# 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 2017

####################################################################### 
# 
# 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_10-2_in_C2c
_database_code_depnum_ccdc_archive 'CCDC 1476397'
_audit_update_record             
;
2017-07-27 deposited with the CCDC.
2017-08-15 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H12 Br0.29 F1.71'
_chemical_formula_iupac          ?
_chemical_formula_weight         307.96

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   12.6657(10)
_cell_length_b                   10.6594(9)
_cell_length_c                   11.1921(9)
_cell_angle_alpha                90
_cell_angle_beta                 115.080(2)
_cell_angle_gamma                90
_cell_volume                     1368.57(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5389
_cell_measurement_theta_min      2.6085
_cell_measurement_theta_max      26.4031
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.423
_exptl_crystal_size_mid          0.278
_exptl_crystal_size_min          0.106
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             630

_exptl_absorpt_coefficient_mu    0.943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  0.91

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  TRIUMPH

_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            10163
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         26.43
_diffrn_reflns_theta_full        26.43
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
Investigated crystal (10-2) contains mixture of F and Br 
substituted 4,4? binaphtyl. During structure refinement 
position and anisotropic temperature factors for all 
non-H atoms were refined. The occupancy ratio of F/Br 
was free to refine. In the F/Br mixed crystals possible 
lowering of the space group symmetry from C2/c to chiral 
C2 was observed. This was tested by structure refinement 
in both C2 (10-1_in_C2 data block) and C2/c (current 
data block) space groups. The C2/c choice gives 
significantly higher R values than corresponding C2 choice.
;

_reflns_number_total             1408
_reflns_number_gt                1259
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.0997
_refine_ls_goodness_of_fit_ref   1.243
_refine_ls_restrained_S_all      1.243
_refine_ls_number_reflns         1408
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0082P)²+2.3910P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.178
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX2 V2014 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX2 V2014 (Bruker AXS Inc., 2014)'

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 0.0488(4) 0.2830(4) 0.6183(4) 0.0281(7) Uani 0.145(2) 1 d . . P . .
F1 F 0.0731(3) 0.2926(4) 0.5966(4) 0.0344(9) Uani 0.855(2) 1 d . . P . .
C1 C 0.43544(18) 0.30083(18) 0.72572(18) 0.0261(5) Uani 1 1 d . . . . .
C2 C 0.3815(2) 0.20507(19) 0.76166(19) 0.0291(5) Uani 1 1 d . . . . .
H2 H 0.4280 0.1400 0.8170 0.035 Uiso 1 1 calc R U . . .
C3 C 0.2601(2) 0.2007(2) 0.7191(2) 0.0316(5) Uani 1 1 d . . . . .
H3 H 0.2248 0.1342 0.7456 0.038 Uiso 1 1 calc R U . . .
C4 C 0.19446(19) 0.2932(2) 0.6398(2) 0.0295(5) Uani 1 1 d . . . . .
C4A C 0.24145(19) 0.39318(18) 0.59485(19) 0.0256(5) Uani 1 1 d . . . . .
C5 C 0.1707(2) 0.4862(2) 0.5073(2) 0.0300(5) Uani 1 1 d . . . . .
H5 H 0.0887 0.4843 0.4791 0.036 Uiso 1 1 calc R U . . .
C6 C 0.2198(2) 0.5788(2) 0.4632(2) 0.0312(5) Uani 1 1 d . . . . .
H6 H 0.1718 0.6409 0.4043 0.037 Uiso 1 1 calc R U . . .
C7 C 0.3408(2) 0.58247(19) 0.5046(2) 0.0311(5) Uani 1 1 d . . . . .
H7 H 0.3742 0.6469 0.4729 0.037 Uiso 1 1 calc R U . . .
C8 C 0.41151(19) 0.49441(19) 0.59015(19) 0.0272(5) Uani 1 1 d . . . . .
H8 H 0.4934 0.4988 0.6175 0.033 Uiso 1 1 calc R U . . .
C8A C 0.36421(19) 0.39652(18) 0.63863(18) 0.0252(5) Uani 1 1 d . . . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C4 1.760(4) . ?
F1 C4 1.403(4) . ?
C1 C2 1.380(3) . ?
C1 C8A 1.435(3) . ?
C1 C1 1.489(4) 2_656 ?
C2 C3 1.405(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.351(3) . ?
C3 H3 0.9500 . ?
C4 C4A 1.414(3) . ?
C4A C5 1.415(3) . ?
C4A C8A 1.419(3) . ?
C5 C6 1.365(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.401(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.369(3) . ?
C7 H7 0.9500 . ?
C8 C8A 1.420(3) . ?
C8 H8 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 C8A 118.5(2) . . ?
C2 C1 C1 119.79(16) . 2_656 ?
C8A C1 C1 121.67(15) . 2_656 ?
C1 C2 C3 122.1(2) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 H2 118.9 . . ?
C4 C3 C2 118.6(2) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 F1 120.2(2) . . ?
C3 C4 C4A 123.3(2) . . ?
F1 C4 C4A 116.5(2) . . ?
C3 C4 Br1 111.2(2) . . ?
F1 C4 Br1 11.5(2) . . ?
C4A C4 Br1 125.0(2) . . ?
C4 C4A C5 122.5(2) . . ?
C4 C4A C8A 117.46(19) . . ?
C5 C4A C8A 120.06(19) . . ?
C6 C5 C4A 120.4(2) . . ?
C6 C5 H5 119.8 . . ?
C4A C5 H5 119.8 . . ?
C5 C6 C7 120.1(2) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 120.8(2) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C8A 121.0(2) . . ?
C7 C8 H8 119.5 . . ?
C8A C8 H8 119.5 . . ?
C4A C8A C8 117.67(19) . . ?
C4A C8A C1 119.88(18) . . ?
C8 C8A C1 122.4(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8A C1 C2 C3 -2.0(3) . . . . ?
C1 C1 C2 C3 179.73(19) 2_656 . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C3 C4 F1 -179.3(2) . . . . ?
C2 C3 C4 C4A 1.4(3) . . . . ?
C2 C3 C4 Br1 -171.2(2) . . . . ?
C3 C4 C4A C5 177.27(19) . . . . ?
F1 C4 C4A C5 -2.1(3) . . . . ?
Br1 C4 C4A C5 -11.2(3) . . . . ?
C3 C4 C4A C8A -1.4(3) . . . . ?
F1 C4 C4A C8A 179.2(2) . . . . ?
Br1 C4 C4A C8A 170.1(2) . . . . ?
C4 C4A C5 C6 -177.86(19) . . . . ?
C8A C4A C5 C6 0.8(3) . . . . ?
C4A C5 C6 C7 -0.1(3) . . . . ?
C5 C6 C7 C8 -0.5(3) . . . . ?
C6 C7 C8 C8A 0.4(3) . . . . ?
C4 C4A C8A C8 177.89(17) . . . . ?
C5 C4A C8A C8 -0.8(3) . . . . ?
C4 C4A C8A C1 -0.3(3) . . . . ?
C5 C4A C8A C1 -178.99(17) . . . . ?
C7 C8 C8A C4A 0.2(3) . . . . ?
C7 C8 C8A C1 178.36(18) . . . . ?
C2 C1 C8A C4A 1.9(3) . . . . ?
C1 C1 C8A C4A -179.87(18) 2_656 . . . ?
C2 C1 C8A C8 -176.16(18) . . . . ?
C1 C1 C8A C8 2.0(3) 2_656 . . . ?

####################################################################### 
# 
# 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_22
_database_code_depnum_ccdc_archive 'CCDC 1528855'
_audit_update_record             
;
2017-07-27 deposited with the CCDC.
2017-08-15 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H12 Br2'
_chemical_formula_iupac          ?
_chemical_formula_weight         412.12

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_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                   7.3184(5)
_cell_length_b                   12.8258(9)
_cell_length_c                   18.0272(13)
_cell_angle_alpha                109.369(2)
_cell_angle_beta                 90.011(2)
_cell_angle_gamma                102.874(2)
_cell_volume                     1551.16(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9937
_cell_measurement_theta_min      2.4030
_cell_measurement_theta_max      25.4012
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.239
_exptl_crystal_size_mid          0.161
_exptl_crystal_size_min          0.126
_exptl_crystal_density_diffrn    1.765
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808

_exptl_absorpt_coefficient_mu    5.219
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS V2012 (Bruker AXS Inc., 2012)'
_exptl_absorpt_correction_T_min  0.37
_exptl_absorpt_correction_T_max  0.56

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  TRIUMPH

_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            31460
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_theta_min         2.40
_diffrn_reflns_theta_max         25.42
_diffrn_reflns_theta_full        25.42
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       21

_refine_special_details          'Refined as a 2-component twin.'

_reflns_number_total             5699
_reflns_number_gt                5121
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0316
_refine_ls_wR_factor_gt          0.0631
_refine_ls_wR_factor_ref         0.0664
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_refine_ls_number_reflns         5699
_refine_ls_number_parameters     398
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0245P)²+2.4259P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.751
_refine_diff_density_min         -0.396
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX2 V2014 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX2 V2014 (Bruker AXS Inc., 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1A 0.59008(6) 0.37188(4) 0.52057(3) 0.02118(12) Uani d . . . 1 . .
C C1A 0.2163(6) 0.2596(4) 0.4547(3) 0.0157(10) Uani d . . . 1 . .
C C2A 0.3926(6) 0.3065(4) 0.4390(3) 0.0167(10) Uani d . . . 1 . .
C C3A 0.4360(7) 0.3086(4) 0.3632(3) 0.0201(10) Uani d . . . 1 . .
H H3A 0.5596 0.3427 0.3545 0.024 Uiso calc U . R 1 . .
C C4A 0.3005(6) 0.2618(4) 0.3033(3) 0.0218(10) Uani d . . . 1 . .
H H4A 0.3303 0.263 0.2522 0.026 Uiso calc U . R 1 . .
C C4AA 0.1145(7) 0.2109(4) 0.3145(3) 0.0187(10) Uani d . . . 1 . .
C C5A -0.0282(7) 0.1609(4) 0.2520(3) 0.0239(11) Uani d . . . 1 . .
H H5A 0.0006 0.1595 0.2003 0.029 Uiso calc U . R 1 . .
C C6A -0.2065(7) 0.1145(4) 0.2646(3) 0.0278(11) Uani d . . . 1 . .
H H6A -0.3008 0.0801 0.2219 0.033 Uiso calc U . R 1 . .
C C7A -0.2502(7) 0.1179(4) 0.3411(3) 0.0237(11) Uani d . . . 1 . .
H H7A -0.3758 0.0879 0.3501 0.028 Uiso calc U . R 1 . .
C C8A -0.1159(6) 0.1632(4) 0.4025(3) 0.0191(10) Uani d . . . 1 . .
H H8A -0.1483 0.163 0.4535 0.023 Uiso calc U . R 1 . .
C C8AA 0.0717(6) 0.2106(4) 0.3914(3) 0.0147(10) Uani d . . . 1 . .
Br Br1B 0.28257(7) 0.04704(4) 0.48925(3) 0.02281(12) Uani d . . . 1 . .
C C1B 0.1723(6) 0.2559(4) 0.5345(3) 0.0139(9) Uani d . . . 1 . .
C C2B 0.1868(6) 0.1668(4) 0.5578(3) 0.0167(10) Uani d . . . 1 . .
C C3B 0.1378(6) 0.1591(4) 0.6313(3) 0.0171(10) Uani d . . . 1 . .
H H3B 0.1444 0.0935 0.6437 0.021 Uiso calc U . R 1 . .
C C4B 0.0807(6) 0.2465(4) 0.6847(3) 0.0171(10) Uani d . . . 1 . .
H H4B 0.05 0.2425 0.7351 0.02 Uiso calc U . R 1 . .
C C4AB 0.0666(6) 0.3429(4) 0.6660(3) 0.0159(10) Uani d . . . 1 . .
C C5B 0.0103(6) 0.4359(4) 0.7211(3) 0.0171(10) Uani d . . . 1 . .
H H5B -0.0196 0.4333 0.7718 0.021 Uiso calc U . R 1 . .
C C6B -0.0015(7) 0.5286(4) 0.7025(3) 0.0214(11) Uani d . . . 1 . .
H H6B -0.0405 0.5899 0.74 0.026 Uiso calc U . R 1 . .
C C7B 0.0434(6) 0.5337(4) 0.6286(3) 0.0188(11) Uani d . . . 1 . .
H H7B 0.0372 0.5995 0.6165 0.023 Uiso calc U . R 1 . .
C C8B 0.0965(6) 0.4458(4) 0.5730(3) 0.0166(10) Uani d . . . 1 . .
H H8B 0.1245 0.4506 0.5226 0.02 Uiso calc U . R 1 . .
C C8AB 0.1097(6) 0.3479(4) 0.5903(3) 0.0133(10) Uani d . . . 1 . .
Br Br1C 0.75854(7) 0.04168(4) 0.78225(3) 0.02665(12) Uani d . . . 1 . .
C C1C 0.6664(6) 0.2572(4) 0.8451(3) 0.0156(10) Uani d . . . 1 . .
C C2C 0.6742(6) 0.1696(4) 0.7782(3) 0.0182(10) Uani d . . . 1 . .
C C3C 0.6289(6) 0.1697(4) 0.7012(3) 0.0220(11) Uani d . . . 1 . .
H H3C 0.6365 0.1073 0.6557 0.026 Uiso calc U . R 1 . .
C C4C 0.5749(6) 0.2605(4) 0.6945(3) 0.0202(11) Uani d . . . 1 . .
H H4C 0.544 0.2614 0.6436 0.024 Uiso calc U . R 1 . .
C C4AC 0.5635(6) 0.3540(4) 0.7616(3) 0.0161(10) Uani d . . . 1 . .
C C5C 0.5093(6) 0.4502(4) 0.7548(3) 0.0211(11) Uani d . . . 1 . .
H H5C 0.4786 0.4516 0.704 0.025 Uiso calc U . R 1 . .
C C6C 0.5006(7) 0.5403(5) 0.8196(3) 0.0230(12) Uani d . . . 1 . .
H H6C 0.4619 0.6034 0.814 0.028 Uiso calc U . R 1 . .
C C7C 0.5492(7) 0.5403(4) 0.8953(3) 0.0218(11) Uani d . . . 1 . .
H H7C 0.5454 0.6041 0.9406 0.026 Uiso calc U . R 1 . .
C C8C 0.6017(6) 0.4489(4) 0.9039(3) 0.0182(10) Uani d . . . 1 . .
H H8C 0.6335 0.4498 0.9553 0.022 Uiso calc U . R 1 . .
C C8AC 0.6095(6) 0.3527(4) 0.8374(3) 0.0160(10) Uani d . . . 1 . .
Br Br1D 1.08361(7) 0.36805(4) 0.91675(3) 0.02436(12) Uani d . . . 1 . .
C C1D 0.7088(6) 0.2529(4) 0.9247(3) 0.0154(10) Uani d . . . 1 . .
C C2D 0.8833(6) 0.2980(4) 0.9638(3) 0.0195(10) Uani d . . . 1 . .
C C3D 0.9250(7) 0.2939(5) 1.0391(3) 0.0255(11) Uani d . . . 1 . .
H H3D 1.0477 0.3274 1.0649 0.031 Uiso calc U . R 1 . .
C C4D 0.7868(7) 0.2413(4) 1.0744(3) 0.0257(11) Uani d . . . 1 . .
H H4D 0.8146 0.2382 1.125 0.031 Uiso calc U . R 1 . .
C C4AD 0.6028(7) 0.1912(4) 1.0371(3) 0.0223(11) Uani d . . . 1 . .
C C5D 0.4584(8) 0.1360(4) 1.0721(3) 0.0315(13) Uani d . . . 1 . .
H H5D 0.4842 0.13 1.122 0.038 Uiso calc U . R 1 . .
C C6D 0.2823(8) 0.0911(5) 1.0353(4) 0.0389(15) Uani d . . . 1 . .
H H6D 0.1864 0.054 1.0597 0.047 Uiso calc U . R 1 . .
C C7D 0.2411(7) 0.0989(5) 0.9622(4) 0.0372(14) Uani d . . . 1 . .
H H7D 0.1173 0.0676 0.9373 0.045 Uiso calc U . R 1 . .
C C8D 0.3781(6) 0.1514(4) 0.9261(3) 0.0243(11) Uani d . . . 1 . .
H H8D 0.3481 0.156 0.8761 0.029 Uiso calc U . R 1 . .
C C8AD 0.5629(7) 0.1988(4) 0.9618(3) 0.0191(11) Uani d . . . 1 . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1A C2A . 1.897(5) ?
C1A C2A . 1.369(6) ?
C1A C8AA . 1.429(6) ?
C1A C1B . 1.487(6) ?
C2A C3A . 1.410(6) ?
C3A C4A . 1.348(7) ?
C3A H3A . 0.95 ?
C4A C4AA . 1.418(6) ?
C4A H4A . 0.95 ?
C4AA C5A . 1.412(7) ?
C4AA C8AA . 1.422(7) ?
C5A C6A . 1.361(7) ?
C5A H5A . 0.95 ?
C6A C7A . 1.405(8) ?
C6A H6A . 0.95 ?
C7A C8A . 1.359(7) ?
C7A H7A . 0.95 ?
C8A C8AA . 1.416(6) ?
C8A H8A . 0.95 ?
Br1B C2B . 1.897(4) ?
C1B C2B . 1.365(6) ?
C1B C8AB . 1.438(6) ?
C2B C3B . 1.403(7) ?
C3B C4B . 1.361(7) ?
C3B H3B . 0.95 ?
C4B C4AB . 1.410(6) ?
C4B H4B . 0.95 ?
C4AB C5B . 1.419(6) ?
C4AB C8AB . 1.419(7) ?
C5B C6B . 1.357(7) ?
C5B H5B . 0.95 ?
C6B C7B . 1.392(7) ?
C6B H6B . 0.95 ?
C7B C8B . 1.368(7) ?
C7B H7B . 0.95 ?
C8B C8AB . 1.413(6) ?
C8B H8B . 0.95 ?
Br1C C2C . 1.900(5) ?
C1C C2C . 1.360(7) ?
C1C C8AC . 1.425(6) ?
C1C C1D . 1.491(6) ?
C2C C3C . 1.427(7) ?
C3C C4C . 1.351(7) ?
C3C H3C . 0.95 ?
C4C C4AC . 1.411(7) ?
C4C H4C . 0.95 ?
C4AC C8AC . 1.415(7) ?
C4AC C5C . 1.418(7) ?
C5C C6C . 1.357(7) ?
C5C H5C . 0.95 ?
C6C C7C . 1.411(7) ?
C6C H6C . 0.95 ?
C7C C8C . 1.366(7) ?
C7C H7C . 0.95 ?
C8C C8AC . 1.420(6) ?
C8C H8C . 0.95 ?
Br1D C2D . 1.896(5) ?
C1D C2D . 1.365(7) ?
C1D C8AD . 1.430(7) ?
C2D C3D . 1.411(7) ?
C3D C4D . 1.366(7) ?
C3D H3D . 0.95 ?
C4D C4AD . 1.417(7) ?
C4D H4D . 0.95 ?
C4AD C5D . 1.408(7) ?
C4AD C8AD . 1.428(7) ?
C5D C6D . 1.360(8) ?
C5D H5D . 0.95 ?
C6D C7D . 1.391(9) ?
C6D H6D . 0.95 ?
C7D C8D . 1.369(7) ?
C7D H7D . 0.95 ?
C8D C8AD . 1.410(7) ?
C8D H8D . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2A C1A C8AA . . 118.3(4) ?
C2A C1A C1B . . 122.2(4) ?
C8AA C1A C1B . . 119.5(4) ?
C1A C2A C3A . . 122.6(5) ?
C1A C2A Br1A . . 120.1(4) ?
C3A C2A Br1A . . 117.3(4) ?
C4A C3A C2A . . 119.3(5) ?
C4A C3A H3A . . 120.4 ?
C2A C3A H3A . . 120.4 ?
C3A C4A C4AA . . 121.7(5) ?
C3A C4A H4A . . 119.2 ?
C4AA C4A H4A . . 119.2 ?
C5A C4AA C4A . . 122.1(5) ?
C5A C4AA C8AA . . 119.4(4) ?
C4A C4AA C8AA . . 118.5(4) ?
C6A C5A C4AA . . 121.0(5) ?
C6A C5A H5A . . 119.5 ?
C4AA C5A H5A . . 119.5 ?
C5A C6A C7A . . 119.6(5) ?
C5A C6A H6A . . 120.2 ?
C7A C6A H6A . . 120.2 ?
C8A C7A C6A . . 121.1(5) ?
C8A C7A H7A . . 119.4 ?
C6A C7A H7A . . 119.4 ?
C7A C8A C8AA . . 120.8(5) ?
C7A C8A H8A . . 119.6 ?
C8AA C8A H8A . . 119.6 ?
C8A C8AA C4AA . . 118.1(4) ?
C8A C8AA C1A . . 122.3(4) ?
C4AA C8AA C1A . . 119.7(4) ?
C2B C1B C8AB . . 117.3(4) ?
C2B C1B C1A . . 122.6(4) ?
C8AB C1B C1A . . 120.1(4) ?
C1B C2B C3B . . 123.6(4) ?
C1B C2B Br1B . . 119.4(4) ?
C3B C2B Br1B . . 117.0(3) ?
C4B C3B C2B . . 119.3(4) ?
C4B C3B H3B . . 120.3 ?
C2B C3B H3B . . 120.3 ?
C3B C4B C4AB . . 120.5(4) ?
C3B C4B H4B . . 119.7 ?
C4AB C4B H4B . . 119.7 ?
C4B C4AB C5B . . 121.6(4) ?
C4B C4AB C8AB . . 119.6(4) ?
C5B C4AB C8AB . . 118.8(5) ?
C6B C5B C4AB . . 121.1(4) ?
C6B C5B H5B . . 119.5 ?
C4AB C5B H5B . . 119.5 ?
C5B C6B C7B . . 119.9(5) ?
C5B C6B H6B . . 120.0 ?
C7B C6B H6B . . 120.0 ?
C8B C7B C6B . . 121.3(5) ?
C8B C7B H7B . . 119.3 ?
C6B C7B H7B . . 119.3 ?
C7B C8B C8AB . . 120.2(5) ?
C7B C8B H8B . . 119.9 ?
C8AB C8B H8B . . 119.9 ?
C8B C8AB C4AB . . 118.7(4) ?
C8B C8AB C1B . . 121.7(4) ?
C4AB C8AB C1B . . 119.5(4) ?
C2C C1C C8AC . . 118.2(4) ?
C2C C1C C1D . . 121.5(4) ?
C8AC C1C C1D . . 120.3(4) ?
C1C C2C C3C . . 122.8(4) ?
C1C C2C Br1C . . 121.2(4) ?
C3C C2C Br1C . . 115.9(4) ?
C4C C3C C2C . . 118.6(5) ?
C4C C3C H3C . . 120.7 ?
C2C C3C H3C . . 120.7 ?
C3C C4C C4AC . . 121.4(5) ?
C3C C4C H4C . . 119.3 ?
C4AC C4C H4C . . 119.3 ?
C4C C4AC C8AC . . 119.3(5) ?
C4C C4AC C5C . . 121.6(4) ?
C8AC C4AC C5C . . 119.1(5) ?
C6C C5C C4AC . . 121.2(5) ?
C6C C5C H5C . . 119.4 ?
C4AC C5C H5C . . 119.4 ?
C5C C6C C7C . . 120.0(5) ?
C5C C6C H6C . . 120.0 ?
C7C C6C H6C . . 120.0 ?
C8C C7C C6C . . 120.3(5) ?
C8C C7C H7C . . 119.9 ?
C6C C7C H7C . . 119.9 ?
C7C C8C C8AC . . 121.1(5) ?
C7C C8C H8C . . 119.5 ?
C8AC C8C H8C . . 119.5 ?
C4AC C8AC C8C . . 118.3(4) ?
C4AC C8AC C1C . . 119.7(4) ?
C8C C8AC C1C . . 121.9(4) ?
C2D C1D C8AD . . 118.3(4) ?
C2D C1D C1C . . 122.4(4) ?
C8AD C1D C1C . . 119.3(4) ?
C1D C2D C3D . . 122.8(5) ?
C1D C2D Br1D . . 120.2(4) ?
C3D C2D Br1D . . 117.0(4) ?
C4D C3D C2D . . 119.2(5) ?
C4D C3D H3D . . 120.4 ?
C2D C3D H3D . . 120.4 ?
C3D C4D C4AD . . 121.3(5) ?
C3D C4D H4D . . 119.4 ?
C4AD C4D H4D . . 119.4 ?
C5D C4AD C4D . . 122.3(5) ?
C5D C4AD C8AD . . 119.3(5) ?
C4D C4AD C8AD . . 118.4(5) ?
C6D C5D C4AD . . 120.6(5) ?
C6D C5D H5D . . 119.7 ?
C4AD C5D H5D . . 119.7 ?
C5D C6D C7D . . 120.7(5) ?
C5D C6D H6D . . 119.6 ?
C7D C6D H6D . . 119.6 ?
C8D C7D C6D . . 120.4(5) ?
C8D C7D H7D . . 119.8 ?
C6D C7D H7D . . 119.8 ?
C7D C8D C8AD . . 121.0(5) ?
C7D C8D H8D . . 119.5 ?
C8AD C8D H8D . . 119.5 ?
C8D C8AD C4AD . . 118.0(5) ?
C8D C8AD C1D . . 122.0(5) ?
C4AD C8AD C1D . . 120.0(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8AA C1A C2A C3A . . . . 0.3(7) ?
C1B C1A C2A C3A . . . . 178.9(5) ?
C8AA C1A C2A Br1A . . . . -179.7(3) ?
C1B C1A C2A Br1A . . . . -1.0(6) ?
C1A C2A C3A C4A . . . . -0.8(8) ?
Br1A C2A C3A C4A . . . . 179.2(4) ?
C2A C3A C4A C4AA . . . . 0.4(7) ?
C3A C4A C4AA C5A . . . . -179.5(5) ?
C3A C4A C4AA C8AA . . . . 0.5(7) ?
C4A C4AA C5A C6A . . . . -178.7(4) ?
C8AA C4AA C5A C6A . . . . 1.3(7) ?
C4AA C5A C6A C7A . . . . 0.9(8) ?
C5A C6A C7A C8A . . . . -2.3(8) ?
C6A C7A C8A C8AA . . . . 1.3(7) ?
C7A C8A C8AA C4AA . . . . 0.9(7) ?
C7A C8A C8AA C1A . . . . 179.6(4) ?
C5A C4AA C8AA C8A . . . . -2.2(7) ?
C4A C4AA C8AA C8A . . . . 177.8(4) ?
C5A C4AA C8AA C1A . . . . 179.0(4) ?
C4A C4AA C8AA C1A . . . . -0.9(7) ?
C2A C1A C8AA C8A . . . . -178.1(4) ?
C1B C1A C8AA C8A . . . . 3.2(7) ?
C2A C1A C8AA C4AA . . . . 0.5(7) ?
C1B C1A C8AA C4AA . . . . -178.1(4) ?
C2A C1A C1B C2B . . . . -90.4(6) ?
C8AA C1A C1B C2B . . . . 88.2(5) ?
C2A C1A C1B C8AB . . . . 90.4(5) ?
C8AA C1A C1B C8AB . . . . -91.0(5) ?
C8AB C1B C2B C3B . . . . 2.3(7) ?
C1A C1B C2B C3B . . . . -176.9(4) ?
C8AB C1B C2B Br1B . . . . -176.3(3) ?
C1A C1B C2B Br1B . . . . 4.4(6) ?
C1B C2B C3B C4B . . . . -3.2(7) ?
Br1B C2B C3B C4B . . . . 175.5(3) ?
C2B C3B C4B C4AB . . . . 1.4(7) ?
C3B C4B C4AB C5B . . . . -179.0(4) ?
C3B C4B C4AB C8AB . . . . 1.0(7) ?
C4B C4AB C5B C6B . . . . 179.6(4) ?
C8AB C4AB C5B C6B . . . . -0.4(7) ?
C4AB C5B C6B C7B . . . . -0.5(8) ?
C5B C6B C7B C8B . . . . 1.3(8) ?
C6B C7B C8B C8AB . . . . -1.1(7) ?
C7B C8B C8AB C4AB . . . . 0.1(6) ?
C7B C8B C8AB C1B . . . . -177.4(4) ?
C4B C4AB C8AB C8B . . . . -179.4(4) ?
C5B C4AB C8AB C8B . . . . 0.6(6) ?
C4B C4AB C8AB C1B . . . . -1.8(6) ?
C5B C4AB C8AB C1B . . . . 178.2(4) ?
C2B C1B C8AB C8B . . . . 177.7(4) ?
C1A C1B C8AB C8B . . . . -3.0(6) ?
C2B C1B C8AB C4AB . . . . 0.2(6) ?
C1A C1B C8AB C4AB . . . . 179.4(4) ?
C8AC C1C C2C C3C . . . . 0.3(7) ?
C1D C1C C2C C3C . . . . 178.0(4) ?
C8AC C1C C2C Br1C . . . . 177.3(3) ?
C1D C1C C2C Br1C . . . . -4.9(6) ?
C1C C2C C3C C4C . . . . -0.3(7) ?
Br1C C2C C3C C4C . . . . -177.6(3) ?
C2C C3C C4C C4AC . . . . 0.2(7) ?
C3C C4C C4AC C8AC . . . . 0.0(7) ?
C3C C4C C4AC C5C . . . . 179.1(4) ?
C4C C4AC C5C C6C . . . . -179.3(5) ?
C8AC C4AC C5C C6C . . . . -0.2(7) ?
C4AC C5C C6C C7C . . . . 1.2(8) ?
C5C C6C C7C C8C . . . . -1.2(8) ?
C6C C7C C8C C8AC . . . . 0.3(7) ?
C4C C4AC C8AC C8C . . . . 178.4(4) ?
C5C C4AC C8AC C8C . . . . -0.8(6) ?
C4C C4AC C8AC C1C . . . . -0.1(7) ?
C5C C4AC C8AC C1C . . . . -179.2(4) ?
C7C C8C C8AC C4AC . . . . 0.7(7) ?
C7C C8C C8AC C1C . . . . 179.1(4) ?
C2C C1C C8AC C4AC . . . . -0.1(6) ?
C1D C1C C8AC C4AC . . . . -177.9(4) ?
C2C C1C C8AC C8C . . . . -178.5(4) ?
C1D C1C C8AC C8C . . . . 3.7(7) ?
C2C C1C C1D C2D . . . . 94.3(6) ?
C8AC C1C C1D C2D . . . . -88.0(6) ?
C2C C1C C1D C8AD . . . . -85.1(6) ?
C8AC C1C C1D C8AD . . . . 92.6(6) ?
C8AD C1D C2D C3D . . . . -0.4(7) ?
C1C C1D C2D C3D . . . . -179.7(5) ?
C8AD C1D C2D Br1D . . . . 178.7(3) ?
C1C C1D C2D Br1D . . . . -0.6(7) ?
C1D C2D C3D C4D . . . . 1.1(8) ?
Br1D C2D C3D C4D . . . . -178.0(4) ?
C2D C3D C4D C4AD . . . . -0.2(8) ?
C3D C4D C4AD C5D . . . . 179.7(5) ?
C3D C4D C4AD C8AD . . . . -1.2(7) ?
C4D C4AD C5D C6D . . . . 178.5(5) ?
C8AD C4AD C5D C6D . . . . -0.6(8) ?
C4AD C5D C6D C7D . . . . -0.1(9) ?
C5D C6D C7D C8D . . . . 0.4(10) ?
C6D C7D C8D C8AD . . . . -0.1(9) ?
C7D C8D C8AD C4AD . . . . -0.5(7) ?
C7D C8D C8AD C1D . . . . 179.3(5) ?
C5D C4AD C8AD C8D . . . . 0.8(7) ?
C4D C4AD C8AD C8D . . . . -178.3(4) ?
C5D C4AD C8AD C1D . . . . -179.0(4) ?
C4D C4AD C8AD C1D . . . . 1.9(7) ?
C2D C1D C8AD C8D . . . . 179.1(4) ?
C1C C1D C8AD C8D . . . . -1.5(7) ?
C2D C1D C8AD C4AD . . . . -1.1(7) ?
C1C C1D C8AD C4AD . . . . 178.3(5) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C3C H3C Br1B 2_656 0.95 2.86 3.796(5) 168.2 ?

