Heteroannulation Enabled by a Bimetallic Rh(III)/Ag(I) Relay Catalysis: Application in Total Synthesis of Aristolactams BII
Ji, Wei-Wei; Lin, E.; Li, Qingjiang; Wang, Honggen; Chem. Commun.  (2017) –; doi:10.1039/C7CC02105D

data_7120058
_publ_section_title
;
 Heteroannulation Enabled by a Bimetallic Rh(III)/Ag(I) Relay Catalysis:
 Application in Total Synthesis of Aristolactams BII
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC02105D
_journal_year                    2017
_chemical_formula_moiety         'C16 H12 O5 S'
_chemical_formula_sum            'C16 H12 O5 S'
_chemical_formula_weight         316.34
_chemical_name_systematic
'(E)-(3-oxoisobenzofuran-1(3H)-ylidene)methyl 4-methylbenzenesulfonate'
_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_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-08-24
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-10-10 deposited with the CCDC.
2017-05-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.5457(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.99567(15)
_cell_length_b                   20.3803(3)
_cell_length_c                   8.08882(13)
_cell_measurement_reflns_used    4932
_cell_measurement_theta_max      72.0530
_cell_measurement_theta_min      2.1920
_cell_volume                     1447.55(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  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.2417
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.9583
_diffrn_measured_fraction_theta_max 0.9583
_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     19.00 114.00   1.00    2.00    --   44.52  57.00   0.00   95
  2  \w     85.00 114.00   1.00    2.00    --   44.52 125.00 120.00   29
  3  \w     30.00 119.00   1.00    3.00    --  100.00 -45.00  60.00   89
  4  \w     33.00 114.00   1.00    3.00    --  100.00-125.00 -60.00   81
  5  \w     27.00 121.00   1.00    3.00    --  100.00-125.00 -30.00   94
  6  \w     69.00 160.00   1.00    3.00    --  100.00  77.00-150.00   91
  7  \w     73.00  98.00   1.00    2.00    --   44.52 125.00-180.00   25
  8  \w   -115.00 -84.00   1.00    2.00    --  -44.52-125.00   0.00   31
  9  \w   -125.00-100.00   1.00    2.00    --  -44.52 -99.00  60.00   25
 10  \w   -141.00-115.00   1.00    3.00    --  -90.00 -45.00   0.00   26
 11  \w   -144.00 -86.00   1.00    3.00    --  -90.00 -61.00 -60.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1450441000
_diffrn_orient_matrix_UB_12      0.0373045000
_diffrn_orient_matrix_UB_13      -0.0865989000
_diffrn_orient_matrix_UB_21      -0.0951014000
_diffrn_orient_matrix_UB_22      -0.0432604000
_diffrn_orient_matrix_UB_23      0.0942805000
_diffrn_orient_matrix_UB_31      0.0260816000
_diffrn_orient_matrix_UB_32      0.0495648000
_diffrn_orient_matrix_UB_33      0.1471957000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            6373
_diffrn_reflns_theta_full        72.3225
_diffrn_reflns_theta_max         72.32
_diffrn_reflns_theta_min         4.34
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.193
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.02694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.4514
_exptl_crystal_F_000             659.5614
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethyl acetate/petroleum ether'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.3160
_refine_diff_density_min         -0.4892
_refine_diff_density_rms         0.0566
_refine_ls_d_res_high            0.8091
_refine_ls_d_res_low             10.1901
_refine_ls_goodness_of_fit_ref   1.0436
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    22
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2732
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0436
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.0864
_refine_ls_shift/su_mean         0.0014
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0678P)^2^+0.5779P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1099
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              24
_reflns_limit_k_min              0
_reflns_limit_l_max              9
_reflns_limit_l_min              0
_reflns_number_gt                2536
_reflns_number_total             2732
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c7cc02105d2.cif
_cod_data_source_block           jww_160815
_cod_database_code               7120058
_reflns_odcompleteness_completeness 99.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C18(H18), C13(H13), C8(H8), C9(H9), C21(H21), C1(H1), C19(H19),
 C7(H7)
2.b Idealised Me refined as rotating group:
 C11(H11a,H11b,H11c)
;
_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 39.314
_oxdiff_exptl_absorpt_empirical_full_min 0.537