# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_MF71FMI
_database_code_depnum_ccdc_archive 'CCDC 2180015'
loop_
_audit_author_name
_audit_author_address
'James C. Fettinger'
;UC Davis
United States of America
;
_audit_update_record             
;
2022-06-18 deposited with the CCDC.	2022-08-12 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H51 B'
_chemical_formula_sum            'C30 H51 B'
_chemical_formula_weight         422.52
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_space_group_crystal_system      trigonal
_space_group_IT_number           146
_space_group_name_H-M_alt        'R 3 :H'
_space_group_name_Hall           'R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'

_cell_length_a                   16.905(5)
_cell_length_b                   16.905(5)
_cell_length_c                   8.039(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1989.6(16)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    4161
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      27.89
_cell_measurement_theta_min      2.89
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.942
_exptl_absorpt_coefficient_mu    0.058
_exptl_absorpt_correction_T_max  0.9749
_exptl_absorpt_correction_T_min  0.8129
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5 (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.058
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             708
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.649
_exptl_crystal_size_min          0.464
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4323
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.891
_diffrn_reflns_theta_min         2.891
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.966
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                2032
_reflns_number_total             2086
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT (8.34a) (Bruker, 2013)'
_computing_data_collection       'Apex2 (2013.6-2) (Bruker, 2013)'
_computing_data_reduction        'SAINT (8.34a) (Bruker, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 966 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.4(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     96
_refine_ls_number_reflns         2086
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0364
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0523P)²+0.7685P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0927
_refine_special_details          ?
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.33333 0.66667 0.2377(3) 0.0143(5) Uani 1 3 d S T P . .
C1 C 0.25126(10) 0.56486(10) 0.22770(19) 0.0170(3) Uani 1 1 d . . . . .
H1A H 0.1991 0.5620 0.2889 0.020 Uiso 1 1 calc R U . . .
H1B H 0.2327 0.5515 0.1096 0.020 Uiso 1 1 calc R U . . .
C2 C 0.26559(11) 0.48758(10) 0.2937(2) 0.0185(3) Uani 1 1 d . . . . .
H2 H 0.3225 0.4954 0.2404 0.022 Uiso 1 1 calc R U . . .
C3 C 0.18689(13) 0.39079(12) 0.2440(2) 0.0272(4) Uani 1 1 d . . . . .
H3A H 0.1338 0.3962 0.2082 0.033 Uiso 1 1 calc R U . . .
H3B H 0.2072 0.3695 0.1469 0.033 Uiso 1 1 calc R U . . .
C4 C 0.15470(14) 0.31652(12) 0.3822(2) 0.0295(4) Uani 1 1 d . . . . .
H4A H 0.0872 0.2847 0.3899 0.035 Uiso 1 1 calc R U . . .
H4B H 0.1722 0.2708 0.3505 0.035 Uiso 1 1 calc R U . . .
C5 C 0.19535(12) 0.35580(12) 0.5530(2) 0.0241(4) Uani 1 1 d . . . . .
H5 H 0.1745 0.3104 0.6459 0.029 Uiso 1 1 calc R U . . .
C6 C 0.30045(12) 0.41635(14) 0.5338(3) 0.0320(4) Uani 1 1 d . . . . .
H6A H 0.3269 0.3964 0.4444 0.038 Uiso 1 1 calc R U . . .
H6B H 0.3349 0.4279 0.6391 0.038 Uiso 1 1 calc R U . . .
C7 C 0.28168(10) 0.49420(11) 0.4819(2) 0.0204(3) Uani 1 1 d . . . . .
H7 H 0.3281 0.5563 0.5225 0.025 Uiso 1 1 calc R U . . .
C8 C 0.19256(11) 0.44494(11) 0.5905(2) 0.0215(3) Uani 1 1 d . . . . .
C9 C 0.10590(12) 0.44712(13) 0.5454(2) 0.0271(4) Uani 1 1 d . . . . .
H9A H 0.0553 0.4035 0.6153 0.041 Uiso 1 1 calc R U . . .
H9B H 0.0910 0.4305 0.4281 0.041 Uiso 1 1 calc R U . . .
H9C H 0.1158 0.5087 0.5639 0.041 Uiso 1 1 calc R U . . .
C10 C 0.21452(16) 0.47417(15) 0.7725(2) 0.0371(5) Uani 1 1 d . . . . .
H10A H 0.2697 0.4729 0.8057 0.056 Uiso 1 1 calc R U . . .
H10B H 0.1632 0.4321 0.8428 0.056 Uiso 1 1 calc R U . . .
