# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

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

data_9
_database_code_depnum_ccdc_archive 'CCDC 1457937'
_audit_update_record             
;
2016-03-04 deposited with the CCDC.
2016-03-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            Pentaphenyl-1,2-oxaborine
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H25 B O'
_chemical_formula_sum            'C34 H25 B O'
_chemical_formula_weight         460.35

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.7747(5)
_cell_length_b                   11.2285(5)
_cell_length_c                   12.0790(6)
_cell_angle_alpha                86.4386(15)
_cell_angle_beta                 70.8147(14)
_cell_angle_gamma                85.0255(14)
_cell_volume                     1246.59(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9022
_cell_measurement_theta_min      2.348
_cell_measurement_theta_max      29.233

_exptl_crystal_description       prism
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_F_000             484
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.254
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.154
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28438
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.348
_diffrn_reflns_theta_max         28.699
_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             6434
_reflns_number_gt                4380
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (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)+(0.0541P)²+0.2336P] 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         6434
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1190
_refine_ls_wR_factor_gt          0.1039
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_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
O1 O 0.86464(9) 0.15380(8) 0.02416(8) 0.0270(2) Uani 1 1 d . . . . .
B1 B 0.99592(15) 0.19955(13) -0.04034(13) 0.0236(3) Uani 1 1 d . . . . .
C1 C 1.06777(13) 0.26879(11) 0.02587(11) 0.0239(3) Uani 1 1 d . . . . .
C2 C 0.99460(13) 0.28575(11) 0.14402(11) 0.0234(3) Uani 1 1 d . . . . .
C3 C 0.85363(13) 0.23975(11) 0.20231(11) 0.0235(3) Uani 1 1 d . . . . .
C4 C 0.79591(13) 0.17084(12) 0.14042(11) 0.0256(3) Uani 1 1 d . . . . .
C11 C 1.21192(13) 0.32072(12) -0.02886(11) 0.0245(3) Uani 1 1 d . . . . .
C12 C 1.33798(14) 0.24762(13) -0.07631(11) 0.0281(3) Uani 1 1 d . . . . .
H12 H 1.3322 0.1637 -0.0776 0.034 Uiso 1 1 calc R U . . .
C13 C 1.47195(15) 0.29605(14) -0.12175(12) 0.0340(3) Uani 1 1 d . . . . .
H13 H 1.5571 0.2449 -0.1529 0.041 Uiso 1 1 calc R U . . .
C14 C 1.48257(16) 0.41836(15) -0.12204(12) 0.0372(4) Uani 1 1 d . . . . .
H14 H 1.5746 0.4511 -0.1525 0.045 Uiso 1 1 calc R U . . .
C15 C 1.35797(16) 0.49214(14) -0.07754(12) 0.0359(3) Uani 1 1 d . . . . .
H15 H 1.3642 0.5762 -0.0785 0.043 Uiso 1 1 calc R U . . .
C16 C 1.22379(15) 0.44412(12) -0.03145(12) 0.0301(3) Uani 1 1 d . . . . .
H16 H 1.1389 0.4958 -0.0013 0.036 Uiso 1 1 calc R U . . .
C21 C 1.06268(13) 0.34740(12) 0.21764(11) 0.0239(3) Uani 1 1 d . . . . .
C22 C 1.18249(13) 0.28989(12) 0.24110(12) 0.0276(3) Uani 1 1 d . . . . .
H22 H 1.2217 0.2150 0.2077 0.033 Uiso 1 1 calc R U . . .
C23 C 1.24533(15) 0.34058(14) 0.31270(12) 0.0337(3) Uani 1 1 d . . . . .
H23 H 1.3264 0.3000 0.3290 0.040 Uiso 1 1 calc R U . . .
C24 C 1.18978(16) 0.45024(14) 0.36032(13) 0.0371(4) Uani 1 1 d . . . . .
H24 H 1.2322 0.4851 0.4098 0.045 Uiso 1 1 calc R U . . .
