# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_exp_10919
_audit_block_doi                 10.5517/ccdc.csd.cc249jqq
_database_code_depnum_ccdc_archive 'CCDC 1975373'
loop_
_audit_author_name
_audit_author_address
'Xin-Xing Wu' lzu
_audit_update_record             
;
2020-01-04 deposited with the CCDC.	2020-08-19 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         ?
_chemical_formula_sum            'C16 H16 F3 N O'
_chemical_formula_weight         295.30

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

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

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

_cell_length_a                   15.8851(9)
_cell_length_b                   11.9332(7)
_cell_length_c                   16.3548(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3100.2(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1815
_cell_measurement_theta_min      5.3520
_cell_measurement_theta_max      64.7500

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_F_000             1232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.882
_shelx_estimated_absorpt_T_min   0.901
_shelx_estimated_absorpt_T_max   0.909
_exptl_absorpt_correction_T_min  0.92275
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7304
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         5.368
_diffrn_reflns_theta_max         67.232
_diffrn_reflns_theta_full        67.232
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2779
_reflns_number_gt                1649
_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       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXL-2018/3 (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)+(0.1005P)²+0.8084P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0013(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2779
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1070
_refine_ls_R_factor_gt           0.0699
_refine_ls_wR_factor_ref         0.2299
_refine_ls_wR_factor_gt          0.1909
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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 0.57732(17) 0.6490(3) 0.5791(2) 0.1699(14) Uani 1 1 d . . . . .
F2 F 0.45389(19) 0.6233(2) 0.5480(2) 0.1486(12) Uani 1 1 d . . . . .
F3 F 0.4874(3) 0.6208(3) 0.6687(2) 0.211(2) Uani 1 1 d . . . . .
N1 N 0.4216(2) 1.1311(2) 0.62739(17) 0.0819(9) Uani 1 1 d . . . . .
O1 O 0.29252(17) 1.2149(2) 0.63213(15) 0.0948(9) Uani 1 1 d . . . . .
C1 C 0.5013(3) 0.6751(4) 0.6028(3) 0.1006(13) Uani 1 1 d . . . . .
C2 C 0.4844(2) 0.7963(3) 0.6081(2) 0.0776(10) Uani 1 1 d . . . . .
C3 C 0.5497(2) 0.8719(4) 0.6111(2) 0.0962(13) Uani 1 1 d . . . . .
H3 H 0.604847 0.845877 0.608438 0.115 Uiso 1 1 calc R U . . .
C4 C 0.5351(2) 0.9859(4) 0.6181(2) 0.0955(12) Uani 1 1 d . . . . .
H4 H 0.579387 1.036696 0.620729 0.115 Uiso 1 1 calc R U . . .
C5 C 0.4529(2) 1.0215(3) 0.62104(19) 0.0746(9) Uani 1 1 d . . . . .
C6 C 0.38589(19) 0.9462(3) 0.61789(17) 0.0640(8) Uani 1 1 d . . . . .
