Iodo-Cycloisomerization of Aryl(indol-3-yl)methane-Tethered Propargyl Alcohols to 3-Iodocarbazoles via Selective 1,2-Alkyl Migration.
Yaragorla, Srinivasarao; Bag, Debojyoti; Dada, Ravikrishna; Jose, K. V. Jovan; ACS omega 3 (2018) 15024–15034; doi:10.1021/acsomega.8b02393

data_4516096
_publ_section_title
;
 Iodo-Cycloisomerization of Aryl(indol-3-yl)methane-Tethered Propargyl
 Alcohols to 3-Iodocarbazoles via Selective 1,2-Alkyl Migration.
;
_journal_issue                   11
_journal_name_full               'ACS omega'
_journal_page_first              15024
_journal_page_last               15034
_journal_paper_doi               10.1021/acsomega.8b02393
_journal_volume                  3
_journal_year                    2018
_chemical_formula_moiety         'C36 H27 I N2 O'
_chemical_formula_sum            'C36 H27 I N2 O'
_chemical_formula_weight         630.49
_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
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 92.120(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.8788(8)
_cell_length_b                   9.3570(4)
_cell_length_c                   21.2905(9)
_cell_measurement_reflns_used    1029
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      59.6380
_cell_measurement_theta_min      4.1510
_cell_volume                     3161.1(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0886
_diffrn_reflns_av_unetI/netI     0.1442
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11205
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.577
_diffrn_reflns_theta_max         66.577
_diffrn_reflns_theta_min         5.090
_exptl_absorpt_coefficient_mu    8.175
_exptl_absorpt_correction_T_max  0.3208
_exptl_absorpt_correction_T_min  0.2917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadbas
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.772
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         5563
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.1362
_refine_ls_R_factor_gt           0.0746
_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^)+(0.0762P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1787
_refine_ls_wR_factor_ref         0.2304
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3027
_reflns_number_total             5563
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao8b02393_si_004.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4516096
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.292
_shelx_estimated_absorpt_t_max   0.321
_shelx_res_checksum              14890
_shelx_hkl_checksum              2404