# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_ls_16_k7
_database_code_depnum_ccdc_archive 'CCDC 2101143'
loop_
_audit_author_name
_audit_author_address
'Audrius Bucinskas'
;Kaunas University of Technology
Lithuania
;
_audit_update_record             
;
2021-08-03 deposited with the CCDC.	2022-02-15 downloaded from the CCDC.
;
_audit_creation_date             2021-08-03
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        
10,10'-(2,5-bis(trifluoromethyl)-1,4-phenylene)bis(10H-phenoxazine)
_chemical_formula_moiety         '0.4(C32 H18 F6 N2 O2)'
_chemical_formula_sum            'C12.80 H7.20 F2.40 N0.80 O0.80'
_chemical_formula_weight         230.59
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.547(7)
_cell_length_b                   13.589(7)
_cell_length_c                   6.839(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.17(5)
_cell_angle_gamma                90
_cell_volume                     1257.1(12)
_cell_formula_units_Z            5
_cell_measurement_reflns_used    461
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.7370
_cell_measurement_theta_min      3.0690
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45369
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             588
_exptl_crystal_preparation       'material was dissolved in THF solvent'
_exptl_crystal_recrystallization_method 'slow evaporation'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0855
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4677
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         2.998
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -71.00 111.00   1.00    4.50    --   30.10  54.00  60.00  182
  2  ω     40.00  79.00   1.00    4.50    --   30.10  54.00 -30.00   39
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0515586000
_diffrn_orient_matrix_UB_12      -0.0074467000
_diffrn_orient_matrix_UB_13      -0.0161395000
_diffrn_orient_matrix_UB_21      -0.0049294000
_diffrn_orient_matrix_UB_22      -0.0007582000
_diffrn_orient_matrix_UB_23      0.1028235000
_diffrn_orient_matrix_UB_31      -0.0076812000
_diffrn_orient_matrix_UB_32      0.0516459000
_diffrn_orient_matrix_UB_33      0.0001025000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1056
_reflns_number_total             2465
_reflns_odcompleteness_completeness 98.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.31a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.31a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2465
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1636
_refine_ls_R_factor_gt           0.0798
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1320P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2037
_refine_ls_wR_factor_ref         0.2847
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.4205(3) 0.3933(3) 0.0329(5) 0.1209(15) Uani 1 1 d . . . . .
F2 F 0.5065(2) 0.2849(2) 0.1879(5) 0.0939(12) Uani 1 1 d . . . . .
F3 F 0.3584(2) 0.3045(3) 0.2507(7) 0.1293(17) Uani 1 1 d . . . . .
O1 O 0.1036(2) 0.4709(3) 0.2247(5) 0.0752(11) Uani 1 1 d . . . . .
N1 N 0.2984(2) 0.4898(3) 0.3701(6) 0.0553(10) Uani 1 1 d . . . . .
C1 C 0.1633(3) 0.5423(3) 0.1452(7) 0.0551(12) Uani 1 1 d . . . . .
C2 C 0.1230(3) 0.5990(4) -0.0040(8) 0.0668(14) Uani 1 1 d . . . . .
H2 H 0.057067 0.590860 -0.046148 0.080 Uiso 1 1 calc R U . . .
C3 C 0.1807(4) 0.6689(4) -0.0927(8) 0.0698(14) Uani 1 1 d . . . . .
H3 H 0.154097 0.708287 -0.193532 0.084 Uiso 1 1 calc R U . . .
C4 C 0.2784(3) 0.6782(4) -0.0273(7) 0.0621(13) Uani 1 1 d . . . . .
H4 H 0.318110 0.724313 -0.085702 0.075 Uiso 1 1 calc R U . . .
C5 C 0.3186(3) 0.6201(3) 0.1240(7) 0.0550(12) Uani 1 1 d . . . . .
H5 H 0.384814 0.627553 0.164925 0.066 Uiso 1 1 calc R U . . .
C6 C 0.2612(3) 0.5514(3) 0.2145(6) 0.0465(10) Uani 1 1 d . . . . .
C7 C 0.2293(3) 0.4407(3) 0.4835(7) 0.0496(11) Uani 1 1 d . . . . .
C8 C 0.2548(3) 0.3989(4) 0.6631(8) 0.0628(13) Uani 1 1 d . . . . .
H8 H 0.319284 0.404440 0.716020 0.075 Uiso 1 1 calc R U . . .
C9 C 0.1842(4) 0.3483(4) 0.7662(8) 0.0707(15) Uani 1 1 d . . . . .
H9 H 0.202184 0.319487 0.886288 0.085 Uiso 1 1 calc R U . . .
C10 C 0.0899(4) 0.3413(4) 0.6914(9) 0.0730(15) Uani 1 1 d . . . . .
H10 H 0.042965 0.307869 0.760043 0.088 Uiso 1 1 calc R U . . .
