# Electronic Supplementary Material (ESI) for Molecular Systems Design & Engineering.
# 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_BPF1a
_database_code_depnum_ccdc_archive 'CCDC 2163090'
loop_
_audit_author_name
_audit_author_address
'Magali Allain'
;MOLTECH Anjou, University of Angers
France
;
_audit_update_record             
;
2022-03-29 deposited with the CCDC.	2022-05-26 downloaded from the CCDC.
;

_audit_creation_date             2021-09-06T15:24:51-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C17 H6 F5 N O'
_chemical_formula_sum            'C17 H6 F5 N O'
_chemical_formula_weight         335.23
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.2934(2)
_cell_length_b                   7.4260(2)
_cell_length_c                   28.4033(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1327.42(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    200.00(10)
_cell_measurement_reflns_used    2658
_cell_measurement_theta_min      3.092
_cell_measurement_theta_max      71.822

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.293
_exptl_crystal_size_mid          0.194
_exptl_crystal_size_min          0.046
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_F_000             672

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.356
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.7325
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      200.00(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_detector_area_resol_mean 5.199
_diffrn_measurement_device_type  'SuperNova, Single source at offset, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0103
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_number            3348
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.112
_diffrn_reflns_theta_max         71.949
_diffrn_reflns_theta_full        70
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.99
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.858
_diffrn_reflns_point_group_measured_fraction_max 0.839
_reflns_Friedel_fraction_full    0.664
_reflns_Friedel_fraction_max     0.642
_reflns_Friedel_coverage         0.449
_reflns_number_total             2179
_reflns_number_gt                2155
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'DIAMOND 3.2k (Crystal Impact GbR, 2014)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0465P)²+0.2021P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2179
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0286
_refine_ls_wR_factor_ref         0.076
_refine_ls_wR_factor_gt          0.0757
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 662 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(6)
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.042

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.1788(4) 0.4660(3) 0.62401(8) 0.0336(4) Uani 1 1 d . . . . .
H1 H 0.060013 0.420202 0.639364 0.04 Uiso 1 1 calc R U . . .
C2 C 0.1894(4) 0.4786(3) 0.57529(8) 0.0402(5) Uani 1 1 d . . . . .
H2 H 0.074451 0.440189 0.557336 0.048 Uiso 1 1 calc R U . . .
C3 C 0.3691(4) 0.5478(3) 0.55260(7) 0.0401(5) Uani 1 1 d . . . . .
H3 H 0.370524 0.555094 0.519912 0.048 Uiso 1 1 calc R U . . .
C4 C 0.5451(4) 0.6057(3) 0.57783(7) 0.0352(5) Uani 1 1 d . . . . .
H4 H 0.664818 0.650088 0.562545 0.042 Uiso 1 1 calc R U . . .
C5 C 0.5369(3) 0.5951(2) 0.62719(7) 0.0275(4) Uani 1 1 d . . . . .
C6 C 0.3546(3) 0.5253(2) 0.64814(7) 0.0271(4) Uani 1 1 d . . . . .
C7 C 0.6782(3) 0.6381(2) 0.66508(6) 0.0272(4) Uani 1 1 d . . . . .
H7 H 0.813538 0.687576 0.662602 0.033 Uiso 1 1 calc R U . . .
C8 C 0.5762(3) 0.5927(2) 0.70501(6) 0.0252(4) Uani 1 1 d . . . . .
C9 C 0.6410(3) 0.6021(2) 0.75422(6) 0.0252(4) Uani 1 1 d . . . . .
C10 C 0.8519(3) 0.6723(3) 0.76128(6) 0.0282(4) Uani 1 1 d . . . . .
C11 C 0.5123(3) 0.5585(2) 0.79017(7) 0.0269(4) Uani 1 1 d . . . . .
H11 H 0.373049 0.527962 0.782612 0.032 Uiso 1 1 calc R U . . .
C12 C 0.5700(3) 0.5542(2) 0.84031(6) 0.0256(4) Uani 1 1 d . . . . .
C13 C 0.7595(3) 0.4829(2) 0.85740(7) 0.0273(4) Uani 1 1 d . . . . .
C14 C 0.8051(4) 0.4748(3) 0.90483(7) 0.0310(4) Uani 1 1 d . . . . .
C15 C 0.6592(4) 0.5371(3) 0.93708(7) 0.0338(5) Uani 1 1 d . . . . .
C16 C 0.4678(4) 0.6056(3) 0.92182(7) 0.0320(4) Uani 1 1 d . . . . .
C17 C 0.4257(3) 0.6122(3) 0.87412(7) 0.0282(4) Uani 1 1 d . . . . .
N1 N 1.0166(3) 0.7364(3) 0.76622(6) 0.0382(4) Uani 1 1 d . . . . .
O1 O 0.3775(2) 0.52276(18) 0.69639(5) 0.0278(3) Uani 1 1 d . . . . .
F1 F 0.2387(2) 0.67993(18) 0.86045(4) 0.0372(3) Uani 1 1 d . . . . .
F2 F 0.3254(2) 0.6650(2) 0.95294(4) 0.0461(4) Uani 1 1 d . . . . .
F3 F 0.7019(3) 0.5287(2) 0.98301(4) 0.0507(4) Uani 1 1 d . . . . .
F4 F 0.9889(2) 0.40403(19) 0.91963(5) 0.0430(3) Uani 1 1 d . . . . .
F5 F 0.9011(2) 0.41072(16) 0.82784(4) 0.0353(3) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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
C1 C6 1.374(3) . ?
C1 C2 1.389(3) . ?
C1 H1 0.93 . ?
C2 C3 1.399(4) . ?
C2 H2 0.93 . ?
C3 C4 1.388(3) . ?
C3 H3 0.93 . ?
C4 C5 1.405(3) . ?
C4 H4 0.93 . ?
C5 C6 1.393(3) . ?
C5 C7 1.433(3) . ?
C6 O1 1.378(2) . ?
C7 C8 1.346(3) . ?
C7 H7 0.93 . ?
C8 O1 1.376(2) . ?
C8 C9 1.458(2) . ?
C9 C11 1.343(3) . ?
C9 C10 1.440(3) . ?
C10 N1 1.149(3) . ?
C11 C12 1.470(2) . ?
C11 H11 0.93 . ?
C12 C17 1.390(3) . ?
C12 C13 1.392(3) . ?
C13 F5 1.337(2) . ?
C13 C14 1.379(3) . ?
C14 F4 1.338(3) . ?
C14 C15 1.377(3) . ?
C15 F3 1.333(2) . ?
C15 C16 1.378(3) . ?
C16 F2 1.334(2) . ?
C16 C17 1.381(3) . ?
C17 F1 1.338(2) . ?

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 C1 C2 115.9(2) . . ?
C6 C1 H1 122 . . ?
C2 C1 H1 122 . . ?
C1 C2 C3 121.5(2) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C4 C3 C2 121.4(2) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 117.9(2) . . ?
C3 C4 H4 121 . . ?
C5 C4 H4 121 . . ?
C6 C5 C4 118.5(2) . . ?
C6 C5 C7 105.88(17) . . ?
C4 C5 C7 135.6(2) . . ?
C1 C6 O1 125.2(2) . . ?
C1 C6 C5 124.71(19) . . ?
O1 C6 C5 110.12(17) . . ?
C8 C7 C5 106.30(18) . . ?
C8 C7 H7 126.9 . . ?
C5 C7 H7 126.9 . . ?
C7 C8 O1 112.23(17) . . ?
C7 C8 C9 131.46(19) . . ?
O1 C8 C9 116.31(16) . . ?
C11 C9 C10 122.51(17) . . ?
C11 C9 C8 123.27(19) . . ?
C10 C9 C8 114.13(17) . . ?
N1 C10 C9 176.6(2) . . ?
C9 C11 C12 126.3(2) . . ?
C9 C11 H11 116.8 . . ?
C12 C11 H11 116.8 . . ?
C17 C12 C13 115.89(17) . . ?
C17 C12 C11 120.07(18) . . ?
C13 C12 C11 123.90(18) . . ?
F5 C13 C14 117.23(19) . . ?
F5 C13 C12 120.31(17) . . ?
C14 C13 C12 122.38(19) . . ?
F4 C14 C15 119.95(18) . . ?
F4 C14 C13 120.3(2) . . ?
C15 C14 C13 119.8(2) . . ?
F3 C15 C14 120.1(2) . . ?
F3 C15 C16 120.1(2) . . ?
C14 C15 C16 119.84(18) . . ?
F2 C16 C15 120.07(19) . . ?
F2 C16 C17 120.6(2) . . ?
C15 C16 C17 119.30(19) . . ?
F1 C17 C16 117.82(18) . . ?
F1 C17 C12 119.39(17) . . ?
C16 C17 C12 122.8(2) . . ?
C8 O1 C6 105.48(15) . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_BPF3a
_database_code_depnum_ccdc_archive 'CCDC 2163091'
loop_
_audit_author_name
_audit_author_address
'Magali Allain' 'MOLTECH Anjou, University of Angers'
_audit_update_record             
;
2022-03-29 deposited with the CCDC.	2022-05-26 downloaded from the CCDC.
;

