H66 119.7 . . ?
C65 C66 C61 120.7(3) . . ?
C65 C66 H66 119.7 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_190320_cp_315_0m
_database_code_depnum_ccdc_archive 'CCDC 2087904'
loop_
_audit_author_name
_audit_author_address
'Chromanone-fused Bicycle'
;ZheJiang University of Science and Technolgoy
China
;
_audit_update_record             
;
2021-06-03 deposited with the CCDC.	2021-09-13 downloaded from the CCDC.
;
_audit_creation_date             2019-03-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 O3'
_chemical_formula_sum            'C20 H14 O3'
_chemical_formula_weight         302.31
_chemical_absolute_configuration unk
_chemical_melting_point          ?
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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'

_cell_length_a                   6.932(2)
_cell_length_b                   11.065(4)
_cell_length_c                   19.212(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1473.5(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9910
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.81
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7181
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0754 before and 0.0494 after correction.
The Ratio of minimum to maximum transmission is 0.9631.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0196
_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       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            18145
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.488
_diffrn_reflns_theta_min         2.808
_diffrn_ambient_temperature      170.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.729
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3223
_reflns_number_total             3362
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 1310 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3362
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0306
_refine_ls_restrained_S_all      1.042
_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)+(0.0375P)²+0.3297P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0749
_refine_ls_wR_factor_ref         0.0766
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C14(H14), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.76831(19) 0.37393(12) 0.53678(7) 0.0290(3) Uani 1 1 d . . . . .
O2 O 0.5034(2) 0.31001(11) 0.58624(7) 0.0262(3) Uani 1 1 d . . . . .
O3 O 0.3192(2) 0.73235(13) 0.68158(8) 0.0340(3) Uani 1 1 d . . . . .
C1 C 0.1921(3) 0.26095(17) 0.62474(10) 0.0268(4) Uani 1 1 d . . . . .
H1 H 0.174146 0.218147 0.582361 0.032 Uiso 1 1 calc R . . . .
C2 C 0.0491(3) 0.26180(18) 0.67536(10) 0.0288(4) Uani 1 1 d . . . . .
H2 H -0.067878 0.219011 0.667879 0.035 Uiso 1 1 calc R . . . .
C3 C 0.0771(3) 0.32504(17) 0.73677(10) 0.0264(4) Uani 1 1 d . . . . .
H3 H -0.019624 0.324116 0.771810 0.032 Uiso 1 1 calc R . . . .
C4 C 0.2466(3) 0.38993(16) 0.74717(9) 0.0227(3) Uani 1 1 d . . . . .
H4 H 0.263063 0.434538 0.789006 0.027 Uiso 1 1 calc R . . . .
C5 C 0.3930(2) 0.39069(14) 0.69731(9) 0.0190(3) Uani 1 1 d . . . . .
C6 C 0.3612(2) 0.32375(15) 0.63730(9) 0.0213(3) Uani 1 1 d . . . . .
C7 C 0.6494(3) 0.39104(15) 0.58089(9) 0.0214(3) Uani 1 1 d . . . . .
C8 C 0.6502(2) 0.49530(14) 0.63122(9) 0.0191(3) Uani 1 1 d . . . . .
C9 C 0.5783(2) 0.46310(15) 0.70532(9) 0.0196(3) Uani 1 1 d . . . . .
H9 H 0.677992 0.418209 0.732669 0.024 Uiso 1 1 calc R . . . .
C10 C 0.5343(3) 0.58791(15) 0.73698(9) 0.0232(4) Uani 1 1 d . . . . .
H10A H 0.444759 0.581025 0.776920 0.028 Uiso 1 1 calc R . . . .
H10B H 0.653995 0.628681 0.752465 0.028 Uiso 1 1 calc R . . . .
C11 C 0.4415(2) 0.65501(15) 0.67694(9) 0.0215(3) Uani 1 1 d . . . . .
C12 C 0.5292(2) 0.61057(14) 0.60902(9) 0.0191(3) Uani 1 1 d . . . . .
H12 H 0.442602 0.603460 0.567579 0.023 Uiso 1 1 calc R . . . .
C13 C 0.7256(2) 0.67091(15) 0.59900(9) 0.0207(3) Uani 1 1 d . . . . .
C14 C 0.8259(2) 0.57597(15) 0.62234(9) 0.0223(3) Uani 1 1 d . . . . .
H14 H 0.959609 0.563399 0.630482 0.027 Uiso 1 1 calc R . . . .
C15 C 0.7668(3) 0.79605(15) 0.57903(9) 0.0212(3) Uani 1 1 d . . . . .
C16 C 0.6168(3) 0.87255(16) 0.55892(10) 0.0274(4) Uani 1 1 d . . . . .
H16 H 0.489469 0.841596 0.554700 0.033 Uiso 1 1 calc R . . . .
C17 C 0.6527(3) 0.99429(16) 0.54495(11) 0.0307(4) Uani 1 1 d . . . . .
H17 H 0.550228 1.045888 0.530965 0.037 Uiso 1 1 calc R . . . .
C18 C 0.8380(3) 1.03971(16) 0.55152(10) 0.0294(4) Uani 1 1 d . . . . .
H18 H 0.862033 1.123014 0.543264 0.035 Uiso 1 1 calc R . . . .
C19 C 0.9884(3) 0.96364(17) 0.57015(9) 0.0273(4) Uani 1 1 d . . . . .
H19 H 1.115642 0.994913 0.573950 0.033 Uiso 1 1 calc R . . . .
C20 C 0.9544(3) 0.84208(16) 0.58329(9) 0.0225(3) Uani 1 1 d . . . . .
H20 H 1.058465 0.790181 0.595166 0.027 Uiso 1 1 calc R . . . .


