#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/84/2228475.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228475
loop_
_publ_author_name
'Pourayoubi, Mehrdad'
'Tarahhomi, Atekeh'
'Rheingold, Arnold L.'
'Golen, James A.'
_publ_section_title
;
 N,N'-Di-tert-butyl-N''-(2,6-difluorobenzoyl)phosphoric
 triamide
;
_journal_coeditor_code           NG5051
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3159
_journal_paper_doi               10.1107/S1600536810045927
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H24 F2 N3 O2 P'
_chemical_formula_moiety         'C15 H24 F2 N3 O2 P'
_chemical_formula_sum            'C15 H24 F2 N3 O2 P'
_chemical_formula_weight         347.34
_chemical_name_systematic
;
N,N'-Di-tert-butyl-N''-(2,6-
difluorobenzoyl)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           SHELXL-97
_cell_angle_alpha                117.171(4)
_cell_angle_beta                 98.636(4)
_cell_angle_gamma                97.988(3)
_cell_formula_units_Z            2
_cell_length_a                   9.8142(12)
_cell_length_b                   10.2886(13)
_cell_length_c                   10.6091(16)
_cell_measurement_reflns_used    2837
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.85
_cell_measurement_theta_min      2.16
_cell_volume                     915.6(2)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'GIS (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008b)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008b)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008b)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008b)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker SMART X2S benchtop CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  'doubly curved silicon crystal'
_diffrn_radiation_source         'micro focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_sigmaI/netI    0.0431
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7847
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.90
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  0.9649
_exptl_absorpt_correction_T_min  0.9480
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(TWINABS; Sheldrick, 2008a)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.265
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         4225
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0494
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0548P)²+0.3384P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1206
_reflns_number_gt                3525
_reflns_number_total             4225
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ng5051.cif
_cod_data_source_block           I
_cod_database_code               2228475
_cod_database_fobs_code          2228475
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_disorder_assembly
_atom_site_disorder_group
P P1 0.18621(6) 0.39181(6) 0.41180(6) 0.02191(14) Uani d . 1 . .
F F1 0.4134(2) 0.6847(2) 0.94162(17) 0.0611(5) Uani d . 1 . .
F F2 0.23506(19) 0.89470(17) 0.66107(18) 0.0523(4) Uani d . 1 . .
O O1 0.45094(16) 0.62402(19) 0.64132(18) 0.0363(4) Uani d . 1 . .
O O2 0.03152(16) 0.32970(16) 0.36977(17) 0.0305(4) Uani d . 1 . .
N N1 0.20980(18) 0.55903(19) 0.56848(19) 0.0241(4) Uani d D 1 . .
H H1N 0.1375(17) 0.592(3) 0.595(3) 0.029 Uiso d D 1 . .
N N2 0.2528(2) 0.4227(2) 0.29337(19) 0.0276(4) Uani d D 1 . .
H H2N 0.3378(14) 0.411(3) 0.293(3) 0.033 Uiso d D 1 . .
N N3 0.28600(19) 0.2910(2) 0.4441(2) 0.0260(4) Uani d D 1 . .
H H3N 0.3739(13) 0.318(3) 0.449(3) 0.031 Uiso d D 1 . .
C C1 0.3611(3) 0.7959(3) 0.9332(3) 0.0404(6) Uani d . 1 . .
C C2 0.3480(4) 0.9159(4) 1.0587(3) 0.0597(9) Uani d . 1 . .
H H2A 0.3767 0.9216 1.1511 0.072 Uiso calc R 1 . .
C C3 0.2927(4) 1.0271(4) 1.0475(4) 0.0675(10) Uani d . 1 . .
H H3A 0.2807 1.1087 1.1327 0.081 Uiso calc R 1 . .
C C4 0.2544(3) 1.0216(3) 0.9142(4) 0.0593(9) Uani d . 1 . .
H H4A 0.2183 1.0995 0.9069 0.071 Uiso calc R 1 . .
C C5 0.2699(3) 0.8998(3) 0.7919(3) 0.0386(6) Uani d . 1 . .
C C6 0.3228(2) 0.7840(2) 0.7961(2) 0.0283(5) Uani d . 1 . .
C C7 0.3352(2) 0.6488(2) 0.6613(2) 0.0243(4) Uani d . 1 . .
C C8 0.1874(3) 0.4811(3) 0.1991(2) 0.0353(5) Uani d . 1 . .
C C9 0.1621(4) 0.6356(3) 0.2928(3) 0.0580(9) Uani d . 1 . .
H H9A 0.2518 0.7042 0.3598 0.087 Uiso calc R 1 . .
