A new synthetic route to substituted tetracenes and pentacenes via stereoselective [4+2] cycloadditions of 1,4-dihydro-1,4-epoxynaphthalene and isobenzofuran
Shohei Eda; Fumiaki Eguchi; Hiroshi Haneda; Toshiyuki Hamura; Chem.Commun. 51 (2015) 5963–; doi:10.1039/C5cc00077G

data_7116835
_publ_section_title
;
 A new synthetic route to substituted tetracenes and pentacenes via
 stereoselective [4+2] cycloadditions of 1,4-dihydro-1,4-epoxynaphthalene
 and isobenzofuran
;
_journal_name_full               Chem.Commun.
_journal_page_first              5963
_journal_paper_doi               10.1039/C5cc00077G
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C42 H30 O2'
_chemical_formula_sum            'C42 H30 O2'
_chemical_formula_weight         566.66
_chemical_name_common            sample2
_chemical_name_systematic
1,3,10,12-tetraphenyl-19,20-dioxahexacycloicosahexaene
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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
_audit_update_record
;
2015-01-05 deposited with the CCDC.
2015-02-25 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 91.5250(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5584(2)
_cell_length_b                   9.5420(2)
_cell_length_c                   29.2511(5)
_cell_measurement_reflns_used    33671
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.18
_cell_measurement_theta_min      3.02
_cell_volume                     2945.95(10)
_computing_cell_refinement       RAPID-AUTO
_computing_data_collection       RAPID-AUTO
_computing_data_reduction        RAPID-AUTO
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_pressure         101.3
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID2'
_diffrn_measurement_method       \w-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_av_sigmaI/netI    0.0567
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            33671
_diffrn_reflns_theta_full        68.18
_diffrn_reflns_theta_max         68.18
_diffrn_reflns_theta_min         3.02
_diffrn_source                   'rotating anode x-ray'
_diffrn_source_type              rigaku
_exptl_absorpt_coefficient_mu    0.598
_exptl_absorpt_correction_T_max  0.9881
_exptl_absorpt_correction_T_min  0.8203
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   abscore,T.Higashi,RIGAKU
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         5331
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.1312
_refine_ls_R_factor_gt           0.0768
_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^)+(0.1498P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1988
_refine_ls_wR_factor_ref         0.2783
_reflns_number_gt                2803
_reflns_number_total             5331
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc00077g2.cif
_cod_data_source_block           C42H30O2_anti-endo
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7116835