# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_2a
_database_code_depnum_ccdc_archive 'CCDC 1998059'
loop_
_audit_author_name
_audit_author_address
'Chan Hoishan'
;The Chinese University of Hong Kong
Hong Kong
;
_audit_update_record             
;
2020-04-20 deposited with the CCDC.	2020-09-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H20 B10'
_chemical_formula_weight         260.37

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                   7.7202(4)
_cell_length_b                   21.9059(12)
_cell_length_c                   9.0867(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.1207(17)
_cell_angle_gamma                90
_cell_volume                     1521.31(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    348
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.054
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6806
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER D8VENTURE DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31142
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.448
_diffrn_reflns_theta_max         25.238
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2749
_reflns_number_gt                2494
_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 D8VENTURE DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_reduction        'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'BRUKER SHELXTL'
_computing_publication_material  'BRUKER SHELXTL'
_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)+(0.1000P)²+0.9950P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2749
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0701
_refine_ls_wR_factor_ref         0.1936
_refine_ls_wR_factor_gt          0.1889
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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 0.2190(2) 0.38733(9) 0.7097(2) 0.0338(5) Uani 1 1 d . . . . .
C2 C 0.0433(2) 0.37778(8) 0.5874(2) 0.0299(4) Uani 1 1 d . . . . .
C11 C 0.3717(3) 0.39332(12) 0.6232(2) 0.0457(6) Uani 1 1 d . . . . .
H11A H 0.4419 0.3564 0.6328 0.055 Uiso 1 1 calc R U . . .
H11B H 0.4452 0.4274 0.6603 0.055 Uiso 1 1 calc R U . . .
C12 C 0.2932(3) 0.40405(10) 0.4567(2) 0.0431(5) Uani 1 1 d . . . . .
H12A H 0.2856 0.4482 0.4392 0.052 Uiso 1 1 calc R U . . .
C13 C 0.1025(3) 0.37751(10) 0.4350(2) 0.0400(5) Uani 1 1 d . . . . .
H13A H 0.0255 0.4026 0.3662 0.048 Uiso 1 1 calc R U . . .
H13B H 0.1015 0.3363 0.3959 0.048 Uiso 1 1 calc R U . . .
C14 C 0.4103(3) 0.37696(10) 0.3529(2) 0.0391(5) Uani 1 1 d . . . . .
C15 C 0.4481(3) 0.31616(11) 0.3502(3) 0.0549(6) Uani 1 1 d . . . . .
H15A H 0.3935 0.2896 0.4090 0.066 Uiso 1 1 calc R U . . .
C16 C 0.5636(3) 0.29302(13) 0.2639(3) 0.0612(7) Uani 1 1 d . . . . .
H16A H 0.5856 0.2513 0.2632 0.073 Uiso 1 1 calc R U . . .
C17 C 0.6467(3) 0.33172(13) 0.1782(3) 0.0587(7) Uani 1 1 d . . . . .
H17A H 0.7271 0.3159 0.1211 0.070 Uiso 1 1 calc R U . . .
C18 C 0.6139(3) 0.39312(13) 0.1751(3) 0.0602(7) Uani 1 1 d . . . . .
H18A H 0.6704 0.4190 0.1161 0.072 Uiso 1 1 calc R U . . .
C19 C 0.4941(3) 0.41604(12) 0.2619(3) 0.0549(6) Uani 1 1 d . . . . .
H19A H 0.4691 0.4576 0.2599 0.066 Uiso 1 1 calc R U . . .
B3 B 0.1219(3) 0.31644(10) 0.6953(3) 0.0402(6) Uani 1 1 d . . . . .
H3 H 0.1799 0.2753 0.6531 0.048 Uiso 1 1 calc R U . . .
B4 B 0.2046(3) 0.34821(12) 0.8700(3) 0.0417(6) Uani 1 1 d . . . . .
H4 H 0.3159 0.3275 0.9417 0.050 Uiso 1 1 calc R U . . .
B5 B 0.1763(3) 0.42876(11) 0.8589(2) 0.0397(6) Uani 1 1 d . . . . .
H5 H 0.2699 0.4599 0.9234 0.048 Uiso 1 1 calc R U . . .
B6 B 0.0751(3) 0.44710(10) 0.6777(2) 0.0358(5) Uani 1 1 d . . . . .
H6 H 0.1029 0.4903 0.6239 0.043 Uiso 1 1 calc R U . . .
B7 B -0.1052(3) 0.33207(11) 0.6556(3) 0.0383(5) Uani 1 1 d . . . . .
H7 H -0.1958 0.3010 0.5879 0.046 Uiso 1 1 calc R U . . .
B8 B -0.0062(4) 0.31367(12) 0.8394(3) 0.0464(6) Uani 1 1 d . . . . .
H8 H -0.0338 0.2704 0.8928 0.056 Uiso 1 1 calc R U . . .
B9 B 0.0271(3) 0.38341(12) 0.9422(3) 0.0443(6) Uani 1 1 d . . . . .
H9 H 0.0213 0.3853 1.0624 0.053 Uiso 1 1 calc R U . . .
B10 B -0.0525(3) 0.44439(12) 0.8217(3) 0.0422(6) Uani 1 1 d . . . . .
H10 H -0.1100 0.4858 0.8635 0.051 Uiso 1 1 calc R U . . .
B11 B -0.1331(3) 0.41258(11) 0.6446(2) 0.0354(5) Uani 1 1 d . . . . .
H11 H -0.2415 0.4332 0.5695 0.042 Uiso 1 1 calc R U . . .
B12 B -0.1640(3) 0.37327(12) 0.8091(3) 0.0434(6) Uani 1 1 d . . . . .
H12 H -0.2946 0.3685 0.8431 0.052 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 C11 1.512(3) . ?
C1 C2 1.641(2) . ?
C1 B5 1.702(3) . ?
C1 B4 1.707(3) . ?
C1 B6 1.715(3) . ?
C1 B3 1.721(3) . ?
C2 C13 1.519(3) . ?
C2 B7 1.703(3) . ?
C2 B11 1.705(3) . ?
C2 B3 1.722(3) . ?
C2 B6 1.727(3) . ?
C11 C12 1.566(3) . ?
C12 C14 1.517(3) . ?
