# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# 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. 
# 
#######################################################################

data_rm2017
_database_code_depnum_ccdc_archive 'CCDC 1996990'
loop_
_audit_author_name
_audit_author_address
'Ayan Dasgupta'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2020-04-15 deposited with the CCDC.	2020-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H19 N'
_chemical_formula_sum            'C25 H19 N'
_chemical_formula_weight         333.41

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   8.7417(5)
_cell_length_b                   11.0177(6)
_cell_length_c                   19.0730(11)
_cell_angle_alpha                90
_cell_angle_beta                 101.123(6)
_cell_angle_gamma                90
_cell_volume                     1802.48(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    199.9(2)
_cell_measurement_reflns_used    5213
_cell_measurement_theta_min      3.6000
_cell_measurement_theta_max      29.0270

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.426
_exptl_crystal_size_mid          0.204
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.071
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_T_min  0.477
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.50a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      199.9(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16139
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.353
_diffrn_reflns_theta_max         29.855
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.873
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.873
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.873
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4525
_reflns_number_gt                3406
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_structure_solution    SHELX
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.0435P)²+0.7513P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4525
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1331
_refine_ls_wR_factor_gt          0.1227
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.03219(17) 0.02949(14) 0.22490(8) 0.0367(3) Uani 1 1 d . . . . .
C2 C 0.0073(2) -0.06387(17) 0.17511(9) 0.0463(4) Uani 1 1 d . . . . .
H2 H 0.068048 -0.133774 0.181073 0.056 Uiso 1 1 calc R U . . .
C3 C -0.1118(2) -0.0488(2) 0.11611(10) 0.0590(5) Uani 1 1 d . . . . .
H3 H -0.131523 -0.110009 0.081967 0.071 Uiso 1 1 calc R U . . .
C4 C -0.2019(2) 0.0558(2) 0.10706(10) 0.0616(5) Uani 1 1 d . . . . .
H4 H -0.280051 0.063723 0.066646 0.074 Uiso 1 1 calc R U . . .
C5 C -0.1782(2) 0.14767(19) 0.15647(10) 0.0550(5) Uani 1 1 d . . . . .
H5 H -0.240005 0.217004 0.150044 0.066 Uiso 1 1 calc R U . . .
C6 C -0.05942(18) 0.13531(15) 0.21672(9) 0.0413(4) Uani 1 1 d . . . . .
C7 C -0.00044(17) 0.21160(14) 0.27740(9) 0.0409(4) Uani 1 1 d . . . . .
C8 C -0.0426(2) 0.32546(16) 0.29882(12) 0.0531(5) Uani 1 1 d . . . . .
H8 H -0.125087 0.367763 0.271412 0.064 Uiso 1 1 calc R U . . .
C9 C 0.0393(2) 0.37442(16) 0.36099(12) 0.0596(5) Uani 1 1 d . . . . .
H9 H 0.012593 0.450860 0.375448 0.072 Uiso 1 1 calc R U . . .
