# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_wpl2020082902_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2075782'
loop_
_audit_author_name
_audit_author_address
'Mengjun Huang'
;Nanjing University
China
;
_audit_update_record             
;
2021-04-07 deposited with the CCDC.	2022-08-25 downloaded from the CCDC.
;
_audit_creation_date             2020-09-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H11 F3 N2'
_chemical_formula_sum            'C18 H11 F3 N2'
_chemical_formula_weight         312.29
_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/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                   11.3732(4)
_cell_length_b                   7.0194(3)
_cell_length_c                   17.8991(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.7770(10)
_cell_angle_gamma                90
_cell_volume                     1403.74(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5442
_cell_measurement_temperature    193
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      3.51
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1638 before and 0.0847 after correction.
The Ratio of minimum to maximum transmission is 0.9485.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12337
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.503
_diffrn_reflns_theta_min         2.335
_diffrn_ambient_temperature      193
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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           40.0
_diffrn_source_power             2.0
_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                2725
_reflns_number_total             3191
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         3191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0381
_refine_ls_restrained_S_all      1.068
_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)+(0.0456P)²+0.4826P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1029
_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:
 C1(H1), C2(H2), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.78364(8) 0.80951(13) 0.49139(5) 0.0447(2) Uani 1 1 d . . . . .
F2 F 0.96044(7) 0.76961(15) 0.46792(5) 0.0470(3) Uani 1 1 d . . . . .
F3 F 0.89184(7) 0.57832(13) 0.54246(5) 0.0391(2) Uani 1 1 d . . . . .
N1 N 0.49089(9) 0.24222(16) 0.43439(6) 0.0274(2) Uani 1 1 d . . . . .
N2 N -0.21940(11) 1.0436(2) 0.28251(8) 0.0455(4) Uani 1 1 d . . . . .
C00N C 0.86127(11) 0.6774(2) 0.47750(8) 0.0295(3) Uani 1 1 d . . . . .
C1 C 0.70508(11) 0.26862(19) 0.44944(8) 0.0289(3) Uani 1 1 d . . . . .
H1 H 0.780477 0.208700 0.465465 0.035 Uiso 1 1 calc R U . . .
C2 C 0.59888(12) 0.17217(19) 0.45648(8) 0.0299(3) Uani 1 1 d . . . . .
H2 H 0.605924 0.048698 0.478607 0.036 Uiso 1 1 calc R U . . .
C3 C 0.69950(10) 0.44821(19) 0.41957(7) 0.0245(3) Uani 1 1 d . . . . .
C4 C 0.58451(10) 0.53302(18) 0.39651(7) 0.0220(3) Uani 1 1 d . . . . .
C5 C 0.48301(10) 0.42266(18) 0.40454(7) 0.0225(3) Uani 1 1 d . . . . .
C6 C 0.36720(10) 0.50011(18) 0.38213(7) 0.0234(3) Uani 1 1 d . . . . .
H6 H 0.299463 0.424065 0.385925 0.028 Uiso 1 1 calc R U . . .
C7 C 0.35035(10) 0.68310(18) 0.35496(7) 0.0223(3) Uani 1 1 d . . . . .
C8 C 0.45245(11) 0.79343(18) 0.34839(7) 0.0248(3) Uani 1 1 d . . . . .
H8 H 0.442084 0.920963 0.330618 0.030 Uiso 1 1 calc R U . . .
C9 C 0.56513(11) 0.72012(19) 0.36706(7) 0.0245(3) Uani 1 1 d . . . . .
H9 H 0.631646 0.795604 0.360232 0.029 Uiso 1 1 calc R U . . .
C10 C 0.22847(10) 0.76578(18) 0.33443(7) 0.0228(3) Uani 1 1 d . . . . .
C11 C 0.20782(11) 0.95736(19) 0.34848(8) 0.0282(3) Uani 1 1 d . . . . .
H11 H 0.273090 1.037795 0.368976 0.034 Uiso 1 1 calc R U . . .
