# 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 2021

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

data_7_ben
_database_code_depnum_ccdc_archive 'CCDC 2112954'
loop_
_audit_author_name
_audit_author_address
'Kazuo Tanaka'
;Kyoto University
Japan
;
_audit_update_record             
;
2021-10-25 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_RINTA01_7_ben               
;
PROBLEM: The value of Rint is greater than 0.12
RESPONSE: The large value of Rint might be due to
the decomposition of the material during the 
measurement.
;
_vrf_PLAT020_7_ben               
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.152 Report
RESPONSE: Please see our response for RINTA01
;
_vrf_PLAT026_7_ben               
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        48% Check 
RESPONSE: The low value might be due to
the decomposition of the material during the 
measurement.
;
_vrf_PLAT340_7_ben               
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0057 Ang.  
RESPONSE: The low bond precision might be due to
the low quality of the crystal.
;
_vrf_PLAT906_7_ben               
;
PROBLEM: Large K Value in the Analysis of Variance ......     27.014 Check 
RESPONSE: The K value is large only for weak reflections with Fc/Fcmax 
lower than 0.021.
;
_vrf_PLAT910_7_ben               
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).          7 Note  
RESPONSE: Data completeness is 99.2%, which is enough
for a good refinement of data.
;
_vrf_PLAT911_7_ben               
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         24 Report
RESPONSE: Data completeness is 99.5%, which is enough
for a good refinement of data.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19.33 H17 B0.33'
_chemical_formula_weight         252.93

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/c'
_space_group_name_Hall           '-P 2yc'

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

_cell_length_a                   13.734(6)
_cell_length_b                   12.910(6)
_cell_length_c                   12.794(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.017(9)
_cell_angle_gamma                90
_cell_volume                     2190.8(17)
_cell_formula_units_Z            6
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    664
_cell_measurement_theta_min      5.30
_cell_measurement_theta_max      25.26

