# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2204725'
loop_
_audit_author_name
_audit_author_address
leipound
;Zhejiang University of Technology
China
;
_audit_update_record             
;
2022-09-01 deposited with the CCDC.	2023-08-06 downloaded from the CCDC.
;
_audit_creation_date             2022-07-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H13 F3'
_chemical_formula_sum            'C16 H13 F3'
_chemical_formula_weight         262.26
_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 0.0137 0.0067 '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 0.0583 0.0400 '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                   4.8272(4)
_cell_length_b                   9.3359(8)
_cell_length_c                   14.3768(13)
_cell_angle_alpha                87.031(4)
_cell_angle_beta                 80.964(4)
_cell_angle_gamma                77.047(3)
_cell_volume                     623.49(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5257
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      60.00
_cell_measurement_theta_min      4.98
_shelx_estimated_absorpt_T_max   0.942
_shelx_estimated_absorpt_T_min   0.926
_exptl_absorpt_coefficient_mu    0.601
_exptl_absorpt_correction_T_max  0.7518
_exptl_absorpt_correction_T_min  0.3920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1637 before and 0.0959 after correction.
The Ratio of minimum to maximum transmission is 0.5214.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.0551
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6808
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.150
_diffrn_reflns_theta_min         4.984
_diffrn_ambient_temperature      193.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Metaljet PHOTON II'
_diffrn_measurement_method       'ω and φ shutterless scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   MetalJet
_diffrn_source_current           2.86
_diffrn_source_power             0.19937059999999998
_diffrn_source_type              'Liquid Metal source'
_diffrn_source_voltage           69.71
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2296
_reflns_number_total             2690
_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, 2019)'
_computing_data_collection       'APEX4 V2021.10-0 (Bruker, 2021)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       0.105(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2690
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0715
_refine_ls_restrained_S_all      1.088
_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)+(0.1547P)²+0.0543P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2043
_refine_ls_wR_factor_ref         0.2135
_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 Ternary CH refined with riding coordinates:
 C13(H13)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C11(H11), C2(H2), C5(H5), C4(H4), C3(H3)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C15(H15A,H15B,H15C)
;
_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
F3 F 0.43187(19) 0.74850(11) 0.61557(8) 0.0425(4) Uani 1 1 d . . . . .
F2 F 0.8613(2) 0.78177(12) 0.57664(9) 0.0459(4) Uani 1 1 d . . . . .
F1 F 0.7392(3) 0.59930(13) 0.52213(8) 0.0474(4) Uani 1 1 d . . . . .
C12 C 0.6298(3) 0.46703(16) 0.70812(12) 0.0290(4) Uani 1 1 d . . . . .
C7 C 0.4776(3) 0.48839(17) 0.79942(12) 0.0288(4) Uani 1 1 d . . . . .
C8 C 0.3039(3) 0.39287(18) 0.83721(13) 0.0320(4) Uani 1 1 d . . . . .
H8 H 0.197529 0.408749 0.898644 0.038 Uiso 1 1 calc R U . . .
C13 C 0.8013(3) 0.58471(16) 0.68294(12) 0.0292(4) Uani 1 1 d . . . . .
H13 H 1.011162 0.538601 0.669861 0.035 Uiso 1 1 calc R U . . .
C6 C 0.5436(3) 0.61545(16) 0.83932(12) 0.0294(4) Uani 1 1 d . . . . .
C11 C 0.6126(3) 0.34962(18) 0.65603(13) 0.0336(4) Uani 1 1 d . . . . .
H11 H 0.716298 0.335455 0.594133 0.040 Uiso 1 1 calc R U . . .
C1 C 0.7365(3) 0.67300(17) 0.77238(12) 0.0297(4) Uani 1 1 d . . . . .
C2 C 0.8396(3) 0.79276(18) 0.79337(14) 0.0353(4) Uani 1 1 d . . . . .
H2 H 0.970258 0.831932 0.748271 0.042 Uiso 1 1 calc R U . . .
