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_4034189
_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            'C29 H22 I2 O S'
_chemical_formula_weight         672.32
_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   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                109.4120(10)
_cell_angle_beta                 99.5180(10)
_cell_angle_gamma                91.8440(10)
_cell_formula_units_Z            2
_cell_length_a                   8.5401(2)
_cell_length_b                   12.1446(3)
_cell_length_c                   13.2015(4)
_cell_measurement_reflns_used    9750
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      54.965
_cell_measurement_theta_min      4.858
_cell_volume                     1267.99(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22018
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         1.786
_exptl_absorpt_coefficient_mu    2.582
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6153
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.761
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.642
_refine_diff_density_min         -0.649
_refine_diff_density_rms         0.074
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4971
_refine_ls_number_restraints     38
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0346
_refine_ls_shift/su_max          0.042
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0346P)^2^+1.4319P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0872
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4243
_reflns_number_total             4971
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01418_si_004.cif
_cod_data_source_block           mo_d8v18541_0m
_cod_database_code               4034189
_shelx_estimated_absorpt_t_min   0.668
_shelx_estimated_absorpt_t_max   0.782
_shelxl_version_number           2013-4
_shelx_res_checksum              43104
_shelx_hkl_checksum              94532