C10 C 0.1615(2) 0.31154(17) 0.40253(11) 0.0555(5) Uani 1 1 d . . . . .
H10 H 0.214837 0.346916 0.444450 0.067 Uiso 1 1 calc R U . . .
C11 C 0.2064(2) 0.19735(16) 0.38341(9) 0.0455(4) Uani 1 1 d . . . . .
H11 H 0.287486 0.155189 0.411904 0.055 Uiso 1 1 calc R U . . .
C12 C 0.12494(17) 0.14870(14) 0.31977(8) 0.0370(3) Uani 1 1 d . . . . .
C13 C 0.25709(16) -0.05733(13) 0.31285(8) 0.0334(3) Uani 1 1 d . . . . .
H13 H 0.264697 -0.106872 0.270992 0.040 Uiso 1 1 calc R U . . .
C14 C 0.41944(16) -0.00257(13) 0.33848(8) 0.0348(3) Uani 1 1 d . . . . .
C15 C 0.47506(19) 0.07786(15) 0.29309(9) 0.0418(4) Uani 1 1 d . . . . .
H15 H 0.413878 0.095989 0.248808 0.050 Uiso 1 1 calc R U . . .
C16 C 0.6199(2) 0.13115(16) 0.31287(10) 0.0483(4) Uani 1 1 d . . . . .
H16 H 0.655741 0.184800 0.282026 0.058 Uiso 1 1 calc R U . . .
C17 C 0.71176(19) 0.10461(17) 0.37876(11) 0.0520(4) Uani 1 1 d . . . . .
H17 H 0.808928 0.140993 0.392486 0.062 Uiso 1 1 calc R U . . .
C18 C 0.65868(19) 0.02442(18) 0.42363(10) 0.0521(4) Uani 1 1 d . . . . .
H18 H 0.720920 0.005631 0.467561 0.063 Uiso 1 1 calc R U . . .
C19 C 0.51255(18) -0.02902(16) 0.40397(9) 0.0434(4) Uani 1 1 d . . . . .
H19 H 0.477255 -0.082729 0.434956 0.052 Uiso 1 1 calc R U . . .
C20 C 0.20091(16) -0.14228(13) 0.36532(8) 0.0333(3) Uani 1 1 d . . . . .
C21 C 0.27412(19) -0.25377(15) 0.38028(9) 0.0427(4) Uani 1 1 d . . . . .
H21 H 0.355238 -0.275161 0.357551 0.051 Uiso 1 1 calc R U . . .
C22 C 0.2287(2) -0.33331(16) 0.42820(10) 0.0487(4) Uani 1 1 d . . . . .
H22 H 0.279317 -0.407446 0.437715 0.058 Uiso 1 1 calc R U . . .
C23 C 0.1082(2) -0.30279(16) 0.46202(9) 0.0474(4) Uani 1 1 d . . . . .
H23 H 0.078457 -0.355595 0.495015 0.057 Uiso 1 1 calc R U . . .
C24 C 0.03200(19) -0.19386(16) 0.44672(9) 0.0464(4) Uani 1 1 d . . . . .
H24 H -0.050584 -0.173806 0.468813 0.056 Uiso 1 1 calc R U . . .
C25 C 0.07778(17) -0.11367(15) 0.39846(9) 0.0395(3) Uani 1 1 d . . . . .
H25 H 0.025467 -0.040355 0.388335 0.047 Uiso 1 1 calc R U . . .
N1 N 0.14464(14) 0.03838(11) 0.28707(6) 0.0352(3) 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 C2 1.388(2) . ?
C1 N1 1.3901(19) . ?
C1 C6 1.406(2) . ?
C2 C3 1.387(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.399(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.443(2) . ?
C7 C8 1.391(2) . ?
C7 C12 1.412(2) . ?
C8 C9 1.372(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.386(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.388(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.391(2) . ?
C11 H11 0.9300 . ?
C12 N1 1.3920(19) . ?
C13 N1 1.4606(18) . ?
C13 C20 1.519(2) . ?
C13 C14 1.5328(19) . ?
C13 H13 0.9800 . ?
C14 C19 1.384(2) . ?
C14 C15 1.391(2) . ?
C15 C16 1.380(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.386(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.372(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.391(2) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C25 1.386(2) . ?
C20 C21 1.389(2) . ?
C21 C22 1.379(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.379(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.376(2) . ?
C23 H23 0.9300 . ?
C24 C25 1.389(2) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?

