The Synthesis of Bicyclo[4.2.1]nona-2,4,7-trienes by [6π + 2π]-Cycloaddition of 1-Substituted 1,3,5-Cycloheptatrienes Catalyzed by Titanium and Cobalt Complexes.
D'yakonov, Vladimir A.; Kadikova, Gulnara N.; Nasretdinov, Ramil N.; Dzhemileva, Lilya U.; Dzhemilev, Usein M.; The Journal of organic chemistry 84 (2019) 9058–9066; doi:10.1021/acs.joc.9b00996

data_4034200
_publ_section_title
;
 The Synthesis of Bicyclo[4.2.1]nona-2,4,7-trienes by [6\p +
 2\p]-Cycloaddition of 1-Substituted 1,3,5-Cycloheptatrienes Catalyzed by
 Titanium and Cobalt Complexes.
;
_journal_issue                   14
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9058
_journal_page_last               9066
_journal_paper_doi               10.1021/acs.joc.9b00996
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C25 H28 Si'
_chemical_formula_sum            'C25 H28 Si'
_chemical_formula_weight         356.56
_chemical_melting_point          376
_chemical_name_systematic
Trimethyl(6-benzyl-8-phenylbicyclo[4.2.1]nona-2,4,7-trien-7-yl)silane
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                80.472(7)
_cell_angle_beta                 77.833(7)
_cell_angle_gamma                76.994(8)
_cell_formula_units_Z            4
_cell_length_a                   12.2208(10)
_cell_length_b                   12.8625(12)
_cell_length_c                   13.9416(11)
_cell_measurement_reflns_used    4356
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.1210
_cell_measurement_theta_min      2.5990
_cell_volume                     2071.2(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXD (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0854
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega   21.00   59.00   1.0000   21.9450
omega____ theta____ kappa____ phi______ frames
    -       17.0261   57.0000  -60.0000 38

  2 omega    0.00   26.00   1.0000   21.9450
omega____ theta____ kappa____ phi______ frames
    -      -16.2449   95.0000  -24.0000 26

  3 omega    0.00   84.00   1.0000   21.9450
omega____ theta____ kappa____ phi______ frames
    -       17.0261   57.0000 -120.0000 84

  4 omega  -15.00   23.00   1.0000   21.9450
omega____ theta____ kappa____ phi______ frames
    -      -16.2449  -99.0000   60.0000 38

  5 omega  -51.00   42.00   1.0000   21.9450
omega____ theta____ kappa____ phi______ frames
    -       17.0261  -77.0000  120.0000 93

  6 omega  -45.00  -17.00   1.0000   21.9450
omega____ theta____ kappa____ phi______ frames
    -      -16.2449   95.0000  -24.0000 28

  7 omega  -63.00  -33.00   1.0000   21.9450
omega____ theta____ kappa____ phi______ frames
    -      -16.2449  178.0000 -150.0000 30

  8 omega   39.00   89.00   1.0000   21.9450
omega____ theta____ kappa____ phi______ frames
    -       17.0261  178.0000  120.0000 50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0140932000
_diffrn_orient_matrix_UB_12      -0.0568738000
_diffrn_orient_matrix_UB_13      0.0094409000
_diffrn_orient_matrix_UB_21      -0.0108449000
_diffrn_orient_matrix_UB_22      -0.0041061000
_diffrn_orient_matrix_UB_23      -0.0471126000
_diffrn_orient_matrix_UB_31      0.0578948000
_diffrn_orient_matrix_UB_32      0.0013058000
_diffrn_orient_matrix_UB_33      -0.0210314000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_unetI/netI     0.1338
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.851
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17402
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.253
_diffrn_reflns_theta_min         1.506
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_type              'XCalibur E'
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62338
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.143
_exptl_crystal_description       plank
_exptl_crystal_F_000             768.0
_exptl_crystal_recrystallization_method 'petroleum ether'
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     556
_refine_ls_number_reflns         9598
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.958
_refine_ls_R_factor_all          0.1517
_refine_ls_R_factor_gt           0.0726
_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^)+(0.0540P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1441
_refine_ls_wR_factor_ref         0.1787
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4424
_reflns_number_total             9598
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00996_si_002.cif
_cod_data_source_block           nrn-380-37
_cod_database_code               4034200
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
;