# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1469162'
_audit_update_record             
;
2016-03-17 deposited with the CCDC.
2017-06-26 downloaded from the CCDC.
;
_audit_creation_date             2016-03-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H15 F2 N3 O2'
_chemical_formula_sum            'C23 H15 F2 N3 O2'
_chemical_formula_weight         403.38
_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'
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   13.178(7)
_cell_length_b                   9.598(5)
_cell_length_c                   28.580(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3615(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    ?
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.948
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_colour_lustre     ?
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             1664
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.121
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_av_unetI/netI     0.0902
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            9388
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.352
_diffrn_reflns_theta_min         3.092
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Rigaku Saturn70 diffractometer'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2183
_reflns_number_total             3267
_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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS-1997 (Sheldrick, 2008)'
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3267
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1263
_refine_ls_R_factor_gt           0.0844
_refine_ls_restrained_S_all      1.143
_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)+(0.0164P)²+3.1793P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1225
_refine_ls_wR_factor_ref         0.1441
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2A), C2(H2B), C3(H3), C4(H4), C5(H5), C8(H8), C11(H11), C13(H13),
 C15(H15), C17(H17), C19(H19), C20(H20), C22(H22), C23(H23)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.4294(2) 0.8880(3) 0.54327(12) 0.1032(11) Uani 1 1 d . . . . .
F2 F 0.7543(2) 0.7479(3) 0.49929(9) 0.0843(9) Uani 1 1 d . . . . .
O1 O 0.67042(19) -0.0139(2) 0.62989(9) 0.0449(7) Uani 1 1 d . . . . .
O2 O 1.2429(2) -0.0867(2) 0.76848(10) 0.0501(7) Uani 1 1 d . . . . .
H2 H 1.2714 -0.0317 0.7861 0.075 Uiso 1 1 calc GR . . . .
N1 N 0.4361(2) 0.3841(3) 0.58263(10) 0.0387(8) Uani 1 1 d . . . . .
N2 N 0.7595(2) 0.1811(3) 0.64609(9) 0.0343(7) Uani 1 1 d . . . . .
H2A H 0.7645 0.2701 0.6435 0.041 Uiso 1 1 calc R . . . .
N3 N 0.8362(2) 0.1046(3) 0.66647(10) 0.0361(8) Uani 1 1 d . . . . .
C1 C 0.4137(3) 0.2614(4) 0.60458(12) 0.0375(9) Uani 1 1 d . . . . .
C2 C 0.3092(3) 0.2290(4) 0.61086(14) 0.0468(11) Uani 1 1 d . . . . .
H2B H 0.2599 0.2878 0.5985 0.056 Uiso 1 1 calc R . . . .
C3 C 0.2811(3) 0.1139(4) 0.63453(14) 0.0517(11) Uani 1 1 d . . . . .
H3 H 0.2127 0.0922 0.6377 0.062 Uiso 1 1 calc R . . . .
C4 C 0.3545(3) 0.0273(4) 0.65429(15) 0.0533(12) Uani 1 1 d . . . . .
H4 H 0.3343 -0.0490 0.6721 0.064 Uiso 1 1 calc R . . . .
C5 C 0.4549(3) 0.0526(4) 0.64802(14) 0.0461(10) Uani 1 1 d . . . . .
H5 H 0.5025 -0.0075 0.6611 0.055 Uiso 1 1 calc R . . . .
C6 C 0.4881(3) 0.1690(4) 0.62193(12) 0.0336(9) Uani 1 1 d . . . . .
C7 C 0.5920(3) 0.2058(3) 0.61395(11) 0.0309(8) Uani 1 1 d . . . . .
C8 C 0.6120(3) 0.3283(3) 0.59068(12) 0.0347(9) Uani 1 1 d . . . . .
H8 H 0.6789 0.3532 0.5845 0.042 Uiso 1 1 calc R . . . .
C9 C 0.5324(3) 0.4166(4) 0.57606(12) 0.0354(9) Uani 1 1 d . . . . .
C10 C 0.5543(3) 0.5557(4) 0.55518(12) 0.0383(9) Uani 1 1 d . . . . .
C11 C 0.4800(3) 0.6574(4) 0.55725(14) 0.0518(11) Uani 1 1 d . . . . .
H11 H 0.4168 0.6383 0.5702 0.062 Uiso 1 1 calc R . . . .
C12 C 0.5018(4) 0.7868(5) 0.53974(17) 0.0662(14) Uani 1 1 d . . . . .
C13 C 0.5924(4) 0.8219(4) 0.52060(16) 0.0627(14) Uani 1 1 d . . . . .
H13 H 0.6056 0.9110 0.5093 0.075 Uiso 1 1 calc R . . . .
C14 C 0.6627(3) 0.7182(5) 0.51900(14) 0.0521(11) Uani 1 1 d . . . . .
