# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_CM230PVTm34_a
_database_code_depnum_ccdc_archive 'CCDC 2149815'
loop_
_audit_author_name
_audit_author_address
'Kazutaka Shoyama'
;University of Wuerzburg
Germany
;
_audit_update_record             
;
2022-02-03 deposited with the CCDC.	2024-04-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H28 B2'
_chemical_formula_sum            'C40 H28 B2'
_chemical_formula_weight         530.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0022 0.0012 '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'
B B 0.0008 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   6.788(3)
_cell_length_b                   8.682(2)
_cell_length_c                   12.145(3)
_cell_angle_alpha                81.222(4)
_cell_angle_beta                 80.922(9)
_cell_angle_gamma                72.872(4)
_cell_volume                     671.1(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5385
_cell_measurement_theta_min      1.490
_cell_measurement_theta_max      23.735

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_F_000             278
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.057
_shelx_estimated_absorpt_T_min   0.994
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.61992
_diffrn_radiation_type           synchrotron
_diffrn_source                   'P11@PETRA III, DESY, Hamburg, Germany'
_diffrn_measurement_device_type  
;
Eiger2 X 16M, High Precision 1-Axis Goniostat with Staeubli sample changing
robot
;
_diffrn_measurement_method       '180° π scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3028
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_av_R_equivalents  0.074
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.490
_diffrn_reflns_theta_max         23.735
_diffrn_reflns_theta_full        21.836
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3028
_reflns_number_gt                2328
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'costum designed PXII GUI'
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_reduction        'XDS (Kabsch, 2010)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1629P)²+0.1331P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3028
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0714
_refine_ls_wR_factor_ref         0.2389
_refine_ls_wR_factor_gt          0.2171
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2466(3) 0.1261(2) 0.31900(15) 0.0403(4) Uani 1 1 d . . . . .
H1 H 0.158352 0.065718 0.305558 0.048 Uiso 1 1 calc R U . . .
C2 C 0.2479(3) 0.2647(2) 0.25113(15) 0.0410(4) Uani 1 1 d . . . . .
H2 H 0.164268 0.297138 0.191345 0.049 Uiso 1 1 calc R U . . .
C3 C 0.5161(3) 0.3011(2) 0.36762(14) 0.0386(4) Uani 1 1 d . . . . .
C4 C 0.6452(3) 0.3832(2) 0.39366(15) 0.0410(4) Uani 1 1 d . . . . .
H4 H 0.647785 0.485016 0.352470 0.049 Uiso 1 1 calc R U . . .
C5 C 0.7738(3) 0.3199(2) 0.48004(15) 0.0439(5) Uani 1 1 d . . . . .
H5 H 0.863424 0.377904 0.495255 0.053 Uiso 1 1 calc R U . . .
C6 C 0.7696(3) 0.1759(2) 0.54143(15) 0.0409(4) Uani 1 1 d . . . . .
H6 H 0.857746 0.134546 0.598890 0.049 Uiso 1 1 calc R U . . .
C7 C 0.6361(3) 0.0852(2) 0.52185(14) 0.0374(4) Uani 1 1 d . . . . .
C8 C 0.5066(3) 0.1489(2) 0.43350(13) 0.0362(4) Uani 1 1 d . . . . .
C9 C 0.3723(3) 0.0634(2) 0.41163(14) 0.0377(4) Uani 1 1 d . . . . .
C10 C 0.3802(3) 0.5381(2) 0.19746(14) 0.0383(4) Uani 1 1 d . . . . .
C11 C 0.5495(3) 0.5655(2) 0.12584(15) 0.0398(4) Uani 1 1 d . . . . .
C12 C 0.5354(3) 0.7201(2) 0.06181(15) 0.0431(5) Uani 1 1 d . . . . .
H12 H 0.653005 0.737055 0.013085 0.052 Uiso 1 1 calc R U . . .
C13 C 0.3575(3) 0.8433(2) 0.06921(16) 0.0449(5) Uani 1 1 d . . . . .
H13 H 0.353033 0.945083 0.026296 0.054 Uiso 1 1 calc R U . . .
C14 C 0.1788(3) 0.8219(2) 0.13994(15) 0.0395(4) Uani 1 1 d . . . . .
C15 C -0.0092(3) 0.9483(2) 0.14813(16) 0.0444(5) Uani 1 1 d . . . . .
H15 H -0.015923 1.050567 0.105443 0.053 Uiso 1 1 calc R U . . .
C16 C -0.1805(3) 0.9254(2) 0.21627(16) 0.0460(5) Uani 1 1 d . . . . .
H16 H -0.305900 1.010789 0.219969 0.055 Uiso 1 1 calc R U . . .