_audit_creation_date             2022-03-09T09:37:56-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C18 H10 F3 N O'
_chemical_formula_sum            'C18 H10 F3 N O'
_chemical_formula_weight         313.27

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.4098(3)
_cell_length_b                   7.2975(5)
_cell_length_c                   15.8052(8)
_cell_angle_alpha                84.237(5)
_cell_angle_beta                 81.645(4)
_cell_angle_gamma                79.261(5)
_cell_volume                     716.59(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    25E1(4)
_cell_measurement_reflns_used    2691
_cell_measurement_theta_min      5.679
_cell_measurement_theta_max      71.682

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.297
_exptl_crystal_size_mid          0.201
_exptl_crystal_size_min          0.054
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_F_000             320

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.004
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.41.118a (Rigaku Oxford Diffraction, 2021)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.68518
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      25E1(4)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_detector_area_resol_mean 5.199
_diffrn_measurement_device_type  'SuperNova, Single source at offset, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.03
_diffrn_reflns_number            4815
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.834
_diffrn_reflns_theta_max         83.888
_diffrn_reflns_theta_full        70
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.831
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.831
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.831
_reflns_Friedel_coverage         0
_reflns_number_total             2682
_reflns_number_gt                2243
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'DIAMOND 3.2k (Crystal Impact GbR, 2014)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0791P)²+0.2748P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2682
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_ref         0.1625
_refine_ls_wR_factor_gt          0.1405
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.057

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.2449(4) 0.2542(3) 1.06423(15) 0.0501(6) Uani 1 1 d . . . . .
C2 C 0.3098(4) 0.2390(3) 0.97010(14) 0.0422(5) Uani 1 1 d . . . . .
C3 C 0.5049(4) 0.2818(3) 0.93151(15) 0.0481(5) Uani 1 1 d . . . . .
H3 H 0.597635 0.317363 0.964377 0.058 Uiso 1 1 calc R U . . .
C4 C 0.5614(4) 0.2717(3) 0.84440(15) 0.0468(5) Uani 1 1 d . . . . .
H4 H 0.693681 0.29837 0.819063 0.056 Uiso 1 1 calc R U . . .
C5 C 0.4230(3) 0.2220(3) 0.79358(13) 0.0394(5) Uani 1 1 d . . . . .
C6 C 0.2275(3) 0.1772(3) 0.83362(14) 0.0422(5) Uani 1 1 d . . . . .
H6 H 0.134242 0.141041 0.801191 0.051 Uiso 1 1 calc R U . . .
C7 C 0.1725(4) 0.1865(3) 0.92095(14) 0.0432(5) Uani 1 1 d . . . . .
H7 H 0.041866 0.15708 0.946967 0.052 Uiso 1 1 calc R U . . .
C8 C 0.4900(3) 0.2153(3) 0.70111(14) 0.0413(5) Uani 1 1 d . . . . .
H8 H 0.635682 0.177384 0.684307 0.05 Uiso 1 1 calc R U . . .
C9 C 0.3664(3) 0.2574(3) 0.63758(13) 0.0381(5) Uani 1 1 d . . . . .
C10 C 0.1393(3) 0.3235(3) 0.65371(14) 0.0437(5) Uani 1 1 d . . . . .
C11 C 0.4489(3) 0.2526(3) 0.54706(13) 0.0376(5) Uani 1 1 d . . . . .
C12 C 0.3557(3) 0.3081(3) 0.47557(14) 0.0417(5) Uani 1 1 d . . . . .
H12 H 0.212377 0.359307 0.472924 0.05 Uiso 1 1 calc R U . . .
C13 C 0.5204(3) 0.2731(3) 0.40406(14) 0.0399(5) Uani 1 1 d . . . . .
C14 C 0.7059(3) 0.1964(3) 0.44013(13) 0.0387(5) Uani 1 1 d . . . . .
C15 C 0.9030(4) 0.1437(3) 0.39264(15) 0.0474(5) Uani 1 1 d . . . . .
H15 H 1.024175 0.091583 0.418436 0.057 Uiso 1 1 calc R U . . .
C16 C 0.9098(4) 0.1728(3) 0.30493(15) 0.0505(6) Uani 1 1 d . . . . .
H16 H 1.039431 0.140491 0.270418 0.061 Uiso 1 1 calc R U . . .
C17 C 0.7274(4) 0.2495(3) 0.26651(15) 0.0504(6) Uani 1 1 d . . . . .
H17 H 0.738258 0.267625 0.207053 0.06 Uiso 1 1 calc R U . . .
C18 C 0.5305(4) 0.2991(3) 0.31497(15) 0.0477(5) Uani 1 1 d . . . . .
H18 H 0.408803 0.348223 0.289002 0.057 Uiso 1 1 calc R U . . .
N1 N -0.0404(3) 0.3794(3) 0.66416(15) 0.0598(6) Uani 1 1 d . . . . .
O1 O 0.6646(2) 0.1829(2) 0.52813(9) 0.0417(4) Uani 1 1 d . . . . .
F1 F 0.1260(3) 0.1277(3) 1.09922(10) 0.0820(6) Uani 1 1 d . . . . .
F2 F 0.4102(3) 0.2281(3) 1.10881(10) 0.0832(6) Uani 1 1 d . . . . .
F3 F 0.1337(3) 0.4206(2) 1.08194(11) 0.0828(6) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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
C1 F3 1.323(3) . ?
C1 F2 1.330(3) . ?
C1 F1 1.332(3) . ?
C1 C2 1.495(3) . ?
C2 C7 1.382(3) . ?
C2 C3 1.385(3) . ?
C3 C4 1.378(3) . ?
C3 H3 0.93 . ?
C4 C5 1.396(3) . ?
C4 H4 0.93 . ?
C5 C6 1.399(3) . ?
C5 C8 1.465(3) . ?
C6 C7 1.379(3) . ?
C6 H6 0.93 . ?
C7 H7 0.93 . ?
C8 C9 1.345(3) . ?
C8 H8 0.93 . ?
C9 C10 1.439(3) . ?
C9 C11 1.453(3) . ?
C10 N1 1.142(3) . ?
C11 C12 1.346(3) . ?
C11 O1 1.381(2) . ?
C12 C13 1.438(3) . ?
C12 H12 0.93 . ?
C13 C14 1.391(3) . ?
C13 C18 1.396(3) . ?
C14 O1 1.375(2) . ?
C14 C15 1.382(3) . ?
C15 C16 1.377(3) . ?
C15 H15 0.93 . ?
C16 C17 1.394(4) . ?
C16 H16 0.93 . ?
C17 C18 1.384(3) . ?
C17 H17 0.93 . ?
C18 H18 0.93 . ?

