Phosphorus Radical-Initiated Cascade Reaction To Access 2-Phosphoryl-Substituted Quinoxalines.
Liu, Yan; Chen, Xiao-Lan; Zeng, Fan-Lin; Sun, Kai; Qu, Chen; Fan, Lu-Lu; An, Zi-Long; Li, Rui; Jing, Chun-Feng; Wei, Sheng-Kai; Qu, Ling-Bo; Yu, Bing; Sun, Yuan-Qiang; Zhao, Yu-Fen; The Journal of organic chemistry 83 (2018) 11727–11735; doi:10.1021/acs.joc.8b01657

data_4035277
_publ_section_title
;
 Phosphorus Radical-Initiated Cascade Reaction To Access
 2-Phosphoryl-Substituted Quinoxalines.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11727
_journal_page_last               11735
_journal_paper_doi               10.1021/acs.joc.8b01657
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C21 H17 N2 O2 P'
_chemical_formula_sum            'C21 H17 N2 O2 P'
_chemical_formula_weight         360.33
_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     iterative
_audit_creation_date             2018-06-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.400(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.2306(4)
_cell_length_b                   12.4787(4)
_cell_length_c                   17.0064(5)
_cell_measurement_reflns_used    4838
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.7550
_cell_measurement_theta_min      3.5400
_cell_volume                     3656.55(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -70.00   34.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   19.0000  -30.0000 104

  2 omega  -17.00   34.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000    0.0000 51

  3 omega   29.00   76.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000 -180.0000 47

  4 omega   42.00   68.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -90.0000 26

  5 omega   33.00   62.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  -60.0000 29

  6 omega   17.00   53.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000   60.0000 36

  7 omega   49.00   75.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000 -120.0000 26

  8 omega  -32.00    9.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000   60.0000 41

  9 omega   -1.00   24.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -90.0000 25

 10 omega   16.00   76.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   90.0000 60

 11 omega   66.00  103.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  -60.0000 37

 12 omega   37.00  106.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 69

 13 omega   86.00  115.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 29

 14 omega   83.00  158.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   60.0000 75

 15 omega   44.00   70.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 26

 16 omega   39.00   79.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 40

 17 omega   46.00   71.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   60.0000 25

 18 omega   38.00   85.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 47

 19 omega   37.00   73.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 36

 20 omega   88.00  166.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  150.0000 78

 21 omega  111.00  177.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000    0.0000 66

 22 omega   62.00   88.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 26

 23 omega   78.00  136.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   60.0000 58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0103097000
_diffrn_orient_matrix_UB_12      -0.0811588000
_diffrn_orient_matrix_UB_13      0.0673679000
_diffrn_orient_matrix_UB_21      -0.0085950000
_diffrn_orient_matrix_UB_22      0.0931134000
_diffrn_orient_matrix_UB_23      0.0589041000
_diffrn_orient_matrix_UB_31      -0.0883413000
_diffrn_orient_matrix_UB_32      0.0004892000
_diffrn_orient_matrix_UB_33      -0.0141590000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15699
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.077
_diffrn_reflns_theta_max         67.077
_diffrn_reflns_theta_min         4.375
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.473
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88599
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       prism
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         6526
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0570
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0763P)^2^+1.3421P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1502
_refine_ls_wR_factor_ref         0.1662
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4915
_reflns_number_total             6526
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01657_si_002.cif
_cod_data_source_block           201806288
_cod_original_cell_volume        3656.53(18)
_cod_database_code               4035277
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C15H15O3N1P1
_shelx_estimated_absorpt_t_max   0.832
_shelx_estimated_absorpt_t_min   0.747
_reflns_odcompleteness_completeness 99.94
_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. Restrained distances
 C19'-C20'
 1.38 with sigma of 0.02
 C20'-C15'
 1.38 with sigma of 0.02
 C19-C20
 1.38 with sigma of 0.02
 C20-C15
 1.38 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C14(H14), C17(H17), C19(H19), C20(H20), C2'(H2'), C3'(H3'), C4'(H4'),
  C5'(H5'), C6'(H6'), C8'(H8'), C9'(H9'), C10'(H10'), C11'(H11'), C12'(H12'),
 C14'(H14'), C17'(H17'), C19'(H19'), C20'(H20')
3.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C21'(H21D,H21E,H21F)
;
_olex2_submission_special_instructions 'No special instructions were received'