# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_pop_0m_c_a
_database_code_depnum_ccdc_archive 'CCDC 2322306'
loop_
_audit_author_name
_audit_author_address
'Shashank Singh'
;Indian Institute of Technology, Delhi
India
;
_audit_update_record             
;
2023-12-28 deposited with the CCDC.	2025-01-31 downloaded from the CCDC.
;
_audit_creation_date             2023-12-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H11 F3 N2'
_chemical_formula_sum            'C14 H11 F3 N2'
_chemical_formula_weight         264.25
_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                   7.639(17)
_cell_length_b                   21.17(3)
_cell_length_c                   8.402(14)
_cell_angle_alpha                90
_cell_angle_beta                 99.33(4)
_cell_angle_gamma                90
_cell_volume                     1341(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1920
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.49
_cell_measurement_theta_min      2.64
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.999
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6479
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1314 before and 0.0521 after correction.
The Ratio of minimum to maximum transmission is 0.8688.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.013
_exptl_crystal_size_mid          0.012
_exptl_crystal_size_min          0.012
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_unetI/netI     0.0891
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7313
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.252
_diffrn_reflns_theta_min         2.638
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1293
_reflns_number_total             3271
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3271
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1673
_refine_ls_R_factor_gt           0.0558
_refine_ls_restrained_S_all      0.990
_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)+(0.0512P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1602
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F1-C11 \\sim F1A-C11
 with sigma of 0.02
 F2-C11 \\sim F2A-C11
 with sigma of 0.02
 F3-C11 \\sim F3A-C11
 with sigma of 0.02
3. Others
 Fixed Sof: F1(0.5) F2(0.5) F3(0.5) F2A(0.5) F3A(0.5) F1A(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B)
4.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10)
4.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.7188(12) 0.8363(4) 0.4512(9) 0.103(2) Uani 0.5 1 d D . P A 1
F2 F 0.8618(9) 0.7656(3) 0.581(2) 0.146(5) Uani 0.5 1 d D . P A 1
F3 F 0.6798(15) 0.8213(6) 0.6861(11) 0.120(2) Uani 0.5 1 d D . P A 1
N1 N -0.2361(3) 0.52199(10) 0.3404(3) 0.0976(8) Uani 1 1 d . . . . .
N2 N 0.0585(3) 0.63361(11) 0.7234(3) 0.0907(7) Uani 1 1 d . . . . .
C1 C 0.1378(3) 0.61803(10) 0.3260(3) 0.0576(6) Uani 1 1 d . . . . .
C2 C 0.2848(3) 0.66247(10) 0.3890(2) 0.0564(6) Uani 1 1 d . . . . .
C3 C 0.5573(3) 0.74649(11) 0.4993(2) 0.0599(6) Uani 1 1 d . . . . .
C4 C 0.0274(3) 0.59778(10) 0.4256(3) 0.0590(6) Uani 1 1 d . . . . .
C5 C 0.0463(3) 0.61783(11) 0.5918(3) 0.0660(7) Uani 1 1 d . . . . .
C6 C -0.1195(3) 0.55558(11) 0.3757(3) 0.0689(7) Uani 1 1 d . . . . .
C7 C 0.4351(3) 0.64169(11) 0.4906(3) 0.0660(7) Uani 1 1 d . . . . .
H7 H 0.444705 0.599569 0.522317 0.079 Uiso 1 1 calc R U . . .
C8 C 0.2719(3) 0.72534(11) 0.3444(3) 0.0689(7) Uani 1 1 d . . . . .
H8 H 0.171680 0.739636 0.276124 0.083 Uiso 1 1 calc R U . . .
C9 C 0.4069(3) 0.76714(11) 0.4006(3) 0.0694(7) Uani 1 1 d . . . . .
H9 H 0.395849 0.809511 0.371361 0.083 Uiso 1 1 calc R U . . .
C10 C 0.5712(3) 0.68366(12) 0.5451(3) 0.0678(7) Uani 1 1 d . . . . .
H10 H 0.672124 0.669517 0.612693 0.081 Uiso 1 1 calc R U . . .
C11 C 0.7056(4) 0.79063(16) 0.5536(4) 0.0793(7) Uani 1 1 d D . . . .
