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_4038137
_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         'C11 H10 F N O'
_chemical_formula_sum            'C11 H10 F N O'
_chemical_formula_weight         191.20
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-22
_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                   15.8646(10)
_cell_length_b                   5.3549(3)
_cell_length_c                   10.5519(6)
_cell_measurement_reflns_used    4166
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.9610
_cell_measurement_theta_min      3.7840
_cell_volume                     896.42(9)
_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 0.961
_diffrn_measured_fraction_theta_max 0.965
_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     -4.00  52.00   0.50   15.00    --    5.13-118.00  -5.00  112
  2  \w     21.00  74.00   0.50   15.00    --    5.13-159.00-158.00  106
  3  \w    -20.00  41.00   0.50   15.00    --    5.13 -99.00  60.00  122
  4  \w      0.00  75.00   0.50   15.00    --    5.13  19.00  60.00  150
  5  \w     -6.00  68.00   0.50   15.00    --    5.13  57.00  90.00  148
  6  \w      2.00  48.00   0.50   15.00    --    5.13  38.00-180.00   92
  7  \w    -18.00  29.00   0.50   15.00    --   -5.44 -99.00 -90.00   94
  8  \w    -28.00  59.00   0.50   15.00    --   -5.44  77.00-120.00  174
  9  \w    -64.00   2.00   0.50   15.00    --   -5.44 -57.00  90.00  132
 10  \w    -15.00  54.00   0.50   15.00    --   -5.44  57.00-180.00  138
;
_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      -0.0354959000
_diffrn_orient_matrix_UB_12      -0.0108206000
_diffrn_orient_matrix_UB_13      0.0403721000
_diffrn_orient_matrix_UB_21      -0.0264177000
_diffrn_orient_matrix_UB_22      -0.0169517000
_diffrn_orient_matrix_UB_23      -0.0536604000
_diffrn_orient_matrix_UB_31      0.0063446000
_diffrn_orient_matrix_UB_32      -0.1308999000
_diffrn_orient_matrix_UB_33      0.0035874000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14223
_diffrn_reflns_point_group_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.361
_diffrn_reflns_theta_min         3.805
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52177
_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 light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_description       cube
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 580 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         1743
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0590
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1060P)^2^+0.2420P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1610
_refine_ls_wR_factor_ref         0.1710
_reflns_Friedel_coverage         0.864
_reflns_Friedel_fraction_full    0.932
_reflns_Friedel_fraction_max     0.935
_reflns_number_gt                1460
_reflns_number_total             1743
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00023_si_002.cif
_cod_data_source_block           sba-19-08-19
_cod_database_code               4038137
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C44 H36 F4 N4 O4 '
_diffrn_oxdiff_ac3_digest_frames
;
01a9f5072178807467ed799fe8cb15efb7000250e95
;
_diffrn_oxdiff_ac3_digest_hkl
;
0107ccb83ac473616b7c4c9ca027100e3dc488
;
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.04
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C009(H00A,H00B), C00C(H00F,H00G), C00E(H00H,H00I)
2.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C00A(H00C)
;
_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 1.400
_oxdiff_exptl_absorpt_empirical_full_min 0.587