# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_190425_wzc_4343_0m
_database_code_depnum_ccdc_archive 'CCDC 1961660'
loop_
_audit_author_name
_audit_author_address
'Zhichao Wang'
;Zhejiang University
China
;
_audit_update_record             
;
2019-10-28 deposited with the CCDC.	2020-08-10 downloaded from the CCDC.
;
_audit_creation_date             2019-04-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C34 H19 F6 N3'
_chemical_formula_sum            'C34 H19 F6 N3'
_chemical_formula_weight         583.52
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.3025(11)
_cell_length_b                   15.7894(17)
_cell_length_c                   15.9352(16)
_cell_angle_alpha                90
_cell_angle_beta                 92.997(4)
_cell_angle_gamma                90
_cell_volume                     2588.6(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9855
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      26.41
_cell_measurement_theta_min      2.56
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.957
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6259
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1208 before and 0.0713 after correction.
The Ratio of minimum to maximum transmission is 0.8397.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.373
_exptl_crystal_size_mid          0.308
_exptl_crystal_size_min          0.23
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            45677
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.438
_diffrn_reflns_theta_min         2.363
_diffrn_ambient_temperature      169.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_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                4322
_reflns_number_total             5313
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         5313
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0494
_refine_ls_restrained_S_all      1.036
_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)+(0.0615P)²+1.9655P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1324
_refine_ls_wR_factor_ref         0.1422
_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), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12),
 C14(H14), C15(H15), C17(H17), C18(H18), C23(H23), C24(H24), C25(H25), C26(H26),
  C28(H28), C30(H30), C32(H32)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F -0.1316(3) 0.52159(13) 0.19235(16) 0.1119(8) Uani 1 1 d . . . . .
F2 F 0.02803(17) 0.49358(11) 0.12163(17) 0.1024(8) Uani 1 1 d . . . . .
F3 F -0.1399(2) 0.54967(12) 0.06416(14) 0.0986(8) Uani 1 1 d . . . . .
F4 F -0.20233(14) 0.87287(10) 0.19626(10) 0.0623(4) Uani 1 1 d . . . . .
F5 F -0.04581(13) 0.93562(9) 0.13841(11) 0.0624(4) Uani 1 1 d . . . . .
F6 F -0.18182(13) 0.86129(10) 0.06445(9) 0.0546(4) Uani 1 1 d . . . . .
N1 N 0.65891(15) 0.34297(10) 0.44304(10) 0.0293(3) Uani 1 1 d . . . . .
N2 N 0.34787(15) 0.65802(10) 0.28797(10) 0.0286(3) Uani 1 1 d . . . . .
N3 N 0.34199(15) 0.80829(10) 0.26858(10) 0.0295(3) Uani 1 1 d . . . . .
C1 C 0.86268(19) 0.38958(13) 0.52647(13) 0.0348(4) Uani 1 1 d . . . . .
H1 H 0.854909 0.448042 0.513038 0.042 Uiso 1 1 calc R . . . .
C2 C 0.9644(2) 0.35982(15) 0.57811(13) 0.0398(5) Uani 1 1 d . . . . .
H2 H 1.027307 0.398775 0.600629 0.048 Uiso 1 1 calc R . . . .
C3 C 0.9774(2) 0.27407(16) 0.59814(14) 0.0436(5) Uani 1 1 d . . . . .
H3 H 1.049671 0.255377 0.632771 0.052 Uiso 1 1 calc R . . . .
C4 C 0.8865(2) 0.21660(15) 0.56807(13) 0.0402(5) Uani 1 1 d . . . . .
H4 H 0.894879 0.158376 0.582369 0.048 Uiso 1 1 calc R . . . .
C5 C 0.78100(19) 0.24457(13) 0.51605(12) 0.0325(4) Uani 1 1 d . . . . .
C6 C 0.77159(18) 0.33076(12) 0.49469(11) 0.0299(4) Uani 1 1 d . . . . .
C7 C 0.59612(19) 0.26481(12) 0.43235(12) 0.0293(4) Uani 1 1 d . . . . .
C8 C 0.6698(2) 0.20244(12) 0.47672(12) 0.0332(4) Uani 1 1 d . . . . .
C9 C 0.6270(2) 0.11852(13) 0.47494(14) 0.0402(5) Uani 1 1 d . . . . .
H9 H 0.674759 0.076008 0.505377 0.048 Uiso 1 1 calc R . . . .
C10 C 0.5151(2) 0.09815(13) 0.42862(14) 0.0426(5) Uani 1 1 d . . . . .
H10 H 0.484727 0.041322 0.427802 0.051 Uiso 1 1 calc R . . . .
C11 C 0.4452(2) 0.16024(13) 0.38265(13) 0.0377(5) Uani 1 1 d . . . . .
H11 H 0.369464 0.144395 0.349848 0.045 Uiso 1 1 calc R . . . .
C12 C 0.48403(19) 0.24416(13) 0.38389(12) 0.0320(4) Uani 1 1 d . . . . .
H12 H 0.436058 0.286133 0.352866 0.038 Uiso 1 1 calc R . . . .
C13 C 0.61207(17) 0.42170(11) 0.41148(11) 0.0271(4) Uani 1 1 d . . . . .
C14 C 0.48028(18) 0.44116(12) 0.41480(11) 0.0283(4) Uani 1 1 d . . . . .
H14 H 0.422288 0.401188 0.436982 0.034 Uiso 1 1 calc R . . . .
C15 C 0.43423(18) 0.51841(12) 0.38589(11) 0.0282(4) Uani 1 1 d . . . . .
H15 H 0.343836 0.530179 0.386248 0.034 Uiso 1 1 calc R . . . .
C16 C 0.51815(18) 0.57963(12) 0.35609(11) 0.0276(4) Uani 1 1 d . . . . .
C17 C 0.64941(18) 0.55901(12) 0.35176(12) 0.0297(4) Uani 1 1 d . . . . .
H17 H 0.707781 0.599465 0.330774 0.036 Uiso 1 1 calc R . . . .
C18 C 0.69565(17) 0.48041(12) 0.37765(12) 0.0289(4) Uani 1 1 d . . . . .
H18 H 0.784557 0.466497 0.372330 0.035 Uiso 1 1 calc R . . . .
C19 C 0.46276(18) 0.66249(12) 0.32893(11) 0.0275(4) Uani 1 1 d . . . . .
C20 C 0.29229(18) 0.73178(12) 0.26097(11) 0.0283(4) Uani 1 1 d . . . . .
C21 C 0.46062(18) 0.81426(12) 0.31045(11) 0.0286(4) Uani 1 1 d . . . . .
C22 C 0.52500(18) 0.74182(12) 0.34546(11) 0.0281(4) Uani 1 1 d . . . . .
C23 C 0.64364(19) 0.75404(13) 0.39375(13) 0.0332(4) Uani 1 1 d . . . . .
H23 H 0.685340 0.707226 0.421186 0.040 Uiso 1 1 calc R . . . .
C24 C 0.6976(2) 0.83266(13) 0.40078(13) 0.0380(5) Uani 1 1 d . . . . .
H24 H 0.777058 0.840045 0.432983 0.046 Uiso 1 1 calc R . . . .
C25 C 0.6374(2) 0.90326(13) 0.36096(13) 0.0365(5) Uani 1 1 d . . . . .
H25 H 0.678396 0.957119 0.364227 0.044 Uiso 1 1 calc R . . . .
C26 C 0.5202(2) 0.89441(13) 0.31772(13) 0.0340(4) Uani 1 1 d . . . . .
H26 H 0.478698 0.942473 0.292459 0.041 Uiso 1 1 calc R . . . .
C27 C 0.16316(18) 0.72330(12) 0.21562(12) 0.0293(4) Uani 1 1 d . . . . .
C28 C 0.11383(19) 0.64370(13) 0.19352(12) 0.0332(4) Uani 1 1 d . . . . .
H28 H 0.162986 0.594230 0.207215 0.040 Uiso 1 1 calc R . . . .
