# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_190920mww_0m
_database_code_depnum_ccdc_archive 'CCDC 2120630'
loop_
_audit_author_name
_audit_author_address
maww
;University of Science and Technology of China
China
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2022-01-14 downloaded from the CCDC.
;
_audit_creation_date             2019-09-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H23 F3 N2 O'
_chemical_formula_sum            'C22 H23 F3 N2 O'
_chemical_formula_weight         388.42
_chemical_absolute_configuration rmad
_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 0.0148 0.0070 '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'
N N 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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      trigonal
_space_group_IT_number           161
_space_group_name_H-M_alt        'R 3 c'
_space_group_name_Hall           'R 3 -2"c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+7/6'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'

_cell_length_a                   32.7473(4)
_cell_length_b                   32.7473(4)
_cell_length_c                   9.72720(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     9033.8(2)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    9864
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      53.983
_cell_measurement_theta_min      4.700
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.939
_exptl_absorpt_coefficient_mu    0.529
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6203
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1273 before and 0.0610 after correction. The Ratio of minimum to maximum transmission is 0.8262. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             3672
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            32549
_diffrn_reflns_point_group_measured_fraction_full 0.929
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.925
_diffrn_reflns_theta_min         4.699
_diffrn_ambient_temperature      170.04
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.845
_reflns_Friedel_fraction_full    0.858
_reflns_Friedel_fraction_max     0.852
_reflns_number_gt                3163
_reflns_number_total             3536
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         0.108
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 1287 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3536
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0336
_refine_ls_restrained_S_all      1.106
_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)+(0.0378P)²+1.8553P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0729
_refine_ls_wR_factor_ref         0.0771
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;
_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 0.29340(6) 0.56488(6) 0.5977(2) 0.0570(5) Uani 1 1 d . . . . .
F2 F 0.31312(5) 0.55880(6) 0.80422(17) 0.0521(4) Uani 1 1 d . . . . .
F3 F 0.35088(6) 0.62475(6) 0.69660(19) 0.0571(5) Uani 1 1 d . . . . .
O1 O 0.43379(7) 0.53613(6) 0.19459(18) 0.0399(4) Uani 1 1 d . . . . .
N1 N 0.38880(7) 0.55280(7) 0.3999(2) 0.0339(5) Uani 1 1 d . . . . .
N2 N 0.43282(7) 0.55475(8) 0.4181(2) 0.0358(5) Uani 1 1 d . . . . .
H2 H 0.446262 0.560250 0.499563 0.043 Uiso 1 1 calc R . . . .
C1 C 0.34847(8) 0.50666(8) 0.4441(3) 0.0336(5) Uani 1 1 d . . . . .
H1 H 0.355856 0.480957 0.426497 0.040 Uiso 1 1 calc R . . . .
C2 C 0.34458(8) 0.51223(9) 0.5981(3) 0.0327(5) Uani 1 1 d . . . . .
C3 C 0.36527(8) 0.56456(8) 0.6270(3) 0.0333(6) Uani 1 1 d . . . . .
H3 H 0.391449 0.574665 0.695163 0.040 Uiso 1 1 calc R . . . .
C4 C 0.38635(10) 0.58851(9) 0.4881(3) 0.0381(6) Uani 1 1 d . . . . .
H4A H 0.366153 0.599431 0.444760 0.046 Uiso 1 1 calc R . . . .
H4B H 0.418247 0.616067 0.501682 0.046 Uiso 1 1 calc R . . . .
C5 C 0.33073(9) 0.57801(9) 0.6806(3) 0.0418(6) Uani 1 1 d . . . . .
C6 C 0.30498(10) 0.49779(10) 0.3596(3) 0.0453(7) Uani 1 1 d . . . . .
H6 H 0.301013 0.526010 0.369442 0.054 Uiso 1 1 calc R . . . .
C7 C 0.31321(12) 0.49251(11) 0.2080(3) 0.0571(9) Uani 1 1 d . . . . .
