# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_4Br
_database_code_depnum_ccdc_archive 'CCDC 1887275'
loop_
_audit_author_name
_audit_author_address
'Ryonosuke Sato'
;Tokyo Institute of Technology
Japan
;
_audit_update_record             
;
2018-12-25 deposited with the CCDC.	2019-02-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        4Br4Ph
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C46 H26 Br4'
_chemical_formula_sum            'C46 H26 Br4'
_chemical_formula_weight         898.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   10.3811(3)
_cell_length_b                   13.2135(4)
_cell_length_c                   13.8306(4)
_cell_angle_alpha                81.924(2)
_cell_angle_beta                 77.158(2)
_cell_angle_gamma                72.986(2)
_cell_volume                     1762.94(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    20752
_cell_measurement_theta_min      3.288
_cell_measurement_theta_max      68.228

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.692
_exptl_crystal_F_000             884
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.099
_exptl_crystal_size_mid          0.048
_exptl_crystal_size_min          0.033
_exptl_absorpt_coefficient_mu    5.826
_shelx_estimated_absorpt_T_min   0.596
_shelx_estimated_absorpt_T_max   0.831
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.445
_exptl_absorpt_correction_T_max  0.831
_exptl_absorpt_process_details   'abscor T.Higashi RIGAKU'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rortating anode x-ray'
_diffrn_measurement_device_type  'RIGAKU VM-SPIDER'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            20752
_diffrn_reflns_av_unetI/netI     0.1285
_diffrn_reflns_av_R_equivalents  0.1139
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.288
_diffrn_reflns_theta_max         68.228
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             6332
_reflns_number_gt                3937
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       RAPID-AUTO
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        RAPID-AUTO
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0915P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6332
_refine_ls_number_parameters     451
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0905
_refine_ls_R_factor_gt           0.0685
_refine_ls_wR_factor_ref         0.1983
_refine_ls_wR_factor_gt          0.1592
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.30080(7) 0.13431(5) 0.83856(5) 0.0347(2) Uani 1 1 d . . . . .
C1 C 0.2836(6) 0.2521(5) 0.7416(4) 0.0297(15) Uani 1 1 d . . . . .
Br2 Br 0.06625(7) 0.36436(6) 0.88976(5) 0.0356(2) Uani 1 1 d . . . . .
C2 C 0.1830(6) 0.3500(5) 0.7631(4) 0.0323(15) Uani 1 1 d . . . . .
Br3 Br 0.79571(7) 0.62127(7) -0.21493(5) 0.0460(3) Uani 1 1 d . . . . .
C3 C 0.1700(6) 0.4342(5) 0.6931(4) 0.0295(15) Uani 1 1 d . . . . .
H3 H 0.100798 0.498134 0.708622 0.035 Uiso 1 1 calc R U . . .
Br4 Br 0.62418(8) 0.86537(6) -0.13748(5) 0.0493(3) Uani 1 1 d . . . . .
C4 C 0.2576(6) 0.4292(5) 0.5972(5) 0.0270(14) Uani 1 1 d . . . . .
C5 C 0.2438(6) 0.5124(5) 0.5233(4) 0.0283(15) Uani 1 1 d . . . . .
C6 C 0.3353(6) 0.5042(5) 0.4306(4) 0.0298(15) Uani 1 1 d . . . . .
C7 C 0.3319(6) 0.5879(5) 0.3556(4) 0.0326(16) Uani 1 1 d . . . . .
H7 H 0.263998 0.653248 0.367669 0.039 Uiso 1 1 calc R U . . .
C8 C 0.4230(6) 0.5802(5) 0.2641(4) 0.0291(15) Uani 1 1 d . . . . .
C9 C 0.4184(6) 0.6692(5) 0.1913(4) 0.0293(15) Uani 1 1 d . . . . .
C10 C 0.5149(6) 0.6600(5) 0.1041(5) 0.0299(15) Uani 1 1 d . . . . .
C11 C 0.5241(6) 0.7501(5) 0.0341(4) 0.0333(16) Uani 1 1 d . . . . .
H11 H 0.466260 0.818250 0.050484 0.040 Uiso 1 1 calc R U . . .
C12 C 0.6125(6) 0.7410(5) -0.0545(4) 0.0305(15) Uani 1 1 d . . . . .
C13 C 0.6945(6) 0.6389(6) -0.0828(5) 0.0348(16) Uani 1 1 d . . . . .
C14 C 0.6976(6) 0.5510(5) -0.0172(4) 0.0278(14) Uani 1 1 d . . . . .
H14 H 0.756282 0.484049 -0.036430 0.033 Uiso 1 1 calc R U . . .
C15 C 0.6126(6) 0.5585(5) 0.0814(4) 0.0323(16) Uani 1 1 d . . . . .
C16 C 0.6204(6) 0.4704(5) 0.1508(4) 0.0278(15) Uani 1 1 d . . . . .
C17 C 0.5272(6) 0.4805(5) 0.2444(4) 0.0269(14) Uani 1 1 d . . . . .
C18 C 0.5289(6) 0.3961(5) 0.3185(4) 0.0295(15) Uani 1 1 d . . . . .
H18 H 0.595546 0.330254 0.306133 0.035 Uiso 1 1 calc R U . . .
C19 C 0.4377(6) 0.4045(5) 0.4090(4) 0.0257(14) Uani 1 1 d . . . . .
C20 C 0.4463(6) 0.3161(5) 0.4817(4) 0.0254(14) Uani 1 1 d . . . . .
C21 C 0.3591(6) 0.3276(5) 0.5750(4) 0.0232(13) Uani 1 1 d . . . . .
C22 C 0.3657(6) 0.2414(5) 0.6505(4) 0.0283(14) Uani 1 1 d . . . . .
H22 H 0.429420 0.174654 0.636362 0.034 Uiso 1 1 calc R U . . .
C23 C 0.5373(6) 0.2086(5) 0.4545(4) 0.0283(15) Uani 1 1 d . . . . .
C24 C 0.6619(7) 0.1647(5) 0.4863(5) 0.0339(16) Uani 1 1 d . . . . .
H24 H 0.688986 0.202635 0.528193 0.041 Uiso 1 1 calc R U . . .
C25 C 0.7462(7) 0.0678(5) 0.4585(5) 0.0441(18) Uani 1 1 d . . . . .
H25 H 0.830062 0.038046 0.481667 0.053 Uiso 1 1 calc R U . . .
C26 C 0.7062(8) 0.0141(5) 0.3957(5) 0.0447(19) Uani 1 1 d . . . . .
H26 H 0.763884 -0.052496 0.374779 0.054 Uiso 1 1 calc R U . . .
C27 C 0.5839(7) 0.0567(5) 0.3636(5) 0.0430(18) Uani 1 1 d . . . . .
H27 H 0.556876 0.018686 0.321786 0.052 Uiso 1 1 calc R U . . .
C28 C 0.5006(7) 0.1534(5) 0.3915(5) 0.0389(17) Uani 1 1 d . . . . .
H28 H 0.417295 0.182878 0.367576 0.047 Uiso 1 1 calc R U . . .
C29 C 0.7239(7) 0.3668(5) 0.1302(4) 0.0270(14) Uani 1 1 d . . . . .
C30 C 0.6822(8) 0.2785(6) 0.1208(5) 0.0447(19) Uani 1 1 d . . . . .
H30 H 0.587234 0.285169 0.126370 0.054 Uiso 1 1 calc R U . . .
C31 C 0.7772(8) 0.1800(6) 0.1033(5) 0.051(2) Uani 1 1 d . . . . .
H31 H 0.746467 0.120928 0.096111 0.061 Uiso 1 1 calc R U . . .
C32 C 0.9133(8) 0.1685(6) 0.0965(5) 0.048(2) Uani 1 1 d . . . . .
H32 H 0.977928 0.101855 0.083692 0.058 Uiso 1 1 calc R U . . .
C33 C 0.9576(7) 0.2553(6) 0.1086(5) 0.0403(18) Uani 1 1 d . . . . .
H33 H 1.052350 0.247289 0.105647 0.048 Uiso 1 1 calc R U . . .
C34 C 0.8637(7) 0.3529(5) 0.1248(4) 0.0346(16) Uani 1 1 d . . . . .
H34 H 0.894979 0.411490 0.132502 0.042 Uiso 1 1 calc R U . . .
C35 C 0.3035(6) 0.7671(5) 0.2107(4) 0.0309(16) Uani 1 1 d . . . . .
C36 C 0.1784(8) 0.7732(6) 0.1880(6) 0.058(2) Uani 1 1 d . . . . .
H36 H 0.168244 0.716798 0.157233 0.070 Uiso 1 1 calc R U . . .
C37 C 0.0674(8) 0.8608(7) 0.2095(7) 0.067(3) Uani 1 1 d . . . . .
H37 H -0.018441 0.862275 0.195041 0.080 Uiso 1 1 calc R U . . .
C38 C 0.0783(7) 0.9446(6) 0.2510(5) 0.0463(19) Uani 1 1 d . . . . .
H38 H 0.001845 1.004673 0.264599 0.056 Uiso 1 1 calc R U . . .
C39 C 0.2017(7) 0.9403(6) 0.2724(5) 0.0438(18) Uani 1 1 d . . . . .
H39 H 0.211077 0.997494 0.302442 0.053 Uiso 1 1 calc R U . . .
C40 C 0.3140(7) 0.8534(5) 0.2508(5) 0.0393(17) Uani 1 1 d . . . . .
H40 H 0.400022 0.853456 0.263881 0.047 Uiso 1 1 calc R U . . .
C41 C 0.1290(6) 0.6113(5) 0.5409(4) 0.0259(14) Uani 1 1 d . . . . .
C42 C 0.1198(6) 0.6792(5) 0.6118(4) 0.0274(14) Uani 1 1 d . . . . .
H42 H 0.187895 0.662454 0.651847 0.033 Uiso 1 1 calc R U . . .
C43 C 0.0127(6) 0.7712(5) 0.6250(4) 0.0315(15) Uani 1 1 d . . . . .
H43 H 0.009513 0.817529 0.672645 0.038 Uiso 1 1 calc R U . . .
C44 C -0.0888(7) 0.7957(5) 0.5696(5) 0.0377(17) Uani 1 1 d . . . . .
H44 H -0.163802 0.857327 0.580292 0.045 Uiso 1 1 calc R U . . .