C12 C 0.1196(3) 0.59875(12) 0.1521(3) 0.0754(7) Uani 1 1 d . . . . .
H12A H 0.111516 0.636446 0.085685 0.090 Uiso 1 1 calc R U . . .
H12B H 0.009943 0.575321 0.123097 0.090 Uiso 1 1 calc R U . . .
C13 C 0.2740(4) 0.55810(12) 0.1148(3) 0.0885(8) Uani 1 1 d . . . . .
H13A H 0.261729 0.552465 -0.001088 0.106 Uiso 1 1 calc R U . . .
H13B H 0.384246 0.580502 0.149929 0.106 Uiso 1 1 calc R U . . .
C14 C 0.2849(4) 0.49426(14) 0.1937(4) 0.1128(10) Uani 1 1 d . . . . .
H14A H 0.378238 0.470200 0.158903 0.169 Uiso 1 1 calc R U . . .
H14B H 0.174120 0.472515 0.164050 0.169 Uiso 1 1 calc R U . . .
H14C H 0.309224 0.499268 0.308778 0.169 Uiso 1 1 calc R U . . .
F2A F 0.8374(16) 0.7817(9) 0.4782(18) 0.184(7) Uani 0.5 1 d D . P A 2
F3A F 0.7862(16) 0.7819(7) 0.7033(9) 0.133(3) Uani 0.5 1 d D . P A 2
F1A F 0.6651(14) 0.8498(3) 0.546(3) 0.200(5) Uani 0.5 1 d D . P A 2


_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 C11 1.308(6) . ?
F2 C11 1.291(7) . ?
F3 C11 1.330(6) . ?
N1 C6 1.141(3) . ?
N2 C5 1.144(3) . ?
C1 C2 1.495(3) . ?
C1 C4 1.351(3) . ?
C1 C12 1.501(4) . ?
C2 C7 1.387(3) . ?
C2 C8 1.382(4) . ?
C3 C9 1.375(4) . ?
C3 C10 1.384(4) . ?
C3 C11 1.483(4) . ?
C4 C5 1.444(4) . ?
C4 C6 1.442(4) . ?
C7 H7 0.9300 . ?
C7 C10 1.388(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.382(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 F2A 1.288(7) . ?
C11 F3A 1.321(6) . ?
C11 F1A 1.289(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.533(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.502(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C2 C1 C12 117.5(2) . . ?
C4 C1 C2 119.3(2) . . ?
C4 C1 C12 123.2(2) . . ?
C7 C2 C1 121.2(2) . . ?
C8 C2 C1 119.6(2) . . ?
C8 C2 C7 119.2(2) . . ?
C9 C3 C10 119.5(2) . . ?
C9 C3 C11 120.5(3) . . ?
C10 C3 C11 120.0(2) . . ?
C1 C4 C5 122.1(2) . . ?
C1 C4 C6 123.4(2) . . ?
C6 C4 C5 114.5(2) . . ?
N2 C5 C4 179.0(3) . . ?
N1 C6 C4 178.2(3) . . ?
C2 C7 H7 120.0 . . ?
C2 C7 C10 120.1(2) . . ?
C10 C7 H7 120.0 . . ?
C2 C8 H8 119.7 . . ?
C2 C8 C9 120.5(2) . . ?
C9 C8 H8 119.7 . . ?
C3 C9 C8 120.4(2) . . ?
C3 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C3 C10 C7 120.3(2) . . ?
C3 C10 H10 119.9 . . ?
C7 C10 H10 119.9 . . ?
F1 C11 F3 103.2(5) . . ?
F1 C11 C3 113.5(3) . . ?
F2 C11 F1 104.6(6) . . ?
F2 C11 F3 108.1(5) . . ?
F2 C11 C3 115.8(4) . . ?
F3 C11 C3 110.8(4) . . ?
F2A C11 C3 112.1(4) . . ?
F2A C11 F3A 99.6(6) . . ?
F2A C11 F1A 108.6(7) . . ?
F3A C11 C3 114.8(3) . . ?
F1A C11 C3 115.6(5) . . ?
F1A C11 F3A 104.7(6) . . ?