C12 C13 1.569(3) . ?
C14 C15 1.364(3) . ?
C14 C19 1.409(3) . ?
C15 C16 1.365(3) . ?
C16 C17 1.370(4) . ?
C17 C18 1.368(4) . ?
C18 C19 1.391(3) . ?
B3 B8 1.750(4) . ?
B3 B4 1.768(3) . ?
B3 B7 1.773(3) . ?
B4 B9 1.776(4) . ?
B4 B5 1.779(3) . ?
B4 B8 1.781(4) . ?
B5 B6 1.766(3) . ?
B5 B9 1.770(3) . ?
B5 B10 1.784(3) . ?
B6 B10 1.747(3) . ?
B6 B11 1.764(3) . ?
B7 B12 1.773(3) . ?
B7 B11 1.778(3) . ?
B7 B8 1.782(3) . ?
B8 B12 1.781(4) . ?
B8 B9 1.790(4) . ?
B9 B10 1.781(4) . ?
B9 B12 1.785(3) . ?
B10 B12 1.776(4) . ?
B10 B11 1.783(3) . ?
B11 B12 1.770(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 C1 C2 106.82(15) . . ?
C11 C1 B5 128.37(17) . . ?
C2 C1 B5 111.91(15) . . ?
C11 C1 B4 129.54(17) . . ?
C2 C1 B4 111.50(15) . . ?
B5 C1 B4 62.91(14) . . ?
C11 C1 B6 112.29(17) . . ?
C2 C1 B6 61.90(12) . . ?
B5 C1 B6 62.26(13) . . ?
B4 C1 B6 114.17(15) . . ?
C11 C1 B3 113.67(17) . . ?
C2 C1 B3 61.57(12) . . ?
B5 C1 B3 114.25(16) . . ?
B4 C1 B3 62.10(13) . . ?
B6 C1 B3 114.29(15) . . ?
C13 C2 C1 106.97(15) . . ?
C13 C2 B7 129.35(16) . . ?
C1 C2 B7 111.29(14) . . ?
C13 C2 B11 129.49(16) . . ?
C1 C2 B11 110.86(14) . . ?
B7 C2 B11 62.89(13) . . ?
C13 C2 B3 112.88(16) . . ?
C1 C2 B3 61.52(12) . . ?
B7 C2 B3 62.32(13) . . ?
B11 C2 B3 114.08(15) . . ?
C13 C2 B6 113.31(16) . . ?
C1 C2 B6 61.16(12) . . ?
B7 C2 B6 113.71(15) . . ?
B11 C2 B6 61.84(12) . . ?
B3 C2 B6 113.64(15) . . ?
C1 C11 C12 106.95(16) . . ?
C14 C12 C11 111.02(18) . . ?
C14 C12 C13 114.07(18) . . ?
C11 C12 C13 107.12(17) . . ?
C2 C13 C12 106.33(16) . . ?
C15 C14 C19 117.7(2) . . ?
C15 C14 C12 122.7(2) . . ?
C19 C14 C12 119.4(2) . . ?
C14 C15 C16 122.1(2) . . ?
C15 C16 C17 119.5(3) . . ?
C18 C17 C16 121.3(2) . . ?
C17 C18 C19 118.6(2) . . ?
C18 C19 C14 120.7(2) . . ?
C1 B3 C2 56.90(11) . . ?
C1 B3 B8 105.08(16) . . ?
C2 B3 B8 105.18(16) . . ?
C1 B3 B4 58.56(12) . . ?
C2 B3 B4 104.91(15) . . ?
B8 B3 B4 60.80(14) . . ?
C1 B3 B7 104.40(15) . . ?
C2 B3 B7 58.32(12) . . ?
B8 B3 B7 60.76(14) . . ?
B4 B3 B7 109.13(17) . . ?
C1 B4 B3 59.35(12) . . ?
C1 B4 B9 104.10(16) . . ?
B3 B4 B9 107.63(17) . . ?
C1 B4 B5 58.39(12) . . ?
B3 B4 B5 108.28(16) . . ?
B9 B4 B5 59.72(14) . . ?
C1 B4 B8 104.37(15) . . ?
B3 B4 B8 59.10(14) . . ?
B9 B4 B8 60.43(15) . . ?
B5 B4 B8 108.09(17) . . ?
C1 B5 B6 59.24(12) . . ?
C1 B5 B9 104.61(16) . . ?
B6 B5 B9 107.31(17) . . ?
C1 B5 B4 58.70(12) . . ?
B6 B5 B4 108.25(15) . . ?
B9 B5 B4 60.07(14) . . ?
C1 B5 B10 104.44(15) . . ?
B6 B5 B10 58.95(13) . . ?
B9 B5 B10 60.12(14) . . ?
B4 B5 B10 108.14(17) . . ?
C1 B6 C2 56.94(11) . . ?
C1 B6 B10 105.50(15) . . ?
C2 B6 B10 105.57(16) . . ?
C1 B6 B11 104.74(15) . . ?
C2 B6 B11 58.46(12) . . ?
B10 B6 B11 61.05(13) . . ?
C1 B6 B5 58.51(12) . . ?
C2 B6 B5 104.90(15) . . ?
B10 B6 B5 61.04(13) . . ?
B11 B6 B5 109.50(16) . . ?
C2 B7 B3 59.36(12) . . ?
C2 B7 B12 104.31(16) . . ?
B3 B7 B12 107.13(17) . . ?
C2 B7 B11 58.59(12) . . ?
B3 B7 B11 108.16(15) . . ?
B12 B7 B11 59.78(13) . . ?
C2 B7 B8 104.62(16) . . ?
B3 B7 B8 59.00(14) . . ?
B12 B7 B8 60.11(14) . . ?
B11 B7 B8 108.03(17) . . ?
B3 B8 B12 107.79(16) . . ?
B3 B8 B4 60.10(14) . . ?
B12 B8 B4 107.63(18) . . ?
B3 B8 B7 60.24(13) . . ?
B12 B8 B7 59.71(14) . . ?
B4 B8 B7 108.17(16) . . ?
B3 B8 B9 107.83(17) . . ?
B12 B8 B9 59.98(15) . . ?
B4 B8 B9 59.67(14) . . ?
B7 B8 B9 107.88(17) . . ?
