Asymmetric Catalytic Synthesis of Thiochromenes via an Acyl Transfer-Initiated Cascade.
Ahlemeyer, Nicholas A.; Birman, Vladimir B.; Organic letters 18 (2016) 3454–3457; doi:10.1021/acs.orglett.6b01639

data_1555622
_publ_section_title
;
 Asymmetric Catalytic Synthesis of Thiochromenes via an Acyl
 Transfer-Initiated Cascade.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3454
_journal_page_last               3457
_journal_paper_doi               10.1021/acs.orglett.6b01639
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H15 N O S'
_chemical_formula_sum            'C19 H15 N O S'
_chemical_formula_weight         305.38
_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'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.5711(2)
_cell_length_b                   6.5999(2)
_cell_length_c                   40.0657(12)
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      40.23
_cell_measurement_theta_min      3.05
_cell_volume                     1473.16(8)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2013 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_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  0.0330
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       72
_diffrn_reflns_limit_l_min       -72
_diffrn_reflns_number            74764
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         40.295
_diffrn_reflns_theta_min         2.033
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_T_max  0.8628
_exptl_absorpt_correction_T_min  0.8254
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'sadabs v2014/5'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.459
_exptl_crystal_size_mid          0.372
_exptl_crystal_size_min          0.283
_refine_diff_density_max         0.525
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
; 
 Flack x determined using 3616 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.020(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         9271
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0317
_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^)+(0.0486P)^2^+0.1401P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0841
_reflns_Friedel_coverage         0.752
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                8879
_reflns_number_total             9271
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01639_si_002.cif
_cod_data_source_block           v23315
_cod_database_code               1555622
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.906
_shelx_estimated_absorpt_t_max   0.940
_shelx_res_checksum              80582
_shelx_hkl_checksum              39354