C25 C 1.07241(16) 0.50907(14) 0.33586(13) 0.0373(4) Uani 1 1 d . . . . .
H25 H 1.0353 0.5851 0.3676 0.045 Uiso 1 1 calc R U . . .
C26 C 1.00838(15) 0.45791(12) 0.26518(12) 0.0299(3) Uani 1 1 d . . . . .
H26 H 0.9272 0.4986 0.2493 0.036 Uiso 1 1 calc R U . . .
C31 C 0.76845(13) 0.26895(11) 0.32623(11) 0.0244(3) Uani 1 1 d . . . . .
C32 C 0.82038(15) 0.23895(12) 0.42015(12) 0.0291(3) Uani 1 1 d . . . . .
H32 H 0.9143 0.1996 0.4058 0.035 Uiso 1 1 calc R U . . .
C33 C 0.73650(16) 0.26590(13) 0.53374(12) 0.0329(3) Uani 1 1 d . . . . .
H33 H 0.7733 0.2452 0.5966 0.039 Uiso 1 1 calc R U . . .
C34 C 0.59951(16) 0.32278(13) 0.55607(13) 0.0349(3) Uani 1 1 d . . . . .
H34 H 0.5416 0.3404 0.6342 0.042 Uiso 1 1 calc R U . . .
C35 C 0.54710(15) 0.35397(13) 0.46387(12) 0.0318(3) Uani 1 1 d . . . . .
H35 H 0.4531 0.3933 0.4789 0.038 Uiso 1 1 calc R U . . .
C36 C 0.63105(14) 0.32805(12) 0.35012(12) 0.0274(3) Uani 1 1 d . . . . .
H36 H 0.5946 0.3508 0.2875 0.033 Uiso 1 1 calc R U . . .
C41 C 0.65921(13) 0.10758(11) 0.18562(11) 0.0248(3) Uani 1 1 d . . . . .
C42 C 0.61942(15) 0.04798(12) 0.29522(12) 0.0312(3) Uani 1 1 d . . . . .
H42 H 0.6795 0.0482 0.3431 0.037 Uiso 1 1 calc R U . . .
C43 C 0.49296(16) -0.01152(13) 0.33471(13) 0.0347(3) Uani 1 1 d . . . . .
H43 H 0.4665 -0.0515 0.4096 0.042 Uiso 1 1 calc R U . . .
C44 C 0.40489(15) -0.01286(13) 0.26525(13) 0.0333(3) Uani 1 1 d . . . . .
H44 H 0.3177 -0.0530 0.2928 0.040 Uiso 1 1 calc R U . . .
C45 C 0.44451(14) 0.04452(13) 0.15565(13) 0.0314(3) Uani 1 1 d . . . . .
H45 H 0.3847 0.0430 0.1077 0.038 Uiso 1 1 calc R U . . .
C46 C 0.57086(14) 0.10414(12) 0.11557(12) 0.0281(3) Uani 1 1 d . . . . .
H46 H 0.5976 0.1429 0.0401 0.034 Uiso 1 1 calc R U . . .
C51 C 1.04255(14) 0.17114(12) -0.17353(12) 0.0272(3) Uani 1 1 d . . . . .
C52 C 0.97246(15) 0.08509(14) -0.21000(13) 0.0358(3) Uani 1 1 d . . . . .
H52 H 0.9002 0.0425 -0.1528 0.043 Uiso 1 1 calc R U . . .
C53 C 1.00567(16) 0.06044(15) -0.32744(14) 0.0409(4) Uani 1 1 d . . . . .
H53 H 0.9566 0.0014 -0.3496 0.049 Uiso 1 1 calc R U . . .
C54 C 1.10993(16) 0.12151(15) -0.41221(13) 0.0404(4) Uani 1 1 d . . . . .
H54 H 1.1321 0.1053 -0.4927 0.048 Uiso 1 1 calc R U . . .
