# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1039305'
_audit_update_record             
;
2014-12-15 deposited with the CCDC.
2015-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C19 H13 B O2), C7 H8'
_chemical_formula_sum            'C45 H34 B2 O4'
_chemical_formula_weight         660.34

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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5900(6)
_cell_length_b                   9.4711(7)
_cell_length_c                   12.6798(10)
_cell_angle_alpha                107.793(3)
_cell_angle_beta                 92.053(3)
_cell_angle_gamma                114.166(3)
_cell_volume                     880.65(11)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1952
_cell_measurement_theta_min      3.43
_cell_measurement_theta_max      24.85

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             346
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9839
_exptl_absorpt_correction_T_max  0.9877
_exptl_absorpt_process_details   'SADABS (Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7132
_diffrn_reflns_av_R_equivalents  0.0748
_diffrn_reflns_av_sigmaI/netI    0.1024
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         25.03
_reflns_number_total             3040
_reflns_number_gt                1676
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0452P)²+0.1019P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.042(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3040
_refine_ls_number_parameters     239
_refine_ls_number_restraints     51
_refine_ls_R_factor_all          0.1270
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1261
_refine_ls_wR_factor_gt          0.0993
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.018
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3330(3) 0.2637(3) 0.1922(2) 0.0298(6) Uani 1 1 d . . .
C2 C 0.3186(3) 0.2151(3) 0.2962(2) 0.0299(6) Uani 1 1 d . . .
C3 C 0.4351(4) 0.3024(4) 0.3989(2) 0.0375(7) Uani 1 1 d . . .
H3 H 0.5337 0.4041 0.4105 0.045 Uiso 1 1 calc R . .
C4 C 0.4013(4) 0.2348(4) 0.4834(2) 0.0476(8) Uani 1 1 d . . .
H4 H 0.4789 0.2904 0.5539 0.057 Uiso 1 1 calc R . .
C5 C 0.2566(4) 0.0878(4) 0.4666(3) 0.0498(8) Uani 1 1 d . . .
H5 H 0.2367 0.0436 0.5254 0.060 Uiso 1 1 calc R . .
C6 C 0.1408(4) 0.0047(4) 0.3656(2) 0.0410(8) Uani 1 1 d . . .
H6 H 0.0405 -0.0951 0.3554 0.049 Uiso 1 1 calc R . .
C7 C 0.1722(3) 0.0684(3) 0.2784(2) 0.0318(7) Uani 1 1 d . . .
B1 B 0.0793(4) 0.0149(4) 0.1571(3) 0.0339(8) Uani 1 1 d . . .
C9 C 0.5898(3) 0.4375(3) 0.1407(2) 0.0337(7) Uani 1 1 d . . .
C10 C 0.4989(3) 0.2810(3) 0.1468(2) 0.0312(7) Uani 1 1 d . . .
C11 C 0.5650(4) 0.1658(4) 0.1175(2) 0.0398(7) Uani 1 1 d . . .
H11 H 0.5041 0.0594 0.1225 0.048 Uiso 1 1 calc R . .
C12 C 0.7226(4) 0.2101(4) 0.0806(2) 0.0479(8) Uani 1 1 d . . .
H12 H 0.7696 0.1327 0.0596 0.058 Uiso 1 1 calc R . .
C13 C 0.8117(4) 0.3646(4) 0.0740(2) 0.0481(8) Uani 1 1 d . . .
H13 H 0.9191 0.3921 0.0482 0.058 Uiso 1 1 calc R . .
C14 C 0.7468(4) 0.4808(4) 0.1046(2) 0.0414(8) Uani 1 1 d . . .
H14 H 0.8091 0.5877 0.1007 0.050 Uiso 1 1 calc R . .
C15 C 0.4890(3) 0.5316(3) 0.1791(2) 0.0324(7) Uani 1 1 d . . .
C16 C 0.3396(3) 0.4317(3) 0.2083(2) 0.0311(7) Uani 1 1 d . . .
C17 C 0.2203(4) 0.4886(4) 0.2476(2) 0.0397(7) Uani 1 1 d . . .
H17 H 0.1181 0.4199 0.2671 0.048 Uiso 1 1 calc R . .
C18 C 0.2545(4) 0.6498(4) 0.2576(3) 0.0485(8) Uani 1 1 d . . .
H18 H 0.1742 0.6914 0.2839 0.058 Uiso 1 1 calc R . .
C19 C 0.4041(4) 0.7500(4) 0.2296(3) 0.0493(8) Uani 1 1 d . . .
H19 H 0.4251 0.8595 0.2372 0.059 Uiso 1 1 calc R . .
C20 C 0.5238(4) 0.6930(4) 0.1905(2) 0.0424(8) Uani 1 1 d . . .
H20 H 0.6268 0.7623 0.1720 0.051 Uiso 1 1 calc R . .
C21 C 0.0942(5) 0.6580(6) 0.5756(3) 0.0735(10) Uani 0.50 1 d PDU A 1
C24 C 0.1908(10) 0.8152(9) 0.6464(6) 0.069(2) Uani 0.50 1 d PDU A 1
H24A H 0.1587 0.8901 0.6222 0.103 Uiso 0.50 1 calc PR A 1
H24B H 0.3141 0.8452 0.6451 0.103 Uiso 0.50 1 calc PR A 1
H24C H 0.1697 0.8242 0.7231 0.103 Uiso 0.50 1 calc PR A 1
C21' C 0.0942(5) 0.6580(6) 0.5756(3) 0.0735(10) Uani 0.50 1 d PU A 2
H21A H 0.1590 0.7670 0.6283 0.088 Uiso 0.50 1 calc PR A 2
C22 C -0.0208(5) 0.6291(6) 0.4834(3) 0.0756(11) Uani 1 1 d DU . .
H22A H -0.0343 0.7183 0.4720 0.091 Uiso 1 1 calc R A 1
C23 C 0.1139(5) 0.5272(6) 0.5904(3) 0.0721(11) Uani 1 1 d DU . .
H23A H 0.1938 0.5470 0.6532 0.087 Uiso 1 1 calc R A 1
O1 O 0.1778(2) 0.1308(2) 0.11032(14) 0.0329(5) Uani 1 1 d . . .
O2 O -0.0699(2) -0.1176(2) 0.09973(16) 0.0433(6) Uani 1 1 d D . .
H2 H -0.104(4) -0.122(4) 0.0359(17) 0.052 Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.473(3) . ?
C1 C2 1.518(3) . ?
C1 C16 1.518(3) . ?
C1 C10 1.522(3) . ?
C2 C7 1.386(4) . ?
C2 C3 1.397(4) . ?
C3 C4 1.391(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.378(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.398(3) . ?
C6 H6 0.9500 . ?
C7 B1 1.538(4) . ?
B1 O2 1.344(4) . ?
B1 O1 1.394(3) . ?
C9 C14 1.379(4) . ?
C9 C10 1.393(4) . ?
C9 C15 1.476(4) . ?
C10 C11 1.388(4) . ?
C11 C12 1.388(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.377(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(4) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.390(4) . ?
C15 C20 1.391(4) . ?
C16 C17 1.383(3) . ?
C17 C18 1.395(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.385(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.386(4) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C24 1.352(7) . ?
C21 C23 1.383(5) . ?
C21 C22 1.384(5) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C22 C23 1.355(5) 2_566 ?
C22 H22A 0.9500 . ?
C23 C22 1.355(5) 2_566 ?
C23 H23A 0.9500 . ?
O2 H2 0.833(17) . ?