C45 C -0.0801(7) 0.7291(5) 0.4980(5) 0.0408(18) Uani 1 1 d . . . . .
H45 H -0.149311 0.746706 0.458919 0.049 Uiso 1 1 calc R U . . .
C46 C 0.0258(6) 0.6382(5) 0.4820(5) 0.0331(16) Uani 1 1 d . . . . .
H46 H 0.029888 0.594098 0.432116 0.040 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 C1 1.900(6) . ?
C1 C22 1.355(8) . ?
C1 C2 1.425(8) . ?
Br2 C2 1.894(6) . ?
C2 C3 1.365(8) . ?
Br3 C13 1.902(6) . ?
C3 C4 1.430(8) . ?
C3 H3 0.9500 . ?
Br4 C12 1.887(6) . ?
C4 C5 1.390(8) . ?
C4 C21 1.467(8) . ?
C5 C6 1.412(8) . ?
C5 C41 1.495(8) . ?
C6 C7 1.404(8) . ?
C6 C19 1.451(8) . ?
C7 C8 1.398(8) . ?
C7 H7 0.9500 . ?
C8 C9 1.433(8) . ?
C8 C17 1.455(8) . ?
C9 C10 1.381(8) . ?
C9 C35 1.489(8) . ?
C10 C11 1.437(8) . ?
C10 C15 1.452(8) . ?
C11 C12 1.355(8) . ?
C11 H11 0.9500 . ?
C12 C13 1.423(9) . ?
C13 C14 1.368(8) . ?
C14 C15 1.449(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.396(8) . ?
C16 C17 1.430(8) . ?
C16 C29 1.491(8) . ?
C17 C18 1.403(8) . ?
C18 C19 1.387(8) . ?
C18 H18 0.9500 . ?
C19 C20 1.426(8) . ?
C20 C21 1.401(8) . ?
C20 C23 1.503(8) . ?
C21 C22 1.429(8) . ?
C22 H22 0.9500 . ?
C23 C28 1.388(8) . ?
C23 C24 1.395(8) . ?
C24 C25 1.374(8) . ?
C24 H24 0.9500 . ?
C25 C26 1.392(9) . ?
C25 H25 0.9500 . ?
C26 C27 1.374(9) . ?
C26 H26 0.9500 . ?
C27 C28 1.368(8) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 C30 1.388(8) . ?
C29 C34 1.395(8) . ?
C30 C31 1.399(9) . ?
C30 H30 0.9500 . ?
C31 C32 1.360(10) . ?
C31 H31 0.9500 . ?
C32 C33 1.397(10) . ?
C32 H32 0.9500 . ?
C33 C34 1.382(8) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C35 C40 1.378(8) . ?
C35 C36 1.380(9) . ?
C36 C37 1.385(9) . ?
C36 H36 0.9500 . ?
C37 C38 1.360(10) . ?
C37 H37 0.9500 . ?
C38 C39 1.361(9) . ?
C38 H38 0.9500 . ?
C39 C40 1.387(9) . ?
C39 H39 0.9500 . ?
C40 H40 0.9500 . ?
C41 C42 1.390(7) . ?
C41 C46 1.422(8) . ?
C42 C43 1.389(8) . ?
C42 H42 0.9500 . ?
C43 C44 1.375(8) . ?
C43 H43 0.9500 . ?
C44 C45 1.386(8) . ?
C44 H44 0.9500 . ?
C45 C46 1.376(8) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C22 C1 C2 120.1(6) . . ?
C22 C1 Br1 119.3(5) . . ?
C2 C1 Br1 120.6(5) . . ?
C3 C2 C1 120.5(6) . . ?
C3 C2 Br2 119.3(5) . . ?
C1 C2 Br2 120.2(5) . . ?
C2 C3 C4 121.9(6) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 123.2(6) . . ?
C5 C4 C21 119.5(5) . . ?
C3 C4 C21 117.1(5) . . ?
C4 C5 C6 120.9(6) . . ?
C4 C5 C41 119.8(5) . . ?
C6 C5 C41 119.3(5) . . ?
C7 C6 C5 123.5(6) . . ?
C7 C6 C19 117.0(6) . . ?
C5 C6 C19 119.6(6) . . ?
C8 C7 C6 123.6(6) . . ?
C8 C7 H7 118.2 . . ?
C6 C7 H7 118.2 . . ?
C7 C8 C9 121.4(6) . . ?
C7 C8 C17 118.8(6) . . ?
C9 C8 C17 119.8(6) . . ?
C10 C9 C8 119.6(6) . . ?
C10 C9 C35 122.3(6) . . ?
C8 C9 C35 118.1(5) . . ?
C9 C10 C11 121.5(6) . . ?
C9 C10 C15 120.6(6) . . ?
C11 C10 C15 117.9(6) . . ?
C12 C11 C10 122.1(6) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C11 C12 C13 119.9(6) . . ?
C11 C12 Br4 118.7(5) . . ?
C13 C12 Br4 121.5(5) . . ?
C14 C13 C12 120.8(6) . . ?
C14 C13 Br3 118.6(5) . . ?
C12 C13 Br3 120.5(5) . . ?
C13 C14 C15 120.8(6) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C16 C15 C14 121.3(6) . . ?
C16 C15 C10 121.1(6) . . ?
C14 C15 C10 117.6(6) . . ?
C15 C16 C17 118.9(6) . . ?
C15 C16 C29 121.7(5) . . ?
C17 C16 C29 119.4(5) . . ?
C18 C17 C16 122.5(6) . . ?
C18 C17 C8 117.7(5) . . ?
C16 C17 C8 119.8(6) . . ?
C19 C18 C17 123.0(6) . . ?
C19 C18 H18 118.5 . . ?
C17 C18 H18 118.5 . . ?
C18 C19 C20 120.2(6) . . ?
C18 C19 C6 119.9(6) . . ?
C20 C19 C6 119.8(5) . . ?
C21 C20 C19 119.6(5) . . ?
C21 C20 C23 120.1(5) . . ?
C19 C20 C23 119.9(5) . . ?
C20 C21 C22 121.4(6) . . ?
C20 C21 C4 120.3(5) . . ?
C22 C21 C4 118.3(5) . . ?
C1 C22 C21 121.9(6) . . ?
C1 C22 H22 119.1 . . ?
C21 C22 H22 119.1 . . ?
C28 C23 C24 118.6(6) . . ?
C28 C23 C20 119.4(5) . . ?
C24 C23 C20 121.9(6) . . ?
C25 C24 C23 121.5(6) . . ?
C25 C24 H24 119.3 . . ?
C23 C24 H24 119.3 . . ?
C24 C25 C26 118.5(7) . . ?
C24 C25 H25 120.7 . . ?
C26 C25 H25 120.7 . . ?
C27 C26 C25 120.5(6) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C28 C27 C26 120.6(6) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C27 C28 C23 120.3(6) . . ?
C27 C28 H28 119.9 . . ?
C23 C28 H28 119.9 . . ?
C30 C29 C34 117.5(6) . . ?
C30 C29 C16 120.3(6) . . ?
C34 C29 C16 122.1(6) . . ?
C29 C30 C31 121.3(7) . . ?
C29 C30 H30 119.3 . . ?
C31 C30 H30 119.3 . . ?
C32 C31 C30 120.2(7) . . ?
C32 C31 H31 119.9 . . ?
C30 C31 H31 119.9 . . ?
C31 C32 C33 119.6(7) . . ?
C31 C32 H32 120.2 . . ?
C33 C32 H32 120.2 . . ?
C34 C33 C32 120.1(7) . . ?
C34 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
C33 C34 C29 121.2(7) . . ?
C33 C34 H34 119.4 . . ?
C29 C34 H34 119.4 . . ?
C40 C35 C36 117.1(6) . . ?
C40 C35 C9 123.7(6) . . ?
C36 C35 C9 119.2(6) . . ?
C35 C36 C37 120.7(7) . . ?
C35 C36 H36 119.6 . . ?
C37 C36 H36 119.6 . . ?
C38 C37 C36 121.6(7) . . ?
C38 C37 H37 119.2 . . ?
C36 C37 H37 119.2 . . ?
C37 C38 C39 118.3(7) . . ?
C37 C38 H38 120.9 . . ?
C39 C38 H38 120.9 . . ?
C38 C39 C40 120.8(7) . . ?
C38 C39 H39 119.6 . . ?
C40 C39 H39 119.6 . . ?
C35 C40 C39 121.4(6) . . ?
C35 C40 H40 119.3 . . ?
C39 C40 H40 119.3 . . ?
C42 C41 C46 118.4(5) . . ?
C42 C41 C5 122.7(5) . . ?
C46 C41 C5 119.0(5) . . ?
C43 C42 C41 121.0(5) . . ?
C43 C42 H42 119.5 . . ?
C41 C42 H42 119.5 . . ?
C44 C43 C42 120.5(6) . . ?
C44 C43 H43 119.7 . . ?
C42 C43 H43 119.7 . . ?
C43 C44 C45 119.0(6) . . ?
C43 C44 H44 120.5 . . ?
C45 C44 H44 120.5 . . ?
C46 C45 C44 122.0(6) . . ?
C46 C45 H45 119.0 . . ?
C44 C45 H45 119.0 . . ?
C45 C46 C41 119.1(6) . . ?
C45 C46 H46 120.4 . . ?
C41 C46 H46 120.4 . . ?

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
C22 C1 C2 C3 -1.2(9) . . . . ?
Br1 C1 C2 C3 -179.5(5) . . . . ?
C22 C1 C2 Br2 179.0(5) . . . . ?
Br1 C1 C2 Br2 0.8(7) . . . . ?
C1 C2 C3 C4 -1.5(9) . . . . ?
Br2 C2 C3 C4 178.3(4) . . . . ?
C2 C3 C4 C5 177.7(6) . . . . ?
C2 C3 C4 C21 2.5(9) . . . . ?
C3 C4 C5 C6 178.4(6) . . . . ?
C21 C4 C5 C6 -6.6(9) . . . . ?
C3 C4 C5 C41 -2.8(9) . . . . ?
C21 C4 C5 C41 172.2(5) . . . . ?
C4 C5 C6 C7 -175.8(6) . . . . ?
C41 C5 C6 C7 5.4(9) . . . . ?
C4 C5 C6 C19 5.4(9) . . . . ?
C41 C5 C6 C19 -173.4(5) . . . . ?
C5 C6 C7 C8 179.5(6) . . . . ?
