Aminocatalytic asymmetric [4+2]-annulation to access functionally rich hexahydrospiroindole pyrazolones
Madavi, Shiva Prasad; Murugesan, Sivaprakash; Alagarsamy, Palanichamy; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01085B

data_7158785
_publ_section_title
;
 Aminocatalytic asymmetric [4+2]-annulation to access functionally rich
 hexahydrospiroindole pyrazolones
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01085B
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C42 H40 Br N3 O5 S'
_chemical_formula_sum            'C42 H40 Br N3 O5 S'
_chemical_formula_weight         778.74
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-06-10 deposited with the CCDC.	2022-07-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.659(7)
_cell_length_b                   17.867(9)
_cell_length_c                   31.896(16)
_cell_measurement_reflns_used    9740
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      26.06
_cell_measurement_theta_min      2.80
_cell_volume                     7784(7)
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
'Bruker D8 VENTURE diffractometer with PHOTON II detector'
_diffrn_measurement_method       '\w and \f scan'
_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  0.1249
_diffrn_reflns_av_unetI/netI     0.1109
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            81398
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.428
_exptl_absorpt_coefficient_mu    1.157
_exptl_absorpt_correction_T_max  0.7361
_exptl_absorpt_correction_T_min  0.5933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             3232
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 2436 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.040(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     956
_refine_ls_number_reflns         13677
_refine_ls_number_restraints     154
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1354
_refine_ls_R_factor_gt           0.0649
_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^)+(0.0594P)^2^+2.0611P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1580
_reflns_Friedel_coverage         0.822
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                7640
_reflns_number_total             13677
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01085b2.cif
_cod_data_source_block           shelx
_cod_database_code               7158785
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.846
_shelx_estimated_absorpt_t_max   0.893
_shelx_res_checksum              72000