One-pot synthesis of benzoxaborole derivatives from the palladium-catalyzed cross-coupling reaction of alkoxydiboron with unprotected o-bromobenzylalcohols.
Zhu, Jianan; Wei, Ying; Lin, Dongqing; Ou, Changjin; Xie, Linghai; Zhao, Yu; Huang, Wei; Organic & biomolecular chemistry 13 (2015) 11362–11368; doi:10.1039/c5ob01781e

data_7154727
_publ_section_title
;
 One-pot synthesis of benzoxaborole derivatives from the
 palladium-catalyzed cross-coupling reaction of alkoxydiboron with
 unprotected o-bromobenzylalcohols.
;
_journal_issue                   46
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              11362
_journal_page_last               11368
_journal_paper_doi               10.1039/c5ob01781e
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         '2(C19 H13 B O2), C7 H8'
_chemical_formula_sum            'C45 H34 B2 O4'
_chemical_formula_weight         660.34
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-12-15 deposited with the CCDC.
2015-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                107.793(3)
_cell_angle_beta                 92.053(3)
_cell_angle_gamma                114.166(3)
_cell_formula_units_Z            1
_cell_length_a                   8.5900(6)
_cell_length_b                   9.4711(7)
_cell_length_c                   12.6798(10)
_cell_measurement_reflns_used    1952
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.85
_cell_measurement_theta_min      3.43
_cell_volume                     880.65(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0748
_diffrn_reflns_av_sigmaI/netI    0.1024
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7132
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9877
_exptl_absorpt_correction_T_min  0.9839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2000)'
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             346
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.042(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3040
_refine_ls_number_restraints     51
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1270
_refine_ls_R_factor_gt           0.0531
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0452P)^2^+0.1019P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1261
_reflns_number_gt                1676
_reflns_number_total             3040
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob01781e2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 7154727.cif.
;
_cod_original_cell_volume        880.65(11)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7154727