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_4513960
_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         'C11 H13 N O3 S'
_chemical_formula_sum            'C11 H13 N O3 S'
_chemical_formula_weight         239.28
_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
_audit_creation_date             2015-09-22
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.09.21 svn.r3230 for OlexSys, GUI svn.r5097)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.9032(12)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.45565(11)
_cell_length_b                   18.07717(20)
_cell_length_c                   13.18336(16)
_cell_measurement_reflns_used    8187
_cell_measurement_temperature    180.00(14)
_cell_measurement_theta_max      73.4040
_cell_measurement_theta_min      4.1980
_cell_volume                     2187.43(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'SIR2004 (Burla et al., 2007)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details
;
  1 omega  -48.00   32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365   38.0000   30.0000 80

  2 omega   67.00  128.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.9365  178.0000 -180.0000 61

  3 omega   86.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.9365  178.0000  -90.0000 26

  4 omega   69.00   95.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.9365  178.0000  -60.0000 26

  5 omega  123.00  165.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  111.0000  -30.0000 42

  6 omega   91.00  174.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   30.0000 -120.0000 83

  7 omega   83.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000 -180.0000 95

  8 omega   72.00  108.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -94.0000  -30.0000 36

  9 omega   90.00  116.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499 -111.0000 -120.0000 26

 10 omega   59.00   89.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -30.0000 -150.0000 30

 11 omega   55.00  143.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -77.0000 -150.0000 88

 12 omega   49.00  108.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499 -111.0000 -180.0000 59

 13 omega   38.00   92.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -45.0000  -60.0000 54

 14 omega   41.00   67.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -94.0000  -30.0000 26

 15 omega   35.00   97.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -45.0000   30.0000 62

 16 omega   50.00  109.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -94.0000   60.0000 59

 17 omega   31.00   91.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -30.0000   60.0000 60

 18 omega   29.00   90.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -30.0000  120.0000 61

 19 omega   27.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.9365 -124.0000  -44.0000 57

 20 omega   28.00   60.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499 -111.0000 -120.0000 32

 21 omega   32.00   88.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -30.0000 -180.0000 56

 22 omega -131.00   24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365    0.0000    0.0000 155
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0197784000
_diffrn_orient_matrix_UB_12      0.0845942000
_diffrn_orient_matrix_UB_13      0.0055142000
_diffrn_orient_matrix_UB_21      0.1103706000
_diffrn_orient_matrix_UB_22      -0.0077740000
_diffrn_orient_matrix_UB_23      0.1064197000
_diffrn_orient_matrix_UB_31      0.1248819000
_diffrn_orient_matrix_UB_32      -0.0064000000
_diffrn_orient_matrix_UB_33      -0.0560889000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14538
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.680
_diffrn_reflns_theta_max         73.372
_diffrn_reflns_theta_min         4.233
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.579
_exptl_absorpt_correction_T_max  0.889
_exptl_absorpt_correction_T_min  0.504
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.453
_exptl_crystal_description       plate
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.4011
_exptl_crystal_size_mid          0.2527
_exptl_crystal_size_min          0.046
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4336
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0361
_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^)+(0.0524P)^2^+0.6060P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.0974
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3862
_reflns_number_total             4336
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs6b02238_si_003.cif
_cod_data_source_block           vb274
_cod_depositor_comments
'Adding full bibliography for 4513960--4513963.cif.'
_cod_database_code               4513960
_chemical_oxdiff_formula         'C11 H13 N O3 S'
_reflns_odcompleteness_completeness 99.93
_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:
 C10B(H10B), C10A(H10A), C6B(H6B), C6A(H6A)
2.b Secondary CH2 refined with riding coordinates:
 C9A(H9AA,H9AB), C8B(H8BA,H8BB), C9B(H9BA,H9BB), C8A(H8AA,H8AB)
2.c Aromatic/amide H refined with riding coordinates:
 C13B(H13B), C12A(H12A), C12B(H12B), C15B(H15B), C14B(H14B), C15A(H15A),
 C13A(H13A), C14A(H14A)
2.d Idealised Me refined as rotating group:
 C4A(H4AA,H4AB,H4AC), C4B(H4BA,H4BB,H4BC)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'