C12 C 0.09304(12) 1.0309(2) 0.33276(8) 0.0306(3) Uani 1 1 d . . . . .
H12 H 0.079534 1.160975 0.343145 0.037 Uiso 1 1 calc R U . . .
C13 C -0.00265(11) 0.9144(2) 0.30175(7) 0.0274(3) Uani 1 1 d . . . . .
C14 C 0.01664(11) 0.7245(2) 0.28523(7) 0.0280(3) Uani 1 1 d . . . . .
H14 H -0.048354 0.645710 0.262770 0.034 Uiso 1 1 calc R U . . .
C15 C 0.13178(11) 0.65169(19) 0.30194(7) 0.0261(3) Uani 1 1 d . . . . .
H15 H 0.145204 0.521860 0.291102 0.031 Uiso 1 1 calc R U . . .
C16 C -0.12354(12) 0.9876(2) 0.28982(8) 0.0329(3) Uani 1 1 d . . . . .
C17 C 0.81257(11) 0.5527(2) 0.41094(8) 0.0282(3) Uani 1 1 d . . . . .
H17A H 0.8732(14) 0.464(2) 0.4050(9) 0.035(4) Uiso 1 1 d . . . . .
H17B H 0.7992(13) 0.631(2) 0.3652(9) 0.034(4) Uiso 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
F1 C00N 1.3353(16) . ?
F2 C00N 1.3388(15) . ?
F3 C00N 1.3437(16) . ?
N1 C2 1.3134(16) . ?
N1 C5 1.3711(16) . ?
N2 C16 1.1431(17) . ?
C00N C17 1.4986(19) . ?
C1 H1 0.9500 . ?
C1 C2 1.4107(18) . ?
C1 C3 1.3661(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.4259(16) . ?
C3 C17 1.5132(17) . ?
C4 C5 1.4197(17) . ?
C4 C9 1.4169(18) . ?
C5 C6 1.4120(16) . ?
C6 H6 0.9500 . ?
C6 C7 1.3742(18) . ?
C7 C8 1.4188(17) . ?
C7 C10 1.4842(16) . ?
C8 H8 0.9500 . ?
C8 C9 1.3634(17) . ?
C9 H9 0.9500 . ?
C10 C11 1.3960(18) . ?
C10 C15 1.3963(17) . ?
C11 H11 0.9500 . ?
C11 C12 1.3829(17) . ?
C12 H12 0.9500 . ?
C12 C13 1.3913(19) . ?
C13 C14 1.392(2) . ?
C13 C16 1.4460(17) . ?
C14 H14 0.9500 . ?
C14 C15 1.3852(17) . ?
C15 H15 0.9500 . ?
C17 H17A 0.952(17) . ?
C17 H17B 0.975(17) . ?

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 N1 C5 116.90(11) . . ?
F1 C00N F2 106.88(12) . . ?
F1 C00N F3 105.75(11) . . ?
F1 C00N C17 113.25(10) . . ?
F2 C00N F3 105.85(10) . . ?
F2 C00N C17 112.06(11) . . ?
F3 C00N C17 112.51(12) . . ?
C2 C1 H1 120.0 . . ?
C3 C1 H1 120.0 . . ?
C3 C1 C2 120.00(12) . . ?
N1 C2 C1 124.16(12) . . ?
N1 C2 H2 117.9 . . ?
C1 C2 H2 117.9 . . ?
C1 C3 C4 118.14(11) . . ?
C1 C3 C17 120.60(11) . . ?
C4 C3 C17 121.27(12) . . ?
C5 C4 C3 117.51(11) . . ?
C9 C4 C3 124.41(11) . . ?
C9 C4 C5 118.07(11) . . ?
N1 C5 C4 123.26(11) . . ?
N1 C5 C6 117.12(11) . . ?
C6 C5 C4 119.61(11) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.42(11) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 C8 118.52(11) . . ?
C6 C7 C10 121.01(11) . . ?