H10C H 0.2248 0.5362 0.7857 0.056 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
B1 C1 1.5828(16) 2_665 ?
B1 C1 1.5828(16) 3_565 ?
B1 C1 1.5829(16) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.537(2) . ?
C2 H2 1.0000 . ?
C2 C3 1.559(2) . ?
C2 C7 1.532(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.557(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.530(3) . ?
C5 H5 1.0000 . ?
C5 C6 1.552(2) . ?
C5 C8 1.560(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.557(2) . ?
C7 H7 1.0000 . ?
C7 C8 1.572(2) . ?
C8 C9 1.527(2) . ?
C8 C10 1.530(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 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
C1 B1 C1 119.742(19) 2_665 3_565 ?
C1 B1 C1 119.74(2) 3_565 . ?
C1 B1 C1 119.744(19) 2_665 . ?
B1 C1 H1A 107.6 . . ?
B1 C1 H1B 107.6 . . ?
H1A C1 H1B 107.1 . . ?
C2 C1 B1 118.78(11) . . ?
C2 C1 H1A 107.6 . . ?
C2 C1 H1B 107.6 . . ?
C1 C2 H2 106.8 . . ?
C1 C2 C3 112.91(13) . . ?
C3 C2 H2 106.8 . . ?
C7 C2 C1 112.11(13) . . ?
C7 C2 H2 106.8 . . ?
C7 C2 C3 110.91(13) . . ?
C2 C3 H3A 108.3 . . ?
C2 C3 H3B 108.3 . . ?
H3A C3 H3B 107.4 . . ?
C4 C3 C2 115.75(14) . . ?
C4 C3 H3A 108.3 . . ?
C4 C3 H3B 108.3 . . ?
C3 C4 H4A 109.0 . . ?
C3 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 C3 112.98(14) . . ?
C5 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
C4 C5 H5 115.3 . . ?
C4 C5 C6 108.32(15) . . ?
C4 C5 C8 111.61(13) . . ?
C6 C5 H5 115.3 . . ?
C6 C5 C8 87.69(13) . . ?
C8 C5 H5 115.3 . . ?
C5 C6 H6A 114.3 . . ?
C5 C6 H6B 114.3 . . ?
C5 C6 C7 86.23(12) . . ?
H6A C6 H6B 111.4 . . ?
C7 C6 H6A 114.3 . . ?
C7 C6 H6B 114.3 . . ?
C2 C7 C6 107.85(14) . . ?
C2 C7 H7 114.6 . . ?
C2 C7 C8 114.93(13) . . ?
C6 C7 H7 114.6 . . ?
C6 C7 C8 87.14(12) . . ?
C8 C7 H7 114.6 . . ?
C5 C8 C7 85.45(12) . . ?
C9 C8 C5 118.04(14) . . ?
C9 C8 C7 122.18(14) . . ?
C9 C8 C10 107.44(15) . . ?
C10 C8 C5 112.14(15) . . ?
C10 C8 C7 110.27(14) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
B1 C1 C2 C3 -168.46(15) . . . . ?
B1 C1 C2 C7 65.39(19) . . . . ?
C1 B1 C1 C2 30.0(3) 2_665 . . . ?
C1 B1 C1 C2 -160.08(14) 3_565 . . . ?
C1 C2 C3 C4 -138.60(16) . . . . ?
C1 C2 C7 C6 -177.02(13) . . . . ?
C1 C2 C7 C8 87.71(17) . . . . ?
C2 C3 C4 C5 9.8(2) . . . . ?
C2 C7 C8 C5 81.23(15) . . . . ?
C2 C7 C8 C9 -39.2(2) . . . . ?
C2 C7 C8 C10 -166.82(15) . . . . ?
C3 C2 C7 C6 55.75(16) . . . . ?
C3 C2 C7 C8 -39.52(19) . . . . ?
C3 C4 C5 C6 -51.1(2) . . . . ?
C3 C4 C5 C8 43.8(2) . . . . ?
C4 C5 C6 C7 84.56(16) . . . . ?
C4 C5 C8 C7 -81.60(15) . . . . ?
C4 C5 C8 C9 42.66(19) . . . . ?
C4 C5 C8 C10 168.35(15) . . . . ?
C5 C6 C7 C2 -88.04(14) . . . . ?
C5 C6 C7 C8 27.26(13) . . . . ?
C6 C5 C8 C7 27.21(12) . . . . ?
C6 C5 C8 C9 151.47(16) . . . . ?
C6 C5 C8 C10 -82.84(16) . . . . ?
C6 C7 C8 C5 -27.14(13) . . . . ?
