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_4036773
_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         'C36 H20 O2, 2(C H Cl3)'
_chemical_formula_sum            'C38 H22 Cl6 O2'
_chemical_formula_weight         723.25
_chemical_name_common            'Compound 10'
_chemical_name_systematic
;
 7,14-diphenylnaphtho[2,3-k]fluoranthene-8,13-dione bis(chloroform)
 solvate
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.5451(7)
_cell_length_b                   29.7417(18)
_cell_length_c                   8.8141(5)
_cell_measurement_reflns_used    9831
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.1030
_cell_measurement_theta_min      2.4101
_cell_volume                     3288.7(3)
_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>DIAMOND</i> (Brandenburg & Putz, 2012)'
_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_detector_area_resol_mean 8.3660
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_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  0.0495
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            57195
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        29.100
_diffrn_reflns_theta_max         29.179
_diffrn_reflns_theta_min         2.410
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.558
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '<i>SADABS</i> (Bruker AXS, 2013b)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_exptl_transmission_factor_max   0.971
_exptl_transmission_factor_min   0.792
_refine_diff_density_max         0.659
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         4485
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0482
_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^)+(0.0618P)^2^+1.5531P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1242
_refine_ls_wR_factor_ref         0.1326
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3729
_reflns_number_total             4485
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b00492_si_002.cif
_cod_data_source_block           rap060_1m_a
_cod_database_code               4036773
_shelx_estimated_absorpt_t_min   0.837
_shelx_estimated_absorpt_t_max   0.962
_shelxl_version_number           2013-2
_shelx_res_checksum              94036
_shelx_hkl_checksum              9628