Synthesis of Polysubstituted Cyclopentene and Cyclopenta[ b]carbazole Analogues from Unsymmetrical 4-Arylidene-3,6-diarylhex-2-en-5-ynal and Indole Derivatives via an Iodine Mediated Electrocyclization Reaction.
Bandi, Vijayalakshmi; Kavala, Veerababurao; Konala, Ashok; Hsu, Che-Hao; Villuri, Bharath Kumar; Reddy, Sabbasani Rajasekhara; Lin, LiChun; Kuo, Chun-Wei; Yao, Ching-Fa; The Journal of organic chemistry 84 (2019) 3036–3044; doi:10.1021/acs.joc.8b02168

data_4036025
_publ_section_title
;
 Synthesis of Polysubstituted Cyclopentene and Cyclopenta[ b]carbazole
 Analogues from Unsymmetrical 4-Arylidene-3,6-diarylhex-2-en-5-ynal and
 Indole Derivatives via an Iodine Mediated Electrocyclization Reaction.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3036
_journal_page_last               3044
_journal_paper_doi               10.1021/acs.joc.8b02168
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C42 H30 Br2 N2'
_chemical_formula_sum            'C42 H30 Br2 N2'
_chemical_formula_weight         722.50
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                80.4220(10)
_cell_angle_beta                 80.6500(10)
_cell_angle_gamma                89.9930(10)
_cell_formula_units_Z            2
_cell_length_a                   9.4052(4)
_cell_length_b                   12.5506(5)
_cell_length_c                   16.5291(7)
_cell_measurement_reflns_used    9983
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.19
_cell_measurement_theta_min      2.347
_cell_volume                     1897.62(14)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2005)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'D8 Venture'
_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  0.0677
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            67740
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    2.165
_exptl_absorpt_correction_T_max  0.9580
_exptl_absorpt_correction_T_min  0.5264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             732
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_platon_squeeze_details
;
;
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.562
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         6691
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0374
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0517P)^2^+0.0245P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.0971
_reflns_number_gt                5124
_reflns_number_total             6691
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b02168_si_002.cif
_cod_data_source_block           d20250
_cod_original_cell_volume        1897.63(14)
_cod_database_code               4036025