C11 C 0.0634(3) 0.3844(4) 0.5111(8) 0.0684(15) Uani 1 1 d . . . . .
H11 H -0.001674 0.380512 0.460552 0.082 Uiso 1 1 calc R U . . .
C12 C 0.1330(3) 0.4329(3) 0.4074(7) 0.0546(12) Uani 1 1 d . . . . .
C13 C 0.4006(3) 0.4942(3) 0.4363(6) 0.0483(11) Uani 1 1 d . . . . .
C14 C 0.4689(3) 0.4297(3) 0.3634(6) 0.0485(11) Uani 1 1 d . . . . .
C15 C 0.5674(3) 0.4364(3) 0.4257(7) 0.0562(12) Uani 1 1 d . . . . .
H15 H 0.613014 0.393694 0.374375 0.067 Uiso 1 1 calc R U . . .
C16 C 0.4380(3) 0.3536(4) 0.2093(9) 0.0678(14) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C16 1.330(6) . ?
F2 C16 1.331(6) . ?
F3 C16 1.312(6) . ?
O1 C1 1.392(5) . ?
O1 C12 1.390(5) . ?
N1 C6 1.423(5) . ?
N1 C7 1.416(5) . ?
N1 C13 1.435(5) . ?
C1 C2 1.369(6) . ?
C1 C6 1.390(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.390(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.389(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(6) . ?
C7 C8 1.379(6) . ?
C7 C12 1.382(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.399(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.353(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.394(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.379(6) . ?
C13 C14 1.387(5) . ?
C13 C15 1.387(6) 3_666 ?
C14 C15 1.382(5) . ?
C14 C16 1.518(6) . ?
C15 H15 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O1 C1 117.8(3) . . ?
C6 N1 C13 120.5(3) . . ?
C7 N1 C6 118.0(3) . . ?
C7 N1 C13 120.1(4) . . ?
C2 C1 O1 117.9(4) . . ?
C2 C1 C6 122.5(4) . . ?
C6 C1 O1 119.6(4) . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 120.0(4) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.8 . . ?
C4 C3 C2 118.3(5) . . ?
C4 C3 H3 120.8 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.3(4) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.7(4) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 N1 119.6(4) . . ?
C5 C6 N1 123.2(4) . . ?
C5 C6 C1 117.2(4) . . ?
C8 C7 N1 122.8(4) . . ?
C8 C7 C12 119.2(4) . . ?
C12 C7 N1 117.9(4) . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.4(4) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.1(5) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.8(5) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.3(4) . . ?
C12 C11 H11 119.8 . . ?
C7 C12 O1 121.9(4) . . ?
C11 C12 O1 118.0(4) . . ?
C11 C12 C7 120.1(4) . . ?
C14 C13 N1 120.8(4) . . ?
C14 C13 C15 119.1(3) . 3_666 ?
C15 C13 N1 120.1(4) 3_666 . ?
C13 C14 C16 121.1(4) . . ?
C15 C14 C13 120.0(4) . . ?
C15 C14 C16 118.9(4) . . ?
C13 C15 H15 119.5 3_666 . ?
C14 C15 C13 121.0(4) . 3_666 ?
C14 C15 H15 119.5 . . ?
F1 C16 F2 105.9(5) . . ?
F1 C16 C14 112.5(4) . . ?
F2 C16 C14 112.7(4) . . ?
F3 C16 F1 107.1(5) . . ?
F3 C16 F2 104.7(4) . . ?
F3 C16 C14 113.3(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -177.8(4) . . . . ?
O1 C1 C6 N1 -2.0(6) . . . . ?
O1 C1 C6 C5 176.9(4) . . . . ?
N1 C7 C8 C9 -177.9(4) . . . . ?
N1 C7 C12 O1 0.5(6) . . . . ?
N1 C7 C12 C11 179.1(4) . . . . ?
N1 C13 C14 C15 178.6(4) . . . . ?
N1 C13 C14 C16 0.9(7) . . . . ?
C1 O1 C12 C7 -19.2(6) . . . . ?
C1 O1 C12 C11 162.1(4) . . . . ?
C1 C2 C3 C4 0.5(8) . . . . ?
C2 C1 C6 N1 -179.9(4) . . . . ?
C2 C1 C6 C5 -1.0(7) . . . . ?
C2 C3 C4 C5 -0.4(8) . . . . ?
C3 C4 C5 C6 -0.4(7) . . . . ?
C4 C5 C6 N1 180.0(4) . . . . ?
C4 C5 C6 C1 1.1(6) . . . . ?
C6 N1 C7 C8 -164.1(4) . . . . ?
C6 N1 C7 C12 17.4(6) . . . . ?
C6 N1 C13 C14 -94.5(5) . . . . ?
