# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2121453'
loop_
_audit_author_name
_audit_author_address
'Anderson Pagliari'
;UFSM
Brazil
;
_audit_update_record             
;
2021-11-11 deposited with the CCDC.	2022-06-21 downloaded from the CCDC.
;

_audit_creation_date             2021-11-10T14:55:07-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
        '2,3,4,5,6-pentafluoro-N-(perfluorophenyl)benzamide'
;
_chemical_name_common            'bispentafluor amide'
_chemical_formula_moiety         'C13 H F10 N O'
_chemical_formula_sum            'C13 H F10 N O'
_chemical_formula_weight         377.15
_chemical_melting_point          none
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   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      1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   4.7948(2)
_cell_length_b                   10.5652(5)
_cell_length_c                   12.8318(6)
_cell_angle_alpha                83.206(2)
_cell_angle_beta                 81.269(2)
_cell_angle_gamma                87.894(2)
_cell_volume                     637.87(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    7559
_cell_measurement_theta_min      2.3805
_cell_measurement_theta_max      24.9885
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.287
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.108
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.964
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368

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

_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2016/2 - Bruker AXS area detector scaling and absorption
        correction. Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M. &
        Stalke D., J. Appl. Cryst. 48 (2015) 3-10.
;
_exptl_absorpt_correction_T_min  0.7055
_exptl_absorpt_correction_T_max  0.7458
_exptl_transmission_factor_max   none
_exptl_transmission_factor_min   none
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.976