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1476385'
_audit_update_record             
;
2017-07-27 deposited with the CCDC.
2017-08-15 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H12 F2'
_chemical_formula_iupac          ?
_chemical_formula_weight         290.30

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   12.4551(9)
_cell_length_b                   10.6234(8)
_cell_length_c                   11.1894(8)
_cell_angle_alpha                90
_cell_angle_beta                 115.4835(16)
_cell_angle_gamma                90
_cell_volume                     1336.49(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4067
_cell_measurement_theta_min      3.3033
_cell_measurement_theta_max      26.4021
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.342
_exptl_crystal_size_mid          0.303
_exptl_crystal_size_min          0.094
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600

_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  TRIUMPH

_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            5379
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_theta_min         3.62
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
;

_reflns_number_total             1239
_reflns_number_gt                1137
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1010
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_number_reflns         1239
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0561P)²+1.1309P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.187
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0059(16)

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'

_computing_data_collection       'APEX2 V2013 (Bruker AXS Inc., 2013)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX2 V2013 (Bruker AXS Inc., 2013)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 0.06756(7) 0.79454(7) 0.09168(8) 0.0230(3) Uani d . . . 1 . .
C C1 0.43367(10) 0.80209(11) 0.22431(11) 0.0134(3) Uani d . . . 1 . .
C C2 0.37844(11) 0.70652(11) 0.25923(12) 0.0151(3) Uani d . . . 1 . .
H H2 0.4257 0.6413 0.3153 0.018 Uiso calc U . R 1 . .
C C3 0.25391(12) 0.70212(11) 0.21452(12) 0.0163(3) Uani d . . . 1 . .
H H3 0.2174 0.6355 0.2402 0.02 Uiso calc U . R 1 . .
C C4 0.18782(11) 0.79533(12) 0.13414(12) 0.0151(3) Uani d . . . 1 . .
C C4A 0.23638(11) 0.89556(11) 0.09044(11) 0.0138(3) Uani d . . . 1 . .
C C5 0.16507(11) 0.98982(12) 0.00230(12) 0.0154(3) Uani d . . . 1 . .
H H5 0.0813 0.9883 -0.0272 0.019 Uiso calc U . R 1 . .
C C6 0.21577(12) 1.08269(12) -0.04055(12) 0.0172(3) Uani d . . . 1 . .
H H6 0.1672 1.1452 -0.1 0.021 Uiso calc U . R 1 . .
C C7 0.34010(11) 1.08603(12) 0.00327(12) 0.0168(3) Uani d . . . 1 . .
H H7 0.3749 1.1506 -0.0272 0.02 Uiso calc U . R 1 . .
C C8 0.41113(11) 0.99675(11) 0.08948(12) 0.0149(3) Uani d . . . 1 . .
H H8 0.4948 1.0008 0.1184 0.018 Uiso calc U . R 1 . .
C C8A 0.36240(11) 0.89841(11) 0.13649(11) 0.0133(3) Uani d . . . 1 . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C4 . 1.3626(14) ?
C1 C2 . 1.3740(17) ?
C1 C8A . 1.4318(17) ?
C1 C1 2_655 1.498(2) ?
C2 C3 . 1.4108(18) ?
C2 H2 . 0.95 ?
C3 C4 . 1.3528(19) ?
C3 H3 . 0.95 ?
C4 C4A . 1.4118(18) ?
C4A C5 . 1.4178(17) ?
C4A C8A . 1.4263(17) ?
C5 C6 . 1.3648(19) ?
C5 H5 . 0.95 ?
C6 C7 . 1.4094(18) ?
C6 H6 . 0.95 ?
C7 C8 . 1.3705(18) ?
C7 H7 . 0.95 ?
C8 C8A . 1.4181(17) ?
C8 H8 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C8A . . 119.00(11) ?
C2 C1 C1 . 2_655 119.70(9) ?
C8A C1 C1 . 2_655 121.28(9) ?
C1 C2 C3 . . 122.16(11) ?
C1 C2 H2 . . 118.9 ?
C3 C2 H2 . . 118.9 ?
C4 C3 C2 . . 118.24(11) ?
C4 C3 H3 . . 120.9 ?
C2 C3 H3 . . 120.9 ?
C3 C4 F1 . . 119.37(11) ?
C3 C4 C4A . . 123.61(12) ?
F1 C4 C4A . . 117.02(11) ?
C4 C4A C5 . . 122.69(11) ?
C4 C4A C8A . . 117.37(11) ?
C5 C4A C8A . . 119.93(11) ?
C6 C5 C4A . . 120.59(12) ?
C6 C5 H5 . . 119.7 ?
C4A C5 H5 . . 119.7 ?
C5 C6 C7 . . 120.08(11) ?
C5 C6 H6 . . 120.0 ?
C7 C6 H6 . . 120.0 ?
C8 C7 C6 . . 120.48(11) ?
C8 C7 H7 . . 119.8 ?
C6 C7 H7 . . 119.8 ?
C7 C8 C8A . . 121.42(12) ?
C7 C8 H8 . . 119.3 ?
C8A C8 H8 . . 119.3 ?
C8 C8A C4A . . 117.50(11) ?
C8 C8A C1 . . 122.90(11) ?
C4A C8A C1 . . 119.59(11) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8A C1 C2 C3 . . . . -1.92(18) ?
C1 C1 C2 C3 2_655 . . . 179.58(11) ?
C1 C2 C3 C4 . . . . 0.35(18) ?
C2 C3 C4 F1 . . . . -178.74(10) ?
C2 C3 C4 C4A . . . . 1.26(19) ?
C3 C4 C4A C5 . . . . 177.63(12) ?
F1 C4 C4A C5 . . . . -2.37(17) ?
C3 C4 C4A C8A . . . . -1.18(18) ?
F1 C4 C4A C8A . . . . 178.82(10) ?
C4 C4A C5 C6 . . . . -177.89(11) ?
C8A C4A C5 C6 . . . . 0.89(18) ?
C4A C5 C6 C7 . . . . -0.34(18) ?
C5 C6 C7 C8 . . . . -0.30(18) ?
C6 C7 C8 C8A . . . . 0.39(18) ?
C7 C8 C8A C4A . . . . 0.15(17) ?
C7 C8 C8A C1 . . . . 178.62(11) ?
C4 C4A C8A C8 . . . . 178.06(10) ?
C5 C4A C8A C8 . . . . -0.78(17) ?
C4 C4A C8A C1 . . . . -0.46(17) ?
C5 C4A C8A C1 . . . . -179.30(10) ?
C2 C1 C8A C8 . . . . -176.50(11) ?
C1 C1 C8A C8 2_655 . . . 1.98(19) ?
C2 C1 C8A C4A . . . . 1.94(17) ?
C1 C1 C8A C4A 2_655 . . . -179.58(11) ?

####################################################################### 
# 
# 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_9-1
_database_code_depnum_ccdc_archive 'CCDC 1476392'
_audit_update_record             
;
2017-07-27 deposited with the CCDC.
2017-08-15 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H12 Cl0.33 F1.67'
_chemical_formula_iupac          ?
_chemical_formula_weight         295.68

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   12.6621(9)
_cell_length_b                   10.6518(8)
_cell_length_c                   11.1730(8)
_cell_angle_alpha                90
_cell_angle_beta                 115.065(2)
_cell_angle_gamma                90
_cell_volume                     1365.04(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5187
_cell_measurement_theta_min      2.6097
_cell_measurement_theta_max      26.4408
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.596
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.128
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             610

_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  TRIUMPH

_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            8166
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0115
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
Investigated crystal (9-1) contains mixture of F and Cl 
substituted 4,4? binaphtyl. During structure refinement 
position and anisotropic temperature factors for all 
non-H atoms were refined. The occupancy ratio of F/Cl 
was free to refine. 
;

_reflns_number_total             1207
_reflns_number_gt                1102
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0890
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_refine_ls_number_reflns         1207
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0491P)²+0.6197P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.145
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX2 V2014 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX2 V2014 (Bruker AXS Inc., 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.0549(8) 0.2862(6) 0.6102(7) 0.0201(11) Uani d . P . 0.164(6) . .
F F1 0.0717(3) 0.2920(3) 0.5981(3) 0.0367(16) Uani d . P . 0.836(6) . .
C C1 0.19416(11) 0.29318(11) 0.64007(12) 0.0250(3) Uani d . . . 1.0 . .
C C2 0.26030(12) 0.20032(11) 0.71927(12) 0.0263(3) Uani d . . . 1.0 . .
H H2 0.2254 0.1333 0.7457 0.032 Uiso calc U . R 1.0 . .
C C3 0.38173(12) 0.20526(11) 0.76152(12) 0.0248(3) Uani d . . . 1.0 . .
H H3 0.4284 0.1402 0.8168 0.03 Uiso calc U . R 1.0 . .
C C4 0.43527(11) 0.30089(11) 0.72565(11) 0.0220(3) Uani d . . . 1.0 . .
C C4A 0.36415(10) 0.39650(10) 0.63834(11) 0.0214(3) Uani d . . . 1.0 . .
C C5 0.41100(11) 0.49447(11) 0.58980(12) 0.0238(3) Uani d . . . 1.0 . .
H H5 0.4929 0.4991 0.6174 0.029 Uiso calc U . R 1.0 . .
C C6 0.34033(11) 0.58259(12) 0.50387(12) 0.0271(3) Uani d . . . 1.0 . .
H H6 0.3737 0.6469 0.4719 0.032 Uiso calc U . R 1.0 . .
C C7 0.21909(11) 0.57888(12) 0.46259(12) 0.0268(3) Uani d . . . 1.0 . .
H H7 0.1709 0.6408 0.4035 0.032 Uiso calc U . R 1.0 . .
C C8 0.17037(11) 0.48654(11) 0.50720(12) 0.0250(3) Uani d . . . 1.0 . .
H H8 0.0883 0.4848 0.4793 0.03 Uiso calc U . R 1.0 . .
C C8A 0.24089(10) 0.39312(11) 0.59478(11) 0.0222(3) Uani d . . . 1.0 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C1 . 1.652(11) ?
F1 C1 . 1.417(4) ?
C1 C2 . 1.3545(18) ?
C1 C8A . 1.4117(17) ?
C2 C3 . 1.4052(18) ?
C2 H2 . 0.95 ?
C3 C4 . 1.3741(17) ?
C3 H3 . 0.95 ?
C4 C4A . 1.4336(17) ?
C4 C4 2_656 1.493(2) ?
C4A C5 . 1.4169(17) ?
C4A C8A . 1.4250(17) ?
C5 C6 . 1.3695(17) ?
C5 H5 . 0.95 ?
C6 C7 . 1.4039(18) ?
C6 H6 . 0.95 ?
C7 C8 . 1.3627(18) ?
C7 H7 . 0.95 ?
C8 C8A . 1.4159(17) ?
C8 H8 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C8A . . 123.22(12) ?
C2 C1 F1 . . 119.80(18) ?
C8A C1 F1 . . 116.99(17) ?
C2 C1 Cl1 . . 114.3(3) ?
C8A C1 Cl1 . . 122.4(3) ?
F1 C1 Cl1 . . 7.2(4) ?
C1 C2 C3 . . 118.54(11) ?
C1 C2 H2 . . 120.7 ?
C3 C2 H2 . . 120.7 ?
C4 C3 C2 . . 122.31(12) ?
C4 C3 H3 . . 118.8 ?
C2 C3 H3 . . 118.8 ?
C3 C4 C4A . . 118.67(12) ?
C3 C4 C4 . 2_656 119.67(9) ?
C4A C4 C4 . 2_656 121.62(9) ?
C5 C4A C8A . . 117.61(11) ?
C5 C4A C4 . . 122.65(11) ?
C8A C4A C4 . . 119.72(10) ?
C6 C5 C4A . . 121.20(12) ?
C6 C5 H5 . . 119.4 ?
C4A C5 H5 . . 119.4 ?
C5 C6 C7 . . 120.65(11) ?
C5 C6 H6 . . 119.7 ?
C7 C6 H6 . . 119.7 ?
C8 C7 C6 . . 120.10(11) ?
C8 C7 H7 . . 119.9 ?
C6 C7 H7 . . 119.9 ?
C7 C8 C8A . . 120.62(12) ?
C7 C8 H8 . . 119.7 ?
C8A C8 H8 . . 119.7 ?
C1 C8A C8 . . 122.71(12) ?
C1 C8A C4A . . 117.47(11) ?
C8 C8A C4A . . 119.81(11) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8A C1 C2 C3 . . . . 1.78(18) ?
F1 C1 C2 C3 . . . . -178.72(19) ?
Cl1 C1 C2 C3 . . . . -173.6(3) ?
C1 C2 C3 C4 . . . . 0.22(18) ?
C2 C3 C4 C4A . . . . -2.21(17) ?
C2 C3 C4 C4 . . . 2_656 179.75(11) ?
C3 C4 C4A C5 . . . . -176.17(10) ?
C4 C4 C4A C5 2_656 . . . 1.83(18) ?
C3 C4 C4A C8A . . . . 2.30(16) ?
C4 C4 C4A C8A 2_656 . . . -179.71(10) ?
C8A C4A C5 C6 . . . . -0.15(17) ?
C4 C4A C5 C6 . . . . 178.34(11) ?
C4A C5 C6 C7 . . . . 0.72(18) ?
C5 C6 C7 C8 . . . . -0.47(18) ?
C6 C7 C8 C8A . . . . -0.35(18) ?
C2 C1 C8A C8 . . . . 177.06(11) ?
F1 C1 C8A C8 . . . . -2.5(2) ?
Cl1 C1 C8A C8 . . . . -8.0(4) ?
C2 C1 C8A C4A . . . . -1.62(17) ?
F1 C1 C8A C4A . . . . 178.86(18) ?
Cl1 C1 C8A C4A . . . . 173.4(3) ?
C7 C8 C8A C1 . . . . -177.75(11) ?
C7 C8 C8A C4A . . . . 0.90(17) ?
C5 C4A C8A C1 . . . . 178.08(10) ?
C4 C4A C8A C1 . . . . -0.46(16) ?
C5 C4A C8A C8 . . . . -0.65(16) ?
C4 C4A C8A C8 . . . . -179.19(10) ?

####################################################################### 
# 
# 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_13
_database_code_depnum_ccdc_archive 'CCDC 1476390'
_audit_update_record             
;
2017-07-27 deposited with the CCDC.
2017-08-15 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H12 F6'
_chemical_formula_iupac          ?
_chemical_formula_weight         390.32

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.6675(11)
_cell_length_b                   8.1974(7)
_cell_length_c                   14.9831(12)
_cell_angle_alpha                90
_cell_angle_beta                 90.5433(19)
_cell_angle_gamma                90
_cell_volume                     1678.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9943
_cell_measurement_theta_min      3.0887
_cell_measurement_theta_max      25.3440
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.422
_exptl_crystal_size_mid          0.407
_exptl_crystal_size_min          0.214
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792

_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  TRIUMPH

_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            23667
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_unetI/netI     0.0116
_diffrn_reflns_theta_min         2.98
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;
;

_reflns_number_total             2958
_reflns_number_gt                2651
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_gt          0.0746
_refine_ls_wR_factor_ref         0.0788
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_number_reflns         2958
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0348P)²+0.7556P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.220
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0059(8)

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'

