Highly Torquoselective Electrocyclizations and Competing 1,7-Hydrogen Shifts of 1-Azatrienes with Silyl Substitution at the Allylic Carbon.
Ma, Zhi-Xiong; Patel, Ashay; Houk, K. N.; Hsung, Richard P.; Organic letters  (2015) 150410083922001–; doi:10.1021/acs.orglett.5b00727

data_1519624
_publ_section_title
;
 Highly Torquoselective Electrocyclizations and Competing 1,7-Hydrogen
 Shifts of 1-Azatrienes with Silyl Substitution at the Allylic Carbon.
;
_journal_name_full               'Organic letters'
_journal_page_first              150410083922001
_journal_paper_doi               10.1021/acs.orglett.5b00727
_journal_year                    2015
_chemical_formula_moiety         'C34 H39 N O Si, 0.5(C5 H12)'
_chemical_formula_sum            'C36.5 H45 N O Si'
_chemical_formula_weight         541.82
_chemical_name_common            14051d
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 93.087(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.2248(13)
_cell_length_b                   7.9565(6)
_cell_length_c                   45.621(3)
_cell_measurement_reflns_used    2854
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      78.71
_cell_measurement_theta_min      3.88
_cell_volume                     6243.2(8)
_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    'SHELXT-2013 (Sheldrick 2013)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker Photon-100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1127
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       57
_diffrn_reflns_limit_l_min       -54
_diffrn_reflns_number            46088
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.490
_diffrn_reflns_theta_min         2.569
_diffrn_source                   'ImuS microfocus'
_exptl_absorpt_coefficient_mu    0.866
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2012/1 (Sheldrick, 2012)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_description       Block
_exptl_crystal_F_000             2344
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.090
_refine_diff_density_max         1.165
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     722
_refine_ls_number_reflns         12375
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0650
_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^)+(0.0768P)^2^+6.2708P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1663
_refine_ls_wR_factor_ref         0.1775
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10021
_reflns_number_total             12375
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b00727_si_004.cif
_cod_data_source_block           14051d
_cod_depositor_comments
;

2019-02-17
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        6243.3(8)
_cod_original_formula_moiety     '2(C34 H39 N O Si), C5 H12'
_cod_original_formula_sum        'C73 H90 N2 O2 Si2'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     1083.64
_cod_database_code               1519624
_shelx_estimated_absorpt_t_min   0.846
_shelx_estimated_absorpt_t_max   0.926
_shelxl_version_number           2013-3
_shelx_res_checksum              44234
_shelx_hkl_checksum              57202