Synthesis of Medium Ring Nitrogen Heterocycles via a Tandem Copper-Catalyzed C-N Bond Formation-Ring-Expansion Process
Artis Klapars; Sean Parris; Kevin W. Anderson; Stephen L. Buchwald; Journal of the American Chemical Society 126 (2004) 3529–3533; doi:10.1021/ja038565t

data_4112351
_publ_section_title
;
 Synthesis of Medium Ring Nitrogen Heterocycles via a Tandem
 Copper-Catalyzed C-N Bond Formation-Ring-Expansion Process
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3529
_journal_page_last               3533
_journal_paper_doi               10.1021/ja038565t
_journal_volume                  126
_journal_year                    2004
_chemical_formula_sum            'C27 H30 N2 O'
_chemical_formula_weight         398.53
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_symmetry_cell_setting           rhombohedral
_symmetry_space_group_name_Hall  '-R 3'
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_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   28.661(2)
_cell_length_b                   28.661(2)
_cell_length_c                   14.6656(17)
_cell_measurement_reflns_used    3277
_cell_measurement_temperature    194(2)
_cell_measurement_theta_max      23.24
_cell_measurement_theta_min      2.46
_cell_volume                     10433.1(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      194(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0470
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16033
_diffrn_reflns_theta_full        23.32
_diffrn_reflns_theta_max         23.32
_diffrn_reflns_theta_min         1.42
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.142
_exptl_crystal_density_meas      0
_exptl_crystal_description       prism
_exptl_crystal_F_000             3852
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.39
_refine_diff_density_max         1.268
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3360
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.140
_refine_ls_R_factor_all          0.1146
_refine_ls_R_factor_gt           0.0963
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1810P)^2^+16.1724P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2802
_refine_ls_wR_factor_ref         0.2952
_reflns_number_gt                2658
_reflns_number_total             3360
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja038565tsi20030922_100846.cif
_cod_data_source_block           ylidt
_cod_original_cell_volume        10433.2(17)
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               4112351