#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/78/2227835.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_2227835
loop_
_publ_author_name
'Pourayoubi, Mehrdad'
'Tarahhomi, Atekeh'
'Rheingold, Arnold L.'
'Golen, James A.'
_publ_section_title
;
 N,N'-Dibenzyl-N''-(2,6-difluorobenzoyl)-N,N'-dimethylphosphoric
 triamide
;
_journal_coeditor_code           NG5027
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2524
_journal_paper_doi               10.1107/S1600536810035725
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C23 H24 F2 N3 O2 P'
_chemical_formula_moiety         'C23 H24 F2 N3 O2 P'
_chemical_formula_sum            'C23 H24 F2 N3 O2 P'
_chemical_formula_weight         443.42
_chemical_name_systematic
;
N,N'-Dibenzyl-N''-(2,6-difluorobenzoyl)-
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           SHELXL-97
_cell_angle_alpha                89.101(4)
_cell_angle_beta                 67.826(4)
_cell_angle_gamma                71.664(4)
_cell_formula_units_Z            2
_cell_length_a                   9.9370(11)
_cell_length_b                   11.1093(15)
_cell_length_c                   11.5902(14)
_cell_measurement_reflns_used    5531
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.83
_cell_measurement_theta_min      2.35
_cell_volume                     1116.9(2)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'SMART (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker SMART X2S benchtop CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'curved silicon crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_sigmaI/netI    0.0480
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13602
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.83
_diffrn_reflns_theta_min         2.35
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_T_max  0.9679
_exptl_absorpt_correction_T_min  0.9524
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2005)'
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.320
_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     286
_refine_ls_number_reflns         5173
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0483
_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/[σ²(Fo²)+(0.0603P)²+0.2218P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1153
_refine_ls_wR_factor_ref         0.1256
_reflns_number_gt                3851
_reflns_number_total             5173
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ng5027.cif
_cod_data_source_block           I
_cod_database_code               2227835
_cod_database_fobs_code          2227835
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 0.66485(5) 0.42270(4) 0.29906(4) 0.02461(13) Uani d . 1 . .
F F1 0.41237(17) 0.18210(16) 0.50507(15) 0.0723(5) Uani d . 1 . .
F F2 0.16095(14) 0.43844(12) 0.27352(13) 0.0532(4) Uani d . 1 . .
O O1 0.50833(16) 0.27969(15) 0.19272(13) 0.0445(4) Uani d . 1 . .
O O2 0.68882(13) 0.46617(12) 0.40757(12) 0.0323(3) Uani d . 1 . .
N N1 0.48905(16) 0.40601(15) 0.35526(15) 0.0277(3) Uani d . 1 . .
N N2 0.79630(15) 0.28474(13) 0.22927(13) 0.0246(3) Uani d . 1 . .
N N3 0.66719(17) 0.52094(15) 0.19333(15) 0.0358(4) Uani d . 1 . .
C C1 0.2810(2) 0.2390(2) 0.4858(2) 0.0449(5) Uani d . 1 . .
C C2 0.1464(3) 0.2189(3) 0.5632(2) 0.0583(7) Uani d . 1 . .
H H2A 0.1443 0.1678 0.6299 0.070 Uiso calc R 1 . .
C C3 0.0152(3) 0.2755(3) 0.5402(2) 0.0573(7) Uani d . 1 . .
H H3A -0.0785 0.2634 0.5924 0.069 Uiso calc R 1 . .
C C4 0.0174(2) 0.3490(2) 0.4434(2) 0.0485(6) Uani d . 1 . .
H H4A -0.0733 0.3880 0.4282 0.058 Uiso calc R 1 . .
C C5 0.1560(2) 0.3646(2) 0.36861(19) 0.0370(5) Uani d . 1 . .
C C6 0.2916(2) 0.31110(18) 0.38644(17) 0.0315(4) Uani d . 1 . .
C C7 0.4403(2) 0.32953(18) 0.30107(17) 0.0309(4) Uani d . 1 . .
C C8 0.86123(19) 0.24379(17) 0.09447(16) 0.0280(4) Uani d . 1 . .
H H8A 0.8268 0.3173 0.0509 0.034 Uiso calc R 1 . .
H H8B 0.8212 0.1771 0.0792 0.034 Uiso calc R 1 . .
C C9 1.03733(19) 0.19106(16) 0.03916(16) 0.0250(4) Uani d . 1 . .
C C10 1.1236(2) 0.22336(17) 0.09620(17) 0.0296(4) Uani d . 1 . .
H H10A 1.0727 0.2797 0.1720 0.035 Uiso calc R 1 . .
C C11 1.2842(2) 0.17395(19) 0.04339(18) 0.0341(4) Uani d . 1 . .
H H11A 1.3419 0.1964 0.0836 0.041 Uiso calc R 1 . .
