# Electronic Supplementary Material (ESI) for Materials Horizons.
# 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_mo_210517a_0m
_database_code_depnum_ccdc_archive 'CCDC 2094578'
loop_
_audit_author_name
_audit_author_address
TPM
;Wuhan University
China
;
_audit_update_record             
;
2021-07-06 deposited with the CCDC.	2021-09-06 downloaded from the CCDC.
;
_audit_creation_date             2021-05-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        TPM
_chemical_formula_moiety         'C21 H18'
_chemical_formula_sum            'C21 H18'
_chemical_formula_weight         270.35
_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'

_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                   8.321(3)
_cell_length_b                   9.678(4)
_cell_length_c                   9.879(4)
_cell_angle_alpha                94.541(6)
_cell_angle_beta                 96.864(6)
_cell_angle_gamma                94.634(6)
_cell_volume                     784.1(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3086
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      30.64
_cell_measurement_theta_min      2.48
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6598
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1300 before and 0.0429 after correction.
The Ratio of minimum to maximum transmission is 0.8841.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.895
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8429
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.922
_diffrn_reflns_theta_min         2.085
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.895
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3414
_reflns_number_total             4854
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         4854
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0584
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1114P)²+0.0803P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1754
_refine_ls_wR_factor_ref         0.1992
_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:
 C4(H4), C11(H11), C17(H17), C18(H18), C21(H21), C15(H15), C8(H8), C12(H12),
 C20(H20), C19(H19), C5(H5), C6(H6), C7(H7), C14(H14), C13(H13)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.032
;
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
C9 C 0.42661(15) 0.65598(13) 0.76258(12) 0.0391(3) Uani 1 1 d . . . . .
C10 C 0.27544(15) 0.67831(13) 0.82638(13) 0.0403(3) Uani 1 1 d . . . . .
C2 C 0.46551(15) 0.52950(13) 0.71872(13) 0.0400(3) Uani 1 1 d . . . . .
C3 C 0.34724(16) 0.40268(13) 0.70850(13) 0.0407(3) Uani 1 1 d . . . . .
C16 C 0.53340(15) 0.78677(13) 0.75674(13) 0.0395(3) Uani 1 1 d . . . . .
C4 C 0.39431(19) 0.27896(14) 0.75559(15) 0.0489(3) Uani 1 1 d . . . . .
H4 H 0.499828 0.276346 0.798066 0.059 Uiso 1 1 calc R U . . .
C11 C 0.24594(17) 0.61983(14) 0.94601(14) 0.0463(3) Uani 1 1 d . . . . .
H11 H 0.317855 0.560714 0.984430 0.056 Uiso 1 1 calc R U . . .
C17 C 0.58602(16) 0.87257(15) 0.87614(14) 0.0464(3) Uani 1 1 d . . . . .
H17 H 0.559652 0.845194 0.959496 0.056 Uiso 1 1 calc R U . . .
C18 C 0.67670(18) 0.99759(16) 0.87262(17) 0.0546(4) Uani 1 1 d . . . . .
H18 H 0.712915 1.052652 0.953685 0.065 Uiso 1 1 calc R U . . .
C1 C 0.62920(17) 0.50538(15) 0.67400(16) 0.0493(3) Uani 1 1 d . . . . .
H1A H 0.615348 0.473262 0.578512 0.074 Uiso 1 1 calc R U . . .
H1B H 0.677894 0.436626 0.726270 0.074 Uiso 1 1 calc R U . . .
H1C H 0.698328 0.590927 0.688809 0.074 Uiso 1 1 calc R U . . .
C21 C 0.5737(2) 0.83125(15) 0.63406(15) 0.0515(3) Uani 1 1 d . . . . .
H21 H 0.540830 0.775452 0.552857 0.062 Uiso 1 1 calc R U . . .
C15 C 0.16511(17) 0.76525(15) 0.77062(17) 0.0520(3) Uani 1 1 d . . . . .
H15 H 0.183468 0.806942 0.691549 0.062 Uiso 1 1 calc R U . . .
C8 C 0.18930(18) 0.40283(15) 0.64372(15) 0.0512(3) Uani 1 1 d . . . . .
H8 H 0.154875 0.483912 0.609850 0.061 Uiso 1 1 calc R U . . .
C12 C 0.11031(19) 0.64865(17) 1.00888(17) 0.0562(4) Uani 1 1 d . . . . .
H12 H 0.093550 0.610931 1.090305 0.067 Uiso 1 1 calc R U . . .
C20 C 0.6625(2) 0.95827(16) 0.63163(18) 0.0578(4) Uani 1 1 d . . . . .
H20 H 0.687550 0.987599 0.548619 0.069 Uiso 1 1 calc R U . . .
C19 C 0.71381(18) 1.04128(15) 0.75079(19) 0.0554(4) Uani 1 1 d . . . . .
H19 H 0.773305 1.126481 0.748622 0.066 Uiso 1 1 calc R U . . .
C5 C 0.2882(2) 0.15899(16) 0.74104(17) 0.0572(4) Uani 1 1 d . . . . .
H5 H 0.322341 0.077515 0.774265 0.069 Uiso 1 1 calc R U . . .
C6 C 0.1328(2) 0.16129(17) 0.67737(19) 0.0623(4) Uani 1 1 d . . . . .
H6 H 0.061272 0.081131 0.666607 0.075 Uiso 1 1 calc R U . . .
C7 C 0.0828(2) 0.28340(19) 0.62916(19) 0.0623(4) Uani 1 1 d . . . . .
H7 H -0.022891 0.285251 0.586768 0.075 Uiso 1 1 calc R U . . .
C14 C 0.0273(2) 0.79021(18) 0.8325(2) 0.0653(4) Uani 1 1 d . . . . .
H14 H -0.047523 0.846377 0.793147 0.078 Uiso 1 1 calc R U . . .
C13 C 0.00131(19) 0.73237(19) 0.9514(2) 0.0646(4) Uani 1 1 d . . . . .
H13 H -0.090467 0.750116 0.992780 0.077 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
C9 C10 1.4960(18) . ?
C9 C2 1.3434(18) . ?
C9 C16 1.4958(17) . ?
C10 C11 1.3894(19) . ?
C10 C15 1.3898(19) . ?
C2 C3 1.4989(17) . ?
C2 C1 1.5111(19) . ?
C3 C4 1.3871(19) . ?
C3 C8 1.391(2) . ?
C16 C17 1.3911(18) . ?
C16 C21 1.3867(19) . ?
C4 H4 0.9300 . ?
C4 C5 1.388(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.389(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.378(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.368(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C21 H21 0.9300 . ?
C21 C20 1.386(2) . ?
C15 H15 0.9300 . ?
C15 C14 1.391(2) . ?
C8 H8 0.9300 . ?
C8 C7 1.386(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.368(3) . ?
C20 H20 0.9300 . ?
C20 C19 1.374(2) . ?
C19 H19 0.9300 . ?
C5 H5 0.9300 . ?
C5 C6 1.372(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.385(3) . ?
C7 H7 0.9300 . ?
C14 H14 0.9300 . ?
C14 C13 1.373(3) . ?
C13 H13 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C9 C10 123.05(11) . . ?
C2 C9 C16 123.05(12) . . ?
C16 C9 C10 113.86(10) . . ?
C11 C10 C9 121.38(12) . . ?
C11 C10 C15 118.35(13) . . ?
C15 C10 C9 120.17(12) . . ?
C9 C2 C3 121.88(12) . . ?
C9 C2 C1 122.67(12) . . ?
C3 C2 C1 115.45(11) . . ?
C4 C3 C2 121.17(12) . . ?
C4 C3 C8 117.76(13) . . ?
C8 C3 C2 120.95(12) . . ?
C17 C16 C9 119.71(11) . . ?
C21 C16 C9 122.09(11) . . ?
C21 C16 C17 118.06(12) . . ?
C3 C4 H4 119.1 . . ?
C3 C4 C5 121.80(14) . . ?
C5 C4 H4 119.1 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.75(14) . . ?
C12 C11 H11 119.6 . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 120.93(13) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.49(13) . . ?
C19 C18 H18 119.8 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C16 C21 H21 119.8 . . ?
C20 C21 C16 120.44(13) . . ?
C20 C21 H21 119.8 . . ?
C10 C15 H15 119.8 . . ?
C10 C15 C14 120.33(15) . . ?
C14 C15 H15 119.8 . . ?
C3 C8 H8 119.7 . . ?
C7 C8 C3 120.67(14) . . ?
C7 C8 H8 119.7 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.17(15) . . ?
C13 C12 H12 119.9 . . ?
C21 C20 H20 119.7 . . ?
C19 C20 C21 120.59(14) . . ?
C19 C20 H20 119.7 . . ?
C18 C19 C20 119.47(14) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.60(15) . . ?
C6 C5 H5 120.2 . . ?
C5 C6 H6 120.1 . . ?
C5 C6 C7 119.77(14) . . ?
C7 C6 H6 120.1 . . ?
C8 C7 H7 119.8 . . ?
C6 C7 C8 120.39(15) . . ?
C6 C7 H7 119.8 . . ?
C15 C14 H14 119.8 . . ?
C13 C14 C15 120.34(15) . . ?
C13 C14 H14 119.8 . . ?
C12 C13 C14 120.02(15) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 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
C9 C10 C11 C12 175.84(12) . . . . ?
C9 C10 C15 C14 -177.69(13) . . . . ?
C9 C2 C3 C4 -135.04(14) . . . . ?
C9 C2 C3 C8 49.00(18) . . . . ?
