# Electronic Supplementary Material (ESI) for ChemComm.
# 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_3ga
_database_code_depnum_ccdc_archive 'CCDC 2193498'
loop_
_audit_author_name
_audit_author_address
'Biao Xiong'
;Nantong University
China
;
_audit_update_record             
;
2022-07-29 deposited with the CCDC.	2022-10-17 downloaded from the CCDC.
;
_audit_creation_date             2022-07-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H12 F3 N O'
_chemical_formula_sum            'C19 H12 F3 N O'
_chemical_formula_weight         327.30
_chemical_melting_point          389.15
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/n 1'
_space_group_name_Hall           '-P 2yn'
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                   7.2901(13)
_cell_length_b                   7.7946(13)
_cell_length_c                   26.574(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.936(15)
_cell_angle_gamma                90
_cell_volume                     1501.9(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    883
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.5440
_cell_measurement_theta_min      2.6920
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59782
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_unetI/netI     0.1097
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.856
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            8471
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.856
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.286
_diffrn_reflns_theta_min         2.724
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.856
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      6.00  38.40   0.90   10.00    --   15.49  57.00 -90.00   36
  2  ω    -23.00  22.00   0.90   10.00    --  -16.28 -99.00  90.00   50
  3  ω    -20.00   5.20   0.90   10.00    --  -16.28 -99.00   0.00   28
  4  ω    -84.00  -3.00   0.90   10.00    --  -16.28 -57.00-150.00   90
  5  ω    -82.00 -46.90   0.90   10.00    --  -16.28 -77.00 150.00   39
  6  ω     38.00  87.50   0.90   10.00    --   15.49 178.00 150.00   55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0218367000
_diffrn_orient_matrix_UB_12      0.0461294000
_diffrn_orient_matrix_UB_13      -0.0228259000
_diffrn_orient_matrix_UB_21      0.0130992000
_diffrn_orient_matrix_UB_22      -0.0754938000
_diffrn_orient_matrix_UB_23      -0.0140858000
_diffrn_orient_matrix_UB_31      -0.0945419000
_diffrn_orient_matrix_UB_32      -0.0210734000
_diffrn_orient_matrix_UB_33      0.0004468000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\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                1566
_reflns_number_total             3506
_reflns_odcompleteness_completeness 99.88
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3506
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1837
_refine_ls_R_factor_gt           0.0776
_refine_ls_restrained_S_all      1.043
_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)+(0.0381P)²+0.8047P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1367
_refine_ls_wR_factor_ref         0.1780
_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:
 C12(H12), C2(H2), C16(H16), C3(H3), C8(H8), C13(H13), C14(H14), C18(H18),
 C5(H5), C7(H7), C6(H6), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
N1 N 0.9153(4) 0.8079(3) 0.09166(10) 0.0340(7) Uani 1 1 d . . . . .
F3 F 0.7853(3) 0.6642(3) -0.03723(8) 0.0741(8) Uani 1 1 d . . . . .
C10 C 1.0696(5) 0.7382(4) 0.12321(13) 0.0355(8) Uani 1 1 d . . . . .
O1 O 1.2517(4) 0.7423(3) 0.05312(10) 0.0546(8) Uani 1 1 d . . . . .
F1 F 0.6396(4) 0.6432(4) 0.02730(10) 0.0941(10) Uani 1 1 d . . . . .
C1 C 1.2334(5) 0.7088(4) 0.10351(14) 0.0421(9) Uani 1 1 d . . . . .
C9 C 1.0537(5) 0.6984(4) 0.17488(14) 0.0396(9) Uani 1 1 d . . . . .
C11 C 0.8786(5) 0.9878(4) 0.10186(12) 0.0344(8) Uani 1 1 d . . . . .
F2 F 0.6682(4) 0.8841(4) -0.00748(10) 0.1019(12) Uani 1 1 d . . . . .
C4 C 1.2093(6) 0.6263(5) 0.20376(15) 0.0497(11) Uani 1 1 d . . . . .
C17 C 0.9304(5) 0.7673(4) 0.03960(13) 0.0381(9) Uani 1 1 d . . . . .
C12 C 1.0168(5) 1.0973(5) 0.11966(13) 0.0433(10) Uani 1 1 d . . . . .
H12 H 1.1376 1.0577 0.1244 0.052 Uiso 1 1 calc R . . . .
C2 C 1.3860(6) 0.6395(5) 0.13217(17) 0.0563(11) Uani 1 1 d . . . . .
H2 H 1.4951 0.6207 0.1177 0.068 Uiso 1 1 calc R . . . .
C16 C 0.6979(5) 1.0469(5) 0.09464(14) 0.0491(10) Uani 1 1 d . . . . .
H16 H 0.6023 0.9728 0.0835 0.059 Uiso 1 1 calc R . . . .
C3 C 1.3743(6) 0.6000(5) 0.18092(18) 0.0581(12) Uani 1 1 d . . . . .
H3 H 1.4767 0.5545 0.2001 0.070 Uiso 1 1 calc R . . . .
C8 C 0.8905(6) 0.7258(5) 0.19812(15) 0.0502(11) Uani 1 1 d . . . . .
H8 H 0.7883 0.7741 0.1795 0.060 Uiso 1 1 calc R . . . .
C13 C 0.9793(6) 1.2659(5) 0.13059(15) 0.0548(11) Uani 1 1 d . . . . .
H13 H 1.0742 1.3387 0.1432 0.066 Uiso 1 1 calc R . . . .
C14 C 0.8026(6) 1.3258(5) 0.12281(15) 0.0560(12) Uani 1 1 d . . . . .
H14 H 0.7772 1.4396 0.1300 0.067 Uiso 1 1 calc R . . . .
C18 C 1.0890(6) 0.7394(5) 0.02236(15) 0.0496(10) Uani 1 1 d . . . . .
H18 H 1.0916 0.7169 -0.0119 0.060 Uiso 1 1 calc R . . . .
C5 C 1.1937(7) 0.5827(6) 0.25435(18) 0.0707(14) Uani 1 1 d . . . . .
H5 H 1.2947 0.5356 0.2737 0.085 Uiso 1 1 calc R . . . .
C7 C 0.8810(7) 0.6824(6) 0.24754(16) 0.0681(13) Uani 1 1 d . . . . .
H7 H 0.7733 0.7020 0.2626 0.082 Uiso 1 1 calc R . . . .
C19 C 0.7574(6) 0.7412(6) 0.00617(15) 0.0511(11) Uani 1 1 d . . . . .
C6 C 1.0350(8) 0.6077(7) 0.27558(17) 0.0789(16) Uani 1 1 d . . . . .
H6 H 1.0277 0.5753 0.3090 0.095 Uiso 1 1 calc R . . . .
C15 C 0.6620(6) 1.2182(5) 0.10429(15) 0.0580(12) Uani 1 1 d . . . . .
H15 H 0.5424 1.2602 0.0982 0.070 Uiso 1 1 calc R . . . .