C29 C -0.0069(2) 0.63677(14) 0.15158(13) 0.0362(5) Uani 1 1 d . . . . .
C30 C -0.08060(19) 0.70835(14) 0.13136(13) 0.0365(5) Uani 1 1 d . . . . .
H30 H -0.163185 0.703286 0.102376 0.044 Uiso 1 1 calc R . . . .
C31 C -0.03155(18) 0.78713(13) 0.15417(12) 0.0330(4) Uani 1 1 d . . . . .
C32 C 0.08929(18) 0.79507(13) 0.19617(12) 0.0312(4) Uani 1 1 d . . . . .
H32 H 0.121560 0.849548 0.211631 0.037 Uiso 1 1 calc R . . . .
C33 C -0.0612(2) 0.55095(15) 0.13121(17) 0.0501(6) Uani 1 1 d . . . . .
C34 C -0.1143(2) 0.86402(14) 0.13828(14) 0.0398(5) 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 C33 1.328(3) . ?
F2 C33 1.305(3) . ?
F3 C33 1.307(3) . ?
F4 C34 1.336(3) . ?
F5 C34 1.333(3) . ?
F6 C34 1.336(3) . ?
N1 C6 1.401(2) . ?
N1 C7 1.400(2) . ?
N1 C13 1.416(2) . ?
N2 C19 1.323(2) . ?
N2 C20 1.358(2) . ?
N3 C20 1.315(2) . ?
N3 C21 1.365(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.381(3) . ?
C1 C6 1.396(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.396(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.373(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.403(3) . ?
C5 C6 1.405(3) . ?
C5 C8 1.440(3) . ?
C7 C8 1.411(3) . ?
C7 C12 1.394(3) . ?
C8 C9 1.396(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.375(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.400(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.396(3) . ?
C13 C18 1.393(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.379(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.397(3) . ?
C16 C17 1.396(3) . ?
C16 C19 1.483(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.385(3) . ?
C18 H18 0.9500 . ?
C19 C22 1.425(3) . ?
C20 C27 1.486(3) . ?
C21 C22 1.422(3) . ?
C21 C26 1.409(3) . ?
C22 C23 1.423(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.363(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.411(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.365(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.394(3) . ?
C27 C32 1.391(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.385(3) . ?
C29 C30 1.390(3) . ?
C29 C33 1.495(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.384(3) . ?
C31 C32 1.388(3) . ?
C31 C34 1.497(3) . ?
C32 H32 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
C6 N1 C13 125.87(16) . . ?
C7 N1 C6 108.28(15) . . ?
C7 N1 C13 125.73(15) . . ?
C19 N2 C20 117.52(16) . . ?
C20 N3 C21 116.28(16) . . ?
C2 C1 H1 121.2 . . ?
C2 C1 C6 117.7(2) . . ?
C6 C1 H1 121.2 . . ?
C1 C2 H2 119.1 . . ?
C1 C2 C3 121.8(2) . . ?
C3 C2 H2 119.1 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.4(2) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C6 119.3(2) . . ?
C4 C5 C8 133.3(2) . . ?
C6 C5 C8 107.39(17) . . ?
N1 C6 C5 108.67(17) . . ?
C1 C6 N1 129.95(18) . . ?
C1 C6 C5 121.32(18) . . ?
N1 C7 C8 108.75(17) . . ?
C12 C7 N1 129.64(17) . . ?
C12 C7 C8 121.53(18) . . ?
C7 C8 C5 106.90(17) . . ?
C9 C8 C5 133.67(19) . . ?
C9 C8 C7 119.4(2) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 C8 119.2(2) . . ?
C10 C9 H9 120.4 . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.7(2) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 119.2 . . ?
C12 C11 C10 121.5(2) . . ?
C12 C11 H11 119.2 . . ?
C7 C12 H12 121.2 . . ?
C11 C12 C7 117.53(19) . . ?
C11 C12 H12 121.2 . . ?
C14 C13 N1 119.59(17) . . ?
C18 C13 N1 121.03(16) . . ?
C18 C13 C14 119.37(17) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.02(17) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 119.4 . . ?
C14 C15 C16 121.16(17) . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C19 118.31(16) . . ?
C17 C16 C15 118.29(17) . . ?
C17 C16 C19 123.39(17) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.89(17) . . ?
C18 C17 H17 119.6 . . ?
C13 C18 H18 119.9 . . ?
C17 C18 C13 120.12(17) . . ?
C17 C18 H18 119.9 . . ?
N2 C19 C16 114.68(16) . . ?
N2 C19 C22 121.34(17) . . ?
C22 C19 C16 123.98(16) . . ?
N2 C20 C27 115.39(16) . . ?
N3 C20 N2 127.08(17) . . ?
N3 C20 C27 117.50(16) . . ?
N3 C21 C22 121.59(17) . . ?
N3 C21 C26 118.51(17) . . ?
C26 C21 C22 119.89(17) . . ?
C21 C22 C19 116.00(17) . . ?
C21 C22 C23 118.23(17) . . ?
C23 C22 C19 125.77(17) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.23(18) . . ?
C24 C23 H23 119.9 . . ?
C23 C24 H24 119.5 . . ?
C23 C24 C25 120.98(19) . . ?
C25 C24 H24 119.5 . . ?
C24 C25 H25 119.9 . . ?
C26 C25 C24 120.20(19) . . ?
C26 C25 H25 119.9 . . ?
C21 C26 H26 119.9 . . ?
C25 C26 C21 120.21(18) . . ?
C25 C26 H26 119.9 . . ?
C28 C27 C20 120.61(17) . . ?
C32 C27 C20 120.02(17) . . ?
C32 C27 C28 119.36(17) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 C27 119.95(18) . . ?
C29 C28 H28 120.0 . . ?
C28 C29 C30 120.90(19) . . ?
C28 C29 C33 119.49(19) . . ?
C30 C29 C33 119.55(18) . . ?
C29 C30 H30 120.6 . . ?
C31 C30 C29 118.84(18) . . ?
C31 C30 H30 120.6 . . ?
C30 C31 C32 120.92(18) . . ?
C30 C31 C34 119.18(18) . . ?
C32 C31 C34 119.77(19) . . ?
C27 C32 H32 120.0 . . ?
C31 C32 C27 120.02(19) . . ?
C31 C32 H32 120.0 . . ?
F1 C33 C29 111.7(2) . . ?
F2 C33 F1 105.0(2) . . ?
F2 C33 F3 107.7(2) . . ?
F2 C33 C29 113.4(2) . . ?
F3 C33 F1 104.7(2) . . ?
F3 C33 C29 113.6(2) . . ?
F4 C34 F6 105.74(17) . . ?
F4 C34 C31 111.66(18) . . ?
F5 C34 F4 106.78(19) . . ?
F5 C34 F6 106.26(18) . . ?
F5 C34 C31 113.02(17) . . ?
F6 C34 C31 112.87(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_190528_wzc_4349_0m
_database_code_depnum_ccdc_archive 'CCDC 1961672'
loop_
_audit_author_name
_audit_author_address
'Zhichao Wang'
;Zhejiang University
China
;
_audit_update_record             
;
2019-10-28 deposited with the CCDC.	2020-08-10 downloaded from the CCDC.
;
_audit_creation_date             2019-05-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C H2 Cl2, C34 H19 F6 N3 O'
_chemical_formula_sum            'C35 H21 Cl2 F6 N3 O'
_chemical_formula_weight         684.45
_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'
Cl Cl 0.1484 0.1585 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.437(4)
_cell_length_b                   11.159(4)
_cell_length_c                   26.443(8)
_cell_angle_alpha                90
_cell_angle_beta                 93.920(12)
_cell_angle_gamma                90
_cell_volume                     3072.6(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9946
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      26.36
_cell_measurement_theta_min      2.40
_shelx_estimated_absorpt_T_max   0.952
_shelx_estimated_absorpt_T_min   0.892
_exptl_absorpt_coefficient_mu    0.283
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0793 before and 0.0433 after correction.
