Enantioselective synthesis of 2,3-disubstituted trans-2,3-dihydrobenzofurans using a Brønsted base/thiourea bifunctional catalyst.
Barrios Antúnez, Diego-Javier; Greenhalgh, Mark D.; Fallan, Charlene; Slawin, Alexandra M. Z.; Smith, Andrew D.; Organic & biomolecular chemistry 14 (2016) 7268–7274; doi:10.1039/c6ob01326k

data_7155202
_publ_section_title
;
 Enantioselective synthesis of 2,3-disubstituted
 trans-2,3-dihydrobenzofurans using a Br\/onsted base/thiourea
 bifunctional catalyst.
;
_journal_issue                   30
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7268
_journal_page_last               7274
_journal_paper_doi               10.1039/c6ob01326k
_journal_volume                  14
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H22 O3'
_chemical_formula_sum            'C21 H22 O3'
_chemical_formula_weight         322.40
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-03-20
_audit_creation_method           'by CrystalStructure 4.1'
_audit_update_record
;
2016-03-17 deposited with the CCDC.
2016-07-08 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   9.2519(11)
_cell_length_b                   9.9263(12)
_cell_length_c                   18.4119(19)
_cell_measurement_reflns_used    2349
_cell_measurement_temperature    125
_cell_measurement_theta_max      76.50
_cell_measurement_theta_min      25.60
_cell_volume                     1690.9(3)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b32'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b32'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_diffrn_ambient_temperature      125
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8282
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         68.251
_diffrn_reflns_theta_min         5.062
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             688.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.17
_refine_ls_abs_structure_details
;
 Flack x determined using 1216 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, S., Flack, H.D. and Wagner, T., Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(5)
_refine_ls_extinction_coef       0.0260(19)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3021
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0260
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0455P)^2^+0.2254P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0704
_refine_ls_wR_factor_ref         0.0708
_reflns_number_gt                2977
_reflns_number_total             3021
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c6ob01326k2.cif
_cod_data_source_block           19
_cod_depositor_comments          'Adding full bibliography for 7155202.cif.'
_cod_database_code               7155202
_shelx_res_checksum              92841