#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/81/2018166.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_2018166
loop_
_publ_author_name
'Pourayoubi, Mehrdad'
'Tarahhomi, Atekeh'
'Saneei, Anahid'
'Rheingold, Arnold L.'
'Golen, James A.'
_publ_section_title
;
 Different cyclic motifs in phosphoric triamides containing a
 C(O)NHP(O)(NH)₂ skeleton and an R₂²(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
;
N,N'-bis(2-chlorobenzyl)-N''-(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 et al.,
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      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       'φ and ω'
_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/[σ²(Fo²)+(0.0446P)²+2.5057P] where P=(Fo²+2Fc²)/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>2σ(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
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.56322(4) 0.82496(15) 0.57320(3) 0.02548(18) Uani d . 1 1 . .
Cl Cl2 -0.01375(4) 0.77969(15) 0.44276(3) 0.02530(18) Uani d . 1 1 . .
P P1 0.27115(4) 0.74413(14) 0.50981(3) 0.01593(17) Uani d . 1 1 . .
F F1 0.15953(8) 0.9940(3) 0.65322(7) 0.0252(4) Uani d . 1 1 . .
F F2 0.32417(9) 0.3325(4) 0.73647(8) 0.0287(4) Uani d . 1 1 . .
O O1 0.25395(10) 0.3553(4) 0.60992(9) 0.0214(4) Uani d . 1 1 . .
O O2 0.27054(10) 1.0164(4) 0.48287(9) 0.0201(4) Uani d . 1 1 . .
N N1 0.26151(12) 0.7935(5) 0.58611(10) 0.0175(5) Uani d D 1 1 . .
H H1N 0.2581(16) 0.949(4) 0.6011(13) 0.021 Uiso d D 1 1 . .
N N2 0.34085(12) 0.5706(5) 0.51076(11) 0.0184(5) Uani d D 1 1 . .
H H2N 0.3346(16) 0.411(4) 0.4998(14) 0.022 Uiso d D 1 1 . .
N N3 0.20998(12) 0.5420(5) 0.47405(11) 0.0190(5) Uani d D 1 1 . .
H H3N 0.2201(16) 0.383(4) 0.4815(14) 0.023 Uiso d D 1 1 . .
C C1 0.19795(15) 0.8613(6) 0.70344(13) 0.0205(6) Uani d . 1 1 . .
C C2 0.18783(15) 0.9231(6) 0.76331(14) 0.0252(7) Uani d . 1 1 . .
H H2A 0.1558 1.0587 0.7692 0.030 Uiso calc R 1 1 . .
C C3 0.22578(16) 0.7818(6) 0.81506(13) 0.0262(7) Uani d . 1 1 . .
H H3A 0.2205 0.8238 0.8569 0.031 Uiso calc R 1 1 . .
C C4 0.27096(16) 0.5812(7) 0.80576(13) 0.0266(7) Uani d . 1 1 . .
H H4A 0.2963 0.4823 0.8408 0.032 Uiso calc R 1 1 . .
C C5 0.27869(15) 0.5265(6) 0.74460(13) 0.0222(6) Uani d . 1 1 . .
C C6 0.24330(14) 0.6648(6) 0.69125(12) 0.0184(6) Uani d . 1 1 . .
C C7 0.25292(14) 0.5913(6) 0.62590(12) 0.0184(6) Uani d . 1 1 . .
C C8 0.41113(14) 0.6730(6) 0.53326(12) 0.0198(6) Uani d . 1 1 . .
H H8A 0.4082 0.8641 0.5449 0.024 Uiso calc R 1 1 . .
H H8B 0.4362 0.6641 0.4979 0.024 Uiso calc R 1 1 . .
C C9 0.45316(15) 0.5247(6) 0.58983(12) 0.0193(6) Uani d . 1 1 . .
C C10 0.52358(15) 0.5791(6) 0.61148(13) 0.0200(6) Uani d . 1 1 . .
C C11 0.56409(16) 0.4456(6) 0.66265(13) 0.0248(7) Uani d . 1 1 . .
H H11A 0.6120 0.4879 0.6764 0.030 Uiso calc R 1 1 . .
