# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_220191199fzy_0m
_database_code_depnum_ccdc_archive 'CCDC 1974930'
loop_
_audit_author_name
_audit_author_address
'Zaiyong Zhang'
;Chinese Academy of Sciences, Shanghai 
China
;
_audit_update_record             
;
2019-12-31 deposited with the CCDC.	2020-12-22 downloaded from the CCDC.
;
_audit_creation_date             2019-11-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H20 F N'
_chemical_formula_sum            'C23 H20 F N'
_chemical_formula_weight         329.40
_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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   23.0769(10)
_cell_length_b                   6.4038(2)
_cell_length_c                   24.0305(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.876(2)
_cell_angle_gamma                90
_cell_volume                     3517.7(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2840
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.225
_cell_measurement_theta_min      2.295
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1413 before and 0.0517 after correction. The Ratio of minimum to maximum transmission is 0.9174. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_av_unetI/netI     0.0590
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            12779
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.424
_diffrn_reflns_theta_min         2.295
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'D8 VENTURE '
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2367
_reflns_number_total             3570
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.187
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3570
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0503
_refine_ls_restrained_S_all      1.035
_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)+(0.0433P)²+2.2622P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1235
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C9(H9), C11(H11), C7(H7), C2(H2), C19(H19), C22(H22), C21(H21),
 C4(H4), C20(H20), C6(H6), C5(H5)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C16(H16A,H16B,H16C)
;
_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 0.70726(5) 0.53465(18) 0.45194(5) 0.0440(3) Uani 1 1 d . . . . .
N1 N 0.56833(7) 0.3799(3) 0.45805(7) 0.0322(4) Uani 1 1 d . . . . .
C18 C 0.55881(7) 0.7248(3) 0.42650(8) 0.0278(4) Uani 1 1 d . . . . .
C15 C 0.59876(8) 0.4947(3) 0.49556(8) 0.0283(4) Uani 1 1 d . . . . .
C23 C 0.54274(8) 0.5187(3) 0.41486(8) 0.0278(4) Uani 1 1 d . . . . .
C10 C 0.75708(8) 0.7656(3) 0.36275(8) 0.0297(5) Uani 1 1 d . . . . .
C13 C 0.65721(8) 0.8286(3) 0.48132(8) 0.0294(4) Uani 1 1 d . . . . .
H13A H 0.651204 0.978774 0.472565 0.035 Uiso 1 1 calc R . . . .
H13B H 0.679441 0.819090 0.519512 0.035 Uiso 1 1 calc R . . . .
C12 C 0.69406(8) 0.7399(3) 0.44111(8) 0.0297(5) Uani 1 1 d . . . . .
C14 C 0.59653(7) 0.7279(3) 0.48277(8) 0.0271(4) Uani 1 1 d . . . . .
C1 C 0.78306(8) 0.5639(3) 0.36546(8) 0.0329(5) Uani 1 1 d . . . . .
H1 H 0.773417 0.466391 0.392531 0.039 Uiso 1 1 calc R . . . .
C3 C 0.83699(8) 0.6471(3) 0.28838(8) 0.0311(5) Uani 1 1 d . . . . .
C9 C 0.77213(8) 0.9037(3) 0.32309(8) 0.0304(5) Uani 1 1 d . . . . .
H9 H 0.755362 1.039472 0.321002 0.037 Uiso 1 1 calc R . . . .
C8 C 0.81182(8) 0.8497(3) 0.28535(8) 0.0302(5) Uani 1 1 d . . . . .
C11 C 0.71602(8) 0.8377(3) 0.40027(8) 0.0310(5) Uani 1 1 d . . . . .
H11 H 0.703112 0.977713 0.394189 0.037 Uiso 1 1 calc R . . . .
C17 C 0.56653(8) 0.8445(3) 0.52709(8) 0.0333(5) Uani 1 1 d . . . . .
H17A H 0.560464 0.990840 0.515823 0.050 Uiso 1 1 calc GR . . . .