C55 C 1.18170(16) 0.20629(15) -0.37916(13) 0.0390(4) Uani 1 1 d . . . . .
H55 H 1.2540 0.2482 -0.4371 0.047 Uiso 1 1 calc R U . . .
C56 C 1.14884(15) 0.23059(13) -0.26178(12) 0.0317(3) Uani 1 1 d . . . . .
H56 H 1.1996 0.2890 -0.2406 0.038 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
O1 C4 1.3605(15) . ?
O1 B1 1.3875(17) . ?
B1 C1 1.5094(19) . ?
B1 C51 1.567(2) . ?
C1 C2 1.3870(18) . ?
C1 C11 1.4983(17) . ?
C2 C3 1.4498(17) . ?
C2 C21 1.5027(17) . ?
C3 C4 1.3786(18) . ?
C3 C31 1.4952(18) . ?
C4 C41 1.4917(18) . ?
C11 C12 1.3926(18) . ?
C11 C16 1.3979(19) . ?
C12 C13 1.3877(19) . ?
C13 C14 1.386(2) . ?
C14 C15 1.382(2) . ?
C15 C16 1.3879(19) . ?
C21 C26 1.3875(18) . ?
C21 C22 1.3904(18) . ?
C22 C23 1.3857(19) . ?
C23 C24 1.381(2) . ?
C24 C25 1.381(2) . ?
C25 C26 1.3874(19) . ?
C31 C36 1.3936(18) . ?
C31 C32 1.3999(19) . ?
C32 C33 1.3840(19) . ?
C33 C34 1.382(2) . ?
C34 C35 1.386(2) . ?
C35 C36 1.3831(19) . ?
C41 C42 1.3959(19) . ?
C41 C46 1.3976(18) . ?
C42 C43 1.3848(19) . ?
C43 C44 1.387(2) . ?
C44 C45 1.385(2) . ?
C45 C46 1.3849(18) . ?
C51 C52 1.4011(19) . ?
C51 C56 1.4020(19) . ?
C52 C53 1.387(2) . ?
C53 C54 1.380(2) . ?
C54 C55 1.380(2) . ?
C55 C56 1.386(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
C4 O1 B1 124.41(10) . . ?
O1 B1 C1 116.69(12) . . ?
O1 B1 C51 112.39(11) . . ?
C1 B1 C51 130.91(12) . . ?
C2 C1 C11 118.54(11) . . ?
C2 C1 B1 117.61(11) . . ?
C11 C1 B1 123.84(11) . . ?
C1 C2 C3 121.55(11) . . ?
C1 C2 C21 120.83(11) . . ?
C3 C2 C21 117.55(11) . . ?
C4 C3 C2 118.92(11) . . ?
C4 C3 C31 119.76(11) . . ?
C2 C3 C31 121.29(11) . . ?
O1 C4 C3 120.60(11) . . ?
O1 C4 C41 111.84(10) . . ?
C3 C4 C41 127.56(12) . . ?
C12 C11 C16 118.16(12) . . ?
C12 C11 C1 121.12(12) . . ?
C16 C11 C1 120.70(12) . . ?
C13 C12 C11 120.69(13) . . ?
C14 C13 C12 120.58(14) . . ?
C15 C14 C13 119.31(13) . . ?
C14 C15 C16 120.35(14) . . ?
C15 C16 C11 120.89(13) . . ?
C26 C21 C22 118.95(12) . . ?
C26 C21 C2 122.49(11) . . ?
C22 C21 C2 118.54(11) . . ?
C23 C22 C21 120.77(13) . . ?
C24 C23 C22 119.81(13) . . ?
C25 C24 C23 119.85(13) . . ?
C24 C25 C26 120.42(14) . . ?
C25 C26 C21 120.17(13) . . ?
C36 C31 C32 118.18(12) . . ?
C36 C31 C3 118.99(12) . . ?
C32 C31 C3 122.83(11) . . ?
C33 C32 C31 120.78(13) . . ?
C34 C33 C32 120.27(13) . . ?
