# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2020

####################################################################### 
# 
# 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_Pro_F_fin
_database_code_depnum_ccdc_archive 'CCDC 1988466'
loop_
_audit_author_name
_audit_author_address
'Anna Pietrzak'
;Lodz University of Technology
Poland
;
_audit_update_record             
;
2020-03-05 deposited with the CCDC.	2020-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H11 F3 N3 O'
_chemical_formula_sum            'C20 H11 F3 N3 O'
_chemical_formula_weight         366.32

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 0.0000 0.0000 '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'
N N 0.0311 0.0180 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.5809(2)
_cell_length_b                   19.0996(2)
_cell_length_c                   11.1263(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.022(2)
_cell_angle_gamma                90
_cell_volume                     1563.00(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(1)
_cell_measurement_reflns_used    22656
_cell_measurement_theta_min      4.0710
_cell_measurement_theta_max      78.9140

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_F_000             748
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.158
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.038
_exptl_absorpt_coefficient_mu    1.055
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.782
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.880
_oxdiff_exptl_absorpt_empirical_full_max 1.209
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100.0(1)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32254
_diffrn_reflns_av_unetI/netI     0.0111
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.630
_diffrn_reflns_theta_max         79.110
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3349
_reflns_number_gt                3158
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0582P)²+0.5161P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3349
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.1036
_refine_ls_wR_factor_gt          0.1020
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.32205(15) 0.61932(5) 0.83014(10) 0.0201(2) Uani 1 1 d . . . . .
C2 C 0.20038(15) 0.67398(6) 0.78979(11) 0.0226(2) Uani 1 1 d . . . . .
H2 H 0.186180 0.709160 0.844472 0.027 Uiso 1 1 calc R U . . .
C3 C 0.10041(15) 0.67561(6) 0.66740(11) 0.0225(2) Uani 1 1 d . . . . .
H3 H 0.018901 0.711905 0.639783 0.027 Uiso 1 1 calc R U . . .
C4 C 0.12246(14) 0.62310(5) 0.58679(10) 0.0189(2) Uani 1 1 d . . . . .
O5 O 0.01832(10) 0.62767(4) 0.46679(7) 0.02159(18) Uani 1 1 d . . . . .
C6 C 0.04697(14) 0.57827(5) 0.38286(10) 0.0190(2) Uani 1 1 d . . . . .
C7 C -0.04652(15) 0.58426(6) 0.26029(10) 0.0224(2) Uani 1 1 d . . . . .
H7 H -0.127581 0.620938 0.234587 0.027 Uiso 1 1 calc R U . . .
C8 C -0.01706(15) 0.53411(6) 0.17534(10) 0.0239(2) Uani 1 1 d . . . . .
H8 H -0.078281 0.538355 0.092462 0.029 Uiso 1 1 calc R U . . .
C9 C 0.10046(15) 0.47852(6) 0.21136(10) 0.0218(2) Uani 1 1 d . . . . .
H9 H 0.118425 0.446246 0.152873 0.026 Uiso 1 1 calc R U . . .
C00R C 0.42319(16) 0.61487(6) 0.96340(10) 0.0237(2) Uani 1 1 d . . . . .
C10 C 0.19282(14) 0.47074(6) 0.33629(10) 0.0184(2) Uani 1 1 d . . . . .
C11 C 0.16520(13) 0.52227(5) 0.42024(9) 0.0172(2) Uani 1 1 d . . . . .
N12 N 0.30254(12) 0.41389(5) 0.37677(8) 0.01813(19) Uani 1 1 d . . . . .
C13 C 0.37949(13) 0.41225(5) 0.49833(9) 0.0162(2) Uani 1 1 d . . . . .
C14 C 0.49406(13) 0.35068(5) 0.54762(9) 0.0167(2) Uani 1 1 d . . . . .
C15 C 0.51989(14) 0.29736(6) 0.46772(10) 0.0196(2) Uani 1 1 d . . . . .
H15 H 0.465526 0.300620 0.383483 0.023 Uiso 1 1 calc R U . . .
C16 C 0.62621(15) 0.23947(6) 0.51316(10) 0.0230(2) Uani 1 1 d . . . . .
H16 H 0.641196 0.203869 0.459465 0.028 Uiso 1 1 calc R U . . .
