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_7156294
_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         'C29 H21 N2, F6 P, C H2 Cl2'
_chemical_formula_sum            'C30 H23 Cl2 F6 N2 P'
_chemical_formula_weight         627.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-09-08
_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                90
_cell_angle_beta                 99.002(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7632(9)
_cell_length_b                   12.7539(9)
_cell_length_c                   16.2519(13)
_cell_measurement_reflns_used    3829
_cell_measurement_temperature    135.00(10)
_cell_measurement_theta_max      22.7500
_cell_measurement_theta_min      3.5190
_cell_volume                     2817.6(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29c (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 0.998
_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    -62.00 -36.00   1.00    4.61    --   11.08 -38.00 -60.00   26
  2  \w      7.00  82.00   1.00    4.61    --   11.08  38.00 120.00   75
  3  \w     54.00  95.00   1.00    4.61    --   11.08-178.00 -30.00   41
  4  \w    -13.00  38.00   1.00    4.61    --   11.08  38.00-120.00   51
  5  \w    -25.00   6.00   1.00    4.61    --   11.08  19.00  60.00   31
  6  \w     64.00  90.00   1.00    4.61    --   11.08  19.00  60.00   26
  7  \w    -11.00  27.00   1.00    4.61    --   11.08 -38.00 -30.00   38
  8  \w    -12.00  40.00   1.00    4.61    --   11.08  38.00  60.00   52
  9  \w     51.00  78.00   1.00    4.61    --   11.08  77.00-150.00   27
 10  \w    -18.00  29.00   1.00    4.61    --  -11.24 -99.00-180.00   47
;
_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      0.0035277000
_diffrn_orient_matrix_UB_12      0.0515025000
_diffrn_orient_matrix_UB_13      0.0167011000
_diffrn_orient_matrix_UB_21      0.0241515000
_diffrn_orient_matrix_UB_22      0.0167496000
_diffrn_orient_matrix_UB_23      -0.0331865000
_diffrn_orient_matrix_UB_31      -0.0461163000
_diffrn_orient_matrix_UB_32      0.0126478000
_diffrn_orient_matrix_UB_33      -0.0239254000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0846
_diffrn_reflns_av_unetI/netI     0.0744
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            25911
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.010
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_min         3.396
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.351
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38320
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.868
_refine_diff_density_min         -0.623
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       0.0013(4)
_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   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         4962
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.1155
_refine_ls_R_factor_gt           0.0775
_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^)+(0.0590P)^2^+8.8603P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1685
_refine_ls_wR_factor_ref         0.1937
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3394
_reflns_number_total             4962
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob01182f2.cif
_cod_data_source_block           a170907c
_cod_depositor_comments
'Adding full bibliography for 7156292--7156294.cif.'
_cod_database_code               7156294
_reflns_odcompleteness_completeness 99.70
_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, All N(H) groups
2. Restrained distances
 P1-F2A = P1-F2 = P1-F6A = P1-F6 = P1-F3A = P1-F3 = P1-F4A = P1-F4 = P1-F5A =
 P1-F5 = P1-F1 = P1-F1A
 1.59 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(F2) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F4) \\sim Ueq, Uanis(F1) \\sim
Ueq, Uanis(F6) \\sim Ueq, Uanis(F5) \\sim Ueq: with sigma of 0.005 and sigma
for terminal atoms of 0.002
Uanis(F6A) = Uanis(F6)
Uanis(F2) = Uanis(F2A)
Uanis(F1) = Uanis(F1A)
Uanis(F5) = Uanis(F5A)
Uanis(F4) = Uanis(F4A)
Uanis(F3A) = Uanis(F3)
4. Others
 Sof(F2A)=Sof(F6A)=Sof(F5A)=Sof(F4A)=Sof(F1A)=Sof(F3A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=Sof(F4)=Sof(F5)=Sof(F6)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B)
5.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C25(H25),
  C26(H26), C27(H27), C28(H28), C29(H29)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2017-09-07
_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 1.715
_oxdiff_exptl_absorpt_empirical_full_min 0.742