C17 C -0.1715(3) 0.7746(2) 0.28132(16) 0.0450(5) Uani 1 1 d . . . . .
H17 H -0.290419 0.758831 0.329332 0.054 Uiso 1 1 calc R U . . .
C18 C 0.0094(3) 0.6508(2) 0.27512(15) 0.0411(4) Uani 1 1 d . . . . .
H18 H 0.013084 0.550199 0.319641 0.049 Uiso 1 1 calc R U . . .
C19 C 0.1896(3) 0.6680(2) 0.20489(14) 0.0380(4) Uani 1 1 d . . . . .
C20 C 0.7519(3) 0.4364(2) 0.10669(16) 0.0445(5) Uani 1 1 d . . . . .
H20A H 0.865869 0.475415 0.121241 0.067 Uiso 1 1 calc R U . . .
H20B H 0.774482 0.411763 0.028820 0.067 Uiso 1 1 calc R U . . .
H20C H 0.746929 0.338126 0.157549 0.067 Uiso 1 1 calc R U . . .
B1 B 0.3825(3) 0.3697(3) 0.26954(17) 0.0404(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
C1 C2 1.353(2) . ?
C1 C9 1.460(2) . ?
C1 H1 0.9500 . ?
C2 B1 1.527(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(3) . ?
C3 C8 1.450(2) . ?
C3 B1 1.550(3) . ?
C4 C5 1.412(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.359(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.430(3) . ?
C6 H6 0.9500 . ?
C7 C9 1.426(2) 2_656 ?
C7 C8 1.435(2) . ?
C8 C9 1.409(3) . ?
C10 C11 1.384(3) . ?
C10 C19 1.446(2) . ?
C10 B1 1.582(3) . ?
C11 C12 1.430(3) . ?
C11 C20 1.506(2) . ?
C12 C13 1.358(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.414(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.418(2) . ?
C14 C19 1.433(2) . ?
C15 C16 1.364(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.412(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.374(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.409(3) . ?
C18 H18 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C9 124.12(17) . . ?
C2 C1 H1 117.9 . . ?
C9 C1 H1 117.9 . . ?
C1 C2 B1 120.72(15) . . ?
C1 C2 H2 119.6 . . ?
B1 C2 H2 119.6 . . ?
C4 C3 C8 119.03(15) . . ?
C4 C3 B1 120.78(16) . . ?
C8 C3 B1 120.18(17) . . ?
C3 C4 C5 121.64(16) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 120.13(17) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 121.76(16) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C9 C7 C6 121.67(15) 2_656 . ?
C9 C7 C8 120.15(17) 2_656 . ?
C6 C7 C8 118.17(16) . . ?
C9 C8 C7 119.97(16) . . ?
C9 C8 C3 120.79(15) . . ?
C7 C8 C3 119.23(17) . . ?
C8 C9 C7 119.87(15) . 2_656 ?
C8 C9 C1 119.58(16) . . ?
C7 C9 C1 120.53(17) 2_656 . ?
C11 C10 C19 118.61(16) . . ?
C11 C10 B1 123.32(16) . . ?
C19 C10 B1 118.05(16) . . ?
C10 C11 C12 120.33(17) . . ?
C10 C11 C20 123.17(16) . . ?
C12 C11 C20 116.45(16) . . ?
C13 C12 C11 121.38(18) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C13 C14 120.86(17) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C13 C14 C15 121.82(17) . . ?
C13 C14 C19 118.66(16) . . ?
C15 C14 C19 119.52(17) . . ?
C16 C15 C14 121.07(17) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 119.96(17) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C16 119.94(18) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 122.15(17) . . ?
C17 C18 H18 118.9 . . ?
C19 C18 H18 118.9 . . ?
C18 C19 C14 117.34(16) . . ?
C18 C19 C10 122.51(16) . . ?
C14 C19 C10 120.15(16) . . ?
C11 C20 H20A 109.5 . . ?
C11 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C11 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C2 B1 C3 114.55(16) . . ?
C2 B1 C10 122.92(15) . . ?
C3 B1 C10 122.50(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 C1 C2 B1 -1.4(3) . . . . ?
C8 C3 C4 C5 2.4(3) . . . . ?
B1 C3 C4 C5 -177.67(17) . . . . ?
C3 C4 C5 C6 -1.3(3) . . . . ?
C4 C5 C6 C7 -0.4(3) . . . . ?
C5 C6 C7 C9 -178.23(17) . . . 2_656 ?
C5 C6 C7 C8 0.9(3) . . . . ?
C9 C7 C8 C9 -0.7(3) 2_656 . . . ?
C6 C7 C8 C9 -179.83(16) . . . . ?
C9 C7 C8 C3 179.39(15) 2_656 . . . ?