C6 C7 C8 C9 -147.62(17) . . . . ?
C6 C7 C8 C10 84.80(17) . . . . ?
C7 C2 C3 C4 -11.8(2) . . . . ?
C8 C5 C6 C7 -27.46(13) . . . . ?

####################################################################### 
# 
# 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_MF106FMI
_database_code_depnum_ccdc_archive 'CCDC 2180016'
loop_
_audit_author_name
_audit_author_address
'James C. Fettinger'
;UC Davis
United States of America
;
_audit_update_record             
;
2022-06-18 deposited with the CCDC.	2022-08-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H60 B P'
_chemical_formula_sum            'C33 H60 B P'
_chemical_formula_weight         498.59

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           146
_space_group_name_H-M_alt        'R 3 :H'
_space_group_name_Hall           'R 3'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'

_cell_length_a                   18.590(2)
_cell_length_b                   18.590(2)
_cell_length_c                   7.7698(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2325.5(6)
_cell_formula_units_Z            3
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    5435
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.50

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.068
_exptl_crystal_F_000             834
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.859
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.115
_exptl_absorpt_coefficient_mu    0.108
_shelx_estimated_absorpt_T_min   0.913
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8884
_exptl_absorpt_correction_T_max  0.9716
_exptl_absorpt_process_details   'SADABS 2014/5 (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART1000 CCD'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5548
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.911
_diffrn_reflns_theta_max         27.506
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             2144
_reflns_number_gt                2120
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.978
_reflns_Friedel_fraction_max     0.965
_reflns_Friedel_fraction_full    0.970

_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       'SMART (Version 5.054) (Bruker, 2002)'
_computing_cell_refinement       'SAINT (8.34a) (Bruker, 2013)'
_computing_data_reduction        'SAINT (8.34a) (Bruker, 2013)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0341P)²+0.7033P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 956 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.03(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2144
_refine_ls_number_parameters     187
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0251
_refine_ls_wR_factor_ref         0.0614
_refine_ls_wR_factor_gt          0.0608
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
P1 P 0.333333 0.666667 0.19168(11) 0.01735(19) Uani 1 3 d S T P . .
B1 B 0.333333 0.666667 0.4530(5) 0.0138(6) Uani 1 3 d S T P . .
C1 C 0.41967(12) 0.66996(12) 0.5118(3) 0.0179(4) Uani 1 1 d . . . . .
H1A H 0.419(2) 0.663(2) 0.632(6) 0.042(9) Uiso 1 1 d . . . . .
H1B H 0.4204(18) 0.6213(18) 0.473(4) 0.030(7) Uiso 1 1 d . . . . .
C2 C 0.50355(11) 0.74992(13) 0.4703(3) 0.0195(4) Uani 1 1 d . . . . .
H2 H 0.4904(16) 0.7826(17) 0.385(4) 0.019(6) Uiso 1 1 d . . . . .
C3 C 0.54051(12) 0.80782(12) 0.6254(3) 0.0201(4) Uani 1 1 d . . . . .
H3 H 0.4999(16) 0.8150(16) 0.684(4) 0.020(7) Uiso 1 1 d . . . . .
C4 C 0.59910(12) 0.78961(13) 0.7409(3) 0.0221(5) Uani 1 1 d . . . . .
C5 C 0.66708(11) 0.84056(14) 0.6045(3) 0.0229(5) Uani 1 1 d . . . . .
H5 H 0.7251(15) 0.8717(17) 0.650(3) 0.022(6) Uiso 1 1 d . . . . .
C6 C 0.66052(13) 0.78846(15) 0.4486(3) 0.0260(5) Uani 1 1 d . . . . .
H6B H 0.685(2) 0.752(2) 0.474(5) 0.038(8) Uiso 1 1 d . . . . .
H6A H 0.694(2) 0.826(2) 0.350(5) 0.041(9) Uiso 1 1 d . . . . .
C7 C 0.56954(14) 0.73165(16) 0.3876(3) 0.0281(5) Uani 1 1 d . . . . .
H7A H 0.5529(19) 0.673(2) 0.409(4) 0.031(8) Uiso 1 1 d . . . . .
H7B H 0.566(2) 0.737(2) 0.261(5) 0.036(8) Uiso 1 1 d . . . . .
C8 C 0.61988(14) 0.88765(14) 0.5641(4) 0.0295(6) Uani 1 1 d . . . . .
H8A H 0.6207(19) 0.9036(19) 0.443(4) 0.027(7) Uiso 1 1 d . . . . .
