# 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_t_a
_database_code_depnum_ccdc_archive 'CCDC 2224422'
loop_
_audit_author_name
_audit_author_address
'Siqi Dong'
;Shanghai Jiao Tong University
China
;
_audit_update_record             
;
2022-12-05 deposited with the CCDC.	2023-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H20 F N O3'
_chemical_formula_sum            'C22 H20 F N O3'
_chemical_formula_weight         365.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   5.7149(9)
_cell_length_b                   15.8503(10)
_cell_length_c                   19.6731(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1782.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9969
_cell_measurement_theta_min      3.58
_cell_measurement_theta_max      67.97

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   0.5744
_exptl_transmission_factor_max   0.7530
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.802
_shelx_estimated_absorpt_T_min   0.843
_shelx_estimated_absorpt_T_max   0.869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13794
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.581
_diffrn_reflns_theta_max         68.203
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3237
_reflns_number_gt                3130
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.708
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.996

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0567P)²+0.1435P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1268 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(7)
_chemical_absolute_configuration AD
_refine_ls_number_reflns         3237
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0883
_refine_ls_wR_factor_gt          0.0871
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.9068(3) 0.03035(8) 0.00359(7) 0.0426(4) Uani 1 1 d . . . . .
C1 C 0.8286(4) 0.10002(12) 0.03688(10) 0.0292(5) Uani 1 1 d . . . . .
N1 N 0.6039(3) 0.40217(10) 0.28221(8) 0.0253(4) Uani 1 1 d . . . . .
O1 O 0.3793(2) 0.34040(9) 0.12842(8) 0.0341(4) Uani 1 1 d . . . . .
O2 O 0.8522(3) 0.28939(9) 0.27169(7) 0.0326(4) Uani 1 1 d . . . . .
C2 C 0.6145(4) 0.13208(13) 0.01874(10) 0.0298(4) Uani 1 1 d . . . . .
H2 H 0.522088 0.105606 -0.015261 0.036 Uiso 1 1 calc R U . . .
O3 O 0.4079(3) 0.36614(11) 0.55815(7) 0.0385(4) Uani 1 1 d . . . . .
C3 C 0.5372(3) 0.20430(13) 0.05154(9) 0.0260(4) Uani 1 1 d . . . . .
H3 H 0.388645 0.227404 0.040430 0.031 Uiso 1 1 calc R U . . .
C4 C 0.6762(3) 0.24345(12) 0.10091(9) 0.0232(4) Uani 1 1 d . . . . .
C7 C 0.5842(3) 0.32187(12) 0.13356(9) 0.0233(4) Uani 1 1 d . . . . .
C6 C 0.9683(4) 0.13534(13) 0.08607(10) 0.0294(4) Uani 1 1 d . . . . .
H6 H 1.113808 0.110366 0.097929 0.035 Uiso 1 1 calc R U . . .
C5 C 0.8917(3) 0.20848(12) 0.11808(10) 0.0265(4) Uani 1 1 d . . . . .
H5 H 0.986528 0.234618 0.151695 0.032 Uiso 1 1 calc R U . . .
C9 C 0.7465(3) 0.34936(12) 0.24830(10) 0.0236(4) Uani 1 1 d . . . . .
C8 C 0.7507(3) 0.37810(12) 0.17353(9) 0.0224(4) Uani 1 1 d . . . . .
H8 H 0.912736 0.374715 0.154566 0.027 Uiso 1 1 calc R U . . .
C10 C 0.5037(3) 0.47054(12) 0.23986(9) 0.0251(4) Uani 1 1 d . . . . .
H10 H 0.343423 0.453556 0.224746 0.030 Uiso 1 1 calc R U . . .
C11 C 0.6686(3) 0.47027(12) 0.17791(9) 0.0228(4) Uani 1 1 d . . . . .
H11 H 0.582609 0.486982 0.135735 0.027 Uiso 1 1 calc R U . . .
C12 C 0.8764(4) 0.52838(13) 0.19024(10) 0.0283(4) Uani 1 1 d . . . . .