C6 C7 C8 C3 0.2(3) . . . . ?
C4 C3 C8 C9 178.21(16) . . . . ?
B1 C3 C8 C9 -1.7(3) . . . . ?
C4 C3 C8 C7 -1.8(3) . . . . ?
B1 C3 C8 C7 178.22(15) . . . . ?
C7 C8 C9 C7 0.7(3) . . . 2_656 ?
C3 C8 C9 C7 -179.40(15) . . . 2_656 ?
C7 C8 C9 C1 -177.80(15) . . . . ?
C3 C8 C9 C1 2.2(3) . . . . ?
C2 C1 C9 C8 -0.6(3) . . . . ?
C2 C1 C9 C7 -179.04(17) . . . 2_656 ?
C19 C10 C11 C12 0.7(3) . . . . ?
B1 C10 C11 C12 179.01(17) . . . . ?
C19 C10 C11 C20 -176.59(15) . . . . ?
B1 C10 C11 C20 1.7(3) . . . . ?
C10 C11 C12 C13 -0.1(3) . . . . ?
C20 C11 C12 C13 177.42(17) . . . . ?
C11 C12 C13 C14 -0.7(3) . . . . ?
C12 C13 C14 C15 -179.36(17) . . . . ?
C12 C13 C14 C19 0.7(3) . . . . ?
C13 C14 C15 C16 179.61(18) . . . . ?
C19 C14 C15 C16 -0.5(3) . . . . ?
C14 C15 C16 C17 0.9(3) . . . . ?
C15 C16 C17 C18 -0.6(3) . . . . ?
C16 C17 C18 C19 -0.2(3) . . . . ?
C17 C18 C19 C14 0.7(3) . . . . ?
C17 C18 C19 C10 -179.69(17) . . . . ?
C13 C14 C19 C18 179.61(16) . . . . ?
C15 C14 C19 C18 -0.3(3) . . . . ?
C13 C14 C19 C10 0.0(3) . . . . ?
C15 C14 C19 C10 -179.97(15) . . . . ?
C11 C10 C19 C18 179.70(16) . . . . ?
B1 C10 C19 C18 1.3(3) . . . . ?
C11 C10 C19 C14 -0.7(3) . . . . ?
B1 C10 C19 C14 -179.04(15) . . . . ?
C1 C2 B1 C3 1.6(3) . . . . ?
C1 C2 B1 C10 -176.27(17) . . . . ?
C4 C3 B1 C2 179.92(17) . . . . ?
C8 C3 B1 C2 -0.1(3) . . . . ?
C4 C3 B1 C10 -2.2(3) . . . . ?
C8 C3 B1 C10 177.78(16) . . . . ?
C11 C10 B1 C2 -114.5(2) . . . . ?
C19 C10 B1 C2 63.8(3) . . . . ?
C11 C10 B1 C3 67.7(3) . . . . ?
C19 C10 B1 C3 -114.0(2) . . . . ?

_refine_diff_density_max         0.476
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.071



_exptl_crystal_recrystallization_method Sublimation
####################################################################### 
# 
# 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_CM303PVTK3_a
_database_code_depnum_ccdc_archive 'CCDC 2149817'
loop_
_audit_author_name
_audit_author_address
'Kazutaka Shoyama'
;University of Wuerzburg
Germany
;
_audit_update_record             
;
2022-02-03 deposited with the CCDC.	2024-04-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H32 B2'
_chemical_formula_sum            'C44 H32 B2'
_chemical_formula_weight         582.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

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

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

_cell_length_a                   19.3031(6)
_cell_length_b                   16.0030(5)
_cell_length_c                   9.7381(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3008.17(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9835
_cell_measurement_theta_min      3.59
_cell_measurement_theta_max      79.66

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             1224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.797
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.026
_exptl_absorpt_coefficient_mu    0.540
_shelx_estimated_absorpt_T_min   0.673
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5686
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_process_details   Bruker-SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   Cu/K(alpha)_ImuS_Microsource
_diffrn_measurement_device_type  Bruker-Kappa-D8Quest_PhotonII
_diffrn_measurement_method       omega_and_phi_scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35755
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_av_R_equivalents  0.0880
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.588
_diffrn_reflns_theta_max         80.782
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3289
_reflns_number_gt                2821
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0187P)²+4.3108P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3289
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0669
_refine_ls_wR_factor_ref         0.1467
_refine_ls_wR_factor_gt          0.1424
_refine_ls_goodness_of_fit_ref   1.200
_refine_ls_restrained_S_all      1.200
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.66699(13) 0.72870(15) 0.9661(2) 0.0286(5) Uani 1 1 d . . . . .
