Nazarov Cyclization/Internal Redox Cyclization Sequence for the Synthesis of N-Heterocyclic Bridged Ring Systems.
Huang, Yu-Wen; Frontier, Alison J.; Organic letters 18 (2016) 4896–4899; doi:10.1021/acs.orglett.6b02369

data_1555755
_publ_section_title
;
 Nazarov Cyclization/Internal Redox Cyclization Sequence for the Synthesis
 of N-Heterocyclic Bridged Ring Systems.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4896
_journal_page_last               4899
_journal_paper_doi               10.1021/acs.orglett.6b02369
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C28 H27 N O2'
_chemical_formula_sum            'C28 H27 N O2'
_chemical_formula_weight         409.50
_chemical_name_common            froywh06
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                96.567(2)
_cell_angle_beta                 95.824(2)
_cell_angle_gamma                102.162(3)
_cell_formula_units_Z            4
_cell_length_a                   11.3527(13)
_cell_length_b                   11.6672(13)
_cell_length_c                   16.7434(19)
_cell_measurement_reflns_used    4083
_cell_measurement_temperature    100.0(5)
_cell_measurement_theta_max      24.65
_cell_measurement_theta_min      2.32
_cell_volume                     2135.7(4)
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick 2008)'
_computing_publication_material  'SHELXTL (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick 2008)'
_diffrn_ambient_temperature      100.0(5)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD platform'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0977
_diffrn_reflns_av_unetI/netI     0.0893
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            28374
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.028
_diffrn_reflns_theta_max         25.265
_diffrn_reflns_theta_min         1.235
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6390
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       needle
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     569
_refine_ls_number_reflns         7725
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.1046
_refine_ls_R_factor_gt           0.0512
_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^)+(0.0390P)^2^+0.1175P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.1119
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4690
_reflns_number_total             7725
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02369_si_002.cif
_cod_data_source_block           froywh06
_cod_database_code               1555755
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.981
_shelx_estimated_absorpt_t_max   0.986
_shelx_res_checksum              4988
_shelx_hkl_checksum              12621