# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_shelx
_audit_block_doi                 10.5517/ccdc.csd.cc27lhw7
_database_code_depnum_ccdc_archive 'CCDC 2073369'
loop_
_audit_author_name
_audit_author_address
'Matija Gredicak'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2021-03-26 deposited with the CCDC.	2021-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H26 F3 N O2'
_chemical_formula_weight         453.49

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      tetragonal
_space_group_IT_number           96
_space_group_name_H-M_alt        'P 43 21 2'
_space_group_name_Hall           'P 4nw 2abw'

_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'
'-y+1/2, x+1/2, z+3/4'
'-x, -y, z+1/2'
'y+1/2, -x+1/2, z+1/4'
'x+1/2, -y+1/2, -z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   10.0976(4)
_cell_length_b                   10.0976(4)
_cell_length_c                   48.799(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4975.7(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7242
_cell_measurement_theta_min      3.293
_cell_measurement_theta_max      75.870

_exptl_crystal_description       needles
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_F_000             1904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.759
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Xcalibur
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17868
_diffrn_reflns_av_unetI/netI     0.0620
_diffrn_reflns_av_R_equivalents  0.0880
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -57
_diffrn_reflns_limit_l_max       56
_diffrn_reflns_theta_min         3.623
_diffrn_reflns_theta_max         68.046
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             4356
_reflns_number_gt                2789
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.637
_reflns_Friedel_fraction_max     0.951
_reflns_Friedel_fraction_full    0.960

_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    ?
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_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)+(0.1594P)²+5.5433P] 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-2016/4 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0024(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 701 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(3)
_chemical_absolute_configuration S
_refine_ls_number_reflns         4356
_refine_ls_number_parameters     304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1483
_refine_ls_R_factor_gt           0.1186
_refine_ls_wR_factor_ref         0.3612
_refine_ls_wR_factor_gt          0.3375
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.002