H1 H 0.647233 0.674798 0.954437 0.034 Uiso 1 1 calc R U . . .
C2 C 0.70284(13) 0.74593(16) 1.0842(3) 0.0308(5) Uani 1 1 d . . . . .
H2 H 0.708508 0.703683 1.151771 0.037 Uiso 1 1 calc R U . . .
C3 C 0.73133(13) 0.82577(16) 1.1060(3) 0.0317(5) Uani 1 1 d . . . . .
H3 H 0.756331 0.837378 1.187813 0.038 Uiso 1 1 calc R U . . .
C4 C 0.72285(13) 0.88657(16) 1.0087(3) 0.0315(5) Uani 1 1 d . . . . .
H4 H 0.741632 0.940611 1.024337 0.038 Uiso 1 1 calc R U . . .
C5 C 0.68652(12) 0.87034(15) 0.8850(3) 0.0297(5) Uani 1 1 d . . . . .
C6 C 0.67551(13) 0.93429(15) 0.7866(3) 0.0320(6) Uani 1 1 d . . . . .
H6 H 0.694777 0.988156 0.801500 0.038 Uiso 1 1 calc R U . . .
C7 C 0.63754(13) 0.91949(15) 0.6706(3) 0.0319(5) Uani 1 1 d . . . . .
H7 H 0.629526 0.963362 0.606815 0.038 Uiso 1 1 calc R U . . .
C8 C 0.61022(13) 0.83902(15) 0.6455(2) 0.0281(5) Uani 1 1 d . . . . .
C9 C 0.56728(13) 0.81850(15) 0.5182(3) 0.0287(5) Uani 1 1 d . . . . .
C10 C 0.55095(12) 0.72667(15) 0.5419(2) 0.0265(5) Uani 1 1 d . . . . .
C11 C 0.50926(12) 0.67836(14) 0.4644(2) 0.0259(5) Uani 1 1 d . . . . .
H11 H 0.483483 0.703462 0.392208 0.031 Uiso 1 1 calc R U . . .
C12 C 0.50250(12) 0.58908(14) 0.4877(2) 0.0238(5) Uani 1 1 d . . . . .
C13 C 0.54454(12) 0.54873(14) 0.5880(2) 0.0231(5) Uani 1 1 d . . . . .
C14 C 0.45691(12) 0.54060(14) 0.4040(2) 0.0233(5) Uani 1 1 d . . . . .
C15 C 0.41100(12) 0.58034(14) 0.3102(2) 0.0249(5) Uani 1 1 d . . . . .
H15 H 0.411239 0.639573 0.303740 0.030 Uiso 1 1 calc R U . . .
C16 C 0.36680(12) 0.53601(15) 0.2294(2) 0.0259(5) Uani 1 1 d . . . . .
H16 H 0.335540 0.564345 0.170188 0.031 Uiso 1 1 calc R U . . .
C17 C 0.36742(12) 0.44849(14) 0.2338(2) 0.0252(5) Uani 1 1 d . . . . .
H17 H 0.337103 0.418486 0.174818 0.030 Uiso 1 1 calc R U . . .
C18 C 0.41054(12) 0.40419(14) 0.3207(2) 0.0239(5) Uani 1 1 d . . . . .
C19 C 0.62182(12) 0.77245(14) 0.7355(2) 0.0265(5) Uani 1 1 d . . . . .
C20 C 0.65858(12) 0.78882(15) 0.8614(2) 0.0269(5) Uani 1 1 d . . . . .
C21 C 0.61177(16) 0.82753(17) 0.3882(3) 0.0383(6) Uani 1 1 d . . . . .
H21A H 0.584666 0.810509 0.307852 0.058 Uiso 1 1 calc R U . . .
H21B H 0.652880 0.791932 0.396121 0.058 Uiso 1 1 calc R U . . .
H21C H 0.626131 0.885926 0.377788 0.058 Uiso 1 1 calc R U . . .
C22 C 0.50301(15) 0.87400(15) 0.5087(3) 0.0365(6) Uani 1 1 d . . . . .
H22A H 0.473812 0.855132 0.432433 0.055 Uiso 1 1 calc R U . . .
H22B H 0.517175 0.932014 0.492898 0.055 Uiso 1 1 calc R U . . .
H22C H 0.476822 0.870437 0.594725 0.055 Uiso 1 1 calc R U . . .
B1 B 0.58943(14) 0.69271(17) 0.6666(3) 0.0266(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
C1 C2 1.370(3) . ?
C1 C20 1.411(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.407(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.367(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.418(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.418(4) . ?
C5 C20 1.430(3) . ?
C6 C7 1.367(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.413(3) . ?
C7 H7 0.9500 . ?
