Concise synthesis of N-phosphorylated amides through three-component reactions
Zhu, Yuan-Yuan; Zhang, Tao; Zhou, Linlin; Yang, Shang-Dong; Green Chemistry 23 (2021) 9417–9421; doi:10.1039/D1GC03065E

data_7243783
_publ_section_title
;
 Concise synthesis of N-phosphorylated amides through three-component
 reactions
;
_journal_issue                   23
_journal_name_full               'Green Chemistry'
_journal_page_first              9417
_journal_page_last               9421
_journal_paper_doi               10.1039/D1GC03065E
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C26 H22 N O2 P'
_chemical_formula_sum            'C26 H22 N O2 P'
_chemical_formula_weight         411.41
_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     direct
_audit_creation_date             2020-04-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-07-09 deposited with the CCDC.	2021-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.164(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.6285(3)
_cell_length_b                   9.3057(2)
_cell_length_c                   14.6152(2)
_cell_measurement_reflns_used    3091
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.8670
_cell_measurement_theta_min      5.5310
_cell_volume                     2116.92(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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     37.00  68.00   1.00    1.00    --    0.00  57.00  30.00   31
  2  \w     31.00 123.00   1.00    1.00    --   54.00  38.00 120.00   92
  3  \w    108.00 133.00   1.00    5.00    --  108.00 -38.00   0.00   25
  4  \w    109.00 168.00   1.00    5.00    --  108.00 -12.00 -60.00   59
  5  \w     80.00 125.00   1.00    5.00    --  108.00 -50.00-180.00   45
  6  \w     49.00 115.00   1.00    5.00    --  108.00 -91.00 -60.00   66
  7  \w     61.00  87.00   1.00    1.00    --   54.00-125.00   0.00   26
  8  \w     41.00 129.00   1.00    5.00    --  108.00 -63.00   0.00   88
  9  \w     59.00  84.00   1.00    5.00    --  108.00 -38.00   0.00   25
 10  \w     37.00  90.00   1.00    5.00    --  108.00 -12.00 -60.00   53
 11  \w     37.00  69.00   1.00    1.00    --   54.00  57.00-120.00   32
 12  \w     25.00  63.00   1.00    1.00    --    0.00  57.00 -90.00   38
 13  \w    -13.00  27.00   1.00    1.00    --    0.00  57.00  30.00   40
 14  \w    -18.00  79.00   1.00    1.00    --   54.00 -38.00 -60.00   97
 15  \w     41.00 114.00   1.00    5.00    --  108.00-111.00 -90.00   73
 16  \w     24.00  68.00   1.00    1.00    --   54.00-125.00-150.00   44
 17  \w     41.00 107.00   1.00    5.00    --  108.00 -63.00 120.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0269746000
_diffrn_orient_matrix_UB_12      0.1360953000
_diffrn_orient_matrix_UB_13      -0.0501584000
_diffrn_orient_matrix_UB_21      0.0726981000
_diffrn_orient_matrix_UB_22      0.0261067000
_diffrn_orient_matrix_UB_23      0.0765847000
_diffrn_orient_matrix_UB_31      0.0614472000
_diffrn_orient_matrix_UB_32      -0.0905688000
_diffrn_orient_matrix_UB_33      -0.0531997000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7576
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.587
_diffrn_reflns_theta_max         66.587
_diffrn_reflns_theta_min         5.539
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.325
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59462
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.291
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3736
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0608P)^2^+0.2344P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1137
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3147
_reflns_number_total             3736
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc03065e2.cif
_cod_data_source_block           zhuyy-1_0414_pl
_cod_depositor_comments
'Adding full bibliography for 7243782--7243783.cif.'
_cod_database_code               7243783
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C43(H43A,H43B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C18(H18), C22(H22), C23(H23), C25(H25), C26(H26), C29(H29),
 C30(H30), C31(H31), C38(H38), C40(H40), C42(H42), C46(H46), C50(H50), C51(H51),
  C52(H52), C53(H53), C56(H56), C57(H57), C60(H60)
;
_shelx_res_checksum              71299
_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 1.862
_oxdiff_exptl_absorpt_empirical_full_min 0.517