Catalytic asymmetric synthesis of 3-aryl phthalides enabled by arylation-lactonization of 2-formylbenzoates.
Carlos, Andressa M. M.; Stieler, Rafael; Lüdtke, Diogo S; Organic & biomolecular chemistry 17 (2019) 283–289; doi:10.1039/c8ob02872a

data_7156643
_publ_section_title
;
 Catalytic asymmetric synthesis of 3-aryl phthalides enabled by
 arylation-lactonization of 2-formylbenzoates.
;
_journal_issue                   2
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              283
_journal_page_last               289
_journal_paper_doi               10.1039/c8ob02872a
_journal_volume                  17
_journal_year                    2019
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C14  H9  O2  Br1'
_chemical_formula_sum            'C14 H9 Br O2'
_chemical_formula_weight         289.12
_chemical_name_systematic
;
(R)-3-(4-bromophenyl)isobenzofuran-1(3H)-one
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/ccdc.csd.cc20r9hl
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2017-08-28T14:30:46-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2018-09-24 deposited with the CCDC.
2018-12-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1663(3)
_cell_length_b                   11.1767(6)
_cell_length_c                   16.5802(8)
_cell_measurement_reflns_used    9456
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      79.09
_cell_measurement_theta_min      3.96
_cell_measurement_wavelength     1.54178
_cell_volume                     1142.69(10)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX3 v2015.5-2 (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics
'Diamond (version 3.2i; Crystal Impact GbR, Bonn, Germany)'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture Photon100'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            43921
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.536
_diffrn_reflns_theta_min         4.771
_exptl_absorpt_coefficient_mu    4.786
_exptl_absorpt_correction_T_max  0.7542
_exptl_absorpt_correction_T_min  0.4336
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; SADABS (version 2014/5; Bruker, 2014) was used to perform the multi-scan
 absorption correction.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.612
_exptl_crystal_size_mid          0.292
_exptl_crystal_size_min          0.243
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1006 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.008(4)
_refine_ls_extinction_coef       0.0124(6)
_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   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2474
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0189
_refine_ls_R_factor_gt           0.0188
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0243P)^2^+0.3589P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0492
_refine_ls_wR_factor_ref         0.0492
_reflns_number_gt                2456
_reflns_number_total             2474
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob02872a2.cif
_cod_data_source_block           ACPBr
_cod_database_code               7156643