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

_diffrn_source                   'fine-focus sealed tube'
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.039
_diffrn_reflns_number            23309
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         29.141
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.931
_diffrn_reflns_point_group_measured_fraction_max 0.891
_reflns_Friedel_fraction_full    0.866
_reflns_Friedel_fraction_max     0.785
_reflns_Friedel_coverage         0.788
_reflns_number_total             6147
_reflns_number_gt                3783
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'BRUKER APEX-III'
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_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                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_special_details          none
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0689P)²+0.1542P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6147
_refine_ls_number_parameters     451
_refine_ls_number_restraints     3
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1418
_refine_ls_wR_factor_gt          0.1218
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1407 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(2)
_refine_diff_density_max         0.37
_refine_diff_density_min         -0.202
_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 0.0033 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'
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'
F F 0.0171 0.0103 '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
F7 F 1.8257(7) 0.6863(4) -0.3062(3) 0.0774(11) Uani 1 1 d . . . . .
F1 F 0.8915(8) 0.5415(3) 0.1299(3) 0.0661(9) Uani 1 1 d . . . . .
F1' F -0.5886(7) 0.3783(3) 1.1023(3) 0.0625(9) Uani 1 1 d . . . . .
F5 F 1.4142(8) 0.8451(3) 0.2542(3) 0.0740(11) Uani 1 1 d . . . . .
F2 F 0.6277(8) 0.4803(4) 0.3259(3) 0.0775(11) Uani 1 1 d . . . . .
F3 F 0.7584(9) 0.5972(5) 0.4887(3) 0.0852(12) Uani 1 1 d . . . . .
F5' F 0.0282(7) 0.0258(4) 1.1438(3) 0.0748(11) Uani 1 1 d . . . . .
F3' F -0.6446(9) 0.1237(5) 1.4256(3) 0.0874(13) Uani 1 1 d . . . . .
F6 F 1.6048(8) 0.6179(4) -0.1062(3) 0.0732(11) Uani 1 1 d . . . . .
C4 C 0.8215(12) 0.5696(5) 0.3071(5) 0.0523(15) Uani 1 1 d . . . . .
O1 O 1.5684(6) 0.7659(4) 0.0637(3) 0.0636(10) Uani 1 1 d . . . . .
F10 F 0.9408(7) 0.9571(4) -0.1283(3) 0.0718(10) Uani 1 1 d . . . . .
O1' O 0.1435(6) 0.2177(4) 0.9862(3) 0.0664(10) Uani 1 1 d . . . . .
F6' F 0.1235(8) 0.4530(4) 0.8681(3) 0.0729(10) Uani 1 1 d . . . . .
F10' F -0.4477(8) 0.1523(4) 0.7655(4) 0.0802(12) Uani 1 1 d . . . . .
F4 F 1.1593(9) 0.7768(4) 0.4518(4) 0.0883(13) Uani 1 1 d . . . . .
F9 F 1.1522(10) 1.0154(4) -0.3331(3) 0.0828(12) Uani 1 1 d . . . . .
F4' F -0.1974(9) -0.0179(4) 1.3474(3) 0.0821(12) Uani 1 1 d . . . . .
C7' C -0.1796(11) 0.1024(6) 1.1813(5) 0.0549(15) Uani 1 1 d . . . . .
C6 C 1.0909(13) 0.7193(6) 0.3715(5) 0.0576(15) Uani 1 1 d . . . . .
F8 F 1.6023(10) 0.8825(5) -0.4234(3) 0.0856(12) Uani 1 1 d . . . . .
F2' F -0.8444(7) 0.3200(4) 1.3001(3) 0.0725(11) Uani 1 1 d . . . . .
N1 N 1.1518(9) 0.7536(5) -0.0013(4) 0.0541(13) Uani 1 1 d . . . . .