C17 C 0.71037(15) 0.23458(6) 0.63881(10) 0.0226(2) Uani 1 1 d . . . . .
H17 H 0.781375 0.195802 0.669309 0.027 Uiso 1 1 calc R U . . .
C18 C 0.68752(15) 0.28801(6) 0.71824(10) 0.0214(2) Uani 1 1 d . . . . .
H18 H 0.745069 0.285215 0.802016 0.026 Uiso 1 1 calc R U . . .
C19 C 0.57962(14) 0.34554(5) 0.67383(10) 0.0191(2) Uani 1 1 d . . . . .
H19 H 0.564076 0.380783 0.728022 0.023 Uiso 1 1 calc R U . . .
N20 N 0.36847(11) 0.45991(4) 0.58492(8) 0.01683(19) Uani 1 1 d . . . . .
N21 N 0.25961(11) 0.51537(4) 0.54327(8) 0.01644(19) Uani 1 1 d . . . . .
C22 C 0.24367(14) 0.56794(5) 0.62784(10) 0.0171(2) Uani 1 1 d . . . . .
C23 C 0.34488(14) 0.56608(5) 0.75035(10) 0.0180(2) Uani 1 1 d . . . . .
H23 H 0.426341 0.529797 0.778183 0.022 Uiso 1 1 calc R U . . .
F24 F 0.59086(11) 0.58853(5) 0.97827(7) 0.0405(2) Uani 1 1 d . . . . .
F25 F 0.33918(13) 0.57427(5) 1.02985(7) 0.0474(2) Uani 1 1 d . . . . .
F26 F 0.44500(11) 0.67721(4) 1.01936(7) 0.0371(2) 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
C1 C23 1.3881(14) . ?
C1 C2 1.3933(15) . ?
C1 C00R 1.4975(15) . ?
C2 C3 1.3891(16) . ?
C2 H2 0.9300 . ?
C3 C4 1.3823(15) . ?
C3 H3 0.9300 . ?
C4 O5 1.3793(13) . ?
C4 C22 1.3998(14) . ?
O5 C6 1.3813(13) . ?
C6 C7 1.3809(15) . ?
C6 C11 1.3927(15) . ?
C7 C8 1.4011(17) . ?
C7 H7 0.9300 . ?
C8 C9 1.3815(16) . ?
C8 H8 0.9300 . ?
C9 C10 1.4046(14) . ?
C9 H9 0.9300 . ?
C00R F25 1.3348(14) . ?
C00R F26 1.3352(13) . ?
C00R F24 1.3395(14) . ?
C10 N12 1.3755(14) . ?
C10 C11 1.4071(15) . ?
C11 N21 1.3887(13) . ?
N12 C13 1.3373(13) . ?
C13 N20 1.3427(13) . ?
C13 C14 1.4855(14) . ?
C14 C15 1.3966(14) . ?
C14 C19 1.4004(14) . ?
C15 C16 1.3894(15) . ?
C15 H15 0.9300 . ?
C16 C17 1.3922(16) . ?
C16 H16 0.9300 . ?
C17 C18 1.3880(15) . ?
C17 H17 0.9300 . ?
C18 C19 1.3874(15) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
N20 N21 1.3537(12) . ?
N21 C22 1.4012(13) . ?
C22 C23 1.3933(14) . ?
C23 H23 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C23 C1 C2 121.21(10) . . ?
C23 C1 C00R 118.58(9) . . ?
C2 C1 C00R 120.11(10) . . ?
C3 C2 C1 119.60(10) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 119.79(10) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
O5 C4 C3 116.83(9) . . ?
O5 C4 C22 122.68(9) . . ?
C3 C4 C22 120.48(10) . . ?
C4 O5 C6 117.67(8) . . ?
C7 C6 O5 118.94(9) . . ?
C7 C6 C11 119.86(10) . . ?
O5 C6 C11 121.19(9) . . ?
C6 C7 C8 118.81(10) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 H7 120.6 . . ?
C9 C8 C7 121.79(10) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C8 C9 C10 120.01(10) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
F25 C00R F26 106.36(9) . . ?
F25 C00R F24 106.21(10) . . ?
F26 C00R F24 105.72(9) . . ?
F25 C00R C1 112.50(9) . . ?
F26 C00R C1 112.76(9) . . ?
F24 C00R C1 112.73(9) . . ?
N12 C10 C9 121.63(10) . . ?
N12 C10 C11 120.68(9) . . ?
C9 C10 C11 117.66(10) . . ?
N21 C11 C6 120.53(9) . . ?
N21 C11 C10 117.64(9) . . ?
C6 C11 C10 121.83(10) . . ?
C13 N12 C10 115.51(9) . . ?
N12 C13 N20 128.47(9) . . ?
N12 C13 C14 117.69(9) . . ?
N20 C13 C14 113.84(9) . . ?
C15 C14 C19 119.01(9) . . ?
C15 C14 C13 120.12(9) . . ?
C19 C14 C13 120.86(9) . . ?
C16 C15 C14 120.48(10) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 120.20(10) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 119.51(10) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C19 C18 C17 120.62(10) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C14 120.17(9) . . ?
C18 C19 H19 119.9 . . ?
C14 C19 H19 119.9 . . ?
C13 N20 N21 115.06(8) . . ?
N20 N21 C11 122.52(8) . . ?
N20 N21 C22 118.39(8) . . ?
C11 N21 C22 119.09(9) . . ?
C23 C22 C4 120.05(9) . . ?
C23 C22 N21 121.47(9) . . ?
C4 C22 N21 118.48(9) . . ?
C1 C23 C22 118.86(9) . . ?
C1 C23 H23 120.6 . . ?
C22 C23 H23 120.6 . . ?

_refine_diff_density_max         0.294
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.045


_exptl_crystal_preparation       'Magnetic properties'
