####################################################################### 
# 
# 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_bo2
_audit_block_doi                 10.5517/ccywcx2
_database_code_depnum_ccdc_archive 'CCDC 890255'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/om500799d 2015
_audit_update_record             
;
2012-07-04 deposited with the CCDC.
2015-09-23 downloaded from the CCDC.
;
#TrackingRef 'web_deposit_cif_file_0_Ho-YoungJung_1341378097.BO2.CIF'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H27 B O2'
_chemical_formula_sum            'C18 H27 B O2'
_chemical_formula_weight         286.21

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c '
_symmetry_space_group_name_Hall  '-P 2ybc '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.3010(16)
_cell_length_b                   6.1240(8)
_cell_length_c                   24.187(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.165(7)
_cell_angle_gamma                90.00
_cell_volume                     1817.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8124
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      25.32

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.046
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9782
_exptl_absorpt_correction_T_max  0.9884
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            29230
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0212
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         28.48
_reflns_number_total             4474
_reflns_number_gt                3025
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0985P)²+0.3039P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4474
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1908
_refine_ls_wR_factor_gt          0.1679
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
O1 O 0.16591(9) 0.5993(2) 0.01803(5) 0.0624(4) Uani 1 1 d . . .
O2 O 0.34167(9) 0.4929(2) 0.03643(5) 0.0588(3) Uani 1 1 d . . .
B1 B 0.25727(14) 0.6123(3) 0.05326(7) 0.0463(4) Uani 1 1 d . . .
C1 C 0.26341(12) 0.7485(2) 0.10820(6) 0.0473(4) Uani 1 1 d . . .
C2 C 0.37333(12) 0.7862(2) 0.13720(6) 0.0472(4) Uani 1 1 d . . .
C3 C 0.42605(15) 0.6223(3) 0.16868(7) 0.0617(4) Uani 1 1 d . . .
H3 H 0.3915 0.4884 0.1723 0.074 Uiso 1 1 calc R . .
C4 C 0.52837(16) 0.6537(4) 0.19468(8) 0.0708(5) Uani 1 1 d . . .
H4 H 0.5616 0.5420 0.2158 0.085 Uiso 1 1 calc R . .
C5 C 0.58146(16) 0.8492(4) 0.18959(8) 0.0718(5) Uani 1 1 d . . .
H5 H 0.6504 0.8705 0.2072 0.086 Uiso 1 1 calc R . .
C6 C 0.53175(17) 1.0133(4) 0.15815(8) 0.0702(5) Uani 1 1 d . . .
H6 H 0.5674 1.1458 0.1544 0.084 Uiso 1 1 calc R . .
C7 C 0.42864(15) 0.9820(3) 0.13198(7) 0.0587(4) Uani 1 1 d . . .
H7 H 0.3962 1.0938 0.1106 0.070 Uiso 1 1 calc R . .
C8 C 0.16863(13) 0.8191(3) 0.12566(7) 0.0533(4) Uani 1 1 d . . .
H8 H 0.1085 0.7866 0.1015 0.064 Uiso 1 1 calc R . .
C9 C 0.14037(15) 0.9421(3) 0.17733(8) 0.0638(5) Uani 1 1 d . . .
C10 C 0.2050(3) 0.8617(8) 0.22910(11) 0.1642(19) Uani 1 1 d . . .
H10A H 0.1911 0.7090 0.2341 0.246 Uiso 1 1 calc R . .
H10B H 0.1834 0.9414 0.2607 0.246 Uiso 1 1 calc R . .
H10C H 0.2813 0.8838 0.2253 0.246 Uiso 1 1 calc R . .
C11 C 0.0220(2) 0.8997(6) 0.18644(13) 0.1334(14) Uani 1 1 d . . .
H11A H 0.0097 0.7451 0.1884 0.200 Uiso 1 1 calc R . .
H11B H -0.0232 0.9601 0.1562 0.200 Uiso 1 1 calc R . .
H11C H 0.0042 0.9668 0.2205 0.200 Uiso 1 1 calc R . .
C12 C 0.1613(4) 1.1771(5) 0.17183(18) 0.191(2) Uani 1 1 d . . .
H12A H 0.1435 1.2509 0.2050 0.286 Uiso 1 1 calc R . .
H12B H 0.1172 1.2340 0.1408 0.286 Uiso 1 1 calc R . .
H12C H 0.2369 1.1999 0.1661 0.286 Uiso 1 1 calc R . .
C13 C 0.31130(13) 0.4140(3) -0.01965(7) 0.0534(4) Uani 1 1 d . . .
C14 C 0.18393(14) 0.4306(3) -0.02305(7) 0.0553(4) Uani 1 1 d . . .
C15 C 0.36402(18) 0.5653(4) -0.05892(9) 0.0794(6) Uani 1 1 d . . .
H15A H 0.3358 0.7103 -0.0551 0.119 Uiso 1 1 calc R . .
H15B H 0.3484 0.5157 -0.0963 0.119 Uiso 1 1 calc R . .
H15C H 0.4414 0.5664 -0.0503 0.119 Uiso 1 1 calc R . .
C16 C 0.3556(2) 0.1868(4) -0.02535(9) 0.0819(6) Uani 1 1 d . . .
H16A H 0.3216 0.0906 -0.0004 0.123 Uiso 1 1 calc R . .
H16B H 0.4329 0.1878 -0.0165 0.123 Uiso 1 1 calc R . .
H16C H 0.3405 0.1371 -0.0628 0.123 Uiso 1 1 calc R . .
C17 C 0.1275(2) 0.2275(4) -0.00434(11) 0.0883(7) Uani 1 1 d . . .
H17A H 0.1608 0.1811 0.0308 0.132 Uiso 1 1 calc R . .
H17B H 0.1339 0.1137 -0.0312 0.132 Uiso 1 1 calc R . .
H17C H 0.0518 0.2587 -0.0007 0.132 Uiso 1 1 calc R . .
C18 C 0.1318(2) 0.5058(4) -0.07831(9) 0.0871(7) Uani 1 1 d . . .
H18A H 0.1683 0.6346 -0.0900 0.131 Uiso 1 1 calc R . .
H18B H 0.0563 0.5382 -0.0747 0.131 Uiso 1 1 calc R . .
H18C H 0.1377 0.3924 -0.1053 0.131 Uiso 1 1 calc R . .


