# 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_210330a_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2076180'
loop_
_audit_author_name
_audit_author_address
'xiao hu'
;fudan university
China
;
_audit_update_record             
;
2021-04-08 deposited with the CCDC.	2021-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H13 F2 N O'
_chemical_formula_weight         309.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0583 0.0400 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.982(5)
_cell_length_b                   13.786(5)
_cell_length_c                   13.975(3)
_cell_angle_alpha                112.81(3)
_cell_angle_beta                 107.33(3)
_cell_angle_gamma                96.28(3)
_cell_volume                     1472.2(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9894
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      56.99

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.552
_shelx_estimated_absorpt_T_min   0.699
_shelx_estimated_absorpt_T_max   0.927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6659
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_process_details   
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.34138
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44799
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_av_R_equivalents  0.0697
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.349
_diffrn_reflns_theta_max         56.499
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5927
_reflns_number_gt                4918
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0629P)²+0.3470P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0116(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5927
_refine_ls_number_parameters     444
_refine_ls_number_restraints     76
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1250
_refine_ls_wR_factor_gt          0.1168
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.16384(14) 0.16502(9) 0.77589(10) 0.0614(3) Uani 1 1 d . . . . .
F2 F -0.00817(13) 0.13458(9) 0.61455(10) 0.0619(3) Uani 1 1 d . . . . .
N1 N 0.63028(14) 0.51554(10) 0.80362(10) 0.0306(3) Uani 1 1 d . . . . .
O1 O 0.49650(13) 0.51714(9) 0.63604(9) 0.0396(3) Uani 1 1 d . . . . .
C1 C 0.49751(17) 0.47895(11) 0.70233(12) 0.0309(3) Uani 1 1 d . . . . .
C2 C 0.37299(17) 0.39480(11) 0.68906(12) 0.0301(3) Uani 1 1 d . . . . .
C3 C 0.20673(17) 0.32091(12) 0.60640(13) 0.0347(3) Uani 1 1 d . . . . .
H3A H 0.204532 0.269380 0.532853 0.042 Uiso 1 1 calc R U . . .
H3B H 0.119556 0.358780 0.598611 0.042 Uiso 1 1 calc R U . . .
C4 C 0.22511(18) 0.27484(12) 0.69234(12) 0.0337(3) Uani 1 1 d . . . . .
C5 C 0.38276(17) 0.35359(11) 0.76343(12) 0.0294(3) Uani 1 1 d . . . . .
C6 C 0.51693(17) 0.39133(11) 0.86618(12) 0.0301(3) Uani 1 1 d . . . . .
C7 C 0.53071(19) 0.35198(13) 0.94613(12) 0.0358(3) Uani 1 1 d . . . . .
H7 H 0.446315 0.295116 0.933412 0.043 Uiso 1 1 calc R U . . .
C8 C 0.6657(2) 0.39506(14) 1.04314(13) 0.0413(4) Uani 1 1 d . . . . .
H8 H 0.675646 0.367301 1.096619 0.050 Uiso 1 1 calc R U . . .
C9 C 0.7876(2) 0.47978(14) 1.06191(13) 0.0422(4) Uani 1 1 d . . . . .
H9 H 0.879846 0.510310 1.129303 0.051 Uiso 1 1 calc R U . . .
C10 C 0.77693(18) 0.52023(13) 0.98461(13) 0.0378(3) Uani 1 1 d . . . . .
H10 H 0.861634 0.578061 0.999458 0.045 Uiso 1 1 calc R U . . .
C11 C 0.64205(17) 0.47671(11) 0.88419(12) 0.0307(3) Uani 1 1 d . . . . .
C12 C 0.76495(18) 0.60003(13) 0.82103(13) 0.0371(3) Uani 1 1 d . . . . .
H12A H 0.761298 0.593722 0.747300 0.045 Uiso 1 1 calc R U . . .
H12B H 0.867989 0.586527 0.857377 0.045 Uiso 1 1 calc R U . . .
C13 C 0.7623(2) 0.71470(13) 0.89180(13) 0.0390(4) Uani 1 1 d . . . . .
C14 C 0.6201(2) 0.74801(14) 0.87498(15) 0.0466(4) Uani 1 1 d . . . . .
H14 H 0.521509 0.696686 0.821436 0.056 Uiso 1 1 calc R U . . .
C15 C 0.6199(3) 0.85503(16) 0.93513(18) 0.0656(6) Uani 1 1 d . . . . .
H15 H 0.521707 0.876659 0.922972 0.079 Uiso 1 1 calc R U . . .
C16 C 0.7623(4) 0.92964(18) 1.01243(19) 0.0788(7) Uani 1 1 d . U . . .
H16 H 0.762398 1.003062 1.053416 0.095 Uiso 1 1 calc R U . . .
C17 C 0.9046(3) 0.89873(17) 1.03081(16) 0.0749(7) Uani 1 1 d . U . . .
H17 H 1.002463 0.950746 1.084586 0.090 Uiso 1 1 calc R U . . .
C18 C 0.9057(2) 0.79073(15) 0.97044(14) 0.0533(5) Uani 1 1 d . . . . .
H18 H 1.004122 0.769494 0.983206 0.064 Uiso 1 1 calc R U . . .
C19 C 0.1335(2) 0.19607(14) 0.69489(14) 0.0428(4) Uani 1 1 d . . . . .
N2 N 0.66690(14) 0.30969(10) 0.55316(10) 0.0300(3) Uani 1 1 d . . . . .