C6 N1 C13 C15 85.2(5) . . . 3_666 ?
C6 C1 C2 C3 0.2(8) . . . . ?
C7 N1 C6 C1 -16.7(6) . . . . ?
C7 N1 C6 C5 164.4(4) . . . . ?
C7 N1 C13 C14 99.0(5) . . . . ?
C7 N1 C13 C15 -81.3(5) . . . 3_666 ?
C7 C8 C9 C10 -1.0(8) . . . . ?
C8 C7 C12 O1 -178.1(4) . . . . ?
C8 C7 C12 C11 0.5(7) . . . . ?
C8 C9 C10 C11 0.2(8) . . . . ?
C9 C10 C11 C12 1.0(8) . . . . ?
C10 C11 C12 O1 177.3(5) . . . . ?
C10 C11 C12 C7 -1.3(7) . . . . ?
C12 O1 C1 C2 -162.3(4) . . . . ?
C12 O1 C1 C6 19.7(6) . . . . ?
C12 C7 C8 C9 0.7(7) . . . . ?
C13 N1 C6 C1 176.4(4) . . . . ?
C13 N1 C6 C5 -2.4(6) . . . . ?
C13 N1 C7 C8 2.8(6) . . . . ?
C13 N1 C7 C12 -175.8(4) . . . . ?
C13 C14 C15 C13 1.2(7) . . . 3_666 ?
C13 C14 C16 F1 74.2(6) . . . . ?
C13 C14 C16 F2 -166.1(4) . . . . ?
C13 C14 C16 F3 -47.4(6) . . . . ?
C15 C13 C14 C15 -1.2(7) 3_666 . . . ?
C15 C13 C14 C16 -178.8(4) 3_666 . . . ?
C15 C14 C16 F1 -103.5(5) . . . . ?
C15 C14 C16 F2 16.2(7) . . . . ?
C15 C14 C16 F3 134.9(5) . . . . ?
C16 C14 C15 C13 178.9(4) . . . 3_666 ?

_olex2_exptl_crystal_mounting_method 
'single crystal was mounted using glass stick with glue'
_olex2_submission_original_sample_id 2PO-2CF3Ph
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.950
_oxdiff_exptl_absorpt_empirical_full_min 0.496
####################################################################### 
# 
# 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_ls17_k1
_database_code_depnum_ccdc_archive 'CCDC 2108558'
loop_
_audit_author_name
_audit_author_address
'Audrius Bucinskas'
;Kaunas University of Technology
Lithuania
;
_audit_update_record             
;
2021-09-08 deposited with the CCDC.	2022-02-15 downloaded from the CCDC.
;
_audit_creation_date             2021-09-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        
10,10'-(2,5-bis(trifluoromethyl)-1,4-phenylene)bis(10H-phenothiazine)
_chemical_formula_moiety         '0.286(C32 H18 F6 N2 S2)'
_chemical_formula_sum            'C9.14 H5.14 F1.71 N0.57 S0.57'
_chemical_formula_weight         173.89
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.328(3)
_cell_length_b                   12.3912(17)
_cell_length_c                   13.580(2)
_cell_angle_alpha                90
_cell_angle_beta                 109.089(18)
_cell_angle_gamma                90
_cell_volume                     3232.6(9)
_cell_formula_units_Z            14
_cell_measurement_reflns_used    2295
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.9560
_cell_measurement_theta_min      2.6610
_shelx_estimated_absorpt_T_max   0.936
_shelx_estimated_absorpt_T_min   0.917
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35602
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1240
_exptl_crystal_preparation       'material was dissolved in THF solvent'
_exptl_crystal_recrystallization_method 'slow evaporation'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5571
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_min         2.120
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -67.00 114.00   1.00   17.43    --   30.10  54.00-150.00  181
  2  ω      6.00  31.00   1.00   17.43    --   30.10  54.00 -30.00   25
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0124191000
_diffrn_orient_matrix_UB_12      0.0486970000
_diffrn_orient_matrix_UB_13      -0.0150777000
_diffrn_orient_matrix_UB_21      0.0080987000
_diffrn_orient_matrix_UB_22      -0.0278907000
_diffrn_orient_matrix_UB_23      -0.0402300000
_diffrn_orient_matrix_UB_31      -0.0337882000
_diffrn_orient_matrix_UB_32      0.0109724000
_diffrn_orient_matrix_UB_33      -0.0348933000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2151
_reflns_number_total             3174
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.31a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.31a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0549
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0862P)²+0.9854P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1654
_refine_ls_wR_factor_ref         0.1873
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.20304(4) 0.62741(6) 0.18410(7) 0.0631(3) Uani 1 1 d . . . . .
F1 F 0.40604(10) 0.54979(16) 0.42067(16) 0.0829(6) Uani 1 1 d . . . . .