B5 B9 B4 60.21(14) . . ?
B5 B9 B10 60.33(14) . . ?
B4 B9 B10 108.42(16) . . ?
B5 B9 B12 107.80(16) . . ?
B4 B9 B12 107.63(17) . . ?
B10 B9 B12 59.74(14) . . ?
B5 B9 B8 108.07(17) . . ?
B4 B9 B8 59.90(15) . . ?
B10 B9 B8 107.93(17) . . ?
B12 B9 B8 59.75(15) . . ?
B6 B10 B12 107.52(16) . . ?
B6 B10 B9 107.69(16) . . ?
B12 B10 B9 60.25(14) . . ?
B6 B10 B11 59.93(12) . . ?
B12 B10 B11 59.64(13) . . ?
B9 B10 B11 107.93(17) . . ?
B6 B10 B5 60.01(13) . . ?
B12 B10 B5 107.58(17) . . ?
B9 B10 B5 59.54(14) . . ?
B11 B10 B5 107.81(15) . . ?
C2 B11 B6 59.69(12) . . ?
C2 B11 B12 104.40(16) . . ?
B6 B11 B12 107.06(16) . . ?
C2 B11 B7 58.52(12) . . ?
B6 B11 B7 108.39(15) . . ?
B12 B11 B7 59.98(13) . . ?
C2 B11 B10 104.95(15) . . ?
B6 B11 B10 59.02(13) . . ?
B12 B11 B10 59.97(14) . . ?
B7 B11 B10 108.23(16) . . ?
B11 B12 B7 60.24(13) . . ?
B11 B12 B10 60.38(13) . . ?
B7 B12 B10 108.77(16) . . ?
B11 B12 B8 108.45(16) . . ?
B7 B12 B8 60.18(14) . . ?
B10 B12 B8 108.56(17) . . ?
B11 B12 B9 108.32(17) . . ?
B7 B12 B9 108.48(17) . . ?
B10 B12 B9 60.01(14) . . ?
B8 B12 B9 60.27(14) . . ?

_refine_diff_density_max         0.765
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.050

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_2r
_database_code_depnum_ccdc_archive 'CCDC 1998061'
loop_
_audit_author_name
_audit_author_address
'Chan Hoishan'
;The Chinese University of Hong Kong
Hong Kong
;
_audit_update_record             
;
2020-04-20 deposited with the CCDC.	2020-09-02 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         ?
_chemical_formula_sum            'C13 H24 B10'
_chemical_formula_weight         288.42

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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   18.2149(7)
_cell_length_b                   8.1437(4)
_cell_length_c                   12.0108(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1781.64(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2073
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.075
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          40.000
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.052
_shelx_estimated_absorpt_T_min   0.231
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6784
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER D8VENTURE DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19395
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.236
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3208
_reflns_number_gt                2858
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.900
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.994

_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 D8VENTURE DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_reduction        'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'BRUKER SHELXTL'
_computing_publication_material  'BRUKER SHELXTL'
_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)+(0.0695P)²+0.0886P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1219 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3208
_refine_ls_number_parameters     208
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1131
_refine_ls_wR_factor_gt          0.1066
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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 0.41009(12) 0.1257(3) 0.30261(19) 0.0474(5) Uani 1 1 d . . . . .
C2 C 0.32991(12) 0.1866(3) 0.25823(18) 0.0459(5) Uani 1 1 d . . . . .
C11 C 0.43809(14) 0.2545(3) 0.3824(2) 0.0600(7) Uani 1 1 d . . . . .
H11A H 0.486018 0.293145 0.358970 0.072 Uiso 1 1 calc R U . . .
H11B H 0.442526 0.208692 0.456695 0.072 Uiso 1 1 calc R U . . .
C12 C 0.38216(13) 0.3985(3) 0.3824(2) 0.0524(6) Uani 1 1 d . . . . .
H12A H 0.405330 0.492946 0.346078 0.063 Uiso 1 1 calc R U . . .
C13 C 0.31350(15) 0.3492(3) 0.3130(2) 0.0581(7) Uani 1 1 d . . . . .
H13A H 0.270925 0.339387 0.361084 0.070 Uiso 1 1 calc R U . . .
H13B H 0.303345 0.431996 0.257052 0.070 Uiso 1 1 calc R U . . .
C14 C 0.36066(15) 0.4492(4) 0.4995(2) 0.0598(6) Uani 1 1 d . . . . .
H14A H 0.341127 0.354190 0.538182 0.072 Uiso 1 1 calc R U . . .
H14B H 0.321843 0.530433 0.494960 0.072 Uiso 1 1 calc R U . . .
C15 C 0.42412(16) 0.5203(4) 0.5677(2) 0.0611(7) Uani 1 1 d . . . . .
H15A H 0.467196 0.451766 0.558031 0.073 Uiso 1 1 calc R U . . .
H15B H 0.435816 0.629146 0.540122 0.073 Uiso 1 1 calc R U . . .
C16 C 0.40601(13) 0.5310(3) 0.6894(2) 0.0507(6) Uani 1 1 d . . . . .
C17 C 0.41788(17) 0.3988(4) 0.7595(3) 0.0684(7) Uani 1 1 d . . . . .
H17A H 0.438338 0.303187 0.730644 0.082 Uiso 1 1 calc R U . . .
C18 C 0.40011(19) 0.4052(5) 0.8712(3) 0.0799(9) Uani 1 1 d . . . . .
H18A H 0.408637 0.314832 0.916680 0.096 Uiso 1 1 calc R U . . .
C19 C 0.37000(17) 0.5446(5) 0.9144(2) 0.0767(9) Uani 1 1 d . . . . .
H19A H 0.358298 0.550024 0.989715 0.092 Uiso 1 1 calc R U . . .
C20 C 0.35726(16) 0.6746(4) 0.8475(3) 0.0726(8) Uani 1 1 d . . . . .
H20A H 0.336337 0.769081 0.877282 0.087 Uiso 1 1 calc R U . . .
C21 C 0.37464(14) 0.6701(3) 0.7362(2) 0.0609(6) Uani 1 1 d . . . . .
H21A H 0.365260 0.761236 0.691738 0.073 Uiso 1 1 calc R U . . .