C14 C 0.7095(3) 0.67808(18) 0.59945(13) 0.0336(4) Uani 1 1 d . . . . .
C10 C 0.4424(3) 0.25174(17) 0.69463(13) 0.0340(5) Uani 1 1 d . . . . .
C9 C 0.2849(3) 0.27493(17) 0.78599(13) 0.0336(4) Uani 1 1 d . . . . .
C5 C 0.4529(4) 0.67781(18) 0.92752(13) 0.0346(4) Uani 1 1 d . . . . .
H5 H 0.321709 0.639474 0.972918 0.042 Uiso 1 1 calc R U . . .
C16 C 0.1012(4) 0.1704(2) 0.82886(16) 0.0419(5) Uani 1 1 d . . . . .
H16A H 0.011907 0.201630 0.892696 0.063 Uiso 1 1 calc R U . . .
H16B H 0.221253 0.070985 0.831551 0.063 Uiso 1 1 calc R U . . .
H16C H -0.048938 0.170505 0.790190 0.063 Uiso 1 1 calc R U . . .
C4 C 0.5583(4) 0.79763(19) 0.94795(14) 0.0391(5) Uani 1 1 d . . . . .
H4 H 0.499294 0.841030 1.008187 0.047 Uiso 1 1 calc R U . . .
C3 C 0.7471(4) 0.85445(19) 0.88217(15) 0.0393(5) Uani 1 1 d . . . . .
H3 H 0.815108 0.936843 0.897580 0.047 Uiso 1 1 calc R U . . .
C15 C 0.4289(5) 0.1230(2) 0.63851(16) 0.0472(5) Uani 1 1 d . . . . .
H15A H 0.232144 0.132512 0.625579 0.071 Uiso 1 1 calc R U . . .
H15B H 0.485799 0.031859 0.674414 0.071 Uiso 1 1 calc R U . . .
H15C H 0.559876 0.120609 0.578891 0.071 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
F3 C14 1.3438(17) . ?
F2 C14 1.338(2) . ?
F1 C14 1.336(2) . ?
C12 C7 1.400(2) . ?
C12 C13 1.515(2) . ?
C12 C11 1.384(2) . ?
C7 C8 1.391(2) . ?
C7 C6 1.461(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.383(2) . ?
C13 H13 1.0000 . ?
C13 C1 1.516(2) . ?
C13 C14 1.511(2) . ?
C6 C1 1.404(2) . ?
C6 C5 1.388(2) . ?
C11 H11 0.9500 . ?
C11 C10 1.400(2) . ?
C1 C2 1.386(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.394(3) . ?
C10 C9 1.412(3) . ?
C10 C15 1.501(2) . ?
C9 C16 1.508(2) . ?
C5 H5 0.9500 . ?
C5 C4 1.390(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C4 H4 0.9500 . ?
C4 C3 1.379(3) . ?
C3 H3 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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 C12 C13 109.98(14) . . ?
C11 C12 C7 120.27(16) . . ?
C11 C12 C13 129.74(16) . . ?
C12 C7 C6 108.83(14) . . ?
C8 C7 C12 119.88(15) . . ?
C8 C7 C6 131.29(16) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.48(17) . . ?
C9 C8 H8 119.8 . . ?
C12 C13 H13 110.0 . . ?
C12 C13 C1 102.57(13) . . ?
C1 C13 H13 110.0 . . ?
C14 C13 C12 112.14(13) . . ?
C14 C13 H13 110.0 . . ?
C14 C13 C1 111.87(13) . . ?
C1 C6 C7 108.78(15) . . ?
C5 C6 C7 130.72(16) . . ?
C5 C6 C1 120.48(15) . . ?
C12 C11 H11 120.0 . . ?
C12 C11 C10 119.94(17) . . ?
C10 C11 H11 120.0 . . ?
C6 C1 C13 109.80(14) . . ?
C2 C1 C13 129.65(16) . . ?
