Catalyst-Controlled Switch in Diastereoselectivities: Enantioselective Construction of Functionalized 3,4-Dihydro-2H-thiopyrano[2,3-b]quinolines with Three Contiguous Stereocenters.
Ping, Xin-Ni; Wei, Pei-Shun; Zhu, Xiao-Qian; Xie, Jian-Wu; The Journal of organic chemistry 82 (2017) 2205–2210; doi:10.1021/acs.joc.6b02688

data_4032283
_publ_section_title
;
 Catalyst-Controlled Switch in Diastereoselectivities: Enantioselective
 Construction of Functionalized 3,4-Dihydro-2H-thiopyrano[2,3-b]quinolines
 with Three Contiguous Stereocenters.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2205
_journal_page_last               2210
_journal_paper_doi               10.1021/acs.joc.6b02688
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C19 H16 N2 O4 S'
_chemical_formula_sum            'C19 H16 N2 O4 S'
_chemical_formula_weight         368.39
_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_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.112(5)
_cell_length_b                   10.996(6)
_cell_length_c                   15.378(8)
_cell_measurement_reflns_used    1085
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.62
_cell_measurement_theta_min      3.33
_cell_volume                     1709.9(15)
_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      296(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
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_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0722
_diffrn_reflns_av_sigmaI/netI    0.0857
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12115
_diffrn_reflns_theta_full        27.59
_diffrn_reflns_theta_max         27.59
_diffrn_reflns_theta_min         3.33
_exptl_absorpt_coefficient_mu    0.217
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(12)
_refine_ls_extinction_coef       0.0016(10)
_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   1.011
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3944
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.1030
_refine_ls_R_factor_gt           0.0561
_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^)+(0.0387P)^2^+0.1459P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1175
_reflns_number_gt                2507
_reflns_number_total             3944
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02688_si_003.cif
_cod_data_source_block           a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/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 

2020-10-09
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_original_formula_moiety     'C3.45 H2.91 N0.36 O0.73 S0.18'
_cod_original_formula_sum        'C3.45 H2.91 N0.36 O0.73 S0.18'
_cod_original_formula_units_Z    22
_cod_original_formula_weight     66.98
_cod_database_code               4032283