Reactions of Piperazin-2-one, Morpholin-3-one, and Thiomorpholin-3-one with Triethyl Phosphite Prompted by Phosphoryl Chloride: Scope and Limitations.
Argüello-Velasco, Rubén Oswaldo; Dziuk, Błażej; Zarychta, Bartosz; Ordóñez, Mario; Kafarski, Paweł; ACS omega 4 (2019) 9056–9064; doi:10.1021/acsomega.9b01137

data_4515014
_publ_section_title
;
 Reactions of Piperazin-2-one, Morpholin-3-one, and Thiomorpholin-3-one
 with Triethyl Phosphite Prompted by Phosphoryl Chloride: Scope and
 Limitations.
;
_journal_issue                   5
_journal_name_full               'ACS omega'
_journal_page_first              9056
_journal_page_last               9064
_journal_paper_doi               10.1021/acsomega.9b01137
_journal_volume                  4
_journal_year                    2019
_chemical_formula_sum            'C22 H28 N3 O8 P S2'
_chemical_formula_weight         557.56
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                83.029(3)
_cell_angle_beta                 74.675(3)
_cell_angle_gamma                73.050(3)
_cell_formula_units_Z            2
_cell_length_a                   9.4026(4)
_cell_length_b                   10.4466(3)
_cell_length_c                   13.9332(5)
_cell_measurement_reflns_used    8588
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      25.998
_cell_measurement_theta_min      3.035
_cell_volume                     1261.13(8)
_computing_cell_refinement       'CrysAlisCCD (Oxford Diffraction Ltd., 2008)'
_computing_data_collection       'CrysAlisCCD (Oxford Diffraction Ltd., 2008)'
_computing_data_reduction        'CrysAlisCCD (Oxford Diffraction Ltd., 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector_area_resol_mean '1024 x 1024 with blocks 2 x 2'
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  Xcalibur
_diffrn_measurement_method       \w--scan
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0686
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8588
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         3.035
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.327
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4868
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.951
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0475P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0875
_refine_ls_wR_factor_ref         0.0949
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3422
_reflns_number_total             4876
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao9b01137_si_002.cif
_cod_data_source_block           BD191_a
_cod_database_code               4515014
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              58748
_shelx_hkl_checksum              6301