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   0.1101
_exptl_transmission_factor_max   0.9995
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.064
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1101
_exptl_absorpt_correction_T_max  0.9995
_exptl_absorpt_process_details   
;
Higashi, T. (1995). Program for Absorption Correction.
Rigaku Corporation, Tokyo, Japan
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku FR-E & Rapid'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11986
_diffrn_reflns_av_unetI/netI     0.1598
_diffrn_reflns_av_R_equivalents  0.1519
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.156
_diffrn_reflns_theta_max         25.345
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3989
_reflns_number_gt                1898
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'RAPID AUTO (Rigaku, 2017)'
_computing_cell_refinement       'RAPID AUTO (Rigaku, 2017)'
_computing_data_reduction        'RAPID AUTO (Rigaku, 2017)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ShelXle (J. Appl. Cryst., 44, (2011) 1281-1284.)'
_computing_publication_material  
'ShelXle (J. Appl. Cryst., 44, (2011) 1281-1284.)'
_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)+(0.0615P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3989
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1622
_refine_ls_R_factor_gt           0.0722
_refine_ls_wR_factor_ref         0.1752
_refine_ls_wR_factor_gt          0.1418
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_restrained_S_all      0.935
_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 0.5513(3) 0.8549(3) 0.2381(3) 0.0291(9) Uani 1 1 d . . . . .
B1 B 0.5000 0.6802(4) 0.2500 0.0276(14) Uani 1 2 d S T P . .
C2 C 0.5853(3) 0.7565(3) 0.2286(3) 0.0305(9) Uani 1 1 d . . . . .
C3 C 0.6056(3) 0.9542(3) 0.2327(3) 0.0278(9) Uani 1 1 d . . . . .
C4 C 0.6374(3) 0.9812(3) 0.1411(3) 0.0342(9) Uani 1 1 d . . . . .
H4 H 0.6258 0.9365 0.0821 0.041 Uiso 1 1 calc R U . . .
C5 C 0.6865(3) 1.0750(3) 0.1379(3) 0.0409(11) Uani 1 1 d . . . . .
H5 H 0.7087 1.0920 0.0773 0.049 Uiso 1 1 calc R U . . .
C6 C 0.7027(3) 1.1435(3) 0.2243(3) 0.0378(10) Uani 1 1 d . . . . .
H6 H 0.7349 1.2064 0.2215 0.045 Uiso 1 1 calc R U . . .
C8 C 0.6206(3) 1.0243(3) 0.3182(3) 0.0310(9) Uani 1 1 d . . . . .
H8 H 0.5970 1.0085 0.3782 0.037 Uiso 1 1 calc R U . . .
C7 C 0.6703(3) 1.1174(3) 0.3148(3) 0.0350(9) Uani 1 1 d . . . . .
H7 H 0.6820 1.1623 0.3736 0.042 Uiso 1 1 calc R U . . .
C9 C 0.6839(3) 0.7349(3) 0.2043(3) 0.0276(9) Uani 1 1 d . . . . .
C10 C 0.7714(3) 0.7853(3) 0.2611(3) 0.0287(9) Uani 1 1 d . . . . .
H10 H 0.7684 0.8303 0.3169 0.034 Uiso 1 1 calc R U . . .
C11 C 0.8631(3) 0.7700(3) 0.2362(3) 0.0327(9) Uani 1 1 d . . . . .
H11 H 0.9206 0.8046 0.2748 0.039 Uiso 1 1 calc R U . . .
C12 C 0.8682(3) 0.7021(3) 0.1524(3) 0.0350(10) Uani 1 1 d . . . . .
H12 H 0.9291 0.6918 0.1349 0.042 Uiso 1 1 calc R U . . .
C13 C 0.7821(3) 0.6501(3) 0.0955(3) 0.0365(10) Uani 1 1 d . . . . .
H13 H 0.7853 0.6050 0.0398 0.044 Uiso 1 1 calc R U . . .
C14 C 0.6907(3) 0.6657(3) 0.1221(3) 0.0329(9) Uani 1 1 d . . . . .
H14 H 0.6336 0.6296 0.0848 0.039 Uiso 1 1 calc R U . . .
C15 C 0.5000 0.5584(4) 0.2500 0.0238(11) Uani 1 2 d S T P . .
C16 C 0.4130(3) 0.5015(3) 0.1899(3) 0.0281(9) Uani 1 1 d . . . . .
C17 C 0.4169(3) 0.3925(3) 0.1883(3) 0.0315(9) Uani 1 1 d . . . . .
H17 H 0.3631 0.3556 0.1453 0.038 Uiso 1 1 calc R U . . .
C18 C 0.5000 0.3393(4) 0.2500 0.0281(12) Uani 1 2 d S T P . .
H18 H 0.5000 0.2673 0.2500 0.034 Uiso 1 2 calc R U P . .
C19 C 0.3183(3) 0.5519(3) 0.1255(3) 0.0271(8) Uani 1 1 d . . . . .
C20 C 0.2246(3) 0.5251(3) 0.1465(3) 0.0288(9) Uani 1 1 d . . . . .
C21 C 0.1354(3) 0.5699(3) 0.0856(3) 0.0312(9) Uani 1 1 d . . . . .
H21 H 0.0748 0.5513 0.1002 0.037 Uiso 1 1 calc R U . . .
C22 C 0.1337(3) 0.6420(3) 0.0032(3) 0.0304(9) Uani 1 1 d . . . . .
C23 C 0.2269(3) 0.6653(3) -0.0173(3) 0.0308(9) Uani 1 1 d . . . . .
H23 H 0.2282 0.7128 -0.0716 0.037 Uiso 1 1 calc R U . . .
C24 C 0.3174(3) 0.6208(3) 0.0398(3) 0.0271(9) Uani 1 1 d . . . . .
C25 C 0.4124(3) 0.6465(3) 0.0049(3) 0.0358(9) Uani 1 1 d . . . . .
H25A H 0.3945 0.6659 -0.0701 0.054 Uiso 1 1 calc R U . . .
H25B H 0.4557 0.5869 0.0150 0.054 Uiso 1 1 calc R U . . .
H25C H 0.4471 0.7028 0.0478 0.054 Uiso 1 1 calc R U . . .
C26 C 0.2162(3) 0.4485(3) 0.2343(3) 0.0339(9) Uani 1 1 d . . . . .
H26A H 0.1591 0.4661 0.2610 0.051 Uiso 1 1 calc R U . . .