C8 C7 C10 120.47(11) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.34(12) . . ?
C9 C8 H8 119.3 . . ?
C4 C9 H9 119.5 . . ?
C8 C9 C4 120.98(11) . . ?
C8 C9 H9 119.5 . . ?
C11 C10 C7 120.86(11) . . ?
C11 C10 C15 118.79(11) . . ?
C15 C10 C7 120.34(11) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.47(12) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.00(13) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C14 120.35(11) . . ?
C12 C13 C16 120.07(13) . . ?
C14 C13 C16 119.52(12) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 C13 119.18(12) . . ?
C15 C14 H14 120.4 . . ?
C10 C15 H15 119.4 . . ?
C14 C15 C10 121.16(12) . . ?
C14 C15 H15 119.4 . . ?
N2 C16 C13 177.93(15) . . ?
C00N C17 C3 113.39(11) . . ?
C00N C17 H17A 107.7(10) . . ?
C00N C17 H17B 108.3(10) . . ?
C3 C17 H17A 109.9(10) . . ?
C3 C17 H17B 110.9(9) . . ?
H17A C17 H17B 106.3(13) . . ?

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
F1 C00N C17 C3 -58.29(16) . . . . ?
F2 C00N C17 C3 -179.30(11) . . . . ?
F3 C00N C17 C3 61.56(14) . . . . ?
N1 C5 C6 C7 176.88(11) . . . . ?
C1 C3 C4 C5 -1.47(17) . . . . ?
C1 C3 C4 C9 177.77(12) . . . . ?
C1 C3 C17 C00N -93.10(15) . . . . ?
C2 N1 C5 C4 0.33(18) . . . . ?
C2 N1 C5 C6 -178.75(11) . . . . ?
C2 C1 C3 C4 0.23(19) . . . . ?
C2 C1 C3 C17 -179.40(12) . . . . ?
C3 C1 C2 N1 1.5(2) . . . . ?
C3 C4 C5 N1 1.26(18) . . . . ?
C3 C4 C5 C6 -179.68(11) . . . . ?
C3 C4 C9 C8 -177.97(12) . . . . ?
C4 C3 C17 C00N 87.28(15) . . . . ?
C4 C5 C6 C7 -2.23(18) . . . . ?
C5 N1 C2 C1 -1.7(2) . . . . ?
C5 C4 C9 C8 1.27(18) . . . . ?
C5 C6 C7 C8 1.13(18) . . . . ?
C5 C6 C7 C10 -177.56(11) . . . . ?
C6 C7 C8 C9 1.22(18) . . . . ?
C6 C7 C10 C11 143.25(13) . . . . ?
C6 C7 C10 C15 -35.52(17) . . . . ?
C7 C8 C9 C4 -2.43(19) . . . . ?
C7 C10 C11 C12 -176.68(12) . . . . ?
C7 C10 C15 C14 177.37(12) . . . . ?
C8 C7 C10 C11 -35.41(17) . . . . ?
C8 C7 C10 C15 145.83(12) . . . . ?
C9 C4 C5 N1 -178.04(11) . . . . ?
C9 C4 C5 C6 1.02(17) . . . . ?
C10 C7 C8 C9 179.91(11) . . . . ?
C10 C11 C12 C13 -0.9(2) . . . . ?
C11 C10 C15 C14 -1.42(19) . . . . ?
C11 C12 C13 C14 -1.1(2) . . . . ?
C11 C12 C13 C16 176.03(12) . . . . ?
C12 C13 C14 C15 1.7(2) . . . . ?
C13 C14 C15 C10 -0.48(19) . . . . ?
C15 C10 C11 C12 2.11(19) . . . . ?
C16 C13 C14 C15 -175.37(12) . . . . ?
C17 C3 C4 C5 178.15(11) . . . . ?
C17 C3 C4 C9 -2.60(19) . . . . ?