The Ratio of minimum to maximum transmission is 0.9301.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.412
_exptl_crystal_size_mid          0.188
_exptl_crystal_size_min          0.174
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            21209
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.264
_diffrn_reflns_theta_min         2.391
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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                5178
_reflns_number_total             6189
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.039
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         6189
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0541
_refine_ls_restrained_S_all      1.052
_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)+(0.0618P)²+3.4357P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1373
_refine_ls_wR_factor_ref         0.1463
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C35(H35A,H35B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C10(H10), C12(H12), C14(H14), C18(H18),
 C19(H19), C21(H21), C22(H22), C24(H24), C25(H25), C26(H26), C27(H27), C31(H31),
  C32(H32), C33(H33), C34(H34)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.23409(8) 0.63033(7) 0.39731(3) 0.0596(2) Uani 1 1 d . . . . .
Cl2 Cl 0.24081(8) 0.42528(7) 0.32871(3) 0.0568(2) Uani 1 1 d . . . . .
C35 C 0.1636(3) 0.5601(3) 0.34315(11) 0.0594(9) Uani 1 1 d . . . . .
H35A H 0.166278 0.615385 0.313970 0.071 Uiso 1 1 calc R . . . .
H35B H 0.072363 0.543151 0.348363 0.071 Uiso 1 1 calc R . . . .
F1 F 0.92980(17) 1.0930(2) 0.33191(8) 0.0733(6) Uani 1 1 d . . . . .
F2 F 0.7974(2) 1.22663(18) 0.34962(8) 0.0849(7) Uani 1 1 d . . . . .
F3 F 0.78912(19) 1.15120(19) 0.27508(6) 0.0686(6) Uani 1 1 d . . . . .
F4 F 0.5386(2) 0.7852(3) 0.24026(8) 0.1012(9) Uani 1 1 d . . . . .
F5 F 0.4709(3) 0.6855(2) 0.29850(9) 0.1050(10) Uani 1 1 d . . . . .
F6 F 0.3723(2) 0.8387(3) 0.27495(12) 0.1273(13) Uani 1 1 d . . . . .
O1 O 0.05596(17) 0.19082(14) 0.59517(7) 0.0373(4) Uani 1 1 d . . . . .
N1 N 0.68073(16) 0.97269(15) 0.49672(6) 0.0232(4) Uani 1 1 d . . . . .
N2 N 0.53457(16) 0.80990(15) 0.47650(6) 0.0227(4) Uani 1 1 d . . . . .
N3 N 0.19622(19) 0.39790(18) 0.57129(7) 0.0331(4) Uani 1 1 d . . . . .
C1 C 0.7415(2) 1.0218(2) 0.58371(8) 0.0277(4) Uani 1 1 d . . . . .
H1 H 0.790698 1.087561 0.572965 0.033 Uiso 1 1 calc R . . . .
C2 C 0.7373(2) 0.9972(2) 0.63447(8) 0.0313(5) Uani 1 1 d . . . . .
H2 H 0.785742 1.044995 0.658599 0.038 Uiso 1 1 calc R . . . .
C3 C 0.6618(2) 0.9018(2) 0.65129(8) 0.0317(5) Uani 1 1 d . . . . .
H3 H 0.659736 0.886190 0.686550 0.038 Uiso 1 1 calc R . . . .
C4 C 0.5913(2) 0.8315(2) 0.61695(8) 0.0272(4) Uani 1 1 d . . . . .
H4 H 0.539304 0.768609 0.628494 0.033 Uiso 1 1 calc R . . . .
C5 C 0.59647(18) 0.85296(18) 0.56410(8) 0.0220(4) Uani 1 1 d . . . . .
C6 C 0.67242(18) 0.94888(18) 0.54733(7) 0.0218(4) Uani 1 1 d . . . . .
C7 C 0.61418(18) 0.90200(18) 0.46464(8) 0.0216(4) Uani 1 1 d . . . . .
C8 C 0.52671(18) 0.78552(18) 0.52522(8) 0.0218(4) Uani 1 1 d . . . . .
C9 C 0.62522(19) 0.92243(19) 0.40917(8) 0.0236(4) Uani 1 1 d . . . . .
C10 C 0.7059(2) 1.01174(19) 0.39254(8) 0.0262(4) Uani 1 1 d . . . . .
H10 H 0.753836 1.060276 0.416524 0.031 Uiso 1 1 calc R . . . .
C11 C 0.7164(2) 1.0300(2) 0.34079(8) 0.0299(5) Uani 1 1 d . . . . .
C12 C 0.6472(2) 0.9599(2) 0.30488(8) 0.0318(5) Uani 1 1 d . . . . .
H12 H 0.654711 0.972694 0.269688 0.038 Uiso 1 1 calc R . . . .
C13 C 0.5669(2) 0.8709(2) 0.32160(8) 0.0307(5) Uani 1 1 d . . . . .
C14 C 0.5550(2) 0.85219(19) 0.37321(8) 0.0267(4) Uani 1 1 d . . . . .
H14 H 0.499107 0.791580 0.384010 0.032 Uiso 1 1 calc R . . . .
C15 C 0.8061(3) 1.1252(2) 0.32397(9) 0.0404(6) Uani 1 1 d . . . . .
C16 C 0.4876(2) 0.7975(2) 0.28348(9) 0.0396(6) Uani 1 1 d . . . . .
C17 C 0.44052(19) 0.68488(18) 0.53777(7) 0.0220(4) Uani 1 1 d . . . . .
C18 C 0.4904(2) 0.5817(2) 0.56149(9) 0.0313(5) Uani 1 1 d . . . . .
H18 H 0.579864 0.576222 0.570632 0.038 Uiso 1 1 calc R . . . .
C19 C 0.4099(2) 0.4866(2) 0.57185(9) 0.0329(5) Uani 1 1 d . . . . .
H19 H 0.444467 0.415455 0.587076 0.040 Uiso 1 1 calc R . . . .
C20 C 0.2782(2) 0.49629(19) 0.55975(8) 0.0272(4) Uani 1 1 d . . . . .
C21 C 0.2274(2) 0.5993(2) 0.53693(9) 0.0291(5) Uani 1 1 d . . . . .
H21 H 0.137438 0.606104 0.529300 0.035 Uiso 1 1 calc R . . . .
C22 C 0.3089(2) 0.69293(19) 0.52520(8) 0.0269(4) Uani 1 1 d . . . . .
H22 H 0.274482 0.762461 0.508571 0.032 Uiso 1 1 calc R . . . .
C23 C 0.1699(2) 0.3736(2) 0.62195(8) 0.0290(5) Uani 1 1 d . . . . .
C24 C 0.2077(2) 0.4498(2) 0.66190(9) 0.0370(5) Uani 1 1 d . . . . .
H24 H 0.251476 0.522204 0.655349 0.044 Uiso 1 1 calc R . . . .
C25 C 0.1816(3) 0.4206(3) 0.71166(10) 0.0454(6) Uani 1 1 d . . . . .
H25 H 0.207846 0.473417 0.738581 0.054 Uiso 1 1 calc R . . . .
C26 C 0.1180(3) 0.3154(3) 0.72201(10) 0.0453(6) Uani 1 1 d . . . . .
H26 H 0.102107 0.295092 0.755901 0.054 Uiso 1 1 calc R . . . .
C27 C 0.0776(2) 0.2399(2) 0.68214(10) 0.0383(6) Uani 1 1 d . . . . .
H27 H 0.033173 0.167918 0.688831 0.046 Uiso 1 1 calc R . . . .
C28 C 0.1019(2) 0.2690(2) 0.63287(9) 0.0298(5) Uani 1 1 d . . . . .
C29 C 0.0674(2) 0.22539(19) 0.54505(9) 0.0284(5) Uani 1 1 d . . . . .
C30 C 0.13874(19) 0.32587(19) 0.53217(8) 0.0262(4) Uani 1 1 d . . . . .
