Thermal 1,3-Trityl Migrations in Diels-Alder Domino Reactions of 1-Trityl-4-vinyl-1H-imidazoles
Lynsey J. Cotterill; Ross W. Harrington; William Clegg; Michael J. Hall; Journal of Organic Chemistry 75 (2010) 4604–4607; doi:10.1021/jo100416c

data_4025511
_publ_section_title
;
 Thermal 1,3-Trityl Migrations in Diels-Alder Domino Reactions of
 1-Trityl-4-vinyl-1H-imidazoles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4604
_journal_page_last               4607
_journal_paper_doi               10.1021/jo100416c
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C41 H43 N3 O3 Si, C4 H10 O'
_chemical_formula_sum            'C45 H53 N3 O4 Si'
_chemical_formula_weight         727.99
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 113.381(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   14.6807(3)
_cell_length_b                   9.97200(13)
_cell_length_c                   15.8925(4)
_cell_measurement_reflns_used    8935
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      62.2767
_cell_measurement_theta_min      3.0269
_cell_volume                     2135.55(9)
_computing_cell_refinement
;
'Mon Mar 01 03:48:25 2010'
;
_computing_data_collection
;
'Mon Mar 01 03:48:25 2010'
;
_computing_data_reduction
;
'Mon Mar 01 03:48:25 2010'
;
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'thick-slice \w scans'
_diffrn_radiation_monochromator  none
_diffrn_radiation_source         'sealed tube with Enhance Ultra optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0387
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15857
_diffrn_reflns_theta_full        62.37
_diffrn_reflns_theta_max         62.37
_diffrn_reflns_theta_min         3.03
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.823
_exptl_absorpt_correction_T_max  0.9678
_exptl_absorpt_correction_T_min  0.7787
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
'Mon Mar 01 03:48:25 2010'
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.132
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             780
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.704
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_extinction_coef       0.0016(3)
_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   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     484
_refine_ls_number_reflns         6621
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0946P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1261
_refine_ls_wR_factor_ref         0.1317
_reflns_number_gt                5765
_reflns_number_total             6621
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo100416c_si_005.cif
_cod_data_source_block           mjh23
_cod_original_cell_volume        2135.56(7)
_cod_database_code               4025511