_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
N1 C10 1.438(4) . ?
N1 C11 1.458(4) . ?
N1 C17 1.435(4) . ?
F3 C19 1.334(4) . ?
C10 C1 1.372(5) . ?
C10 C9 1.424(5) . ?
O1 C1 1.384(4) . ?
O1 C18 1.369(4) . ?
F1 C19 1.318(5) . ?
C1 C2 1.391(5) . ?
C9 C4 1.419(5) . ?
C9 C8 1.412(5) . ?
C11 C12 1.367(5) . ?
C11 C16 1.390(5) . ?
F2 C19 1.322(5) . ?
C4 C3 1.417(6) . ?
C4 C5 1.403(6) . ?
C17 C18 1.305(5) . ?
C17 C19 1.480(5) . ?
C12 C13 1.379(5) . ?
C2 C3 1.343(5) . ?
C16 C15 1.389(5) . ?
C8 C7 1.365(5) . ?
C13 C14 1.366(5) . ?
C14 C15 1.375(5) . ?
C5 C6 1.352(6) . ?
C7 C6 1.408(6) . ?

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
C10 N1 C11 113.7(3) . . ?
C17 N1 C10 110.2(3) . . ?
C17 N1 C11 115.2(3) . . ?
C1 C10 N1 120.0(3) . . ?
C1 C10 C9 119.5(3) . . ?
C9 C10 N1 120.5(3) . . ?
C18 O1 C1 114.2(3) . . ?
C10 C1 O1 120.8(3) . . ?
C10 C1 C2 122.3(4) . . ?
O1 C1 C2 116.8(4) . . ?
C4 C9 C10 117.9(4) . . ?
C8 C9 C10 123.0(3) . . ?
C8 C9 C4 119.1(4) . . ?
C12 C11 N1 121.5(3) . . ?
C12 C11 C16 119.6(3) . . ?
C16 C11 N1 118.9(3) . . ?
C3 C4 C9 119.5(4) . . ?
C5 C4 C9 118.3(4) . . ?
C5 C4 C3 122.2(4) . . ?
N1 C17 C19 117.6(3) . . ?
C18 C17 N1 122.3(3) . . ?
C18 C17 C19 119.8(4) . . ?
C11 C12 C13 120.9(4) . . ?
C3 C2 C1 119.4(4) . . ?
C15 C16 C11 119.1(4) . . ?
C2 C3 C4 121.4(4) . . ?
C7 C8 C9 120.8(4) . . ?
C14 C13 C12 119.9(4) . . ?
C13 C14 C15 120.1(4) . . ?
C17 C18 O1 122.1(4) . . ?
C6 C5 C4 121.5(4) . . ?
C8 C7 C6 119.6(5) . . ?
F3 C19 C17 112.6(4) . . ?
F1 C19 F3 105.8(3) . . ?
F1 C19 F2 106.4(4) . . ?
F1 C19 C17 112.1(3) . . ?
F2 C19 F3 104.9(3) . . ?
F2 C19 C17 114.4(3) . . ?
C5 C6 C7 120.6(4) . . ?
C14 C15 C16 120.3(4) . . ?

_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 1.553
_oxdiff_exptl_absorpt_empirical_full_min 0.673
