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_7127340
_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_moiety         'C29 H23 N O S'
_chemical_formula_sum            'C29 H23 N O S'
_chemical_formula_weight         433.54
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-06-04 deposited with the CCDC.	2020-09-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.0966(5)
_cell_length_b                   16.0127(8)
_cell_length_c                   27.6462(14)
_cell_measurement_reflns_used    9415
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      80.54
_cell_measurement_theta_min      4.23
_cell_volume                     4469.7(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Photon II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            81260
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         80.688
_diffrn_reflns_theta_min         3.189
_exptl_absorpt_coefficient_mu    1.444
_exptl_absorpt_correction_T_max  0.9363
_exptl_absorpt_correction_T_min  0.6711
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description       block
_exptl_crystal_F_000             1824
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ether, PE'
_exptl_crystal_size_max          0.318
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.125
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
; 
 Flack x determined using 4030 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.010(3)
_refine_ls_extinction_coef       0.00149(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     578
_refine_ls_number_reflns         9717
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0305
_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^)+(0.0214P)^2^+1.0788P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0672
_refine_ls_wR_factor_ref         0.0691
_reflns_Friedel_coverage         0.791
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                9356
_reflns_number_total             9717
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc05667g2.cif
_cod_data_source_block           cys006
_cod_depositor_comments
;
Adding full bibliography for 7127337--7127340.cif.

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C29 H23 N O S)'
_cod_original_formula_sum        'C58 H46 N2 O2 S2'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     867.09
_cod_database_code               7127340
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.657
_shelx_estimated_absorpt_t_max   0.840
_shelx_res_checksum              81969