# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_arb_2a_auto
_database_code_depnum_ccdc_archive 'CCDC 2215386'
loop_
_audit_author_name
_audit_author_address
'Matija Gredicak'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2022-10-26 deposited with the CCDC.	2023-03-28 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H20 F2 N2 O'
_chemical_formula_sum            'C31 H19 F2 N O'
_chemical_formula_weight         459.47
_chemical_absolute_configuration R
_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 0.0181 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'
F F 0.0727 0.0534 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.43750(10)
_cell_length_b                   14.8172(2)
_cell_length_c                   21.9398(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2417.83(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8467
_cell_measurement_temperature    295(2)
_cell_measurement_theta_min      3.5850
_cell_measurement_theta_max      79.3310
_exptl_absorpt_coefficient_mu    0.707
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needles
_exptl_crystal_F_000             952
_exptl_crystal_size_min          ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_number            11789
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_min         3.600
_diffrn_reflns_theta_max         79.655
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  XtaLab
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.623
_reflns_Friedel_fraction_full    0.902
_reflns_Friedel_fraction_max     0.813
_reflns_number_gt                4459
_reflns_number_total             4787
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_computing_structure_solution    
;
SHELXT, Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.
;
_refine_diff_density_min         -0.128
_refine_diff_density_max         0.141
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details 
;
 Flack x determined using 1644 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(8)
_refine_ls_extinction_coef       0.0026(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4787
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0324
_refine_ls_restrained_S_all      1.051
_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)+(0.0495P)²+0.1205P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0882
_refine_ls_wR_factor_ref         0.0902
_refine_special_details          ?
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
N14 N 0.4460(2) 0.37158(9) 0.35179(6) 0.0425(3) Uani 1 1 d . . . . .
H14 H 0.420003 0.315448 0.347174 0.051 Uiso 1 1 calc R U . . .
O35 O 0.6091(3) 0.68289(9) 0.16923(6) 0.0653(4) Uani 1 1 d . . . . .
N9 N 0.5831(2) 0.63561(9) 0.26871(7) 0.0460(3) Uani 1 1 d . . . . .
H9 H 0.478952 0.658731 0.275568 0.055 Uiso 1 1 calc R U . . .
F34 F 0.7732(3) 0.88147(9) 0.40687(9) 0.1058(7) Uani 1 1 d . . . . .
F33 F 0.9544(3) 0.62651(14) 0.51473(7) 0.1069(7) Uani 1 1 d . . . . .
C13 C 0.5662(2) 0.41805(10) 0.31654(7) 0.0383(3) Uani 1 1 d . . . . .
C12 C 0.5721(2) 0.50534(10) 0.33866(7) 0.0384(3) Uani 1 1 d . . . . .
C2 C 0.8485(2) 0.55822(10) 0.27862(8) 0.0394(3) Uani 1 1 d . . . . .
C1 C 0.6822(2) 0.58430(10) 0.31519(8) 0.0387(3) Uani 1 1 d . . . . .
C21 C 0.6500(2) 0.37268(10) 0.26391(8) 0.0405(3) Uani 1 1 d . . . . .
C7 C 0.8389(3) 0.59503(10) 0.22073(8) 0.0450(4) Uani 1 1 d . . . . .
C8 C 0.6669(3) 0.64375(10) 0.21474(8) 0.0464(4) Uani 1 1 d . . . . .
C27 C 0.7410(3) 0.64598(11) 0.36791(8) 0.0438(4) Uani 1 1 d . . . . .
C10 C 0.3727(3) 0.42655(11) 0.39549(8) 0.0440(4) Uani 1 1 d . . . . .
C11 C 0.4496(3) 0.50981(11) 0.38819(8) 0.0450(4) Uani 1 1 d . . . . .
H11 H 0.425711 0.560650 0.411686 0.054 Uiso 1 1 calc R U . . .
C32 C 0.7263(3) 0.73903(12) 0.36379(10) 0.0537(5) Uani 1 1 d . . . . .
H32 H 0.675828 0.765837 0.329498 0.064 Uiso 1 1 calc R U . . .
C3 C 0.9959(3) 0.50703(12) 0.29541(9) 0.0493(4) Uani 1 1 d . . . . .
H3 H 1.004114 0.481959 0.334174 0.059 Uiso 1 1 calc R U . . .
C15 C 0.2313(3) 0.39547(11) 0.43714(9) 0.0490(4) Uani 1 1 d . . . . .
