Diastereoselective synthesis of spiro[benzo[d]pyrrolo[2,1-b]thiazole-3,3'-indolines] via cycloaddition reaction of N-phenacylbenzothiazolium bromides and 3-methyleneoxindoles.
Shen, Guo-Liang; Sun, Jing; Yan, Chao-Guo; Organic & biomolecular chemistry 13 (2015) 10929–10938; doi:10.1039/c5ob01374g

data_7154694
_publ_section_title
;
 Diastereoselective synthesis of
 spiro[benzo[d]pyrrolo[2,1-b]thiazole-3,3'-indolines] via cycloaddition
 reaction of N-phenacylbenzothiazolium bromides and 3-methyleneoxindoles.
;
_journal_issue                   44
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10929
_journal_page_last               10938
_journal_paper_doi               10.1039/c5ob01374g
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C38 H25 Cl3 N2 O3 S'
_chemical_formula_sum            'C38 H25 Cl3 N2 O3 S'
_chemical_formula_weight         696.01
_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_block_doi                 10.5517/cc1jbsqc
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-07-05 deposited with the CCDC.
2015-09-03 downloaded from the CCDC.
;
_cell_angle_alpha                68.243(3)
_cell_angle_beta                 77.852(3)
_cell_angle_gamma                74.805(3)
_cell_formula_units_Z            2
_cell_length_a                   9.7111(10)
_cell_length_b                   13.1409(15)
_cell_length_c                   14.4778(16)
_cell_measurement_reflns_used    8270
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.81
_cell_measurement_theta_min      2.44
_cell_volume                     1642.7(3)
_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, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_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  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0503
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23783
_diffrn_reflns_theta_full        27.61
_diffrn_reflns_theta_max         27.61
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    0.384
_exptl_absorpt_correction_T_max  0.920
_exptl_absorpt_correction_T_min  0.900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             716
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         7507
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1022
_refine_ls_R_factor_gt           0.0534
_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^)+(0.0575P)^2^+0.5570P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1174
_refine_ls_wR_factor_ref         0.1357
_reflns_number_gt                4639
_reflns_number_total             7507
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob01374g2.cif
_cod_data_source_block           3n
_cod_depositor_comments
'Adding full bibliography for 7154692--7154698.cif.'
_cod_database_code               7154694