#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/96/2019685.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2019685
loop_
_publ_author_name
'Pourayoubi, Mehrdad'
'Tarahhomi, Atekeh'
'Rheingold, Arnold L.'
'Golen, James A.'
_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          'C19 H28 F2 N3 O2 P'
_chemical_formula_moiety         'C19 H28 F2 N3 O2 P'
_chemical_formula_sum            'C19 H28 F2 N3 O2 P'
_chemical_formula_weight         399.41
_chemical_name_systematic
;
N-(2,6-difluorobenzoyl)-N',N''-bis(4-methylpiperidin-1-yl)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                75.392(3)
_cell_angle_beta                 77.744(4)
_cell_angle_gamma                88.084(4)
_cell_formula_units_Z            2
_cell_length_a                   9.6501(12)
_cell_length_b                   10.0580(13)
_cell_length_c                   10.9947(15)
_cell_measurement_reflns_used    4849
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      26.41
_cell_measurement_theta_min      2.59
_cell_volume                     1008.9(2)
_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 et al.,
2004)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9054
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.43
_diffrn_reflns_theta_min         2.48
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  0.9829
_exptl_absorpt_correction_T_min  0.9580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.361
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3952
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0335
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0405P)²+0.4226P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0869
_reflns_number_gt                3370
_reflns_number_total             3952
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            uk3104sup1.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2019685
_cod_database_fobs_code          2019685
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
P P1 0.51614(4) 0.38074(4) 0.69930(3) 0.01150(10) Uani d . 1 1
F F1 0.44221(10) 0.85378(9) 0.75579(9) 0.0280(2) Uani d . 1 1
F F2 0.85888(10) 0.70839(10) 0.52388(9) 0.0274(2) Uani d . 1 1
O O1 0.62555(12) 0.59114(11) 0.82726(10) 0.0221(3) Uani d . 1 1
O O2 0.52053(11) 0.33666(10) 0.57979(9) 0.0147(2) Uani d . 1 1
N N1 0.56551(13) 0.54963(12) 0.64944(12) 0.0128(3) Uani d D 1 1
H H1N 0.5505(17) 0.5919(16) 0.5760(14) 0.015 Uiso d D 1 1
N N2 0.35810(12) 0.35880(12) 0.79196(12) 0.0140(3) Uani d . 1 1
N N3 0.62586(12) 0.30814(12) 0.78784(11) 0.0143(3) Uani d . 1 1