C33 C34 C35 119.62(13) . . ?
C36 C35 C34 120.29(13) . . ?
C35 C36 C31 120.85(13) . . ?
C42 C41 C46 118.89(12) . . ?
C42 C41 C4 121.47(12) . . ?
C46 C41 C4 119.60(12) . . ?
C43 C42 C41 120.47(13) . . ?
C42 C43 C44 120.18(14) . . ?
C45 C44 C43 119.79(13) . . ?
C46 C45 C44 120.33(13) . . ?
C45 C46 C41 120.32(13) . . ?
C52 C51 C56 116.57(13) . . ?
C52 C51 B1 119.69(12) . . ?
C56 C51 B1 123.70(12) . . ?
C53 C52 C51 121.80(14) . . ?
C54 C53 C52 120.13(14) . . ?
C55 C54 C53 119.53(14) . . ?
C54 C55 C56 120.32(14) . . ?
C55 C56 C51 121.65(14) . . ?

_refine_diff_density_max         0.240
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.045

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_9Ph
_database_code_depnum_ccdc_archive 'CCDC 1457938'
_audit_update_record             
;
2016-03-04 deposited with the CCDC.
2016-03-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            Biphenyl-1,2-oxaborine
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H29 B O'
_chemical_formula_sum            'C40 H29 B O'
_chemical_formula_weight         536.44

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.5923(5)
_cell_length_b                   11.7946(7)
_cell_length_c                   12.5909(7)
_cell_angle_alpha                91.8608(17)
_cell_angle_beta                 94.7506(15)
_cell_angle_gamma                113.4778(15)
_cell_volume                     1434.13(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9011
_cell_measurement_theta_min      2.403
_cell_measurement_theta_max      28.986

_exptl_crystal_description       prism
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_F_000             564
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.237
_exptl_crystal_size_mid          0.194
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.871
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26298
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.191
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5856
_reflns_number_gt                4417
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (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)+(0.0643P)²+0.3468P] 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         5856
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1281
_refine_ls_wR_factor_gt          0.1101
_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
O1 O 0.21959(10) 0.47094(9) 0.47286(8) 0.0233(2) Uani 1 1 d . . . . .
B1 B 0.10660(18) 0.35877(15) 0.45718(14) 0.0234(4) Uani 1 1 d . . . . .
C1 C 0.09235(15) 0.28005(13) 0.35456(12) 0.0237(3) Uani 1 1 d . . . . .
C2 C 0.20168(15) 0.32085(13) 0.29297(12) 0.0233(3) Uani 1 1 d . . . . .
C3 C 0.31979(15) 0.43748(13) 0.32055(12) 0.0231(3) Uani 1 1 d . . . . .
C4 C 0.32194(15) 0.51091(14) 0.40761(12) 0.0226(3) Uani 1 1 d . . . . .
C11 C -0.03232(16) 0.16348(14) 0.32211(11) 0.0252(3) Uani 1 1 d . . . . .
C12 C -0.16134(17) 0.16782(15) 0.29996(13) 0.0313(4) Uani 1 1 d . . . . .
H12 H -0.1691 0.2452 0.3057 0.038 Uiso 1 1 calc R U . . .
C13 C -0.27868(17) 0.06057(16) 0.26956(13) 0.0352(4) Uani 1 1 d . . . . .
H13 H -0.3656 0.0654 0.2540 0.042 Uiso 1 1 calc R U . . .
C14 C -0.26973(18) -0.05286(16) 0.26188(13) 0.0360(4) Uani 1 1 d . . . . .
H14 H -0.3502 -0.1261 0.2411 0.043 Uiso 1 1 calc R U . . .
C15 C -0.14267(18) -0.05916(15) 0.28464(13) 0.0335(4) Uani 1 1 d . . . . .
H15 H -0.1359 -0.1371 0.2800 0.040 Uiso 1 1 calc R U . . .