H26B H 0.2764 0.4514 0.2926 0.051 Uiso 1 1 calc R U . . .
H26C H 0.2079 0.3797 0.2048 0.051 Uiso 1 1 calc R U . . .
C27 C 0.0374(3) 0.6934(3) -0.0588(3) 0.0427(11) Uani 1 1 d . . . . .
H27A H 0.0300 0.7587 -0.0257 0.064 Uiso 1 1 calc R U . . .
H27B H -0.0188 0.6496 -0.0578 0.064 Uiso 1 1 calc R U . . .
H27C H 0.0399 0.7046 -0.1322 0.064 Uiso 1 1 calc R U . . .
C28 C 0.9324(3) 1.0169(3) 0.4010(3) 0.0497(11) Uani 1 1 d . . . . .
H28 H 0.8873 1.0285 0.3340 0.060 Uiso 1 1 calc R U . . .
C29 C 0.8999(3) 1.0234(3) 0.4947(3) 0.0497(11) Uani 1 1 d . . . . .
H29 H 0.8330 1.0388 0.4912 0.060 Uiso 1 1 calc R U . . .
C30 C 0.9680(3) 1.0067(4) 0.5930(4) 0.0514(12) Uani 1 1 d . . . . .
H30 H 0.9468 1.0113 0.6562 0.062 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.369(5) . ?
C1 C3 1.493(4) . ?
C1 C1 1.517(6) 2_655 ?
B1 C15 1.573(7) . ?
B1 C2 1.607(5) 2_655 ?
B1 C2 1.607(5) . ?
C2 C9 1.492(5) . ?
C3 C8 1.393(5) . ?
C3 C4 1.398(4) . ?
C4 C5 1.392(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.385(5) . ?
C6 H6 0.9300 . ?
C8 C7 1.389(5) . ?
C8 H8 0.9300 . ?
C7 H7 0.9300 . ?
C9 C10 1.394(5) . ?
C9 C14 1.402(5) . ?
C10 C11 1.391(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.400(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.390(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.398(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.442(4) . ?
C15 C16 1.442(4) 2_655 ?
C16 C17 1.409(5) . ?
C16 C19 1.497(5) . ?
C17 C18 1.389(4) . ?
C17 H17 0.9300 . ?
C18 C17 1.389(4) 2_655 ?
C18 H18 0.9300 . ?
C19 C24 1.410(5) . ?
C19 C20 1.423(4) . ?
C20 C21 1.396(5) . ?
C20 C26 1.523(5) . ?
C21 C22 1.402(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.404(5) . ?
C22 C27 1.508(5) . ?
C23 C24 1.393(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.522(4) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 C30 1.384(6) 3_776 ?
C28 C29 1.387(5) . ?
C28 H28 0.9300 . ?
C29 C30 1.376(6) . ?
C29 H29 0.9300 . ?
C30 C28 1.384(6) 3_776 ?
C30 H30 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C3 127.3(3) . . ?
C2 C1 C1 111.92(19) . 2_655 ?
C3 C1 C1 120.66(17) . 2_655 ?
C15 B1 C2 127.8(2) . 2_655 ?
C15 B1 C2 127.8(2) . . ?
C2 B1 C2 104.4(4) 2_655 . ?
C1 C2 C9 122.7(3) . . ?
C1 C2 B1 105.8(3) . . ?
C9 C2 B1 131.4(3) . . ?
C8 C3 C4 118.8(3) . . ?
C8 C3 C1 119.7(3) . . ?
C4 C3 C1 121.5(3) . . ?
C5 C4 C3 120.0(4) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C7 C6 C5 119.4(3) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C7 C8 C3 120.8(3) . . ?
C7 C8 H8 119.6 . . ?
C3 C8 H8 119.6 . . ?
C6 C7 C8 120.2(4) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C10 C9 C14 118.2(3) . . ?
C10 C9 C2 120.8(3) . . ?
C14 C9 C2 121.0(3) . . ?
C11 C10 C9 121.6(3) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C12 119.4(4) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C13 C12 C11 120.0(3) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 119.9(3) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C9 120.8(4) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?
C16 C15 C16 118.8(4) . 2_655 ?
C16 C15 B1 120.6(2) . . ?
C16 C15 B1 120.6(2) 2_655 . ?
C17 C16 C15 119.1(4) . . ?
C17 C16 C19 117.2(3) . . ?
C15 C16 C19 123.7(3) . . ?
C18 C17 C16 120.9(4) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C17 120.8(5) 2_655 . ?
C17 C18 H18 119.6 2_655 . ?
C17 C18 H18 119.6 . . ?
C24 C19 C20 118.3(3) . . ?
C24 C19 C16 122.2(3) . . ?
C20 C19 C16 119.4(3) . . ?
C21 C20 C19 120.0(3) . . ?
C21 C20 C26 117.3(3) . . ?
C19 C20 C26 122.8(3) . . ?
C20 C21 C22 122.4(3) . . ?
C20 C21 H21 118.8 . . ?
C22 C21 H21 118.8 . . ?
C21 C22 C23 116.4(3) . . ?
C21 C22 C27 121.9(3) . . ?
C23 C22 C27 121.6(3) . . ?
C24 C23 C22 123.1(3) . . ?
C24 C23 H23 118.5 . . ?
C22 C23 H23 118.5 . . ?
C23 C24 C19 119.7(3) . . ?
C23 C24 C25 118.2(3) . . ?
C19 C24 C25 122.1(3) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C20 C26 H26A 109.5 . . ?
C20 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C20 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C22 C27 H27A 109.5 . . ?
C22 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C22 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C30 C28 C29 120.0(4) 3_776 . ?
C30 C28 H28 120.0 3_776 . ?
C29 C28 H28 120.0 . . ?
C30 C29 C28 119.1(4) . . ?
C30 C29 H29 120.5 . . ?
C28 C29 H29 120.5 . . ?
C29 C30 C28 120.9(4) . 3_776 ?
C29 C30 H30 119.5 . . ?
C28 C30 H30 119.5 3_776 . ?

