Conjugate Addition-Initiated Nazarov Cyclization
Joshua L. Brooks; Patrick A. Caruana; Alison J. Frontier; Journal of the American Chemical Society 133 (2011) 12454–12457; doi:10.1021/ja205440x

data_4106580
_publ_section_title
;
 Conjugate Addition-Initiated Nazarov Cyclization
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12454
_journal_page_last               12457
_journal_paper_doi               10.1021/ja205440x
_journal_volume                  133
_journal_year                    2011
_chemical_formula_moiety         'C19 H25 N O2'
_chemical_formula_sum            'C19 H25 N O2'
_chemical_formula_weight         299.40
_chemical_name_common            frojb01
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                84.292(2)
_cell_angle_beta                 87.090(2)
_cell_angle_gamma                78.703(2)
_cell_formula_units_Z            2
_cell_length_a                   6.3098(6)
_cell_length_b                   8.9274(9)
_cell_length_c                   14.8070(15)
_cell_measurement_reflns_used    4006
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      37.85
_cell_measurement_theta_min      2.60
_cell_volume                     813.45(14)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      100.0(1)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD Platform'
_diffrn_measurement_method       'area detector, \w scans per \f'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            23162
_diffrn_reflns_theta_full        36.32
_diffrn_reflns_theta_max         36.32
_diffrn_reflns_theta_min         2.34
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9754
_exptl_absorpt_correction_T_min  0.9723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_description       needle
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.599
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         7771
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0504
_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^)+(0.0912P)^2^+0.0048P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1363
_refine_ls_wR_factor_ref         0.1513
_reflns_number_gt                5816
_reflns_number_total             7771
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja205440x_si_001.cif
_cod_data_source_block           frojb01
_cod_database_code               4106580