_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_11_a
_database_code_depnum_ccdc_archive 'CCDC 2126072'
loop_
_audit_author_name
_audit_author_address
H-M
;Nanjing University
China
;
_audit_update_record             
;
2021-12-03 deposited with the CCDC.	2022-08-25 downloaded from the CCDC.
;
_audit_creation_date             2021-12-03
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C8 H5 F3 N2 O2 S'
_chemical_formula_sum            'C8 H5 F3 N2 O2 S'
_chemical_formula_weight         250.20
_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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   10.810(2)
_cell_length_b                   5.693(2)
_cell_length_c                   16.013(3)
_cell_angle_alpha                90.00(3)
_cell_angle_beta                 93.45(3)
_cell_angle_gamma                90.00(3)
_cell_volume                     983.7(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4716
_cell_measurement_temperature    193.0
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.55
_exptl_absorpt_coefficient_mu    0.360
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6059
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1368 before and 0.0714 after correction.
The Ratio of minimum to maximum transmission is 0.8126.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8493
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.55
_diffrn_ambient_temperature      193.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                1975
_reflns_number_total             2243
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0364
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0350P)²+0.4812P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.0987
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C1(H1), C2(H2), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S001 S 0.32470(4) 0.74265(7) 0.34953(2) 0.02980(14) Uani 1 1 d . . .
F3 F 0.48293(11) 0.4002(2) 0.37236(8) 0.0496(3) Uani 1 1 d . . .
F1 F 0.53487(11) 0.7155(2) 0.43818(7) 0.0477(3) Uani 1 1 d . . .
O2 O 0.27275(12) 0.6220(2) 0.27854(7) 0.0398(3) Uani 1 1 d . . .
F2 F 0.54954(12) 0.6957(3) 0.30501(8) 0.0626(4) Uani 1 1 d . . .
O1 O 0.33625(14) 0.9899(2) 0.35424(9) 0.0461(4) Uani 1 1 d . . .
N1 N 0.25781(13) 0.6483(2) 0.43256(8) 0.0261(3) Uani 1 1 d . . .
N2 N -0.02095(16) 0.0190(3) 0.65216(10) 0.0427(4) Uani 1 1 d . . .
C3 C 0.15633(14) 0.4767(3) 0.57925(9) 0.0257(3) Uani 1 1 d . . .
C4 C 0.14135(14) 0.3563(3) 0.49955(9) 0.0256(3) Uani 1 1 d . . .
H4 H 0.0950 0.2145 0.4962 0.031 Uiso 1 1 calc R . .
C5 C 0.19040(14) 0.4375(3) 0.43056(9) 0.0258(3) Uani 1 1 d . . .
H5 H 0.1795 0.3519 0.3797 0.031 Uiso 1 1 calc R . .
C1 C 0.27049(16) 0.7768(3) 0.50792(10) 0.0294(3) Uani 1 1 d . . .
H1 H 0.3134 0.9225 0.5092 0.035 Uiso 1 1 calc R . .
C2 C 0.22302(15) 0.6966(3) 0.57735(10) 0.0296(3) Uani 1 1 d . . .
H2 H 0.2333 0.7868 0.6272 0.036 Uiso 1 1 calc R . .
C6 C 0.10993(15) 0.3949(3) 0.65093(10) 0.0322(4) Uani 1 1 d . . .
H6 H 0.1258 0.4798 0.7015 0.039 Uiso 1 1 calc R . .
C7 C 0.03854(16) 0.1862(3) 0.65201(10) 0.0340(4) Uani 1 1 d . . .
C8 C 0.48349(16) 0.6308(3) 0.36731(10) 0.0340(4) 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
S001 O2 1.4149(14) . ?
S001 O1 1.4149(15) . ?
S001 N1 1.6417(13) . ?
S001 C8 1.8369(19) . ?
F3 C8 1.315(2) . ?
F1 C8 1.324(2) . ?
F2 C8 1.314(2) . ?
N1 C5 1.403(2) . ?
N1 C1 1.411(2) . ?
N2 C7 1.149(3) . ?