H H9B 0.0940 0.6275 0.3491 0.087 Uiso calc R 1 . .
H H9C 0.1241 0.6747 0.2297 0.087 Uiso calc R 1 . .
C C10 0.0477(3) 0.3691(4) 0.0967(3) 0.0569(8) Uani d . 1 . .
H H10A -0.0227 0.3709 0.1536 0.085 Uiso calc R 1 . .
H H10B 0.0640 0.2677 0.0478 0.085 Uiso calc R 1 . .
H H10C 0.0126 0.3972 0.0234 0.085 Uiso calc R 1 . .
C C11 0.2913(4) 0.4907(4) 0.1095(3) 0.0535(7) Uani d . 1 . .
H H11A 0.3809 0.5611 0.1750 0.080 Uiso calc R 1 . .
H H11B 0.2515 0.5263 0.0439 0.080 Uiso calc R 1 . .
H H11C 0.3084 0.3911 0.0518 0.080 Uiso calc R 1 . .
C C12 0.2566(3) 0.1929(3) 0.5095(3) 0.0336(5) Uani d . 1 . .
C C13 0.1325(3) 0.0588(3) 0.4049(4) 0.0579(8) Uani d . 1 . .
H H13A 0.1533 0.0073 0.3088 0.087 Uiso calc R 1 . .
H H13B 0.0460 0.0945 0.3956 0.087 Uiso calc R 1 . .
H H13C 0.1188 -0.0112 0.4433 0.087 Uiso calc R 1 . .
C C14 0.2251(5) 0.2791(4) 0.6581(4) 0.0677(10) Uani d . 1 . .
H H14A 0.3057 0.3642 0.7232 0.102 Uiso calc R 1 . .
H H14B 0.2093 0.2123 0.6997 0.102 Uiso calc R 1 . .
H H14C 0.1400 0.3165 0.6470 0.102 Uiso calc R 1 . .
C C15 0.3893(3) 0.1343(4) 0.5243(4) 0.0525(7) Uani d . 1 . .
H H15A 0.4090 0.0802 0.4280 0.079 Uiso calc R 1 . .
H H15B 0.3742 0.0661 0.5645 0.079 Uiso calc R 1 . .
H H15C 0.4701 0.2191 0.5898 0.079 Uiso calc R 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 P1 N3 . . 116.57(10) ?
O2 P1 N2 . . 115.98(9) ?
N3 P1 N2 . . 102.21(9) ?
O2 P1 N1 . . 103.22(8) ?
N3 P1 N1 . . 109.37(9) ?
N2 P1 N1 . . 109.43(10) ?
C7 N1 P1 . . 126.27(14) ?
C7 N1 H1N . . 113.8(16) ?
P1 N1 H1N . . 119.9(16) ?
C8 N2 P1 . . 127.01(16) ?
C8 N2 H2N . . 118.1(19) ?
P1 N2 H2N . . 114.6(19) ?
C12 N3 P1 . . 128.21(15) ?
C12 N3 H3N . . 114.1(19) ?
P1 N3 H3N . . 114.8(18) ?
F1 C1 C2 . . 119.7(3) ?
F1 C1 C6 . . 117.6(2) ?
C2 C1 C6 . . 122.7(3) ?
C3 C2 C1 . . 118.8(3) ?
C3 C2 H2A . . 120.6 ?
C1 C2 H2A . . 120.6 ?
C2 C3 C4 . . 120.9(3) ?
C2 C3 H3A . . 119.5 ?
C4 C3 H3A . . 119.5 ?
C3 C4 C5 . . 118.3(3) ?
C3 C4 H4A . . 120.9 ?
C5 C4 H4A . . 120.9 ?
F2 C5 C4 . . 118.7(3) ?
F2 C5 C6 . . 117.9(2) ?
C4 C5 C6 . . 123.4(3) ?
C5 C6 C1 . . 116.0(2) ?
C5 C6 C7 . . 123.1(2) ?
C1 C6 C7 . . 120.9(2) ?
O1 C7 N1 . . 124.00(18) ?
O1 C7 C6 . . 121.48(18) ?
N1 C7 C6 . . 114.52(17) ?
N2 C8 C11 . . 106.6(2) ?
N2 C8 C9 . . 110.46(19) ?
C11 C8 C9 . . 110.4(2) ?
N2 C8 C10 . . 109.0(2) ?
C11 C8 C10 . . 109.5(2) ?
C9 C8 C10 . . 110.8(2) ?
C8 C9 H9A . . 109.5 ?
C8 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C8 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C8 C10 H10A . . 109.5 ?
C8 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C8 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C8 C11 H11A . . 109.5 ?
