# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_yzh
_database_code_depnum_ccdc_archive 'CCDC 1917454'
loop_
_audit_author_name
_audit_author_address
'Li menghua'
;Fuzhou University
China
;
_audit_update_record             
;
2019-09-09 deposited with the CCDC.	2019-12-19 downloaded from the CCDC.
;
_audit_creation_date             2019-09-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H21 F3 N2'
_chemical_formula_sum            'C30 H21 F3 N2'
_chemical_formula_weight         466.49
_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                   10.4176(9)
_cell_length_b                   15.2392(12)
_cell_length_c                   14.2987(15)
_cell_angle_alpha                90
_cell_angle_beta                 101.812(10)
_cell_angle_gamma                90
_cell_volume                     2221.9(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1742
_cell_measurement_temperature    293.7(4)
_cell_measurement_theta_max      22.7320
_cell_measurement_theta_min      2.9700
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98308
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_av_unetI/netI     0.1163
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.840
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16350
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.840
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.319
_diffrn_reflns_theta_min         2.589
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.7(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.840
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     42.00  80.00   0.50   15.00    --   -9.60  55.00  90.00   76
  2  ω    -75.00 -44.00   0.50   15.00    --   -9.60  55.00  30.00   62
  3  ω     16.00  64.00   0.50   15.00    --   -9.60  55.00  30.00   96
  4  ω    -91.00   0.00   0.50   15.00    --   -9.60  55.00 -60.00  182
  5  ω      7.00  33.00   0.50   15.00    --   -9.60  55.00 -60.00   52
  6  ω    -99.00 -36.00   0.50   15.00    --   -9.60  55.00  90.00  126
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0015727000
_diffrn_orient_matrix_UB_12      -0.0419132000
_diffrn_orient_matrix_UB_13      -0.0212659000
_diffrn_orient_matrix_UB_21      -0.0027610000
_diffrn_orient_matrix_UB_22      0.0201266000
_diffrn_orient_matrix_UB_23      -0.0451088000
_diffrn_orient_matrix_UB_31      0.0694939000
_diffrn_orient_matrix_UB_32      0.0017998000
_diffrn_orient_matrix_UB_33      0.0090623000
_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                2361
_reflns_number_total             5122
_reflns_odcompleteness_completeness 99.28
_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 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (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    ?
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         5122
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1598
_refine_ls_R_factor_gt           0.0593
_refine_ls_restrained_S_all      0.967
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0612P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1507
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C17(H17)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C8(H8), C12(H12), C20(H20), C21(H21), C22(H22), C23(H23),
 C24(H24), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31),
  C32(H32), C33(H33), C34(H34), C35(H35)
;
_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 0.81655(14) 0.06804(9) 0.31891(10) 0.0553(4) Uani 1 1 d . . . . .
F2 F 0.74941(13) -0.06042(9) 0.27236(11) 0.0583(4) Uani 1 1 d . . . . .
F3 F 0.90287(14) -0.04496(10) 0.39499(11) 0.0625(5) Uani 1 1 d . . . . .
N2 N 1.07954(19) -0.24388(12) 0.21934(15) 0.0423(5) Uani 1 1 d . . . . .
H2 H 1.134666 -0.286182 0.233838 0.051 Uiso 1 1 calc R . . . .
C5 C 0.9358(2) 0.04778(14) 0.16412(17) 0.0353(6) Uani 1 1 d . . . . .
N1 N 0.98372(19) 0.15310(13) 0.06806(14) 0.0454(6) Uani 1 1 d . . . . .
H1 H 1.028569 0.189869 0.042218 0.055 Uiso 1 1 calc R . . . .
C7 C 0.9062(2) -0.16489(15) 0.14789(17) 0.0350(6) Uani 1 1 d . . . . .
C8 C 0.7902(2) -0.15196(16) 0.08090(18) 0.0423(6) Uani 1 1 d . . . . .
H8 H 0.747490 -0.098116 0.077266 0.051 Uiso 1 1 calc R . . . .
C9 C 1.2098(2) -0.14429(16) 0.33578(17) 0.0413(6) Uani 1 1 d . . . . .
C10 C 0.9846(2) -0.11202(14) 0.22113(16) 0.0346(6) Uani 1 1 d . . . . .
C11 C 1.0901(2) -0.16251(15) 0.26346(17) 0.0384(6) Uani 1 1 d . . . . .
C12 C 0.6809(2) 0.06156(16) 0.09461(19) 0.0471(7) Uani 1 1 d . . . . .
H12 H 0.652710 0.020365 0.133986 0.057 Uiso 1 1 calc R . . . .