C3 C4 1.449(2) . ?
C3 C2 1.446(2) . ?
C3 C6 1.362(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.336(2) . ?
C5 H5 0.9500 . ?
C1 H1 0.9500 . ?
C1 C2 1.333(2) . ?
C2 H2 0.9500 . ?
C6 H6 0.9500 . ?
C6 C7 1.417(3) . ?

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
O2 S001 N1 108.60(8) . . ?
O2 S001 C8 106.16(9) . . ?
O1 S001 O2 123.72(9) . . ?
O1 S001 N1 108.92(8) . . ?
O1 S001 C8 104.96(9) . . ?
N1 S001 C8 102.36(8) . . ?
C5 N1 S001 120.99(10) . . ?
C5 N1 C1 119.12(13) . . ?
C1 N1 S001 119.87(11) . . ?
C2 C3 C4 114.87(13) . . ?
C6 C3 C4 123.56(15) . . ?
C6 C3 C2 121.56(15) . . ?
C3 C4 H4 118.8 . . ?
C5 C4 C3 122.37(15) . . ?
C5 C4 H4 118.8 . . ?
N1 C5 H5 119.7 . . ?
C4 C5 N1 120.56(14) . . ?
C4 C5 H5 119.7 . . ?
N1 C1 H1 119.6 . . ?
C2 C1 N1 120.88(15) . . ?
C2 C1 H1 119.6 . . ?
C3 C2 H2 118.9 . . ?
C1 C2 C3 122.12(14) . . ?
C1 C2 H2 118.9 . . ?
C3 C6 H6 119.1 . . ?
C3 C6 C7 121.70(15) . . ?
C7 C6 H6 119.1 . . ?
N2 C7 C6 178.8(2) . . ?
F3 C8 S001 110.36(12) . . ?
F3 C8 F1 108.30(15) . . ?
F1 C8 S001 110.27(12) . . ?
F2 C8 S001 109.27(13) . . ?
F2 C8 F3 109.39(15) . . ?
F2 C8 F1 109.22(15) . . ?

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
S001 N1 C5 C4 176.73(12) . . . . ?
S001 N1 C1 C2 -176.11(13) . . . . ?
O2 S001 N1 C5 16.77(15) . . . . ?
O2 S001 N1 C1 -164.87(12) . . . . ?
O2 S001 C8 F3 -53.56(14) . . . . ?
O2 S001 C8 F1 -173.18(11) . . . . ?
O2 S001 C8 F2 66.76(15) . . . . ?
O1 S001 N1 C5 154.03(13) . . . . ?
O1 S001 N1 C1 -27.60(15) . . . . ?
O1 S001 C8 F3 173.93(12) . . . . ?
O1 S001 C8 F1 54.32(14) . . . . ?
O1 S001 C8 F2 -65.74(15) . . . . ?
N1 S001 C8 F3 60.22(13) . . . . ?
N1 S001 C8 F1 -59.39(14) . . . . ?
N1 S001 C8 F2 -179.45(13) . . . . ?
N1 C1 C2 C3 -0.2(3) . . . . ?
C3 C4 C5 N1 -1.0(2) . . . . ?
C3 C6 C7 N2 -71(9) . . . . ?
C4 C3 C2 C1 -2.2(2) . . . . ?
C4 C3 C6 C7 -2.3(3) . . . . ?
C5 N1 C1 C2 2.3(2) . . . . ?
C1 N1 C5 C4 -1.6(2) . . . . ?
C2 C3 C4 C5 2.9(2) . . . . ?
C2 C3 C6 C7 176.38(16) . . . . ?
C6 C3 C4 C5 -178.33(16) . . . . ?
C6 C3 C2 C1 178.95(16) . . . . ?
C8 S001 N1 C5 -95.21(14) . . . . ?
C8 S001 N1 C1 83.15(14) . . . . ?

