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_4515012
_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            'C4 H13 Cl N2 O6 P2'
_chemical_formula_weight         282.55
_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                98.880(5)
_cell_angle_beta                 99.850(6)
_cell_angle_gamma                97.871(6)
_cell_formula_units_Z            2
_cell_length_a                   7.9283(6)
_cell_length_b                   8.0672(4)
_cell_length_c                   8.2847(5)
_cell_measurement_reflns_used    3463
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      25.998
_cell_measurement_theta_min      3.281
_cell_volume                     508.50(6)
_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 0.986
_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  0.0400
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            3463
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         3.281
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.703
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.845
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.987
_refine_diff_density_min         -0.700
_refine_diff_density_rms         0.141
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         1957
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0553
_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^)+(0.0931P)^2^+0.5214P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1491
_refine_ls_wR_factor_ref         0.1542
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1622
_reflns_number_total             1966
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao9b01137_si_002.cif
_cod_data_source_block           BD189_a
_cod_database_code               4515012
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              87149
_shelx_hkl_checksum              98490