F2 F 0.49243(10) 0.64307(18) 0.51344(15) 0.0831(6) Uani 1 1 d . . . . .
F3 F 0.40134(10) 0.72178(15) 0.41584(15) 0.0805(6) Uani 1 1 d . . . . .
N1 N 0.35416(10) 0.63392(14) 0.20279(17) 0.0410(5) Uani 1 1 d . . . . .
C1 C 0.25466(18) 0.3341(2) 0.1116(2) 0.0606(8) Uani 1 1 d . . . . .
H1 H 0.232489 0.268147 0.091459 0.073 Uiso 1 1 calc R U . . .
C2 C 0.32449(18) 0.3441(2) 0.1291(3) 0.0614(8) Uani 1 1 d . . . . .
H2 H 0.349870 0.284248 0.120931 0.074 Uiso 1 1 calc R U . . .
C3 C 0.35801(15) 0.4418(2) 0.1588(2) 0.0518(7) Uani 1 1 d . . . . .
H3 H 0.405542 0.446857 0.169887 0.062 Uiso 1 1 calc R U . . .
C4 C 0.32168(12) 0.53213(19) 0.17210(19) 0.0399(6) Uani 1 1 d . . . . .
C5 C 0.25067(13) 0.5207(2) 0.15626(19) 0.0451(6) Uani 1 1 d . . . . .
C6 C 0.21777(15) 0.4224(2) 0.1241(2) 0.0549(7) Uani 1 1 d . . . . .
H6 H 0.170044 0.416585 0.110898 0.066 Uiso 1 1 calc R U . . .
C7 C 0.31754(13) 0.73217(19) 0.16733(19) 0.0412(6) Uani 1 1 d . . . . .
C8 C 0.35055(15) 0.8253(2) 0.1513(2) 0.0516(7) Uani 1 1 d . . . . .
H8 H 0.398212 0.824306 0.162691 0.062 Uiso 1 1 calc R U . . .
C9 C 0.31338(18) 0.9193(2) 0.1187(2) 0.0622(8) Uani 1 1 d . . . . .
H9 H 0.336531 0.981230 0.109285 0.075 Uiso 1 1 calc R U . . .
C10 C 0.24343(17) 0.9229(3) 0.1000(2) 0.0616(8) Uani 1 1 d . . . . .
H10 H 0.218713 0.986350 0.076918 0.074 Uiso 1 1 calc R U . . .
C11 C 0.20992(15) 0.8318(2) 0.1156(2) 0.0572(7) Uani 1 1 d . . . . .
H11 H 0.162088 0.833617 0.102615 0.069 Uiso 1 1 calc R U . . .
C12 C 0.24611(12) 0.7373(2) 0.1503(2) 0.0455(6) Uani 1 1 d . . . . .
C13 C 0.42792(12) 0.63740(17) 0.2273(2) 0.0388(6) Uani 1 1 d . . . . .
C14 C 0.47196(12) 0.63836(17) 0.3308(2) 0.0387(6) Uani 1 1 d . . . . .
C15 C 0.54350(13) 0.63799(18) 0.3535(2) 0.0416(6) Uani 1 1 d . . . . .
H15 H 0.572580 0.638137 0.422441 0.050 Uiso 1 1 calc R U . . .
C16 C 0.44260(14) 0.6381(2) 0.4197(2) 0.0525(7) Uani 1 1 d . . . . .


_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
S1 C5 1.751(3) . ?
S1 C12 1.760(3) . ?
F1 C16 1.325(3) . ?
F2 C16 1.344(3) . ?
F3 C16 1.324(3) . ?
N1 C4 1.421(3) . ?
N1 C7 1.426(3) . ?
N1 C13 1.426(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.366(4) . ?
C1 C6 1.368(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.383(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.386(3) . ?
C4 C5 1.395(3) . ?
C5 C6 1.390(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.387(3) . ?
C7 C12 1.395(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.381(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.361(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.371(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.381(4) . ?
C13 C14 1.398(4) . ?
C13 C15 1.398(4) 2_655 ?
C14 C15 1.385(3) . ?
C14 C16 1.513(4) . ?
C15 H15 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 S1 C12 99.81(12) . . ?
C4 N1 C7 121.2(2) . . ?
C4 N1 C13 116.56(18) . . ?
C7 N1 C13 116.47(18) . . ?
C2 C1 H1 120.4 . . ?
C2 C1 C6 119.1(3) . . ?
C6 C1 H1 120.4 . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 121.0(3) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 N1 122.6(2) . . ?
C3 C4 C5 117.8(2) . . ?
C5 C4 N1 119.5(2) . . ?
C4 C5 S1 120.50(19) . . ?
C6 C5 S1 119.1(2) . . ?
C6 C5 C4 120.3(2) . . ?
C1 C6 C5 120.9(3) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C8 C7 N1 122.5(2) . . ?
