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_7156601
_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_formula_sum            'C16 H12 Br N'
_chemical_formula_weight         298.18
_chemical_name_systematic        3-arylquinoline
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc1zlgst
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_audit_update_record
;
2018-04-05 deposited with the CCDC.
2018-12-04 downloaded from the CCDC.
;
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_cell_angle_gamma                90
_cell_formula_units_Z            8
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_cell_length_c                   28.807(3)
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_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.0130
_cell_measurement_theta_min      3.7550
_cell_volume                     2587.6(6)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_av_R_equivalents  0.1221
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_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
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_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
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_diffrn_reflns_theta_max         25.050
_diffrn_reflns_theta_min         2.940
_exptl_absorpt_coefficient_mu    3.157
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_restraints     0
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0100P)^2^+0.0900P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1334
_reflns_Friedel_coverage         0.000
_reflns_number_gt                911
_reflns_number_total             2283
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob02872a2.cif
_cod_data_source_block           exp_4183
_cod_depositor_comments          'Adding full bibliography for 7156601.cif.'
_cod_original_cell_volume        2587.5(6)
_cod_database_code               7156601
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              39374