C31 C 0.1521(2) 0.3486(2) 0.48089(9) 0.0298(5) Uani 1 1 d . . . . .
H31 H 0.200719 0.415762 0.471223 0.036 Uiso 1 1 calc R . . . .
C32 C 0.0946(2) 0.2734(2) 0.44363(9) 0.0345(5) Uani 1 1 d . . . . .
H32 H 0.105154 0.289326 0.408862 0.041 Uiso 1 1 calc R . . . .
C33 C 0.0224(2) 0.1759(2) 0.45716(10) 0.0358(5) Uani 1 1 d . . . . .
H33 H -0.017099 0.125108 0.431808 0.043 Uiso 1 1 calc R . . . .
C34 C 0.0083(2) 0.1529(2) 0.50799(10) 0.0330(5) Uani 1 1 d . . . . .
H34 H -0.042420 0.086926 0.517441 0.040 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
Cl1 C35 1.750(3) . ?
Cl2 C35 1.761(3) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
F1 C15 1.343(3) . ?
F2 C15 1.325(3) . ?
F3 C15 1.325(3) . ?
F4 C16 1.300(3) . ?
F5 C16 1.327(4) . ?
F6 C16 1.294(3) . ?
O1 C28 1.386(3) . ?
O1 C29 1.393(3) . ?
N1 C6 1.373(3) . ?
N1 C7 1.321(3) . ?
N2 C7 1.371(3) . ?
N2 C8 1.325(3) . ?
N3 C20 1.437(3) . ?
N3 C23 1.412(3) . ?
N3 C30 1.411(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.374(3) . ?
C1 C6 1.419(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.415(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.375(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.423(3) . ?
C5 C6 1.421(3) . ?
C5 C8 1.432(3) . ?
C7 C9 1.497(3) . ?
C8 C17 1.490(3) . ?
C9 C10 1.395(3) . ?
C9 C14 1.400(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.395(3) . ?
C11 C12 1.393(3) . ?
C11 C15 1.503(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.392(3) . ?
C13 C14 1.394(3) . ?
C13 C16 1.502(3) . ?
C14 H14 0.9500 . ?
C17 C18 1.395(3) . ?
C17 C22 1.394(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.393(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.394(3) . ?
C20 C21 1.387(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.395(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.392(3) . ?
C23 C28 1.406(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.400(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.385(4) . ?
C26 H26 0.9500 . ?
C26 C27 1.393(4) . ?
C27 H27 0.9500 . ?
C27 C28 1.383(3) . ?
C29 C30 1.401(3) . ?
C29 C34 1.383(3) . ?
C30 C31 1.396(3) . ?
C31 H31 0.9500 . ?
C31 C32 1.398(3) . ?
C32 H32 0.9500 . ?
C32 C33 1.385(3) . ?
C33 H33 0.9500 . ?
C33 C34 1.386(4) . ?
C34 H34 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
Cl1 C35 Cl2 112.79(16) . . ?
Cl1 C35 H35A 109.0 . . ?
Cl1 C35 H35B 109.0 . . ?
Cl2 C35 H35A 109.0 . . ?
Cl2 C35 H35B 109.0 . . ?
H35A C35 H35B 107.8 . . ?
C28 O1 C29 117.53(17) . . ?
C7 N1 C6 116.43(17) . . ?
C8 N2 C7 117.07(17) . . ?
C23 N3 C20 120.36(18) . . ?
C30 N3 C20 120.59(18) . . ?
C30 N3 C23 119.04(18) . . ?
C2 C1 H1 120.0 . . ?
C2 C1 C6 120.0(2) . . ?
C6 C1 H1 120.0 . . ?
C1 C2 H2 119.6 . . ?
C1 C2 C3 120.9(2) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.9(2) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C8 124.40(19) . . ?
C6 C5 C4 119.54(18) . . ?
C6 C5 C8 116.04(18) . . ?
N1 C6 C1 119.13(18) . . ?
N1 C6 C5 121.59(18) . . ?
C1 C6 C5 119.28(18) . . ?
N1 C7 N2 126.94(18) . . ?
N1 C7 C9 117.80(18) . . ?
N2 C7 C9 115.27(18) . . ?
N2 C8 C5 121.86(18) . . ?
N2 C8 C17 116.72(18) . . ?
C5 C8 C17 121.42(18) . . ?
C10 C9 C7 120.42(19) . . ?
C10 C9 C14 119.01(19) . . ?
C14 C9 C7 120.57(19) . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.2(2) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C15 119.1(2) . . ?
C12 C11 C10 121.0(2) . . ?
C12 C11 C15 120.0(2) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 C11 118.7(2) . . ?
C13 C12 H12 120.7 . . ?
C12 C13 C14 120.9(2) . . ?
C12 C13 C16 119.5(2) . . ?
C14 C13 C16 119.6(2) . . ?
C9 C14 H14 119.9 . . ?
C13 C14 C9 120.2(2) . . ?
C13 C14 H14 119.9 . . ?
F1 C15 C11 112.1(2) . . ?
F2 C15 F1 104.3(2) . . ?
F2 C15 C11 112.7(2) . . ?
F3 C15 F1 105.9(2) . . ?
F3 C15 F2 107.7(2) . . ?
F3 C15 C11 113.5(2) . . ?
F4 C16 F5 103.5(3) . . ?
F4 C16 C13 114.1(2) . . ?
F5 C16 C13 113.0(2) . . ?
F6 C16 F4 108.4(3) . . ?
F6 C16 F5 104.3(3) . . ?
F6 C16 C13 112.8(2) . . ?
C18 C17 C8 120.64(18) . . ?
C22 C17 C8 119.89(18) . . ?
C22 C17 C18 119.47(19) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.4(2) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 120.2 . . ?
C18 C19 C20 119.6(2) . . ?
C20 C19 H19 120.2 . . ?
C19 C20 N3 118.9(2) . . ?
C21 C20 N3 120.7(2) . . ?
C21 C20 C19 120.4(2) . . ?
C20 C21 H21 120.1 . . ?
C20 C21 C22 119.8(2) . . ?
C22 C21 H21 120.1 . . ?
C17 C22 C21 120.3(2) . . ?
C17 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C24 C23 N3 122.6(2) . . ?
C24 C23 C28 118.2(2) . . ?
C28 C23 N3 119.2(2) . . ?
C23 C24 H24 119.7 . . ?
C23 C24 C25 120.5(2) . . ?
C25 C24 H24 119.7 . . ?
C24 C25 H25 119.7 . . ?
C26 C25 C24 120.6(3) . . ?
C26 C25 H25 119.7 . . ?
C25 C26 H26 120.4 . . ?
C25 C26 C27 119.2(2) . . ?
C27 C26 H26 120.4 . . ?
C26 C27 H27 119.8 . . ?
C28 C27 C26 120.4(2) . . ?
C28 C27 H27 119.8 . . ?
O1 C28 C23 122.0(2) . . ?
C27 C28 O1 117.0(2) . . ?
C27 C28 C23 121.1(2) . . ?
O1 C29 C30 122.3(2) . . ?
C34 C29 O1 116.7(2) . . ?
C34 C29 C30 121.0(2) . . ?
C29 C30 N3 119.0(2) . . ?
C31 C30 N3 122.89(19) . . ?
C31 C30 C29 118.1(2) . . ?
C30 C31 H31 119.7 . . ?
C30 C31 C32 120.6(2) . . ?
C32 C31 H31 119.7 . . ?
C31 C32 H32 119.8 . . ?
C33 C32 C31 120.3(2) . . ?
C33 C32 H32 119.8 . . ?
C32 C33 H33 120.3 . . ?
C32 C33 C34 119.5(2) . . ?
C34 C33 H33 120.3 . . ?
C29 C34 C33 120.5(2) . . ?
C29 C34 H34 119.8 . . ?
C33 C34 H34 119.8 . . ?