C19 C6 C7 C8 -1.6(9) . . . . ?
C6 C7 C8 C9 -177.7(6) . . . . ?
C6 C7 C8 C17 0.2(9) . . . . ?
C7 C8 C9 C10 176.5(6) . . . . ?
C17 C8 C9 C10 -1.4(8) . . . . ?
C7 C8 C9 C35 -7.0(9) . . . . ?
C17 C8 C9 C35 175.1(5) . . . . ?
C8 C9 C10 C11 -172.9(5) . . . . ?
C35 C9 C10 C11 10.7(9) . . . . ?
C8 C9 C10 C15 5.8(8) . . . . ?
C35 C9 C10 C15 -170.6(6) . . . . ?
C9 C10 C11 C12 -175.8(6) . . . . ?
C15 C10 C11 C12 5.4(9) . . . . ?
C10 C11 C12 C13 3.5(9) . . . . ?
C10 C11 C12 Br4 -176.3(4) . . . . ?
C11 C12 C13 C14 -7.9(9) . . . . ?
Br4 C12 C13 C14 171.9(5) . . . . ?
C11 C12 C13 Br3 169.3(5) . . . . ?
Br4 C12 C13 Br3 -11.0(7) . . . . ?
C12 C13 C14 C15 3.0(9) . . . . ?
Br3 C13 C14 C15 -174.3(4) . . . . ?
C13 C14 C15 C16 -176.5(6) . . . . ?
C13 C14 C15 C10 5.9(9) . . . . ?
C9 C10 C15 C16 -6.3(9) . . . . ?
C11 C10 C15 C16 172.5(6) . . . . ?
C9 C10 C15 C14 171.3(6) . . . . ?
C11 C10 C15 C14 -9.9(8) . . . . ?
C14 C15 C16 C17 -175.5(5) . . . . ?
C10 C15 C16 C17 2.0(9) . . . . ?
C14 C15 C16 C29 5.0(9) . . . . ?
C10 C15 C16 C29 -177.5(5) . . . . ?
C15 C16 C17 C18 -179.5(5) . . . . ?
C29 C16 C17 C18 0.0(9) . . . . ?
C15 C16 C17 C8 2.4(8) . . . . ?
C29 C16 C17 C8 -178.0(5) . . . . ?
C7 C8 C17 C18 1.1(8) . . . . ?
C9 C8 C17 C18 179.0(5) . . . . ?
C7 C8 C17 C16 179.2(6) . . . . ?
C9 C8 C17 C16 -2.8(8) . . . . ?
C16 C17 C18 C19 -179.0(5) . . . . ?
C8 C17 C18 C19 -0.9(8) . . . . ?
C17 C18 C19 C20 -179.0(5) . . . . ?
C17 C18 C19 C6 -0.5(9) . . . . ?
C7 C6 C19 C18 1.7(8) . . . . ?
C5 C6 C19 C18 -179.4(5) . . . . ?
C7 C6 C19 C20 -179.7(5) . . . . ?
C5 C6 C19 C20 -0.8(8) . . . . ?
C18 C19 C20 C21 176.1(5) . . . . ?
C6 C19 C20 C21 -2.4(8) . . . . ?
C18 C19 C20 C23 -10.6(8) . . . . ?
C6 C19 C20 C23 170.9(5) . . . . ?
C19 C20 C21 C22 -179.2(5) . . . . ?
C23 C20 C21 C22 7.5(9) . . . . ?
C19 C20 C21 C4 1.3(8) . . . . ?
C23 C20 C21 C4 -172.1(5) . . . . ?
C5 C4 C21 C20 3.3(8) . . . . ?
C3 C4 C21 C20 178.6(5) . . . . ?
C5 C4 C21 C22 -176.3(5) . . . . ?
C3 C4 C21 C22 -1.0(8) . . . . ?
C2 C1 C22 C21 2.8(9) . . . . ?
Br1 C1 C22 C21 -179.0(4) . . . . ?
C20 C21 C22 C1 178.8(6) . . . . ?
C4 C21 C22 C1 -1.6(9) . . . . ?
C21 C20 C23 C28 102.6(7) . . . . ?
C19 C20 C23 C28 -70.7(8) . . . . ?
C21 C20 C23 C24 -80.9(8) . . . . ?
C19 C20 C23 C24 105.8(7) . . . . ?
C28 C23 C24 C25 -1.5(9) . . . . ?
C20 C23 C24 C25 -178.0(6) . . . . ?
C23 C24 C25 C26 1.2(10) . . . . ?
C24 C25 C26 C27 -1.0(11) . . . . ?
C25 C26 C27 C28 1.2(11) . . . . ?
C26 C27 C28 C23 -1.5(10) . . . . ?
C24 C23 C28 C27 1.7(10) . . . . ?
C20 C23 C28 C27 178.2(6) . . . . ?
C15 C16 C29 C30 -113.7(7) . . . . ?
C17 C16 C29 C30 66.8(8) . . . . ?
C15 C16 C29 C34 69.8(8) . . . . ?
C17 C16 C29 C34 -109.8(7) . . . . ?
C34 C29 C30 C31 -2.1(9) . . . . ?
C16 C29 C30 C31 -178.8(6) . . . . ?
C29 C30 C31 C32 1.0(11) . . . . ?
C30 C31 C32 C33 0.9(11) . . . . ?
C31 C32 C33 C34 -1.6(10) . . . . ?
C32 C33 C34 C29 0.4(9) . . . . ?
C30 C29 C34 C33 1.4(9) . . . . ?
C16 C29 C34 C33 178.0(5) . . . . ?
C10 C9 C35 C40 -86.3(8) . . . . ?
C8 C9 C35 C40 97.4(7) . . . . ?
C10 C9 C35 C36 93.9(8) . . . . ?
C8 C9 C35 C36 -82.5(8) . . . . ?
C40 C35 C36 C37 -3.1(12) . . . . ?
C9 C35 C36 C37 176.8(7) . . . . ?
C35 C36 C37 C38 1.9(14) . . . . ?
C36 C37 C38 C39 -0.8(13) . . . . ?
C37 C38 C39 C40 1.2(12) . . . . ?
C36 C35 C40 C39 3.4(10) . . . . ?
C9 C35 C40 C39 -176.4(6) . . . . ?
C38 C39 C40 C35 -2.5(11) . . . . ?
C4 C5 C41 C42 65.9(8) . . . . ?
C6 C5 C41 C42 -115.2(7) . . . . ?
C4 C5 C41 C46 -115.1(7) . . . . ?
C6 C5 C41 C46 63.7(8) . . . . ?
C46 C41 C42 C43 0.0(9) . . . . ?
C5 C41 C42 C43 179.0(6) . . . . ?
C41 C42 C43 C44 1.6(9) . . . . ?
C42 C43 C44 C45 -2.2(10) . . . . ?
C43 C44 C45 C46 1.2(10) . . . . ?
C44 C45 C46 C41 0.5(10) . . . . ?
C42 C41 C46 C45 -1.1(9) . . . . ?
C5 C41 C46 C45 179.9(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C3 H3 Br3 0.95 3.13 3.986(6) 151.3 1_456 yes

_refine_diff_density_max         2.259
_refine_diff_density_min         -1.648
_refine_diff_density_rms         0.180



####################################################################### 
# 
# 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_4Cl
_database_code_depnum_ccdc_archive 'CCDC 1887276'
loop_
_audit_author_name
_audit_author_address
'Ryonosuke Sato'
;Tokyo Institute of Technology
Japan
;
_audit_update_record             
;
2018-12-25 deposited with the CCDC.	2019-02-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        4Cl4Ph
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C46 H26 Cl4'
_chemical_formula_sum            'C46 H26 Cl4'
_chemical_formula_weight         720.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.3770(13)
_cell_length_b                   12.874(2)
_cell_length_c                   13.3509(17)
_cell_angle_alpha                86.033(6)
_cell_angle_beta                 77.911(4)
_cell_angle_gamma                74.579(5)
_cell_volume                     1681.1(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    11849
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      27.52

_exptl_crystal_description       platelet
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_F_000             740
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.122
_exptl_crystal_size_mid          0.071
_exptl_crystal_size_min          0.031
_exptl_absorpt_coefficient_mu    0.388
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.648
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   'Absorption was corrected by ABSCOR'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode X-ray tube'
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID IP Area Detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16286
_diffrn_reflns_av_unetI/netI     0.1035
_diffrn_reflns_av_R_equivalents  0.0693
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.008
_diffrn_reflns_theta_max         27.470
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             7546
_reflns_number_gt                4618
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'PROCESS-AUTO (Rigaku, 1998)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1321P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7546
_refine_ls_number_parameters     451
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1153
_refine_ls_R_factor_gt           0.0694
_refine_ls_wR_factor_ref         0.2304
_refine_ls_wR_factor_gt          0.1680
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.29370(9) 0.16047(8) 0.84171(7) 0.0222(2) Uani 1 1 d . . . . .
Cl2 Cl 0.63390(10) 0.81626(9) -0.14746(8) 0.0270(3) Uani 1 1 d . . . . .
Cl3 Cl 0.07447(9) 0.38005(8) 0.88869(7) 0.0234(2) Uani 1 1 d . . . . .
Cl4 Cl 0.81407(9) 0.58409(9) -0.21558(7) 0.0256(3) Uani 1 1 d . . . . .
C1 C 0.6230(4) 0.7059(3) -0.0659(3) 0.0216(8) Uani 1 1 d . . . . .
C2 C 0.5305(4) 0.7199(3) 0.0217(3) 0.0200(8) Uani 1 1 d . . . . .
H2 H 0.468229 0.788494 0.035876 0.024 Uiso 1 1 calc R U . . .
C3 C 0.5234(4) 0.6329(3) 0.0953(3) 0.0174(8) Uani 1 1 d . . . . .
C4 C 0.4251(4) 0.6475(3) 0.1842(3) 0.0207(8) Uani 1 1 d . . . . .
C5 C 0.4291(4) 0.5618(3) 0.2598(3) 0.0183(8) Uani 1 1 d . . . . .
C6 C 0.3394(4) 0.5757(3) 0.3526(3) 0.0195(8) Uani 1 1 d . . . . .
H6 H 0.272657 0.642567 0.364843 0.023 Uiso 1 1 calc R U . . .
C7 C 0.3411(4) 0.4956(3) 0.4310(3) 0.0201(8) Uani 1 1 d . . . . .
