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_4038304
_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         'C23 H27 F N O5 P'
_chemical_formula_sum            'C23 H27 F N O5 P'
_chemical_formula_weight         447.42
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-11-07T15:38:34-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                71.639(3)
_cell_angle_beta                 88.416(3)
_cell_angle_gamma                72.869(3)
_cell_formula_units_Z            4
_cell_length_a                   11.5648(5)
_cell_length_b                   12.9060(5)
_cell_length_c                   17.0405(5)
_cell_measurement_reflns_used    16507
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      74.298
_cell_measurement_theta_min      3.865
_cell_volume                     2300.85(16)
_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    'ShelXS (Sheldrick, 2008)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.998
_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      4.00  29.00   1.00    3.50    --   40.00  88.00  73.20   25
  2  \w   -109.00 -56.00   1.00    3.50    --  -42.13 -57.00-150.00   53
  3  \w    -70.00  31.00   1.00    3.50    --  -42.13  57.00   0.00  101
  4  \w   -113.00 -49.00   1.00    3.50    --  -42.13 -38.00 -60.00   64
  5  \w    -52.00 -14.00   1.00    3.50    --  -42.13 -57.00-150.00   38
  6  \w    -48.00 -18.00   1.00    3.50    --  -42.13 -38.00 -60.00   30
  7  \w     78.00 112.00   1.00    3.50    --   42.13  43.00  32.00   34
  8  \w     17.00  61.00   1.00    3.50    --   42.13  43.00  32.00   44
  9  \w      3.00  96.00   1.00    3.50    --   42.13-125.00-180.00   93
 10  \w     10.00  35.00   1.00    3.50    --   44.00  81.00 166.79   25
 11  \w     10.00  35.00   1.00    3.50    --   44.00  81.00 -55.84   25
 12  \w     14.00  39.00   1.00    3.50    --   48.00  83.00  -9.45   25
 13  \w     14.00  39.00   1.00    3.50    --   48.00  83.00 175.78   25
 14  \w     14.00  39.00   1.00    3.50    --   48.00  83.00 109.81   25
 15  \w     14.00  39.00   1.00    3.50    --   48.00  83.00-104.06   25
 16  \w     19.00  45.00   1.00    3.50    --   52.00  80.00  11.48   26
 17  \w     19.00  44.00   1.00    3.50    --   52.00  80.00 -85.84   25
 18  \w     19.00  44.00   1.00    3.50    --   52.00  80.00  62.61   25
 19  \w     32.00  57.00   1.00    3.50    --   64.00  77.00 -39.87   25
 20  \w     31.00  57.00   1.00    3.50    --   64.00  77.00 152.73   26
 21  \w     32.00  59.00   1.00    3.50    --   64.00  76.00 123.28   27
 22  \w    110.00 143.00   1.00    3.50    --   68.00  75.00-156.67   33
 23  \w    110.00 137.00   1.00    3.50    --   68.00  75.00 -11.91   27
 24  \w     37.00  64.00   1.00    3.50    --   68.00  76.00  48.62   27
 25  \w     36.00  62.00   1.00    3.50    --   68.00  76.00  93.69   26
 26  \w     36.00  62.00   1.00    3.50    --   68.00  75.00-156.67   26
 27  \w     37.00  64.00   1.00    3.50    --   68.00  75.00 -11.91   27
 28  \w    100.00 147.00   1.00    3.50    --   72.00  76.00  21.44   47
 29  \w     41.00  66.00   1.00    3.50    --   72.00  76.00  21.44   25
 30  \w     41.00  71.00   1.00    3.50    --   72.00  75.00-100.31   30
 31  \w     39.00  65.00   1.00    3.50    --   72.00  77.00 166.77   26
 32  \w     39.00  65.00   1.00    3.50    --   72.00  77.00 -82.85   26
 33  \w     46.00  71.00   1.00   14.00    --   76.00  70.00-175.62   25
 34  \w    112.00 139.00   1.00   14.00    --   76.00  72.00-138.89   27
 35  \w     45.00  71.00   1.00   14.00    --   76.00  72.00-138.89   26
 36  \w     51.00  79.00   1.00   14.00    --   80.00  63.00 -47.01   28
 37  \w     50.00  77.00   1.00   14.00    --   80.00  67.00  -2.68   27
 38  \w     54.00  79.00   1.00   14.00    --   84.00  69.00  43.30   25
 39  \w     52.00  79.00   1.00   14.00    --   84.00  75.00 105.23   27
 40  \w     56.00  93.00   1.00   14.00    --   84.00  56.00 -79.29   37
 41  \w    129.00 154.00   1.00   14.00    --   84.00  69.00  43.30   25