C C12 1.3599(2) 0.09219(18) -0.06744(19) 0.0358(5) Uani d . 1 . .
H H12A 1.4693 0.0584 -0.1033 0.043 Uiso calc R 1 . .
C C13 1.2756(2) 0.06030(19) -0.12524(19) 0.0393(5) Uani d . 1 . .
H H13A 1.3270 0.0049 -0.2017 0.047 Uiso calc R 1 . .
C C14 1.1147(2) 0.10908(18) -0.07202(18) 0.0336(4) Uani d . 1 . .
H H14A 1.0575 0.0859 -0.1123 0.040 Uiso calc R 1 . .
C C15 0.8149(2) 0.18153(18) 0.30902(18) 0.0351(4) Uani d . 1 . .
H H15A 0.9229 0.1261 0.2767 0.053 Uiso calc R 1 . .
H H15B 0.7497 0.1313 0.3084 0.053 Uiso calc R 1 . .
H H15C 0.7842 0.2184 0.3951 0.053 Uiso calc R 1 . .
C C16 0.5493(2) 0.56887(19) 0.14191(18) 0.0382(5) Uani d . 1 . .
H H16A 0.4917 0.5083 0.1535 0.046 Uiso calc R 1 . .
H H16B 0.6010 0.5705 0.0506 0.046 Uiso calc R 1 . .
C C17 0.4345(2) 0.70157(17) 0.20021(17) 0.0290(4) Uani d . 1 . .
C C18 0.3442(2) 0.76890(19) 0.13718(19) 0.0360(5) Uani d . 1 . .
H H18A 0.3538 0.7308 0.0604 0.043 Uiso calc R 1 . .
C C19 0.2409(2) 0.8908(2) 0.1858(2) 0.0402(5) Uani d . 1 . .
H H19A 0.1796 0.9355 0.1426 0.048 Uiso calc R 1 . .
C C20 0.2266(2) 0.9478(2) 0.2971(2) 0.0414(5) Uani d . 1 . .
H H20A 0.1568 1.0319 0.3297 0.050 Uiso calc R 1 . .
C C21 0.3144(2) 0.88166(19) 0.36020(18) 0.0399(5) Uani d . 1 . .
H H21A 0.3047 0.9202 0.4368 0.048 Uiso calc R 1 . .
C C22 0.4176(2) 0.75831(18) 0.31215(18) 0.0344(4) Uani d . 1 . .
H H22A 0.4767 0.7130 0.3569 0.041 Uiso calc R 1 . .
C C23 0.7939(3) 0.5743(2) 0.1510(3) 0.0603(7) Uani d . 1 . .
H H23A 0.8498 0.5537 0.0599 0.091 Uiso calc R 1 . .
H H23B 0.8646 0.5376 0.1925 0.091 Uiso calc R 1 . .
H H23C 0.7516 0.6673 0.1724 0.091 Uiso calc R 1 . .
H H1A 0.429(2) 0.442(2) 0.427(2) 0.038(6) Uiso d . 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 . . 114.81(8) ?
O2 P1 N2 . . 110.54(7) ?
N3 P1 N2 . . 107.66(8) ?
O2 P1 N1 . . 107.11(8) ?
N3 P1 N1 . . 107.24(8) ?
N2 P1 N1 . . 109.34(8) ?
C7 N1 P1 . . 126.79(13) ?
C7 N1 H1A . . 116.4(14) ?
P1 N1 H1A . . 116.5(14) ?
C8 N2 C15 . . 115.44(14) ?
C8 N2 P1 . . 125.15(12) ?
C15 N2 P1 . . 116.63(11) ?
C16 N3 C23 . . 116.19(17) ?
C16 N3 P1 . . 126.13(14) ?
C23 N3 P1 . . 117.53(14) ?
F1 C1 C6 . . 117.31(18) ?
F1 C1 C2 . . 119.0(2) ?
C6 C1 C2 . . 123.7(2) ?
C3 C2 C1 . . 117.9(2) ?
C3 C2 H2A . . 121.1 ?
C1 C2 H2A . . 121.1 ?
C4 C3 C2 . . 121.4(2) ?
C4 C3 H3A . . 119.3 ?
C2 C3 H3A . . 119.3 ?
C3 C4 C5 . . 118.0(2) ?
C3 C4 H4A . . 121.0 ?
C5 C4 H4A . . 121.0 ?
F2 C5 C6 . . 117.05(18) ?
F2 C5 C4 . . 119.21(19) ?
C6 C5 C4 . . 123.7(2) ?
C5 C6 C1 . . 115.30(18) ?
C5 C6 C7 . . 121.65(18) ?
C1 C6 C7 . . 123.04(17) ?
O1 C7 N1 . . 123.93(17) ?
O1 C7 C6 . . 121.61(16) ?
