Synthesis of Fluorinated β-Aminophosphonates and γ-Lactams
Concepción Alonso; María González; María Fuertes; Gloria Rubiales; Jose María Ezpeleta; Francisco Palacios; Journal of Organic Chemistry 78 (2013) 3858–3866; doi:10.1021/jo400281e

data_4028162
_publ_contact_author_address
;
Departamento de Quimica Organica I
Facultad de Farmacia
UPV/EHU
Paseo de la Universidad, 7
01006 Vitoria-Gasteiz
Spain
;
_publ_contact_author_email       francisco.palacios@ehu.es
_publ_contact_author_name        'Palacios, Francisco'
_publ_section_title
;
 Synthesis of Fluorinated \b-Aminophosphonates and \g-Lactams
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3858
_journal_page_last               3866
_journal_paper_doi               10.1021/jo400281e
_journal_volume                  78
_journal_year                    2013
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C15 H18 F3 N2 O6 P1'
_chemical_formula_sum            'C15 H18 F3 N2 O6 P'
_chemical_formula_weight         410.28
_chemical_name_systematic
;
4-Diethoxyphosphinyl-5-trifluoromethyl-1-
(4-nitrophenyl)pyrrolidin-2-one
;
_space_group_IT_number           14
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-11-20T15:05:14-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 105.625(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5576(3)
_cell_length_b                   7.9815(2)
_cell_length_c                   20.4407(4)
_cell_measurement_reflns_used    4425
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.2497
_cell_measurement_theta_min      2.2425
_cell_measurement_wavelength     0.71073
_cell_volume                     1815.91(8)
_computing_cell_refinement
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4023
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0057997
_diffrn_orient_matrix_UB_12      0.1655467
_diffrn_orient_matrix_UB_13      0.0377346
_diffrn_orient_matrix_UB_21      0.1358833
_diffrn_orient_matrix_UB_22      0.0251236
_diffrn_orient_matrix_UB_23      0.0102923
_diffrn_orient_matrix_UB_31      -0.0256027
_diffrn_orient_matrix_UB_32      0.0959928
_diffrn_orient_matrix_UB_33      -0.0677926
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8577
_diffrn_reflns_theta_full        70
_diffrn_reflns_theta_max         70
_diffrn_reflns_theta_min         4
_exptl_absorpt_coefficient_mu    1.961
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_correction_T_min  0.931
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
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)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_description       prism
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.2298
_exptl_crystal_size_mid          0.1754
_exptl_crystal_size_min          0.0965
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.00040(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3434
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0301
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0457P)^2^+0.6252P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0855
_reflns_number_gt                2978
_reflns_number_total             3434
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo400281e_si_003.cif
_cod_data_source_block           mf353a
_cod_original_cell_volume        1815.91(7)
_cod_database_code               4028162