# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2024

####################################################################### 
# 
# 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_xl_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2080255'
loop_
_audit_author_name
_audit_author_address
'Zuoqin Liang'
;Suzhou university of scinece and technology
China
;
_audit_update_record             
;
2021-04-27 deposited with the CCDC.	2024-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H15 Cl'
_chemical_formula_weight         290.77

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'
Cl Cl 0.1484 0.1585 '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'

_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                   9.406(3)
_cell_length_b                   12.232(3)
_cell_length_c                   15.420(4)
_cell_angle_alpha                72.748(4)
_cell_angle_beta                 73.634(4)
_cell_angle_gamma                69.980(4)
_cell_volume                     1559.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2394
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      23.24

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.235
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8906
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.411
_diffrn_reflns_theta_max         27.460
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             6770
_reflns_number_gt                4138
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_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)+(0.2100P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6770
_refine_ls_number_parameters     379
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1135
_refine_ls_R_factor_gt           0.0752
_refine_ls_wR_factor_ref         0.3248
_refine_ls_wR_factor_gt          0.2820
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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 0.2438(2) 0.91170(10) 0.96076(9) 0.1090(5) Uani 1 1 d . . . . .
Cl2 Cl 0.81423(15) 1.07036(9) 0.77783(9) 0.0981(5) Uani 1 1 d . . . . .
C1 C 0.9396(4) 0.8603(3) 0.5995(2) 0.0632(8) Uani 1 1 d . . . . .
H1 H 1.021398 0.842018 0.550605 0.076 Uiso 1 1 calc R U . . .
C2 C 0.9374(4) 0.9406(3) 0.6464(3) 0.0690(9) Uani 1 1 d . . . . .
H2 H 1.016932 0.976467 0.629082 0.083 Uiso 1 1 calc R U . . .
C3 C 0.8182(4) 0.9677(3) 0.7184(2) 0.0624(9) Uani 1 1 d . . . . .
C4 C 0.7000(4) 0.9151(3) 0.7449(2) 0.0656(9) Uani 1 1 d . . . . .
H4 H 0.618936 0.934169 0.793895 0.079 Uiso 1 1 calc R U . . .
C5 C 0.7028(4) 0.8338(3) 0.6981(2) 0.0604(8) Uani 1 1 d . . . . .
H5 H 0.623936 0.797240 0.716572 0.073 Uiso 1 1 calc R U . . .
C6 C 0.8225(4) 0.8058(3) 0.6235(2) 0.0541(7) Uani 1 1 d . . . . .
C7 C 0.8182(4) 0.7264(3) 0.5678(2) 0.0584(8) Uani 1 1 d . . . . .
C8 C 0.8133(4) 0.6133(3) 0.6048(2) 0.0640(8) Uani 1 1 d . . . . .
H8 H 0.794997 0.576043 0.566172 0.077 Uiso 1 1 calc R U . . .
C9 C 0.8324(4) 0.5410(3) 0.6961(2) 0.0554(7) Uani 1 1 d . . . . .
C10 C 0.9217(4) 0.5511(3) 0.7497(2) 0.0626(8) Uani 1 1 d . . . . .
H10 H 0.971428 0.610788 0.727631 0.075 Uiso 1 1 calc R U . . .
C11 C 0.9388(4) 0.4751(3) 0.8347(3) 0.0737(10) Uani 1 1 d . . . . .
H11 H 0.999264 0.484924 0.868623 0.088 Uiso 1 1 calc R U . . .
C12 C 0.8701(5) 0.3873(4) 0.8694(3) 0.0811(10) Uani 1 1 d . U . . .
H12 H 0.881888 0.337738 0.927271 0.097 Uiso 1 1 calc R U . . .
C13 C 0.7821(5) 0.3706(3) 0.8194(3) 0.0817(10) Uani 1 1 d . U . . .
H13 H 0.736206 0.308637 0.842949 0.098 Uiso 1 1 calc R U . . .
C14 C 0.7616(4) 0.4461(3) 0.7337(3) 0.0731(10) Uani 1 1 d . . . . .
H14 H 0.701120 0.434702 0.700519 0.088 Uiso 1 1 calc R U . . .
C15 C 0.8042(4) 0.7817(3) 0.4682(2) 0.0587(8) Uani 1 1 d . . . . .
C16 C 0.8551(5) 0.7168(4) 0.4005(3) 0.0748(10) Uani 1 1 d . . . . .
H16 H 0.907053 0.636085 0.415520 0.090 Uiso 1 1 calc R U . . .
C17 C 0.8319(6) 0.7665(5) 0.3126(3) 0.0960(14) Uani 1 1 d . . . . .
H17 H 0.865941 0.720039 0.268749 0.115 Uiso 1 1 calc R U . . .
C18 C 0.7564(6) 0.8879(5) 0.2887(3) 0.0936(14) Uani 1 1 d . . . . .
H18 H 0.738248 0.922791 0.229001 0.112 Uiso 1 1 calc R U . . .
C19 C 0.7091(5) 0.9557(4) 0.3543(3) 0.0841(12) Uani 1 1 d . . . . .
H19 H 0.661142 1.037110 0.338339 0.101 Uiso 1 1 calc R U . . .
C20 C 0.7325(4) 0.9035(3) 0.4431(2) 0.0663(9) Uani 1 1 d . . . . .
H20 H 0.700253 0.949939 0.486901 0.080 Uiso 1 1 calc R U . . .
C21 C 0.4216(4) 0.6067(3) 0.8778(3) 0.0682(9) Uani 1 1 d . . . . .
H21 H 0.507412 0.540802 0.884736 0.082 Uiso 1 1 calc R U . . .
C22 C 0.4016(4) 0.6995(3) 0.9155(2) 0.0686(9) Uani 1 1 d . . . . .
H22 H 0.473221 0.697102 0.947543 0.082 Uiso 1 1 calc R U . . .
C23 C 0.2741(5) 0.7976(3) 0.9059(2) 0.0657(9) Uani 1 1 d . . . . .
C24 C 0.1694(5) 0.8040(3) 0.8577(3) 0.0726(10) Uani 1 1 d . . . . .
H24 H 0.084399 0.870737 0.851451 0.087 Uiso 1 1 calc R U . . .
C25 C 0.1908(4) 0.7101(3) 0.8181(3) 0.0681(9) Uani 1 1 d . . . . .
H25 H 0.121042 0.714803 0.783793 0.082 Uiso 1 1 calc R U . . .
C26 C 0.3171(4) 0.6078(3) 0.8294(2) 0.0616(8) Uani 1 1 d . . . . .
C27 C 0.3332(4) 0.4990(3) 0.7961(2) 0.0623(8) Uani 1 1 d . . . . .
C28 C 0.3365(4) 0.5011(3) 0.7094(3) 0.0693(9) Uani 1 1 d . . . . .
H28 H 0.334451 0.430234 0.699754 0.083 Uiso 1 1 calc R U . . .
C29 C 0.3431(4) 0.5988(3) 0.6248(2) 0.0614(8) Uani 1 1 d . . . . .
C30 C 0.2878(6) 0.5923(4) 0.5523(3) 0.0918(13) Uani 1 1 d . . . . .
H30 H 0.244795 0.530953 0.560588 0.110 Uiso 1 1 calc R U . . .
C31 C 0.2948(8) 0.6734(6) 0.4691(3) 0.1186(19) Uani 1 1 d . . . . .
H31 H 0.253841 0.668379 0.422556 0.142 Uiso 1 1 calc R U . . .
C32 C 0.3626(6) 0.7624(5) 0.4547(3) 0.1043(18) Uani 1 1 d . . . . .
H32 H 0.371360 0.816573 0.397916 0.125 Uiso 1 1 calc R U . . .
C33 C 0.4173(5) 0.7693(4) 0.5267(4) 0.0912(14) Uani 1 1 d . . . . .
H33 H 0.461355 0.830065 0.518283 0.109 Uiso 1 1 calc R U . . .
C34 C 0.4085(4) 0.6902(4) 0.6087(3) 0.0764(10) Uani 1 1 d . . . . .
H34 H 0.447224 0.697153 0.655391 0.092 Uiso 1 1 calc R U . . .
C35 C 0.3321(4) 0.3862(3) 0.8662(3) 0.0620(8) Uani 1 1 d . . . . .
C36 C 0.2506(5) 0.3911(3) 0.9559(3) 0.0705(9) Uani 1 1 d . . . . .
H36 H 0.203589 0.464646 0.971896 0.085 Uiso 1 1 calc R U . . .
C37 C 0.2384(5) 0.2876(4) 1.0218(3) 0.0832(11) Uani 1 1 d . . . . .
H37 H 0.183381 0.292636 1.081624 0.100 Uiso 1 1 calc R U . . .
C38 C 0.3060(6) 0.1786(4) 1.0003(3) 0.0859(12) Uani 1 1 d . . . . .
H38 H 0.294503 0.109801 1.044425 0.103 Uiso 1 1 calc R U . . .
C39 C 0.3899(6) 0.1715(3) 0.9143(3) 0.0855(12) Uani 1 1 d . . . . .
H39 H 0.438775 0.097066 0.899849 0.103 Uiso 1 1 calc R U . . .
C40 C 0.4040(5) 0.2727(3) 0.8477(3) 0.0757(10) Uani 1 1 d . . . . .
H40 H 0.462765 0.265567 0.789006 0.091 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 C23 1.743(3) . ?
Cl2 C3 1.747(3) . ?
C1 C2 1.375(5) . ?
C1 C6 1.386(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.364(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(5) . ?
C4 C5 1.380(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.491(4) . ?
