Catalytic [2 + 2 + 2] and Thermal [4 + 2] Cycloaddition of 1,2-Bis(arylpropiolyl)benzenes
Ken Tanaka; Takeshi Suda; Keiichi Noguchi; Masao Hirano; Journal of Organic Chemistry 72 (2007) 2243–2246; doi:10.1021/jo0624546

data_4022803
_publ_contact_author_address
;
Department of Applied Chemistry
Graduate School of Engineering
Tokyo University of Agriculture and Technology
Koganei
Tokyo 184-8588
Japan
;
_publ_contact_author_email       tanaka-k@cc.tuat.ac.jp
_publ_contact_author_fax         +81-42-388-7037
_publ_contact_author_name        'Dr Ken Tanaka'
_publ_contact_author_phone       +81-42-388-7037
_publ_section_title
;
 Catalytic [2 + 2 + 2] and Thermal [4 + 2] Cycloaddition
 of 1,2-Bis(arylpropiolyl)benzenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2243
_journal_page_last               2246
_journal_paper_doi               10.1021/jo0624546
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C37 H27 Br O4'
_chemical_formula_sum            'C37 H27 Br O4'
_chemical_formula_weight         615.50
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2006-10-20
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.539(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.8942(7)
_cell_length_b                   8.4501(4)
_cell_length_c                   25.2995(13)
_cell_measurement_reflns_used    45026
_cell_measurement_temperature    193
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      3.2
_cell_volume                     2937.4(3)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      193
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotaing anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0319
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            55913
_diffrn_reflns_theta_full        68.20
_diffrn_reflns_theta_max         68.20
_diffrn_reflns_theta_min         3.22
_exptl_absorpt_coefficient_mu    2.228
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.689
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
    Higashi, T. (1999). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.911
_refine_diff_density_min         -1.108
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881. 4863 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     802
_refine_ls_number_reflns         10634
_refine_ls_number_restraints     163
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0695
_refine_ls_shift/su_max          0.047
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1262P)^2^+2.3874P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2001
_refine_ls_wR_factor_ref         0.2333
_reflns_number_gt                7221
_reflns_number_total             10634
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0624546si20061201_110211.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4022803