# 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. 
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#######################################################################

data_mo_20180828-zh-227_0m
_database_code_depnum_ccdc_archive 'CCDC 1974572'
loop_
_audit_author_name
_audit_author_address
'Chuanle Zhu'
;South China University of Technology
China
;
_audit_update_record             
;
2019-12-29 deposited with the CCDC.	2020-04-09 downloaded from the CCDC.
;
_audit_creation_date             2018-09-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H19 F4 N'
_chemical_formula_sum            'C26 H19 F4 N'
_chemical_formula_weight         421.42
_chemical_absolute_configuration .
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   14.572(2)
_cell_length_b                   6.7351(12)
_cell_length_c                   21.402(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2100.5(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    378
_cell_measurement_temperature    210
_cell_measurement_theta_max      24.099
_cell_measurement_theta_min      3.111
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0693 before and 0.0471 after correction. The Ratio of minimum to maximum transmission is 0.7829. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0950
_diffrn_reflns_av_unetI/netI     0.1180
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12001
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.466
_diffrn_reflns_theta_min         1.903
_diffrn_ambient_temperature      210
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.746
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2620
_reflns_number_total             4245
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.1(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1075
_refine_ls_R_factor_gt           0.0579
_refine_ls_restrained_S_all      0.958
_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)+(0.0372P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1323
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.1(14)
 -0.1(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C6(H6A,H6B)
3.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.4051(2) 0.9325(4) 0.47117(13) 0.0559(8) Uani 1 1 d . . . . .
F2 F 0.48621(19) 0.9898(4) 0.38929(13) 0.0573(8) Uani 1 1 d . . . . .
F3 F 0.4368(2) 1.0111(5) 0.12207(14) 0.0707(10) Uani 1 1 d . . . . .
F4 F 0.3199(2) 1.0171(4) 0.06166(13) 0.0632(9) Uani 1 1 d . . . . .
N1 N 0.3782(3) 1.1719(6) 0.2626(2) 0.0451(11) Uani 1 1 d . . . . .
C1 C 0.3549(3) 0.9302(7) 0.1121(2) 0.0450(13) Uani 1 1 d . . . . .
C2 C 0.3176(3) 0.7896(6) 0.1443(2) 0.0305(10) Uani 1 1 d . . . . .
C3 C 0.3685(3) 0.7053(6) 0.1998(2) 0.0323(10) Uani 1 1 d . . . . .
H3A H 0.4342 0.7306 0.1943 0.039 Uiso 1 1 calc R . . . .
H3B H 0.3596 0.5610 0.2005 0.039 Uiso 1 1 calc R . . . .
C4 C 0.3377(3) 0.7921(5) 0.26388(19) 0.0273(10) Uani 1 1 d . . . . .
C5 C 0.3598(3) 1.0073(7) 0.26321(19) 0.0322(10) Uani 1 1 d . . . . .
C6 C 0.3985(3) 0.6944(6) 0.31526(19) 0.0309(10) Uani 1 1 d . . . . .
H6A H 0.3955 0.5499 0.3102 0.037 Uiso 1 1 calc R . . . .
H6B H 0.4623 0.7347 0.3084 0.037 Uiso 1 1 calc R . . . .
C7 C 0.3724(3) 0.7451(5) 0.3815(2) 0.0295(10) Uani 1 1 d . . . . .
C8 C 0.4171(3) 0.8823(6) 0.4115(2) 0.0381(11) Uani 1 1 d . . . . .
C9 C 0.2280(3) 0.7080(6) 0.1249(2) 0.0344(11) Uani 1 1 d . . . . .
C10 C 0.1516(3) 0.8279(7) 0.1192(2) 0.0467(13) Uani 1 1 d . . . . .
H10 H 0.1557 0.9625 0.1305 0.056 Uiso 1 1 calc R . . . .
C11 C 0.0697(4) 0.7542(10) 0.0973(2) 0.0621(16) Uani 1 1 d . . . . .
H11 H 0.0183 0.8379 0.0940 0.075 Uiso 1 1 calc R . . . .
C12 C 0.0632(4) 0.5580(11) 0.0804(3) 0.0705(19) Uani 1 1 d . . . . .
H12 H 0.0078 0.5080 0.0642 0.085 Uiso 1 1 calc R . . . .
C13 C 0.1369(5) 0.4364(8) 0.0870(2) 0.0608(16) Uani 1 1 d . . . . .
H13 H 0.1315 0.3013 0.0765 0.073 Uiso 1 1 calc R . . . .
C14 C 0.2200(3) 0.5091(7) 0.1089(2) 0.0444(12) Uani 1 1 d . . . . .
H14 H 0.2707 0.4239 0.1129 0.053 Uiso 1 1 calc R . . . .
C15 C 0.1760(3) 0.9151(6) 0.2878(2) 0.0338(11) Uani 1 1 d . . . . .
H15 H 0.1978 1.0464 0.2873 0.041 Uiso 1 1 calc R . . . .
C16 C 0.0853(3) 0.8802(8) 0.3000(2) 0.0476(13) Uani 1 1 d . . . . .
H16 H 0.0454 0.9876 0.3071 0.057 Uiso 1 1 calc R . . . .
C17 C 0.0520(4) 0.6890(8) 0.3022(3) 0.0490(13) Uani 1 1 d . . . . .
H17 H -0.0101 0.6647 0.3113 0.059 Uiso 1 1 calc R . . . .