C8 C7 C12 117.8(2) . . ?
C12 C7 N1 119.7(2) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.7(3) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.1(3) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 120.5 . . ?
C9 C10 C11 119.1(3) . . ?
C11 C10 H10 120.5 . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 121.0(3) . . ?
C12 C11 H11 119.5 . . ?
C7 C12 S1 120.06(19) . . ?
C11 C12 S1 119.4(2) . . ?
C11 C12 C7 120.3(2) . . ?
C14 C13 N1 120.9(2) . . ?
C14 C13 C15 119.6(2) . 2_655 ?
C15 C13 N1 119.5(2) 2_655 . ?
C13 C14 C16 120.9(2) . . ?
C15 C14 C13 120.3(2) . . ?
C15 C14 C16 118.8(2) . . ?
C13 C15 H15 120.0 2_655 . ?
C14 C15 C13 120.1(2) . 2_655 ?
C14 C15 H15 120.0 . . ?
F1 C16 F2 106.3(2) . . ?
F1 C16 C14 112.2(2) . . ?
F2 C16 C14 112.6(2) . . ?
F3 C16 F1 107.3(2) . . ?
F3 C16 F2 105.9(2) . . ?
F3 C16 C14 112.1(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C5 C6 C1 -173.4(2) . . . . ?
N1 C4 C5 S1 -5.2(3) . . . . ?
N1 C4 C5 C6 178.6(2) . . . . ?
N1 C7 C8 C9 -178.9(2) . . . . ?
N1 C7 C12 S1 6.1(3) . . . . ?
N1 C7 C12 C11 -179.8(2) . . . . ?
N1 C13 C14 C15 177.8(2) . . . . ?
N1 C13 C14 C16 -1.3(3) . . . . ?
C1 C2 C3 C4 0.4(5) . . . . ?
C2 C1 C6 C5 -1.3(4) . . . . ?
C2 C3 C4 N1 179.8(2) . . . . ?
C2 C3 C4 C5 1.0(4) . . . . ?
C3 C4 C5 S1 173.6(2) . . . . ?
C3 C4 C5 C6 -2.5(4) . . . . ?
C4 N1 C7 C8 -148.6(2) . . . . ?
C4 N1 C7 C12 33.1(3) . . . . ?
C4 N1 C13 C14 -101.7(3) . . . . ?
C4 N1 C13 C15 77.2(3) . . . 2_655 ?
C4 C5 C6 C1 2.7(4) . . . . ?
C5 S1 C12 C7 -34.5(2) . . . . ?
C5 S1 C12 C11 151.3(2) . . . . ?
C6 C1 C2 C3 -0.2(5) . . . . ?
C7 N1 C4 C3 147.6(2) . . . . ?
C7 N1 C4 C5 -33.6(3) . . . . ?
C7 N1 C13 C14 104.7(3) . . . . ?
C7 N1 C13 C15 -76.4(3) . . . 2_655 ?
C7 C8 C9 C10 -0.9(5) . . . . ?
C8 C7 C12 S1 -172.3(2) . . . . ?
C8 C7 C12 C11 1.9(4) . . . . ?
C8 C9 C10 C11 1.0(5) . . . . ?
C9 C10 C11 C12 0.3(4) . . . . ?
C10 C11 C12 S1 172.4(2) . . . . ?
C10 C11 C12 C7 -1.8(4) . . . . ?
C12 S1 C5 C4 34.2(2) . . . . ?
C12 S1 C5 C6 -149.7(2) . . . . ?
C12 C7 C8 C9 -0.6(4) . . . . ?
C13 N1 C4 C3 -4.6(4) . . . . ?
C13 N1 C4 C5 174.2(2) . . . . ?
C13 N1 C7 C8 3.6(4) . . . . ?
C13 N1 C7 C12 -174.7(2) . . . . ?
C13 C14 C15 C13 0.4(3) . . . 2_655 ?
C13 C14 C16 F1 62.4(3) . . . . ?
C13 C14 C16 F2 -177.8(2) . . . . ?
C13 C14 C16 F3 -58.5(3) . . . . ?
C15 C13 C14 C15 -1.1(3) 2_655 . . . ?
C15 C13 C14 C16 179.8(2) 2_655 . . . ?
C15 C14 C16 F1 -116.7(3) . . . . ?
C15 C14 C16 F2 3.2(3) . . . . ?
C15 C14 C16 F3 122.5(3) . . . . ?
C16 C14 C15 C13 179.5(2) . . . 2_655 ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.500 -0.251 407.5 124.9 ?
