A Simple and Straightforward Approach to Quinoxalines by Iron/Sulfur-Catalyzed Redox Condensation ofo-Nitroanilines and Phenethylamines
Nguyen, Thanh Binh; Retailleau, Pascal; Al-Mourabit, Ali; Organic Letters 15 (2013) 5238–; doi:10.1021/ol402435c

data_1512574
_publ_section_title
;
 A Simple and Straightforward Approach to Quinoxalines by
 Iron/Sulfur-Catalyzed Redox Condensation ofo-Nitroanilines and
 Phenethylamines
;
_journal_issue                   20
_journal_name_full               'Organic Letters'
_journal_page_first              5238
_journal_paper_doi               10.1021/ol402435c
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C15 H12 N2 '
_chemical_formula_sum            'C15 H12 N2'
_chemical_formula_weight         220.27
_chemical_name_systematic
; 
 8-methyl-2-phenylquinoxaline 
;
_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                 95.190(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.4850(10)
_cell_length_b                   19.949(2)
_cell_length_c                   12.9720(10)
_cell_measurement_reflns_used    2027
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.726
_cell_measurement_theta_min      0.407
_cell_volume                     1155.9(3)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)'
_computing_structure_solution    'SIR97 (Altomare, et al. 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Nonius kappa-CCD diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_sigmaI/netI    0.0591
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7602
_diffrn_reflns_theta_full        25.36
_diffrn_reflns_theta_max         25.36
_diffrn_reflns_theta_min         3.76
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Nonius Kappa CCD'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2108
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.984
_refine_ls_R_factor_all          0.1178
_refine_ls_R_factor_gt           0.0538
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0866P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1297
_refine_ls_wR_factor_ref         0.1633
_reflns_number_gt                1090
_reflns_number_total             2112
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol402435c_si_002.cif
_cod_data_source_block           compound_3fa-8
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C15 H12 N2 '
_cod_database_code               1512574