_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_190326_wzc_4328_0m_sq
_database_code_depnum_ccdc_archive 'CCDC 1961661'
loop_
_audit_author_name
_audit_author_address
'Zhichao Wang'
;Zhejiang University
China
;
_audit_update_record             
;
2019-10-28 deposited with the CCDC.	2020-08-10 downloaded from the CCDC.
;
_audit_creation_date             2019-03-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C34 H21 F6 N3'
_chemical_formula_sum            'C34 H21 F6 N3'
_chemical_formula_weight         585.54
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.459(3)
_cell_length_b                   12.647(3)
_cell_length_c                   13.633(3)
_cell_angle_alpha                92.321(11)
_cell_angle_beta                 107.307(12)
_cell_angle_gamma                92.887(13)
_cell_volume                     1552.5(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9981
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      26.36
_cell_measurement_theta_min      2.26
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.949
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7185
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0821 before and 0.0351 after correction.
The Ratio of minimum to maximum transmission is 0.9639.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.532
_exptl_crystal_size_mid          0.237
_exptl_crystal_size_min          0.195
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17779
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.420
_diffrn_reflns_theta_min         2.260
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5569
_reflns_number_total             6324
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.758
_refine_diff_density_min         -0.600
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         6324
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0622
_refine_ls_restrained_S_all      1.064
_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)+(0.0885P)²+1.0243P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1738
_refine_ls_wR_factor_ref         0.1796
_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), C3(H3), C4(H4), C10(H10), C11(H11), C13(H13), C14(H14),
 C16(H16), C18(H18), C20(H20), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28),
  C30(H30), C31(H31), C32(H32), C33(H33), C34(H34)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.5585(4) 0.2577(3) 0.91754(15) 0.1585(15) Uani 1 1 d . . . . .
F2 F 0.5534(3) 0.1006(2) 0.95837(19) 0.1338(12) Uani 1 1 d . . . . .
F3 F 0.7341(2) 0.20142(17) 1.03027(11) 0.0819(6) Uani 1 1 d . . . . .
F4 F 1.14123(19) 0.0924(3) 0.77829(18) 0.1232(10) Uani 1 1 d . . . . .
F5 F 1.13866(19) 0.0640(2) 0.93029(13) 0.1037(8) Uani 1 1 d . . . . .
F6 F 1.0667(3) -0.0529(2) 0.8115(2) 0.1408(12) Uani 1 1 d . . . . .
N1 N 0.66513(15) 0.10057(11) 0.49844(11) 0.0260(3) Uani 1 1 d . . . . .
N2 N 0.45597(15) 0.15431(11) 0.54853(11) 0.0257(3) Uani 1 1 d . . . . .
N3 N -0.16349(17) 0.35734(13) 0.42308(12) 0.0333(4) Uani 1 1 d . . . . .
C1 C 0.6528(2) 0.08314(15) 0.32056(14) 0.0320(4) Uani 1 1 d . . . . .
H1 H 0.751081 0.060541 0.339241 0.038 Uiso 1 1 calc R . . . .
C2 C 0.5759(2) 0.08982(16) 0.21933(15) 0.0364(4) Uani 1 1 d . . . . .
H2 H 0.621189 0.071991 0.167856 0.044 Uiso 1 1 calc R . . . .
C3 C 0.4296(2) 0.12300(16) 0.19026(15) 0.0364(4) Uani 1 1 d . . . . .
H3 H 0.377097 0.126916 0.119429 0.044 Uiso 1 1 calc R . . . .
C4 C 0.3629(2) 0.14954(14) 0.26330(14) 0.0313(4) Uani 1 1 d . . . . .
H4 H 0.264116 0.171243 0.242895 0.038 Uiso 1 1 calc R . . . .
C5 C 0.44019(18) 0.14483(13) 0.36917(13) 0.0257(3) Uani 1 1 d . . . . .
C6 C 0.58642(18) 0.10983(13) 0.39796(13) 0.0260(3) Uani 1 1 d . . . . .
C7 C 0.59633(18) 0.12251(12) 0.56712(13) 0.0245(3) Uani 1 1 d . . . . .
C8 C 0.38043(18) 0.16846(13) 0.45190(13) 0.0252(3) Uani 1 1 d . . . . .
C9 C 0.23334(18) 0.21198(13) 0.43600(13) 0.0261(3) Uani 1 1 d . . . . .
C10 C 0.19302(19) 0.29991(14) 0.37797(14) 0.0289(4) Uani 1 1 d . . . . .
H10 H 0.256130 0.327776 0.341231 0.035 Uiso 1 1 calc R . . . .
C11 C 0.06237(19) 0.34734(14) 0.37299(14) 0.0297(4) Uani 1 1 d . . . . .
H11 H 0.037823 0.408105 0.334161 0.036 Uiso 1 1 calc R . . . .
C12 C -0.03315(18) 0.30644(14) 0.42459(14) 0.0285(4) Uani 1 1 d . . . . .
C13 C 0.00382(19) 0.21561(15) 0.47924(15) 0.0321(4) Uani 1 1 d . . . . .
H13 H -0.062708 0.184481 0.511748 0.038 Uiso 1 1 calc R . . . .
C14 C 0.13659(19) 0.17065(14) 0.48639(14) 0.0303(4) Uani 1 1 d . . . . .
H14 H 0.162104 0.110690 0.526261 0.036 Uiso 1 1 calc R . . . .
C15 C 0.68220(18) 0.11673(13) 0.67734(13) 0.0265(4) Uani 1 1 d . . . . .
C16 C 0.6211(2) 0.14618(14) 0.75473(14) 0.0300(4) Uani 1 1 d . . . . .
H16 H 0.521663 0.166373 0.737289 0.036 Uiso 1 1 calc R . . . .
C17 C 0.7052(2) 0.14608(15) 0.85729(14) 0.0355(4) Uani 1 1 d . . . . .
C18 C 0.8498(2) 0.11631(17) 0.88475(15) 0.0405(5) Uani 1 1 d . . . . .
H18 H 0.906973 0.116594 0.955061 0.049 Uiso 1 1 calc R . . . .
C19 C 0.9097(2) 0.08585(18) 0.80681(16) 0.0408(5) Uani 1 1 d . . . . .
C20 C 0.8272(2) 0.08584(15) 0.70433(14) 0.0321(4) Uani 1 1 d . . . . .
H20 H 0.869653 0.064684 0.652231 0.039 Uiso 1 1 calc R . . . .
C21 C 0.6373(3) 0.1779(2) 0.93918(16) 0.0472(5) Uani 1 1 d . . . . .
C22 C 1.0644(3) 0.0509(3) 0.83311(19) 0.0663(8) Uani 1 1 d . . . . .
C23 C -0.22954(19) 0.41961(15) 0.33816(15) 0.0327(4) Uani 1 1 d . . . . .
C24 C -0.2726(3) 0.37355(19) 0.23901(17) 0.0498(6) Uani 1 1 d . . . . .
H24 H -0.258719 0.300728 0.227588 0.060 Uiso 1 1 calc R . . . .
C25 C -0.3358(3) 0.4337(2) 0.1566(2) 0.0680(8) Uani 1 1 d . . . . .
H25 H -0.364468 0.402050 0.088607 0.082 Uiso 1 1 calc R . . . .
C26 C -0.3577(3) 0.5393(2) 0.1725(2) 0.0637(7) Uani 1 1 d . . . . .
H26 H -0.401956 0.580048 0.115657 0.076 Uiso 1 1 calc R . . . .
C27 C -0.3150(2) 0.58537(18) 0.27095(18) 0.0456(5) Uani 1 1 d . . . . .
H27 H -0.330103 0.658028 0.282077 0.055 Uiso 1 1 calc R . . . .
C28 C -0.2502(2) 0.52599(15) 0.35388(16) 0.0347(4) Uani 1 1 d . . . . .
H28 H -0.219895 0.558252 0.421663 0.042 Uiso 1 1 calc R . . . .
