Hairpin Furans and Giant Biaryls.
Geng, Xin; Mague, Joel T.; Donahue, James P.; Pascal, Jr, Robert A; The Journal of organic chemistry 81 (2016) 3838–3847; doi:10.1021/acs.joc.6b00492

data_4036776
_publ_section_title
;
 Hairpin Furans and Giant Biaryls.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3838
_journal_page_last               3847
_journal_paper_doi               10.1021/acs.joc.6b00492
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C76 H40 O5, 2(C7 H8)'
_chemical_formula_sum            'C90 H56 O5'
_chemical_formula_weight         1217.34
_chemical_name_common            'Compound 19'
_chemical_name_systematic
;
 12,12'-epoxy-11,11'-bis(9,16-diphenylnaphtho[2,3-b]triphenylene-10,15-
 dione) di(toluene) solvate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                83.3780(9)
_cell_angle_beta                 82.6460(10)
_cell_angle_gamma                70.8910(9)
_cell_formula_units_Z            2
_cell_length_a                   13.7401(10)
_cell_length_b                   15.1398(10)
_cell_length_c                   15.9430(11)
_cell_measurement_reflns_used    9975
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.484
_cell_measurement_theta_min      2.334
_cell_volume                     3098.4(4)
_computing_cell_refinement       '<i>SAINT</i> (Bruker AXS, 2013a)'
_computing_data_collection       '<i>APEX2</i> (Bruker AXS, 2013)'
_computing_data_reduction        '<i>SAINT</i> (Bruker AXS, 2013a)'
_computing_molecular_graphics
'<i>XP - Interactive Molecular Graphics - Version 5.1<i>'
_computing_publication_material  '<i>SHELXTL</i> (Bruker AXS, 2008)'
_computing_structure_refinement  '<i>SHELXL-2013</i> (Sheldrick, 2013)'
_computing_structure_solution    '<i>SHELXT</i> (Bruker AXS 2013c)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker Smart APEX CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_av_unetI/netI     0.0576
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            54053
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.617
_diffrn_reflns_theta_min         1.759
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2013)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_description       block
_exptl_crystal_F_000             1276
_exptl_crystal_size_max          0.115
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.083
_refine_diff_density_max         0.691
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     856
_refine_ls_number_reflns         14281
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0576
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0662P)^2^+1.5265P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1369
_refine_ls_wR_factor_ref         0.1589
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9687
_reflns_number_total             14281
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b00492_si_002.cif
_cod_data_source_block           RAP094_0m_a
_cod_database_code               4036776
_shelx_estimated_absorpt_t_min   0.991
_shelx_estimated_absorpt_t_max   0.993
_shelxl_version_number           2013-4
_shelx_res_checksum              13659
_shelx_hkl_checksum              78543