_computing_data_collection       'APEX2 V2013 (Bruker AXS Inc., 2013)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Diamond 3.2 (Crystal Impact GbR, 2014)'
_computing_publication_material  'APEX2 V2013 (Bruker AXS Inc., 2013)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.27245(9) 0.24479(17) 1.00116(9) 0.0224(3) Uani d . . . 1 . .
C C2 0.30018(11) 0.14981(19) 1.07218(9) 0.0286(3) Uani d . . . 1 . .
H H2 0.2795 0.0393 1.0745 0.034 Uiso calc U . R 1 . .
C C3 0.35864(11) 0.2127(2) 1.14156(10) 0.0314(3) Uani d . . . 1 . .
H H3 0.3766 0.1444 1.1903 0.038 Uiso calc U . R 1 . .
C C4 0.38994(10) 0.37010(19) 1.13996(9) 0.0270(3) Uani d . . . 1 . .
H H4 0.4296 0.4105 1.1874 0.032 Uiso calc U . R 1 . .
C C4A 0.36383(9) 0.47463(18) 1.06795(9) 0.0223(3) Uani d . . . 1 . .
C C5 0.39498(10) 0.64030(18) 1.06101(9) 0.0253(3) Uani d . . . 1 . .
C C6 0.37023(10) 0.73369(18) 0.98862(10) 0.0285(3) Uani d . . . 1 . .
H H6 0.393 0.8429 0.9848 0.034 Uiso calc U . R 1 . .
C C7 0.31119(11) 0.66883(18) 0.91979(10) 0.0279(3) Uani d . . . 1 . .
H H7 0.2942 0.7344 0.8697 0.033 Uiso calc U . R 1 . .
C C8 0.27849(10) 0.51260(17) 0.92482(9) 0.0233(3) Uani d . . . 1 . .
H H8 0.2377 0.4709 0.8785 0.028 Uiso calc U . R 1 . .
C C8A 0.30389(9) 0.41071(17) 0.99765(9) 0.0214(3) Uani d . . . 1 . .
C C9 0.45423(10) 0.7157(2) 1.13488(10) 0.0311(4) Uani d . . . 1 . .
F F1 0.40570(6) 0.71806(13) 1.21270(6) 0.0436(3) Uani d . . . 1 . .
F F2 0.47912(7) 0.87048(12) 1.11814(7) 0.0466(3) Uani d . . . 1 . .
F F3 0.53822(6) 0.63684(12) 1.15175(6) 0.0350(2) Uani d . . . 1 . .
C C1' 0.21103(10) 0.17370(17) 0.92763(9) 0.0218(3) Uani d . . . 1 . .
C C2' 0.25476(10) 0.09346(18) 0.85853(9) 0.0254(3) Uani d . . . 1 . .
H H2' 0.3241 0.0852 0.8572 0.031 Uiso calc U . R 1 . .
C C3' 0.19861(10) 0.02309(18) 0.78949(9) 0.0266(3) Uani d . . . 1 . .
H H3' 0.2304 -0.0338 0.7428 0.032 Uiso calc U . R 1 . .
C C4' 0.09930(10) 0.03534(17) 0.78868(9) 0.0230(3) Uani d . . . 1 . .
H H4' 0.0625 -0.0129 0.7415 0.028 Uiso calc U . R 1 . .
C C4A' 0.05037(10) 0.11984(16) 0.85799(8) 0.0197(3) Uani d . . . 1 . .
C C5' -0.05331(10) 0.14163(16) 0.85971(9) 0.0212(3) Uani d . . . 1 . .
C C6' -0.09713(10) 0.22318(18) 0.92823(9) 0.0256(3) Uani d . . . 1 . .
H H6' -0.1661 0.2373 0.9279 0.031 Uiso calc U . R 1 . .
C C7' -0.04064(10) 0.2861(2) 0.99899(9) 0.0297(3) Uani d . . . 1 . .
H H7' -0.0718 0.3408 1.0469 0.036 Uiso calc U . R 1 . .
C C8' 0.05845(10) 0.26906(18) 0.99945(9) 0.0258(3) Uani d . . . 1 . .
H H8' 0.0957 0.3122 1.0478 0.031 Uiso calc U . R 1 . .
C C8A' 0.10685(10) 0.18797(17) 0.92897(9) 0.0209(3) Uani d . . . 1 . .
C C9' -0.11545(10) 0.07550(18) 0.78547(9) 0.0244(3) Uani d . . . 1 . .
F F1' -0.08734(6) 0.12981(11) 0.70489(5) 0.0319(2) Uani d . . . 1 . .
F F2' -0.20996(6) 0.11780(11) 0.79258(5) 0.0295(2) Uani d . . . 1 . .
F F3' -0.11362(6) -0.08794(10) 0.78088(6) 0.0318(2) Uani d . . . 1 . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.369(2) ?
C1 C8A . 1.427(2) ?
C1 C1' . 1.4968(19) ?
C2 C3 . 1.403(2) ?
C2 H2 . 0.95 ?
C3 C4 . 1.360(2) ?
C3 H3 . 0.95 ?
C4 C4A . 1.421(2) ?
C4 H4 . 0.95 ?
C4A C5 . 1.427(2) ?
C4A C8A . 1.4280(19) ?
C5 C6 . 1.367(2) ?
C5 C9 . 1.499(2) ?
C6 C7 . 1.408(2) ?
C6 H6 . 0.95 ?
C7 C8 . 1.359(2) ?
C7 H7 . 0.95 ?
C8 C8A . 1.4147(19) ?
C8 H8 . 0.95 ?
C9 F2 . 1.3380(19) ?
C9 F3 . 1.3394(17) ?
C9 F1 . 1.3469(18) ?
C1' C2' . 1.369(2) ?
C1' C8A' . 1.4290(19) ?
C2' C3' . 1.406(2) ?
C2' H2' . 0.95 ?
C3' C4' . 1.361(2) ?
C3' H3' . 0.95 ?
C4' C4A' . 1.4209(19) ?
C4' H4' . 0.95 ?
C4A' C8A' . 1.4224(19) ?
C4A' C5' . 1.4286(19) ?
C5' C6' . 1.3679(19) ?
C5' C9' . 1.4949(19) ?
C6' C7' . 1.404(2) ?
C6' H6' . 0.95 ?
C7' C8' . 1.361(2) ?
C7' H7' . 0.95 ?
C8' C8A' . 1.4171(19) ?
C8' H8' . 0.95 ?
C9' F3' . 1.3417(17) ?
C9' F2' . 1.3427(16) ?
C9' F1' . 1.3462(16) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C8A . . 119.29(13) ?
C2 C1 C1' . . 119.99(13) ?
C8A C1 C1' . . 120.71(12) ?
C1 C2 C3 . . 121.23(14) ?
C1 C2 H2 . . 119.4 ?
C3 C2 H2 . . 119.4 ?
C4 C3 C2 . . 120.83(14) ?
C4 C3 H3 . . 119.6 ?
C2 C3 H3 . . 119.6 ?
C3 C4 C4A . . 120.60(13) ?
C3 C4 H4 . . 119.7 ?
C4A C4 H4 . . 119.7 ?
C4 C4A C5 . . 123.80(13) ?
C4 C4A C8A . . 118.50(13) ?
C5 C4A C8A . . 117.70(13) ?
C6 C5 C4A . . 121.25(13) ?
C6 C5 C9 . . 118.87(14) ?
C4A C5 C9 . . 119.87(13) ?
C5 C6 C7 . . 120.36(14) ?
C5 C6 H6 . . 119.8 ?
C7 C6 H6 . . 119.8 ?
C8 C7 C6 . . 120.13(14) ?
C8 C7 H7 . . 119.9 ?
C6 C7 H7 . . 119.9 ?
C7 C8 C8A . . 121.39(13) ?
C7 C8 H8 . . 119.3 ?
C8A C8 H8 . . 119.3 ?
C8 C8A C1 . . 121.28(12) ?
C8 C8A C4A . . 119.15(13) ?
C1 C8A C4A . . 119.55(12) ?
F2 C9 F3 . . 105.90(12) ?
F2 C9 F1 . . 106.07(12) ?
F3 C9 F1 . . 105.77(12) ?
F2 C9 C5 . . 112.90(13) ?
F3 C9 C5 . . 113.36(12) ?
F1 C9 C5 . . 112.22(12) ?
C2' C1' C8A' . . 119.49(13) ?
C2' C1' C1 . . 119.86(12) ?
C8A' C1' C1 . . 120.64(12) ?
C1' C2' C3' . . 120.96(13) ?
C1' C2' H2' . . 119.5 ?
C3' C2' H2' . . 119.5 ?
C4' C3' C2' . . 120.91(13) ?
C4' C3' H3' . . 119.5 ?
C2' C3' H3' . . 119.5 ?
C3' C4' C4A' . . 120.38(13) ?
C3' C4' H4' . . 119.8 ?
C4A' C4' H4' . . 119.8 ?
C4' C4A' C8A' . . 118.81(12) ?
C4' C4A' C5' . . 123.22(12) ?
C8A' C4A' C5' . . 117.96(12) ?
C6' C5' C4A' . . 121.06(12) ?
C6' C5' C9' . . 119.08(12) ?
C4A' C5' C9' . . 119.86(12) ?
C5' C6' C7' . . 120.32(13) ?
C5' C6' H6' . . 119.8 ?
C7' C6' H6' . . 119.8 ?
C8' C7' C6' . . 120.41(13) ?
C8' C7' H7' . . 119.8 ?
C6' C7' H7' . . 119.8 ?
C7' C8' C8A' . . 121.04(13) ?
C7' C8' H8' . . 119.5 ?
C8A' C8' H8' . . 119.5 ?
C8' C8A' C4A' . . 119.17(12) ?
C8' C8A' C1' . . 121.41(12) ?
C4A' C8A' C1' . . 119.42(12) ?
F3' C9' F2' . . 106.28(11) ?
F3' C9' F1' . . 106.18(11) ?
F2' C9' F1' . . 105.59(11) ?
F3' C9' C5' . . 112.92(11) ?
F2' C9' C5' . . 112.80(11) ?
F1' C9' C5' . . 112.48(11) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8A C1 C2 C3 . . . . 0.2(2) ?
C1' C1 C2 C3 . . . . 179.28(13) ?
C1 C2 C3 C4 . . . . -0.3(2) ?
C2 C3 C4 C4A . . . . 0.2(2) ?
C3 C4 C4A C5 . . . . -179.08(13) ?
C3 C4 C4A C8A . . . . 0.2(2) ?
C4 C4A C5 C6 . . . . 177.80(13) ?
C8A C4A C5 C6 . . . . -1.46(19) ?
C4 C4A C5 C9 . . . . -3.5(2) ?
C8A C4A C5 C9 . . . . 177.27(12) ?
C4A C5 C6 C7 . . . . 1.4(2) ?
C9 C5 C6 C7 . . . . -177.32(13) ?
C5 C6 C7 C8 . . . . -0.1(2) ?
C6 C7 C8 C8A . . . . -1.1(2) ?
C7 C8 C8A C1 . . . . -177.64(13) ?
C7 C8 C8A C4A . . . . 1.1(2) ?
C2 C1 C8A C8 . . . . 178.87(13) ?
C1' C1 C8A C8 . . . . -0.24(19) ?
C2 C1 C8A C4A . . . . 0.18(19) ?
C1' C1 C8A C4A . . . . -178.93(12) ?
C4 C4A C8A C8 . . . . -179.06(12) ?
C5 C4A C8A C8 . . . . 0.23(18) ?
C4 C4A C8A C1 . . . . -0.35(18) ?
C5 C4A C8A C1 . . . . 178.95(12) ?
C6 C5 C9 F2 . . . . -2.21(19) ?
C4A C5 C9 F2 . . . . 179.04(12) ?
C6 C5 C9 F3 . . . . -122.64(15) ?
C4A C5 C9 F3 . . . . 58.61(18) ?
C6 C5 C9 F1 . . . . 117.61(15) ?
C4A C5 C9 F1 . . . . -61.15(17) ?
C2 C1 C1' C2' . . . . -85.88(17) ?
C8A C1 C1' C2' . . . . 93.22(16) ?
C2 C1 C1' C8A' . . . . 93.80(16) ?
C8A C1 C1' C8A' . . . . -87.10(16) ?
C8A' C1' C2' C3' . . . . -0.8(2) ?
C1 C1' C2' C3' . . . . 178.85(13) ?
C1' C2' C3' C4' . . . . 1.2(2) ?
C2' C3' C4' C4A' . . . . 0.0(2) ?
C3' C4' C4A' C8A' . . . . -1.4(2) ?
C3' C4' C4A' C5' . . . . 177.96(13) ?
C4' C4A' C5' C6' . . . . 179.62(13) ?
C8A' C4A' C5' C6' . . . . -1.05(19) ?
C4' C4A' C5' C9' . . . . -0.73(19) ?
C8A' C4A' C5' C9' . . . . 178.60(12) ?
C4A' C5' C6' C7' . . . . -0.6(2) ?
C9' C5' C6' C7' . . . . 179.77(13) ?
C5' C6' C7' C8' . . . . 1.1(2) ?
C6' C7' C8' C8A' . . . . 0.0(2) ?
C7' C8' C8A' C4A' . . . . -1.6(2) ?
C7' C8' C8A' C1' . . . . 178.17(14) ?
C4' C4A' C8A' C8' . . . . -178.51(12) ?
C5' C4A' C8A' C8' . . . . 2.13(19) ?
C4' C4A' C8A' C1' . . . . 1.67(19) ?
C5' C4A' C8A' C1' . . . . -177.69(12) ?
C2' C1' C8A' C8' . . . . 179.60(13) ?
C1 C1' C8A' C8' . . . . -0.1(2) ?
C2' C1' C8A' C4A' . . . . -0.6(2) ?
C1 C1' C8A' C4A' . . . . 179.73(12) ?
C6' C5' C9' F3' . . . . -115.43(14) ?
C4A' C5' C9' F3' . . . . 64.91(16) ?
C6' C5' C9' F2' . . . . 5.10(18) ?
C4A' C5' C9' F2' . . . . -174.56(11) ?
C6' C5' C9' F1' . . . . 124.41(14) ?
C4A' C5' C9' F1' . . . . -55.25(17) ?

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
C2 H2 F2' 0.95 2.56 3.2382(17) 128.4 3_557
C3 H3 F3 0.95 2.63 3.4468(17) 144.5 2_647
C7' H7' F1' 0.95 2.39 3.2307(16) 147.1 4_566


####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1476387'
_audit_update_record             
;
2017-07-27 deposited with the CCDC.
2017-08-15 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H12 Br2'
_chemical_formula_iupac          ?
_chemical_formula_weight         412.12

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   13.6190(7)
_cell_length_b                   10.5374(6)
_cell_length_c                   11.4528(6)
_cell_angle_alpha                90
_cell_angle_beta                 115.2950(10)
_cell_angle_gamma                90
_cell_volume                     1485.99(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9426
_cell_measurement_theta_min      2.5442
_cell_measurement_theta_max      26.4162
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.477
_exptl_crystal_size_mid          0.197
_exptl_crystal_size_min          0.156
_exptl_crystal_density_diffrn    1.842
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808

_exptl_absorpt_coefficient_mu    5.448
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.26
_exptl_absorpt_correction_T_max  0.48

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  TRIUMPH

_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            16534
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_theta_min         2.54
_diffrn_reflns_theta_max         26.42
_diffrn_reflns_theta_full        26.42
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?

_refine_special_details          
;
Data scaling was based on two twin domains refined to 
0.2752:0.7248 ratio. Structure refinement was based on
the merged hkl file with the instruction HKLF4.
;

_reflns_number_total             1536
_reflns_number_gt                1400
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0812
_refine_ls_goodness_of_fit_ref   1.167
_refine_ls_restrained_S_all      1.167
_refine_ls_number_reflns         1536
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0316P)²+8.3428P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.600
_refine_diff_density_min         -0.419
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX2 V2014 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX2 V2014 (Bruker AXS Inc., 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.06668(3) 0.28637(3) 0.62452(3) 0.02354(14) Uani d . . . 1 . .
C C1 0.4397(3) 0.2944(3) 0.7283(3) 0.0158(6) Uani d . . . 1 . .
C C2 0.3934(3) 0.1991(3) 0.7689(3) 0.0184(7) Uani d . . . 1 . .
H H2 0.4382 0.1332 0.8215 0.022 Uiso calc U . R 1 . .
C C3 0.2808(3) 0.1960(3) 0.7348(3) 0.0183(7) Uani d . . . 1 . .
H H3 0.2506 0.1293 0.7648 0.022 Uiso calc U . R 1 . .
C C4 0.2160(3) 0.2892(3) 0.6585(3) 0.0171(6) Uani d . . . 1 . .
C C4A 0.2565(2) 0.3866(3) 0.6060(3) 0.0147(6) Uani d . . . 1 . .
C C5 0.1897(3) 0.4795(3) 0.5189(3) 0.0172(6) Uani d . . . 1 . .
H H5 0.1138 0.4792 0.4955 0.021 Uiso calc U . R 1 . .
C C6 0.2321(3) 0.5695(3) 0.4679(3) 0.0194(7) Uani d . . . 1 . .
H H6 0.1858 0.6304 0.4087 0.023 Uiso calc U . R 1 . .
C C7 0.3440(3) 0.5720(3) 0.5030(3) 0.0191(7) Uani d . . . 1 . .
H H7 0.3732 0.6343 0.4668 0.023 Uiso calc U . R 1 . .
C C8 0.4118(3) 0.4853(3) 0.5890(3) 0.0167(7) Uani d . . . 1 . .
H H8 0.4877 0.4896 0.6129 0.02 Uiso calc U . R 1 . .
C C8A 0.3709(3) 0.3896(3) 0.6428(3) 0.0151(6) Uani d . . . 1 . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C4 . 1.901(3) ?
C1 C2 . 1.369(5) ?
C1 C8A . 1.435(4) ?
C1 C1 2_656 1.498(6) ?
C2 C3 . 1.412(5) ?
C2 H2 . 0.95 ?
C3 C4 . 1.359(5) ?
C3 H3 . 0.95 ?
C4 C4A . 1.415(4) ?
C4A C5 . 1.416(4) ?
C4A C8A . 1.431(4) ?
C5 C6 . 1.365(5) ?
C5 H5 . 0.95 ?
C6 C7 . 1.401(5) ?
C6 H6 . 0.95 ?
C7 C8 . 1.371(5) ?
C7 H7 . 0.95 ?
C8 C8A . 1.414(4) ?
C8 H8 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C8A . . 118.9(3) ?
C2 C1 C1 . 2_656 119.1(3) ?
C8A C1 C1 . 2_656 122.0(2) ?
C1 C2 C3 . . 121.8(3) ?
C1 C2 H2 . . 119.1 ?
C3 C2 H2 . . 119.1 ?
C4 C3 C2 . . 119.4(3) ?
C4 C3 H3 . . 120.3 ?
C2 C3 H3 . . 120.3 ?
C3 C4 C4A . . 122.3(3) ?
C3 C4 Br1 . . 117.6(2) ?
C4A C4 Br1 . . 120.1(2) ?
C4 C4A C5 . . 123.5(3) ?
C4 C4A C8A . . 117.6(3) ?
C5 C4A C8A . . 118.9(3) ?
C6 C5 C4A . . 121.3(3) ?
C6 C5 H5 . . 119.3 ?
C4A C5 H5 . . 119.3 ?
C5 C6 C7 . . 119.9(3) ?
C5 C6 H6 . . 120.1 ?
C7 C6 H6 . . 120.1 ?
C8 C7 C6 . . 120.7(3) ?
C8 C7 H7 . . 119.7 ?
C6 C7 H7 . . 119.7 ?
C7 C8 C8A . . 121.3(3) ?
C7 C8 H8 . . 119.4 ?
C8A C8 H8 . . 119.4 ?
C8 C8A C4A . . 118.0(3) ?
C8 C8A C1 . . 122.2(3) ?
C4A C8A C1 . . 119.8(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8A C1 C2 C3 . . . . -3.6(5) ?
C1 C1 C2 C3 2_656 . . . 178.0(3) ?
C1 C2 C3 C4 . . . . 0.7(5) ?
C2 C3 C4 C4A . . . . 3.4(5) ?
C2 C3 C4 Br1 . . . . -176.1(2) ?
C3 C4 C4A C5 . . . . 175.3(3) ?
Br1 C4 C4A C5 . . . . -5.3(4) ?
C3 C4 C4A C8A . . . . -4.2(5) ?
Br1 C4 C4A C8A . . . . 175.3(2) ?
C4 C4A C5 C6 . . . . -178.1(3) ?
C8A C4A C5 C6 . . . . 1.4(5) ?
C4A C5 C6 C7 . . . . -0.8(5) ?
C5 C6 C7 C8 . . . . -0.5(5) ?
C6 C7 C8 C8A . . . . 1.3(5) ?
C7 C8 C8A C4A . . . . -0.7(5) ?
C7 C8 C8A C1 . . . . 177.0(3) ?
C4 C4A C8A C8 . . . . 178.9(3) ?
C5 C4A C8A C8 . . . . -0.6(4) ?
C4 C4A C8A C1 . . . . 1.1(4) ?
C5 C4A C8A C1 . . . . -178.4(3) ?
C2 C1 C8A C8 . . . . -175.1(3) ?
C1 C1 C8A C8 2_656 . . . 3.3(5) ?
C2 C1 C8A C4A . . . . 2.6(4) ?
C1 C1 C8A C4A 2_656 . . . -178.9(3) ?

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1476386'
_audit_update_record             
;
2017-07-27 deposited with the CCDC.
2017-08-15 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H12 Cl2'
_chemical_formula_iupac          ?
_chemical_formula_weight         323.20

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   13.1656(10)
_cell_length_b                   10.6206(8)
_cell_length_c                   11.2471(9)
_cell_angle_alpha                90
_cell_angle_beta                 115.0519(18)
_cell_angle_gamma                90
_cell_volume                     1424.70(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6466
_cell_measurement_theta_min      3.4164
_cell_measurement_theta_max      26.4166
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.414
_exptl_crystal_size_mid          0.129
_exptl_crystal_size_min          0.086
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664

_exptl_absorpt_coefficient_mu    0.447
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  0.96

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  TRIUMPH

_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            11706
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_theta_min         3.42
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
;

_reflns_number_total             1403
_reflns_number_gt                1228
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_gt          0.0786
_refine_ls_wR_factor_ref         0.0831
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_number_reflns         1403
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0369P)²+2.3680P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.229
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX2 V2013 (Bruker AXS Inc., 2013)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX2 V2013 (Bruker AXS Inc., 2013)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.06393(3) 0.28611(4) 0.11703(4) 0.02215(16) Uani d . . . 1 . .
C C1 0.43778(13) 0.29711(16) 0.22780(16) 0.0148(4) Uani d . . . 1 . .
C C2 0.38907(15) 0.20107(16) 0.26650(17) 0.0165(4) Uani d . . . 1 . .
H H2 0.4351 0.1355 0.3195 0.02 Uiso calc U . R 1 . .
C C3 0.27259(15) 0.19667(17) 0.23011(17) 0.0173(4) Uani d . . . 1 . .
H H3 0.241 0.1295 0.2591 0.021 Uiso calc U . R 1 . .
C C4 0.20613(14) 0.28943(17) 0.15322(17) 0.0159(4) Uani d . . . 1 . .
C C4A 0.24883(14) 0.38853(16) 0.10261(16) 0.0137(4) Uani d . . . 1 . .
C C5 0.17930(14) 0.48074(17) 0.01484(16) 0.0159(4) Uani d . . . 1 . .
H H5 0.1008 0.4794 -0.0097 0.019 Uiso calc U . R 1 . .
C C6 0.22385(15) 0.57170(17) -0.03499(17) 0.0179(4) Uani d . . . 1 . .
H H6 0.1763 0.6325 -0.0946 0.021 Uiso calc U . R 1 . .
C C7 0.34025(15) 0.57507(17) 0.00218(17) 0.0175(4) Uani d . . . 1 . .
H H7 0.3708 0.638 -0.0332 0.021 Uiso calc U . R 1 . .
C C8 0.40994(14) 0.48876(17) 0.08871(17) 0.0162(4) Uani d . . . 1 . .
H H8 0.4884 0.4938 0.1137 0.019 Uiso calc U . R 1 . .
C C8A 0.36727(14) 0.39200(16) 0.14169(16) 0.0139(4) Uani d . . . 1 . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C4 . 1.7397(17) ?
C1 C2 . 1.370(2) ?
C1 C8A . 1.433(2) ?
C1 C1 2_655 1.497(3) ?
C2 C3 . 1.411(2) ?
C2 H2 . 0.95 ?
C3 C4 . 1.358(3) ?
C3 H3 . 0.95 ?
C4 C4A . 1.421(2) ?
C4A C5 . 1.416(2) ?
C4A C8A . 1.430(2) ?
C5 C6 . 1.367(3) ?
C5 H5 . 0.95 ?
C6 C7 . 1.408(2) ?
C6 H6 . 0.95 ?
C7 C8 . 1.369(3) ?
C7 H7 . 0.95 ?
C8 C8A . 1.418(2) ?
C8 H8 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C8A . . 118.80(16) ?
C2 C1 C1 . 2_655 119.17(13) ?
C8A C1 C1 . 2_655 121.98(13) ?
C1 C2 C3 . . 122.01(16) ?
C1 C2 H2 . . 119.0 ?
C3 C2 H2 . . 119.0 ?
C4 C3 C2 . . 119.28(16) ?
C4 C3 H3 . . 120.4 ?
C2 C3 H3 . . 120.4 ?
C3 C4 C4A . . 122.34(16) ?
C3 C4 Cl1 . . 118.28(14) ?
C4A C4 Cl1 . . 119.37(13) ?
C5 C4A C4 . . 122.87(16) ?
C5 C4A C8A . . 119.68(15) ?
C4 C4A C8A . . 117.44(15) ?
C6 C5 C4A . . 120.76(16) ?
C6 C5 H5 . . 119.6 ?
C4A C5 H5 . . 119.6 ?
C5 C6 C7 . . 119.88(16) ?
C5 C6 H6 . . 120.1 ?
C7 C6 H6 . . 120.1 ?
C8 C7 C6 . . 120.78(16) ?
C8 C7 H7 . . 119.6 ?
C6 C7 H7 . . 119.6 ?
C7 C8 C8A . . 121.25(16) ?
C7 C8 H8 . . 119.4 ?
C8A C8 H8 . . 119.4 ?
C8 C8A C4A . . 117.64(15) ?
C8 C8A C1 . . 122.36(15) ?
C4A C8A C1 . . 119.96(15) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8A C1 C2 C3 . . . . -3.6(3) ?
C1 C1 C2 C3 2_655 . . . 178.82(17) ?
C1 C2 C3 C4 . . . . 0.7(3) ?
C2 C3 C4 C4A . . . . 3.0(3) ?
C2 C3 C4 Cl1 . . . . -176.66(13) ?
C3 C4 C4A C5 . . . . 175.38(17) ?
Cl1 C4 C4A C5 . . . . -5.0(2) ?
C3 C4 C4A C8A . . . . -3.5(2) ?
Cl1 C4 C4A C8A . . . . 176.09(12) ?
C4 C4A C5 C6 . . . . -177.61(16) ?
C8A C4A C5 C6 . . . . 1.3(2) ?
C4A C5 C6 C7 . . . . -0.7(3) ?
C5 C6 C7 C8 . . . . -0.5(3) ?
C6 C7 C8 C8A . . . . 1.2(3) ?
C7 C8 C8A C4A . . . . -0.7(2) ?
C7 C8 C8A C1 . . . . 177.12(17) ?
C5 C4A C8A C8 . . . . -0.6(2) ?
C4 C4A C8A C8 . . . . 178.37(15) ?
C5 C4A C8A C1 . . . . -178.39(15) ?
C4 C4A C8A C1 . . . . 0.5(2) ?
C2 C1 C8A C8 . . . . -174.84(16) ?
C1 C1 C8A C8 2_655 . . . 2.7(3) ?
C2 C1 C8A C4A . . . . 2.9(2) ?
C1 C1 C8A C4A 2_655 . . . -179.60(16) ?

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1476388'
_audit_update_record             
;
2017-07-27 deposited with the CCDC.
2017-08-15 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H12 I2'
_chemical_formula_iupac          ?
_chemical_formula_weight         506.10

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   27.406(3)
_cell_length_b                   6.3564(6)
_cell_length_c                   9.5554(9)
_cell_angle_alpha                90
_cell_angle_beta                 106.7452(17)
_cell_angle_gamma                90
_cell_volume                     1594.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6283
_cell_measurement_theta_min      3.1049
_cell_measurement_theta_max      26.3781
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       planar
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.355
_exptl_crystal_size_mid          0.231
_exptl_crystal_size_min          0.018
_exptl_crystal_density_diffrn    2.109
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             952

_exptl_absorpt_coefficient_mu    3.939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_T_max  0.93

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  TRIUMPH

_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            10852
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11

_refine_special_details          
;
;

_reflns_number_total             1416
_reflns_number_gt                1045
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0205
_refine_ls_wR_factor_gt          0.0476
_refine_ls_wR_factor_ref         0.0538
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_refine_ls_number_reflns         1416
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0200P)²+5.7347P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.540
_refine_diff_density_min         -0.345
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX2 V2014 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX2 V2014 (Bruker AXS Inc., 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I I1 0.20935(2) -0.00021(5) 0.79899(2) 0.02344(10) Uani d . . . 1 . .
C C1 0.02799(13) 0.1026(6) 0.7543(4) 0.0136(7) Uani d . . . 1 . .
C C2 0.04576(14) -0.0626(6) 0.6905(4) 0.0158(8) Uani d . . . 1 . .
H H2 0.0222 -0.1631 0.6362 0.019 Uiso calc U . R 1 . .
C C3 0.09788(14) -0.0877(6) 0.7031(4) 0.0166(8) Uani d . . . 1 . .
H H3 0.1092 -0.2038 0.6582 0.02 Uiso calc U . R 1 . .
C C4 0.13192(14) 0.0562(6) 0.7803(4) 0.0165(8) Uani d . . . 1 . .
C C4A 0.11623(14) 0.2342(5) 0.8468(4) 0.0145(7) Uani d . . . 1 . .
C C5 0.15036(14) 0.3921(6) 0.9243(4) 0.0183(8) Uani d . . . 1 . .
H H5 0.1856 0.3814 0.932 0.022 Uiso calc U . R 1 . .
C C6 0.13345(15) 0.5574(6) 0.9874(4) 0.0193(9) Uani d . . . 1 . .
H H6 0.1569 0.6605 1.0387 0.023 Uiso calc U . R 1 . .
C C7 0.08118(15) 0.5771(6) 0.9771(4) 0.0169(8) Uani d . . . 1 . .
H H7 0.0697 0.6924 1.0224 0.02 Uiso calc U . R 1 . .
C C8 0.04727(15) 0.4306(6) 0.9023(4) 0.0163(8) Uani d . . . 1 . .
H H8 0.0122 0.4458 0.8962 0.02 Uiso calc U . R 1 . .
C C8A 0.06294(14) 0.2559(5) 0.8331(4) 0.0137(7) Uani d . . . 1 . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
I1 C4 . 2.108(4) ?
C1 C2 . 1.372(5) ?
C1 C8A . 1.421(5) ?
C1 C1 2_556 1.512(7) ?
C2 C3 . 1.408(5) ?
C2 H2 . 0.95 ?
C3 C4 . 1.362(5) ?
C3 H3 . 0.95 ?
C4 C4A . 1.424(5) ?
C4A C5 . 1.425(5) ?
C4A C8A . 1.435(5) ?
C5 C6 . 1.358(5) ?
C5 H5 . 0.95 ?
C6 C7 . 1.413(5) ?
C6 H6 . 0.95 ?
C7 C8 . 1.363(5) ?
C7 H7 . 0.95 ?
C8 C8A . 1.420(5) ?
C8 H8 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C8A . . 119.3(3) ?
C2 C1 C1 . 2_556 117.4(3) ?
C8A C1 C1 . 2_556 123.2(3) ?
C1 C2 C3 . . 122.0(3) ?
C1 C2 H2 . . 119.0 ?
C3 C2 H2 . . 119.0 ?
C4 C3 C2 . . 119.4(3) ?
C4 C3 H3 . . 120.3 ?
C2 C3 H3 . . 120.3 ?
C3 C4 C4A . . 121.8(3) ?
C3 C4 I1 . . 116.6(3) ?
C4A C4 I1 . . 121.6(3) ?
C4 C4A C5 . . 123.6(3) ?
C4 C4A C8A . . 117.8(3) ?
C5 C4A C8A . . 118.6(3) ?
C6 C5 C4A . . 121.2(4) ?
C6 C5 H5 . . 119.4 ?
C4A C5 H5 . . 119.4 ?
C5 C6 C7 . . 120.4(3) ?
C5 C6 H6 . . 119.8 ?
C7 C6 H6 . . 119.8 ?
C8 C7 C6 . . 120.0(4) ?
C8 C7 H7 . . 120.0 ?
C6 C7 H7 . . 120.0 ?
C7 C8 C8A . . 121.7(4) ?
C7 C8 H8 . . 119.1 ?
C8A C8 H8 . . 119.1 ?
C8 C8A C1 . . 122.3(3) ?
C8 C8A C4A . . 118.0(3) ?
C1 C8A C4A . . 119.7(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8A C1 C2 C3 . . . . 1.3(5) ?
C1 C1 C2 C3 2_556 . . . -174.4(3) ?
C1 C2 C3 C4 . . . . -0.3(5) ?
C2 C3 C4 C4A . . . . -1.2(5) ?
C2 C3 C4 I1 . . . . 178.0(3) ?
C3 C4 C4A C5 . . . . -177.8(3) ?
I1 C4 C4A C5 . . . . 3.0(5) ?
C3 C4 C4A C8A . . . . 1.5(5) ?
I1 C4 C4A C8A . . . . -177.7(2) ?
C4 C4A C5 C6 . . . . -179.1(3) ?
C8A C4A C5 C6 . . . . 1.6(5) ?
C4A C5 C6 C7 . . . . -0.2(5) ?
C5 C6 C7 C8 . . . . -0.7(5) ?
C6 C7 C8 C8A . . . . 0.0(5) ?
C7 C8 C8A C1 . . . . -179.8(3) ?
C7 C8 C8A C4A . . . . 1.4(5) ?
C2 C1 C8A C8 . . . . -179.8(3) ?
C1 C1 C8A C8 2_556 . . . -4.4(5) ?
C2 C1 C8A C4A . . . . -1.0(5) ?
C1 C1 C8A C4A 2_556 . . . 174.5(3) ?
C4 C4A C8A C8 . . . . 178.5(3) ?
C5 C4A C8A C8 . . . . -2.1(5) ?
C4 C4A C8A C1 . . . . -0.4(5) ?
C5 C4A C8A C1 . . . . 179.0(3) ?