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
C2 C1 N1 128.86(15) . . ?
C2 C1 C6 121.85(15) . . ?
N1 C1 C6 109.28(14) . . ?
C3 C2 C1 117.41(17) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C2 C3 C4 121.28(19) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 121.36(17) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 118.85(18) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C1 119.25(17) . . ?
C5 C6 C7 134.10(16) . . ?
C1 C6 C7 106.64(13) . . ?
C8 C7 C12 119.68(17) . . ?
C8 C7 C6 133.40(16) . . ?
C12 C7 C6 106.92(14) . . ?
C9 C8 C7 118.99(18) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 C10 120.91(17) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C9 C10 C11 121.93(18) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C10 C11 C12 117.10(17) . . ?
C10 C11 H11 121.5 . . ?
C12 C11 H11 121.5 . . ?
C11 C12 N1 129.85(15) . . ?
C11 C12 C7 121.38(15) . . ?
N1 C12 C7 108.77(14) . . ?
N1 C13 C20 112.61(12) . . ?
N1 C13 C14 110.17(12) . . ?
C20 C13 C14 115.43(12) . . ?
N1 C13 H13 106.0 . . ?
C20 C13 H13 106.0 . . ?
C14 C13 H13 106.0 . . ?
C19 C14 C15 118.74(14) . . ?
C19 C14 C13 123.51(14) . . ?
C15 C14 C13 117.75(13) . . ?
C16 C15 C14 120.88(16) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 119.91(16) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C16 119.68(16) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C19 120.54(17) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C14 C19 C18 120.26(16) . . ?
C14 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C25 C20 C21 118.36(14) . . ?
C25 C20 C13 122.59(13) . . ?
C21 C20 C13 119.04(13) . . ?
C22 C21 C20 121.20(15) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C21 C22 C23 119.92(16) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C24 C23 C22 119.70(16) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C23 C24 C25 120.38(16) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C20 C25 C24 120.40(15) . . ?
C20 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C1 N1 C12 108.39(12) . . ?
C1 N1 C13 123.75(12) . . ?
C12 N1 C13 127.81(12) . . ?

_refine_diff_density_max         0.175
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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_rm2018
_database_code_depnum_ccdc_archive 'CCDC 1996991'
loop_
_audit_author_name
_audit_author_address
'Ayan Dasgupta'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2020-04-15 deposited with the CCDC.	2020-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H19 F2 N'
_chemical_formula_sum            'C23 H19 F2 N'
_chemical_formula_weight         347.39

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   8.9007(4)
_cell_length_b                   11.1893(4)
_cell_length_c                   18.1967(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.764(4)
_cell_angle_gamma                90
_cell_volume                     1808.35(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    199.9(2)
_cell_measurement_reflns_used    6206
_cell_measurement_theta_min      4.2530
_cell_measurement_theta_max      29.4230