_refine_diff_density_max         0.275
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_B_blue_a_sq
_database_code_depnum_ccdc_archive 'CCDC 2112955'
loop_
_audit_author_name
_audit_author_address
'Kazuo Tanaka'
;Kyoto University
Japan
;
_audit_update_record             
;
2021-10-25 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT906_B_blue_a_sq         
;
PROBLEM: Large K Value in the Analysis of Variance ......     14.967 Check 
RESPONSE: The K value is large only for weak reflections with Fc/Fcmax 
lower than 0.021.
;
_vrf_PLAT911_B_blue_a_sq         
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report
RESPONSE: Data completeness is 99.5%, which is enough
for a good refinement of data.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         'C52 H45 B, 0.5 (C6 H14)'
_chemical_formula_sum            'C55 H52 B'
_chemical_formula_weight         723.8258

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/c'
_space_group_name_Hall           '-P 2yc'

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

_cell_length_a                   13.6520(9)
_cell_length_b                   12.8989(6)
_cell_length_c                   12.7196(7)
_cell_angle_alpha                90
_cell_angle_beta                 106.517(7)
_cell_angle_gamma                90
_cell_volume                     2147.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    11509
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.119
_exptl_crystal_F_000             724
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.063
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.4370
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'ABSCOR, (Rigaku, 1995)'
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Rigaku Raxis Rapid'
_diffrn_measurement_method       'oscillation method'
_diffrn_reflns_number            20177
_diffrn_reflns_av_unetI/netI     0.0815
_diffrn_reflns_av_R_equivalents  0.0947
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.217
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4916
_reflns_number_gt                3317
_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.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'RAPID AUTO (Rigaku, 2017)'
_computing_cell_refinement       'RAPID AUTO (Rigaku, 2017)'
_computing_data_reduction        'RAPID AUTO (Rigaku, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ShelXle (J. Appl. Cryst., 44, (2011) 1281-1284.)'
_computing_publication_material  
'ShelXle (J. Appl. Cryst., 44, (2011) 1281-1284.)'
_refine_special_details          ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 -0.000 0.023 320 66 C6H14
2 0.971 0.190 0.059 9 0 ' '
3 0.029 0.190 0.440 10 0 ' '
4 0.971 0.810 0.559 9 0 ' '
5 0.029 0.810 0.940 9 0 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          
;
The unit cell contains one hexane molecule which have been treated
as a diffuse contribution to the overall scattering without specific atom
positions by SQUEEZE/PLATON. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0909P)²+1.1530P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4916
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1264
_refine_ls_R_factor_gt           0.0796
_refine_ls_wR_factor_ref         0.2060
_refine_ls_wR_factor_gt          0.1786
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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 0.08485(18) 0.75698(19) 0.2294(2) 0.0191(5) Uani 1 1 d . . . . .
C3 C 0.10542(18) 0.95350(19) 0.2345(2) 0.0206(5) Uani 1 1 d . . . . .
C4 C 0.1343(2) 0.9826(2) 0.1428(2) 0.0287(6) Uani 1 1 d . . . . .
H4 H 0.118779 0.939084 0.079938 0.034 Uiso 1 1 calc R U . . .
C5 C 0.1861(3) 1.0753(2) 0.1426(3) 0.0430(8) Uani 1 1 d . . . . .
H5 H 0.204984 1.095460 0.079270 0.052 Uiso 1 1 calc R U . . .
C6 C 0.2101(3) 1.1382(2) 0.2343(3) 0.0402(8) Uani 1 1 d . . . . .
H6 H 0.246419 1.201043 0.234042 0.048 Uiso 1 1 calc R U . . .
C7 C 0.1818(2) 1.1103(2) 0.3259(2) 0.0319(7) Uani 1 1 d . . . . .
H7 H 0.198793 1.153332 0.389177 0.038 Uiso 1 1 calc R U . . .
C8 C 0.1281(2) 1.01890(19) 0.3251(2) 0.0240(6) Uani 1 1 d . . . . .
H8 H 0.106442 1.000694 0.387370 0.029 Uiso 1 1 calc R U . . .
C9 C 0.18287(18) 0.73462(18) 0.2059(2) 0.0196(5) Uani 1 1 d . . . . .
C10 C 0.18883(19) 0.66557(19) 0.1238(2) 0.0232(6) Uani 1 1 d . . . . .
H10 H 0.129326 0.628855 0.084565 0.028 Uiso 1 1 calc R U . . .
C11 C 0.2797(2) 0.6492(2) 0.0980(2) 0.0279(6) Uani 1 1 d . . . . .
H11 H 0.281665 0.602726 0.040685 0.034 Uiso 1 1 calc R U . . .
C12 C 0.3669(2) 0.7004(2) 0.1554(2) 0.0274(6) Uani 1 1 d . . . . .
H12 H 0.429503 0.688715 0.138486 0.033 Uiso 1 1 calc R U . . .
C13 C 0.3632(2) 0.7689(2) 0.2376(2) 0.0258(6) Uani 1 1 d . . . . .
H13 H 0.423181 0.805068 0.276640 0.031 Uiso 1 1 calc R U . . .
C14 C 0.27264(19) 0.7852(2) 0.2635(2) 0.0223(6) Uani 1 1 d . . . . .
H14 H 0.271418 0.831463 0.321195 0.027 Uiso 1 1 calc R U . . .
C15 C 0.000000 0.5590(3) 0.250000 0.0196(7) Uani 1 2 d S T P . .
C16 C 0.08680(18) 0.50156(18) 0.3117(2) 0.0194(5) Uani 1 1 d . . . . .
C17 C 0.08297(19) 0.39388(19) 0.3129(2) 0.0213(6) Uani 1 1 d . . . . .
H17 H 0.139209 0.356694 0.358517 0.026 Uiso 1 1 calc R U . . .
C18 C 0.000000 0.3394(3) 0.250000 0.0223(8) Uani 1 2 d S T P . .
H18 H 0.000001 0.265770 0.250000 0.027 Uiso 1 2 calc R U P . .
C19 C 0.18434(18) 0.55186(19) 0.3777(2) 0.0191(5) Uani 1 1 d . . . . .
C20 C 0.18663(19) 0.62130(19) 0.4641(2) 0.0204(5) Uani 1 1 d . . . . .
C21 C 0.27947(19) 0.66436(19) 0.5232(2) 0.0224(6) Uani 1 1 d . . . . .
H21 H 0.280206 0.712430 0.580050 0.027 Uiso 1 1 calc R U . . .
C22 C 0.37111(19) 0.6395(2) 0.5021(2) 0.0233(6) Uani 1 1 d . . . . .
C23 C 0.36748(19) 0.56922(19) 0.4190(2) 0.0221(6) Uani 1 1 d . . . . .
H23 H 0.429455 0.550342 0.404037 0.026 Uiso 1 1 calc R U . . .
C24 C 0.27693(18) 0.52518(19) 0.3565(2) 0.0194(5) Uani 1 1 d . . . . .
C25 C 0.09269(19) 0.6472(2) 0.4986(2) 0.0236(6) Uani 1 1 d . . . . .
H25A H 0.054231 0.702101 0.451333 0.035 Uiso 1 1 calc R U . . .
H25B H 0.113005 0.670904 0.574961 0.035 Uiso 1 1 calc R U . . .
H25C H 0.049719 0.585268 0.492034 0.035 Uiso 1 1 calc R U . . .
C26 C 0.4700(2) 0.6885(2) 0.5665(3) 0.0347(7) Uani 1 1 d . . . . .
H26A H 0.477247 0.756500 0.535212 0.052 Uiso 1 1 calc R U . . .
H26B H 0.527202 0.643954 0.563150 0.052 Uiso 1 1 calc R U . . .
H26C H 0.469934 0.696846 0.643041 0.052 Uiso 1 1 calc R U . . .
C27 C 0.28307(19) 0.4492(2) 0.2679(2) 0.0256(6) Uani 1 1 d . . . . .
H27A H 0.220266 0.453231 0.206982 0.038 Uiso 1 1 calc R U . . .
H27B H 0.291126 0.378768 0.297965 0.038 Uiso 1 1 calc R U . . .
H27C H 0.341805 0.466502 0.241356 0.038 Uiso 1 1 calc R U . . .
B1 B 0.000000 0.6804(3) 0.250000 0.0194(8) Uani 1 2 d S T P . .
C2 C 0.05155(18) 0.85387(19) 0.2389(2) 0.0195(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 1.347(3) . ?
C1 C9 1.480(3) . ?
C1 B1 1.600(3) . ?
C3 C4 1.385(4) . ?
C3 C8 1.390(4) . ?
C3 C2 1.490(3) . ?
C4 C5 1.389(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.377(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.387(4) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.393(3) . ?
C9 C14 1.398(3) . ?
C10 C11 1.386(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.377(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.382(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.428(3) 2 ?
C15 C16 1.428(3) . ?
C15 B1 1.566(5) . ?
C16 C17 1.390(3) . ?
C16 C19 1.504(3) . ?
C17 C18 1.379(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C24 1.408(3) . ?
C19 C20 1.412(3) . ?
C20 C21 1.392(4) . ?
C20 C25 1.506(3) . ?
C21 C22 1.390(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.383(4) . ?
C22 C26 1.504(4) . ?
C23 C24 1.387(3) . ?
C23 H23 0.9500 . ?
C24 C27 1.514(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C2 C2 1.512(5) 2 ?