C2 C1 C6 120.54(16) . . ?
C1 C2 H2 120.8 . . ?
C1 C2 C3 118.48(17) . . ?
C3 C2 H2 120.8 . . ?
F3 C14 C13 112.21(14) . . ?
F2 C14 F3 106.41(13) . . ?
F2 C14 C13 112.38(13) . . ?
F1 C14 F3 106.12(13) . . ?
F1 C14 F2 106.61(14) . . ?
F1 C14 C13 112.64(13) . . ?
C11 C10 C9 119.74(15) . . ?
C11 C10 C15 119.72(18) . . ?
C9 C10 C15 120.55(17) . . ?
C8 C9 C10 119.68(16) . . ?
C8 C9 C16 119.82(18) . . ?
C10 C9 C16 120.49(16) . . ?
C6 C5 H5 120.7 . . ?
C6 C5 C4 118.51(17) . . ?
C4 C5 H5 120.7 . . ?
C9 C16 H16A 109.5 . . ?
C9 C16 H16B 109.5 . . ?
C9 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C5 C4 H4 119.5 . . ?
C3 C4 C5 121.04(18) . . ?
C3 C4 H4 119.5 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 120.96(16) . . ?
C4 C3 H3 119.5 . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C12 C7 C8 C9 1.3(2) . . . . ?
C12 C7 C6 C1 0.17(16) . . . . ?
C12 C7 C6 C5 -178.22(14) . . . . ?
C12 C13 C1 C6 -1.78(14) . . . . ?
C12 C13 C1 C2 177.76(14) . . . . ?
C12 C13 C14 F3 60.41(18) . . . . ?
C12 C13 C14 F2 -179.71(13) . . . . ?
C12 C13 C14 F1 -59.27(18) . . . . ?
C12 C11 C10 C9 1.1(2) . . . . ?
C12 C11 C10 C15 -178.87(13) . . . . ?
C7 C12 C13 C1 1.89(14) . . . . ?
C7 C12 C13 C14 -118.29(14) . . . . ?
C7 C12 C11 C10 0.0(2) . . . . ?
C7 C8 C9 C10 -0.2(2) . . . . ?
C7 C8 C9 C16 178.55(13) . . . . ?
C7 C6 C1 C13 1.08(16) . . . . ?
C7 C6 C1 C2 -178.51(12) . . . . ?
C7 C6 C5 C4 177.96(14) . . . . ?
C8 C7 C6 C1 178.86(14) . . . . ?
C8 C7 C6 C5 0.5(3) . . . . ?
C13 C12 C7 C8 179.78(12) . . . . ?
C13 C12 C7 C6 -1.35(16) . . . . ?
C13 C12 C11 C10 178.74(12) . . . . ?
C13 C1 C2 C3 -179.55(14) . . . . ?
C6 C7 C8 C9 -177.24(13) . . . . ?
C6 C1 C2 C3 0.0(2) . . . . ?
C6 C5 C4 C3 0.5(2) . . . . ?
C11 C12 C7 C8 -1.3(2) . . . . ?
C11 C12 C7 C6 177.61(12) . . . . ?
C11 C12 C13 C1 -176.93(14) . . . . ?
C11 C12 C13 C14 62.9(2) . . . . ?
C11 C10 C9 C8 -1.1(2) . . . . ?
C11 C10 C9 C16 -179.78(13) . . . . ?
C1 C13 C14 F3 -54.20(18) . . . . ?
C1 C13 C14 F2 65.68(17) . . . . ?
C1 C13 C14 F1 -173.89(13) . . . . ?
C1 C6 C5 C4 -0.3(2) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C14 C13 C1 C6 118.59(14) . . . . ?
C14 C13 C1 C2 -61.9(2) . . . . ?
C5 C6 C1 C13 179.66(12) . . . . ?
C5 C6 C1 C2 0.1(2) . . . . ?
C5 C4 C3 C2 -0.5(3) . . . . ?
