A rhodium-catalysed three-component reaction to access C1-substituted tetrahydroisoquinolines
Zhang, Dan; Liu, Junwen; Kang, Zhenghui; Qiu, Huang; Hu, Wenhao; Organic & Biomolecular Chemistry  (2019) –; doi:10.1039/C9OB02303H

data_7157191
_publ_section_title
;
 A rhodium-catalysed three-component reaction to access C1-substituted
 tetrahydroisoquinolines
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/C9OB02303H
_journal_year                    2019
_chemical_formula_moiety         'C26 H26 Br N3 O3'
_chemical_formula_sum            'C26 H26 Br N3 O3'
_chemical_formula_weight         508.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-10-12 deposited with the CCDC.	2019-11-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.380(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.9877(2)
_cell_length_b                   8.49500(10)
_cell_length_c                   19.3047(3)
_cell_measurement_reflns_used    9901
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.2160
_cell_measurement_theta_min      3.1670
_cell_volume                     2288.74(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.938
_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    -99.00 -74.00   0.50    0.05    --  -46.62 -57.00  10.00   50
  2  \w    -63.00  26.00   0.50    0.05    --  -46.62  57.00 151.00  178
  3  \w    -24.00  45.00   0.50    0.05    --   46.62 -57.00  10.00  138
  4  \w     43.00 100.00   0.50    0.05    --   46.62  57.00 151.00  114
  5  \w   -170.00 -88.00   0.50    0.05    -- -100.00 -57.00  10.00  164
  6  \w   -116.00 -27.00   0.50    0.05    -- -100.00  57.00 151.00  178
  7  \w     42.00  68.00   0.50    0.05    --  107.00 -57.00  10.00   52
  8  \w    108.00 135.00   0.50    0.05    --  107.00  57.00 151.00   54
  9  \w   -117.00 -72.00   0.50    0.05    --  -46.62-125.00-180.00   90
 10  \w   -118.00 -72.00   0.50    0.05    --  -46.62-125.00 150.00   92
 11  \w   -137.00 -85.00   0.50    0.05    -- -100.00 -15.00 -90.00  104
 12  \w   -160.00-122.00   0.50    0.05    -- -100.00 -94.00  90.00   76
 13  \w   -117.00 -91.00   0.50    0.05    -- -100.00  61.00   0.00   52
 14  \w    -69.00 -35.00   0.50    0.05    -- -100.00  61.00   0.00   68
 15  \w   -115.00 -28.00   0.50    0.05    -- -100.00  30.00 150.00  174
 16  \w   -114.00 -40.00   0.50    0.05    -- -100.00  15.00 -30.00  148
 17  \w     47.00  73.00   0.50    0.05    --  107.00 -94.00-120.00   52
 18  \w     35.00 101.00   0.50    0.05    --  107.00 -94.00-150.00  132
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0604594000
_diffrn_orient_matrix_UB_12      -0.0200750000
_diffrn_orient_matrix_UB_13      0.0490541000
_diffrn_orient_matrix_UB_21      0.0722153000
_diffrn_orient_matrix_UB_22      -0.1223782000
_diffrn_orient_matrix_UB_23      0.0477436000
_diffrn_orient_matrix_UB_31      0.0575416000
_diffrn_orient_matrix_UB_32      0.1324602000
_diffrn_orient_matrix_UB_33      0.0514919000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15072
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.512
_diffrn_reflns_theta_min         3.167
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.724
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.888
_refine_diff_density_min         -0.792
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4519
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0435
_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^)+(0.0602P)^2^+2.2579P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1172
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4067
_reflns_number_total             4519
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob02303h2.cif
_cod_data_source_block           liujw_190322_3
_cod_database_code               7157191
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.772
_shelx_estimated_absorpt_t_min   0.495
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 N11(H11), N20(H20), C29(H29), C31(H31), C25(H25), C33(H33), C4(H4), C32(H32),
 C22(H22), C30(H30), C7(H7), C5(H5), C6(H6), C23(H23), C24(H24)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_shelx_res_checksum              86645
_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 2.094
_oxdiff_exptl_absorpt_empirical_full_min 0.453