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_4513962
_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_formula_moiety         'C19 H17 N O4 S'
_chemical_formula_sum            'C19 H17 N O4 S'
_chemical_formula_weight         355.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-06-17
_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                 90.4024(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.28582(14)
_cell_length_b                   9.52978(12)
_cell_length_c                   16.5640(2)
_cell_measurement_reflns_used    9295
_cell_measurement_temperature    180.2(7)
_cell_measurement_theta_max      74.2011
_cell_measurement_theta_min      4.2984
_cell_volume                     1623.59(4)
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      180.2(7)
_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 0.984
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

--------------------------------------------------------------------------
  1  \w    -52.00  34.00   1.00    1.00    --  -41.08  77.00 150.00   86
  2  \w   -115.00 -42.00   1.00    1.00    --  -41.08 -38.00  60.00   73
  3  \w   -113.00 -78.00   1.00    1.00    --  -41.08-135.00 103.00   35
  4  \w    151.00 176.00   1.00    2.00    --  108.11 125.00 150.00   25
  5  \w    105.00 175.00   1.00    2.00    --  108.11 125.00 -30.00   70
  6  \w    139.00 168.00   1.00    2.00    --  108.11 125.00 -90.00   29
  7  \w    115.00 144.00   1.00    2.00    --  108.11  61.00-150.00   29
  8  \w     84.00 167.00   1.00    2.00    --  108.11  30.00-180.00   83
  9  \w     70.00 109.00   1.00    2.00    --  108.11 -94.00 -30.00   39
 10  \w     76.00 101.00   1.00    1.00    --   41.08-133.00  12.00   25
 11  \w     39.00 132.00   1.00    2.00    --  108.11 -45.00   0.00   93
 12  \w     94.00 121.00   1.00    2.00    --  108.11-125.00-180.00   27
 13  \w     37.00  63.00   1.00    2.00    --  108.11 -45.00-120.00   26
 14  \w    -37.00  -8.00   1.00    1.00    --  -41.08 -77.00-150.00   29
 15  \w   -115.00 -85.00   1.00    1.00    --  -41.08 -77.00-180.00   30
 16  \w   -114.00 -79.00   1.00    1.00    --  -41.08 -57.00-120.00   35
 17  \w   -121.00 -40.00   1.00    1.00    --  -41.08 178.00-180.00   81
 18  \w    -57.00  -8.00   1.00    1.00    --  -41.08 -77.00  90.00   49
 19  \w    -89.00 -18.00   1.00    1.00    --  -41.08 -38.00-120.00   71
 20  \w    -64.00 -12.00   1.00    1.00    --  -41.08 -77.00-180.00   52
 21  \w   -117.00 -68.00   1.00    1.00    --  -41.08 -77.00-150.00   49
 22  \w    -86.00  -9.00   1.00    1.00    --  -41.08 -77.00   0.00   77
 23  \w    -39.00 -14.00   1.00    1.00    --  -41.08 -57.00-120.00   25
 24  \w     62.00  88.00   1.00    1.00    --   41.08 178.00  90.00   26
 25  \w     57.00 107.00   1.00    1.00    --   41.08 178.00 150.00   50
 26  \w     26.00  63.00   1.00    1.00    --   41.08  19.00  90.00   37
 27  \w     77.00 104.00   1.00    2.00    --  108.11  77.00 120.00   27
 28  \w     79.00 105.00   1.00    2.00    --  108.11  61.00-180.00   26
 29  \w     76.00 175.00   1.00    2.00    --  108.11  77.00 -60.00   99
 30  \w     76.00 102.00   1.00    2.00    --  108.11  77.00  30.00   26
 31  \w    147.00 174.00   1.00    2.00    --  108.11  77.00 150.00   27
 32  \w     76.00 106.00   1.00    2.00    --  108.11  77.00  90.00   30
 33  \w    111.00 172.00   1.00    2.00    --  108.11  77.00 -90.00   61
 34  \w     76.00 102.00   1.00    2.00    --  108.11  77.00 -90.00   26
 35  \w     76.00 102.00   1.00    2.00    --  108.11  77.00 150.00   26
 36  \w     76.00 102.00   1.00    2.00    --  108.11  77.00   0.00   26
 37  \w     79.00 136.00   1.00    2.00    --  108.11  61.00   0.00   57
 38  \w     76.00 102.00   1.00    2.00    --  108.11  77.00-120.00   26
 39  \w    110.00 141.00   1.00    2.00    --  108.11  77.00-120.00   31
;
_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      0.0011826000
_diffrn_orient_matrix_UB_12      -0.1181851000
_diffrn_orient_matrix_UB_13      -0.0635043000
_diffrn_orient_matrix_UB_21      0.0000227000
_diffrn_orient_matrix_UB_22      0.1104065000
_diffrn_orient_matrix_UB_23      -0.0679241000
_diffrn_orient_matrix_UB_31      0.1497366000
_diffrn_orient_matrix_UB_32      0.0008440000
_diffrn_orient_matrix_UB_33      0.0011968000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15454
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.197
_diffrn_reflns_theta_min         4.298
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.990
_exptl_absorpt_correction_T_max  0.873
_exptl_absorpt_correction_T_min  0.593
_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    1.454
_exptl_crystal_description       prism
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.496
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.072
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3251
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0333
_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^)+(0.0477P)^2^+0.7426P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0914
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2995
_reflns_number_total             3251
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs6b02238_si_007.cif
_cod_data_source_block           gb1085
_cod_depositor_comments
'Adding full bibliography for 4513960--4513963.cif.'
_cod_database_code               4513962
_chemical_oxdiff_formula         'C19 H17 O4 S1 N1'
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 Ternary CH refined with riding coordinates:
 C12(H12), C13(H13), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C18(H18), C19(H19), C22(H22), C23(H23),
 C25(H25)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_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 1.297
_oxdiff_exptl_absorpt_empirical_full_min 0.585