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 123.1(2) . . ?
C2 C1 B1 106.2(2) . . ?
C9 C1 B1 130.6(2) . . ?
C4 C3 C8 119.0(2) . . ?
C4 C3 C2 121.8(2) . . ?
C8 C3 C2 119.2(2) . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.3(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C7 C6 C5 120.3(3) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 119.4(3) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C7 C8 C3 121.0(2) . . ?
C7 C8 H8 119.5 . . ?
C3 C8 H8 119.5 . . ?
C10 C9 C14 117.5(2) . . ?
C10 C9 C1 121.7(2) . . ?
C14 C9 C1 120.8(2) . . ?
C11 C10 C9 121.5(2) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C12 C11 C10 119.9(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 119.7(2) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C14 120.3(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C9 121.0(2) . . ?
C13 C14 H14 119.5 . . ?
C9 C14 H14 119.5 . . ?
C16 C15 C16 117.5(3) 2 . ?
C16 C15 B1 121.26(15) 2 . ?
C16 C15 B1 121.26(15) . . ?
C17 C16 C15 119.8(2) . . ?
C17 C16 C19 117.0(2) . . ?
C15 C16 C19 123.2(2) . . ?
C18 C17 C16 122.0(3) . . ?
C18 C17 H17 119.0 . . ?
C16 C17 H17 119.0 . . ?
C17 C18 C17 118.8(3) . 2 ?
C17 C18 H18 120.6 . . ?
C17 C18 H18 120.6 2 . ?
C24 C19 C20 118.8(2) . . ?
C24 C19 C16 119.2(2) . . ?
C20 C19 C16 121.9(2) . . ?
C21 C20 C19 119.3(2) . . ?
C21 C20 C25 118.3(2) . . ?
C19 C20 C25 122.4(2) . . ?
C22 C21 C20 122.3(2) . . ?
C22 C21 H21 118.8 . . ?
C20 C21 H21 118.8 . . ?
C23 C22 C21 117.4(2) . . ?
C23 C22 C26 121.5(2) . . ?
C21 C22 C26 121.0(2) . . ?
C22 C23 C24 122.6(2) . . ?
C22 C23 H23 118.7 . . ?
C24 C23 H23 118.7 . . ?
C23 C24 C19 119.5(2) . . ?
C23 C24 C27 117.5(2) . . ?
C19 C24 C27 122.9(2) . . ?
C20 C25 H25A 109.5 . . ?
C20 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C20 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C22 C26 H26A 109.5 . . ?
C22 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C22 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C15 B1 C1 128.14(14) . 2 ?
C15 B1 C1 128.14(14) . . ?
C1 B1 C1 103.7(3) 2 . ?
C1 C2 C3 127.9(2) . . ?
C1 C2 C2 111.88(14) . 2 ?
C3 C2 C2 120.19(13) . 2 ?

_refine_diff_density_max         0.325
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.061







####################################################################### 
# 
# 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_ydkr
_database_code_depnum_ccdc_archive 'CCDC 2112956'
loop_
_audit_author_name
_audit_author_address
'Kazuo Tanaka'
;Kyoto University
Japan
;
_audit_update_record             
;
2021-10-25 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT230_ydkr                
;
PROBLEM: Hirshfeld Test Diff for    C25      --C26      .        9.0 s.u.  
RESPONSE: This might be caused by vibration of a complete phenyl group, 
and is not derived from wrong assignment.
;
_vrf_PLAT906_ydkr                
;
PROBLEM: Large K Value in the Analysis of Variance ......      7.594 Check 
RESPONSE: The K value is large only for weak reflections with Fc/Fcmax 
lower than 0.008.
;
_vrf_PLAT910_ydkr                
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).          7 Note  
RESPONSE: Data completeness is 99.5%, which is enough
for a good refinement of data.
;
_vrf_PLAT911_ydkr                
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          3 Report
RESPONSE: Data completeness is 99.5%, which is enough
for a good refinement of data.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         'C52 H45 B, 0.5(C6 H14)'
_chemical_formula_sum            'C55 H52 B'
_chemical_formula_weight         723.78