C1 C12 H12A 108.9 . . ?
C1 C12 H12B 108.9 . . ?
C1 C12 C13 113.5(2) . . ?
H12A C12 H12B 107.7 . . ?
C13 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
C12 C13 H13A 108.8 . . ?
C12 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 C12 113.8(2) . . ?
C14 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
C1 C2 C7 C10 178.8(2) . . . . ?
C1 C2 C8 C9 -179.6(2) . . . . ?
C1 C12 C13 C14 66.4(3) . . . . ?
C2 C1 C4 C5 0.2(3) . . . . ?
C2 C1 C4 C6 179.2(2) . . . . ?
C2 C1 C12 C13 67.0(3) . . . . ?
C2 C7 C10 C3 0.4(3) . . . . ?
C2 C8 C9 C3 1.2(4) . . . . ?
C4 C1 C2 C7 74.6(3) . . . . ?
C4 C1 C2 C8 -105.9(3) . . . . ?
C4 C1 C12 C13 -113.7(3) . . . . ?
C7 C2 C8 C9 -0.1(3) . . . . ?
C8 C2 C7 C10 -0.7(3) . . . . ?
C9 C3 C10 C7 0.6(3) . . . . ?
C9 C3 C11 F1 -29.3(8) . . . . ?
C9 C3 C11 F2 -150.3(10) . . . . ?
C9 C3 C11 F3 86.2(9) . . . . ?
C9 C3 C11 F2A -104.7(12) . . . . ?
C9 C3 C11 F3A 142.5(10) . . . . ?
C9 C3 C11 F1A 20.4(14) . . . . ?
C10 C3 C9 C8 -1.4(3) . . . . ?
C10 C3 C11 F1 149.2(7) . . . . ?
C10 C3 C11 F2 28.2(11) . . . . ?
C10 C3 C11 F3 -95.2(9) . . . . ?
C10 C3 C11 F2A 73.9(12) . . . . ?
C10 C3 C11 F3A -38.9(10) . . . . ?
C10 C3 C11 F1A -161.0(14) . . . . ?
C11 C3 C9 C8 177.2(2) . . . . ?
C11 C3 C10 C7 -178.0(2) . . . . ?
C12 C1 C2 C7 -106.1(3) . . . . ?
C12 C1 C2 C8 73.4(3) . . . . ?
C12 C1 C4 C5 -179.0(2) . . . . ?
C12 C1 C4 C6 -0.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_fdfgdh_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2322456'
loop_
_audit_author_name
_audit_author_address
'Shashank Singh'
;Indian Institute of Technology, Delhi
India
;
_audit_update_record             
;
2023-12-29 deposited with the CCDC.	2025-01-31 downloaded from the CCDC.
;
_audit_creation_date             2023-12-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H11 F3 N2'
_chemical_formula_sum            'C19 H11 F3 N2'
_chemical_formula_weight         324.30
_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                   13.1854(9)
_cell_length_b                   8.7585(6)
_cell_length_c                   14.5343(11)
_cell_angle_alpha                90
_cell_angle_beta                 101.895(3)
_cell_angle_gamma                90
_cell_volume                     1642.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4943
_cell_measurement_temperature    303(2)
_cell_measurement_theta_max      20.54
_cell_measurement_theta_min      2.73
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.999
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6414
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0992 before and 0.0742 after correction.
The Ratio of minimum to maximum transmission is 0.8601.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.013
_exptl_crystal_size_mid          0.012
_exptl_crystal_size_min          0.012
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0993
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            53234
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.336
_diffrn_reflns_theta_min         2.731
_diffrn_ambient_temperature      303.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2137
_reflns_number_total             4093
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         4093
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1351
_refine_ls_R_factor_gt           0.0826
_refine_ls_restrained_S_all      1.066
_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)+(0.1322P)²+0.6936P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2457
_refine_ls_wR_factor_ref         0.2981
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C18-F2 \\sim C18-F2A
 with sigma of 0.04
 C18-F3 \\sim C18-F3A
 with sigma of 0.02
 F2-F3 \\sim F2-F3A
 with sigma of 0.02
 C18-F1 \\sim C18-F1A
 with sigma of 0.02
 F1-F3 \\sim F1A-F3
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F2) = Uanis(F3A) = Uanis(F3) = Uanis(F1) = Uanis(F1A) = Uanis(F2A)
4. Others
 Fixed Sof: F1(0.5) F2(0.5) F3(0.5) F2A(0.5) F3A(0.5) F1A(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13),
 C15(H15), C16(H16), C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C1 C 0.1489(2) 0.0725(3) 0.38449(18) 0.0592(7) Uani 1 1 d . . . . .