C C12 0.53366(17) 0.2495(6) 0.69349(13) 0.0272(7) Uani d . 1 1 . .
H H12A 0.5609 0.1542 0.7282 0.033 Uiso calc R 1 1 . .
C C13 0.46341(16) 0.1924(6) 0.67365(13) 0.0250(7) Uani d . 1 1 . .
H H13A 0.4424 0.0599 0.6953 0.030 Uiso calc R 1 1 . .
C C14 0.42361(15) 0.3286(6) 0.62220(13) 0.0217(6) Uani d . 1 1 . .
H H14A 0.3755 0.2875 0.6089 0.026 Uiso calc R 1 1 . .
C C15 0.13673(14) 0.6099(6) 0.47053(12) 0.0204(6) Uani d . 1 1 . .
H H15A 0.1306 0.8062 0.4654 0.024 Uiso calc R 1 1 . .
H H15B 0.1234 0.5578 0.5108 0.024 Uiso calc R 1 1 . .
C C16 0.08956(14) 0.4695(6) 0.41556(12) 0.0194(6) Uani d . 1 1 . .
C C17 0.01876(15) 0.5362(6) 0.39907(13) 0.0210(6) Uani d . 1 1 . .
C C18 -0.02593(15) 0.4159(6) 0.34858(13) 0.0244(7) Uani d . 1 1 . .
H H18A -0.0734 0.4693 0.3377 0.029 Uiso calc R 1 1 . .
C C19 -0.00137(16) 0.2176(6) 0.31399(13) 0.0248(7) Uani d . 1 1 . .
H H19A -0.0319 0.1332 0.2794 0.030 Uiso calc R 1 1 . .
C C20 0.06798(15) 0.1425(6) 0.32998(13) 0.0230(6) Uani d . 1 1 . .
H H20A 0.0849 0.0052 0.3066 0.028 Uiso calc R 1 1 . .
C C21 0.11285(15) 0.2674(6) 0.38021(12) 0.0198(6) Uani d . 1 1 . .
H H21A 0.1603 0.2142 0.3907 0.024 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'
Cl Cl 0.1484 0.1585 '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 N2 . . 115.79(12) y
O2 P1 N3 . . 116.04(12) y
N2 P1 N3 . . 102.33(13) y
O2 P1 N1 . . 104.51(11) y
N2 P1 N1 . . 109.20(12) y
N3 P1 N1 . . 108.83(12) y
C7 N1 P1 . . 123.5(2) y
C7 N1 H1N . . 114(2) ?
P1 N1 H1N . . 122(2) ?
C8 N2 P1 . . 123.93(19) y
C8 N2 H2N . . 120(2) ?
P1 N2 H2N . . 116(2) ?
C15 N3 P1 . . 120.01(19) y
C15 N3 H3N . . 115(2) ?
P1 N3 H3N . . 112(2) ?
F1 C1 C2 . . 118.0(3) ?
F1 C1 C6 . . 117.9(2) ?
C2 C1 C6 . . 124.0(3) ?
C1 C2 C3 . . 118.3(3) ?
C1 C2 H2A . . 120.8 ?
C3 C2 H2A . . 120.8 ?
C4 C3 C2 . . 120.3(3) ?
C4 C3 H3A . . 119.9 ?
C2 C3 H3A . . 119.9 ?
C3 C4 C5 . . 118.9(3) ?
C3 C4 H4A . . 120.6 ?
C5 C4 H4A . . 120.6 ?
F2 C5 C4 . . 118.1(3) ?
F2 C5 C6 . . 118.5(2) ?
C4 C5 C6 . . 123.4(3) ?
C1 C6 C5 . . 115.1(2) ?
C1 C6 C7 . . 124.1(2) ?
C5 C6 C7 . . 120.7(3) ?
O1 C7 N1 . . 121.7(2) y
O1 C7 C6 . . 120.6(2) ?
N1 C7 C6 . . 117.7(2) ?
N2 C8 C9 . . 114.6(2) ?
N2 C8 H8A . . 108.6 ?
C9 C8 H8A . . 108.6 ?
N2 C8 H8B . . 108.6 ?
C9 C8 H8B . . 108.6 ?
