# 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_yanagi-re
_audit_block_doi                 10.5517/ccdc.csd.cc2b50sb
_database_code_depnum_ccdc_archive 'CCDC 2149781'
loop_
_audit_author_name
_audit_author_address
'Yoshihiko Yamamoto'
;Nagoya University
Japan
;
_audit_update_record             
;
2022-02-03 deposited with the CCDC.	2022-03-15 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C24 H21 F2 N O'
_chemical_formula_moiety         'C24 H21 F2 N O'
_chemical_formula_weight         377.43
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   10.2403(5)
_cell_length_b                   15.5996(8)
_cell_length_c                   12.3812(6)
_cell_angle_alpha                90.0000
_cell_angle_beta                 102.080(7)
_cell_angle_gamma                90.0000
_cell_volume                     1934.01(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    20076
_cell_measurement_theta_min      3.65
_cell_measurement_theta_max      68.24
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792.00
_exptl_absorpt_coefficient_mu    0.754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.669
_exptl_absorpt_correction_T_max  0.860

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            21888
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_theta_max         68.240
_diffrn_reflns_theta_min         4.623
_diffrn_reflns_theta_full        68.240
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3537
_reflns_number_gt                3231
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1243
_refine_ls_wR_factor_gt          0.1211
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3537
_refine_ls_number_parameters     253
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0609P)²+1.0356P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.40
_refine_diff_density_min         -0.40
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.32494(9) 0.53738(7) 0.16860(8) 0.0364(3) Uani 1 1 d . . .
F2 F 0.32975(10) 0.66584(7) 0.24004(8) 0.0392(3) Uani 1 1 d . . .
O3 O 0.42612(12) 0.59497(8) 0.43046(9) 0.0344(3) Uani 1 1 d . . .
N4 N 0.52031(14) 0.48427(9) 0.35660(11) 0.0297(3) Uani 1 1 d . . .
H4 H 0.5460 0.4645 0.4225 0.036 Uiso 1 1 calc R . .
C5 C 0.55817(16) 0.43410(11) 0.27283(13) 0.0282(4) Uani 1 1 d . . .
C6 C 0.45063(16) 0.55787(11) 0.34956(13) 0.0296(4) Uani 1 1 d . . .
C7 C 0.82320(17) 0.68676(11) -0.00070(14) 0.0319(4) Uani 1 1 d . . .
H7 H 0.8122 0.7302 -0.0532 0.038 Uiso 1 1 calc R . .
C8 C 0.85286(17) 0.55584(11) 0.15297(14) 0.0314(4) Uani 1 1 d . . .
H8 H 0.8634 0.5111 0.2037 0.038 Uiso 1 1 calc R . .
C9 C 0.40672(17) 0.59600(11) 0.23352(14) 0.0313(4) Uani 1 1 d . . .
C10 C 0.96283(17) 0.58612(11) 0.11554(14) 0.0326(4) Uani 1 1 d . . .
H10 H 1.0464 0.5619 0.1422 0.039 Uiso 1 1 calc R . .
C11 C 0.56114(17) 0.34563(11) 0.29038(14) 0.0319(4) Uani 1 1 d . . .
H11 H 0.5352 0.3236 0.3524 0.038 Uiso 1 1 calc R . .
C12 C 0.60208(17) 0.29059(11) 0.21687(15) 0.0331(4) Uani 1 1 d . . .
H12 H 0.6049 0.2318 0.2298 0.040 Uiso 1 1 calc R . .
C13 C 1.07049(18) 0.68585(13) 0.00015(15) 0.0370(4) Uani 1 1 d . . .
H13A H 1.0436 0.7299 -0.0541 0.044 Uiso 1 1 calc R . .
H13B H 1.1120 0.6399 -0.0318 0.044 Uiso 1 1 calc R . .
H13C H 1.1329 0.7091 0.0620 0.044 Uiso 1 1 calc R . .
C14 C 0.60021(15) 0.46893(11) 0.18098(13) 0.0274(4) Uani 1 1 d . . .
C15 C 0.63871(16) 0.41093(11) 0.10681(13) 0.0300(4) Uani 1 1 d . . .
H15 H 0.6648 0.4322 0.0444 0.036 Uiso 1 1 calc R . .
C16 C 0.61123(16) 0.56216(11) 0.16228(13) 0.0278(4) Uani 1 1 d . . .
C17 C 0.94965(17) 0.65239(11) 0.03840(14) 0.0306(4) Uani 1 1 d . . .
C18 C 0.72637(16) 0.59168(11) 0.11548(13) 0.0284(4) Uani 1 1 d . . .
C19 C 0.71280(17) 0.65717(11) 0.03755(14) 0.0312(4) Uani 1 1 d . . .
H19 H 0.6293 0.6814 0.0108 0.037 Uiso 1 1 calc R . .
C20 C 0.52409(17) 0.61991(11) 0.18662(13) 0.0300(4) Uani 1 1 d . . .
H20 H 0.5379 0.6776 0.1735 0.036 Uiso 1 1 calc R . .
