Six-Component Reactions for the Stereoselective Synthesis of 3-Arylidene-2-oxindoles via Sequential One-Pot Ugi/Heck Carbocyclization/Sonogashira/Nucleophilic Addition
Morteza Bararjanian; Saeed Balalaie; Frank Rominger; Barahman Movassagh; Hamid Reza Bijanzadeh; Journal of Organic Chemistry 75 (2010) 2806–2812; doi:10.1021/jo902713x

data_4025402
_publ_contact_author_address
;      Department of Chemistry, Faculty of Science
       K. N. Toosi University of Technology
       P. O. Box: 15875-4416 
       Tehran
       Iran
;
_publ_contact_author_email       balalaie@yahoo.com
_publ_contact_author_fax         '+98 21 22853650'
_publ_contact_author_name        'Balalaie, Saeed'
_publ_contact_author_phone       '+98 21 22850266'
_publ_section_title
;
 Six-Component Reactions for the Stereoselective Synthesis of
 3-Arylidene-2-oxindoles via Sequential One-Pot Ugi/Heck
 Carbocyclization/Sonogashira/Nucleophilic Addition
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2806
_journal_page_last               2812
_journal_paper_doi               10.1021/jo902713x
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C35 H30 N2 O2'
_chemical_formula_weight         510.61
_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                111.777(8)
_cell_angle_beta                 111.332(7)
_cell_angle_gamma                92.411(9)
_cell_formula_units_Z            2
_cell_length_a                   10.483(4)
_cell_length_b                   12.555(5)
_cell_length_c                   12.698(5)
_cell_measurement_reflns_used    1948
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      22.40
_cell_measurement_theta_min      2.48
_cell_volume                     1415.0(10)
_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      200(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_sigmaI/netI    0.0748
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12768
_diffrn_reflns_theta_full        26.41
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.9941
_exptl_absorpt_correction_T_min  0.9673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;

Sheldrick, G. M. (2008). <i>SADABS</i>. University of G\"ottingen, Germany.

;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       polyhedron
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.190
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         5772
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.190
_refine_ls_R_factor_all          0.1385
_refine_ls_R_factor_gt           0.0908
_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^)+(0.0442P)^2^+0.5453P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1512
_refine_ls_wR_factor_ref         0.1671
_reflns_number_gt                3846
_reflns_number_total             5772
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo902713x_si_001.cif
_cod_data_source_block           sba45
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        1415.1(9)
_cod_database_code               4025402