C19 C 0.1806(2) 0.0965(3) 0.48745(18) 0.0613(7) Uani 1 1 d . . . . .
C2 C 0.2310(2) 0.2363(3) 0.5249(2) 0.0694(8) Uani 1 1 d . . . . .
H2 H 0.239631 0.252137 0.589318 0.083 Uiso 1 1 calc R U . . .
C3 C 0.2661(2) 0.3444(3) 0.4750(2) 0.0671(7) Uani 1 1 d . . . . .
H3 H 0.254375 0.331630 0.410187 0.080 Uiso 1 1 calc R U . . .
C4 C 0.1646(2) -0.0158(3) 0.5478(2) 0.0671(7) Uani 1 1 d . . . . .
N006 N 0.0667(3) -0.2660(4) 0.4983(2) 0.1024(11) Uani 1 1 d . . . . .
C5 C 0.0867(2) 0.1780(4) 0.3284(2) 0.0712(8) Uani 1 1 d . . . . .
H5 H 0.065727 0.265706 0.355421 0.085 Uiso 1 1 calc R U . . .
C6 C 0.3217(2) 0.4818(3) 0.5147(2) 0.0702(8) Uani 1 1 d . . . . .
C7 C 0.1800(2) -0.0563(4) 0.3422(2) 0.0711(8) Uani 1 1 d . . . . .
H7 H 0.221882 -0.128709 0.378341 0.085 Uiso 1 1 calc R U . . .
C8 C 0.1103(3) -0.1551(4) 0.5179(2) 0.0749(8) Uani 1 1 d . . . . .
C9 C 0.1981(3) -0.0023(4) 0.6475(2) 0.0834(10) Uani 1 1 d . . . . .
N00C N 0.2248(3) 0.0056(4) 0.7265(2) 0.1154(12) Uani 1 1 d . . . . .
C10 C 0.0556(3) 0.1548(4) 0.2335(2) 0.0798(9) Uani 1 1 d . . . . .
H10 H 0.013257 0.226411 0.196942 0.096 Uiso 1 1 calc R U . . .
C11 C 0.1488(3) -0.0770(4) 0.2465(2) 0.0825(9) Uani 1 1 d . . . . .
H11 H 0.170550 -0.163022 0.218413 0.099 Uiso 1 1 calc R U . . .
C12 C 0.0859(3) 0.0281(4) 0.1922(2) 0.0847(10) Uani 1 1 d . . . . .
H12 H 0.064315 0.012772 0.127771 0.102 Uiso 1 1 calc R U . . .
C13 C 0.3645(3) 0.5776(4) 0.4582(3) 0.0902(11) Uani 1 1 d . . . . .
H13 H 0.354467 0.557175 0.394157 0.108 Uiso 1 1 calc R U . . .
C14 C 0.4354(3) 0.7352(4) 0.5888(3) 0.1006(13) Uani 1 1 d . . . . .
C15 C 0.3345(3) 0.5187(4) 0.6089(3) 0.0934(11) Uani 1 1 d . . . . .
H15 H 0.304638 0.456866 0.648094 0.112 Uiso 1 1 calc R U . . .
C16 C 0.4217(4) 0.7027(5) 0.4944(3) 0.1085(14) Uani 1 1 d . . . . .
H16 H 0.451150 0.765227 0.455286 0.130 Uiso 1 1 calc R U . . .
C17 C 0.3901(4) 0.6441(5) 0.6457(3) 0.1076(13) Uani 1 1 d . . . . .
H17 H 0.397240 0.667493 0.709081 0.129 Uiso 1 1 calc R U . . .
C18 C 0.4965(6) 0.8621(7) 0.6321(5) 0.150(2) Uani 1 1 d D . . . .
