Direct Access to Furoindolines by Palladium-Catalyzed Intermolecular Carboamination
Bizet, Vincent; Borrajo-Calleja, Gustavo M.; Besnard, Céline; Mazet, Clément; ACS Catalysis 6 (2016) 7183–; doi:10.1021/acscatal.6b02238

data_4513963
_publ_section_title
;
 Direct Access to Furoindolines by Palladium-Catalyzed Intermolecular
 Carboamination
;
_journal_issue                   10
_journal_name_full               'ACS Catalysis'
_journal_page_first              7183
_journal_paper_doi               10.1021/acscatal.6b02238
_journal_volume                  6
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H19 N O4 S'
_chemical_formula_sum            'C18 H19 N O4 S'
_chemical_formula_weight         345.40
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-06-13
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   5.45149(6)
_cell_length_b                   15.70940(12)
_cell_length_c                   38.6948(3)
_cell_measurement_reflns_used    26181
_cell_measurement_temperature    180.00(14)
_cell_measurement_theta_max      74.2650
_cell_measurement_theta_min      3.5780
_cell_volume                     3313.81(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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      180.00(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4679
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

--------------------------------------------------------------------------
  1  \w    -66.00 -30.00   1.00    4.50    --  -41.08 -19.00  60.00   36
  2  \w   -112.00 -23.00   1.00    4.50    --  -41.08 -38.00  30.00   89
  3  \w     44.00  69.00   1.00    4.50    --   41.08 -99.00-180.00   25
  4  \w     75.00 106.00   1.00   20.00    --  108.11 -94.00  30.00   31
  5  \w     40.00 134.00   1.00   20.00    --  108.11 -30.00  60.00   94
  6  \w     87.00 114.00   1.00   20.00    --  108.11  45.00 -90.00   27
  7  \w    115.00 148.00   1.00   20.00    --  108.11  45.00 -90.00   33
  8  \w    124.00 162.00   1.00   20.00    --  108.11 125.00-150.00   38
  9  \w     26.00  63.00   1.00   20.00    --  108.11 -94.00  30.00   37
 10  \w   -112.00  -8.00   1.00    4.50    --  -41.08 -77.00-180.00  104
 11  \w    -64.00 -11.00   1.00    4.50    --  -41.08 -77.00  30.00   53
 12  \w   -116.00 -89.00   1.00    4.50    --  -41.08 -77.00 120.00   27
 13  \w   -113.00 -13.00   1.00    4.50    --  -41.08 -57.00 -60.00  100
 14  \w    -64.00  33.00   1.00    4.50    --  -41.08  38.00-120.00   97
 15  \w   -111.00 -69.00   1.00    4.50    --  -41.08-137.00-100.00   42
 16  \w    -63.00  -8.00   1.00    4.50    --  -41.08 -77.00 120.00   55
 17  \w   -111.00  -8.00   1.00    4.50    --  -41.08 -77.00 -90.00  103
 18  \w     64.00  99.00   1.00    4.50    --   41.08 178.00-150.00   35
 19  \w     78.00 122.00   1.00    4.50    --   41.08 178.00 120.00   44
 20  \w     63.00 117.00   1.00    4.50    --   41.08 178.00  30.00   54
 21  \w     79.00 130.00   1.00   20.00    --  108.11  61.00 -60.00   51
 22  \w     80.00 105.00   1.00   20.00    --  108.11  61.00-150.00   25
 23  \w     79.00 105.00   1.00   20.00    --  108.11  61.00-180.00   26
 24  \w     79.00 124.00   1.00   20.00    --  108.11  61.00   0.00   45
 25  \w     26.00 106.00   1.00   20.00    --  108.11 -94.00 -90.00   80
 26  \w     79.00 105.00   1.00   20.00    --  108.11  61.00  90.00   26
 27  \w     47.00 106.00   1.00   20.00    --  108.11 -94.00-180.00   59
 28  \w     76.00 102.00   1.00   20.00    --  108.11  77.00-120.00   26
 29  \w    108.00 165.00   1.00   20.00    --  108.11  61.00-120.00   57
 30  \w     80.00 106.00   1.00   20.00    --  108.11  61.00-120.00   26
 31  \w     75.00 106.00   1.00   20.00    --  108.11 -94.00  90.00   31
 32  \w     82.00 157.00   1.00   20.00    --  108.11  61.00 150.00   75
 33  \w     76.00 102.00   1.00   20.00    --  108.11  77.00 150.00   26
 34  \w     79.00 105.00   1.00   20.00    --  108.11  61.00  30.00   26
 35  \w    128.00 155.00   1.00   20.00    --  108.11  61.00  30.00   27
 36  \w     79.00 140.00   1.00   20.00    --  108.11  61.00  60.00   61