C9 C16 C17 C18 -176.23(12) . . . . ?
C9 C16 C21 C20 174.99(13) . . . . ?
C10 C9 C2 C3 10.52(19) . . . . ?
C10 C9 C2 C1 -170.64(12) . . . . ?
C10 C9 C16 C17 54.97(16) . . . . ?
C10 C9 C16 C21 -120.54(14) . . . . ?
C10 C11 C12 C13 1.8(2) . . . . ?
C10 C15 C14 C13 1.8(2) . . . . ?
C2 C9 C10 C11 60.46(18) . . . . ?
C2 C9 C10 C15 -123.18(15) . . . . ?
C2 C9 C16 C17 -122.92(14) . . . . ?
C2 C9 C16 C21 61.57(18) . . . . ?
C2 C3 C4 C5 -176.94(13) . . . . ?
C2 C3 C8 C7 177.07(13) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
C3 C8 C7 C6 -0.9(2) . . . . ?
C16 C9 C10 C11 -117.43(13) . . . . ?
C16 C9 C10 C15 58.93(16) . . . . ?
C16 C9 C2 C3 -171.78(11) . . . . ?
C16 C9 C2 C1 7.06(19) . . . . ?
C16 C17 C18 C19 1.4(2) . . . . ?
C16 C21 C20 C19 0.8(2) . . . . ?
C4 C3 C8 C7 1.0(2) . . . . ?
C4 C5 C6 C7 -0.5(3) . . . . ?
C11 C10 C15 C14 -1.2(2) . . . . ?
C11 C12 C13 C14 -1.2(2) . . . . ?
C17 C16 C21 C20 -0.6(2) . . . . ?
C17 C18 C19 C20 -1.2(2) . . . . ?
C1 C2 C3 C4 46.04(17) . . . . ?
C1 C2 C3 C8 -129.92(14) . . . . ?
C21 C16 C17 C18 -0.5(2) . . . . ?
C21 C20 C19 C18 0.1(2) . . . . ?
C15 C10 C11 C12 -0.58(19) . . . . ?
C15 C14 C13 C12 -0.6(3) . . . . ?
C8 C3 C4 C5 -0.9(2) . . . . ?
C5 C6 C7 C8 0.6(3) . . . . ?

_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_y
_database_code_depnum_ccdc_archive 'CCDC 2094580'
loop_
_audit_author_name
_audit_author_address
TPMBr
;Wuhan University
China
;
_audit_update_record             
;
2021-07-06 deposited with the CCDC.	2021-09-06 downloaded from the CCDC.
;
_audit_creation_date             2021-05-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        TPMBr
_chemical_formula_moiety         'C21 H17 Br'
_chemical_formula_sum            'C21 H17 Br'
_chemical_formula_weight         349.26
_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'
Br Br -0.2901 2.4595 '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                   8.773(4)
_cell_length_b                   9.273(5)
_cell_length_c                   20.333(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.317(8)
_cell_angle_gamma                90
_cell_volume                     1654.3(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5722
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      28.42
_cell_measurement_theta_min      2.32
_shelx_estimated_absorpt_T_max   0.790
_shelx_estimated_absorpt_T_min   0.523
_exptl_absorpt_coefficient_mu    2.479
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.5295
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0888 before and 0.0487 after correction.
The Ratio of minimum to maximum transmission is 0.7095.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.943
_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       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            17055
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.824
_diffrn_reflns_theta_min         2.003
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3754
_reflns_number_total             5324
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.767
_refine_diff_density_rms         0.157
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         5324
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0500
_refine_ls_restrained_S_all      1.045
_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)+(0.0559P)²+0.4015P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1182
_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:
 C18(H18), C11(H11), C21(H21), C20(H20), C12(H12), C15(H15), C8(H8), C17(H17),
 C13(H13), C4(H4), C5(H5), C7(H7), C14(H14), C6(H6)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Br22 Br 0.21717(3) 0.22136(3) 0.33647(2) 0.04820(11) Uani 1 1 d . . . . .
C10 C 0.3022(2) 0.7712(2) 0.10998(9) 0.0273(4) Uani 1 1 d . . . . .
C16 C 0.2653(2) 0.5178(2) 0.15187(9) 0.0268(4) Uani 1 1 d . . . . .
C9 C 0.2766(2) 0.6166(2) 0.09410(9) 0.0278(4) Uani 1 1 d . . . . .
C19 C 0.2372(2) 0.3413(2) 0.26154(9) 0.0283(4) Uani 1 1 d . . . . .
C18 C 0.3707(3) 0.4163(3) 0.25203(10) 0.0342(5) Uani 1 1 d . . . . .
H18 H 0.451280 0.407115 0.281651 0.041 Uiso 1 1 calc R U . . .
C2 C 0.2589(3) 0.5669(2) 0.03203(9) 0.0308(4) Uani 1 1 d . . . . .
C3 C 0.2368(3) 0.6653(3) -0.02528(10) 0.0329(5) Uani 1 1 d . . . . .
C11 C 0.4096(3) 0.8536(2) 0.07667(10) 0.0330(5) Uani 1 1 d . . . . .
H11 H 0.469569 0.810789 0.044559 0.040 Uiso 1 1 calc R U . . .
C21 C 0.1323(2) 0.4401(2) 0.16318(10) 0.0312(4) Uani 1 1 d . . . . .
H21 H 0.051816 0.447146 0.133390 0.037 Uiso 1 1 calc R U . . .
C20 C 0.1173(2) 0.3522(2) 0.21799(10) 0.0315(4) Uani 1 1 d . . . . .
H20 H 0.027480 0.301517 0.225182 0.038 Uiso 1 1 calc R U . . .
C12 C 0.4281(3) 0.9985(3) 0.09078(11) 0.0419(6) Uani 1 1 d . . . . .
H12 H 0.499641 1.052504 0.067853 0.050 Uiso 1 1 calc R U . . .
C15 C 0.2193(3) 0.8368(3) 0.15965(11) 0.0355(5) Uani 1 1 d . . . . .
H15 H 0.150336 0.782561 0.183870 0.043 Uiso 1 1 calc R U . . .
C8 C 0.1292(3) 0.7744(3) -0.02263(13) 0.0438(6) Uani 1 1 d . . . . .
H8 H 0.075239 0.789517 0.015999 0.053 Uiso 1 1 calc R U . . .
C17 C 0.3835(2) 0.5058(3) 0.19773(10) 0.0331(5) Uani 1 1 d . . . . .
H17 H 0.472398 0.558725 0.191773 0.040 Uiso 1 1 calc R U . . .
C13 C 0.3409(3) 1.0634(3) 0.13874(12) 0.0435(6) Uani 1 1 d . . . . .
H13 H 0.351597 1.161395 0.147416 0.052 Uiso 1 1 calc R U . . .
C4 C 0.3137(3) 0.6444(3) -0.08412(10) 0.0432(6) Uani 1 1 d . . . . .
H4 H 0.385336 0.570888 -0.087254 0.052 Uiso 1 1 calc R U . . .
C5 C 0.2852(4) 0.7316(3) -0.13820(12) 0.0556(8) Uani 1 1 d . . . . .
H5 H 0.338068 0.716590 -0.177111 0.067 Uiso 1 1 calc R U . . .
C1 C 0.2548(4) 0.4083(3) 0.01531(12) 0.0486(6) Uani 1 1 d . . . . .
H1A H 0.268314 0.352637 0.054715 0.073 Uiso 1 1 calc R U . . .
H1B H 0.335206 0.386462 -0.014934 0.073 Uiso 1 1 calc R U . . .
H1C H 0.158314 0.385050 -0.004480 0.073 Uiso 1 1 calc R U . . .
C7 C 0.1009(4) 0.8617(3) -0.07687(15) 0.0568(8) Uani 1 1 d . . . . .
H7 H 0.028857 0.934968 -0.074291 0.068 Uiso 1 1 calc R U . . .
C14 C 0.2379(3) 0.9821(3) 0.17363(12) 0.0424(5) Uani 1 1 d . . . . .
H14 H 0.180627 1.024741 0.206699 0.051 Uiso 1 1 calc R U . . .
C6 C 0.1794(4) 0.8397(4) -0.13447(14) 0.0601(9) Uani 1 1 d . . . . .
H6 H 0.160574 0.898155 -0.170768 0.072 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
Br22 C19 1.895(2) . ?
C10 C9 1.487(3) . ?
C10 C11 1.392(3) . ?
C10 C15 1.388(3) . ?
C16 C9 1.493(3) . ?
C16 C21 1.392(3) . ?
C16 C17 1.395(3) . ?
C9 C2 1.351(3) . ?
C19 C18 1.377(3) . ?
C19 C20 1.375(3) . ?
C18 H18 0.9300 . ?
C18 C17 1.386(3) . ?
C2 C3 1.492(3) . ?
C2 C1 1.510(3) . ?
C3 C8 1.385(4) . ?
C3 C4 1.390(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.383(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.387(3) . ?
C20 H20 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.381(4) . ?
C15 H15 0.9300 . ?
C15 C14 1.386(4) . ?
C8 H8 0.9300 . ?
C8 C7 1.389(4) . ?
C17 H17 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.377(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.386(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.368(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C7 H7 0.9300 . ?
C7 C6 1.377(5) . ?
C14 H14 0.9300 . ?
C6 H6 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 C10 C9 121.72(18) . . ?
C15 C10 C9 120.10(19) . . ?
C15 C10 C11 118.2(2) . . ?
C21 C16 C9 120.45(18) . . ?
C21 C16 C17 117.96(18) . . ?