B3 B 0.40337(18) 0.1936(4) 0.1686(2) 0.0571(7) Uani 1 1 d . . . . .
H3 H 0.428789 0.306891 0.137069 0.068 Uiso 1 1 calc R U . . .
B4 B 0.45627(17) 0.0192(4) 0.2030(3) 0.0614(8) Uani 1 1 d . . . . .
H4 H 0.516341 0.018242 0.193708 0.074 Uiso 1 1 calc R U . . .
B5 B 0.41335(18) -0.0825(4) 0.3148(3) 0.0605(8) Uani 1 1 d . . . . .
H5 H 0.445763 -0.149037 0.377524 0.073 Uiso 1 1 calc R U . . .
B6 B 0.33307(17) 0.0270(4) 0.3509(3) 0.0562(7) Uani 1 1 d . . . . .
H6 H 0.313125 0.032096 0.437276 0.067 Uiso 1 1 calc R U . . .
B7 B 0.31588(18) 0.1286(4) 0.1238(3) 0.0610(8) Uani 1 1 d . . . . .
H7 H 0.284315 0.199594 0.062288 0.073 Uiso 1 1 calc R U . . .
B8 B 0.3954(2) 0.0149(4) 0.0869(3) 0.0681(9) Uani 1 1 d . . . . .
H8 H 0.415551 0.009672 0.000625 0.082 Uiso 1 1 calc R U . . .
B9 B 0.40124(19) -0.1556(4) 0.1770(3) 0.0682(9) Uani 1 1 d . . . . .
H9 H 0.425399 -0.272377 0.149152 0.082 Uiso 1 1 calc R U . . .
B10 B 0.32535(19) -0.1502(4) 0.2694(3) 0.0668(9) Uani 1 1 d . . . . .
H10 H 0.300124 -0.263207 0.301880 0.080 Uiso 1 1 calc R U . . .
B11 B 0.27207(17) 0.0266(4) 0.2370(3) 0.0623(8) Uani 1 1 d . . . . .
H11 H 0.212237 0.031854 0.248861 0.075 Uiso 1 1 calc R U . . .
B12 B 0.31389(19) -0.0894(4) 0.1286(3) 0.0682(9) Uani 1 1 d . . . . .
H12 H 0.281029 -0.162219 0.069674 0.082 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 C11 1.510(3) . ?
C1 C2 1.632(3) . ?
C1 B4 1.700(4) . ?
C1 B5 1.703(4) . ?
C1 B3 1.706(4) . ?
C1 B6 1.718(4) . ?
C2 C13 1.509(3) . ?
C2 B11 1.694(4) . ?
C2 B7 1.702(4) . ?
C2 B6 1.712(4) . ?
C2 B3 1.718(4) . ?
C11 C12 1.553(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C14 1.517(4) . ?
C12 C13 1.555(3) . ?
C12 H12A 0.9800 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.531(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.501(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.384(4) . ?
C16 C21 1.387(4) . ?
C17 C18 1.381(4) . ?
C17 H17A 0.9300 . ?
C18 C19 1.364(5) . ?
C18 H18A 0.9300 . ?
C19 C20 1.350(5) . ?
C19 H19A 0.9300 . ?
C20 C21 1.375(4) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?
B3 B8 1.761(4) . ?
B3 B7 1.764(4) . ?
B3 B4 1.765(5) . ?
B3 H3 1.1000 . ?
B4 B5 1.760(5) . ?
B4 B9 1.769(5) . ?
B4 B8 1.783(5) . ?
B4 H4 1.1000 . ?
B5 B6 1.767(4) . ?
B5 B9 1.772(5) . ?
B5 B10 1.781(5) . ?
B5 H5 1.1000 . ?
B6 B10 1.749(5) . ?
B6 B11 1.762(5) . ?
B6 H6 1.1000 . ?
B7 B8 1.775(5) . ?
B7 B12 1.777(5) . ?
B7 B11 1.782(5) . ?
B7 H7 1.1000 . ?
B8 B9 1.765(6) . ?
B8 B12 1.782(5) . ?
B8 H8 1.1000 . ?
B9 B10 1.773(5) . ?
B9 B12 1.778(5) . ?
B9 H9 1.1000 . ?
B10 B12 1.775(5) . ?
B10 B11 1.780(5) . ?
B10 H10 1.1000 . ?
B11 B12 1.780(5) . ?
B11 H11 1.1000 . ?
B12 H12 1.1000 . ?

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 C1 C2 107.38(18) . . ?
C11 C1 B4 129.3(2) . . ?
C2 C1 B4 111.59(19) . . ?
C11 C1 B5 128.7(2) . . ?
C2 C1 B5 111.22(19) . . ?
B4 C1 B5 62.31(19) . . ?
C11 C1 B3 113.5(2) . . ?
C2 C1 B3 61.91(16) . . ?
B4 C1 B3 62.42(18) . . ?
B5 C1 B3 114.0(2) . . ?
C11 C1 B6 112.7(2) . . ?
C2 C1 B6 61.42(15) . . ?
B4 C1 B6 113.8(2) . . ?
B5 C1 B6 62.20(17) . . ?
B3 C1 B6 114.3(2) . . ?
C13 C2 C1 107.54(18) . . ?
C13 C2 B11 128.1(2) . . ?
C1 C2 B11 111.85(19) . . ?
C13 C2 B7 128.9(2) . . ?
C1 C2 B7 111.11(19) . . ?
B11 C2 B7 63.30(19) . . ?
C13 C2 B6 112.9(2) . . ?
C1 C2 B6 61.76(15) . . ?
B11 C2 B6 62.31(18) . . ?
B7 C2 B6 114.3(2) . . ?
C13 C2 B3 113.5(2) . . ?
C1 C2 B3 61.16(16) . . ?
B11 C2 B3 114.6(2) . . ?
B7 C2 B3 62.09(17) . . ?
B6 C2 B3 114.0(2) . . ?
C1 C11 C12 107.62(19) . . ?
C1 C11 H11A 110.2 . . ?
C12 C11 H11A 110.2 . . ?
C1 C11 H11B 110.2 . . ?
C12 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
C14 C12 C11 112.0(2) . . ?
C14 C12 C13 111.1(2) . . ?