H12A H 0.979855 0.527507 0.149886 0.034 Uiso 1 1 calc R U . . .
H12B H 0.967337 0.507298 0.229546 0.034 Uiso 1 1 calc R U . . .
C13 C 0.7989(4) 0.61898(13) 0.20413(11) 0.0344(5) Uani 1 1 d . . . . .
H13A H 0.934856 0.652666 0.219506 0.041 Uiso 1 1 calc R U . . .
H13B H 0.738610 0.644519 0.161676 0.041 Uiso 1 1 calc R U . . .
C14 C 0.6132(4) 0.62093(14) 0.25714(11) 0.0352(5) Uani 1 1 d . . . . .
H14 H 0.581952 0.673175 0.278996 0.042 Uiso 1 1 calc R U . . .
C15 C 0.4886(4) 0.55423(14) 0.27572(11) 0.0320(5) Uani 1 1 d . . . . .
H15 H 0.385369 0.559499 0.313325 0.038 Uiso 1 1 calc R U . . .
C16 C 0.5459(4) 0.39146(13) 0.35285(9) 0.0250(4) Uani 1 1 d . . . . .
C17 C 0.3421(3) 0.35140(13) 0.37185(10) 0.0266(4) Uani 1 1 d . . . . .
H17 H 0.238495 0.330398 0.338101 0.032 Uiso 1 1 calc R U . . .
C18 C 0.2875(3) 0.34158(13) 0.44076(10) 0.0282(4) Uani 1 1 d . . . . .
H18 H 0.146971 0.314049 0.453945 0.034 Uiso 1 1 calc R U . . .
C19 C 0.4397(4) 0.37227(13) 0.48950(9) 0.0275(4) Uani 1 1 d . . . . .
C20 C 0.6447(4) 0.41278(14) 0.46996(10) 0.0315(5) Uani 1 1 d . . . . .
H20 H 0.748696 0.434066 0.503517 0.038 Uiso 1 1 calc R U . . .
C21 C 0.6976(4) 0.42214(13) 0.40191(10) 0.0292(4) Uani 1 1 d . . . . .
H21 H 0.838102 0.449654 0.388707 0.035 Uiso 1 1 calc R U . . .
C22 C 0.2054(4) 0.32333(17) 0.58196(11) 0.0400(5) Uani 1 1 d . . . . .
H22A H 0.065048 0.352146 0.565230 0.060 Uiso 1 1 calc R U . . .
H22B H 0.204785 0.323249 0.631769 0.060 Uiso 1 1 calc R U . . .
H22C H 0.206769 0.265066 0.565290 0.060 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.359(2) . ?
C1 C2 1.372(3) . ?
C1 C6 1.374(3) . ?
N1 C9 1.345(2) . ?
N1 C16 1.439(2) . ?
N1 C10 1.482(2) . ?
O1 C7 1.212(2) . ?
O2 C9 1.217(2) . ?
C2 C3 1.386(3) . ?
O3 C19 1.366(2) . ?
O3 C22 1.421(3) . ?
C3 C4 1.400(3) . ?
C4 C5 1.392(3) . ?
C4 C7 1.495(3) . ?
C7 C8 1.522(3) . ?
C6 C5 1.390(3) . ?
C9 C8 1.540(3) . ?
C8 C11 1.537(3) . ?
C10 C15 1.505(3) . ?
C10 C11 1.541(2) . ?
C11 C12 1.522(3) . ?
C12 C13 1.527(3) . ?
C13 C14 1.488(3) . ?
C14 C15 1.326(3) . ?
C16 C17 1.378(3) . ?
C16 C21 1.386(3) . ?
C17 C18 1.400(3) . ?
C18 C19 1.383(3) . ?
C19 C20 1.391(3) . ?
C20 C21 1.380(3) . ?

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
F1 C1 C2 117.96(19) . . ?
F1 C1 C6 118.64(19) . . ?
C2 C1 C6 123.40(19) . . ?
