Tandem C-N Bond Formation through Condensation and Metal-Free N-Arylation: Protocol for Synthesizing Diverse Functionalized Quinoxalines.
Jiao, Yan-Xiao; Wu, Ling-Ling; Zhu, Hai-Miao; Qin, Jiang-Ke; Pan, Cheng-Xue; Mo, Dong-Liang; Su, Gui-Fa; The Journal of organic chemistry 82 (2017) 4407–4414; doi:10.1021/acs.joc.7b00011

data_4037470
_publ_section_title
;
 Tandem C-N Bond Formation through Condensation and Metal-Free
 N-Arylation: Protocol for Synthesizing Diverse Functionalized
 Quinoxalines.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4407
_journal_page_last               4414
_journal_paper_doi               10.1021/acs.joc.7b00011
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C16 H14 N2 O2'
_chemical_formula_sum            'C16 H14 N2 O2'
_chemical_formula_weight         266.29
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-09-15
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 117.632(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.177(3)
_cell_length_b                   8.5411(14)
_cell_length_c                   14.152(4)
_cell_measurement_reflns_used    2426
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.2418
_cell_measurement_theta_min      2.8799
_cell_volume                     1304.0(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9784
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -84.00   -7.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0354  -57.0000  120.0000 77

  2 omega  -85.00   12.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0354  -77.0000    0.0000 97

  3 omega    4.00   55.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0354   19.0000  120.0000 51

  4 omega  -67.00   10.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0354  -77.0000 -150.0000 77

  5 omega   19.00   50.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0354   57.0000   30.0000 31

  6 omega  -46.00  -20.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.3635  -38.0000 -120.0000 26

  7 omega   -2.00   40.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.3635  -38.0000 -120.0000 42

  8 omega    1.00   26.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.3635   57.0000  150.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0072080000
_diffrn_orient_matrix_UB_12      -0.0263374000
_diffrn_orient_matrix_UB_13      0.0461431000
_diffrn_orient_matrix_UB_21      0.0131030000
_diffrn_orient_matrix_UB_22      0.0766274000
_diffrn_orient_matrix_UB_23      0.0217817000
_diffrn_orient_matrix_UB_31      -0.0618076000
_diffrn_orient_matrix_UB_32      0.0191263000
_diffrn_orient_matrix_UB_33      -0.0247108000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.1126
_diffrn_reflns_av_unetI/netI     0.0775
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10005
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.89
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47831
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_crystal_size_max          3.00
_exptl_crystal_size_mid          3.00
_exptl_crystal_size_min          2.00
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.775
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2668
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.775
_refine_ls_R_factor_all          0.1195
_refine_ls_R_factor_gt           0.0697
_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^)+(0.0100P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1171
_refine_ls_wR_factor_ref         0.1453
_reflns_number_gt                1460
_reflns_number_total             2668
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b00011_si_002.cif
_cod_data_source_block           0915-sgf-jyx-001aaa
_cod_original_cell_volume        1304.0(5)
_cod_database_code               4037470
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32