C17 C16 C9 121.51(18) . . ?
C10 C9 C16 115.55(16) . . ?
C2 C9 C10 123.23(18) . . ?
C2 C9 C16 121.19(19) . . ?
C18 C19 Br22 119.49(15) . . ?
C20 C19 Br22 119.14(16) . . ?
C20 C19 C18 121.38(19) . . ?
C19 C18 H18 120.4 . . ?
C19 C18 C17 119.14(18) . . ?
C17 C18 H18 120.4 . . ?
C9 C2 C3 122.3(2) . . ?
C9 C2 C1 123.0(2) . . ?
C3 C2 C1 114.66(18) . . ?
C8 C3 C2 120.2(2) . . ?
C8 C3 C4 118.0(2) . . ?
C4 C3 C2 121.7(2) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.8(2) . . ?
C12 C11 H11 119.6 . . ?
C16 C21 H21 119.3 . . ?
C20 C21 C16 121.33(19) . . ?
C20 C21 H21 119.3 . . ?
C19 C20 C21 119.0(2) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.3(2) . . ?
C13 C12 H12 119.8 . . ?
C10 C15 H15 119.6 . . ?
C14 C15 C10 120.9(2) . . ?
C14 C15 H15 119.6 . . ?
C3 C8 H8 119.6 . . ?
C3 C8 C7 120.9(3) . . ?
C7 C8 H8 119.6 . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.14(19) . . ?
C18 C17 H17 119.4 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.5(2) . . ?
C14 C13 H13 120.2 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.0(3) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C8 C7 H7 120.0 . . ?
C6 C7 C8 120.1(3) . . ?
C6 C7 H7 120.0 . . ?
C15 C14 H14 119.9 . . ?
C13 C14 C15 120.2(2) . . ?
C13 C14 H14 119.9 . . ?
C5 C6 C7 119.9(2) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?

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
Br22 C19 C18 C17 -178.87(17) . . . . ?
Br22 C19 C20 C21 -179.98(16) . . . . ?
C10 C9 C2 C3 -10.8(3) . . . . ?
C10 C9 C2 C1 171.3(2) . . . . ?
C10 C11 C12 C13 0.6(3) . . . . ?
C10 C15 C14 C13 -0.8(4) . . . . ?
C16 C9 C2 C3 166.8(2) . . . . ?
C16 C9 C2 C1 -11.2(4) . . . . ?
C16 C21 C20 C19 -0.6(3) . . . . ?
C9 C10 C11 C12 177.9(2) . . . . ?
C9 C10 C15 C14 -177.8(2) . . . . ?
C9 C16 C21 C20 -177.37(19) . . . . ?
C9 C16 C17 C18 178.5(2) . . . . ?
C9 C2 C3 C8 -49.0(3) . . . . ?
C9 C2 C3 C4 135.9(2) . . . . ?
C19 C18 C17 C16 -1.8(3) . . . . ?
C18 C19 C20 C21 0.5(3) . . . . ?
C2 C3 C8 C7 -176.2(2) . . . . ?
C2 C3 C4 C5 176.1(2) . . . . ?
C3 C8 C7 C6 0.5(4) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C11 C10 C9 C16 134.8(2) . . . . ?
C11 C10 C9 C2 -47.5(3) . . . . ?
C11 C10 C15 C14 2.9(3) . . . . ?
C11 C12 C13 C14 1.6(4) . . . . ?
C21 C16 C9 C10 118.5(2) . . . . ?
C21 C16 C9 C2 -59.3(3) . . . . ?
C21 C16 C17 C18 1.7(3) . . . . ?
C20 C19 C18 C17 0.7(3) . . . . ?
C12 C13 C14 C15 -1.5(4) . . . . ?
C15 C10 C9 C16 -44.5(3) . . . . ?
C15 C10 C9 C2 133.3(2) . . . . ?
C15 C10 C11 C12 -2.8(3) . . . . ?
C8 C3 C4 C5 0.9(4) . . . . ?
C8 C7 C6 C5 0.1(4) . . . . ?
C17 C16 C9 C10 -58.3(3) . . . . ?
C17 C16 C9 C2 124.0(2) . . . . ?
C17 C16 C21 C20 -0.5(3) . . . . ?
C4 C3 C8 C7 -1.0(4) . . . . ?
C4 C5 C6 C7 -0.1(4) . . . . ?
C1 C2 C3 C8 129.1(3) . . . . ?
C1 C2 C3 C4 -46.0(3) . . . . ?

_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_mo_210529p_0m
_database_code_depnum_ccdc_archive 'CCDC 2094582'
loop_
_audit_author_name
_audit_author_address
TPF
;Wuhan University
China
;
_audit_update_record             
;
2021-07-06 deposited with the CCDC.	2021-09-06 downloaded from the CCDC.
;
_audit_creation_date             2021-06-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '4(C21 H15 F3)'
_chemical_formula_sum            'C84 H60 F12'
_chemical_formula_weight         1297.32
_chemical_absolute_configuration ?
_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 0.0030 0.0020 '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 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   31.90(3)
_cell_length_b                   8.761(9)
_cell_length_c                   5.796(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1620(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    5777
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.16
_cell_measurement_theta_min      2.32
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4918
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1577 before and 0.0837 after correction.
The Ratio of minimum to maximum transmission is 0.6598.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            10202
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.340
_diffrn_reflns_theta_min         2.411
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    0.929
_reflns_Friedel_fraction_max     0.923
_reflns_number_gt                2654
_reflns_number_total             3134
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 856 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3134
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0636
_refine_ls_restrained_S_all      1.132
_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)+(0.0148P)²+1.5028P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1387
_refine_ls_wR_factor_ref         0.1444
_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), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F -0.70709(10) -0.6977(5) 0.1524(10) 0.0972(16) Uani 1 1 d . . . . .
F2 F -0.70501(11) -0.6611(5) -0.2041(10) 0.0928(14) Uani 1 1 d . . . . .
F3 F -0.72027(9) -0.4777(4) 0.0208(9) 0.0853(14) Uani 1 1 d . . . . .
C1 C -0.50473(15) -0.2917(6) -0.0034(12) 0.0530(13) Uani 1 1 d . . . . .
H1 H -0.476865 -0.261405 0.008137 0.064 Uiso 1 1 calc R U . . .
C2 C -0.52351(16) -0.3677(6) 0.1747(11) 0.0510(13) Uani 1 1 d . . . . .
H2 H -0.508363 -0.388084 0.308222 0.061 Uiso 1 1 calc R U . . .
C3 C -0.56505(16) -0.4148(6) 0.1584(9) 0.0463(12) Uani 1 1 d . . . . .
H3 H -0.577309 -0.467781 0.279986 0.056 Uiso 1 1 calc R U . . .
C4 C -0.58839(13) -0.3832(5) -0.0391(9) 0.0385(10) Uani 1 1 d . . . . .
C5 C -0.63366(14) -0.4259(5) -0.0617(9) 0.0389(10) Uani 1 1 d . . . . .
C6 C -0.64878(14) -0.5609(6) 0.0097(9) 0.0420(11) Uani 1 1 d . . . . .
C7 C -0.62221(14) -0.6943(5) 0.0789(9) 0.0390(11) Uani 1 1 d . . . . .
C8 C -0.59289(14) -0.7496(6) -0.0754(9) 0.0449(11) Uani 1 1 d . . . . .
H8 H -0.589189 -0.700656 -0.216240 0.054 Uiso 1 1 calc R U . . .
C9 C -0.56898(15) -0.8767(6) -0.0236(11) 0.0506(13) Uani 1 1 d . . . . .
H9 H -0.549432 -0.912627 -0.129537 0.061 Uiso 1 1 calc R U . . .
C10 C -0.57407(16) -0.9507(6) 0.1857(12) 0.0550(14) Uani 1 1 d . . . . .
H10 H -0.558167 -1.036556 0.220724 0.066 Uiso 1 1 calc R U . . .
C11 C -0.70531(19) -0.0738(8) -0.3827(16) 0.079(2) Uani 1 1 d . . . . .
H11 H -0.720876 0.003459 -0.451840 0.094 Uiso 1 1 calc R U . . .
C12 C -0.70227(19) -0.2153(8) -0.4864(14) 0.0712(18) Uani 1 1 d . . . . .
H12 H -0.715532 -0.232924 -0.626825 0.085 Uiso 1 1 calc R U . . .
C13 C -0.67973(17) -0.3300(7) -0.3829(10) 0.0587(15) Uani 1 1 d . . . . .
H13 H -0.678021 -0.425153 -0.453466 0.070 Uiso 1 1 calc R U . . .
C14 C -0.65954(14) -0.3055(6) -0.1748(10) 0.0442(12) Uani 1 1 d . . . . .
C15 C -0.52730(16) -0.2604(6) -0.1995(11) 0.0517(13) Uani 1 1 d . . . . .
H15 H -0.514559 -0.209367 -0.321391 0.062 Uiso 1 1 calc R U . . .
C16 C -0.56897(15) -0.3044(6) -0.2172(9) 0.0462(12) Uani 1 1 d . . . . .
H16 H -0.584036 -0.280759 -0.349863 0.055 Uiso 1 1 calc R U . . .
C17 C -0.69527(15) -0.5963(6) -0.0012(13) 0.0571(15) Uani 1 1 d . . . . .
C18 C -0.62633(16) -0.7696(6) 0.2899(11) 0.0501(13) Uani 1 1 d . . . . .
H18 H -0.645387 -0.733806 0.398557 0.060 Uiso 1 1 calc R U . . .