C7 C8 1.343(5) . ?
C7 C15 1.507(5) . ?
C8 C9 1.446(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.387(5) . ?
C9 C14 1.428(5) . ?
C10 C11 1.379(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.340(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.374(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.391(6) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.379(5) . ?
C15 C20 1.393(5) . ?
C16 C17 1.356(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.395(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.378(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.374(5) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.358(5) . ?
C21 C26 1.387(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.381(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.360(5) . ?
C24 C25 1.387(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.406(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.510(4) . ?
C27 C28 1.320(5) . ?
C27 C35 1.481(5) . ?
C28 C29 1.489(5) . ?
C28 H28 0.9300 . ?
C29 C34 1.382(5) . ?
C29 C30 1.391(5) . ?
C30 C31 1.371(7) . ?
C30 H30 0.9300 . ?
C31 C32 1.375(9) . ?
C31 H31 0.9300 . ?
C32 C33 1.383(8) . ?
C32 H32 0.9300 . ?
C33 C34 1.345(6) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
C35 C36 1.386(5) . ?
C35 C40 1.396(5) . ?
C36 C37 1.386(5) . ?
C36 H36 0.9300 . ?
C37 C38 1.362(6) . ?
C37 H37 0.9300 . ?
C38 C39 1.350(6) . ?
C38 H38 0.9300 . ?
C39 C40 1.374(5) . ?
C39 H39 0.9300 . ?
C40 H40 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 C6 121.4(3) . . ?
C2 C1 H1 119.3 . . ?
C6 C1 H1 119.3 . . ?
C3 C2 C1 119.8(3) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 120.8(3) . . ?
C2 C3 Cl2 120.0(3) . . ?
C4 C3 Cl2 119.2(3) . . ?
C3 C4 C5 119.4(3) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 117.8(3) . . ?
C1 C6 C7 121.3(3) . . ?
C5 C6 C7 120.8(3) . . ?
C8 C7 C6 122.7(3) . . ?
C8 C7 C15 120.0(3) . . ?
C6 C7 C15 117.0(3) . . ?
C7 C8 C9 129.3(3) . . ?
C7 C8 H8 115.3 . . ?
C9 C8 H8 115.3 . . ?
C10 C9 C14 116.0(3) . . ?
C10 C9 C8 125.6(3) . . ?
C14 C9 C8 118.3(3) . . ?
C11 C10 C9 121.8(3) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C12 C11 C10 121.4(4) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 119.9(4) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C14 120.2(4) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C9 120.6(4) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
C16 C15 C20 117.9(3) . . ?
C16 C15 C7 123.1(3) . . ?
C20 C15 C7 119.0(3) . . ?
C17 C16 C15 122.3(4) . . ?
C17 C16 H16 118.9 . . ?
C15 C16 H16 118.9 . . ?
C16 C17 C18 119.4(4) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C19 C18 C17 119.5(4) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C20 C19 C18 120.2(4) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C15 120.7(4) . . ?
C19 C20 H20 119.7 . . ?
C15 C20 H20 119.7 . . ?
C22 C21 C26 121.6(3) . . ?
C22 C21 H21 119.2 . . ?
C26 C21 H21 119.2 . . ?
C21 C22 C23 119.6(3) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C24 C23 C22 121.2(3) . . ?
C24 C23 Cl1 119.8(3) . . ?
C22 C23 Cl1 119.0(3) . . ?
C23 C24 C25 119.3(3) . . ?
C23 C24 H24 120.3 . . ?
C25 C24 H24 120.3 . . ?
C24 C25 C26 120.5(3) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C21 C26 C25 117.8(3) . . ?
C21 C26 C27 120.7(3) . . ?
C25 C26 C27 121.4(3) . . ?
C28 C27 C35 118.3(3) . . ?
C28 C27 C26 123.6(3) . . ?
C35 C27 C26 117.8(3) . . ?
C27 C28 C29 130.3(3) . . ?
C27 C28 H28 114.8 . . ?
C29 C28 H28 114.8 . . ?
C34 C29 C30 116.9(3) . . ?
C34 C29 C28 126.4(3) . . ?
C30 C29 C28 116.5(3) . . ?
C31 C30 C29 122.0(5) . . ?
C31 C30 H30 119.0 . . ?
C29 C30 H30 119.0 . . ?
C30 C31 C32 119.7(5) . . ?
C30 C31 H31 120.2 . . ?
C32 C31 H31 120.2 . . ?
C31 C32 C33 118.4(4) . . ?
C31 C32 H32 120.8 . . ?
C33 C32 H32 120.8 . . ?
C34 C33 C32 121.7(5) . . ?
C34 C33 H33 119.2 . . ?
C32 C33 H33 119.2 . . ?
C33 C34 C29 121.3(4) . . ?
C33 C34 H34 119.3 . . ?
C29 C34 H34 119.3 . . ?
C36 C35 C40 116.6(3) . . ?
C36 C35 C27 119.1(3) . . ?
C40 C35 C27 124.2(3) . . ?
C37 C36 C35 120.8(4) . . ?
C37 C36 H36 119.6 . . ?
C35 C36 H36 119.6 . . ?
C38 C37 C36 120.9(4) . . ?
C38 C37 H37 119.6 . . ?
C36 C37 H37 119.6 . . ?
C39 C38 C37 119.4(4) . . ?
C39 C38 H38 120.3 . . ?
C37 C38 H38 120.3 . . ?
C38 C39 C40 120.8(4) . . ?
C38 C39 H39 119.6 . . ?
C40 C39 H39 119.6 . . ?
C39 C40 C35 121.5(4) . . ?
C39 C40 H40 119.3 . . ?
C35 C40 H40 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
C6 C1 C2 C3 0.2(5) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C1 C2 C3 Cl2 -179.6(3) . . . . ?
C2 C3 C4 C5 0.2(5) . . . . ?
Cl2 C3 C4 C5 -179.9(2) . . . . ?
C3 C4 C5 C6 -1.0(5) . . . . ?
C2 C1 C6 C5 -1.0(5) . . . . ?
C2 C1 C6 C7 174.9(3) . . . . ?
C4 C5 C6 C1 1.4(5) . . . . ?
C4 C5 C6 C7 -174.5(3) . . . . ?
C1 C6 C7 C8 123.9(4) . . . . ?
C5 C6 C7 C8 -60.3(4) . . . . ?
C1 C6 C7 C15 -61.7(4) . . . . ?
C5 C6 C7 C15 114.0(3) . . . . ?
C6 C7 C8 C9 -9.4(5) . . . . ?
C15 C7 C8 C9 176.4(3) . . . . ?
C7 C8 C9 C10 -29.6(6) . . . . ?
C7 C8 C9 C14 154.2(4) . . . . ?
C14 C9 C10 C11 -1.0(5) . . . . ?
C8 C9 C10 C11 -177.3(3) . . . . ?
C9 C10 C11 C12 0.3(6) . . . . ?
C10 C11 C12 C13 0.9(6) . . . . ?
C11 C12 C13 C14 -1.3(6) . . . . ?
C12 C13 C14 C9 0.6(6) . . . . ?
C10 C9 C14 C13 0.5(5) . . . . ?
C8 C9 C14 C13 177.1(3) . . . . ?
C8 C7 C15 C16 -30.5(5) . . . . ?
C6 C7 C15 C16 155.0(3) . . . . ?
C8 C7 C15 C20 147.5(3) . . . . ?
C6 C7 C15 C20 -27.1(4) . . . . ?
C20 C15 C16 C17 -2.7(6) . . . . ?
C7 C15 C16 C17 175.3(4) . . . . ?
C15 C16 C17 C18 1.1(7) . . . . ?
C16 C17 C18 C19 1.1(7) . . . . ?
C17 C18 C19 C20 -1.6(7) . . . . ?
C18 C19 C20 C15 0.0(6) . . . . ?
C16 C15 C20 C19 2.2(6) . . . . ?
C7 C15 C20 C19 -176.0(3) . . . . ?
C26 C21 C22 C23 0.2(6) . . . . ?
C21 C22 C23 C24 -1.3(5) . . . . ?
C21 C22 C23 Cl1 176.0(3) . . . . ?
C22 C23 C24 C25 0.4(6) . . . . ?
Cl1 C23 C24 C25 -176.9(3) . . . . ?
C23 C24 C25 C26 1.6(6) . . . . ?
C22 C21 C26 C25 1.7(6) . . . . ?
C22 C21 C26 C27 -174.1(3) . . . . ?
C24 C25 C26 C21 -2.6(5) . . . . ?
C24 C25 C26 C27 173.1(3) . . . . ?
C21 C26 C27 C28 -127.3(4) . . . . ?
C25 C26 C27 C28 57.2(5) . . . . ?
C21 C26 C27 C35 57.9(4) . . . . ?
C25 C26 C27 C35 -117.6(4) . . . . ?
C35 C27 C28 C29 -177.9(3) . . . . ?
C26 C27 C28 C29 7.3(6) . . . . ?
C27 C28 C29 C34 28.6(6) . . . . ?
C27 C28 C29 C30 -156.4(4) . . . . ?
C34 C29 C30 C31 -1.2(7) . . . . ?
C28 C29 C30 C31 -176.6(4) . . . . ?
C29 C30 C31 C32 2.1(8) . . . . ?
C30 C31 C32 C33 -2.2(8) . . . . ?
C31 C32 C33 C34 1.4(7) . . . . ?
C32 C33 C34 C29 -0.5(7) . . . . ?
C30 C29 C34 C33 0.3(6) . . . . ?
C28 C29 C34 C33 175.3(4) . . . . ?
C28 C27 C35 C36 -145.8(4) . . . . ?
C26 C27 C35 C36 29.2(5) . . . . ?
C28 C27 C35 C40 31.7(5) . . . . ?
C26 C27 C35 C40 -153.3(3) . . . . ?
C40 C35 C36 C37 -2.0(6) . . . . ?
C27 C35 C36 C37 175.7(4) . . . . ?
C35 C36 C37 C38 -0.1(6) . . . . ?
C36 C37 C38 C39 2.1(7) . . . . ?
C37 C38 C39 C40 -1.9(7) . . . . ?
C38 C39 C40 C35 -0.3(7) . . . . ?
C36 C35 C40 C39 2.2(6) . . . . ?
C27 C35 C40 C39 -175.4(4) . . . . ?