C8 C19 1.398(3) . ?
C8 C9 1.527(3) . ?
C9 C10 1.521(3) . ?
C9 C22 1.529(4) . ?
C9 C21 1.536(4) . ?
C10 C11 1.347(3) . ?
C10 B1 1.524(4) . ?
C11 C12 1.453(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.425(3) . ?
C12 C14 1.428(3) . ?
C13 C14 1.432(3) 5_666 ?
C13 C18 1.452(3) 5_666 ?
C14 C15 1.423(3) . ?
C15 C16 1.360(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.401(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.383(3) . ?
C17 H17 0.9500 . ?
C18 B1 1.556(3) 5_666 ?
C19 C20 1.440(3) . ?
C19 B1 1.571(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C20 121.8(2) . . ?
C2 C1 H1 119.1 . . ?
C20 C1 H1 119.1 . . ?
C1 C2 C3 120.5(2) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 119.6(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 121.1(2) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 121.1(2) . . ?
C4 C5 C20 119.4(2) . . ?
C6 C5 C20 119.5(2) . . ?
C7 C6 C5 120.9(2) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 120.1(2) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C19 C8 C7 121.8(2) . . ?
C19 C8 C9 115.6(2) . . ?
C7 C8 C9 122.6(2) . . ?
C10 C9 C8 101.36(19) . . ?
C10 C9 C22 113.7(2) . . ?
C8 C9 C22 111.4(2) . . ?
C10 C9 C21 109.4(2) . . ?
C8 C9 C21 110.2(2) . . ?
C22 C9 C21 110.5(2) . . ?
C11 C10 C9 126.4(2) . . ?
C11 C10 B1 122.2(2) . . ?
C9 C10 B1 111.4(2) . . ?
C10 C11 C12 122.0(2) . . ?
C10 C11 H11 119.0 . . ?
C12 C11 H11 119.0 . . ?
C13 C12 C14 119.7(2) . . ?
C13 C12 C11 120.1(2) . . ?
C14 C12 C11 120.0(2) . . ?
C12 C13 C14 118.6(2) . 5_666 ?
C12 C13 C18 121.6(2) . 5_666 ?
C14 C13 C18 119.8(2) 5_666 5_666 ?
C15 C14 C12 120.5(2) . . ?
C15 C14 C13 117.9(2) . 5_666 ?
C12 C14 C13 121.6(2) . 5_666 ?
C16 C15 C14 121.9(2) . . ?
C16 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
C15 C16 C17 119.9(2) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C16 122.4(2) . . ?
C18 C17 H17 118.8 . . ?
C16 C17 H17 118.8 . . ?
C17 C18 C13 117.9(2) . 5_666 ?
C17 C18 B1 124.0(2) . 5_666 ?
C13 C18 B1 117.9(2) 5_666 5_666 ?
C8 C19 C20 118.3(2) . . ?
C8 C19 B1 106.7(2) . . ?
C20 C19 B1 135.0(2) . . ?
C1 C20 C5 117.5(2) . . ?
C1 C20 C19 123.2(2) . . ?
C5 C20 C19 119.3(2) . . ?
C9 C21 H21A 109.5 . . ?
C9 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C9 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C9 C22 H22A 109.5 . . ?
C9 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C9 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C10 B1 C18 114.8(2) . 5_666 ?
C10 B1 C19 104.2(2) . . ?
C18 B1 C19 140.9(2) 5_666 . ?

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
C20 C1 C2 C3 1.5(4) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C3 C4 C5 C6 177.6(2) . . . . ?
C3 C4 C5 C20 -0.3(4) . . . . ?
C4 C5 C6 C7 -176.8(2) . . . . ?
C20 C5 C6 C7 1.1(4) . . . . ?
C5 C6 C7 C8 -1.7(4) . . . . ?
C6 C7 C8 C19 -1.1(4) . . . . ?
C6 C7 C8 C9 179.8(2) . . . . ?
C19 C8 C9 C10 1.3(3) . . . . ?
C7 C8 C9 C10 -179.5(2) . . . . ?
C19 C8 C9 C22 122.6(2) . . . . ?
C7 C8 C9 C22 -58.2(3) . . . . ?
C19 C8 C9 C21 -114.4(2) . . . . ?
C7 C8 C9 C21 64.7(3) . . . . ?
C8 C9 C10 C11 174.5(2) . . . . ?
C22 C9 C10 C11 54.9(3) . . . . ?
C21 C9 C10 C11 -69.1(3) . . . . ?
C8 C9 C10 B1 -6.6(3) . . . . ?
C22 C9 C10 B1 -126.2(2) . . . . ?
C21 C9 C10 B1 109.8(2) . . . . ?