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
C1 C 1.074(3) 0.473(2) 1.0158(4) 0.235(15) Uani 1 1 d . . . . .
H1A H 1.007761 0.530690 1.023077 0.352 Uiso 1 1 calc R U . . .
H1B H 1.154294 0.521802 1.012624 0.352 Uiso 1 1 calc R U . . .
H1C H 1.091657 0.402936 1.028720 0.352 Uiso 1 1 calc R U . . .
C2 C 1.131(3) 0.367(3) 0.9725(5) 0.30(2) Uani 1 1 d . . . . .
H2A H 1.193621 0.436417 0.969205 0.452 Uiso 1 1 calc R U . . .
H2B H 1.094224 0.337460 0.955431 0.452 Uiso 1 1 calc R U . . .
H2C H 1.174716 0.294013 0.981388 0.452 Uiso 1 1 calc R U . . .
C3 C 0.9547(11) 0.8464(8) 0.9409(2) 0.076(3) Uani 1 1 d . . . . .
C4 C 0.9797(9) 0.6264(10) 0.9649(2) 0.083(3) Uani 1 1 d . . . . .
H4 H 1.068345 0.648582 0.967324 0.100 Uiso 1 1 calc R U . . .
C5 C 0.7290(12) 1.1289(10) 0.9292(3) 0.092(3) Uani 1 1 d . . . . .
H5 H 0.699420 1.199151 0.939873 0.110 Uiso 1 1 calc R U . . .
C7 C 0.8543(10) 0.9283(10) 0.9247(2) 0.079(3) Uani 1 1 d . . . . .
C8 C 0.7099(10) 0.5622(9) 0.9577(2) 0.078(3) Uani 1 1 d . . . . .
C9 C 0.9321(10) 0.5061(8) 0.9752(2) 0.080(3) Uani 1 1 d . . . . .
C10 C 0.7643(11) 0.6827(11) 0.9481(2) 0.086(3) Uani 1 1 d . . . . .
H10 H 0.709390 0.743297 0.939316 0.103 Uiso 1 1 calc R U . . .
C11 C 0.8963(10) 0.7125(8) 0.9514(2) 0.076(3) Uani 1 1 d . . . . .
C12 C 1.0784(10) 0.8243(10) 0.9246(2) 0.078(3) Uani 1 1 d . . . . .
C13 C 0.7166(13) 1.0063(12) 0.8886(3) 0.099(4) Uani 1 1 d . . . . .
H13 H 0.680049 0.995209 0.871276 0.119 Uiso 1 1 calc R U . . .
C14 C 1.1863(13) 0.9066(11) 0.9258(3) 0.094(3) Uani 1 1 d . . . . .
H14 H 1.186969 0.974967 0.938562 0.113 Uiso 1 1 calc R U . . .
C15 C 1.0834(13) 0.7225(12) 0.9050(3) 0.102(4) Uani 1 1 d . . . . .
H15 H 1.012481 0.664154 0.903607 0.122 Uiso 1 1 calc R U . . .
C16 C 0.5701(11) 0.5239(12) 0.9532(3) 0.102(4) Uani 1 1 d . . . . .
H16 H 0.546520 0.455389 0.966556 0.123 Uiso 1 1 calc R U . . .
C17 C 0.6820(15) 1.1122(12) 0.9035(3) 0.109(4) Uani 1 1 d . . . . .
H17 H 0.624842 1.174878 0.896121 0.130 Uiso 1 1 calc R U . . .
C18 C 1.1910(15) 0.7067(13) 0.8878(3) 0.112(4) Uani 1 1 d . . . . .
H18 H 1.193323 0.636130 0.875561 0.134 Uiso 1 1 calc R U . . .
C19 C 0.8074(14) 0.9111(11) 0.8986(3) 0.098(4) Uani 1 1 d . . . . .
H19 H 0.834139 0.839787 0.887823 0.118 Uiso 1 1 calc R U . . .
C20 C 0.8221(12) 1.0402(9) 0.9396(2) 0.081(3) Uani 1 1 d . . . . .
C21 C 0.8019(9) 0.4751(8) 0.9706(2) 0.075(3) Uani 1 1 d . . . . .
C22 C 0.8922(11) 1.0360(9) 0.9661(2) 0.076(3) Uani 1 1 d . . . . .
C24 C 1.0274(13) 0.4149(11) 0.9897(3) 0.109(4) Uani 1 1 d . . . . .
H24 H 0.975375 0.336780 0.994857 0.131 Uiso 1 1 calc R U . . .
C26 C 1.2946(12) 0.7952(11) 0.8888(3) 0.097(3) Uani 1 1 d . . . . .
C28 C 0.4780(12) 0.6451(19) 0.9577(4) 0.143(6) Uani 1 1 d . . . . .
H28A H 0.479748 0.700480 0.941727 0.215 Uiso 1 1 calc R U . . .
H28B H 0.508183 0.694659 0.973286 0.215 Uiso 1 1 calc R U . . .
H28C H 0.389163 0.614954 0.960897 0.215 Uiso 1 1 calc R U . . .
C30 C 0.5462(15) 0.4712(15) 0.9254(4) 0.138(6) Uani 1 1 d . . . . .
H30A H 0.612513 0.406360 0.921108 0.207 Uiso 1 1 calc R U . . .
H30B H 0.550268 0.542168 0.912367 0.207 Uiso 1 1 calc R U . . .
H30C H 0.460201 0.430756 0.924745 0.207 Uiso 1 1 calc R U . . .
C31 C 1.408(2) 0.773(2) 0.8696(4) 0.153(7) Uani 1 1 d . . . . .
C32 C 1.2957(15) 0.8913(13) 0.9084(3) 0.109(4) Uani 1 1 d . . . . .
H32 H 1.368823 0.946478 0.910253 0.131 Uiso 1 1 calc R U . . .
N6 N 0.9744(8) 0.9335(7) 0.96486(18) 0.080(2) Uani 1 1 d . . . . .
H6 H 1.034282 0.919003 0.977029 0.096 Uiso 1 1 calc R U . . .
O1 O 0.7455(7) 0.3544(7) 0.97888(19) 0.098(2) Uani 1 1 d . . . . .
H1 H 0.804231 0.303516 0.983733 0.147 Uiso 1 1 calc R U . . .
O2 O 0.8835(8) 1.1178(7) 0.98514(15) 0.091(2) Uani 1 1 d . . . . .
F1 F 1.5294(11) 0.7562(14) 0.8828(3) 0.195(5) Uani 1 1 d . . . . .
F2 F 1.4374(11) 0.8912(11) 0.8564(2) 0.169(4) Uani 1 1 d . . . . .
F3 F 1.3945(17) 0.689(2) 0.8521(4) 0.308(13) Uani 1 1 d . . . . .