H8B H 0.6365(16) 0.9385(17) 0.634(4) 0.023(7) Uiso 1 1 d . . . . .
C9 C 0.61707(17) 0.8354(2) 0.9123(4) 0.0373(6) Uani 1 1 d . . . . .
H9B H 0.6681(18) 0.841(2) 0.965(4) 0.034(7) Uiso 1 1 d . . . . .
H9A H 0.572(2) 0.810(2) 1.001(5) 0.045(10) Uiso 1 1 d . . . . .
H9C H 0.626(3) 0.891(3) 0.887(6) 0.058(11) Uiso 1 1 d . . . . .
C10 C 0.57885(14) 0.70098(14) 0.7775(4) 0.0274(5) Uani 1 1 d . . . . .
H10A H 0.627(2) 0.700(2) 0.834(5) 0.048(10) Uiso 1 1 d . . . . .
H10B H 0.564(2) 0.666(2) 0.672(5) 0.040(8) Uiso 1 1 d . . . . .
H10C H 0.531(2) 0.674(2) 0.863(5) 0.048(9) Uiso 1 1 d . . . . .
C11 C 0.23120(13) 0.61702(16) 0.0913(3) 0.0234(4) Uani 1 1 d . . . . .
H11C H 0.203(2) 0.645(2) 0.122(5) 0.047(10) Uiso 1 1 d . . . . .
H11A H 0.199(2) 0.561(2) 0.131(5) 0.046(10) Uiso 1 1 d . . . . .
H11B H 0.2371(17) 0.6174(19) -0.031(4) 0.026(7) Uiso 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
P1 C11 1.820(2) 3_565 ?
P1 C11 1.820(2) . ?
P1 C11 1.820(2) 2_665 ?
P1 B1 2.030(4) . ?
B1 C1 1.640(2) 2_665 ?
B1 C1 1.640(2) 3_565 ?
B1 C1 1.640(2) . ?
C1 C2 1.558(3) . ?
C1 H1A 0.94(4) . ?
C1 H1B 0.96(3) . ?
C2 C3 1.531(3) . ?
C2 C7 1.565(3) . ?
C2 H2 1.01(3) . ?
C3 C8 1.555(3) . ?
C3 C4 1.573(3) . ?
C3 H3 0.94(3) . ?
C4 C10 1.522(3) . ?
C4 C9 1.525(4) . ?
C4 C5 1.556(3) . ?
C5 C6 1.517(4) . ?
C5 C8 1.550(3) . ?
C5 H5 1.00(3) . ?
C6 C7 1.554(3) . ?
C6 H6B 1.00(3) . ?
C6 H6A 1.01(4) . ?
C7 H7A 0.99(3) . ?
C7 H7B 0.99(4) . ?
C8 H8A 0.99(3) . ?
C8 H8B 1.00(3) . ?
C9 H9B 0.99(3) . ?
C9 H9A 1.01(4) . ?
C9 H9C 0.98(4) . ?
C10 H10A 1.00(4) . ?
C10 H10B 1.00(4) . ?
C10 H10C 1.02(4) . ?
C11 H11C 0.95(4) . ?
C11 H11A 0.95(4) . ?
C11 H11B 0.95(3) . ?

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
C11 P1 C11 102.99(10) 3_565 . ?
C11 P1 C11 102.98(10) 3_565 2_665 ?
C11 P1 C11 102.99(10) . 2_665 ?
C11 P1 B1 115.37(8) 3_565 . ?
C11 P1 B1 115.37(8) . . ?
C11 P1 B1 115.37(8) 2_665 . ?
C1 B1 C1 112.55(13) 2_665 3_565 ?
C1 B1 C1 112.55(13) 2_665 . ?
C1 B1 C1 112.55(13) 3_565 . ?
C1 B1 P1 106.19(15) 2_665 . ?
C1 B1 P1 106.19(15) 3_565 . ?
C1 B1 P1 106.19(15) . . ?
C2 C1 B1 118.15(16) . . ?
C2 C1 H1A 106(2) . . ?
B1 C1 H1A 109(2) . . ?
C2 C1 H1B 110.7(18) . . ?
B1 C1 H1B 110.5(18) . . ?
H1A C1 H1B 101(3) . . ?
C3 C2 C1 113.02(18) . . ?
C3 C2 C7 110.54(16) . . ?
C1 C2 C7 113.39(19) . . ?
C3 C2 H2 104.5(16) . . ?
C1 C2 H2 106.4(15) . . ?
C7 C2 H2 108.4(16) . . ?
C2 C3 C8 107.9(2) . . ?
C2 C3 C4 114.43(16) . . ?
