# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_exp_1461
_database_code_depnum_ccdc_archive 'CCDC 2048733'
loop_
_audit_author_name
_audit_author_address
'huamin Wang'
;University of South China
China
;
_audit_update_record             
;
2020-12-07 deposited with the CCDC.	2021-03-30 downloaded from the CCDC.
;
_audit_creation_date             2020-10-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H10 F3 N3 O'
_chemical_formula_sum            'C14 H10 F3 N3 O'
_chemical_formula_weight         293.25
_chemical_absolute_configuration unk
_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 0.0181 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'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.65470(10)
_cell_length_b                   8.3977(2)
_cell_length_c                   21.0738(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1354.66(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7735
_cell_measurement_temperature    292.62(10)
_cell_measurement_theta_max      73.2550
_cell_measurement_theta_min      5.6610
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.058
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.26
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12707
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.073
_diffrn_reflns_theta_max         67.073
_diffrn_reflns_theta_min         4.196
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.62(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -35.00  16.00   1.00    1.00    --    0.00 -38.00  60.00   51
  2  ω    -36.00  19.00   1.00    1.00    --    0.00 -38.00 120.00   55
  3  ω    -87.00 -51.00   1.00    1.00    --    0.00 -38.00 -30.00   36
  4  ω    -87.00 -47.00   1.00    1.00    --    0.00 -38.00  60.00   40
  5  ω    -85.00 -50.00   1.00    1.00    --    0.00 -38.00 120.00   35
  6  ω    -26.00  18.00   1.00    1.00    --    0.00 -38.00 -30.00   44
  7  ω     84.00 114.00   1.00    1.00    --   95.80 -30.00 -60.00   30
  8  ω      6.00  43.00   1.00    1.00    --   95.80 -30.00 -60.00   37
  9  ω     43.00 128.00   1.00    1.00    --   95.80 -82.00 -90.00   85
 10  ω     44.00  71.00   1.00    1.00    --   95.80 -82.00   0.00   27
 11  ω     90.00 122.00   1.00    1.00    --   95.80 -82.00   0.00   32
 12  ω     86.00 128.00   1.00    1.00    --   95.80 -82.00-180.00   42
 13  ω     44.00 116.00   1.00    1.00    --   95.80 -45.00 150.00   72
 14  ω      7.00  57.00   1.00    1.00    --   95.80 -30.00 -30.00   50
 15  ω     77.00 174.00   1.00    1.00    --   95.80  30.00 -90.00   97
 16  ω     69.00 111.00   1.00    1.00    --   95.80 -30.00 -30.00   42
 17  ω     16.00 107.00   1.00    1.00    --   95.80 -61.00 120.00   91
 18  ω      7.00  33.00   1.00    1.00    --   95.80 -82.00-180.00   26
 19  ω      6.00 118.00   1.00    1.00    --   95.80 -82.00 120.00  112
 20  ω    146.00 171.00   1.00    1.00    --   95.80  30.00-120.00   25
 21  ω     27.00  53.00   1.00    1.00    --   95.80 -82.00 -60.00   26
 22  ω     60.00 124.00   1.00    1.00    --   95.80 -82.00 -60.00   64
 23  ω      6.00  74.00   1.00    1.00    --   95.80 -82.00 -30.00   68
 24  ω     99.00 124.00   1.00    1.00    --   95.80 -82.00 -30.00   25
 25  ω    106.00 183.00   1.00    1.00    --   95.80  30.00-180.00   77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0123917000
_diffrn_orient_matrix_UB_12      0.1017106000
_diffrn_orient_matrix_UB_13      0.0606315000
_diffrn_orient_matrix_UB_21      0.0043145000
_diffrn_orient_matrix_UB_22      -0.1525624000
_diffrn_orient_matrix_UB_23      0.0405576000
_diffrn_orient_matrix_UB_31      0.2009329000
_diffrn_orient_matrix_UB_32      -0.0030181000
_diffrn_orient_matrix_UB_33      -0.0046226000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.700
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2283
_reflns_number_total             2394
_reflns_odcompleteness_completeness 99.45
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details 
;
 Flack x determined using 893 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.40(7)
_refine_ls_extinction_coef       0.0032(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2394
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0302
_refine_ls_restrained_S_all      1.082
_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)+(0.0452P)²+0.1113P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0842
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C9(H9), C8(H8), C6(H6), C4(H4), C5(H5)
;
_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
F2 F 0.3775(2) 0.73895(19) 0.59566(7) 0.0770(5) Uani 1 1 d . . . . .
F3 F 0.4093(2) 0.5127(2) 0.64135(7) 0.0803(5) Uani 1 1 d . . . . .
F1 F 0.1801(2) 0.6494(2) 0.65826(8) 0.0912(6) Uani 1 1 d . . . . .
O1 O 0.1110(2) 0.3244(2) 0.46346(8) 0.0720(5) Uani 1 1 d . . . . .
N1 N 0.0741(2) 0.6346(2) 0.53300(10) 0.0621(5) Uani 1 1 d . . . . .
N2 N -0.0761(3) 0.5862(3) 0.53465(11) 0.0718(6) Uani 1 1 d . . . . .
C2 C 0.6323(3) 0.3417(2) 0.33823(9) 0.0466(5) Uani 1 1 d . . . . .
C10 C 0.3659(3) 0.3324(2) 0.40100(9) 0.0456(5) Uani 1 1 d . . . . .
C1 C 0.5337(3) 0.3868(2) 0.39186(9) 0.0459(5) Uani 1 1 d . . . . .