H17B H 0.591365 0.837737 0.563551 0.050 Uiso 1 1 calc GR . . . .
H17C H 0.528679 0.779209 0.530085 0.050 Uiso 1 1 calc GR . . . .
C7 C 0.82667(8) 0.9916(3) 0.24403(8) 0.0358(5) Uani 1 1 d . . . . .
H7 H 0.810549 1.128281 0.241958 0.043 Uiso 1 1 calc R . . . .
C2 C 0.82170(8) 0.5081(3) 0.32977(8) 0.0346(5) Uani 1 1 d . . . . .
H2 H 0.838692 0.372742 0.332813 0.041 Uiso 1 1 calc R . . . .
C19 C 0.53873(8) 0.8828(3) 0.39016(9) 0.0358(5) Uani 1 1 d . . . . .
H19 H 0.549673 1.023699 0.398250 0.043 Uiso 1 1 calc R . . . .
C22 C 0.50480(8) 0.4662(3) 0.36678(8) 0.0348(5) Uani 1 1 d . . . . .
H22 H 0.492821 0.325865 0.359383 0.042 Uiso 1 1 calc R . . . .
C21 C 0.48505(9) 0.6264(3) 0.32999(9) 0.0398(5) Uani 1 1 d . . . . .
H21 H 0.459521 0.595009 0.296575 0.048 Uiso 1 1 calc R . . . .
C16 C 0.63065(9) 0.4073(3) 0.54842(9) 0.0410(5) Uani 1 1 d . . . . .
H16A H 0.614936 0.467925 0.580689 0.062 Uiso 1 1 calc GR . . . .
H16B H 0.672335 0.441153 0.550787 0.062 Uiso 1 1 calc GR . . . .
H16C H 0.625701 0.255358 0.548618 0.062 Uiso 1 1 calc GR . . . .
C4 C 0.87510(8) 0.5918(4) 0.24927(9) 0.0394(5) Uani 1 1 d . . . . .
H4 H 0.891821 0.456044 0.250498 0.047 Uiso 1 1 calc R . . . .
C20 C 0.50207(9) 0.8314(4) 0.34133(9) 0.0430(6) Uani 1 1 d . . . . .
H20 H 0.488461 0.938204 0.315346 0.052 Uiso 1 1 calc R . . . .
C6 C 0.86380(9) 0.9332(4) 0.20741(9) 0.0417(5) Uani 1 1 d . . . . .
H6 H 0.873419 1.029435 0.180006 0.050 Uiso 1 1 calc R . . . .
C5 C 0.88801(9) 0.7311(4) 0.20994(9) 0.0441(6) Uani 1 1 d . . . . .
H5 H 0.913582 0.691511 0.183980 0.053 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 C12 1.366(2) . ?
N1 C15 1.293(2) . ?
N1 C23 1.431(2) . ?
C18 C23 1.389(3) . ?
C18 C14 1.505(3) . ?
C18 C19 1.375(3) . ?
C15 C14 1.524(3) . ?
C15 C16 1.487(3) . ?
C23 C22 1.392(3) . ?
C10 C1 1.422(3) . ?
C10 C9 1.379(3) . ?
C10 C11 1.469(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C12 1.485(3) . ?
C13 C14 1.546(2) . ?
C12 C11 1.322(3) . ?
C14 C17 1.541(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.367(3) . ?
C3 C8 1.419(3) . ?
C3 C2 1.415(3) . ?
C3 C4 1.417(3) . ?
C9 H9 0.9500 . ?
C9 C8 1.417(3) . ?
C8 C7 1.422(3) . ?
C11 H11 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C7 H7 0.9500 . ?
C7 C6 1.362(3) . ?
C2 H2 0.9500 . ?
C19 H19 0.9500 . ?
C19 C20 1.389(3) . ?
C22 H22 0.9500 . ?
C22 C21 1.390(3) . ?
C21 H21 0.9500 . ?
C21 C20 1.387(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C4 H4 0.9500 . ?
C4 C5 1.362(3) . ?
C20 H20 0.9500 . ?
