A Benzannulation Protocol To Prepare Substituted Aryl Amines Using a Michael-Aldol Reaction of β-Keto Sulfones
Sezgin Kiren; Albert Padwa; Journal of Organic Chemistry 74 (2009) 7781–7789; doi:10.1021/jo9017793

data_4024934
_publ_section_title
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A Benzannulation Protocol To Prepare Substituted Aryl Amines Using a
Michael-Aldol Reaction of \b-Keto Sulfones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7781
_journal_page_last               7789
_journal_paper_doi               10.1021/jo9017793
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C19 H21 N O3 S'
_chemical_formula_sum            'C19 H21 N O3 S'
_chemical_formula_weight         343.43
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.5358(6)
_cell_length_b                   15.504(3)
_cell_length_c                   19.766(2)
_cell_measurement_reflns_used    1272
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      55.97
_cell_measurement_theta_min      8.50
_cell_volume                     1696.5(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.848
_diffrn_measured_fraction_theta_max 0.849
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_sigmaI/netI    0.0653
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7901
_diffrn_reflns_theta_full        65.87
_diffrn_reflns_theta_max         65.87
_diffrn_reflns_theta_min         8.50
_exptl_absorpt_coefficient_mu    1.834
_exptl_absorpt_correction_T_max  0.9303
_exptl_absorpt_correction_T_min  0.5275
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(3)
_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     217
_refine_ls_number_reflns         2429
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0473
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0530P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.1022
_reflns_number_gt                1953
_reflns_number_total             2429
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9017793_si_001.cif
_cod_data_source_block           sk01s
_cod_depositor_comments
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The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
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_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4024934