2 0.500 0.000 -0.517 407.5 124.9 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_exptl_crystal_mounting_method 
'single crystal was mounted using glass stick with glue'
_olex2_submission_original_sample_id 2PS-2CF3Ph
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.635
_oxdiff_exptl_absorpt_empirical_full_min 0.527
####################################################################### 
# 
# 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_sl_19_k2
_database_code_depnum_ccdc_archive 'CCDC 2108557'
loop_
_audit_author_name
_audit_author_address
'Audrius Bucinskas'
;Kaunas University of Technology
Lithuania
;
_audit_update_record             
;
2021-09-08 deposited with the CCDC.	2022-02-15 downloaded from the CCDC.
;
_audit_creation_date             2021-09-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        
10,10'-(2,5-bis(trifluoromethyl)-1,4-phenylene)bis(9,9-dimethyl-9,10-dihydroacridine)
_chemical_formula_moiety         '0.333(C38 H30 F6 N2)'
_chemical_formula_sum            'C12.67 H10 F2 N0.67'
_chemical_formula_weight         209.55
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.5633(10)
_cell_length_b                   19.424(3)
_cell_length_c                   10.2942(14)
_cell_angle_alpha                90
_cell_angle_beta                 96.059(13)
_cell_angle_gamma                90
_cell_volume                     1503.9(4)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    1913
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.3260
_cell_measurement_theta_min      2.3000
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.948
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74662
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             652
_exptl_crystal_preparation       'material was dissolved in THF solvent'
_exptl_crystal_recrystallization_method 'slow evaporation'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5798
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_min         2.097
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -73.00 109.00   1.00   12.50    --   30.10  54.00  90.00  182
  2  ω     14.00  59.00   1.00   12.50    --   30.10  54.00   0.00   45
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0354677000
_diffrn_orient_matrix_UB_12      -0.0311565000
_diffrn_orient_matrix_UB_13      -0.0223931000
_diffrn_orient_matrix_UB_21      -0.0863164000
_diffrn_orient_matrix_UB_22      -0.0147706000
_diffrn_orient_matrix_UB_23      -0.0061045000
_diffrn_orient_matrix_UB_31      -0.0142673000
_diffrn_orient_matrix_UB_32      0.0119413000
_diffrn_orient_matrix_UB_33      -0.0652372000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1882
_reflns_number_total             2950
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.31a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.31a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2950
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0957
_refine_ls_R_factor_gt           0.0565
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0827P)²+0.0132P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1476
_refine_ls_wR_factor_ref         0.1894
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C19(H19), C15(H15), C12(H12), C13(H13), C1(H1), C14(H14), C3(H3),
 C2(H2)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.2164(3) 0.35054(8) 0.4533(2) 0.0764(6) Uani 1 1 d . . . . .
F3 F 0.0663(3) 0.43608(10) 0.37466(19) 0.0747(6) Uani 1 1 d . . . . .
F2 F 0.0942(3) 0.41925(11) 0.57994(19) 0.0817(7) Uani 1 1 d . . . . .
N1 N 0.4183(3) 0.42417(10) 0.26725(19) 0.0406(6) Uani 1 1 d . . . . .
C5 C 0.5197(4) 0.36505(12) 0.2451(2) 0.0398(6) Uani 1 1 d . . . . .
C10 C 0.2930(4) 0.42613(12) 0.0413(2) 0.0386(6) Uani 1 1 d . . . . .
C11 C 0.3383(3) 0.46142(12) 0.1583(2) 0.0387(6) Uani 1 1 d . . . . .
C6 C 0.4762(4) 0.32801(12) 0.1297(3) 0.0413(6) Uani 1 1 d . . . . .
C16 C 0.4584(4) 0.46182(11) 0.3858(2) 0.0393(6) Uani 1 1 d . . . . .
C17 C 0.3474(4) 0.45978(12) 0.4855(2) 0.0397(6) Uani 1 1 d . . . . .
C4 C 0.6587(4) 0.34345(13) 0.3335(3) 0.0471(7) Uani 1 1 d . . . . .
H4 H 0.684961 0.367514 0.411290 0.057 Uiso 1 1 calc R U . . .
C7 C 0.3131(4) 0.34765(13) 0.0408(3) 0.0459(7) Uani 1 1 d . . . . .
C19 C 0.3889(4) 0.49779(12) 0.5988(3) 0.0420(6) Uani 1 1 d . . . . .
H19 H 0.314156 0.496237 0.664881 0.050 Uiso 1 1 calc R U . . .
C18 C 0.1821(4) 0.41689(14) 0.4736(3) 0.0513(7) Uani 1 1 d . . . . .
C15 C 0.2225(4) 0.46397(15) -0.0647(2) 0.0494(7) Uani 1 1 d . . . . .
H15 H 0.192191 0.441475 -0.143714 0.059 Uiso 1 1 calc R U . . .
C12 C 0.3069(4) 0.53179(13) 0.1657(3) 0.0475(7) Uani 1 1 d . . . . .
H12 H 0.333708 0.554783 0.244594 0.057 Uiso 1 1 calc R U . . .
