Silver-catalyzed cyclization of nitrones with 2-azetine: a radical approach to 2,3-disubstituted quinolines
Yan, Hao; Li, Xincheng; Wang, Chunxiang; Wan, Boshun; Organic Chemistry Frontiers 4 (2017) 1833–; doi:10.1039/C7QO00405B

data_1553813
_publ_section_title
;
 Silver-catalyzed cyclization of nitrones with 2-azetine: a radical
 approach to 2,3-disubstituted quinolines
;
_journal_issue                   9
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1833
_journal_paper_doi               10.1039/C7QO00405B
_journal_volume                  4
_journal_year                    2017
_chemical_formula_sum            'C21 H21 Br N2 O2'
_chemical_formula_weight         413.31
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2017-01-10 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;
_cell_angle_alpha                73.395(18)
_cell_angle_beta                 81.56(2)
_cell_angle_gamma                78.69(2)
_cell_formula_units_Z            2
_cell_length_a                   5.095(8)
_cell_length_b                   12.261(19)
_cell_length_c                   17.00(3)
_cell_measurement_reflns_used    326
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      32.816
_cell_measurement_theta_min      4.823
_cell_volume                     993(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.916
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1751
_diffrn_reflns_av_unetI/netI     0.3460
_diffrn_reflns_Laue_measured_fraction_full 0.916
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4250
_diffrn_reflns_point_group_measured_fraction_full 0.916
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.757
_exptl_absorpt_coefficient_mu    2.085
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3425
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.110
_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   0.963
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3288
_refine_ls_number_restraints     78
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.2545
_refine_ls_R_factor_gt           0.0911
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=exp[3.(sin\q/\l)^2^)]/[\s^2^(Fo^2^)+(0.1051P)^2^]where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2098
_refine_ls_wR_factor_ref         0.2887
_reflns_Friedel_coverage         0.000
_reflns_number_gt                971
_reflns_number_total             3288
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00405b2.cif
_cod_data_source_block           cd16158m_a
_cod_database_code               1553813
_shelx_estimated_absorpt_t_min   0.731
_shelx_estimated_absorpt_t_max   0.921
_shelxl_version_number           2013-4
_shelx_res_checksum              28807
_shelx_hkl_checksum              58301