C6 H6 0.9500 . ?
C6 C5 1.408(3) . ?
C5 H5 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
C15 N1 C23 106.43(16) . . ?
C23 C18 C14 107.41(17) . . ?
C19 C18 C23 120.92(18) . . ?
C19 C18 C14 131.63(19) . . ?
N1 C15 C14 114.61(16) . . ?
N1 C15 C16 122.63(18) . . ?
C16 C15 C14 122.67(17) . . ?
C18 C23 N1 111.84(17) . . ?
C18 C23 C22 121.12(18) . . ?
C22 C23 N1 127.02(18) . . ?
C1 C10 C11 124.11(17) . . ?
C9 C10 C1 118.01(18) . . ?
C9 C10 C11 117.86(18) . . ?
H13A C13 H13B 107.3 . . ?
C12 C13 H13A 108.0 . . ?
C12 C13 H13B 108.0 . . ?
C12 C13 C14 117.14(16) . . ?
C14 C13 H13A 108.0 . . ?
C14 C13 H13B 108.0 . . ?
F1 C12 C13 112.14(16) . . ?
C11 C12 F1 119.92(17) . . ?
C11 C12 C13 127.86(19) . . ?
C18 C14 C15 99.65(15) . . ?
C18 C14 C13 113.54(15) . . ?
C18 C14 C17 111.59(15) . . ?
C15 C14 C13 114.06(15) . . ?
C15 C14 C17 109.98(15) . . ?
C17 C14 C13 107.90(15) . . ?
C10 C1 H1 119.5 . . ?
C2 C1 C10 121.08(19) . . ?
C2 C1 H1 119.5 . . ?
C2 C3 C8 118.13(18) . . ?
C2 C3 C4 123.09(19) . . ?
C4 C3 C8 118.77(18) . . ?
C10 C9 H9 118.9 . . ?
C10 C9 C8 122.10(19) . . ?
C8 C9 H9 118.9 . . ?
C3 C8 C7 118.93(18) . . ?
C9 C8 C3 119.11(18) . . ?
C9 C8 C7 121.96(19) . . ?
C10 C11 H11 114.7 . . ?
C12 C11 C10 130.68(19) . . ?
C12 C11 H11 114.7 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C8 C7 H7 119.7 . . ?
C6 C7 C8 120.6(2) . . ?
C6 C7 H7 119.7 . . ?
C1 C2 C3 121.6(2) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C18 C19 H19 120.8 . . ?
C18 C19 C20 118.4(2) . . ?
C20 C19 H19 120.8 . . ?
C23 C22 H22 121.2 . . ?
C21 C22 C23 117.65(19) . . ?
C21 C22 H22 121.2 . . ?
C22 C21 H21 119.5 . . ?
C20 C21 C22 120.95(19) . . ?
C20 C21 H21 119.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.7(2) . . ?
C5 C4 H4 119.6 . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 120.9(2) . . ?
C21 C20 H20 119.5 . . ?
C7 C6 H6 119.8 . . ?
C7 C6 C5 120.4(2) . . ?
C5 C6 H6 119.8 . . ?
C4 C5 C6 120.6(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_220191262_0m
_database_code_depnum_ccdc_archive 'CCDC 1974934'
loop_
_audit_author_name
_audit_author_address
'Zaiyong Zhang'
;Chinese Academy of Sciences, Shanghai 
China
;
_audit_update_record             
;
2019-12-31 deposited with the CCDC.	2020-12-22 downloaded from the CCDC.