C9 C10 C11 C12 173.7(2) . . . . ?
B1 C10 C11 C12 -5.1(4) . . . . ?
C10 C11 C12 C13 -4.9(4) . . . . ?
C10 C11 C12 C14 179.1(2) . . . . ?
C14 C12 C13 C14 4.0(4) . . . 5_666 ?
C11 C12 C13 C14 -172.0(2) . . . 5_666 ?
C14 C12 C13 C18 -177.4(2) . . . 5_666 ?
C11 C12 C13 C18 6.7(3) . . . 5_666 ?
C13 C12 C14 C15 175.5(2) . . . . ?
C11 C12 C14 C15 -8.5(3) . . . . ?
C13 C12 C14 C13 -4.1(4) . . . 5_666 ?
C11 C12 C14 C13 171.8(2) . . . 5_666 ?
C12 C14 C15 C16 -179.8(2) . . . . ?
C13 C14 C15 C16 -0.1(3) 5_666 . . . ?
C14 C15 C16 C17 -2.3(4) . . . . ?
C15 C16 C17 C18 1.7(4) . . . . ?
C16 C17 C18 C13 1.2(3) . . . 5_666 ?
C16 C17 C18 B1 177.2(2) . . . 5_666 ?
C7 C8 C19 C20 4.4(4) . . . . ?
C9 C8 C19 C20 -176.5(2) . . . . ?
C7 C8 C19 B1 -175.0(2) . . . . ?
C9 C8 C19 B1 4.1(3) . . . . ?
C2 C1 C20 C5 -2.6(3) . . . . ?
C2 C1 C20 C19 179.3(2) . . . . ?
C4 C5 C20 C1 2.0(3) . . . . ?
C6 C5 C20 C1 -176.0(2) . . . . ?
C4 C5 C20 C19 -179.9(2) . . . . ?
C6 C5 C20 C19 2.2(3) . . . . ?
C8 C19 C20 C1 173.2(2) . . . . ?
B1 C19 C20 C1 -7.7(4) . . . . ?
C8 C19 C20 C5 -4.8(3) . . . . ?
B1 C19 C20 C5 174.3(2) . . . . ?
C11 C10 B1 C18 12.3(3) . . . 5_666 ?
C9 C10 B1 C18 -166.6(2) . . . 5_666 ?
C11 C10 B1 C19 -172.0(2) . . . . ?
C9 C10 B1 C19 9.0(3) . . . . ?
C8 C19 B1 C10 -7.8(3) . . . . ?
C20 C19 B1 C10 173.0(3) . . . . ?
C8 C19 B1 C18 166.0(3) . . . 5_666 ?
C20 C19 B1 C18 -13.2(5) . . . 5_666 ?

_refine_diff_density_max         0.340
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.055



_exptl_crystal_recrystallization_method Sublimation
####################################################################### 
# 
# 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_CM226_a
_database_code_depnum_ccdc_archive 'CCDC 2149816'
loop_
_audit_author_name
_audit_author_address
'Kazutaka Shoyama'
;University of Wuerzburg
Germany
;
_audit_update_record             
;
2022-02-03 deposited with the CCDC.	2024-04-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H32 B2'
_chemical_formula_sum            'C36 H32 B2'
_chemical_formula_weight         486.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.6564(4)
_cell_length_b                   23.1604(10)
_cell_length_c                   6.9901(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.488(2)
_cell_angle_gamma                90
_cell_volume                     1343.79(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9886
_cell_measurement_theta_min      3.82
_cell_measurement_theta_max      71.96

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_F_000             516
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.177
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_min          0.109
_exptl_absorpt_coefficient_mu    0.497
_shelx_estimated_absorpt_T_min   0.917
_shelx_estimated_absorpt_T_max   0.948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6491
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   Bruker-SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   Cu/K(alpha)_ImuS_Microsource
_diffrn_measurement_device_type  Bruker-Kappa-D8Quest_PhotonII
_diffrn_measurement_method       omega_and_phi_scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22572
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.817
_diffrn_reflns_theta_max         72.046
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2655
_reflns_number_gt                2179
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0345P)²+1.1458P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2655
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0582
_refine_ls_wR_factor_ref         0.1307
_refine_ls_wR_factor_gt          0.1193
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_restrained_S_all      1.127
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8784(2) 0.59363(8) 0.6895(3) 0.0302(4) Uani 1 1 d . . . . .
H1 H 0.934527 0.602693 0.823828 0.036 Uiso 1 1 calc R U . . .
C2 C 0.7470(3) 0.62576(9) 0.5987(3) 0.0325(4) Uani 1 1 d . . . . .
H2 H 0.714041 0.656156 0.669530 0.039 Uiso 1 1 calc R U . . .