_refine_diff_density_max         0.524
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.052



####################################################################### 
# 
# 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_xl1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2080256'
loop_
_audit_author_name
_audit_author_address
'Zuoqin Liang'
;Suzhou university of scinece and technology
China
;
_audit_update_record             
;
2021-04-27 deposited with the CCDC.	2024-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16'
_chemical_formula_weight         256.33

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   8.4084(18)
_cell_length_b                   16.183(3)
_cell_length_c                   10.936(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.264(3)
_cell_angle_gamma                90
_cell_volume                     1486.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2795
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      23.86

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.065
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7295
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.249
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.960
_reflns_number_total             2580
_reflns_number_gt                1932
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_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)+(0.2800P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2580
_refine_ls_number_parameters     181
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0848
_refine_ls_wR_factor_ref         0.3348
_refine_ls_wR_factor_gt          0.2955
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.041
_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
C1 C 0.3469(4) 0.1794(2) 0.7292(3) 0.0785(9) Uani 1 1 d . . . . .
H1 H 0.350485 0.220525 0.788606 0.094 Uiso 1 1 calc R U . . .
C2 C 0.2868(4) 0.1022(2) 0.7572(3) 0.0840(10) Uani 1 1 d . . . . .
H2 H 0.252283 0.091745 0.835461 0.101 Uiso 1 1 calc R U . . .
C3 C 0.2780(3) 0.04206(19) 0.6713(4) 0.0810(10) Uani 1 1 d . . . . .
H3 H 0.234716 -0.009086 0.689873 0.097 Uiso 1 1 calc R U . . .
C4 C 0.3330(3) 0.05640(17) 0.5566(3) 0.0758(9) Uani 1 1 d . . . . .
H4 H 0.328464 0.014636 0.498171 0.091 Uiso 1 1 calc R U . . .
C5 C 0.3949(3) 0.13246(18) 0.5279(3) 0.0721(8) Uani 1 1 d . . . . .
H5 H 0.432671 0.141671 0.450280 0.086 Uiso 1 1 calc R U . . .
C6 C 0.4012(4) 0.19605(17) 0.6149(3) 0.0688(8) Uani 1 1 d . U . . .
C7 C 0.4504(4) 0.28302(19) 0.5883(3) 0.0735(7) Uani 1 1 d . U . . .
C8 C 0.5837(4) 0.3005(2) 0.5318(3) 0.0760(8) Uani 1 1 d . U . . .
H8 H 0.597986 0.355745 0.511441 0.091 Uiso 1 1 calc R U . . .
C9 C 0.7145(3) 0.24256(18) 0.4965(2) 0.0662(8) Uani 1 1 d . U . . .
C10 C 0.7736(4) 0.1740(2) 0.5610(3) 0.0751(9) Uani 1 1 d . . . . .
H10 H 0.723613 0.156452 0.630736 0.090 Uiso 1 1 calc R U . . .
C11 C 0.9052(4) 0.1322(2) 0.5226(3) 0.0833(10) Uani 1 1 d . . . . .
H11 H 0.945482 0.087969 0.568453 0.100 Uiso 1 1 calc R U . . .
C12 C 0.9774(4) 0.1548(2) 0.4175(4) 0.0867(10) Uani 1 1 d . . . . .
H12 H 1.063334 0.124839 0.390184 0.104 Uiso 1 1 calc R U . . .
C13 C 0.9219(5) 0.2218(3) 0.3536(3) 0.0964(11) Uani 1 1 d . . . . .
H13 H 0.970303 0.237877 0.282387 0.116 Uiso 1 1 calc R U . . .
C14 C 0.7946(5) 0.2656(2) 0.3941(4) 0.0869(10) Uani 1 1 d . . . . .
H14 H 0.761040 0.312439 0.351142 0.104 Uiso 1 1 calc R U . . .
C15 C 0.3450(4) 0.35398(18) 0.6154(3) 0.0705(8) Uani 1 1 d . . . . .
C16 C 0.4013(4) 0.4286(2) 0.6623(3) 0.0847(10) Uani 1 1 d . . . . .
H16 H 0.509565 0.435123 0.680308 0.102 Uiso 1 1 calc R U . . .
C17 C 0.2991(5) 0.4926(2) 0.6823(4) 0.0954(12) Uani 1 1 d . . . . .
H17 H 0.339241 0.542489 0.712285 0.115 Uiso 1 1 calc R U . . .
C18 C 0.1416(6) 0.4843(2) 0.6592(4) 0.0947(12) Uani 1 1 d . U . . .
H18 H 0.073279 0.528010 0.674584 0.114 Uiso 1 1 calc R U . . .
C19 C 0.0819(4) 0.4113(2) 0.6129(3) 0.0892(10) Uani 1 1 d . U . . .
H19 H -0.026770 0.405846 0.595528 0.107 Uiso 1 1 calc R U . . .
C20 C 0.1838(4) 0.34555(18) 0.5919(3) 0.0770(9) Uani 1 1 d . . . . .
H20 H 0.142875 0.295799 0.561910 0.092 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
C1 C6 1.374(5) . ?
C1 C2 1.386(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.353(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.401(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.499(4) . ?
C7 C8 1.332(5) . ?
C7 C15 1.487(4) . ?
C8 C9 1.507(4) . ?
C8 H8 0.9300 . ?
C9 C14 1.380(5) . ?
C9 C10 1.395(4) . ?
C10 C11 1.377(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.370(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.362(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.372(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C20 1.376(5) . ?
C15 C16 1.387(4) . ?
C16 C17 1.369(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.346(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.373(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.391(5) . ?
C19 H19 0.9300 . ?
C20 H20 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
C6 C1 C2 121.0(3) . . ?
C6 C1 H1 119.5 . . ?
C2 C1 H1 119.5 . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 120.1(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.2(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.4(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 117.9(3) . . ?
C1 C6 C7 117.7(2) . . ?
C5 C6 C7 124.1(3) . . ?
C8 C7 C15 116.6(3) . . ?
C8 C7 C6 122.2(3) . . ?
C15 C7 C6 121.0(3) . . ?
C7 C8 C9 128.5(3) . . ?
C7 C8 H8 115.7 . . ?
C9 C8 H8 115.7 . . ?
C14 C9 C10 116.7(3) . . ?
C14 C9 C8 115.1(3) . . ?
C10 C9 C8 127.9(3) . . ?
C11 C10 C9 120.8(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 120.8(3) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 119.3(3) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C14 120.1(3) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C9 122.3(3) . . ?
C13 C14 H14 118.8 . . ?
C9 C14 H14 118.8 . . ?
C20 C15 C16 118.3(3) . . ?
C20 C15 C7 118.5(3) . . ?
C16 C15 C7 123.2(3) . . ?
C17 C16 C15 120.7(3) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C16 121.0(3) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C19 119.8(3) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C20 120.1(3) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C15 C20 C19 120.1(3) . . ?
C15 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?

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
C6 C1 C2 C3 -1.2(5) . . . . ?
C1 C2 C3 C4 1.9(5) . . . . ?
C2 C3 C4 C5 -1.1(4) . . . . ?
C3 C4 C5 C6 -0.5(4) . . . . ?
C2 C1 C6 C5 -0.4(5) . . . . ?
C2 C1 C6 C7 174.5(3) . . . . ?
C4 C5 C6 C1 1.2(4) . . . . ?
C4 C5 C6 C7 -173.4(3) . . . . ?
C1 C6 C7 C8 135.2(3) . . . . ?
C5 C6 C7 C8 -50.2(5) . . . . ?
C1 C6 C7 C15 -49.6(4) . . . . ?
C5 C6 C7 C15 124.9(3) . . . . ?
C15 C7 C8 C9 177.9(3) . . . . ?
C6 C7 C8 C9 -6.8(5) . . . . ?
C7 C8 C9 C14 150.4(4) . . . . ?
C7 C8 C9 C10 -36.5(5) . . . . ?
C14 C9 C10 C11 -0.2(5) . . . . ?
C8 C9 C10 C11 -173.2(3) . . . . ?
C9 C10 C11 C12 -2.5(5) . . . . ?
C10 C11 C12 C13 2.8(5) . . . . ?
C11 C12 C13 C14 -0.3(6) . . . . ?
C12 C13 C14 C9 -2.6(6) . . . . ?
C10 C9 C14 C13 2.8(5) . . . . ?
C8 C9 C14 C13 176.7(4) . . . . ?
C8 C7 C15 C20 135.6(3) . . . . ?
C6 C7 C15 C20 -39.7(4) . . . . ?
C8 C7 C15 C16 -43.8(4) . . . . ?
C6 C7 C15 C16 140.8(3) . . . . ?
C20 C15 C16 C17 -1.3(5) . . . . ?
C7 C15 C16 C17 178.2(3) . . . . ?
C15 C16 C17 C18 1.2(6) . . . . ?
C16 C17 C18 C19 -1.1(6) . . . . ?
C17 C18 C19 C20 1.1(6) . . . . ?
C16 C15 C20 C19 1.2(5) . . . . ?
C7 C15 C20 C19 -178.2(3) . . . . ?
C18 C19 C20 C15 -1.2(5) . . . . ?

_refine_diff_density_max         0.727
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.052



