The rapid construction and biological evaluation of densely substituted pyrrolo[1,2-<i>a</i>]indoles <i>via</i> a BF<sub>3</sub>·OEt<sub>2</sub>-assisted cascade approach.
Mali, Ghanshyam; Kumar Yadav, Vinay; Priya, Himani; Shukla, Manjari; Pandey, Peeyush; Kumar, Akhilesh; Paranjothy, Manikandan; Bhattacharyya, Sudipta; Erande, Rohan D.; Organic & biomolecular chemistry 21 (2023) 9659–9668; doi:10.1039/d3ob01457f

data_7159689
_publ_section_title
;
 The rapid construction and biological evaluation of densely substituted
 pyrrolo[1,2-<i>a</i>]indoles <i>via</i> a
 BF<sub>3</sub>&#xb7;OEt<sub>2</sub>-assisted cascade approach.
;
_journal_issue                   48
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9659
_journal_page_last               9668
_journal_paper_doi               10.1039/d3ob01457f
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C28 H30 N2 O4'
_chemical_formula_sum            'C28 H30 N2 O4'
_chemical_formula_weight         458.54
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2021-06-01
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-06-02 deposited with the CCDC.	2023-11-20 downloaded from the CCDC.
;
_cell_angle_alpha                75.760(3)
_cell_angle_beta                 78.824(3)
_cell_angle_gamma                69.309(3)
_cell_formula_units_Z            2
_cell_length_a                   8.3294(19)
_cell_length_b                   9.907(2)
_cell_length_c                   16.337(4)
_cell_measurement_reflns_used    5314
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.11
_cell_measurement_theta_min      2.24
_cell_volume                     1213.9(5)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_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  0.0468
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            30389
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.055
_diffrn_reflns_theta_min         1.295
_diffrn_source                   'fine focused sealed tube'
_diffrn_source_current           0.6
_diffrn_source_power             0.03
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6604
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1038 before and 0.0564 after correction.
The Ratio of minimum to maximum transmission is 0.8858.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   0.7455
_exptl_transmission_factor_min   0.6604
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         5317
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0486
_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^)+(0.0564P)^2^+0.3102P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1345
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3728
_reflns_number_total             5317
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01457f2.cif
_cod_data_source_block           rde_gm_23_om
_cod_depositor_comments
'Adding full bibliography for 7159689--7159690.cif.'
_cod_database_code               7159689
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   27.055
_shelx_estimated_absorpt_t_min   0.996
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C2(H2A), C17(H17), C18(H18), C19(H19), C20(H20), C23(H23),
 C24(H24)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C21(H21A,H21B,H21C), C25(H25A,H25B,H25C), C28(H28A,H28B,
 H28C)
;
_shelx_res_checksum              95332
_olex2_submission_special_instructions 'No special instructions were received'