_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_2_a
_database_code_depnum_ccdc_archive 'CCDC 2075783'
loop_
_audit_author_name
_audit_author_address
'Mengjun Huang'
;Nanjing University
China
;
_audit_update_record             
;
2021-04-07 deposited with the CCDC.	2022-08-25 downloaded from the CCDC.
;
_audit_creation_date             2021-04-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H19 F3 N2 O'
_chemical_formula_sum            'C21 H19 F3 N2 O'
_chemical_formula_weight         372.38
_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'
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                   8.832(2)
_cell_length_b                   11.476(2)
_cell_length_c                   17.721(4)
_cell_angle_alpha                90.00(3)
_cell_angle_beta                 91.06(3)
_cell_angle_gamma                90.00(3)
_cell_volume                     1796.0(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3840
_cell_measurement_temperature    293.0
_cell_measurement_theta_max      27.17
_cell_measurement_theta_min      2.30
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6604
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1018 before and 0.0509 after correction.
The Ratio of minimum to maximum transmission is 0.8857.
The λ/2 correction factor is Not present.
;
_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    1.377
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16006
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         2.114
_diffrn_ambient_temperature      293.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2840
_reflns_number_total             4117
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4117
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0462
_refine_ls_restrained_S_all      1.020
_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)+(0.0397P)²+0.7205P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1138
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H009(0.029) H00A(0.032) H00B(0.032) H00C(0.034) H00D(0.034)
 H00E(0.039) H00H(0.042) H00I(0.044) H00J(0.043) H00K(0.047) H00L(0.048)
 H00M(0.045) H00N(0.048) H00F(0.067) H00G(0.067) H00O(0.067) H00P(0.062)
 H00Q(0.058) H00R(0.065)
 Fixed X: H009(0.3462) H00A(0.2808) H00B(0.1228) H00C(0.0606) H00D(0.2164)
 H00E(0.4437) H00H(-0.0462) H00I(0.4264) H00J(0.3365) H00K(-0.0388)
 H00L(0.6464) H00M(0.6545) H00N(0.4764) H00F(0.0464) H00G(0.198) H00O(0.1226)
 H00P(0.7252) H00Q(0.586) H00R(0.7792)
 Fixed Y: H009(0.3954) H00A(0.5717) H00B(0.521) H00C(0.4885) H00D(0.5436)
 H00E(0.4939) H00H(0.3409) H00I(0.2515) H00J(0.1429) H00K(0.2286) H00L(0.3436)
 H00M(0.4653) H00N(0.2131) H00F(0.1072) H00G(0.0371) H00O(0.0536) H00P(0.1911)
 H00Q(0.1178) H00R(0.1451)
 Fixed Z: H009(0.4152) H00A(0.4746) H00B(0.4954) H00C(0.366) H00D(0.3451)
 H00E(0.3007) H00H(0.2877) H00I(0.0908) H00J(0.3055) H00K(0.1803) H00L(0.1254)
 H00M(0.2306) H00N(0.5168) H00F(0.4688) H00G(0.4776) H00O(0.3976) H00P(0.481)
 H00Q(0.2707) H00R(0.3577)
;
_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
F001 F 0.43779(12) 0.43560(11) 0.56319(6) 0.0424(3) Uani 1 1 d . . . . .
F002 F 0.27845(14) 0.54828(11) 0.61601(7) 0.0532(4) Uani 1 1 d . . . . .
F003 F 0.22107(14) 0.37113(11) 0.59293(7) 0.0527(4) Uani 1 1 d . . . . .
O004 O 0.01969(13) 0.30559(11) 0.45812(7) 0.0335(3) Uani 1 1 d . . . . .
N005 N 0.22779(16) 0.19755(13) 0.43564(8) 0.0297(3) Uani 1 1 d . . . . .
N006 N 0.16904(19) 0.25445(14) 0.15351(9) 0.0382(4) Uani 1 1 d . . . . .
C007 C 0.3015(2) 0.38733(15) 0.24092(9) 0.0271(4) Uani 1 1 d . . . . .