C15 C10 C9 C8 178.94(13) . . . . ?
C15 C10 C9 C16 0.2(2) . . . . ?

_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_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2204726'
loop_
_audit_author_name
_audit_author_address
CHEN
;Zhejiang University of Technology
China
;
_audit_update_record             
;
2022-09-01 deposited with the CCDC.	2023-08-06 downloaded from the CCDC.
;
_audit_creation_date             2022-07-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H13 F3'
_chemical_formula_sum            'C16 H13 F3'
_chemical_formula_weight         262.26
_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 0.0137 0.0067 '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 0.0583 0.0400 '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                   12.8122(6)
_cell_length_b                   4.8770(2)
_cell_length_c                   20.0701(9)
_cell_angle_alpha                90
_cell_angle_beta                 98.304(2)
_cell_angle_gamma                90
_cell_volume                     1240.93(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5284
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      59.66
_cell_measurement_theta_min      3.03
_shelx_estimated_absorpt_T_max   0.942
_shelx_estimated_absorpt_T_min   0.926
_exptl_absorpt_coefficient_mu    0.604
_exptl_absorpt_correction_T_max  0.7518
_exptl_absorpt_correction_T_min  0.5867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1269 before and 0.0680 after correction.
The Ratio of minimum to maximum transmission is 0.7804.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7925
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.381
_diffrn_reflns_theta_min         3.033
_diffrn_ambient_temperature      193.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Metaljet PHOTON II'
_diffrn_measurement_method       'ω and φ shutterless scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   MetalJet
_diffrn_source_current           2.85
_diffrn_source_power             0.1986735
_diffrn_source_type              'Liquid Metal source'
_diffrn_source_voltage           69.71
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2214
_reflns_number_total             2603
_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, 2019)'
_computing_data_collection       'APEX4 V2021.10-0 (Bruker, 2021)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2603
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0578
_refine_ls_restrained_S_all      1.100
_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)+(0.1239P)²+0.4004P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1846
_refine_ls_wR_factor_ref         0.1934
_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 Ternary CH refined with riding coordinates:
 C13(H13)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C8(H8), C3(H3), C5(H5), C10(H10), C4(H4)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_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
F2 F 0.22228(11) 0.2291(3) 0.21268(6) 0.0447(4) Uani 1 1 d . . . . .
F1 F 0.22610(11) 0.6451(3) 0.24704(6) 0.0463(4) Uani 1 1 d . . . . .
F3 F 0.08687(10) 0.4019(3) 0.24783(6) 0.0479(4) Uani 1 1 d . . . . .
C1 C 0.35397(14) 0.2939(4) 0.33994(9) 0.0264(4) Uani 1 1 d . . . . .
C7 C 0.30568(14) 0.6175(4) 0.41503(8) 0.0261(4) Uani 1 1 d . . . . .
C13 C 0.23438(14) 0.2972(4) 0.33059(9) 0.0261(4) Uani 1 1 d . . . . .
H13 H 0.206100 0.111436 0.339180 0.031 Uiso 1 1 calc R U . . .
C6 C 0.39391(14) 0.4892(4) 0.38776(8) 0.0267(4) Uani 1 1 d . . . . .
C12 C 0.21094(14) 0.5002(4) 0.38419(8) 0.0261(4) Uani 1 1 d . . . . .
C2 C 0.42082(15) 0.1327(4) 0.30814(9) 0.0314(4) Uani 1 1 d . . . . .
H2 H 0.393478 -0.000527 0.275710 0.038 Uiso 1 1 calc R U . . .
C8 C 0.30699(15) 0.8123(4) 0.46540(9) 0.0297(4) Uani 1 1 d . . . . .
H8 H 0.371607 0.893534 0.484952 0.036 Uiso 1 1 calc R U . . .
C3 C 0.52933(16) 0.1709(4) 0.32492(10) 0.0357(5) Uani 1 1 d . . . . .
H3 H 0.576484 0.060563 0.304069 0.043 Uiso 1 1 calc R U . . .