####################################################################### 
# 
# 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_lc1_a
_database_code_depnum_ccdc_archive 'CCDC 2285411'
loop_
_audit_author_name
_audit_author_address
Lzc
;Suzhou University of Science and Technology
China
;
_audit_update_record             
;
2023-07-30 deposited with the CCDC.	2024-06-18 downloaded from the CCDC.
;
_audit_creation_date             2022-11-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C20 H15 Br)'
_chemical_formula_sum            'C40 H30 Br2'
_chemical_formula_weight         670.46
_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'
Br Br -0.2901 2.4595 '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                   9.380(2)
_cell_length_b                   12.428(4)
_cell_length_c                   15.481(4)
_cell_angle_alpha                72.298(5)
_cell_angle_beta                 72.889(4)
_cell_angle_gamma                70.044(3)
_cell_volume                     1579.2(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2410
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.64
_cell_measurement_theta_min      2.36
_shelx_estimated_absorpt_T_max   0.682
_shelx_estimated_absorpt_T_min   0.652
_exptl_absorpt_coefficient_mu    2.594
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_unetI/netI     0.1103
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14415
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.598
_diffrn_reflns_theta_min         2.013
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3028
_reflns_number_total             7197
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.651
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         7197
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.1615
_refine_ls_R_factor_gt           0.0615
_refine_ls_restrained_S_all      1.009
_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)+(0.0700P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1531
_refine_ls_wR_factor_ref         0.1880
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H2(0.078) H3(0.071) H6(0.085) H8(0.089) H9(0.102) H10(0.105)
 H12(0.078) H13(0.109) H14(0.127) H15(0.112) H16(0.095) H17(0.093) H18(0.077)
 H19(0.076) H20(0.078) H22(0.085) H23(0.087) H26(0.088) H28(0.091) H29(0.115)
 H30(0.118) H31(0.087) H32(0.079) H34(0.084) H35(0.103) H36(0.109) H37(0.105)
 H38(0.09) H39(0.132) H40(0.109)
 Fixed X: H2(0.374387) H3(0.374623) H6(0.205706) H8(0.30024) H9(0.258913)
 H10(0.11962) H12(0.296466) H13(0.344176) H14(0.264864) H15(0.142409)
 H16(0.097912) H17(-0.000978) H18(0.028473) H19(-0.025612) H20(-0.025061)
 H22(0.914649) H23(0.877025) H26(0.66083) H28(0.560353) H29(0.542575)
 H30(0.629322) H31(0.494976) H32(0.525663) H34(0.794787) H35(0.821935)
 H36(0.702196) H37(0.564528) H38(0.536591) H39(0.732253) H40(0.746815)
 Fixed Y: H2(0.067636) H3(0.204595) H6(0.420419) H8(0.560933) H9(0.688625)
 H10(0.659513) H12(0.057246) H13(-0.033885) H14(0.081128) H15(0.277987)
 H16(0.360426) H17(0.515453) H18(0.389551) H19(0.165446) H20(0.031553)
 H22(0.136087) H23(0.289154) H26(0.569763) H28(0.298897) H29(0.170282)
 H30(0.185416) H31(0.461699) H32(0.308296) H34(0.536426) H35(0.703386)
 H36(0.885043) H37(0.897837) H38(0.730034) H39(0.339416) H40(0.473273)
 Fixed Z: H2(0.21) H3(0.283108) H6(0.4355) H8(0.300926) H9(0.160278)
 H10(0.077621) H12(0.512535) H13(0.661111) H14(0.771799) H15(0.731267)
 H16(0.5891) H17(0.136035) H18(0.273703) H19(0.453643) H20(0.378282)
 H22(0.15052) H23(0.216193) H26(0.297846) H28(0.345892) H29(0.482753)
 H30(0.602965) H31(0.118304) H32(0.054068) H34(0.028263) H35(-0.080274) H36(-
 0.045989) H37(0.100516) H38(0.212586) H39(0.580116) H40(0.437512)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.17614(8) -0.07422(5) 0.22717(5) 0.0937(3) Uani 1 1 d . . . . .
Br2 Br 0.75834(9) 0.08867(5) 0.03425(5) 0.1046(3) Uani 1 1 d . . . . .
C1 C 0.1747(6) 0.0379(4) 0.2874(4) 0.0592(13) Uani 1 1 d . . . . .
C2 C 0.2934(6) 0.0879(4) 0.2592(4) 0.0647(14) Uani 1 1 d . . . . .
H2 H 0.374387 0.067636 0.210000 0.078 Uiso 1 1 calc R U . . .
C3 C 0.2942(5) 0.1692(4) 0.3036(3) 0.0595(13) Uani 1 1 d . . . . .
H3 H 0.374623 0.204595 0.283108 0.071 Uiso 1 1 calc R U . . .
C4 C 0.1756(5) 0.1981(4) 0.3784(3) 0.0537(12) Uani 1 1 d . . . . .
C5 C 0.1807(5) 0.2783(5) 0.4333(4) 0.0621(12) Uani 1 1 d . U . . .
C6 C 0.1862(5) 0.3843(5) 0.3973(4) 0.0711(15) Uani 1 1 d . . . . .
H6 H 0.205706 0.420419 0.435500 0.085 Uiso 1 1 calc R U . . .
C7 C 0.1668(5) 0.4573(4) 0.3059(3) 0.0541(12) Uani 1 1 d . . . . .
C8 C 0.2383(6) 0.5505(5) 0.2687(4) 0.0744(16) Uani 1 1 d . . . . .
H8 H 0.300240 0.560933 0.300926 0.089 Uiso 1 1 calc R U . . .
C9 C 0.2148(7) 0.6262(5) 0.1837(5) 0.0853(18) Uani 1 1 d . . . . .
H9 H 0.258913 0.688625 0.160278 0.102 Uiso 1 1 calc R U . . .
C10 C 0.1303(7) 0.6103(6) 0.1355(5) 0.0878(18) Uani 1 1 d . . . . .
H10 H 0.119620 0.659513 0.077621 0.105 Uiso 1 1 calc R U . . .
C11 C 0.1985(5) 0.2213(4) 0.5340(4) 0.0591(12) Uani 1 1 d . U . . .
C12 C 0.2679(5) 0.1014(5) 0.5569(4) 0.0651(13) Uani 1 1 d . . . . .
H12 H 0.296466 0.057246 0.512535 0.078 Uiso 1 1 calc R U . . .
C13 C 0.2954(6) 0.0462(6) 0.6459(5) 0.0905(19) Uani 1 1 d . . . . .
H13 H 0.344176 -0.033885 0.661111 0.109 Uiso 1 1 calc R U . . .
