A solvent controlled regioselective synthesis of 2- and 4-substituted α-carbolines under palladium catalysis.
Chatterjee, Sarat; Khatun, Rousunara; Ali, Mahammad; Chowdhury, Chinmay; Chemical communications (Cambridge, England) 60 (2024) 7427–7430; doi:10.1039/d4cc00668b

data_7133224
_publ_section_title
;
 A solvent controlled regioselective synthesis of 2- and 4-substituted
 &#x3b1;-carbolines under palladium catalysis.
;
_journal_issue                   58
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7427
_journal_page_last               7430
_journal_paper_doi               10.1039/d4cc00668b
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C18 H13 N3 O2'
_chemical_formula_sum            'C18 H13 N3 O2'
_chemical_formula_weight         303.31
_chemical_name_systematic        SC_3_52A_2_a
_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             2023-07-26
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-11-17 deposited with the CCDC.	2024-06-11 downloaded from the CCDC.
;
_cell_angle_alpha                66.241(4)
_cell_angle_beta                 89.878(3)
_cell_angle_gamma                76.826(3)
_cell_formula_units_Z            4
_cell_length_a                   6.9020(6)
_cell_length_b                   13.8797(12)
_cell_length_c                   16.3061(14)
_cell_measurement_reflns_used    8124
_cell_measurement_temperature    106.00
_cell_measurement_theta_max      68.31
_cell_measurement_theta_min      2.98
_cell_volume                     1385.0(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      106.00
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_unetI/netI     0.0610
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12890
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.820
_diffrn_reflns_theta_min         2.976
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.795
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5576
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1355 before and 0.0724 after correction.
The Ratio of minimum to maximum transmission is 0.7404.
The \l/2 correction factor is Not present.
;
_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    1.455
_exptl_crystal_description       needle
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         4911
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.141
_refine_ls_R_factor_all          0.1010
_refine_ls_R_factor_gt           0.0959
_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^)+(0.0498P)^2^+12.6914P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2987
_refine_ls_wR_factor_ref         0.3005
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4431
_reflns_number_total             4911
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00668b2.cif
_cod_data_source_block           sc_3_52a_2_a
_cod_depositor_comments
'Adding full bibliography for 7133224--7133225.cif.'
_cod_database_code               7133224
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.911
_shelx_estimated_absorpt_t_min   0.897
_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 Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C13(H13), C14(H14),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C26(H26), C27(H27),
  C30(H30), C31(H31), C33(H33), C34(H34)
2.b Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C), C35(H35A,H35B,H35C)
;
_olex2_submission_special_instructions 'No special instructions were received'