Iodine-Catalyzed Three-Component Cascade Reaction for the Synthesis of Substituted 2-Phenylnaphtho[1,3]selenazoles under Transition-Metal-Free Conditions.
Chen, Wenqi; Zhu, Xiaoming; Wang, Fei; Yang, Yuan; Deng, Guobo; Liang, Yun; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03154

data_4037943
_publ_section_title
;
 Iodine-Catalyzed Three-Component Cascade Reaction for the Synthesis of
 Substituted 2-Phenylnaphtho[1,3]selenazoles under Transition-Metal-Free
 Conditions.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03154
_journal_year                    2020
_chemical_formula_sum            'C18 H13 N Se'
_chemical_formula_weight         322.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 96.210(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.885(5)
_cell_length_b                   13.354(7)
_cell_length_c                   21.226(10)
_cell_measurement_reflns_used    9967
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.77
_cell_measurement_theta_min      2.57
_cell_volume                     2785(2)
_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-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.999
_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  0.0716
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            27972
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_min         2.460
_exptl_absorpt_coefficient_mu    2.684
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.230
_refine_diff_density_max         0.948
_refine_diff_density_min         -0.720
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       0.0012(4)
_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   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         4904
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0414
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0656P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1082
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3949
_reflns_number_total             4904
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03154_si_002.cif
_cod_data_source_block           zxm334
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4037943
_shelx_estimated_absorpt_t_min   0.500
_shelx_estimated_absorpt_t_max   0.577
_shelxl_version_number           2014-3
_shelx_res_checksum              71739
_shelx_hkl_checksum              11503