C21 C 0.63917(17) 0.32332(11) 0.12333(14) 0.0325(4) Uani 1 1 d . . .
H21 H 0.6642 0.2865 0.0722 0.039 Uiso 1 1 calc R . .
C22 C 1.13750(19) 0.39338(12) 0.52748(18) 0.0423(5) Uani 1 1 d . . .
H22 H 1.1685 0.4019 0.6028 0.051 Uiso 1 1 calc R . .
C23 C 0.9597(2) 0.37287(13) 0.37105(18) 0.0457(5) Uani 1 1 d . . .
H23 H 0.8692 0.3662 0.3406 0.055 Uiso 1 1 calc R . .
C24 C 1.2267(2) 0.38892(12) 0.45794(18) 0.0447(5) Uani 1 1 d . . .
H24 H 1.3177 0.3938 0.4877 0.054 Uiso 1 1 calc R . .
C25 C 1.0007(2) 0.38506(11) 0.48450(18) 0.0422(5) Uani 1 1 d . . .
C26 C 1.1842(2) 0.37734(14) 0.3451(2) 0.0535(5) Uani 1 1 d . . .
H26 H 1.2454 0.3744 0.2993 0.064 Uiso 1 1 calc R . .
C27 C 0.9037(2) 0.38910(14) 0.5590(2) 0.0529(5) Uani 1 1 d . . .
H27A H 0.9126 0.3386 0.6043 0.063 Uiso 1 1 calc R . .
H27B H 0.8145 0.3923 0.5155 0.063 Uiso 1 1 calc R . .
H27C H 0.9217 0.4389 0.6052 0.063 Uiso 1 1 calc R . .
C28 C 1.0502(2) 0.37038(15) 0.3027(2) 0.0575(6) Uani 1 1 d . . .
H28 H 1.0198 0.3639 0.2270 0.069 Uiso 1 1 calc R . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C9 1.379(2) . ?
F2 C9 1.357(2) . ?
O3 C6 1.227(2) . ?
N4 C6 1.345(2) . ?
N4 C5 1.417(2) . ?
N4 H4 0.8600 . ?
C5 C11 1.396(2) . ?
C5 C14 1.407(2) . ?
C6 C9 1.533(2) . ?
C7 C17 1.391(2) . ?
C7 C19 1.393(2) . ?
C7 H7 0.9300 . ?
C8 C10 1.387(2) . ?
C8 C18 1.398(2) . ?
C8 H8 0.9300 . ?
C9 C20 1.488(2) . ?
C10 C17 1.395(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.379(2) . ?
C11 H11 0.9300 . ?
C12 C21 1.389(3) . ?
C12 H12 0.9300 . ?
C13 C17 1.508(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.403(2) . ?
C14 C16 1.481(2) . ?
C15 C21 1.382(2) . ?
C15 H15 0.9300 . ?
C16 C20 1.346(2) . ?
C16 C18 1.491(2) . ?
C18 C19 1.392(2) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C24 1.382(3) . ?
C22 C25 1.397(3) . ?
C22 H22 0.9300 . ?
C23 C28 1.381(3) . ?
C23 C25 1.392(3) . ?
C23 H23 0.9300 . ?
C24 C26 1.385(3) . ?
C24 H24 0.9300 . ?
C25 C27 1.491(3) . ?
C26 C28 1.367(3) . ?
C26 H26 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28 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
C6 N4 C5 130.31(14) . . ?
C6 N4 H4 114.8 . . ?
C5 N4 H4 114.8 . . ?
C11 C5 C14 120.47(15) . . ?
C11 C5 N4 115.62(14) . . ?
C14 C5 N4 123.74(15) . . ?
O3 C6 N4 123.09(15) . . ?
O3 C6 C9 120.78(15) . . ?
N4 C6 C9 116.09(14) . . ?
C17 C7 C19 121.10(16) . . ?
C17 C7 H7 119.5 . . ?
C19 C7 H7 119.5 . . ?
C10 C8 C18 120.90(16) . . ?
C10 C8 H8 119.5 . . ?
C18 C8 H8 119.5 . . ?
F2 C9 F1 106.11(13) . . ?
F2 C9 C20 110.41(14) . . ?
F1 C9 C20 112.36(13) . . ?
F2 C9 C6 108.42(13) . . ?
F1 C9 C6 108.19(14) . . ?
C20 C9 C6 111.14(14) . . ?
C8 C10 C17 120.80(16) . . ?
C8 C10 H10 119.6 . . ?
C17 C10 H10 119.6 . . ?
C12 C11 C5 120.82(16) . . ?
C12 C11 H11 119.6 . . ?
C5 C11 H11 119.6 . . ?
C11 C12 C21 119.70(16) . . ?
C11 C12 H12 120.2 . . ?
C21 C12 H12 120.2 . . ?
C17 C13 H13A 109.5 . . ?
C17 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C17 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C5 117.09(15) . . ?
C15 C14 C16 119.34(14) . . ?
C5 C14 C16 123.51(15) . . ?
C21 C15 C14 122.25(15) . . ?
C21 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
C20 C16 C14 123.14(15) . . ?