C008 C 0.15376(18) 0.30074(15) 0.44176(9) 0.0251(4) Uani 1 1 d . . . . .
C009 C 0.23976(18) 0.41296(14) 0.42494(9) 0.0238(4) Uani 1 1 d . . . . .
H009 H 0.3462 0.3954 0.4152 0.029 Uiso 1 1 calc R . . . .
C00A C 0.22864(19) 0.50121(15) 0.48948(9) 0.0265(4) Uani 1 1 d . . . . .
H00A H 0.2808 0.5717 0.4746 0.032 Uiso 1 1 calc R . . . .
H00B H 0.1228 0.5210 0.4954 0.032 Uiso 1 1 calc R . . . .
C00B C 0.3829(2) 0.18382(15) 0.41415(10) 0.0286(4) Uani 1 1 d . . . . .
C00C C 0.1652(2) 0.47056(15) 0.35484(9) 0.0283(4) Uani 1 1 d . . . . .
H00C H 0.0606 0.4885 0.3660 0.034 Uiso 1 1 calc R . . . .
H00D H 0.2164 0.5436 0.3451 0.034 Uiso 1 1 calc R . . . .
C00D C 0.1684(2) 0.39715(15) 0.28456(10) 0.0278(4) Uani 1 1 d . . . . .
C00E C 0.4389(2) 0.44426(16) 0.25923(10) 0.0321(4) Uani 1 1 d . . . . .
H00E H 0.4437 0.4939 0.3007 0.039 Uiso 1 1 calc R . . . .
C00F C 0.29050(19) 0.46459(16) 0.56406(10) 0.0298(4) Uani 1 1 d . . . . .
C00G C 0.2967(2) 0.31376(16) 0.17610(10) 0.0313(4) Uani 1 1 d . . . . .
C00H C 0.0429(2) 0.33653(17) 0.26063(11) 0.0349(4) Uani 1 1 d . . . . .
H00H H -0.0462 0.3409 0.2877 0.042 Uiso 1 1 calc R . . . .
C00I C 0.4289(2) 0.29918(17) 0.13322(10) 0.0368(4) Uani 1 1 d . . . . .
H00I H 0.4264 0.2515 0.0908 0.044 Uiso 1 1 calc R . . . .
C00J C 0.4147(2) 0.15329(17) 0.34071(11) 0.0360(4) Uani 1 1 d . . . . .
H00J H 0.3365 0.1429 0.3055 0.043 Uiso 1 1 calc R . . . .
C00K C 0.0489(2) 0.26771(18) 0.19520(11) 0.0394(5) Uani 1 1 d . . . . .
H00K H -0.0388 0.2286 0.1803 0.047 Uiso 1 1 calc R . . . .
C00L C 0.5598(2) 0.35445(18) 0.15366(11) 0.0397(5) Uani 1 1 d . . . . .
H00L H 0.6464 0.3436 0.1254 0.048 Uiso 1 1 calc R . . . .
C00M C 0.5647(2) 0.42777(18) 0.21716(11) 0.0377(5) Uani 1 1 d . . . . .
H00M H 0.6545 0.4653 0.2306 0.045 Uiso 1 1 calc R . . . .
C00N C 0.4984(2) 0.19567(17) 0.46696(12) 0.0403(5) Uani 1 1 d . . . . .
H00N H 0.4764 0.2131 0.5168 0.048 Uiso 1 1 calc R . . . .
C00O C 0.1412(2) 0.08951(17) 0.44580(13) 0.0449(5) Uani 1 1 d . . . . .
H00F H 0.0464 0.1072 0.4688 0.067 Uiso 1 1 calc GR . . . .
H00G H 0.1980 0.0371 0.4776 0.067 Uiso 1 1 calc GR . . . .
H00O H 0.1226 0.0536 0.3976 0.067 Uiso 1 1 calc GR . . . .
C00P C 0.6469(2) 0.1816(2) 0.44567(14) 0.0520(6) Uani 1 1 d . . . . .