C9 N1 C16 123.03(16) . . ?
C9 N1 C10 114.22(15) . . ?
C16 N1 C10 122.70(15) . . ?
C1 C2 C3 117.97(19) . . ?
C19 O3 C22 117.92(17) . . ?
C2 C3 C4 120.53(18) . . ?
C5 C4 C3 119.60(18) . . ?
C5 C4 C7 122.56(17) . . ?
C3 C4 C7 117.84(17) . . ?
O1 C7 C4 120.39(17) . . ?
O1 C7 C8 120.35(18) . . ?
C4 C7 C8 119.27(16) . . ?
C1 C6 C5 118.43(19) . . ?
C6 C5 C4 120.05(18) . . ?
O2 C9 N1 126.82(18) . . ?
O2 C9 C8 125.79(17) . . ?
N1 C9 C8 107.39(15) . . ?
C7 C8 C11 113.25(16) . . ?
C7 C8 C9 108.09(15) . . ?
C11 C8 C9 102.88(15) . . ?
N1 C10 C15 113.77(15) . . ?
N1 C10 C11 101.91(14) . . ?
C15 C10 C11 114.10(16) . . ?
C12 C11 C8 110.25(15) . . ?
C12 C11 C10 110.45(15) . . ?
C8 C11 C10 103.51(15) . . ?
C11 C12 C13 111.80(17) . . ?
C14 C13 C12 110.58(18) . . ?
C15 C14 C13 124.0(2) . . ?
C14 C15 C10 122.88(19) . . ?
C17 C16 C21 120.10(17) . . ?
C17 C16 N1 120.74(18) . . ?
C21 C16 N1 119.17(18) . . ?
C16 C17 C18 120.16(18) . . ?
C19 C18 C17 119.47(18) . . ?
O3 C19 C18 125.21(19) . . ?
O3 C19 C20 114.72(18) . . ?
C18 C19 C20 120.06(18) . . ?
C21 C20 C19 120.14(19) . . ?
C20 C21 C16 120.07(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C2 C3 -178.49(17) . . . . ?
C6 C1 C2 C3 0.6(3) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C2 C3 C4 C5 -1.3(3) . . . . ?
C2 C3 C4 C7 179.06(17) . . . . ?
C5 C4 C7 O1 -164.22(19) . . . . ?
C3 C4 C7 O1 15.4(3) . . . . ?
C5 C4 C7 C8 15.6(3) . . . . ?
C3 C4 C7 C8 -164.75(16) . . . . ?
F1 C1 C6 C5 177.49(17) . . . . ?
C2 C1 C6 C5 -1.6(3) . . . . ?
C1 C6 C5 C4 1.1(3) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C7 C4 C5 C6 179.91(18) . . . . ?
C16 N1 C9 O2 -3.5(3) . . . . ?
C10 N1 C9 O2 178.87(19) . . . . ?
C16 N1 C9 C8 176.01(17) . . . . ?
C10 N1 C9 C8 -1.6(2) . . . . ?
O1 C7 C8 C11 -24.7(3) . . . . ?
C4 C7 C8 C11 155.44(16) . . . . ?
O1 C7 C8 C9 88.6(2) . . . . ?
C4 C7 C8 C9 -91.26(19) . . . . ?
O2 C9 C8 C7 80.0(2) . . . . ?
N1 C9 C8 C7 -99.46(17) . . . . ?
O2 C9 C8 C11 -159.92(19) . . . . ?
N1 C9 C8 C11 20.6(2) . . . . ?
C9 N1 C10 C15 -141.18(17) . . . . ?
C16 N1 C10 C15 41.2(2) . . . . ?
C9 N1 C10 C11 -17.9(2) . . . . ?
C16 N1 C10 C11 164.45(17) . . . . ?
C7 C8 C11 C12 -155.98(15) . . . . ?
C9 C8 C11 C12 87.60(17) . . . . ?
C7 C8 C11 C10 85.87(18) . . . . ?
