Brönsted Acid Catalyzed Multicomponent Synthesis of Phosphorus and Fluorine-Derived γ-Lactam Derivatives.
Del Corte, Xabier; López-Francés, Adrián; Maestro, Aitor; Martinez de Marigorta, Edorta; Palacios, Francisco; Vicario, Javier; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00280

data_4038306
_publ_section_title
;
 Br\"onsted Acid Catalyzed Multicomponent Synthesis of Phosphorus and
 Fluorine-Derived \g-Lactam Derivatives.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00280
_journal_year                    2020
_chemical_formula_moiety         'C25 H33 N2 O4 P'
_chemical_formula_sum            'C25 H33 N2 O4 P'
_chemical_formula_weight         456.5
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-30T21:29:58-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 103.667(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7968(4)
_cell_length_b                   20.6201(13)
_cell_length_c                   15.4863(7)
_cell_measurement_reflns_used    2382
_cell_measurement_temperature    150.6(9)
_cell_measurement_theta_max      66.203
_cell_measurement_theta_min      3.582
_cell_volume                     2419.2(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2012
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_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    -79.00  11.00   1.00    3.25    --  -42.38 108.00  28.00   90
  2  \w     -6.00  86.00   1.00    3.25    --   42.38-108.00 -68.00   92
  3  \w     33.00 112.00   1.00   12.00    --  107.93-108.00 -68.00   79
  4  \w    112.00 138.00   1.00   12.00    --  107.93 108.00  28.00   26
  5  \w      5.00  30.00   1.00    3.25    --   40.00  86.00  62.41   25
  6  \w   -108.00 -56.00   1.00    3.25    --  -42.38 -77.00 -90.00   52
  7  \w   -109.00 -21.00   1.00    3.25    --  -42.38 -38.00   0.00   88
  8  \w    -67.00 -14.00   1.00    3.25    --  -42.38 -57.00 -90.00   53
  9  \w    -37.00 -10.00   1.00    3.25    --  -42.38 -77.00 -90.00   27
 10  \w     20.00  72.00   1.00    3.25    --   42.38  38.00  30.00   52
 11  \w     15.00  42.00   1.00    3.25    --   44.00  61.00  84.60   27
 12  \w     56.00 115.00   1.00    3.25    --   44.00  61.00  84.60   59
 13  \w      7.00  32.00   1.00    3.25    --   44.00  89.00 -44.67   25
 14  \w     18.00  43.00   1.00    3.25    --   52.00  82.00   3.24   25
 15  \w     18.00  43.00   1.00    3.25    --   52.00  82.00-108.91   25
 16  \w     18.00  44.00   1.00    3.25    --   52.00  81.00-155.29   26
 17  \w     19.00  45.00   1.00    3.25    --   52.00  80.00 168.97   26
 18  \w     19.00  44.00   1.00    3.25    --   52.00  80.00 -69.46   25
 19  \w     19.00  44.00   1.00    3.25    --   52.00  80.00  98.35   25
 20  \w     18.00  43.00   1.00    3.25    --   52.00  82.00 132.94   25
 21  \w     18.00  43.00   1.00    3.25    --   52.00  82.00  57.66   25
 22  \w     29.00  56.00   1.00    3.25    --   60.00  77.00  24.82   27
 23  \w     31.00  72.00   1.00    3.25    --   64.00  77.00 -57.24   41
 24  \w     31.00  58.00   1.00    3.25    --   64.00  77.00  48.73   27
 25  \w     33.00  59.00   1.00    3.25    --   64.00  75.00  86.18   26
 26  \w     36.00  62.00   1.00    3.25    --   68.00  77.00 -23.06   26
 27  \w     36.00  72.00   1.00    3.25    --   68.00  76.00 177.33   36
 28  \w     40.00  67.00   1.00    3.25    --   72.00  77.00-130.53   27
 29  \w     39.00  66.00   1.00    3.25    --   72.00  77.00 106.31   27
 30  \w     93.00 130.00   1.00    3.25    --   72.00  77.00 106.31   37
 31  \w     40.00  66.00   1.00    3.25    --   72.00  75.00 -97.58   26
 32  \w     39.00  65.00   1.00    3.25    --   72.00  77.00-160.76   26
 33  \w     46.00  73.00   1.00   12.00    --   76.00  65.00  68.12   27
 34  \w     44.00  70.00   1.00   12.00    --   76.00  76.00 119.77   26
 35  \w     51.00  78.00   1.00   12.00    --   80.00  68.00 -17.43   27
 36  \w     48.00  74.00   1.00   12.00    --   80.00  74.00 -50.34   26
 37  \w    119.00 152.00   1.00   12.00    --   80.00  74.00 -50.34   33
 38  \w     49.00 122.00   1.00   12.00    --   80.00  72.00 144.57   73
 39  \w     49.00 152.00   1.00   12.00    --   80.00  71.00 -82.31  103
 40  \w     53.00  80.00   1.00   12.00    --   84.00  70.00 -46.02   27
