# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 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_yaojia170830
_database_code_depnum_ccdc_archive 'CCDC 1572376'
_audit_update_record             
;
2017-09-04 deposited with the CCDC.	2020-01-09 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 F3 N O'
_chemical_formula_iupac          ?
_chemical_formula_weight         347.37

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   6.3469(6)
_cell_length_b                   21.271(2)
_cell_length_c                   25.867(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3492.2(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2363
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      25.32
_cell_measurement_temperature    173.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1456

_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      173.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'PHOTON 100 CMOS detector'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            14382
_diffrn_reflns_av_R_equivalents  0.1135
_diffrn_reflns_av_unetI/netI     0.0931
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_full        25.34
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       26

_reflns_number_total             3158
_reflns_number_gt                1792
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1269
_refine_ls_R_factor_gt           0.0525
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.1140
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_number_reflns         3158
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0378P)²+0.4708P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.229
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0077(6)

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2016)'
_computing_structure_solution    'SHELXT (Bruker AXS Inc., 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2016)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.6194(4) 0.19385(12) 0.34857(10) 0.0257(6) Uani d . . . 1 . .
C C2 0.5839(4) 0.13212(11) 0.34561(9) 0.0260(6) Uani d . . . 1 . .
H H2 0.455486 0.113562 0.334539 0.031 Uiso calc U . R 1 . .
C C3 0.7762(4) 0.09608(11) 0.36230(9) 0.0247(6) Uani d . . . 1 . .
C C4 0.9154(5) 0.15021(12) 0.38581(10) 0.0277(7) Uani d . . . 1 . .
H H4 1.058496 0.147674 0.369753 0.033 Uiso calc U . R 1 . .
C C5 0.4856(5) 0.24780(12) 0.33594(10) 0.0280(7) Uani d . . . 1 . .
C C6 0.2999(5) 0.23983(12) 0.30822(10) 0.0284(7) Uani d . . . 1 . .
H H6 0.260769 0.198973 0.296924 0.034 Uiso calc U . R 1 . .
C C7 0.1713(5) 0.29045(12) 0.29680(10) 0.0328(7) Uani d . . . 1 . .
H H7 0.044032 0.283728 0.278287 0.039 Uiso calc U . R 1 . .
C C8 0.2255(5) 0.35113(12) 0.31204(10) 0.0356(7) Uani d . . . 1 . .
C C9 0.4114(5) 0.35889(13) 0.33906(11) 0.0419(8) Uani d . . . 1 . .
H H9 0.45165 0.399936 0.349647 0.05 Uiso calc U . R 1 . .
C C10 0.5415(5) 0.30840(13) 0.35124(11) 0.0382(8) Uani d . . . 1 . .
H H10 0.668252 0.315194 0.369951 0.046 Uiso calc U . R 1 . .
C C11 0.0863(6) 0.40615(13) 0.29773(12) 0.0511(9) Uani d . . . 1 . .
H H11A -0.047984 0.402863 0.316245 0.077 Uiso calc U . R 1 . .
H H11B 0.060066 0.405731 0.260396 0.077 Uiso calc U . R 1 . .
H H11C 0.156538 0.445493 0.30728 0.077 Uiso calc U . R 1 . .
C C12 0.8867(5) 0.07250(13) 0.31371(10) 0.0319(7) Uani d . . . 1 . .
C C13 0.7357(4) 0.03928(11) 0.39733(9) 0.0252(7) Uani d . . . 1 . .
C C14 0.8999(5) 0.00927(12) 0.42321(10) 0.0305(7) Uani d . . . 1 . .
H H14 1.03915 0.025283 0.420501 0.037 Uiso calc U . R 1 . .
C C15 0.8616(5) -0.04364(13) 0.45282(11) 0.0375(8) Uani d . . . 1 . .
H H15 0.97501 -0.063422 0.470432 0.045 Uiso calc U . R 1 . .
C C16 0.6634(5) -0.06780(14) 0.45707(12) 0.0456(9) Uani d . . . 1 . .
H H16 0.638892 -0.104321 0.477338 0.055 Uiso calc U . R 1 . .
C C17 0.4991(5) -0.03894(15) 0.43182(12) 0.0510(9) Uani d . . . 1 . .
H H17 0.360469 -0.055403 0.434669 0.061 Uiso calc U . R 1 . .
