Synthesis of biaryl-based carbazoles <i>via</i> C-H functionalization and exploration of their anticancer activities.
Kaur, Ramandeep; Dilip, Haritha; Kirubakaran, Sivapriya; Babu, Srinivasarao Arulananda; Organic & biomolecular chemistry 22 (2024) 8916–8944; doi:10.1039/d4ob01392a

data_7160171
_publ_section_title
;
 Synthesis of biaryl-based carbazoles <i>via</i> C-H functionalization and
 exploration of their anticancer activities.
;
_journal_issue                   45
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8916
_journal_page_last               8944
_journal_paper_doi               10.1039/d4ob01392a
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C31 H25 N3 O3 S'
_chemical_formula_sum            'C31 H27 N3 O3 S'
_chemical_formula_weight         521.61
_chemical_name_systematic        c31h27n3o3S
_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             2024-07-06
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-08-18 deposited with the CCDC.	2024-10-03 downloaded from the CCDC.
;
_cell_angle_alpha                92.965(7)
_cell_angle_beta                 109.135(8)
_cell_angle_gamma                96.379(8)
_cell_formula_units_Z            2
_cell_length_a                   8.8101(9)
_cell_length_b                   12.3193(11)
_cell_length_c                   13.1329(10)
_cell_measurement_reflns_used    2255
_cell_measurement_temperature    273
_cell_measurement_theta_max      25.9230
_cell_measurement_theta_min      2.8690
_cell_volume                     1332.4(2)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.837
_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    -66.00  26.00   1.00   12.03    --   29.89  54.00  30.00   92
  2  \w     94.00 119.00   1.00   12.03    --   29.89  54.00-180.00   25
  3  \w    -69.00 114.00   1.00   12.03    --   29.89  54.00 -90.00  183
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0374059000
_diffrn_orient_matrix_UB_12      -0.0483730000
_diffrn_orient_matrix_UB_13      0.0090188000
_diffrn_orient_matrix_UB_21      -0.0229772000
_diffrn_orient_matrix_UB_22      -0.0130878000
_diffrn_orient_matrix_UB_23      -0.0567083000
_diffrn_orient_matrix_UB_31      0.0739684000
_diffrn_orient_matrix_UB_32      0.0295820000
_diffrn_orient_matrix_UB_33      0.0002638000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0691
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.837
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10115
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.709
_diffrn_reflns_theta_min         2.788
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87595
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dull brownish brown'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_description       block
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         8214
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1261
_refine_ls_R_factor_gt           0.0599
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0724P)^2^+0.0292P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1460
_refine_ls_wR_factor_ref         0.1980
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4088
_reflns_number_total             8214
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01392a2.cif
_cod_data_source_block           rd319
_cod_depositor_comments          'Adding full bibliography for 7160171.cif.'
_cod_database_code               7160171
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N005(H005), C00A(H00A), C00I(H00I), C00J(H00J), C00L(H00L), C00M(H00M),
 C00N(H00N), C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V),
 C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z)
2.b Idealised Me refined as rotating group:
 C010(H01A,H01B,H01C), C011(H01D,H01E,H01F), C012(H01G,H01H,H01I)
;
_shelx_res_checksum              53674
_olex2_submission_original_sample_id 'rd 319'
_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 1.212
_oxdiff_exptl_absorpt_empirical_full_min 0.862