C8 C 0.2504(4) 0.5121(3) 0.5248(3) 0.0189(8) Uani 1 1 d . . . . .
C9 C 0.2640(4) 0.4315(3) 0.6031(3) 0.0208(8) Uani 1 1 d . . . . .
C10 C 0.1754(4) 0.4427(3) 0.6980(3) 0.0198(8) Uani 1 1 d . . . . .
H10 H 0.105769 0.507737 0.712290 0.024 Uiso 1 1 calc R U . . .
C11 C 0.1854(4) 0.3630(3) 0.7709(3) 0.0231(8) Uani 1 1 d . . . . .
C12 C 0.2868(4) 0.2635(3) 0.7497(3) 0.0196(8) Uani 1 1 d . . . . .
C13 C 0.3736(4) 0.2473(3) 0.6582(3) 0.0195(8) Uani 1 1 d . . . . .
H13 H 0.438694 0.179799 0.644761 0.023 Uiso 1 1 calc R U . . .
C14 C 0.3689(4) 0.3314(3) 0.5801(3) 0.0190(8) Uani 1 1 d . . . . .
C15 C 0.4546(4) 0.3116(3) 0.4854(3) 0.0203(8) Uani 1 1 d . . . . .
C16 C 0.4472(4) 0.3950(3) 0.4087(3) 0.0193(8) Uani 1 1 d . . . . .
C17 C 0.5374(4) 0.3809(3) 0.3159(3) 0.0195(8) Uani 1 1 d . . . . .
H17 H 0.604505 0.314235 0.303858 0.023 Uiso 1 1 calc R U . . .
C18 C 0.5348(4) 0.4617(3) 0.2369(3) 0.0196(8) Uani 1 1 d . . . . .
C19 C 0.6294(4) 0.4462(3) 0.1448(3) 0.0207(8) Uani 1 1 d . . . . .
C20 C 0.6252(4) 0.5302(3) 0.0712(3) 0.0210(8) Uani 1 1 d . . . . .
C21 C 0.7116(4) 0.5181(3) -0.0262(3) 0.0205(8) Uani 1 1 d . . . . .
H21 H 0.771590 0.449557 -0.045132 0.025 Uiso 1 1 calc R U . . .
C22 C 0.7112(4) 0.6021(3) -0.0939(3) 0.0236(8) Uani 1 1 d . . . . .
C23 C 0.3093(4) 0.7466(3) 0.2036(3) 0.0196(8) Uani 1 1 d . . . . .
C24 C 0.3288(4) 0.8461(3) 0.2215(3) 0.0228(8) Uani 1 1 d . . . . .
H24 H 0.418385 0.852772 0.219138 0.027 Uiso 1 1 calc R U . . .
C25 C 0.2176(4) 0.9366(4) 0.2430(3) 0.0264(9) Uani 1 1 d . . . . .
H25 H 0.231972 1.003966 0.255564 0.032 Uiso 1 1 calc R U . . .
C26 C 0.0864(4) 0.9279(4) 0.2460(3) 0.0281(9) Uani 1 1 d . . . . .
H26 H 0.010981 0.989108 0.261236 0.034 Uiso 1 1 calc R U . . .
C27 C 0.0652(4) 0.8301(4) 0.2269(3) 0.0289(10) Uani 1 1 d . . . . .
H27 H -0.024500 0.824534 0.227924 0.035 Uiso 1 1 calc R U . . .
C28 C 0.1756(4) 0.7397(4) 0.2062(3) 0.0231(8) Uani 1 1 d . . . . .
H28 H 0.160256 0.672706 0.193602 0.028 Uiso 1 1 calc R U . . .
C29 C 0.1319(4) 0.6103(3) 0.5428(3) 0.0192(8) Uani 1 1 d . . . . .
C30 C 0.1165(4) 0.6832(3) 0.6191(3) 0.0213(8) Uani 1 1 d . . . . .
H30 H 0.183266 0.672033 0.660540 0.026 Uiso 1 1 calc R U . . .
C31 C 0.0044(4) 0.7726(4) 0.6357(3) 0.0259(9) Uani 1 1 d . . . . .
H31 H -0.005788 0.821315 0.688826 0.031 Uiso 1 1 calc R U . . .
C32 C -0.0927(4) 0.7904(4) 0.5742(3) 0.0267(9) Uani 1 1 d . . . . .
H32 H -0.169085 0.851400 0.585293 0.032 Uiso 1 1 calc R U . . .
C33 C -0.0780(4) 0.7196(4) 0.4974(3) 0.0264(9) Uani 1 1 d . . . . .
H33 H -0.145122 0.731650 0.456246 0.032 Uiso 1 1 calc R U . . .
C34 C 0.0348(4) 0.6301(3) 0.4793(3) 0.0190(8) Uani 1 1 d . . . . .
H34 H 0.045868 0.582955 0.424629 0.023 Uiso 1 1 calc R U . . .
C35 C 0.5495(4) 0.2039(3) 0.4591(3) 0.0202(8) Uani 1 1 d . . . . .
C36 C 0.5218(5) 0.1416(4) 0.3893(3) 0.0285(9) Uani 1 1 d . . . . .
H36 H 0.442727 0.168118 0.360511 0.034 Uiso 1 1 calc R U . . .
C37 C 0.6080(5) 0.0411(4) 0.3612(4) 0.0356(11) Uani 1 1 d . . . . .
H37 H 0.588171 -0.000820 0.313416 0.043 Uiso 1 1 calc R U . . .
C38 C 0.7242(5) 0.0021(4) 0.4037(4) 0.0395(12) Uani 1 1 d . . . . .
H38 H 0.782852 -0.066953 0.385046 0.047 Uiso 1 1 calc R U . . .
C39 C 0.7545(4) 0.0628(4) 0.4723(4) 0.0323(11) Uani 1 1 d . . . . .
H39 H 0.834413 0.036149 0.500114 0.039 Uiso 1 1 calc R U . . .
C40 C 0.6669(4) 0.1639(4) 0.5008(3) 0.0255(9) Uani 1 1 d . . . . .
H40 H 0.686947 0.205669 0.548617 0.031 Uiso 1 1 calc R U . . .
C41 C 0.7391(4) 0.3425(3) 0.1243(3) 0.0204(8) Uani 1 1 d . . . . .
C42 C 0.7068(4) 0.2434(4) 0.1237(3) 0.0238(9) Uani 1 1 d . . . . .
H42 H 0.613854 0.241813 0.135783 0.029 Uiso 1 1 calc R U . . .
C43 C 0.8079(4) 0.1480(4) 0.1058(3) 0.0291(9) Uani 1 1 d . . . . .
H43 H 0.783944 0.081838 0.105077 0.035 Uiso 1 1 calc R U . . .
C44 C 0.9451(4) 0.1490(4) 0.0887(3) 0.0288(9) Uani 1 1 d . . . . .
H44 H 1.014572 0.083751 0.075131 0.035 Uiso 1 1 calc R U . . .
C45 C 0.9791(4) 0.2446(4) 0.0915(3) 0.0269(9) Uani 1 1 d . . . . .
H45 H 1.072249 0.245365 0.081533 0.032 Uiso 1 1 calc R U . . .
C46 C 0.8769(4) 0.3409(4) 0.1091(3) 0.0227(8) Uani 1 1 d . . . . .
H46 H 0.901633 0.406622 0.110841 0.027 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
Cl1 C12 1.741(4) . ?
Cl2 C1 1.743(4) . ?
Cl3 C11 1.733(4) . ?
Cl4 C22 1.739(4) . ?
C1 C2 1.338(6) . ?
C1 C22 1.427(6) . ?
C2 C3 1.444(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.381(5) . ?
C3 C20 1.463(6) . ?
C4 C5 1.440(5) . ?
C4 C23 1.496(5) . ?
C5 C6 1.377(5) . ?
C5 C18 1.456(5) . ?
C6 C7 1.417(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.391(5) . ?
C7 C16 1.460(6) . ?
C8 C9 1.423(5) . ?
C8 C29 1.502(5) . ?
C9 C10 1.392(6) . ?
C9 C14 1.453(6) . ?
C10 C11 1.363(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.428(6) . ?
C12 C13 1.350(5) . ?
C13 C14 1.448(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.381(5) . ?
C15 C16 1.429(5) . ?
C15 C35 1.487(6) . ?
C16 C17 1.379(5) . ?
C17 C18 1.427(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.393(6) . ?
C19 C20 1.409(6) . ?
C19 C41 1.505(6) . ?
C20 C21 1.409(6) . ?
C21 C22 1.361(6) . ?
C21 H21 0.9500 . ?
C23 C24 1.393(6) . ?
C23 C28 1.407(5) . ?
C24 C25 1.401(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.388(6) . ?
C25 H25 0.9500 . ?
C26 C27 1.382(7) . ?
C26 H26 0.9500 . ?
C27 C28 1.395(6) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 C30 1.390(6) . ?
C29 C34 1.411(5) . ?
C30 C31 1.394(6) . ?
C30 H30 0.9500 . ?
C31 C32 1.392(6) . ?
C31 H31 0.9500 . ?
C32 C33 1.377(7) . ?
C32 H32 0.9500 . ?
C33 C34 1.400(6) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C35 C36 1.390(6) . ?
C35 C40 1.403(6) . ?
C36 C37 1.387(7) . ?
C36 H36 0.9500 . ?
C37 C38 1.397(7) . ?
C37 H37 0.9500 . ?
C38 C39 1.378(8) . ?
C38 H38 0.9500 . ?
C39 C40 1.401(6) . ?
C39 H39 0.9500 . ?
C40 H40 0.9500 . ?
C41 C46 1.397(5) . ?
C41 C42 1.402(6) . ?
C42 C43 1.384(6) . ?
C42 H42 0.9500 . ?
C43 C44 1.397(6) . ?
C43 H43 0.9500 . ?
C44 C45 1.373(7) . ?
C44 H44 0.9500 . ?
C45 C46 1.398(6) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C22 121.0(4) . . ?
C2 C1 Cl2 119.1(3) . . ?
C22 C1 Cl2 119.8(3) . . ?
C1 C2 C3 121.4(4) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C4 C3 C2 120.9(4) . . ?
C4 C3 C20 122.3(3) . . ?
C2 C3 C20 116.9(3) . . ?
C3 C4 C5 119.1(4) . . ?
C3 C4 C23 122.9(3) . . ?
C5 C4 C23 118.0(3) . . ?