O2 O 0.90745(13) 0.39099(9) 0.70377(9) 0.0437(3) Uani 1 1 d . . . . .
C20 C 0.77655(17) 0.32232(12) 0.65480(12) 0.0325(3) Uani 1 1 d . . . . .
C21 C 0.71729(19) 0.24871(13) 0.69266(12) 0.0355(3) Uani 1 1 d . . . . .
C22 C 0.7633(2) 0.22077(15) 0.79095(14) 0.0469(4) Uani 1 1 d . . . . .
H22A H 0.775328 0.280308 0.863329 0.056 Uiso 1 1 calc R U . . .
H22B H 0.854657 0.186439 0.797960 0.056 Uiso 1 1 calc R U . . .
C23 C 0.5958(2) 0.14040(14) 0.72598(15) 0.0448(4) Uani 1 1 d D . . . .
C24 C 0.57254(19) 0.17501(12) 0.63645(13) 0.0347(3) Uani 1 1 d . . . . .
C25 C 0.46426(18) 0.15871(12) 0.53037(12) 0.0331(3) Uani 1 1 d . . . . .
C26 C 0.3161(2) 0.08032(13) 0.46571(14) 0.0414(4) Uani 1 1 d . . . . .
H26 H 0.279931 0.032461 0.492721 0.050 Uiso 1 1 calc R U . . .
C27 C 0.2228(2) 0.07201(14) 0.36395(15) 0.0470(4) Uani 1 1 d . . . . .
H27 H 0.122670 0.018684 0.320537 0.056 Uiso 1 1 calc R U . . .
C28 C 0.2765(2) 0.14264(15) 0.32471(14) 0.0456(4) Uani 1 1 d . . . . .
H28 H 0.212193 0.136280 0.253857 0.055 Uiso 1 1 calc R U . . .
C29 C 0.42037(18) 0.22127(14) 0.38638(13) 0.0383(3) Uani 1 1 d . . . . .
H29 H 0.453474 0.269153 0.358453 0.046 Uiso 1 1 calc R U . . .
C30 C 0.51844(17) 0.23087(11) 0.49057(12) 0.0306(3) Uani 1 1 d . . . . .
C31 C 0.71665(18) 0.38469(12) 0.51037(12) 0.0337(3) Uani 1 1 d . . . . .
H31A H 0.798040 0.449943 0.573663 0.040 Uiso 1 1 calc R U . . .
H31B H 0.621916 0.408695 0.478725 0.040 Uiso 1 1 calc R U . . .
C32 C 0.78658(16) 0.33608(12) 0.42184(12) 0.0313(3) Uani 1 1 d . . . . .
C33 C 0.83856(18) 0.40137(13) 0.37705(14) 0.0389(4) Uani 1 1 d . . . . .
H33 H 0.828589 0.474125 0.402318 0.047 Uiso 1 1 calc R U . . .
C34 C 0.9045(2) 0.36183(16) 0.29628(15) 0.0472(4) Uani 1 1 d . . . . .
H34 H 0.940359 0.407489 0.266949 0.057 Uiso 1 1 calc R U . . .
C35 C 0.9181(2) 0.25574(17) 0.25831(15) 0.0521(5) Uani 1 1 d . . . . .
H35 H 0.962141 0.227970 0.202204 0.062 Uiso 1 1 calc R U . . .
C36 C 0.8675(2) 0.19036(15) 0.30239(15) 0.0488(4) Uani 1 1 d . . . . .
H36 H 0.876858 0.117469 0.276513 0.059 Uiso 1 1 calc R U . . .
C37 C 0.80276(19) 0.23055(13) 0.38442(13) 0.0384(3) Uani 1 1 d . . . . .
H37 H 0.769476 0.185258 0.414923 0.046 Uiso 1 1 calc R U . . .
C38 C 0.5005(16) 0.0754(5) 0.7455(7) 0.0549(16) Uani 0.79(4) 1 d . U P A 1
F3 F 0.3506(15) 0.0160(4) 0.6797(8) 0.0710(16) Uani 0.79(4) 1 d . U P A 1
F4 F 0.5449(19) 0.0580(7) 0.8360(8) 0.0828(19) Uani 0.79(4) 1 d . . P A 1
C38' C 0.545(3) 0.0756(18) 0.7605(18) 0.048(4) Uani 0.21(4) 1 d D U P A 2
F3' F 0.401(3) 0.008(2) 0.695(2) 0.072(4) Uani 0.21(4) 1 d D U P A 2
F4' F 0.609(4) 0.076(2) 0.8579(18) 0.068(4) Uani 0.21(4) 1 d D U 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 C19 1.325(2) . ?
F2 C19 1.332(2) . ?
N1 C11 1.4051(19) . ?
N1 C1 1.411(2) . ?
N1 C12 1.475(2) . ?
O1 C1 1.2287(17) . ?
C1 C2 1.434(2) . ?
C2 C5 1.351(2) . ?
C2 C3 1.526(2) . ?
C3 C4 1.539(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C19 1.307(2) . ?
C4 C5 1.470(2) . ?
C5 C6 1.427(2) . ?
C6 C7 1.400(2) . ?
C6 C11 1.423(2) . ?
C7 C8 1.379(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.394(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.380(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.404(2) . ?
C10 H10 0.9500 . ?
C12 C13 1.512(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.390(3) . ?
C13 C18 1.390(3) . ?
C14 C15 1.387(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.374(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.375(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.401(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
N2 C20 1.3984(19) . ?
N2 C30 1.405(2) . ?
N2 C31 1.4709(18) . ?
O2 C20 1.234(2) . ?
C20 C21 1.435(2) . ?
C21 C24 1.350(2) . ?
C21 C22 1.521(2) . ?
C22 C23 1.535(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C38' 1.270(16) . ?
C23 C38 1.331(7) . ?
C23 C24 1.472(2) . ?
C24 C25 1.424(2) . ?
C25 C26 1.403(2) . ?
C25 C30 1.421(2) . ?
C26 C27 1.371(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.396(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.376(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.405(2) . ?
C29 H29 0.9500 . ?
C31 C32 1.512(2) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C37 1.383(2) . ?
C32 C33 1.393(2) . ?
C33 C34 1.383(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.383(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.381(3) . ?
C35 H35 0.9500 . ?
C36 C37 1.390(2) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?
C38 F3 1.329(7) . ?
C38 F4 1.330(6) . ?
C38' F4' 1.304(17) . ?
C38' F3' 1.321(18) . ?