C3 C 0.7250(2) 0.56519(8) 0.2809(3) 0.0252(4) Uani 1 1 d . . . . .
C4 C 0.6541(2) 0.55099(8) 0.0831(3) 0.0266(4) Uani 1 1 d . . . . .
H4 H 0.561418 0.571664 0.009821 0.032 Uiso 1 1 calc R U . . .
C5 C 0.7156(2) 0.50672(8) -0.0128(3) 0.0287(4) Uani 1 1 d . . . . .
H5 H 0.665815 0.498539 -0.149577 0.034 Uiso 1 1 calc R U . . .
C6 C 0.8468(2) 0.47555(8) 0.0907(3) 0.0268(4) Uani 1 1 d . . . . .
H6 H 0.886274 0.445574 0.024578 0.032 Uiso 1 1 calc R U . . .
C7 C 0.9260(2) 0.48700(8) 0.2965(3) 0.0233(4) Uani 1 1 d . . . . .
C8 C 0.8644(2) 0.53317(7) 0.3912(3) 0.0235(4) Uani 1 1 d . . . . .
C9 C 0.9392(2) 0.54620(8) 0.5949(3) 0.0243(4) Uani 1 1 d . . . . .
C10 C 0.4883(2) 0.64413(8) 0.2741(3) 0.0248(4) Uani 1 1 d . . . . .
C11 C 0.3464(2) 0.62984(8) 0.3239(3) 0.0269(4) Uani 1 1 d . . . . .
C12 C 0.2000(2) 0.65521(8) 0.2214(3) 0.0279(4) Uani 1 1 d . . . . .
H12 H 0.104850 0.644525 0.254659 0.034 Uiso 1 1 calc R U . . .
C13 C 0.1903(2) 0.69574(8) 0.0718(3) 0.0274(4) Uani 1 1 d . . . . .
C14 C 0.3316(2) 0.71074(8) 0.0255(3) 0.0270(4) Uani 1 1 d . . . . .
H14 H 0.327194 0.738744 -0.075157 0.032 Uiso 1 1 calc R U . . .
C15 C 0.4783(2) 0.68569(8) 0.1232(3) 0.0254(4) Uani 1 1 d . . . . .
C16 C 0.3498(3) 0.58762(9) 0.4902(3) 0.0370(5) Uani 1 1 d . . . . .
H16A H 0.426371 0.556552 0.489056 0.055 Uiso 1 1 calc R U . . .
H16B H 0.242045 0.571202 0.470645 0.055 Uiso 1 1 calc R U . . .
H16C H 0.383070 0.607752 0.618728 0.055 Uiso 1 1 calc R U . . .
C17 C 0.0322(2) 0.72393(9) -0.0364(3) 0.0342(4) Uani 1 1 d . . . . .
H17A H -0.053648 0.708696 0.015413 0.051 Uiso 1 1 calc R U . . .
H17B H 0.006929 0.715593 -0.179440 0.051 Uiso 1 1 calc R U . . .
H17C H 0.040686 0.765781 -0.015403 0.051 Uiso 1 1 calc R U . . .
C18 C 0.6288(2) 0.70442(8) 0.0710(3) 0.0305(4) Uani 1 1 d . . . . .
H18A H 0.712604 0.714625 0.193319 0.046 Uiso 1 1 calc R U . . .
H18B H 0.604337 0.738056 -0.017533 0.046 Uiso 1 1 calc R U . . .
H18C H 0.667109 0.672723 0.003484 0.046 Uiso 1 1 calc R U . . .
B1 B 0.6522(3) 0.61325(9) 0.3836(3) 0.0261(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.357(3) . ?
C1 C9 1.456(3) . ?
C1 H1 0.9500 . ?
C2 B1 1.522(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(3) . ?
C3 C8 1.440(2) . ?
C3 B1 1.552(3) . ?
C4 C5 1.409(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.366(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.432(2) . ?
C6 H6 0.9500 . ?
C7 C9 1.423(3) 3_766 ?
C7 C8 1.437(2) . ?
C8 C9 1.419(2) . ?
C10 C11 1.407(3) . ?
C10 C15 1.413(3) . ?
C10 B1 1.579(3) . ?
C11 C12 1.396(3) . ?
C11 C16 1.513(3) . ?
C12 C13 1.390(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.395(3) . ?
C13 C17 1.511(3) . ?
C14 C15 1.387(3) . ?
C14 H14 0.9500 . ?
C15 C18 1.513(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C9 124.36(18) . . ?
C2 C1 H1 117.8 . . ?
C9 C1 H1 117.8 . . ?
C1 C2 B1 120.22(18) . . ?
C1 C2 H2 119.9 . . ?