C C1 0.56440(17) 0.88440(16) 0.66585(15) 0.0195(3) Uani d . 1 1
C C2 0.5968(2) 1.01962(16) 0.60307(16) 0.0261(4) Uani d . 1 1
H H2B 0.5357 1.0909 0.6223 0.031 Uiso calc R 1 1
C C3 0.7214(2) 1.04863(17) 0.51091(16) 0.0293(4) Uani d . 1 1
H H3A 0.7460 1.1414 0.4661 0.035 Uiso calc R 1 1
C C4 0.81098(19) 0.94496(18) 0.48282(16) 0.0281(4) Uani d . 1 1
H H4A 0.8968 0.9653 0.4199 0.034 Uiso calc R 1 1
C C5 0.77203(17) 0.81166(16) 0.54872(15) 0.0208(3) Uani d . 1 1
C C6 0.64865(16) 0.77592(15) 0.64142(14) 0.0159(3) Uani d . 1 1
C C7 0.61155(15) 0.62938(15) 0.71690(14) 0.0145(3) Uani d . 1 1
C C8 0.32035(16) 0.41758(16) 0.90464(14) 0.0177(3) Uani d . 1 1
H H8A 0.4082 0.4395 0.9293 0.021 Uiso calc R 1 1
H H8B 0.2647 0.3485 0.9780 0.021 Uiso calc R 1 1
C C9 0.23452(16) 0.54700(16) 0.87722(15) 0.0192(3) Uani d . 1 1
H H9A 0.2962 0.6213 0.8149 0.023 Uiso calc R 1 1
H H9B 0.2019 0.5766 0.9578 0.023 Uiso calc R 1 1
C C10 0.10571(16) 0.52607(15) 0.82302(15) 0.0183(3) Uani d . 1 1
H H10A 0.0414 0.4557 0.8899 0.022 Uiso calc R 1 1
C C11 0.15441(16) 0.46872(15) 0.70523(15) 0.0175(3) Uani d . 1 1
H H11A 0.0709 0.4501 0.6725 0.021 Uiso calc R 1 1
H H11B 0.2164 0.5374 0.6364 0.021 Uiso calc R 1 1
C C12 0.23517(15) 0.33648(15) 0.73969(15) 0.0168(3) Uani d . 1 1
H H12A 0.1708 0.2659 0.8041 0.020 Uiso calc R 1 1
H H12B 0.2679 0.3018 0.6619 0.020 Uiso calc R 1 1
C C13 0.02303(18) 0.65775(17) 0.79406(17) 0.0264(4) Uani d . 1 1
H H13A -0.0038 0.6917 0.8717 0.040 Uiso calc R 1 1
H H13B -0.0626 0.6391 0.7661 0.040 Uiso calc R 1 1
H H13C 0.0823 0.7273 0.7257 0.040 Uiso calc R 1 1
C C14 0.77889(15) 0.33638(15) 0.74004(15) 0.0179(3) Uani d . 1 1
H H14A 0.8137 0.3892 0.7927 0.021 Uiso calc R 1 1
H H14B 0.7966 0.3926 0.6500 0.021 Uiso calc R 1 1
C C15 0.85850(16) 0.20273(15) 0.74646(15) 0.0176(3) Uani d . 1 1
H H15A 0.9616 0.2235 0.7184 0.021 Uiso calc R 1 1
H H15B 0.8306 0.1549 0.6866 0.021 Uiso calc R 1 1
C C16 0.82804(16) 0.10832(15) 0.88181(15) 0.0186(3) Uani d . 1 1
H H16A 0.8655 0.1540 0.9395 0.022 Uiso calc R 1 1
C C17 0.66810(16) 0.08714(15) 0.93067(15) 0.0193(3) Uani d . 1 1
H H17A 0.6314 0.0324 0.8806 0.023 Uiso calc R 1 1
H H17B 0.6487 0.0342 1.0218 0.023 Uiso calc R 1 1
C C18 0.58979(16) 0.22228(15) 0.91992(14) 0.0158(3) Uani d . 1 1
H H18A 0.4862 0.2034 0.9451 0.019 Uiso calc R 1 1
H H18B 0.6160 0.2718 0.9793 0.019 Uiso calc R 1 1
C C19 0.90183(19) -0.02812(17) 0.88444(18) 0.0289(4) Uani d . 1 1
H H19A 1.0044 -0.0116 0.8543 0.043 Uiso calc R 1 1
H H19B 0.8665 -0.0743 0.8281 0.043 Uiso calc R 1 1
H H19C 0.8821 -0.0863 0.9725 0.043 Uiso calc R 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O2 P1 N3 116.74(6) yes