C14 C 0.2474(8) 0.1151(8) 0.7121(4) 0.106(2) Uani 1 1 d . . . . .
H14 H 0.264864 0.081128 0.771799 0.127 Uiso 1 1 calc R U . . .
C15 C 0.1749(8) 0.2322(7) 0.6877(5) 0.0929(19) Uani 1 1 d . . . . .
H15 H 0.142409 0.277987 0.731267 0.112 Uiso 1 1 calc R U . . .
C16 C 0.1506(6) 0.2810(5) 0.6027(5) 0.0788(16) Uani 1 1 d . . . . .
H16 H 0.097912 0.360426 0.589100 0.095 Uiso 1 1 calc R U . . .
C17 C 0.0605(6) 0.5239(5) 0.1696(4) 0.0771(16) Uani 1 1 d . . . . .
H17 H -0.000978 0.515453 0.136035 0.093 Uiso 1 1 calc R U . . .
C18 C 0.0779(5) 0.4490(4) 0.2522(4) 0.0643(13) Uani 1 1 d . . . . .
H18 H 0.028473 0.389551 0.273703 0.077 Uiso 1 1 calc R U . . .
C19 C 0.0562(5) 0.1462(4) 0.4046(3) 0.0635(13) Uani 1 1 d . . . . .
H19 H -0.025612 0.165446 0.453643 0.076 Uiso 1 1 calc R U . . .
C20 C 0.0561(6) 0.0661(4) 0.3595(4) 0.0647(13) Uani 1 1 d . . . . .
H20 H -0.025061 0.031553 0.378282 0.078 Uiso 1 1 calc R U . . .
C21 C 0.7235(6) 0.2089(4) 0.0957(3) 0.0606(13) Uani 1 1 d . . . . .
C22 C 0.8295(6) 0.2017(4) 0.1442(4) 0.0705(14) Uani 1 1 d . . . . .
H22 H 0.914649 0.136087 0.150520 0.085 Uiso 1 1 calc R U . . .
C23 C 0.8065(6) 0.2936(5) 0.1829(4) 0.0725(15) Uani 1 1 d . . . . .
H23 H 0.877025 0.289154 0.216193 0.087 Uiso 1 1 calc R U . . .
C24 C 0.6830(6) 0.3915(5) 0.1742(4) 0.0673(13) Uani 1 1 d . U . . .
C25 C 0.6647(6) 0.5008(4) 0.2072(4) 0.0648(12) Uani 1 1 d . U . . .
C26 C 0.6606(6) 0.4993(5) 0.2886(4) 0.0730(13) Uani 1 1 d . U . . .
H26 H 0.660830 0.569763 0.297846 0.088 Uiso 1 1 calc R U . . .
C27 C 0.6550(5) 0.4000(5) 0.3760(4) 0.0639(12) Uani 1 1 d . U . . .
C28 C 0.5952(6) 0.3081(5) 0.3929(4) 0.0759(16) Uani 1 1 d . . . . .
H28 H 0.560353 0.298897 0.345892 0.091 Uiso 1 1 calc R U . . .
C29 C 0.5850(7) 0.2313(5) 0.4742(6) 0.096(2) Uani 1 1 d . . . . .
H29 H 0.542575 0.170282 0.482753 0.115 Uiso 1 1 calc R U . . .
C30 C 0.6362(8) 0.2401(7) 0.5465(5) 0.099(2) Uani 1 1 d . . . . .
H30 H 0.629322 0.185416 0.602965 0.118 Uiso 1 1 calc R U . . .
C31 C 0.5794(6) 0.3957(4) 0.1252(4) 0.0722(15) Uani 1 1 d . . . . .
H31 H 0.494976 0.461699 0.118304 0.087 Uiso 1 1 calc R U . . .
C32 C 0.5975(6) 0.3047(4) 0.0861(4) 0.0654(13) Uani 1 1 d . . . . .
H32 H 0.525663 0.308296 0.054068 0.079 Uiso 1 1 calc R U . . .
C33 C 0.6677(5) 0.6131(4) 0.1341(4) 0.0632(12) Uani 1 1 d . U . . .
C34 C 0.7491(6) 0.6088(5) 0.0443(4) 0.0699(15) Uani 1 1 d . . . . .
H34 H 0.794787 0.536426 0.028263 0.084 Uiso 1 1 calc R U . . .
C35 C 0.7635(7) 0.7087(6) -0.0209(4) 0.0862(17) Uani 1 1 d . . . . .
H35 H 0.821935 0.703386 -0.080274 0.103 Uiso 1 1 calc R U . . .
C36 C 0.6933(8) 0.8173(6) -0.0005(5) 0.0907(18) Uani 1 1 d . . . . .
H36 H 0.702196 0.885043 -0.045989 0.109 Uiso 1 1 calc R U . . .
C37 C 0.6112(7) 0.8246(5) 0.0860(5) 0.0873(17) Uani 1 1 d . . . . .
H37 H 0.564528 0.897837 0.100516 0.105 Uiso 1 1 calc R U . . .
C38 C 0.5957(6) 0.7237(5) 0.1536(4) 0.0754(15) Uani 1 1 d . . . . .
H38 H 0.536591 0.730034 0.212586 0.090 Uiso 1 1 calc R U . . .
C39 C 0.6972(9) 0.3311(8) 0.5329(5) 0.110(2) Uani 1 1 d . . . . .
H39 H 0.732253 0.339416 0.580116 0.132 Uiso 1 1 calc R U . . .
C40 C 0.7059(7) 0.4112(5) 0.4470(5) 0.0906(18) Uani 1 1 d . . . . .
H40 H 0.746815 0.473273 0.437512 0.109 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 1.893(5) . ?
Br2 C21 1.895(5) . ?
C1 C2 1.355(7) . ?
C1 C20 1.359(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.389(6) . ?
C4 C5 1.513(6) . ?
C4 C19 1.379(6) . ?
C5 C6 1.277(7) . ?
C5 C11 1.536(7) . ?
C6 H6 0.9300 . ?
C6 C7 1.455(7) . ?
C7 C8 1.421(7) . ?
C7 C18 1.385(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.394(8) . ?
C9 H9 0.9300 . ?
C9 C10 1.330(8) . ?
C10 H10 0.9300 . ?
C10 C17 1.338(8) . ?
C11 C12 1.387(7) . ?
C11 C16 1.362(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.396(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.408(9) . ?
C14 H14 0.9300 . ?
C14 C15 1.365(9) . ?
C15 H15 0.9300 . ?
C15 C16 1.323(8) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C17 C18 1.350(7) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C19 C20 1.380(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.378(7) . ?
C21 C32 1.369(7) . ?
C22 H22 0.9300 . ?
C22 C23 1.372(7) . ?
C23 H23 0.9300 . ?
C23 C24 1.367(7) . ?
C24 C25 1.533(7) . ?
C24 C31 1.377(7) . ?
C25 C26 1.244(6) . ?
C25 C33 1.510(7) . ?
C26 H26 0.9300 . ?
C26 C27 1.531(7) . ?
C27 C28 1.362(7) . ?
C27 C40 1.379(7) . ?
C28 H28 0.9300 . ?
C28 C29 1.329(8) . ?
C29 H29 0.9300 . ?
C29 C30 1.387(9) . ?
C30 H30 0.9300 . ?
C30 C39 1.370(9) . ?
C31 H31 0.9300 . ?
C31 C32 1.377(7) . ?
C32 H32 0.9300 . ?
C33 C34 1.382(7) . ?
C33 C38 1.390(7) . ?
C34 H34 0.9300 . ?
C34 C35 1.361(7) . ?
C35 H35 0.9300 . ?
C35 C36 1.372(8) . ?
C36 H36 0.9300 . ?
C36 C37 1.347(8) . ?
C37 H37 0.9300 . ?
C37 C38 1.388(7) . ?
C38 H38 0.9300 . ?
C39 H39 0.9300 . ?
C39 C40 1.397(9) . ?
C40 H40 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 Br1 119.6(4) . . ?
C2 C1 C20 120.7(5) . . ?
C20 C1 Br1 119.7(4) . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 120.0(5) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.5(4) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 121.5(4) . . ?
C19 C4 C3 117.8(4) . . ?
C19 C4 C5 120.6(4) . . ?
C4 C5 C11 116.2(4) . . ?
C6 C5 C4 123.2(5) . . ?
C6 C5 C11 120.3(5) . . ?
C5 C6 H6 115.0 . . ?
