Iridium catalyzed intramolecular cyclization of allyl alcohol-indole hybrids: rapid access to photoluminescent 5<i>H</i>-benzo[<i>b</i>]carbazoles.
Jaiswal, Gaurav; Pan, Subhas Chandra; Chemical communications (Cambridge, England) 61 (2025) 15011–15014; doi:10.1039/d5cc04137f

data_7134918
_publ_section_title
;
 Iridium catalyzed intramolecular cyclization of allyl alcohol-indole
 hybrids: rapid access to photoluminescent
 5<i>H</i>-benzo[<i>b</i>]carbazoles.
;
_journal_issue                   77
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              15011
_journal_page_last               15014
_journal_paper_doi               10.1039/d5cc04137f
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         '2(C18 H15 N)'
_chemical_formula_sum            'C36 H30 N2'
_chemical_formula_weight         490.62
_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_date             2024-12-10
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2025-03-17 deposited with the CCDC.	2025-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.617(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.3157(7)
_cell_length_b                   34.868(5)
_cell_length_c                   16.652(2)
_cell_measurement_reflns_used    9890
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      2.34
_cell_volume                     3076.4(7)
_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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      295.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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_unetI/netI     0.0609
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5424
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.139
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.061
_exptl_absorpt_correction_T_max  0.7414
_exptl_absorpt_correction_T_min  0.6682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1450 before and 0.0872 after correction.
The Ratio of minimum to maximum transmission is 0.9013.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.059
_exptl_crystal_description       needle
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         5424
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.1717
_refine_ls_R_factor_gt           0.0988
_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^)+(0.0100P)^2^+6.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1745
_refine_ls_wR_factor_ref         0.1919
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3044
_reflns_number_total             5424
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc04137f2.cif
_cod_data_source_block           grv_carb_0ma_a
_cod_depositor_comments          'Adding full bibliography for 7134918.cif.'
_cod_database_code               7134918
_shelx_shelxl_version_number     2019/1
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.689(3)
 0.311(3)
2. 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
3.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C35(H35A,H35B)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2A), C2(H2), C3(H3), C4(H4), C1(H1A), C9(H9), C13(H13), C14(H14),
 C15(H15), C16(H16), C20(H20), C21(H21), C22(H22), C23(H23), C27(H27), C31(H31),
  C32(H32), C33(H33), C34(H34)
3.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C36(H36A,H36B,H36C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              51211
_shelx_hkl_checksum              26479
_shelx_fab_checksum              60167
_olex2_submission_special_instructions 'No special instructions were received'