H8A C8 H8B . . 107.6 ?
C10 C9 C14 . . 117.3(3) ?
C10 C9 C8 . . 120.7(3) ?
C14 C9 C8 . . 122.0(3) ?
C11 C10 C9 . . 122.5(3) ?
C11 C10 Cl1 . . 118.2(2) ?
C9 C10 Cl1 . . 119.3(2) ?
C12 C11 C10 . . 119.0(3) ?
C12 C11 H11A . . 120.5 ?
C10 C11 H11A . . 120.5 ?
C11 C12 C13 . . 120.0(3) ?
C11 C12 H12A . . 120.0 ?
C13 C12 H12A . . 120.0 ?
C12 C13 C14 . . 120.2(3) ?
C12 C13 H13A . . 119.9 ?
C14 C13 H13A . . 119.9 ?
C13 C14 C9 . . 121.0(3) ?
C13 C14 H14A . . 119.5 ?
C9 C14 H14A . . 119.5 ?
N3 C15 C16 . . 111.6(2) ?
N3 C15 H15A . . 109.3 ?
C16 C15 H15A . . 109.3 ?
N3 C15 H15B . . 109.3 ?
C16 C15 H15B . . 109.3 ?
H15A C15 H15B . . 108.0 ?
C21 C16 C17 . . 117.0(3) ?
C21 C16 C15 . . 122.8(3) ?
C17 C16 C15 . . 120.1(3) ?
C18 C17 C16 . . 122.0(3) ?
C18 C17 Cl2 . . 118.9(2) ?
C16 C17 Cl2 . . 119.1(2) ?
C17 C18 C19 . . 119.8(3) ?
C17 C18 H18A . . 120.1 ?
C19 C18 H18A . . 120.1 ?
C18 C19 C20 . . 119.7(3) ?
C18 C19 H19A . . 120.1 ?
C20 C19 H19A . . 120.1 ?
C19 C20 C21 . . 120.2(3) ?
C19 C20 H20A . . 119.9 ?
C21 C20 H20A . . 119.9 ?
C20 C21 C16 . . 121.3(3) ?
C20 C21 H21A . . 119.4 ?
C16 C21 H21A . . 119.4 ?
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
Cl1 C10 . 1.747(3) ?
Cl2 C17 . 1.736(3) ?
P1 O2 . 1.475(2) y
P1 N2 . 1.616(2) y
P1 N3 . 1.632(2) y
P1 N1 . 1.707(2) y
F1 C1 . 1.353(3) ?
F2 C5 . 1.353(3) ?
O1 C7 . 1.227(3) y
N1 C7 . 1.355(4) y
N1 H1N . 0.850(18) ?
N2 C8 . 1.457(4) y
N2 H2N . 0.833(18) ?
N3 C15 . 1.465(4) y
N3 H3N . 0.826(18) ?
C1 C2 . 1.377(4) ?
C1 C6 . 1.386(4) ?
C2 C3 . 1.394(4) ?
C2 H2A . 0.9500 ?
C3 C4 . 1.379(4) ?
C3 H3A . 0.9500 ?
C4 C5 . 1.381(4) ?
C4 H4A . 0.9500 ?
C5 C6 . 1.393(4) ?
C6 C7 . 1.501(4) ?
C8 C9 . 1.512(4) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 C10 . 1.391(4) ?
C9 C14 . 1.395(4) ?
C10 C11 . 1.385(4) ?
C11 C12 . 1.385(4) ?
C11 H11A . 0.9500 ?
C12 C13 . 1.386(4) ?
C12 H12A . 0.9500 ?
C13 C14 . 1.390(4) ?
C13 H13A . 0.9500 ?
C14 H14A . 0.9500 ?
C15 C16 . 1.512(4) ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
C16 C21 . 1.395(4) ?
C16 C17 . 1.402(4) ?
C17 C18 . 1.382(4) ?
C18 C19 . 1.383(4) ?
C18 H18A . 0.9500 ?
C19 C20 . 1.385(4) ?
C19 H19A . 0.9500 ?
C20 C21 . 1.390(4) ?
C20 H20A . 0.9500 ?
C21 H21A . 0.9500 ?
