Pd-catalyzed tandem sp2-sp3 coupling reactions of chiral stannolanes: an efficient preparation of optically active tetrahydrobenz[f]isoindoles.
Kamimura, Akio; So, Masahiro; Ishikawa, Shingo; Uno, Hidemitsu; Organic letters 15 (2013) 1402–1405; doi:10.1021/ol4003948

data_1511902
_publ_section_title
;
 Pd-catalyzed tandem sp2-sp3 coupling reactions of chiral stannolanes: an
 efficient preparation of optically active tetrahydrobenz[f]isoindoles.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1402
_journal_page_last               1405
_journal_paper_doi               10.1021/ol4003948
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C20 H21 N O3 S'
_chemical_formula_sum            'C20 H21 N O3 S'
_chemical_formula_weight         355.45
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 101.281(6)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   7.062(3)
_cell_length_b                   9.027(4)
_cell_length_c                   13.891(7)
_cell_measurement_reflns_used    3646
_cell_measurement_temperature    100
_cell_measurement_theta_max      31.28
_cell_measurement_theta_min      1.50
_cell_volume                     868.4(7)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 7.111
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0429
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7152
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             376.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.230
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1740 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.01(6)
_refine_ls_extinction_coef       0.020(2)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3842
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0320
_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^)+(0.0395P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0691
_refine_ls_wR_factor_ref         0.0711
_reflns_number_gt                3472
_reflns_number_total             3842
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol4003948_si_003.cif
_cod_data_source_block           sou07130A-1
_cod_depositor_comments
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The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 
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_cod_database_code               1511902