_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 B1 1.363(2) . ?
O1 C14 1.4612(19) . ?
O2 B1 1.356(2) . ?
O2 C13 1.4626(18) . ?
B1 C1 1.566(2) . ?
C1 C8 1.340(2) . ?
C1 C2 1.495(2) . ?
C2 C7 1.389(2) . ?
C2 C3 1.391(2) . ?
C3 C4 1.379(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.389(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.521(2) . ?
C8 H8 0.9300 . ?
C9 C12 1.470(4) . ?
C9 C11 1.511(3) . ?
C9 C10 1.516(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C16 1.504(3) . ?
C13 C15 1.507(3) . ?
C13 C14 1.566(2) . ?
C14 C17 1.510(3) . ?
C14 C18 1.512(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

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
B1 O1 C14 107.92(12) . . ?
B1 O2 C13 107.87(12) . . ?
O2 B1 O1 113.29(13) . . ?
O2 B1 C1 123.44(14) . . ?
O1 B1 C1 123.27(14) . . ?
C8 C1 C2 125.48(13) . . ?
C8 C1 B1 116.72(14) . . ?
C2 C1 B1 117.79(12) . . ?
C7 C2 C3 117.43(15) . . ?
C7 C2 C1 121.51(14) . . ?
C3 C2 C1 121.01(14) . . ?
C4 C3 C2 121.49(17) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C5 C4 C3 120.34(18) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.39(17) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C7 120.36(18) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C2 C7 C6 120.99(17) . . ?
C2 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C1 C8 C9 132.43(15) . . ?
C1 C8 H8 113.8 . . ?
C9 C8 H8 113.8 . . ?
C12 C9 C11 111.0(3) . . ?
C12 C9 C10 107.9(3) . . ?
C11 C9 C10 106.1(3) . . ?
C12 C9 C8 111.02(19) . . ?
C11 C9 C8 108.35(16) . . ?
C10 C9 C8 112.36(18) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 C16 108.71(14) . . ?
O2 C13 C15 106.79(14) . . ?
C16 C13 C15 109.61(17) . . ?
O2 C13 C14 102.38(12) . . ?
C16 C13 C14 115.01(15) . . ?
C15 C13 C14 113.68(16) . . ?
O1 C14 C17 106.42(15) . . ?
O1 C14 C18 108.08(15) . . ?
C17 C14 C18 109.96(18) . . ?
O1 C14 C13 102.17(11) . . ?
C17 C14 C13 114.26(16) . . ?
C18 C14 C13 115.12(16) . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        28.48
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.034