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
_geom_hbond_publ_flag
N1 H1N O1 1_565 0.850(18) 2.04(2) 2.858(3) 162(3) y
N1 H1N F1 . 0.850(18) 2.44(3) 2.881(3) 113(2) y
N2 H2N O2 1_545 0.833(18) 2.32(2) 3.092(3) 154(3) y
N3 H3N O2 1_545 0.826(18) 2.08(2) 2.869(3) 161(3) y
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 . . . . 173.6(2) y
N2 P1 N1 C7 . . . . -61.9(3) y
N3 P1 N1 C7 . . . . 49.1(3) y
O2 P1 N2 C8 . . . . 47.4(2) ?
N3 P1 N2 C8 . . . . 174.6(2) ?
N1 P1 N2 C8 . . . . -70.2(2) ?
O2 P1 N3 C15 . . . . -60.8(2) ?
N2 P1 N3 C15 . . . . 172.2(2) ?
N1 P1 N3 C15 . . . . 56.7(2) ?
F1 C1 C2 C3 . . . . 178.2(3) ?
C6 C1 C2 C3 . . . . 0.6(5) ?
C1 C2 C3 C4 . . . . -1.5(4) ?
C2 C3 C4 C5 . . . . 1.1(5) ?
C3 C4 C5 F2 . . . . 178.8(3) ?
C3 C4 C5 C6 . . . . 0.3(5) ?
F1 C1 C6 C5 . . . . -176.9(2) ?
C2 C1 C6 C5 . . . . 0.7(4) ?
F1 C1 C6 C7 . . . . 0.5(4) ?
C2 C1 C6 C7 . . . . 178.1(3) ?
F2 C5 C6 C1 . . . . -179.7(2) ?
C4 C5 C6 C1 . . . . -1.1(4) ?
F2 C5 C6 C7 . . . . 2.8(4) ?
C4 C5 C6 C7 . . . . -178.7(3) ?
P1 N1 C7 O1 . . . . 2.6(4) y
P1 N1 C7 C6 . . . . -178.51(19) ?
C1 C6 C7 O1 . . . . -133.9(3) ?
C5 C6 C7 O1 . . . . 43.4(4) ?
C1 C6 C7 N1 . . . . 47.1(4) ?
C5 C6 C7 N1 . . . . -135.6(3) ?
P1 N2 C8 C9 . . . . 118.4(2) ?
N2 C8 C9 C10 . . . . 172.1(2) ?
N2 C8 C9 C14 . . . . -7.6(4) ?
C14 C9 C10 C11 . . . . 0.5(4) ?
C8 C9 C10 C11 . . . . -179.2(3) ?
C14 C9 C10 Cl1 . . . . -179.4(2) ?
C8 C9 C10 Cl1 . . . . 0.8(4) ?
C9 C10 C11 C12 . . . . 0.2(4) ?
Cl1 C10 C11 C12 . . . . -179.8(2) ?
C10 C11 C12 C13 . . . . -1.0(4) ?
C11 C12 C13 C14 . . . . 1.0(4) ?
C12 C13 C14 C9 . . . . -0.2(4) ?
C10 C9 C14 C13 . . . . -0.5(4) ?
C8 C9 C14 C13 . . . . 179.2(3) ?
P1 N3 C15 C16 . . . . 156.82(19) ?
N3 C15 C16 C21 . . . . 10.1(4) ?
N3 C15 C16 C17 . . . . -171.5(2) ?
C21 C16 C17 C18 . . . . -2.5(4) ?
C15 C16 C17 C18 . . . . 179.0(3) ?
C21 C16 C17 Cl2 . . . . 178.2(2) ?
C15 C16 C17 Cl2 . . . . -0.3(4) ?
C16 C17 C18 C19 . . . . 2.0(4) ?
Cl2 C17 C18 C19 . . . . -178.7(2) ?
C17 C18 C19 C20 . . . . -0.5(4) ?
C18 C19 C20 C21 . . . . -0.6(4) ?
C19 C20 C21 C16 . . . . 0.1(4) ?
C17 C16 C21 C20 . . . . 1.4(4) ?
C15 C16 C21 C20 . . . . 179.9(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654317
