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_4036774
_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         'C72 H38 O4, 2(C H Cl3)'
_chemical_formula_sum            'C74 H40 Cl6 O4'
_chemical_formula_weight         1205.76
_chemical_name_common            'Compound 13'
_chemical_name_systematic
;
 9,9'-bis(7,14-diphenylnaphtho[2,3-k]fluoranthene-8,13-dione)
 bis(chloroform) 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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                87.9610(7)
_cell_angle_beta                 69.6210(7)
_cell_angle_gamma                68.6830(7)
_cell_formula_units_Z            4
_cell_length_a                   18.3157(10)
_cell_length_b                   18.8183(10)
_cell_length_c                   21.1243(12)
_cell_measurement_reflns_used    9922
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5395
_cell_measurement_theta_min      2.2668
_cell_volume                     6323.6(6)
_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 0.990
_diffrn_measured_fraction_theta_max 0.959
_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  0.0471
_diffrn_reflns_av_unetI/netI     0.0844
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            56717
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        27.000
_diffrn_reflns_theta_max         27.838
_diffrn_reflns_theta_min         1.034
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.321
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '<i>SADABS</i> (Bruker AXS, 2013b)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2472
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.040
_exptl_transmission_factor_max   0.971
_exptl_transmission_factor_min   0.744
_refine_diff_density_max         1.312
_refine_diff_density_min         -0.934
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1513
_refine_ls_number_reflns         28829
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1285
_refine_ls_R_factor_gt           0.0689
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1084P)^2^+0.1147P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1813
_refine_ls_wR_factor_ref         0.2191
_reflns_Friedel_coverage         0.000
_reflns_number_gt                15773
_reflns_number_total             28829
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b00492_si_002.cif
_cod_data_source_block           rap070_0m_a_sq_s
_cod_database_code               4036774
_shelx_estimated_absorpt_t_min   0.953
_shelx_estimated_absorpt_t_max   0.987
_shelxl_version_number           2013-3
_shelx_res_checksum              30661
_shelx_hkl_checksum              67770
_shelx_fab_checksum              39282