C19 C -0.60244(18) -0.8966(6) 0.3386(11) 0.0544(13) Uani 1 1 d . . . . .
H19 H -0.605885 -0.945990 0.479272 0.065 Uiso 1 1 calc R U . . .
C20 C -0.66274(15) -0.1627(6) -0.0767(11) 0.0535(14) Uani 1 1 d . . . . .
H20 H -0.649159 -0.143837 0.062423 0.064 Uiso 1 1 calc R U . . .
C21 C -0.68528(19) -0.0479(6) -0.1776(16) 0.0703(19) Uani 1 1 d . . . . .
H21 H -0.686983 0.047325 -0.107237 0.084 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
F1 C17 1.313(7) . ?
F2 C17 1.342(8) . ?
F3 C17 1.317(6) . ?
C1 H1 0.9300 . ?
C1 C2 1.366(8) . ?
C1 C15 1.373(9) . ?
C2 H2 0.9300 . ?
C2 C3 1.391(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.393(7) . ?
C4 C5 1.497(6) . ?
C4 C16 1.388(7) . ?
C5 C6 1.343(7) . ?
C5 C14 1.491(7) . ?
C6 C7 1.498(7) . ?
C6 C17 1.516(7) . ?
C7 C8 1.382(7) . ?
C7 C18 1.396(8) . ?
C8 H8 0.9300 . ?
C8 C9 1.383(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.385(9) . ?
C10 H10 0.9300 . ?
C10 C19 1.352(8) . ?
C11 H11 0.9300 . ?
C11 C12 1.381(10) . ?
C11 C21 1.368(11) . ?
C12 H12 0.9300 . ?
C12 C13 1.374(9) . ?
C13 H13 0.9300 . ?
C13 C14 1.384(8) . ?
C14 C20 1.378(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.388(7) . ?
C16 H16 0.9300 . ?
C18 H18 0.9300 . ?
C18 C19 1.377(7) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C20 C21 1.368(8) . ?
C21 H21 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 120.3 . . ?
C2 C1 C15 119.5(5) . . ?
C15 C1 H1 120.3 . . ?
C1 C2 H2 119.6 . . ?
C1 C2 C3 120.7(5) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.4(5) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 122.5(4) . . ?
C16 C4 C3 118.1(4) . . ?
C16 C4 C5 119.3(4) . . ?
C6 C5 C4 122.6(4) . . ?
C6 C5 C14 124.0(4) . . ?
C14 C5 C4 113.3(4) . . ?
C5 C6 C7 124.5(4) . . ?
C5 C6 C17 121.3(4) . . ?
C7 C6 C17 113.9(4) . . ?
C8 C7 C6 118.9(5) . . ?
C8 C7 C18 117.7(5) . . ?
C18 C7 C6 123.4(4) . . ?
C7 C8 H8 119.5 . . ?
C7 C8 C9 121.0(5) . . ?
C9 C8 H8 119.5 . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.1(5) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 120.4 . . ?
C19 C10 C9 119.2(5) . . ?
C19 C10 H10 120.4 . . ?
C12 C11 H11 120.2 . . ?
C21 C11 H11 120.2 . . ?
C21 C11 C12 119.6(6) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.2(7) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.7(6) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 C5 122.1(5) . . ?
C20 C14 C5 120.1(5) . . ?
C20 C14 C13 117.8(5) . . ?
C1 C15 H15 119.7 . . ?
C1 C15 C16 120.6(5) . . ?
C16 C15 H15 119.7 . . ?
C4 C16 H16 119.7 . . ?
C15 C16 C4 120.7(5) . . ?
C15 C16 H16 119.7 . . ?
F1 C17 F2 104.0(5) . . ?
F1 C17 F3 107.1(5) . . ?
F1 C17 C6 113.0(5) . . ?
F2 C17 C6 110.4(5) . . ?
F3 C17 F2 106.1(5) . . ?
F3 C17 C6 115.3(4) . . ?
C7 C18 H18 119.7 . . ?
C19 C18 C7 120.6(5) . . ?
C19 C18 H18 119.7 . . ?
C10 C19 C18 121.3(6) . . ?
C10 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C14 C20 H20 119.0 . . ?
C21 C20 C14 122.0(6) . . ?
C21 C20 H20 119.0 . . ?
C11 C21 H21 120.2 . . ?
C20 C21 C11 119.7(6) . . ?
C20 C21 H21 120.2 . . ?

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
C1 C2 C3 C4 -1.0(8) . . . . ?
C1 C15 C16 C4 -1.2(8) . . . . ?
C2 C1 C15 C16 0.4(8) . . . . ?
C2 C3 C4 C5 -177.5(5) . . . . ?
C2 C3 C4 C16 0.2(7) . . . . ?
C3 C4 C5 C6 -42.2(7) . . . . ?
C3 C4 C5 C14 139.0(5) . . . . ?
C3 C4 C16 C15 0.9(7) . . . . ?
C4 C5 C6 C7 -11.6(8) . . . . ?
C4 C5 C6 C17 175.9(5) . . . . ?
C4 C5 C14 C13 117.0(5) . . . . ?
C4 C5 C14 C20 -60.6(6) . . . . ?
C5 C4 C16 C15 178.6(5) . . . . ?
C5 C6 C7 C8 -55.7(7) . . . . ?
C5 C6 C7 C18 126.4(6) . . . . ?
C5 C6 C17 F1 -153.7(5) . . . . ?
C5 C6 C17 F2 90.3(6) . . . . ?
C5 C6 C17 F3 -30.0(9) . . . . ?
C5 C14 C20 C21 178.3(5) . . . . ?
C6 C5 C14 C13 -61.7(7) . . . . ?
C6 C5 C14 C20 120.6(6) . . . . ?
C6 C7 C8 C9 -177.0(5) . . . . ?
C6 C7 C18 C19 176.6(5) . . . . ?
C7 C6 C17 F1 33.1(7) . . . . ?
C7 C6 C17 F2 -83.0(6) . . . . ?
C7 C6 C17 F3 156.8(5) . . . . ?
C7 C8 C9 C10 -0.1(8) . . . . ?
C7 C18 C19 C10 0.8(8) . . . . ?
C8 C7 C18 C19 -1.3(7) . . . . ?
C8 C9 C10 C19 -0.4(8) . . . . ?
C9 C10 C19 C18 0.1(8) . . . . ?
C11 C12 C13 C14 -0.5(10) . . . . ?
C12 C11 C21 C20 -0.5(10) . . . . ?
C12 C13 C14 C5 -177.9(5) . . . . ?
C12 C13 C14 C20 -0.2(8) . . . . ?
C13 C14 C20 C21 0.6(8) . . . . ?
C14 C5 C6 C7 167.0(5) . . . . ?
C14 C5 C6 C17 -5.5(8) . . . . ?
C14 C20 C21 C11 -0.2(10) . . . . ?
C15 C1 C2 C3 0.6(8) . . . . ?
C16 C4 C5 C6 140.2(5) . . . . ?
C16 C4 C5 C14 -38.6(6) . . . . ?
C17 C6 C7 C8 117.3(5) . . . . ?
C17 C6 C7 C18 -60.6(7) . . . . ?
C18 C7 C8 C9 1.0(7) . . . . ?
C21 C11 C12 C13 0.8(10) . . . . ?

_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_mo_210529a_0m
_database_code_depnum_ccdc_archive 'CCDC 2094587'
loop_
_audit_author_name
_audit_author_address
TPFBr
;Wuhan University
China
;
_audit_update_record             
;
2021-07-06 deposited with the CCDC.	2021-09-06 downloaded from the CCDC.
;
_audit_creation_date             2021-05-29
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H14 Br F3'
_chemical_formula_sum            'C21 H14 Br F3'
_chemical_formula_weight         403.23
_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'
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'

_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                   13.672(5)
_cell_length_b                   7.976(3)
_cell_length_c                   16.909(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.786(6)
_cell_angle_gamma                90
_cell_volume                     1817.0(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4760
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.92
_cell_measurement_theta_min      2.65
_shelx_estimated_absorpt_T_max   0.956
_shelx_estimated_absorpt_T_min   0.803
_exptl_absorpt_coefficient_mu    2.291
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.4776
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0694
_diffrn_reflns_av_unetI/netI     0.0817
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            18198
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.898
_diffrn_reflns_theta_min         1.511
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2735
_reflns_number_total             5840
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         1.324
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         5840
_refine_ls_number_restraints     39
_refine_ls_R_factor_all          0.1680
_refine_ls_R_factor_gt           0.0743
_refine_ls_restrained_S_all      1.040
_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)+(0.0895P)²+0.8164P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1737
_refine_ls_wR_factor_ref         0.2098
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C21-F5 \\sim C21-F2
 with sigma of 0.02
 C21-F4 \\sim C21-F1
 with sigma of 0.02
 C21-F6 \\sim C21-F3
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F2) \\sim Ueq, Uanis(F4) \\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F3) \\sim
Ueq, Uanis(F6) \\sim Ueq, Uanis(F5) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Sof(F1)=Sof(F2)=Sof(F3)=1-FVAR(1)
 Sof(F4)=Sof(F5)=Sof(F6)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C13(H13),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Br1 Br 0.01917(4) 0.11988(7) 0.11409(3) 0.0809(3) Uani 1 1 d . . . . .
C1 C -0.3341(3) -0.4538(5) 0.1843(2) 0.0476(8) Uani 1 1 d . . . . .
C2 C -0.2963(3) -0.5630(6) 0.2447(2) 0.0628(11) Uani 1 1 d . . . . .