C13 C 0.2366(4) 0.56747(15) 0.0575(3) 0.0530(8) Uani 1 1 d . . . . .
H13 H 0.217305 0.614619 0.062987 0.064 Uiso 1 1 calc R U . . .
C1 C 0.5813(5) 0.27087(14) 0.1081(3) 0.0584(8) Uani 1 1 d . . . . .
H1 H 0.555699 0.245805 0.031412 0.070 Uiso 1 1 calc R U . . .
C14 C 0.1950(4) 0.53405(14) -0.0582(3) 0.0520(8) Uani 1 1 d . . . . .
H14 H 0.148538 0.558264 -0.131991 0.062 Uiso 1 1 calc R U . . .
C3 C 0.7593(4) 0.28664(14) 0.3082(3) 0.0563(8) Uani 1 1 d . . . . .
H3 H 0.853594 0.273089 0.368052 0.068 Uiso 1 1 calc R U . . .
C8 C 0.1491(4) 0.31575(14) 0.0973(3) 0.0568(8) Uani 1 1 d . . . . .
H8A H 0.140828 0.333672 0.183361 0.085 Uiso 1 1 calc R U . . .
H8B H 0.161926 0.266612 0.101673 0.085 Uiso 1 1 calc R U . . .
H8C H 0.043183 0.327264 0.041790 0.085 Uiso 1 1 calc R U . . .
C2 C 0.7205(5) 0.25034(16) 0.1951(3) 0.0635(9) Uani 1 1 d . . . . .
H2 H 0.787887 0.212068 0.177505 0.076 Uiso 1 1 calc R U . . .
C9 C 0.3207(5) 0.32031(16) -0.0991(3) 0.0669(10) Uani 1 1 d . . . . .
H9A H 0.211005 0.330663 -0.151117 0.100 Uiso 1 1 calc R U . . .
H9B H 0.338458 0.271369 -0.096474 0.100 Uiso 1 1 calc R U . . .
H9C H 0.417408 0.341873 -0.136900 0.100 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C18 1.335(3) . ?
F3 C18 1.325(3) . ?
F2 C18 1.340(3) . ?
N1 C5 1.413(3) . ?
N1 C11 1.415(3) . ?
N1 C16 1.428(3) . ?
C5 C6 1.398(3) . ?
C5 C4 1.381(4) . ?
C10 C11 1.397(3) . ?
C10 C7 1.532(3) . ?
C10 C15 1.376(4) . ?
C11 C12 1.391(4) . ?
C6 C7 1.506(4) . ?
C6 C1 1.397(4) . ?
C16 C17 1.393(4) . ?
C16 C19 1.391(4) 3_666 ?
C17 C19 1.388(3) . ?
C17 C18 1.497(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.381(4) . ?
C7 C8 1.553(4) . ?
C7 C9 1.542(4) . ?
C19 H19 0.9300 . ?
C15 H15 0.9300 . ?
C15 C14 1.380(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.371(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.364(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.367(4) . ?
C14 H14 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.366(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C2 H2 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

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
C5 N1 C11 118.8(2) . . ?
C5 N1 C16 119.0(2) . . ?
C11 N1 C16 116.74(19) . . ?
C6 C5 N1 118.2(2) . . ?
C4 C5 N1 122.0(2) . . ?
C4 C5 C6 119.9(2) . . ?
C11 C10 C7 118.4(2) . . ?
C15 C10 C11 117.5(2) . . ?
C15 C10 C7 124.0(2) . . ?
C10 C11 N1 118.5(2) . . ?
C12 C11 N1 121.3(2) . . ?
C12 C11 C10 120.1(2) . . ?
C5 C6 C7 119.4(2) . . ?
C1 C6 C5 117.3(3) . . ?
C1 C6 C7 123.2(2) . . ?
C17 C16 N1 121.7(2) . . ?
C19 C16 N1 119.0(2) 3_666 . ?
C19 C16 C17 119.3(2) 3_666 . ?
C16 C17 C18 121.2(2) . . ?
C19 C17 C16 120.2(2) . . ?
C19 C17 C18 118.5(3) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 C5 121.0(3) . . ?
C3 C4 H4 119.5 . . ?
C10 C7 C8 108.2(2) . . ?
C10 C7 C9 111.1(2) . . ?
C6 C7 C10 109.0(2) . . ?
C6 C7 C8 107.9(2) . . ?
C6 C7 C9 111.8(3) . . ?
C9 C7 C8 108.8(2) . . ?
C16 C19 H19 119.8 3_666 . ?
C17 C19 C16 120.5(3) . 3_666 ?
C17 C19 H19 119.8 . . ?
F1 C18 F2 106.4(2) . . ?
F1 C18 C17 112.1(3) . . ?
F3 C18 F1 105.9(2) . . ?
