Copper-Catalyzed Multicomponent Cascade Process for the Synthesis of Hexahydro-1H-isoindolones
Lei Zhang; Helena C. Malinakova; Journal of Organic Chemistry 72 (2007) 1484–1487; doi:10.1021/jo0621773

data_4022691
_publ_contact_author
; 
   Prof. Helena Malinakova 
   Department of Chemistry -- University of Kansas
   Malott Hall
   1251 Wescoe Hall Dr, Rm 2010 
   Lawrence, KS  66045-7582  USA 
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_publ_contact_author_email       hmalinakova@ku.edu
_publ_contact_author_fax         1(785)8645396
_publ_contact_author_phone       1(785)8644743
_publ_section_title
;
 Copper-Catalyzed Multicomponent Cascade Process for the Synthesis
 of Hexahydro-1H-isoindolones
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_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1484
_journal_page_last               1487
_journal_paper_doi               10.1021/jo0621773
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C22 H22 Br N O'
_chemical_formula_weight         396.32
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                83.4900(10)
_cell_angle_beta                 71.0780(10)
_cell_angle_gamma                60.6110(10)
_cell_formula_units_Z            2
_cell_length_a                   9.9446(8)
_cell_length_b                   9.9850(8)
_cell_length_c                   11.1069(8)
_cell_measurement_reflns_used    5532
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.483
_cell_measurement_theta_min      2.453
_cell_volume                     907.62(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_sigmaI/netI    0.0493
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11045
_diffrn_reflns_theta_full        30.54
_diffrn_reflns_theta_max         30.54
_diffrn_reflns_theta_min         2.45
_diffrn_standards_decay_%        0.00
_exptl_absorpt_coefficient_mu    2.274
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.718
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Irregular plate'
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.976
_refine_diff_density_min         -0.818
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     314
_refine_ls_number_reflns         5450
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.969
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0350
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0477P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0834
_reflns_number_gt                4463
_reflns_number_total             5450
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0621773si20061019_111822.cif
_cod_data_source_block           k88b(11.1)
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value '/' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
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_cod_database_code               4022691