Copper-catalysed enantioselective intramolecular etherification of propargylic esters: synthetic approach to chiral isochromans
Liu, Shiyao; Nakajima, Kazunari; Nishibayashi, Yoshiaki; RSC Advances 9 (2019) 18918–; doi:10.1039/C9RA03880A

data_7232912
_publ_section_title
;
 Copper-catalysed enantioselective intramolecular etherification of
 propargylic esters: synthetic approach to chiral isochromans
;
_journal_issue                   33
_journal_name_full               'RSC Advances'
_journal_page_first              18918
_journal_paper_doi               10.1039/C9RA03880A
_journal_volume                  9
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H16 Cl N3 O'
_chemical_formula_sum            'C18 H16 Cl N3 O'
_chemical_formula_weight         325.80
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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
;
2019-04-18 deposited with the CCDC.    2019-06-11 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 102.989(7)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   12.1916(6)
_cell_length_b                   5.5082(3)
_cell_length_c                   12.3900(6)
_cell_measurement_reflns_used    7326
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      1.72
_cell_volume                     810.75(7)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, 2018)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_structure_refinement  'SHELXL Version 2016/6 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXD Version 2013/2 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.983
_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  0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7587
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.455
_diffrn_reflns_theta_min         2.662
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             340.00
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.55
_refine_diff_density_min         -0.44
_refine_ls_abs_structure_details
;
 Flack x determined using 1202 quotients [(I+)-(I-)]/[(I+)+(I-)]
;
_refine_ls_abs_structure_Flack   0.09(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3593
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0485
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+0.5080P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.0965
_reflns_Friedel_coverage         0.788
_reflns_Friedel_fraction_full    0.975
_reflns_Friedel_fraction_max     0.954
_reflns_number_gt                3259
_reflns_number_total             3593
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c9ra03880a2.cif
_cod_data_source_block           1910939
_cod_original_cell_volume        810.74(8)
_cod_database_code               7232912
_shelx_res_checksum              55820