Asymmetric synthesis of dihydrocoumarins via catalytic sequential 1,6-addition/transesterification of α-isocyanoacetates with para-quinone methides.
Zhao, Mei-Xin; Xiang, Juan; Zhao, Zi-Qiang; Zhao, Xiao-Li; Shi, Min; Organic & biomolecular chemistry 18 (2020) 1637–1646; doi:10.1039/c9ob02652e

data_7157343
_publ_section_title
;
 Asymmetric synthesis of dihydrocoumarins via catalytic sequential
 1,6-addition/transesterification of \a-isocyanoacetates with para-quinone
 methides.
;
_journal_issue                   8
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1637
_journal_page_last               1646
_journal_paper_doi               10.1039/c9ob02652e
_journal_volume                  18
_journal_year                    2020
_chemical_formula_sum            'C60 H60 Br2 N2 O6'
_chemical_formula_weight         1064.92
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2019-06-20 deposited with the CCDC.	2020-01-31 downloaded from the CCDC.
;
_cell_angle_alpha                81.3050(10)
_cell_angle_beta                 75.309(2)
_cell_angle_gamma                88.6410(10)
_cell_formula_units_Z            2
_cell_length_a                   9.5271(2)
_cell_length_b                   15.9359(2)
_cell_length_c                   18.6928(4)
_cell_measurement_reflns_used    25933
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.9420
_cell_measurement_theta_min      4.0330
_cell_volume                     2713.35(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0802
_diffrn_reflns_av_sigmaI/netI    0.0504
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            68287
_diffrn_reflns_theta_full        74.61
_diffrn_reflns_theta_max         74.61
_diffrn_reflns_theta_min         4.01
_exptl_absorpt_coefficient_mu    2.300
_exptl_absorpt_correction_T_max  0.8374
_exptl_absorpt_correction_T_min  0.5862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.925
_refine_diff_density_min         -1.020
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       0.00034(9)
_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   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     650
_refine_ls_number_reflns         10851
_refine_ls_number_restraints     27
_refine_ls_restrained_S_all      1.149
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0548
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0565P)^2^+4.0119P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1376
_refine_ls_wR_factor_ref         0.1416
_reflns_number_gt                9239
_reflns_number_total             10851
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9ob02652e2.cif
_cod_data_source_block           exp_903
_cod_depositor_comments          'Adding full bibliography for 7157343.cif.'
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7157343