C5 C6 C7 130.0(5) . . ?
C7 C6 H6 115.0 . . ?
C8 C7 C6 118.1(5) . . ?
C18 C7 C6 126.2(5) . . ?
C18 C7 C8 115.6(5) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 C7 119.6(5) . . ?
C9 C8 H8 120.2 . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 120.9(6) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C17 120.5(6) . . ?
C17 C10 H10 119.7 . . ?
C12 C11 C5 118.3(5) . . ?
C16 C11 C5 124.3(5) . . ?
C16 C11 C12 117.5(5) . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.7(5) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 120.9 . . ?
C12 C13 C14 118.2(6) . . ?
C14 C13 H13 120.9 . . ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.4(6) . . ?
C15 C14 H14 120.3 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.5(6) . . ?
C16 C15 H15 119.8 . . ?
C11 C16 H16 118.2 . . ?
C15 C16 C11 123.6(6) . . ?
C15 C16 H16 118.2 . . ?
C10 C17 H17 119.5 . . ?
C10 C17 C18 120.9(6) . . ?
C18 C17 H17 119.5 . . ?
C7 C18 H18 118.8 . . ?
C17 C18 C7 122.4(5) . . ?
C17 C18 H18 118.8 . . ?
C4 C19 H19 119.4 . . ?
C4 C19 C20 121.2(5) . . ?
C20 C19 H19 119.4 . . ?
C1 C20 C19 119.8(4) . . ?
C1 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C22 C21 Br2 119.7(4) . . ?
C32 C21 Br2 118.8(4) . . ?
C32 C21 C22 121.4(5) . . ?
C21 C22 H22 120.8 . . ?
C23 C22 C21 118.4(5) . . ?
C23 C22 H22 120.8 . . ?
C22 C23 H23 119.0 . . ?
C24 C23 C22 122.1(5) . . ?
C24 C23 H23 119.0 . . ?
C23 C24 C25 122.9(4) . . ?
C23 C24 C31 117.9(5) . . ?
C31 C24 C25 118.8(5) . . ?
C26 C25 C24 123.7(5) . . ?
C26 C25 C33 118.9(5) . . ?
C33 C25 C24 117.1(5) . . ?
C25 C26 H26 114.9 . . ?
C25 C26 C27 130.3(6) . . ?
C27 C26 H26 114.9 . . ?
C28 C27 C26 126.9(5) . . ?
C28 C27 C40 117.5(5) . . ?
C40 C27 C26 115.4(5) . . ?
C27 C28 H28 118.9 . . ?
C29 C28 C27 122.2(6) . . ?
C29 C28 H28 118.9 . . ?
C28 C29 H29 119.3 . . ?
C28 C29 C30 121.5(6) . . ?
C30 C29 H29 119.3 . . ?
C29 C30 H30 120.8 . . ?
C39 C30 C29 118.4(6) . . ?
C39 C30 H30 120.8 . . ?
C24 C31 H31 119.1 . . ?
C32 C31 C24 121.8(5) . . ?
C32 C31 H31 119.1 . . ?
C21 C32 C31 118.4(5) . . ?
C21 C32 H32 120.8 . . ?
C31 C32 H32 120.8 . . ?
C34 C33 C25 120.1(5) . . ?
C34 C33 C38 117.2(5) . . ?
C38 C33 C25 122.6(5) . . ?
C33 C34 H34 119.5 . . ?
C35 C34 C33 121.1(5) . . ?
C35 C34 H34 119.5 . . ?
C34 C35 H35 119.5 . . ?
C34 C35 C36 121.0(6) . . ?
C36 C35 H35 119.5 . . ?
C35 C36 H36 120.3 . . ?
C37 C36 C35 119.3(6) . . ?
C37 C36 H36 120.3 . . ?
C36 C37 H37 119.8 . . ?
C36 C37 C38 120.4(6) . . ?
C38 C37 H37 119.8 . . ?
C33 C38 H38 119.6 . . ?
C37 C38 C33 120.8(5) . . ?
C37 C38 H38 119.6 . . ?
C30 C39 H39 120.5 . . ?
C30 C39 C40 119.0(6) . . ?
C40 C39 H39 120.5 . . ?
C27 C40 C39 121.3(6) . . ?
C27 C40 H40 119.3 . . ?
C39 C40 H40 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
Br1 C1 C2 C3 -179.3(3) . . . . ?
Br1 C1 C20 C19 178.8(4) . . . . ?
Br2 C21 C22 C23 175.9(4) . . . . ?
Br2 C21 C32 C31 -175.2(4) . . . . ?
C1 C2 C3 C4 1.4(7) . . . . ?
C2 C1 C20 C19 -0.2(8) . . . . ?
C2 C3 C4 C5 174.5(4) . . . . ?
C2 C3 C4 C19 -1.9(7) . . . . ?
C3 C4 C5 C6 60.3(7) . . . . ?
C3 C4 C5 C11 -112.7(5) . . . . ?
C3 C4 C19 C20 1.4(7) . . . . ?
C4 C5 C6 C7 9.9(8) . . . . ?
C4 C5 C11 C12 25.0(6) . . . . ?
C4 C5 C11 C16 -155.1(5) . . . . ?
C4 C19 C20 C1 -0.4(8) . . . . ?
C5 C4 C19 C20 -175.1(4) . . . . ?
C5 C6 C7 C8 -154.6(5) . . . . ?
C5 C6 C7 C18 28.8(8) . . . . ?
C5 C11 C12 C13 176.2(4) . . . . ?
C5 C11 C16 C15 -175.8(5) . . . . ?
C6 C5 C11 C12 -148.2(5) . . . . ?
C6 C5 C11 C16 31.7(7) . . . . ?
C6 C7 C8 C9 -176.4(5) . . . . ?
C6 C7 C18 C17 176.9(5) . . . . ?
C7 C8 C9 C10 -2.0(8) . . . . ?
C8 C7 C18 C17 0.3(7) . . . . ?
C8 C9 C10 C17 2.8(9) . . . . ?
C9 C10 C17 C18 -2.0(9) . . . . ?
C10 C17 C18 C7 0.5(8) . . . . ?
C11 C5 C6 C7 -177.4(4) . . . . ?
C11 C12 C13 C14 1.5(8) . . . . ?
C12 C11 C16 C15 4.1(8) . . . . ?
C12 C13 C14 C15 0.6(9) . . . . ?
C13 C14 C15 C16 -0.4(10) . . . . ?
C14 C15 C16 C11 -2.1(10) . . . . ?
C16 C11 C12 C13 -3.7(7) . . . . ?
C18 C7 C8 C9 0.5(7) . . . . ?
C19 C4 C5 C6 -123.4(5) . . . . ?
C19 C4 C5 C11 63.7(6) . . . . ?
C20 C1 C2 C3 -0.3(7) . . . . ?
C21 C22 C23 C24 -0.5(8) . . . . ?
C22 C21 C32 C31 1.0(8) . . . . ?
C22 C23 C24 C25 -172.9(5) . . . . ?
C22 C23 C24 C31 0.5(8) . . . . ?
C23 C24 C25 C26 -57.9(8) . . . . ?
C23 C24 C25 C33 116.0(6) . . . . ?
C23 C24 C31 C32 0.3(8) . . . . ?
C24 C25 C26 C27 -6.9(9) . . . . ?
C24 C25 C33 C34 -28.1(6) . . . . ?
C24 C25 C33 C38 154.4(5) . . . . ?
C24 C31 C32 C21 -1.0(8) . . . . ?
C25 C24 C31 C32 173.9(5) . . . . ?
C25 C26 C27 C28 -27.4(9) . . . . ?
C25 C26 C27 C40 157.8(6) . . . . ?
C25 C33 C34 C35 -174.8(5) . . . . ?
C25 C33 C38 C37 175.0(5) . . . . ?
C26 C25 C33 C34 146.1(5) . . . . ?
C26 C25 C33 C38 -31.3(7) . . . . ?
C26 C27 C28 C29 -174.6(5) . . . . ?
C26 C27 C40 C39 175.6(5) . . . . ?
C27 C28 C29 C30 -0.5(9) . . . . ?
C28 C27 C40 C39 0.3(8) . . . . ?
C28 C29 C30 C39 0.5(9) . . . . ?
C29 C30 C39 C40 -0.2(10) . . . . ?
C30 C39 C40 C27 -0.3(10) . . . . ?
C31 C24 C25 C26 128.8(6) . . . . ?
C31 C24 C25 C33 -57.3(6) . . . . ?
C32 C21 C22 C23 -0.3(8) . . . . ?
C33 C25 C26 C27 179.2(5) . . . . ?
C33 C34 C35 C36 -2.2(8) . . . . ?
C34 C33 C38 C37 -2.5(8) . . . . ?
C34 C35 C36 C37 1.3(9) . . . . ?
C35 C36 C37 C38 -1.0(10) . . . . ?
C36 C37 C38 C33 1.6(9) . . . . ?
C38 C33 C34 C35 2.8(7) . . . . ?
C40 C27 C28 C29 0.1(8) . . . . ?