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
C11 N1 C1 125.22(12) . . ?
C11 N1 C12 119.98(12) . . ?
C1 N1 C12 114.79(12) . . ?
O1 C1 N1 121.28(13) . . ?
O1 C1 C2 126.71(14) . . ?
N1 C1 C2 112.01(13) . . ?
C5 C2 C1 124.15(14) . . ?
C5 C2 C3 95.22(12) . . ?
C1 C2 C3 140.62(13) . . ?
C2 C3 C4 82.87(11) . . ?
C2 C3 H3A 114.8 . . ?
C4 C3 H3A 114.8 . . ?
C2 C3 H3B 114.8 . . ?
C4 C3 H3B 114.8 . . ?
H3A C3 H3B 111.9 . . ?
C19 C4 C5 137.24(15) . . ?
C19 C4 C3 132.75(15) . . ?
C5 C4 C3 90.00(11) . . ?
C2 C5 C6 123.65(13) . . ?
C2 C5 C4 91.89(12) . . ?
C6 C5 C4 144.46(14) . . ?
C7 C6 C11 120.39(14) . . ?
C7 C6 C5 125.42(14) . . ?
C11 C6 C5 114.18(13) . . ?
C8 C7 C6 120.55(15) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 119.27(15) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C10 C9 C8 121.36(15) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C11 120.62(15) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C11 N1 121.46(14) . . ?
C10 C11 C6 117.79(14) . . ?
N1 C11 C6 120.75(13) . . ?
N1 C12 C13 113.71(12) . . ?
N1 C12 H12A 108.8 . . ?
C13 C12 H12A 108.8 . . ?
N1 C12 H12B 108.8 . . ?
C13 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 C18 118.84(17) . . ?
C14 C13 C12 121.18(15) . . ?
C18 C13 C12 119.85(17) . . ?
C15 C14 C13 121.02(19) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C16 C15 C14 119.7(2) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 120.4(2) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C18 120.2(2) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C13 C18 C17 119.8(2) . . ?
C13 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C4 C19 F1 126.56(16) . . ?
C4 C19 F2 124.15(16) . . ?
F1 C19 F2 109.28(14) . . ?
C20 N2 C30 124.90(13) . . ?
C20 N2 C31 115.69(13) . . ?
C30 N2 C31 119.40(12) . . ?
O2 C20 N2 121.64(14) . . ?
O2 C20 C21 126.00(14) . . ?
N2 C20 C21 112.35(13) . . ?
C24 C21 C20 124.00(14) . . ?
C24 C21 C22 95.07(14) . . ?
C20 C21 C22 140.89(16) . . ?
C21 C22 C23 83.27(13) . . ?
C21 C22 H22A 114.8 . . ?
C23 C22 H22A 114.8 . . ?
C21 C22 H22B 114.8 . . ?
C23 C22 H22B 114.8 . . ?
H22A C22 H22B 111.8 . . ?
C38' C23 C24 148.5(10) . . ?
C38 C23 C24 133.7(6) . . ?
C38' C23 C22 121.5(10) . . ?
C38 C23 C22 136.2(5) . . ?
C24 C23 C22 89.70(13) . . ?
C21 C24 C25 123.56(14) . . ?
C21 C24 C23 91.93(14) . . ?
C25 C24 C23 144.51(16) . . ?
C26 C25 C30 119.83(14) . . ?
C26 C25 C24 126.20(15) . . ?
C30 C25 C24 113.97(14) . . ?
C27 C26 C25 120.73(16) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C26 C27 C28 119.40(16) . . ?
C26 C27 H27 120.3 . . ?
C28 C27 H27 120.3 . . ?
C29 C28 C27 121.47(16) . . ?
C29 C28 H28 119.3 . . ?
C27 C28 H28 119.3 . . ?
C28 C29 C30 120.14(16) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
C29 C30 N2 120.49(13) . . ?
C29 C30 C25 118.42(14) . . ?
N2 C30 C25 121.08(13) . . ?
N2 C31 C32 114.05(12) . . ?
N2 C31 H31A 108.7 . . ?
C32 C31 H31A 108.7 . . ?
N2 C31 H31B 108.7 . . ?
C32 C31 H31B 108.7 . . ?
H31A C31 H31B 107.6 . . ?
C37 C32 C33 118.71(14) . . ?
C37 C32 C31 123.08(13) . . ?
C33 C32 C31 118.21(13) . . ?
C34 C33 C32 120.95(15) . . ?
C34 C33 H33 119.5 . . ?
C32 C33 H33 119.5 . . ?
C35 C34 C33 119.90(15) . . ?
C35 C34 H34 120.1 . . ?
C33 C34 H34 120.1 . . ?
C36 C35 C34 119.65(16) . . ?
C36 C35 H35 120.2 . . ?
C34 C35 H35 120.2 . . ?
C35 C36 C37 120.41(17) . . ?
C35 C36 H36 119.8 . . ?
C37 C36 H36 119.8 . . ?
C32 C37 C36 120.38(15) . . ?
C32 C37 H37 119.8 . . ?
C36 C37 H37 119.8 . . ?
F3 C38 F4 108.8(5) . . ?
F3 C38 C23 127.2(6) . . ?
F4 C38 C23 124.0(6) . . ?
C23 C38' F4' 127.9(18) . . ?
C23 C38' F3' 115.6(17) . . ?
F4' C38' F3' 116.0(18) . . ?