C15 C 0.6468(3) 0.5869(4) 0.53551(13) 0.0486(11) Uani 1 1 d . . . . .
H15 H 0.6975 0.5197 0.5335 0.058 Uiso 1 1 calc R . . . .
C16 C 0.6761(3) 0.1138(4) 0.63018(12) 0.0334(9) Uani 1 1 d . . . . .
C17 C 0.9167(3) 0.1703(4) 0.67703(13) 0.0379(9) Uani 1 1 d . . . . .
H17 H 0.9207 0.2649 0.6701 0.046 Uiso 1 1 calc R . . . .
C18 C 1.0031(3) 0.1032(4) 0.69950(12) 0.0348(9) Uani 1 1 d . . . . .
C19 C 1.0134(3) -0.0404(4) 0.70041(13) 0.0391(9) Uani 1 1 d . . . . .
H19 H 0.9649 -0.0959 0.6858 0.047 Uiso 1 1 calc R . . . .
C20 C 1.0947(3) -0.1019(4) 0.72269(12) 0.0394(10) Uani 1 1 d . . . . .
H20 H 1.1021 -0.1983 0.7221 0.047 Uiso 1 1 calc R . . . .
C21 C 1.1652(3) -0.0207(3) 0.74595(12) 0.0342(9) Uani 1 1 d . . . . .
C22 C 1.1561(3) 0.1222(3) 0.74455(12) 0.0352(9) Uani 1 1 d . . . . .
H22 H 1.2042 0.1776 0.7594 0.042 Uiso 1 1 calc R . . . .
C23 C 1.0766(3) 0.1829(4) 0.72139(13) 0.0389(9) Uani 1 1 d . . . . .
H23 H 1.0719 0.2796 0.7204 0.047 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 1.365(5) . ?
F2 C14 1.362(4) . ?
O1 C16 1.229(4) . ?
O2 H2 0.8200 . ?
O2 C21 1.366(4) . ?
N1 C1 1.367(4) . ?
N1 C9 1.321(4) . ?
N2 H2A 0.8600 . ?
N2 N3 1.378(4) . ?
N2 C16 1.353(4) . ?
N3 C17 1.272(4) . ?
C1 C2 1.422(5) . ?
C1 C6 1.412(5) . ?
C2 H2B 0.9300 . ?
C2 C3 1.347(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.395(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.357(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.413(5) . ?
C6 C7 1.433(5) . ?
C7 C8 1.376(4) . ?
C7 C16 1.490(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.412(5) . ?
C9 C10 1.491(5) . ?
C10 C11 1.383(5) . ?
C10 C15 1.376(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.370(5) . ?
C12 C13 1.356(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.360(6) . ?
C14 C15 1.362(5) . ?
C15 H15 0.9300 . ?
C17 H17 0.9300 . ?
C17 C18 1.457(5) . ?
C18 C19 1.385(5) . ?
C18 C23 1.384(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.379(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.383(5) . ?
C21 C22 1.377(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.370(4) . ?
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
C21 O2 H2 109.5 . . ?
C9 N1 C1 118.4(3) . . ?
N3 N2 H2A 120.5 . . ?
C16 N2 H2A 120.5 . . ?
C16 N2 N3 118.9(3) . . ?
C17 N3 N2 116.6(3) . . ?
N1 C1 C2 117.1(4) . . ?
N1 C1 C6 123.5(3) . . ?
C6 C1 C2 119.4(3) . . ?
C1 C2 H2B 119.7 . . ?
C3 C2 C1 120.6(4) . . ?
C3 C2 H2B 119.7 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.0(4) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.1(4) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.8(4) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 117.9(3) . . ?
C1 C6 C7 116.9(3) . . ?
C5 C6 C7 125.1(3) . . ?
C6 C7 C16 121.0(3) . . ?
C8 C7 C6 118.1(3) . . ?
C8 C7 C16 120.9(3) . . ?
C7 C8 H8 119.5 . . ?
C7 C8 C9 120.9(3) . . ?
C9 C8 H8 119.5 . . ?
N1 C9 C8 122.0(3) . . ?
N1 C9 C10 117.0(3) . . ?
C8 C9 C10 120.9(3) . . ?
C11 C10 C9 118.6(3) . . ?
C15 C10 C9 122.0(4) . . ?
C15 C10 C11 119.4(4) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 C10 118.4(4) . . ?
C12 C11 H11 120.8 . . ?
F1 C12 C11 118.1(5) . . ?
C13 C12 F1 117.9(4) . . ?
C13 C12 C11 123.9(5) . . ?
C12 C13 H13 122.2 . . ?
C12 C13 C14 115.6(4) . . ?
C14 C13 H13 122.2 . . ?
C13 C14 F2 117.7(4) . . ?
C13 C14 C15 124.1(4) . . ?
C15 C14 F2 118.2(4) . . ?
C10 C15 H15 120.7 . . ?
C14 C15 C10 118.6(4) . . ?
