Lewis acid catalysed asymmetric cascade reaction of cyclopropyl ketones: concise synthesis of pyrrolobenzothiazoles.
Chang, Fenzhen; Shen, Bin; Wang, Sijing; Lin, Lili; Feng, Xiaoming; Chemical communications (Cambridge, England) 56 (2020) 13429–13432; doi:10.1039/d0cc05667g

data_7127337
_publ_section_title
;
 Lewis acid catalysed asymmetric cascade reaction of cyclopropyl ketones:
 concise synthesis of pyrrolobenzothiazoles.
;
_journal_issue                   87
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              13429
_journal_page_last               13432
_journal_paper_doi               10.1039/d0cc05667g
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C29 H22 Br N O S'
_chemical_formula_weight         512.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2020-04-17 deposited with the CCDC.	2020-09-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.216(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.6630(14)
_cell_length_b                   9.0225(9)
_cell_length_c                   12.3447(16)
_cell_measurement_reflns_used    4211
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      26.34
_cell_measurement_theta_min      2.52
_cell_volume                     1187.6(2)
_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-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'BRUKER D8 VENTURE PHOTON II'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0601
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8989
_diffrn_reflns_point_group_measured_fraction_full 0.943
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.398
_diffrn_reflns_theta_min         2.796
_exptl_absorpt_coefficient_mu    1.841
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6288
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             524
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ???????'
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 1386 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.042(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4595
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+0.3678P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.0908
_reflns_Friedel_coverage         0.781
_reflns_Friedel_fraction_full    0.890
_reflns_Friedel_fraction_max     0.880
_reflns_number_gt                3812
_reflns_number_total             4595
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc05667g2.cif
_cod_data_source_block           mo_20190514_CFZ_01_0m_a
_cod_depositor_comments
'Adding full bibliography for 7127337--7127340.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7127337
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              40955