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_4035276
_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, 0.25(H2 O)'
_chemical_formula_sum            'C21 H17.5 N2 O2.25 P'
_chemical_formula_weight         364.84
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                75.454(2)
_cell_angle_beta                 77.788(2)
_cell_angle_gamma                89.162(2)
_cell_formula_units_Z            4
_cell_length_a                   8.6441(2)
_cell_length_b                   14.5300(3)
_cell_length_c                   15.1708(3)
_cell_measurement_reflns_used    6469
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      72.8510
_cell_measurement_theta_min      3.8020
_cell_volume                     1801.13(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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.951
_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     20.00  78.00   0.50    0.50    --    0.00  57.00 150.00  116
  2  \w     -4.00  28.00   0.50    0.50    --    0.00 -57.00  60.00   64
  3  \w    -89.00 -57.00   0.50    0.50    --    0.00 -57.00-150.00   64
  4  \w    -19.00   9.00   0.50    0.50    --    0.00  57.00 150.00   56
  5  \w    -18.00  26.00   0.50    0.50    --    0.00 -57.00-150.00   88
  6  \w    102.00 128.00   0.50    1.30    --   97.60 -30.00  60.00   52
  7  \w     15.00  70.00   0.50    1.30    --   97.60 -30.00  60.00  110
  8  \w     55.00 128.00   0.50    1.30    --   97.60 -77.00 -60.00  146
  9  \w    114.00 142.00   0.50    1.30    --   97.60  45.00  90.00   56
 10  \w    147.00 173.00   0.50    1.30    --   97.60  45.00  90.00   52
 11  \w     82.00 130.00   0.50    1.30    --   97.60 -82.00 -30.00   96
 12  \w     73.00 131.00   0.50    1.30    --   97.60 -77.00  30.00  116
 13  \w      8.00 135.00   0.50    1.30    --   97.60 -82.00 150.00  254
 14  \w     81.00 128.00   0.50    1.30    --   97.60 -82.00-120.00   94
 15  \w     10.00 129.00   0.50    1.30    --   97.60 -30.00 -60.00  238
 16  \w     12.00  46.00   0.50    1.30    --   97.60 -82.00-120.00   68
 17  \w     12.00  59.00   0.50    1.30    --   97.60 -82.00 -30.00   94
 18  \w      8.00  45.00   0.50    1.30    --   97.60 -77.00 -60.00   74
 19  \w     12.00 126.00   0.50    1.30    --   97.60 -61.00 150.00  228
 20  \w     61.00 184.00   0.50    1.30    --   97.60  15.00  60.00  246
;
_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      0.0172759000
_diffrn_orient_matrix_UB_12      0.1079936000
_diffrn_orient_matrix_UB_13      -0.0114931000
_diffrn_orient_matrix_UB_21      -0.1200127000
_diffrn_orient_matrix_UB_22      -0.0096538000
_diffrn_orient_matrix_UB_23      0.0930350000
_diffrn_orient_matrix_UB_31      0.1363986000
_diffrn_orient_matrix_UB_32      -0.0162021000
_diffrn_orient_matrix_UB_33      0.0524480000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14738
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.258
_diffrn_reflns_theta_min         3.804
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.512
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97426
_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_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_description       needle
_exptl_crystal_F_000             762
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     483
_refine_ls_number_reflns         6888
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0406
_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^)+(0.0414P)^2^+0.7781P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1069
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5626
_reflns_number_total             6888
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01657_si_004.cif
_cod_data_source_block           hy
_cod_depositor_comments
;

2025-10-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_weight         729.68
_cod_original_formula_moiety         '2(C21 H17 N2 O2 P), 0.5(H2 O)'
_cod_original_formula_units_Z            2
_cod_original_formula_sum        'C42 H35 N4 O4.50 P2'
_cod_database_code               4035276
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C H O S N P'
_chemical_oxdiff_usercomment     'C H O'
_shelx_estimated_absorpt_t_max   0.863
_shelx_estimated_absorpt_t_min   0.660
_reflns_odcompleteness_completeness 98.39
_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, All O(H,H) groups
2. Restrained distances
 H00Z-H1B
 2.3 with sigma of 0.02
3. Others
 Fixed Sof: O1(0.5) H1A(0.5) H1B(0.5)
4.a Free rotating group:
 O1(H1A,H1B)
4.b Aromatic/amide H refined with riding coordinates:
 C00L(H00L), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00S(H00S),
 C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y),
 C00Z(H00Z), C010(H010), C011(H011), C012(H012), C013(H013), C014(H014),
 C015(H015), C016(H016), C017(H017), C019(H019), C01A(H01D), C01B(H01E),
 C01D(H01I), C01E(H01J), C01F(H01K), C01G(H01L)
4.c Idealised Me refined as rotating group:
 C018(H01A,H01B,H01C), C01C(H01F,H01G,H01H)
;
_shelx_res_checksum              35386
_shelx_hkl_checksum              8192
_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 1.475
_oxdiff_exptl_absorpt_empirical_full_min 0.893