C16 C -0.02564(17) 0.04767(15) 0.31403(13) 0.0294(4) Uani 1 1 d . . . . .
H16 H 0.0611 0.0422 0.3290 0.035 Uiso 1 1 calc R U . . .
C21 C 0.19912(16) 0.24781(14) 0.19242(12) 0.0265(3) Uani 1 1 d . . . . .
C22 C 0.11495(18) 0.24753(16) 0.10196(13) 0.0354(4) Uani 1 1 d . . . . .
H22 H 0.0621 0.2963 0.1032 0.042 Uiso 1 1 calc R U . . .
C23 C 0.1073(2) 0.17661(18) 0.00967(15) 0.0475(5) Uani 1 1 d . . . . .
H23 H 0.0499 0.1776 -0.0521 0.057 Uiso 1 1 calc R U . . .
C24 C 0.1827(2) 0.10482(18) 0.00726(16) 0.0504(5) Uani 1 1 d . . . . .
H24 H 0.1768 0.0558 -0.0558 0.060 Uiso 1 1 calc R U . . .
C25 C 0.2667(2) 0.10441(17) 0.09674(16) 0.0473(5) Uani 1 1 d . . . . .
H25 H 0.3189 0.0550 0.0952 0.057 Uiso 1 1 calc R U . . .
C26 C 0.27558(19) 0.17598(16) 0.18928(14) 0.0370(4) Uani 1 1 d . . . . .
H26 H 0.3342 0.1757 0.2505 0.044 Uiso 1 1 calc R U . . .
C31 C 0.43743(15) 0.47858(14) 0.25273(12) 0.0240(3) Uani 1 1 d . . . . .
C32 C 0.54254(17) 0.43669(16) 0.27026(13) 0.0319(4) Uani 1 1 d . . . . .
H32 H 0.5369 0.3795 0.3230 0.038 Uiso 1 1 calc R U . . .
C33 C 0.65505(18) 0.47767(17) 0.21153(14) 0.0388(4) Uani 1 1 d . . . . .
H33 H 0.7266 0.4489 0.2244 0.047 Uiso 1 1 calc R U . . .
C34 C 0.66389(19) 0.56023(18) 0.13430(15) 0.0435(5) Uani 1 1 d . . . . .
H34 H 0.7415 0.5886 0.0943 0.052 Uiso 1 1 calc R U . . .
C35 C 0.5598(2) 0.60131(17) 0.11545(15) 0.0422(4) Uani 1 1 d . . . . .
H35 H 0.5656 0.6578 0.0621 0.051 Uiso 1 1 calc R U . . .
C36 C 0.44645(17) 0.56045(15) 0.17413(13) 0.0318(4) Uani 1 1 d . . . . .
H36 H 0.3747 0.5887 0.1604 0.038 Uiso 1 1 calc R U . . .
C41 C 0.42371(15) 0.63734(13) 0.44426(11) 0.0234(3) Uani 1 1 d . . . . .
C42 C 0.56646(16) 0.67594(14) 0.44296(12) 0.0271(3) Uani 1 1 d . . . . .
H42 H 0.6026 0.6207 0.4150 0.032 Uiso 1 1 calc R U . . .
C43 C 0.65541(17) 0.79439(15) 0.48230(13) 0.0317(4) Uani 1 1 d . . . . .
H43 H 0.7524 0.8195 0.4817 0.038 Uiso 1 1 calc R U . . .
C44 C 0.60503(18) 0.87642(15) 0.52231(13) 0.0351(4) Uani 1 1 d . . . . .
H44 H 0.6669 0.9579 0.5484 0.042 Uiso 1 1 calc R U . . .
C45 C 0.46376(18) 0.83937(15) 0.52422(13) 0.0336(4) Uani 1 1 d . . . . .
H45 H 0.4285 0.8957 0.5516 0.040 Uiso 1 1 calc R U . . .
C46 C 0.37384(17) 0.72084(14) 0.48649(12) 0.0278(3) Uani 1 1 d . . . . .