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
F3 C1 F2 105.6(2) . . ?
F3 C1 F1 107.1(2) . . ?
F2 C1 F1 105.2(2) . . ?
F3 C1 C2 112.3(2) . . ?
F2 C1 C2 113.4(2) . . ?
F1 C1 C2 112.6(2) . . ?
C7 C2 C3 119.8(2) . . ?
C7 C2 C1 119.9(2) . . ?
C3 C2 C1 120.3(2) . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 H3 120 . . ?
C2 C3 H3 120 . . ?
C3 C4 C5 121.0(2) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 118.4(2) . . ?
C4 C5 C8 118.79(19) . . ?
C6 C5 C8 122.8(2) . . ?
C7 C6 C5 120.3(2) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C2 120.5(2) . . ?
C6 C7 H7 119.7 . . ?
C2 C7 H7 119.7 . . ?
C9 C8 C5 127.84(19) . . ?
C9 C8 H8 116.1 . . ?
C5 C8 H8 116.1 . . ?
C8 C9 C10 122.3(2) . . ?
C8 C9 C11 123.87(18) . . ?
C10 C9 C11 113.74(19) . . ?
N1 C10 C9 177.9(3) . . ?
C12 C11 O1 111.74(18) . . ?
C12 C11 C9 132.19(19) . . ?
O1 C11 C9 116.05(17) . . ?
C11 C12 C13 106.76(18) . . ?
C11 C12 H12 126.6 . . ?
C13 C12 H12 126.6 . . ?
C14 C13 C18 119.1(2) . . ?
C14 C13 C12 105.32(19) . . ?
C18 C13 C12 135.6(2) . . ?
O1 C14 C15 125.6(2) . . ?
O1 C14 C13 110.62(18) . . ?
C15 C14 C13 123.7(2) . . ?
C16 C15 C14 116.2(2) . . ?
C16 C15 H15 121.9 . . ?
C14 C15 H15 121.9 . . ?
C15 C16 C17 121.7(2) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 H16 119.1 . . ?
C18 C17 C16 121.4(2) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 C13 117.9(2) . . ?
C17 C18 H18 121.1 . . ?
C13 C18 H18 121.1 . . ?
C14 O1 C11 105.56(15) . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_BPF3b
_database_code_depnum_ccdc_archive 'CCDC 2164117'
loop_
_audit_author_name
_audit_author_address
'Magali Allain'
;MOLTECH Anjou, University of Angers
France
;
_audit_update_record             
;
2022-04-03 deposited with the CCDC.	2022-05-26 downloaded from the CCDC.
;

_audit_creation_date             2016-06-28T09:54:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#------------------ CHEMICAL INFORMATION ------------------------------------#

_chemical_formula_moiety         'C18 H10 F3 N1 O1'
_chemical_formula_sum            'C18 H10 F3 N O'
_chemical_formula_weight         313.27

#------------------ UNIT CELL INFORMATION -----------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7868(5)
_cell_length_b                   8.5364(8)
_cell_length_c                   13.0400(10)
_cell_angle_alpha                86.970(7)
_cell_angle_beta                 86.932(7)
_cell_angle_gamma                78.760(7)
_cell_volume                     739.22(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5616
_cell_measurement_theta_min      3.76
_cell_measurement_theta_max      27.5

#------------------ CRYSTAL INFORMATION -------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.17
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.764
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   
;
 '(SADABS (Sheldrick, Bruker, 2008))'
;

#------------------ DATA COLLECTION INFORMATION -----------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            18618
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.76
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_full        27.5
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_reflns_number_total             3347
_reflns_number_gt                2308
_reflns_threshold_expression     >2sigma(I)

#------------------ COMPUTER PROGRAMS USED ----------------------------------#

_computing_data_collection       'Collect (Hooft, 2008)'
_computing_cell_refinement       'Dirax (Duisenberg, 1992)'
_computing_data_reduction        'EvalCCD (Duisenberg et al., 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'DIAMOND 3.2k (Crystal Impact GbR, 2014)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#------------------ REFINEMENT INFORMATION ----------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1246P)²+0.3563P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3347
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1066
_refine_ls_R_factor_gt           0.0764
_refine_ls_wR_factor_gt          0.2139
_refine_ls_wR_factor_ref         0.2478
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0
_refine_diff_density_max         0.761
_refine_diff_density_min         -0.405

#------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
_atom_site_disorder_assembly
C1 C 0.3822(4) 0.4208(3) 0.64870(18) 0.0499(6) Uani 1 d . . .
C2 C 0.2081(5) 0.5034(3) 0.6959(2) 0.0665(8) Uani 1 d . . .
H2 H 0.0818 0.5061 0.6707 0.08 Uiso 1 calc R . .
C3 C 0.2337(6) 0.5816(4) 0.7828(2) 0.0783(10) Uani 1 d . . .
H3 H 0.1213 0.6372 0.8182 0.094 Uiso 1 calc R . .
C4 C 0.4237(6) 0.5793(4) 0.8187(2) 0.0798(10) Uani 1 d . . .
H4 H 0.4348 0.6328 0.8778 0.096 Uiso 1 calc R . .
C5 C 0.5947(5) 0.5004(4) 0.7694(2) 0.0728(9) Uani 1 d . . .
H5 H 0.721 0.5008 0.7938 0.087 Uiso 1 calc R . .
C6 C 0.5740(4) 0.4186(3) 0.68093(19) 0.0541(6) Uani 1 d . . .
C7 C 0.7069(4) 0.3259(3) 0.6081(2) 0.0561(6) Uani 1 d . . .
H7 H 0.8466 0.3032 0.6079 0.067 Uiso 1 calc R . .
C8 C 0.5907(4) 0.2775(3) 0.53952(18) 0.0472(6) Uani 1 d . . .
C9 C 0.6507(3) 0.1829(3) 0.45170(18) 0.0465(5) Uani 1 d . . .
H9 H 0.7887 0.1564 0.4377 0.056 Uiso 1 calc R . .
C10 C 0.5359(3) 0.1263(3) 0.38592(17) 0.0438(5) Uani 1 d . . .
C11 C 0.3210(4) 0.1584(3) 0.4004(2) 0.0518(6) Uani 1 d . . .
C12 C 0.6199(3) 0.0291(3) 0.29746(17) 0.0438(5) Uani 1 d . . .
C13 C 0.8255(4) -0.0260(3) 0.2833(2) 0.0603(7) Uani 1 d . . .
H13 H 0.9119 -0.0057 0.3318 0.072 Uiso 1 calc R . .
C14 C 0.9036(4) -0.1104(4) 0.1983(2) 0.0639(7) Uani 1 d . . .
H14 H 1.0419 -0.1449 0.1897 0.077 Uiso 1 calc R . .
C15 C 0.7784(5) -0.1441(3) 0.1257(2) 0.0579(7) Uani 1 d . . .
C16 C 0.5739(5) -0.0949(4) 0.1407(2) 0.0680(8) Uani 1 d . . .
H16 H 0.4882 -0.1191 0.0931 0.082 Uiso 1 calc R . .
C17 C 0.4944(4) -0.0097(3) 0.2255(2) 0.0599(7) Uani 1 d . . .
H17 H 0.3558 0.022 0.2347 0.072 Uiso 1 calc R . .
C18 C 0.8632(6) -0.2293(4) 0.0318(2) 0.0757(9) Uani 1 d . . .
F1 F 1.0318(5) -0.3236(5) 0.0441(2) 0.1778(18) Uani 1 d . . .
F2 F 0.8813(5) -0.1318(3) -0.04747(17) 0.1376(12) Uani 1 d . . .
F3 F 0.7463(5) -0.3198(4) -0.0032(2) 0.1494(13) Uani 1 d . . .
N1 N 0.1495(4) 0.1766(4) 0.4089(2) 0.0799(8) Uani 1 d . . .
O1 O 0.3895(2) 0.3345(2) 0.56188(13) 0.0500(5) Uani 1 d . . .



#------------------ 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
C1 O1 1.377(3) . ?
C1 C2 1.384(4) . ?
C1 C6 1.385(4) . ?
C2 C3 1.380(5) . ?
C2 H2 0.93 . ?
C3 C4 1.391(5) . ?
C3 H3 0.93 . ?
C4 C5 1.370(5) . ?
C4 H4 0.93 . ?
C5 C6 1.407(4) . ?
C5 H5 0.93 . ?
C6 C7 1.433(4) . ?
C7 C8 1.354(3) . ?
C7 H7 0.93 . ?
C8 O1 1.378(3) . ?
C8 C9 1.431(3) . ?
C9 C10 1.356(3) . ?
C9 H9 0.93 . ?
C10 C11 1.435(3) . ?
C10 C12 1.480(3) . ?
C11 N1 1.144(3) . ?
C12 C13 1.389(3) . ?
C12 C17 1.394(3) . ?
C13 C14 1.379(4) . ?
C13 H13 0.93 . ?
C14 C15 1.383(4) . ?
C14 H14 0.93 . ?
C15 C16 1.376(4) . ?
C15 C18 1.488(4) . ?
C16 C17 1.382(4) . ?
C16 H16 0.93 . ?
C17 H17 0.93 . ?
C18 F1 1.277(4) . ?
C18 F2 1.308(4) . ?
C18 F3 1.323(5) . ?

