A one-pot ultrasound-assisted regio and stereoselective synthesis of indenoquinoxaline engrafted spiropyrrolidines.
Bokam, Ramesh; Munipalle, Kiran; Appa Rao Annam, S Ch V; Gundoju, Narayanarao; Raju Chowhan, L.; Ponnapalli, Mangala Gowri; Organic & biomolecular chemistry 22 (2024) 5150–5158; doi:10.1039/d4ob00288a

data_7159973
_publ_section_title
;
 A one-pot ultrasound-assisted regio and stereoselective synthesis of
 indenoquinoxaline engrafted spiropyrrolidines.
;
_journal_issue                   25
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5150
_journal_page_last               5158
_journal_paper_doi               10.1039/d4ob00288a
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C30 H19 Br Cl2 N4 O2'
_chemical_formula_sum            'C30 H19 Br Cl2 N4 O2'
_chemical_formula_weight         618.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2024-04-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-05-18 deposited with the CCDC.	2024-05-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.484(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.744(4)
_cell_length_b                   18.229(8)
_cell_length_c                   13.664(5)
_cell_measurement_reflns_used    8341
_cell_measurement_temperature    294.0
_cell_measurement_theta_max      27.14
_cell_measurement_theta_min      2.21
_cell_volume                     2659.0(18)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      294.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            54414
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.339
_diffrn_reflns_theta_min         1.908
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.783
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.664
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.073
_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     352
_refine_ls_number_reflns         6610
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0482
_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^)+(0.0580P)^2^+1.9264P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1171
_refine_ls_wR_factor_ref         0.1308
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4893
_reflns_number_total             6610
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00288a2.cif
_cod_data_source_block           lrcbr8_02
_cod_depositor_comments          'Adding full bibliography for 7159973.cif.'
_cod_original_cell_volume        2659.1(19)
_cod_database_code               7159973
_shelxl_version_number           2012-9
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16), C17(H17), C18(H18)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C1(H1), C2(H2), C3(H3A), C6(H6), C12(H12), C13(H13), C14(H14),
 C15(H15), C20(H20), C21(H21), C22(H22), C23(H23), C26(H26), C27(H27), C28(H28)
;
_shelx_res_checksum              57027
_olex2_submission_special_instructions 'No special instructions were received'