H2 H -0.247211 -0.639152 0.237154 0.075 Uiso 1 1 calc R U . . .
C3 C -0.3313(4) -0.5596(6) 0.3170(3) 0.0666(11) Uani 1 1 d . . . . .
H3 H -0.303533 -0.630043 0.358582 0.080 Uiso 1 1 calc R U . . .
C4 C -0.4065(4) -0.4533(6) 0.3274(3) 0.0663(12) Uani 1 1 d . . . . .
H4 H -0.431841 -0.454484 0.375087 0.080 Uiso 1 1 calc R U . . .
C5 C -0.4441(4) -0.3450(6) 0.2669(3) 0.0684(12) Uani 1 1 d . . . . .
H5 H -0.494796 -0.271600 0.274038 0.082 Uiso 1 1 calc R U . . .
C6 C -0.4083(3) -0.3435(6) 0.1965(2) 0.0595(10) Uani 1 1 d . . . . .
H6 H -0.433802 -0.267936 0.156393 0.071 Uiso 1 1 calc R U . . .
C7 C -0.2903(3) -0.4420(5) 0.1091(2) 0.0452(8) Uani 1 1 d . . . . .
C8 C -0.2177(2) -0.3038(5) 0.1083(2) 0.0433(8) Uani 1 1 d . . . . .
C9 C -0.2263(3) -0.1835(5) 0.0478(2) 0.0549(9) Uani 1 1 d . . . . .
H9 H -0.278981 -0.189626 0.005156 0.066 Uiso 1 1 calc R U . . .
C10 C -0.1585(3) -0.0562(5) 0.0501(2) 0.0576(10) Uani 1 1 d . . . . .
H10 H -0.166019 0.025183 0.010087 0.069 Uiso 1 1 calc R U . . .
C11 C -0.0786(3) -0.0500(5) 0.1126(2) 0.0487(8) Uani 1 1 d . . . . .
C12 C -0.0680(3) -0.1669(5) 0.1723(2) 0.0523(9) Uani 1 1 d . . . . .
H12 H -0.014017 -0.162114 0.213913 0.063 Uiso 1 1 calc R U . . .
C13 C -0.1373(3) -0.2912(5) 0.1708(2) 0.0524(9) Uani 1 1 d . . . . .
H13 H -0.130568 -0.368871 0.212428 0.063 Uiso 1 1 calc R U . . .
C14 C -0.3120(3) -0.5482(5) 0.0470(2) 0.0449(8) Uani 1 1 d . . . . .
C15 C -0.2582(3) -0.5425(4) -0.0242(2) 0.0424(8) Uani 1 1 d . . . . .
C16 C -0.3055(4) -0.4949(6) -0.0996(2) 0.0645(11) Uani 1 1 d . . . . .
H16 H -0.372301 -0.465831 -0.107957 0.077 Uiso 1 1 calc R U . . .
C17 C -0.2528(5) -0.4908(7) -0.1625(3) 0.0861(16) Uani 1 1 d . . . . .
H17 H -0.283553 -0.455044 -0.212946 0.103 Uiso 1 1 calc R U . . .
C18 C -0.1545(4) -0.5398(6) -0.1502(3) 0.0733(14) Uani 1 1 d . . . . .
H18 H -0.119555 -0.538871 -0.192861 0.088 Uiso 1 1 calc R U . . .
C19 C -0.1090(4) -0.5890(6) -0.0772(3) 0.0743(14) Uani 1 1 d . . . . .
H19 H -0.042943 -0.622465 -0.069476 0.089 Uiso 1 1 calc R U . . .
C20 C -0.1605(3) -0.5898(5) -0.0131(3) 0.0550(10) Uani 1 1 d . . . . .
H20 H -0.128521 -0.622597 0.037476 0.066 Uiso 1 1 calc R U . . .
C21 C -0.3846(3) -0.6899(5) 0.0465(2) 0.0550(10) Uani 1 1 d D . . . .
F1 F -0.3749(17) -0.8069(18) -0.0038(12) 0.080(5) Uani 0.31(2) 1 d D U P A 2
F2 F -0.4791(9) -0.654(3) 0.034(2) 0.128(8) Uani 0.31(2) 1 d D U P A 2
F3 F -0.3764(18) -0.788(3) 0.1100(7) 0.106(7) Uani 0.31(2) 1 d D U P A 2
F4 F -0.4207(10) -0.7393(19) -0.0266(4) 0.115(4) Uani 0.69(2) 1 d D U P A 1
F5 F -0.4605(6) -0.6544(9) 0.0795(6) 0.087(3) Uani 0.69(2) 1 d D U P A 1
F6 F -0.3425(7) -0.8178(9) 0.0866(9) 0.128(4) Uani 0.69(2) 1 d D U P A 1


_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
Br1 C11 1.900(4) . ?
C1 C2 1.375(6) . ?
C1 C6 1.384(5) . ?
C1 C7 1.498(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.386(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.366(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.370(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.363(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.485(5) . ?
C7 C14 1.342(5) . ?
C8 C9 1.393(5) . ?
C8 C13 1.393(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.371(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.386(5) . ?
C11 C12 1.364(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.368(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.514(4) . ?
C14 C21 1.504(6) . ?
C15 C16 1.381(6) . ?
C15 C20 1.370(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.382(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.381(8) . ?
C18 H18 0.9300 . ?
C18 C19 1.344(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.388(6) . ?
C20 H20 0.9300 . ?
C21 F1 1.285(11) . ?
C21 F2 1.306(12) . ?
C21 F3 1.315(12) . ?
C21 F4 1.311(7) . ?
C21 F5 1.291(6) . ?
C21 F6 1.303(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.0(3) . . ?
C2 C1 C7 121.1(3) . . ?
C6 C1 C7 119.7(3) . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 120.0(4) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(4) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.3(4) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.8(4) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.4(4) . . ?
C5 C6 H6 119.8 . . ?
C8 C7 C1 114.7(3) . . ?
C14 C7 C1 123.9(3) . . ?
C14 C7 C8 121.4(3) . . ?
C9 C8 C7 123.0(3) . . ?
C13 C8 C7 119.3(3) . . ?
C13 C8 C9 117.7(3) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.2(3) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 120.4 . . ?
C9 C10 C11 119.3(4) . . ?
C11 C10 H10 120.4 . . ?
C10 C11 Br1 119.8(3) . . ?
C12 C11 Br1 119.5(3) . . ?
C12 C11 C10 120.7(4) . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.7(3) . . ?
C13 C12 H12 120.1 . . ?
C8 C13 H13 119.3 . . ?
C12 C13 C8 121.4(3) . . ?
C12 C13 H13 119.3 . . ?
C7 C14 C15 122.0(3) . . ?
C7 C14 C21 122.5(3) . . ?
C21 C14 C15 115.3(3) . . ?
C16 C15 C14 121.9(3) . . ?
C20 C15 C14 118.5(3) . . ?
C20 C15 C16 119.6(3) . . ?
C15 C16 H16 120.2 . . ?
C15 C16 C17 119.6(4) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 119.9(5) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.4(4) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.1(5) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 C19 120.3(4) . . ?
C15 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
F1 C21 C14 114.0(7) . . ?
F1 C21 F2 105.3(12) . . ?
F1 C21 F3 96.1(10) . . ?
F2 C21 C14 118.1(10) . . ?
F2 C21 F3 101.9(13) . . ?
F3 C21 C14 118.4(9) . . ?
F4 C21 C14 111.9(5) . . ?
F5 C21 C14 114.3(4) . . ?
F5 C21 F4 105.8(6) . . ?
F5 C21 F6 105.3(6) . . ?
F6 C21 C14 110.6(5) . . ?
F6 C21 F4 108.5(7) . . ?

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
Br1 C11 C12 C13 -178.9(3) . . . . ?
C1 C2 C3 C4 2.9(7) . . . . ?
C1 C7 C8 C9 -125.6(4) . . . . ?
C1 C7 C8 C13 53.9(4) . . . . ?
C1 C7 C14 C15 -173.6(3) . . . . ?
C1 C7 C14 C21 1.0(6) . . . . ?
C2 C1 C6 C5 -0.9(7) . . . . ?
C2 C1 C7 C8 -96.9(4) . . . . ?
C2 C1 C7 C14 81.8(5) . . . . ?
C2 C3 C4 C5 -2.7(7) . . . . ?
C3 C4 C5 C6 0.7(7) . . . . ?
C4 C5 C6 C1 1.1(7) . . . . ?
C6 C1 C2 C3 -1.1(7) . . . . ?
C6 C1 C7 C8 77.6(4) . . . . ?
C6 C1 C7 C14 -103.7(5) . . . . ?
C7 C1 C2 C3 173.4(4) . . . . ?
C7 C1 C6 C5 -175.5(4) . . . . ?
C7 C8 C9 C10 178.9(4) . . . . ?
C7 C8 C13 C12 179.4(3) . . . . ?
C7 C14 C15 C16 -112.5(5) . . . . ?
C7 C14 C15 C20 69.0(5) . . . . ?
C7 C14 C21 F1 -159.9(14) . . . . ?
C7 C14 C21 F2 76(2) . . . . ?
C7 C14 C21 F3 -48.0(14) . . . . ?
C7 C14 C21 F4 157.7(9) . . . . ?
C7 C14 C21 F5 37.4(8) . . . . ?
C7 C14 C21 F6 -81.2(9) . . . . ?
C8 C7 C14 C15 5.0(5) . . . . ?
C8 C7 C14 C21 179.6(3) . . . . ?
C8 C9 C10 C11 1.8(6) . . . . ?