C11 C12 C13 109.43(19) . . ?
C14 C12 H12A 108.1 . . ?
C11 C12 H12A 108.1 . . ?
C13 C12 H12A 108.1 . . ?
C2 C13 C12 107.51(19) . . ?
C2 C13 H13A 110.2 . . ?
C12 C13 H13A 110.2 . . ?
C2 C13 H13B 110.2 . . ?
C12 C13 H13B 110.2 . . ?
H13A C13 H13B 108.5 . . ?
C12 C14 C15 113.9(2) . . ?
C12 C14 H14A 108.8 . . ?
C15 C14 H14A 108.8 . . ?
C12 C14 H14B 108.8 . . ?
C15 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C16 C15 C14 112.2(2) . . ?
C16 C15 H15A 109.2 . . ?
C14 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C17 C16 C21 117.0(2) . . ?
C17 C16 C15 120.8(3) . . ?
C21 C16 C15 122.1(3) . . ?
C18 C17 C16 121.6(3) . . ?
C18 C17 H17A 119.2 . . ?
C16 C17 H17A 119.2 . . ?
C19 C18 C17 119.7(3) . . ?
C19 C18 H18A 120.1 . . ?
C17 C18 H18A 120.1 . . ?
C20 C19 C18 119.7(3) . . ?
C20 C19 H19A 120.2 . . ?
C18 C19 H19A 120.2 . . ?
C19 C20 C21 121.3(3) . . ?
C19 C20 H20A 119.4 . . ?
C21 C20 H20A 119.4 . . ?
C20 C21 C16 120.7(3) . . ?
C20 C21 H21A 119.7 . . ?
C16 C21 H21A 119.7 . . ?
C1 B3 C2 56.93(14) . . ?
C1 B3 B8 105.3(2) . . ?
C2 B3 B8 104.9(2) . . ?
C1 B3 B7 104.8(2) . . ?
C2 B3 B7 58.51(17) . . ?
B8 B3 B7 60.45(19) . . ?
C1 B3 B4 58.63(16) . . ?
C2 B3 B4 104.6(2) . . ?
B8 B3 B4 60.7(2) . . ?
B7 B3 B4 108.9(2) . . ?
C1 B3 H3 124.5 . . ?
C2 B3 H3 124.9 . . ?
B8 B3 H3 122.4 . . ?
B7 B3 H3 121.8 . . ?
B4 B3 H3 121.7 . . ?
C1 B4 B5 58.92(17) . . ?
C1 B4 B3 58.95(16) . . ?
B5 B4 B3 108.3(2) . . ?
C1 B4 B9 104.7(2) . . ?
B5 B4 B9 60.3(2) . . ?
B3 B4 B9 107.3(2) . . ?
C1 B4 B8 104.6(2) . . ?
B5 B4 B8 108.1(2) . . ?
B3 B4 B8 59.53(19) . . ?
B9 B4 B8 59.6(2) . . ?
C1 B4 H4 124.6 . . ?
B5 B4 H4 121.1 . . ?
B3 B4 H4 121.7 . . ?
B9 B4 H4 122.7 . . ?
B8 B4 H4 122.6 . . ?
C1 B5 B4 58.77(17) . . ?
C1 B5 B6 59.32(16) . . ?
B4 B5 B6 108.5(2) . . ?
C1 B5 B9 104.5(2) . . ?
B4 B5 B9 60.10(19) . . ?
B6 B5 B9 107.2(2) . . ?
C1 B5 B10 104.5(2) . . ?
B4 B5 B10 108.2(3) . . ?
B6 B5 B10 59.09(18) . . ?
B9 B5 B10 59.9(2) . . ?
C1 B5 H5 124.6 . . ?
B4 B5 H5 121.1 . . ?
B6 B5 H5 121.6 . . ?
B9 B5 H5 122.7 . . ?
B10 B5 H5 122.7 . . ?
C2 B6 C1 56.82(14) . . ?
C2 B6 B10 105.0(2) . . ?
C1 B6 B10 105.2(2) . . ?
C2 B6 B11 58.35(17) . . ?
C1 B6 B11 104.7(2) . . ?
B10 B6 B11 60.90(19) . . ?
C2 B6 B5 104.5(2) . . ?
C1 B6 B5 58.48(16) . . ?
B10 B6 B5 60.86(18) . . ?
B11 B6 B5 109.3(2) . . ?
C2 B6 H6 125.0 . . ?
C1 B6 H6 124.8 . . ?
B10 B6 H6 122.2 . . ?
B11 B6 H6 121.6 . . ?
B5 B6 H6 121.6 . . ?
C2 B7 B3 59.40(15) . . ?
C2 B7 B8 105.0(2) . . ?
B3 B7 B8 59.71(19) . . ?
C2 B7 B12 104.4(2) . . ?
B3 B7 B12 108.0(2) . . ?
B8 B7 B12 60.2(2) . . ?
C2 B7 B11 58.15(16) . . ?
B3 B7 B11 108.1(2) . . ?
B8 B7 B11 108.2(2) . . ?
B12 B7 B11 60.0(2) . . ?
C2 B7 H7 124.7 . . ?
B3 B7 H7 121.3 . . ?
B8 B7 H7 122.2 . . ?
B12 B7 H7 122.4 . . ?
B11 B7 H7 121.5 . . ?
B3 B8 B9 107.6(2) . . ?
B3 B8 B7 59.84(18) . . ?
B9 B8 B7 107.9(3) . . ?
B3 B8 B12 107.8(2) . . ?
B9 B8 B12 60.2(2) . . ?
B7 B8 B12 59.9(2) . . ?
B3 B8 B4 59.72(19) . . ?
B9 B8 B4 59.8(2) . . ?
B7 B8 B4 107.6(2) . . ?
B12 B8 B4 107.9(3) . . ?
B3 B8 H8 122.0 . . ?
B9 B8 H8 121.8 . . ?
B7 B8 H8 121.9 . . ?
B12 B8 H8 121.6 . . ?
B4 B8 H8 122.0 . . ?
B8 B9 B4 60.6(2) . . ?
B8 B9 B5 108.4(2) . . ?
B4 B9 B5 59.62(19) . . ?
B8 B9 B10 108.5(2) . . ?
B4 B9 B10 108.1(2) . . ?
