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_7154692
_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         'C33 H25 Cl N2 O3 S'
_chemical_formula_sum            'C33 H25 Cl N2 O3 S'
_chemical_formula_weight         565.06
_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/cc1jbsn9
_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                107.265(15)
_cell_angle_beta                 98.346(15)
_cell_angle_gamma                94.368(16)
_cell_formula_units_Z            2
_cell_length_a                   9.858(5)
_cell_length_b                   10.060(5)
_cell_length_c                   15.468(8)
_cell_measurement_reflns_used    6025
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.30
_cell_measurement_theta_min      2.16
_cell_volume                     1437.8(13)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_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  0.0552
_diffrn_reflns_av_sigmaI/netI    0.0738
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19415
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.40
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_correction_T_min  0.935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             588
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         6370
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1205
_refine_ls_R_factor_gt           0.0569
_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^)+(0.0773P)^2^+0.1736P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1365
_refine_ls_wR_factor_ref         0.1599
_reflns_number_gt                3675
_reflns_number_total             6370
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob01374g2.cif
_cod_data_source_block           3e
_cod_depositor_comments
'Adding full bibliography for 7154692--7154698.cif.'
_cod_original_cell_volume        1437.7(12)
_cod_database_code               7154692