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_4035275
_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         'C20 H15 N2 O P'
_chemical_formula_sum            'C20 H15 N2 O P'
_chemical_formula_weight         330.32
_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
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-04-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_cell_angle_alpha                110.835(4)
_cell_angle_beta                 102.211(4)
_cell_angle_gamma                92.540(4)
_cell_formula_units_Z            2
_cell_length_a                   8.4116(3)
_cell_length_b                   10.4562(5)
_cell_length_c                   10.4805(5)
_cell_measurement_reflns_used    6965
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.8950
_cell_measurement_theta_min      2.1100
_cell_volume                     834.78(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.8816
_diffrn_measured_fraction_theta_max 0.8772
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w     57.00  88.00   0.50    0.80    --   10.60  57.00  60.00   62
  2  \w    -40.00  77.00   0.50    0.80    --  -10.90  57.00 -30.00  234
  3  \w     47.00  73.00   0.50    0.80    --  -10.90  57.00  30.00   52
  4  \w    -97.00 -27.00   0.50    0.80    --  -10.90 -38.00 120.00  140
  5  \w      8.00  34.00   0.50    0.80    --  -10.90 -38.00 120.00   52
  6  \w    -25.00   2.00   0.50    0.80    --  -10.90  57.00  30.00   54
  7  \w    -95.00  31.00   0.50    0.80    --  -10.90 -82.00-120.00  252
  8  \w    -98.00   7.00   0.50    0.80    --  -10.90 -57.00  60.00  210
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0320282000
_diffrn_orient_matrix_UB_12      -0.0294011000
_diffrn_orient_matrix_UB_13      0.0499339000
_diffrn_orient_matrix_UB_21      0.0790643000
_diffrn_orient_matrix_UB_22      0.0079607000
_diffrn_orient_matrix_UB_23      -0.0120225000
_diffrn_orient_matrix_UB_31      0.0172154000
_diffrn_orient_matrix_UB_32      0.0665741000
_diffrn_orient_matrix_UB_33      0.0541853000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10862
_diffrn_reflns_theta_full        28.9479
_diffrn_reflns_theta_max         28.95
_diffrn_reflns_theta_min         2.10
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83411
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.27b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.3141
_exptl_crystal_F_000             344.3391
_refine_diff_density_max         0.3531
_refine_diff_density_min         -0.3324
_refine_diff_density_rms         0.0496
_refine_ls_d_res_high            0.7342
_refine_ls_d_res_low             9.6884
_refine_ls_goodness_of_fit_ref   1.0501
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3880
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0501
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0346
_refine_ls_shift/su_max          0.0020
_refine_ls_shift/su_mean         0.0005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0377P)^2^+0.3797P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0898
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              12
_reflns_limit_k_min              -14
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                3500
_reflns_number_total             3880
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo8b01657_si_003.cif
_cod_data_source_block           HY
_cod_depositor_comments
;

2020-08-18
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '0.5(C20 H15 N2 O P)'
_cod_original_formula_sum        'C10 H7.5 N O0.5 P0.5'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     165.16
_cod_database_code               4035275
_chemical_oxdiff_usercomment     'C H O'
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5aa(H5aa), C6aa(H6aa), C8aa(H8aa), C9aa(H9aa), C3ba(H3ba), C4ba(H4ba),
 C5ba(H5ba), C6ba(H6ba), C7ba(H7ba), C8ba(H8ba), C9ba(H9ba), C0ca(H0ca),
 C1ca(H1ca), C2ca(H2ca), C3ca(H3ca)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.272
_oxdiff_exptl_absorpt_empirical_full_min 0.669