C6 C5 C4 121.0(4) . . ?
C6 C5 C18 120.9(3) . . ?
C4 C5 C18 118.1(3) . . ?
C5 C6 C7 123.5(4) . . ?
C5 C6 H6 118.2 . . ?
C7 C6 H6 118.2 . . ?
C8 C7 C6 122.4(4) . . ?
C8 C7 C16 121.7(3) . . ?
C6 C7 C16 115.9(3) . . ?
C7 C8 C9 119.6(4) . . ?
C7 C8 C29 121.3(3) . . ?
C9 C8 C29 119.0(3) . . ?
C10 C9 C8 122.4(4) . . ?
C10 C9 C14 119.2(3) . . ?
C8 C9 C14 118.3(4) . . ?
C11 C10 C9 122.0(4) . . ?
C11 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C10 C11 C12 119.9(4) . . ?
C10 C11 Cl3 120.8(3) . . ?
C12 C11 Cl3 119.3(3) . . ?
C13 C12 C11 120.7(4) . . ?
C13 C12 Cl1 120.0(3) . . ?
C11 C12 Cl1 119.3(3) . . ?
C12 C13 C14 121.0(4) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C15 C14 C13 120.0(4) . . ?
C15 C14 C9 122.5(4) . . ?
C13 C14 C9 117.2(3) . . ?
C14 C15 C16 119.3(4) . . ?
C14 C15 C35 121.7(3) . . ?
C16 C15 C35 119.0(3) . . ?
C17 C16 C15 120.9(4) . . ?
C17 C16 C7 120.7(3) . . ?
C15 C16 C7 118.3(3) . . ?
C16 C17 C18 123.2(4) . . ?
C16 C17 H17 118.4 . . ?
C18 C17 H17 118.4 . . ?
C19 C18 C17 121.9(4) . . ?
C19 C18 C5 122.3(3) . . ?
C17 C18 C5 115.8(3) . . ?
C18 C19 C20 119.5(4) . . ?
C18 C19 C41 121.0(3) . . ?
C20 C19 C41 119.5(4) . . ?
C19 C20 C21 122.7(4) . . ?
C19 C20 C3 118.7(3) . . ?
C21 C20 C3 118.6(3) . . ?
C22 C21 C20 121.6(4) . . ?
C22 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
C21 C22 C1 119.8(4) . . ?
C21 C22 Cl4 120.8(3) . . ?
C1 C22 Cl4 119.4(3) . . ?
C24 C23 C28 118.3(4) . . ?
C24 C23 C4 122.1(3) . . ?
C28 C23 C4 119.6(4) . . ?
C23 C24 C25 120.7(4) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C26 C25 C24 120.1(4) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C27 C26 C25 120.1(4) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C26 C27 C28 120.0(4) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C27 C28 C23 120.8(4) . . ?
C27 C28 H28 119.6 . . ?
C23 C28 H28 119.6 . . ?
C30 C29 C34 119.0(4) . . ?
C30 C29 C8 121.8(3) . . ?
C34 C29 C8 119.2(4) . . ?
C29 C30 C31 120.8(4) . . ?
C29 C30 H30 119.6 . . ?
C31 C30 H30 119.6 . . ?
C32 C31 C30 119.9(4) . . ?
C32 C31 H31 120.1 . . ?
C30 C31 H31 120.1 . . ?
C33 C32 C31 120.0(4) . . ?
C33 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
C32 C33 C34 120.7(4) . . ?
C32 C33 H33 119.6 . . ?
C34 C33 H33 119.6 . . ?
C33 C34 C29 119.5(4) . . ?
C33 C34 H34 120.2 . . ?
C29 C34 H34 120.2 . . ?
C36 C35 C40 119.0(4) . . ?
C36 C35 C15 118.6(4) . . ?
C40 C35 C15 122.4(4) . . ?
C37 C36 C35 120.9(4) . . ?
C37 C36 H36 119.6 . . ?
C35 C36 H36 119.6 . . ?
C36 C37 C38 119.5(5) . . ?
C36 C37 H37 120.2 . . ?
C38 C37 H37 120.2 . . ?
C39 C38 C37 120.7(4) . . ?
C39 C38 H38 119.6 . . ?
C37 C38 H38 119.6 . . ?
C38 C39 C40 119.6(4) . . ?
C38 C39 H39 120.2 . . ?
C40 C39 H39 120.2 . . ?
C39 C40 C35 120.3(4) . . ?
C39 C40 H40 119.8 . . ?
C35 C40 H40 119.8 . . ?
C46 C41 C42 117.5(4) . . ?
C46 C41 C19 121.1(4) . . ?
C42 C41 C19 121.4(3) . . ?
C43 C42 C41 121.3(4) . . ?
C43 C42 H42 119.4 . . ?
C41 C42 H42 119.4 . . ?
C42 C43 C44 120.0(4) . . ?
C42 C43 H43 120.0 . . ?
C44 C43 H43 120.0 . . ?
C45 C44 C43 119.7(4) . . ?
C45 C44 H44 120.1 . . ?
C43 C44 H44 120.1 . . ?
C44 C45 C46 120.1(4) . . ?
C44 C45 H45 120.0 . . ?
C46 C45 H45 120.0 . . ?
C41 C46 C45 121.3(4) . . ?
C41 C46 H46 119.3 . . ?
C45 C46 H46 119.3 . . ?

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
C22 C1 C2 C3 5.1(6) . . . . ?
Cl2 C1 C2 C3 -175.7(3) . . . . ?
C1 C2 C3 C4 -178.2(4) . . . . ?
C1 C2 C3 C20 2.2(6) . . . . ?
C2 C3 C4 C5 -174.5(3) . . . . ?
C20 C3 C4 C5 5.1(6) . . . . ?
C2 C3 C4 C23 8.9(6) . . . . ?
C20 C3 C4 C23 -171.5(4) . . . . ?
C3 C4 C5 C6 175.2(4) . . . . ?
C23 C4 C5 C6 -8.0(6) . . . . ?
C3 C4 C5 C18 -2.1(5) . . . . ?
C23 C4 C5 C18 174.7(3) . . . . ?
C4 C5 C6 C7 -178.0(4) . . . . ?
C18 C5 C6 C7 -0.8(6) . . . . ?
C5 C6 C7 C8 179.2(4) . . . . ?
C5 C6 C7 C16 0.9(6) . . . . ?
C6 C7 C8 C9 -175.3(4) . . . . ?
C16 C7 C8 C9 2.8(6) . . . . ?
C6 C7 C8 C29 9.0(6) . . . . ?
C16 C7 C8 C29 -172.9(4) . . . . ?
C7 C8 C9 C10 -179.1(4) . . . . ?
C29 C8 C9 C10 -3.3(6) . . . . ?
C7 C8 C9 C14 -3.2(5) . . . . ?
C29 C8 C9 C14 172.5(3) . . . . ?
C8 C9 C10 C11 177.0(4) . . . . ?
C14 C9 C10 C11 1.2(6) . . . . ?
C9 C10 C11 C12 -1.8(6) . . . . ?
C9 C10 C11 Cl3 179.3(3) . . . . ?
C10 C11 C12 C13 0.3(6) . . . . ?
Cl3 C11 C12 C13 179.2(3) . . . . ?
C10 C11 C12 Cl1 -177.3(3) . . . . ?
Cl3 C11 C12 Cl1 1.6(5) . . . . ?
C11 C12 C13 C14 1.8(6) . . . . ?
Cl1 C12 C13 C14 179.4(3) . . . . ?
C12 C13 C14 C15 -177.2(4) . . . . ?
C12 C13 C14 C9 -2.3(6) . . . . ?
C10 C9 C14 C15 175.6(4) . . . . ?
C8 C9 C14 C15 -0.4(6) . . . . ?
C10 C9 C14 C13 0.8(5) . . . . ?
C8 C9 C14 C13 -175.2(3) . . . . ?
C13 C14 C15 C16 179.1(3) . . . . ?
C9 C14 C15 C16 4.4(6) . . . . ?
C13 C14 C15 C35 2.4(6) . . . . ?
C9 C14 C15 C35 -172.2(4) . . . . ?
C14 C15 C16 C17 175.5(4) . . . . ?
C35 C15 C16 C17 -7.8(6) . . . . ?
C14 C15 C16 C7 -4.8(6) . . . . ?
C35 C15 C16 C7 171.9(4) . . . . ?
C8 C7 C16 C17 -179.0(4) . . . . ?
C6 C7 C16 C17 -0.8(6) . . . . ?
C8 C7 C16 C15 1.2(6) . . . . ?
C6 C7 C16 C15 179.5(3) . . . . ?
C15 C16 C17 C18 -179.7(4) . . . . ?
C7 C16 C17 C18 0.5(6) . . . . ?
C16 C17 C18 C19 178.4(4) . . . . ?
C16 C17 C18 C5 -0.4(6) . . . . ?
C6 C5 C18 C19 -178.3(4) . . . . ?
C4 C5 C18 C19 -1.0(6) . . . . ?
C6 C5 C18 C17 0.5(6) . . . . ?
C4 C5 C18 C17 177.7(3) . . . . ?
C17 C18 C19 C20 -177.6(4) . . . . ?
C5 C18 C19 C20 1.1(6) . . . . ?
C17 C18 C19 C41 0.2(6) . . . . ?
C5 C18 C19 C41 178.9(4) . . . . ?
C18 C19 C20 C21 -175.8(4) . . . . ?
C41 C19 C20 C21 6.4(6) . . . . ?
C18 C19 C20 C3 1.8(6) . . . . ?
C41 C19 C20 C3 -176.0(3) . . . . ?
C4 C3 C20 C19 -5.0(6) . . . . ?
C2 C3 C20 C19 174.6(3) . . . . ?
C4 C3 C20 C21 172.7(4) . . . . ?
C2 C3 C20 C21 -7.8(5) . . . . ?
C19 C20 C21 C22 -176.1(4) . . . . ?
C3 C20 C21 C22 6.3(6) . . . . ?
C20 C21 C22 C1 0.9(6) . . . . ?
C20 C21 C22 Cl4 -177.5(3) . . . . ?
C2 C1 C22 C21 -6.8(6) . . . . ?
Cl2 C1 C22 C21 173.9(3) . . . . ?
C2 C1 C22 Cl4 171.6(3) . . . . ?
Cl2 C1 C22 Cl4 -7.6(5) . . . . ?