H00P H 0.7252 0.1911 0.4810 0.062 Uiso 1 1 calc R . . . .
C00Q C 0.5638(2) 0.13833(19) 0.32002(13) 0.0487(6) Uani 1 1 d . . . . .
H00Q H 0.5860 0.1178 0.2707 0.058 Uiso 1 1 calc R . . . .
C00R C 0.6791(2) 0.1537(2) 0.37216(15) 0.0542(6) Uani 1 1 d . . . . .
H00R H 0.7792 0.1451 0.3577 0.065 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
F001 C00F 1.343(2) . ?
F002 C00F 1.336(2) . ?
F003 C00F 1.342(2) . ?
O004 C008 1.226(2) . ?
N005 C008 1.358(2) . ?
N005 C00B 1.438(2) . ?
N005 C00O 1.470(2) . ?
N006 C00G 1.371(2) . ?
N006 C00K 1.313(2) . ?
C007 C00D 1.424(2) . ?
C007 C00E 1.410(3) . ?
C007 C00G 1.426(2) . ?
C008 C009 1.527(2) . ?
C009 C00A 1.532(2) . ?
C009 C00C 1.544(2) . ?
C00A C00F 1.482(3) . ?
C00B C00J 1.382(3) . ?
C00B C00N 1.378(3) . ?
C00C C00D 1.504(2) . ?
C00D C00H 1.369(3) . ?
C00E C00M 1.363(3) . ?
C00G C00I 1.415(3) . ?
C00H C00K 1.405(3) . ?
C00I C00L 1.362(3) . ?
C00J C00Q 1.384(3) . ?
C00L C00M 1.405(3) . ?
C00N C00P 1.381(3) . ?
C00P C00R 1.376(3) . ?
C00Q C00R 1.374(3) . ?

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
C008 N005 C00B 125.41(14) . . ?
C008 N005 C00O 118.25(15) . . ?
C00B N005 C00O 116.16(15) . . ?
C00K N006 C00G 116.56(16) . . ?
C00D C007 C00G 118.16(16) . . ?
C00E C007 C00D 123.64(16) . . ?
C00E C007 C00G 118.18(16) . . ?
O004 C008 N005 121.82(16) . . ?
O004 C008 C009 119.60(15) . . ?
N005 C008 C009 118.54(14) . . ?
C008 C009 C00A 111.88(13) . . ?
C008 C009 C00C 108.17(14) . . ?
C00A C009 C00C 106.57(14) . . ?
C00F C00A C009 116.79(15) . . ?
C00J C00B N005 119.24(16) . . ?
C00N C00B N005 120.43(17) . . ?
C00N C00B C00J 120.27(18) . . ?
C00D C00C C009 114.33(14) . . ?
C007 C00D C00C 121.49(16) . . ?
C00H C00D C007 117.61(16) . . ?
C00H C00D C00C 120.89(16) . . ?
C00M C00E C007 121.09(18) . . ?
F001 C00F C00A 113.65(15) . . ?
F002 C00F F001 105.99(14) . . ?
F002 C00F F003 105.62(15) . . ?
F002 C00F C00A 112.20(16) . . ?
F003 C00F F001 104.83(15) . . ?
F003 C00F C00A 113.79(15) . . ?
N006 C00G C007 122.79(17) . . ?
N006 C00G C00I 117.84(17) . . ?
C00I C00G C007 119.36(17) . . ?
C00D C00H C00K 119.90(18) . . ?
C00L C00I C00G 120.46(18) . . ?
C00B C00J C00Q 119.45(19) . . ?
N006 C00K C00H 124.96(18) . . ?
C00I C00L C00M 120.36(18) . . ?
C00E C00M C00L 120.53(19) . . ?
C00B C00N C00P 119.9(2) . . ?
C00R C00P C00N 120.0(2) . . ?
C00R C00Q C00J 120.2(2) . . ?
C00Q C00R C00P 120.2(2) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