;
_audit_creation_date             2019-12-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H23 F O'
_chemical_formula_sum            'C27 H23 F O'
_chemical_formula_weight         382.45
_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'
O O 0.0106 0.0060 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.3789(4)
_cell_length_b                   9.7180(3)
_cell_length_c                   22.5084(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.325(2)
_cell_angle_gamma                90
_cell_volume                     2018.29(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2685
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.077
_cell_measurement_theta_min      2.288
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6378
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1219 before and 0.0681 after correction. The Ratio of minimum to maximum transmission is 0.8556. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0759
_diffrn_reflns_av_unetI/netI     0.0733
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            15178
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.392
_diffrn_reflns_theta_min         2.207
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2564
_reflns_number_total             4068
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.211
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4068
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1022
_refine_ls_R_factor_gt           0.0519
_refine_ls_restrained_S_all      1.020
_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)+(0.0581P)²+0.3815P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1435
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C22(H22), C25(H25), C24(H24), C5(H5), C23(H23), C8(H8), C1(H1), C19(H19),
 C13(H13), C12(H12), C11(H11), C2(H2), C9(H9), C4(H4), C3(H3)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C)
;
_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 0.63476(14) 0.83587(13) 0.62072(6) 0.0449(4) Uani 1 1 d . . . . .
O1 O 0.8819(2) 0.94176(16) 0.56136(8) 0.0552(5) Uani 1 1 d . . . . .
C20 C 0.6862(2) 0.59384(19) 0.48081(9) 0.0267(5) Uani 1 1 d . . . . .
C21 C 0.7726(2) 0.5775(2) 0.53828(9) 0.0258(5) Uani 1 1 d . . . . .
C22 C 0.7829(2) 0.4486(2) 0.56464(9) 0.0318(5) Uani 1 1 d . . . . .
H22 H 0.839929 0.436697 0.603653 0.038 Uiso 1 1 calc R . . . .
C25 C 0.6162(2) 0.4794(2) 0.45142(9) 0.0306(5) Uani 1 1 d . . . . .
H25 H 0.559000 0.489881 0.412339 0.037 Uiso 1 1 calc R . . . .
C6 C 0.1258(2) 0.7613(2) 0.78815(9) 0.0281(5) Uani 1 1 d . . . . .
C14 C 0.7095(2) 0.7291(2) 0.65179(9) 0.0313(5) Uani 1 1 d . . . . .
C7 C 0.2604(2) 0.73796(19) 0.76401(9) 0.0282(5) Uani 1 1 d . . . . .
C24 C 0.6288(2) 0.3515(2) 0.47835(10) 0.0327(5) Uani 1 1 d . . . . .
H24 H 0.580904 0.274258 0.457888 0.039 Uiso 1 1 calc R . . . .
C10 C 0.5159(2) 0.6901(2) 0.71498(9) 0.0312(5) Uani 1 1 d . . . . .
C16 C 0.8614(2) 0.6973(2) 0.56788(9) 0.0310(5) Uani 1 1 d . . . . .
C5 C 0.0823(2) 0.6707(2) 0.82973(9) 0.0322(5) Uani 1 1 d . . . . .
H5 H 0.140016 0.592074 0.842385 0.039 Uiso 1 1 calc R . . . .
C23 C 0.7113(2) 0.3363(2) 0.53512(10) 0.0336(5) Uani 1 1 d . . . . .
H23 H 0.719242 0.248628 0.554091 0.040 Uiso 1 1 calc R . . . .
C8 C 0.2770(2) 0.7894(2) 0.70768(9) 0.0325(5) Uani 1 1 d . . . . .
H8 H 0.200617 0.841799 0.684966 0.039 Uiso 1 1 calc R . . . .
C1 C 0.0369(2) 0.8749(2) 0.77040(9) 0.0310(5) Uani 1 1 d . . . . .
H1 H 0.064162 0.938880 0.742551 0.037 Uiso 1 1 calc R . . . .
C19 C 0.6655(2) 0.7290(2) 0.45383(9) 0.0329(5) Uani 1 1 d . . . . .
H19 H 0.604894 0.736212 0.415330 0.040 Uiso 1 1 calc R . . . .
C13 C 0.6514(2) 0.6645(2) 0.69315(9) 0.0347(5) Uani 1 1 d . . . . .
H13 H 0.706494 0.589120 0.711812 0.042 Uiso 1 1 calc R . . . .
C15 C 0.8550(2) 0.7119(2) 0.63620(9) 0.0327(5) Uani 1 1 d . . . . .