 41  \w     54.00  89.00   1.00   12.00    --   84.00  66.00   2.17   35
 42  \w     53.00  80.00   1.00   12.00    --   84.00  69.00-159.70   27
 43  \w    121.00 148.00   1.00   12.00    --   84.00  66.00   2.17   27
 44  \w    132.00 158.00   1.00   12.00    --   84.00  70.00 -46.02   26
 45  \w     58.00  85.00   1.00   12.00    --   88.00  65.00  80.89   27
 46  \w     60.00  87.00   1.00   12.00    --   92.00  73.00  39.55   27
 47  \w     63.00 151.00   1.00   12.00    --   96.00  77.00 151.13   88
 48  \w     31.00  99.00   1.00   12.00    --  107.93 -94.00-150.00   68
 49  \w     27.00 104.00   1.00   12.00    --  107.93 -94.00 150.00   77
 50  \w     81.00 141.00   1.00   12.00    --  107.93  61.00  90.00   60
 51  \w     75.00 146.00   1.00   12.00    --  107.93  77.00  90.00   71
 52  \w     81.00 109.00   1.00   12.00    --  107.93  61.00 -90.00   28
 53  \w    109.00 157.00   1.00   12.00    --  107.93  77.00 -30.00   48
 54  \w     75.00 155.00   1.00   12.00    --  107.93  77.00 120.00   80
 55  \w     75.00 105.00   1.00   12.00    --  107.93  77.00 -30.00   30
 56  \w     75.00 147.00   1.00   12.00    --  107.93  77.00   0.00   72
 57  \w     40.00  74.00   1.00   12.00    --  107.93 -45.00-120.00   34
 58  \w     79.00 106.00   1.00   12.00    --  107.93  61.00   0.00   27
 59  \w     81.00 109.00   1.00   12.00    --  107.93  61.00-150.00   28
 60  \w     75.00 148.00   1.00   12.00    --  107.93  77.00-150.00   73
 61  \w     75.00 149.00   1.00   12.00    --  107.93  77.00-120.00   74
 62  \w     26.00 105.00   1.00   12.00    --  107.93 -94.00 -30.00   79
 63  \w     31.00 108.00   1.00   12.00    --  107.93 -94.00  60.00   77
 64  \w     75.00 147.00   1.00   12.00    --  107.93  77.00 -60.00   72
 65  \w     75.00 148.00   1.00   12.00    --  107.93  77.00 -90.00   73
 66  \w     76.00 103.00   1.00   12.00    --  107.93  77.00  60.00   27
 67  \w     35.00  75.00   1.00   12.00    --  107.93 -45.00-180.00   40
 68  \w     40.00  65.00   1.00   12.00    --  107.93 -45.00 -60.00   25
 69  \w     42.00  68.00   1.00   12.00    --  107.93 -45.00  60.00   26
 70  \w    107.00 152.00   1.00   12.00    --  107.93  77.00-180.00   45
 71  \w     91.00 116.00   1.00   12.00    --  107.93-125.00  60.00   25
 72  \w     41.00  77.00   1.00   12.00    --  107.93-125.00  60.00   36
 73  \w     75.00 101.00   1.00   12.00    --  107.93  77.00-180.00   26
 74  \w     79.00 146.00   1.00   12.00    --  107.93  77.00  30.00   67
 75  \w     36.00  75.00   1.00   12.00    --  107.93 -45.00  30.00   39
 76  \w     35.00  68.00   1.00   12.00    --  107.93 -45.00 120.00   33
;
_diffrn_measurement_device       'four-circle\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1606711
_diffrn_orient_matrix_UB_12      0.0445122
_diffrn_orient_matrix_UB_13      0.004747
_diffrn_orient_matrix_UB_21      -0.1060599
_diffrn_orient_matrix_UB_22      0.0580014
_diffrn_orient_matrix_UB_23      0.022547
_diffrn_orient_matrix_UB_31      0.0656441
_diffrn_orient_matrix_UB_32      -0.0152015
_diffrn_orient_matrix_UB_33      0.0997748
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.2437
_diffrn_reflns_av_unetI/netI     0.4341
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            47617
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.993
_diffrn_reflns_theta_min         3.636
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    1.271
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.904
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_description       needle
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.289
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.048
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         4500
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1292
_refine_ls_R_factor_gt           0.065
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0420P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1355
_refine_ls_wR_factor_ref         0.1665
_reflns_Friedel_coverage         0
_reflns_number_gt                2545
_reflns_number_total             4500
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00280_si_004.cif
_cod_data_source_block           a20190280_xd323
_cod_database_code               4038306