Three new phosphoric triamides with a [C(O)NH]P(O)[N(C)(C)]~2~ skeleton: a database analysis of C—N—C and P—N—C bond angles
Pourayoubi, Mehrdad; Tarahhomi, Atekeh; Rheingold, Arnold L.; Golen, James A.; Acta Crystallographica Section C 70 (2014) 998–1002; doi:10.1107/S2053229614020488

data_2019686
_publ_section_title
;
 Three new phosphoric triamides with a [C(O)NH]P(O)[N(C)(C)]~2~ skeleton:
 a database analysis of C---N---C and P---N---C bond angles
;
_journal_coeditor_code           UK3104
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              998
_journal_page_last               1002
_journal_paper_doi               10.1107/S2053229614020488
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C21 H33 F N3 O2 P'
_chemical_formula_moiety         'C21 H33 F N3 O2 P'
_chemical_formula_sum            'C21 H33 F N3 O2 P'
_chemical_formula_weight         409.47
_chemical_name_systematic
;
N,N'-dicyclohexyl-N''-(2-fluorobenzoyl)-N,N'-dimethylphosphoric 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                67.9150(10)
_cell_angle_beta                 77.9020(10)
_cell_angle_gamma                79.9780(10)
_cell_formula_units_Z            2
_cell_length_a                   10.3245(2)
_cell_length_b                   10.5131(2)
_cell_length_c                   11.3253(2)
_cell_measurement_reflns_used    8116
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      68.17
_cell_measurement_theta_min      4.27
_cell_volume                     1107.61(4)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 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      90(2)
_diffrn_measured_fraction_theta_full 0.942
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10794
_diffrn_reflns_theta_full        68.16
_diffrn_reflns_theta_max         68.16
_diffrn_reflns_theta_min         4.27
_exptl_absorpt_coefficient_mu    1.339
_exptl_absorpt_correction_T_max  0.8778
_exptl_absorpt_correction_T_min  0.8244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.434
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         3824
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0386
_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^)+(0.0581P)^2^+0.4562P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1025
_reflns_number_gt                3710
_reflns_number_total             3824
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            uk3104sup1.cif
_cod_data_source_block           III
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2019686
_cod_database_fobs_code          2019686