H1 H 0.972891 0.742546 0.014203 0.065 Uiso 1 1 calc R U . . .
N1' N -0.2836(9) 0.2647(5) 0.9307(4) 0.0527(13) Uani 1 1 d . . . . .
H2 H -0.463872 0.266565 0.948384 0.063 Uiso 1 1 calc R U . . .
C4' C -0.6234(11) 0.2498(6) 1.2627(5) 0.0504(14) Uani 1 1 d . . . . .
F9' F -0.2335(11) 0.2192(5) 0.5613(4) 0.1078(17) Uani 1 1 d . . . . .
F7' F 0.3494(9) 0.5123(4) 0.6658(4) 0.0895(13) Uani 1 1 d . . . . .
C5' C -0.5251(13) 0.1495(6) 1.3258(5) 0.0573(16) Uani 1 1 d . . . . .
C9 C 1.4937(11) 0.7214(5) -0.1587(5) 0.0468(13) Uani 1 1 d . . . . .
C13' C -0.2510(11) 0.2433(6) 0.7397(5) 0.0568(16) Uani 1 1 d . . . . .
C2' C -0.2728(10) 0.2026(5) 1.1155(4) 0.0412(12) Uani 1 1 d . . . . .
C5 C 0.8892(12) 0.6288(6) 0.3898(5) 0.0553(16) Uani 1 1 d . . . . .
F8' F 0.1819(10) 0.3983(5) 0.5113(3) 0.1002(15) Uani 1 1 d . . . . .
C12 C 1.2642(12) 0.9186(6) -0.2756(5) 0.0538(15) Uani 1 1 d . . . . .
C1 C 1.3101(11) 0.7384(6) 0.0768(5) 0.0504(14) Uani 1 1 d . . . . .
C2 C 1.1563(10) 0.6991(5) 0.1838(4) 0.0427(12) Uani 1 1 d . . . . .
C8' C -0.1691(10) 0.2994(5) 0.8215(4) 0.0437(13) Uani 1 1 d . . . . .
C1' C -0.1248(11) 0.2299(5) 1.0056(4) 0.0442(12) Uani 1 1 d . . . . .
C8 C 1.2692(11) 0.7874(5) -0.1088(5) 0.0461(13) Uani 1 1 d . . . . .
C7 C 1.2234(10) 0.7536(6) 0.2678(5) 0.0487(14) Uani 1 1 d . . . . .
C9' C 0.0398(11) 0.3919(5) 0.7948(5) 0.0469(13) Uani 1 1 d . . . . .
C3 C 0.9606(11) 0.6051(6) 0.2076(5) 0.0482(14) Uani 1 1 d . . . . .
C3' C -0.4944(11) 0.2765(5) 1.1585(4) 0.0462(13) Uani 1 1 d . . . . .
C6' C -0.3005(13) 0.0776(6) 1.2852(5) 0.0572(16) Uani 1 1 d . . . . .
C11 C 1.4912(13) 0.8509(6) -0.3212(5) 0.0548(15) Uani 1 1 d . . . . .
C10 C 1.6070(11) 0.7533(6) -0.2624(5) 0.0537(15) Uani 1 1 d . . . . .
C12' C -0.1419(13) 0.2771(7) 0.6378(5) 0.0644(18) Uani 1 1 d . . . . .
C13 C 1.1604(10) 0.8890(5) -0.1715(4) 0.0454(13) Uani 1 1 d . . . . .
C11' C 0.0648(14) 0.3656(7) 0.6112(5) 0.0638(18) Uani 1 1 d . . . . .
C10' C 0.1519(11) 0.4216(6) 0.6888(5) 0.0569(16) 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
F7 C10 1.333(7) . ?
F1 C3 1.353(7) . ?
F1' C3' 1.326(7) . ?
F5 C7 1.333(6) . ?
F2 C4 1.324(7) . ?
F3 C5 1.338(7) . ?
F5' C7' 1.329(7) . ?
F3' C5' 1.323(7) . ?
F6 C9 1.352(7) . ?
C4 C3 1.365(9) . ?
C4 C5 1.378(9) . ?
O1 C1 1.264(6) . ?
F10 C13 1.340(6) . ?
O1' C1' 1.277(6) . ?
F6' C9' 1.319(7) . ?
F10' C13' 1.349(8) . ?
F4 C6 1.342(8) . ?
F9 C12 1.335(7) . ?
F4' C6' 1.339(7) . ?
C7' C6' 1.369(9) . ?
C7' C2' 1.380(8) . ?
C6 C5 1.361(9) . ?
C6 C7 1.397(9) . ?
F8 C11 1.346(7) . ?
F2' C4' 1.333(7) . ?
N1 C1 1.338(7) . ?
N1 C8 1.418(8) . ?
N1 H1 0.86 . ?
N1' C1' 1.325(7) . ?
N1' C8' 1.435(7) . ?
N1' H2 0.86 . ?
C4' C5' 1.370(9) . ?
C4' C3' 1.386(9) . ?
F9' C12' 1.350(8) . ?
F7' C10' 1.348(7) . ?
C5' C6' 1.368(9) . ?
C9 C10 1.367(8) . ?
C9 C8 1.376(8) . ?
C13' C12' 1.345(10) . ?
C13' C8' 1.376(9) . ?
C2' C3' 1.380(8) . ?
C2' C1' 1.480(8) . ?
F8' C11' 1.331(7) . ?
C12 C13 1.357(9) . ?
C12 C11 1.374(9) . ?
C1 C2 1.477(8) . ?
C2 C7 1.365(9) . ?
C2 C3 1.367(8) . ?
C8' C9' 1.402(8) . ?
C8 C13 1.397(8) . ?
C9' C10' 1.387(9) . ?
C11 C10 1.357(9) . ?
C12' C11' 1.365(10) . ?
C11' C10' 1.342(10) . ?