H7A H 0.342243 0.520447 0.177233 0.086 Uiso 1 1 calc GR . . . .
H7B H 0.286517 0.489288 0.153835 0.086 Uiso 1 1 calc GR . . . .
H7C H 0.316166 0.464408 0.195404 0.086 Uiso 1 1 calc GR . . . .
C8 C 0.26004(10) 0.45480(13) 0.4116(4) 0.0640(9) Uani 1 1 d . . . . .
H8A H 0.263340 0.426739 0.404328 0.096 Uiso 1 1 calc GR . . . .
H8B H 0.233180 0.450373 0.355871 0.096 Uiso 1 1 calc GR . . . .
H8C H 0.254742 0.459689 0.507829 0.096 Uiso 1 1 calc GR . . . .
C9 C 0.32922(9) 0.47935(9) 0.6953(3) 0.0381(6) Uani 1 1 d . . . . .
H9 H 0.330218 0.489746 0.787011 0.046 Uiso 1 1 calc R . . . .
C10 C 0.31068(9) 0.42811(9) 0.6757(3) 0.0371(6) Uani 1 1 d . . . . .
C11 C 0.33763(9) 0.41101(9) 0.6169(3) 0.0387(6) Uani 1 1 d . . . . .
H11 H 0.368825 0.432493 0.587339 0.046 Uiso 1 1 calc R . . . .
C12 C 0.31977(11) 0.36300(10) 0.6006(3) 0.0464(7) Uani 1 1 d . . . . .
H12 H 0.338653 0.351755 0.559897 0.056 Uiso 1 1 calc R . . . .
C13 C 0.27457(11) 0.33157(10) 0.6434(3) 0.0487(7) Uani 1 1 d . . . . .
H13 H 0.262103 0.298662 0.631084 0.058 Uiso 1 1 calc R . . . .
C14 C 0.24774(11) 0.34781(11) 0.7035(4) 0.0557(8) Uani 1 1 d . . . . .
H14 H 0.216700 0.326146 0.733906 0.067 Uiso 1 1 calc R . . . .
C15 C 0.26556(11) 0.39553(10) 0.7203(4) 0.0523(8) Uani 1 1 d . . . . .
H15 H 0.246664 0.406383 0.763035 0.063 Uiso 1 1 calc R . . . .
C16 C 0.45333(9) 0.54797(8) 0.3077(3) 0.0329(5) Uani 1 1 d . . . . .
C17 C 0.50187(9) 0.55577(9) 0.3287(3) 0.0348(6) Uani 1 1 d . . . . .
C18 C 0.53246(9) 0.58663(10) 0.4277(3) 0.0427(7) Uani 1 1 d . . . . .
H18 H 0.522004 0.602232 0.488439 0.051 Uiso 1 1 calc R . . . .
C19 C 0.57809(10) 0.59464(12) 0.4378(3) 0.0551(8) Uani 1 1 d . . . . .
H19 H 0.598939 0.615867 0.505039 0.066 Uiso 1 1 calc R . . . .
C20 C 0.59321(12) 0.57185(12) 0.3505(4) 0.0611(9) Uani 1 1 d . . . . .
H20 H 0.624624 0.577664 0.356789 0.073 Uiso 1 1 calc R . . . .
C21 C 0.56287(12) 0.54062(12) 0.2540(4) 0.0625(9) Uani 1 1 d . . . . .
H21 H 0.573235 0.524330 0.195695 0.075 Uiso 1 1 calc R . . . .
C22 C 0.51730(11) 0.53277(10) 0.2414(3) 0.0478(7) Uani 1 1 d . . . . .
H22 H 0.496763 0.511743 0.173268 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 C5 1.343(3) . ?
F2 C5 1.346(3) . ?
F3 C5 1.339(3) . ?
O1 C16 1.234(3) . ?
N1 N2 1.422(3) . ?