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
O1 C1 C2 125.0(3) . . ?
O1 C1 C6 110.8(2) . . ?
C2 C1 C6 124.2(3) . . ?
C3 C2 C1 115.8(3) . . ?
C3 C2 H2 122.1 . . ?
C1 C2 H2 122.1 . . ?
C2 C3 C4 121.6(3) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 121.8(3) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 118.1(3) . . ?
C4 C5 H5 121 . . ?
C6 C5 H5 121 . . ?
C1 C6 C5 118.5(3) . . ?
C1 C6 C7 105.3(2) . . ?
C5 C6 C7 136.2(3) . . ?
C8 C7 C6 107.1(2) . . ?
C8 C7 H7 126.5 . . ?
C6 C7 H7 126.5 . . ?
C7 C8 O1 111.1(2) . . ?
C7 C8 C9 129.0(2) . . ?
O1 C8 C9 119.8(2) . . ?
C10 C9 C8 129.5(2) . . ?
C10 C9 H9 115.3 . . ?
C8 C9 H9 115.3 . . ?
C9 C10 C11 120.3(2) . . ?
C9 C10 C12 123.5(2) . . ?
C11 C10 C12 116.3(2) . . ?
N1 C11 C10 176.2(3) . . ?
C13 C12 C17 117.9(2) . . ?
C13 C12 C10 121.3(2) . . ?
C17 C12 C10 120.9(2) . . ?
C14 C13 C12 121.0(3) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 120.7(3) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 118.9(2) . . ?
C16 C15 C18 120.5(3) . . ?
C14 C15 C18 120.6(3) . . ?
C15 C16 C17 120.8(3) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C16 C17 C12 120.7(3) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?
F1 C18 F2 108.9(4) . . ?
F1 C18 F3 104.7(3) . . ?
F2 C18 F3 101.8(3) . . ?
F1 C18 C15 113.9(3) . . ?
F2 C18 C15 112.8(3) . . ?
F3 C18 C15 113.8(3) . . ?
C1 O1 C8 105.68(18) . . ?

_chemical_properties_physical    Light-sensitive
####################################################################### 
# 
# 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_BPF2a
_database_code_depnum_ccdc_archive 'CCDC 2164116'
loop_
_audit_author_name
_audit_author_address
'Magali Allain'
;MOLTECH Anjou, University of Angers
France
;
_audit_update_record             
;
2022-04-03 deposited with the CCDC.	2022-05-26 downloaded from the CCDC.
;

_audit_creation_date             2016-07-06T12:12:26-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#------------------ CHEMICAL INFORMATION ------------------------------------#

_chemical_formula_moiety         'C17 H6 Br F4 N O'
_chemical_formula_sum            'C17 H6 Br F4 N O'
_chemical_formula_weight         396.14

#------------------ UNIT CELL INFORMATION -----------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.292(2)
_cell_length_b                   7.628(2)
_cell_length_c                   30.394(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.960(10)
_cell_angle_gamma                90
_cell_volume                     1456.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5884
_cell_measurement_theta_min      3.79
_cell_measurement_theta_max      28

#------------------ CRYSTAL INFORMATION -------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.376
_exptl_crystal_size_mid          0.179
_exptl_crystal_size_min          0.087
_exptl_crystal_density_diffrn    1.806
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    2.871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.448
_exptl_absorpt_correction_T_max  0.779
_exptl_absorpt_process_details   
;
 '(SADABS (Sheldrick, Bruker, 2008))'
;

#------------------ DATA COLLECTION INFORMATION -----------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            12588
_diffrn_reflns_av_R_equivalents  0.041
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         3.79
_diffrn_reflns_theta_max         28
_diffrn_reflns_theta_full        26
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measured_fraction_theta_full 0.985
_reflns_number_total             3321
_reflns_number_gt                2093
_reflns_threshold_expression     >2sigma(I)

#------------------ COMPUTER PROGRAMS USED ----------------------------------#

_computing_data_collection       'Collect (Hooft, 2008)'
_computing_cell_refinement       'Dirax (Duisenberg, 1992)'
_computing_data_reduction        'EvalCCD (Duisenberg et al., 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'DIAMOND 3.2k (Crystal Impact GbR, 2014)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#------------------ REFINEMENT INFORMATION ----------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0361P)²+1.3981P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3321
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.1124
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.605

#------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
_atom_site_disorder_assembly
C1 C -0.1780(5) 0.8164(4) 0.15824(9) 0.0379(7) Uani 1 d . . .
C2 C -0.3601(6) 0.8774(5) 0.13615(10) 0.0502(8) Uani 1 d . . .
H2 H -0.4725 0.9253 0.1508 0.06 Uiso 1 calc R . .
C3 C -0.3649(7) 0.8628(5) 0.09049(11) 0.0580(10) Uani 1 d . . .
H3 H -0.4839 0.9027 0.074 0.07 Uiso 1 calc R . .
C4 C -0.1971(7) 0.7903(5) 0.06883(11) 0.0611(10) Uani 1 d . . .
H4 H -0.2066 0.7818 0.0383 0.073 Uiso 1 calc R . .
C5 C -0.0160(6) 0.7304(5) 0.09177(10) 0.0542(9) Uani 1 d . . .
H5 H 0.096 0.6824 0.077 0.065 Uiso 1 calc R . .
C6 C -0.0054(5) 0.7439(4) 0.13788(9) 0.0408(7) Uani 1 d . . .
C7 C 0.1487(5) 0.7002(4) 0.17267(9) 0.0420(7) Uani 1 d . . .
H7 H 0.2811 0.6485 0.1698 0.05 Uiso 1 calc R . .
C8 C 0.0616(5) 0.7496(4) 0.21064(9) 0.0375(7) Uani 1 d . . .
C9 C 0.1428(5) 0.7416(4) 0.25635(9) 0.0374(7) Uani 1 d . . .
C10 C 0.3562(5) 0.6736(4) 0.26195(9) 0.0408(7) Uani 1 d . . .
C11 C 0.0249(5) 0.7834(4) 0.29065(9) 0.0387(7) Uani 1 d . . .
H11 H -0.1165 0.8133 0.2842 0.046 Uiso 1 calc R . .
C12 C 0.0989(5) 0.7861(4) 0.33736(9) 0.0371(7) Uani 1 d . . .
C13 C 0.2905(5) 0.8559(4) 0.35322(9) 0.0394(7) Uani 1 d . . .
C14 C 0.3516(5) 0.8601(4) 0.39741(10) 0.0453(8) Uani 1 d . . .
C15 C 0.2176(6) 0.7943(5) 0.42818(9) 0.0520(9) Uani 1 d . . .
C16 C 0.0251(6) 0.7267(5) 0.41364(9) 0.0494(8) Uani 1 d . . .
C17 C -0.0347(5) 0.7241(4) 0.36934(10) 0.0428(7) Uani 1 d . . .
Br1 Br 0.30191(8) 0.79666(8) 0.488056(11) 0.0928(2) Uani 1 d . . .
F1 F 0.4233(3) 0.9308(3) 0.32504(6) 0.0551(5) Uani 1 d . . .
F2 F 0.5396(3) 0.9321(3) 0.41008(6) 0.0656(6) Uani 1 d . . .
F3 F -0.1116(4) 0.6624(3) 0.44260(6) 0.0735(7) Uani 1 d . . .
F4 F -0.2291(3) 0.6541(2) 0.35715(5) 0.0475(5) Uani 1 d . . .
N1 N 0.5215(5) 0.6122(4) 0.26560(9) 0.0580(8) Uani 1 d . . .
O1 O -0.1378(3) 0.8214(3) 0.20326(6) 0.0410(5) Uani 1 d . . .



