# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_cu_g6p_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2235083'
loop_
_audit_author_name
_audit_author_address
'Ye Tao'
;,,
China
;
_audit_update_record             
;
2023-01-09 deposited with the CCDC.	2023-02-07 downloaded from the CCDC.
;
_audit_creation_date             2022-12-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6392)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H15 F O2'
_chemical_formula_sum            'C21 H15 F O2'
_chemical_formula_weight         318.33
_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 0.0181 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'
O O 0.0492 0.0322 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   5.7182(11)
_cell_length_b                   18.987(3)
_cell_length_c                   15.264(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.241(10)
_cell_angle_gamma                90
_cell_volume                     1657.2(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4078
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      68.29
_cell_measurement_theta_min      3.72
_shelx_estimated_absorpt_T_max   0.931
_shelx_estimated_absorpt_T_min   0.931
_exptl_absorpt_coefficient_mu    0.725
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0594 before and 0.0441 after correction.
The Ratio of minimum to maximum transmission is 0.8806.
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    1.276
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7022
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.362
_diffrn_reflns_theta_min         3.715
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'BRUKER D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2484
_reflns_number_total             2944
_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 (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2944
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0450
_refine_ls_restrained_S_all      1.059
_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)+(0.0781P)²+0.1644P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1311
_refine_ls_wR_factor_ref         0.1383
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D), C00F(H00F),
 C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N), C00O(H00O)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O001 O 0.8460(2) 0.50391(6) 0.41949(7) 0.0728(4) Uani 1 1 d . . . . .
F002 F 0.9458(3) 0.14207(6) 0.39824(10) 0.1045(4) Uani 1 1 d . . . . .
O003 O 0.6878(3) 0.51582(6) 0.28735(9) 0.1047(6) Uani 1 1 d . . . . .
C004 C 0.4813(3) 0.38991(7) 0.21575(9) 0.0539(3) Uani 1 1 d . . . . .
C005 C 0.6104(2) 0.36120(7) 0.29307(9) 0.0518(3) Uani 1 1 d . . . . .
C006 C 0.6079(3) 0.28350(7) 0.30242(9) 0.0530(3) Uani 1 1 d . . . . .
C007 C 0.8763(3) 0.57723(8) 0.42497(9) 0.0581(4) Uani 1 1 d . . . . .
C008 C 0.7204(3) 0.40177(8) 0.35246(9) 0.0575(4) Uani 1 1 d . . . . .
H008 H 0.789040 0.379082 0.401713 0.069 Uiso 1 1 calc R U . . .
C009 C 0.7419(3) 0.47858(8) 0.34663(9) 0.0585(4) Uani 1 1 d . . . . .
C00A C 1.0704(3) 0.60786(9) 0.38894(11) 0.0665(4) Uani 1 1 d . . . . .
H00A H 1.182642 0.580220 0.358740 0.080 Uiso 1 1 calc R U . . .
C00B C 0.7865(3) 0.24789(8) 0.34644(10) 0.0618(4) Uani 1 1 d . . . . .
H00B H 0.915923 0.272850 0.370304 0.074 Uiso 1 1 calc R U . . .
C00C C 0.5610(4) 0.37675(10) 0.13189(11) 0.0753(5) Uani 1 1 d . . . . .
H00C H 0.700947 0.350694 0.123503 0.090 Uiso 1 1 calc R U . . .
C00D C 0.4227(3) 0.24449(8) 0.26748(10) 0.0625(4) Uani 1 1 d . . . . .
H00D H 0.300543 0.267975 0.236866 0.075 Uiso 1 1 calc R U . . .
C00E C 0.7714(3) 0.17600(9) 0.35456(11) 0.0694(4) Uani 1 1 d . . . . .
C00F C 1.0995(3) 0.67990(9) 0.39746(12) 0.0732(5) Uani 1 1 d . . . . .
H00F H 1.232719 0.702052 0.372728 0.088 Uiso 1 1 calc R U . . .
C00G C 0.9375(4) 0.71948(9) 0.44130(12) 0.0742(5) Uani 1 1 d . . . . .
