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_4038305
_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_absolute_configuration unk
_chemical_formula_moiety         'C26 H24 N2 O'
_chemical_formula_sum            'C26 H24 N2 O'
_chemical_formula_weight         380.47
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-12-02T16:57:55-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 115.110(12)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.2516(13)
_cell_length_b                   7.1055(5)
_cell_length_c                   13.0019(12)
_cell_measurement_reflns_used    3222
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      74.067
_cell_measurement_theta_min      3.732
_cell_volume                     1024.90(19)
_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 1
_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     -3.00  22.00   1.00    4.00    --   36.00  96.00 122.98   25
  2  \w     -4.00  21.00   1.00    4.00    --   36.00  97.00 -26.02   25
  3  \w    -95.00 -14.00   1.00    4.00    --  -41.88 -57.00  30.00   81
  4  \w    -53.00 -17.00   1.00    4.00    --  -41.88 -38.00  60.00   36
  5  \w    -74.00  31.00   1.00    4.00    --  -41.88  77.00-180.00  105
  6  \w   -117.00  -2.00   1.00    4.00    --  -41.88 -19.00 150.00  115
  7  \w      9.00  40.00   1.00    4.00    --   41.88  77.00-150.00   31
  8  \w     80.00 108.00   1.00    4.00    --   41.88  77.00-150.00   28
  9  \w      3.00  98.00   1.00    4.00    --   41.88-125.00  30.00   95
 10  \w     14.00  40.00   1.00    4.00    --   48.00  83.00-106.02   26
 11  \w     14.00  39.00   1.00    4.00    --   48.00  81.00-161.33   25
 12  \w     19.00  44.00   1.00    4.00    --   52.00  80.00 -21.35   25
 13  \w     19.00  44.00   1.00    4.00    --   52.00  80.00  83.18   25
 14  \w     19.00  44.00   1.00    4.00    --   52.00  80.00  10.44   25
 15  \w     19.00  44.00   1.00    4.00    --   52.00  80.00 148.42   25
 16  \w     24.00  61.00   1.00    4.00    --   56.00  77.00-113.15   37
 17  \w     33.00  58.00   1.00    4.00    --   64.00  75.00 103.01   25
 18  \w     85.00 119.00   1.00    4.00    --   64.00  75.00 103.01   34
 19  \w     35.00  61.00   1.00    4.00    --   68.00  77.00   0.11   26
 20  \w     36.00  64.00   1.00    4.00    --   68.00  73.00 133.45   28
 21  \w     40.00  68.00   1.00    4.00    --   68.00  69.00-154.15   28
 22  \w     35.00  61.00   1.00    4.00    --   68.00  77.00 168.59   26
 23  \w     37.00  64.00   1.00    4.00    --   68.00  76.00 -90.97   27
 24  \w     36.00  61.00   1.00    4.00    --   68.00  77.00 -67.67   25
 25  \w     35.00  62.00   1.00    4.00    --   68.00  77.00  67.55   27
 26  \w     91.00 139.00   1.00    4.00    --   68.00  69.00-154.15   48
 27  \w    105.00 147.00   1.00    4.00    --   72.00  75.00-127.88   42
 28  \w     41.00  66.00   1.00    4.00    --   72.00  75.00-127.88   25
 29  \w     41.00  66.00   1.00    4.00    --   72.00  76.00 -47.08   25
 30  \w     40.00  66.00   1.00    4.00    --   72.00  75.00  28.57   26
 31  \w     43.00  73.00   1.00    4.00    --   72.00  69.00 175.01   30
 32  \w     49.00 102.00   1.00   16.00    --   80.00  71.00 -46.03   53
 33  \w     53.00  81.00   1.00   16.00    --   84.00  76.00  49.56   28
 34  \w    100.00 158.00   1.00   16.00    --   84.00  74.00  32.03   58
 35  \w     53.00  78.00   1.00   16.00    --   84.00  74.00  32.03   25
 36  \w     58.00  83.00   1.00   16.00    --   88.00  69.00-127.35   25
 37  \w     63.00  88.00   1.00   16.00    --   88.00  61.00  -3.41   25
 38  \w     57.00  89.00   1.00   16.00    --   88.00  70.00  81.90   32
 39  \w     60.00  93.00   1.00   16.00    --   92.00  76.00-110.75   33
 40  \w     74.00 107.00   1.00   16.00    --  104.00  66.00 109.97   33