C9 C8 C11 C10 -30.54(18) . . . . ?
N1 C10 C11 C12 -88.71(17) . . . . ?
C15 C10 C11 C12 34.4(2) . . . . ?
N1 C10 C11 C8 29.29(17) . . . . ?
C15 C10 C11 C8 152.36(16) . . . . ?
C8 C11 C12 C13 -172.55(16) . . . . ?
C10 C11 C12 C13 -58.8(2) . . . . ?
C11 C12 C13 C14 49.7(2) . . . . ?
C12 C13 C14 C15 -17.1(3) . . . . ?
C13 C14 C15 C10 -6.7(3) . . . . ?
N1 C10 C15 C14 113.9(2) . . . . ?
C11 C10 C15 C14 -2.4(3) . . . . ?
C9 N1 C16 C17 -96.5(2) . . . . ?
C10 N1 C16 C17 81.0(2) . . . . ?
C9 N1 C16 C21 83.7(2) . . . . ?
C10 N1 C16 C21 -98.9(2) . . . . ?
C21 C16 C17 C18 0.0(3) . . . . ?
N1 C16 C17 C18 -179.84(18) . . . . ?
C16 C17 C18 C19 -0.1(3) . . . . ?
C22 O3 C19 C18 1.5(3) . . . . ?
C22 O3 C19 C20 -178.21(19) . . . . ?
C17 C18 C19 O3 -179.43(19) . . . . ?
C17 C18 C19 C20 0.2(3) . . . . ?
O3 C19 C20 C21 179.4(2) . . . . ?
C18 C19 C20 C21 -0.3(3) . . . . ?
C19 C20 C21 C16 0.2(3) . . . . ?
C17 C16 C21 C20 -0.1(3) . . . . ?
N1 C16 C21 C20 179.76(19) . . . . ?

_refine_diff_density_max         0.176
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_t_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2236044'
loop_
_audit_author_name
_audit_author_address
'Siqi Dong flouration'
;Shanghai Jiao Tong University
China
;
_audit_update_record             
;
2023-01-13 deposited with the CCDC.	2023-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H20 F N O3'
_chemical_formula_sum            'C22 H20 F N O3'
_chemical_formula_weight         365.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   15.6267(6)
_cell_length_b                   6.7549(3)
_cell_length_c                   17.7452(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.358(2)
_cell_angle_gamma                90
_cell_volume                     1864.94(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    4588
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      68.30

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.767
_shelx_estimated_absorpt_T_min   0.874
_shelx_estimated_absorpt_T_max   0.900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6376
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12076
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.840
_diffrn_reflns_theta_max         68.391
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             3368
_reflns_number_gt                2548
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0562P)²+0.2735P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3368
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1149
_refine_ls_wR_factor_gt          0.1017
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C9 C 0.84083(11) 0.7184(2) 0.63394(10) 0.0415(4) Uani 1 1 d . . . . .
C10 C 0.93640(11) 0.7147(3) 0.64071(10) 0.0453(4) Uani 1 1 d . . . . .
C11 C 0.97723(13) 0.8576(3) 0.60029(11) 0.0594(5) Uani 1 1 d . . . . .
H11 H 0.944620 0.951319 0.571993 0.071 Uiso 1 1 calc R U . . .
C12 C 1.06542(14) 0.8613(4) 0.60184(14) 0.0748(6) Uani 1 1 d . . . . .
H12 H 1.092180 0.959604 0.575822 0.090 Uiso 1 1 calc R U . . .
C13 C 1.11404(14) 0.7200(4) 0.64180(14) 0.0754(7) Uani 1 1 d . . . . .
H13 H 1.173509 0.720027 0.641400 0.090 Uiso 1 1 calc R U . . .
C14 C 1.07480(14) 0.5793(4) 0.68217(13) 0.0717(6) Uani 1 1 d . . . . .
H14 H 1.107932 0.484303 0.709290 0.086 Uiso 1 1 calc R U . . .