H00G H 0.957942 0.768958 0.446502 0.089 Uiso 1 1 calc R U . . .
C00H C 0.5901(4) 0.13709(8) 0.32084(11) 0.0713(5) Uani 1 1 d . . . . .
H00H H 0.585511 0.087369 0.327629 0.086 Uiso 1 1 calc R U . . .
C00I C 0.7146(3) 0.61584(10) 0.46947(12) 0.0730(5) Uani 1 1 d . . . . .
H00I H 0.581989 0.593636 0.494587 0.088 Uiso 1 1 calc R U . . .
C00J C 0.2752(3) 0.42739(10) 0.22550(12) 0.0718(4) Uani 1 1 d . . . . .
H00J H 0.217728 0.436963 0.282586 0.086 Uiso 1 1 calc R U . . .
C00K C 0.4150(3) 0.17231(9) 0.27685(11) 0.0711(4) Uani 1 1 d . . . . .
H00K H 0.287583 0.146620 0.252713 0.085 Uiso 1 1 calc R U . . .
C00L C 0.7464(4) 0.68776(11) 0.47756(13) 0.0804(5) Uani 1 1 d . . . . .
H00L H 0.634918 0.715226 0.508427 0.096 Uiso 1 1 calc R U . . .
C00M C 0.1525(4) 0.45096(12) 0.15327(17) 0.0923(6) Uani 1 1 d . . . . .
H00M H 0.010412 0.476132 0.160881 0.111 Uiso 1 1 calc R U . . .
C00N C 0.2344(5) 0.43823(12) 0.07067(16) 0.0995(7) Uani 1 1 d . . . . .
H00N H 0.150336 0.454945 0.021053 0.119 Uiso 1 1 calc R U . . .
C00O C 0.4362(5) 0.40165(13) 0.05982(13) 0.0998(7) Uani 1 1 d . . . . .
H00O H 0.492882 0.392956 0.002409 0.120 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
O001 C007 1.4053(18) . ?
O001 C009 1.3481(18) . ?
F002 C00E 1.360(2) . ?
O003 C009 1.1884(19) . ?
C004 C005 1.493(2) . ?
C004 C00C 1.383(2) . ?
C004 C00J 1.385(2) . ?
C005 C006 1.482(2) . ?
C005 C008 1.344(2) . ?
C006 C00B 1.395(2) . ?
C006 C00D 1.396(2) . ?
C007 C00A 1.370(2) . ?
C007 C00I 1.363(2) . ?
C008 H008 0.9500 . ?
C008 C009 1.466(2) . ?
C00A H00A 0.9500 . ?
C00A C00F 1.384(2) . ?
C00B H00B 0.9500 . ?
C00B C00E 1.373(2) . ?
C00C H00C 0.9500 . ?
C00C C00O 1.391(3) . ?
C00D H00D 0.9500 . ?
C00D C00K 1.379(2) . ?
C00E C00H 1.371(3) . ?
C00F H00F 0.9500 . ?
C00F C00G 1.370(3) . ?
C00G H00G 0.9500 . ?
C00G C00L 1.367(3) . ?
C00H H00H 0.9500 . ?
C00H C00K 1.376(3) . ?
C00I H00I 0.9500 . ?
C00I C00L 1.383(3) . ?
C00J H00J 0.9500 . ?
C00J C00M 1.379(3) . ?
C00K H00K 0.9500 . ?
C00L H00L 0.9500 . ?
C00M H00M 0.9500 . ?
C00M C00N 1.368(4) . ?
C00N H00N 0.9500 . ?
C00N C00O 1.358(4) . ?
C00O H00O 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
C009 O001 C007 117.16(11) . . ?
C00C C004 C005 120.13(14) . . ?
C00C C004 C00J 118.43(15) . . ?
C00J C004 C005 121.39(14) . . ?
C006 C005 C004 115.76(12) . . ?
C008 C005 C004 123.54(13) . . ?
C008 C005 C006 120.68(13) . . ?
