Palladium-Catalyzed [2 + 2 + 2] Cycloadditions of 3,4-Didehydrophenanthrene and 1,2-Didehydrotriphenylene
Carmen Romero; Diego Peña; Dolores Pérez; Enrique Guitián; Journal of Organic Chemistry 73 (2008) 7996–8000; doi:10.1021/jo8013947

data_4023750
_publ_section_title
;
 Palladium-Catalyzed [2 + 2 + 2] Cycloadditions of
 3,4-Didehydrophenanthrene and 1,2-Didehydrotriphenylene
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7996
_journal_page_last               8000
_journal_paper_doi               10.1021/jo8013947
_journal_volume                  73
_journal_year                    2008
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C34 H22 O4'
_chemical_formula_structural     'C34 H22 O4'
_chemical_formula_sum            'C34 H22 O4'
_chemical_formula_weight         494.52
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/cifdics/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.1
_audit_creation_date             2000-06-05T14:01:15-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2008-05-22 # Formatted by publCIF
;
_cell_angle_alpha                90
_cell_angle_beta                 92.398(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.5259(8)
_cell_length_b                   8.8322(5)
_cell_length_c                   18.6777(12)
_cell_measurement_reflns_used    22
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      42.43
_cell_measurement_theta_min      21.3
_cell_measurement_wavelength     1.54184
_cell_volume                     2394.2(2)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_orient_matrix_type
;
  x-axis points to radiation source
  the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_UB_11      -0.24944E-1
_diffrn_orient_matrix_UB_12      -0.96761E-1
_diffrn_orient_matrix_UB_13      -0.20554E-1
_diffrn_orient_matrix_UB_21      0.6811E-2
_diffrn_orient_matrix_UB_22      -0.48537E-1
_diffrn_orient_matrix_UB_23      0.48229E-1
_diffrn_orient_matrix_UB_31      -0.63908E-1
_diffrn_orient_matrix_UB_32      0.32806E-1
_diffrn_orient_matrix_UB_33      0.10776E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0644
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            4967
_diffrn_reflns_theta_full        75.91
_diffrn_reflns_theta_max         75.91
_diffrn_reflns_theta_min         3.78
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        3
_diffrn_standards_interval_count 176
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.716
_exptl_absorpt_correction_T_max  0.9449
_exptl_absorpt_correction_T_min  0.6898
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
        Number of psi-scan sets used was   7
        Theta correction was applied.
        Weighted transmission curves were used.
        No Fourier smoothing was applied.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.210
_refine_ls_extinction_coef       0.0033(3)
_refine_ls_extinction_expression
Fc\^*\^=kFc[1+0.001xFc\^2\^\l\^3\^/sin(2\q)]\^-1/4\^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     394
_refine_ls_number_reflns         4787
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.1252
_refine_ls_R_factor_gt           0.0498
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;  
 calc w=1/[\s\^2\^(Fo\^2\^)+(0.0817P)\^2\^+0.4765P] 
 where P=(Fo\^2\^+2Fc\^2\^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1303
_refine_ls_wR_factor_ref         0.1638
_reflns_number_gt                3600
_reflns_number_total             4787
_reflns_threshold_expression     I>2u(I)
_cod_data_source_file            jo8013947_si_001.cif
_cod_data_source_block           2000gt01
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4023750
_diffrn_standards_decay_corr_max 1.062
_diffrn_standards_decay_corr_min 0.964
_exptl_absorpt_correction_t_ave  0.9055
_exptl_absorpt_factor_mur        0.057