Iron-Promoted Tandem Reaction of Anilines with Styrene Oxides via C-C Cleavage for the Synthesis of Quinolines.
Zhang, Yicheng; Wang, Min; Li, Pinhua; Wang, Lei; Organic letters 14 (2012) 2206–2209; doi:10.1021/ol300391t

data_1507576
_publ_section_title
;
 Iron-Promoted Tandem Reaction of Anilines with Styrene Oxides via C-C
 Cleavage for the Synthesis of Quinolines.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2206
_journal_page_last               2209
_journal_paper_doi               10.1021/ol300391t
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C15 H10 Br N'
_chemical_formula_sum            'C15 H10 Br N'
_chemical_formula_weight         284.15
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 109.122(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.1173(12)
_cell_length_b                   5.8848(7)
_cell_length_c                   14.7685(14)
_cell_measurement_reflns_used    1580
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4080
_cell_measurement_theta_min      2.9162
_cell_volume                     1159.2(2)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w 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  0.0963
_diffrn_reflns_av_sigmaI/netI    0.1008
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7446
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         3.47
_exptl_absorpt_coefficient_mu    3.519
_exptl_absorpt_correction_T_max  0.4983
_exptl_absorpt_correction_T_min  0.3004
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis PRO (Oxford Diffraction, 2010) 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       0.0097(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2111
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.1148
_refine_ls_R_factor_gt           0.0550
_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^)+(0.0398P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1271
_reflns_number_gt                1160
_reflns_number_total             2111
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol300391t_si_002.cif
_cod_data_source_block           110706_wlbao
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1507576