C00B C006 C005 121.43(13) . . ?
C00B C006 C00D 118.65(14) . . ?
C00D C006 C005 119.92(13) . . ?
C00A C007 O001 119.76(15) . . ?
C00I C007 O001 118.60(15) . . ?
C00I C007 C00A 121.59(15) . . ?
C005 C008 H008 117.7 . . ?
C005 C008 C009 124.64(13) . . ?
C009 C008 H008 117.7 . . ?
O001 C009 C008 109.98(12) . . ?
O003 C009 O001 121.91(14) . . ?
O003 C009 C008 128.05(14) . . ?
C007 C00A H00A 120.7 . . ?
C007 C00A C00F 118.62(16) . . ?
C00F C00A H00A 120.7 . . ?
C006 C00B H00B 120.7 . . ?
C00E C00B C006 118.61(15) . . ?
C00E C00B H00B 120.7 . . ?
C004 C00C H00C 120.0 . . ?
C004 C00C C00O 120.03(19) . . ?
C00O C00C H00C 120.0 . . ?
C006 C00D H00D 119.6 . . ?
C00K C00D C006 120.81(15) . . ?
C00K C00D H00D 119.6 . . ?
F002 C00E C00B 117.95(16) . . ?
F002 C00E C00H 118.72(15) . . ?
C00B C00E C00H 123.33(16) . . ?
C00A C00F H00F 119.8 . . ?
C00G C00F C00A 120.46(17) . . ?
C00G C00F H00F 119.8 . . ?
C00F C00G H00G 120.0 . . ?
C00L C00G C00F 119.98(16) . . ?
C00L C00G H00G 120.0 . . ?
C00E C00H H00H 121.0 . . ?
C00E C00H C00K 117.92(15) . . ?
C00K C00H H00H 121.0 . . ?
C007 C00I H00I 120.4 . . ?
C007 C00I C00L 119.11(16) . . ?
C00L C00I H00I 120.4 . . ?
C004 C00J H00J 119.6 . . ?
C00M C00J C004 120.73(18) . . ?
C00M C00J H00J 119.6 . . ?
C00D C00K H00K 119.7 . . ?
C00H C00K C00D 120.67(15) . . ?
C00H C00K H00K 119.7 . . ?
C00G C00L C00I 120.24(17) . . ?
C00G C00L H00L 119.9 . . ?
C00I C00L H00L 119.9 . . ?
C00J C00M H00M 119.9 . . ?
C00N C00M C00J 120.3(2) . . ?
C00N C00M H00M 119.9 . . ?
C00M C00N H00N 120.1 . . ?
C00O C00N C00M 119.83(19) . . ?
C00O C00N H00N 120.1 . . ?
C00C C00O H00O 119.6 . . ?
C00N C00O C00C 120.7(2) . . ?
C00N C00O H00O 119.6 . . ?

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
O001 C007 C00A C00F -178.14(14) . . . . ?
O001 C007 C00I C00L 178.06(15) . . . . ?
F002 C00E C00H C00K 179.98(16) . . . . ?
C004 C005 C006 C00B 153.88(14) . . . . ?
C004 C005 C006 C00D -26.76(19) . . . . ?
C004 C005 C008 C009 -4.2(2) . . . . ?
C004 C00C C00O C00N -0.8(4) . . . . ?
C004 C00J C00M C00N -0.7(3) . . . . ?
C005 C004 C00C C00O 177.94(18) . . . . ?
C005 C004 C00J C00M -177.16(16) . . . . ?
C005 C006 C00B C00E 178.56(14) . . . . ?
C005 C006 C00D C00K -178.82(14) . . . . ?
C005 C008 C009 O001 175.33(15) . . . . ?
C005 C008 C009 O003 -7.4(3) . . . . ?
C006 C005 C008 C009 176.95(14) . . . . ?
C006 C00B C00E F002 -179.49(15) . . . . ?
C006 C00B C00E C00H 0.6(3) . . . . ?
C006 C00D C00K C00H -0.1(3) . . . . ?