C3 C4 C23 C24 -70.1(5) . . . . ?
C5 C4 C23 C24 113.3(4) . . . . ?
C3 C4 C23 C28 111.3(4) . . . . ?
C5 C4 C23 C28 -65.4(5) . . . . ?
C28 C23 C24 C25 1.0(6) . . . . ?
C4 C23 C24 C25 -177.7(4) . . . . ?
C23 C24 C25 C26 -0.4(6) . . . . ?
C24 C25 C26 C27 -0.6(6) . . . . ?
C25 C26 C27 C28 1.0(7) . . . . ?
C26 C27 C28 C23 -0.5(6) . . . . ?
C24 C23 C28 C27 -0.5(6) . . . . ?
C4 C23 C28 C27 178.2(4) . . . . ?
C7 C8 C29 C30 -120.2(4) . . . . ?
C9 C8 C29 C30 64.1(5) . . . . ?
C7 C8 C29 C34 58.6(5) . . . . ?
C9 C8 C29 C34 -117.1(4) . . . . ?
C34 C29 C30 C31 2.4(5) . . . . ?
C8 C29 C30 C31 -178.8(3) . . . . ?
C29 C30 C31 C32 -1.0(6) . . . . ?
C30 C31 C32 C33 0.2(6) . . . . ?
C31 C32 C33 C34 -0.8(6) . . . . ?
C32 C33 C34 C29 2.2(6) . . . . ?
C30 C29 C34 C33 -3.0(5) . . . . ?
C8 C29 C34 C33 178.2(3) . . . . ?
C14 C15 C35 C36 108.8(4) . . . . ?
C16 C15 C35 C36 -67.9(5) . . . . ?
C14 C15 C35 C40 -72.4(5) . . . . ?
C16 C15 C35 C40 111.0(4) . . . . ?
C40 C35 C36 C37 0.2(6) . . . . ?
C15 C35 C36 C37 179.1(4) . . . . ?
C35 C36 C37 C38 0.0(7) . . . . ?
C36 C37 C38 C39 -0.6(7) . . . . ?
C37 C38 C39 C40 0.9(7) . . . . ?
C38 C39 C40 C35 -0.6(6) . . . . ?
C36 C35 C40 C39 0.0(6) . . . . ?
C15 C35 C40 C39 -178.8(4) . . . . ?
C18 C19 C41 C46 -117.2(4) . . . . ?
C20 C19 C41 C46 60.6(5) . . . . ?
C18 C19 C41 C42 60.2(5) . . . . ?
C20 C19 C41 C42 -121.9(4) . . . . ?
C46 C41 C42 C43 -1.8(6) . . . . ?
C19 C41 C42 C43 -179.4(4) . . . . ?
C41 C42 C43 C44 0.5(6) . . . . ?
C42 C43 C44 C45 1.2(7) . . . . ?
C43 C44 C45 C46 -1.5(6) . . . . ?
C42 C41 C46 C45 1.5(6) . . . . ?
C19 C41 C46 C45 179.1(4) . . . . ?
C44 C45 C46 C41 0.1(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C10 H10 Cl4 0.95 2.90 3.681(4) 140.8 1_456 yes
C21 H21 Cl3 0.95 2.98 3.682(4) 131.3 1_654 yes

_refine_diff_density_max         0.769
_refine_diff_density_min         -0.969
_refine_diff_density_rms         0.147



####################################################################### 
# 
# 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_4F
_database_code_depnum_ccdc_archive 'CCDC 1887277'
loop_
_audit_author_name
_audit_author_address
'Ryonosuke Sato'
;Tokyo Institute of Technology
Japan
;
_audit_update_record             
;
2018-12-25 deposited with the CCDC.	2019-02-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            4F4Ph
_chemical_melting_point          ?
_chemical_formula_moiety         'C46 H26 F4'
_chemical_formula_sum            'C46 H26 F4'
_chemical_formula_weight         654.67

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.0390(2)
_cell_length_b                   13.0700(2)
_cell_length_c                   13.4090(2)
_cell_angle_alpha                112.6580(10)
_cell_angle_beta                 103.9430(10)
_cell_angle_gamma                92.2560(10)
_cell_volume                     1558.51(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    18385
_cell_measurement_theta_min      3.71
_cell_measurement_theta_max      68.25

_exptl_crystal_description       platelet
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_F_000             676
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.070
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9469
_exptl_absorpt_correction_T_max  0.9844
_exptl_absorpt_process_details   'absorption was corrected by ABSCOR'

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating anode X-ray tube'
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID-II IP Area Detector'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            18385
_diffrn_reflns_av_unetI/netI     0.0607
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.705
_diffrn_reflns_theta_max         68.254
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             5593
_reflns_number_gt                2763
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;


_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998) '
_computing_data_reduction        'PROCESS-AUTO (Rigaku, 1998) '
_computing_structure_solution    'SHELXS (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1998)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1361P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5593
_refine_ls_number_parameters     451
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1144
_refine_ls_R_factor_gt           0.0677
_refine_ls_wR_factor_ref         0.2312
_refine_ls_wR_factor_gt          0.1814
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_restrained_S_all      0.968
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F47 F 0.55653(19) 0.10876(15) -0.32401(15) 0.0560(6) Uani 1 1 d . . . . .
F50 F 1.1590(2) -0.25882(15) 0.56306(16) 0.0572(6) Uani 1 1 d . . . . .
F48 F 0.7362(2) 0.29583(15) -0.21671(16) 0.0562(6) Uani 1 1 d . . . . .
F49 F 1.32431(19) -0.06349(16) 0.67731(16) 0.0584(6) Uani 1 1 d . . . . .
C22 C 0.8383(3) -0.0010(2) 0.0703(3) 0.0382(7) Uani 1 1 d . . . . .
C9 C 0.9328(3) 0.1041(2) 0.1313(3) 0.0387(7) Uani 1 1 d . . . . .
C21 C 0.8490(3) -0.0793(2) 0.1186(3) 0.0391(8) Uani 1 1 d . . . . .
H21 H 0.788302 -0.148560 0.079580 0.047 Uiso 1 1 calc R U . . .
C10 C 1.0305(3) 0.1200(3) 0.2321(3) 0.0405(8) Uani 1 1 d . . . . .
H10 H 1.094537 0.187525 0.269836 0.049 Uiso 1 1 calc R U . . .
C1 C 0.7421(3) -0.0206(2) -0.0339(3) 0.0362(7) Uani 1 1 d . . . . .
C17 C 1.0577(3) -0.2051(2) 0.4161(3) 0.0383(7) Uani 1 1 d . . . . .
H17 H 0.997815 -0.274721 0.377236 0.046 Uiso 1 1 calc R U . . .
C8 C 0.9287(3) 0.1858(2) 0.0867(3) 0.0366(7) Uani 1 1 d . . . . .
C3 C 0.6466(3) 0.0441(2) -0.1827(2) 0.0368(7) Uani 1 1 d . . . . .
H3 H 0.580324 -0.022028 -0.221876 0.044 Uiso 1 1 calc R U . . .
C20 C 0.9450(3) -0.0610(2) 0.2219(3) 0.0373(7) Uani 1 1 d . . . . .
C11 C 1.0388(3) 0.0419(2) 0.2805(2) 0.0356(7) Uani 1 1 d . . . . .
C19 C 0.9503(3) -0.1441(2) 0.2668(3) 0.0374(7) Uani 1 1 d . . . . .
C18 C 1.0491(3) -0.1245(2) 0.3680(3) 0.0374(7) Uani 1 1 d . . . . .
C13 C 1.1445(3) -0.0195(2) 0.4280(3) 0.0397(8) Uani 1 1 d . . . . .
C12 C 1.1400(3) 0.0615(2) 0.3838(3) 0.0385(8) Uani 1 1 d . . . . .
C4 C 0.6462(3) 0.1212(3) -0.2256(3) 0.0443(8) Uani 1 1 d . . . . .
C6 C 0.8336(3) 0.2437(2) -0.0692(3) 0.0400(8) Uani 1 1 d . . . . .
H6 H 0.895354 0.312516 -0.031610 0.048 Uiso 1 1 calc R U . . .
C2 C 0.7430(3) 0.0586(2) -0.0806(3) 0.0385(7) Uani 1 1 d . . . . .
C14 C 1.2383(3) -0.0015(3) 0.5339(3) 0.0422(8) Uani 1 1 d . . . . .
H14 H 1.300752 0.066692 0.575291 0.051 Uiso 1 1 calc R U . . .
C41 C 0.8481(3) -0.2502(2) 0.2082(3) 0.0396(8) Uani 1 1 d . . . . .
C16 C 1.1500(3) -0.1837(3) 0.5161(3) 0.0462(8) Uani 1 1 d . . . . .
C23 C 0.6362(3) -0.1248(2) -0.0918(3) 0.0374(7) Uani 1 1 d . . . . .
C7 C 0.8390(3) 0.1635(2) -0.0196(3) 0.0384(7) Uani 1 1 d . . . . .
C5 C 0.7421(3) 0.2217(3) -0.1681(3) 0.0427(8) Uani 1 1 d . . . . .
C15 C 1.2393(3) -0.0804(3) 0.5759(3) 0.0452(8) Uani 1 1 d . . . . .
C35 C 1.2426(3) 0.1682(3) 0.4447(3) 0.0416(8) Uani 1 1 d . . . . .
C29 C 1.0110(3) 0.3002(2) 0.1579(3) 0.0416(8) Uani 1 1 d . . . . .
C24 C 0.5436(3) -0.1465(3) -0.0376(3) 0.0453(8) Uani 1 1 d . . . . .
H24 H 0.547483 -0.095154 0.036341 0.054 Uiso 1 1 calc R U . . .
C28 C 0.6275(3) -0.2010(2) -0.2012(3) 0.0450(8) Uani 1 1 d . . . . .
H28 H 0.689719 -0.187673 -0.239642 0.054 Uiso 1 1 calc R U . . .
C36 C 1.2001(3) 0.2731(2) 0.4791(3) 0.0448(8) Uani 1 1 d . . . . .
H36 H 1.103704 0.278219 0.463095 0.054 Uiso 1 1 calc R U . . .
C26 C 0.4381(4) -0.3178(3) -0.1979(3) 0.0562(10) Uani 1 1 d . . . . .
H26 H 0.371743 -0.384002 -0.233126 0.067 Uiso 1 1 calc R U . . .