####################################################################### 
# 
# 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_10-2_in_C2
_database_code_depnum_ccdc_archive 'CCDC 1476396'
_audit_update_record             
;
2017-07-27 deposited with the CCDC.
2017-08-15 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H24 Br0.57 F3.43'
_chemical_formula_iupac          ?
_chemical_formula_weight         615.31
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   12.6657(10)
_cell_length_b                   10.6594(9)
_cell_length_c                   11.1921(9)
_cell_angle_alpha                90
_cell_angle_beta                 115.080(2)
_cell_angle_gamma                90
_cell_volume                     1368.57(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5389
_cell_measurement_theta_min      2.6085
_cell_measurement_theta_max      26.4031
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.423
_exptl_crystal_size_mid          0.278
_exptl_crystal_size_min          0.106
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             630

_exptl_absorpt_coefficient_mu    0.928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  0.91

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  TRIUMPH

_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            10514
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         26.43
_diffrn_reflns_theta_full        26.43
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
Investigated crystal (10-2) contains mixture of F and Br 
substituted 4,4? binaphtyl. During structure refinement 
position and anisotropic temperature factors for all 
non-H atoms were refined. The occupancy ratio of F/Br 
was free to refine. In the F/Br mixed crystals possible 
lowering of the space group symmetry from C2/c to chiral 
C2 was observed. This was tested by structure refinement 
in both C2 (current data block) and C2/c (10-1_in_C2c 
data block) space groups. In the C2 choice crystal is 
twinned by the inversion with twin component ratio 
refined to 0.80(3) and 0.20(3). The C2 choice gives 
significantly lower R values than corresponding C2/c 
choice.
;

_reflns_number_total             2815
_reflns_number_gt                2382
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0938
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_number_reflns         2815
_refine_ls_number_parameters     220
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0432P)²+0.3754P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.162
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Refined as an inversion twin.'
_refine_ls_abs_structure_Flack   0.20(3)

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX2 V2014 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX2 V2014 (Bruker AXS Inc., 2014)'

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
Br1A Br 0.4525(4) 0.4714(4) 0.1323(4) 0.0273(9) Uani 0.191(3) 1 d . . P . .
F1A F 0.4268(5) 0.4608(7) 0.1520(6) 0.0365(17) Uani 0.809(3) 1 d . . P . .
C1A C 0.0646(3) 0.4523(4) 0.0243(3) 0.0270(9) Uani 1 1 d . . . . .
C2A C 0.1179(3) 0.5468(4) -0.0122(3) 0.0303(9) Uani 1 1 d . . . . .
H2A H 0.0708 0.6112 -0.0681 0.036 Uiso 1 1 calc R U . . .
C3A C 0.2391(3) 0.5526(4) 0.0294(3) 0.0327(9) Uani 1 1 d . . . . .
H3A H 0.2735 0.6195 0.0022 0.039 Uiso 1 1 calc R U . . .
C4A C 0.3054(3) 0.4612(5) 0.1086(3) 0.0308(8) Uani 1 1 d . . . . .
C4AA C 0.2588(3) 0.3599(4) 0.1548(3) 0.0278(9) Uani 1 1 d . . . . .
C5A C 0.3294(4) 0.2676(4) 0.2420(4) 0.0332(11) Uani 1 1 d . . . . .
H5A H 0.4114 0.2694 0.2694 0.040 Uiso 1 1 calc R U . . .
C6A C 0.2808(4) 0.1755(4) 0.2874(4) 0.0340(10) Uani 1 1 d . . . . .
H6A H 0.3294 0.1144 0.3473 0.041 Uiso 1 1 calc R U . . .
C7A C 0.1611(4) 0.1705(4) 0.2466(5) 0.0351(12) Uani 1 1 d . . . . .
H7A H 0.1283 0.1059 0.2788 0.042 Uiso 1 1 calc R U . . .
C8A C 0.0894(3) 0.2583(4) 0.1602(3) 0.0306(9) Uani 1 1 d . . . . .
H8A H 0.0075 0.2530 0.1322 0.037 Uiso 1 1 calc R U . . .
C8AA C 0.1367(3) 0.3570(3) 0.1121(3) 0.0252(9) Uani 1 1 d . . . . .
Br1B Br 0.0519(10) 0.5379(11) 0.3693(9) 0.0268(19) Uani 0.094(3) 1 d . . P . .
F1B F 0.0729(5) 0.5463(6) 0.3456(5) 0.0332(14) Uani 0.906(3) 1 d . . P . .
C1B C 0.4356(3) 0.5539(4) 0.4756(3) 0.0257(8) Uani 1 1 d . . . . .
C2B C 0.3810(3) 0.4572(4) 0.5111(3) 0.0284(9) Uani 1 1 d . . . . .
H2B H 0.4272 0.3919 0.5662 0.034 Uiso 1 1 calc R U . . .
C3B C 0.2595(3) 0.4533(4) 0.4677(3) 0.0299(9) Uani 1 1 d . . . . .
H3B H 0.2236 0.3866 0.4932 0.036 Uiso 1 1 calc R U . . .
C4B C 0.1940(3) 0.5476(4) 0.3881(3) 0.0276(8) Uani 1 1 d . . . . .
C4AB C 0.2418(3) 0.6461(3) 0.3446(3) 0.0244(8) Uani 1 1 d . . . . .
C5B C 0.1709(4) 0.7406(4) 0.2568(4) 0.0266(10) Uani 1 1 d . . . . .
H5B H 0.0887 0.7392 0.2283 0.032 Uiso 1 1 calc R U . . .
C6B C 0.2212(3) 0.8334(4) 0.2134(4) 0.0291(9) Uani 1 1 d . . . . .
H6B H 0.1741 0.8961 0.1547 0.035 Uiso 1 1 calc R U . . .
C7B C 0.3425(4) 0.8352(4) 0.2559(4) 0.0285(10) Uani 1 1 d . . . . .
H7B H 0.3767 0.8995 0.2251 0.034 Uiso 1 1 calc R U . . .
C8B C 0.4121(3) 0.7471(4) 0.3401(3) 0.0255(8) Uani 1 1 d . . . . .
H8B H 0.4939 0.7512 0.3671 0.031 Uiso 1 1 calc R U . . .
C8AB C 0.3655(3) 0.6492(3) 0.3889(3) 0.0257(9) Uani 1 1 d . . . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1A C4A 1.771(5) . ?
F1A C4A 1.403(6) . ?
C1A C2A 1.367(5) . ?
C1A C8AA 1.440(5) . ?
C1A C1A 1.490(6) 2 ?
C2A C3A 1.405(5) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.345(6) . ?
C3A H3A 0.9500 . ?
C4A C4AA 1.428(5) . ?
C4AA C5A 1.407(7) . ?
C4AA C8AA 1.412(5) . ?
C5A C6A 1.366(6) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.387(6) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.375(6) . ?
C7A H7A 0.9500 . ?
C8A C8AA 1.424(5) . ?
C8A H8A 0.9500 . ?
Br1B C4B 1.725(11) . ?
F1B C4B 1.400(6) . ?
C1B C2B 1.389(5) . ?
C1B C8AB 1.426(5) . ?
C1B C1B 1.485(6) 2_656 ?
C2B C3B 1.405(5) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.366(5) . ?
C3B H3B 0.9500 . ?
C4B C4AB 1.398(5) . ?
C4AB C5B 1.428(6) . ?
C4AB C8AB 1.430(5) . ?
C5B C6B 1.373(6) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.402(6) . ?
C6B H6B 0.9500 . ?
C7B C8B 1.358(6) . ?
C7B H7B 0.9500 . ?
C8B C8AB 1.417(5) . ?
C8B H8B 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
C2A C1A C8AA 118.3(3) . . ?
C2A C1A C1A 119.7(3) . 2 ?
C8AA C1A C1A 122.0(2) . 2 ?
C1A C2A C3A 122.8(4) . . ?
C1A C2A H2A 118.6 . . ?
C3A C2A H2A 118.6 . . ?
C4A C3A C2A 118.4(4) . . ?
C4A C3A H3A 120.8 . . ?
C2A C3A H3A 120.8 . . ?
C3A C4A F1A 121.1(4) . . ?
C3A C4A C4AA 123.3(3) . . ?
F1A C4A C4AA 115.6(5) . . ?
C3A C4A Br1A 112.1(3) . . ?
F1A C4A Br1A 11.1(3) . . ?
C4AA C4A Br1A 124.2(4) . . ?
C5A C4AA C8AA 120.2(3) . . ?
C5A C4AA C4A 122.7(4) . . ?
C8AA C4AA C4A 117.1(3) . . ?
C6A C5A C4AA 120.4(4) . . ?
C6A C5A H5A 119.8 . . ?
C4AA C5A H5A 119.8 . . ?
C5A C6A C7A 120.5(4) . . ?
C5A C6A H6A 119.8 . . ?
C7A C6A H6A 119.8 . . ?
C8A C7A C6A 120.6(4) . . ?
C8A C7A H7A 119.7 . . ?
C6A C7A H7A 119.7 . . ?
C7A C8A C8AA 120.7(4) . . ?
C7A C8A H8A 119.7 . . ?
C8AA C8A H8A 119.7 . . ?
C4AA C8AA C8A 117.7(3) . . ?
C4AA C8AA C1A 120.1(3) . . ?
C8A C8AA C1A 122.2(3) . . ?
C2B C1B C8AB 118.8(3) . . ?
C2B C1B C1B 119.8(3) . 2_656 ?
C8AB C1B C1B 121.3(3) . 2_656 ?
C1B C2B C3B 121.9(4) . . ?
C1B C2B H2B 119.0 . . ?
C3B C2B H2B 119.0 . . ?
C4B C3B C2B 118.4(4) . . ?
C4B C3B H3B 120.8 . . ?
C2B C3B H3B 120.8 . . ?
C3B C4B C4AB 123.2(3) . . ?
C3B C4B F1B 119.2(4) . . ?
C4AB C4B F1B 117.6(4) . . ?
C3B C4B Br1B 110.4(4) . . ?
C4AB C4B Br1B 125.9(5) . . ?
F1B C4B Br1B 11.9(5) . . ?
C4B C4AB C5B 122.0(3) . . ?
C4B C4AB C8AB 118.0(3) . . ?
C5B C4AB C8AB 120.0(3) . . ?
C6B C5B C4AB 120.1(4) . . ?
C6B C5B H5B 120.0 . . ?
C4AB C5B H5B 120.0 . . ?
C5B C6B C7B 119.8(4) . . ?
C5B C6B H6B 120.1 . . ?
C7B C6B H6B 120.1 . . ?
C8B C7B C6B 121.4(4) . . ?
C8B C7B H7B 119.3 . . ?
C6B C7B H7B 119.3 . . ?
C7B C8B C8AB 121.5(4) . . ?
C7B C8B H8B 119.2 . . ?
C8AB C8B H8B 119.2 . . ?
C8B C8AB C1B 123.1(3) . . ?
C8B C8AB C4AB 117.2(3) . . ?
C1B C8AB C4AB 119.6(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
C8AA C1A C2A C3A 1.8(5) . . . . ?
C1A C1A C2A C3A -179.7(3) 2 . . . ?
C1A C2A C3A C4A -0.1(5) . . . . ?
C2A C3A C4A F1A 179.1(4) . . . . ?
C2A C3A C4A C4AA -1.3(5) . . . . ?
C2A C3A C4A Br1A 171.8(3) . . . . ?
C3A C4A C4AA C5A -177.4(4) . . . . ?
F1A C4A C4AA C5A 2.2(6) . . . . ?
Br1A C4A C4AA C5A 10.4(6) . . . . ?
C3A C4A C4AA C8AA 0.9(5) . . . . ?
F1A C4A C4AA C8AA -179.5(4) . . . . ?
Br1A C4A C4AA C8AA -171.3(3) . . . . ?
C8AA C4AA C5A C6A -0.9(6) . . . . ?
C4A C4AA C5A C6A 177.3(3) . . . . ?
C4AA C5A C6A C7A 1.0(6) . . . . ?
C5A C6A C7A C8A -0.1(6) . . . . ?
C6A C7A C8A C8AA -0.9(6) . . . . ?
C5A C4AA C8AA C8A -0.1(5) . . . . ?
C4A C4AA C8AA C8A -178.4(3) . . . . ?
C5A C4AA C8AA C1A 179.2(4) . . . . ?
C4A C4AA C8AA C1A 0.9(5) . . . . ?
C7A C8A C8AA C4AA 1.0(5) . . . . ?
C7A C8A C8AA C1A -178.3(4) . . . . ?
C2A C1A C8AA C4AA -2.2(5) . . . . ?
C1A C1A C8AA C4AA 179.4(3) 2 . . . ?
C2A C1A C8AA C8A 177.1(3) . . . . ?
C1A C1A C8AA C8A -1.3(5) 2 . . . ?
C8AB C1B C2B C3B -2.3(5) . . . . ?
C1B C1B C2B C3B 179.8(3) 2_656 . . . ?
C1B C2B C3B C4B 0.2(5) . . . . ?
C2B C3B C4B C4AB 1.8(5) . . . . ?
C2B C3B C4B F1B -179.0(4) . . . . ?
C2B C3B C4B Br1B -170.2(4) . . . . ?
C3B C4B C4AB C5B 177.2(3) . . . . ?
F1B C4B C4AB C5B -2.0(5) . . . . ?
Br1B C4B C4AB C5B -12.0(6) . . . . ?
C3B C4B C4AB C8AB -1.6(5) . . . . ?
F1B C4B C4AB C8AB 179.2(4) . . . . ?
Br1B C4B C4AB C8AB 169.1(5) . . . . ?
C4B C4AB C5B C6B -177.9(3) . . . . ?
C8AB C4AB C5B C6B 0.8(5) . . . . ?
C4AB C5B C6B C7B -0.2(5) . . . . ?
C5B C6B C7B C8B -0.3(5) . . . . ?
C6B C7B C8B C8AB 0.1(6) . . . . ?
C7B C8B C8AB C1B 178.9(3) . . . . ?
C7B C8B C8AB C4AB 0.6(5) . . . . ?
C2B C1B C8AB C8B -175.8(3) . . . . ?
C1B C1B C8AB C8B 2.1(5) 2_656 . . . ?
C2B C1B C8AB C4AB 2.4(5) . . . . ?
C1B C1B C8AB C4AB -179.7(3) 2_656 . . . ?
C4B C4AB C8AB C8B 177.8(3) . . . . ?
C5B C4AB C8AB C8B -1.0(5) . . . . ?
C4B C4AB C8AB C1B -0.5(4) . . . . ?
C5B C4AB C8AB C1B -179.4(3) . . . . ?

####################################################################### 
# 
# 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_10-1_in_C2
_database_code_depnum_ccdc_archive 'CCDC 1476394'
_audit_update_record             
;
2017-07-27 deposited with the CCDC.
2017-08-15 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H24 Br0.55 F3.45'
_chemical_formula_iupac          ?
_chemical_formula_weight         614.09
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   12.6575(11)
_cell_length_b                   10.6532(9)
_cell_length_c                   11.1899(10)
_cell_angle_alpha                90
_cell_angle_beta                 115.098(2)
_cell_angle_gamma                90
_cell_volume                     1366.4(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4790
_cell_measurement_theta_min      2.6103
_cell_measurement_theta_max      26.4162
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.395
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.076
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             629

_exptl_absorpt_coefficient_mu    0.901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.94

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  TRIUMPH

_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            10738
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         26.42
_diffrn_reflns_theta_full        26.42
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
Investigated crystal (10-1) contains mixture of F and Br 
substituted 4,4? binaphtyl. During structure refinement 
position and anisotropic temperature factors for all 
non-H atoms were refined. The occupancy ratio of F/Br 
was free to refine. In the F/Br mixed crystals possible 
lowering of the space group symmetry from C2/c to chiral 
C2 was observed. This was tested by structure refinement 
in both C2 (current data block) and C2/c (10-1_in_C2c 
data block) space groups. In the C2 choice crystal is 
twinned by the inversion with twin component ratio 
refined to 0.53(3) and 0.47(3). The C2 choice gives 
significantly lower R values than corresponding C2/c 
choice.
;

_reflns_number_total             2812
_reflns_number_gt                2359
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0815
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.039
_refine_ls_number_reflns         2812
_refine_ls_number_parameters     220
_refine_ls_number_restraints     2
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0358P)²+0.6309P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.152
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Refined as an inversion twin.'
_refine_ls_abs_structure_Flack   0.47(3)

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX2 V2014 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX2 V2014 (Bruker AXS Inc., 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1A 0.4526(5) 0.4689(7) 0.1324(6) 0.0289(10) Uani d . P . 0.194(3) . .
F F1A 0.4288(6) 0.4591(10) 0.1527(7) 0.036(2) Uani d . P . 0.806(3) . .
C C1A 0.0655(3) 0.4488(4) 0.0247(3) 0.0258(9) Uani d . . . 1.0 . .
C C2A 0.1182(3) 0.5453(4) -0.0126(3) 0.0301(9) Uani d . . . 1.0 . .
H H2A 0.0712 0.6101 -0.0681 0.036 Uiso calc U . R 1.0 . .
C C3A 0.2390(3) 0.5495(4) 0.0296(3) 0.0317(9) Uani d . . . 1.0 . .
H H3A 0.2738 0.6164 0.0029 0.038 Uiso calc U . R 1.0 . .
C C4A 0.3058(3) 0.4578(5) 0.1084(3) 0.0305(8) Uani d . . . 1.0 . .
C C4AA 0.2591(3) 0.3580(4) 0.1551(3) 0.0270(9) Uani d . . . 1.0 . .
C C5A 0.3303(4) 0.2654(4) 0.2421(4) 0.0290(10) Uani d . . . 1.0 . .
H H5A 0.4123 0.2666 0.2691 0.035 Uiso calc U . R 1.0 . .
C C6A 0.2812(4) 0.1742(4) 0.2870(4) 0.0339(10) Uani d . . . 1.0 . .
H H6A 0.3299 0.1129 0.3466 0.041 Uiso calc U . R 1.0 . .
C C7A 0.1614(5) 0.1685(4) 0.2479(5) 0.0336(11) Uani d . . . 1.0 . .
H H7A 0.129 0.1043 0.2811 0.04 Uiso calc U . R 1.0 . .
C C8A 0.0895(3) 0.2564(4) 0.1604(3) 0.0296(9) Uani d . . . 1.0 . .
H H8A 0.0075 0.2511 0.1326 0.035 Uiso calc U . R 1.0 . .
C C8AA 0.1362(3) 0.3552(3) 0.1113(3) 0.0249(9) Uani d . . . 1.0 . .
Br Br1B 0.0499(9) 0.5346(13) 0.3685(11) 0.021(2) Uani d . P D 0.081(3) . .
F F1B 0.0748(4) 0.5450(7) 0.3470(5) 0.0308(13) Uani d . P . 0.919(3) . .
C C1B 0.4358(3) 0.5504(4) 0.4756(3) 0.0259(8) Uani d . . . 1.0 . .
C C2B 0.3809(3) 0.4558(4) 0.5102(3) 0.0281(9) Uani d . . . 1.0 . .
H H2B 0.4272 0.3907 0.5656 0.034 Uiso calc U . R 1.0 . .
C C3B 0.2595(3) 0.4504(4) 0.4677(3) 0.0297(9) Uani d . . . 1.0 . .
H H3B 0.2241 0.3836 0.4937 0.036 Uiso calc U . R 1.0 . .
C C4B 0.1942(3) 0.5445(4) 0.3881(3) 0.0277(8) Uani d . . D 1.0 . .
C C4AB 0.2416(3) 0.6442(4) 0.3445(3) 0.0253(9) Uani d . . . 1.0 . .
C C5B 0.1718(4) 0.7383(4) 0.2563(4) 0.0292(10) Uani d . . . 1.0 . .
H H5B 0.0895 0.736 0.2267 0.035 Uiso calc U . R 1.0 . .
C C6B 0.2208(3) 0.8322(4) 0.2130(4) 0.0279(9) Uani d . . . 1.0 . .
H H6B 0.1735 0.8954 0.1549 0.034 Uiso calc U . R 1.0 . .
C C7B 0.3430(4) 0.8333(4) 0.2564(5) 0.0294(10) Uani d . . . 1.0 . .
H H7B 0.3777 0.8976 0.2261 0.035 Uiso calc U . R 1.0 . .
C C8B 0.4122(3) 0.7450(4) 0.3401(3) 0.0256(8) Uani d . . . 1.0 . .
H H8B 0.4942 0.7484 0.3672 0.031 Uiso calc U . R 1.0 . .
C C8AB 0.3643(3) 0.6477(3) 0.3880(3) 0.0253(9) Uani d . . . 1.0 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1A C4A . 1.765(6) ?
F1A C4A . 1.420(8) ?
C1A C2A . 1.382(5) ?
C1A C8AA . 1.414(5) ?
C1A C1A 2 1.510(7) ?
C2A C3A . 1.398(5) ?
C2A H2A . 0.95 ?
C3A C4A . 1.347(6) ?
C3A H3A . 0.95 ?
C4A C4AA . 1.420(5) ?
C4AA C5A . 1.411(6) ?
C4AA C8AA . 1.419(5) ?
C5A C6A . 1.360(6) ?
C5A H5A . 0.95 ?
C6A C7A . 1.390(6) ?
C6A H6A . 0.95 ?
C7A C8A . 1.381(6) ?
C7A H7A . 0.95 ?
C8A C8AA . 1.427(5) ?
C8A H8A . 0.95 ?
Br1B C4B . 1.748(9) ?
F1B C4B . 1.380(6) ?
C1B C2B . 1.370(6) ?
C1B C8AB . 1.450(5) ?
C1B C1B 2_656 1.478(7) ?
C2B C3B . 1.403(5) ?
C2B H2B . 0.95 ?
C3B C4B . 1.363(5) ?
C3B H3B . 0.95 ?
C4B C4AB . 1.404(5) ?
C4AB C8AB . 1.418(5) ?
C4AB C5B . 1.421(6) ?
C5B C6B . 1.370(6) ?
C5B H5B . 0.95 ?
C6B C7B . 1.411(6) ?
C6B H6B . 0.95 ?
C7B C8B . 1.354(6) ?
C7B H7B . 0.95 ?
C8B C8AB . 1.416(5) ?
C8B H8B . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2A C1A C8AA . . 119.0(3) ?
C2A C1A C1A . 2 119.0(3) ?
C8AA C1A C1A . 2 121.9(3) ?
C1A C2A C3A . . 121.4(4) ?
C1A C2A H2A . . 119.3 ?
C3A C2A H2A . . 119.3 ?
C4A C3A C2A . . 119.4(4) ?
C4A C3A H3A . . 120.3 ?
C2A C3A H3A . . 120.3 ?
C3A C4A C4AA . . 122.7(3) ?
C3A C4A F1A . . 120.8(5) ?
C4AA C4A F1A . . 116.4(5) ?
C3A C4A Br1A . . 112.2(4) ?
C4AA C4A Br1A . . 124.8(4) ?
F1A C4A Br1A . . 11.0(4) ?
C5A C4AA C8AA . . 120.7(3) ?
C5A C4AA C4A . . 122.2(4) ?
C8AA C4AA C4A . . 117.1(3) ?
C6A C5A C4AA . . 119.7(4) ?
C6A C5A H5A . . 120.1 ?
C4AA C5A H5A . . 120.1 ?
C5A C6A C7A . . 121.6(4) ?
C5A C6A H6A . . 119.2 ?
C7A C6A H6A . . 119.2 ?
C8A C7A C6A . . 119.7(4) ?
C8A C7A H7A . . 120.1 ?
C6A C7A H7A . . 120.1 ?
C7A C8A C8AA . . 121.2(4) ?
C7A C8A H8A . . 119.4 ?
C8AA C8A H8A . . 119.4 ?
C1A C8AA C4AA . . 120.3(3) ?
C1A C8AA C8A . . 122.6(3) ?
C4AA C8AA C8A . . 117.1(3) ?
C2B C1B C8AB . . 118.1(3) ?
C2B C1B C1B . 2_656 120.4(3) ?
C8AB C1B C1B . 2_656 121.5(3) ?
C1B C2B C3B . . 123.3(4) ?
C1B C2B H2B . . 118.4 ?
C3B C2B H2B . . 118.4 ?
C4B C3B C2B . . 117.7(4) ?
C4B C3B H3B . . 121.2 ?
C2B C3B H3B . . 121.2 ?
C3B C4B F1B . . 119.7(4) ?
C3B C4B C4AB . . 123.6(3) ?
F1B C4B C4AB . . 116.7(4) ?
C3B C4B Br1B . . 110.4(5) ?
F1B C4B Br1B . . 11.6(5) ?
C4AB C4B Br1B . . 125.4(5) ?
C4B C4AB C8AB . . 117.9(3) ?
C4B C4AB C5B . . 122.9(4) ?
C8AB C4AB C5B . . 119.2(3) ?
C6B C5B C4AB . . 121.3(4) ?
C6B C5B H5B . . 119.3 ?
C4AB C5B H5B . . 119.3 ?
C5B C6B C7B . . 118.6(4) ?
C5B C6B H6B . . 120.7 ?
C7B C6B H6B . . 120.7 ?
C8B C7B C6B . . 121.7(4) ?
C8B C7B H7B . . 119.1 ?
C6B C7B H7B . . 119.1 ?
C7B C8B C8AB . . 121.0(3) ?
C7B C8B H8B . . 119.5 ?
C8AB C8B H8B . . 119.5 ?
C8B C8AB C4AB . . 118.2(3) ?
C8B C8AB C1B . . 122.3(3) ?
C4AB C8AB C1B . . 119.5(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8AA C1A C2A C3A . . . . 2.3(5) ?
C1A C1A C2A C3A 2 . . . -179.6(3) ?
C1A C2A C3A C4A . . . . -0.1(5) ?
C2A C3A C4A C4AA . . . . -2.3(5) ?
C2A C3A C4A F1A . . . . 179.8(5) ?
C2A C3A C4A Br1A . . . . 172.1(4) ?
C3A C4A C4AA C5A . . . . -177.3(4) ?
F1A C4A C4AA C5A . . . . 0.7(6) ?
Br1A C4A C4AA C5A . . . . 9.0(6) ?
C3A C4A C4AA C8AA . . . . 2.2(5) ?
F1A C4A C4AA C8AA . . . . -179.7(5) ?
Br1A C4A C4AA C8AA . . . . -171.4(4) ?
C8AA C4AA C5A C6A . . . . -1.7(6) ?
C4A C4AA C5A C6A . . . . 177.9(3) ?
C4AA C5A C6A C7A . . . . 1.0(6) ?
C5A C6A C7A C8A . . . . 0.5(6) ?
C6A C7A C8A C8AA . . . . -1.3(6) ?
C2A C1A C8AA C4AA . . . . -2.3(5) ?
C1A C1A C8AA C4AA 2 . . . 179.7(3) ?
C2A C1A C8AA C8A . . . . 176.4(3) ?
C1A C1A C8AA C8A 2 . . . -1.6(5) ?
C5A C4AA C8AA C1A . . . . 179.7(4) ?
C4A C4AA C8AA C1A . . . . 0.1(5) ?
C5A C4AA C8AA C8A . . . . 0.9(5) ?
C4A C4AA C8AA C8A . . . . -178.7(3) ?
C7A C8A C8AA C1A . . . . -178.1(4) ?
C7A C8A C8AA C4AA . . . . 0.6(5) ?
C8AB C1B C2B C3B . . . . -1.7(5) ?
C1B C1B C2B C3B 2_656 . . . 179.8(3) ?
C1B C2B C3B C4B . . . . 0.1(5) ?
C2B C3B C4B F1B . . . . -178.1(4) ?
C2B C3B C4B C4AB . . . . 1.4(5) ?
C2B C3B C4B Br1B . . . . -170.4(5) ?
C3B C4B C4AB C8AB . . . . -1.2(5) ?
F1B C4B C4AB C8AB . . . . 178.4(4) ?
Br1B C4B C4AB C8AB . . . . 169.3(5) ?
C3B C4B C4AB C5B . . . . 176.9(4) ?
F1B C4B C4AB C5B . . . . -3.6(6) ?
Br1B C4B C4AB C5B . . . . -12.6(7) ?
C4B C4AB C5B C6B . . . . -178.2(3) ?
C8AB C4AB C5B C6B . . . . -0.2(6) ?
C4AB C5B C6B C7B . . . . 0.8(5) ?
C5B C6B C7B C8B . . . . -0.7(5) ?
C6B C7B C8B C8AB . . . . -0.2(6) ?
C7B C8B C8AB C4AB . . . . 0.8(5) ?
C7B C8B C8AB C1B . . . . 178.7(4) ?
C4B C4AB C8AB C8B . . . . 177.4(3) ?
C5B C4AB C8AB C8B . . . . -0.7(5) ?
C4B C4AB C8AB C1B . . . . -0.5(5) ?
C5B C4AB C8AB C1B . . . . -178.6(4) ?
C2B C1B C8AB C8B . . . . -176.0(3) ?
C1B C1B C8AB C8B 2_656 . . . 2.5(5) ?
C2B C1B C8AB C4AB . . . . 1.8(5) ?
C1B C1B C8AB C4AB 2_656 . . . -179.6(3) ?

