Enantioselective addition of arylboronic acids to methyl 2-formylbenzoates by using a ruthenium/Me-BIPAM catalyst for synthesis of chiral 3-aryl-isobenzofuranones.
Yohda, Masaaki; Yamamoto, Yasunori; Organic & biomolecular chemistry 13 (2015) 10874–10880; doi:10.1039/c5ob01661d

data_7154705
_publ_section_title
;
 Enantioselective addition of arylboronic acids to methyl
 2-formylbenzoates by using a ruthenium/Me-BIPAM catalyst for synthesis of
 chiral 3-aryl-isobenzofuranones.
;
_journal_issue                   44
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10874
_journal_page_last               10880
_journal_paper_doi               10.1039/c5ob01661d
_journal_volume                  13
_journal_year                    2015
_chemical_absolute_configuration S
_chemical_formula_moiety         'C12 H8 O2 S'
_chemical_formula_sum            'C12 H8 O2 S'
_chemical_formula_weight         216.25
_chemical_melting_point          387(2)
_chemical_name_systematic
(S)-3-(thiophen-3-yl)-1,3-dihydro-2-benzofuran-1-one
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2015-08-27 deposited with the CCDC.
2015-09-04 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 91.935(5)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   6.1577(10)
_cell_length_b                   7.3665(13)
_cell_length_c                   11.253(2)
_cell_measurement_reflns_used    3629
_cell_measurement_temperature    123
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.31
_cell_volume                     510.15(15)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4978
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.48
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_T_max  0.949
_exptl_absorpt_correction_T_min  0.549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             224.00
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: diethylether/hexane'
_exptl_crystal_size_max          0.672
_exptl_crystal_size_mid          0.195
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.400
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  878 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.13(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     140
_refine_ls_number_reflns         2133
_refine_ls_number_restraints     1
_refine_ls_R_factor_gt           0.0442
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0629P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1171
_reflns_number_gt                1660
_reflns_number_total             2133
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c5ob01661d2.cif
_cod_data_source_block           yamamoto0826
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '385-389' was changed to '387(2)' -
the average value was taken and precision was estimated.

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

 Adding full bibliography for 7154705.cif.
;
_cod_database_code               7154705