H46 H 0.2772 0.6957 0.4892 0.033 Uiso 1 1 calc R U . . .
C51 C 0.01578(15) 0.33011(13) 0.55314(12) 0.0226(3) Uani 1 1 d . . . . .
C52 C 0.01990(15) 0.42793(14) 0.62180(12) 0.0241(3) Uani 1 1 d . . . . .
H52 H 0.0736 0.5107 0.6063 0.029 Uiso 1 1 calc R U . . .
C53 C -0.05140(15) 0.40812(14) 0.71120(12) 0.0245(3) Uani 1 1 d . . . . .
H53 H -0.0476 0.4769 0.7548 0.029 Uiso 1 1 calc R U . . .
C54 C -0.12915(15) 0.28779(14) 0.73818(12) 0.0229(3) Uani 1 1 d . . . . .
C55 C -0.13380(16) 0.18919(14) 0.67129(12) 0.0259(3) Uani 1 1 d . . . . .
H55 H -0.1851 0.1066 0.6884 0.031 Uiso 1 1 calc R U . . .
C56 C -0.06474(16) 0.20986(14) 0.58037(12) 0.0252(3) Uani 1 1 d . . . . .
H56 H -0.0721 0.1409 0.5353 0.030 Uiso 1 1 calc R U . . .
C61 C -0.20407(16) 0.26589(14) 0.83513(12) 0.0258(3) Uani 1 1 d . . . . .
C62 C -0.14152(17) 0.33666(16) 0.93099(13) 0.0340(4) Uani 1 1 d . . . . .
H62 H -0.0497 0.3981 0.9343 0.041 Uiso 1 1 calc R U . . .
C63 C -0.21145(19) 0.31837(19) 1.02111(14) 0.0426(5) Uani 1 1 d . . . . .
H63 H -0.1677 0.3677 1.0855 0.051 Uiso 1 1 calc R U . . .
C64 C -0.34454(19) 0.22883(18) 1.01811(14) 0.0394(4) Uani 1 1 d . . . . .
H64 H -0.3921 0.2159 1.0803 0.047 Uiso 1 1 calc R U . . .
C65 C -0.40828(18) 0.15790(16) 0.92374(14) 0.0339(4) Uani 1 1 d . . . . .
H65 H -0.5003 0.0969 0.9208 0.041 Uiso 1 1 calc R U . . .
C66 C -0.33793(17) 0.17586(15) 0.83377(13) 0.0311(4) Uani 1 1 d . . . . .
H66 H -0.3819 0.1257 0.7698 0.037 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
O1 C4 1.3558(17) . ?
O1 B1 1.380(2) . ?
B1 C1 1.527(2) . ?
B1 C51 1.568(2) . ?
C1 C2 1.379(2) . ?
C1 C11 1.493(2) . ?
C2 C3 1.450(2) . ?
C2 C21 1.500(2) . ?
C3 C4 1.368(2) . ?
C3 C31 1.496(2) . ?
C4 C41 1.480(2) . ?
C11 C12 1.393(2) . ?
C11 C16 1.396(2) . ?
C12 C13 1.389(2) . ?
C13 C14 1.379(3) . ?
C14 C15 1.384(2) . ?
C15 C16 1.382(2) . ?
C21 C22 1.386(2) . ?
C21 C26 1.387(2) . ?
C22 C23 1.387(2) . ?
C23 C24 1.377(3) . ?
C24 C25 1.378(3) . ?
C25 C26 1.391(2) . ?
C31 C36 1.387(2) . ?
C31 C32 1.392(2) . ?
C32 C33 1.382(2) . ?
C33 C34 1.381(3) . ?
C34 C35 1.377(3) . ?
C35 C36 1.389(2) . ?
C41 C42 1.396(2) . ?
C41 C46 1.399(2) . ?
C42 C43 1.383(2) . ?
C43 C44 1.378(2) . ?
C44 C45 1.384(2) . ?
C45 C46 1.381(2) . ?