####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 1476389'
_audit_update_record             
;
2017-07-27 deposited with the CCDC.
2017-08-15 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H22'
_chemical_formula_iupac          ?
_chemical_formula_weight         406.49

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.1208(4)
_cell_length_b                   25.0267(10)
_cell_length_c                   33.4392(14)
_cell_angle_alpha                90
_cell_angle_beta                 92.0165(13)
_cell_angle_gamma                90
_cell_volume                     8464.6(6)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    9857
_cell_measurement_theta_min      2.645
_cell_measurement_theta_max      66.532
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       planar
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.323
_exptl_crystal_size_mid          0.243
_exptl_crystal_size_min          0.014
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3424

_exptl_absorpt_coefficient_mu    0.547
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'INCOATEC I\mS micro--focus source'
_diffrn_source_type              ?

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  mirror

_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            105660
_diffrn_reflns_av_R_equivalents  0.0762
_diffrn_reflns_av_unetI/netI     0.0591
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         64.97
_diffrn_reflns_theta_full        64.97
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?

_refine_special_details          
;
;

_reflns_number_total             14332
_reflns_number_gt                8319
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1097
_refine_ls_R_factor_gt           0.0694
_refine_ls_wR_factor_gt          0.1648
_refine_ls_wR_factor_ref         0.2076
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_number_reflns         14332
_refine_ls_number_parameters     1154
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0845P)²+5.5788P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.269
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00019(3)

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 0.0000 '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'