B5 B9 B10 60.30(19) . . ?
B8 B9 B12 60.4(2) . . ?
B4 B9 B12 108.7(2) . . ?
B5 B9 B12 108.4(2) . . ?
B10 B9 B12 60.0(2) . . ?
B8 B9 H9 121.2 . . ?
B4 B9 H9 121.5 . . ?
B5 B9 H9 121.7 . . ?
B10 B9 H9 121.6 . . ?
B12 B9 H9 121.4 . . ?
B6 B10 B9 107.9(2) . . ?
B6 B10 B12 108.2(2) . . ?
B9 B10 B12 60.1(2) . . ?
B6 B10 B11 59.92(18) . . ?
B9 B10 B11 108.0(3) . . ?
B12 B10 B11 60.1(2) . . ?
B6 B10 B5 60.06(18) . . ?
B9 B10 B5 59.8(2) . . ?
B12 B10 B5 108.1(2) . . ?
B11 B10 B5 107.9(2) . . ?
B6 B10 H10 121.7 . . ?
B9 B10 H10 121.8 . . ?
B12 B10 H10 121.5 . . ?
B11 B10 H10 121.8 . . ?
B5 B10 H10 121.8 . . ?
C2 B11 B6 59.34(16) . . ?
C2 B11 B10 104.5(2) . . ?
B6 B11 B10 59.18(19) . . ?
C2 B11 B12 104.6(2) . . ?
B6 B11 B12 107.4(2) . . ?
B10 B11 B12 59.8(2) . . ?
C2 B11 B7 58.56(16) . . ?
B6 B11 B7 108.0(2) . . ?
B10 B11 B7 107.4(2) . . ?
B12 B11 B7 59.8(2) . . ?
C2 B11 H11 124.5 . . ?
B6 B11 H11 121.6 . . ?
B10 B11 H11 122.9 . . ?
B12 B11 H11 122.6 . . ?
B7 B11 H11 121.6 . . ?
B10 B12 B7 107.9(2) . . ?
B10 B12 B9 59.9(2) . . ?
B7 B12 B9 107.2(2) . . ?
B10 B12 B11 60.07(19) . . ?
B7 B12 B11 60.13(18) . . ?
B9 B12 B11 107.7(2) . . ?
B10 B12 B8 107.6(2) . . ?
B7 B12 B8 59.83(19) . . ?
B9 B12 B8 59.4(2) . . ?
B11 B12 B8 108.0(2) . . ?
B10 B12 H12 121.8 . . ?
B7 B12 H12 121.9 . . ?
B9 B12 H12 122.3 . . ?
B11 B12 H12 121.6 . . ?
B8 B12 H12 122.0 . . ?

_refine_diff_density_max         0.118
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.024

####################################################################### 
# 
# 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_2p
_database_code_depnum_ccdc_archive 'CCDC 1998060'
loop_
_audit_author_name
_audit_author_address
'Chan Hoishan'
;The Chinese University of Hong Kong
Hong Kong
;
_audit_update_record             
;
2020-04-20 deposited with the CCDC.	2020-09-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H26 B10'
_chemical_formula_weight         302.45

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   9.7246(5)
_cell_length_b                   9.0634(4)
_cell_length_c                   21.3352(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.9612(15)
_cell_angle_gamma                90
_cell_volume                     1866.58(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    168
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.076
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.052
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6364
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER D8VENTURE DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21874
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.423
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3366
_reflns_number_gt                2714
_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 D8VENTURE DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_reduction        'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'BRUKER SHELXTL'
_computing_publication_material  'BRUKER SHELXTL'
_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)+(0.1125P)²+0.5081P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3366
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0624
_refine_ls_wR_factor_ref         0.1982
_refine_ls_wR_factor_gt          0.1804
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.107
_refine_ls_shift/su_max          0.002
_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 0.6975(2) 0.1766(2) 0.08155(10) 0.0474(5) Uani 1 1 d . . . . .
C2 C 0.64083(18) 0.1172(2) 0.14612(8) 0.0368(4) Uani 1 1 d . . . . .
C11 C 0.5911(2) 0.2835(2) 0.05037(10) 0.0501(5) Uani 1 1 d . . . . .
H11A H 0.5708 0.2618 0.0057 0.060 Uiso 1 1 calc R U . . .
H11B H 0.6252 0.3840 0.0551 0.060 Uiso 1 1 calc R U . . .
C12 C 0.46016(19) 0.2642(2) 0.08380(8) 0.0397(5) Uani 1 1 d . . . . .
H12A H 0.4002 0.1930 0.0590 0.048 Uiso 1 1 calc R U . . .
C13 C 0.3777(2) 0.4043(2) 0.08733(8) 0.0405(5) Uani 1 1 d . . . . .
C14 C 0.4356(2) 0.5301(2) 0.11623(10) 0.0515(5) Uani 1 1 d . . . . .
H14A H 0.5285 0.5295 0.1328 0.062 Uiso 1 1 calc R U . . .
C15 C 0.3590(3) 0.6550(2) 0.12092(12) 0.0639(6) Uani 1 1 d . . . . .
H15A H 0.4006 0.7384 0.1403 0.077 Uiso 1 1 calc R U . . .
C16 C 0.2231(3) 0.6590(3) 0.09759(13) 0.0714(7) Uani 1 1 d . . . . .
H16A H 0.1714 0.7441 0.1015 0.086 Uiso 1 1 calc R U . . .
C17 C 0.1623(3) 0.5370(3) 0.06822(13) 0.0716(7) Uani 1 1 d . . . . .
H17A H 0.0693 0.5397 0.0517 0.086 Uiso 1 1 calc R U . . .
C18 C 0.2392(2) 0.4090(3) 0.06306(10) 0.0559(6) Uani 1 1 d . . . . .
H18A H 0.1973 0.3263 0.0432 0.067 Uiso 1 1 calc R U . . .
C19 C 0.50205(18) 0.19444(19) 0.15033(8) 0.0362(4) Uani 1 1 d . . . . .
H19A H 0.5178 0.2747 0.1811 0.043 Uiso 1 1 calc R U . . .
C20 C 0.38761(19) 0.0960(2) 0.16996(9) 0.0432(5) Uani 1 1 d . . . . .