C14 C 0.19231(16) 0.3937(4) 0.26007(9) 0.0319(4) Uani 1 1 d . . . . .
C9 C 0.21247(16) 0.8879(4) 0.48707(9) 0.0317(4) Uani 1 1 d . . . . .
C11 C 0.11543(14) 0.5657(4) 0.40612(9) 0.0298(4) Uani 1 1 d . . . . .
C5 C 0.50207(14) 0.5273(4) 0.40398(9) 0.0321(4) Uani 1 1 d . . . . .
H5 H 0.529579 0.659939 0.436526 0.038 Uiso 1 1 calc R U . . .
C10 C 0.11934(16) 0.7614(4) 0.45724(10) 0.0336(5) Uani 1 1 d . . . . .
H10 H 0.055203 0.811372 0.472582 0.040 Uiso 1 1 calc R U . . .
C15 C 0.01275(15) 0.4268(5) 0.38000(11) 0.0382(5) Uani 1 1 d . . . . .
H15A H -0.020335 0.520217 0.339101 0.057 Uiso 1 1 calc R U . . .
H15B H -0.034392 0.435115 0.414300 0.057 Uiso 1 1 calc R U . . .
H15C H 0.026111 0.234806 0.369598 0.057 Uiso 1 1 calc R U . . .
C4 C 0.56924(16) 0.3672(4) 0.37153(10) 0.0360(5) Uani 1 1 d . . . . .
H4 H 0.643355 0.392931 0.381485 0.043 Uiso 1 1 calc R U . . .
C16 C 0.21092(18) 1.0951(4) 0.54249(11) 0.0407(5) Uani 1 1 d . . . . .
H16A H 0.278803 1.092344 0.572092 0.061 Uiso 1 1 calc R U . . .
H16B H 0.154286 1.049697 0.568616 0.061 Uiso 1 1 calc R U . . .
H16C H 0.198649 1.278317 0.522843 0.061 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
F2 C14 1.342(2) . ?
F1 C14 1.339(2) . ?
F3 C14 1.338(2) . ?
C1 C13 1.517(2) . ?
C1 C6 1.396(3) . ?
C1 C2 1.384(3) . ?
C7 C6 1.466(2) . ?
C7 C12 1.403(2) . ?
C7 C8 1.385(2) . ?
C13 H13 1.0000 . ?
C13 C12 1.523(2) . ?
C13 C14 1.515(2) . ?
C6 C5 1.389(2) . ?
C12 C11 1.396(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.395(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.394(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(3) . ?
C9 C10 1.399(3) . ?
C9 C16 1.505(3) . ?
C11 C10 1.397(3) . ?
C11 C15 1.505(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.392(3) . ?
C10 H10 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C4 H4 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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
C6 C1 C13 109.95(15) . . ?
C2 C1 C13 129.07(17) . . ?
C2 C1 C6 120.98(18) . . ?
C12 C7 C6 109.02(16) . . ?
C8 C7 C6 129.54(17) . . ?
C8 C7 C12 121.36(17) . . ?
C1 C13 H13 110.7 . . ?
C1 C13 C12 102.61(14) . . ?
C12 C13 H13 110.7 . . ?
C14 C13 C1 109.61(15) . . ?
C14 C13 H13 110.7 . . ?
C14 C13 C12 112.21(15) . . ?
C1 C6 C7 108.80(16) . . ?
C5 C6 C1 120.44(17) . . ?
C5 C6 C7 130.71(17) . . ?
C7 C12 C13 109.30(15) . . ?
C11 C12 C7 120.64(17) . . ?
C11 C12 C13 129.98(17) . . ?
C1 C2 H2 120.8 . . ?
C1 C2 C3 118.31(18) . . ?
C3 C2 H2 120.8 . . ?
C7 C8 H8 120.4 . . ?
C7 C8 C9 119.29(18) . . ?
C9 C8 H8 120.4 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 120.91(18) . . ?
