Construction of heterocycle-fused tetrahydrocarbazoles through a formal [3 + 3]-annulation of 2-indolylmethanols with <i>para</i>-quinone methides.
Singh, Gurdeep; Sharma, Sonam; Pandey, Rajat; Rekha, ?; Vijaya Anand, Ramasamy; Organic & biomolecular chemistry 21 (2023) 2493–2498; doi:10.1039/d3ob00124e

data_7159198
_publ_section_title
;
 Construction of heterocycle-fused tetrahydrocarbazoles through a formal
 [3 + 3]-annulation of 2-indolylmethanols with <i>para</i>-quinone
 methides.
;
_journal_issue                   12
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2493
_journal_page_last               2498
_journal_paper_doi               10.1039/d3ob00124e
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C41 H40 N O S'
_chemical_formula_sum            'C42 H43 Cl2 N O S'
_chemical_formula_weight         680.73
_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             2022-07-29
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-08-02 deposited with the CCDC.	2023-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                109.223(4)
_cell_angle_beta                 90.262(4)
_cell_angle_gamma                104.830(4)
_cell_formula_units_Z            2
_cell_length_a                   9.2987(4)
_cell_length_b                   12.1896(5)
_cell_length_c                   17.6436(8)
_cell_measurement_reflns_used    3732
_cell_measurement_temperature    298.0(1)
_cell_measurement_theta_max      22.9750
_cell_measurement_theta_min      2.9430
_cell_volume                     1816.78(15)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -69.00 118.20   0.30   15.00    --   29.89  54.00 -90.00  624
  2  \w    -69.00 118.20   0.30   15.00    --   29.89  54.00   0.00  624
  3  \w    -69.00 118.20   0.30   15.00    --   29.89  54.00   0.00  624
  4  \w    -69.00 118.20   0.30   15.00    --   29.89  54.00 150.00  624
  5  \w    -69.00  54.00   0.30   15.00    --   29.89  54.00  60.00  410
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0062293000
_diffrn_orient_matrix_UB_12      -0.0624508000
_diffrn_orient_matrix_UB_13      -0.0185289000
_diffrn_orient_matrix_UB_21      0.0601547000
_diffrn_orient_matrix_UB_22      0.0138839000
_diffrn_orient_matrix_UB_23      -0.0228813000
_diffrn_orient_matrix_UB_31      0.0512700000
_diffrn_orient_matrix_UB_32      0.0031294000
_diffrn_orient_matrix_UB_33      0.0310345000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_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       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            25964
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.054
_diffrn_reflns_theta_min         2.457
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.244
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     404
_refine_ls_number_reflns         6428
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0575
_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^)+(0.1020P)^2^+0.2820P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1586
_refine_ls_wR_factor_ref         0.1808
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4714
_reflns_number_total             6428
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00124e2.cif
_cod_data_source_block           xxgs-78_rt
_cod_depositor_comments
'Adding full bibliography for 7159197--7159199.cif.'
_cod_database_code               7159198
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C42H42Cl2N1O1S1
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.974
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C7(H7), C41(H41), C24(H24), C35(H35), C31(H31), C37(H37), C38(H38),
 C40(H40), C39(H39), C32(H32), C25(H25), C27(H27), C34(H34), C17(H17), C26(H26),
  C18(H18), C33(H33)
2.c Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C6(H6A,H6B,H6C), C14(H14A,H14B,H14C), C12(H12A,H12B,
 H12C), C5(H5A,H5B,H5C), C4(H4A,H4B,H4C), C13(H13A,H13B,H13C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.273
_oxdiff_exptl_absorpt_empirical_full_min 0.863