A Highly Enantioselective Access to Chiral Chromanones and Thiochromanones by Copper-Catalyzed Asymmetric Conjugated Reduction of Chromones and Thiochromones
Xiong, Donglu; Zhou, Wenxi; Lu, Zhiwu; Zeng, Suping; Wang, Jun; Chem. Commun.  (2017) –; doi:10.1039/C7CC03939E

data_7120216
_publ_section_title
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 A Highly Enantioselective Access to Chiral Chromanones and
 Thiochromanones by Copper-Catalyzed Asymmetric Conjugated Reduction of
 Chromones and Thiochromones
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC03939E
_journal_year                    2017
_chemical_formula_sum            'C11 H12 O S'
_chemical_formula_weight         192.27
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-04-28 deposited with the CCDC.
2017-05-31 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9966(4)
_cell_length_b                   10.5907(6)
_cell_length_c                   11.7348(6)
_cell_measurement_reflns_used    7270
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      28.98
_cell_measurement_theta_min      2.59
_cell_volume                     993.82(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13948
_diffrn_reflns_theta_full        29.62
_diffrn_reflns_theta_max         29.62
_diffrn_reflns_theta_min         2.59
_exptl_absorpt_coefficient_mu    0.281
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.7067
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   SAINT
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(9)
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2794
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0377
_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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1172
_refine_ls_wR_factor_ref         0.1280
_reflns_number_gt                2319
_reflns_number_total             2794
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7cc03939e1.cif
_cod_data_source_block           lml2
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7120216