C C18 0.5362(5) 0.01429(13) 0.40217(11) 0.0392(8) Uani d . . . 1 . .
H H18 0.42184 0.033929 0.384852 0.047 Uiso calc U . R 1 . .
C C19 0.7451(5) 0.15997(13) 0.46897(11) 0.0426(9) Uani d . . . 1 . .
H H19A 0.685914 0.20119 0.46028 0.064 Uiso calc U . R 1 . .
H H19B 0.773593 0.158046 0.506171 0.064 Uiso calc U . R 1 . .
H H19C 0.644222 0.126996 0.459609 0.064 Uiso calc U . R 1 . .
C C20 1.1014(6) 0.19637(14) 0.45581(12) 0.0505(9) Uani d . . . 1 . .
H H20A 1.23233 0.187958 0.436941 0.076 Uiso calc U . R 1 . .
H H20B 1.127409 0.192904 0.49305 0.076 Uiso calc U . R 1 . .
H H20C 1.052018 0.238889 0.447713 0.076 Uiso calc U . R 1 . .
F F1 0.9285(3) 0.11874(7) 0.27989(6) 0.0438(5) Uani d . . . 1 . .
F F2 1.0744(3) 0.04509(8) 0.32335(6) 0.0445(5) Uani d . . . 1 . .
F F3 0.7705(3) 0.02981(7) 0.28837(6) 0.0443(5) Uani d . . . 1 . .
N N1 0.9409(4) 0.15056(10) 0.44047(8) 0.0315(6) Uani d . . . 1 . .
O O1 0.8146(3) 0.20841(8) 0.36787(7) 0.0328(5) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.334(3) ?
C1 O1 . 1.371(3) ?
C1 C5 . 1.465(4) ?
C2 C3 . 1.504(4) ?
C2 H2 . 0.95 ?
C3 C12 . 1.524(4) ?
C3 C13 . 1.532(3) ?
C3 C4 . 1.574(4) ?
C4 N1 . 1.423(3) ?
C4 O1 . 1.469(3) ?
C4 H4 . 1.0 ?
C5 C6 . 1.390(4) ?
C5 C10 . 1.394(4) ?
C6 C7 . 1.383(4) ?
C6 H6 . 0.95 ?
C7 C8 . 1.393(4) ?
C7 H7 . 0.95 ?
C8 C9 . 1.382(4) ?
C8 C11 . 1.512(4) ?
C9 C10 . 1.391(4) ?
C9 H9 . 0.95 ?
C10 H10 . 0.95 ?
C11 H11A . 0.98 ?
C11 H11B . 0.98 ?
C11 H11C . 0.98 ?
C12 F3 . 1.341(3) ?
C12 F1 . 1.343(3) ?
C12 F2 . 1.349(3) ?
C13 C18 . 1.379(4) ?
C13 C14 . 1.393(4) ?
C14 C15 . 1.383(4) ?
C14 H14 . 0.95 ?
C15 C16 . 1.364(4) ?
C15 H15 . 0.95 ?
C16 C17 . 1.375(4) ?
C16 H16 . 0.95 ?
C17 C18 . 1.388(4) ?
C17 H17 . 0.95 ?
C18 H18 . 0.95 ?
C19 N1 . 1.459(4) ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C19 H19C . 0.98 ?
C20 N1 . 1.465(4) ?
C20 H20A . 0.98 ?
C20 H20B . 0.98 ?
C20 H20C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 O1 . . 113.3(2) ?
C2 C1 C5 . . 131.3(3) ?
O1 C1 C5 . . 115.3(2) ?
C1 C2 C3 . . 110.4(2) ?
C1 C2 H2 . . 124.8 ?
C3 C2 H2 . . 124.8 ?
C2 C3 C12 . . 107.7(2) ?
C2 C3 C13 . . 115.8(2) ?
C12 C3 C13 . . 107.8(2) ?
C2 C3 C4 . . 101.2(2) ?
C12 C3 C4 . . 107.5(2) ?
C13 C3 C4 . . 116.3(2) ?
N1 C4 O1 . . 111.0(2) ?
N1 C4 C3 . . 116.8(2) ?
O1 C4 C3 . . 104.5(2) ?
N1 C4 H4 . . 108.1 ?
O1 C4 H4 . . 108.1 ?
C3 C4 H4 . . 108.1 ?
C6 C5 C10 . . 118.3(3) ?
C6 C5 C1 . . 120.7(2) ?
C10 C5 C1 . . 120.9(3) ?
C7 C6 C5 . . 121.0(3) ?
C7 C6 H6 . . 119.5 ?
C5 C6 H6 . . 119.5 ?
C6 C7 C8 . . 121.0(3) ?
C6 C7 H7 . . 119.5 ?
C8 C7 H7 . . 119.5 ?
C9 C8 C7 . . 117.7(3) ?
C9 C8 C11 . . 122.0(3) ?
C7 C8 C11 . . 120.2(3) ?
C8 C9 C10 . . 122.0(3) ?
C8 C9 H9 . . 119.0 ?
C10 C9 H9 . . 119.0 ?
C9 C10 C5 . . 119.9(3) ?
C9 C10 H10 . . 120.0 ?
C5 C10 H10 . . 120.0 ?
C8 C11 H11A . . 109.5 ?
C8 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C8 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
F3 C12 F1 . . 106.6(2) ?
F3 C12 F2 . . 106.4(2) ?
F1 C12 F2 . . 105.2(2) ?
F3 C12 C3 . . 111.9(2) ?
F1 C12 C3 . . 112.8(2) ?
F2 C12 C3 . . 113.3(2) ?
C18 C13 C14 . . 117.8(3) ?
C18 C13 C3 . . 120.8(2) ?
C14 C13 C3 . . 121.3(2) ?
C15 C14 C13 . . 120.5(3) ?
C15 C14 H14 . . 119.7 ?
C13 C14 H14 . . 119.7 ?
C16 C15 C14 . . 120.9(3) ?
C16 C15 H15 . . 119.6 ?
C14 C15 H15 . . 119.6 ?
C15 C16 C17 . . 119.5(3) ?
C15 C16 H16 . . 120.2 ?
C17 C16 H16 . . 120.2 ?
C16 C17 C18 . . 119.9(3) ?
C16 C17 H17 . . 120.1 ?
C18 C17 H17 . . 120.1 ?
C13 C18 C17 . . 121.4(3) ?
C13 C18 H18 . . 119.3 ?
C17 C18 H18 . . 119.3 ?
N1 C19 H19A . . 109.5 ?
N1 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
N1 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
N1 C20 H20A . . 109.5 ?
N1 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
N1 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C4 N1 C19 . . 114.0(2) ?
C4 N1 C20 . . 110.6(2) ?
C19 N1 C20 . . 111.4(2) ?
C1 O1 C4 . . 108.56(19) ?

