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_4038307
_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 ad
_chemical_formula_moiety         'C23 H29 N2 O4 P'
_chemical_formula_sum            'C23 H29 N2 O4 P'
_chemical_formula_weight         428.45
_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             2019-12-05T09:00:51-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 99.544(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.7426(9)
_cell_length_b                   6.4084(5)
_cell_length_c                   18.2313(14)
_cell_measurement_reflns_used    2455
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      72.05
_cell_measurement_theta_min      4.567
_cell_volume                     1122.51(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 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   -119.00 -18.00   1.00    8.00    --  -42.38 -77.00   0.00  101
  2  \w    -32.00  36.00   1.00    8.00    --   42.38 -38.00  60.00   68
  3  \w     39.00  84.00   1.00    8.00    --   42.38  38.00 -90.00   45
  4  \w     13.00  92.00   1.00    8.00    --   42.38-125.00-150.00   79
  5  \w     23.00  91.00   1.00    8.00    --   42.38-125.00   0.00   68
  6  \w     37.00  64.00   1.00   32.00    --  107.93 -30.00 -60.00   27
  7  \w     35.00  69.00   1.00   32.00    --  107.93 -30.00-180.00   34
  8  \w    114.00 141.00   1.00   32.00    --  107.93  15.00 -90.00   27
  9  \w     38.00  65.00   1.00   32.00    --  107.93 -45.00 120.00   27
 10  \w     32.00  57.00   1.00   32.00    --  107.93 -30.00  60.00   25
 11  \w     32.00  67.00   1.00   32.00    --  107.93 -30.00   0.00   35
 12  \w     32.00  66.00   1.00   32.00    --  107.93 -30.00 -30.00   34
 13  \w     37.00  64.00   1.00   32.00    --  107.93 -30.00  30.00   27
 14  \w     80.00 157.00   1.00   32.00    --  107.93  30.00 -60.00   77
 15  \w     28.00 100.00   1.00   32.00    --  107.93 -94.00 -30.00   72
 16  \w     89.00 114.00   1.00   32.00    --  107.93  30.00 -90.00   25
 17  \w     82.00 145.00   1.00   32.00    --  107.93  61.00 150.00   63
 18  \w     79.00 158.00   1.00   32.00    --  107.93  61.00  90.00   79
 19  \w     36.00 134.00   1.00   32.00    --  107.93 -69.00  10.00   98
 20  \w     84.00 111.00   1.00   32.00    --  107.93  45.00-120.00   27
 21  \w     55.00  92.00   1.00   32.00    --  107.93  15.00 -90.00   37
 22  \w     58.00 117.00   1.00   32.00    --  107.93-125.00 -90.00   59
 23  \w     64.00  89.00   1.00   32.00    --  107.93 -15.00  90.00   25
 24  \w     28.00  55.00   1.00    8.00    --   42.38  38.00 -90.00   27
 25  \w     73.00 100.00   1.00    8.00    --   42.38  38.00 -90.00   27
 26  \w     50.00  98.00   1.00   32.00    --  107.93-125.00 -30.00   48
 27  \w     88.00 115.00   1.00   32.00    --  107.93-125.00 120.00   27
 28  \w     33.00  67.00   1.00   32.00    --  107.93 -30.00 -90.00   34
 29  \w     32.00  57.00   1.00   32.00    --  107.93 -30.00  90.00   25
 30  \w     75.00 137.00   1.00   32.00    --  107.93 -77.00  90.00   62
 31  \w   -119.00 -55.00   1.00    8.00    --  -42.38 -77.00 150.00   64
 32  \w   -119.00 -10.00   1.00    8.00    --  -42.38 -77.00-150.00  109
 33  \w   -116.00 -14.00   1.00    8.00    --  -42.38 -57.00-120.00  102
 34  \w   -117.00 -18.00   1.00    8.00    --  -42.38 -38.00  30.00   99
 35  \w      2.00  98.00   1.00    8.00    --   42.38-125.00 -60.00   96
 36  \w     10.00 119.00   1.00    8.00    --   42.38  77.00 120.00  109
;
_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      -0.1031227
_diffrn_orient_matrix_UB_12      -0.0412742
_diffrn_orient_matrix_UB_13      -0.0722148
_diffrn_orient_matrix_UB_21      -0.0636125
_diffrn_orient_matrix_UB_22      -0.1825054
_diffrn_orient_matrix_UB_23      0.0379107
_diffrn_orient_matrix_UB_31      -0.1050785
_diffrn_orient_matrix_UB_32      0.1509179
_diffrn_orient_matrix_UB_33      0.0262204
_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  0.0978
_diffrn_reflns_av_unetI/netI     0.1879
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12322
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.985
_diffrn_reflns_theta_min         4.602
_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    1.343
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_correction_T_min  0.727
_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            colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description       needle
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.544
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.033
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 2853 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
 The Friedel pair coverage of the experiment is almost complete
 (99%). Analysis of the absolute structure using likelihood methods
 (Hooft, Straver & Spek, 2008) was performed using PLATON
 (Spek, 2009). The resulting value was y=-0.14(4)
;
_refine_ls_abs_structure_Flack   0.14(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         4158
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.01
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.066
_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^)+(0.0378P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1512
_reflns_Friedel_coverage         0.819
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                3071
_reflns_number_total             4158
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00280_si_002.cif
_cod_data_source_block           a20190409_xd376crist3
_cod_database_code               4038307