C007 O001 C009 O003 3.6(3) . . . . ?
C007 O001 C009 C008 -178.93(14) . . . . ?
C007 C00A C00F C00G 0.2(3) . . . . ?
C007 C00I C00L C00G 0.0(3) . . . . ?
C008 C005 C006 C00B -27.2(2) . . . . ?
C008 C005 C006 C00D 152.17(15) . . . . ?
C009 O001 C007 C00A -86.24(19) . . . . ?
C009 O001 C007 C00I 96.35(18) . . . . ?
C00A C007 C00I C00L 0.7(3) . . . . ?
C00A C00F C00G C00L 0.5(3) . . . . ?
C00B C006 C00D C00K 0.6(2) . . . . ?
C00B C00E C00H C00K -0.1(3) . . . . ?
C00C C004 C005 C006 -66.90(19) . . . . ?
C00C C004 C005 C008 114.20(18) . . . . ?
C00C C004 C00J C00M 0.0(3) . . . . ?
C00D C006 C00B C00E -0.8(2) . . . . ?
C00E C00H C00K C00D -0.2(3) . . . . ?
C00F C00G C00L C00I -0.6(3) . . . . ?
C00I C007 C00A C00F -0.8(2) . . . . ?
C00J C004 C005 C006 110.24(16) . . . . ?
C00J C004 C005 C008 -68.7(2) . . . . ?
C00J C004 C00C C00O 0.7(3) . . . . ?
C00J C00M C00N C00O 0.6(4) . . . . ?
C00M C00N C00O C00C 0.1(4) . . . . ?

_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_2022101301_0m
_database_code_depnum_ccdc_archive 'CCDC 2235100'
loop_
_audit_author_name
_audit_author_address
'Ye tao'
;,,
China
;
_audit_update_record             
;
2023-01-09 deposited with the CCDC.	2023-02-07 downloaded from the CCDC.
;
_audit_creation_date             2022-10-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
lywang@zjnu.edu.cn
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H18 O2'
_chemical_formula_sum            'C22 H18 O2'
_chemical_formula_weight         314.36
_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 0.0181 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'
O O 0.0492 0.0322 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   5.7762(2)
_cell_length_b                   21.0127(8)
_cell_length_c                   14.0970(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.487(3)
_cell_angle_gamma                90
_cell_volume                     1703.16(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2499
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      66.692
_cell_measurement_theta_min      3.788
_shelx_estimated_absorpt_T_max   0.930
_shelx_estimated_absorpt_T_min   0.903
_exptl_absorpt_coefficient_mu    0.610
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6134
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0993 before and 0.0786 after correction.
The Ratio of minimum to maximum transmission is 0.8145.
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    1.226
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0874
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13261
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.165
_diffrn_reflns_theta_min         3.788
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2082
_reflns_number_total             3082
_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 (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0058(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3082
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0563
_refine_ls_restrained_S_all      1.038
_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)+(0.0503P)²+0.5484P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1282
_refine_ls_wR_factor_ref         0.1511
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C005(H005), C007(H007), C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D),
 C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J),
 C00L(H00L), C00M(H00M), C00N(H00N)
2.b Idealised Me refined as rotating group:
 C00O(H00K,H00O,H00P)
;
_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
O001 O 0.7210(3) 0.67869(8) 0.37408(12) 0.0641(5) Uani 1 1 d . . . . .
O002 O 0.6358(4) 0.72623(9) 0.23155(13) 0.0741(6) Uani 1 1 d . . . . .
C003 C 0.3237(4) 0.83536(10) 0.23736(16) 0.0478(6) Uani 1 1 d . . . . .
C004 C 0.3284(4) 0.81132(11) 0.33689(16) 0.0492(6) Uani 1 1 d . . . . .
C005 C 0.1262(4) 0.82714(11) 0.17406(17) 0.0542(6) Uani 1 1 d . . . . .
H005 H -0.002633 0.806280 0.193963 0.065 Uiso 1 1 calc R U . . .