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
O1 C1 C2 103.5(2) . . ?
O1 C1 C16 110.91(19) . . ?
C2 C1 C16 115.6(2) . . ?
O1 C1 C10 111.7(2) . . ?
C2 C1 C10 114.3(2) . . ?
C16 C1 C10 101.2(2) . . ?
C7 C2 C3 122.2(2) . . ?
C7 C2 C1 111.7(2) . . ?
C3 C2 C1 126.2(2) . . ?
C4 C3 C2 117.4(3) . . ?
C4 C3 H3 121.3 . . ?
C2 C3 H3 121.3 . . ?
C5 C4 C3 121.1(3) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 119.4(3) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C2 C7 C6 119.0(3) . . ?
C2 C7 B1 105.7(2) . . ?
C6 C7 B1 135.3(3) . . ?
O2 B1 O1 122.6(3) . . ?
O2 B1 C7 129.2(3) . . ?
O1 B1 C7 108.2(2) . . ?
C14 C9 C10 120.7(3) . . ?
C14 C9 C15 131.4(3) . . ?
C10 C9 C15 107.9(2) . . ?
C11 C10 C9 120.7(2) . . ?
C11 C10 C1 128.0(2) . . ?
C9 C10 C1 111.2(2) . . ?
C12 C11 C10 118.2(3) . . ?
C12 C11 H11 120.9 . . ?
C10 C11 H11 120.9 . . ?
C13 C12 C11 121.0(3) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 120.9(3) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C9 C14 C13 118.5(3) . . ?
C9 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
C16 C15 C20 120.7(2) . . ?
C16 C15 C9 108.6(2) . . ?
C20 C15 C9 130.7(3) . . ?
C17 C16 C15 121.2(2) . . ?
C17 C16 C1 127.8(2) . . ?
C15 C16 C1 111.0(2) . . ?
C16 C17 C18 118.1(3) . . ?
C16 C17 H17 121.0 . . ?
C18 C17 H17 121.0 . . ?
C19 C18 C17 120.8(3) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 121.1(3) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C19 C20 C15 118.2(3) . . ?
C19 C20 H20 120.9 . . ?
C15 C20 H20 120.9 . . ?
C24 C21 C23 121.4(5) . . ?
C24 C21 C22 119.0(5) . . ?
C23 C21 C22 119.5(4) . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C22 C21 119.7(4) 2_566 . ?
C23 C22 H22A 120.2 2_566 . ?
C21 C22 H22A 120.2 . . ?
C22 C23 C21 120.8(4) 2_566 . ?
C22 C23 H23A 119.6 2_566 . ?
C21 C23 H23A 119.6 . . ?
B1 O1 C1 111.0(2) . . ?
B1 O2 H2 116(2) . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.043
