Asymmetric Synthesis of 4-Aryl-3,4-dihydrocoumarins by N-Heterocyclic Carbene Catalyzed Annulation of Phenols with Enals.
Li, Guo-Tai; Li, Zhi-Ke; Gu, Qing; You, Shu-Li; Organic letters 19 (2017) 1318–1321; doi:10.1021/acs.orglett.7b00088

data_1545323
_publ_section_title
;
 Asymmetric Synthesis of 4-Aryl-3,4-dihydrocoumarins by N-Heterocyclic
 Carbene Catalyzed Annulation of Phenols with Enals.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1318
_journal_page_last               1321
_journal_paper_doi               10.1021/acs.orglett.7b00088
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_sum            'C18 H18 O5'
_chemical_formula_weight         314.32
_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
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90.062(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.9588(9)
_cell_length_b                   5.6834(6)
_cell_length_c                   17.1239(19)
_cell_measurement_reflns_used    2994
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      56.684
_cell_measurement_theta_min      5.118
_cell_volume                     774.57(15)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4723
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.988
_diffrn_reflns_theta_min         2.379
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6252
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.123
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
; 
 Flack x determined using 1226 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   1.3(5)
_refine_ls_extinction_coef       0.155(13)
_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   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2993
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0317
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0604P)^2^+0.0430P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0908
_reflns_Friedel_coverage         0.790
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                2843
_reflns_number_total             2993
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00088_si_002.cif
_cod_data_source_block           cd214665
_cod_depositor_comments          'Adding full bibliography for 1545323.cif.'
_cod_database_code               1545323
_shelxl_version_number           2013-4
_shelx_res_checksum              73524
_shelx_hkl_checksum              25026