_computing_data_collection       'APEX2 V2014 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX2 V2014 (Bruker AXS Inc., 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1A 0.7339(2) 0.29181(11) 0.77081(8) 0.0227(6) Uani d . . . 1 . .
C C2A 0.6524(3) 0.33252(11) 0.78191(8) 0.0230(6) Uani d . . . 1 . .
H H2A 0.6123 0.3547 0.7619 0.028 Uiso calc U . R 1 . .
C C3A 0.6269(3) 0.34212(11) 0.82249(8) 0.0229(6) Uani d . . . 1 . .
H H3A 0.5697 0.3706 0.8292 0.028 Uiso calc U . R 1 . .
C C4A 0.6833(3) 0.31098(11) 0.85256(8) 0.0240(6) Uani d . . . 1 . .
C C5A 0.8135(3) 0.22839(11) 0.87018(8) 0.0266(6) Uani d . . . 1 . .
H H5A 0.795 0.2329 0.8976 0.032 Uiso calc U . R 1 . .
C C6A 0.8871(3) 0.18599(11) 0.85910(9) 0.0294(6) Uani d . . . 1 . .
H H6A 0.919 0.1614 0.8788 0.035 Uiso calc U . R 1 . .
C C7A 0.9170(3) 0.17790(11) 0.81873(8) 0.0263(6) Uani d . . . 1 . .
H H7A 0.9698 0.1483 0.8114 0.032 Uiso calc U . R 1 . .
C C8A 0.8696(2) 0.21282(11) 0.79018(8) 0.0238(6) Uani d . . . 1 . .
H H8A 0.8908 0.2075 0.763 0.029 Uiso calc U . R 1 . .
C C9A 0.7887(2) 0.25724(11) 0.80049(8) 0.0225(6) Uani d . . . 1 . .
C C10A 0.7634(3) 0.26623(11) 0.84200(8) 0.0244(6) Uani d . . . 1 . .
C C11A 0.7628(2) 0.28651(11) 0.72741(8) 0.0220(6) Uani d . . . 1 . .
C C12A 0.8398(3) 0.32439(11) 0.70941(8) 0.0241(6) Uani d . . . 1 . .
H H12A 0.879 0.352 0.7253 0.029 Uiso calc U . R 1 . .
C C13A 0.8621(3) 0.32337(11) 0.66823(8) 0.0241(6) Uani d . . . 1 . .
H H13A 0.9169 0.3499 0.6571 0.029 Uiso calc U . R 1 . .
C C14A 0.8070(2) 0.28527(11) 0.64377(8) 0.0227(6) Uani d . . . 1 . .
C C15A 0.6547(3) 0.20673(11) 0.63661(8) 0.0249(6) Uani d . . . 1 . .
H H15A 0.6621 0.2072 0.6084 0.03 Uiso calc U . R 1 . .
C C16A 0.5761(3) 0.16909(11) 0.65363(8) 0.0247(6) Uani d . . . 1 . .
H H16A 0.5296 0.144 0.6371 0.03 Uiso calc U . R 1 . .
C C17A 0.5638(3) 0.16720(11) 0.69519(8) 0.0254(6) Uani d . . . 1 . .
H H17A 0.5127 0.1398 0.7068 0.031 Uiso calc U . R 1 . .
C C18A 0.6248(3) 0.20450(11) 0.71906(8) 0.0237(6) Uani d . . . 1 . .
H H18A 0.6134 0.2034 0.7471 0.028 Uiso calc U . R 1 . .
C C19A 0.7060(3) 0.24539(11) 0.70254(8) 0.0234(6) Uani d . . . 1 . .
C C20A 0.7254(2) 0.24525(10) 0.66033(8) 0.0213(6) Uani d . . . 1 . .
C C21A 0.6593(3) 0.32494(11) 0.89498(8) 0.0228(6) Uani d . . . 1 . .
C C22A 0.5301(3) 0.33321(11) 0.90729(8) 0.0248(6) Uani d . . . 1 . .
H H22A 0.458 0.329 0.8886 0.03 Uiso calc U . R 1 . .
C C23A 0.5066(3) 0.34743(11) 0.94636(8) 0.0281(6) Uani d . . . 1 . .
H H23A 0.4181 0.3521 0.9544 0.034 Uiso calc U . R 1 . .
C C24A 0.6094(3) 0.35497(12) 0.97384(9) 0.0294(6) Uani d . . . 1 . .
H H24A 0.592 0.3653 1.0005 0.035 Uiso calc U . R 1 . .
C C25A 0.7393(3) 0.34729(12) 0.96234(8) 0.0299(6) Uani d . . . 1 . .
H H25A 0.8108 0.3523 0.9811 0.036 Uiso calc U . R 1 . .
C C26A 0.7635(3) 0.33232(12) 0.92345(8) 0.0277(6) Uani d . . . 1 . .
H H26A 0.8521 0.3269 0.9158 0.033 Uiso calc U . R 1 . .
C C27A 0.8335(2) 0.28811(11) 0.59947(8) 0.0240(6) Uani d . . . 1 . .
C C28A 0.8709(3) 0.24425(12) 0.57766(8) 0.0272(6) Uani d . . . 1 . .
H H28A 0.8789 0.2103 0.5903 0.033 Uiso calc U . R 1 . .
C C29A 0.8971(3) 0.24948(13) 0.53674(8) 0.0287(6) Uani d . . . 1 . .
H H29A 0.9217 0.2191 0.5217 0.034 Uiso calc U . R 1 . .
C C30A 0.8869(3) 0.29899(13) 0.51865(9) 0.0323(7) Uani d . . . 1 . .
H H30A 0.9033 0.3027 0.491 0.039 Uiso calc U . R 1 . .
C C31A 0.8530(3) 0.34295(12) 0.54079(8) 0.0299(7) Uani d . . . 1 . .
H H31A 0.8482 0.3771 0.5285 0.036 Uiso calc U . R 1 . .
C C32A 0.8258(3) 0.33773(12) 0.58071(9) 0.0280(6) Uani d . . . 1 . .
H H32A 0.8016 0.3683 0.5956 0.034 Uiso calc U . R 1 . .
C C1B 0.2337(2) 0.34286(11) 0.76645(8) 0.0234(6) Uani d . . . 1 . .
C C2B 0.1638(3) 0.30352(11) 0.78476(8) 0.0241(6) Uani d . . . 1 . .
H H2B 0.1293 0.2746 0.7692 0.029 Uiso calc U . R 1 . .
C C3B 0.1418(3) 0.30480(11) 0.82572(8) 0.0235(6) Uani d . . . 1 . .
H H3B 0.0907 0.2771 0.837 0.028 Uiso calc U . R 1 . .
C C4B 0.1913(2) 0.34467(11) 0.85061(8) 0.0219(6) Uani d . . . 1 . .
C C5B 0.3276(3) 0.42901(11) 0.85491(8) 0.0226(6) Uani d . . . 1 . .
H H5B 0.3179 0.43 0.8831 0.027 Uiso calc U . R 1 . .
C C6B 0.3996(3) 0.46834(11) 0.83702(8) 0.0249(6) Uani d . . . 1 . .
H H6B 0.4361 0.4968 0.8526 0.03 Uiso calc U . R 1 . .
C C7B 0.4193(3) 0.46650(11) 0.79560(8) 0.0245(6) Uani d . . . 1 . .
H H7B 0.47 0.4934 0.7833 0.029 Uiso calc U . R 1 . .
C C8B 0.3658(3) 0.42623(11) 0.77332(8) 0.0244(6) Uani d . . . 1 . .
H H8B 0.381 0.4252 0.7455 0.029 Uiso calc U . R 1 . .
C C9B 0.2878(3) 0.38558(10) 0.79023(8) 0.0216(6) Uani d . . . 1 . .
C C10B 0.2674(3) 0.38700(11) 0.83247(8) 0.0232(6) Uani d . . . 1 . .
C C11B 0.2607(3) 0.33793(11) 0.72295(8) 0.0231(6) Uani d . . . 1 . .
C C12B 0.3420(3) 0.29718(11) 0.71073(8) 0.0235(6) Uani d . . . 1 . .
H H12B 0.3827 0.2744 0.7303 0.028 Uiso calc U . R 1 . .
C C13B 0.3659(3) 0.28866(11) 0.67026(8) 0.0256(6) Uani d . . . 1 . .
H H13B 0.4247 0.2609 0.6632 0.031 Uiso calc U . R 1 . .
C C14B 0.3071(3) 0.31905(11) 0.64056(8) 0.0237(6) Uani d . . . 1 . .
C C15B 0.1662(3) 0.39840(11) 0.62242(8) 0.0265(6) Uani d . . . 1 . .
H H15B 0.1806 0.3925 0.5948 0.032 Uiso calc U . R 1 . .
C C16B 0.0900(3) 0.44043(11) 0.63376(9) 0.0277(6) Uani d . . . 1 . .
H H16B 0.0528 0.4638 0.614 0.033 Uiso calc U . R 1 . .
C C17B 0.0662(3) 0.44944(11) 0.67429(8) 0.0249(6) Uani d . . . 1 . .
H H17B 0.0113 0.4783 0.6817 0.03 Uiso calc U . R 1 . .
C C18B 0.1217(3) 0.41678(11) 0.70320(8) 0.0246(6) Uani d . . . 1 . .
H H18B 0.1065 0.4238 0.7306 0.029 Uiso calc U . R 1 . .
C C19B 0.2019(3) 0.37238(11) 0.69285(8) 0.0236(6) Uani d . . . 1 . .
C C20B 0.2247(3) 0.36307(11) 0.65179(8) 0.0221(6) Uani d . . . 1 . .
C C21B 0.1653(2) 0.34311(11) 0.89392(8) 0.0228(6) Uani d . . . 1 . .
C C22B 0.1773(3) 0.29385(12) 0.91409(8) 0.0260(6) Uani d . . . 1 . .
H H22B 0.2041 0.2631 0.8998 0.031 Uiso calc U . R 1 . .
C C23B 0.1511(3) 0.28924(12) 0.95430(8) 0.0295(6) Uani d . . . 1 . .
H H23B 0.1604 0.2556 0.9673 0.035 Uiso calc U . R 1 . .
C C24B 0.1118(3) 0.33288(12) 0.97543(8) 0.0302(7) Uani d . . . 1 . .
H H24B 0.0929 0.3296 1.003 0.036 Uiso calc U . R 1 . .
C C25B 0.0996(3) 0.38218(12) 0.95639(8) 0.0289(6) Uani d . . . 1 . .
H H25B 0.0738 0.4127 0.9711 0.035 Uiso calc U . R 1 . .
C C26B 0.1248(3) 0.38694(11) 0.91613(8) 0.0245(6) Uani d . . . 1 . .
H H26B 0.1143 0.4207 0.9034 0.029 Uiso calc U . R 1 . .
C C27B 0.3310(3) 0.30460(11) 0.59829(8) 0.0233(6) Uani d . . . 1 . .
C C28B 0.2275(3) 0.29411(11) 0.57037(9) 0.0286(6) Uani d . . . 1 . .
H H28B 0.1385 0.2994 0.5775 0.034 Uiso calc U . R 1 . .
C C29B 0.2551(3) 0.27600(12) 0.53225(9) 0.0293(6) Uani d . . . 1 . .
H H29B 0.1841 0.268 0.5139 0.035 Uiso calc U . R 1 . .
C C30B 0.3834(3) 0.26948(12) 0.52054(9) 0.0291(6) Uani d . . . 1 . .
H H30B 0.4005 0.2576 0.4943 0.035 Uiso calc U . R 1 . .
C C31B 0.4878(3) 0.28053(12) 0.54761(9) 0.0291(6) Uani d . . . 1 . .
H H31B 0.5766 0.2763 0.5399 0.035 Uiso calc U . R 1 . .
C C32B 0.4609(3) 0.29796(11) 0.58631(8) 0.0262(6) Uani d . . . 1 . .
H H32B 0.5322 0.3054 0.6047 0.031 Uiso calc U . R 1 . .
C C1C 0.7390(3) 0.40853(10) 0.28330(8) 0.0213(6) Uani d . . . 1 . .
C C2C 0.6636(3) 0.44731(11) 0.29953(8) 0.0272(6) Uani d . . . 1 . .
H H2C 0.6259 0.4742 0.2827 0.033 Uiso calc U . R 1 . .
C C3C 0.6398(3) 0.44848(11) 0.34092(8) 0.0268(6) Uani d . . . 1 . .
H H3C 0.5837 0.4753 0.3511 0.032 Uiso calc U . R 1 . .
C C4C 0.6956(3) 0.41200(11) 0.36651(8) 0.0235(6) Uani d . . . 1 . .
C C5C 0.8474(3) 0.33315(11) 0.37557(8) 0.0249(6) Uani d . . . 1 . .
H H5C 0.8407 0.3358 0.4038 0.03 Uiso calc U . R 1 . .
C C6C 0.9237(3) 0.29407(11) 0.36027(8) 0.0256(6) Uani d . . . 1 . .
H H6C 0.9688 0.2696 0.3777 0.031 Uiso calc U . R 1 . .
C C7C 0.9362(3) 0.28971(11) 0.31828(9) 0.0255(6) Uani d . . . 1 . .
H H7C 0.987 0.2616 0.3075 0.031 Uiso calc U . R 1 . .
C C8C 0.8747(2) 0.32628(11) 0.29326(8) 0.0229(6) Uani d . . . 1 . .
H H8C 0.8849 0.3237 0.2652 0.027 Uiso calc U . R 1 . .
C C9C 0.7958(2) 0.36794(11) 0.30888(8) 0.0227(6) Uani d . . . 1 . .
C C10C 0.7777(3) 0.37001(11) 0.35069(8) 0.0234(6) Uani d . . . 1 . .
C C11C 0.7665(2) 0.41134(11) 0.23932(8) 0.0209(6) Uani d . . . 1 . .
C C12C 0.8479(3) 0.45120(11) 0.22653(8) 0.0236(6) Uani d . . . 1 . .
H H12C 0.8898 0.4741 0.2457 0.028 Uiso calc U . R 1 . .
C C13C 0.8707(3) 0.45890(11) 0.18598(8) 0.0249(6) Uani d . . . 1 . .
H H13C 0.9266 0.4873 0.1783 0.03 Uiso calc U . R 1 . .
C C14C 0.8145(3) 0.42646(11) 0.15702(8) 0.0234(6) Uani d . . . 1 . .
C C15C 0.6852(3) 0.34266(11) 0.14184(8) 0.0266(6) Uani d . . . 1 . .
H H15C 0.7045 0.3455 0.1143 0.032 Uiso calc U . R 1 . .
C C16C 0.6095(3) 0.30116(12) 0.15443(9) 0.0264(6) Uani d . . . 1 . .
H H16C 0.5776 0.2753 0.1357 0.032 Uiso calc U . R 1 . .
C C17C 0.5782(3) 0.29631(12) 0.19506(8) 0.0275(6) Uani d . . . 1 . .
H H17C 0.5226 0.2681 0.2033 0.033 Uiso calc U . R 1 . .
C C18C 0.6276(3) 0.33196(11) 0.22235(8) 0.0238(6) Uani d . . . 1 . .
H H18C 0.6067 0.328 0.2497 0.029 Uiso calc U . R 1 . .
C C19C 0.7100(3) 0.37512(11) 0.21099(8) 0.0243(6) Uani d . . . 1 . .
C C20C 0.7357(2) 0.38190(11) 0.16939(8) 0.0226(6) Uani d . . . 1 . .
C C21C 0.6684(3) 0.41611(11) 0.40995(8) 0.0256(6) Uani d . . . 1 . .
C C22C 0.6763(3) 0.46649(12) 0.42861(9) 0.0283(6) Uani d . . . 1 . .
H H22C 0.7018 0.4969 0.4138 0.034 Uiso calc U . R 1 . .
C C23C 0.6470(3) 0.47180(14) 0.46853(9) 0.0390(8) Uani d . . . 1 . .
H H23C 0.6542 0.5059 0.4808 0.047 Uiso calc U . R 1 . .
C C24C 0.6082(3) 0.42927(14) 0.49054(9) 0.0372(8) Uani d . . . 1 . .
H H24C 0.5873 0.4339 0.5178 0.045 Uiso calc U . R 1 . .
C C25C 0.5994(3) 0.37886(14) 0.47286(10) 0.0369(7) Uani d . . . 1 . .
H H25C 0.5738 0.3489 0.4882 0.044 Uiso calc U . R 1 . .
C C26C 0.6283(3) 0.37263(12) 0.43283(9) 0.0286(6) Uani d . . . 1 . .
H H26C 0.6206 0.3383 0.4208 0.034 Uiso calc U . R 1 . .
C C27C 0.8349(3) 0.43882(11) 0.11415(8) 0.0230(6) Uani d . . . 1 . .
C C28C 0.7274(3) 0.44189(11) 0.08653(8) 0.0271(6) Uani d . . . 1 . .
H H28C 0.6405 0.4345 0.0949 0.033 Uiso calc U . R 1 . .
C C29C 0.7480(3) 0.45564(12) 0.04713(8) 0.0305(7) Uani d . . . 1 . .
H H29C 0.6745 0.4586 0.0288 0.037 Uiso calc U . R 1 . .
C C30C 0.8730(3) 0.46511(12) 0.03412(9) 0.0307(7) Uani d . . . 1 . .
H H30C 0.8855 0.4739 0.0069 0.037 Uiso calc U . R 1 . .
C C31C 0.9813(3) 0.46185(12) 0.06081(9) 0.0318(7) Uani d . . . 1 . .
H H31C 1.0682 0.4679 0.0519 0.038 Uiso calc U . R 1 . .
C C32C 0.9610(3) 0.44958(11) 0.10065(8) 0.0270(6) Uani d . . . 1 . .
H H32C 1.0345 0.4485 0.1191 0.032 Uiso calc U . R 1 . .
C C1D 0.2394(2) 0.46116(11) 0.28164(8) 0.0221(6) Uani d . . . 1 . .
C C2D 0.1607(3) 0.42116(11) 0.29537(8) 0.0245(6) Uani d . . . 1 . .
H H2D 0.1203 0.3972 0.2767 0.029 Uiso calc U . R 1 . .
C C3D 0.1378(3) 0.41445(11) 0.33631(8) 0.0235(6) Uani d . . . 1 . .
H H3D 0.0804 0.3867 0.3444 0.028 Uiso calc U . R 1 . .
C C4D 0.1959(3) 0.44682(11) 0.36474(8) 0.0244(6) Uani d . . . 1 . .
C C5D 0.3380(3) 0.52624(11) 0.37975(9) 0.0264(6) Uani d . . . 1 . .
H H5D 0.3243 0.5217 0.4075 0.032 Uiso calc U . R 1 . .
C C6D 0.4153(3) 0.56789(11) 0.36765(9) 0.0287(6) Uani d . . . 1 . .
H H161 0.4545 0.5917 0.3868 0.034 Uiso calc U . R 1 . .
C C7D 0.4361(3) 0.57502(11) 0.32649(9) 0.0273(6) Uani d . . . 1 . .
H H6D 0.489 0.6039 0.3179 0.033 Uiso calc U . R 1 . .
C C8D 0.3805(3) 0.54053(11) 0.29878(8) 0.0232(6) Uani d . . . 1 . .
H H7D 0.3961 0.5457 0.2712 0.028 Uiso calc U . R 1 . .
C C9D 0.2995(2) 0.49699(11) 0.31068(8) 0.0223(6) Uani d . . . 1 . .
C C10D 0.2778(2) 0.48988(11) 0.35225(8) 0.0213(6) Uani d . . . 1 . .
C C11D 0.2667(3) 0.46361(11) 0.23831(8) 0.0240(6) Uani d . . . 1 . .
C C12D 0.3381(3) 0.42327(11) 0.22128(8) 0.0245(6) Uani d . . . 1 . .
H H12D 0.374 0.3956 0.2378 0.029 Uiso calc U . R 1 . .
C C13D 0.3588(3) 0.42225(11) 0.17984(8) 0.0230(6) Uani d . . . 1 . .
H H13D 0.4085 0.3939 0.169 0.028 Uiso calc U . R 1 . .
C C14D 0.3081(2) 0.46182(11) 0.15458(8) 0.0223(6) Uani d . . . 1 . .
C C15D 0.1704(2) 0.54442(11) 0.14697(8) 0.0224(6) Uani d . . . 1 . .
H H15D 0.1802 0.5437 0.1188 0.027 Uiso calc U . R 1 . .
C C16D 0.0975(3) 0.58423(11) 0.16353(8) 0.0242(6) Uani d . . . 1 . .
H H16D 0.06 0.6115 0.147 0.029 Uiso calc U . R 1 . .
C C17D 0.0780(3) 0.58498(11) 0.20473(8) 0.0253(6) Uani d . . . 1 . .
H H17D 0.0264 0.6125 0.216 0.03 Uiso calc U . R 1 . .
C C18D 0.1327(3) 0.54625(11) 0.22888(8) 0.0229(6) Uani d . . . 1 . .
H H18D 0.1179 0.5469 0.2568 0.027 Uiso calc U . R 1 . .
C C19D 0.2118(2) 0.50490(11) 0.21285(8) 0.0219(6) Uani d . . . 1 . .
C C20D 0.2318(3) 0.50399(11) 0.17113(8) 0.0239(6) Uani d . . . 1 . .
C C21D 0.1701(3) 0.43542(11) 0.40792(8) 0.0238(6) Uani d . . . 1 . .
C C22D 0.2731(3) 0.42175(12) 0.43489(8) 0.0274(6) Uani d . . . 1 . .
H H22D 0.3619 0.4229 0.4265 0.033 Uiso calc U . R 1 . .
C C23D 0.2471(3) 0.40651(12) 0.47388(9) 0.0305(7) Uani d . . . 1 . .
H H23D 0.3174 0.3963 0.4918 0.037 Uiso calc U . R 1 . .
C C24D 0.1172(3) 0.40634(13) 0.48637(9) 0.0335(7) Uani d . . . 1 . .
H H24D 0.0985 0.3968 0.5131 0.04 Uiso calc U . R 1 . .
C C25D 0.0163(3) 0.42008(13) 0.45983(9) 0.0357(7) Uani d . . . 1 . .
H H25D -0.0723 0.4202 0.4683 0.043 Uiso calc U . R 1 . .
C C26D 0.0429(3) 0.43372(12) 0.42071(9) 0.0299(6) Uani d . . . 1 . .
H H26D -0.0282 0.442 0.4025 0.036 Uiso calc U . R 1 . .
C C27D 0.3323(3) 0.45783(11) 0.11077(8) 0.0240(6) Uani d . . . 1 . .
C C28D 0.3731(3) 0.50108(11) 0.08800(8) 0.0250(6) Uani d . . . 1 . .
H H28D 0.3893 0.5346 0.1007 0.03 Uiso calc U . R 1 . .
C C29D 0.3908(3) 0.49612(12) 0.04697(8) 0.0276(6) Uani d . . . 1 . .
H H29D 0.4173 0.5261 0.0318 0.033 Uiso calc U . R 1 . .
C C30D 0.3692(3) 0.44669(12) 0.02820(8) 0.0288(6) Uani d . . . 1 . .
H H30D 0.3803 0.4429 0.0002 0.035 Uiso calc U . R 1 . .
C C31D 0.3320(3) 0.40386(12) 0.05076(9) 0.0291(6) Uani d . . . 1 . .
H H31D 0.3184 0.3702 0.0382 0.035 Uiso calc U . R 1 . .
C C32D 0.3137(3) 0.40864(11) 0.09143(9) 0.0269(6) Uani d . . . 1 . .
H H32D 0.2882 0.3783 0.1064 0.032 Uiso calc U . R 1 . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1A C2A . 1.370(4) ?
C1A C9A . 1.415(4) ?
C1A C11A . 1.496(4) ?
C2A C3A . 1.411(4) ?
C2A H2A . 0.95 ?
C3A C4A . 1.380(4) ?
C3A H3A . 0.95 ?
C4A C10A . 1.434(4) ?
C4A C21A . 1.489(4) ?
C5A C6A . 1.356(4) ?
C5A C10A . 1.417(4) ?
C5A H5A . 0.95 ?
C6A C7A . 1.408(4) ?
C6A H6A . 0.95 ?
C7A C8A . 1.369(4) ?
C7A H7A . 0.95 ?
C8A C9A . 1.430(4) ?
C8A H8A . 0.95 ?
C9A C10A . 1.438(4) ?
C11A C12A . 1.379(4) ?
C11A C19A . 1.431(4) ?
C12A C13A . 1.404(4) ?
C12A H12A . 0.95 ?
C13A C14A . 1.363(4) ?
C13A H13A . 0.95 ?
C14A C20A . 1.422(4) ?
C14A C27A . 1.517(4) ?
C15A C16A . 1.369(4) ?
C15A C20A . 1.425(4) ?
C15A H15A . 0.95 ?
C16A C17A . 1.400(4) ?
C16A H16A . 0.95 ?
C17A C18A . 1.362(4) ?
C17A H17A . 0.95 ?
C18A C19A . 1.435(4) ?
C18A H18A . 0.95 ?
C19A C20A . 1.432(4) ?
C21A C22A . 1.399(4) ?
C21A C26A . 1.408(4) ?
C22A C23A . 1.383(4) ?
C22A H22A . 0.95 ?
C23A C24A . 1.377(4) ?
C23A H23A . 0.95 ?
C24A C25A . 1.396(4) ?
C24A H24A . 0.95 ?
C25A C26A . 1.384(4) ?
C25A H25A . 0.95 ?
C26A H26A . 0.95 ?
C27A C28A . 1.378(4) ?
C27A C32A . 1.392(4) ?
C28A C29A . 1.409(4) ?
C28A H28A . 0.95 ?
C29A C30A . 1.381(4) ?
C29A H29A . 0.95 ?
C30A C31A . 1.376(4) ?
C30A H30A . 0.95 ?
C31A C32A . 1.379(4) ?
C31A H31A . 0.95 ?
C32A H32A . 0.95 ?
C1B C2B . 1.370(4) ?
C1B C9B . 1.430(4) ?
C1B C11B . 1.494(4) ?
C2B C3B . 1.396(4) ?
C2B H2B . 0.95 ?
C3B C4B . 1.382(4) ?
C3B H3B . 0.95 ?
C4B C10B . 1.455(4) ?
C4B C21B . 1.482(4) ?
C5B C6B . 1.374(4) ?
C5B C10B . 1.417(4) ?
C5B H5B . 0.95 ?
C6B C7B . 1.407(4) ?
C6B H6B . 0.95 ?
C7B C8B . 1.355(4) ?
C7B H7B . 0.95 ?
C8B C9B . 1.417(4) ?
C8B H8B . 0.95 ?
C9B C10B . 1.435(4) ?
C11B C12B . 1.381(4) ?
C11B C19B . 1.438(4) ?
C12B C13B . 1.400(4) ?
C12B H12B . 0.95 ?
C13B C14B . 1.370(4) ?
C13B H13B . 0.95 ?
C14B C20B . 1.439(4) ?
C14B C27B . 1.487(4) ?
C15B C16B . 1.366(4) ?
C15B C20B . 1.434(4) ?
C15B H15B . 0.95 ?
C16B C17B . 1.403(4) ?
C16B H16B . 0.95 ?
C17B C18B . 1.371(4) ?
C17B H17B . 0.95 ?
C18B C19B . 1.426(4) ?
C18B H18B . 0.95 ?
C19B C20B . 1.420(4) ?
C21B C26B . 1.394(4) ?
C21B C22B . 1.409(4) ?
C22B C23B . 1.385(4) ?
C22B H22B . 0.95 ?
C23B C24B . 1.368(4) ?
C23B H23B . 0.95 ?
C24B C25B . 1.392(4) ?
C24B H24B . 0.95 ?
C25B C26B . 1.384(4) ?
C25B H25B . 0.95 ?
C26B H26B . 0.95 ?
C27B C32B . 1.397(4) ?
C27B C28B . 1.403(4) ?
C28B C29B . 1.390(4) ?
C28B H28B . 0.95 ?
C29B C30B . 1.379(4) ?
C29B H29B . 0.95 ?
C30B C31B . 1.395(4) ?
C30B H30B . 0.95 ?
C31B C32B . 1.401(4) ?
C31B H31B . 0.95 ?
C32B H32B . 0.95 ?
C1C C2C . 1.360(4) ?
C1C C9C . 1.435(4) ?
C1C C11C . 1.508(4) ?
C2C C3C . 1.413(4) ?
C2C H2C . 0.95 ?
C3C C4C . 1.361(4) ?
C3C H3C . 0.95 ?
C4C C10C . 1.451(4) ?
C4C C21C . 1.491(4) ?
C5C C6C . 1.357(4) ?
C5C C10C . 1.414(4) ?
C5C H5C . 0.95 ?
C6C C7C . 1.418(4) ?
C6C H6C . 0.95 ?
C7C C8C . 1.374(4) ?
C7C H7C . 0.95 ?
C8C C9C . 1.424(4) ?
C8C H8C . 0.95 ?
C9C C10C . 1.417(4) ?
C11C C12C . 1.372(4) ?
C11C C19C . 1.417(4) ?
C12C C13C . 1.397(4) ?
C12C H12C . 0.95 ?
C13C C14C . 1.372(4) ?
C13C H13C . 0.95 ?
C14C C20C . 1.440(4) ?
C14C C27C . 1.488(4) ?
C15C C16C . 1.366(4) ?
C15C C20C . 1.429(4) ?
C15C H15C . 0.95 ?
C16C C17C . 1.411(4) ?
C16C H16C . 0.95 ?
C17C C18C . 1.359(4) ?
C17C H17C . 0.95 ?
C18C C19C . 1.424(4) ?
C18C H18C . 0.95 ?
C19C C20C . 1.434(4) ?
C21C C26C . 1.399(4) ?
C21C C22C . 1.408(4) ?
C22C C23C . 1.384(4) ?
C22C H22C . 0.95 ?
C23C C24C . 1.360(5) ?
C23C H23C . 0.95 ?
C24C C25C . 1.395(5) ?
C24C H24C . 0.95 ?
C25C C26C . 1.389(4) ?
C25C H25C . 0.95 ?
C26C H26C . 0.95 ?
C27C C32C . 1.395(4) ?
C27C C28C . 1.404(4) ?
C28C C29C . 1.385(4) ?
C28C H28C . 0.95 ?
C29C C30C . 1.373(4) ?
C29C H29C . 0.95 ?
C30C C31C . 1.392(4) ?
C30C H30C . 0.95 ?
C31C C32C . 1.389(4) ?
C31C H31C . 0.95 ?
C32C H32C . 0.95 ?
C1D C2D . 1.368(4) ?
C1D C9D . 1.441(4) ?
C1D C11D . 1.486(4) ?
C2D C3D . 1.406(4) ?
C2D H2D . 0.95 ?
C3D C4D . 1.366(4) ?
C3D H3D . 0.95 ?
C4D C10D . 1.431(4) ?
C4D C21D . 1.503(4) ?
C5D C6D . 1.373(4) ?
C5D C10D . 1.416(4) ?
C5D H5D . 0.95 ?
C6D C7D . 1.411(4) ?
C6D H161 . 0.95 ?
C7D C8D . 1.373(4) ?
C7D H6D . 0.95 ?
C8D C9D . 1.428(4) ?
C8D H7D . 0.95 ?
C9D C10D . 1.426(4) ?
C11D C12D . 1.376(4) ?
C11D C19D . 1.438(4) ?
C12D C13D . 1.409(4) ?
C12D H12D . 0.95 ?
C13D C14D . 1.388(4) ?
C13D H13D . 0.95 ?
C14D C20D . 1.431(4) ?
C14D C27D . 1.497(4) ?
C15D C16D . 1.368(4) ?
C15D C20D . 1.424(4) ?
C15D H15D . 0.95 ?
C16D C17D . 1.399(4) ?
C16D H16D . 0.95 ?
C17D C18D . 1.367(4) ?
C17D H17D . 0.95 ?
C18D C19D . 1.425(4) ?
C18D H18D . 0.95 ?
C19D C20D . 1.417(4) ?
C21D C26D . 1.371(4) ?
C21D C22D . 1.397(4) ?
C22D C23D . 1.392(4) ?
C22D H22D . 0.95 ?
C23D C24D . 1.394(4) ?
C23D H23D . 0.95 ?
C24D C25D . 1.373(4) ?
C24D H24D . 0.95 ?
C25D C26D . 1.388(4) ?
C25D H25D . 0.95 ?
C26D H26D . 0.95 ?
C27D C28D . 1.395(4) ?
C27D C32D . 1.400(4) ?
C28D C29D . 1.395(4) ?
C28D H28D . 0.95 ?
C29D C30D . 1.401(4) ?
C29D H29D . 0.95 ?
C30D C31D . 1.371(4) ?
C30D H30D . 0.95 ?
C31D C32D . 1.384(4) ?
C31D H31D . 0.95 ?
C32D H32D . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2A C1A C9A . . 119.3(2) ?
C2A C1A C11A . . 118.0(2) ?
C9A C1A C11A . . 122.7(2) ?
C1A C2A C3A . . 121.3(2) ?
C1A C2A H2A . . 119.3 ?
C3A C2A H2A . . 119.3 ?
C4A C3A C2A . . 121.3(2) ?
C4A C3A H3A . . 119.4 ?
C2A C3A H3A . . 119.4 ?
C3A C4A C10A . . 119.0(2) ?
C3A C4A C21A . . 119.0(2) ?
C10A C4A C21A . . 122.0(2) ?
C6A C5A C10A . . 121.9(3) ?
C6A C5A H5A . . 119.1 ?
C10A C5A H5A . . 119.1 ?
C5A C6A C7A . . 120.9(3) ?
C5A C6A H6A . . 119.6 ?
C7A C6A H6A . . 119.6 ?
C8A C7A C6A . . 119.7(3) ?
C8A C7A H7A . . 120.2 ?
C6A C7A H7A . . 120.2 ?
C7A C8A C9A . . 121.2(3) ?
C7A C8A H8A . . 119.4 ?
C9A C8A H8A . . 119.4 ?
C1A C9A C8A . . 121.3(2) ?
C1A C9A C10A . . 120.2(2) ?
C8A C9A C10A . . 118.5(2) ?
C5A C10A C4A . . 123.4(2) ?
C5A C10A C9A . . 117.8(2) ?
C4A C10A C9A . . 118.8(2) ?
C12A C11A C19A . . 117.5(2) ?
C12A C11A C1A . . 119.7(2) ?
C19A C11A C1A . . 122.6(2) ?
C11A C12A C13A . . 121.9(2) ?
C11A C12A H12A . . 119.0 ?
C13A C12A H12A . . 119.0 ?
C14A C13A C12A . . 121.7(3) ?
C14A C13A H13A . . 119.2 ?
C12A C13A H13A . . 119.2 ?
C13A C14A C20A . . 119.3(2) ?
C13A C14A C27A . . 118.1(2) ?
C20A C14A C27A . . 122.6(2) ?
C16A C15A C20A . . 121.5(3) ?
C16A C15A H15A . . 119.3 ?
C20A C15A H15A . . 119.3 ?
C15A C16A C17A . . 120.6(3) ?
C15A C16A H16A . . 119.7 ?
C17A C16A H16A . . 119.7 ?
C18A C17A C16A . . 120.3(3) ?
C18A C17A H17A . . 119.9 ?
C16A C17A H17A . . 119.9 ?
C17A C18A C19A . . 121.1(3) ?
C17A C18A H18A . . 119.4 ?
C19A C18A H18A . . 119.4 ?
C11A C19A C20A . . 120.6(2) ?
C11A C19A C18A . . 120.9(2) ?
C20A C19A C18A . . 118.5(2) ?