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
C11 N1 C1 O1 -179.97(13) . . . . ?
C12 N1 C1 O1 -1.01(19) . . . . ?
C11 N1 C1 C2 -0.66(19) . . . . ?
C12 N1 C1 C2 178.30(12) . . . . ?
O1 C1 C2 C5 177.91(14) . . . . ?
N1 C1 C2 C5 -1.36(19) . . . . ?
O1 C1 C2 C3 -0.2(3) . . . . ?
N1 C1 C2 C3 -179.43(16) . . . . ?
C5 C2 C3 C4 -1.21(11) . . . . ?
C1 C2 C3 C4 177.19(18) . . . . ?
C2 C3 C4 C19 -178.01(18) . . . . ?
C2 C3 C4 C5 1.11(10) . . . . ?
C1 C2 C5 C6 1.9(2) . . . . ?
C3 C2 C5 C6 -179.30(13) . . . . ?
C1 C2 C5 C4 -177.52(13) . . . . ?
C3 C2 C5 C4 1.26(11) . . . . ?
C19 C4 C5 C2 177.8(2) . . . . ?
C3 C4 C5 C2 -1.24(11) . . . . ?
C19 C4 C5 C6 -1.4(3) . . . . ?
C3 C4 C5 C6 179.56(19) . . . . ?
C2 C5 C6 C7 179.02(14) . . . . ?
C4 C5 C6 C7 -1.9(3) . . . . ?
C2 C5 C6 C11 -0.4(2) . . . . ?
C4 C5 C6 C11 178.68(18) . . . . ?
C11 C6 C7 C8 -0.2(2) . . . . ?
C5 C6 C7 C8 -179.55(14) . . . . ?
C6 C7 C8 C9 1.1(2) . . . . ?
C7 C8 C9 C10 -1.0(2) . . . . ?
C8 C9 C10 C11 0.0(2) . . . . ?
C9 C10 C11 N1 -178.90(13) . . . . ?
C9 C10 C11 C6 1.0(2) . . . . ?
C1 N1 C11 C10 -177.98(13) . . . . ?
C12 N1 C11 C10 3.1(2) . . . . ?
C1 N1 C11 C6 2.2(2) . . . . ?
C12 N1 C11 C6 -176.75(12) . . . . ?
C7 C6 C11 C10 -0.8(2) . . . . ?
C5 C6 C11 C10 178.58(12) . . . . ?
C7 C6 C11 N1 179.02(12) . . . . ?
C5 C6 C11 N1 -1.56(18) . . . . ?
C11 N1 C12 C13 -84.42(17) . . . . ?
C1 N1 C12 C13 96.56(15) . . . . ?
N1 C12 C13 C14 -44.2(2) . . . . ?
N1 C12 C13 C18 140.04(15) . . . . ?
C18 C13 C14 C15 0.0(2) . . . . ?
C12 C13 C14 C15 -175.85(16) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
C14 C15 C16 C17 -0.3(3) . . . . ?
C15 C16 C17 C18 0.2(3) . . . . ?
C14 C13 C18 C17 -0.1(2) . . . . ?
C12 C13 C18 C17 175.82(15) . . . . ?
C16 C17 C18 C13 0.0(3) . . . . ?
C5 C4 C19 F1 1.9(3) . . . . ?
C3 C4 C19 F1 -179.38(15) . . . . ?
C5 C4 C19 F2 -178.74(16) . . . . ?
C3 C4 C19 F2 0.0(3) . . . . ?
C30 N2 C20 O2 177.57(13) . . . . ?
C31 N2 C20 O2 -1.18(19) . . . . ?
C30 N2 C20 C21 -3.10(19) . . . . ?
C31 N2 C20 C21 178.16(11) . . . . ?
O2 C20 C21 C24 179.68(14) . . . . ?
N2 C20 C21 C24 0.4(2) . . . . ?
O2 C20 C21 C22 2.6(3) . . . . ?
N2 C20 C21 C22 -176.71(17) . . . . ?
C24 C21 C22 C23 -1.57(12) . . . . ?
C20 C21 C22 C23 176.01(19) . . . . ?
C21 C22 C23 C38' 176.9(15) . . . . ?
C21 C22 C23 C38 -171.6(6) . . . . ?
C21 C22 C23 C24 1.43(11) . . . . ?
C20 C21 C24 C25 2.7(2) . . . . ?
C22 C21 C24 C25 -179.17(13) . . . . ?
C20 C21 C24 C23 -176.53(14) . . . . ?
C22 C21 C24 C23 1.62(12) . . . . ?
C38' C23 C24 C21 -174(2) . . . . ?
C38 C23 C24 C21 171.7(5) . . . . ?
C22 C23 C24 C21 -1.60(12) . . . . ?
C38' C23 C24 C25 7(2) . . . . ?
C38 C23 C24 C25 -7.2(6) . . . . ?
C22 C23 C24 C25 179.5(2) . . . . ?
C21 C24 C25 C26 176.87(14) . . . . ?
C23 C24 C25 C26 -4.5(3) . . . . ?
C21 C24 C25 C30 -2.9(2) . . . . ?
C23 C24 C25 C30 175.74(19) . . . . ?
C30 C25 C26 C27 0.3(2) . . . . ?
C24 C25 C26 C27 -179.41(14) . . . . ?
C25 C26 C27 C28 -0.1(2) . . . . ?
C26 C27 C28 C29 -0.6(3) . . . . ?
C27 C28 C29 C30 1.0(2) . . . . ?
C28 C29 C30 N2 178.87(14) . . . . ?
C28 C29 C30 C25 -0.7(2) . . . . ?
C20 N2 C30 C29 -176.71(13) . . . . ?
C31 N2 C30 C29 1.99(19) . . . . ?
C20 N2 C30 C25 2.9(2) . . . . ?
C31 N2 C30 C25 -178.42(12) . . . . ?
C26 C25 C30 C29 0.1(2) . . . . ?
C24 C25 C30 C29 179.84(13) . . . . ?
C26 C25 C30 N2 -179.53(13) . . . . ?
C24 C25 C30 N2 0.24(19) . . . . ?
C20 N2 C31 C32 98.99(15) . . . . ?
C30 N2 C31 C32 -79.82(16) . . . . ?
N2 C31 C32 C37 -0.1(2) . . . . ?
N2 C31 C32 C33 -179.40(13) . . . . ?
C37 C32 C33 C34 0.3(2) . . . . ?
C31 C32 C33 C34 179.62(14) . . . . ?
C32 C33 C34 C35 0.6(2) . . . . ?
C33 C34 C35 C36 -0.8(3) . . . . ?
C34 C35 C36 C37 0.1(3) . . . . ?
C33 C32 C37 C36 -1.0(2) . . . . ?
C31 C32 C37 C36 179.74(15) . . . . ?
C35 C36 C37 C32 0.8(3) . . . . ?
C24 C23 C38 F3 4.4(9) . . . . ?
C22 C23 C38 F3 174.8(4) . . . . ?
C24 C23 C38 F4 -177.3(5) . . . . ?
C22 C23 C38 F4 -7.0(11) . . . . ?
C24 C23 C38' F4' -177.6(15) . . . . ?
C22 C23 C38' F4' 11(3) . . . . ?
C24 C23 C38' F3' -7(4) . . . . ?
C22 C23 C38' F3' -177.9(16) . . . . ?

