Different cyclic motifs in phosphoric triamides containing a C(O)NHP(O)(NH)~2~ skeleton and an <i>R</i>~2~^2^(10) graph set in three new compounds: a database analysis of hydrogen-bond strengths based on motifs
Pourayoubi, Mehrdad; Tarahhomi, Atekeh; Saneei, Anahid; Rheingold, Arnold L.; Golen, James A.; Acta Crystallographica Section C 67 (2011) o265–o272; doi:10.1107/S0108270111019755

data_2018166
_publ_section_title
;
 Different cyclic motifs in phosphoric triamides containing a
 C(O)NHP(O)(NH)~2~ skeleton and an <i>R</i>~2~^2^(10) graph set in
 three new compounds: a database analysis of hydrogen-bond strengths
 based on motifs
;
_journal_coeditor_code           YP3002
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o265
_journal_page_last               o272
_journal_paper_doi               10.1107/S0108270111019755
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C21 H18 Cl2 F2 N3 O2 P'
_chemical_formula_moiety         'C21 H18 Cl2 F2 N3 O2 P'
_chemical_formula_sum            'C21 H18 Cl2 F2 N3 O2 P'
_chemical_formula_weight         484.25
_chemical_name_systematic
;
<i>N</i>,<i>N</i>'-bis(2-chlorobenzyl)-<i>N</i>''-(2,6-
difluorobenzoyl)phosphoric triamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.056(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.643(3)
_cell_length_b                   4.9874(6)
_cell_length_c                   21.482(3)
_cell_measurement_reflns_used    7966
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.81
_cell_measurement_theta_min      3.36
_cell_volume                     2058.1(5)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and Mercury (Macrae <i>et al.</i>,
2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and enCIFer (Allen <i>et al.</i>,
2004)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       '\f and \w'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0741
_diffrn_reflns_av_sigmaI/netI    0.0622
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            25048
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.94
_diffrn_reflns_theta_min         1.06
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.436
_exptl_absorpt_correction_T_max  0.9577
_exptl_absorpt_correction_T_min  0.8987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.652
_refine_diff_density_min         -0.476
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4821
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0523
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0446P)^2^+2.5057P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1279
_reflns_number_gt                3463
_reflns_number_total             4821
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            yp3002.cif
_cod_data_source_block           I
_cod_original_cell_volume        2058.2(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2018166
_cod_database_fobs_code          2018166