Base-promoted intermolecular cyclization of substituted 3-aryl-3-chloropropenals with tetrahydro-β-carboline: a method for the synthesis of indolizino[8,7-<i>b</i>]indole compounds.
Chen, Kairong; Yang, Miao; Chen, Shuang; Gong, Yanchuan; Xu, Junnan; Ye, Meixiang; Zhang, Jie; Guo, Liang; Organic & biomolecular chemistry 24 (2026) 2655–2659; doi:10.1039/d6ob00015k

data_7161057
_publ_section_title
;
 Base-promoted intermolecular cyclization of substituted
 3-aryl-3-chloropropenals with tetrahydro-&#x3b2;-carboline: a method for
 the synthesis of indolizino[8,7-<i>b</i>]indole compounds.
;
_journal_issue                   13
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2655
_journal_page_last               2659
_journal_paper_doi               10.1039/d6ob00015k
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C27 H20 F2 N2'
_chemical_formula_sum            'C27 H20 F2 N2'
_chemical_formula_weight         410.45
_chemical_melting_point          188.7(9)
_chemical_name_systematic
11-(4-Fluorobenzyl)-3-(4-fluorophenyl)-5,6-dihydroindolizino[8,7-b]indole
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-05-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2025-10-30 deposited with the CCDC.	2026-03-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.6398(13)
_cell_length_b                   9.8340(9)
_cell_length_c                   27.715(3)
_cell_measurement_reflns_used    3695
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      71.26
_cell_measurement_theta_min      3.19
_cell_volume                     3990.1(7)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298.0
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1172
_diffrn_reflns_av_unetI/netI     0.0755
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18150
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.077
_diffrn_reflns_theta_min         3.189
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6352
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1141 before and 0.0785 after correction.
The Ratio of minimum to maximum transmission is 0.8429.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_F_000             1712
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0018(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3867
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.1182
_refine_ls_R_factor_gt           0.0750
_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^)+(0.0729P)^2^+2.6084P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1697
_refine_ls_wR_factor_ref         0.1940
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2504
_reflns_number_total             3867
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6ob00015k2.cif
_cod_data_source_block           11_CCDC1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '187.8-189.6' was changed
to '188.7(9)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7161056--7161057.cif.
;
_cod_original_cell_volume        3990.1(6)
_cod_database_code               7161057
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.901
_shelx_estimated_absorpt_t_min   0.882
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C15(H15A,H15B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12),
 C18(H18), C19(H19), C23(H23), C24(H24), C26(H26), C27(H27)
;
_shelx_res_checksum              71416
_olex2_submission_special_instructions 'No special instructions were received'