C29 C -0.2113(2) 0.36783(14) 0.51195(15) 0.0309(4) Uani 1 1 d . . . . .
C30 C -0.3607(2) 0.38327(15) 0.50029(17) 0.0368(4) Uani 1 1 d . . . . .
H30 H -0.429095 0.383184 0.433235 0.044 Uiso 1 1 calc R . . . .
C31 C -0.4095(2) 0.39860(16) 0.5853(2) 0.0450(5) Uani 1 1 d . . . . .
H31 H -0.511008 0.409902 0.576077 0.054 Uiso 1 1 calc R . . . .
C32 C -0.3126(3) 0.39774(17) 0.6836(2) 0.0494(6) Uani 1 1 d . . . . .
H32 H -0.346618 0.408944 0.741874 0.059 Uiso 1 1 calc R . . . .
C33 C -0.1648(3) 0.38027(17) 0.69596(17) 0.0439(5) Uani 1 1 d . . . . .
H33 H -0.097647 0.378219 0.763258 0.053 Uiso 1 1 calc R . . . .
C34 C -0.1140(2) 0.36578(15) 0.61110(16) 0.0368(4) Uani 1 1 d . . . . .
H34 H -0.012382 0.354394 0.620656 0.044 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C21 1.277(3) . ?
F2 C21 1.311(3) . ?
F3 C21 1.317(3) . ?
F4 C22 1.296(4) . ?
F5 C22 1.301(3) . ?
F6 C22 1.336(4) . ?
N1 C6 1.364(2) . ?
N1 C7 1.318(2) . ?
N2 C7 1.360(2) . ?
N2 C8 1.323(2) . ?
N3 C12 1.415(2) . ?
N3 C23 1.430(2) . ?
N3 C29 1.418(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.363(3) . ?
C1 C6 1.417(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.412(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.368(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.416(2) . ?
C5 C6 1.420(2) . ?
C5 C8 1.432(2) . ?
C7 C15 1.487(2) . ?
C8 C9 1.481(2) . ?
C9 C10 1.394(2) . ?
C9 C14 1.392(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.386(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.393(2) . ?
C12 C13 1.397(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.383(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.392(2) . ?
C15 C20 1.391(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.388(3) . ?
C17 C18 1.383(3) . ?
C17 C21 1.496(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.395(3) . ?
C19 C20 1.383(3) . ?
C19 C22 1.494(3) . ?
C20 H20 0.9500 . ?
C23 C24 1.384(3) . ?
C23 C28 1.387(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.383(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.380(4) . ?
C26 H26 0.9500 . ?
C26 C27 1.377(4) . ?
C27 H27 0.9500 . ?
C27 C28 1.386(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.398(3) . ?
C29 C34 1.393(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.379(3) . ?
C31 H31 0.9500 . ?
C31 C32 1.381(4) . ?
C32 H32 0.9500 . ?
C32 C33 1.388(3) . ?
C33 H33 0.9500 . ?
C33 C34 1.388(3) . ?
C34 H34 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
C7 N1 C6 116.37(14) . . ?
C8 N2 C7 117.47(14) . . ?
C12 N3 C23 118.75(15) . . ?
C12 N3 C29 121.62(15) . . ?
C29 N3 C23 118.16(14) . . ?
C2 C1 H1 119.9 . . ?
C2 C1 C6 120.13(17) . . ?
C6 C1 H1 119.9 . . ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.64(17) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.51(17) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.34(17) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 118.93(16) . . ?
C4 C5 C8 125.12(16) . . ?
C6 C5 C8 115.89(15) . . ?
N1 C6 C1 118.78(15) . . ?
N1 C6 C5 121.78(15) . . ?
C1 C6 C5 119.44(16) . . ?
N1 C7 N2 126.98(15) . . ?
N1 C7 C15 117.16(15) . . ?
N2 C7 C15 115.80(14) . . ?
N2 C8 C5 121.39(15) . . ?
N2 C8 C9 115.72(15) . . ?
C5 C8 C9 122.88(15) . . ?
C10 C9 C8 121.49(15) . . ?
C14 C9 C8 120.01(15) . . ?
C14 C9 C10 118.29(15) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.07(16) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.37(16) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 N3 120.42(16) . . ?
C11 C12 C13 118.70(15) . . ?
C13 C12 N3 120.86(16) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.50(16) . . ?
C14 C13 H13 119.8 . . ?
C9 C14 H14 119.5 . . ?
C13 C14 C9 120.96(16) . . ?
C13 C14 H14 119.5 . . ?
C16 C15 C7 120.63(15) . . ?
C20 C15 C7 120.17(15) . . ?
C20 C15 C16 119.15(16) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.12(17) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C21 119.23(18) . . ?
C18 C17 C16 121.09(18) . . ?
C18 C17 C21 119.68(18) . . ?
C17 C18 H18 120.8 . . ?
C17 C18 C19 118.45(18) . . ?
C19 C18 H18 120.8 . . ?
C18 C19 C22 120.21(19) . . ?
C20 C19 C18 121.02(18) . . ?
C20 C19 C22 118.76(19) . . ?
C15 C20 H20 119.9 . . ?
C19 C20 C15 120.16(17) . . ?
C19 C20 H20 119.9 . . ?
F1 C21 F2 107.5(3) . . ?
F1 C21 F3 106.4(2) . . ?
F1 C21 C17 113.25(19) . . ?
F2 C21 F3 102.3(2) . . ?
F2 C21 C17 112.4(2) . . ?
F3 C21 C17 114.2(2) . . ?
F4 C22 F5 109.8(3) . . ?
F4 C22 F6 102.4(3) . . ?
F4 C22 C19 113.3(2) . . ?
F5 C22 F6 104.1(3) . . ?
F5 C22 C19 114.4(2) . . ?
F6 C22 C19 111.9(3) . . ?
C24 C23 N3 119.77(18) . . ?
C24 C23 C28 119.52(18) . . ?
C28 C23 N3 120.71(18) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 C23 119.9(2) . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 119.8 . . ?
C26 C25 C24 120.5(2) . . ?
C26 C25 H25 119.8 . . ?
C25 C26 H26 120.1 . . ?
C27 C26 C25 119.8(2) . . ?
C27 C26 H26 120.1 . . ?
C26 C27 H27 119.9 . . ?
C26 C27 C28 120.1(2) . . ?
C28 C27 H27 119.9 . . ?
C23 C28 H28 119.9 . . ?
C27 C28 C23 120.2(2) . . ?
C27 C28 H28 119.9 . . ?
C30 C29 N3 119.15(17) . . ?
C34 C29 N3 122.29(16) . . ?
C34 C29 C30 118.55(18) . . ?
C29 C30 H30 119.7 . . ?
C31 C30 C29 120.6(2) . . ?
C31 C30 H30 119.7 . . ?
C30 C31 H31 119.6 . . ?
C30 C31 C32 120.8(2) . . ?
C32 C31 H31 119.6 . . ?
C31 C32 H32 120.5 . . ?
C31 C32 C33 119.0(2) . . ?
C33 C32 H32 120.5 . . ?
C32 C33 H33 119.6 . . ?
C34 C33 C32 120.7(2) . . ?
C34 C33 H33 119.6 . . ?
C29 C34 H34 119.9 . . ?
C33 C34 C29 120.29(19) . . ?
C33 C34 H34 119.9 . . ?

_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_190523_wzc_4345_0m
_database_code_depnum_ccdc_archive 'CCDC 1961663'
loop_
_audit_author_name
_audit_author_address
'Zhichao Wang'
;Zhejiang University
China
;
_audit_update_record             
;
2019-10-28 deposited with the CCDC.	2020-08-10 downloaded from the CCDC.
;
_audit_creation_date             2019-05-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H25 F6 N3 O2'
_chemical_formula_sum            'C36 H25 F6 N3 O2'
_chemical_formula_weight         645.59
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.488(3)
_cell_length_b                   9.778(3)
_cell_length_c                   16.834(6)
_cell_angle_alpha                105.688(17)
_cell_angle_beta                 97.397(17)
_cell_angle_gamma                94.639(12)
_cell_volume                     1480.2(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9899
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      26.38
_cell_measurement_theta_min      2.55
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.951
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7212
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1180 before and 0.0368 after correction.