 42  \w     58.00  84.00   1.00   14.00    --   88.00  66.00-139.98   26
 43  \w     61.00  89.00   1.00   14.00    --   88.00  55.00  82.14   28
 44  \w    104.00 144.00   1.00   14.00    --   96.00  65.00 109.95   40
 45  \w     67.00  92.00   1.00   14.00    --   96.00  65.00 109.95   25
 46  \w     74.00 103.00   1.00   14.00    --   96.00  63.00 121.33   29
 47  \w     63.00 157.00   1.00   14.00    --   96.00  77.00 159.00   94
 48  \w     38.00  66.00   1.00   14.00    --  107.93 -45.00 -30.00   28
 49  \w     79.00 106.00   1.00   14.00    --  107.93  61.00 -60.00   27
 50  \w     37.00  92.00   1.00   14.00    --  107.93 -94.00   0.00   55
 51  \w     40.00  67.00   1.00   14.00    --  107.93 -45.00 150.00   27
 52  \w    110.00 156.00   1.00   14.00    --  107.93  77.00 -90.00   46
 53  \w     76.00 101.00   1.00   14.00    --  107.93  77.00 -90.00   25
 54  \w     25.00 107.00   1.00   14.00    --  107.93 -94.00 -90.00   82
 55  \w     76.00 148.00   1.00   14.00    --  107.93  77.00-150.00   72
 56  \w     40.00 118.00   1.00   14.00    --  107.93-125.00 120.00   78
 57  \w     76.00 158.00   1.00   14.00    --  107.93  77.00 120.00   82
 58  \w     75.00 158.00   1.00   14.00    --  107.93  77.00-120.00   83
 59  \w     35.00 117.00   1.00   14.00    --  107.93-125.00 -90.00   82
 60  \w     35.00  67.00   1.00   14.00    --  107.93 -45.00 -90.00   32
 61  \w     75.00 133.00   1.00   14.00    --  107.93  77.00 -60.00   58
 62  \w     77.00 156.00   1.00   14.00    --  107.93  77.00  60.00   79
 63  \w     75.00 152.00   1.00   14.00    --  107.93  77.00 -30.00   77
 64  \w     43.00 122.00   1.00   14.00    --  107.93 -77.00  90.00   79
 65  \w     39.00  64.00   1.00   14.00    --  107.93 -43.00-118.00   25
 66  \w     83.00 110.00   1.00   14.00    --  107.93  61.00   0.00   27
 67  \w     37.00  69.00   1.00   14.00    --  107.93 -30.00  90.00   32
 68  \w     76.00 136.00   1.00   14.00    --  107.93  77.00  30.00   60
 69  \w     75.00 146.00   1.00   14.00    --  107.93  77.00-180.00   71
 70  \w     36.00  79.00   1.00   14.00    --  107.93-125.00  90.00   43
 71  \w     76.00 144.00   1.00   14.00    --  107.93  77.00   0.00   68
 72  \w     33.00  60.00   1.00   14.00    --  107.93 -30.00 120.00   27
;
_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      -0.0966014
_diffrn_orient_matrix_UB_12      0.1170187
_diffrn_orient_matrix_UB_13      -0.0372787
_diffrn_orient_matrix_UB_21      -0.1004275
_diffrn_orient_matrix_UB_22      -0.0543383
_diffrn_orient_matrix_UB_23      0.0349043
_diffrn_orient_matrix_UB_31      0.0106907
_diffrn_orient_matrix_UB_32      0.0274159
_diffrn_orient_matrix_UB_33      0.0807006
_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  0.0485
_diffrn_reflns_av_unetI/netI     0.0796
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            41413
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.988
_diffrn_reflns_theta_min         3.785
_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    1.419
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.981
_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    1.292
_exptl_crystal_description       needle
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.197
_exptl_crystal_size_min          0.043
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     586
_refine_ls_number_reflns         8534
_refine_ls_number_restraints     46
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.055
_refine_ls_R_factor_gt           0.0389
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0466P)^2^+0.8603P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.0988
_reflns_Friedel_coverage         0
_reflns_number_gt                6763
_reflns_number_total             8534
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00280_si_003.cif
_cod_data_source_block           a20190279_xd303
_cod_original_cell_volume        2300.86(15)
_cod_database_code               4038304