C22 C 0.6241(3) 0.40566(13) 0.20558(9) 0.0520(4) Uani 1 1 d . . . . .
H22 H 0.557010 0.457914 0.199812 0.062 Uiso 1 1 calc R U . . .
C26 C 0.7492(3) 0.29410(12) 0.27119(11) 0.0547(5) Uani 1 1 d . . . . .
H26 H 0.768295 0.270731 0.310002 0.066 Uiso 1 1 calc R U . . .
C28 C 0.8179(3) 0.60749(14) 0.41949(9) 0.0548(5) Uani 1 1 d . . . . .
H28 H 0.828371 0.545192 0.423207 0.066 Uiso 1 1 calc R U . . .
C4 C 1.1307(3) 0.49423(15) 0.25290(12) 0.0645(6) Uani 1 1 d . . . . .
H4 H 1.230716 0.459857 0.263344 0.077 Uiso 1 1 calc R U . . .
C31 C 0.7879(4) 0.79096(14) 0.41138(12) 0.0689(7) Uani 1 1 d . . . . .
C20 C 0.2132(4) 0.43396(16) 0.49430(10) 0.0702(6) Uani 1 1 d . . . . .
H20 H 0.292634 0.479000 0.506422 0.084 Uiso 1 1 calc R U . . .
C30 C 0.8643(4) 0.75613(17) 0.46270(11) 0.0758(7) Uani 1 1 d . . . . .
H30 H 0.904588 0.792714 0.494312 0.091 Uiso 1 1 calc R U . . .
C6 C 0.9740(3) 0.58248(15) 0.17814(10) 0.0627(5) Uani 1 1 d . . . . .
H6 H 0.965997 0.607684 0.139414 0.075 Uiso 1 1 calc R U . . .
C29 C 0.8782(4) 0.66405(18) 0.46494(10) 0.0699(6) Uani 1 1 d . . . . .
C16 C 0.1119(4) 0.32864(15) 0.42057(11) 0.0659(6) Uani 1 1 d . . . . .
H16 H 0.121676 0.301569 0.382469 0.079 Uiso 1 1 calc R U . . .
C25 C 0.8200(3) 0.25031(15) 0.22071(14) 0.0725(7) Uani 1 1 d . . . . .
H25 H 0.886139 0.197608 0.225945 0.087 Uiso 1 1 calc R U . . .
C24 C 0.7937(4) 0.28370(19) 0.16356(13) 0.0775(8) Uani 1 1 d . . . . .
H24 H 0.841069 0.253689 0.129969 0.093 Uiso 1 1 calc R U . . .
C23 C 0.6971(4) 0.36168(18) 0.15567(10) 0.0709(6) Uani 1 1 d . . . . .
H23 H 0.680650 0.385083 0.116741 0.085 Uiso 1 1 calc R U . . .
C5 C 1.1203(4) 0.53153(17) 0.19496(12) 0.0721(6) Uani 1 1 d . . . . .
H5 H 1.213034 0.521977 0.167286 0.087 Uiso 1 1 calc R U . . .
C18 C -0.0384(5) 0.3403(2) 0.51683(14) 0.0913(9) Uani 1 1 d . . . . .
H18 H -0.128250 0.321701 0.543511 0.110 Uiso 1 1 calc R U . . .
C19 C 0.0792(5) 0.4065(2) 0.53352(12) 0.0910(9) Uani 1 1 d . . . . .
H19 H 0.068792 0.433314 0.571684 0.109 Uiso 1 1 calc R U . . .
C17 C -0.0230(4) 0.3014(2) 0.46031(15) 0.0886(9) Uani 1 1 d . . . . .
H17 H -0.103282 0.256609 0.448545 0.106 Uiso 1 1 calc R U . . .


_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
N14 C13 1.368(2) . ?
N14 C10 1.371(2) . ?
O35 C8 1.232(2) . ?
N9 C1 1.470(2) . ?
N9 C8 1.344(2) . ?
F34 C31 1.349(3) . ?
F33 C29 1.351(3) . ?
C13 C12 1.382(2) . ?
C13 C21 1.474(2) . ?
C12 C1 1.518(2) . ?
C12 C11 1.420(2) . ?
C2 C1 1.524(2) . ?
C2 C7 1.384(2) . ?
C2 C3 1.383(3) . ?
C1 C27 1.538(2) . ?
