# Electronic Supplementary Material (ESI) for Molecular Systems Design & Engineering.
# This journal is © The Royal Society of Chemistry 2022

#\#CIF_1.1
 
#  CIF produced by WinGX routine CIF_UPDATE
#  Created on 2021-09-06 at 15:24:51
#  Using CIFtbx version 3.0.4  1 Sep 2006
 
#  Dictionary name : cif_core.dic
#  Dictionary vers : 2.4.3
#  Request file    : c:\program files (x86)\wingx\files\archive.reqdat
#  CIF files read  : BPF1a
 
#------------------ SECTION 1. GLOBAL INFORMATION ---------------------------#
 
data_global
 
#------------------ AUDIT DETAILS -------------------------------------------#
 
_audit_creation_date            2021-09-06
_audit_creation_method          'WinGX routine CIF_UPDATE'
_audit_conform_dict_name        cif_core.dic
_audit_conform_dict_version     2.4
_audit_conform_dict_location    ftp://ftp.iucr.org/pub/cif_core.dic
_audit_update_record            ?
 
#==============================================================================
#
# SUBMISSION DETAILS
# Name and address of author for correspondence
 
_publ_contact_author_name       ' ,  '
_publ_contact_author_address
;
 
;
_publ_contact_author_email       ' '
_publ_contact_author_fax         ' '
_publ_contact_author_phone       ' '
 
 
_publ_contact_letter
;
 Submission dated :2021-09-06
 
Please consider this CIF for submission to the Cambridge Crystallographic
Data Centre. I certify that all authors have seen and approved of this
submission, that all have made significant scientific contributions to the
work reported, and that all share responsibility and accountability for
the results.
 
This CIF  is submitted as a personal communication
 
This CIF is submitted as part of a journal submission
<Insert Journal details here>
 
<Insert NAME here>
;
 
 
#==============================================================================
#
# TITLE AND AUTHOR LIST
 
_publ_section_title
; ?
;
_publ_section_title_footnote
; ?
;
 
# The loop structure below should contain the names and addresses of all
# authors, in the required order of publication. Repeat as necessary.
 
loop_
 _publ_author_name
 _publ_author_footnote
 _publ_author_address
?
?
;?
;
 
#------------------  SECTION 2. COMPOUND(S) DETAILS -------------------------#
 
data_BPF1a
 
_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
