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_7157821
_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         'C22 H21 N O2 S'
_chemical_formula_sum            'C23.5 H22.5 N1.5 O3.5 S'
_chemical_formula_weight         413.99
_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   geom
_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                86.787(2)
_cell_angle_beta                 70.290(2)
_cell_angle_gamma                89.647(2)
_cell_formula_units_Z            4
_cell_length_a                   11.5475(3)
_cell_length_b                   11.5869(3)
_cell_length_c                   16.7480(3)
_cell_measurement_reflns_used    21469
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.4610
_cell_measurement_theta_min      3.8120
_cell_volume                     2106.08(9)
_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      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.985
_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   -104.00 -17.00   0.50    3.66    --  -38.50 150.00 -39.00  174
  2  \w    -85.00  -3.00   0.50    3.66    --  -38.50 122.00 158.00  164
  3  \w     25.00  98.00   0.50    3.66    --   48.56-122.00  77.00  146
  4  \w     39.00 116.00   0.50    3.66    --   48.56-150.00 -84.00  154
  5  \w     41.00 110.00   0.50    3.66    --  106.21-122.00  77.00  138
  6  \w     83.00 166.00   0.50    3.66    --  106.21 150.00 -39.00  166
  7  \w     99.00 172.00   0.50    3.66    --  106.21 122.00 158.00  146
  8  \w    -42.00  28.00   0.50    3.66    --  -38.50  37.00  60.00  140
  9  \w    -42.00  28.00   0.50    3.66    --  -38.50  37.00 120.00  140
 10  \w   -105.00 -35.00   0.50    3.66    --  -38.50 -37.00 -90.00  140
 11  \w     37.00 112.00   0.50    3.66    --   48.56  57.00-180.00  150
 12  \w     37.00 112.00   0.50    3.66    --   48.56  57.00 -90.00  150
 13  \w     45.00 115.00   0.50    3.66    --   48.56  37.00-180.00  140
 14  \w     42.00 111.00   0.50    3.66    --  106.21 -45.00   0.00  138
 15  \w     38.00 110.00   0.50    3.66    --  106.21 -30.00 -90.00  144
 16  \w     38.00 110.00   0.50    3.66    --  106.21 -30.00  60.00  144
 17  \w     37.00 109.00   0.50    3.66    --  106.21-111.00   0.00  144
 18  \w    102.00 171.00   0.50    3.66    --  106.21  45.00-180.00  138
 19  \w     42.00 130.00   0.50    3.66    --  106.21 -77.00   0.00  176
 20  \w     38.00 106.00   0.50    3.66    --  106.21 -94.00  60.00  136
 21  \w     38.00 114.00   0.50    3.66    --  106.21 -15.00 120.00  152
 22  \w     42.00 111.00   0.50    3.66    --  106.21 -45.00-180.00  138
 23  \w    103.00 171.00   0.50    3.66    --  106.21  77.00-150.00  136
 24  \w    104.00 176.00   0.50    3.66    --  106.21 111.00 -60.00  144
 25  \w     58.00  84.00   0.50    3.66    --  106.21 -94.00 -90.00   52
 26  \w     47.00 114.00   0.50    3.66    --  106.21 -15.00-120.00  134
 27  \w     69.00 119.00   0.50    3.66    --  106.21 -61.00  60.00  100
 28  \w    106.00 165.00   0.50    3.66    --  106.21  77.00  60.00  118
 29  \w     57.00 106.00   0.50    3.66    --  106.21 -94.00   0.00   98
 30  \w     47.00  93.00   0.50    3.66    --  106.21-111.00 150.00   92
 31  \w    103.00 167.00   0.50    3.66    --  106.21  15.00 -90.00  128
 32  \w    113.00 175.00   0.50    3.66    --  106.21 111.00 -90.00  124
 33  \w     72.00 109.00   0.50    3.66    --  106.21-111.00-120.00   74
 34  \w     41.00 106.00   0.50    3.66    --  106.21 -94.00-120.00  130
 35  \w     74.00 103.00   0.50    3.66    --  106.21 -94.00 120.00   58
 36  \w     64.00 113.00   0.50    3.66    --  106.21 -61.00-150.00   98
 37  \w    141.00 171.00   0.50    3.66    --  106.21  45.00  90.00   60
 38  \w     74.00  99.00   0.50    3.66    --  106.21-150.00 -84.00   50
;
_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      0.0570922000
_diffrn_orient_matrix_UB_12      -0.1092685000
_diffrn_orient_matrix_UB_13      -0.0453052000
_diffrn_orient_matrix_UB_21      -0.0378567000
_diffrn_orient_matrix_UB_22      -0.0694762000
_diffrn_orient_matrix_UB_23      0.0862386000
_diffrn_orient_matrix_UB_31      -0.1240726000
_diffrn_orient_matrix_UB_32      -0.0311439000
_diffrn_orient_matrix_UB_33      -0.0094334000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1143
_diffrn_reflns_av_unetI/netI     0.0613
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            28843
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.250
_diffrn_reflns_theta_min         3.821
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.599
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40302
_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            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_description       plate
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.933
_refine_diff_density_min         -0.820
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         7581
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1033
_refine_ls_R_factor_gt           0.0996
_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^)+(0.1570P)^2^+4.0003P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2653
_refine_ls_wR_factor_ref         0.2693
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6925
_reflns_number_total             7581
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob02385j5.cif
_cod_data_source_block           pcr-np-231
_cod_depositor_comments
;
Adding full bibliography for 7157820--7157821.cif.

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C47 H45 N3 O7 S2'
_cod_original_formula_weight         827.98
_cod_original_formula_moiety         '2(C22 H21 N O2 S)'
_cod_original_formula_units_Z            2
_cod_database_code               7157821
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C59 H59 N59 O59 S59 '
_diffrn_oxdiff_digest_frames
;
01b7b3a3fd3baef4154724fdf772ba3dcd00028c42c
;
_diffrn_oxdiff_digest_hkl
;
01c2a4c05cbe2fd299b17abaad833259f2c4a3
;
_reflns_odcompleteness_completeness 99.94
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 C01I, C01K, C01J, C00U, C016, C01G
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
3.a Ternary CH refined with riding coordinates:
 C00J(H00J), C00M(H00M)
3.b Secondary CH2 refined with riding coordinates:
 C00V(H00D,H00F), C010(H01E,H01F), C014(H01K,H01L), C017(H01A,H01B)
3.c Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00G(H00G), C00I(H00I), C00K(H00K), C00N(H00N), C00O(H00O),
 C00Q(H00Q), C00W(H00W), C00X(H00X), C00Z(H00Z), C012(H012), C013(H013),
 C015(H015), C016(H016), C018(H018), C019(H019), C01B(H01M), C01C(H01C),
 C01D(H01D), C01E(H01N), C01F(H01O), C01G(H01P), C01H(H01H), C01I(H01Q),
 C01J(H01R), C01K(H01S)
3.d Idealised Me refined as rotating group:
 C00S(H00A,H00B,H00C), C011(H01G,H01I,H01J)
;
_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 3.532
_oxdiff_exptl_absorpt_empirical_full_min 0.276