O2 P1 N2 111.60(6) yes
N3 P1 N2 106.71(6) yes
O2 P1 N1 105.13(6) yes
N3 P1 N1 105.32(6) yes
N2 P1 N1 111.20(6) yes
C7 N1 P1 128.36(10) no
C7 N1 H1N 115.7(11) no
P1 N1 H1N 115.6(11) no
C12 N2 C8 113.25(11) yes
C12 N2 P1 119.95(10) yes
C8 N2 P1 121.62(10) yes
C18 N3 C14 113.40(11) yes
C18 N3 P1 126.95(10) yes
C14 N3 P1 119.46(10) yes
F1 C1 C2 118.75(14) no
F1 C1 C6 117.48(14) no
C2 C1 C6 123.76(15) no
C1 C2 C3 117.86(16) no
C1 C2 H2B 121.1 no
C3 C2 H2B 121.1 no
C2 C3 C4 121.22(16) no
C2 C3 H3A 119.4 no
C4 C3 H3A 119.4 no
C5 C4 C3 118.02(16) no
C5 C4 H4A 121.0 no
C3 C4 H4A 121.0 no
F2 C5 C4 119.11(15) no
F2 C5 C6 117.36(14) no
C4 C5 C6 123.53(15) no
C5 C6 C1 115.60(14) no
C5 C6 C7 122.53(13) no
C1 C6 C7 121.78(14) no
O1 C7 N1 125.50(13) no
O1 C7 C6 120.29(12) no
N1 C7 C6 114.20(12) no
N2 C8 C9 111.80(12) no
N2 C8 H8A 109.3 no
C9 C8 H8A 109.3 no
N2 C8 H8B 109.3 no
C9 C8 H8B 109.3 no
H8A C8 H8B 107.9 no
C8 C9 C10 112.57(12) no
C8 C9 H9A 109.1 no
C10 C9 H9A 109.1 no
C8 C9 H9B 109.1 no
C10 C9 H9B 109.1 no
H9A C9 H9B 107.8 no
C13 C10 C11 112.49(13) no
C13 C10 C9 111.58(13) no
C11 C10 C9 109.18(12) no
C13 C10 H10A 107.8 no
C11 C10 H10A 107.8 no
C9 C10 H10A 107.8 no
C12 C11 C10 110.37(12) no
C12 C11 H11A 109.6 no
C10 C11 H11A 109.6 no
C12 C11 H11B 109.6 no
C10 C11 H11B 109.6 no
H11A C11 H11B 108.1 no
N2 C12 C11 111.36(12) no
N2 C12 H12A 109.4 no
C11 C12 H12A 109.4 no
N2 C12 H12B 109.4 no
C11 C12 H12B 109.4 no
H12A C12 H12B 108.0 no
C10 C13 H13A 109.5 no
C10 C13 H13B 109.5 no
H13A C13 H13B 109.5 no
C10 C13 H13C 109.5 no
H13A C13 H13C 109.5 no
H13B C13 H13C 109.5 no
N3 C14 C15 110.33(12) no
N3 C14 H14A 109.6 no
C15 C14 H14A 109.6 no
N3 C14 H14B 109.6 no
C15 C14 H14B 109.6 no
H14A C14 H14B 108.1 no
C14 C15 C16 111.84(12) no
C14 C15 H15A 109.2 no
C16 C15 H15A 109.2 no
C14 C15 H15B 109.2 no
C16 C15 H15B 109.2 no
H15A C15 H15B 107.9 no
C19 C16 C15 110.95(13) no
C19 C16 C17 111.25(13) no
C15 C16 C17 109.51(12) no
C19 C16 H16A 108.3 no
C15 C16 H16A 108.3 no
C17 C16 H16A 108.3 no
C18 C17 C16 112.56(12) no
C18 C17 H17A 109.1 no
C16 C17 H17A 109.1 no
C18 C17 H17B 109.1 no
C16 C17 H17B 109.1 no
H17A C17 H17B 107.8 no
N3 C18 C17 110.36(12) no
N3 C18 H18A 109.6 no
C17 C18 H18A 109.6 no
N3 C18 H18B 109.6 no
C17 C18 H18B 109.6 no
H18A C18 H18B 108.1 no
C16 C19 H19A 109.5 no
C16 C19 H19B 109.5 no
H19A C19 H19B 109.5 no
C16 C19 H19C 109.5 no
H19A C19 H19C 109.5 no
H19B C19 H19C 109.5 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
P1 O2 1.4812(10) yes
P1 N3 1.6215(12) yes
P1 N2 1.6315(12) yes
P1 N1 1.6989(12) yes
F1 C1 1.3560(18) no
F2 C5 1.3578(18) no