_refine_diff_density_max         0.232
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_mo_HX_0731_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2076891'
loop_
_audit_author_name
_audit_author_address
'xiao hu'
;fudan university
China
;
_audit_update_record             
;
2021-04-12 deposited with the CCDC.	2021-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H15 Br F3 N O'
_chemical_formula_weight         410.23

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'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   25.323(2)
_cell_length_b                   5.9171(4)
_cell_length_c                   25.206(2)
_cell_angle_alpha                90
_cell_angle_beta                 114.569(2)
_cell_angle_gamma                90
_cell_volume                     3434.9(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1548
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      24.32

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_F_000             1648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    2.430
_shelx_estimated_absorpt_T_min   0.811
_shelx_estimated_absorpt_T_max   0.829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.523
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9443
_diffrn_reflns_av_unetI/netI     0.1072
_diffrn_reflns_av_R_equivalents  0.1075
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.984
_diffrn_reflns_theta_max         25.070
_diffrn_reflns_theta_full        25.070
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             2997
_reflns_number_gt                2075
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+12.9768P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2997
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.1251
_refine_ls_wR_factor_gt          0.1066
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Br01 Br 0.62487(3) 0.42708(9) 0.52648(3) 0.0292(2) Uani 1 1 d . . . . .
F002 F 0.71793(14) -0.1300(5) 0.53357(15) 0.0337(9) Uani 1 1 d . . . . .
F003 F 0.62834(14) -0.0596(5) 0.48159(14) 0.0318(8) Uani 1 1 d . . . . .
F004 F 0.69509(16) 0.1486(6) 0.47554(15) 0.0398(9) Uani 1 1 d . . . . .
O005 O 0.73695(18) 0.5431(7) 0.70714(18) 0.0389(11) Uani 1 1 d . . . . .
N006 N 0.64601(19) 0.4041(7) 0.68070(18) 0.0209(10) Uani 1 1 d . . . . .
C007 C 0.6014(2) 0.2445(9) 0.6492(2) 0.0194(12) Uani 1 1 d . . . . .
C008 C 0.6098(2) 0.0777(9) 0.6139(2) 0.0198(12) Uani 1 1 d . . . . .
C009 C 0.6809(2) 0.0317(9) 0.5126(2) 0.0252(14) Uani 1 1 d . . . . .
C00A C 0.5645(2) -0.0650(9) 0.5818(2) 0.0227(12) Uani 1 1 d . . . . .
H00A H 0.570107 -0.176132 0.557452 0.027 Uiso 1 1 calc R U . . .
C00B C 0.6675(2) 0.0579(8) 0.6110(2) 0.0177(12) Uani 1 1 d . . . . .
H00B H 0.678875 -0.104773 0.612901 0.021 Uiso 1 1 calc R U . . .
C00C C 0.6792(2) 0.1809(9) 0.5619(2) 0.0204(12) Uani 1 1 d . . . . .
C00D C 0.7012(2) 0.3940(10) 0.6826(2) 0.0267(14) Uani 1 1 d . . . . .
C00E C 0.7380(3) 0.2635(10) 0.6089(2) 0.0266(14) Uani 1 1 d . . . . .
H00C H 0.771784 0.176023 0.610064 0.032 Uiso 1 1 calc R U . . .
H00D H 0.744487 0.427857 0.607307 0.032 Uiso 1 1 calc R U . . .
C00F C 0.6261(2) 0.5386(9) 0.7651(2) 0.0214(13) Uani 1 1 d . . . . .
C00G C 0.5476(2) 0.2571(10) 0.6517(2) 0.0278(14) Uani 1 1 d . . . . .
H00G H 0.541368 0.368446 0.675639 0.033 Uiso 1 1 calc R U . . .
C00H C 0.5030(3) 0.1112(10) 0.6201(3) 0.0319(15) Uani 1 1 d . . . . .
H00H H 0.466762 0.121204 0.622863 0.038 Uiso 1 1 calc R U . . .
C00I C 0.5112(2) -0.0488(9) 0.5846(2) 0.0273(13) Uani 1 1 d . . . . .
H00I H 0.480444 -0.147548 0.562042 0.033 Uiso 1 1 calc R U . . .
C00J C 0.7177(2) 0.1954(9) 0.6563(2) 0.0215(13) Uani 1 1 d . . . . .
H00J H 0.746644 0.096240 0.686686 0.026 Uiso 1 1 calc R U . . .
C00K C 0.6321(3) 0.5946(9) 0.7093(2) 0.0255(13) Uani 1 1 d . . . . .
H00E H 0.595225 0.662772 0.681561 0.031 Uiso 1 1 calc R U . . .
H00F H 0.662848 0.710257 0.718166 0.031 Uiso 1 1 calc R U . . .
C00L C 0.6501(2) 0.3431(9) 0.7969(2) 0.0261(14) Uani 1 1 d . . . . .
H00L H 0.669796 0.237922 0.783070 0.031 Uiso 1 1 calc R U . . .
C00M C 0.6167(3) 0.4523(11) 0.8696(3) 0.0372(16) Uani 1 1 d . . . . .
H00M H 0.613247 0.422928 0.905039 0.045 Uiso 1 1 calc R U . . .
C00N C 0.6450(3) 0.3027(10) 0.8493(2) 0.0322(15) Uani 1 1 d . . . . .
H00N H 0.661460 0.169683 0.870965 0.039 Uiso 1 1 calc R U . . .
C00O C 0.5984(3) 0.6888(10) 0.7866(3) 0.0367(16) Uani 1 1 d . . . . .
H00O H 0.582487 0.823853 0.765652 0.044 Uiso 1 1 calc R U . . .
C00P C 0.5932(3) 0.6462(11) 0.8383(3) 0.0447(19) Uani 1 1 d . . . . .
H00P H 0.573452 0.750797 0.852280 0.054 Uiso 1 1 calc R U . . .


_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
Br01 C00C 1.947(5) . ?
F002 C009 1.289(6) . ?
F003 C009 1.344(6) . ?
F004 C009 1.326(6) . ?
O005 C00D 1.231(6) . ?
N006 C00D 1.379(7) . ?
N006 C007 1.433(7) . ?
N006 C00K 1.458(7) . ?
C007 C00G 1.393(8) . ?
C007 C008 1.403(7) . ?
C008 C00A 1.383(7) . ?
C008 C00B 1.497(7) . ?
C009 C00C 1.541(8) . ?
C00A C00I 1.383(8) . ?
C00A H00A 0.9500 . ?
C00B C00J 1.541(7) . ?
C00B C00C 1.565(7) . ?
C00B H00B 1.0000 . ?
C00C C00E 1.546(8) . ?
C00D C00J 1.492(8) . ?
C00E C00J 1.538(7) . ?
C00E H00C 0.9900 . ?
C00E H00D 0.9900 . ?
C00F C00O 1.376(8) . ?
C00F C00L 1.395(8) . ?
C00F C00K 1.512(7) . ?
C00G C00H 1.380(8) . ?
C00G H00G 0.9500 . ?
C00H C00I 1.378(8) . ?
C00H H00H 0.9500 . ?
C00I H00I 0.9500 . ?
C00J H00J 1.0000 . ?
C00K H00E 0.9900 . ?
C00K H00F 0.9900 . ?
C00L C00N 1.399(8) . ?
C00L H00L 0.9500 . ?
C00M C00N 1.365(8) . ?
C00M C00P 1.379(9) . ?
C00M H00M 0.9500 . ?
C00N H00N 0.9500 . ?
C00O C00P 1.387(9) . ?
C00O H00O 0.9500 . ?
C00P H00P 0.9500 . ?