C15 C 0.98644(13) 0.5770(3) 0.68305(12) 0.0596(5) Uani 1 1 d . . . . .
H15 H 0.960518 0.483411 0.711926 0.072 Uiso 1 1 calc R U . . .
C16 C 0.55675(11) 0.7450(2) 0.66024(10) 0.0437(4) Uani 1 1 d . . . . .
C17 C 0.48697(11) 0.6524(2) 0.68824(10) 0.0454(4) Uani 1 1 d . . . . .
H17 H 0.494540 0.533293 0.714269 0.054 Uiso 1 1 calc R U . . .
C18 C 0.40655(11) 0.7370(3) 0.67748(10) 0.0467(4) Uani 1 1 d . . . . .
H18 H 0.359875 0.673786 0.695855 0.056 Uiso 1 1 calc R U . . .
C19 C 0.39466(11) 0.9160(3) 0.63940(10) 0.0456(4) Uani 1 1 d . . . . .
C20 C 0.46422(12) 1.0069(3) 0.61050(11) 0.0516(4) Uani 1 1 d . . . . .
H20 H 0.456712 1.125677 0.584208 0.062 Uiso 1 1 calc R U . . .
C21 C 0.54469(12) 0.9207(3) 0.62083(11) 0.0508(4) Uani 1 1 d . . . . .
H21 H 0.591100 0.981509 0.601096 0.061 Uiso 1 1 calc R U . . .
C22 C 0.29700(15) 1.1718(3) 0.59493(14) 0.0719(6) Uani 1 1 d . . . . .
H22A H 0.237802 1.208134 0.596503 0.108 Uiso 1 1 calc R U . . .
H22B H 0.309525 1.159329 0.543198 0.108 Uiso 1 1 calc R U . . .
H22C H 0.333095 1.272123 0.619527 0.108 Uiso 1 1 calc R U . . .
F1 F 0.83918(7) 0.62500(16) 0.76339(6) 0.0545(3) Uani 1 1 d . . . . .
O1 O 0.80002(8) 0.79907(18) 0.58095(7) 0.0518(3) Uani 1 1 d . . . . .
N1 N 0.64037(9) 0.6578(2) 0.67142(8) 0.0449(3) Uani 1 1 d . . . . .
C1 C 0.71025(11) 0.7556(2) 0.70232(10) 0.0436(4) Uani 1 1 d . . . . .
O2 O 0.71273(8) 0.91807(18) 0.73176(8) 0.0567(4) Uani 1 1 d . . . . .
C2 C 0.78887(11) 0.6248(2) 0.69407(9) 0.0411(4) Uani 1 1 d . . . . .
O3 O 0.31278(8) 0.9870(2) 0.63299(8) 0.0595(4) Uani 1 1 d . . . . .
C3 C 0.75107(11) 0.4185(2) 0.67710(10) 0.0452(4) Uani 1 1 d . . . . .
H3 H 0.747218 0.355015 0.726336 0.054 Uiso 1 1 calc R U . . .
C4 C 0.65822(12) 0.4568(2) 0.64432(11) 0.0479(4) Uani 1 1 d . . . . .
H4 H 0.620023 0.362252 0.666368 0.057 Uiso 1 1 calc R U . . .
C5 C 0.64508(16) 0.4431(3) 0.55957(13) 0.0652(6) Uani 1 1 d . . . . .
H5 H 0.591953 0.479981 0.535713 0.078 Uiso 1 1 calc R U . . .
C6 C 0.70512(19) 0.3814(3) 0.51679(13) 0.0741(7) Uani 1 1 d . . . . .
H6 H 0.691670 0.379274 0.464630 0.089 Uiso 1 1 calc R U . . .
C7 C 0.79196(17) 0.3158(3) 0.54673(13) 0.0714(6) Uani 1 1 d . . . . .
H7A H 0.833227 0.417937 0.537217 0.086 Uiso 1 1 calc R U . . .
H7B H 0.806971 0.197385 0.519966 0.086 Uiso 1 1 calc R U . . .
