Facile C—N Bond Cleavage Promoted by Cuprous Oxide: Formation of C—C-Coupled Biimidazole from Its Methylene-Bridged Congener
Sabiah, Shahulhameed; Lee, Chen-Shiang; Hwang, Wen-Shu; Lin, Ivan J. B.; Organometallics 29 (2010) 290–293; doi:10.1021/om9010406

data_4063347
_publ_section_title
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 Facile C---N Bond Cleavage Promoted by Cuprous Oxide:
 Formation of C---C-Coupled Biimidazole from Its Methylene-Bridged Congener
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_journal_coden_ASTM              ORGND7
_journal_issue                   2
_journal_name_full               Organometallics
_journal_page_first              290
_journal_page_last               293
_journal_paper_doi               10.1021/om9010406
_journal_volume                  29
_journal_year                    2010
_chemical_formula_sum            'C18 H24 Cu2 F12 N8 P2'
_chemical_formula_weight         769.47
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.292(5)
_cell_length_b                   13.006(4)
_cell_length_c                   12.943(4)
_cell_measurement_reflns_used    9921
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.10
_cell_measurement_theta_min      2.21
_cell_volume                     2910.9(15)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       '\w and \f scan'
_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  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0151
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_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            32834
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.97
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    1.673
_exptl_absorpt_correction_T_max  0.722
_exptl_absorpt_correction_T_min  0.601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.756
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       square
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.809
_refine_diff_density_min         -1.092
_refine_diff_density_rms         0.178
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2688
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.164
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0676
_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^)+(0.1361P)^2^+6.5411P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2103
_refine_ls_wR_factor_ref         0.2261
_reflns_number_gt                2289
_reflns_number_total             2688
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om9010406_si_002.cif
_cod_data_source_block           714908
_cod_depositor_comments
;
 Updated bibliographic information.

 Antanas Vaitkus,
 2019-09-23
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_cod_original_sg_symbol_H-M      Pnma
_cod_database_code               4063347