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_1555756
_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_absolute_configuration syn
_chemical_formula_moiety         'C24 H23 N O3'
_chemical_formula_sum            'C24 H23 N O3'
_chemical_formula_weight         373.43
_chemical_name_common            froywh05
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.9578(15)
_cell_length_b                   11.041(2)
_cell_length_c                   24.685(5)
_cell_measurement_reflns_used    1481
_cell_measurement_temperature    100.0(5)
_cell_measurement_theta_max      18.50
_cell_measurement_theta_min      2.48
_cell_volume                     1896.3(7)
_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, 2014b)'
_computing_structure_solution    'SIR2011 (Burla et al., 2012)'
_diffrn_ambient_temperature      100.0(5)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.2471
_diffrn_reflns_av_unetI/netI     0.1363
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            25991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.028
_diffrn_reflns_theta_max         25.115
_diffrn_reflns_theta_min         2.021
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6279
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014a)'
_exptl_crystal_colour            'pale orange'
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       needle
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
; 
 Flack x determined using 566 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_extinction_coef       0.014(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick, 2014b)'
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3389
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.1409
_refine_ls_R_factor_gt           0.0644
_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^)+(0.0539P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.1444
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                1943
_reflns_number_total             3389
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02369_si_001.cif
_cod_data_source_block           froywh05
_cod_database_code               1555756
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.976
_shelx_estimated_absorpt_t_max   0.997
_shelx_res_checksum              87412
_shelx_hkl_checksum              57746