Allylic Amination and N-Arylation-Based Domino Reactions Providing Rapid Three-Component Strategies to Fused Pyrroles with Different Substituted Patterns
Bo Jiang; Ying Li; Man-Su Tu; Shu-Liang Wang; Shu-Jiang Tu; Guigen Li; Journal of Organic Chemistry 77 (2012) 7497–7505; doi:10.1021/jo301323r

data_4027463
_publ_section_title
;
 Allylic Amination and N-Arylation-Based Domino Reactions Providing Rapid
 Three-Component Strategies to Fused Pyrroles with Different Substituted
 Patterns
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7497
_journal_page_last               7505
_journal_paper_doi               10.1021/jo301323r
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C28 H23 Br Cl F N2 O'
_chemical_formula_weight         537.84
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_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                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.7159(18)
_cell_length_b                   9.6703(9)
_cell_length_c                   29.114(3)
_cell_measurement_reflns_used    3429
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.314
_cell_measurement_theta_min      2.5
_cell_volume                     4987.8(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0621
_diffrn_reflns_av_sigmaI/netI    0.0688
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            21232
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.50
_exptl_absorpt_coefficient_mu    1.786
_exptl_absorpt_correction_T_max  0.6946
_exptl_absorpt_correction_T_min  0.5352
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_description       block
_exptl_crystal_F_000             2192
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.888
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4407
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1201
_refine_ls_R_factor_gt           0.0557
_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^)+(0.0720P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1372
_refine_ls_wR_factor_ref         0.1549
_reflns_number_gt                2249
_reflns_number_total             4407
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301323r_si_002.cif
_cod_data_source_block           110514c
_cod_original_cell_volume        4987.8(8)
_cod_database_code               4027463