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.333
_exptl_crystal_size_mid          0.263
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_T_min  0.646
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.50a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      199.9(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17487
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.312
_diffrn_reflns_theta_max         29.819
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.879
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.879
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4569
_reflns_number_gt                3627
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_structure_solution    SHELXS
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.0549P)²+0.9291P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4569
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1425
_refine_ls_wR_factor_gt          0.1323
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.3006(2) 0.62092(18) 0.82842(10) 0.0486(5) Uani 1 1 d . . . . .
H1A H 0.229775 0.614408 0.865808 0.073 Uiso 1 1 calc R U . . .
H1B H 0.278790 0.691254 0.799434 0.073 Uiso 1 1 calc R U . . .
H1C H 0.400739 0.626356 0.851171 0.073 Uiso 1 1 calc R U . . .
C2 C 0.28878(17) 0.51343(15) 0.78004(8) 0.0341(3) Uani 1 1 d . . . . .
C3 C 0.20278(18) 0.41366(15) 0.78651(9) 0.0362(4) Uani 1 1 d . . . . .
C4 C 0.1015(2) 0.3840(2) 0.84662(11) 0.0516(5) Uani 1 1 d . . . . .
H4A H 0.134619 0.311044 0.870240 0.077 Uiso 1 1 calc R U . . .
H4B H 0.000200 0.374496 0.825981 0.077 Uiso 1 1 calc R U . . .
H4C H 0.104982 0.447568 0.882144 0.077 Uiso 1 1 calc R U . . .
C5 C 0.22887(17) 0.33878(14) 0.72487(9) 0.0340(3) Uani 1 1 d . . . . .
C6 C 0.1687(2) 0.22875(15) 0.70076(11) 0.0427(4) Uani 1 1 d . . . . .
H6 H 0.100688 0.188375 0.728491 0.051 Uiso 1 1 calc R U . . .
C7 C 0.2112(2) 0.18127(16) 0.63575(12) 0.0478(4) Uani 1 1 d . . . . .
H7 H 0.170487 0.108866 0.619134 0.057 Uiso 1 1 calc R U . . .
C8 C 0.3148(2) 0.24028(15) 0.59426(10) 0.0433(4) Uani 1 1 d . . . . .
H8 H 0.342004 0.206162 0.550455 0.052 Uiso 1 1 calc R U . . .
C9 C 0.37819(19) 0.34833(15) 0.61671(9) 0.0364(3) Uani 1 1 d . . . . .
H9 H 0.447755 0.386873 0.588980 0.044 Uiso 1 1 calc R U . . .
C10 C 0.33397(17) 0.39738(13) 0.68242(8) 0.0312(3) Uani 1 1 d . . . . .
C11 C 0.46631(16) 0.60088(13) 0.69232(8) 0.0295(3) Uani 1 1 d . . . . .
H11 H 0.501623 0.645535 0.736455 0.035 Uiso 1 1 calc R U . . .
C12 C 0.60729(16) 0.55342(13) 0.65885(8) 0.0296(3) Uani 1 1 d . . . . .
C13 C 0.70466(18) 0.48026(15) 0.70151(9) 0.0353(3) Uani 1 1 d . . . . .
H13 H 0.681219 0.459874 0.748969 0.042 Uiso 1 1 calc R U . . .
C14 C 0.83602(18) 0.43736(15) 0.67430(9) 0.0382(4) Uani 1 1 d . . . . .
H14 H 0.900766 0.388199 0.702832 0.046 Uiso 1 1 calc R U . . .
C15 C 0.86825(17) 0.46910(15) 0.60433(9) 0.0361(4) Uani 1 1 d . . . . .
C16 C 0.77610(19) 0.54116(17) 0.56055(10) 0.0416(4) Uani 1 1 d . . . . .
H16 H 0.800939 0.561598 0.513317 0.050 Uiso 1 1 calc R U . . .
C17 C 0.64471(18) 0.58290(16) 0.58848(9) 0.0370(4) Uani 1 1 d . . . . .
H17 H 0.580493 0.631634 0.559369 0.044 Uiso 1 1 calc R U . . .
C18 C 0.37832(17) 0.68963(13) 0.64289(8) 0.0303(3) Uani 1 1 d . . . . .
C19 C 0.4377(2) 0.80343(15) 0.63504(10) 0.0406(4) Uani 1 1 d . . . . .
H19 H 0.526372 0.824353 0.661807 0.049 Uiso 1 1 calc R U . . .
C20 C 0.3669(2) 0.88609(16) 0.58803(11) 0.0476(4) Uani 1 1 d . . . . .
H20 H 0.406974 0.962116 0.582725 0.057 Uiso 1 1 calc R U . . .
C21 C 0.2362(2) 0.85296(17) 0.54954(10) 0.0471(5) Uani 1 1 d . . . . .
C22 C 0.1726(2) 0.74262(18) 0.55615(10) 0.0486(5) Uani 1 1 d . . . . .
H22 H 0.083155 0.722983 0.529611 0.058 Uiso 1 1 calc R U . . .
C23 C 0.24522(19) 0.66047(15) 0.60361(10) 0.0395(4) Uani 1 1 d . . . . .
H23 H 0.203655 0.584964 0.608976 0.047 Uiso 1 1 calc R U . . .
N1 N 0.37201(14) 0.50394(11) 0.71788(7) 0.0315(3) Uani 1 1 d . . . . .
F1 F 0.99712(11) 0.42745(10) 0.57745(6) 0.0494(3) Uani 1 1 d . . . . .
F2 F 0.16498(17) 0.93424(12) 0.50382(7) 0.0719(4) 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 C2 1.490(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.363(2) . ?
C2 N1 1.3963(19) . ?
C3 C5 1.431(2) . ?
C3 C4 1.499(2) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.402(2) . ?
C5 C10 1.413(2) . ?
C6 C7 1.373(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.396(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.384(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.396(2) . ?
C9 H9 0.9300 . ?
C10 N1 1.387(2) . ?
C11 N1 1.4659(19) . ?
C11 C18 1.522(2) . ?
C11 C12 1.526(2) . ?
C11 H11 0.9800 . ?
C12 C17 1.384(2) . ?
C12 C13 1.391(2) . ?
C13 C14 1.385(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.370(2) . ?
C14 H14 0.9300 . ?
C15 F1 1.3586(17) . ?
C15 C16 1.368(2) . ?
C16 C17 1.386(2) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C23 1.382(2) . ?
C18 C19 1.390(2) . ?
C19 C20 1.383(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.369(3) . ?
C20 H20 0.9300 . ?
C21 F2 1.361(2) . ?
C21 C22 1.367(3) . ?
C22 C23 1.391(2) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?