C8 C 0.79807(14) 0.2727(3) 0.63024(13) 0.0598(5) Uani 1 1 d . . . . .
H8A H 0.858270 0.271198 0.649394 0.072 Uiso 1 1 calc R U . . .
H8B H 0.775215 0.141284 0.637495 0.072 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
C9 O1 1.215(2) . ?
C9 C10 1.487(2) . ?
C9 C2 1.536(2) . ?
C10 C15 1.390(3) . ?
C10 C11 1.392(3) . ?
C11 C12 1.376(3) . ?
C12 C13 1.375(4) . ?
C13 C14 1.369(3) . ?
C14 C15 1.382(3) . ?
C16 C21 1.382(2) . ?
C16 C17 1.388(2) . ?
C16 N1 1.430(2) . ?
C17 C18 1.377(2) . ?
C18 C19 1.389(2) . ?
C19 O3 1.361(2) . ?
C19 C20 1.388(2) . ?
C20 C21 1.382(3) . ?
C22 O3 1.430(2) . ?
F1 C2 1.3966(19) . ?
N1 C1 1.348(2) . ?
N1 C4 1.476(2) . ?
C1 O2 1.214(2) . ?
C1 C2 1.531(2) . ?
C2 C3 1.533(2) . ?
C3 C8 1.521(2) . ?
C3 C4 1.534(3) . ?
C4 C5 1.502(3) . ?
C5 C6 1.328(3) . ?
C6 C7 1.478(4) . ?
C7 C8 1.504(3) . ?

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
O1 C9 C10 121.37(15) . . ?
O1 C9 C2 116.68(15) . . ?
C10 C9 C2 121.94(15) . . ?
C15 C10 C11 118.73(17) . . ?
C15 C10 C9 124.40(16) . . ?
C11 C10 C9 116.86(16) . . ?
C12 C11 C10 120.6(2) . . ?
C13 C12 C11 120.1(2) . . ?
C14 C13 C12 119.9(2) . . ?
C13 C14 C15 120.7(2) . . ?
C14 C15 C10 119.9(2) . . ?
C21 C16 C17 119.56(16) . . ?
C21 C16 N1 120.25(15) . . ?
C17 C16 N1 120.18(15) . . ?
C18 C17 C16 120.04(16) . . ?
C17 C18 C19 120.48(16) . . ?
O3 C19 C20 125.15(16) . . ?
O3 C19 C18 115.43(15) . . ?
C20 C19 C18 119.42(16) . . ?
C21 C20 C19 119.91(17) . . ?
C16 C21 C20 120.56(16) . . ?
C1 N1 C16 123.32(14) . . ?
C1 N1 C4 114.40(13) . . ?
C16 N1 C4 122.12(13) . . ?
O2 C1 N1 127.59(16) . . ?
O2 C1 C2 124.66(15) . . ?
N1 C1 C2 107.75(14) . . ?
F1 C2 C1 107.82(13) . . ?
F1 C2 C3 110.41(13) . . ?
C1 C2 C3 104.22(13) . . ?
F1 C2 C9 108.71(13) . . ?
C1 C2 C9 108.06(13) . . ?
C3 C2 C9 117.17(14) . . ?
C19 O3 C22 117.80(15) . . ?
C8 C3 C2 119.94(15) . . ?
C8 C3 C4 112.94(16) . . ?
C2 C3 C4 104.75(13) . . ?
N1 C4 C5 111.75(15) . . ?
N1 C4 C3 103.44(13) . . ?
C5 C4 C3 113.92(17) . . ?
C6 C5 C4 123.6(2) . . ?
C5 C6 C7 124.2(2) . . ?
C6 C7 C8 112.55(19) . . ?
C7 C8 C3 115.08(16) . . ?

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
O1 C9 C10 C15 -157.91(18) . . . . ?
C2 C9 C10 C15 23.4(3) . . . . ?
O1 C9 C10 C11 20.8(2) . . . . ?
C2 C9 C10 C11 -157.91(16) . . . . ?
