Intramolecular reductive double cyclization of o,o'-bis(arylcarbonyl)diphenylacetylenes: synthesis of ladder pi-conjugated skeletons.
Zhang, Hongyu; Karasawa, Takashi; Yamada, Hiroshi; Wakamiya, Atsushi; Yamaguchi, Shigehiro; Organic letters 11 (2009) 3076–3079; doi:10.1021/ol901148p

data_1504018
_publ_section_title
;
 Intramolecular reductive double cyclization of
 o,o'-bis(arylcarbonyl)diphenylacetylenes: synthesis of ladder
 pi-conjugated skeletons.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3076
_journal_page_last               3079
_journal_paper_doi               10.1021/ol901148p
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C43 H31 Cl3 O2'
_chemical_formula_weight         686.03
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 112.669(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.962(4)
_cell_length_b                   9.9317(18)
_cell_length_c                   20.157(4)
_cell_measurement_reflns_used    7570
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      31.5050
_cell_measurement_theta_min      2.0508
_cell_volume                     3318.1(12)
_computing_molecular_graphics    'ORTEP 3 for windows'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
;
Saturn70 CCD (4x4 bin mode) with MicroMax-007
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_sigmaI/netI    0.0475
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            21868
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_coefficient_mu    0.315
_exptl_absorpt_correction_T_max  0.9397
_exptl_absorpt_correction_T_min  0.9397
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     454
_refine_ls_number_reflns         5840
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.145
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0613
_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^)+(0.0522P)^2^+1.4898P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1317
_reflns_number_gt                4799
_reflns_number_total             5840
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol901148p_si_002.cif
_cod_data_source_block           comp7
_cod_original_cell_volume        3318.2(11)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1504018