_shelx_SHELXL_version_number     2016/6
_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_xl2_a
_database_code_depnum_ccdc_archive 'CCDC 2087955'
loop_
_audit_author_name
_audit_author_address
'Zuoqin Liang'
;Suzhou university of scinece and technology
China
;
_audit_update_record             
;
2021-06-04 deposited with the CCDC.	2024-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H14 F'
_chemical_formula_weight         273.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.104(9)
_cell_length_b                   8.521(4)
_cell_length_c                   19.345(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2984(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1506
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      19.16

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_F_000             1144
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17376
_diffrn_reflns_av_unetI/netI     0.0571
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.106
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3407
_reflns_number_gt                1731
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_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)+(0.0600P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3407
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1185
_refine_ls_R_factor_gt           0.0546
_refine_ls_wR_factor_ref         0.1461
_refine_ls_wR_factor_gt          0.1200
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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
F1 F 0.09237(16) 0.2653(3) 0.01327(15) 0.1116(11) Uani 0.5 1 d . . P . .
F2 F 0.59147(12) 0.3301(3) 0.14515(12) 0.0804(7) Uani 0.5 1 d . . P . .
C1 C 0.32429(12) 0.1463(3) 0.40478(10) 0.0688(6) Uani 1 1 d . . . . .
H1 H 0.294043 0.059065 0.399059 0.083 Uiso 1 1 calc R U . . .
C2 C 0.36840(13) 0.1571(3) 0.46264(11) 0.0809(7) Uani 1 1 d . . . . .
H2 H 0.368180 0.076544 0.495052 0.097 Uiso 1 1 calc R U . . .
C3 C 0.41229(13) 0.2848(3) 0.47275(12) 0.0798(7) Uani 1 1 d . . . . .
H3 H 0.442178 0.291280 0.511744 0.096 Uiso 1 1 calc R U . . .
C4 C 0.41211(12) 0.4042(3) 0.42486(11) 0.0775(7) Uani 1 1 d . . . . .
H4 H 0.441330 0.492618 0.431752 0.093 Uiso 1 1 calc R U . . .
C5 C 0.36851(12) 0.3925(3) 0.36659(11) 0.0694(6) Uani 1 1 d . . . . .
H5 H 0.368895 0.473516 0.334364 0.083 Uiso 1 1 calc R U . . .
C6 C 0.32423(10) 0.2628(2) 0.35513(10) 0.0565(5) Uani 1 1 d . . . . .
C7 C 0.27770(11) 0.2505(2) 0.29274(10) 0.0607(5) Uani 1 1 d . . . . .
H7 H 0.228528 0.223310 0.299772 0.073 Uiso 1 1 calc R U . . .
C8 C 0.29835(10) 0.2741(2) 0.22736(10) 0.0510(5) Uani 1 1 d . . . . .
C9 C 0.24287(10) 0.2746(2) 0.17040(10) 0.0530(5) Uani 1 1 d . . . . .
C10 C 0.25976(11) 0.2139(3) 0.10564(10) 0.0629(6) Uani 1 1 d . . . . .
H10 H 0.306472 0.172249 0.097633 0.075 Uiso 1 1 calc R U . . .
C11 C 0.20827(15) 0.2144(3) 0.05297(11) 0.0785(7) Uani 1 1 d . . . . .
H11 H 0.220353 0.174166 0.009743 0.094 Uiso 1 1 calc R U . . .
C12 C 0.13919(15) 0.2747(3) 0.06486(14) 0.0817(7) Uani 1 1 d . . . . .
C13 C 0.12121(13) 0.3359(3) 0.12806(16) 0.0838(7) Uani 1 1 d . . . . .
H13 H 0.074331 0.377060 0.135681 0.101 Uiso 1 1 calc R U . . .
C14 C 0.17288(11) 0.3363(2) 0.18031(12) 0.0684(6) Uani 1 1 d . . . . .
H14 H 0.160538 0.378770 0.223066 0.082 Uiso 1 1 calc R U . . .
C15 C 0.37755(10) 0.2958(2) 0.20672(9) 0.0469(5) Uani 1 1 d . . . . .
C16 C 0.43166(11) 0.1961(2) 0.23132(9) 0.0560(5) Uani 1 1 d . . . . .
H16 H 0.418874 0.117307 0.262356 0.067 Uiso 1 1 calc R U . . .
C17 C 0.50394(12) 0.2110(3) 0.21086(11) 0.0672(6) Uani 1 1 d . . . . .
H17 H 0.539773 0.143277 0.228100 0.081 Uiso 1 1 calc R U . . .
C18 C 0.52284(11) 0.3266(3) 0.16476(11) 0.0651(6) Uani 1 1 d . . . . .
C19 C 0.47056(11) 0.4290(3) 0.13971(10) 0.0637(6) Uani 1 1 d . . . . .
H19 H 0.483856 0.508229 0.109090 0.076 Uiso 1 1 calc R U . . .
C20 C 0.39817(10) 0.4125(2) 0.16062(9) 0.0541(5) Uani 1 1 d . . . . .
H20 H 0.362534 0.480791 0.143509 0.065 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 C12 1.312(3) . ?
F2 C18 1.299(3) . ?
C1 C2 1.378(3) . ?
C1 C6 1.381(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.361(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.476(3) . ?
C7 C8 1.334(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.491(3) . ?
C8 C15 1.500(3) . ?
C9 C14 1.385(3) . ?
C9 C10 1.390(3) . ?
C10 C11 1.381(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.371(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.369(4) . ?
C13 C14 1.377(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.381(3) . ?
C15 C20 1.387(2) . ?
C16 C17 1.373(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.372(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.376(3) . ?
C19 C20 1.379(3) . ?
C19 H19 0.9300 . ?
C20 H20 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 C6 121.1(2) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
C3 C2 C1 120.6(2) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 119.5(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 119.9(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 121.3(2) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 117.5(2) . . ?
C1 C6 C7 121.20(19) . . ?
C5 C6 C7 121.25(19) . . ?
C8 C7 C6 127.21(18) . . ?
C8 C7 H7 116.4 . . ?
C6 C7 H7 116.4 . . ?
C7 C8 C9 120.82(18) . . ?
C7 C8 C15 122.60(17) . . ?
C9 C8 C15 116.55(16) . . ?
C14 C9 C10 117.86(19) . . ?
C14 C9 C8 121.00(19) . . ?
C10 C9 C8 121.14(18) . . ?
C11 C10 C9 121.0(2) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C12 C11 C10 119.5(2) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
F1 C12 C13 123.3(3) . . ?
F1 C12 C11 116.0(3) . . ?
C13 C12 C11 120.6(2) . . ?
C12 C13 C14 119.7(2) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C9 121.3(2) . . ?
C13 C14 H14 119.4 . . ?
C9 C14 H14 119.4 . . ?
C16 C15 C20 118.14(18) . . ?
C16 C15 C8 120.70(17) . . ?
C20 C15 C8 121.12(16) . . ?
C17 C16 C15 121.32(19) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C18 C17 C16 119.43(19) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
F2 C18 C17 116.4(2) . . ?
F2 C18 C19 122.7(2) . . ?
C17 C18 C19 120.84(19) . . ?
C18 C19 C20 119.07(19) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C19 C20 C15 121.18(18) . . ?
C19 C20 H20 119.4 . . ?
C15 C20 H20 119.4 . . ?