H15A H 0.900262 0.629212 0.657339 0.039 Uiso 1 1 calc R . . . .
H15B H 0.914862 0.792132 0.652221 0.039 Uiso 1 1 calc R . . . .
C17 C 0.8238(3) 0.8373(2) 0.53742(10) 0.0366(6) Uani 1 1 d . . . . .
C12 C 0.3753(2) 0.6605(2) 0.79484(10) 0.0371(6) Uani 1 1 d . . . . .
H12 H 0.368633 0.622890 0.833209 0.044 Uiso 1 1 calc R . . . .
C11 C 0.4985(3) 0.6371(2) 0.77082(10) 0.0409(6) Uani 1 1 d . . . . .
H11 H 0.574114 0.583082 0.793088 0.049 Uiso 1 1 calc R . . . .
C2 C -0.0899(3) 0.8962(2) 0.79251(10) 0.0382(6) Uani 1 1 d . . . . .
H2 H -0.149443 0.973292 0.779290 0.046 Uiso 1 1 calc R . . . .
C9 C 0.4003(2) 0.7667(2) 0.68410(9) 0.0351(5) Uani 1 1 d . . . . .
H9 H 0.406909 0.804186 0.645709 0.042 Uiso 1 1 calc R . . . .
C4 C -0.0426(3) 0.6930(2) 0.85284(10) 0.0395(6) Uani 1 1 d . . . . .
H4 H -0.068621 0.631195 0.881819 0.047 Uiso 1 1 calc R . . . .
C18 C 0.7257(3) 0.8451(2) 0.47913(10) 0.0368(6) Uani 1 1 d . . . . .
C26 C 1.0209(2) 0.6706(2) 0.56205(11) 0.0437(6) Uani 1 1 d . . . . .
H26A H 1.054293 0.584772 0.582893 0.066 Uiso 1 1 calc GR . . . .
H26B H 1.081463 0.747063 0.580296 0.066 Uiso 1 1 calc GR . . . .
H26C H 1.028024 0.662856 0.519266 0.066 Uiso 1 1 calc GR . . . .
C3 C -0.1299(3) 0.8053(2) 0.83379(10) 0.0420(6) Uani 1 1 d . . . . .
H3 H -0.216847 0.819728 0.849040 0.050 Uiso 1 1 calc R . . . .
C27 C 0.6958(3) 0.9842(2) 0.45141(12) 0.0600(8) Uani 1 1 d . . . . .
H27A H 0.638330 0.974499 0.410736 0.090 Uiso 1 1 calc GR . . . .
H27B H 0.787597 1.030090 0.448991 0.090 Uiso 1 1 calc GR . . . .
H27C H 0.641692 1.039350 0.476326 0.090 Uiso 1 1 calc GR . . . .


_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 C14 1.372(2) . ?
O1 C17 1.230(2) . ?
C20 C21 1.407(3) . ?
C20 C25 1.396(3) . ?
C20 C19 1.446(3) . ?
C21 C22 1.382(3) . ?
C21 C16 1.515(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.386(3) . ?
C25 H25 0.9500 . ?
C25 C24 1.379(3) . ?
C6 C7 1.479(3) . ?
C6 C5 1.398(3) . ?
C6 C1 1.397(3) . ?
C14 C13 1.319(3) . ?
C14 C15 1.479(3) . ?
C7 C8 1.397(3) . ?
C7 C12 1.393(3) . ?
C24 H24 0.9500 . ?
C24 C23 1.378(3) . ?
C10 C13 1.464(3) . ?
C10 C11 1.394(3) . ?
C10 C9 1.394(3) . ?
C16 C15 1.556(3) . ?
C16 C17 1.536(3) . ?
C16 C26 1.547(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.381(3) . ?
C23 H23 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.374(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.385(3) . ?
C19 H19 0.9500 . ?
C19 C18 1.341(3) . ?
C13 H13 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C17 C18 1.463(3) . ?
C12 H12 0.9500 . ?
C12 C11 1.379(3) . ?
