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_7116833
_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         'C30 H22 O2'
_chemical_formula_sum            'C30 H22 O2'
_chemical_formula_weight         414.48
_chemical_name_systematic        syn-exo_2Ph
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -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                102.716(2)
_cell_angle_beta                 104.883(2)
_cell_angle_gamma                113.218(2)
_cell_formula_units_Z            4
_cell_length_a                   11.7482(8)
_cell_length_b                   13.7728(8)
_cell_length_c                   15.9289(9)
_cell_measurement_reflns_used    2087
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.06
_cell_volume                     2134.1(2)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998) '
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'PROCESS-AUTO (Rigaku, 1998) '
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS (Sheldrick, 1997)'
_diffrn_ambient_pressure         101.3
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID IP area detector system'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_sigmaI/netI    0.0745
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20870
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.06
_diffrn_source                   'rotating anode X-ray tube'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9968
_exptl_absorpt_correction_T_min  0.9689
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'absorption was corrected by ABSCOR'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     577
_refine_ls_number_reflns         9629
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0626
_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^)+(0.0873P)^2^+0.0564P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1486
_refine_ls_wR_factor_ref         0.1751
_reflns_number_gt                6070
_reflns_number_total             9629
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc00077g2.cif
_cod_data_source_block           C30H22O2_syn-exo
_cod_database_code               7116833