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'
B B 0.0013 0.0007 '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                   10.8870(5)
_cell_length_b                   11.6042(5)
_cell_length_c                   32.5768(14)
_cell_angle_alpha                90
_cell_angle_beta                 92.690(7)
_cell_angle_gamma                90
_cell_volume                     4111.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    26955
_cell_measurement_theta_min      1.75
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_F_000             1548
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5470
_exptl_absorpt_correction_T_max  0.7379
_exptl_absorpt_process_details   'ABSCOR, (Rigaku, 1995)'
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Rigaku Raxis Rapid'
_diffrn_measurement_method       'oscillation method'
_diffrn_reflns_number            36369
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         2.567
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9366
_reflns_number_gt                6702
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'RAPID AUTO (Rigaku, 2017)'
_computing_cell_refinement       'RAPID AUTO (Rigaku, 2017)'
_computing_data_reduction        'RAPID AUTO (Rigaku, 2017)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ShelXle (J. Appl. Cryst., 44, (2011) 1281-1284.)'
_computing_publication_material  
'ShelXle (J. Appl. Cryst., 44, (2011) 1281-1284.)'
_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)+(0.0542P)²+1.4564P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9366
_refine_ls_number_parameters     511
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0533
_refine_ls_wR_factor_ref         0.1270
_refine_ls_wR_factor_gt          0.1143
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.22374(13) 0.36492(13) 0.34034(4) 0.0206(3) Uani 1 1 d . . . . .
C4 C 0.24142(13) 0.17845(13) 0.38341(5) 0.0222(3) Uani 1 1 d . . . . .
H4 H 0.217613 0.195801 0.412038 0.027 Uiso 1 1 calc R U . . .
C5 C 0.17167(14) 0.46273(13) 0.36643(5) 0.0211(3) Uani 1 1 d . . . . .
C6 C 0.19157(14) 0.57900(13) 0.35775(5) 0.0233(3) Uani 1 1 d . . . . .
H6 H 0.244388 0.599238 0.336499 0.028 Uiso 1 1 calc R U . . .
C7 C 0.13561(15) 0.66534(14) 0.37960(5) 0.0283(4) Uani 1 1 d . . . . .
H7 H 0.149336 0.743798 0.372866 0.034 Uiso 1 1 calc R U . . .
C8 C 0.06012(16) 0.63816(15) 0.41105(5) 0.0330(4) Uani 1 1 d . . . . .
H8 H 0.020526 0.697361 0.425632 0.040 Uiso 1 1 calc R U . . .
C9 C 0.04271(16) 0.52328(16) 0.42115(5) 0.0332(4) Uani 1 1 d . . . . .
H9 H -0.007054 0.503826 0.443310 0.040 Uiso 1 1 calc R U . . .
C10 C 0.09733(15) 0.43708(14) 0.39914(5) 0.0269(4) Uani 1 1 d . . . . .
H10 H 0.084201 0.358863 0.406342 0.032 Uiso 1 1 calc R U . . .
C11 C 0.02257(14) 0.30090(13) 0.29785(5) 0.0225(3) Uani 1 1 d . . . . .
C12 C -0.03406(14) 0.40783(15) 0.29231(5) 0.0269(4) Uani 1 1 d . . . . .
H12 H -0.011298 0.469829 0.310127 0.032 Uiso 1 1 calc R U . . .
C13 C -0.12353(16) 0.42486(17) 0.26098(6) 0.0347(4) Uani 1 1 d . . . . .
H13 H -0.162682 0.497719 0.257914 0.042 Uiso 1 1 calc R U . . .
C14 C -0.15559(17) 0.33604(19) 0.23433(6) 0.0401(5) Uani 1 1 d . . . . .
H14 H -0.216284 0.347716 0.212820 0.048 Uiso 1 1 calc R U . . .
C2 C 0.12011(13) 0.27860(13) 0.33032(4) 0.0199(3) Uani 1 1 d . . . . .
C15 C -0.09887(17) 0.23035(18) 0.23917(5) 0.0396(4) Uani 1 1 d . . . . .
H15 H -0.120142 0.169246 0.220778 0.047 Uiso 1 1 calc R U . . .
C16 C -0.01119(16) 0.21279(16) 0.27066(5) 0.0315(4) Uani 1 1 d . . . . .
H16 H 0.026606 0.139319 0.273763 0.038 Uiso 1 1 calc R U . . .
C17 C 0.02110(14) 0.10359(13) 0.35992(5) 0.0223(3) Uani 1 1 d . . . . .
C18 C 0.02938(16) -0.01476(15) 0.35494(6) 0.0341(4) Uani 1 1 d . . . . .
H18 H 0.104848 -0.048136 0.347499 0.041 Uiso 1 1 calc R U . . .
C19 C -0.07136(17) -0.08477(16) 0.36072(7) 0.0467(5) Uani 1 1 d . . . . .
H19 H -0.064734 -0.165599 0.356747 0.056 Uiso 1 1 calc R U . . .
C20 C -0.18114(17) -0.03835(17) 0.37218(7) 0.0430(5) Uani 1 1 d . . . . .
H20 H -0.249752 -0.086898 0.376272 0.052 Uiso 1 1 calc R U . . .
C21 C -0.19061(15) 0.07888(17) 0.37763(5) 0.0334(4) Uani 1 1 d . . . . .
H21 H -0.265787 0.111495 0.385711 0.040 Uiso 1 1 calc R U . . .
C22 C -0.09101(14) 0.14889(15) 0.37138(5) 0.0264(3) Uani 1 1 d . . . . .
H22 H -0.098809 0.229767 0.374949 0.032 Uiso 1 1 calc R U . . .
C23 C 0.30390(14) 0.06179(14) 0.38375(5) 0.0264(4) Uani 1 1 d . . . . .
C24 C 0.30219(17) -0.00975(16) 0.41806(6) 0.0364(4) Uani 1 1 d . . . . .
H24 H 0.262123 0.015542 0.441732 0.044 Uiso 1 1 calc R U . . .
C25 C 0.35772(19) -0.11682(17) 0.41829(7) 0.0467(5) Uani 1 1 d . . . . .
H25 H 0.354943 -0.164798 0.441858 0.056 Uiso 1 1 calc R U . . .
C26 C 0.41695(18) -0.15376(17) 0.38438(8) 0.0522(6) Uani 1 1 d . . . . .
H26 H 0.456264 -0.226866 0.384708 0.063 Uiso 1 1 calc R U . . .
C27 C 0.41958(17) -0.08480(17) 0.34968(8) 0.0475(5) Uani 1 1 d . . . . .
H27 H 0.460183 -0.110633 0.326192 0.057 Uiso 1 1 calc R U . . .
C28 C 0.36248(16) 0.02234(15) 0.34944(6) 0.0348(4) Uani 1 1 d . . . . .
H28 H 0.363493 0.069179 0.325546 0.042 Uiso 1 1 calc R U . . .
C29 C 0.45706(14) 0.31131(13) 0.36957(5) 0.0211(3) Uani 1 1 d . . . . .
C30 C 0.52052(14) 0.31051(13) 0.33255(5) 0.0234(3) Uani 1 1 d . . . . .