C8 C3 C4 87.23(16) . . ?
C2 C3 H3 111.5(17) . . ?
C8 C3 H3 117.2(16) . . ?
C4 C3 H3 116.3(18) . . ?
C10 C4 C9 107.9(2) . . ?
C10 C4 C5 118.17(19) . . ?
C9 C4 C5 111.74(19) . . ?
C10 C4 C3 121.09(17) . . ?
C9 C4 C3 111.1(2) . . ?
C5 C4 C3 85.37(16) . . ?
C6 C5 C8 108.1(2) . . ?
C6 C5 C4 111.95(18) . . ?
C8 C5 C4 88.00(17) . . ?
C6 C5 H5 111.6(16) . . ?
C8 C5 H5 119.8(16) . . ?
C4 C5 H5 115.3(15) . . ?
C5 C6 C7 112.96(18) . . ?
C5 C6 H6B 111(2) . . ?
C7 C6 H6B 107.7(19) . . ?
C5 C6 H6A 109.9(18) . . ?
C7 C6 H6A 109.1(19) . . ?
H6B C6 H6A 106(3) . . ?
C6 C7 C2 115.6(2) . . ?
C6 C7 H7A 109.3(18) . . ?
C2 C7 H7A 108.8(18) . . ?
C6 C7 H7B 110.1(19) . . ?
C2 C7 H7B 106.4(19) . . ?
H7A C7 H7B 106(3) . . ?
C5 C8 C3 86.20(16) . . ?
C5 C8 H8A 115.8(18) . . ?
C3 C8 H8A 116.4(18) . . ?
C5 C8 H8B 115.4(16) . . ?
C3 C8 H8B 115.8(18) . . ?
H8A C8 H8B 107(2) . . ?
C4 C9 H9B 110.4(19) . . ?
C4 C9 H9A 116(2) . . ?
H9B C9 H9A 108(3) . . ?
C4 C9 H9C 107(3) . . ?
H9B C9 H9C 109(3) . . ?
H9A C9 H9C 107(3) . . ?
C4 C10 H10A 111(2) . . ?
C4 C10 H10B 113(2) . . ?
H10A C10 H10B 108(3) . . ?
C4 C10 H10C 110(2) . . ?
H10A C10 H10C 106(3) . . ?
H10B C10 H10C 109(3) . . ?
P1 C11 H11C 110(2) . . ?
P1 C11 H11A 110(2) . . ?
H11C C11 H11A 107(3) . . ?
P1 C11 H11B 109.5(17) . . ?
H11C C11 H11B 110(3) . . ?
H11A C11 H11B 110(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 B1 C1 C2 -49.3(4) 2_665 . . . ?
C1 B1 C1 C2 -177.79(16) 3_565 . . . ?
P1 B1 C1 C2 66.43(19) . . . . ?
B1 C1 C2 C3 100.5(2) . . . . ?
B1 C1 C2 C7 -132.7(2) . . . . ?
C1 C2 C3 C8 -175.79(17) . . . . ?
C7 C2 C3 C8 55.9(2) . . . . ?
C1 C2 C3 C4 89.0(2) . . . . ?
C7 C2 C3 C4 -39.3(2) . . . . ?
C2 C3 C4 C10 -38.7(3) . . . . ?
C8 C3 C4 C10 -147.1(2) . . . . ?
C2 C3 C4 C9 -166.86(19) . . . . ?
C8 C3 C4 C9 84.7(2) . . . . ?
C2 C3 C4 C5 81.60(19) . . . . ?
C8 C3 C4 C5 -26.86(18) . . . . ?
C10 C4 C5 C6 41.1(3) . . . . ?
C9 C4 C5 C6 167.3(2) . . . . ?
C3 C4 C5 C6 -81.84(19) . . . . ?
C10 C4 C5 C8 149.9(2) . . . . ?
C9 C4 C5 C8 -84.0(2) . . . . ?
C3 C4 C5 C8 26.93(17) . . . . ?
C8 C5 C6 C7 -52.7(3) . . . . ?
C4 C5 C6 C7 42.6(3) . . . . ?
C5 C6 C7 C2 11.6(3) . . . . ?
C3 C2 C7 C6 -12.9(3) . . . . ?
C1 C2 C7 C6 -141.1(2) . . . . ?
C6 C5 C8 C3 85.2(2) . . . . ?
C4 C5 C8 C3 -27.24(18) . . . . ?
C2 C3 C8 C5 -87.9(2) . . . . ?
C4 C3 C8 C5 26.93(18) . . . . ?

_refine_diff_density_max         0.163
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.027