C21 C22 1.383(3) . ?
C21 C26 1.388(2) . ?
C7 C8 1.474(3) . ?
C7 C6 1.385(3) . ?
C27 C32 1.386(2) . ?
C27 C28 1.390(3) . ?
C10 C11 1.369(2) . ?
C10 C15 1.467(2) . ?
C32 C31 1.376(3) . ?
C3 C4 1.383(3) . ?
C15 C20 1.384(3) . ?
C15 C16 1.379(3) . ?
C22 C23 1.385(3) . ?
C26 C25 1.387(3) . ?
C28 C29 1.377(3) . ?
C4 C5 1.388(4) . ?
C31 C30 1.363(4) . ?
C20 C19 1.378(4) . ?
C30 C29 1.369(4) . ?
C6 C5 1.375(4) . ?
C16 C17 1.389(3) . ?
C25 C24 1.362(4) . ?
C24 C23 1.371(4) . ?
C18 C19 1.364(5) . ?
C18 C17 1.372(4) . ?

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
C13 N14 C10 110.87(13) . . ?
C8 N9 C1 115.14(15) . . ?
N14 C13 C12 107.06(13) . . ?
N14 C13 C21 119.32(13) . . ?
C12 C13 C21 133.48(15) . . ?
C13 C12 C1 128.27(15) . . ?
C13 C12 C11 106.98(14) . . ?
C11 C12 C1 124.74(14) . . ?
C7 C2 C1 109.94(15) . . ?
C3 C2 C1 129.94(16) . . ?
C3 C2 C7 120.11(17) . . ?
N9 C1 C12 111.30(14) . . ?
N9 C1 C2 99.96(13) . . ?
N9 C1 C27 110.92(13) . . ?
C12 C1 C2 114.89(13) . . ?
C12 C1 C27 110.88(14) . . ?
C2 C1 C27 108.41(14) . . ?
C22 C21 C13 120.31(15) . . ?
C22 C21 C26 118.48(17) . . ?
C26 C21 C13 121.14(17) . . ?
C2 C7 C8 108.65(16) . . ?
C2 C7 C6 121.91(18) . . ?
C6 C7 C8 129.42(17) . . ?
O35 C8 N9 126.47(19) . . ?
O35 C8 C7 127.25(18) . . ?
N9 C8 C7 106.27(15) . . ?
C32 C27 C1 121.31(17) . . ?
C32 C27 C28 119.58(18) . . ?
C28 C27 C1 119.04(15) . . ?
N14 C10 C15 122.29(15) . . ?
C11 C10 N14 106.69(15) . . ?
C11 C10 C15 130.93(16) . . ?
C10 C11 C12 108.40(14) . . ?
C31 C32 C27 118.7(2) . . ?
C4 C3 C2 118.06(18) . . ?
C20 C15 C10 120.31(19) . . ?
C16 C15 C10 121.52(18) . . ?
C16 C15 C20 118.2(2) . . ?
C21 C22 C23 120.7(2) . . ?
C25 C26 C21 120.1(2) . . ?
C29 C28 C27 118.3(2) . . ?
C3 C4 C5 121.5(2) . . ?
F34 C31 C32 118.3(3) . . ?
F34 C31 C30 118.1(2) . . ?
C30 C31 C32 123.6(2) . . ?
C19 C20 C15 120.9(2) . . ?
C31 C30 C29 116.0(2) . . ?
C5 C6 C7 117.8(2) . . ?
F33 C29 C28 118.1(2) . . ?
F33 C29 C30 118.1(2) . . ?
C30 C29 C28 123.8(2) . . ?
C15 C16 C17 120.5(2) . . ?
C24 C25 C26 120.7(2) . . ?
C25 C24 C23 119.8(2) . . ?
C24 C23 C22 120.1(2) . . ?
C6 C5 C4 120.6(2) . . ?
C19 C18 C17 119.4(2) . . ?
C18 C19 C20 120.6(2) . . ?
C18 C17 C16 120.4(3) . . ?

_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N14(H14), N9(H9), C11(H11), C32(H32), C3(H3), C22(H22), C26(H26), C28(H28),
 C4(H4), C20(H20), C30(H30), C6(H6), C16(H16), C25(H25), C24(H24), C23(H23),
 C5(H5), C18(H18), C19(H19), C17(H17)
;
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_shelx_SHELXL_version_number     2016/6
_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.
;