C4 C3 H3 119.5 . . ?
F2 C14 C13 112.13(16) . . ?
F1 C14 F2 106.00(16) . . ?
F1 C14 C13 112.69(15) . . ?
F3 C14 F2 105.79(15) . . ?
F3 C14 F1 106.45(16) . . ?
F3 C14 C13 113.22(16) . . ?
C8 C9 C10 118.41(17) . . ?
C8 C9 C16 120.85(19) . . ?
C10 C9 C16 120.72(18) . . ?
C12 C11 C10 116.60(17) . . ?
C12 C11 C15 123.32(18) . . ?
C10 C11 C15 120.00(17) . . ?
C6 C5 H5 120.7 . . ?
C6 C5 C4 118.58(18) . . ?
C4 C5 H5 120.7 . . ?
C9 C10 H10 118.2 . . ?
C11 C10 C9 123.61(18) . . ?
C11 C10 H10 118.2 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C3 C4 C5 120.77(19) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C9 C16 H16A 109.5 . . ?
C9 C16 H16B 109.5 . . ?
C9 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
C1 C13 C12 C7 5.45(18) . . . . ?
C1 C13 C12 C11 -171.27(17) . . . . ?
C1 C13 C14 F2 60.3(2) . . . . ?
C1 C13 C14 F1 -59.2(2) . . . . ?
C1 C13 C14 F3 179.90(15) . . . . ?
C1 C6 C5 C4 0.0(3) . . . . ?
C1 C2 C3 C4 -0.8(3) . . . . ?
C7 C6 C5 C4 177.30(18) . . . . ?
C7 C12 C11 C10 3.1(3) . . . . ?
C7 C12 C11 C15 -173.75(17) . . . . ?
C7 C8 C9 C10 0.5(3) . . . . ?
C7 C8 C9 C16 178.94(17) . . . . ?
C13 C1 C6 C7 3.33(19) . . . . ?
C13 C1 C6 C5 -178.87(16) . . . . ?
C13 C1 C2 C3 179.14(17) . . . . ?
C13 C12 C11 C10 179.48(17) . . . . ?
C13 C12 C11 C15 2.6(3) . . . . ?
C6 C1 C13 C12 -5.30(18) . . . . ?
C6 C1 C13 C14 114.10(17) . . . . ?
C6 C1 C2 C3 -0.2(3) . . . . ?
C6 C7 C12 C13 -3.8(2) . . . . ?
C6 C7 C12 C11 173.31(16) . . . . ?
C6 C7 C8 C9 -174.51(17) . . . . ?
C6 C5 C4 C3 -1.1(3) . . . . ?
C12 C7 C6 C1 0.3(2) . . . . ?
C12 C7 C6 C5 -177.20(18) . . . . ?
C12 C7 C8 C9 1.7(3) . . . . ?
C12 C13 C14 F2 173.61(15) . . . . ?
C12 C13 C14 F1 54.1(2) . . . . ?
C12 C13 C14 F3 -66.8(2) . . . . ?
C12 C11 C10 C9 -0.9(3) . . . . ?
C2 C1 C13 C12 175.29(17) . . . . ?
C2 C1 C13 C14 -65.3(2) . . . . ?
C2 C1 C6 C7 -177.21(16) . . . . ?
C2 C1 C6 C5 0.6(3) . . . . ?
C2 C3 C4 C5 1.5(3) . . . . ?
C8 C7 C6 C1 176.87(18) . . . . ?
C8 C7 C6 C5 -0.6(3) . . . . ?
C8 C7 C12 C13 179.32(15) . . . . ?
C8 C7 C12 C11 -3.6(3) . . . . ?
C8 C9 C10 C11 -0.9(3) . . . . ?
C14 C13 C12 C7 -112.13(17) . . . . ?
C14 C13 C12 C11 71.2(2) . . . . ?
C15 C11 C10 C9 176.06(18) . . . . ?
C16 C9 C10 C11 -179.35(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