N1 C7 C6 . . 114.46(15) ?
N2 C8 C9 . . 112.58(14) ?
N2 C8 H8A . . 109.1 ?
C9 C8 H8A . . 109.1 ?
N2 C8 H8B . . 109.1 ?
C9 C8 H8B . . 109.1 ?
H8A C8 H8B . . 107.8 ?
C14 C9 C10 . . 118.49(16) ?
C14 C9 C8 . . 119.50(15) ?
C10 C9 C8 . . 122.01(15) ?
C9 C10 C11 . . 120.73(17) ?
C9 C10 H10A . . 119.6 ?
C11 C10 H10A . . 119.6 ?
C12 C11 C10 . . 120.19(18) ?
C12 C11 H11A . . 119.9 ?
C10 C11 H11A . . 119.9 ?
C13 C12 C11 . . 119.55(17) ?
C13 C12 H12A . . 120.2 ?
C11 C12 H12A . . 120.2 ?
C12 C13 C14 . . 120.31(18) ?
C12 C13 H13A . . 119.8 ?
C14 C13 H13A . . 119.8 ?
C9 C14 C13 . . 120.73(18) ?
C9 C14 H14A . . 119.6 ?
C13 C14 H14A . . 119.6 ?
N2 C15 H15A . . 109.5 ?
N2 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
N2 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
N3 C16 C17 . . 114.79(16) ?
N3 C16 H16A . . 108.6 ?
C17 C16 H16A . . 108.6 ?
N3 C16 H16B . . 108.6 ?
C17 C16 H16B . . 108.6 ?
H16A C16 H16B . . 107.5 ?
C22 C17 C18 . . 118.77(17) ?
C22 C17 C16 . . 122.46(16) ?
C18 C17 C16 . . 118.76(17) ?
C19 C18 C17 . . 120.47(19) ?
C19 C18 H18A . . 119.8 ?
C17 C18 H18A . . 119.8 ?
C20 C19 C18 . . 120.37(18) ?
C20 C19 H19A . . 119.8 ?
C18 C19 H19A . . 119.8 ?
C21 C20 C19 . . 119.48(19) ?
C21 C20 H20A . . 120.3 ?
C19 C20 H20A . . 120.3 ?
C20 C21 C22 . . 120.33(19) ?
C20 C21 H21A . . 119.8 ?
C22 C21 H21A . . 119.8 ?
C17 C22 C21 . . 120.56(18) ?
C17 C22 H22A . . 119.7 ?
C21 C22 H22A . . 119.7 ?
N3 C23 H23A . . 109.5 ?
N3 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
N3 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 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 . 1.4796(13) ?
P1 N3 . 1.6266(16) ?
P1 N2 . 1.6405(14) ?
P1 N1 . 1.6886(15) ?
F1 C1 . 1.360(2) ?
F2 C5 . 1.359(2) ?
O1 C7 . 1.219(2) ?
N1 C7 . 1.362(2) ?
N1 H1A . 0.83(2) ?
N2 C8 . 1.463(2) ?
N2 C15 . 1.471(2) ?
N3 C16 . 1.462(2) ?
N3 C23 . 1.474(3) ?
C1 C6 . 1.383(3) ?
C1 C2 . 1.386(3) ?
C2 C3 . 1.380(4) ?
C2 H2A . 0.9500 ?
C3 C4 . 1.375(3) ?
C3 H3A . 0.9500 ?
C4 C5 . 1.386(3) ?
C4 H4A . 0.9500 ?
C5 C6 . 1.383(3) ?
C6 C7 . 1.512(3) ?
C8 C9 . 1.529(2) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 C14 . 1.389(2) ?
C9 C10 . 1.389(2) ?
C10 C11 . 1.395(2) ?
C10 H10A . 0.9500 ?
C11 C12 . 1.385(3) ?
C11 H11A . 0.9500 ?
C12 C13 . 1.377(3) ?
C12 H12A . 0.9500 ?
C13 C14 . 1.397(3) ?
C13 H13A . 0.9500 ?
C14 H14A . 0.9500 ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
C16 C17 . 1.524(3) ?
C16 H16A . 0.9900 ?
C16 H16B . 0.9900 ?
C17 C22 . 1.380(3) ?
C17 C18 . 1.397(3) ?
C18 C19 . 1.385(3) ?
C18 H18A . 0.9500 ?
C19 C20 . 1.384(3) ?
C19 H19A . 0.9500 ?
C20 C21 . 1.378(3) ?
C20 H20A . 0.9500 ?
C21 C22 . 1.396(3) ?
C21 H21A . 0.9500 ?
C22 H22A . 0.9500 ?
C23 H23A . 0.9800 ?
C23 H23B . 0.9800 ?
C23 H23C . 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 H1A O2 2_666 0.83(2) 1.92(2) 2.752(2) 173(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656286