C7 C 0.4006(2) 0.8332(3) 0.61155(18) 0.0697(9) Uani 1 1 d . . . . .
H7 H 0.356183 0.782420 0.609622 0.084 Uiso 1 1 calc R U . . .
C8 C 0.3358(2) 1.1310(3) 0.62741(19) 0.0742(9) Uani 1 1 d . . . . .
C9 C 0.3043(2) 1.0103(3) 0.62220(18) 0.0643(8) Uani 1 1 d . . . . .
C10 C 0.4719(3) 1.2322(4) 0.6336(3) 0.1136(15) Uani 1 1 d . . . . .
H10A H 0.435468 1.295706 0.640528 0.170 Uiso 1 1 calc R U . . .
H10B H 0.504485 1.241348 0.584660 0.170 Uiso 1 1 calc R U . . .
H10C H 0.508927 1.226425 0.679796 0.170 Uiso 1 1 calc R U . . .
C11 C 0.2501(2) 0.9952(3) 0.5457(2) 0.0815(10) Uani 1 1 d . . . . .
H11A H 0.202208 1.044033 0.548636 0.122 Uiso 1 1 calc R U . . .
H11B H 0.231422 0.918855 0.542257 0.122 Uiso 1 1 calc R U . . .
H11C H 0.282797 1.013267 0.498068 0.122 Uiso 1 1 calc R U . . .
C12 C 0.2530(2) 0.9833(3) 0.69907(19) 0.0707(9) Uani 1 1 d . . . . .
H12A H 0.204784 1.033046 0.701383 0.085 Uiso 1 1 calc R U . . .
H12B H 0.231969 0.907167 0.694954 0.085 Uiso 1 1 calc R U . . .
C13 C 0.3017(2) 0.9945(3) 0.7760(2) 0.0805(10) Uani 1 1 d . . . . .
H13 H 0.326008 1.064153 0.785630 0.097 Uiso 1 1 calc R U . . .
C14 C 0.3146(2) 0.9170(3) 0.8328(2) 0.0783(10) Uani 1 1 d . . . . .
H14 H 0.347237 0.938180 0.877363 0.094 Uiso 1 1 calc R U . . .
C15 C 0.2836(2) 0.8042(3) 0.8329(2) 0.0775(9) Uani 1 1 d . . . . .
H15 H 0.257211 0.778004 0.785878 0.093 Uiso 1 1 calc R U . . .
C16 C 0.2903(3) 0.7355(4) 0.8953(3) 0.0993(12) Uani 1 1 d . . . . .
H16A H 0.316414 0.759210 0.943152 0.119 Uiso 1 1 calc R U . . .
H16B H 0.268939 0.663100 0.891609 0.119 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 1.305(5) . ?
F2 C1 1.323(5) . ?
F3 C1 1.278(5) . ?
N1 C8 1.363(5) . ?
N1 C5 1.403(4) . ?
N1 C10 1.451(5) . ?
O1 C8 1.217(4) . ?
C1 C2 1.474(6) . ?
C2 C3 1.376(5) . ?
C2 C7 1.404(4) . ?
C3 C4 1.385(5) . ?
C4 C5 1.374(5) . ?
C5 C6 1.394(4) . ?
C6 C7 1.373(4) . ?
C6 C9 1.507(4) . ?
C8 C9 1.527(4) . ?
C9 C11 1.529(4) . ?
C9 C12 1.532(4) . ?
C12 C13 1.483(4) . ?
C13 C14 1.326(5) . ?
C14 C15 1.433(5) . ?
C15 C16 1.313(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C5 110.7(3) . . ?
C8 N1 C10 123.5(3) . . ?
C5 N1 C10 125.8(3) . . ?
F3 C1 F1 106.8(4) . . ?
F3 C1 F2 103.7(5) . . ?
F1 C1 F2 102.4(4) . . ?
F3 C1 C2 114.6(4) . . ?
F1 C1 C2 114.8(4) . . ?
F2 C1 C2 113.2(3) . . ?
C3 C2 C7 120.6(4) . . ?
C3 C2 C1 120.5(4) . . ?
C7 C2 C1 118.9(4) . . ?
C2 C3 C4 121.3(4) . . ?
C5 C4 C3 117.8(4) . . ?
C4 C5 C6 121.7(3) . . ?
C4 C5 N1 128.9(3) . . ?
C6 C5 N1 109.5(3) . . ?
C7 C6 C5 120.4(3) . . ?
C7 C6 C9 130.4(3) . . ?
C5 C6 C9 109.2(3) . . ?
C6 C7 C2 118.2(3) . . ?
O1 C8 N1 124.3(3) . . ?
O1 C8 C9 126.5(3) . . ?
N1 C8 C9 109.2(3) . . ?
C6 C9 C8 101.5(3) . . ?
C6 C9 C11 112.7(2) . . ?
C8 C9 C11 109.9(3) . . ?
C6 C9 C12 112.9(2) . . ?
C8 C9 C12 109.1(2) . . ?
C11 C9 C12 110.3(3) . . ?
C13 C12 C9 113.6(3) . . ?
C14 C13 C12 127.7(3) . . ?
C13 C14 C15 127.1(3) . . ?
C16 C15 C14 124.0(4) . . ?

_refine_diff_density_max         0.428
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.038