C51 C52 1.403(2) . ?
C51 C56 1.405(2) . ?
C52 C53 1.382(2) . ?
C53 C54 1.398(2) . ?
C54 C55 1.396(2) . ?
C54 C61 1.485(2) . ?
C55 C56 1.386(2) . ?
C61 C66 1.390(2) . ?
C61 C62 1.398(2) . ?
C62 C63 1.382(2) . ?
C63 C64 1.381(3) . ?
C64 C65 1.386(2) . ?
C65 C66 1.383(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
C4 O1 B1 124.47(12) . . ?
O1 B1 C1 116.79(14) . . ?
O1 B1 C51 113.00(13) . . ?
C1 B1 C51 130.13(14) . . ?
C2 C1 C11 120.99(13) . . ?
C2 C1 B1 116.76(13) . . ?
C11 C1 B1 122.24(13) . . ?
C1 C2 C3 121.43(13) . . ?
C1 C2 C21 120.69(13) . . ?
C3 C2 C21 117.84(13) . . ?
C4 C3 C2 119.72(13) . . ?
C4 C3 C31 120.12(13) . . ?
C2 C3 C31 120.15(13) . . ?
O1 C4 C3 120.34(13) . . ?
O1 C4 C41 110.74(12) . . ?
C3 C4 C41 128.92(13) . . ?
C12 C11 C16 117.73(14) . . ?
C12 C11 C1 119.93(14) . . ?
C16 C11 C1 122.33(14) . . ?
C13 C12 C11 120.92(15) . . ?
C14 C13 C12 120.40(16) . . ?
C13 C14 C15 119.50(15) . . ?
C16 C15 C14 120.13(16) . . ?
C15 C16 C11 121.31(16) . . ?
C22 C21 C26 118.99(15) . . ?
C22 C21 C2 119.84(14) . . ?
C26 C21 C2 121.12(15) . . ?
C21 C22 C23 120.53(17) . . ?
C24 C23 C22 120.22(19) . . ?
C23 C24 C25 119.73(17) . . ?
C24 C25 C26 120.31(18) . . ?
C21 C26 C25 120.21(18) . . ?
C36 C31 C32 118.86(14) . . ?
C36 C31 C3 121.53(14) . . ?
C32 C31 C3 119.59(14) . . ?
C33 C32 C31 120.48(16) . . ?
C34 C33 C32 120.25(16) . . ?
C35 C34 C33 119.80(16) . . ?
C34 C35 C36 120.25(17) . . ?
C31 C36 C35 120.36(16) . . ?
C42 C41 C46 118.45(14) . . ?
C42 C41 C4 123.64(13) . . ?
C46 C41 C4 117.85(13) . . ?
C43 C42 C41 120.24(15) . . ?
C44 C43 C42 120.81(15) . . ?
C43 C44 C45 119.58(15) . . ?
C46 C45 C44 120.23(15) . . ?
C45 C46 C41 120.68(15) . . ?
C52 C51 C56 116.31(13) . . ?
C52 C51 B1 119.67(13) . . ?
C56 C51 B1 123.87(13) . . ?
C53 C52 C51 122.30(14) . . ?
C52 C53 C54 120.65(14) . . ?
C55 C54 C53 117.92(13) . . ?
C55 C54 C61 121.17(13) . . ?
C53 C54 C61 120.91(13) . . ?
C56 C55 C54 121.07(14) . . ?
C55 C56 C51 121.72(14) . . ?
C66 C61 C62 117.91(14) . . ?
C66 C61 C54 121.58(14) . . ?
C62 C61 C54 120.51(14) . . ?
C63 C62 C61 120.88(16) . . ?
C64 C63 C62 120.38(17) . . ?
C63 C64 C65 119.55(16) . . ?
C66 C65 C64 120.01(16) . . ?
C65 C66 C61 121.26(16) . . ?

_refine_diff_density_max         0.305
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.055

_shelxl_version_number           2013-4