_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 C7 1.197(2) . ?
O2 C6 1.399(2) . ?
O2 C7 1.356(2) . ?
O3 C11 1.207(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.388(3) . ?
C1 C6 1.384(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.392(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.395(2) . ?
C5 C6 1.388(2) . ?
C5 C9 1.522(2) . ?
C7 C8 1.505(2) . ?
C8 C9 1.550(2) . ?
C8 C12 1.585(2) . ?
C8 C14 1.519(2) . ?
C9 H9 1.0000 . ?
C9 C10 1.540(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.515(3) . ?
C11 C12 1.521(2) . ?
C12 H12 1.0000 . ?
C12 C13 1.529(2) . ?
C13 C14 1.337(2) . ?
C13 C15 1.465(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.395(3) . ?
C15 C20 1.399(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.396(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.385(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.387(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.389(3) . ?
C20 H20 0.9500 . ?

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
C7 O2 C6 120.48(13) . . ?
C2 C1 H1 120.7 . . ?
C6 C1 H1 120.7 . . ?
C6 C1 C2 118.62(17) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.02(17) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.06(17) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.23(16) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C9 123.19(15) . . ?
C6 C5 C4 116.85(15) . . ?
C6 C5 C9 119.93(15) . . ?
C1 C6 O2 114.83(15) . . ?
C1 C6 C5 123.17(16) . . ?
C5 C6 O2 121.92(15) . . ?
O1 C7 O2 117.59(15) . . ?
O1 C7 C8 124.98(16) . . ?
O2 C7 C8 117.44(14) . . ?
C7 C8 C9 114.37(14) . . ?
C7 C8 C12 116.21(14) . . ?
C7 C8 C14 112.40(14) . . ?
C9 C8 C12 105.19(13) . . ?
C14 C8 C9 119.73(14) . . ?
C14 C8 C12 85.50(12) . . ?
C5 C9 C8 107.43(13) . . ?
C5 C9 H9 112.0 . . ?
C5 C9 C10 110.18(14) . . ?
C8 C9 H9 112.0 . . ?
C10 C9 C8 102.73(13) . . ?
C10 C9 H9 112.0 . . ?
C9 C10 H10A 111.2 . . ?
C9 C10 H10B 111.2 . . ?
H10A C10 H10B 109.1 . . ?
C11 C10 C9 102.88(14) . . ?
C11 C10 H10A 111.2 . . ?
C11 C10 H10B 111.2 . . ?
O3 C11 C10 126.09(17) . . ?
O3 C11 C12 124.95(17) . . ?
C10 C11 C12 108.96(14) . . ?
C8 C12 H12 117.9 . . ?
C11 C12 C8 103.93(13) . . ?
C11 C12 H12 117.9 . . ?
C11 C12 C13 108.83(13) . . ?
C13 C12 C8 85.04(12) . . ?
C13 C12 H12 117.9 . . ?
C14 C13 C12 94.46(14) . . ?
C14 C13 C15 136.83(17) . . ?
C15 C13 C12 128.25(15) . . ?
C8 C14 H14 132.6 . . ?
C13 C14 C8 94.73(14) . . ?
C13 C14 H14 132.6 . . ?
C16 C15 C13 120.06(16) . . ?
C16 C15 C20 119.21(15) . . ?
C20 C15 C13 120.65(16) . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.38(18) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.87(18) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 120.04(16) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.44(18) . . ?
C20 C19 H19 119.8 . . ?
C15 C20 H20 120.0 . . ?
C19 C20 C15 120.01(17) . . ?
C19 C20 H20 120.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