The Ratio of minimum to maximum transmission is 0.9675.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.267
_exptl_crystal_size_min          0.152
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17781
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.386
_diffrn_reflns_theta_min         2.180
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5404
_reflns_number_total             6012
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.525
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     426
_refine_ls_number_reflns         6012
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.028
_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)+(0.0586P)²+0.9220P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1205
_refine_ls_wR_factor_ref         0.1248
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14), C16(H16),
 C17(H17), C19(H19), C20(H20), C22(H22), C23(H23), C25(H25), C26(H26), C29(H29),
  C30(H30), C32(H32), C33(H33)
2.b Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C34(H34A,H34B,H34C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F -0.29342(15) 0.80819(15) 1.08229(9) 0.0708(5) Uani 1 1 d . . . . .
F2 F -0.36209(13) 0.58907(13) 1.02750(9) 0.0568(4) Uani 1 1 d . . . . .
F3 F -0.38926(16) 0.7318(2) 0.95396(10) 0.0865(6) Uani 1 1 d . . . . .
F4 F 0.20624(15) 0.95889(15) 1.10524(9) 0.0705(5) Uani 1 1 d . . . . .
F5 F 0.32900(15) 0.78728(16) 1.07601(10) 0.0703(4) Uani 1 1 d . . . . .
F6 F 0.28976(18) 0.90639(18) 0.99019(8) 0.0794(5) Uani 1 1 d . . . . .
O1 O 0.57933(14) 0.07713(14) 0.24543(7) 0.0372(3) Uani 1 1 d . . . . .
O2 O 1.10037(13) 0.76660(13) 0.74070(8) 0.0377(3) Uani 1 1 d . . . . .
N1 N 0.63923(14) 0.34275(14) 0.58835(8) 0.0239(3) Uani 1 1 d . . . . .
N2 N 0.12229(13) 0.40130(14) 0.79591(8) 0.0229(3) Uani 1 1 d . . . . .
N3 N -0.12186(13) 0.31524(14) 0.79560(8) 0.0233(3) Uani 1 1 d . . . . .
C1 C -0.14621(17) 0.56132(16) 0.92115(9) 0.0249(3) Uani 1 1 d . . . . .
H1 H -0.229410 0.496169 0.894610 0.030 Uiso 1 1 calc R . . . .
C2 C -0.15569(18) 0.68092(17) 0.98640(10) 0.0272(3) Uani 1 1 d . . . . .
C3 C -0.03528(18) 0.77671(17) 1.02676(10) 0.0285(3) Uani 1 1 d . . . . .
H3 H -0.042176 0.858061 1.071559 0.034 Uiso 1 1 calc R . . . .
C4 C 0.09555(18) 0.75136(17) 1.00038(10) 0.0280(3) Uani 1 1 d . . . . .
C5 C 0.10631(17) 0.63297(17) 0.93452(9) 0.0251(3) Uani 1 1 d . . . . .
H5 H 0.196269 0.617677 0.916752 0.030 Uiso 1 1 calc R . . . .
C6 C -0.01501(16) 0.53660(16) 0.89450(9) 0.0230(3) Uani 1 1 d . . . . .
C7 C -0.00576(16) 0.40821(16) 0.82445(9) 0.0218(3) Uani 1 1 d . . . . .
C8 C 0.13206(16) 0.29098(16) 0.73195(9) 0.0219(3) Uani 1 1 d . . . . .
C9 C 0.01773(16) 0.17619(16) 0.69858(9) 0.0220(3) Uani 1 1 d . . . . .
C10 C -0.11062(16) 0.19564(16) 0.73335(9) 0.0221(3) Uani 1 1 d . . . . .
C11 C -0.22896(17) 0.08741(17) 0.70451(10) 0.0262(3) Uani 1 1 d . . . . .
H11 H -0.315975 0.101019 0.726240 0.031 Uiso 1 1 calc R . . . .
C12 C -0.21781(17) -0.03688(17) 0.64525(10) 0.0286(3) Uani 1 1 d . . . . .
H12 H -0.297466 -0.109162 0.625960 0.034 Uiso 1 1 calc R . . . .
C13 C -0.08876(18) -0.05860(17) 0.61252(10) 0.0288(3) Uani 1 1 d . . . . .
H13 H -0.081731 -0.146344 0.572518 0.035 Uiso 1 1 calc R . . . .
C14 C 0.02611(17) 0.04560(17) 0.63794(10) 0.0265(3) Uani 1 1 d . . . . .
H14 H 0.111743 0.030388 0.614873 0.032 Uiso 1 1 calc R . . . .
C15 C 0.26517(16) 0.29530(15) 0.69502(9) 0.0218(3) Uani 1 1 d . . . . .
C16 C 0.25857(16) 0.26776(16) 0.60895(9) 0.0229(3) Uani 1 1 d . . . . .
H16 H 0.168538 0.237778 0.573716 0.028 Uiso 1 1 calc R . . . .
C17 C 0.38106(16) 0.28331(15) 0.57374(9) 0.0221(3) Uani 1 1 d . . . . .
H17 H 0.373660 0.265571 0.514928 0.027 Uiso 1 1 calc R . . . .
C18 C 0.51546(16) 0.32486(15) 0.62393(9) 0.0208(3) Uani 1 1 d . . . . .
C19 C 0.52304(16) 0.34727(16) 0.71065(9) 0.0234(3) Uani 1 1 d . . . . .
H19 H 0.613593 0.370709 0.745638 0.028 Uiso 1 1 calc R . . . .
C20 C 0.39975(16) 0.33544(16) 0.74536(9) 0.0234(3) Uani 1 1 d . . . . .
H20 H 0.406442 0.354838 0.804240 0.028 Uiso 1 1 calc R . . . .
C21 C 0.63110(15) 0.27819(15) 0.50007(9) 0.0213(3) Uani 1 1 d . . . . .
C22 C 0.62248(16) 0.12986(16) 0.46858(9) 0.0234(3) Uani 1 1 d . . . . .
H22 H 0.628436 0.072020 0.505768 0.028 Uiso 1 1 calc R . . . .
C23 C 0.60525(16) 0.06680(16) 0.38319(10) 0.0258(3) Uani 1 1 d . . . . .
H23 H 0.597636 -0.034387 0.361959 0.031 Uiso 1 1 calc R . . . .
C24 C 0.59902(16) 0.15087(18) 0.32822(9) 0.0259(3) Uani 1 1 d . . . . .
C25 C 0.61257(17) 0.29910(18) 0.35947(10) 0.0272(3) Uani 1 1 d . . . . .
H25 H 0.611982 0.357323 0.322510 0.033 Uiso 1 1 calc R . . . .
C26 C 0.62697(17) 0.36146(16) 0.44522(10) 0.0254(3) Uani 1 1 d . . . . .
H26 H 0.634088 0.462613 0.466498 0.030 Uiso 1 1 calc R . . . .
C27 C 0.5491(2) 0.1561(3) 0.18668(11) 0.0453(5) Uani 1 1 d . . . . .
H27A H 0.534572 0.091194 0.129867 0.068 Uiso 1 1 calc GR . . . .
H27B H 0.629701 0.229696 0.193295 0.068 Uiso 1 1 calc GR . . . .
H27C H 0.462269 0.201815 0.196505 0.068 Uiso 1 1 calc GR . . . .
C28 C 0.75321(16) 0.45368(15) 0.62869(9) 0.0223(3) Uani 1 1 d . . . . .
C29 C 0.88964(17) 0.44122(16) 0.60642(10) 0.0264(3) Uani 1 1 d . . . . .
H29 H 0.905390 0.358567 0.565047 0.032 Uiso 1 1 calc R . . . .