H20A H 0.2998 0.1465 0.1597 0.052 Uiso 1 1 calc R U . . .
H20B H 0.3842 0.0067 0.1448 0.052 Uiso 1 1 calc R U . . .
C21 C 0.4014(2) 0.0521(2) 0.23930(10) 0.0514(5) Uani 1 1 d . . . . .
H21A H 0.4904 0.0049 0.2506 0.062 Uiso 1 1 calc R U . . .
H21B H 0.3988 0.1402 0.2649 0.062 Uiso 1 1 calc R U . . .
C22 C 0.2886(3) -0.0510(3) 0.25373(12) 0.0633(6) Uani 1 1 d . . . . .
H22A H 0.3015 -0.0755 0.2978 0.095 Uiso 1 1 calc R U . . .
H22B H 0.2002 -0.0040 0.2435 0.095 Uiso 1 1 calc R U . . .
H22C H 0.2919 -0.1393 0.2291 0.095 Uiso 1 1 calc R U . . .
B3 B 0.6390(3) -0.0019(3) 0.08366(11) 0.0484(6) Uani 1 1 d . . . . .
H3 H 0.5443 -0.0438 0.0559 0.058 Uiso 1 1 calc R U . . .
B4 B 0.7883(3) 0.0435(3) 0.04776(14) 0.0673(8) Uani 1 1 d . . . . .
H4 H 0.7914 0.0303 -0.0033 0.081 Uiso 1 1 calc R U . . .
B5 B 0.8724(3) 0.1926(4) 0.09031(16) 0.0697(8) Uani 1 1 d . . . . .
H5 H 0.9293 0.2759 0.0662 0.084 Uiso 1 1 calc R U . . .
B6 B 0.7769(2) 0.2395(3) 0.15308(13) 0.0529(6) Uani 1 1 d . . . . .
H6 H 0.7719 0.3535 0.1703 0.063 Uiso 1 1 calc R U . . .
B7 B 0.6902(3) -0.0619(3) 0.16179(11) 0.0476(6) Uani 1 1 d . . . . .
H7 H 0.6296 -0.1436 0.1849 0.057 Uiso 1 1 calc R U . . .
B8 B 0.7890(3) -0.1100(3) 0.09999(14) 0.0644(7) Uani 1 1 d . . . . .
H8 H 0.7940 -0.2241 0.0829 0.077 Uiso 1 1 calc R U . . .
B9 B 0.9351(3) 0.0113(4) 0.10518(17) 0.0778(9) Uani 1 1 d . . . . .
H9 H 1.0355 -0.0243 0.0916 0.093 Uiso 1 1 calc R U . . .
B10 B 0.9260(3) 0.1322(4) 0.16927(17) 0.0714(8) Uani 1 1 d . . . . .
H10 H 1.0199 0.1754 0.1972 0.086 Uiso 1 1 calc R U . . .
B11 B 0.7742(2) 0.0877(3) 0.20451(12) 0.0508(6) Uani 1 1 d . . . . .
H11 H 0.7670 0.1023 0.2552 0.061 Uiso 1 1 calc R U . . .
B12 B 0.8736(3) -0.0539(3) 0.17481(15) 0.0639(7) Uani 1 1 d . . . . .
H12 H 0.9339 -0.1323 0.2065 0.077 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 C11 1.511(3) . ?
C1 C2 1.636(3) . ?
C1 B5 1.695(3) . ?
C1 B4 1.705(3) . ?
C1 B3 1.717(3) . ?
C1 B6 1.722(3) . ?
C2 C19 1.533(2) . ?
C2 B11 1.707(3) . ?
C2 B3 1.713(3) . ?
C2 B7 1.714(3) . ?
C2 B6 1.718(3) . ?
C11 C12 1.543(3) . ?
C12 C13 1.508(2) . ?
C12 C19 1.562(2) . ?
C13 C14 1.383(3) . ?
C13 C18 1.384(3) . ?
C14 C15 1.366(3) . ?
C15 C16 1.356(4) . ?
C16 C17 1.369(4) . ?
C17 C18 1.392(3) . ?
C19 C20 1.524(3) . ?
C20 C21 1.522(3) . ?
C21 C22 1.501(3) . ?
B3 B8 1.757(3) . ?
B3 B7 1.767(3) . ?
B3 B4 1.770(4) . ?
B4 B5 1.772(5) . ?
B4 B8 1.782(4) . ?
B4 B9 1.789(5) . ?
B5 B9 1.768(4) . ?
B5 B6 1.771(4) . ?
B5 B10 1.788(5) . ?
B6 B10 1.745(4) . ?
B6 B11 1.762(4) . ?
B7 B12 1.773(4) . ?
B7 B11 1.776(3) . ?
B7 B8 1.777(4) . ?
B8 B12 1.779(4) . ?
B8 B9 1.789(5) . ?
B9 B10 1.763(5) . ?
B9 B12 1.769(4) . ?
B10 B12 1.770(4) . ?
B10 B11 1.783(4) . ?
B11 B12 1.770(4) . ?

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 C1 C2 107.43(15) . . ?
C11 C1 B5 128.13(18) . . ?
C2 C1 B5 111.79(17) . . ?
C11 C1 B4 128.99(19) . . ?
C2 C1 B4 111.58(16) . . ?
B5 C1 B4 62.81(18) . . ?
C11 C1 B3 113.86(17) . . ?
C2 C1 B3 61.41(12) . . ?
B5 C1 B3 114.16(17) . . ?
B4 C1 B3 62.30(15) . . ?
C11 C1 B6 112.79(17) . . ?
C2 C1 B6 61.51(12) . . ?
B5 C1 B6 62.45(16) . . ?
B4 C1 B6 114.14(18) . . ?
B3 C1 B6 113.76(16) . . ?
C19 C2 C1 106.73(14) . . ?
C19 C2 B11 128.71(16) . . ?
C1 C2 B11 111.28(15) . . ?
C19 C2 B3 114.00(14) . . ?
C1 C2 B3 61.64(13) . . ?
B11 C2 B3 113.85(16) . . ?
C19 C2 B7 130.46(16) . . ?
C1 C2 B7 111.15(15) . . ?
B11 C2 B7 62.55(13) . . ?