 41  \w     29.00 109.00   1.00   16.00    --  109.18 -94.00 120.00   80
 42  \w     39.00 121.00   1.00   16.00    --  109.18 -61.00 -30.00   82
 43  \w     84.00 156.00   1.00   16.00    --  109.18  77.00 150.00   72
 44  \w     80.00 113.00   1.00   16.00    --  109.18  61.00 150.00   33
 45  \w    119.00 157.00   1.00   16.00    --  109.18  61.00  90.00   38
 46  \w     41.00  70.00   1.00   16.00    --  109.18 -45.00 120.00   29
 47  \w     77.00 150.00   1.00   16.00    --  109.18  77.00 -90.00   73
 48  \w     36.00  77.00   1.00   16.00    --  109.18 -45.00 -90.00   41
 49  \w     78.00 158.00   1.00   16.00    --  109.18  77.00-150.00   80
 50  \w     40.00  74.00   1.00   16.00    --  109.18 -45.00  90.00   34
 51  \w     77.00 145.00   1.00   16.00    --  109.18  77.00  30.00   68
 52  \w     41.00  85.00   1.00   16.00    --  109.18-118.00-122.00   44
 53  \w     80.00 107.00   1.00   16.00    --  109.18  61.00   0.00   27
 54  \w     85.00 112.00   1.00   16.00    --  109.18  61.00  90.00   27
 55  \w     72.00 108.00   1.00   16.00    --  109.18 -94.00  30.00   36
 56  \w     77.00 147.00   1.00   16.00    --  109.18  77.00 -60.00   70
 57  \w     77.00 158.00   1.00   16.00    --  109.18  77.00-180.00   81
 58  \w     41.00 124.00   1.00   16.00    --  109.18-133.00 -61.00   83
 59  \w     82.00 109.00   1.00   16.00    --  109.18  61.00-180.00   27
 60  \w     78.00 156.00   1.00   16.00    --  109.18  77.00   0.00   78
 61  \w     83.00 150.00   1.00   16.00    --  109.18  77.00-120.00   67
 62  \w    111.00 148.00   1.00   16.00    --  109.18  77.00  60.00   37
 63  \w     77.00 103.00   1.00   16.00    --  109.18  77.00  60.00   26
 64  \w     77.00 158.00   1.00   16.00    --  109.18  77.00 120.00   81
 65  \w    109.00 156.00   1.00   16.00    --  109.18  77.00 -30.00   47
 66  \w     77.00 103.00   1.00   16.00    --  109.18  77.00 -30.00   26
 67  \w     27.00 106.00   1.00   16.00    --  109.18 -94.00 -60.00   79
;
_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      -0.0671699
_diffrn_orient_matrix_UB_12      -0.0449129
_diffrn_orient_matrix_UB_13      0.0739338
_diffrn_orient_matrix_UB_21      0.0016547
_diffrn_orient_matrix_UB_22      0.2103362
_diffrn_orient_matrix_UB_23      0.0294371
_diffrn_orient_matrix_UB_31      -0.12151
_diffrn_orient_matrix_UB_32      0.0273678
_diffrn_orient_matrix_UB_33      -0.1038686
_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  0.102
_diffrn_reflns_av_unetI/netI     0.1625
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17410
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69
_diffrn_reflns_theta_min         3.755
_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    0.590
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.907
_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. Reid.
(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            yellow
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       prism
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.243
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.076
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 979 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3794
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0537
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0484P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1279
_reflns_Friedel_coverage         0.834
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                2855
_reflns_number_total             3794
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00280_si_005.cif
_cod_data_source_block           a20190401_xd373b4
_cod_original_cell_volume        1024.89(16)
_cod_database_code               4038305