#------------------ 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
C1 C2 1.379(4) . ?
C1 O1 1.379(3) . ?
C1 C6 1.392(4) . ?
C2 C3 1.391(5) . ?
C2 H2 0.93 . ?
C3 C4 1.388(6) . ?
C3 H3 0.93 . ?
C4 C5 1.382(5) . ?
C4 H4 0.93 . ?
C5 C6 1.404(4) . ?
C5 H5 0.93 . ?
C6 C7 1.436(4) . ?
C7 C8 1.356(4) . ?
C7 H7 0.93 . ?
C8 O1 1.377(4) . ?
C8 C9 1.457(4) . ?
C9 C11 1.348(4) . ?
C9 C10 1.442(5) . ?
C10 N1 1.141(4) . ?
C11 C12 1.471(4) . ?
C11 H11 0.93 . ?
C12 C13 1.381(4) . ?
C12 C17 1.400(4) . ?
C13 F1 1.354(3) . ?
C13 C14 1.378(4) . ?
C14 F2 1.343(4) . ?
C14 C15 1.385(5) . ?
C15 C16 1.368(5) . ?
C15 Br1 1.869(3) . ?
C16 F3 1.354(4) . ?
C16 C17 1.379(4) . ?
C17 F4 1.368(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
C2 C1 O1 125.4(3) . . ?
C2 C1 C6 124.4(3) . . ?
O1 C1 C6 110.2(3) . . ?
C1 C2 C3 115.7(3) . . ?
C1 C2 H2 122.2 . . ?
C3 C2 H2 122.2 . . ?
C4 C3 C2 121.8(3) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C5 C4 C3 121.3(3) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 118.4(3) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C1 C6 C5 118.4(3) . . ?
C1 C6 C7 106.1(2) . . ?
C5 C6 C7 135.5(3) . . ?
C8 C7 C6 105.9(3) . . ?
C8 C7 H7 127 . . ?
C6 C7 H7 127 . . ?
C7 C8 O1 112.1(2) . . ?
C7 C8 C9 131.5(3) . . ?
O1 C8 C9 116.3(2) . . ?
C11 C9 C10 122.7(3) . . ?
C11 C9 C8 123.2(3) . . ?
C10 C9 C8 114.0(3) . . ?
N1 C10 C9 176.6(4) . . ?
C9 C11 C12 126.2(3) . . ?
C9 C11 H11 116.9 . . ?
C12 C11 H11 116.9 . . ?
C13 C12 C17 115.6(3) . . ?
C13 C12 C11 124.7(3) . . ?
C17 C12 C11 119.6(3) . . ?
F1 C13 C14 117.2(3) . . ?
F1 C13 C12 119.9(2) . . ?
C14 C13 C12 122.9(3) . . ?
F2 C14 C13 119.1(3) . . ?
F2 C14 C15 120.8(3) . . ?
C13 C14 C15 120.0(3) . . ?
C16 C15 C14 118.5(3) . . ?
C16 C15 Br1 121.3(3) . . ?
C14 C15 Br1 120.1(3) . . ?
F3 C16 C15 120.5(3) . . ?
F3 C16 C17 118.6(3) . . ?
C15 C16 C17 120.9(3) . . ?
F4 C17 C16 117.7(3) . . ?
F4 C17 C12 120.3(3) . . ?
C16 C17 C12 121.9(3) . . ?
C8 O1 C1 105.6(2) . . ?

_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_BPF1b
_database_code_depnum_ccdc_archive 'CCDC 2164115'
loop_
_audit_author_name
_audit_author_address
'Magali Allain'
;MOLTECH Anjou, University of Angers
France
;
_audit_update_record             
;
2022-04-03 deposited with the CCDC.	2022-05-26 downloaded from the CCDC.
;

_audit_creation_date             2016-02-23T15:06:06-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#------------------ CHEMICAL INFORMATION ------------------------------------#

_chemical_formula_moiety         'C17 H6 F5 N1 O1'
_chemical_formula_sum            'C17 H6 F5 N O'
_chemical_formula_weight         335.23

#------------------ UNIT CELL INFORMATION -----------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_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                   6.8261(4)
_cell_length_b                   28.701(2)
_cell_length_c                   6.9455(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.958(7)
_cell_angle_gamma                90
_cell_volume                     1331.21(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    200.0(1)
_cell_measurement_reflns_used    2395
_cell_measurement_theta_min      6.711
_cell_measurement_theta_max      76.015

#------------------ CRYSTAL INFORMATION -------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.3866
_exptl_crystal_size_mid          0.0529
_exptl_crystal_size_min          0.035
_exptl_crystal_density_diffrn    1.673
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    1.352
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.81104
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
        (compiled Dec  9 2014,15:38:47)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

#------------------ DATA COLLECTION INFORMATION -----------------------------#

_diffrn_ambient_temperature      200.0(1)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Single source at offset, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.199
_diffrn_reflns_number            5905
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         6.17
_diffrn_reflns_theta_max         76.21
_diffrn_reflns_theta_full        74
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.98
_reflns_number_total             2695
_reflns_number_gt                2253
_reflns_threshold_expression     >2sigma(I)

#------------------ COMPUTER PROGRAMS USED ----------------------------------#

_computing_data_collection       
'CrysAlisPro, Agilent Technologies, V1.171.37.35g'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies, V1.171.37.35g'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies, V1.171.37.35g'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'DIAMOND 3.2k (Crystal Impact GbR, 2014)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#------------------ REFINEMENT INFORMATION ----------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0781P)²+0.5577P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2695
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.063
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_gt          0.1453
_refine_ls_wR_factor_ref         0.1546
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.278

#------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
_atom_site_disorder_assembly
C1 C 0.9216(3) -0.11936(8) 0.7110(3) 0.0350(5) Uani 1 d . . .
C2 C 0.7785(3) -0.15426(9) 0.6708(4) 0.0428(5) Uani 1 d . . .
H2 H 0.6426 -0.1477 0.6316 0.051 Uiso 1 calc R . .
C3 C 0.8508(4) -0.19934(9) 0.6927(4) 0.0480(6) Uani 1 d . . .
H3 H 0.761 -0.2241 0.6674 0.058 Uiso 1 calc R . .
C4 C 1.0539(4) -0.20871(9) 0.7515(4) 0.0492(6) Uani 1 d . . .
H4 H 1.0968 -0.2395 0.7652 0.059 Uiso 1 calc R . .
C5 C 1.1934(4) -0.17353(9) 0.7899(4) 0.0451(5) Uani 1 d . . .
H5 H 1.3291 -0.1802 0.8295 0.054 Uiso 1 calc R . .
C6 C 1.1259(3) -0.12735(8) 0.7680(3) 0.0363(5) Uani 1 d . . .
C7 C 1.2184(3) -0.08243(8) 0.7893(3) 0.0377(5) Uani 1 d . . .
H7 H 1.3548 -0.0761 0.8246 0.045 Uiso 1 calc R . .
C8 C 1.0694(3) -0.05112(8) 0.7483(3) 0.0366(5) Uani 1 d . . .
C9 C 1.0805(3) -0.00049(8) 0.7496(3) 0.0356(5) Uani 1 d . . .
H9 H 1.2058 0.0123 0.7498 0.043 Uiso 1 calc R . .
C10 C 0.9307(3) 0.03030(8) 0.7507(3) 0.0335(4) Uani 1 d . . .
C11 C 0.7326(3) 0.01362(8) 0.7560(3) 0.0376(5) Uani 1 d . . .
C12 C 0.9608(3) 0.08146(7) 0.7563(3) 0.0335(4) Uani 1 d . . .
C13 C 0.8032(3) 0.11238(8) 0.6912(3) 0.0364(5) Uani 1 d . . .
C14 C 0.8269(3) 0.16005(8) 0.6973(3) 0.0404(5) Uani 1 d . . .
C15 C 1.0127(4) 0.17904(8) 0.7651(3) 0.0399(5) Uani 1 d . . .
C16 C 1.1737(3) 0.15015(9) 0.8298(3) 0.0403(5) Uani 1 d . . .
C17 C 1.1468(3) 0.10243(8) 0.8268(3) 0.0360(5) Uani 1 d . . .
N1 N 0.5766(3) 0.00095(8) 0.7672(4) 0.0544(6) Uani 1 d . . .
O1 O 0.8845(2) -0.07216(5) 0.6999(2) 0.0388(4) Uani 1 d . . .
F1 F 0.61916(19) 0.09648(5) 0.6148(2) 0.0494(4) Uani 1 d . . .
F2 F 0.6687(2) 0.18764(5) 0.6327(3) 0.0544(4) Uani 1 d . . .
F3 F 1.0377(2) 0.22544(5) 0.7680(3) 0.0560(4) Uani 1 d . . .
F4 F 1.3549(2) 0.16831(6) 0.8953(3) 0.0560(4) Uani 1 d . . .
F5 F 1.30885(19) 0.07699(5) 0.9006(2) 0.0483(4) Uani 1 d . . .