B3 C2 B7 62.06(13) . . ?
C19 C2 B6 112.02(15) . . ?
C1 C2 B6 61.72(13) . . ?
B11 C2 B6 61.92(13) . . ?
B3 C2 B6 114.13(16) . . ?
B7 C2 B6 113.53(15) . . ?
C1 C11 C12 106.42(15) . . ?
C13 C12 C11 113.64(16) . . ?
C13 C12 C19 112.15(14) . . ?
C11 C12 C19 109.08(14) . . ?
C14 C13 C18 117.80(18) . . ?
C14 C13 C12 121.74(17) . . ?
C18 C13 C12 120.43(18) . . ?
C15 C14 C13 121.4(2) . . ?
C16 C15 C14 120.7(2) . . ?
C15 C16 C17 119.6(2) . . ?
C16 C17 C18 120.2(2) . . ?
C13 C18 C17 120.3(2) . . ?
C20 C19 C2 115.22(15) . . ?
C20 C19 C12 111.60(14) . . ?
C2 C19 C12 105.44(14) . . ?
C21 C20 C19 116.05(16) . . ?
C22 C21 C20 112.45(18) . . ?
C2 B3 C1 56.95(11) . . ?
C2 B3 B8 105.47(17) . . ?
C1 B3 B8 105.11(18) . . ?
C2 B3 B7 59.00(12) . . ?
C1 B3 B7 104.98(16) . . ?
B8 B3 B7 60.57(14) . . ?
C2 B3 B4 104.96(18) . . ?
C1 B3 B4 58.53(14) . . ?
B8 B3 B4 60.69(16) . . ?
B7 B3 B4 109.11(18) . . ?
C1 B4 B3 59.17(13) . . ?
C1 B4 B5 58.30(15) . . ?
B3 B4 B5 107.91(19) . . ?
C1 B4 B8 104.51(18) . . ?
B3 B4 B8 59.28(15) . . ?
B5 B4 B8 108.0(2) . . ?
C1 B4 B9 103.7(2) . . ?
B3 B4 B9 107.1(2) . . ?
B5 B4 B9 59.55(19) . . ?
B8 B4 B9 60.13(17) . . ?
C1 B5 B9 105.1(2) . . ?
C1 B5 B6 59.52(13) . . ?
B9 B5 B6 106.7(2) . . ?
C1 B5 B4 58.89(15) . . ?
B9 B5 B4 60.72(19) . . ?
B6 B5 B4 108.57(18) . . ?
C1 B5 B10 104.59(18) . . ?
B9 B5 B10 59.43(19) . . ?
B6 B5 B10 58.72(16) . . ?
B4 B5 B10 108.2(2) . . ?
C2 B6 C1 56.78(12) . . ?
C2 B6 B10 105.71(18) . . ?
C1 B6 B10 105.3(2) . . ?
C2 B6 B11 58.72(12) . . ?
C1 B6 B11 104.75(17) . . ?
B10 B6 B11 61.11(16) . . ?
C2 B6 B5 104.42(18) . . ?
C1 B6 B5 58.03(15) . . ?
B10 B6 B5 61.12(17) . . ?
B11 B6 B5 109.43(19) . . ?
C2 B7 B3 58.94(12) . . ?
C2 B7 B12 104.14(17) . . ?
B3 B7 B12 107.37(18) . . ?
C2 B7 B11 58.52(12) . . ?
B3 B7 B11 107.98(17) . . ?
B12 B7 B11 59.81(15) . . ?
C2 B7 B8 104.55(17) . . ?
B3 B7 B8 59.44(14) . . ?
B12 B7 B8 60.16(16) . . ?
B11 B7 B8 108.16(19) . . ?
B3 B8 B7 60.00(13) . . ?
B3 B8 B12 107.54(18) . . ?
B7 B8 B12 59.82(15) . . ?
B3 B8 B4 60.03(15) . . ?
B7 B8 B4 108.13(18) . . ?
B12 B8 B4 107.7(2) . . ?
B3 B8 B9 107.70(19) . . ?
B7 B8 B9 107.5(2) . . ?
B12 B8 B9 59.42(18) . . ?
B4 B8 B9 60.13(18) . . ?
B10 B9 B5 60.84(19) . . ?
B10 B9 B12 60.16(18) . . ?
B5 B9 B12 108.5(2) . . ?
B10 B9 B8 108.4(2) . . ?
B5 B9 B8 107.79(19) . . ?
B12 B9 B8 60.00(17) . . ?
B10 B9 B4 108.58(19) . . ?
B5 B9 B4 59.74(18) . . ?
B12 B9 B4 107.9(2) . . ?
B8 B9 B4 59.73(17) . . ?
B6 B10 B9 108.1(2) . . ?
B6 B10 B12 107.75(18) . . ?
B9 B10 B12 60.08(19) . . ?
B6 B10 B11 59.92(14) . . ?
B9 B10 B11 107.9(2) . . ?
B12 B10 B11 59.74(15) . . ?
B6 B10 B5 60.16(15) . . ?
B9 B10 B5 59.73(19) . . ?
B12 B10 B5 107.5(2) . . ?
B11 B10 B5 107.74(18) . . ?
C2 B11 B6 59.36(12) . . ?
C2 B11 B12 104.61(17) . . ?
B6 B11 B12 107.03(19) . . ?
C2 B11 B7 58.93(12) . . ?
B6 B11 B7 108.48(17) . . ?
B12 B11 B7 60.01(15) . . ?
C2 B11 B10 104.56(18) . . ?
B6 B11 B10 58.98(15) . . ?
B12 B11 B10 59.77(17) . . ?
B7 B11 B10 108.0(2) . . ?
B9 B12 B11 108.29(19) . . ?
B9 B12 B10 59.76(19) . . ?
B11 B12 B10 60.49(16) . . ?
B9 B12 B7 108.55(19) . . ?
B11 B12 B7 60.18(14) . . ?
B10 B12 B7 108.72(18) . . ?
B9 B12 B8 60.57(19) . . ?
B11 B12 B8 108.35(17) . . ?
B10 B12 B8 108.5(2) . . ?
B7 B12 B8 60.03(15) . . ?

_refine_diff_density_max         0.237
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.084

_shelxl_version_number           2014/6

