Diversity-Oriented Asymmetric Catalysis (DOAC): Stereochemically Divergent Synthesis of Thiochromanes Using an Imidazoline-Aminophenol-Nickel-Catalyzed Michael/Henry Reaction.
Arai, Takayoshi; Yamamoto, Yushi; Organic letters 16 (2014) 1700–1703; doi:10.1021/ol500361w

data_1513909
_publ_section_title
;
 Diversity-Oriented Asymmetric Catalysis (DOAC): Stereochemically
 Divergent Synthesis of Thiochromanes Using an
 Imidazoline-Aminophenol-Nickel-Catalyzed Michael/Henry Reaction.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1700
_journal_page_last               1703
_journal_paper_doi               10.1021/ol500361w
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C15 H13 N O3 S'
_chemical_formula_weight         287.32
_chemical_name_common            arai39
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.0289(12)
_cell_length_b                   11.1264(13)
_cell_length_c                   24.230(3)
_cell_measurement_temperature    173.(2)
_cell_volume                     2703.7(6)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173.(2)
_diffrn_measured_fraction_theta_full 0.927
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'graphite '
_diffrn_radiation_type           'MoK\a '
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0474
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            15425
_diffrn_reflns_theta_full        28.48
_diffrn_reflns_theta_max         28.48
_diffrn_reflns_theta_min         1.68
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.246
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.339
_refine_ls_abs_structure_details
;
Flack x determined using 1884 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.05(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     461
_refine_ls_number_reflns         6102
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          3.365
_refine_ls_shift/su_mean         0.276
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0558P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.1060
_reflns_number_gt                5169
_reflns_number_total             6102
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol500361w_si_002.cif
_cod_data_source_block           I
_cod_original_cell_volume        2703.7(5)
_cod_database_code               1513909
_shelx_res_checksum              37510
_shelx_hkl_checksum              81202