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
F2 C4 C3 122.0(6) . . ?
F2 C4 C5 119.8(5) . . ?
C3 C4 C5 118.2(5) . . ?
F5' C7' C6' 118.5(6) . . ?
F5' C7' C2' 120.0(6) . . ?
C6' C7' C2' 121.5(6) . . ?
F4 C6 C5 120.6(6) . . ?
F4 C6 C7 120.1(6) . . ?
C5 C6 C7 119.3(6) . . ?
C1 N1 C8 122.2(5) . . ?
C1 N1 H1 118.9 . . ?
C8 N1 H1 118.9 . . ?
C1' N1' C8' 123.2(4) . . ?
C1' N1' H2 118.4 . . ?
C8' N1' H2 118.4 . . ?
F2' C4' C5' 120.5(5) . . ?
F2' C4' C3' 120.0(6) . . ?
C5' C4' C3' 119.5(5) . . ?
F3' C5' C6' 120.4(6) . . ?
F3' C5' C4' 120.1(6) . . ?
C6' C5' C4' 119.5(5) . . ?
F6 C9 C10 117.2(5) . . ?
F6 C9 C8 120.1(5) . . ?
C10 C9 C8 122.7(6) . . ?
C12' C13' F10' 120.6(6) . . ?
C12' C13' C8' 122.0(6) . . ?
F10' C13' C8' 117.4(6) . . ?
C7' C2' C3' 117.2(5) . . ?
C7' C2' C1' 119.4(5) . . ?
C3' C2' C1' 123.3(5) . . ?
F3 C5 C6 119.5(6) . . ?
F3 C5 C4 120.3(6) . . ?
C6 C5 C4 120.2(5) . . ?
F9 C12 C13 120.4(6) . . ?
F9 C12 C11 119.8(6) . . ?
C13 C12 C11 119.8(6) . . ?
O1 C1 N1 123.4(5) . . ?
O1 C1 C2 120.9(5) . . ?
N1 C1 C2 115.4(5) . . ?
C7 C2 C3 116.1(5) . . ?
C7 C2 C1 118.8(5) . . ?
C3 C2 C1 125.0(6) . . ?
C13' C8' C9' 117.3(5) . . ?
C13' C8' N1' 122.8(5) . . ?
C9' C8' N1' 119.9(6) . . ?
O1' C1' N1' 123.0(5) . . ?
O1' C1' C2' 120.1(5) . . ?
N1' C1' C2' 116.9(5) . . ?
C9 C8 C13 115.7(5) . . ?
C9 C8 N1 122.4(5) . . ?
C13 C8 N1 121.9(5) . . ?
F5 C7 C2 121.3(5) . . ?
F5 C7 C6 116.7(6) . . ?
C2 C7 C6 121.9(5) . . ?
F6' C9' C10' 120.2(5) . . ?
F6' C9' C8' 121.0(5) . . ?
C10' C9' C8' 118.8(6) . . ?
F1 C3 C4 115.7(5) . . ?
F1 C3 C2 120.1(5) . . ?
C4 C3 C2 124.2(6) . . ?
F1' C3' C2' 121.2(5) . . ?
F1' C3' C4' 117.1(5) . . ?
C2' C3' C4' 121.7(6) . . ?
F4' C6' C5' 119.8(6) . . ?
F4' C6' C7' 119.6(6) . . ?
C5' C6' C7' 120.6(6) . . ?
F8 C11 C10 119.9(6) . . ?
F8 C11 C12 120.2(6) . . ?
C10 C11 C12 119.8(5) . . ?
F7 C10 C11 120.3(5) . . ?
F7 C10 C9 119.9(6) . . ?
C11 C10 C9 119.8(6) . . ?
C13' C12' F9' 119.0(7) . . ?
C13' C12' C11' 121.0(7) . . ?
F9' C12' C11' 119.9(6) . . ?
F10 C13 C12 118.8(5) . . ?
F10 C13 C8 119.0(5) . . ?
C12 C13 C8 122.2(5) . . ?
F8' C11' C10' 119.0(7) . . ?
F8' C11' C12' 122.3(7) . . ?
C10' C11' C12' 118.7(6) . . ?
C11' C10' F7' 120.6(6) . . ?
C11' C10' C9' 122.2(6) . . ?
F7' C10' C9' 117.3(6) . . ?