C14A C20A C15A . . 123.1(2) ?
C14A C20A C19A . . 118.9(2) ?
C15A C20A C19A . . 117.8(2) ?
C22A C21A C26A . . 117.9(2) ?
C22A C21A C4A . . 120.0(2) ?
C26A C21A C4A . . 122.1(2) ?
C23A C22A C21A . . 120.7(3) ?
C23A C22A H22A . . 119.7 ?
C21A C22A H22A . . 119.7 ?
C24A C23A C22A . . 120.9(3) ?
C24A C23A H23A . . 119.5 ?
C22A C23A H23A . . 119.5 ?
C23A C24A C25A . . 119.6(3) ?
C23A C24A H24A . . 120.2 ?
C25A C24A H24A . . 120.2 ?
C26A C25A C24A . . 119.7(3) ?
C26A C25A H25A . . 120.1 ?
C24A C25A H25A . . 120.1 ?
C25A C26A C21A . . 121.2(3) ?
C25A C26A H26A . . 119.4 ?
C21A C26A H26A . . 119.4 ?
C28A C27A C32A . . 119.0(3) ?
C28A C27A C14A . . 122.7(3) ?
C32A C27A C14A . . 118.2(3) ?
C27A C28A C29A . . 120.3(3) ?
C27A C28A H28A . . 119.9 ?
C29A C28A H28A . . 119.9 ?
C30A C29A C28A . . 119.7(3) ?
C30A C29A H29A . . 120.2 ?
C28A C29A H29A . . 120.2 ?
C31A C30A C29A . . 119.8(3) ?
C31A C30A H30A . . 120.1 ?
C29A C30A H30A . . 120.1 ?
C30A C31A C32A . . 120.5(3) ?
C30A C31A H31A . . 119.8 ?
C32A C31A H31A . . 119.8 ?
C31A C32A C27A . . 120.7(3) ?
C31A C32A H32A . . 119.6 ?
C27A C32A H32A . . 119.6 ?
C2B C1B C9B . . 118.9(2) ?
C2B C1B C11B . . 119.4(2) ?
C9B C1B C11B . . 121.6(2) ?
C1B C2B C3B . . 121.7(3) ?
C1B C2B H2B . . 119.2 ?
C3B C2B H2B . . 119.2 ?
C4B C3B C2B . . 122.7(3) ?
C4B C3B H3B . . 118.6 ?
C2B C3B H3B . . 118.6 ?
C3B C4B C10B . . 117.4(2) ?
C3B C4B C21B . . 119.8(2) ?
C10B C4B C21B . . 122.8(2) ?
C6B C5B C10B . . 121.7(2) ?
C6B C5B H5B . . 119.1 ?
C10B C5B H5B . . 119.1 ?
C5B C6B C7B . . 120.0(3) ?
C5B C6B H6B . . 120.0 ?
C7B C6B H6B . . 120.0 ?
C8B C7B C6B . . 119.9(3) ?
C8B C7B H7B . . 120.1 ?
C6B C7B H7B . . 120.1 ?
C7B C8B C9B . . 122.1(3) ?
C7B C8B H8B . . 118.9 ?
C9B C8B H8B . . 118.9 ?
C8B C9B C1B . . 121.5(2) ?
C8B C9B C10B . . 118.4(2) ?
C1B C9B C10B . . 120.0(2) ?
C5B C10B C9B . . 117.7(2) ?
C5B C10B C4B . . 122.9(2) ?
C9B C10B C4B . . 119.3(2) ?
C12B C11B C19B . . 118.2(2) ?
C12B C11B C1B . . 118.7(2) ?
C19B C11B C1B . . 123.1(2) ?
C11B C12B C13B . . 121.6(3) ?
C11B C12B H12B . . 119.2 ?
C13B C12B H12B . . 119.2 ?
C14B C13B C12B . . 122.1(3) ?
C14B C13B H13B . . 119.0 ?
C12B C13B H13B . . 119.0 ?
C13B C14B C20B . . 118.5(2) ?
C13B C14B C27B . . 118.2(2) ?
C20B C14B C27B . . 123.3(2) ?
C16B C15B C20B . . 120.6(3) ?
C16B C15B H15B . . 119.7 ?
C20B C15B H15B . . 119.7 ?
C15B C16B C17B . . 120.6(3) ?
C15B C16B H16B . . 119.7 ?
C17B C16B H16B . . 119.7 ?
C18B C17B C16B . . 120.3(3) ?
C18B C17B H17B . . 119.8 ?
C16B C17B H17B . . 119.8 ?
C17B C18B C19B . . 121.1(3) ?
C17B C18B H18B . . 119.5 ?
C19B C18B H18B . . 119.5 ?
C20B C19B C18B . . 118.4(2) ?
C20B C19B C11B . . 120.1(2) ?
C18B C19B C11B . . 121.5(2) ?
C19B C20B C15B . . 118.9(2) ?
C19B C20B C14B . . 119.6(2) ?
C15B C20B C14B . . 121.5(2) ?
C26B C21B C22B . . 117.1(2) ?
C26B C21B C4B . . 124.4(2) ?
C22B C21B C4B . . 118.4(2) ?
C23B C22B C21B . . 121.4(3) ?
C23B C22B H22B . . 119.3 ?
C21B C22B H22B . . 119.3 ?
C24B C23B C22B . . 120.3(3) ?
C24B C23B H23B . . 119.9 ?
C22B C23B H23B . . 119.9 ?
C23B C24B C25B . . 119.6(3) ?
C23B C24B H24B . . 120.2 ?
C25B C24B H24B . . 120.2 ?
C26B C25B C24B . . 120.3(3) ?
C26B C25B H25B . . 119.8 ?
C24B C25B H25B . . 119.8 ?
C25B C26B C21B . . 121.2(3) ?
C25B C26B H26B . . 119.4 ?
C21B C26B H26B . . 119.4 ?
C32B C27B C28B . . 118.3(2) ?
C32B C27B C14B . . 119.2(2) ?
C28B C27B C14B . . 122.4(2) ?
C29B C28B C27B . . 120.1(3) ?
C29B C28B H28B . . 119.9 ?
C27B C28B H28B . . 119.9 ?
C30B C29B C28B . . 121.3(3) ?
C30B C29B H29B . . 119.3 ?
C28B C29B H29B . . 119.3 ?
C29B C30B C31B . . 119.5(3) ?
C29B C30B H30B . . 120.3 ?
C31B C30B H30B . . 120.3 ?
C30B C31B C32B . . 119.6(3) ?
C30B C31B H31B . . 120.2 ?
C32B C31B H31B . . 120.2 ?
C27B C32B C31B . . 121.1(3) ?
C27B C32B H32B . . 119.4 ?
C31B C32B H32B . . 119.4 ?
C2C C1C C9C . . 119.1(2) ?
C2C C1C C11C . . 118.8(2) ?
C9C C1C C11C . . 122.1(2) ?
C1C C2C C3C . . 121.5(3) ?
C1C C2C H2C . . 119.2 ?
C3C C2C H2C . . 119.2 ?
C4C C3C C2C . . 121.4(3) ?
C4C C3C H3C . . 119.3 ?
C2C C3C H3C . . 119.3 ?
C3C C4C C10C . . 119.1(3) ?
C3C C4C C21C . . 118.6(2) ?
C10C C4C C21C . . 122.2(2) ?
C6C C5C C10C . . 121.8(3) ?
C6C C5C H5C . . 119.1 ?
C10C C5C H5C . . 119.1 ?
C5C C6C C7C . . 120.0(3) ?
C5C C6C H6C . . 120.0 ?
C7C C6C H6C . . 120.0 ?
C8C C7C C6C . . 119.8(2) ?
C8C C7C H7C . . 120.1 ?
C6C C7C H7C . . 120.1 ?
C7C C8C C9C . . 120.8(2) ?
C7C C8C H8C . . 119.6 ?
C9C C8C H8C . . 119.6 ?
C10C C9C C8C . . 118.8(2) ?
C10C C9C C1C . . 120.0(2) ?
C8C C9C C1C . . 121.2(2) ?
C5C C10C C9C . . 118.5(2) ?
C5C C10C C4C . . 122.6(3) ?
C9C C10C C4C . . 118.8(2) ?
C12C C11C C19C . . 119.3(2) ?
C12C C11C C1C . . 118.1(2) ?
C19C C11C C1C . . 122.6(2) ?
C11C C12C C13C . . 121.6(3) ?
C11C C12C H12C . . 119.2 ?
C13C C12C H12C . . 119.2 ?
C14C C13C C12C . . 121.7(3) ?
C14C C13C H13C . . 119.2 ?
C12C C13C H13C . . 119.2 ?
C13C C14C C20C . . 118.4(2) ?
C13C C14C C27C . . 119.3(2) ?
C20C C14C C27C . . 122.3(2) ?
C16C C15C C20C . . 121.1(3) ?
C16C C15C H15C . . 119.5 ?
C20C C15C H15C . . 119.5 ?
C15C C16C C17C . . 120.6(3) ?
C15C C16C H16C . . 119.7 ?
C17C C16C H16C . . 119.7 ?
C18C C17C C16C . . 120.0(3) ?
C18C C17C H17C . . 120.0 ?
C16C C17C H17C . . 120.0 ?
C17C C18C C19C . . 121.6(3) ?
C17C C18C H18C . . 119.2 ?
C19C C18C H18C . . 119.2 ?
C11C C19C C18C . . 122.2(3) ?
C11C C19C C20C . . 119.3(3) ?
C18C C19C C20C . . 118.5(2) ?
C15C C20C C19C . . 118.1(2) ?
C15C C20C C14C . . 122.4(2) ?
C19C C20C C14C . . 119.4(2) ?
C26C C21C C22C . . 117.9(3) ?
C26C C21C C4C . . 123.1(3) ?
C22C C21C C4C . . 118.9(3) ?
C23C C22C C21C . . 120.2(3) ?
C23C C22C H22C . . 119.9 ?
C21C C22C H22C . . 119.9 ?
C24C C23C C22C . . 121.5(3) ?
C24C C23C H23C . . 119.2 ?
C22C C23C H23C . . 119.2 ?
C23C C24C C25C . . 119.6(3) ?
C23C C24C H24C . . 120.2 ?
C25C C24C H24C . . 120.2 ?
C26C C25C C24C . . 119.8(3) ?
C26C C25C H25C . . 120.1 ?
C24C C25C H25C . . 120.1 ?
C25C C26C C21C . . 121.0(3) ?
C25C C26C H26C . . 119.5 ?
C21C C26C H26C . . 119.5 ?
C32C C27C C28C . . 118.2(3) ?
C32C C27C C14C . . 120.8(2) ?
C28C C27C C14C . . 121.0(2) ?
C29C C28C C27C . . 120.0(3) ?
C29C C28C H28C . . 120.0 ?
C27C C28C H28C . . 120.0 ?
C30C C29C C28C . . 121.1(3) ?
C30C C29C H29C . . 119.5 ?
C28C C29C H29C . . 119.5 ?
C29C C30C C31C . . 120.0(3) ?
C29C C30C H30C . . 120.0 ?
C31C C30C H30C . . 120.0 ?
C32C C31C C30C . . 119.2(3) ?
C32C C31C H31C . . 120.4 ?
C30C C31C H31C . . 120.4 ?
C31C C32C C27C . . 121.4(3) ?
C31C C32C H32C . . 119.3 ?
C27C C32C H32C . . 119.3 ?
C2D C1D C9D . . 117.8(2) ?
C2D C1D C11D . . 119.2(2) ?
C9D C1D C11D . . 122.9(2) ?
C1D C2D C3D . . 122.1(3) ?
C1D C2D H2D . . 118.9 ?
C3D C2D H2D . . 118.9 ?
C4D C3D C2D . . 121.7(3) ?
C4D C3D H3D . . 119.2 ?
C2D C3D H3D . . 119.2 ?
C3D C4D C10D . . 118.9(2) ?
C3D C4D C21D . . 118.1(2) ?
C10D C4D C21D . . 123.0(2) ?
C6D C5D C10D . . 122.2(3) ?
C6D C5D H5D . . 118.9 ?
C10D C5D H5D . . 118.9 ?
C5D C6D C7D . . 119.3(3) ?
C5D C6D H161 . . 120.3 ?
C7D C6D H161 . . 120.3 ?
C8D C7D C6D . . 120.5(3) ?
C8D C7D H6D . . 119.8 ?
C6D C7D H6D . . 119.8 ?
C7D C8D C9D . . 121.1(3) ?
C7D C8D H7D . . 119.4 ?
C9D C8D H7D . . 119.4 ?
C10D C9D C8D . . 118.5(2) ?
C10D C9D C1D . . 120.2(2) ?
C8D C9D C1D . . 121.3(2) ?
C5D C10D C9D . . 118.4(2) ?
C5D C10D C4D . . 122.3(2) ?
C9D C10D C4D . . 119.3(2) ?
C12D C11D C19D . . 118.7(2) ?
C12D C11D C1D . . 119.4(2) ?
C19D C11D C1D . . 121.7(2) ?
C11D C12D C13D . . 121.2(3) ?
C11D C12D H12D . . 119.4 ?
C13D C12D H12D . . 119.4 ?
C14D C13D C12D . . 121.4(2) ?
C14D C13D H13D . . 119.3 ?
C12D C13D H13D . . 119.3 ?
C13D C14D C20D . . 118.9(2) ?
C13D C14D C27D . . 118.6(2) ?
C20D C14D C27D . . 122.5(2) ?
C16D C15D C20D . . 121.2(3) ?
C16D C15D H15D . . 119.4 ?
C20D C15D H15D . . 119.4 ?
C15D C16D C17D . . 120.4(3) ?
C15D C16D H16D . . 119.8 ?
C17D C16D H16D . . 119.8 ?
C18D C17D C16D . . 120.3(3) ?
C18D C17D H17D . . 119.9 ?
C16D C17D H17D . . 119.9 ?
C17D C18D C19D . . 121.0(2) ?
C17D C18D H18D . . 119.5 ?
C19D C18D H18D . . 119.5 ?
C20D C19D C18D . . 118.9(2) ?
C20D C19D C11D . . 120.4(2) ?
C18D C19D C11D . . 120.7(2) ?
C19D C20D C15D . . 118.2(3) ?
C19D C20D C14D . . 119.4(2) ?
C15D C20D C14D . . 122.4(2) ?
C26D C21D C22D . . 118.6(3) ?
C26D C21D C4D . . 120.1(2) ?
C22D C21D C4D . . 121.1(2) ?
C23D C22D C21D . . 120.7(3) ?
C23D C22D H22D . . 119.7 ?
C21D C22D H22D . . 119.7 ?
C22D C23D C24D . . 119.5(3) ?
C22D C23D H23D . . 120.2 ?
C24D C23D H23D . . 120.2 ?
C25D C24D C23D . . 119.6(3) ?
C25D C24D H24D . . 120.2 ?
C23D C24D H24D . . 120.2 ?
C24D C25D C26D . . 120.4(3) ?
C24D C25D H25D . . 119.8 ?
C26D C25D H25D . . 119.8 ?
C21D C26D C25D . . 121.2(3) ?
C21D C26D H26D . . 119.4 ?
C25D C26D H26D . . 119.4 ?
C28D C27D C32D . . 117.9(3) ?
C28D C27D C14D . . 123.0(3) ?
C32D C27D C14D . . 119.1(2) ?
C27D C28D C29D . . 121.2(3) ?
C27D C28D H28D . . 119.4 ?
C29D C28D H28D . . 119.4 ?
C28D C29D C30D . . 119.7(3) ?
C28D C29D H29D . . 120.1 ?
C30D C29D H29D . . 120.1 ?
C31D C30D C29D . . 119.0(3) ?
C31D C30D H30D . . 120.5 ?
C29D C30D H30D . . 120.5 ?
C30D C31D C32D . . 121.5(3) ?
C30D C31D H31D . . 119.3 ?
C32D C31D H31D . . 119.3 ?
C31D C32D C27D . . 120.6(3) ?
C31D C32D H32D . . 119.7 ?
C27D C32D H32D . . 119.7 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9A C1A C2A C3A . . . . 2.9(4) ?
C11A C1A C2A C3A . . . . -176.1(2) ?
C1A C2A C3A C4A . . . . 0.2(4) ?
C2A C3A C4A C10A . . . . -3.5(4) ?
C2A C3A C4A C21A . . . . 176.4(2) ?
C10A C5A C6A C7A . . . . 0.1(4) ?
C5A C6A C7A C8A . . . . -1.0(4) ?
C6A C7A C8A C9A . . . . -0.7(4) ?
C2A C1A C9A C8A . . . . 177.3(2) ?
C11A C1A C9A C8A . . . . -3.8(4) ?
C2A C1A C9A C10A . . . . -2.6(4) ?
C11A C1A C9A C10A . . . . 176.3(2) ?
C7A C8A C9A C1A . . . . -176.7(2) ?
C7A C8A C9A C10A . . . . 3.2(4) ?
C6A C5A C10A C4A . . . . 178.8(3) ?
C6A C5A C10A C9A . . . . 2.4(4) ?
C3A C4A C10A C5A . . . . -172.7(3) ?
C21A C4A C10A C5A . . . . 7.4(4) ?
C3A C4A C10A C9A . . . . 3.7(4) ?
C21A C4A C10A C9A . . . . -176.2(2) ?
C1A C9A C10A C5A . . . . 175.9(2) ?
C8A C9A C10A C5A . . . . -4.0(4) ?
C1A C9A C10A C4A . . . . -0.6(4) ?
C8A C9A C10A C4A . . . . 179.5(2) ?
C2A C1A C11A C12A . . . . 69.4(3) ?
C9A C1A C11A C12A . . . . -109.6(3) ?
C2A C1A C11A C19A . . . . -106.1(3) ?
C9A C1A C11A C19A . . . . 74.9(3) ?
C19A C11A C12A C13A . . . . 0.3(4) ?
C1A C11A C12A C13A . . . . -175.4(2) ?
C11A C12A C13A C14A . . . . 1.0(4) ?
C12A C13A C14A C20A . . . . -0.4(4) ?
C12A C13A C14A C27A . . . . 178.4(2) ?
C20A C15A C16A C17A . . . . -0.4(4) ?
C15A C16A C17A C18A . . . . 3.2(4) ?
C16A C17A C18A C19A . . . . -2.0(4) ?
C12A C11A C19A C20A . . . . -2.2(4) ?
C1A C11A C19A C20A . . . . 173.4(2) ?
C12A C11A C19A C18A . . . . 179.9(2) ?
C1A C11A C19A C18A . . . . -4.5(4) ?
C17A C18A C19A C11A . . . . 175.9(2) ?
C17A C18A C19A C20A . . . . -2.0(4) ?
C13A C14A C20A C15A . . . . 174.4(2) ?
C27A C14A C20A C15A . . . . -4.4(4) ?
C13A C14A C20A C19A . . . . -1.5(4) ?
C27A C14A C20A C19A . . . . 179.8(2) ?
C16A C15A C20A C14A . . . . -179.4(3) ?
C16A C15A C20A C19A . . . . -3.5(4) ?
C11A C19A C20A C14A . . . . 2.8(4) ?
C18A C19A C20A C14A . . . . -179.3(2) ?
C11A C19A C20A C15A . . . . -173.3(2) ?
C18A C19A C20A C15A . . . . 4.6(4) ?
C3A C4A C21A C22A . . . . 50.8(4) ?
C10A C4A C21A C22A . . . . -129.3(3) ?
C3A C4A C21A C26A . . . . -126.6(3) ?
C10A C4A C21A C26A . . . . 53.3(4) ?
C26A C21A C22A C23A . . . . -0.9(4) ?
C4A C21A C22A C23A . . . . -178.5(3) ?
C21A C22A C23A C24A . . . . 1.5(4) ?
C22A C23A C24A C25A . . . . -1.1(4) ?
C23A C24A C25A C26A . . . . 0.2(4) ?
C24A C25A C26A C21A . . . . 0.4(4) ?
C22A C21A C26A C25A . . . . 0.0(4) ?
C4A C21A C26A C25A . . . . 177.5(3) ?
C13A C14A C27A C28A . . . . 133.0(3) ?
C20A C14A C27A C28A . . . . -48.2(4) ?
C13A C14A C27A C32A . . . . -43.8(3) ?
C20A C14A C27A C32A . . . . 135.0(3) ?
C32A C27A C28A C29A . . . . -1.8(4) ?
C14A C27A C28A C29A . . . . -178.6(2) ?
C27A C28A C29A C30A . . . . 0.8(4) ?
C28A C29A C30A C31A . . . . 0.9(4) ?
C29A C30A C31A C32A . . . . -1.6(4) ?
C30A C31A C32A C27A . . . . 0.6(4) ?
C28A C27A C32A C31A . . . . 1.1(4) ?
C14A C27A C32A C31A . . . . 178.0(2) ?
C9B C1B C2B C3B . . . . 1.4(4) ?
C11B C1B C2B C3B . . . . 176.6(2) ?
C1B C2B C3B C4B . . . . -1.6(4) ?
C2B C3B C4B C10B . . . . 0.9(4) ?
C2B C3B C4B C21B . . . . -179.3(2) ?
C10B C5B C6B C7B . . . . -2.4(4) ?
C5B C6B C7B C8B . . . . 0.8(4) ?
C6B C7B C8B C9B . . . . 0.9(4) ?
C7B C8B C9B C1B . . . . -179.0(3) ?
C7B C8B C9B C10B . . . . -1.1(4) ?
C2B C1B C9B C8B . . . . 177.3(2) ?
C11B C1B C9B C8B . . . . 2.2(4) ?
C2B C1B C9B C10B . . . . -0.5(4) ?
C11B C1B C9B C10B . . . . -175.7(2) ?
C6B C5B C10B C9B . . . . 2.2(4) ?
C6B C5B C10B C4B . . . . 179.6(2) ?
C8B C9B C10B C5B . . . . -0.4(4) ?
C1B C9B C10B C5B . . . . 177.5(2) ?
C8B C9B C10B C4B . . . . -178.0(2) ?
C1B C9B C10B C4B . . . . -0.1(4) ?
C3B C4B C10B C5B . . . . -177.5(2) ?
C21B C4B C10B C5B . . . . 2.7(4) ?
C3B C4B C10B C9B . . . . -0.1(4) ?
C21B C4B C10B C9B . . . . -179.9(2) ?
C2B C1B C11B C12B . . . . -66.0(3) ?
C9B C1B C11B C12B . . . . 109.1(3) ?
C2B C1B C11B C19B . . . . 111.5(3) ?
C9B C1B C11B C19B . . . . -73.4(3) ?
C19B C11B C12B C13B . . . . -0.9(4) ?
C1B C11B C12B C13B . . . . 176.7(2) ?
C11B C12B C13B C14B . . . . -2.0(4) ?
C12B C13B C14B C20B . . . . 3.9(4) ?
C12B C13B C14B C27B . . . . -175.7(2) ?
C20B C15B C16B C17B . . . . -0.8(4) ?
C15B C16B C17B C18B . . . . 1.5(4) ?
C16B C17B C18B C19B . . . . -1.5(4) ?
C17B C18B C19B C20B . . . . 0.9(4) ?
C17B C18B C19B C11B . . . . 179.9(2) ?
C12B C11B C19B C20B . . . . 1.9(4) ?
C1B C11B C19B C20B . . . . -175.6(2) ?
C12B C11B C19B C18B . . . . -177.1(2) ?
C1B C11B C19B C18B . . . . 5.4(4) ?
C18B C19B C20B C15B . . . . -0.2(4) ?
C11B C19B C20B C15B . . . . -179.2(2) ?
C18B C19B C20B C14B . . . . 179.0(2) ?
C11B C19B C20B C14B . . . . -0.1(4) ?
C16B C15B C20B C19B . . . . 0.2(4) ?
C16B C15B C20B C14B . . . . -179.0(3) ?
C13B C14B C20B C19B . . . . -2.8(4) ?
C27B C14B C20B C19B . . . . 176.8(2) ?
C13B C14B C20B C15B . . . . 176.4(2) ?
C27B C14B C20B C15B . . . . -4.0(4) ?
C3B C4B C21B C26B . . . . -134.4(3) ?
C10B C4B C21B C26B . . . . 45.4(4) ?
C3B C4B C21B C22B . . . . 43.2(4) ?
C10B C4B C21B C22B . . . . -137.1(3) ?
C26B C21B C22B C23B . . . . -0.5(4) ?
C4B C21B C22B C23B . . . . -178.3(2) ?
C21B C22B C23B C24B . . . . 0.4(4) ?
C22B C23B C24B C25B . . . . -0.6(4) ?
C23B C24B C25B C26B . . . . 1.1(4) ?
C24B C25B C26B C21B . . . . -1.3(4) ?
C22B C21B C26B C25B . . . . 1.0(4) ?
C4B C21B C26B C25B . . . . 178.6(3) ?
C13B C14B C27B C32B . . . . -51.6(4) ?
C20B C14B C27B C32B . . . . 128.8(3) ?
C13B C14B C27B C28B . . . . 124.4(3) ?
C20B C14B C27B C28B . . . . -55.2(4) ?
C32B C27B C28B C29B . . . . 1.9(4) ?
C14B C27B C28B C29B . . . . -174.1(3) ?
C27B C28B C29B C30B . . . . -2.0(4) ?
C28B C29B C30B C31B . . . . 0.9(4) ?
C29B C30B C31B C32B . . . . 0.2(4) ?
C28B C27B C32B C31B . . . . -0.9(4) ?
C14B C27B C32B C31B . . . . 175.3(3) ?
C30B C31B C32B C27B . . . . -0.2(4) ?
C9C C1C C2C C3C . . . . -0.1(4) ?
C11C C1C C2C C3C . . . . -176.7(2) ?
C1C C2C C3C C4C . . . . 2.6(4) ?
C2C C3C C4C C10C . . . . -2.1(4) ?
C2C C3C C4C C21C . . . . 178.9(3) ?
C10C C5C C6C C7C . . . . 0.6(4) ?
C5C C6C C7C C8C . . . . 2.3(4) ?
C6C C7C C8C C9C . . . . -1.4(4) ?
C7C C8C C9C C10C . . . . -2.2(4) ?
C7C C8C C9C C1C . . . . 175.4(2) ?
C2C C1C C9C C10C . . . . -2.8(4) ?
C11C C1C C9C C10C . . . . 173.8(2) ?
C2C C1C C9C C8C . . . . 179.5(3) ?
C11C C1C C9C C8C . . . . -3.9(4) ?
C6C C5C C10C C9C . . . . -4.3(4) ?
C6C C5C C10C C4C . . . . 180.0(2) ?
C8C C9C C10C C5C . . . . 5.0(4) ?
C1C C9C C10C C5C . . . . -172.7(2) ?
C8C C9C C10C C4C . . . . -179.1(2) ?
C1C C9C C10C C4C . . . . 3.2(4) ?
C3C C4C C10C C5C . . . . 175.0(3) ?
C21C C4C C10C C5C . . . . -6.1(4) ?
C3C C4C C10C C9C . . . . -0.8(4) ?
C21C C4C C10C C9C . . . . 178.2(2) ?
C2C C1C C11C C12C . . . . 69.6(3) ?
C9C C1C C11C C12C . . . . -107.0(3) ?
C2C C1C C11C C19C . . . . -109.4(3) ?
C9C C1C C11C C19C . . . . 74.0(3) ?
C19C C11C C12C C13C . . . . 3.7(4) ?
C1C C11C C12C C13C . . . . -175.4(2) ?
C11C C12C C13C C14C . . . . -1.0(4) ?
C12C C13C C14C C20C . . . . -3.2(4) ?
C12C C13C C14C C27C . . . . 175.8(2) ?
C20C C15C C16C C17C . . . . 0.6(4) ?
C15C C16C C17C C18C . . . . -2.5(4) ?
C16C C17C C18C C19C . . . . 0.8(4) ?
C12C C11C C19C C18C . . . . 178.2(2) ?
C1C C11C C19C C18C . . . . -2.8(4) ?
C12C C11C C19C C20C . . . . -2.0(4) ?
C1C C11C C19C C20C . . . . 177.0(2) ?
C17C C18C C19C C11C . . . . -177.4(2) ?
C17C C18C C19C C20C . . . . 2.7(4) ?
C16C C15C C20C C19C . . . . 2.9(4) ?
C16C C15C C20C C14C . . . . -179.3(2) ?
C11C C19C C20C C15C . . . . 175.7(2) ?
C18C C19C C20C C15C . . . . -4.5(4) ?
C11C C19C C20C C14C . . . . -2.2(4) ?
C18C C19C C20C C14C . . . . 177.6(2) ?
C13C C14C C20C C15C . . . . -173.1(2) ?
C27C C14C C20C C15C . . . . 7.9(4) ?
C13C C14C C20C C19C . . . . 4.8(4) ?
C27C C14C C20C C19C . . . . -174.2(2) ?
C3C C4C C21C C26C . . . . 131.0(3) ?
C10C C4C C21C C26C . . . . -48.0(4) ?
C3C C4C C21C C22C . . . . -45.5(4) ?
C10C C4C C21C C22C . . . . 135.5(3) ?
C26C C21C C22C C23C . . . . 1.1(4) ?
C4C C21C C22C C23C . . . . 177.7(3) ?
C21C C22C C23C C24C . . . . -1.0(5) ?
C22C C23C C24C C25C . . . . 1.0(5) ?
C23C C24C C25C C26C . . . . -1.0(4) ?
C24C C25C C26C C21C . . . . 1.1(4) ?
C22C C21C C26C C25C . . . . -1.1(4) ?
C4C C21C C26C C25C . . . . -177.6(3) ?
C13C C14C C27C C32C . . . . 48.4(4) ?
C20C C14C C27C C32C . . . . -132.6(3) ?
C13C C14C C27C C28C . . . . -129.2(3) ?
C20C C14C C27C C28C . . . . 49.8(4) ?
C32C C27C C28C C29C . . . . -0.4(4) ?
C14C C27C C28C C29C . . . . 177.3(3) ?
C27C C28C C29C C30C . . . . 1.7(4) ?
C28C C29C C30C C31C . . . . -1.1(5) ?
C29C C30C C31C C32C . . . . -0.8(4) ?
C30C C31C C32C C27C . . . . 2.1(4) ?
C28C C27C C32C C31C . . . . -1.5(4) ?
C14C C27C C32C C31C . . . . -179.2(3) ?
C9D C1D C2D C3D . . . . 0.0(4) ?
C11D C1D C2D C3D . . . . 175.8(2) ?
C1D C2D C3D C4D . . . . -1.7(4) ?
C2D C3D C4D C10D . . . . 2.6(4) ?
C2D C3D C4D C21D . . . . -177.6(2) ?
C10D C5D C6D C7D . . . . 0.0(4) ?
C5D C6D C7D C8D . . . . -0.5(4) ?
C6D C7D C8D C9D . . . . 0.5(4) ?
C7D C8D C9D C10D . . . . -0.2(4) ?
C7D C8D C9D C1D . . . . 179.1(2) ?
C2D C1D C9D C10D . . . . 0.7(4) ?
C11D C1D C9D C10D . . . . -174.9(2) ?
C2D C1D C9D C8D . . . . -178.5(2) ?
C11D C1D C9D C8D . . . . 5.9(4) ?
C6D C5D C10D C9D . . . . 0.4(4) ?
C6D C5D C10D C4D . . . . -179.3(3) ?
C8D C9D C10D C5D . . . . -0.3(4) ?
C1D C9D C10D C5D . . . . -179.5(2) ?
C8D C9D C10D C4D . . . . 179.4(2) ?
C1D C9D C10D C4D . . . . 0.1(4) ?
C3D C4D C10D C5D . . . . 177.9(3) ?
C21D C4D C10D C5D . . . . -2.0(4) ?
C3D C4D C10D C9D . . . . -1.7(4) ?
C21D C4D C10D C9D . . . . 178.4(2) ?
C2D C1D C11D C12D . . . . -65.3(3) ?
C9D C1D C11D C12D . . . . 110.2(3) ?
C2D C1D C11D C19D . . . . 109.7(3) ?
C9D C1D C11D C19D . . . . -74.7(3) ?
C19D C11D C12D C13D . . . . 0.6(4) ?
C1D C11D C12D C13D . . . . 175.8(2) ?
C11D C12D C13D C14D . . . . 0.0(4) ?
C12D C13D C14D C20D . . . . -0.9(4) ?
C12D C13D C14D C27D . . . . -179.1(2) ?
C20D C15D C16D C17D . . . . -2.2(4) ?
C15D C16D C17D C18D . . . . 0.7(4) ?
C16D C17D C18D C19D . . . . 0.8(4) ?
C17D C18D C19D C20D . . . . -0.8(4) ?
C17D C18D C19D C11D . . . . -178.6(2) ?
C12D C11D C19D C20D . . . . -0.4(4) ?
C1D C11D C19D C20D . . . . -175.4(2) ?
C12D C11D C19D C18D . . . . 177.4(2) ?
C1D C11D C19D C18D . . . . 2.4(4) ?
C18D C19D C20D C15D . . . . -0.7(4) ?
C11D C19D C20D C15D . . . . 177.2(2) ?
C18D C19D C20D C14D . . . . -178.3(2) ?
C11D C19D C20D C14D . . . . -0.5(4) ?
C16D C15D C20D C19D . . . . 2.2(4) ?
C16D C15D C20D C14D . . . . 179.8(2) ?
C13D C14D C20D C19D . . . . 1.1(4) ?
C27D C14D C20D C19D . . . . 179.3(2) ?
C13D C14D C20D C15D . . . . -176.5(2) ?
C27D C14D C20D C15D . . . . 1.7(4) ?
C3D C4D C21D C26D . . . . -56.3(4) ?
C10D C4D C21D C26D . . . . 123.5(3) ?
C3D C4D C21D C22D . . . . 118.0(3) ?
C10D C4D C21D C22D . . . . -62.2(4) ?
C26D C21D C22D C23D . . . . 0.3(4) ?
C4D C21D C22D C23D . . . . -174.1(3) ?
C21D C22D C23D C24D . . . . -1.8(4) ?
C22D C23D C24D C25D . . . . 1.4(5) ?
C23D C24D C25D C26D . . . . 0.4(5) ?
C22D C21D C26D C25D . . . . 1.6(5) ?
C4D C21D C26D C25D . . . . 176.0(3) ?
C24D C25D C26D C21D . . . . -2.0(5) ?
C13D C14D C27D C28D . . . . -134.4(3) ?
C20D C14D C27D C28D . . . . 47.4(4) ?
C13D C14D C27D C32D . . . . 45.5(4) ?
C20D C14D C27D C32D . . . . -132.7(3) ?
C32D C27D C28D C29D . . . . 2.1(4) ?
C14D C27D C28D C29D . . . . -178.0(2) ?
C27D C28D C29D C30D . . . . -1.0(4) ?
C28D C29D C30D C31D . . . . -0.5(4) ?
C29D C30D C31D C32D . . . . 0.8(4) ?
C30D C31D C32D C27D . . . . 0.3(4) ?
C28D C27D C32D C31D . . . . -1.7(4) ?
C14D C27D C32D C31D . . . . 178.4(2) ?