B1 C2 H2 119.9 . . ?
C4 C3 C8 118.64(17) . . ?
C4 C3 B1 120.65(17) . . ?
C8 C3 B1 120.69(16) . . ?
C3 C4 C5 121.86(17) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 120.13(17) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 121.54(17) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C9 C7 C6 121.48(16) 3_766 . ?
C9 C7 C8 120.75(16) 3_766 . ?
C6 C7 C8 117.77(16) . . ?
C9 C8 C7 119.79(16) . . ?
C9 C8 C3 120.15(16) . . ?
C7 C8 C3 120.04(16) . . ?
C8 C9 C7 119.45(16) . 3_766 ?
C8 C9 C1 119.71(17) . . ?
C7 C9 C1 120.84(16) 3_766 . ?
C11 C10 C15 118.17(17) . . ?
C11 C10 B1 120.05(16) . . ?
C15 C10 B1 121.78(16) . . ?
C12 C11 C10 120.20(17) . . ?
C12 C11 C16 118.87(17) . . ?
C10 C11 C16 120.93(18) . . ?
C13 C12 C11 121.50(17) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C13 C14 118.22(17) . . ?
C12 C13 C17 121.40(18) . . ?
C14 C13 C17 120.37(18) . . ?
C15 C14 C13 121.50(17) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C14 C15 C10 120.39(17) . . ?
C14 C15 C18 119.50(17) . . ?
C10 C15 C18 120.08(17) . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2 B1 C3 114.67(17) . . ?
C2 B1 C10 123.43(17) . . ?
C3 B1 C10 121.84(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 C1 C2 B1 0.0(3) . . . . ?
C8 C3 C4 C5 -0.7(3) . . . . ?
B1 C3 C4 C5 -178.62(18) . . . . ?
C3 C4 C5 C6 1.4(3) . . . . ?
C4 C5 C6 C7 -0.6(3) . . . . ?
C5 C6 C7 C9 178.83(18) . . . 3_766 ?
C5 C6 C7 C8 -0.8(3) . . . . ?
C9 C7 C8 C9 0.5(3) 3_766 . . . ?
C6 C7 C8 C9 -179.87(16) . . . . ?
C9 C7 C8 C3 -178.12(16) 3_766 . . . ?
C6 C7 C8 C3 1.6(2) . . . . ?
C4 C3 C8 C9 -179.39(16) . . . . ?
B1 C3 C8 C9 -1.5(3) . . . . ?
C4 C3 C8 C7 -0.8(3) . . . . ?
B1 C3 C8 C7 177.11(16) . . . . ?
C7 C8 C9 C7 -0.4(3) . . . 3_766 ?
C3 C8 C9 C7 178.13(16) . . . 3_766 ?
C7 C8 C9 C1 178.92(17) . . . . ?
C3 C8 C9 C1 -2.5(3) . . . . ?
C2 C1 C9 C8 3.4(3) . . . . ?
C2 C1 C9 C7 -177.27(19) . . . 3_766 ?
C15 C10 C11 C12 1.8(3) . . . . ?
B1 C10 C11 C12 -177.22(17) . . . . ?
C15 C10 C11 C16 -177.30(17) . . . . ?
B1 C10 C11 C16 3.7(3) . . . . ?
C10 C11 C12 C13 -1.3(3) . . . . ?
C16 C11 C12 C13 177.81(18) . . . . ?
C11 C12 C13 C14 0.0(3) . . . . ?
C11 C12 C13 C17 -178.89(17) . . . . ?
C12 C13 C14 C15 0.8(3) . . . . ?
C17 C13 C14 C15 179.71(18) . . . . ?
C13 C14 C15 C10 -0.3(3) . . . . ?
C13 C14 C15 C18 -178.59(17) . . . . ?
C11 C10 C15 C14 -1.0(3) . . . . ?
B1 C10 C15 C14 177.98(17) . . . . ?
C11 C10 C15 C18 177.26(16) . . . . ?
B1 C10 C15 C18 -3.7(3) . . . . ?
C1 C2 B1 C3 -3.8(3) . . . . ?
C1 C2 B1 C10 173.50(19) . . . . ?
C4 C3 B1 C2 -177.61(17) . . . . ?
C8 C3 B1 C2 4.5(3) . . . . ?
C4 C3 B1 C10 5.1(3) . . . . ?
C8 C3 B1 C10 -172.82(16) . . . . ?
C11 C10 B1 C2 -73.0(2) . . . . ?
C15 C10 B1 C2 108.0(2) . . . . ?
C11 C10 B1 C3 104.1(2) . . . . ?
C15 C10 B1 C3 -74.9(2) . . . . ?

_refine_diff_density_max         0.215
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.048