# END of CIF
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2121454'
loop_
_audit_author_name
_audit_author_address
'Anderson Pagliari'
;UFSM
Brazil
;
_audit_update_record             
;
2021-11-11 deposited with the CCDC.	2022-06-21 downloaded from the CCDC.
;

_audit_creation_date             2021-11-10T15:53:28-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
        '2,3,4,5,6-pentafluoro-N-(perfluorophenyl)benzamide N-phenylbenzamide'
;
_chemical_name_common            'bis-pentafluorbenzamide N-phenylbenzamide'
_chemical_formula_moiety         'C13 H F10 N O, C13 H11 N O'
_chemical_formula_sum            'C26 H12 F10 N2 O2'
_chemical_formula_weight         574.38
_chemical_melting_point          none
_chemical_absolute_configuration unk

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.580(7)
_cell_length_b                   5.800(4)
_cell_length_c                   20.624(17)
_cell_angle_alpha                90
_cell_angle_beta                 91.13(3)
_cell_angle_gamma                90
_cell_volume                     1145.8(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9617
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      29.99
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576

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

_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2016/2 - Bruker AXS area detector scaling and absorption
        correction. Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M. &
        Stalke D., J. Appl. Cryst. 48 (2015) 3-10.
;
_exptl_absorpt_correction_T_min  0.9164
_exptl_absorpt_correction_T_max  0.9669
_exptl_transmission_factor_max   none
_exptl_transmission_factor_min   none
_shelx_estimated_absorpt_T_min   0.916
_shelx_estimated_absorpt_T_max   0.967