#------------------ 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
C1 O1 1.378(3) . ?
C1 C2 1.386(3) . ?
C1 C6 1.388(3) . ?
C2 C3 1.382(4) . ?
C2 H2 0.93 . ?
C3 C4 1.388(4) . ?
C3 H3 0.93 . ?
C4 C5 1.375(4) . ?
C4 H4 0.93 . ?
C5 C6 1.401(3) . ?
C5 H5 0.93 . ?
C6 C7 1.430(3) . ?
C7 C8 1.343(3) . ?
C7 H7 0.93 . ?
C8 O1 1.377(3) . ?
C8 C9 1.455(3) . ?
C9 C10 1.353(3) . ?
C9 H9 0.93 . ?
C10 C11 1.442(3) . ?
C10 C12 1.482(3) . ?
C11 N1 1.143(3) . ?
C12 C13 1.396(3) . ?
C12 C17 1.398(3) . ?
C13 F1 1.338(2) . ?
C13 C14 1.377(3) . ?
C14 F2 1.339(3) . ?
C14 C15 1.371(3) . ?
C15 F3 1.342(3) . ?
C15 C16 1.376(3) . ?
C16 F4 1.333(3) . ?
C16 C17 1.381(3) . ?
C17 F5 1.336(2) . ?

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
O1 C1 C2 125.8(2) . . ?
O1 C1 C6 109.92(19) . . ?
C2 C1 C6 124.2(2) . . ?
C3 C2 C1 115.7(2) . . ?
C3 C2 H2 122.2 . . ?
C1 C2 H2 122.2 . . ?
C2 C3 C4 121.7(2) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 121.6(2) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 118.4(2) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C1 C6 C5 118.4(2) . . ?
C1 C6 C7 106.1(2) . . ?
C5 C6 C7 135.5(2) . . ?
C8 C7 C6 106.42(19) . . ?
C8 C7 H7 126.8 . . ?
C6 C7 H7 126.8 . . ?
C7 C8 O1 111.99(19) . . ?
C7 C8 C9 129.1(2) . . ?
O1 C8 C9 118.91(19) . . ?
C10 C9 C8 127.9(2) . . ?
C10 C9 H9 116.1 . . ?
C8 C9 H9 116.1 . . ?
C9 C10 C11 119.8(2) . . ?
C9 C10 C12 123.12(19) . . ?
C11 C10 C12 116.99(18) . . ?
N1 C11 C10 177.5(3) . . ?
C13 C12 C17 115.0(2) . . ?
C13 C12 C10 121.86(19) . . ?
C17 C12 C10 123.13(19) . . ?
F1 C13 C14 116.47(19) . . ?
F1 C13 C12 120.6(2) . . ?
C14 C13 C12 122.9(2) . . ?
F2 C14 C15 120.3(2) . . ?
F2 C14 C13 119.7(2) . . ?
C15 C14 C13 120.0(2) . . ?
F3 C15 C14 120.3(2) . . ?
F3 C15 C16 120.2(2) . . ?
C14 C15 C16 119.5(2) . . ?
F4 C16 C15 119.9(2) . . ?
F4 C16 C17 120.3(2) . . ?
C15 C16 C17 119.9(2) . . ?
F5 C17 C16 116.05(19) . . ?
F5 C17 C12 121.2(2) . . ?
C16 C17 C12 122.7(2) . . ?
C8 O1 C1 105.59(16) . . ?

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOH'
_chemical_properties_physical    Light-sensitive
####################################################################### 
# 
# 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_jg277-cycloinduit_auto
_database_code_depnum_ccdc_archive 'CCDC 2163092'
loop_
_audit_author_name
_audit_author_address
'Magali Allain' 'MOLTECH Anjou, University of Angers'
_audit_update_record             
;
2022-03-29 deposited with the CCDC.	2022-05-26 downloaded from the CCDC.
;

_audit_creation_date             2021-12-16T17:29:16-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C34 H12 F10 N2 O2, 0.75(C3 H6 O)'
_chemical_formula_sum            'C36.25 H16.50 F10 N2 O2.75'
_chemical_formula_weight         714.01

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.7298(6)
_cell_length_b                   12.3008(7)
_cell_length_c                   12.8705(9)
_cell_angle_alpha                64.625(6)
_cell_angle_beta                 88.736(5)
_cell_angle_gamma                72.512(5)
_cell_volume                     1588.00(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    6637
_cell_measurement_theta_min      4.14
_cell_measurement_theta_max      71.537

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.367
_exptl_crystal_size_mid          0.193
_exptl_crystal_size_min          0.104
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_F_000             720

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.188
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.41.118a (Rigaku Oxford Diffraction, 2021)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.86274
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_detector_area_resol_mean 5.199
_diffrn_measurement_device_type  'SuperNova, Single source at offset, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_number            12415
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.831
_diffrn_reflns_theta_max         71.847
_diffrn_reflns_theta_full        71
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.974
_reflns_Friedel_coverage         0
_reflns_number_total             6071
_reflns_number_gt                5306
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 3.2k (Crystal Impact GbR, 2014)'
_computing_publication_material  'WinGX publication routines (Farrugia, V2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0967P)²+0.3979P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6071
_refine_ls_number_parameters     487
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0547
_refine_ls_wR_factor_ref         0.1631
_refine_ls_wR_factor_gt          0.1554
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.052