F1 F 0.4895(5) 0.8895(7) 0.7268(5) 0.1519(14) Uani 0.5 1 d D . P A 1
F2 F 0.5658(6) 0.9135(9) 0.5612(5) 0.1519(14) Uani 0.5 1 d D . P A 1
F3 F 0.5802(5) 0.8234(7) 0.6956(5) 0.1519(14) Uani 0.5 1 d D . P A 1
F2A F 0.4365(6) 1.0002(9) 0.6003(6) 0.1519(14) Uani 0.5 1 d D . P A 2
F3A F 0.5785(6) 0.8988(9) 0.6180(6) 0.1519(14) Uani 0.5 1 d D . P A 2
F1A F 0.4602(6) 0.9892(10) 0.6469(6) 0.1519(14) Uani 0.5 1 d D . P A 2


_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 C19 1.483(4) . ?
C1 C5 1.384(4) . ?
C1 C7 1.386(4) . ?
C19 C2 1.445(4) . ?
C19 C4 1.363(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.332(4) . ?
C3 H3 0.9300 . ?
C3 C6 1.465(4) . ?
C4 C8 1.436(4) . ?
C4 C9 1.431(4) . ?
N006 C8 1.135(4) . ?
C5 H5 0.9300 . ?
C5 C10 1.371(4) . ?
C6 C13 1.373(5) . ?
C6 C15 1.383(5) . ?
C7 H7 0.9300 . ?
C7 C11 1.378(4) . ?
C9 N00C 1.132(4) . ?
C10 H10 0.9300 . ?
C10 C12 1.361(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.374(5) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C13 C16 1.372(5) . ?
C14 C16 1.377(6) . ?
C14 C17 1.371(6) . ?
C14 C18 1.439(6) . ?
C15 H15 0.9300 . ?
C15 C17 1.366(5) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 F1 1.419(9) . ?
C18 F2 1.576(11) . ?
C18 F3 1.329(8) . ?
C18 F2A 1.467(10) . ?
C18 F3A 1.186(9) . ?
C18 F1A 1.248(10) . ?
F2A F1A 0.691(12) . ?

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 C1 C19 120.6(2) . . ?
C5 C1 C7 118.4(3) . . ?
C7 C1 C19 121.0(2) . . ?
C2 C19 C1 120.8(2) . . ?
C4 C19 C1 119.9(2) . . ?
C4 C19 C2 119.3(2) . . ?
C19 C2 H2 117.2 . . ?
C3 C2 C19 125.6(3) . . ?
C3 C2 H2 117.2 . . ?
C2 C3 H3 117.5 . . ?
C2 C3 C6 124.9(3) . . ?
C6 C3 H3 117.5 . . ?
C19 C4 C8 123.5(3) . . ?
C19 C4 C9 122.4(3) . . ?
C9 C4 C8 114.0(3) . . ?
C1 C5 H5 119.6 . . ?
C10 C5 C1 120.8(3) . . ?
C10 C5 H5 119.6 . . ?
C13 C6 C3 120.0(3) . . ?
C13 C6 C15 117.9(3) . . ?
C15 C6 C3 122.0(3) . . ?
C1 C7 H7 120.0 . . ?
C11 C7 C1 120.1(3) . . ?
C11 C7 H7 120.0 . . ?
N006 C8 C4 176.9(3) . . ?
N00C C9 C4 178.8(4) . . ?
C5 C10 H10 119.6 . . ?
C12 C10 C5 120.7(3) . . ?
C12 C10 H10 119.6 . . ?
C7 C11 H11 119.6 . . ?
C12 C11 C7 120.7(3) . . ?
C12 C11 H11 119.6 . . ?
C10 C12 C11 119.3(3) . . ?
C10 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C6 C13 H13 119.4 . . ?
C16 C13 C6 121.3(4) . . ?
C16 C13 H13 119.4 . . ?
C16 C14 C18 122.8(5) . . ?
C17 C14 C16 119.8(4) . . ?
C17 C14 C18 117.5(5) . . ?
C6 C15 H15 119.3 . . ?
C17 C15 C6 121.4(4) . . ?
C17 C15 H15 119.3 . . ?
C13 C16 C14 119.7(4) . . ?
