Synthesis of Quinoxaline Derivatives via Tandem Oxidative Azidation/Cyclization Reaction of N-Arylenamines.
Ma, Haichao; Li, Dianjun; Yu, Wei; Organic letters 18 (2016) 868–871; doi:10.1021/acs.orglett.6b00148

data_1542666
_publ_section_title
;
 Synthesis of Quinoxaline Derivatives via Tandem Oxidative
 Azidation/Cyclization Reaction of N-Arylenamines.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              868
_journal_page_last               871
_journal_paper_doi               10.1021/acs.orglett.6b00148
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C17 H13 Br N2 O2'
_chemical_formula_sum            'C17 H13 Br N2 O2'
_chemical_formula_weight         357.20
_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'
_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_date             2015-12-03
_audit_creation_method
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Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
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_cell_angle_alpha                90.00
_cell_angle_beta                 92.566(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.4677(2)
_cell_length_b                   16.8234(8)
_cell_length_c                   20.1968(11)
_cell_measurement_reflns_used    1494
_cell_measurement_temperature    294.06(10)
_cell_measurement_theta_max      26.2730
_cell_measurement_theta_min      3.7730
_cell_volume                     1516.51(13)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.06(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -14.00   61.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854    0.0000  120.0000 50

  2 omega   -9.00   22.50   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000    0.0000 21

  3 omega  -43.00   32.00   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -57.0000  120.0000 50

  4 omega  -19.00   24.50   1.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000 -150.0000 29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0435292000
_diffrn_orient_matrix_UB_12      0.0332775000
_diffrn_orient_matrix_UB_13      -0.0197048000
_diffrn_orient_matrix_UB_21      -0.0856327000
_diffrn_orient_matrix_UB_22      -0.0252745000
_diffrn_orient_matrix_UB_23      -0.0216510000
_diffrn_orient_matrix_UB_31      -0.1265615000
_diffrn_orient_matrix_UB_32      0.0056619000
_diffrn_orient_matrix_UB_33      0.0194626000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0673
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            5862
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.77
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.719
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89048
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2999
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0432
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0249P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0838
_reflns_number_gt                2210
_reflns_number_total             2999
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b00148_si_002.cif
_cod_data_source_block           mahaichao_1203
_cod_original_cell_volume        1516.53(13)
_cod_database_code               1542666
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_olex2_date_sample_data_collection 2015-12-03
_olex2_submission_special_instructions 'No special instructions were received'