Unexpected One-Pot Synthesis of Highly Conjugated Pentacyclic Diquinoid Compounds
Alessia Coletti; Sara Lentini; Valeria Conte; Barbara Floris; Olga Bortolini; Fabio Sforza; Fabrizia Grepioni; Pierluca Galloni; Journal of Organic Chemistry 77 (2012) 6873–6879; doi:10.1021/jo300985x

data_4027378
_publ_section_title
;
 Unexpected One-Pot Synthesis of Highly Conjugated Pentacyclic Diquinoid
 Compounds
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6873
_journal_page_last               6879
_journal_paper_doi               10.1021/jo300985x
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C23 H14 O4'
_chemical_formula_weight         354.34
_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                 96.835(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4250(10)
_cell_length_b                   17.223(2)
_cell_length_c                   13.0220(10)
_cell_measurement_temperature    293(2)
_cell_volume                     1653.4(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.0472
_diffrn_reflns_av_sigmaI/netI    0.2273
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5661
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.84
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            deep_red
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_description       needle
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.118
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.897
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         2793
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.897
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0382
_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^)+(0.0240P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0557
_refine_ls_wR_factor_ref         0.0690
_reflns_number_gt                1790
_reflns_number_total             2803
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300985x_si_002.cif
_cod_data_source_block           KuQ
_cod_database_code               4027378