Streamlined Synthesis of Polycyclic Conjugated Hydrocarbons Containing Cyclobutadienoids via C-H Activated Annulation and Aromatization.
Jin, Zexin; Teo, Yew Chin; Zulaybar, Nicolo G.; Smith, Matthew D.; Xia, Yan; Journal of the American Chemical Society 139 (2017) 1806–1809; doi:10.1021/jacs.6b12888

data_4125562
_publ_section_title
;
 Streamlined Synthesis of Polycyclic Conjugated Hydrocarbons Containing
 Cyclobutadienoids via C-H Activated Annulation and Aromatization.
;
_journal_issue                   5
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1806
_journal_page_last               1809
_journal_paper_doi               10.1021/jacs.6b12888
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C60 H66 Si2'
_chemical_formula_sum            'C60 H66 Si2'
_chemical_formula_weight         843.30
_chemical_name_systematic
;
((1,4,9,14-tetramethylnaphtho[2',3':3,4]cyclobuta[1,2-b]naphtho[2',3':3,4]
cyclobuta[1,2-i]anthracene-7,16-diyl)bis(ethyne-2,1-diyl))
bis(triisopropylsilane)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-08-18
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.952(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.3902(4)
_cell_length_b                   21.3216(11)
_cell_length_c                   13.1829(6)
_cell_measurement_reflns_used    9982
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.819
_cell_measurement_theta_min      2.679
_cell_volume                     2357.0(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 Ver. 2014.11-0 (Bruker-AXS, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker Photon100'
_diffrn_detector_area_resol_mean 10.42
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 with PHOTON 100 detector'
_diffrn_measurement_method       '\f and \w shutterless scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.7749
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            31685
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.967
_diffrn_reflns_theta_min         2.680
_diffrn_source                   'Advanced Light Source, station 11.3.1'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  0.5641
_exptl_absorpt_correction_T_min  0.4994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
'SADABS-2014/2 (Bruker,2014/2) was used for absorption correction.
wR2(int) was 0.1319 before and 0.0566 after correction.
The Ratio of minimum to maximum transmission is 0.8853.
The \l/2 correction factor is Not present.'
;
_exptl_crystal_colour            'clear reddish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_description       prism
_exptl_crystal_F_000             908
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         4824
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0473
_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^)+(0.0581P)^2^+1.6028P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1240
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3769
_reflns_number_total             4824
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b12888_si_003.cif
_cod_data_source_block           g1_monop_0p80_a
_cod_depositor_comments          'Adding full bibliography for 4125562.cif.'
_cod_database_code               4125562
_shelxl_version_number           2014-3
_shelx_res_checksum              85599
_shelx_hkl_checksum              98855