C14 C15 H15 120.7 . . ?
O1 C16 N2 121.8(3) . . ?
O1 C16 C7 123.0(3) . . ?
N2 C16 C7 115.2(3) . . ?
N3 C17 H17 118.7 . . ?
N3 C17 C18 122.5(3) . . ?
C18 C17 H17 118.7 . . ?
C19 C18 C17 121.7(3) . . ?
C23 C18 C17 120.1(3) . . ?
C23 C18 C19 118.3(3) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 C18 120.7(4) . . ?
C20 C19 H19 119.6 . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.1(3) . . ?
C21 C20 H20 119.9 . . ?
O2 C21 C20 117.9(3) . . ?
O2 C21 C22 122.7(3) . . ?
C22 C21 C20 119.3(4) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 C21 120.3(3) . . ?
C23 C22 H22 119.9 . . ?
C18 C23 H23 119.4 . . ?
C22 C23 C18 121.2(3) . . ?
C22 C23 H23 119.4 . . ?

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
F1 C12 C13 C14 178.4(4) . . . . ?
F2 C14 C15 C10 -179.5(3) . . . . ?
O2 C21 C22 C23 179.9(3) . . . . ?
N1 C1 C2 C3 -176.2(4) . . . . ?
N1 C1 C6 C5 173.8(3) . . . . ?
N1 C1 C6 C7 -2.6(5) . . . . ?
N1 C9 C10 C11 19.7(5) . . . . ?
N1 C9 C10 C15 -162.6(4) . . . . ?
N2 N3 C17 C18 178.9(3) . . . . ?
N3 N2 C16 O1 -6.1(5) . . . . ?
N3 N2 C16 C7 173.0(3) . . . . ?
N3 C17 C18 C19 16.1(6) . . . . ?
N3 C17 C18 C23 -162.7(4) . . . . ?
C1 N1 C9 C8 0.4(5) . . . . ?
C1 N1 C9 C10 -175.7(3) . . . . ?
C1 C2 C3 C4 1.8(6) . . . . ?
C1 C6 C7 C8 0.8(5) . . . . ?
C1 C6 C7 C16 -178.9(3) . . . . ?
C2 C1 C6 C5 -4.6(5) . . . . ?
C2 C1 C6 C7 179.0(3) . . . . ?
C2 C3 C4 C5 -3.6(7) . . . . ?
C3 C4 C5 C6 1.1(7) . . . . ?
C4 C5 C6 C1 2.9(6) . . . . ?
C4 C5 C6 C7 179.0(4) . . . . ?
C5 C6 C7 C8 -175.3(3) . . . . ?
C5 C6 C7 C16 5.0(6) . . . . ?
C6 C1 C2 C3 2.3(6) . . . . ?
C6 C7 C8 C9 1.4(5) . . . . ?
C6 C7 C16 O1 35.8(5) . . . . ?
C6 C7 C16 N2 -143.2(3) . . . . ?
C7 C8 C9 N1 -2.2(5) . . . . ?
C7 C8 C9 C10 173.8(3) . . . . ?
C8 C7 C16 O1 -143.9(4) . . . . ?
C8 C7 C16 N2 37.1(5) . . . . ?
C8 C9 C10 C11 -156.5(3) . . . . ?
C8 C9 C10 C15 21.3(5) . . . . ?
C9 N1 C1 C2 -179.6(3) . . . . ?
C9 N1 C1 C6 2.0(5) . . . . ?
C9 C10 C11 C12 177.4(4) . . . . ?
C9 C10 C15 C14 -177.1(3) . . . . ?
C10 C11 C12 F1 -177.9(4) . . . . ?
C10 C11 C12 C13 -0.3(7) . . . . ?
C11 C10 C15 C14 0.6(6) . . . . ?
C11 C12 C13 C14 0.9(7) . . . . ?
C12 C13 C14 F2 178.8(4) . . . . ?
C12 C13 C14 C15 -0.7(7) . . . . ?
C13 C14 C15 C10 -0.1(7) . . . . ?
C15 C10 C11 C12 -0.4(6) . . . . ?
C16 N2 N3 C17 173.8(3) . . . . ?
C16 C7 C8 C9 -178.8(3) . . . . ?
C17 C18 C19 C20 -178.7(3) . . . . ?
C17 C18 C23 C22 177.1(3) . . . . ?
C18 C19 C20 C21 2.4(6) . . . . ?
C19 C18 C23 C22 -1.8(5) . . . . ?
C19 C20 C21 O2 178.4(3) . . . . ?
C19 C20 C21 C22 -3.3(5) . . . . ?
C20 C21 C22 C23 1.7(6) . . . . ?
C21 C22 C23 C18 0.8(6) . . . . ?
C23 C18 C19 C20 0.2(6) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_original_sample_id SSB18
_olex2_submission_special_instructions 'No special instructions were received'