C15 C10 C11 C12 0.5(3) . . . . ?
C9 C10 C11 C12 -178.28(19) . . . . ?
C10 C11 C12 C13 1.8(3) . . . . ?
C11 C12 C13 C14 -2.2(4) . . . . ?
C12 C13 C14 C15 0.3(4) . . . . ?
C13 C14 C15 C10 2.0(3) . . . . ?
C11 C10 C15 C14 -2.4(3) . . . . ?
C9 C10 C15 C14 176.27(19) . . . . ?
C21 C16 C17 C18 -0.8(3) . . . . ?
N1 C16 C17 C18 179.88(16) . . . . ?
C16 C17 C18 C19 -0.7(3) . . . . ?
C17 C18 C19 O3 -179.12(16) . . . . ?
C17 C18 C19 C20 1.6(3) . . . . ?
O3 C19 C20 C21 179.77(18) . . . . ?
C18 C19 C20 C21 -1.0(3) . . . . ?
C17 C16 C21 C20 1.4(3) . . . . ?
N1 C16 C21 C20 -179.31(17) . . . . ?
C19 C20 C21 C16 -0.4(3) . . . . ?
C21 C16 N1 C1 53.9(2) . . . . ?
C17 C16 N1 C1 -126.76(19) . . . . ?
C21 C16 N1 C4 -121.17(19) . . . . ?
C17 C16 N1 C4 58.2(2) . . . . ?
C16 N1 C1 O2 8.2(3) . . . . ?
C4 N1 C1 O2 -176.39(18) . . . . ?
C16 N1 C1 C2 -171.79(15) . . . . ?
C4 N1 C1 C2 3.6(2) . . . . ?
O2 C1 C2 F1 45.7(2) . . . . ?
N1 C1 C2 F1 -134.29(14) . . . . ?
O2 C1 C2 C3 163.09(18) . . . . ?
N1 C1 C2 C3 -16.95(18) . . . . ?
O2 C1 C2 C9 -71.6(2) . . . . ?
N1 C1 C2 C9 108.37(16) . . . . ?
O1 C9 C2 F1 -152.24(14) . . . . ?
C10 C9 C2 F1 26.5(2) . . . . ?
O1 C9 C2 C1 -35.47(19) . . . . ?
C10 C9 C2 C1 143.26(15) . . . . ?
O1 C9 C2 C3 81.77(19) . . . . ?
C10 C9 C2 C3 -99.51(19) . . . . ?
C20 C19 O3 C22 -1.4(3) . . . . ?
C18 C19 O3 C22 179.40(18) . . . . ?
F1 C2 C3 C8 -93.32(19) . . . . ?
C1 C2 C3 C8 151.14(17) . . . . ?
C9 C2 C3 C8 31.8(2) . . . . ?
F1 C2 C3 C4 138.60(14) . . . . ?
C1 C2 C3 C4 23.06(17) . . . . ?
C9 C2 C3 C4 -96.24(17) . . . . ?
C1 N1 C4 C5 -111.79(18) . . . . ?
C16 N1 C4 C5 63.7(2) . . . . ?
C1 N1 C4 C3 11.18(19) . . . . ?
C16 N1 C4 C3 -173.33(15) . . . . ?
C8 C3 C4 N1 -153.07(15) . . . . ?
C2 C3 C4 N1 -20.86(17) . . . . ?
C8 C3 C4 C5 -31.6(2) . . . . ?
C2 C3 C4 C5 100.65(16) . . . . ?
N1 C4 C5 C6 124.2(2) . . . . ?
C3 C4 C5 C6 7.5(3) . . . . ?
C4 C5 C6 C7 0.8(3) . . . . ?
C5 C6 C7 C8 15.7(3) . . . . ?
C6 C7 C8 C3 -40.7(2) . . . . ?
C2 C3 C8 C7 -74.8(2) . . . . ?
C4 C3 C8 C7 49.5(2) . . . . ?

_refine_diff_density_max         0.137
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.037

