Substrate-Controlled, One-Pot Synthesis: Access to Chiral Chroman-2-one and Polycyclic Derivatives.
Sun, Xue-Li; Chen, Ying-Han; Zhu, Dan-Yang; Zhang, Yan; Liu, Yan-Kai; Organic letters 18 (2016) 864–867; doi:10.1021/acs.orglett.6b00160

data_1542632
_publ_section_title
;
 Substrate-Controlled, One-Pot Synthesis: Access to Chiral Chroman-2-one
 and Polycyclic Derivatives.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              864
_journal_page_last               867
_journal_paper_doi               10.1021/acs.orglett.6b00160
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration rm
_chemical_formula_sum            'C19 H15 Br O4'
_chemical_formula_weight         387.22
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 113.354(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.8044(14)
_cell_length_b                   6.7767(8)
_cell_length_c                   12.3031(14)
_cell_measurement_reflns_used    901
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.8330
_cell_measurement_theta_min      7.9990
_cell_volume                     827.0(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_sigmaI/netI    0.0631
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2658
_diffrn_reflns_theta_full        67.25
_diffrn_reflns_theta_max         67.25
_diffrn_reflns_theta_min         3.91
_exptl_absorpt_coefficient_mu    3.563
_exptl_absorpt_correction_T_max  0.7885
_exptl_absorpt_correction_T_min  0.7636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.551
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_extinction_coef       0.0189(18)
_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   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2101
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0577
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0745P)^2^+0.4661P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1378
_refine_ls_wR_factor_ref         0.1759
_reflns_number_gt                1576
_reflns_number_total             2101
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b00160_si_002.cif
_cod_data_source_block           exp_6786
_cod_original_cell_volume        827.01(18)
_cod_original_sg_symbol_H-M      P21
_cod_database_code               1542632