Facile and practical synthesis of β-carbolinium salts and γ-carbolinium salts via rhodium-catalyzed three-component reactions.
Wang, Zhuo; Li, Tongyu; Xing, Siyang; Zhu, Bolin; Organic & biomolecular chemistry 16 (2018) 5021–5026; doi:10.1039/c8ob01182f

data_7156293
_publ_section_title
;
 Facile and practical synthesis of \b-carbolinium salts and \g-carbolinium
 salts via rhodium-catalyzed three-component reactions.
;
_journal_issue                   27
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5021
_journal_page_last               5026
_journal_paper_doi               10.1039/c8ob01182f
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C25 H26 Cl Ir N2'
_chemical_formula_sum            'C25 H26 Cl Ir N2'
_chemical_formula_weight         582.13
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-11-08
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-05-14 deposited with the CCDC.
2018-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.742(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5213(2)
_cell_length_b                   16.0289(5)
_cell_length_c                   17.7564(6)
_cell_measurement_reflns_used    10055
_cell_measurement_temperature    135.00(10)
_cell_measurement_theta_max      29.1890
_cell_measurement_theta_min      2.6310
_cell_volume                     2139.69(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      135.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2740
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_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     -8.00  85.00   1.00    1.67    --   11.08  38.00 -60.00   93
  2  \w     50.00  85.00   1.00    1.67    --   11.08  77.00  30.00   35
  3  \w     60.00  90.00   1.00    1.67    --   11.08-178.00  60.00   30
  4  \w    -17.00  78.00   1.00    1.67    --   11.08  57.00  30.00   95
  5  \w     35.00  97.00   1.00    1.67    --   11.08-178.00-120.00   62
  6  \w    -49.00  -9.00   1.00    1.67    --  -11.24 -38.00  30.00   40
  7  \w    -77.00 -51.00   1.00    1.67    --  -11.24 -38.00  30.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0105600000
_diffrn_orient_matrix_UB_12      0.0042505000
_diffrn_orient_matrix_UB_13      0.0393698000
_diffrn_orient_matrix_UB_21      -0.0766426000
_diffrn_orient_matrix_UB_22      -0.0257746000
_diffrn_orient_matrix_UB_23      -0.0023924000
_diffrn_orient_matrix_UB_31      0.0539803000
_diffrn_orient_matrix_UB_32      -0.0357268000
_diffrn_orient_matrix_UB_33      0.0064356000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_unetI/netI     0.0644
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21176
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.500
_diffrn_reflns_theta_min         2.623
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    6.379
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53149
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.807
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.914
_refine_diff_density_min         -0.717
_refine_diff_density_rms         0.127
_refine_ls_abs_structure_details
;
 Flack x determined using 3652 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.007(5)
_refine_ls_extinction_coef       0.00034(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     534
_refine_ls_number_reflns         8862
_refine_ls_number_restraints     85
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0316
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w=1/[\s^2^(Fo^2^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0487
_refine_ls_wR_factor_ref         0.0504
_reflns_Friedel_coverage         0.928
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                8343
_reflns_number_total             8862
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob01182f2.cif
_cod_data_source_block           a171107a
_cod_depositor_comments
'Adding full bibliography for 7156292--7156294.cif.'
_cod_database_code               7156293
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.362
_shelx_estimated_absorpt_t_min   0.298
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Uiso/Uaniso restraints and constraints
C17 \\sim C22 \\sim C18 \\sim C16 \\sim C20 \\sim C19: within 2A with sigma of
0.001 and sigma for terminal atoms of 0.002
Uanis(C19) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C46)
\\sim Ueq, Uanis(C48) \\sim Ueq, Uanis(C49) \\sim Ueq, Uanis(C18) \\sim Ueq,
Uanis(C2) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.002
Uanis(C17) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.002
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C12(H12), C13(H13),
 C14(H14), C15(H15), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32),
  C35(H35), C36(H36), C37(H37), C38(H38), C40(H40)
3.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C25(H25A,H25B,H25C), C46(H46A,H46B,H46C), C47(H47A,H47B,H47C), C48(H48A,
 H48B,H48C), C49(H49A,H49B,H49C), C50(H50A,H50B,H50C)
;
_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 1.677
_oxdiff_exptl_absorpt_empirical_full_min 0.680