Organocatalytic, enantioselective synthesis of benzoxaboroles via Wittig/oxa-Michael reaction Cascade of α-formyl boronic acids.
Hazra, Gurupada; Maity, Sanjay; Bhowmick, Sudipto; Ghorai, Prasanta; Chemical science 8 (2017) 3026–3030; doi:10.1039/c6sc04522g

data_1545174
_publ_section_title
;
 Organocatalytic, enantioselective synthesis of benzoxaboroles via
 Wittig/oxa-Michael reaction Cascade of \a-formyl boronic acids.
;
_journal_issue                   4
_journal_name_full               'Chemical science'
_journal_page_first              3026
_journal_page_last               3030
_journal_paper_doi               10.1039/c6sc04522g
_journal_volume                  8
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_sum            'C15 H12 B Cl O3'
_chemical_formula_weight         286.51
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-06-22 deposited with the CCDC.
2017-01-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0121(10)
_cell_length_b                   5.2339(4)
_cell_length_c                   19.8200(16)
_cell_measurement_reflns_used    9875
_cell_measurement_temperature    142(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.58
_cell_volume                     1349.82(18)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      142(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            30213
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.702
_diffrn_reflns_theta_min         2.583
_exptl_absorpt_coefficient_mu    0.285
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_description       plate
_exptl_crystal_F_000             592
_exptl_crystal_size_max          .15
_exptl_crystal_size_mid          .12
_exptl_crystal_size_min          .09
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1051 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3472
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.969
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1266
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2888
_reflns_number_total             3472
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc04522g2.cif
_cod_data_source_block           C1_a
_cod_depositor_comments
;Adding full bibliography for 1545174.cif.

 Adding full bibliography for 1545174.cif.
;
_cod_database_code               1545174
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              28338