Cobalt-Catalyzed One-Step Access to Pyroquilon and C-7 Alkenylation of Indoline with Activated Alkenes Using Weakly Coordinating Functional Group.
Banjare, Shyam Kumar; Biswal, Pragati; Ravikumar, Ponneri Chandrababu; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00023

data_4038136
_publ_section_title
;
 Cobalt-Catalyzed One-Step Access to Pyroquilon and C-7 Alkenylation of
 Indoline with Activated Alkenes Using Weakly Coordinating Functional
 Group.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00023
_journal_year                    2020
_chemical_formula_moiety         'C17 H21 N O3'
_chemical_formula_sum            'C17 H21 N O3'
_chemical_formula_weight         287.35
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-15
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.6762(8)
_cell_length_b                   15.5082(6)
_cell_length_c                   6.18290(10)
_cell_measurement_reflns_used    5554
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      77.5220
_cell_measurement_theta_min      5.3870
_cell_volume                     1599.01(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46b (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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.971
_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    -91.00  -4.00   0.50    2.00    --  -38.50 127.00 -99.00  174
  2  \w   -100.00 -12.00   0.50    2.00    --  -38.50 143.00  70.00  176
  3  \w     34.00 112.00   0.50    2.00    --   49.56-143.00  14.00  156
  4  \w     25.00 102.00   0.50    2.00    --   49.56-127.00-175.00  154
  5  \w     93.00 172.00   0.50    8.00    --  107.46 127.00 -99.00  158
  6  \w     43.00 119.00   0.50    8.00    --  107.46-127.00-175.00  152
  7  \w     58.00 112.00   0.50    8.00    --  107.46-143.00  14.00  108
  8  \w    103.00 128.00   0.50    8.00    --  107.46 143.00  70.00   50
  9  \w   -100.00 -37.00   0.50    2.00    --  -38.50 -57.00  30.00  126
 10  \w     29.00 112.00   0.50    2.00    --   49.56  77.00-120.00  166
 11  \w     46.00  79.00   0.50    2.00    --   49.56  37.00-180.00   66
 12  \w     54.00 120.00   0.50    8.00    --  107.46 -61.00-180.00  132
 13  \w     40.00 109.00   0.50    8.00    --  107.46 -30.00-120.00  138
 14  \w     45.00 105.00   0.50    8.00    --  107.46 -94.00  30.00  120
 15  \w     41.00 116.00   0.50    8.00    --  107.46 -15.00 150.00  150
 16  \w     40.00 109.00   0.50    8.00    --  107.46 -94.00 150.00  138
 17  \w    114.00 165.00   0.50    8.00    --  107.46  45.00-180.00  102
 18  \w     85.00 172.00   0.50    8.00    --  107.46  77.00 150.00  174
 19  \w    106.00 134.00   0.50    8.00    --  107.46  45.00 -90.00   56
 20  \w     48.00  74.00   0.50    8.00    --  107.46 -30.00 120.00   52
;
_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      0.0674326000
_diffrn_orient_matrix_UB_12      -0.0668685000
_diffrn_orient_matrix_UB_13      -0.0306062000
_diffrn_orient_matrix_UB_21      0.0630056000
_diffrn_orient_matrix_UB_22      0.0724756000
_diffrn_orient_matrix_UB_23      0.0128985000
_diffrn_orient_matrix_UB_31      0.0050859000
_diffrn_orient_matrix_UB_32      -0.0120285000
_diffrn_orient_matrix_UB_33      0.2468158000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1212
_diffrn_reflns_av_unetI/netI     0.0814
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            10754
_diffrn_reflns_point_group_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.504
_diffrn_reflns_theta_min         3.892
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.657
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26614
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46b (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_description       needle
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
;
 Flack x determined using 618 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3051
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0795
_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^)+(0.1490P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1977
_refine_ls_wR_factor_ref         0.2221
_reflns_Friedel_coverage         0.649
_reflns_Friedel_fraction_full    0.902
_reflns_Friedel_fraction_max     0.877
_reflns_number_gt                2240
_reflns_number_total             3051
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00023_si_003.cif
_cod_data_source_block           pcr-sba-heck
_cod_database_code               4038136
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C68 H88 N8 O8 '
_diffrn_oxdiff_ac3_digest_frames
;
019011486c6e70efde3b35a92fb9a3e5e500030e253
;
_diffrn_oxdiff_ac3_digest_hkl
;
019781c4bed29521a5b38317794229c8b20b47
;
_reflns_odcompleteness_completeness 99.31
_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.a Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B), C00C(H00D,H00E)
2.b Aromatic/amide H refined with riding coordinates:
 C00B(H00C), C00D(H00F), C00E(H00G), C00F(H00H), C00G(H00I)
2.c Idealised Me refined as rotating group:
 C00I(H00J,H00K,H00L), C00J(H00M,H00N,H00O), C00K(H00P,H00Q,H00R), C00L(H00S,
 H00T,H00U)
;
_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 5.333
_oxdiff_exptl_absorpt_empirical_full_min 0.133