C33 C 1.0579(4) 0.4715(3) 0.3273(3) 0.0577(10) Uani 1 1 d . . . . .
H33 H 1.037935 0.515418 0.395658 0.069 Uiso 1 1 calc R U . . .
C30 C 1.1164(3) 0.3441(3) 0.1280(3) 0.0489(9) Uani 1 1 d . . . . .
H30 H 1.137625 0.301466 0.059787 0.059 Uiso 1 1 calc R U . . .
C27 C 0.5277(4) -0.2965(3) -0.2537(3) 0.0571(10) Uani 1 1 d . . . . .
H27 H 0.521154 -0.347264 -0.328526 0.069 Uiso 1 1 calc R U . . .
C46 C 0.7077(3) -0.2476(3) 0.1974(3) 0.0490(9) Uani 1 1 d . . . . .
H46 H 0.675136 -0.177242 0.222119 0.059 Uiso 1 1 calc R U . . .
C42 C 0.8933(4) -0.3546(3) 0.1662(3) 0.0516(9) Uani 1 1 d . . . . .
H42 H 0.988658 -0.358698 0.170314 0.062 Uiso 1 1 calc R U . . .
C31 C 1.1904(4) 0.4497(3) 0.1976(3) 0.0568(10) Uani 1 1 d . . . . .
H31 H 1.261803 0.478423 0.175919 0.068 Uiso 1 1 calc R U . . .
C40 C 1.3848(3) 0.1640(3) 0.4675(3) 0.0453(8) Uani 1 1 d . . . . .
H40 H 1.416544 0.093304 0.443449 0.054 Uiso 1 1 calc R U . . .
C43 C 0.7977(4) -0.4521(3) 0.1183(3) 0.0626(11) Uani 1 1 d . . . . .
H43 H 0.828546 -0.522706 0.089559 0.075 Uiso 1 1 calc R U . . .
C39 C 1.4805(4) 0.2607(3) 0.5245(3) 0.0584(10) Uani 1 1 d . . . . .
H39 H 1.576985 0.255939 0.539608 0.070 Uiso 1 1 calc R U . . .
C38 C 1.4361(4) 0.3650(3) 0.5598(3) 0.0629(11) Uani 1 1 d . . . . .
H38 H 1.501431 0.431679 0.599683 0.076 Uiso 1 1 calc R U . . .
C37 C 1.2952(4) 0.3701(3) 0.5360(3) 0.0565(10) Uani 1 1 d . . . . .
H37 H 1.263515 0.440896 0.559022 0.068 Uiso 1 1 calc R U . . .
C34 C 0.9815(3) 0.3661(3) 0.2588(3) 0.0483(9) Uani 1 1 d . . . . .
H34 H 0.909114 0.338395 0.280366 0.058 Uiso 1 1 calc R U . . .
C44 C 0.6597(4) -0.4481(3) 0.1120(3) 0.0679(12) Uani 1 1 d . . . . .
H44 H 0.595890 -0.515427 0.080613 0.081 Uiso 1 1 calc R U . . .
C45 C 0.6139(4) -0.3449(3) 0.1517(3) 0.0628(11) Uani 1 1 d . . . . .
H45 H 0.518466 -0.341226 0.147356 0.075 Uiso 1 1 calc R U . . .
C25 C 0.4461(4) -0.2419(3) -0.0903(3) 0.0545(9) Uani 1 1 d . . . . .
H25 H 0.383744 -0.255559 -0.052131 0.065 Uiso 1 1 calc R U . . .
C32 C 1.1639(4) 0.5133(3) 0.2960(3) 0.0575(10) Uani 1 1 d . . . . .
H32 H 1.216579 0.585170 0.342825 0.069 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
F47 C4 1.353(3) . ?
F50 C16 1.351(3) . ?
F48 C5 1.356(3) . ?
F49 C15 1.350(3) . ?
C22 C21 1.401(4) . ?
C22 C1 1.416(4) . ?
C22 C9 1.455(4) . ?
C9 C10 1.401(4) . ?
C9 C8 1.408(4) . ?
C21 C20 1.409(4) . ?
C21 H21 0.9500 . ?
C10 C11 1.400(4) . ?
C10 H10 0.9500 . ?
C1 C2 1.402(4) . ?
C1 C23 1.504(4) . ?
C17 C16 1.351(4) . ?
C17 C18 1.426(4) . ?
C17 H17 0.9500 . ?
C8 C7 1.403(4) . ?
C8 C29 1.501(4) . ?
C3 C4 1.338(4) . ?
C3 C2 1.411(4) . ?
C3 H3 0.9500 . ?
C20 C19 1.428(4) . ?
C20 C11 1.429(4) . ?
C11 C12 1.430(4) . ?
C19 C18 1.398(4) . ?
C19 C41 1.501(4) . ?
C18 C13 1.457(4) . ?
C13 C12 1.396(4) . ?
C13 C14 1.428(4) . ?
C12 C35 1.509(4) . ?
C4 C5 1.417(4) . ?
C6 C5 1.336(4) . ?
C6 C7 1.439(4) . ?
C6 H6 0.9500 . ?
C2 C7 1.459(4) . ?
C14 C15 1.351(4) . ?
C14 H14 0.9500 . ?
C41 C46 1.385(4) . ?
C41 C42 1.402(4) . ?
C16 C15 1.412(4) . ?
C23 C24 1.391(4) . ?
C23 C28 1.399(4) . ?
C35 C36 1.388(4) . ?
C35 C40 1.394(4) . ?
C29 C30 1.393(4) . ?
C29 C34 1.406(4) . ?
C24 C25 1.380(4) . ?
C24 H24 0.9500 . ?
C28 C27 1.393(4) . ?
C28 H28 0.9500 . ?
C36 C37 1.382(4) . ?
C36 H36 0.9500 . ?
C26 C25 1.380(5) . ?
C26 C27 1.384(5) . ?
C26 H26 0.9500 . ?
C33 C34 1.391(4) . ?
C33 C32 1.397(5) . ?
C33 H33 0.9500 . ?
C30 C31 1.386(4) . ?
C30 H30 0.9500 . ?
C27 H27 0.9500 . ?
C46 C45 1.380(4) . ?
C46 H46 0.9500 . ?
C42 C43 1.390(4) . ?
C42 H42 0.9500 . ?
C31 C32 1.358(5) . ?
C31 H31 0.9500 . ?
C40 C39 1.383(4) . ?
C40 H40 0.9500 . ?
C43 C44 1.372(5) . ?
C43 H43 0.9500 . ?
C39 C38 1.390(5) . ?
C39 H39 0.9500 . ?
C38 C37 1.383(5) . ?
C38 H38 0.9500 . ?
C37 H37 0.9500 . ?
C34 H34 0.9500 . ?
C44 C45 1.388(5) . ?
C44 H44 0.9500 . ?
C45 H45 0.9500 . ?
C25 H25 0.9500 . ?
C32 H32 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21 C22 C1 123.2(3) . . ?
C21 C22 C9 117.2(3) . . ?
C1 C22 C9 119.6(3) . . ?
C10 C9 C8 121.2(3) . . ?
C10 C9 C22 118.7(3) . . ?
C8 C9 C22 120.1(3) . . ?
C22 C21 C20 123.6(3) . . ?
C22 C21 H21 118.2 . . ?
C20 C21 H21 118.2 . . ?
C11 C10 C9 123.6(3) . . ?
C11 C10 H10 118.2 . . ?
C9 C10 H10 118.2 . . ?
C2 C1 C22 120.1(3) . . ?
C2 C1 C23 120.4(3) . . ?
C22 C1 C23 119.5(3) . . ?
C16 C17 C18 120.9(3) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C7 C8 C9 120.1(3) . . ?
C7 C8 C29 120.2(3) . . ?
C9 C8 C29 119.5(3) . . ?
C4 C3 C2 121.7(3) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C21 C20 C19 120.9(3) . . ?
C21 C20 C11 118.8(3) . . ?
C19 C20 C11 120.3(3) . . ?
C10 C11 C20 118.1(3) . . ?
C10 C11 C12 121.8(3) . . ?
C20 C11 C12 120.1(3) . . ?
C18 C19 C20 119.5(3) . . ?
C18 C19 C41 120.0(3) . . ?
C20 C19 C41 120.5(3) . . ?
C19 C18 C17 121.3(3) . . ?
C19 C18 C13 120.3(3) . . ?
C17 C18 C13 118.4(3) . . ?
C12 C13 C14 121.8(3) . . ?
C12 C13 C18 120.3(3) . . ?
C14 C13 C18 117.9(3) . . ?
C13 C12 C11 119.5(3) . . ?
C13 C12 C35 119.8(3) . . ?
C11 C12 C35 120.7(3) . . ?
C3 C4 F47 123.0(3) . . ?
C3 C4 C5 120.6(3) . . ?
F47 C4 C5 116.5(3) . . ?
C5 C6 C7 120.1(3) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C1 C2 C3 122.0(3) . . ?
C1 C2 C7 120.0(3) . . ?
C3 C2 C7 117.8(3) . . ?
C15 C14 C13 120.7(3) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C46 C41 C42 118.5(3) . . ?
C46 C41 C19 120.9(3) . . ?
C42 C41 C19 120.6(3) . . ?
F50 C16 C17 121.7(3) . . ?
F50 C16 C15 117.7(3) . . ?
C17 C16 C15 120.6(3) . . ?
C24 C23 C28 118.7(3) . . ?
C24 C23 C1 120.4(3) . . ?
C28 C23 C1 121.0(3) . . ?
C8 C7 C6 121.9(3) . . ?
C8 C7 C2 119.9(3) . . ?
C6 C7 C2 118.1(3) . . ?
C6 C5 F48 121.0(3) . . ?
C6 C5 C4 121.6(3) . . ?
F48 C5 C4 117.4(3) . . ?
F49 C15 C14 121.5(3) . . ?
F49 C15 C16 117.1(3) . . ?
C14 C15 C16 121.4(3) . . ?
C36 C35 C40 117.8(3) . . ?
C36 C35 C12 121.9(3) . . ?
C40 C35 C12 120.4(3) . . ?
C30 C29 C34 118.4(3) . . ?
C30 C29 C8 122.5(3) . . ?
C34 C29 C8 119.0(3) . . ?
C25 C24 C23 120.6(3) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C27 C28 C23 120.1(3) . . ?
C27 C28 H28 120.0 . . ?