####################################################################### 
# 
# 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_9-2
_database_code_depnum_ccdc_archive 'CCDC 1476393'
_audit_update_record             
;
2017-07-27 deposited with the CCDC.
2017-08-15 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H12 Cl0.33 F1.67'
_chemical_formula_iupac          ?
_chemical_formula_weight         295.68

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   12.6399(11)
_cell_length_b                   10.6517(9)
_cell_length_c                   11.1760(10)
_cell_angle_alpha                90
_cell_angle_beta                 115.128(2)
_cell_angle_gamma                90
_cell_volume                     1362.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4668
_cell_measurement_theta_min      2.6124
_cell_measurement_theta_max      26.3789
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.431
_exptl_crystal_size_mid          0.215
_exptl_crystal_size_min          0.101
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             610

_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  TRIUMPH

_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            7056
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0126
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
Investigated crystal (9-2) contains mixture of F and Cl 
substituted 4,4? binaphtyl. During structure refinement 
position and anisotropic temperature factors for all 
non-H atoms were refined. The occupancy ratio of F/Cl 
was free to refine.
;

_reflns_number_total             1206
_reflns_number_gt                1099
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0880
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_restrained_S_all      1.113
_refine_ls_number_reflns         1206
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0477P)²+0.5759P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.129
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX2 V2014 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX2 V2014 (Bruker AXS Inc., 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.0577(9) 0.2871(5) 0.6083(8) 0.0222(10) Uani d . P . 0.163(6) . .
F F1 0.0706(3) 0.2919(3) 0.5980(3) 0.0418(19) Uani d . P . 0.837(6) . .
C C1 0.19364(11) 0.29340(11) 0.63970(12) 0.0251(3) Uani d . . . 1.0 . .
C C2 0.25981(11) 0.20050(11) 0.71894(12) 0.0263(3) Uani d . . . 1.0 . .
H H2 0.2247 0.1335 0.7453 0.032 Uiso calc U . R 1.0 . .
C C3 0.38147(11) 0.20531(11) 0.76136(11) 0.0248(3) Uani d . . . 1.0 . .
H H3 0.4283 0.1402 0.8167 0.03 Uiso calc U . R 1.0 . .
C C4 0.43516(10) 0.30102(11) 0.72557(11) 0.0224(3) Uani d . . . 1.0 . .
C C4A 0.36395(10) 0.39670(10) 0.63831(11) 0.0217(3) Uani d . . . 1.0 . .
C C5 0.41102(11) 0.49466(11) 0.58979(11) 0.0240(3) Uani d . . . 1.0 . .
H H5 0.4931 0.4992 0.6174 0.029 Uiso calc U . R 1.0 . .
C C6 0.34016(11) 0.58288(11) 0.50376(12) 0.0274(3) Uani d . . . 1.0 . .
H H6 0.3736 0.6472 0.4719 0.033 Uiso calc U . R 1.0 . .
C C7 0.21885(11) 0.57925(11) 0.46234(11) 0.0270(3) Uani d . . . 1.0 . .
H H7 0.1707 0.6412 0.4031 0.032 Uiso calc U . R 1.0 . .
C C8 0.16976(11) 0.48683(11) 0.50691(12) 0.0253(3) Uani d . . . 1.0 . .
H H8 0.0875 0.4852 0.479 0.03 Uiso calc U . R 1.0 . .
C C8A 0.24054(10) 0.39330(10) 0.59453(11) 0.0225(3) Uani d . . . 1.0 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C1 . 1.603(12) ?
F1 C1 . 1.422(4) ?
C1 C2 . 1.3542(18) ?
C1 C8A . 1.4117(17) ?
C2 C3 . 1.4046(18) ?
C2 H2 . 0.95 ?
C3 C4 . 1.3749(17) ?
C3 H3 . 0.95 ?
C4 C4A . 1.4333(16) ?
C4 C4 2_656 1.492(2) ?
C4A C5 . 1.4180(17) ?
C4A C8A . 1.4232(16) ?
C5 C6 . 1.3705(17) ?
C5 H5 . 0.95 ?
C6 C7 . 1.4015(18) ?
C6 H6 . 0.95 ?
C7 C8 . 1.3655(18) ?
C7 H7 . 0.95 ?
C8 C8A . 1.4170(17) ?
C8 H8 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C8A . . 123.24(12) ?
C2 C1 F1 . . 119.48(18) ?
C8A C1 F1 . . 117.28(17) ?
C2 C1 Cl1 . . 114.8(3) ?
C8A C1 Cl1 . . 121.8(3) ?
F1 C1 Cl1 . . 6.1(5) ?
C1 C2 C3 . . 118.53(11) ?
C1 C2 H2 . . 120.7 ?
C3 C2 H2 . . 120.7 ?
C4 C3 C2 . . 122.26(11) ?
C4 C3 H3 . . 118.9 ?
C2 C3 H3 . . 118.9 ?
C3 C4 C4A . . 118.70(12) ?
C3 C4 C4 . 2_656 119.67(9) ?
C4A C4 C4 . 2_656 121.61(9) ?
C5 C4A C8A . . 117.63(10) ?
C5 C4A C4 . . 122.63(11) ?
C8A C4A C4 . . 119.72(10) ?
C6 C5 C4A . . 121.16(12) ?
C6 C5 H5 . . 119.4 ?
C4A C5 H5 . . 119.4 ?
C5 C6 C7 . . 120.68(11) ?
C5 C6 H6 . . 119.7 ?
C7 C6 H6 . . 119.7 ?
C8 C7 C6 . . 120.15(11) ?
C8 C7 H7 . . 119.9 ?
C6 C7 H7 . . 119.9 ?
C7 C8 C8A . . 120.50(12) ?
C7 C8 H8 . . 119.8 ?
C8A C8 H8 . . 119.8 ?
C1 C8A C8 . . 122.63(11) ?
C1 C8A C4A . . 117.49(11) ?
C8 C8A C4A . . 119.86(11) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8A C1 C2 C3 . . . . 1.79(18) ?
F1 C1 C2 C3 . . . . -178.60(18) ?
Cl1 C1 C2 C3 . . . . -174.2(3) ?
C1 C2 C3 C4 . . . . 0.24(18) ?
C2 C3 C4 C4A . . . . -2.19(17) ?
C2 C3 C4 C4 . . . 2_656 179.73(11) ?
C3 C4 C4A C5 . . . . -176.09(10) ?
C4 C4 C4A C5 2_656 . . . 1.95(18) ?
C3 C4 C4A C8A . . . . 2.20(16) ?
C4 C4 C4A C8A 2_656 . . . -179.76(10) ?
C8A C4A C5 C6 . . . . -0.02(16) ?
C4 C4A C5 C6 . . . . 178.30(11) ?
C4A C5 C6 C7 . . . . 0.64(18) ?
C5 C6 C7 C8 . . . . -0.41(18) ?
C6 C7 C8 C8A . . . . -0.45(17) ?
C2 C1 C8A C8 . . . . 177.11(11) ?
F1 C1 C8A C8 . . . . -2.5(2) ?
Cl1 C1 C8A C8 . . . . -7.1(4) ?
C2 C1 C8A C4A . . . . -1.71(17) ?
F1 C1 C8A C4A . . . . 178.67(17) ?
Cl1 C1 C8A C4A . . . . 174.0(3) ?
C7 C8 C8A C1 . . . . -177.73(11) ?
C7 C8 C8A C4A . . . . 1.06(17) ?
C5 C4A C8A C1 . . . . 178.04(10) ?
C4 C4A C8A C1 . . . . -0.33(15) ?
C5 C4A C8A C8 . . . . -0.81(15) ?
C4 C4A C8A C8 . . . . -179.19(10) ?

####################################################################### 
# 
# 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_23
_database_code_depnum_ccdc_archive 'CCDC 1528856'
_audit_update_record             
;
2017-07-27 deposited with the CCDC.
2017-08-15 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H12 Br2'
_chemical_formula_iupac          ?
_chemical_formula_weight         412.12
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   16.4376(11)
_cell_length_b                   12.9727(9)
_cell_length_c                   7.2813(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1552.66(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9898
_cell_measurement_theta_min      2.4782
_cell_measurement_theta_max      25.3774
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.377
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.072
_exptl_crystal_density_diffrn    1.763
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808

_exptl_absorpt_coefficient_mu    5.214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.52
_exptl_absorpt_correction_T_max  0.70

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  TRIUMPH

_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            20544
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8

_refine_special_details          
;
;

_reflns_number_total             2739
_reflns_number_gt                2616
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0182
_refine_ls_R_factor_gt           0.0170
_refine_ls_wR_factor_gt          0.0421
_refine_ls_wR_factor_ref         0.0426
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_refine_ls_number_reflns         2739
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0257P)²+0.1620P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.179
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 1168 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.010(4)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX2 V2014 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX2 V2014 (Bruker AXS Inc., 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.56112(2) 0.77651(2) 0.84744(5) 0.02056(10) Uani d . . . 1 . .
C C1 0.61539(19) 0.6699(3) 0.5281(5) 0.0160(7) Uani d . . . 1 . .
C C2 0.58478(19) 0.6586(3) 0.7005(4) 0.0160(7) Uani d . . . 1 . .
C C3 0.56906(18) 0.5620(2) 0.7808(5) 0.0195(7) Uani d . . . 1 . .
H H3 0.5476 0.5575 0.9017 0.023 Uiso calc U . R 1 . .
C C4 0.5851(2) 0.4751(3) 0.6827(5) 0.0205(7) Uani d . . . 1 . .
H H4 0.5745 0.4096 0.736 0.025 Uiso calc U . R 1 . .
C C4A 0.61736(18) 0.4802(3) 0.5030(5) 0.0185(7) Uani d . . . 1 . .
C C5 0.6346(2) 0.3900(3) 0.3999(5) 0.0235(8) Uani d . . . 1 . .
H H5 0.6245 0.3241 0.452 0.028 Uiso calc U . R 1 . .
C C6 0.6655(2) 0.3971(3) 0.2265(5) 0.0264(9) Uani d . . . 1 . .
H H6 0.6765 0.3362 0.1586 0.032 Uiso calc U . R 1 . .
C C7 0.68099(19) 0.4934(3) 0.1481(5) 0.0244(8) Uani d . . . 1 . .
H H7 0.7031 0.4974 0.0277 0.029 Uiso calc U . R 1 . .
C C8 0.6646(2) 0.5820(3) 0.2432(5) 0.0199(7) Uani d . . . 1 . .
H H8 0.675 0.6469 0.1874 0.024 Uiso calc U . R 1 . .
C C8A 0.63256(18) 0.5785(3) 0.4230(5) 0.0155(7) Uani d . . . 1 . .
Br Br2 0.31247(2) 0.80338(2) 0.31260(5) 0.02356(10) Uani d . . . 1 . .
C C1' 0.62996(19) 0.7732(2) 0.4414(5) 0.0159(7) Uani d . . . 1 . .
C C2' 0.7071(2) 0.8130(2) 0.4316(5) 0.0186(7) Uani d . . . 1 . .
H H2' 0.751 0.7759 0.4847 0.022 Uiso calc U . R 1 . .
C C3' 0.72250(18) 0.9081(2) 0.3438(5) 0.0205(7) Uani d . . . 1 . .
H H3' 0.7761 0.9355 0.3421 0.025 Uiso calc U . R 1 . .
C C4' 0.6607(2) 0.9609(2) 0.2616(5) 0.0194(7) Uani d . . . 1 . .
H H4' 0.6718 1.0239 0.2001 0.023 Uiso calc U . R 1 . .
C C4A' 0.58045(19) 0.9231(2) 0.2669(4) 0.0165(7) Uani d . . . 1 . .
C C5' 0.5149(2) 0.9765(3) 0.1838(4) 0.0187(7) Uani d . . . 1 . .
H H5' 0.5255 1.0387 0.1193 0.022 Uiso calc U . R 1 . .
C C6' 0.43716(19) 0.9410(3) 0.1940(5) 0.0195(7) Uani d . . . 1 . .
H H6' 0.3939 0.9775 0.1369 0.023 Uiso calc U . R 1 . .
C C7' 0.42209(17) 0.8490(2) 0.2910(5) 0.0167(7) Uani d . . . 1 . .
C C8' 0.48244(19) 0.7932(2) 0.3717(4) 0.0145(7) Uani d . . . 1 . .
H H8' 0.47 0.7314 0.4357 0.017 Uiso calc U . R 1 . .
C C8A' 0.56389(18) 0.8279(2) 0.3597(5) 0.0146(6) Uani d . . . 1 . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C2 . 1.907(3) ?
C1 C2 . 1.360(5) ?
C1 C8A . 1.439(5) ?
C1 C1' . 1.500(5) ?
C2 C3 . 1.407(4) ?
C3 C4 . 1.361(5) ?
C3 H3 . 0.95 ?
C4 C4A . 1.413(5) ?
C4 H4 . 0.95 ?
C4A C5 . 1.419(5) ?
C4A C8A . 1.425(5) ?
C5 C6 . 1.364(5) ?
C5 H5 . 0.95 ?
C6 C7 . 1.397(6) ?
C6 H6 . 0.95 ?
C7 C8 . 1.369(5) ?
C7 H7 . 0.95 ?
C8 C8A . 1.412(5) ?
C8 H8 . 0.95 ?
Br2 C7' . 1.903(3) ?
C1' C2' . 1.371(4) ?
C1' C8A' . 1.427(4) ?
C2' C3' . 1.413(4) ?
C2' H2' . 0.95 ?
C3' C4' . 1.364(5) ?
C3' H3' . 0.95 ?
C4' C4A' . 1.407(5) ?
C4' H4' . 0.95 ?
C4A' C5' . 1.417(5) ?
C4A' C8A' . 1.433(4) ?
C5' C6' . 1.360(5) ?
C5' H5' . 0.95 ?
C6' C7' . 1.408(4) ?
C6' H6' . 0.95 ?
C7' C8' . 1.362(4) ?
C8' C8A' . 1.415(4) ?
C8' H8' . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C8A . . 118.3(3) ?
C2 C1 C1' . . 122.9(3) ?
C8A C1 C1' . . 118.7(3) ?
C1 C2 C3 . . 123.2(3) ?
C1 C2 Br1 . . 120.4(2) ?
C3 C2 Br1 . . 116.4(2) ?
C4 C3 C2 . . 119.0(3) ?
C4 C3 H3 . . 120.5 ?
C2 C3 H3 . . 120.5 ?
C3 C4 C4A . . 121.3(3) ?
C3 C4 H4 . . 119.3 ?
C4A C4 H4 . . 119.3 ?
C4 C4A C5 . . 121.8(3) ?
C4 C4A C8A . . 119.1(3) ?
C5 C4A C8A . . 119.1(3) ?
C6 C5 C4A . . 120.6(4) ?
C6 C5 H5 . . 119.7 ?
C4A C5 H5 . . 119.7 ?
C5 C6 C7 . . 120.5(4) ?
C5 C6 H6 . . 119.8 ?
C7 C6 H6 . . 119.8 ?
C8 C7 C6 . . 120.6(3) ?
C8 C7 H7 . . 119.7 ?
C6 C7 H7 . . 119.7 ?
C7 C8 C8A . . 121.0(4) ?
C7 C8 H8 . . 119.5 ?
C8A C8 H8 . . 119.5 ?
C8 C8A C4A . . 118.3(3) ?
C8 C8A C1 . . 122.7(3) ?
C4A C8A C1 . . 119.0(3) ?
C2' C1' C8A' . . 119.6(3) ?
C2' C1' C1 . . 120.4(3) ?
C8A' C1' C1 . . 119.9(3) ?
C1' C2' C3' . . 121.3(3) ?
C1' C2' H2' . . 119.4 ?
C3' C2' H2' . . 119.4 ?
C4' C3' C2' . . 120.2(3) ?
C4' C3' H3' . . 119.9 ?
C2' C3' H3' . . 119.9 ?
C3' C4' C4A' . . 120.7(3) ?
C3' C4' H4' . . 119.6 ?
C4A' C4' H4' . . 119.6 ?
C4' C4A' C5' . . 122.0(3) ?
C4' C4A' C8A' . . 119.4(3) ?
C5' C4A' C8A' . . 118.5(3) ?
C6' C5' C4A' . . 121.7(3) ?
C6' C5' H5' . . 119.1 ?
C4A' C5' H5' . . 119.1 ?
C5' C6' C7' . . 118.6(3) ?
C5' C6' H6' . . 120.7 ?
C7' C6' H6' . . 120.7 ?
C8' C7' C6' . . 122.6(3) ?
C8' C7' Br2 . . 119.2(2) ?
C6' C7' Br2 . . 118.1(2) ?
C7' C8' C8A' . . 119.6(3) ?
C7' C8' H8' . . 120.2 ?
C8A' C8' H8' . . 120.2 ?
C8' C8A' C1' . . 122.4(3) ?
C8' C8A' C4A' . . 118.9(3) ?
C1' C8A' C4A' . . 118.7(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8A C1 C2 C3 . . . . 0.0(5) ?
C1' C1 C2 C3 . . . . 178.3(3) ?
C8A C1 C2 Br1 . . . . 179.7(2) ?
C1' C1 C2 Br1 . . . . -1.9(4) ?
C1 C2 C3 C4 . . . . 0.1(5) ?
Br1 C2 C3 C4 . . . . -179.7(2) ?
C2 C3 C4 C4A . . . . 0.2(5) ?
C3 C4 C4A C5 . . . . 179.8(3) ?
C3 C4 C4A C8A . . . . -0.6(5) ?
C4 C4A C5 C6 . . . . 179.8(3) ?
C8A C4A C5 C6 . . . . 0.2(4) ?
C4A C5 C6 C7 . . . . 0.3(5) ?
C5 C6 C7 C8 . . . . -0.7(5) ?
C6 C7 C8 C8A . . . . 0.6(5) ?
C7 C8 C8A C4A . . . . -0.2(4) ?
C7 C8 C8A C1 . . . . 179.3(3) ?
C4 C4A C8A C8 . . . . -179.9(3) ?
C5 C4A C8A C8 . . . . -0.2(4) ?
C4 C4A C8A C1 . . . . 0.6(4) ?
C5 C4A C8A C1 . . . . -179.7(3) ?
C2 C1 C8A C8 . . . . -179.8(3) ?
C1' C1 C8A C8 . . . . 1.7(4) ?
C2 C1 C8A C4A . . . . -0.3(4) ?
C1' C1 C8A C4A . . . . -178.8(3) ?
C2 C1 C1' C2' . . . . 102.4(4) ?
C8A C1 C1' C2' . . . . -79.2(4) ?
C2 C1 C1' C8A' . . . . -81.0(4) ?
C8A C1 C1' C8A' . . . . 97.4(4) ?
C8A' C1' C2' C3' . . . . 0.8(5) ?
C1 C1' C2' C3' . . . . 177.4(3) ?
C1' C2' C3' C4' . . . . -2.1(5) ?
C2' C3' C4' C4A' . . . . 1.7(5) ?
C3' C4' C4A' C5' . . . . 179.6(3) ?
C3' C4' C4A' C8A' . . . . -0.1(5) ?
C4' C4A' C5' C6' . . . . -178.1(3) ?
C8A' C4A' C5' C6' . . . . 1.6(5) ?
C4A' C5' C6' C7' . . . . 0.4(5) ?
C5' C6' C7' C8' . . . . -1.4(5) ?
C5' C6' C7' Br2 . . . . 177.5(3) ?
C6' C7' C8' C8A' . . . . 0.2(5) ?
Br2 C7' C8' C8A' . . . . -178.6(2) ?
C7' C8' C8A' C1' . . . . 179.9(3) ?
C7' C8' C8A' C4A' . . . . 1.9(5) ?
C2' C1' C8A' C8' . . . . -177.3(3) ?
C1 C1' C8A' C8' . . . . 6.2(5) ?
C2' C1' C8A' C4A' . . . . 0.8(5) ?
C1 C1' C8A' C4A' . . . . -175.8(3) ?
C4' C4A' C8A' C8' . . . . 177.0(3) ?
C5' C4A' C8A' C8' . . . . -2.7(5) ?
C4' C4A' C8A' C1' . . . . -1.1(5) ?
C5' C4A' C8A' C1' . . . . 179.2(3) ?

####################################################################### 
# 
# 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_10-1_in_C2c
_database_code_depnum_ccdc_archive 'CCDC 1476395'
_audit_update_record             
;
2017-07-27 deposited with the CCDC.
2017-08-15 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H12 Br0.28 F1.72'
_chemical_formula_iupac          ?
_chemical_formula_weight         307.50

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   12.6575(11)
_cell_length_b                   10.6532(9)
_cell_length_c                   11.1899(10)
_cell_angle_alpha                90
_cell_angle_beta                 115.098(2)
_cell_angle_gamma                90
_cell_volume                     1366.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4790
_cell_measurement_theta_min      2.6103
_cell_measurement_theta_max      26.4162
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.395
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.076
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             629

_exptl_absorpt_coefficient_mu    0.922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.93

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  TRIUMPH

_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            10373
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         26.42
_diffrn_reflns_theta_full        26.42
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
Investigated crystal (10-1) contains mixture of F and Br 
substituted 4,4? binaphtyl. During structure refinement 
position and anisotropic temperature factors for all 
non-H atoms were refined. The occupancy ratio of F/Br 
was free to refine. In the F/Br mixed crystals possible 
lowering of the space group symmetry from C2/c to chiral 
C2 was observed. This was tested by structure refinement 
in both C2 (10-1_in_C2 data block) and C2/c (current 
data block) space groups. The C2/c choice gives 
significantly higher R values than corresponding C2 choice.
;

_reflns_number_total             1407
_reflns_number_gt                1246
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1026
_refine_ls_goodness_of_fit_ref   1.325
_refine_ls_restrained_S_all      1.325
_refine_ls_number_reflns         1407
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0077P)²+2.9193P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.175
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX2 V2014 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX2 V2014 (Bruker AXS Inc., 2014)'

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 0.0485(4) 0.2827(5) 0.6182(4) 0.0276(8) Uani 0.141(2) 1 d . . P . .
F1 F 0.0728(4) 0.2929(4) 0.5966(4) 0.0332(10) Uani 0.859(2) 1 d . . P . .
C1 C 0.4353(2) 0.3008(2) 0.7257(2) 0.0255(5) Uani 1 1 d . . . . .
C2 C 0.3814(2) 0.2050(2) 0.7615(2) 0.0285(5) Uani 1 1 d . . . . .
H2 H 0.4280 0.1398 0.8167 0.034 Uiso 1 1 calc R U . . .
C3 C 0.2600(2) 0.2007(2) 0.7191(2) 0.0306(6) Uani 1 1 d . . . . .
H3 H 0.2248 0.1341 0.7456 0.037 Uiso 1 1 calc R U . . .
C4 C 0.1944(2) 0.2932(2) 0.6398(2) 0.0291(5) Uani 1 1 d . . . . .
C4A C 0.2411(2) 0.3932(2) 0.5946(2) 0.0253(5) Uani 1 1 d . . . . .
C5 C 0.1706(2) 0.4861(2) 0.5072(2) 0.0292(5) Uani 1 1 d . . . . .
H5 H 0.0885 0.4839 0.4788 0.035 Uiso 1 1 calc R U . . .
C6 C 0.2194(2) 0.5791(2) 0.4630(2) 0.0301(6) Uani 1 1 d . . . . .
H6 H 0.1712 0.6413 0.4044 0.036 Uiso 1 1 calc R U . . .
C7 C 0.3409(2) 0.5828(2) 0.5042(2) 0.0307(6) Uani 1 1 d . . . . .
H7 H 0.3743 0.6471 0.4723 0.037 Uiso 1 1 calc R U . . .
C8 C 0.4117(2) 0.4944(2) 0.5901(2) 0.0264(5) Uani 1 1 d . . . . .
H8 H 0.4936 0.4986 0.6176 0.032 Uiso 1 1 calc R U . . .
C8A C 0.3640(2) 0.3967(2) 0.6385(2) 0.0243(5) Uani 1 1 d . . . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C4 1.762(5) . ?
F1 C4 1.404(5) . ?
C1 C2 1.378(3) . ?
C1 C8A 1.436(3) . ?
C1 C1 1.491(5) 2_656 ?
C2 C3 1.404(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.350(3) . ?
C3 H3 0.9500 . ?
C4 C4A 1.412(3) . ?
C4A C5 1.411(3) . ?
C4A C8A 1.418(3) . ?
C5 C6 1.367(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.406(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.372(3) . ?
C7 H7 0.9500 . ?
C8 C8A 1.421(3) . ?
C8 H8 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 C8A 118.5(2) . . ?
C2 C1 C1 119.76(18) . 2_656 ?
C8A C1 C1 121.67(17) . 2_656 ?
C1 C2 C3 122.1(2) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 H2 118.9 . . ?
C4 C3 C2 118.6(2) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 F1 120.2(3) . . ?
C3 C4 C4A 123.5(2) . . ?
F1 C4 C4A 116.3(3) . . ?
C3 C4 Br1 111.1(2) . . ?
F1 C4 Br1 11.6(3) . . ?
C4A C4 Br1 124.9(2) . . ?
C5 C4A C4 122.6(2) . . ?
C5 C4A C8A 120.0(2) . . ?
C4 C4A C8A 117.4(2) . . ?
C6 C5 C4A 120.6(2) . . ?
C6 C5 H5 119.7 . . ?
C4A C5 H5 119.7 . . ?
C5 C6 C7 120.1(2) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 120.6(2) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C8A 120.9(2) . . ?
C7 C8 H8 119.6 . . ?
C8A C8 H8 119.6 . . ?
C4A C8A C8 117.9(2) . . ?
C4A C8A C1 119.9(2) . . ?
C8 C8A C1 122.2(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8A C1 C2 C3 -2.1(3) . . . . ?
C1 C1 C2 C3 179.7(2) 2_656 . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C2 C3 C4 F1 -179.2(3) . . . . ?
C2 C3 C4 C4A 1.3(3) . . . . ?
C2 C3 C4 Br1 -171.3(2) . . . . ?
C3 C4 C4A C5 177.2(2) . . . . ?
F1 C4 C4A C5 -2.2(4) . . . . ?
Br1 C4 C4A C5 -11.1(4) . . . . ?
C3 C4 C4A C8A -1.5(3) . . . . ?
F1 C4 C4A C8A 179.0(3) . . . . ?
Br1 C4 C4A C8A 170.1(2) . . . . ?
C4 C4A C5 C6 -178.0(2) . . . . ?
C8A C4A C5 C6 0.7(3) . . . . ?
C4A C5 C6 C7 0.2(3) . . . . ?
C5 C6 C7 C8 -0.8(3) . . . . ?
C6 C7 C8 C8A 0.5(3) . . . . ?
C5 C4A C8A C8 -0.9(3) . . . . ?
C4 C4A C8A C8 177.83(19) . . . . ?
C5 C4A C8A C1 -178.92(19) . . . . ?
C4 C4A C8A C1 -0.2(3) . . . . ?
C7 C8 C8A C4A 0.4(3) . . . . ?
C7 C8 C8A C1 178.3(2) . . . . ?
C2 C1 C8A C4A 1.9(3) . . . . ?
C1 C1 C8A C4A -179.9(2) 2_656 . . . ?
C2 C1 C8A C8 -176.0(2) . . . . ?
C1 C1 C8A C8 2.2(3) 2_656 . . . ?