C9 C8 C13 C12 -1.1(5) . . . . ?
C9 C10 C11 Br1 177.3(3) . . . . ?
C9 C10 C11 C12 -1.3(6) . . . . ?
C10 C11 C12 C13 -0.3(6) . . . . ?
C11 C12 C13 C8 1.6(6) . . . . ?
C13 C8 C9 C10 -0.6(6) . . . . ?
C14 C7 C8 C9 55.7(5) . . . . ?
C14 C7 C8 C13 -124.8(4) . . . . ?
C14 C15 C16 C17 179.6(4) . . . . ?
C14 C15 C20 C19 179.0(4) . . . . ?
C15 C14 C21 F1 15.0(15) . . . . ?
C15 C14 C21 F2 -109(2) . . . . ?
C15 C14 C21 F3 126.9(13) . . . . ?
C15 C14 C21 F4 -27.4(10) . . . . ?
C15 C14 C21 F5 -147.7(6) . . . . ?
C15 C14 C21 F6 93.7(8) . . . . ?
C15 C16 C17 C18 2.3(8) . . . . ?
C16 C15 C20 C19 0.4(6) . . . . ?
C16 C17 C18 C19 -1.1(8) . . . . ?
C17 C18 C19 C20 -0.4(7) . . . . ?
C18 C19 C20 C15 0.8(7) . . . . ?
C20 C15 C16 C17 -1.9(6) . . . . ?
C21 C14 C15 C16 72.6(5) . . . . ?
C21 C14 C15 C20 -105.9(4) . . . . ?

_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_mo_201115c_0m
_database_code_depnum_ccdc_archive 'CCDC 2094581'
loop_
_audit_author_name
_audit_author_address
TPMBrd
;Wuhan University
China
;
_audit_update_record             
;
2021-07-06 deposited with the CCDC.	2021-09-06 downloaded from the CCDC.
;
_audit_creation_date             2020-11-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H16 Br2'
_chemical_formula_sum            'C21 H16 Br2'
_chemical_formula_weight         428.14
_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 0.0030 0.0020 '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 -0.2900 2.4600 '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                   12.880(9)
_cell_length_b                   8.745(6)
_cell_length_c                   18.874(10)
_cell_angle_alpha                90
_cell_angle_beta                 121.39(3)
_cell_angle_gamma                90
_cell_volume                     1815(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2529
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.42
_cell_measurement_theta_min      2.22
_shelx_estimated_absorpt_T_max   0.664
_shelx_estimated_absorpt_T_min   0.348
_exptl_absorpt_coefficient_mu    4.464
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.1919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1783
_diffrn_reflns_av_unetI/netI     0.1847
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9888
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        23.998
_diffrn_reflns_theta_max         23.998
_diffrn_reflns_theta_min         1.852
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1561
_reflns_number_total             2773
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_refine_diff_density_max         0.733
_refine_diff_density_min         -1.160
_refine_diff_density_rms         0.170
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2773
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.2159
_refine_ls_R_factor_gt           0.1325
_refine_ls_restrained_S_all      1.049
_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)+(0.1158P)²+17.0489P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2379
_refine_ls_wR_factor_ref         0.2764
_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. Uiso/Uaniso restraints and constraints
Uanis(C10) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C19)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C13(H13),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
3.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_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
Br1 Br 0.35610(12) 0.2681(2) 0.08674(11) 0.0708(8) Uani 1 1 d . . . . .
Br2 Br 1.26010(13) 0.2995(2) 0.29301(12) 0.0598(7) Uani 1 1 d . . . . .
C1 C 0.5171(9) 0.2617(14) 0.1807(8) 0.028(3) Uani 1 1 d . . . . .
C2 C 0.5536(10) 0.1391(15) 0.2299(8) 0.035(3) Uani 1 1 d . U . . .
H2 H 0.5014 0.0569 0.2186 0.042 Uiso 1 1 calc R . . . .
C3 C 0.6697(10) 0.1365(15) 0.2976(8) 0.030(3) Uani 1 1 d . . . . .
H3 H 0.6954 0.0510 0.3319 0.037 Uiso 1 1 calc R . . . .
C4 C 0.7494(9) 0.2552(14) 0.3165(8) 0.026(3) Uani 1 1 d . . . . .
C5 C 0.7081(10) 0.3795(15) 0.2623(8) 0.032(4) Uani 1 1 d . . . . .
H5 H 0.7606 0.4611 0.2728 0.039 Uiso 1 1 calc R . . . .
C6 C 0.5922(11) 0.3852(16) 0.1936(8) 0.035(4) Uani 1 1 d . . . . .
H6 H 0.5656 0.4682 0.1575 0.042 Uiso 1 1 calc R . . . .
C7 C 0.8748(10) 0.2511(14) 0.3889(7) 0.025(3) Uani 1 1 d . . . . .
C8 C 0.9675(9) 0.2666(15) 0.3660(8) 0.028(3) Uani 1 1 d . . . . .
C9 C 0.9634(11) 0.1717(17) 0.3053(8) 0.039(4) Uani 1 1 d . . . . .
H9 H 0.9006 0.1009 0.2793 0.047 Uiso 1 1 calc R . . . .
C10 C 1.0490(11) 0.1785(16) 0.2821(9) 0.039(4) Uani 1 1 d . U . . .
H10 H 1.0442 0.1132 0.2417 0.046 Uiso 1 1 calc R . . . .
C11 C 1.1431(11) 0.2860(17) 0.3209(9) 0.042(4) Uani 1 1 d . . . . .
C12 C 1.1486(10) 0.3827(16) 0.3800(8) 0.036(4) Uani 1 1 d . . . . .
H12 H 1.2104 0.4550 0.4048 0.044 Uiso 1 1 calc R . . . .
C13 C 1.0625(10) 0.3734(16) 0.4029(7) 0.036(4) Uani 1 1 d . . . . .
H13 H 1.0679 0.4390 0.4434 0.043 Uiso 1 1 calc R . . . .
C14 C 0.8981(10) 0.2332(15) 0.4650(8) 0.034(4) Uani 1 1 d . . . . .
C15 C 0.8030(11) 0.2308(15) 0.4852(8) 0.032(3) Uani 1 1 d . . . . .
C16 C 0.7099(10) 0.3416(17) 0.4529(8) 0.036(4) Uani 1 1 d . . . . .
H16 H 0.7112 0.4189 0.4195 0.043 Uiso 1 1 calc R . . . .
C17 C 0.6186(13) 0.340(2) 0.4686(9) 0.057(5) Uani 1 1 d . . . . .
H17 H 0.5572 0.4128 0.4453 0.068 Uiso 1 1 calc R . . . .
C18 C 0.6185(17) 0.226(2) 0.5203(12) 0.069(5) Uani 1 1 d . U . . .
H18 H 0.5566 0.2215 0.5318 0.083 Uiso 1 1 calc R . . . .
C19 C 0.7094(18) 0.123(3) 0.5534(13) 0.087(6) Uani 1 1 d . U . . .
H19 H 0.7107 0.0490 0.5891 0.105 Uiso 1 1 calc R . . . .
C20 C 0.7996(16) 0.124(2) 0.5360(12) 0.064(5) Uani 1 1 d . . . . .
H20 H 0.8603 0.0506 0.5597 0.076 Uiso 1 1 calc R . . . .
C21 C 1.0266(13) 0.2110(18) 0.5425(9) 0.058(5) Uani 1 1 d . . . . .
H21A H 1.0825 0.1840 0.5254 0.088 Uiso 1 1 calc GR . . . .
H21B H 1.0243 0.1309 0.5764 0.088 Uiso 1 1 calc GR . . . .
H21C H 1.0526 0.3044 0.5737 0.088 Uiso 1 1 calc GR . . . .


_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
Br1 C1 1.902(11) . ?
Br2 C11 1.841(14) . ?
C1 C2 1.334(18) . ?
C1 C6 1.385(18) . ?
C2 H2 0.9300 . ?
C2 C3 1.370(16) . ?
C3 H3 0.9300 . ?
C3 C4 1.369(17) . ?
C4 C5 1.395(18) . ?
C4 C7 1.476(15) . ?
C5 H5 0.9300 . ?
C5 C6 1.377(16) . ?
C6 H6 0.9300 . ?
C7 C8 1.473(18) . ?
C7 C14 1.316(18) . ?
C8 C9 1.393(18) . ?
C8 C13 1.402(17) . ?
C9 H9 0.9300 . ?
C9 C10 1.383(19) . ?
C10 H10 0.9300 . ?
C10 C11 1.402(19) . ?
C11 C12 1.37(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.386(19) . ?
C13 H13 0.9300 . ?
C14 C15 1.461(19) . ?
C14 C21 1.547(17) . ?
C15 C16 1.410(18) . ?
C15 C20 1.35(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.35(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.39(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.34(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.36(2) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 Br1 119.4(9) . . ?
C2 C1 C6 123.0(10) . . ?
C6 C1 Br1 117.6(10) . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.7(11) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 118.8 . . ?
C4 C3 C2 122.5(12) . . ?
C4 C3 H3 118.8 . . ?
C3 C4 C5 116.8(11) . . ?
C3 C4 C7 122.3(12) . . ?
C5 C4 C7 120.9(10) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 C4 122.1(11) . . ?
C6 C5 H5 119.0 . . ?
C1 C6 H6 121.5 . . ?
C5 C6 C1 116.9(12) . . ?
C5 C6 H6 121.5 . . ?
C8 C7 C4 113.0(11) . . ?
C14 C7 C4 122.0(11) . . ?