C006 C 0.1615(4) 0.84034(11) 0.39771(16) 0.0503(6) Uani 1 1 d . . . . .
C007 C 0.4719(4) 0.76433(12) 0.37148(18) 0.0570(6) Uani 1 1 d . . . . .
H007 H 0.480343 0.756847 0.436746 0.068 Uiso 1 1 calc R U . . .
C008 C 0.6152(4) 0.72412(12) 0.31591(18) 0.0565(6) Uani 1 1 d . . . . .
C009 C 0.8641(4) 0.63275(11) 0.33689(17) 0.0537(6) Uani 1 1 d . . . . .
C00A C 0.1199(5) 0.84965(12) 0.08214(18) 0.0600(7) Uani 1 1 d . . . . .
H00A H -0.012543 0.843264 0.040290 0.072 Uiso 1 1 calc R U . . .
C00B C 0.0765(4) 0.90139(11) 0.38077(17) 0.0562(6) Uani 1 1 d . . . . .
H00B H 0.127925 0.925049 0.331114 0.067 Uiso 1 1 calc R U . . .
C00C C 0.5107(4) 0.86796(12) 0.20645(19) 0.0611(7) Uani 1 1 d . . . . .
H00C H 0.643378 0.874560 0.248054 0.073 Uiso 1 1 calc R U . . .
C00D C 1.0479(4) 0.64864(13) 0.28747(19) 0.0617(7) Uani 1 1 d . . . . .
H00D H 1.076592 0.690908 0.272923 0.074 Uiso 1 1 calc R U . . .
C00E C 0.8186(5) 0.57053(12) 0.35885(19) 0.0635(7) Uani 1 1 d . . . . .
H00E H 0.692122 0.560402 0.392152 0.076 Uiso 1 1 calc R U . . .
C00F C -0.0834(5) 0.92778(12) 0.43644(18) 0.0628(7) Uani 1 1 d . . . . .
H00F H -0.136087 0.969017 0.423788 0.075 Uiso 1 1 calc R U . . .
C00G C 0.3063(5) 0.88132(13) 0.05155(19) 0.0678(7) Uani 1 1 d . . . . .
H00G H 0.301052 0.896251 -0.010722 0.081 Uiso 1 1 calc R U . . .
C00H C 0.0771(5) 0.80672(12) 0.47250(18) 0.0631(7) Uani 1 1 d . . . . .
H00H H 0.129424 0.765485 0.485519 0.076 Uiso 1 1 calc R U . . .
C00I C 0.5016(5) 0.89083(14) 0.1141(2) 0.0705(8) Uani 1 1 d . . . . .
H00I H 0.628067 0.912744 0.094102 0.085 Uiso 1 1 calc R U . . .
C00J C 1.1906(5) 0.60064(14) 0.2595(2) 0.0697(8) Uani 1 1 d . . . . .
H00J H 1.316371 0.610798 0.225804 0.084 Uiso 1 1 calc R U . . .
C00K C -0.1669(4) 0.89416(13) 0.51060(17) 0.0595(7) Uani 1 1 d . . . . .
C00L C -0.0823(5) 0.83348(13) 0.52748(19) 0.0677(7) Uani 1 1 d . . . . .
H00L H -0.134004 0.809977 0.577215 0.081 Uiso 1 1 calc R U . . .
C00M C 1.1488(5) 0.53851(14) 0.2807(2) 0.0732(8) Uani 1 1 d . . . . .
H00M H 1.245396 0.506578 0.261407 0.088 Uiso 1 1 calc R U . . .
C00N C 0.9632(6) 0.52335(13) 0.3308(2) 0.0744(8) Uani 1 1 d . . . . .
H00N H 0.935278 0.481111 0.345723 0.089 Uiso 1 1 calc R U . . .
C00O C -0.3450(5) 0.92200(16) 0.5700(2) 0.0806(9) Uani 1 1 d . . . . .
H00K H -0.355010 0.967106 0.559662 0.121 Uiso 1 1 calc R U . . .
H00O H -0.299709 0.913740 0.636195 0.121 Uiso 1 1 calc R U . . .
