The double H-atom acceptability of the P=O group in new <i>X</i>P(O)(NHCH~2~C~6~H~4~-2-Cl)~2~ phosphoramidates [<i>X</i> = C~6~H~5~O– and CF~3~C(O)NH–]: a database analysis of compounds having a P(O)(NH<i>R</i>) group
Pourayoubi, Mehrdad; Nečas, Marek; Negari, Monireh; Acta Crystallographica Section C 68 (2012) o51–o56; doi:10.1107/S0108270111052097

data_2018385
_publ_section_title
;
 The double H-atom acceptability of the P=O group in new
 <i>X</i>P(O)(NHCH~2~C~6~H~4~-2-Cl)~2~ phosphoramidates [<i>X</i> =
 C~6~H~5~O-- and CF~3~C(O)NH--]: a database analysis of compounds having a
 P(O)(NH<i>R</i>) group
;
_journal_coeditor_code           SF3159
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o51
_journal_page_last               o56
_journal_paper_doi               10.1107/S0108270111052097
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C16 H15 Cl2 F3 N3 O2 P'
_chemical_formula_moiety         'C16 H15 Cl2 F3 N3 O2 P'
_chemical_formula_sum            'C16 H15 Cl2 F3 N3 O2 P'
_chemical_formula_weight         440.18
_chemical_name_systematic
;
<i>N</i>,<i>N</i>'-bis(2-chlorobenzyl)-<i>N</i>''-(2,2,2-
trifluoroacetyl)phosphoric triamide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                103.714(17)
_cell_angle_beta                 94.636(15)
_cell_angle_gamma                96.099(15)
_cell_formula_units_Z            2
_cell_length_a                   4.8860(8)
_cell_length_b                   12.192(2)
_cell_length_c                   15.838(3)
_cell_measurement_reflns_used    1283
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.6813
_cell_measurement_theta_min      3.4426
_cell_volume                     905.9(3)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'Mercury (Macrae <i>et al.</i>, 2008)'
_computing_publication_material  'enCIFer (Allen <i>et al.</i>, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.4353
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Oxford Xcalibur Sapphire2 (large Be window)'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0894
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5706
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.47
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.494
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65182
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.326
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.810
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3179
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.810
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0375
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0371P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0750
_refine_ls_wR_factor_ref         0.0796
_reflns_number_gt                1971
_reflns_number_total             3179
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            sf3159.cif
_cod_data_source_block           II
_cod_database_code               2018385
_cod_database_fobs_code          2018385