N1 C1 1.489(3) . ?
N1 C4 1.485(3) . ?
N2 H2 0.8800 . ?
N2 C16 1.343(3) . ?
C1 H1 1.0000 . ?
C1 C2 1.522(4) . ?
C1 C6 1.541(3) . ?
C2 C3 1.521(3) . ?
C2 C9 1.328(4) . ?
C3 H3 1.0000 . ?
C3 C4 1.541(4) . ?
C3 C5 1.498(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C6 H6 1.0000 . ?
C6 C7 1.524(4) . ?
C6 C8 1.527(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9 0.9500 . ?
C9 C10 1.484(4) . ?
C10 C11 1.384(4) . ?
C10 C15 1.390(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.385(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.379(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.365(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.377(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.493(4) . ?
C17 C18 1.393(4) . ?
C17 C22 1.387(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.385(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.376(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.378(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.387(4) . ?
C22 H22 0.9500 . ?

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
N2 N1 C1 112.00(18) . . ?
N2 N1 C4 110.20(19) . . ?
C4 N1 C1 105.21(19) . . ?
N1 N2 H2 120.9 . . ?
C16 N2 N1 118.2(2) . . ?
C16 N2 H2 120.9 . . ?
N1 C1 H1 109.8 . . ?
N1 C1 C2 104.34(18) . . ?
N1 C1 C6 107.7(2) . . ?
C2 C1 H1 109.8 . . ?
C2 C1 C6 115.0(2) . . ?
C6 C1 H1 109.8 . . ?
C3 C2 C1 107.5(2) . . ?
C9 C2 C1 128.6(2) . . ?
C9 C2 C3 123.8(2) . . ?
C2 C3 H3 108.7 . . ?
C2 C3 C4 104.2(2) . . ?
C4 C3 H3 108.7 . . ?
C5 C3 C2 114.8(2) . . ?
C5 C3 H3 108.7 . . ?
C5 C3 C4 111.5(2) . . ?
N1 C4 C3 107.02(19) . . ?
N1 C4 H4A 110.3 . . ?
N1 C4 H4B 110.3 . . ?
C3 C4 H4A 110.3 . . ?
C3 C4 H4B 110.3 . . ?
H4A C4 H4B 108.6 . . ?
F1 C5 F2 106.2(2) . . ?
F1 C5 C3 113.4(2) . . ?
F2 C5 C3 112.5(2) . . ?
F3 C5 F1 106.6(2) . . ?
F3 C5 F2 106.4(2) . . ?
F3 C5 C3 111.3(2) . . ?
C1 C6 H6 108.0 . . ?
C7 C6 C1 109.8(2) . . ?
C7 C6 H6 108.0 . . ?
C7 C6 C8 111.1(3) . . ?
C8 C6 C1 111.8(2) . . ?
C8 C6 H6 108.0 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C2 C9 H9 116.5 . . ?
C2 C9 C10 126.9(2) . . ?
C10 C9 H9 116.5 . . ?
C11 C10 C9 121.8(2) . . ?
C11 C10 C15 117.8(3) . . ?
C15 C10 C9 120.4(2) . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 120.9(3) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 119.9(3) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.9(3) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.2(3) . . ?
C15 C14 H14 119.9 . . ?
C10 C15 H15 119.4 . . ?
C14 C15 C10 121.3(3) . . ?
C14 C15 H15 119.4 . . ?
O1 C16 N2 122.8(2) . . ?
O1 C16 C17 121.1(2) . . ?
N2 C16 C17 116.1(2) . . ?
C18 C17 C16 122.5(2) . . ?
C22 C17 C16 118.0(2) . . ?
C22 C17 C18 119.5(3) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.2(3) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.0(3) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.1(3) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.5(3) . . ?
C22 C21 H21 119.8 . . ?
C17 C22 H22 120.2 . . ?
C21 C22 C17 119.7(3) . . ?
C21 C22 H22 120.2 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