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.6923(2) -0.0838(2) 0.28460(19) 0.0481(5) Uani 1 1 d . . . . .
C2 C 0.7449(2) -0.1910(2) 0.3855(2) 0.0559(5) Uani 1 1 d . . . . .
C3 C 0.6749(3) -0.2600(2) 0.4528(2) 0.0581(6) Uani 1 1 d . . . . .
C4 C 0.5545(2) -0.2203(2) 0.4161(2) 0.0542(5) Uani 1 1 d . . . . .
C5 C 0.5025(2) -0.11123(19) 0.31530(18) 0.0459(4) Uani 1 1 d . . . . .
C6 C 0.56922(19) -0.03668(19) 0.24615(17) 0.0430(4) Uani 1 1 d . . . . .
C7 C 0.52181(17) 0.09032(18) 0.13859(17) 0.0406(4) Uani 1 1 d . . . . .
C8 C 0.57946(18) 0.07886(19) 0.03936(18) 0.0436(4) Uani 1 1 d . . . . .
C9 C 0.52979(17) 0.20796(18) 0.15916(16) 0.0394(4) Uani 1 1 d . . . . .
H9 H 0.534666 0.276207 0.082371 0.047 Uiso 1 1 calc R U . . .
C10 C 0.39426(17) 0.23593(18) 0.17976(16) 0.0394(4) Uani 1 1 d . . . . .
C11 C 0.37743(18) 0.16671(19) 0.30179(17) 0.0420(4) Uani 1 1 d . . . . .
C12 C 0.38089(17) 0.15926(18) 0.11016(17) 0.0401(4) Uani 1 1 d . . . . .
H12 H 0.334598 0.09945 0.149265 0.048 Uiso 1 1 calc R U . . .
C13 C 0.33480(18) 0.24120(19) -0.01441(17) 0.0418(4) Uani 1 1 d . . . . .
C14 C 0.23841(19) 0.2547(2) -0.07869(19) 0.0457(4) Uani 1 1 d . . . . .
H14 H 0.182653 0.209082 -0.053456 0.055 Uiso 1 1 calc R U . . .
C15 C 0.2360(2) 0.3517(2) -0.19336(18) 0.0473(5) Uani 1 1 d . . . . .
C16 C 0.3349(2) 0.3887(2) -0.18857(18) 0.0480(5) Uani 1 1 d . . . . .
C17 C 0.3665(3) 0.4792(2) -0.2830(2) 0.0614(6) Uani 1 1 d . . . . .
H17 H 0.436096 0.501741 -0.277652 0.074 Uiso 1 1 calc R U . . .
C18 C 0.2908(3) 0.5347(2) -0.3850(2) 0.0661(7) Uani 1 1 d . . . . .
H18 H 0.309093 0.596855 -0.452171 0.079 Uiso 1 1 calc R U . . .
C19 C 0.1886(3) 0.5025(2) -0.3928(2) 0.0659(7) Uani 1 1 d . . . . .
H19 H 0.138009 0.543974 -0.464525 0.079 Uiso 1 1 calc R U . . .
C20 C 0.1590(2) 0.4109(2) -0.2977(2) 0.0568(5) Uani 1 1 d . . . . .
H20 H 0.089099 0.388878 -0.303035 0.068 Uiso 1 1 calc R U . . .
C21 C 0.31166(18) 0.37184(19) 0.13617(17) 0.0417(4) Uani 1 1 d . . . . .
C22 C 0.18854(19) 0.3954(2) 0.12852(19) 0.0472(5) Uani 1 1 d . . . . .
C23 C 0.1064(2) 0.5153(2) 0.0932(2) 0.0557(5) Uani 1 1 d . . . . .
C24 C 0.1474(2) 0.6173(2) 0.0621(2) 0.0581(6) Uani 1 1 d . . . . .
C25 C 0.2693(2) 0.5976(2) 0.0716(2) 0.0521(5) Uani 1 1 d . . . . .
C26 C 0.34970(19) 0.4765(2) 0.10811(18) 0.0454(4) Uani 1 1 d . . . . .
C27 C 0.62242(17) 0.19410(19) 0.24436(17) 0.0418(4) Uani 1 1 d . . . . .
C28 C 0.64429(18) 0.13755(19) 0.36066(18) 0.0438(4) Uani 1 1 d . . . . .
H28 H 0.596069 0.095787 0.413324 0.053 Uiso 1 1 calc R U . . .
C29 C 0.75440(19) 0.15217(19) 0.39032(18) 0.0447(4) Uani 1 1 d . . . . .
C30 C 0.79140(19) 0.2188(2) 0.28526(18) 0.0464(4) Uani 1 1 d . . . . .
C31 C 0.8950(2) 0.2515(3) 0.2756(2) 0.0597(6) Uani 1 1 d . . . . .
H31 H 0.918225 0.29689 0.202393 0.072 Uiso 1 1 calc R U . . .
C32 C 0.9634(2) 0.2144(3) 0.3786(2) 0.0637(6) Uani 1 1 d . . . . .
H32 H 1.035488 0.235128 0.376099 0.076 Uiso 1 1 calc R U . . .
C33 C 0.9293(2) 0.1475(3) 0.4862(2) 0.0598(6) Uani 1 1 d . . . . .
H33 H 0.978182 0.123757 0.555155 0.072 Uiso 1 1 calc R U . . .
C34 C 0.8250(2) 0.1156(2) 0.4932(2) 0.0531(5) Uani 1 1 d . . . . .
H34 H 0.801876 0.069789 0.566333 0.064 Uiso 1 1 calc R U . . .
C35A C 0.092(2) 0.8992(16) 0.184(2) 0.100(4) Uani 0.365(6) 1 d . . P A 1
H35A H 0.144634 0.93318 0.127094 0.15 Uiso 0.365(6) 1 calc R U P A 1
H35B H 0.082254 0.937565 0.237703 0.15 Uiso 0.365(6) 1 calc R U P A 1
H35C H 0.013276 0.919274 0.143521 0.15 Uiso 0.365(6) 1 calc R U P A 1
C35B C 0.077(2) 0.9537(14) 0.169(2) 0.100(4) Uani 0.385(6) 1 d . . P B 2
H35D H -0.009988 0.997437 0.158743 0.15 Uiso 0.385(6) 1 calc R U P B 2
H35E H 0.10641 0.980034 0.09272 0.15 Uiso 0.385(6) 1 calc R U P B 2
H35F H 0.118519 0.975584 0.218201 0.15 Uiso 0.385(6) 1 calc R U P B 2
C36A C 0.1487(16) 0.7553(14) 0.2512(12) 0.076(3) Uani 0.365(6) 1 d . . P A 1
C36B C 0.1000(15) 0.8157(13) 0.2227(11) 0.076(3) Uani 0.385(6) 1 d . . P B 2
C37A C 0.275(3) 0.710(4) 0.291(4) 0.091(7) Uani 0.365(6) 1 d . . P A 1
H37A H 0.304691 0.616908 0.324277 0.136 Uiso 0.365(6) 1 calc R U P A 1
H37B H 0.288003 0.736575 0.350191 0.136 Uiso 0.365(6) 1 calc R U P A 1
H37C H 0.318774 0.745269 0.225668 0.136 Uiso 0.365(6) 1 calc R U P A 1
C37B C 0.228(2) 0.735(4) 0.282(4) 0.091(7) Uani 0.385(6) 1 d . . P B 2
H37D H 0.235942 0.644512 0.312741 0.136 Uiso 0.385(6) 1 calc R U P B 2
H37E H 0.24566 0.753506 0.345279 0.136 Uiso 0.385(6) 1 calc R U P B 2
H37F H 0.285363 0.754135 0.225316 0.136 Uiso 0.385(6) 1 calc R U P B 2
N1 N 0.35918(19) 0.11541(19) 0.39484(16) 0.0544(5) Uani 1 1 d . . . . .
N2 N 0.62215(19) 0.06811(19) -0.03784(17) 0.0554(5) Uani 1 1 d . . . . .
O1 O 0.71090(13) 0.24627(15) 0.19409(12) 0.0476(3) Uani 1 1 d . . . . .
O2 O 0.39666(14) 0.32304(14) -0.07839(12) 0.0468(3) Uani 1 1 d . . . . .
O3A O 0.0876(12) 0.6887(13) 0.2674(11) 0.118(3) Uani 0.365(6) 1 d . . P A 1
O3B O 0.0256(12) 0.7645(13) 0.2234(11) 0.118(3) Uani 0.385(6) 1 d . . P B 2
F1 F 0.76399(11) -0.02123(13) 0.22010(13) 0.0576(3) Uani 1 1 d . . . . .
F2 F 0.86243(14) -0.22880(15) 0.41968(15) 0.0734(4) Uani 1 1 d . . . . .
F3 F 0.72343(18) -0.36235(14) 0.55257(13) 0.0775(5) Uani 1 1 d . . . . .
F4 F 0.48506(16) -0.28690(14) 0.48033(13) 0.0714(4) Uani 1 1 d . . . . .
F5 F 0.38340(12) -0.07944(12) 0.28868(11) 0.0543(3) Uani 1 1 d . . . . .
F6 F 0.46717(12) 0.46293(12) 0.11727(12) 0.0549(3) Uani 1 1 d . . . . .
F7 F 0.30970(15) 0.69533(13) 0.04824(13) 0.0658(4) Uani 1 1 d . . . . .
F8 F 0.06904(17) 0.73479(14) 0.02284(17) 0.0824(5) Uani 1 1 d . . . . .
F9 F -0.01154(13) 0.53209(15) 0.08975(16) 0.0733(4) Uani 1 1 d . . . . .
F10 F 0.14556(11) 0.29731(12) 0.15847(13) 0.0565(3) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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
C1 F1 1.341(3) . ?
C1 C2 1.373(3) . ?
C1 C6 1.396(3) . ?
C2 F2 1.332(3) . ?
C2 C3 1.379(4) . ?
C3 F3 1.332(3) . ?
C3 C4 1.369(4) . ?
C4 F4 1.345(3) . ?
C4 C5 1.380(3) . ?
C5 F5 1.342(3) . ?
C5 C6 1.395(3) . ?
C6 C7 1.525(3) . ?
C7 C8 1.472(3) . ?
C7 C12 1.582(3) . ?
C7 C9 1.607(3) . ?
C8 N2 1.143(3) . ?
C9 C27 1.481(3) . ?
C9 C10 1.564(2) . ?
C9 H9 1 . ?
C10 C11 1.474(3) . ?
C10 C21 1.515(3) . ?
C10 C12 1.592(3) . ?
C11 N1 1.140(3) . ?
C12 C13 1.485(3) . ?
C12 H12 1 . ?
C13 C14 1.342(3) . ?
C13 O2 1.386(2) . ?
C14 C15 1.440(3) . ?
C14 H14 0.95 . ?
C15 C16 1.380(3) . ?
C15 C20 1.403(3) . ?
C16 O2 1.378(3) . ?
C16 C17 1.387(3) . ?
C17 C18 1.378(4) . ?
C17 H17 0.95 . ?
C18 C19 1.389(4) . ?
C18 H18 0.95 . ?
C19 C20 1.386(4) . ?
C19 H19 0.95 . ?
C20 H20 0.95 . ?
C21 C22 1.382(3) . ?
C21 C26 1.388(3) . ?
C22 F10 1.348(2) . ?
C22 C23 1.378(3) . ?
C23 F9 1.335(3) . ?
C23 C24 1.375(3) . ?
C24 F8 1.336(3) . ?
C24 C25 1.375(4) . ?
C25 F7 1.337(3) . ?
C25 C26 1.380(3) . ?
C26 F6 1.339(2) . ?
C27 C28 1.345(3) . ?
C27 O1 1.387(2) . ?
C28 C29 1.437(3) . ?
C28 H28 0.95 . ?
C29 C30 1.388(3) . ?
C29 C34 1.399(3) . ?
C30 C31 1.378(3) . ?
C30 O1 1.378(3) . ?
C31 C32 1.386(4) . ?
C31 H31 0.95 . ?
C32 C33 1.396(4) . ?
C32 H32 0.95 . ?
C33 C34 1.383(3) . ?
C33 H33 0.95 . ?
C34 H34 0.95 . ?
C35A C36A 1.527(18) . ?
C35A H35A 0.98 . ?
C35A H35B 0.98 . ?
C35A H35C 0.98 . ?
C35B C36B 1.468(14) . ?
C35B H35D 0.98 . ?
C35B H35E 0.98 . ?
C35B H35F 0.98 . ?
C36A O3A 1.194(19) . ?
C36A C37A 1.44(3) . ?
C36B O3B 1.218(18) . ?
C36B C37B 1.53(3) . ?
C37A H37A 0.98 . ?
C37A H37B 0.98 . ?
C37A H37C 0.98 . ?
C37B H37D 0.98 . ?
C37B H37E 0.98 . ?
C37B H37F 0.98 . ?