H00P H -0.493728 0.902893 0.552153 0.121 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
O001 C008 1.364(3) . ?
O001 C009 1.404(3) . ?
O002 C008 1.207(3) . ?
C003 C004 1.489(3) . ?
C003 C005 1.390(3) . ?
C003 C00C 1.384(3) . ?
C004 C006 1.482(3) . ?
C004 C007 1.350(3) . ?
C005 H005 0.9300 . ?
C005 C00A 1.377(3) . ?
C006 C00B 1.386(3) . ?
C006 C00H 1.395(3) . ?
C007 H007 0.9300 . ?
C007 C008 1.462(3) . ?
C009 C00D 1.366(4) . ?
C009 C00E 1.375(3) . ?
C00A H00A 0.9300 . ?
C00A C00G 1.370(4) . ?
C00B H00B 0.9300 . ?
C00B C00F 1.384(3) . ?
C00C H00C 0.9300 . ?
C00C C00I 1.384(4) . ?
C00D H00D 0.9300 . ?
C00D C00J 1.384(4) . ?
C00E H00E 0.9300 . ?
C00E C00N 1.379(4) . ?
C00F H00F 0.9300 . ?
C00F C00K 1.386(4) . ?
C00G H00G 0.9300 . ?
C00G C00I 1.378(4) . ?
C00H H00H 0.9300 . ?
C00H C00L 1.379(4) . ?
C00I H00I 0.9300 . ?
C00J H00J 0.9300 . ?
C00J C00M 1.366(4) . ?
C00K C00L 1.378(4) . ?
C00K C00O 1.506(4) . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00M C00N 1.376(4) . ?
C00N H00N 0.9300 . ?
C00O H00K 0.9600 . ?
C00O H00O 0.9600 . ?
C00O H00P 0.9600 . ?

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
C008 O001 C009 120.16(19) . . ?
C005 C003 C004 120.2(2) . . ?
C00C C003 C004 121.3(2) . . ?
C00C C003 C005 118.4(2) . . ?
C006 C004 C003 116.83(19) . . ?
C007 C004 C003 123.0(2) . . ?
C007 C004 C006 120.2(2) . . ?
C003 C005 H005 119.7 . . ?
C00A C005 C003 120.5(2) . . ?
C00A C005 H005 119.7 . . ?
C00B C006 C004 121.4(2) . . ?
C00B C006 C00H 117.1(2) . . ?
C00H C006 C004 121.5(2) . . ?
C004 C007 H007 117.0 . . ?
C004 C007 C008 126.1(2) . . ?
C008 C007 H007 117.0 . . ?
O001 C008 C007 109.1(2) . . ?
O002 C008 O001 122.5(2) . . ?
O002 C008 C007 128.4(2) . . ?
C00D C009 O001 122.4(2) . . ?
C00D C009 C00E 121.5(2) . . ?
C00E C009 O001 116.0(2) . . ?
C005 C00A H00A 119.6 . . ?
C00G C00A C005 120.8(2) . . ?
C00G C00A H00A 119.6 . . ?
C006 C00B H00B 119.4 . . ?
C00F C00B C006 121.2(2) . . ?
C00F C00B H00B 119.4 . . ?
C003 C00C H00C 119.8 . . ?
C00I C00C C003 120.5(2) . . ?
C00I C00C H00C 119.8 . . ?
C009 C00D H00D 120.6 . . ?
C009 C00D C00J 118.7(2) . . ?
C00J C00D H00D 120.6 . . ?
C009 C00E H00E 120.5 . . ?
C009 C00E C00N 119.0(3) . . ?
C00N C00E H00E 120.5 . . ?
C00B C00F H00F 119.2 . . ?
C00B C00F C00K 121.5(2) . . ?
C00K C00F H00F 119.2 . . ?
C00A C00G H00G 120.4 . . ?
C00A C00G C00I 119.3(3) . . ?
C00I C00G H00G 120.4 . . ?
C006 C00H H00H 119.4 . . ?
