Cobalt-Catalyzed Intermolecular [2 + 2 + 2] Cycloaddition for the Synthesis of 1,3-Cyclohexadienes
Gerhard Hilt; Anna Paul; Klaus Harms; Journal of Organic Chemistry 73 (2008) 5187–5190; doi:10.1021/jo800735x

data_4023520
_publ_section_title
;
 Cobalt-Catalyzed Intermolecular [2 + 2 + 2] Cycloaddition
 for the Synthesis of 1,3-Cyclohexadienes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5187
_journal_page_last               5190
_journal_paper_doi               10.1021/jo800735x
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C13 H16 O4'
_chemical_formula_sum            'C13 H16 O4'
_chemical_formula_weight         236.26
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.466(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3889(19)
_cell_length_b                   6.1262(7)
_cell_length_c                   16.557(2)
_cell_measurement_reflns_used    2443
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.5
_cell_volume                     1198.7(3)
_computing_cell_refinement       'STOE CELL'
_computing_data_collection       'STOE EXPOSE'
_computing_data_reduction        'STOE INTEGRATE'
_computing_molecular_graphics    'DIAMOND 3.1'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'STOE IPDS'
_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  0.0371
_diffrn_reflns_av_sigmaI/netI    0.0808
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4718
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         3.45
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.804
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2319
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.805
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0359
_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^)+(0.0366P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0706
_refine_ls_wR_factor_ref         0.0800
_reflns_number_gt                1249
_reflns_number_total             2319
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800735x-File001_2.cif
_cod_data_source_block           6a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4023520