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_4513961
_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         'C17 H18 N2 O4 S'
_chemical_formula_sum            'C17 H18 N2 O4 S'
_chemical_formula_weight         346.39
_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     direct
_audit_creation_date             2016-06-16
_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                 90.8215(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.81121(10)
_cell_length_b                   8.41417(6)
_cell_length_c                   16.56980(18)
_cell_measurement_reflns_used    16817
_cell_measurement_temperature    180(3)
_cell_measurement_theta_max      74.2530
_cell_measurement_theta_min      4.6010
_cell_volume                     1646.56(3)
_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(3)
_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 0.994
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

--------------------------------------------------------------------------
  1  \w     98.00 178.00   0.50    1.00    --  108.11 125.00  60.00  160
  2  \w    102.00 127.00   0.50    0.50    --   41.08 178.00 -30.00   50
  3  \w     90.00 168.00   0.50    1.00    --  108.11  30.00-120.00  156
  4  \w    105.00 131.00   0.50    1.00    --  108.11 -30.00 -30.00   52
  5  \w     94.00 120.00   0.50    1.00    --  108.11-125.00  60.00   52
  6  \w     47.00  91.00   0.50    1.00    --  108.11 -30.00 -30.00   88
  7  \w     44.00 141.00   0.50    1.00    --  108.11 -77.00 -30.00  194
  8  \w    101.00 128.00   0.50    0.50    --   41.08-178.00 -90.00   54
  9  \w     61.00 134.00   0.50    1.00    --  108.11 -30.00-120.00  146
 10  \w    -31.00  68.00   0.50    0.50    --   41.08 -57.00 120.00  198
 11  \w   -110.00 -12.00   0.50    0.50    --  -41.08 -77.00 -90.00  196
 12  \w    -42.00 -14.00   0.50    0.50    --  -41.08 -57.00 -90.00   56
 13  \w   -115.00 -17.00   0.50    0.50    --  -41.08 -38.00 120.00  196
 14  \w    -99.00 -38.00   0.50    0.50    --  -41.08-178.00 150.00  122
 15  \w    -88.00  -8.00   0.50    0.50    --  -41.08 -77.00   0.00  160
 16  \w   -114.00 -72.00   0.50    0.50    --  -41.08 -57.00 -90.00   84
 17  \w   -115.00  -8.00   0.50    0.50    --  -41.08 -77.00  90.00  214
 18  \w    -61.00  -9.00   0.50    0.50    --  -41.08 -77.00-180.00  104
 19  \w     57.00 107.00   0.50    0.50    --   41.08 178.00-180.00  100
 20  \w      2.00  65.00   0.50    0.50    --   41.08 -99.00   0.00  126
 21  \w     83.00 112.00   0.50    0.50    --   41.08  77.00-180.00   58
 22  \w    111.00 175.00   0.50    1.00    --  108.11  77.00 -90.00  128
 23  \w     76.00 105.00   0.50    1.00    --  108.11  77.00 -90.00   58
 24  \w     25.00 107.00   0.50    1.00    --  108.11 -94.00-150.00  164
 25  \w     76.00 175.00   0.50    1.00    --  108.11  77.00   0.00  198
 26  \w     79.00 110.00   0.50    1.00    --  108.11  61.00 -30.00   62
 27  \w     76.00 133.00   0.50    1.00    --  108.11  77.00 120.00  114
 28  \w     77.00 102.00   0.50    1.00    --  108.11  77.00  30.00   50
 29  \w     79.00 109.00   0.50    1.00    --  108.11  61.00  60.00   60
 30  \w     82.00 123.00   0.50    1.00    --  108.11  61.00-180.00   82
 31  \w     76.00 105.00   0.50    1.00    --  108.11  77.00-180.00   58
 32  \w     80.00 132.00   0.50    1.00    --  108.11  61.00  90.00  104
 33  \w     79.00 106.00   0.50    1.00    --  108.11  61.00  30.00   54
 34  \w     80.00 105.00   0.50    1.00    --  108.11  61.00 120.00   50
 35  \w     76.00 102.00   0.50    1.00    --  108.11  77.00-120.00   52
 36  \w     83.00 135.00   0.50    1.00    --  108.11  61.00 150.00  104
 37  \w     79.00 106.00   0.50    1.00    --  108.11  61.00 -60.00   54
 38  \w     76.00 102.00   0.50    1.00    --  108.11  77.00 -30.00   52
 39  \w     80.00 140.00   0.50    1.00    --  108.11  61.00   0.00  120
 40  \w     79.00 105.00   0.50    1.00    --  108.11  61.00-150.00   52
 41  \w     76.00 102.00   0.50    1.00    --  108.11  77.00-150.00   52
 42  \w    127.00 153.00   0.50    1.00    --  108.11  61.00-120.00   52
 43  \w    116.00 177.00   0.50    1.00    --  108.11  77.00 -60.00  122
 44  \w     77.00 103.00   0.50    1.00    --  108.11  77.00 -60.00   52
 45  \w     48.00 107.00   0.50    1.00    --  108.11 -94.00 120.00  118
 46  \w     76.00 103.00   0.50    1.00    --  108.11  77.00  60.00   54
 47  \w     76.00 102.00   0.50    1.00    --  108.11  77.00 150.00   52
 48  \w     76.00 102.00   0.50    1.00    --  108.11  77.00  90.00   52
 49  \w     79.00 104.00   0.50    1.00    --  108.11  61.00-120.00   50
 50  \w    115.00 178.00   0.50    1.00    --  108.11  77.00  30.00  126
 51  \w     79.00 106.00   0.50    1.00    --  108.11  61.00 -90.00   54
;
_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      -0.0277779000
_diffrn_orient_matrix_UB_12      0.1774641000
_diffrn_orient_matrix_UB_13      -0.0116303000
_diffrn_orient_matrix_UB_21      0.1272980000
_diffrn_orient_matrix_UB_22      0.0374541000
_diffrn_orient_matrix_UB_23      -0.0060868000
_diffrn_orient_matrix_UB_31      -0.0067579000
_diffrn_orient_matrix_UB_32      -0.0248886000
_diffrn_orient_matrix_UB_33      -0.0920447000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0127
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24429
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.223
_diffrn_reflns_theta_min         3.743
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.961
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.345
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
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    1.397
_exptl_crystal_description       plate
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.413
_exptl_crystal_size_min          0.157
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0069(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3339
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0310
_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^)+(0.0423P)^2^+0.6548P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0814
_refine_ls_wR_factor_ref         0.0820
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3232
_reflns_number_total             3339
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs6b02238_si_005.cif
_cod_data_source_block           gb1078
_cod_depositor_comments
'Adding full bibliography for 4513960--4513963.cif.'
_cod_database_code               4513961
_chemical_oxdiff_formula         'C17 H18 N2 O4 S1'
_reflns_odcompleteness_completeness 99.97
_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)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C24(H24A,H24B,H24C)
;
_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 3.330
_oxdiff_exptl_absorpt_empirical_full_min 0.389