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
F1 C1 C2 117.6(2) . . ?
F1 C1 C6 118.61(19) . . ?
C2 C1 C6 123.7(2) . . ?
F2 C2 C1 120.9(2) . . ?
F2 C2 C3 119.6(2) . . ?
C1 C2 C3 119.4(2) . . ?
F3 C3 C4 120.7(2) . . ?
F3 C3 C2 120.4(2) . . ?
C4 C3 C2 118.9(2) . . ?
F4 C4 C3 119.6(2) . . ?
F4 C4 C5 119.4(2) . . ?
C3 C4 C5 121.0(2) . . ?
F5 C5 C4 116.12(18) . . ?
F5 C5 C6 121.75(19) . . ?
C4 C5 C6 122.1(2) . . ?
C5 C6 C1 114.74(19) . . ?
C5 C6 C7 127.37(19) . . ?
C1 C6 C7 117.84(17) . . ?
C8 C7 C6 109.15(16) . . ?
C8 C7 C12 113.49(17) . . ?
C6 C7 C12 118.19(15) . . ?
C8 C7 C9 114.87(15) . . ?
C6 C7 C9 112.99(16) . . ?
C12 C7 C9 86.86(14) . . ?
N2 C8 C7 178.1(2) . . ?
C27 C9 C10 120.95(16) . . ?
C27 C9 C7 122.59(17) . . ?
C10 C9 C7 88.45(13) . . ?
C27 C9 H9 107.7 . . ?
C10 C9 H9 107.7 . . ?
C7 C9 H9 107.7 . . ?
C11 C10 C21 107.34(16) . . ?
C11 C10 C9 113.04(16) . . ?
C21 C10 C9 120.12(15) . . ?
C11 C10 C12 109.58(15) . . ?
C21 C10 C12 117.68(16) . . ?
C9 C10 C12 88.00(13) . . ?
N1 C11 C10 177.1(2) . . ?
C13 C12 C7 115.70(16) . . ?
C13 C12 C10 113.78(16) . . ?
C7 C12 C10 88.36(14) . . ?
C13 C12 H12 112.3 . . ?
C7 C12 H12 112.3 . . ?
C10 C12 H12 112.3 . . ?
C14 C13 O2 111.66(18) . . ?
C14 C13 C12 131.24(17) . . ?
O2 C13 C12 117.06(16) . . ?
C13 C14 C15 106.65(18) . . ?
C13 C14 H14 126.7 . . ?
C15 C14 H14 126.7 . . ?
C16 C15 C20 119.3(2) . . ?
C16 C15 C14 105.67(18) . . ?
C20 C15 C14 135.1(2) . . ?
O2 C16 C15 110.65(18) . . ?
O2 C16 C17 125.6(2) . . ?
C15 C16 C17 123.8(2) . . ?
C18 C17 C16 116.0(2) . . ?
C18 C17 H17 122 . . ?
C16 C17 H17 122 . . ?
C17 C18 C19 122.1(2) . . ?
C17 C18 H18 118.9 . . ?
C19 C18 H18 118.9 . . ?
C20 C19 C18 121.1(2) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C19 C20 C15 117.8(2) . . ?
C19 C20 H20 121.1 . . ?
C15 C20 H20 121.1 . . ?
C22 C21 C26 116.10(19) . . ?
C22 C21 C10 118.81(17) . . ?
C26 C21 C10 125.00(18) . . ?
F10 C22 C23 117.84(19) . . ?
F10 C22 C21 119.15(19) . . ?
C23 C22 C21 123.00(19) . . ?
F9 C23 C24 120.4(2) . . ?
F9 C23 C22 120.4(2) . . ?
C24 C23 C22 119.2(2) . . ?
F8 C24 C25 120.4(2) . . ?
F8 C24 C23 120.0(2) . . ?
C25 C24 C23 119.6(2) . . ?
F7 C25 C24 119.9(2) . . ?
F7 C25 C26 120.0(2) . . ?
C24 C25 C26 120.05(19) . . ?
F6 C26 C25 117.34(18) . . ?
F6 C26 C21 120.70(19) . . ?
C25 C26 C21 122.0(2) . . ?
C28 C27 O1 111.42(17) . . ?
C28 C27 C9 134.86(17) . . ?
O1 C27 C9 113.64(16) . . ?
C27 C28 C29 107.09(17) . . ?
C27 C28 H28 126.5 . . ?
C29 C28 H28 126.5 . . ?
C30 C29 C34 119.00(19) . . ?
C30 C29 C28 105.35(18) . . ?
C34 C29 C28 135.6(2) . . ?
C31 C30 O1 125.6(2) . . ?
C31 C30 C29 123.8(2) . . ?
O1 C30 C29 110.65(17) . . ?
C30 C31 C32 116.2(2) . . ?
C30 C31 H31 121.9 . . ?
C32 C31 H31 121.9 . . ?
C31 C32 C33 121.9(2) . . ?
C31 C32 H32 119.1 . . ?
C33 C32 H32 119.1 . . ?
C34 C33 C32 120.7(2) . . ?
C34 C33 H33 119.7 . . ?
C32 C33 H33 119.7 . . ?
C33 C34 C29 118.5(2) . . ?
C33 C34 H34 120.8 . . ?
C29 C34 H34 120.8 . . ?
C36A C35A H35A 109.5 . . ?
C36A C35A H35B 109.5 . . ?
H35A C35A H35B 109.5 . . ?
C36A C35A H35C 109.5 . . ?
H35A C35A H35C 109.5 . . ?
H35B C35A H35C 109.5 . . ?
C36B C35B H35D 109.5 . . ?
C36B C35B H35E 109.5 . . ?
H35D C35B H35E 109.5 . . ?
C36B C35B H35F 109.5 . . ?
H35D C35B H35F 109.5 . . ?
H35E C35B H35F 109.5 . . ?
O3A C36A C37A 125(2) . . ?
O3A C36A C35A 119.6(17) . . ?
C37A C36A C35A 116(2) . . ?
O3B C36B C35B 124.9(18) . . ?
O3B C36B C37B 119.8(18) . . ?
C35B C36B C37B 115(2) . . ?
C36A C37A H37A 109.5 . . ?
C36A C37A H37B 109.5 . . ?
H37A C37A H37B 109.5 . . ?
C36A C37A H37C 109.5 . . ?
H37A C37A H37C 109.5 . . ?
H37B C37A H37C 109.5 . . ?
C36B C37B H37D 109.5 . . ?
C36B C37B H37E 109.5 . . ?
H37D C37B H37E 109.5 . . ?
C36B C37B H37F 109.5 . . ?
H37D C37B H37F 109.5 . . ?
H37E C37B H37F 109.5 . . ?
C30 O1 C27 105.48(15) . . ?
C16 O2 C13 105.36(15) . . ?