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

_diffrn_source                   'fine-focus sealed tube'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_number            44600
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.327
_diffrn_reflns_theta_max         30.101
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_coverage         0.83
_reflns_number_total             6704
_reflns_number_gt                5415
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'BRUKER APEX-III'
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_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                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_special_details          none
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0613P)²+5.3342P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.016(8)
_refine_ls_number_reflns         6704
_refine_ls_number_parameters     356
_refine_ls_number_restraints     68
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1262
_refine_ls_R_factor_gt           0.1047
_refine_ls_wR_factor_ref         0.2359
_refine_ls_wR_factor_gt          0.223
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.03
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1894 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.18(19)
_refine_diff_density_max         1.54
_refine_diff_density_min         -0.986
_refine_diff_density_rms         0.108

#----------------------------------------------------------------------------#
#                   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 0.0033 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'
N N 0.0061 0.0033 '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'
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_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 -0.4105(8) 0.0047(6) 0.7635(4) 0.078(4) Uani 1 1 d D U . . .
C2 C 0.0754(8) 0.0102(17) 0.7389(4) 0.0407(19) Uani 1 1 d . . . . .
C11 C -0.4953(11) 0.2120(17) 0.6722(4) 0.047(2) Uani 1 1 d . U . . .
C12 C -0.4146(7) 0.4074(18) 0.6655(3) 0.0346(17) Uani 1 1 d . U . . .
H12 H -0.343244 0.441555 0.696654 0.042 Uiso 1 1 calc R U . . .
C13 C -0.4377(7) 0.5547(16) 0.6128(4) 0.0316(15) Uani 1 1 d . U . . .
H13 H -0.384196 0.691688 0.608778 0.038 Uiso 1 1 calc R U . . .
C14 C -0.5386(7) 0.5008(17) 0.5665(4) 0.0322(15) Uani 1 1 d . U . . .
H14 H -0.553638 0.599689 0.530351 0.039 Uiso 1 1 calc R U . . .
C15 C -0.6165(7) 0.3060(18) 0.5727(4) 0.0358(17) Uani 1 1 d . U . . .
H15 H -0.686087 0.270497 0.540859 0.043 Uiso 1 1 calc R U . . .
C16 C -0.5956(10) 0.1598(17) 0.6247(4) 0.044(2) Uani 1 1 d . U . . .
H16 H -0.649697 0.023249 0.628021 0.053 Uiso 1 1 calc R U . . .
C21 C -0.4553(10) -0.1810(6) 0.8158(3) 0.0389(18) Uani 1 1 d D U . . .
C22 C -0.5427(7) -0.3694(17) 0.8098(4) 0.0364(18) Uani 1 1 d . U . . .
H22 H -0.597748 -0.389304 0.771346 0.044 Uiso 1 1 calc R U . . .
C23 C -0.5506(8) -0.5292(17) 0.8593(4) 0.0392(18) Uani 1 1 d . U . . .
H23 H -0.610376 -0.659118 0.854753 0.047 Uiso 1 1 calc R U . . .
C24 C -0.4715(10) -0.4996(19) 0.9154(4) 0.048(2) Uani 1 1 d . U . . .
H24 H -0.476887 -0.609293 0.949419 0.058 Uiso 1 1 calc R U . . .
C25 C -0.3856(7) -0.313(2) 0.9220(4) 0.0393(19) Uani 1 1 d . U . . .
H25 H -0.331798 -0.293428 0.960784 0.047 Uiso 1 1 calc R U . . .
C26 C -0.3762(8) -0.1550(18) 0.8734(4) 0.0358(17) Uani 1 1 d . U . . .
H26 H -0.31566 -0.026228 0.87848 0.043 Uiso 1 1 calc R U . . .
C31 C 0.0108(8) 0.1678(15) 0.6824(3) 0.0296(15) Uani 1 1 d . . . . .
C32 C 0.0762(6) 0.3764(15) 0.6710(3) 0.0225(12) Uani 1 1 d . . . . .
C33 C 0.0477(6) 0.5065(15) 0.6168(3) 0.0198(11) Uani 1 1 d . . . . .
C34 C -0.0538(6) 0.4321(16) 0.5734(3) 0.0234(13) Uani 1 1 d . . . . .
C35 C -0.1234(6) 0.2247(16) 0.5830(3) 0.0239(13) Uani 1 1 d . . . . .
C36 C -0.0898(7) 0.0965(15) 0.6370(3) 0.0227(12) Uani 1 1 d . . . . .
C41 C 0.0219(11) -0.1992(16) 0.8311(3) 0.041(2) Uani 1 1 d . . . . .
C42 C -0.0495(9) -0.4032(17) 0.8380(3) 0.0353(17) Uani 1 1 d . . . . .
C43 C -0.0269(7) -0.5439(15) 0.8884(3) 0.0259(13) Uani 1 1 d . . . . .
C44 C 0.0746(7) -0.4908(15) 0.9354(3) 0.0244(13) Uani 1 1 d . . . . .
C45 C 0.1505(7) -0.2931(16) 0.9304(3) 0.0265(13) Uani 1 1 d . . . . .
C46 C 0.1236(9) -0.1457(16) 0.8780(4) 0.0363(17) Uani 1 1 d . . . . .
N1 N -0.5106(7) 0.0345(19) 0.7294(5) 0.067(2) Uani 1 1 d . . . . .
H1 H -0.589448 -0.039122 0.735937 0.081 Uiso 1 1 calc R U . . .
N2 N -0.0261(7) -0.043(2) 0.7761(5) 0.067(2) Uani 1 1 d . . . . .
H2 H -0.112573 0.004724 0.770281 0.081 Uiso 1 1 calc R U . . .
F11 F 0.1737(5) 0.4537(12) 0.7134(2) 0.0422(12) Uani 1 1 d . . . . .
F12 F 0.1134(4) 0.7067(12) 0.6072(2) 0.0326(9) Uani 1 1 d . . . . .
F13 F -0.0852(6) 0.5605(13) 0.5206(2) 0.0453(12) Uani 1 1 d . . . . .
F14 F -0.2183(4) 0.1515(13) 0.5393(2) 0.0406(12) Uani 1 1 d . . . . .
F15 F -0.1549(5) -0.1068(12) 0.6447(2) 0.0374(10) Uani 1 1 d . . . . .
F21 F -0.1460(5) -0.4632(14) 0.7922(2) 0.0505(14) Uani 1 1 d . . . . .
F22 F -0.0993(5) -0.7426(13) 0.8944(2) 0.0434(12) Uani 1 1 d . . . . .
F23 F 0.0965(6) -0.6339(13) 0.9859(2) 0.0449(12) Uani 1 1 d . . . . .
F24 F 0.2457(5) -0.2376(14) 0.9759(2) 0.0434(12) Uani 1 1 d . . . . .
F25 F 0.1918(7) 0.0557(13) 0.8758(3) 0.0616(17) Uani 1 1 d . . . . .
O1 O -0.2912(5) 0.1000(14) 0.7596(3) 0.0338(12) Uani 1 1 d . . . . .
O2 O 0.1994(4) -0.0325(13) 0.7426(2) 0.0245(9) 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 N1 1.190(12) . ?
C1 O1 1.273(9) . ?
C1 C21 1.5900(8) . ?
C2 O2 1.215(9) . ?
C2 N2 1.288(11) . ?
C2 C31 1.597(12) . ?
C11 C12 1.381(13) . ?
C11 C16 1.392(14) . ?
C11 N1 1.575(13) . ?
C12 C13 1.397(11) . ?
C12 H12 0.95 . ?
C13 C14 1.380(10) . ?
C13 H13 0.95 . ?
C14 C15 1.362(11) . ?
C14 H14 0.95 . ?
C15 C16 1.377(13) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
C21 C22 1.381(11) . ?
C21 C26 1.404(11) . ?
C22 C23 1.382(12) . ?
C22 H22 0.95 . ?
C23 C24 1.381(13) . ?
C23 H23 0.95 . ?
C24 C25 1.364(14) . ?
C24 H24 0.95 . ?
C25 C26 1.363(12) . ?
C25 H25 0.95 . ?
C26 H26 0.95 . ?
C31 C32 1.385(9) . ?
C31 C36 1.392(9) . ?
C32 F11 1.344(7) . ?
C32 C33 1.370(8) . ?
C33 F12 1.338(7) . ?
C33 C34 1.379(8) . ?
C34 F13 1.348(7) . ?
C34 C35 1.391(9) . ?
C35 F14 1.338(7) . ?
C35 C36 1.372(9) . ?
C36 F15 1.345(7) . ?
C41 C42 1.375(12) . ?
C41 C46 1.393(12) . ?
C41 N2 1.516(13) . ?
C42 C43 1.336(10) . ?
C42 F21 1.354(8) . ?
C43 F22 1.352(8) . ?
C43 C44 1.393(9) . ?
C44 F23 1.346(8) . ?
C44 C45 1.363(9) . ?
C45 F24 1.335(8) . ?
C45 C46 1.399(10) . ?
C46 F25 1.340(8) . ?
N1 H1 0.88 . ?
N2 H2 0.88 . ?