C13 C 1.1768(2) 0.09895(17) 0.18016(17) 0.0406(6) Uani 1 1 d . . . . .
C14 C 1.0354(2) 0.09570(15) 0.13949(17) 0.0378(6) Uani 1 1 d . . . . .
C36 C 0.8579(2) -0.01387(16) 0.30661(19) 0.0425(6) Uani 1 1 d . . . . .
C16 C 0.9677(2) -0.24694(15) 0.14885(17) 0.0379(6) Uani 1 1 d . . . . .
C17 C 0.9601(2) -0.01786(14) 0.24593(16) 0.0349(6) Uani 1 1 d . . . . .
H17 H 1.041723 0.001423 0.287948 0.042 Uiso 1 1 calc R . . . .
C18 C 0.8510(2) 0.14365(16) 0.04377(18) 0.0418(6) Uani 1 1 d . . . . .
C19 C 0.8152(2) 0.07884(15) 0.10421(17) 0.0382(6) Uani 1 1 d . . . . .
C20 C 0.9177(3) -0.31433(16) 0.08693(19) 0.0469(7) Uani 1 1 d . . . . .
H20 H 0.961332 -0.367722 0.088372 0.056 Uiso 1 1 calc R . . . .
C21 C 1.3294(3) -0.17577(18) 0.32072(19) 0.0535(7) Uani 1 1 d . . . . .
H21 H 1.331472 -0.208723 0.266310 0.064 Uiso 1 1 calc R . . . .
C22 C 0.7394(2) -0.21864(17) 0.02048(19) 0.0476(7) Uani 1 1 d . . . . .
H22 H 0.661539 -0.209699 -0.023584 0.057 Uiso 1 1 calc R . . . .
C23 C 0.8022(2) -0.29980(18) 0.02366(19) 0.0498(7) Uani 1 1 d . . . . .
H23 H 0.765198 -0.344369 -0.017589 0.060 Uiso 1 1 calc R . . . .
C24 C 0.7603(3) 0.18801(19) -0.02454(19) 0.0566(8) Uani 1 1 d . . . . .
H24 H 0.786688 0.230456 -0.063372 0.068 Uiso 1 1 calc R . . . .
C25 C 1.2341(3) 0.1777(2) 0.21465(19) 0.0571(8) Uani 1 1 d . . . . .
H25 H 1.182632 0.227823 0.211971 0.068 Uiso 1 1 calc R . . . .
C26 C 1.3256(3) -0.07884(19) 0.4810(2) 0.0609(8) Uani 1 1 d . . . . .
H26 H 1.324145 -0.045421 0.535197 0.073 Uiso 1 1 calc R . . . .
C27 C 1.2100(3) -0.09610(18) 0.41761(19) 0.0507(7) Uani 1 1 d . . . . .
H27 H 1.131313 -0.075126 0.429994 0.061 Uiso 1 1 calc R . . . .
C28 C 0.5911(3) 0.10539(18) 0.0272(2) 0.0594(8) Uani 1 1 d . . . . .
H28 H 0.502232 0.093644 0.021437 0.071 Uiso 1 1 calc R . . . .
C29 C 1.2555(3) 0.02610(19) 0.1830(2) 0.0627(8) Uani 1 1 d . . . . .
H29 H 1.218684 -0.027164 0.159589 0.075 Uiso 1 1 calc R . . . .
C30 C 1.4442(3) -0.1591(2) 0.3846(2) 0.0633(8) Uani 1 1 d . . . . .
H30 H 1.523060 -0.180859 0.373237 0.076 Uiso 1 1 calc R . . . .
C31 C 1.4430(3) -0.1102(2) 0.4654(2) 0.0636(8) Uani 1 1 d . . . . .
H31 H 1.520597 -0.098653 0.508841 0.076 Uiso 1 1 calc R . . . .
C32 C 0.6309(3) 0.1672(2) -0.0328(2) 0.0637(8) Uani 1 1 d . . . . .
H32 H 0.568303 0.194767 -0.079230 0.076 Uiso 1 1 calc R . . . .
C33 C 1.3659(3) 0.1825(3) 0.2527(2) 0.0737(10) Uani 1 1 d . . . . .
H33 H 1.403355 0.235402 0.276555 0.088 Uiso 1 1 calc R . . . .
C34 C 1.4423(3) 0.1087(3) 0.2554(2) 0.0867(12) Uani 1 1 d . . . . .
H34 H 1.531629 0.111627 0.281552 0.104 Uiso 1 1 calc R . . . .
C35 C 1.3879(3) 0.0312(3) 0.2199(3) 0.0880(12) Uani 1 1 d . . . . .
H35 H 1.440318 -0.018340 0.220659 0.106 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
F1 C36 1.344(3) . ?