C14 C7 C8 125.0(10) . . ?
C9 C8 C7 119.8(11) . . ?
C9 C8 C13 117.0(12) . . ?
C13 C8 C7 123.2(12) . . ?
C8 C9 H9 118.7 . . ?
C10 C9 C8 122.6(12) . . ?
C10 C9 H9 118.7 . . ?
C9 C10 H10 120.7 . . ?
C9 C10 C11 118.6(14) . . ?
C11 C10 H10 120.7 . . ?
C10 C11 Br2 120.5(12) . . ?
C12 C11 Br2 119.3(10) . . ?
C12 C11 C10 120.2(13) . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.4(12) . . ?
C13 C12 H12 119.8 . . ?
C8 C13 H13 119.4 . . ?
C12 C13 C8 121.2(13) . . ?
C12 C13 H13 119.4 . . ?
C7 C14 C15 122.8(11) . . ?
C7 C14 C21 124.8(12) . . ?
C15 C14 C21 112.4(12) . . ?
C16 C15 C14 121.1(13) . . ?
C20 C15 C14 122.4(13) . . ?
C20 C15 C16 116.5(14) . . ?
C15 C16 H16 118.8 . . ?
C17 C16 C15 122.4(15) . . ?
C17 C16 H16 118.8 . . ?
C16 C17 H17 120.7 . . ?
C16 C17 C18 118.7(15) . . ?
C18 C17 H17 120.7 . . ?
C17 C18 H18 120.5 . . ?
C19 C18 C17 119.0(18) . . ?
C19 C18 H18 120.5 . . ?
C18 C19 H19 119.1 . . ?
C18 C19 C20 122(2) . . ?
C20 C19 H19 119.1 . . ?
C15 C20 C19 121.5(17) . . ?
C15 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C14 C21 H21A 109.5 . . ?
C14 C21 H21B 109.5 . . ?
C14 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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
Br1 C1 C2 C3 -179.7(10) . . . . ?
Br1 C1 C6 C5 179.5(10) . . . . ?
Br2 C11 C12 C13 -179.1(10) . . . . ?
C1 C2 C3 C4 0(2) . . . . ?
C2 C1 C6 C5 -2(2) . . . . ?
C2 C3 C4 C5 -2(2) . . . . ?
C2 C3 C4 C7 -179.2(13) . . . . ?
C3 C4 C5 C6 1(2) . . . . ?
C3 C4 C7 C8 120.6(14) . . . . ?
C3 C4 C7 C14 -58.6(19) . . . . ?
C4 C5 C6 C1 0(2) . . . . ?
C4 C7 C8 C9 -51.7(16) . . . . ?
C4 C7 C8 C13 128.7(13) . . . . ?
C4 C7 C14 C15 -6(2) . . . . ?
C4 C7 C14 C21 173.3(13) . . . . ?
C5 C4 C7 C8 -57.0(16) . . . . ?
C5 C4 C7 C14 123.9(15) . . . . ?
C6 C1 C2 C3 2(2) . . . . ?
C7 C4 C5 C6 179.0(13) . . . . ?
C7 C8 C9 C10 -178.7(12) . . . . ?
C7 C8 C13 C12 179.3(12) . . . . ?
C7 C14 C15 C16 -46.7(19) . . . . ?
C7 C14 C15 C20 133.9(16) . . . . ?
C8 C7 C14 C15 174.9(12) . . . . ?
C8 C7 C14 C21 -6(2) . . . . ?
C8 C9 C10 C11 0(2) . . . . ?
C9 C8 C13 C12 -0.4(19) . . . . ?
C9 C10 C11 Br2 179.7(10) . . . . ?
C9 C10 C11 C12 -1(2) . . . . ?
C10 C11 C12 C13 1(2) . . . . ?
C11 C12 C13 C8 -1(2) . . . . ?
C13 C8 C9 C10 1(2) . . . . ?
C14 C7 C8 C9 127.4(14) . . . . ?
C14 C7 C8 C13 -52.2(19) . . . . ?
C14 C15 C16 C17 178.0(13) . . . . ?
C14 C15 C20 C19 -179.3(16) . . . . ?
C15 C16 C17 C18 2(2) . . . . ?
C16 C15 C20 C19 1(2) . . . . ?
C16 C17 C18 C19 1(3) . . . . ?
C17 C18 C19 C20 -2(3) . . . . ?
C18 C19 C20 C15 1(3) . . . . ?
C20 C15 C16 C17 -3(2) . . . . ?
C21 C14 C15 C16 133.9(13) . . . . ?
C21 C14 C15 C20 -45.5(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_mo_210517f_0m
_database_code_depnum_ccdc_archive 'CCDC 2094588'
loop_
_audit_author_name
_audit_author_address
TPFBrb
;Wuhan University
China
;
_audit_update_record             
;
2021-07-06 deposited with the CCDC.	2021-09-06 downloaded from the CCDC.
;
_audit_creation_date             2021-06-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H13 Br2 F3'
_chemical_formula_sum            'C21 H13 Br2 F3'
_chemical_formula_weight         482.13
_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'
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'

_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                   16.448(5)
_cell_length_b                   6.0973(19)
_cell_length_c                   19.528(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.073(5)
_cell_angle_gamma                90
_cell_volume                     1891.0(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4032
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.45
_cell_measurement_theta_min      2.56
_shelx_estimated_absorpt_T_max   0.919
_shelx_estimated_absorpt_T_min   0.672
_exptl_absorpt_coefficient_mu    4.316
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.3124
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1607 before and 0.0783 after correction.
The Ratio of minimum to maximum transmission is 0.4187.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.693
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0829
_diffrn_reflns_av_unetI/netI     0.0898
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            14925
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_min         2.160
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2480
_reflns_number_total             4519
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.831
_refine_diff_density_min         -0.909
_refine_diff_density_rms         0.130
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4519
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1429
_refine_ls_R_factor_gt           0.0685
_refine_ls_restrained_S_all      1.031
_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)+(0.1176P)²+1.3072P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1851
_refine_ls_wR_factor_ref         0.2271
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F3) \\sim Ueq, Uanis(F1) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(F3) \\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F2) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
3. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C14(H14),
 C15(H15), C16(H16), C18(H18), C19(H19), C21(H21)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Patterson Methods, followed by a Tangent Expansion (ShelXS). RE = 0.3, Nqual =  -1, Ralpha = 0.065
;
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
Br1 Br 0.18617(6) 1.32355(12) 0.60457(4) 0.0632(3) Uani 1 1 d . . . . .
C1 C 0.4183(5) 0.7268(16) 0.4201(3) 0.059(2) Uani 1 1 d . . . . .
F1 F 0.4553(19) 0.943(4) 0.4321(18) 0.086(7) Uani 0.46(6) 1 d . U P A 1
F1A F 0.475(2) 0.851(10) 0.4235(14) 0.145(17) Uani 0.54(6) 1 d . . P A 2
Br2 Br -0.03537(5) 0.83849(16) 0.09763(4) 0.0779(4) Uani 1 1 d . . . . .
C2 C 0.3645(4) 0.6757(9) 0.2880(3) 0.0355(13) Uani 1 1 d . . . . .
F2 F 0.400(2) 0.669(7) 0.4792(19) 0.075(9) Uani 0.46(6) 1 d . U P A 2
F2A F 0.398(2) 0.735(6) 0.4815(13) 0.069(7) Uani 0.54(6) 1 d . . P A 3
C3 C 0.3951(4) 0.4699(11) 0.2760(3) 0.0485(16) Uani 1 1 d . . . . .
H3 H 0.403761 0.363490 0.311288 0.058 Uiso 1 1 calc R U . . .
F3 F 0.4808(10) 0.633(7) 0.4157(8) 0.070(7) Uani 0.46(6) 1 d . U P A 1
F3A F 0.457(2) 0.512(7) 0.4205(10) 0.112(10) Uani 0.54(6) 1 d . . P A 2
C4 C 0.4127(4) 0.4231(13) 0.2125(4) 0.0561(18) Uani 1 1 d . . . . .
H4 H 0.432790 0.284967 0.204990 0.067 Uiso 1 1 calc R U . . .
C5 C 0.4010(4) 0.5773(15) 0.1604(4) 0.0593(19) Uani 1 1 d . . . . .
H5 H 0.412804 0.544134 0.117555 0.071 Uiso 1 1 calc R U . . .
C6 C 0.3721(5) 0.7789(13) 0.1711(4) 0.0546(18) Uani 1 1 d . . . . .
H6 H 0.364272 0.883781 0.135420 0.065 Uiso 1 1 calc R U . . .
C7 C 0.3540(4) 0.8302(10) 0.2343(3) 0.0417(14) Uani 1 1 d . . . . .
H7 H 0.334658 0.969815 0.240986 0.050 Uiso 1 1 calc R U . . .
C8 C 0.3438(4) 0.7380(10) 0.3550(3) 0.0367(13) Uani 1 1 d . . . . .
C9 C 0.2707(4) 0.8188(9) 0.3599(3) 0.0357(13) Uani 1 1 d . . . . .
C10 C 0.2550(4) 0.9297(10) 0.4228(3) 0.0358(13) Uani 1 1 d . . . . .
C11 C 0.2906(4) 1.1324(11) 0.4441(3) 0.0493(17) Uani 1 1 d . . . . .
H11 H 0.328322 1.192437 0.421203 0.059 Uiso 1 1 calc R U . . .
C12 C 0.2713(4) 1.2470(11) 0.4985(3) 0.0479(16) Uani 1 1 d . . . . .