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
N1 C1 O1 127.9(8) . . ?
N1 C1 C21 105.9(8) . . ?
O1 C1 C21 126.3(8) . . ?
O2 C2 N2 131.5(10) . . ?
O2 C2 C31 121.8(7) . . ?
N2 C2 C31 106.7(8) . . ?
C12 C11 C16 119.2(7) . . ?
C12 C11 N1 132.2(8) . . ?
C16 C11 N1 108.2(8) . . ?
C11 C12 C13 120.0(7) . . ?
C11 C12 H12 120 . . ?
C13 C12 H12 120 . . ?
C14 C13 C12 119.8(7) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C15 C14 C13 120.0(7) . . ?
C15 C14 H14 120 . . ?
C13 C14 H14 120 . . ?
C14 C15 C16 120.8(7) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C11 120.1(7) . . ?
C15 C16 H16 120 . . ?
C11 C16 H16 120 . . ?
C22 C21 C26 118.5(7) . . ?
C22 C21 C1 130.3(7) . . ?
C26 C21 C1 110.6(7) . . ?
C21 C22 C23 120.4(6) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C24 C23 C22 119.9(7) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C25 C24 C23 120.2(8) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C26 C25 C24 120.6(7) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C25 C26 C21 120.5(7) . . ?
C25 C26 H26 119.8 . . ?
C21 C26 H26 119.8 . . ?
C32 C31 C36 117.1(6) . . ?
C32 C31 C2 117.0(6) . . ?
C36 C31 C2 125.0(6) . . ?
F11 C32 C33 118.1(6) . . ?
F11 C32 C31 119.5(6) . . ?
C33 C32 C31 122.4(6) . . ?
F12 C33 C32 120.8(5) . . ?
F12 C33 C34 120.2(6) . . ?
C32 C33 C34 119.0(6) . . ?
F13 C34 C33 119.7(6) . . ?
F13 C34 C35 119.6(6) . . ?
C33 C34 C35 120.7(5) . . ?
F14 C35 C36 121.4(6) . . ?
F14 C35 C34 119.9(6) . . ?
C36 C35 C34 118.7(5) . . ?
F15 C36 C35 118.0(5) . . ?
F15 C36 C31 119.8(6) . . ?
C35 C36 C31 122.1(6) . . ?
C42 C41 C46 117.6(6) . . ?
C42 C41 N2 116.5(7) . . ?
C46 C41 N2 125.7(7) . . ?
C43 C42 F21 118.9(7) . . ?
C43 C42 C41 122.2(7) . . ?
F21 C42 C41 118.9(7) . . ?
C42 C43 F22 121.1(7) . . ?
C42 C43 C44 120.4(7) . . ?
F22 C43 C44 118.5(6) . . ?
F23 C44 C45 120.1(6) . . ?
F23 C44 C43 119.9(6) . . ?
C45 C44 C43 120.0(6) . . ?
F24 C45 C44 120.6(6) . . ?
F24 C45 C46 120.6(7) . . ?
C44 C45 C46 118.8(6) . . ?
F25 C46 C41 120.4(7) . . ?
F25 C46 C45 118.4(7) . . ?
C41 C46 C45 121.0(7) . . ?
C1 N1 C11 116.8(8) . . ?
C1 N1 H1 121.6 . . ?
C11 N1 H1 121.6 . . ?
C2 N2 C41 111.6(8) . . ?
C2 N2 H2 124.2 . . ?
C41 N2 H2 124.2 . . ?



# END of CIF
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
