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_7156292
_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         'C30 H23 N2, C H2 Cl2, B F4'
_chemical_formula_sum            'C31 H25 B Cl2 F4 N2'
_chemical_formula_weight         583.24
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-10-31
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2018-05-14 deposited with the CCDC.
2018-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                89.408(6)
_cell_angle_beta                 83.302(6)
_cell_angle_gamma                72.134(7)
_cell_formula_units_Z            2
_cell_length_a                   8.8458(7)
_cell_length_b                   12.0478(9)
_cell_length_c                   13.9043(10)
_cell_measurement_reflns_used    3002
_cell_measurement_temperature    108.5(5)
_cell_measurement_theta_max      26.8110
_cell_measurement_theta_min      4.1140
_cell_volume                     1400.22(19)
_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      108.5(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2740
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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    -10.00  85.00   1.00   16.23    --   11.08  38.00  30.00   95
  2  \w     61.00 100.00   1.00   16.23    --   11.08 178.00-180.00   39
  3  \w     42.00  85.00   1.00   16.23    --   11.08-178.00-120.00   43
  4  \w    -11.00  85.00   1.00   16.23    --   11.08  38.00 -60.00   96
  5  \w    -64.00 -39.00   1.00   16.23    --   11.08 -77.00 -90.00   25
  6  \w    -28.00  -3.00   1.00   16.23    --   11.08  19.00   0.00   25
  7  \w    -20.00  28.00   1.00   16.23    --  -11.24 -99.00  90.00   48
;
_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      -0.0472763000
_diffrn_orient_matrix_UB_12      -0.0227456000
_diffrn_orient_matrix_UB_13      -0.0272615000
_diffrn_orient_matrix_UB_21      0.0690818000
_diffrn_orient_matrix_UB_22      -0.0459218000
_diffrn_orient_matrix_UB_23      -0.0182340000
_diffrn_orient_matrix_UB_31      -0.0138790000
_diffrn_orient_matrix_UB_32      -0.0346830000
_diffrn_orient_matrix_UB_33      0.0395534000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0663
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11854
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.002
_diffrn_reflns_theta_max         25.002
_diffrn_reflns_theta_min         3.430
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.283
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77420
_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            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         4934
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0502
_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^)+(0.0390P)^2^+0.6151P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.1089
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3411
_reflns_number_total             4934
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob01182f2.cif
_cod_data_source_block           a171030c
_cod_depositor_comments
'Adding full bibliography for 7156292--7156294.cif.'
_cod_database_code               7156292
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C31(H31A,H31B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12),
 C13(H13), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C26(H26), C27(H27),
  C28(H28), C29(H29), C30(H30)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2017-10-30
_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 1.486
_oxdiff_exptl_absorpt_empirical_full_min 0.781