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
C00D N006 C007 123.0(5) . . ?
C00D N006 C00K 117.8(5) . . ?
C007 N006 C00K 119.1(4) . . ?
C00G C007 C008 118.4(5) . . ?
C00G C007 N006 120.0(5) . . ?
C008 C007 N006 121.5(5) . . ?
C00A C008 C007 119.5(5) . . ?
C00A C008 C00B 120.9(5) . . ?
C007 C008 C00B 119.7(5) . . ?
F002 C009 F004 108.2(5) . . ?
F002 C009 F003 108.4(4) . . ?
F004 C009 F003 107.1(4) . . ?
F002 C009 C00C 110.7(4) . . ?
F004 C009 C00C 112.1(4) . . ?
F003 C009 C00C 110.2(5) . . ?
C008 C00A C00I 121.2(5) . . ?
C008 C00A H00A 119.4 . . ?
C00I C00A H00A 119.4 . . ?
C008 C00B C00J 116.3(4) . . ?
C008 C00B C00C 120.7(4) . . ?
C00J C00B C00C 88.4(4) . . ?
C008 C00B H00B 109.9 . . ?
C00J C00B H00B 109.9 . . ?
C00C C00B H00B 109.9 . . ?
C009 C00C C00E 117.2(5) . . ?
C009 C00C C00B 116.7(4) . . ?
C00E C00C C00B 88.9(4) . . ?
C009 C00C Br01 108.0(4) . . ?
C00E C00C Br01 112.7(4) . . ?
C00B C00C Br01 112.4(4) . . ?
O005 C00D N006 120.6(5) . . ?
O005 C00D C00J 120.3(5) . . ?
N006 C00D C00J 119.1(5) . . ?
C00J C00E C00C 89.2(4) . . ?
C00J C00E H00C 113.8 . . ?
C00C C00E H00C 113.8 . . ?
C00J C00E H00D 113.8 . . ?
C00C C00E H00D 113.8 . . ?
H00C C00E H00D 111.0 . . ?
C00O C00F C00L 118.7(5) . . ?
C00O C00F C00K 119.3(5) . . ?
C00L C00F C00K 121.9(5) . . ?
C00H C00G C007 121.5(5) . . ?
C00H C00G H00G 119.3 . . ?
C007 C00G H00G 119.3 . . ?
C00I C00H C00G 119.7(6) . . ?
C00I C00H H00H 120.1 . . ?
C00G C00H H00H 120.1 . . ?
C00H C00I C00A 119.6(5) . . ?
C00H C00I H00I 120.2 . . ?
C00A C00I H00I 120.2 . . ?
C00D C00J C00E 112.6(5) . . ?
C00D C00J C00B 116.6(5) . . ?
C00E C00J C00B 90.1(4) . . ?
C00D C00J H00J 111.9 . . ?
C00E C00J H00J 111.9 . . ?
C00B C00J H00J 111.9 . . ?
N006 C00K C00F 115.4(4) . . ?
N006 C00K H00E 108.4 . . ?
C00F C00K H00E 108.4 . . ?
N006 C00K H00F 108.4 . . ?
C00F C00K H00F 108.4 . . ?
H00E C00K H00F 107.5 . . ?
C00F C00L C00N 119.7(5) . . ?
C00F C00L H00L 120.2 . . ?
C00N C00L H00L 120.2 . . ?
C00N C00M C00P 119.7(6) . . ?
C00N C00M H00M 120.2 . . ?
C00P C00M H00M 120.2 . . ?
C00M C00N C00L 120.7(6) . . ?
C00M C00N H00N 119.6 . . ?
C00L C00N H00N 119.6 . . ?
C00F C00O C00P 121.1(6) . . ?
C00F C00O H00O 119.4 . . ?
C00P C00O H00O 119.4 . . ?
C00M C00P C00O 120.0(6) . . ?
C00M C00P H00P 120.0 . . ?
C00O C00P H00P 120.0 . . ?

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
C00D N006 C007 C00G 176.4(5) . . . . ?
C00K N006 C007 C00G -7.4(7) . . . . ?
C00D N006 C007 C008 -5.6(8) . . . . ?
C00K N006 C007 C008 170.6(5) . . . . ?
C00G C007 C008 C00A 1.5(8) . . . . ?
N006 C007 C008 C00A -176.5(5) . . . . ?
C00G C007 C008 C00B -179.1(5) . . . . ?
N006 C007 C008 C00B 2.8(7) . . . . ?
C007 C008 C00A C00I -1.1(8) . . . . ?
C00B C008 C00A C00I 179.6(5) . . . . ?
C00A C008 C00B C00J -169.5(5) . . . . ?
C007 C008 C00B C00J 11.2(7) . . . . ?
C00A C008 C00B C00C 85.6(6) . . . . ?
C007 C008 C00B C00C -93.8(6) . . . . ?
F002 C009 C00C C00E 49.0(6) . . . . ?
F004 C009 C00C C00E -71.9(6) . . . . ?
F003 C009 C00C C00E 168.9(4) . . . . ?
F002 C009 C00C C00B -54.6(6) . . . . ?
F004 C009 C00C C00B -175.5(4) . . . . ?
F003 C009 C00C C00B 65.4(6) . . . . ?
F002 C009 C00C Br01 177.6(3) . . . . ?
F004 C009 C00C Br01 56.7(5) . . . . ?
F003 C009 C00C Br01 -62.4(5) . . . . ?
C008 C00B C00C C009 -105.9(6) . . . . ?
C00J C00B C00C C009 134.2(5) . . . . ?
C008 C00B C00C C00E 133.9(5) . . . . ?
C00J C00B C00C C00E 14.0(4) . . . . ?
C008 C00B C00C Br01 19.7(6) . . . . ?
C00J C00B C00C Br01 -100.2(4) . . . . ?
C007 N006 C00D O005 175.3(5) . . . . ?
C00K N006 C00D O005 -0.9(8) . . . . ?
C007 N006 C00D C00J -6.8(8) . . . . ?
C00K N006 C00D C00J 177.0(5) . . . . ?
C009 C00C C00E C00J -133.8(5) . . . . ?
C00B C00C C00E C00J -14.0(4) . . . . ?
Br01 C00C C00E C00J 99.9(4) . . . . ?
C008 C007 C00G C00H -0.5(8) . . . . ?
N006 C007 C00G C00H 177.5(5) . . . . ?
C007 C00G C00H C00I -0.9(9) . . . . ?
C00G C00H C00I C00A 1.4(9) . . . . ?
C008 C00A C00I C00H -0.4(9) . . . . ?
O005 C00D C00J C00E -59.5(7) . . . . ?
N006 C00D C00J C00E 122.6(5) . . . . ?
O005 C00D C00J C00B -161.6(5) . . . . ?
N006 C00D C00J C00B 20.5(7) . . . . ?
C00C C00E C00J C00D -104.8(5) . . . . ?
C00C C00E C00J C00B 14.2(4) . . . . ?
C008 C00B C00J C00D -22.3(7) . . . . ?
C00C C00B C00J C00D 101.5(5) . . . . ?
C008 C00B C00J C00E -137.9(5) . . . . ?
C00C C00B C00J C00E -14.1(4) . . . . ?
C00D N006 C00K C00F -108.2(5) . . . . ?
C007 N006 C00K C00F 75.4(6) . . . . ?
C00O C00F C00K N006 -162.7(5) . . . . ?
C00L C00F C00K N006 20.2(8) . . . . ?
C00O C00F C00L C00N 0.7(8) . . . . ?
C00K C00F C00L C00N 177.8(5) . . . . ?
C00P C00M C00N C00L -0.5(10) . . . . ?
C00F C00L C00N C00M 0.1(9) . . . . ?
C00L C00F C00O C00P -1.2(9) . . . . ?
C00K C00F C00O C00P -178.4(6) . . . . ?
C00N C00M C00P C00O 0.0(10) . . . . ?
C00F C00O C00P C00M 0.9(10) . . . . ?