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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 N1 109.78(14) . . ?
C3 C2 C1 128.93(15) . . ?
N1 C2 C1 121.29(14) . . ?
C2 C3 C5 106.91(14) . . ?
C2 C3 C4 127.72(17) . . ?
C5 C3 C4 125.35(16) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C10 119.32(15) . . ?
C6 C5 C3 132.94(16) . . ?
C10 C5 C3 107.70(14) . . ?
C7 C6 C5 119.23(16) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C6 C7 C8 120.84(17) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 121.63(17) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C10 117.64(16) . . ?
C8 C9 H9 121.2 . . ?
C10 C9 H9 121.2 . . ?
N1 C10 C9 131.51(15) . . ?
N1 C10 C5 107.14(13) . . ?
C9 C10 C5 121.33(15) . . ?
N1 C11 C18 112.79(12) . . ?
N1 C11 C12 111.85(12) . . ?
C18 C11 C12 113.33(12) . . ?
N1 C11 H11 106.1 . . ?
C18 C11 H11 106.1 . . ?
C12 C11 H11 106.1 . . ?
C17 C12 C13 118.53(14) . . ?
C17 C12 C11 122.72(14) . . ?
C13 C12 C11 118.72(13) . . ?
C14 C13 C12 120.93(15) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C15 C14 C13 118.39(15) . . ?
C15 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
F1 C15 C16 118.73(15) . . ?
F1 C15 C14 118.60(15) . . ?
C16 C15 C14 122.67(15) . . ?
C15 C16 C17 118.23(15) . . ?
C15 C16 H16 120.9 . . ?
C17 C16 H16 120.9 . . ?
C12 C17 C16 121.26(15) . . ?
C12 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C23 C18 C19 118.82(15) . . ?
C23 C18 C11 122.82(14) . . ?
C19 C18 C11 118.32(14) . . ?
C20 C19 C18 121.03(17) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C21 C20 C19 118.20(17) . . ?
C21 C20 H20 120.9 . . ?
C19 C20 H20 120.9 . . ?
F2 C21 C22 118.57(19) . . ?
F2 C21 C20 118.55(18) . . ?
C22 C21 C20 122.86(17) . . ?
C21 C22 C23 118.24(17) . . ?
C21 C22 H22 120.9 . . ?
C23 C22 H22 120.9 . . ?
C18 C23 C22 120.84(17) . . ?
C18 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C10 N1 C2 108.42(13) . . ?
C10 N1 C11 128.01(12) . . ?
C2 N1 C11 123.10(13) . . ?

_refine_diff_density_max         0.251
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.045