C31 C 0.64294(14) 0.34595(14) 0.33314(5) 0.0273(4) Uani 1 1 d . . . . .
H31 H 0.685791 0.345360 0.308405 0.033 Uiso 1 1 calc R U . . .
C32 C 0.70280(14) 0.38193(14) 0.36924(5) 0.0285(4) Uani 1 1 d . . . . .
H32 H 0.785073 0.409069 0.368918 0.034 Uiso 1 1 calc R U . . .
C33 C 0.64338(14) 0.37859(14) 0.40584(5) 0.0264(3) Uani 1 1 d . . . . .
H33 H 0.685807 0.401260 0.430679 0.032 Uiso 1 1 calc R U . . .
C34 C 0.52157(14) 0.34212(13) 0.40640(5) 0.0227(3) Uani 1 1 d . . . . .
C35 C 0.45836(14) 0.26987(14) 0.29306(5) 0.0235(3) Uani 1 1 d . . . . .
C36 C 0.34778(14) 0.32110(13) 0.27804(5) 0.0229(3) Uani 1 1 d . . . . .
C37 C 0.29404(15) 0.28667(14) 0.24051(5) 0.0268(4) Uani 1 1 d . . . . .
H37 H 0.220637 0.323355 0.230460 0.032 Uiso 1 1 calc R U . . .
C38 C 0.34477(17) 0.20013(15) 0.21735(5) 0.0312(4) Uani 1 1 d . . . . .
C39 C 0.45077(17) 0.14670(15) 0.23327(5) 0.0325(4) Uani 1 1 d . . . . .
H39 H 0.485080 0.085648 0.218116 0.039 Uiso 1 1 calc R U . . .
C40 C 0.50885(15) 0.17884(14) 0.27049(5) 0.0280(4) Uani 1 1 d . . . . .
C41 C 0.28753(14) 0.41367(13) 0.30255(5) 0.0223(3) Uani 1 1 d . . . . .
H41A H 0.225819 0.454379 0.284589 0.027 Uiso 1 1 calc R U . . .
H41B H 0.350516 0.470534 0.311978 0.027 Uiso 1 1 calc R U . . .
C42 C 0.2870(2) 0.16571(18) 0.17627(6) 0.0448(5) Uani 1 1 d . . . . .
H42A H 0.292428 0.230033 0.156951 0.067 Uiso 1 1 calc R U . . .
H42B H 0.200423 0.145880 0.179411 0.067 Uiso 1 1 calc R U . . .
H42C H 0.330466 0.098800 0.165721 0.067 Uiso 1 1 calc R U . . .
C43 C 0.61956(16) 0.11128(16) 0.28658(6) 0.0362(4) Uani 1 1 d . . . . .
H43A H 0.622793 0.037373 0.272116 0.054 Uiso 1 1 calc R U . . .
H43B H 0.613177 0.097383 0.316079 0.054 Uiso 1 1 calc R U . . .
H43C H 0.694526 0.155257 0.281988 0.054 Uiso 1 1 calc R U . . .
C44 C 0.45757(13) 0.33374(14) 0.44611(5) 0.0220(3) Uani 1 1 d . . . . .
C45 C 0.38834(14) 0.42547(14) 0.46069(5) 0.0245(3) Uani 1 1 d . . . . .
C46 C 0.32158(15) 0.40881(16) 0.49570(5) 0.0300(4) Uani 1 1 d . . . . .
H46 H 0.271878 0.469946 0.504968 0.036 Uiso 1 1 calc R U . . .
C47 C 0.32525(15) 0.30643(16) 0.51737(5) 0.0307(4) Uani 1 1 d . . . . .
C48 C 0.39946(15) 0.21844(15) 0.50353(5) 0.0287(4) Uani 1 1 d . . . . .
H48 H 0.404647 0.148183 0.518489 0.034 Uiso 1 1 calc R U . . .
C49 C 0.46624(14) 0.23026(14) 0.46849(5) 0.0249(3) Uani 1 1 d . . . . .
C50 C 0.38980(16) 0.54333(14) 0.44110(5) 0.0304(4) Uani 1 1 d . . . . .
H50A H 0.414406 0.536323 0.412656 0.046 Uiso 1 1 calc R U . . .
H50B H 0.448483 0.592793 0.456541 0.046 Uiso 1 1 calc R U . . .
H50C H 0.307474 0.577372 0.441396 0.046 Uiso 1 1 calc R U . . .
C51 C 0.25617(19) 0.2918(2) 0.55603(6) 0.0466(5) Uani 1 1 d . . . . .
H51A H 0.208415 0.361608 0.560959 0.070 Uiso 1 1 calc R U . . .
H51B H 0.314689 0.278537 0.579329 0.070 Uiso 1 1 calc R U . . .
H51C H 0.200467 0.225694 0.552941 0.070 Uiso 1 1 calc R U . . .
C52 C 0.55107(16) 0.13528(15) 0.45570(5) 0.0312(4) Uani 1 1 d . . . . .
H52A H 0.529027 0.112250 0.427358 0.047 Uiso 1 1 calc R U . . .
H52B H 0.543083 0.068906 0.473977 0.047 Uiso 1 1 calc R U . . .
H52C H 0.636175 0.163014 0.457444 0.047 Uiso 1 1 calc R U . . .
C53 C 0.0808(3) 0.7389(2) 0.51616(7) 0.0620(7) Uani 1 1 d . . . . .
H53A H -0.000988 0.707488 0.509005 0.093 Uiso 1 1 calc R U . . .
H53B H 0.092702 0.743500 0.546118 0.093 Uiso 1 1 calc R U . . .
H53C H 0.143620 0.688421 0.505211 0.093 Uiso 1 1 calc R U . . .
C54 C 0.0918(2) 0.8582(2) 0.49782(7) 0.0549(6) Uani 1 1 d . . . . .
H54A H 0.172995 0.890740 0.506445 0.066 Uiso 1 1 calc R U . . .
H54B H 0.088410 0.851570 0.467491 0.066 Uiso 1 1 calc R U . . .
C55 C -0.0058(2) 0.93945(19) 0.51000(7) 0.0536(6) Uani 1 1 d . . . . .
H55A H -0.001285 0.947928 0.540271 0.064 Uiso 1 1 calc R U . . .
H55B H -0.087238 0.906512 0.501898 0.064 Uiso 1 1 calc R U . . .
B1 B 0.31634(16) 0.28533(15) 0.36739(5) 0.0209(4) Uani 1 1 d . . . . .
C3 C 0.12477(13) 0.18502(13) 0.35496(5) 0.0207(3) 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 1.532(2) . ?
C1 C5 1.542(2) . ?
C1 C41 1.548(2) . ?
C1 B1 1.601(2) . ?
C4 C23 1.515(2) . ?
C4 C3 1.539(2) . ?
C4 B1 1.586(2) . ?
C5 C6 1.397(2) . ?
C5 C10 1.400(2) . ?
C6 C7 1.387(2) . ?
C7 C8 1.380(2) . ?
C8 C9 1.388(3) . ?
C9 C10 1.381(2) . ?
C11 C16 1.391(2) . ?
C11 C12 1.393(2) . ?
C11 C2 1.486(2) . ?
C12 C13 1.391(2) . ?
C13 C14 1.382(3) . ?
C14 C15 1.379(3) . ?
C2 C3 1.350(2) . ?
C15 C16 1.383(2) . ?
C17 C18 1.386(2) . ?
C17 C22 1.396(2) . ?
C17 C3 1.487(2) . ?
C18 C19 1.385(3) . ?
C19 C20 1.378(3) . ?
C20 C21 1.376(3) . ?
C21 C22 1.378(2) . ?
C23 C28 1.390(2) . ?
C23 C24 1.393(2) . ?
C24 C25 1.382(3) . ?
C25 C26 1.374(3) . ?
C26 C27 1.386(3) . ?
C27 C28 1.390(3) . ?
C29 C34 1.408(2) . ?
C29 C30 1.418(2) . ?
C29 B1 1.560(2) . ?
C30 C31 1.394(2) . ?
C30 C35 1.501(2) . ?
C31 C32 1.382(2) . ?
C32 C33 1.383(2) . ?
C33 C34 1.393(2) . ?
C34 C44 1.501(2) . ?
C35 C36 1.409(2) . ?
C35 C40 1.413(2) . ?
C36 C37 1.389(2) . ?
C36 C41 1.507(2) . ?
C37 C38 1.386(2) . ?
C38 C39 1.389(3) . ?
C38 C42 1.506(2) . ?
C39 C40 1.392(2) . ?
C40 C43 1.511(2) . ?
C44 C45 1.400(2) . ?
C44 C49 1.406(2) . ?
C45 C46 1.394(2) . ?
C45 C50 1.509(2) . ?
C46 C47 1.382(2) . ?
C47 C48 1.390(2) . ?
C47 C51 1.506(2) . ?
C48 C49 1.389(2) . ?
C49 C52 1.509(2) . ?
C53 C54 1.515(3) . ?
C54 C55 1.488(3) . ?
C55 C55 1.557(4) 3_576 ?