_refine_diff_density_max         0.552
_refine_diff_density_min         -0.601
_refine_diff_density_rms         0.118

####################################################################### 
# 
# 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_ga_210409a_a
_database_code_depnum_ccdc_archive 'CCDC 2076890'
loop_
_audit_author_name
_audit_author_address
'xiao hu'
;fudan university
China
;
_audit_update_record             
;
2021-04-12 deposited with the CCDC.	2021-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H14 F3 N O'
_chemical_formula_weight         329.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0583 0.0400 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

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                   9.0542(7)
_cell_length_b                   10.0870(8)
_cell_length_c                   16.9352(14)
_cell_angle_alpha                90
_cell_angle_beta                 93.412(3)
_cell_angle_gamma                90
_cell_volume                     1543.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9685
_cell_measurement_theta_min      4.44
_cell_measurement_theta_max      57.08

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.609
_shelx_estimated_absorpt_T_min   0.806
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.594
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.34138
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17360
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.441
_diffrn_reflns_theta_max         57.131
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3162
_reflns_number_gt                2779
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0678P)²+0.4860P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3162
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1276
_refine_ls_wR_factor_gt          0.1219
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.54140(14) 0.08931(11) 0.43116(6) 0.0591(3) Uani 1 1 d . . . . .
F2 F 0.54922(17) -0.01963(11) 0.32373(7) 0.0749(4) Uani 1 1 d . . . . .
F3 F 0.69837(12) 0.14316(13) 0.34728(8) 0.0680(4) Uani 1 1 d . . . . .
N1 N 0.27447(12) 0.52349(11) 0.42082(6) 0.0262(3) Uani 1 1 d . . . . .
O1 O 0.06433(11) 0.39520(11) 0.41111(6) 0.0386(3) Uani 1 1 d . . . . .
C1 C 0.19655(15) 0.40723(14) 0.40004(8) 0.0290(3) Uani 1 1 d . . . . .
C2 C 0.28905(15) 0.30974(14) 0.36568(8) 0.0307(3) Uani 1 1 d . . . . .
C3 C 0.28153(18) 0.17103(15) 0.33156(10) 0.0413(4) Uani 1 1 d . . . . .
H3A H 0.213942 0.161359 0.283775 0.050 Uiso 1 1 calc R U . . .
H3B H 0.265470 0.100389 0.370721 0.050 Uiso 1 1 calc R U . . .
C4 C 0.44883(17) 0.19452(15) 0.31406(9) 0.0365(3) Uani 1 1 d . . . . .
H4 H 0.462566 0.201873 0.256070 0.044 Uiso 1 1 calc R U . . .
C5 C 0.43231(15) 0.32982(14) 0.35228(8) 0.0299(3) Uani 1 1 d . . . . .
C6 C 0.50992(14) 0.44895(14) 0.37139(8) 0.0280(3) Uani 1 1 d . . . . .
C7 C 0.65952(16) 0.47384(16) 0.35889(9) 0.0354(3) Uani 1 1 d . . . . .
H7 H 0.716923 0.407570 0.335214 0.042 Uiso 1 1 calc R U . . .
C8 C 0.72367(16) 0.59284(18) 0.38051(9) 0.0410(4) Uani 1 1 d . . . . .
H8 H 0.825599 0.608041 0.373476 0.049 Uiso 1 1 calc R U . . .
C9 C 0.63774(17) 0.69063(17) 0.41277(9) 0.0403(4) Uani 1 1 d . . . . .
H9 H 0.681669 0.773516 0.426824 0.048 Uiso 1 1 calc R U . . .
C10 C 0.48973(16) 0.67033(15) 0.42494(9) 0.0339(3) Uani 1 1 d . . . . .
H10 H 0.432796 0.739541 0.446027 0.041 Uiso 1 1 calc R U . . .
C11 C 0.42361(14) 0.54773(13) 0.40620(7) 0.0264(3) Uani 1 1 d . . . . .
C12 C 0.18963(15) 0.62444(14) 0.46094(8) 0.0299(3) Uani 1 1 d . . . . .
H12A H 0.256329 0.669562 0.500850 0.036 Uiso 1 1 calc R U . . .
H12B H 0.111212 0.579801 0.489412 0.036 Uiso 1 1 calc R U . . .
C13 C 0.11874(14) 0.72764(13) 0.40642(8) 0.0273(3) Uani 1 1 d . . . . .
C14 C 0.13070(15) 0.72681(15) 0.32537(8) 0.0325(3) Uani 1 1 d . . . . .
H14 H 0.190333 0.661750 0.302123 0.039 Uiso 1 1 calc R U . . .
C15 C 0.05643(16) 0.82005(17) 0.27775(10) 0.0405(4) Uani 1 1 d . . . . .
H15 H 0.064182 0.818135 0.222069 0.049 Uiso 1 1 calc R U . . .
C16 C -0.02918(19) 0.91610(17) 0.31166(12) 0.0480(4) Uani 1 1 d . . . . .
H16 H -0.079572 0.980632 0.279301 0.058 Uiso 1 1 calc R U . . .
C17 C -0.04106(19) 0.91776(17) 0.39258(12) 0.0491(4) Uani 1 1 d . . . . .
H17 H -0.099716 0.983580 0.415816 0.059 Uiso 1 1 calc R U . . .
C18 C 0.03192(17) 0.82423(15) 0.43982(10) 0.0378(3) Uani 1 1 d . . . . .
H18 H 0.022898 0.825714 0.495412 0.045 Uiso 1 1 calc R U . . .
C19 C 0.5583(2) 0.10193(16) 0.35393(10) 0.0451(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
F1 C19 1.3319(19) . ?
F2 C19 1.329(2) . ?
F3 C19 1.346(2) . ?
N1 C1 1.4026(18) . ?
N1 C11 1.4086(16) . ?
N1 C12 1.4666(16) . ?
O1 C1 1.2287(17) . ?
C1 C2 1.4370(19) . ?
C2 C5 1.3453(19) . ?
C2 C3 1.514(2) . ?
C3 C4 1.579(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C19 1.494(2) . ?
C4 C5 1.522(2) . ?
C4 H4 1.0000 . ?
C5 C6 1.420(2) . ?
C6 C7 1.4060(19) . ?
C6 C11 1.4163(18) . ?
C7 C8 1.374(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.388(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.383(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.402(2) . ?
C10 H10 0.9500 . ?
C12 C13 1.5092(19) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.383(2) . ?
C13 C18 1.3928(19) . ?
C14 C15 1.387(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.386(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.381(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.380(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?