H1 H 0.583141 0.454704 0.421719 0.055 Uiso 1 1 calc R . . . .
C13 C 0.2061(3) 0.5238(3) 0.55858(9) 0.0456(5) Uani 1 1 d . . . . .
H13 H 0.147982 0.427099 0.573784 0.055 Uiso 1 1 calc R . . . .
C11 C 0.2589(3) 0.3753(3) 0.45752(10) 0.0493(5) Uani 1 1 d . . . . .
C12 C 0.3379(3) 0.4800(3) 0.50778(10) 0.0489(5) Uani 1 1 d . . . . .
H12A H 0.382288 0.576445 0.488239 0.059 Uiso 1 1 calc R . . . .
H12B H 0.435596 0.424969 0.527270 0.059 Uiso 1 1 calc R . . . .
C7 C 0.5557(3) 0.2386(3) 0.29260(9) 0.0512(5) Uani 1 1 d . . . . .
C14 C 0.2933(3) 0.6067(3) 0.61366(10) 0.0556(5) Uani 1 1 d . . . . .
C3 C 0.8064(3) 0.3953(3) 0.32812(11) 0.0564(5) Uani 1 1 d . . . . .
H3 H 0.859377 0.461107 0.357952 0.068 Uiso 1 1 calc R . . . .
C9 C 0.2916(3) 0.2278(3) 0.35527(10) 0.0570(6) Uani 1 1 d . . . . .
H9 H 0.178976 0.189031 0.361200 0.068 Uiso 1 1 calc R . . . .
C8 C 0.3837(3) 0.1842(3) 0.30305(10) 0.0617(6) Uani 1 1 d . . . . .
H8 H 0.332148 0.116808 0.273439 0.074 Uiso 1 1 calc R . . . .
C6 C 0.6547(4) 0.1946(3) 0.23844(11) 0.0643(6) Uani 1 1 d . . . . .
H6 H 0.605915 0.127276 0.208223 0.077 Uiso 1 1 calc R . . . .
C4 C 0.8961(3) 0.3513(3) 0.27520(12) 0.0656(6) Uani 1 1 d . . . . .
H4 H 1.009004 0.388936 0.268808 0.079 Uiso 1 1 calc R . . . .
C5 C 0.8199(4) 0.2499(3) 0.23026(12) 0.0686(7) Uani 1 1 d . . . . .
H5 H 0.883083 0.220124 0.194478 0.082 Uiso 1 1 calc R . . . .
N3 N -0.2174(4) 0.5554(4) 0.5319(2) 0.1254(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
F2 C14 1.339(3) . ?
F3 C14 1.324(3) . ?
F1 C14 1.328(3) . ?
O1 C11 1.216(3) . ?
N1 N2 1.220(3) . ?
N1 C13 1.475(3) . ?
N2 N3 1.113(4) . ?
C2 C1 1.411(3) . ?
C2 C7 1.421(3) . ?
C2 C3 1.422(3) . ?
C10 C1 1.377(3) . ?
C10 C11 1.490(3) . ?
C10 C9 1.422(3) . ?
C1 H1 0.9300 . ?
C13 H13 0.9800 . ?
C13 C12 1.517(3) . ?
C13 C14 1.509(3) . ?
C11 C12 1.503(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C7 C8 1.411(3) . ?
C7 C6 1.419(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.361(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.357(3) . ?
C8 H8 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.358(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.401(4) . ?
C5 H5 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
N2 N1 C13 115.2(2) . . ?
N3 N2 N1 172.4(3) . . ?
C1 C2 C7 118.99(19) . . ?
C1 C2 C3 122.5(2) . . ?
C7 C2 C3 118.6(2) . . ?
C1 C10 C11 122.98(18) . . ?
C1 C10 C9 118.87(19) . . ?
C9 C10 C11 118.14(18) . . ?
C2 C1 H1 119.2 . . ?
C10 C1 C2 121.51(19) . . ?
C10 C1 H1 119.2 . . ?
N1 C13 H13 109.4 . . ?
N1 C13 C12 110.55(17) . . ?
N1 C13 C14 107.09(18) . . ?
C12 C13 H13 109.4 . . ?
C14 C13 H13 109.4 . . ?
C14 C13 C12 111.10(18) . . ?
O1 C11 C10 120.6(2) . . ?
O1 C11 C12 120.5(2) . . ?
C10 C11 C12 118.93(17) . . ?
C13 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C11 C12 C13 111.79(17) . . ?
C11 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
C8 C7 C2 118.5(2) . . ?
C8 C7 C6 122.7(2) . . ?
C6 C7 C2 118.9(2) . . ?
F2 C14 C13 112.18(18) . . ?
F3 C14 F2 107.3(2) . . ?
F3 C14 F1 106.66(19) . . ?
F3 C14 C13 111.18(19) . . ?
F1 C14 F2 106.9(2) . . ?
F1 C14 C13 112.4(2) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C10 C9 H9 119.7 . . ?
C8 C9 C10 120.6(2) . . ?
C8 C9 H9 119.7 . . ?
C7 C8 H8 119.2 . . ?
C9 C8 C7 121.6(2) . . ?
C9 C8 H8 119.2 . . ?
C7 C6 H6 119.7 . . ?
C5 C6 C7 120.7(2) . . ?
C5 C6 H6 119.7 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.6(2) . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 120.6(2) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?

_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 3.490
_oxdiff_exptl_absorpt_empirical_full_min 0.460
