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_7243782
_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         'C21 H18 N O3 P'
_chemical_formula_sum            'C21 H18 N O3 P'
_chemical_formula_weight         363.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_block_doi                 10.5517/ccdc.csd.cc27mnn6
_audit_creation_date             2021-03-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-03-31 deposited with the CCDC.	2021-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.7242(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.52643(9)
_cell_length_b                   14.88162(13)
_cell_length_c                   12.71774(11)
_cell_measurement_reflns_used    9326
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.0460
_cell_measurement_theta_min      3.4590
_cell_volume                     1802.83(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.954
_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     -8.00  32.00   0.50    0.05    --  -43.30  48.00 -16.00   80
  2  \w    -50.00 -25.00   0.50    0.05    -- -100.00  45.00  90.00   50
  3  \w    -53.00 -27.00   0.50    0.05    -- -100.00  45.00 150.00   52
  4  \w    -53.00 -24.00   0.50    0.05    -- -100.00  45.00 120.00   58
  5  \w    -68.00 -40.00   0.50    0.05    -- -100.00  61.00 120.00   56
  6  \w    -53.00 -26.00   0.50    0.05    --  -43.30  48.00 -16.00   54
  7  \w    -57.00 -25.00   0.50    0.05    -- -100.00  48.00 -16.00   64
  8  \w    -53.00 -24.00   0.50    0.05    -- -100.00  45.00 -90.00   58
  9  \w    -54.00 -26.00   0.50    0.05    -- -100.00  45.00-180.00   56
 10  \w    -58.00 -27.00   0.50    0.05    -- -100.00  61.00-180.00   62
 11  \w   -117.00 -21.00   0.50    0.05    --  -43.30 -48.00-164.00  192
 12  \w    -35.00  22.00   0.50    0.05    --   43.30 -19.00  60.00  114
 13  \w     45.00  70.00   0.50    0.05    --   43.30  48.00 -16.00   50
 14  \w    132.00 174.00   0.50    0.05    --  109.88  48.00 -16.00   84
 15  \w    142.00 175.00   0.50    0.05    --  109.88  30.00 -90.00   66
 16  \w    102.00 128.00   0.50    0.05    --  109.88  48.00 -16.00   52
 17  \w     86.00 127.00   0.50    0.05    --  109.88  30.00 -90.00   82
 18  \w     92.00 154.00   0.50    0.05    --  109.88  61.00  60.00  124
 19  \w     66.00  92.00   0.50    0.05    --  109.88 -77.00  30.00   52
 20  \w     53.00 105.00   0.50    0.05    --  109.88-125.00 -30.00  104
 21  \w     41.00  95.00   0.50    0.05    --  109.88 -77.00   0.00  108
 22  \w     37.00  67.00   0.50    0.05    --  109.88 -61.00-120.00   60
 23  \w     37.00  63.00   0.50    0.05    --  109.88 -61.00-180.00   52
 24  \w      8.00  33.00   0.50    0.05    --   43.30 -48.00-164.00   50
 25  \w     37.00  66.00   0.50    0.05    --  109.88 -61.00 -30.00   58
 26  \w     40.00  90.00   0.50    0.05    --  109.88 -77.00 150.00  100
 27  \w    -76.00 -48.00   0.50    0.05    --  -43.30-179.00 -30.00   56
 28  \w   -175.00 -89.00   0.50    0.05    -- -100.00 -48.00-164.00  172
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1522241000
_diffrn_orient_matrix_UB_12      -0.0009619000
_diffrn_orient_matrix_UB_13      -0.0424639000
_diffrn_orient_matrix_UB_21      0.0448325000
_diffrn_orient_matrix_UB_22      -0.0615694000
_diffrn_orient_matrix_UB_23      -0.0909490000
_diffrn_orient_matrix_UB_31      -0.0314488000
_diffrn_orient_matrix_UB_32      -0.0832020000
_diffrn_orient_matrix_UB_33      0.0677923000
_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  0.0196
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11200
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.049
_diffrn_reflns_theta_min         5.514
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.523
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.05963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.339
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3586
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0365
_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^)+(0.0694P)^2^+0.2788P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1077
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3317
_reflns_number_total             3586
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc03065e2.cif
_cod_data_source_block           zhuyy_0316
_cod_depositor_comments
'Adding full bibliography for 7243782--7243783.cif.'
_cod_database_code               7243782
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.901
_shelx_estimated_absorpt_t_min   0.804
_reflns_odcompleteness_completeness 99.55
_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:
 C8(H8A,H8B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
;
_shelx_res_checksum              73806
_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 11.535
_oxdiff_exptl_absorpt_empirical_full_min 0.642