Catalytic Enantioselective Vinylogous Allylic Alkylation of Coumarins.
Kayal, Satavisha; Mukherjee, Santanu; Organic letters 19 (2017) 4944–4947; doi:10.1021/acs.orglett.7b02421

data_1546965
_publ_section_title
;
 Catalytic Enantioselective Vinylogous Allylic Alkylation of Coumarins.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4944
_journal_page_last               4947
_journal_paper_doi               10.1021/acs.orglett.7b02421
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration syn
_chemical_formula_sum            'C23 H18 Br N O4'
_chemical_formula_weight         452.29
_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
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0773(2)
_cell_length_b                   14.9171(6)
_cell_length_c                   21.7733(8)
_cell_measurement_reflns_used    9850
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.21
_cell_volume                     1973.87(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0134
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            45241
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_min         3.121
_exptl_absorpt_coefficient_mu    2.113
_exptl_absorpt_correction_T_max  0.932
_exptl_absorpt_correction_T_min  0.660
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADBAS
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_description       Block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.001(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3467
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0171
_refine_ls_R_factor_gt           0.0166
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0251P)^2^+0.5464P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0429
_refine_ls_wR_factor_ref         0.0431
_reflns_Friedel_coverage         0.715
_reflns_Friedel_fraction_full    0.970
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3409
_reflns_number_total             3467
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02421_si_003.cif
_cod_data_source_block           3ag
_cod_depositor_comments          'Adding full bibliography for 1546965.cif.'
_cod_database_code               1546965
_shelxl_version_number           2013-4
_shelx_res_checksum              50172
_shelx_hkl_checksum              63813