Hypervalent iodine(iii)-promoted N-incorporation into N-aryl vinylogous carbamates to quinoxaline diesters: access to 1,4,5,8-tetraazaphenanthrene.
Sagar, A.; Vidaycharan, Shinde; Shinde, Anand H.; Sharada, Duddu S.; Organic & biomolecular chemistry 14 (2016) 4018–4022; doi:10.1039/c6ob00447d

data_7155068
_publ_section_title
;
 Hypervalent iodine(iii)-promoted N-incorporation into N-aryl vinylogous
 carbamates to quinoxaline diesters: access to
 1,4,5,8-tetraazaphenanthrene.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4018
_journal_page_last               4022
_journal_paper_doi               10.1039/c6ob00447d
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C14 H14 N2 O4'
_chemical_formula_sum            'C14 H14 N2 O4'
_chemical_formula_weight         274.28
_chemical_melting_point          403.15
_chemical_name_common            'dimethyl quinoxaline  dicarboxylate '
_chemical_name_systematic
'Dimethyl 5,8-dimethylquinoxaline-2,3-dicarboxylate '
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_date             2016-02-16
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-02-16 deposited with the CCDC.
2016-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                75.628(13)
_cell_angle_beta                 72.518(13)
_cell_angle_gamma                85.932(12)
_cell_formula_units_Z            2
_cell_length_a                   8.2596(12)
_cell_length_b                   8.9504(13)
_cell_length_c                   10.0044(15)
_cell_measurement_reflns_used    1349
_cell_measurement_temperature    140
_cell_measurement_theta_max      71.9038
_cell_measurement_theta_min      4.7680
_cell_volume                     683.35(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      140
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 0.9605
_diffrn_measured_fraction_theta_max 0.9566
_diffrn_measurement_details
;
  1 omega  -60.00  -29.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   57.0000 -120.0000 31

  2 omega  -44.00   23.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   38.0000  -30.0000 67

  3 omega  -49.00   30.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   38.0000 -150.0000 79

  4 omega -110.00  -36.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  178.0000  -90.0000 74

  5 omega  -50.00   29.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   25.0000  120.0000 79

  6 omega  -27.00   23.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   57.0000 -120.0000 50

  7 omega -110.00  -54.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  178.0000    0.0000 56

  8 omega   47.00  105.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       55.4518 -125.0000  -30.0000 58

  9 omega   77.00  123.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       55.4518   77.0000   90.0000 46

 10 omega   42.00   88.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.9036  -25.0000   30.0000 46

 11 omega   53.00   89.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.9036  -38.0000  120.0000 36

 12 omega   56.00  133.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.9036  -63.0000 -180.0000 77

 13 omega   39.00   89.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.9036  -38.0000  -30.0000 50

 14 omega   61.00  113.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.9036 -111.0000  -30.0000 52

 15 omega   49.00  110.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.9036 -111.0000 -150.0000 61

 16 omega   38.00   83.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.9036  -38.0000   90.0000 45

 17 omega   39.00   81.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.9036  -42.0000  176.0000 42

 18 omega   47.00  104.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.9036  -50.0000  -90.0000 57

 19 omega   42.00   83.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.9036  -50.0000   30.0000 41

 20 omega  100.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.9036    0.0000   60.0000 78

 21 omega   43.00  156.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.9036   12.0000    0.0000 113

 22 omega   46.00  138.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.9036  -91.0000   30.0000 92

 23 omega -113.00  -12.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000  -30.0000 101

 24 omega -111.00  -21.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -57.0000   60.0000 90

 25 omega -111.00  -21.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -57.0000 -120.0000 90

 26 omega -113.00  -12.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000  150.0000 101

 27 omega -110.00  -20.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -63.0000   30.0000 90

 28 omega -111.00  -21.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -57.0000 -180.0000 90
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1759980000
_diffrn_orient_matrix_UB_12      -0.0176198000
_diffrn_orient_matrix_UB_13      0.0254941000
_diffrn_orient_matrix_UB_21      0.0445385000
_diffrn_orient_matrix_UB_22      -0.1273872000
_diffrn_orient_matrix_UB_23      -0.0840683000
_diffrn_orient_matrix_UB_31      0.0726736000
_diffrn_orient_matrix_UB_32      0.1226123000
_diffrn_orient_matrix_UB_33      -0.1411345000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5187
_diffrn_reflns_theta_full        72.0498
_diffrn_reflns_theta_max         72.05
_diffrn_reflns_theta_min         4.77
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.828
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dull whiteish white'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.3329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             289.0376
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane '
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.2662
_refine_diff_density_min         -0.2771
_refine_diff_density_rms         0.0641
_refine_ls_d_res_high            0.8104
_refine_ls_d_res_low             9.2670
_refine_ls_goodness_of_fit_ref   1.1126
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2577
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.1126
_refine_ls_R_factor_all          0.0977
_refine_ls_R_factor_gt           0.0630
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1127P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1780
_refine_ls_wR_factor_ref         0.2209
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -9
_reflns_limit_k_max              10
_reflns_limit_k_min              -10
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                1550
_reflns_number_total             2577
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c6ob00447d2.cif
_cod_data_source_block           exp_6045
_cod_depositor_comments          'Adding full bibliography for 7155068.cif.'
_cod_database_code               7155068
_chemical_oxdiff_formula         'C14 H16 N2 O4'
_reflns_odcompleteness_completeness 99.22
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C10(H10)
2.b Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c), C13(H13a,H13b,H13c), C1(H1a,H1b,H1c), C6(H6a,H6b,H6c)
;
_olex2_submission_special_instructions 'No special instructions were received'