C00L C00H C006 121.2(2) . . ?
C00L C00H H00H 119.4 . . ?
C00C C00I H00I 119.8 . . ?
C00G C00I C00C 120.4(3) . . ?
C00G C00I H00I 119.8 . . ?
C00D C00J H00J 119.6 . . ?
C00M C00J C00D 120.8(3) . . ?
C00M C00J H00J 119.6 . . ?
C00F C00K C00O 121.8(2) . . ?
C00L C00K C00F 117.3(2) . . ?
C00L C00K C00O 120.9(3) . . ?
C00H C00L H00L 119.2 . . ?
C00K C00L C00H 121.7(2) . . ?
C00K C00L H00L 119.2 . . ?
C00J C00M H00M 120.1 . . ?
C00J C00M C00N 119.8(3) . . ?
C00N C00M H00M 120.1 . . ?
C00E C00N H00N 119.9 . . ?
C00M C00N C00E 120.3(3) . . ?
C00M C00N H00N 119.9 . . ?
C00K C00O H00K 109.5 . . ?
C00K C00O H00O 109.5 . . ?
C00K C00O H00P 109.5 . . ?
H00K C00O H00O 109.5 . . ?
H00K C00O H00P 109.5 . . ?
H00O C00O H00P 109.5 . . ?

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
O001 C009 C00D C00J 175.2(2) . . . . ?
O001 C009 C00E C00N -175.2(2) . . . . ?
C003 C004 C006 C00B -25.9(3) . . . . ?
C003 C004 C006 C00H 152.0(2) . . . . ?
C003 C004 C007 C008 -9.6(4) . . . . ?
C003 C005 C00A C00G -0.9(4) . . . . ?
C003 C00C C00I C00G -0.1(4) . . . . ?
C004 C003 C005 C00A 179.5(2) . . . . ?
C004 C003 C00C C00I -179.0(2) . . . . ?
C004 C006 C00B C00F 178.5(2) . . . . ?
C004 C006 C00H C00L -178.5(2) . . . . ?
C004 C007 C008 O001 -174.9(2) . . . . ?
C004 C007 C008 O002 1.8(5) . . . . ?
C005 C003 C004 C006 -63.5(3) . . . . ?
C005 C003 C004 C007 114.9(3) . . . . ?
C005 C003 C00C C00I -1.0(4) . . . . ?
C005 C00A C00G C00I -0.3(4) . . . . ?
C006 C004 C007 C008 168.7(2) . . . . ?
C006 C00B C00F C00K -0.7(4) . . . . ?
C006 C00H C00L C00K 0.6(4) . . . . ?
C007 C004 C006 C00B 155.7(2) . . . . ?
C007 C004 C006 C00H -26.5(4) . . . . ?
C008 O001 C009 C00D 54.7(3) . . . . ?
C008 O001 C009 C00E -129.7(3) . . . . ?
C009 O001 C008 O002 1.3(4) . . . . ?
C009 O001 C008 C007 178.2(2) . . . . ?
C009 C00D C00J C00M 0.0(4) . . . . ?
C009 C00E C00N C00M -0.6(4) . . . . ?
C00A C00G C00I C00C 0.8(4) . . . . ?
C00B C006 C00H C00L -0.5(4) . . . . ?
C00B C00F C00K C00L 0.7(4) . . . . ?
C00B C00F C00K C00O -178.6(3) . . . . ?
C00C C003 C004 C006 114.4(3) . . . . ?
C00C C003 C004 C007 -67.2(3) . . . . ?
C00C C003 C005 C00A 1.6(3) . . . . ?
C00D C009 C00E C00N 0.5(4) . . . . ?
C00D C00J C00M C00N -0.2(4) . . . . ?
C00E C009 C00D C00J -0.2(4) . . . . ?
C00F C00K C00L C00H -0.7(4) . . . . ?
C00H C006 C00B C00F 0.6(4) . . . . ?
C00J C00M C00N C00E 0.5(5) . . . . ?
C00O C00K C00L C00H 178.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