C18 C 0.1112(3) 0.5338(7) 0.2906(2) 0.0432(12) Uani 1 1 d . . . . .
H18 H 0.0893 0.4026 0.2918 0.052 Uiso 1 1 calc R . . . .
C19 C 0.2362(3) 0.7600(6) 0.27605(19) 0.0277(10) Uani 1 1 d . . . . .
C20 C 0.2015(3) 0.5684(6) 0.2774(2) 0.0366(11) Uani 1 1 d . . . . .
H20 H 0.2407 0.4607 0.2691 0.044 Uiso 1 1 calc R . . . .
C21 C 0.2992(3) 0.6296(6) 0.4138(2) 0.0309(10) Uani 1 1 d . . . . .
C22 C 0.2192(3) 0.7167(6) 0.4355(2) 0.0381(11) Uani 1 1 d . . . . .
H22 H 0.2106 0.8542 0.4306 0.046 Uiso 1 1 calc R . . . .
C23 C 0.3094(3) 0.4265(6) 0.4220(2) 0.0455(13) Uani 1 1 d . . . . .
H23 H 0.3631 0.3638 0.4078 0.055 Uiso 1 1 calc R . . . .
C24 C 0.2427(4) 0.3159(7) 0.4505(3) 0.0563(16) Uani 1 1 d . . . . .
H24 H 0.2511 0.1785 0.4556 0.068 Uiso 1 1 calc R . . . .
C25 C 0.1634(4) 0.4042(8) 0.4716(2) 0.0538(14) Uani 1 1 d . . . . .
H25 H 0.1176 0.3279 0.4911 0.065 Uiso 1 1 calc R . . . .
C26 C 0.1520(3) 0.6047(7) 0.4640(2) 0.0473(13) Uani 1 1 d . . . . .
H26 H 0.0981 0.6663 0.4784 0.057 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C8 1.332(5) . ?
F2 C8 1.329(5) . ?
F3 C1 1.330(5) . ?
F4 C1 1.329(5) . ?
N1 C5 1.141(5) . ?
C1 C2 1.292(6) . ?
C2 C3 1.511(6) . ?
C2 C9 1.476(6) . ?
C3 C4 1.558(6) . ?
C4 C5 1.484(6) . ?
C4 C6 1.558(6) . ?
C4 C19 1.517(6) . ?
C6 C7 1.507(6) . ?
C7 C8 1.300(6) . ?
C7 C21 1.491(6) . ?
C9 C10 1.381(6) . ?
C9 C14 1.387(6) . ?
C10 C11 1.374(7) . ?
C11 C12 1.374(8) . ?
C12 C13 1.358(8) . ?
C13 C14 1.388(7) . ?
C15 C16 1.367(7) . ?
C15 C19 1.387(6) . ?
C16 C17 1.377(7) . ?
C17 C18 1.378(7) . ?
C18 C20 1.366(6) . ?
C19 C20 1.386(6) . ?
C21 C22 1.385(6) . ?
C21 C23 1.387(6) . ?
C22 C26 1.379(6) . ?
C23 C24 1.368(7) . ?
C24 C25 1.376(7) . ?
C25 C26 1.370(7) . ?

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
F4 C1 F3 107.2(4) . . ?
C2 C1 F3 126.4(5) . . ?
C2 C1 F4 126.4(4) . . ?
C1 C2 C3 119.2(4) . . ?
C1 C2 C9 119.7(4) . . ?
C9 C2 C3 121.0(4) . . ?
C2 C3 C4 114.2(3) . . ?
C3 C4 C6 107.4(3) . . ?
C5 C4 C3 107.2(3) . . ?
C5 C4 C6 107.2(4) . . ?
C5 C4 C19 110.6(3) . . ?
C19 C4 C3 112.2(3) . . ?
C19 C4 C6 111.9(3) . . ?
N1 C5 C4 178.9(5) . . ?
C7 C6 C4 115.2(3) . . ?
C8 C7 C6 120.0(4) . . ?
C8 C7 C21 120.0(4) . . ?
C21 C7 C6 119.9(4) . . ?
F2 C8 F1 107.8(4) . . ?
C7 C8 F1 126.0(4) . . ?
C7 C8 F2 126.1(4) . . ?
C10 C9 C2 121.3(4) . . ?
C10 C9 C14 118.4(4) . . ?
C14 C9 C2 120.2(4) . . ?
C11 C10 C9 121.2(5) . . ?
C12 C11 C10 119.9(5) . . ?
C13 C12 C11 119.8(5) . . ?
C12 C13 C14 120.8(5) . . ?
C9 C14 C13 119.8(5) . . ?
C16 C15 C19 121.1(4) . . ?
C15 C16 C17 120.5(5) . . ?
C16 C17 C18 118.9(5) . . ?
C20 C18 C17 120.8(4) . . ?
C15 C19 C4 122.7(4) . . ?
C20 C19 C4 119.4(4) . . ?
C20 C19 C15 117.8(4) . . ?
C18 C20 C19 120.9(4) . . ?
C22 C21 C7 122.4(4) . . ?
C22 C21 C23 117.8(4) . . ?
C23 C21 C7 119.8(4) . . ?
C26 C22 C21 120.9(4) . . ?
C24 C23 C21 121.2(5) . . ?
C23 C24 C25 120.5(5) . . ?
C26 C25 C24 119.3(5) . . ?
C25 C26 C22 120.4(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.1(14)
2 -0.1(14)