C13 C16 H16 120.1 . . ?
C14 C16 H16 120.1 . . ?
C14 C17 H17 120.1 . . ?
C15 C17 C14 119.9(4) . . ?
C15 C17 H17 120.1 . . ?
C14 C18 F2 106.5(5) . . ?
C14 C18 F2A 106.4(5) . . ?
F1 C18 C14 114.3(6) . . ?
F1 C18 F2 138.4(5) . . ?
F3 C18 C14 114.6(5) . . ?
F3 C18 F1 65.1(5) . . ?
F3 C18 F2 90.9(7) . . ?
F3A C18 C14 125.7(7) . . ?
F3A C18 F2A 100.0(7) . . ?
F3A C18 F1A 100.6(7) . . ?
F1A C18 C14 124.3(7) . . ?
F1A C18 F2A 28.0(5) . . ?
C18 F3 F1 60.3(5) . . ?
F1A F2A C18 58.1(11) . . ?
F2A F1A C18 93.9(12) . . ?

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
C1 C19 C2 C3 -9.6(5) . . . . ?
C1 C19 C4 C8 -5.1(5) . . . . ?
C1 C19 C4 C9 176.8(3) . . . . ?
C1 C5 C10 C12 -0.6(5) . . . . ?
C1 C7 C11 C12 -0.7(5) . . . . ?
C19 C1 C5 C10 -178.7(3) . . . . ?
C19 C1 C7 C11 179.4(3) . . . . ?
C19 C2 C3 C6 -176.7(3) . . . . ?
C2 C19 C4 C8 176.5(3) . . . . ?
C2 C19 C4 C9 -1.6(5) . . . . ?
C2 C3 C6 C13 172.8(3) . . . . ?
C2 C3 C6 C15 -6.2(5) . . . . ?
C3 C6 C13 C16 -176.5(3) . . . . ?
C3 C6 C15 C17 177.4(4) . . . . ?
C4 C19 C2 C3 168.8(3) . . . . ?
C5 C1 C19 C2 -54.0(4) . . . . ?
C5 C1 C19 C4 127.6(3) . . . . ?
C5 C1 C7 C11 -0.1(5) . . . . ?
C5 C10 C12 C11 -0.3(6) . . . . ?
C6 C13 C16 C14 -1.2(6) . . . . ?
C6 C15 C17 C14 -0.6(7) . . . . ?
C7 C1 C19 C2 126.5(3) . . . . ?
C7 C1 C19 C4 -51.9(4) . . . . ?
C7 C1 C5 C10 0.7(5) . . . . ?
C7 C11 C12 C10 0.9(5) . . . . ?
C13 C6 C15 C17 -1.6(6) . . . . ?
C14 C18 F3 F1 -106.7(7) . . . . ?
C14 C18 F2A F1A 134.2(14) . . . . ?
C14 C18 F1A F2A -56.3(17) . . . . ?
C15 C6 C13 C16 2.5(6) . . . . ?
C16 C14 C17 C15 2.1(7) . . . . ?
C16 C14 C18 F1 171.6(5) . . . . ?
C16 C14 C18 F2 -17.0(8) . . . . ?
C16 C14 C18 F3 -115.9(7) . . . . ?
C16 C14 C18 F2A 72.2(8) . . . . ?
C16 C14 C18 F3A -43.6(10) . . . . ?
C16 C14 C18 F1A 96.2(10) . . . . ?
C17 C14 C16 C13 -1.2(7) . . . . ?
C17 C14 C18 F1 -8.8(8) . . . . ?
C17 C14 C18 F2 162.6(5) . . . . ?
C17 C14 C18 F3 63.7(9) . . . . ?
C17 C14 C18 F2A -108.2(7) . . . . ?
C17 C14 C18 F3A 136.0(8) . . . . ?
C17 C14 C18 F1A -84.2(9) . . . . ?
C18 C14 C16 C13 178.4(5) . . . . ?
C18 C14 C17 C15 -177.5(5) . . . . ?
F2 C18 F3 F1 144.7(5) . . . . ?
F3A C18 F2A F1A -93.8(14) . . . . ?
F3A C18 F1A F2A 91.4(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