H12 H 0.295390 1.383519 0.511950 0.057 Uiso 1 1 calc R U . . .
C13 C 0.2160(4) 1.1574(10) 0.5326(3) 0.0405(14) Uani 1 1 d . . . . .
C14 C 0.1800(4) 0.9568(10) 0.5134(3) 0.0429(15) Uani 1 1 d . . . . .
H14 H 0.143672 0.895815 0.537646 0.051 Uiso 1 1 calc R U . . .
C15 C 0.1983(4) 0.8467(9) 0.4576(3) 0.0397(14) Uani 1 1 d . . . . .
H15 H 0.172032 0.713447 0.443045 0.048 Uiso 1 1 calc R U . . .
C16 C 0.1417(4) 1.0002(10) 0.2825(3) 0.0421(15) Uani 1 1 d . . . . .
H16 H 0.152635 1.119797 0.313107 0.051 Uiso 1 1 calc R U . . .
C17 C 0.1938(4) 0.8192(9) 0.2971(3) 0.0350(13) Uani 1 1 d . . . . .
C18 C 0.1719(4) 0.6372(10) 0.2519(3) 0.0418(15) Uani 1 1 d . . . . .
H18 H 0.204260 0.510255 0.261514 0.050 Uiso 1 1 calc R U . . .
C19 C 0.1037(4) 0.6435(11) 0.1940(3) 0.0469(16) Uani 1 1 d . . . . .
H19 H 0.089824 0.521814 0.164548 0.056 Uiso 1 1 calc R U . . .
C20 C 0.0562(4) 0.8305(11) 0.1799(3) 0.0421(15) Uani 1 1 d . . . . .
C21 C 0.0731(4) 1.0080(11) 0.2231(3) 0.0464(16) Uani 1 1 d . . . . .
H21 H 0.039528 1.132730 0.213155 0.056 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
Br1 C13 1.898(6) . ?
C1 F1 1.45(3) . ?
C1 F1A 1.19(2) . ?
C1 F2 1.31(4) . ?
C1 F2A 1.32(3) . ?
C1 F3 1.20(2) . ?
C1 F3A 1.45(2) . ?
C1 C8 1.520(8) . ?
Br2 C20 1.896(6) . ?
C2 C3 1.394(8) . ?
C2 C7 1.387(8) . ?
C2 C8 1.484(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(9) . ?
C4 H4 0.9300 . ?
C4 C5 1.360(11) . ?
C5 H5 0.9300 . ?
C5 C6 1.353(11) . ?
C6 H6 0.9300 . ?
C6 C7 1.378(9) . ?
C7 H7 0.9300 . ?
C8 C9 1.326(8) . ?
C9 C10 1.482(8) . ?
C9 C17 1.516(8) . ?
C10 C11 1.384(9) . ?
C10 C15 1.385(8) . ?
C11 H11 0.9300 . ?
C11 C12 1.375(9) . ?
C12 H12 0.9300 . ?
C12 C13 1.373(9) . ?
C13 C14 1.368(9) . ?
C14 H14 0.9300 . ?
C14 C15 1.379(8) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.380(8) . ?
C16 C21 1.394(9) . ?
C17 C18 1.405(8) . ?
C18 H18 0.9300 . ?
C18 C19 1.371(9) . ?
C19 H19 0.9300 . ?
C19 C20 1.369(9) . ?
C20 C21 1.355(9) . ?
C21 H21 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 C1 C8 107.9(15) . . ?
F1A C1 F2 118(2) . . ?
F1A C1 F3A 104(2) . . ?
F1A C1 C8 117.7(16) . . ?
F2 C1 F3A 87.4(18) . . ?
F2 C1 C8 115.3(18) . . ?
F2A C1 C8 114.9(16) . . ?
F3 C1 F1 97(2) . . ?
F3 C1 C8 118.8(10) . . ?
F3A C1 C8 107.5(11) . . ?
C3 C2 C8 123.7(5) . . ?
C7 C2 C3 117.6(6) . . ?
C7 C2 C8 118.7(5) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.5(6) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.5(7) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.0(6) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 H6 119.7 . . ?
C5 C6 C7 120.7(7) . . ?
C7 C6 H6 119.7 . . ?
C2 C7 H7 119.7 . . ?
C6 C7 C2 120.6(6) . . ?
C6 C7 H7 119.7 . . ?
C2 C8 C1 114.0(5) . . ?
C9 C8 C1 120.3(5) . . ?
C9 C8 C2 125.4(5) . . ?
C8 C9 C10 125.9(5) . . ?
C8 C9 C17 121.6(5) . . ?
C10 C9 C17 112.4(5) . . ?
C11 C10 C9 120.4(5) . . ?
C11 C10 C15 117.6(5) . . ?
C15 C10 C9 121.7(5) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.5(6) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 H12 120.4 . . ?
C13 C12 C11 119.2(6) . . ?
C13 C12 H12 120.4 . . ?
C12 C13 Br1 118.6(5) . . ?
C14 C13 Br1 120.2(5) . . ?
C14 C13 C12 121.2(6) . . ?
C13 C14 H14 120.6 . . ?
C13 C14 C15 118.9(6) . . ?
C15 C14 H14 120.6 . . ?
C10 C15 H15 119.2 . . ?
C14 C15 C10 121.6(6) . . ?
C14 C15 H15 119.2 . . ?
C17 C16 H16 119.2 . . ?
C17 C16 C21 121.6(6) . . ?
C21 C16 H16 119.2 . . ?
C16 C17 C9 120.7(5) . . ?
C16 C17 C18 117.3(5) . . ?
C18 C17 C9 122.0(5) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 C17 121.1(6) . . ?
C19 C18 H18 119.5 . . ?
C18 C19 H19 120.3 . . ?
C20 C19 C18 119.4(6) . . ?
C20 C19 H19 120.3 . . ?
C19 C20 Br2 118.5(5) . . ?
C21 C20 Br2 119.7(5) . . ?
C21 C20 C19 121.8(6) . . ?
C16 C21 H21 120.6 . . ?
C20 C21 C16 118.8(6) . . ?
C20 C21 H21 120.6 . . ?

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
Br1 C13 C14 C15 175.5(5) . . . . ?
C1 C8 C9 C10 8.2(10) . . . . ?
C1 C8 C9 C17 -176.1(6) . . . . ?
F1 C1 C8 C2 94.5(14) . . . . ?
F1 C1 C8 C9 -79.1(14) . . . . ?
F1A C1 C8 C2 66(4) . . . . ?
F1A C1 C8 C9 -108(4) . . . . ?
Br2 C20 C21 C16 -178.8(5) . . . . ?
C2 C3 C4 C5 0.4(11) . . . . ?
C2 C8 C9 C10 -164.6(6) . . . . ?
C2 C8 C9 C17 11.0(9) . . . . ?
F2 C1 C8 C2 -147(2) . . . . ?
F2 C1 C8 C9 40(2) . . . . ?
F2A C1 C8 C2 -166.0(18) . . . . ?
F2A C1 C8 C9 20(2) . . . . ?
C3 C2 C7 C6 1.1(9) . . . . ?
C3 C2 C8 C1 60.7(8) . . . . ?
C3 C2 C8 C9 -126.1(7) . . . . ?
C3 C4 C5 C6 0.2(11) . . . . ?
F3 C1 C8 C2 -14(2) . . . . ?
F3 C1 C8 C9 173(2) . . . . ?
F3A C1 C8 C2 -51(2) . . . . ?
F3A C1 C8 C9 135(2) . . . . ?
C4 C5 C6 C7 -0.2(11) . . . . ?
C5 C6 C7 C2 -0.5(11) . . . . ?
C7 C2 C3 C4 -1.1(9) . . . . ?
C7 C2 C8 C1 -118.5(7) . . . . ?
C7 C2 C8 C9 54.7(9) . . . . ?
C8 C2 C3 C4 179.8(6) . . . . ?
C8 C2 C7 C6 -179.6(6) . . . . ?
C8 C9 C10 C11 67.9(9) . . . . ?
C8 C9 C10 C15 -118.7(7) . . . . ?
C8 C9 C17 C16 -137.5(6) . . . . ?
C8 C9 C17 C18 43.0(8) . . . . ?
C9 C10 C11 C12 174.4(6) . . . . ?
C9 C10 C15 C14 -176.0(6) . . . . ?
C9 C17 C18 C19 -177.7(6) . . . . ?
C10 C9 C17 C16 38.7(7) . . . . ?
C10 C9 C17 C18 -140.8(6) . . . . ?
C10 C11 C12 C13 0.5(11) . . . . ?
C11 C10 C15 C14 -2.4(9) . . . . ?
C11 C12 C13 Br1 -177.2(5) . . . . ?
C11 C12 C13 C14 0.0(11) . . . . ?
C12 C13 C14 C15 -1.6(10) . . . . ?
C13 C14 C15 C10 2.9(10) . . . . ?
C15 C10 C11 C12 0.7(10) . . . . ?
C16 C17 C18 C19 2.8(9) . . . . ?
C17 C9 C10 C11 -108.1(6) . . . . ?
C17 C9 C10 C15 65.3(7) . . . . ?
C17 C16 C21 C20 1.9(9) . . . . ?
C17 C18 C19 C20 0.1(10) . . . . ?
C18 C19 C20 Br2 177.8(5) . . . . ?
C18 C19 C20 C21 -2.2(10) . . . . ?
C19 C20 C21 C16 1.2(9) . . . . ?
C21 C16 C17 C9 176.7(5) . . . . ?
C21 C16 C17 C18 -3.8(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