C30 C 1.00175(17) 0.54788(18) 0.64397(11) 0.0296(3) Uani 1 1 d . . . . .
H30 H 1.093288 0.538826 0.627308 0.036 Uiso 1 1 calc R . . . .
C31 C 0.98175(17) 0.66848(16) 0.70598(10) 0.0266(3) Uani 1 1 d . . . . .
C32 C 0.84703(17) 0.68261(16) 0.72831(10) 0.0270(3) Uani 1 1 d . . . . .
H32 H 0.832024 0.764450 0.770520 0.032 Uiso 1 1 calc R . . . .
C33 C 0.73383(17) 0.57666(16) 0.68878(10) 0.0261(3) Uani 1 1 d . . . . .
H33 H 0.641136 0.588651 0.703197 0.031 Uiso 1 1 calc R . . . .
C34 C 1.08206(19) 0.89151(18) 0.80367(11) 0.0336(4) Uani 1 1 d . . . . .
H34A H 1.007478 0.940912 0.781344 0.050 Uiso 1 1 calc GR . . . .
H34B H 1.172365 0.955419 0.821254 0.050 Uiso 1 1 calc GR . . . .
H34C H 1.053728 0.864172 0.851758 0.050 Uiso 1 1 calc GR . . . .
C35 C -0.29987(19) 0.70381(19) 1.01205(11) 0.0332(4) Uani 1 1 d . . . . .
C36 C 0.2282(2) 0.8523(2) 1.04249(11) 0.0365(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 C35 1.327(2) . ?
F2 C35 1.329(2) . ?
F3 C35 1.311(2) . ?
F4 C36 1.320(2) . ?
F5 C36 1.338(2) . ?
F6 C36 1.315(2) . ?
O1 C24 1.3657(19) . ?
O1 C27 1.426(2) . ?
O2 C31 1.372(2) . ?
O2 C34 1.424(2) . ?
N1 C18 1.4046(19) . ?
N1 C21 1.4381(19) . ?
N1 C28 1.425(2) . ?
N2 C7 1.3629(19) . ?
N2 C8 1.3211(19) . ?
N3 C7 1.318(2) . ?
N3 C10 1.3652(19) . ?
C1 H1 0.9500 . ?
C1 C2 1.389(2) . ?
C1 C6 1.394(2) . ?
C2 C3 1.388(2) . ?
C2 C35 1.503(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(2) . ?
C4 C5 1.391(2) . ?
C4 C36 1.501(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.396(2) . ?
C6 C7 1.489(2) . ?
C8 C9 1.434(2) . ?
C8 C15 1.480(2) . ?
C9 C10 1.422(2) . ?
C9 C14 1.418(2) . ?
C10 C11 1.416(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.370(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.414(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.369(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.392(2) . ?
C15 C20 1.401(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.387(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.399(2) . ?
C18 C19 1.408(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.383(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.395(2) . ?
C21 C26 1.386(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.385(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.393(2) . ?
C24 C25 1.391(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.391(2) . ?
C26 H26 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C29 1.399(2) . ?
C28 C33 1.389(2) . ?
C29 H29 0.9500 . ?
C29 C30 1.382(2) . ?
C30 H30 0.9500 . ?
C30 C31 1.392(2) . ?
C31 C32 1.385(2) . ?
C32 H32 0.9500 . ?
C32 C33 1.390(2) . ?
C33 H33 0.9500 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?

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
C24 O1 C27 117.29(15) . . ?
C31 O2 C34 117.10(13) . . ?
C18 N1 C21 117.63(12) . . ?
C18 N1 C28 121.95(12) . . ?
C28 N1 C21 117.62(12) . . ?
C8 N2 C7 117.23(13) . . ?
C7 N3 C10 116.58(13) . . ?
C2 C1 H1 119.9 . . ?
C2 C1 C6 120.21(15) . . ?
C6 C1 H1 119.9 . . ?
C1 C2 C35 118.17(15) . . ?
C3 C2 C1 120.92(15) . . ?
C3 C2 C35 120.90(14) . . ?
C2 C3 H3 120.6 . . ?
C2 C3 C4 118.74(14) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 C5 120.95(15) . . ?
C3 C4 C36 120.35(15) . . ?
C5 C4 C36 118.71(15) . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.03(15) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 119.14(14) . . ?
C1 C6 C7 119.89(14) . . ?
C5 C6 C7 120.97(14) . . ?
N2 C7 C6 115.92(13) . . ?
N3 C7 N2 126.94(14) . . ?
N3 C7 C6 117.13(13) . . ?
N2 C8 C9 121.66(13) . . ?
N2 C8 C15 116.23(13) . . ?
C9 C8 C15 122.08(13) . . ?
C10 C9 C8 115.72(13) . . ?
C14 C9 C8 125.28(14) . . ?
C14 C9 C10 118.93(14) . . ?
N3 C10 C9 121.55(14) . . ?
N3 C10 C11 118.80(14) . . ?
C11 C10 C9 119.63(14) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 119.93(14) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.59(15) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.64(15) . . ?
C14 C13 H13 119.7 . . ?
C9 C14 H14 119.9 . . ?
C13 C14 C9 120.22(14) . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C8 120.30(13) . . ?
C16 C15 C20 118.25(13) . . ?
C20 C15 C8 121.34(13) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.18(14) . . ?
C17 C16 H16 119.4 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.70(13) . . ?
C18 C17 H17 119.7 . . ?
N1 C18 C19 121.13(13) . . ?
C17 C18 N1 120.67(13) . . ?
C17 C18 C19 118.20(13) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.57(14) . . ?
C20 C19 H19 119.7 . . ?
C15 C20 H20 119.5 . . ?
C19 C20 C15 121.01(14) . . ?
C19 C20 H20 119.5 . . ?
C22 C21 N1 119.99(13) . . ?
C26 C21 N1 120.69(13) . . ?
C26 C21 C22 119.29(14) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 C21 120.09(14) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 119.8 . . ?
C22 C23 C24 120.39(14) . . ?
C24 C23 H23 119.8 . . ?
O1 C24 C23 115.32(15) . . ?
O1 C24 C25 124.96(15) . . ?
C25 C24 C23 119.72(14) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 C24 119.51(14) . . ?
C26 C25 H25 120.2 . . ?
C21 C26 C25 120.94(14) . . ?
C21 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
O1 C27 H27A 109.5 . . ?
O1 C27 H27B 109.5 . . ?
O1 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C29 C28 N1 119.50(13) . . ?
C33 C28 N1 122.43(14) . . ?
C33 C28 C29 118.05(14) . . ?
C28 C29 H29 119.7 . . ?
C30 C29 C28 120.69(14) . . ?
C30 C29 H29 119.7 . . ?
C29 C30 H30 119.7 . . ?
C29 C30 C31 120.59(15) . . ?
C31 C30 H30 119.7 . . ?
O2 C31 C30 116.14(14) . . ?
O2 C31 C32 124.55(14) . . ?
C32 C31 C30 119.32(15) . . ?
C31 C32 H32 120.1 . . ?
C31 C32 C33 119.80(14) . . ?
C33 C32 H32 120.1 . . ?
C28 C33 C32 121.49(14) . . ?
C28 C33 H33 119.3 . . ?
C32 C33 H33 119.3 . . ?
O2 C34 H34A 109.5 . . ?
O2 C34 H34B 109.5 . . ?
O2 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
F1 C35 F2 104.61(15) . . ?
F1 C35 C2 113.06(15) . . ?
F2 C35 C2 112.04(14) . . ?
F3 C35 F1 108.12(17) . . ?
F3 C35 F2 106.21(17) . . ?
F3 C35 C2 112.28(15) . . ?
F4 C36 F5 104.76(16) . . ?
F4 C36 C4 113.55(15) . . ?
F5 C36 C4 112.13(15) . . ?
F6 C36 F4 108.38(17) . . ?
F6 C36 F5 104.88(18) . . ?
F6 C36 C4 112.50(15) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