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 C5 108.21(12) . . ?
C2 C1 C41 115.01(12) . . ?
C5 C1 C41 111.07(12) . . ?
C2 C1 B1 100.28(12) . . ?
C5 C1 B1 111.07(12) . . ?
C41 C1 B1 110.74(12) . . ?
C23 C4 C3 113.98(13) . . ?
C23 C4 B1 117.61(13) . . ?
C3 C4 B1 100.70(12) . . ?
C6 C5 C10 117.38(14) . . ?
C6 C5 C1 122.32(13) . . ?
C10 C5 C1 120.25(13) . . ?
C7 C6 C5 121.18(15) . . ?
C8 C7 C6 120.49(16) . . ?
C7 C8 C9 119.21(16) . . ?
C10 C9 C8 120.37(16) . . ?
C9 C10 C5 121.29(15) . . ?
C16 C11 C12 118.04(15) . . ?
C16 C11 C2 118.94(14) . . ?
C12 C11 C2 122.98(14) . . ?
C13 C12 C11 120.78(16) . . ?
C14 C13 C12 120.16(17) . . ?
C15 C14 C13 119.53(17) . . ?
C3 C2 C11 124.68(14) . . ?
C3 C2 C1 113.11(13) . . ?
C11 C2 C1 122.15(13) . . ?
C14 C15 C16 120.38(18) . . ?
C15 C16 C11 121.10(17) . . ?
C18 C17 C22 117.83(15) . . ?
C18 C17 C3 124.27(14) . . ?
C22 C17 C3 117.88(14) . . ?
C19 C18 C17 120.60(17) . . ?
C20 C19 C18 120.65(18) . . ?
C21 C20 C19 119.50(17) . . ?
C20 C21 C22 119.96(17) . . ?
C21 C22 C17 121.45(16) . . ?
C28 C23 C24 118.21(16) . . ?
C28 C23 C4 120.75(15) . . ?
C24 C23 C4 121.03(16) . . ?
C25 C24 C23 121.19(19) . . ?
C26 C25 C24 119.9(2) . . ?
C25 C26 C27 120.26(19) . . ?
C26 C27 C28 119.6(2) . . ?
C27 C28 C23 120.81(18) . . ?
C34 C29 C30 118.89(14) . . ?
C34 C29 B1 122.53(13) . . ?
C30 C29 B1 118.48(14) . . ?
C31 C30 C29 119.33(15) . . ?
C31 C30 C35 119.80(14) . . ?
C29 C30 C35 120.86(14) . . ?
C32 C31 C30 120.89(15) . . ?
C31 C32 C33 120.26(15) . . ?
C32 C33 C34 120.26(15) . . ?
C33 C34 C29 120.21(14) . . ?
C33 C34 C44 120.78(14) . . ?
C29 C34 C44 119.00(13) . . ?
C36 C35 C40 118.79(15) . . ?
C36 C35 C30 120.55(14) . . ?
C40 C35 C30 120.66(14) . . ?
C37 C36 C35 120.12(14) . . ?
C37 C36 C41 119.71(14) . . ?
C35 C36 C41 120.17(14) . . ?
C38 C37 C36 121.69(16) . . ?
C37 C38 C39 117.73(16) . . ?
C37 C38 C42 121.02(17) . . ?
C39 C38 C42 121.24(16) . . ?
C38 C39 C40 122.77(16) . . ?
C39 C40 C35 118.79(16) . . ?
C39 C40 C43 119.05(15) . . ?
C35 C40 C43 122.08(15) . . ?
C36 C41 C1 112.55(12) . . ?
C45 C44 C49 119.84(14) . . ?
C45 C44 C34 121.48(14) . . ?
C49 C44 C34 118.67(14) . . ?
C46 C45 C44 118.79(15) . . ?
C46 C45 C50 119.18(15) . . ?
C44 C45 C50 121.93(14) . . ?
C47 C46 C45 122.24(16) . . ?
C46 C47 C48 117.99(15) . . ?
C46 C47 C51 121.37(17) . . ?
C48 C47 C51 120.58(17) . . ?
C49 C48 C47 121.91(16) . . ?
C48 C49 C44 119.06(15) . . ?
C48 C49 C52 120.37(15) . . ?
C44 C49 C52 120.52(14) . . ?
C55 C54 C53 113.8(2) . . ?
C54 C55 C55 112.8(2) . 3_576 ?
C29 B1 C4 130.95(14) . . ?
C29 B1 C1 120.36(13) . . ?
C4 B1 C1 108.18(13) . . ?
C2 C3 C17 124.64(14) . . ?
C2 C3 C4 113.89(13) . . ?
C17 C3 C4 120.82(13) . . ?

_refine_diff_density_max         0.333
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.045