O1 C7 1.2121(18) yes
N1 C7 1.3619(18) yes
N1 H1N 0.852(13) no
N2 C12 1.4699(18) yes
N2 C8 1.4766(18) yes
N3 C18 1.4659(18) yes
N3 C14 1.4700(18) yes
C1 C2 1.374(2) no
C1 C6 1.386(2) no
C2 C3 1.384(3) no
C2 H2B 0.9500 no
C3 C4 1.385(3) no
C3 H3A 0.9500 no
C4 C5 1.375(2) no
C4 H4A 0.9500 no
C5 C6 1.384(2) no
C6 C7 1.510(2) no
C8 C9 1.519(2) no
C8 H8A 0.9900 no
C8 H8B 0.9900 no
C9 C10 1.530(2) no
C9 H9A 0.9900 no
C9 H9B 0.9900 no
C10 C13 1.522(2) no
C10 C11 1.527(2) no
C10 H10A 1.0000 no
C11 C12 1.524(2) no
C11 H11A 0.9900 no
C11 H11B 0.9900 no
C12 H12A 0.9900 no
C12 H12B 0.9900 no
C13 H13A 0.9800 no
C13 H13B 0.9800 no
C13 H13C 0.9800 no
C14 C15 1.519(2) no
C14 H14A 0.9900 no
C14 H14B 0.9900 no
C15 C16 1.524(2) no
C15 H15A 0.9900 no
C15 H15B 0.9900 no
C16 C19 1.521(2) no
C16 C17 1.526(2) no
C16 H16A 1.0000 no
C17 C18 1.523(2) no
C17 H17A 0.9900 no
C17 H17B 0.9900 no
C18 H18A 0.9900 no
C18 H18B 0.9900 no
C19 H19A 0.9800 no
C19 H19B 0.9800 no
C19 H19C 0.9800 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1N O2 2_666 0.852(13) 1.941(14) 2.7786(16) 167.6(16)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
O2 P1 N1 C7 -162.48(12) yes
N3 P1 N1 C7 -38.61(14) yes
N2 P1 N1 C7 76.60(14) yes
O2 P1 N2 C12 -15.99(13) no
N3 P1 N2 C12 -144.59(11) no
N1 P1 N2 C12 101.06(11) no
O2 P1 N2 C8 -168.81(11) no
N3 P1 N2 C8 62.58(13) no
N1 P1 N2 C8 -51.77(13) no
O2 P1 N3 C18 -117.48(12) no
N2 P1 N3 C18 8.08(13) no
N1 P1 N3 C18 126.35(12) no
O2 P1 N3 C14 67.96(12) no
N2 P1 N3 C14 -166.49(11) no
N1 P1 N3 C14 -48.21(12) no
F1 C1 C2 C3 -179.49(14) no
C6 C1 C2 C3 -0.5(2) no
C1 C2 C3 C4 -0.1(2) no
C2 C3 C4 C5 0.4(3) no
C3 C4 C5 F2 -179.27(14) no
C3 C4 C5 C6 -0.1(2) no
F2 C5 C6 C1 178.70(13) no
C4 C5 C6 C1 -0.4(2) no
F2 C5 C6 C7 2.1(2) no
C4 C5 C6 C7 -177.05(14) no
F1 C1 C6 C5 179.78(13) no
C2 C1 C6 C5 0.8(2) no
F1 C1 C6 C7 -3.6(2) no
C2 C1 C6 C7 177.41(14) no
P1 N1 C7 O1 0.2(2) yes
P1 N1 C7 C6 179.18(10) no
C5 C6 C7 O1 103.58(18) no
C1 C6 C7 O1 -72.8(2) no
C5 C6 C7 N1 -75.44(18) no
C1 C6 C7 N1 108.16(16) no
C12 N2 C8 C9 -52.83(16) no
P1 N2 C8 C9 101.65(13) no
N2 C8 C9 C10 52.12(17) no
C8 C9 C10 C13 -178.96(13) no
C8 C9 C10 C11 -53.99(17) no
C13 C10 C11 C12 -179.43(12) no
C9 C10 C11 C12 56.13(16) no
C8 N2 C12 C11 56.01(16) no
P1 N2 C12 C11 -98.95(13) no
C10 C11 C12 N2 -57.73(16) no
C18 N3 C14 C15 57.82(16) no
P1 N3 C14 C15 -126.92(11) no
N3 C14 C15 C16 -55.89(16) no
C14 C15 C16 C19 176.66(13) no
C14 C15 C16 C17 53.47(16) no
C19 C16 C17 C18 -175.72(13) no
C15 C16 C17 C18 -52.71(16) no
C14 N3 C18 C17 -56.67(16) no
P1 N3 C18 C17 128.49(12) no
C16 C17 C18 N3 54.07(17) no