C20 C16 C18 119.70(15) . . ?
C14 C16 C18 117.15(14) . . ?
C7 C17 C10 118.26(15) . . ?
C7 C17 C13 121.50(16) . . ?
C10 C17 C13 120.23(16) . . ?
C19 C18 C8 118.34(15) . . ?
C19 C18 C16 121.57(15) . . ?
C8 C18 C16 120.04(15) . . ?
C18 C19 C7 120.57(16) . . ?
C18 C19 H19 119.7 . . ?
C7 C19 H19 119.7 . . ?
C16 C20 C9 123.18(16) . . ?
C16 C20 H20 118.4 . . ?
C9 C20 H20 118.4 . . ?
C15 C21 C12 119.59(16) . . ?
C15 C21 H21 120.2 . . ?
C12 C21 H21 120.2 . . ?
C24 C22 C25 119.9(2) . . ?
C24 C22 H22 120.0 . . ?
C25 C22 H22 120.0 . . ?
C28 C23 C25 121.50(19) . . ?
C28 C23 H23 119.2 . . ?
C25 C23 H23 119.2 . . ?
C22 C24 C26 121.7(2) . . ?
C22 C24 H24 119.1 . . ?
C26 C24 H24 119.1 . . ?
C23 C25 C22 117.6(2) . . ?
C23 C25 C27 122.04(19) . . ?
C22 C25 C27 120.3(2) . . ?
C28 C26 C24 118.4(2) . . ?
C28 C26 H26 120.8 . . ?
C24 C26 H26 120.8 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 C23 120.7(2) . . ?
C26 C28 H28 119.6 . . ?
C23 C28 H28 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N4 C5 C11 -145.70(17) . . . . ?
C6 N4 C5 C14 38.9(3) . . . . ?
C5 N4 C6 O3 -179.31(16) . . . . ?
C5 N4 C6 C9 -1.6(3) . . . . ?
O3 C6 C9 F2 -6.8(2) . . . . ?
N4 C6 C9 F2 175.47(14) . . . . ?
O3 C6 C9 F1 -121.43(17) . . . . ?
N4 C6 C9 F1 60.80(18) . . . . ?
O3 C6 C9 C20 114.76(18) . . . . ?
N4 C6 C9 C20 -63.01(19) . . . . ?
C18 C8 C10 C17 -0.8(3) . . . . ?
C14 C5 C11 C12 -1.6(3) . . . . ?
N4 C5 C11 C12 -177.17(15) . . . . ?
C5 C11 C12 C21 -0.9(3) . . . . ?
C11 C5 C14 C15 2.8(2) . . . . ?
N4 C5 C14 C15 177.96(15) . . . . ?
C11 C5 C14 C16 -174.39(16) . . . . ?
N4 C5 C14 C16 0.8(3) . . . . ?
C5 C14 C15 C21 -1.6(2) . . . . ?
C16 C14 C15 C21 175.69(15) . . . . ?
C15 C14 C16 C20 145.36(16) . . . . ?
C5 C14 C16 C20 -37.5(2) . . . . ?
C15 C14 C16 C18 -35.4(2) . . . . ?
C5 C14 C16 C18 141.68(16) . . . . ?
C19 C7 C17 C10 1.3(3) . . . . ?
C19 C7 C17 C13 -178.08(16) . . . . ?
C8 C10 C17 C7 -0.6(3) . . . . ?
C8 C10 C17 C13 178.78(16) . . . . ?
C10 C8 C18 C19 1.5(3) . . . . ?
C10 C8 C18 C16 -175.95(16) . . . . ?
C20 C16 C18 C19 -39.6(2) . . . . ?
C14 C16 C18 C19 141.16(16) . . . . ?
C20 C16 C18 C8 137.81(17) . . . . ?
C14 C16 C18 C8 -41.4(2) . . . . ?
C8 C18 C19 C7 -0.8(3) . . . . ?
C16 C18 C19 C7 176.60(16) . . . . ?
C17 C7 C19 C18 -0.6(3) . . . . ?
C14 C16 C20 C9 -0.8(3) . . . . ?
C18 C16 C20 C9 -179.98(14) . . . . ?
F2 C9 C20 C16 -174.29(15) . . . . ?
F1 C9 C20 C16 -56.0(2) . . . . ?
C6 C9 C20 C16 65.4(2) . . . . ?
C14 C15 C21 C12 -0.8(3) . . . . ?
C11 C12 C21 C15 2.1(3) . . . . ?
C25 C22 C24 C26 0.8(3) . . . . ?
C28 C23 C25 C22 -1.0(3) . . . . ?
C28 C23 C25 C27 179.1(2) . . . . ?
C24 C22 C25 C23 -0.3(3) . . . . ?
C24 C22 C25 C27 179.52(18) . . . . ?
C22 C24 C26 C28 0.1(3) . . . . ?
C24 C26 C28 C23 -1.5(3) . . . . ?
C25 C23 C28 C26 2.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N4 H4 O3 . . 3_666 2.8591(18) 0.860 2.010 169.1 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