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
C6 C1 C2 C3 1.0(3) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C2 C1 C6 C5 -1.7(3) . . . . ?
C2 C1 C6 C7 179.3(2) . . . . ?
C4 C5 C6 C1 1.0(3) . . . . ?
C4 C5 C6 C7 -179.93(19) . . . . ?
C1 C6 C7 C8 -131.8(2) . . . . ?
C5 C6 C7 C8 49.2(3) . . . . ?
C6 C7 C8 C9 -173.14(19) . . . . ?
C6 C7 C8 C15 9.0(3) . . . . ?
C7 C8 C9 C14 36.2(3) . . . . ?
C15 C8 C9 C14 -145.84(18) . . . . ?
C7 C8 C9 C10 -144.1(2) . . . . ?
C15 C8 C9 C10 33.9(3) . . . . ?
C14 C9 C10 C11 -0.3(3) . . . . ?
C8 C9 C10 C11 179.97(18) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
C10 C11 C12 F1 -177.3(2) . . . . ?
C10 C11 C12 C13 0.8(3) . . . . ?
F1 C12 C13 C14 177.7(2) . . . . ?
C11 C12 C13 C14 -0.3(4) . . . . ?
C12 C13 C14 C9 -0.5(3) . . . . ?
C10 C9 C14 C13 0.8(3) . . . . ?
C8 C9 C14 C13 -179.47(19) . . . . ?
C7 C8 C15 C16 46.8(3) . . . . ?
C9 C8 C15 C16 -131.12(19) . . . . ?
C7 C8 C15 C20 -135.5(2) . . . . ?
C9 C8 C15 C20 46.5(2) . . . . ?
C20 C15 C16 C17 -0.1(3) . . . . ?
C8 C15 C16 C17 177.56(17) . . . . ?
C15 C16 C17 C18 -0.4(3) . . . . ?
C16 C17 C18 F2 -177.1(2) . . . . ?
C16 C17 C18 C19 1.0(3) . . . . ?
F2 C18 C19 C20 176.9(2) . . . . ?
C17 C18 C19 C20 -1.1(3) . . . . ?
C18 C19 C20 C15 0.6(3) . . . . ?
C16 C15 C20 C19 0.0(3) . . . . ?
C8 C15 C20 C19 -177.66(17) . . . . ?

_refine_diff_density_max         0.138
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.042