F2 C36 1.339(3) . ?
F3 C36 1.341(3) . ?
N2 C11 1.385(3) . ?
N2 C16 1.376(3) . ?
C5 C14 1.373(3) . ?
C5 C17 1.521(3) . ?
C5 C19 1.447(3) . ?
N1 C14 1.369(3) . ?
N1 C18 1.362(3) . ?
C7 C8 1.393(3) . ?
C7 C10 1.437(3) . ?
C7 C16 1.404(3) . ?
C8 C22 1.368(3) . ?
C9 C11 1.474(3) . ?
C9 C21 1.393(3) . ?
C9 C27 1.381(3) . ?
C10 C11 1.376(3) . ?
C10 C17 1.512(3) . ?
C12 C19 1.403(3) . ?
C12 C28 1.372(3) . ?
C13 C14 1.469(3) . ?
C13 C25 1.385(4) . ?
C13 C29 1.376(4) . ?
C36 C17 1.506(3) . ?
C16 C20 1.386(3) . ?
C18 C19 1.412(3) . ?
C18 C24 1.388(3) . ?
C20 C23 1.367(3) . ?
C21 C30 1.372(4) . ?
C22 C23 1.395(3) . ?
C24 C32 1.366(4) . ?
C25 C33 1.372(4) . ?
C26 C27 1.376(4) . ?
C26 C31 1.374(4) . ?
C28 C32 1.393(4) . ?
C29 C35 1.374(4) . ?
C30 C31 1.377(4) . ?
C33 C34 1.374(5) . ?
C34 C35 1.363(5) . ?

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
C16 N2 C11 109.88(19) . . ?
C14 C5 C17 122.1(2) . . ?
C14 C5 C19 106.5(2) . . ?
C19 C5 C17 131.2(2) . . ?
C18 N1 C14 110.3(2) . . ?
C8 C7 C10 134.9(2) . . ?
C8 C7 C16 117.6(2) . . ?
C16 C7 C10 107.6(2) . . ?
C22 C8 C7 119.9(2) . . ?
C21 C9 C11 118.8(2) . . ?
C27 C9 C11 123.3(2) . . ?
C27 C9 C21 117.9(2) . . ?
C7 C10 C17 127.2(2) . . ?
C11 C10 C7 106.9(2) . . ?
C11 C10 C17 125.8(2) . . ?
N2 C11 C9 117.7(2) . . ?
C10 C11 N2 108.6(2) . . ?
C10 C11 C9 133.4(2) . . ?
C28 C12 C19 120.0(2) . . ?
C25 C13 C14 119.6(2) . . ?
C29 C13 C14 121.8(2) . . ?
C29 C13 C25 118.5(2) . . ?
C5 C14 C13 131.7(2) . . ?
N1 C14 C5 109.2(2) . . ?
N1 C14 C13 118.9(2) . . ?
F1 C36 C17 113.35(19) . . ?
F2 C36 F1 105.69(19) . . ?
F2 C36 F3 105.26(19) . . ?
F2 C36 C17 114.3(2) . . ?
F3 C36 F1 105.3(2) . . ?
F3 C36 C17 112.1(2) . . ?
N2 C16 C7 107.1(2) . . ?
N2 C16 C20 130.1(2) . . ?
C20 C16 C7 122.9(2) . . ?
C10 C17 C5 116.96(19) . . ?
C36 C17 C5 112.98(19) . . ?
C36 C17 C10 110.28(18) . . ?
N1 C18 C19 107.4(2) . . ?
N1 C18 C24 129.6(2) . . ?
C24 C18 C19 123.0(2) . . ?
C12 C19 C5 136.4(2) . . ?
C12 C19 C18 117.0(2) . . ?
C18 C19 C5 106.6(2) . . ?
C23 C20 C16 117.9(2) . . ?
C30 C21 C9 121.3(3) . . ?
C8 C22 C23 121.3(2) . . ?
C20 C23 C22 120.5(2) . . ?
C32 C24 C18 117.8(3) . . ?
C33 C25 C13 120.8(3) . . ?
C31 C26 C27 121.0(3) . . ?
C26 C27 C9 120.6(3) . . ?
C12 C28 C32 121.1(3) . . ?
C35 C29 C13 120.7(3) . . ?
C21 C30 C31 120.1(3) . . ?
C26 C31 C30 119.1(3) . . ?
C24 C32 C28 121.1(3) . . ?
C25 C33 C34 119.7(3) . . ?
C35 C34 C33 120.3(3) . . ?
C34 C35 C29 120.0(3) . . ?

_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 1.065
_oxdiff_exptl_absorpt_empirical_full_min 0.939
