Synthesis of Diiodinated All-Carbon 3,3'-Diphenyl-1,1'-spirobiindene Derivatives via Cascade Enyne Cyclization and Electrophilic Aromatic Substitution.
Li, Quanzhe; Yu, Liuzhu; Wei, Yin; Shi, Min; The Journal of organic chemistry 84 (2019) 9282–9296; doi:10.1021/acs.joc.9b01418

data_4034188
_publ_section_title
;
 Synthesis of Diiodinated All-Carbon 3,3'-Diphenyl-1,1'-spirobiindene
 Derivatives via Cascade Enyne Cyclization and Electrophilic Aromatic
 Substitution.
;
_journal_issue                   14
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9282
_journal_page_last               9296
_journal_paper_doi               10.1021/acs.joc.9b01418
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C31 H22 I2'
_chemical_formula_weight         648.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 121.681(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.237(3)
_cell_length_b                   10.8955(10)
_cell_length_c                   20.456(2)
_cell_measurement_reflns_used    4430
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      50.057
_cell_measurement_theta_min      4.680
_cell_volume                     5165.9(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14510
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         1.757
_exptl_absorpt_coefficient_mu    2.451
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6507
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             2512
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.056
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4812
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0375
_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^)+(0.0530P)^2^+4.0902P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.1003
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3857
_reflns_number_total             4812
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01418_si_003.cif
_cod_data_source_block           cd17434
_cod_original_cell_volume        5166.0(9)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4034188
_shelx_estimated_absorpt_t_min   0.667
_shelx_estimated_absorpt_t_max   0.792
_shelxl_version_number           2013-4
_shelx_res_checksum              48292
_shelx_hkl_checksum              73828