C23 C28 H28 120.0 . . ?
C37 C36 C35 121.3(3) . . ?
C37 C36 H36 119.4 . . ?
C35 C36 H36 119.4 . . ?
C25 C26 C27 119.2(3) . . ?
C25 C26 H26 120.4 . . ?
C27 C26 H26 120.4 . . ?
C34 C33 C32 120.4(3) . . ?
C34 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C31 C30 C29 120.1(3) . . ?
C31 C30 H30 119.9 . . ?
C29 C30 H30 119.9 . . ?
C26 C27 C28 120.5(3) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 H27 119.7 . . ?
C45 C46 C41 121.5(3) . . ?
C45 C46 H46 119.3 . . ?
C41 C46 H46 119.3 . . ?
C43 C42 C41 119.6(3) . . ?
C43 C42 H42 120.2 . . ?
C41 C42 H42 120.2 . . ?
C32 C31 C30 121.9(4) . . ?
C32 C31 H31 119.0 . . ?
C30 C31 H31 119.0 . . ?
C39 C40 C35 121.3(3) . . ?
C39 C40 H40 119.4 . . ?
C35 C40 H40 119.4 . . ?
C44 C43 C42 121.2(3) . . ?
C44 C43 H43 119.4 . . ?
C42 C43 H43 119.4 . . ?
C40 C39 C38 120.2(3) . . ?
C40 C39 H39 119.9 . . ?
C38 C39 H39 119.9 . . ?
C37 C38 C39 118.9(3) . . ?
C37 C38 H38 120.5 . . ?
C39 C38 H38 120.5 . . ?
C36 C37 C38 120.5(3) . . ?
C36 C37 H37 119.7 . . ?
C38 C37 H37 119.7 . . ?
C33 C34 C29 120.2(3) . . ?
C33 C34 H34 119.9 . . ?
C29 C34 H34 119.9 . . ?
C43 C44 C45 119.5(3) . . ?
C43 C44 H44 120.2 . . ?
C45 C44 H44 120.2 . . ?
C46 C45 C44 119.7(4) . . ?
C46 C45 H45 120.1 . . ?
C44 C45 H45 120.1 . . ?
C24 C25 C26 120.9(3) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C31 C32 C33 119.0(3) . . ?
C31 C32 H32 120.5 . . ?
C33 C32 H32 120.5 . . ?

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
C21 C22 C9 C10 1.6(5) . . . . ?
C1 C22 C9 C10 -177.7(3) . . . . ?
C21 C22 C9 C8 179.2(3) . . . . ?
C1 C22 C9 C8 -0.1(5) . . . . ?
C1 C22 C21 C20 179.6(3) . . . . ?
C9 C22 C21 C20 0.3(5) . . . . ?
C8 C9 C10 C11 179.7(3) . . . . ?
C22 C9 C10 C11 -2.7(5) . . . . ?
C21 C22 C1 C2 -176.0(3) . . . . ?
C9 C22 C1 C2 3.2(5) . . . . ?
C21 C22 C1 C23 6.1(5) . . . . ?
C9 C22 C1 C23 -174.7(3) . . . . ?
C10 C9 C8 C7 173.9(3) . . . . ?
C22 C9 C8 C7 -3.7(5) . . . . ?
C10 C9 C8 C29 -11.6(5) . . . . ?
C22 C9 C8 C29 170.8(3) . . . . ?
C22 C21 C20 C19 179.7(3) . . . . ?
C22 C21 C20 C11 -1.2(5) . . . . ?
C9 C10 C11 C20 1.8(5) . . . . ?
C9 C10 C11 C12 -179.9(3) . . . . ?
C21 C20 C11 C10 0.1(5) . . . . ?
C19 C20 C11 C10 179.2(3) . . . . ?
C21 C20 C11 C12 -178.2(3) . . . . ?
C19 C20 C11 C12 1.0(5) . . . . ?
C21 C20 C19 C18 178.4(3) . . . . ?
C11 C20 C19 C18 -0.7(5) . . . . ?
C21 C20 C19 C41 -3.5(5) . . . . ?
C11 C20 C19 C41 177.4(3) . . . . ?
C20 C19 C18 C17 179.8(3) . . . . ?
C41 C19 C18 C17 1.7(5) . . . . ?
C20 C19 C18 C13 0.9(5) . . . . ?
C41 C19 C18 C13 -177.2(3) . . . . ?
C16 C17 C18 C19 -177.4(3) . . . . ?
C16 C17 C18 C13 1.5(5) . . . . ?
C19 C18 C13 C12 -1.3(5) . . . . ?
C17 C18 C13 C12 179.8(3) . . . . ?
C19 C18 C13 C14 176.7(3) . . . . ?
C17 C18 C13 C14 -2.2(4) . . . . ?
C14 C13 C12 C11 -176.4(3) . . . . ?
C18 C13 C12 C11 1.5(5) . . . . ?
C14 C13 C12 C35 4.1(5) . . . . ?
C18 C13 C12 C35 -177.9(3) . . . . ?
C10 C11 C12 C13 -179.5(3) . . . . ?
C20 C11 C12 C13 -1.3(5) . . . . ?
C10 C11 C12 C35 -0.1(5) . . . . ?
C20 C11 C12 C35 178.1(3) . . . . ?
C2 C3 C4 F47 178.9(3) . . . . ?
C2 C3 C4 C5 -1.1(5) . . . . ?
C22 C1 C2 C3 -178.2(3) . . . . ?
C23 C1 C2 C3 -0.3(5) . . . . ?
C22 C1 C2 C7 -2.6(5) . . . . ?
C23 C1 C2 C7 175.2(3) . . . . ?
C4 C3 C2 C1 178.6(3) . . . . ?
C4 C3 C2 C7 2.9(5) . . . . ?
C12 C13 C14 C15 178.9(3) . . . . ?
C18 C13 C14 C15 0.9(5) . . . . ?
C18 C19 C41 C46 113.9(3) . . . . ?
C20 C19 C41 C46 -64.2(4) . . . . ?
C18 C19 C41 C42 -64.1(4) . . . . ?
C20 C19 C41 C42 117.8(3) . . . . ?
C18 C17 C16 F50 179.6(3) . . . . ?
C18 C17 C16 C15 0.6(5) . . . . ?
C2 C1 C23 C24 -119.7(3) . . . . ?
C22 C1 C23 C24 58.2(4) . . . . ?
C2 C1 C23 C28 59.5(4) . . . . ?
C22 C1 C23 C28 -122.6(3) . . . . ?
C9 C8 C7 C6 -178.7(3) . . . . ?
C29 C8 C7 C6 6.9(5) . . . . ?
C9 C8 C7 C2 4.3(5) . . . . ?
C29 C8 C7 C2 -170.2(3) . . . . ?
C5 C6 C7 C8 -176.7(3) . . . . ?
C5 C6 C7 C2 0.4(5) . . . . ?
C1 C2 C7 C8 -1.1(5) . . . . ?
C3 C2 C7 C8 174.6(3) . . . . ?
C1 C2 C7 C6 -178.3(3) . . . . ?
C3 C2 C7 C6 -2.5(4) . . . . ?
C7 C6 C5 F48 -179.5(3) . . . . ?
C7 C6 C5 C4 1.5(5) . . . . ?
C3 C4 C5 C6 -1.2(5) . . . . ?
F47 C4 C5 C6 178.8(3) . . . . ?
C3 C4 C5 F48 179.7(3) . . . . ?
F47 C4 C5 F48 -0.4(4) . . . . ?
C13 C14 C15 F49 -178.0(3) . . . . ?
C13 C14 C15 C16 1.2(5) . . . . ?
F50 C16 C15 F49 -1.8(5) . . . . ?
C17 C16 C15 F49 177.2(3) . . . . ?
F50 C16 C15 C14 178.9(3) . . . . ?
C17 C16 C15 C14 -2.0(5) . . . . ?
C13 C12 C35 C36 -123.0(3) . . . . ?
C11 C12 C35 C36 57.6(4) . . . . ?
C13 C12 C35 C40 57.5(4) . . . . ?
C11 C12 C35 C40 -121.9(3) . . . . ?
C7 C8 C29 C30 -66.9(4) . . . . ?
C9 C8 C29 C30 118.6(3) . . . . ?
C7 C8 C29 C34 113.3(3) . . . . ?
C9 C8 C29 C34 -61.3(4) . . . . ?
C28 C23 C24 C25 0.7(5) . . . . ?
C1 C23 C24 C25 179.9(3) . . . . ?
C24 C23 C28 C27 -0.1(4) . . . . ?
C1 C23 C28 C27 -179.3(3) . . . . ?
C40 C35 C36 C37 -1.3(5) . . . . ?
C12 C35 C36 C37 179.2(3) . . . . ?
C34 C29 C30 C31 0.7(4) . . . . ?
C8 C29 C30 C31 -179.2(3) . . . . ?
C25 C26 C27 C28 1.7(5) . . . . ?
C23 C28 C27 C26 -1.1(5) . . . . ?
C42 C41 C46 C45 3.2(5) . . . . ?
C19 C41 C46 C45 -174.8(3) . . . . ?
C46 C41 C42 C43 -2.0(5) . . . . ?
C19 C41 C42 C43 176.1(3) . . . . ?
C29 C30 C31 C32 0.2(5) . . . . ?
C36 C35 C40 C39 1.3(5) . . . . ?
C12 C35 C40 C39 -179.1(3) . . . . ?
C41 C42 C43 C44 -0.3(6) . . . . ?
C35 C40 C39 C38 -0.4(5) . . . . ?
C40 C39 C38 C37 -0.6(6) . . . . ?
C35 C36 C37 C38 0.3(5) . . . . ?
C39 C38 C37 C36 0.7(6) . . . . ?
C32 C33 C34 C29 0.5(5) . . . . ?
C30 C29 C34 C33 -1.0(4) . . . . ?
C8 C29 C34 C33 178.9(3) . . . . ?
C42 C43 C44 C45 1.4(6) . . . . ?
C41 C46 C45 C44 -2.1(6) . . . . ?
C43 C44 C45 C46 -0.2(6) . . . . ?
C23 C24 C25 C26 -0.1(5) . . . . ?
C27 C26 C25 C24 -1.1(5) . . . . ?
C30 C31 C32 C33 -0.7(5) . . . . ?
C34 C33 C32 C31 0.4(5) . . . . ?

_refine_diff_density_max         0.470
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.065