C8 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C8 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
N3 C12 C14 . . 111.4(2) ?
N3 C12 C15 . . 106.2(2) ?
C14 C12 C15 . . 110.4(2) ?
N3 C12 C13 . . 109.3(2) ?
C14 C12 C13 . . 110.8(3) ?
C15 C12 C13 . . 108.5(2) ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C12 C14 H14A . . 109.5 ?
C12 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C12 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C12 C15 H15A . . 109.5 ?
C12 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C12 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 O2 . 1.4761(16) ?
P1 N3 . 1.6301(18) ?
P1 N2 . 1.631(2) ?
P1 N1 . 1.7142(17) ?
F1 C1 . 1.351(3) ?
F2 C5 . 1.353(3) ?
O1 C7 . 1.226(2) ?
N1 C7 . 1.352(3) ?
N1 H1N . 0.858(10) ?
N2 C8 . 1.495(3) ?
N2 H2N . 0.860(10) ?
N3 C12 . 1.485(3) ?
N3 H3N . 0.856(10) ?
C1 C2 . 1.381(4) ?
C1 C6 . 1.390(4) ?
C2 C3 . 1.377(5) ?
C2 H2A . 0.9500 ?
C3 C4 . 1.381(6) ?
C3 H3A . 0.9500 ?
C4 C5 . 1.380(4) ?
C4 H4A . 0.9500 ?
C5 C6 . 1.381(3) ?
C6 C7 . 1.509(3) ?
C8 C11 . 1.517(4) ?
C8 C9 . 1.522(4) ?
C8 C10 . 1.536(4) ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C9 H9C . 0.9800 ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
C11 H11A . 0.9800 ?
C11 H11B . 0.9800 ?
C11 H11C . 0.9800 ?
C12 C14 . 1.520(4) ?
C12 C15 . 1.526(3) ?
C12 C13 . 1.532(4) ?
C13 H13A . 0.9800 ?
C13 H13B . 0.9800 ?
C13 H13C . 0.9800 ?
C14 H14A . 0.9800 ?
C14 H14B . 0.9800 ?
C14 H14C . 0.9800 ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
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_566 0.858(10) 1.956(11) 2.808(2) 172(2)
N2 H2N O1 2_666 0.860(10) 2.219(13) 3.042(2) 160(2)
N3 H3N O1 2_666 0.856(10) 2.224(15) 3.008(2) 152(2)
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O2 P1 N1 C7 . . . . 169.82(18) ?
N3 P1 N1 C7 . . . . 45.1(2) ?
N2 P1 N1 C7 . . . . -66.1(2) ?
O2 P1 N2 C8 . . . . 38.0(2) ?
N3 P1 N2 C8 . . . . 165.93(18) ?
N1 P1 N2 C8 . . . . -78.2(2) ?
O2 P1 N3 C12 . . . . -33.9(2) ?
N2 P1 N3 C12 . . . . -161.48(19) ?
N1 P1 N3 C12 . . . . 82.6(2) ?
F1 C1 C2 C3 . . . . -179.2(3) ?
C6 C1 C2 C3 . . . . 1.1(5) ?
C1 C2 C3 C4 . . . . -1.8(5) ?
C2 C3 C4 C5 . . . . 1.5(5) ?
C3 C4 C5 F2 . . . . -178.8(3) ?
C3 C4 C5 C6 . . . . -0.6(4) ?
F2 C5 C6 C1 . . . . 178.2(2) ?
C4 C5 C6 C1 . . . . 0.0(4) ?
F2 C5 C6 C7 . . . . -3.8(3) ?
C4 C5 C6 C7 . . . . 178.0(2) ?
F1 C1 C6 C5 . . . . -180.0(2) ?
C2 C1 C6 C5 . . . . -0.3(4) ?
F1 C1 C6 C7 . . . . 2.0(3) ?
C2 C1 C6 C7 . . . . -178.3(2) ?
P1 N1 C7 O1 . . . . 3.1(3) ?
P1 N1 C7 C6 . . . . -175.92(16) ?
C5 C6 C7 O1 . . . . 114.8(3) ?
C1 C6 C7 O1 . . . . -67.3(3) ?
C5 C6 C7 N1 . . . . -66.1(3) ?
C1 C6 C7 N1 . . . . 111.8(2) ?
P1 N2 C8 C11 . . . . 179.62(18) ?
P1 N2 C8 C9 . . . . 59.7(3) ?
P1 N2 C8 C10 . . . . -62.3(3) ?
P1 N3 C12 C14 . . . . -55.9(3) ?
P1 N3 C12 C15 . . . . -176.14(19) ?
P1 N3 C12 C13 . . . . 67.0(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656378