F3 C18 F2 105.9(3) . . ?
F3 C18 C17 112.6(2) . . ?
F2 C18 C17 113.3(2) . . ?
C10 C15 H15 118.8 . . ?
C10 C15 C14 122.4(2) . . ?
C14 C15 H15 118.8 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.4(3) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.2(3) . . ?
C14 C13 H13 119.9 . . ?
C6 C1 H1 118.7 . . ?
C2 C1 C6 122.6(3) . . ?
C2 C1 H1 118.7 . . ?
C15 C14 H14 120.3 . . ?
C13 C14 C15 119.3(2) . . ?
C13 C14 H14 120.3 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 C4 120.0(3) . . ?
C2 C3 H3 120.0 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.3(3) . . ?
C3 C2 H2 120.4 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C5 C6 C7 -6.4(4) . . . . ?
N1 C5 C6 C1 178.2(2) . . . . ?
N1 C5 C4 C3 -178.1(3) . . . . ?
N1 C11 C12 C13 177.1(3) . . . . ?
N1 C16 C17 C19 -179.1(2) . . . . ?
N1 C16 C17 C18 1.1(4) . . . . ?
C5 N1 C11 C10 28.0(4) . . . . ?
C5 N1 C11 C12 -151.2(3) . . . . ?
C5 N1 C16 C17 -107.3(3) . . . . ?
C5 N1 C16 C19 73.6(3) . . . 3_666 ?
C5 C6 C7 C10 36.8(3) . . . . ?
C5 C6 C7 C8 -80.4(3) . . . . ?
C5 C6 C7 C9 160.0(2) . . . . ?
C5 C6 C1 C2 0.8(5) . . . . ?
C5 C4 C3 C2 -0.9(5) . . . . ?
C10 C11 C12 C13 -2.1(4) . . . . ?
C10 C15 C14 C13 -0.9(5) . . . . ?
C11 N1 C5 C6 -28.3(4) . . . . ?
C11 N1 C5 C4 151.6(3) . . . . ?
C11 N1 C16 C17 99.2(3) . . . . ?
C11 N1 C16 C19 -79.9(3) . . . 3_666 ?
C11 C10 C7 C6 -36.9(3) . . . . ?
C11 C10 C7 C8 80.2(3) . . . . ?
C11 C10 C7 C9 -160.5(3) . . . . ?
C11 C10 C15 C14 -0.4(4) . . . . ?
C11 C12 C13 C14 0.8(5) . . . . ?
C6 C5 C4 C3 1.8(4) . . . . ?
C6 C1 C2 C3 0.1(5) . . . . ?
C16 N1 C5 C6 178.7(2) . . . . ?
C16 N1 C5 C4 -1.4(4) . . . . ?
C16 N1 C11 C10 -178.5(2) . . . . ?
C16 N1 C11 C12 2.3(4) . . . . ?
C16 C17 C19 C16 -0.1(4) . . . 3_666 ?
C16 C17 C18 F1 57.6(3) . . . . ?
C16 C17 C18 F3 -61.8(3) . . . . ?
C16 C17 C18 F2 178.0(2) . . . . ?
C4 C5 C6 C7 173.7(3) . . . . ?
C4 C5 C6 C1 -1.7(4) . . . . ?
C4 C3 C2 C1 -0.1(5) . . . . ?
C7 C10 C11 N1 6.6(4) . . . . ?
C7 C10 C11 C12 -174.2(3) . . . . ?
C7 C10 C15 C14 175.4(3) . . . . ?
C7 C6 C1 C2 -174.5(3) . . . . ?
C19 C16 C17 C19 0.1(4) 3_666 . . . ?
C19 C16 C17 C18 -179.8(2) 3_666 . . . ?
C19 C17 C18 F1 -122.3(3) . . . . ?
C19 C17 C18 F3 118.3(3) . . . . ?
C19 C17 C18 F2 -1.8(4) . . . . ?
C18 C17 C19 C16 179.8(2) . . . 3_666 ?
C15 C10 C11 N1 -177.3(2) . . . . ?
C15 C10 C11 C12 1.9(4) . . . . ?
C15 C10 C7 C6 147.3(3) . . . . ?
C15 C10 C7 C8 -95.6(3) . . . . ?
C15 C10 C7 C9 23.7(4) . . . . ?
C12 C13 C14 C15 0.7(5) . . . . ?
C1 C6 C7 C10 -148.1(3) . . . . ?
C1 C6 C7 C8 94.7(3) . . . . ?
C1 C6 C7 C9 -24.9(4) . . . . ?

_olex2_exptl_crystal_mounting_method 
'single crystal was mounted using glass stick with glue'
_olex2_submission_original_sample_id 2AC-2CF3Ph
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.738
_oxdiff_exptl_absorpt_empirical_full_min 0.659