C11 H11 0.9500 . ?
C2 H2 0.9500 . ?
C2 C3 1.382(3) . ?
C9 H9 0.9500 . ?
C4 H4 0.9500 . ?
C4 C3 1.386(3) . ?
C18 C27 1.494(3) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C3 H3 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

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
C21 C20 C19 120.04(18) . . ?
C25 C20 C21 119.34(18) . . ?
C25 C20 C19 120.56(19) . . ?
C20 C21 C16 119.87(18) . . ?
C22 C21 C20 118.79(18) . . ?
C22 C21 C16 121.16(18) . . ?
C21 C22 H22 119.4 . . ?
C21 C22 C23 121.13(19) . . ?
C23 C22 H22 119.4 . . ?
C20 C25 H25 119.5 . . ?
C24 C25 C20 120.92(19) . . ?
C24 C25 H25 119.5 . . ?
C5 C6 C7 121.34(19) . . ?
C1 C6 C7 121.38(18) . . ?
C1 C6 C5 117.3(2) . . ?
F1 C14 C15 111.92(18) . . ?
C13 C14 F1 118.8(2) . . ?
C13 C14 C15 129.0(2) . . ?
C8 C7 C6 121.32(19) . . ?
C12 C7 C6 122.33(18) . . ?
C12 C7 C8 116.3(2) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 C25 119.57(19) . . ?
C23 C24 H24 120.2 . . ?
C11 C10 C13 119.3(2) . . ?
C9 C10 C13 124.6(2) . . ?
C9 C10 C11 116.1(2) . . ?
C21 C16 C15 112.89(17) . . ?
C21 C16 C17 114.87(18) . . ?
C21 C16 C26 107.29(16) . . ?
C17 C16 C15 108.31(17) . . ?
C17 C16 C26 105.03(18) . . ?
C26 C16 C15 107.95(17) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 C6 121.5(2) . . ?
C4 C5 H5 119.3 . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.23(19) . . ?
C24 C23 H23 119.9 . . ?
C7 C8 H8 119.0 . . ?
C9 C8 C7 122.1(2) . . ?
C9 C8 H8 119.0 . . ?
C6 C1 H1 119.3 . . ?
C2 C1 C6 121.5(2) . . ?
C2 C1 H1 119.3 . . ?
C20 C19 H19 117.6 . . ?
C18 C19 C20 124.8(2) . . ?
C18 C19 H19 117.6 . . ?
C14 C13 C10 130.5(2) . . ?
C14 C13 H13 114.7 . . ?
C10 C13 H13 114.7 . . ?
C14 C15 C16 116.45(17) . . ?
C14 C15 H15A 108.2 . . ?
C14 C15 H15B 108.2 . . ?
C16 C15 H15A 108.2 . . ?
C16 C15 H15B 108.2 . . ?
H15A C15 H15B 107.3 . . ?
O1 C17 C16 119.2(2) . . ?
O1 C17 C18 120.6(2) . . ?
C18 C17 C16 120.22(18) . . ?
C7 C12 H12 119.3 . . ?
C11 C12 C7 121.4(2) . . ?
C11 C12 H12 119.3 . . ?
C10 C11 H11 118.9 . . ?
C12 C11 C10 122.3(2) . . ?
C12 C11 H11 118.9 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0(2) . . ?
C3 C2 H2 120.0 . . ?
C10 C9 H9 119.1 . . ?
C8 C9 C10 121.8(2) . . ?
C8 C9 H9 119.1 . . ?
C5 C4 H4 120.0 . . ?
C5 C4 C3 120.1(2) . . ?
C3 C4 H4 120.0 . . ?
C19 C18 C17 119.09(19) . . ?
C19 C18 C27 123.4(2) . . ?
C17 C18 C27 117.5(2) . . ?
C16 C26 H26A 109.5 . . ?
C16 C26 H26B 109.5 . . ?
C16 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C2 C3 C4 119.7(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C18 C27 H27A 109.5 . . ?
C18 C27 H27B 109.5 . . ?
C18 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
