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_7159690
_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         'C36 H46 N2 O4'
_chemical_formula_sum            'C36 H46 N2 O4'
_chemical_formula_weight         570.75
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-03-09
_audit_creation_method
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_audit_update_record
;
2023-03-09 deposited with the CCDC.	2023-11-20 downloaded from the CCDC.
;
_cell_angle_alpha                98.1600(10)
_cell_angle_beta                 91.3010(10)
_cell_angle_gamma                111.1680(10)
_cell_formula_units_Z            2
_cell_length_a                   8.3075(3)
_cell_length_b                   10.5823(3)
_cell_length_c                   19.6489(7)
_cell_measurement_reflns_used    7590
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.37
_cell_measurement_theta_min      2.49
_cell_volume                     1589.39(9)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_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  0.0402
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            27606
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.461
_diffrn_reflns_theta_min         2.091
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6863
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1002 before and 0.0497 after correction.
The Ratio of minimum to maximum transmission is 0.9203.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_method    'NOT MEASURED'
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         7957
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0507
_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^)+(0.0521P)^2^+0.8199P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1312
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5953
_reflns_number_total             7957
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01457f2.cif
_cod_data_source_block           6decc_o_0m
_cod_depositor_comments
'Adding full bibliography for 7159689--7159690.cif.'
_cod_database_code               7159690
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.746
_shelx_estimated_absorpt_t_min   0.686
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C18(H18), C28(H28), C30(H30)
1.b Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C32(H32A,H32B), C35(H35A,H35B)
1.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C23(H23), C12(H12), C21(H21), C22(H22), C20(H20)
1.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C26(H26A,H26B,H26C), C3(H3A,H3B,H3C), C33(H33A,H33B,
 H33C), C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C11(H11A,H11B,H11C), C9(H9A,H9B,H9C),
 C36(H36A,H36B,H36C), C10(H10A,H10B,H10C)
;
_shelx_res_checksum              7537
_olex2_submission_special_instructions 'No special instructions were received'