Synthesis of 2,3-Dihydrothieno(2,3-b)quinolines and Thieno(2,3-b)- quinolines via an Unexpected Domino Aza-MBH/Alkylation/Aldol Reaction.
Wei, Pei-Shun; Wang, Meng-Xue; Xu, Dong-Cheng; Xie, Jian-Wu; The Journal of organic chemistry 81 (2016) 1216–1222; doi:10.1021/acs.joc.5b02369

data_4031908
_publ_section_title
;
 Synthesis of 2,3-Dihydrothieno(2,3-b)quinolines and Thieno(2,3-b)-
 quinolines via an Unexpected Domino Aza-MBH/Alkylation/Aldol Reaction.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1216
_journal_page_last               1222
_journal_paper_doi               10.1021/acs.joc.5b02369
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C17 H16 Br N O5 S'
_chemical_formula_sum            'C17 H16 Br N O5 S'
_chemical_formula_weight         426.28
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                86.350(3)
_cell_angle_beta                 84.591(3)
_cell_angle_gamma                85.213(3)
_cell_formula_units_Z            2
_cell_length_a                   9.0005(5)
_cell_length_b                   9.8533(5)
_cell_length_c                   10.2837(5)
_cell_measurement_reflns_used    5440
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.76
_cell_measurement_theta_min      2.80
_cell_volume                     903.35(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-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0428
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15339
_diffrn_reflns_theta_full        27.78
_diffrn_reflns_theta_max         27.78
_diffrn_reflns_theta_min         1.99
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.418
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432
_refine_diff_density_max         0.850
_refine_diff_density_min         -0.843
_refine_diff_density_rms         0.099
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4179
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0489
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1055P)^2^+0.0928P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1434
_refine_ls_wR_factor_ref         0.1626
_reflns_number_gt                3031
_reflns_number_total             4179
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b02369_si_003.cif
_cod_data_source_block           a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/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 4268 2015-11-12 08:31:59Z antanas 

2020-10-09
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_moiety     'C8.50 H8 Br0.50 N0.50 O2.50 S0.50'
_cod_original_formula_sum        'C8.50 H8 Br0.50 N0.50 O2.50 S0.50'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     213.14
_cod_database_code               4031908