 37  \w     76.00 102.00   1.00   20.00    --  108.11  77.00  90.00   26
 38  \w    111.00 177.00   1.00   20.00    --  108.11  77.00  90.00   66
 39  \w     76.00 178.00   1.00   20.00    --  108.11  77.00-180.00  102
 40  \w     79.00 135.00   1.00   20.00    --  108.11  61.00 -30.00   56
 41  \w     76.00 102.00   1.00   20.00    --  108.11  77.00 120.00   26
 42  \w     76.00 105.00   1.00   20.00    --  108.11  77.00  30.00   29
 43  \w     76.00 102.00   1.00   20.00    --  108.11  77.00 -90.00   26
 44  \w    129.00 155.00   1.00   20.00    --  108.11  61.00 120.00   26
 45  \w     76.00 178.00   1.00   20.00    --  108.11  77.00  60.00  102
 46  \w    153.00 178.00   1.00   20.00    --  108.11  77.00 -30.00   25
 47  \w     76.00 102.00   1.00   20.00    --  108.11  77.00-150.00   26
 48  \w     79.00 106.00   1.00   20.00    --  108.11  61.00 120.00   27
 49  \w     76.00 102.00   1.00   20.00    --  108.11  77.00 -30.00   26
 50  \w     76.00 102.00   1.00   20.00    --  108.11  77.00   0.00   26
 51  \w    113.00 178.00   1.00   20.00    --  108.11  77.00   0.00   65
 52  \w     76.00 133.00   1.00   20.00    --  108.11  77.00 -60.00   57
 53  \w    126.00 164.00   1.00   20.00    --  108.11  61.00-150.00   38
 54  \w     82.00 108.00   1.00   20.00    --  108.11  45.00 120.00   26
 55  \w     79.00 106.00   1.00   20.00    --  108.11  61.00 -90.00   27
 56  \w     25.00  91.00   1.00   20.00    --  108.11 -94.00   0.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0268842000
_diffrn_orient_matrix_UB_12      0.0909690000
_diffrn_orient_matrix_UB_13      0.0144152000
_diffrn_orient_matrix_UB_21      -0.0154445000
_diffrn_orient_matrix_UB_22      0.0350699000
_diffrn_orient_matrix_UB_23      -0.0371065000
_diffrn_orient_matrix_UB_31      -0.2808744000
_diffrn_orient_matrix_UB_32      -0.0105829000
_diffrn_orient_matrix_UB_33      0.0006671000
_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     0.0208
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            53917
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.268
_diffrn_reflns_theta_min         3.036
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.929
_exptl_absorpt_correction_T_max  0.946
_exptl_absorpt_correction_T_min  0.602
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.385
_exptl_crystal_description       plate
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.453
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.006(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     438
_refine_ls_number_reflns         6736
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0327
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0377P)^2^+0.9740P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0789
_refine_ls_wR_factor_ref         0.0798
_reflns_Friedel_coverage         0.727
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                6427
_reflns_number_total             6736
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs6b02238_si_004.cif
_cod_data_source_block           gb1060
_cod_depositor_comments
'Adding full bibliography for 4513960--4513963.cif.'
_cod_database_code               4513963
_chemical_oxdiff_formula         'C18 H19 N1 O4 S'
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.994(16) 0.006(16)
2. 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
3.a Ternary CH refined with riding coordinates:
 C12A(H12A), C14A(H14A), C16A(H16A), C12B(H12B), C14B(H14B), C16B(H16B)
3.b Secondary CH2 refined with riding coordinates:
 C13A(H13A,H13B), C13B(H13C,H13D)
3.c Aromatic/amide H refined with riding coordinates:
 C7A(H7A), C8A(H8A), C9A(H9A), C10A(H10A), C18A(H18A), C19A(H19A), C21A(H21A),
 C22A(H22A), C7B(H7B), C8B(H8B), C9B(H9B), C10B(H10B), C18B(H18B), C19B(H19B),
 C21B(H21B), C22B(H22B)
3.d Idealised Me refined as rotating group:
 C2A(H2AA,H2AB,H2AC), C24A(H24A,H24B,H24C), C2B(H2BA,H2BB,H2BC), C24B(H24D,
 H24E,H24F)
;
_shelx_shelxl_version_number     2014/7
_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 1.309
_oxdiff_exptl_absorpt_empirical_full_min 0.506