_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
C1 C24 1.48(2) . ?
C2 C24 1.43(2) . ?
C3 N6 1.475(13) . ?
C3 C12 1.497(15) . ?
C3 C7 1.528(14) . ?
C3 C11 1.561(13) . ?
C4 C11 1.379(13) . ?
C4 C9 1.398(13) . ?
C5 C17 1.349(16) . ?
C5 C20 1.393(15) . ?
C7 C19 1.373(15) . ?
C7 C20 1.381(14) . ?
C8 C10 1.416(14) . ?
C8 C21 1.425(14) . ?
C8 C16 1.480(15) . ?
C9 C21 1.369(14) . ?
C9 C24 1.511(14) . ?
C10 C11 1.376(15) . ?
C12 C14 1.372(15) . ?
C12 C15 1.405(15) . ?
C13 C17 1.340(18) . ?
C13 C19 1.414(17) . ?
C14 C32 1.401(19) . ?
C15 C18 1.383(19) . ?
C16 C30 1.48(2) . ?
C16 C28 1.55(2) . ?
C18 C26 1.377(17) . ?
C20 C22 1.475(15) . ?
C21 O1 1.405(11) . ?
C22 O2 1.246(12) . ?
C22 N6 1.329(13) . ?
C26 C32 1.364(17) . ?
C26 C31 1.50(2) . ?
C31 F3 1.21(2) . ?
C31 F2 1.39(2) . ?
C31 F1 1.40(2) . ?

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
N6 C3 C12 113.4(8) . . ?
N6 C3 C7 100.2(7) . . ?
C12 C3 C7 111.1(8) . . ?
N6 C3 C11 107.9(8) . . ?
C12 C3 C11 111.1(8) . . ?
C7 C3 C11 112.8(8) . . ?
C11 C4 C9 120.6(9) . . ?
C17 C5 C20 119.6(11) . . ?
C19 C7 C20 120.7(9) . . ?
C19 C7 C3 129.9(10) . . ?
C20 C7 C3 109.1(9) . . ?
C10 C8 C21 115.1(9) . . ?
C10 C8 C16 123.0(9) . . ?
C21 C8 C16 121.8(9) . . ?
C21 C9 C4 118.1(9) . . ?
C21 C9 C24 123.3(9) . . ?
C4 C9 C24 118.6(10) . . ?
C11 C10 C8 121.6(10) . . ?
C10 C11 C4 120.6(9) . . ?
C10 C11 C3 121.1(9) . . ?
C4 C11 C3 118.2(9) . . ?
C14 C12 C15 116.2(10) . . ?
C14 C12 C3 123.4(10) . . ?
C15 C12 C3 120.1(9) . . ?
C17 C13 C19 121.7(11) . . ?
C12 C14 C32 122.3(11) . . ?
C18 C15 C12 121.8(11) . . ?
C30 C16 C8 112.8(11) . . ?
C30 C16 C28 108.4(12) . . ?
C8 C16 C28 110.1(11) . . ?
C13 C17 C5 120.8(11) . . ?
C26 C18 C15 120.1(12) . . ?
C7 C19 C13 117.1(11) . . ?
C7 C20 C5 119.6(10) . . ?
C7 C20 C22 108.9(9) . . ?
C5 C20 C22 131.4(10) . . ?
C9 C21 O1 122.8(8) . . ?
C9 C21 C8 123.8(8) . . ?
O1 C21 C8 113.4(8) . . ?
O2 C22 N6 126.4(9) . . ?
O2 C22 C20 127.0(9) . . ?
N6 C22 C20 106.4(9) . . ?
C2 C24 C1 114(2) . . ?
C2 C24 C9 113.5(14) . . ?
C1 C24 C9 111.7(11) . . ?
C32 C26 C18 119.4(13) . . ?
C32 C26 C31 122.7(14) . . ?
C18 C26 C31 117.6(13) . . ?
F3 C31 F2 107(2) . . ?
F3 C31 F1 110(2) . . ?
F2 C31 F1 97.5(14) . . ?
F3 C31 C26 117.5(16) . . ?
F2 C31 C26 108.9(17) . . ?
F1 C31 C26 113.6(16) . . ?
C26 C32 C14 119.9(12) . . ?
C22 N6 C3 114.6(8) . . ?

_refine_diff_density_max         0.298
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.064

