Bismuth(iii)-catalyzed regioselective alkylation of tetrahydroquinolines and indolines towards the synthesis of bioactive core-biaryl oxindoles and CYP19 inhibitors.
Prusty, Namrata; Kinthada, Lakshmana K.; Meena, Rohit; Chebolu, Rajesh; Ravikumar, Ponneri Chandrababu; Organic & biomolecular chemistry 19 (2021) 891–905; doi:10.1039/d0ob02385j

data_7157820
_publ_section_title
;
 Bismuth(iii)-catalyzed regioselective alkylation of tetrahydroquinolines
 and indolines towards the synthesis of bioactive core-biaryl oxindoles
 and CYP19 inhibitors.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              891
_journal_page_last               905
_journal_paper_doi               10.1039/d0ob02385j
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C27 H27 N3 O2'
_chemical_formula_sum            'C27 H27 N3 O2'
_chemical_formula_weight         425.51
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-10-27
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_audit_update_record
;
2020-11-02 deposited with the CCDC.	2020-12-16 downloaded from the CCDC.
;
_cell_angle_alpha                95.916(2)
_cell_angle_beta                 102.954(2)
_cell_angle_gamma                111.833(2)
_cell_formula_units_Z            2
_cell_length_a                   9.8262(2)
_cell_length_b                   10.2492(2)
_cell_length_c                   14.6317(3)
_cell_measurement_reflns_used    16270
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      77.2780
_cell_measurement_theta_min      4.7290
_cell_volume                     1304.44(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_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      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -77.00  14.00   0.50    0.25    --  -38.50 104.00  41.00  182
  2  \w      7.00  87.00   0.50    0.25    --   48.56-104.00 -59.00  160
  3  \w    104.00 175.00   0.50    0.99    --  106.21 104.00  41.00  142
  4  \w     38.00 108.00   0.50    0.99    --  106.21-104.00 -59.00  140
  5  \w    -42.00  28.00   0.50    0.25    --  -38.50  37.00 150.00  140
  6  \w    -50.00  24.00   0.50    0.25    --  -38.50  57.00-120.00  148
  7  \w   -101.00 -22.00   0.50    0.25    --  -38.50 -66.00 -92.81  158
  8  \w    -42.00  28.00   0.50    0.25    --  -38.50  37.00-180.00  140
  9  \w    -62.00  26.00   0.50    0.25    --  -38.50  77.00  30.00  176
 10  \w    -18.00  52.00   0.50    0.25    --   48.56 -37.00 120.00  140
 11  \w     38.00 110.00   0.50    0.99    --  106.21 -30.00 150.00  144
 12  \w    103.00 171.00   0.50    0.99    --  106.21  77.00 120.00  136
 13  \w     42.00 111.00   0.50    0.99    --  106.21 -45.00 120.00  138
 14  \w     37.00 109.00   0.50    0.99    --  106.21-111.00-150.00  144
 15  \w     44.00 119.00   0.50    0.99    --  106.21 -61.00 -30.00  150
 16  \w     38.00 106.00   0.50    0.99    --  106.21 -94.00-180.00  136
 17  \w     38.00 106.00   0.50    0.99    --  106.21 -94.00 -30.00  136
 18  \w    104.00 176.00   0.50    0.99    --  106.21 111.00  60.00  144
 19  \w     37.00 109.00   0.50    0.99    --  106.21-111.00 150.00  144
 20  \w     42.00 111.00   0.50    0.99    --  106.21 -45.00  30.00  138
 21  \w     38.00 114.00   0.50    0.99    --  106.21 -15.00 -90.00  152
 22  \w     37.00 109.00   0.50    0.99    --  106.21-111.00 -90.00  144
 23  \w     37.00 109.00   0.50    0.99    --  106.21-111.00  90.00  144
 24  \w    103.00 174.00   0.50    0.99    --  106.21  30.00-150.00  142
 25  \w     93.00 169.00   0.50    0.99    --  106.21  61.00 -60.00  152
 26  \w    104.00 176.00   0.50    0.99    --  106.21 111.00 150.00  144
 27  \w     37.00 109.00   0.50    0.99    --  106.21-111.00  30.00  144
 28  \w     38.00 110.00   0.50    0.99    --  106.21 -30.00   0.00  144
 29  \w    103.00 171.00   0.50    0.99    --  106.21  77.00  30.00  136
 30  \w    103.00 171.00   0.50    0.99    --  106.21  77.00-180.00  136
 31  \w     38.00 106.00   0.50    0.99    --  106.21 -94.00 120.00  136
 32  \w    103.00 174.00   0.50    0.99    --  106.21  30.00 -30.00  142
 33  \w     37.00 112.00   0.50    0.25    --   48.56  57.00 120.00  150
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0078032000
_diffrn_orient_matrix_UB_12      -0.0473713000
_diffrn_orient_matrix_UB_13      -0.1051324000
_diffrn_orient_matrix_UB_21      0.1608017000
_diffrn_orient_matrix_UB_22      0.1184522000
_diffrn_orient_matrix_UB_23      0.0161062000
_diffrn_orient_matrix_UB_31      0.0715244000
_diffrn_orient_matrix_UB_32      -0.1053938000
_diffrn_orient_matrix_UB_33      0.0296298000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19586
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.250
_diffrn_reflns_theta_min         4.750
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.548
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89169
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic whiteish white'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.083
_exptl_crystal_description       cube
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4776
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0360
_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^)+(0.0400P)^2^+0.6457P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0912
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4531
_reflns_number_total             4776
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob02385j5.cif
_cod_data_source_block           ila-299
_cod_depositor_comments
;
Adding full bibliography for 7157820--7157821.cif.

2025-03-31
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C54 H54 N6 O4'
_cod_original_formula_weight         851.03
_cod_original_formula_moiety         '2(C27 H27 N3 O2)'
_cod_original_formula_units_Z            1
_cod_database_code               7157820
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C62 H70 N6 O8 '
_diffrn_oxdiff_digest_frames
;
0101433b83f6d2f68d090b5652bdfc0b6b00049baee
;
_diffrn_oxdiff_digest_hkl
;
0178e22c03d23a1d0739b4ee4530f18fc8a421
;
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 Riding coordinates:
 N006(H006)
2.b Secondary CH2 refined with riding coordinates:
 C00T(H00A,H00B), C00U(H00D,H00F), C00V(H00G,H00H), C00X(H00S,H00T), C00Y(H00U,
 H00V), C011(H01A,H01B)
2.c Aromatic/amide H refined with riding coordinates:
 N004(H004), N005(H005), C00C(H00C), C00E(H00E), C00J(H00J), C00L(H00L),
 C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00R(H00R)
2.d Idealised Me refined as rotating group:
 C00W(H00I,H00K,H00Q)
;
_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 1.347
_oxdiff_exptl_absorpt_empirical_full_min 0.764