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
C1 N1 C11 125.05(11) . . ?
C1 N1 C12 115.29(11) . . ?
C11 N1 C12 119.66(11) . . ?
O1 C1 N1 121.63(12) . . ?
O1 C1 C2 126.22(13) . . ?
N1 C1 C2 112.16(11) . . ?
C5 C2 C1 123.80(13) . . ?
C5 C2 C3 95.54(12) . . ?
C1 C2 C3 140.62(13) . . ?
C2 C3 C4 84.90(11) . . ?
C2 C3 H3A 114.5 . . ?
C4 C3 H3A 114.5 . . ?
C2 C3 H3B 114.5 . . ?
C4 C3 H3B 114.5 . . ?
H3A C3 H3B 111.6 . . ?
C19 C4 C5 116.61(13) . . ?
C19 C4 C3 116.08(14) . . ?
C5 C4 C3 86.27(10) . . ?
C19 C4 H4 111.9 . . ?
C5 C4 H4 111.9 . . ?
C3 C4 H4 111.9 . . ?
C2 C5 C6 123.92(12) . . ?
C2 C5 C4 93.27(12) . . ?
C6 C5 C4 142.78(13) . . ?
C7 C6 C11 119.83(13) . . ?
C7 C6 C5 125.80(13) . . ?
C11 C6 C5 114.37(12) . . ?
C8 C7 C6 120.78(14) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 119.20(14) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C10 C9 C8 121.60(15) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C9 C10 C11 120.08(14) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 N1 120.94(12) . . ?
C10 C11 C6 118.43(12) . . ?
N1 C11 C6 120.63(12) . . ?
N1 C12 C13 114.26(11) . . ?
N1 C12 H12A 108.7 . . ?
C13 C12 H12A 108.7 . . ?
N1 C12 H12B 108.7 . . ?
C13 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C14 C13 C18 119.12(13) . . ?
C14 C13 C12 123.18(12) . . ?
C18 C13 C12 117.64(12) . . ?
C13 C14 C15 120.60(14) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 119.79(15) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C17 C16 C15 119.87(15) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C18 C17 C16 120.27(15) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C13 120.35(15) . . ?
C17 C18 H18 119.8 . . ?
C13 C18 H18 119.8 . . ?
F2 C19 F1 106.35(14) . . ?
F2 C19 F3 106.86(14) . . ?
F1 C19 F3 106.01(15) . . ?
F2 C19 C4 112.24(15) . . ?
F1 C19 C4 113.05(13) . . ?
F3 C19 C4 111.86(14) . . ?

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
C11 N1 C1 O1 -176.38(12) . . . . ?
C12 N1 C1 O1 3.84(18) . . . . ?
C11 N1 C1 C2 3.53(18) . . . . ?
C12 N1 C1 C2 -176.25(11) . . . . ?
O1 C1 C2 C5 177.52(14) . . . . ?
N1 C1 C2 C5 -2.38(19) . . . . ?
O1 C1 C2 C3 0.0(3) . . . . ?
N1 C1 C2 C3 -179.85(17) . . . . ?
C5 C2 C3 C4 -1.02(11) . . . . ?
C1 C2 C3 C4 176.87(19) . . . . ?
C2 C3 C4 C19 118.80(14) . . . . ?
C2 C3 C4 C5 0.90(10) . . . . ?
C1 C2 C5 C6 0.9(2) . . . . ?
C3 C2 C5 C6 179.27(13) . . . . ?
C1 C2 C5 C4 -177.34(14) . . . . ?
C3 C2 C5 C4 1.05(12) . . . . ?
C19 C4 C5 C2 -118.41(15) . . . . ?
C3 C4 C5 C2 -1.01(11) . . . . ?
C19 C4 C5 C6 64.0(2) . . . . ?
C3 C4 C5 C6 -178.56(19) . . . . ?
C2 C5 C6 C7 179.59(13) . . . . ?
C4 C5 C6 C7 -3.4(3) . . . . ?
C2 C5 C6 C11 -0.2(2) . . . . ?
C4 C5 C6 C11 176.86(17) . . . . ?
C11 C6 C7 C8 0.4(2) . . . . ?
C5 C6 C7 C8 -179.36(13) . . . . ?
C6 C7 C8 C9 -2.0(2) . . . . ?
C7 C8 C9 C10 1.1(2) . . . . ?
C8 C9 C10 C11 1.4(2) . . . . ?
C9 C10 C11 N1 177.69(12) . . . . ?
C9 C10 C11 C6 -3.0(2) . . . . ?
C1 N1 C11 C10 176.17(12) . . . . ?
C12 N1 C11 C10 -4.06(18) . . . . ?
C1 N1 C11 C6 -3.18(19) . . . . ?
C12 N1 C11 C6 176.59(11) . . . . ?
C7 C6 C11 C10 2.08(19) . . . . ?
C5 C6 C11 C10 -178.13(12) . . . . ?
C7 C6 C11 N1 -178.56(12) . . . . ?
C5 C6 C11 N1 1.24(18) . . . . ?
C1 N1 C12 C13 -94.07(14) . . . . ?
C11 N1 C12 C13 86.14(15) . . . . ?
N1 C12 C13 C14 0.78(19) . . . . ?
N1 C12 C13 C18 177.78(12) . . . . ?
C18 C13 C14 C15 -0.5(2) . . . . ?
C12 C13 C14 C15 176.43(13) . . . . ?
C13 C14 C15 C16 0.8(2) . . . . ?
C14 C15 C16 C17 -0.5(2) . . . . ?
C15 C16 C17 C18 0.0(3) . . . . ?
C16 C17 C18 C13 0.3(3) . . . . ?
C14 C13 C18 C17 0.0(2) . . . . ?
C12 C13 C18 C17 -177.15(14) . . . . ?
C5 C4 C19 F2 170.45(14) . . . . ?
C3 C4 C19 F2 70.99(18) . . . . ?
C5 C4 C19 F1 50.1(2) . . . . ?
C3 C4 C19 F1 -49.3(2) . . . . ?
C5 C4 C19 F3 -69.44(17) . . . . ?
C3 C4 C19 F3 -168.90(13) . . . . ?

_refine_diff_density_max         0.228
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.048

