#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/90/2229038.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_2229038
loop_
_publ_author_name
'Pourayoubi, Mehrdad'
'Toghraee, Maryam'
'Divjakovic, Vladimir'
_publ_section_title
;
 N,N'-Bis(2-chlorobenzyl)-N''-(dichloroacetyl)phosphoric
 triamide
;
_journal_coeditor_code           FI2102
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o333
_journal_paper_doi               10.1107/S1600536811000845
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H16 Cl4 N3 O2 P'
_chemical_formula_moiety         'C16 H16 Cl4 N3 O2 P'
_chemical_formula_sum            'C16 H16 Cl4 N3 O2 P'
_chemical_formula_weight         455.09
_chemical_name_systematic
;
N,N'-Bis(2-chlorobenzyl)-N''-(dichloroacetyl)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
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug  2 2010,13:00:58)
;
_cell_angle_alpha                90.403(5)
_cell_angle_beta                 112.851(6)
_cell_angle_gamma                114.084(6)
_cell_formula_units_Z            2
_cell_length_a                   9.9010(10)
_cell_length_b                   10.1790(10)
_cell_length_c                   12.013(2)
_cell_measurement_reflns_used    2802
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.0003
_cell_measurement_theta_min      3.4765
_cell_volume                     998.7(2)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 16.3280
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Oxford Diffraction Xcalibur Sapphire3 Gemini'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6193
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.48
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Oxford Diffraction, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.221
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.105
_refine_diff_density_max         0.955
_refine_diff_density_min         -0.653
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3510
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0608
_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)+(0.0618P)²+1.5174P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1437
_refine_ls_wR_factor_ref         0.1559
_reflns_number_gt                2786
_reflns_number_total             3510
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fi2102.cif
_cod_data_source_block           I
_cod_database_code               2229038
_cod_database_fobs_code          2229038
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 P 0.84901(11) 0.52095(11) 0.59850(8) 0.0398(3) Uani d . 1 . .
Cl Cl1 0.4017(2) 0.3402(3) 0.12756(12) 0.1300(8) Uani d . 1 . .
Cl Cl2 0.5672(2) 0.16627(16) 0.23126(18) 0.1108(6) Uani d . 1 . .
Cl Cl3 0.65788(18) 0.91760(16) 0.50769(15) 0.0893(5) Uani d . 1 . .
Cl Cl4 0.77087(18) 0.44836(16) 1.03178(11) 0.0804(4) Uani d . 1 . .
O O1 1.0238(3) 0.5568(3) 0.6484(2) 0.0543(7) Uani d . 1 . .
O O2 0.5072(3) 0.4115(4) 0.3908(3) 0.0670(9) Uani d . 1 . .
N N1 0.7379(4) 0.4006(4) 0.6531(3) 0.0496(8) Uani d . 1 . .
H H1 0.6627 0.3184 0.6048 0.059 Uiso calc R 1 . .
N N2 0.7656(3) 0.4413(3) 0.4495(3) 0.0427(7) Uani d . 1 . .
H H2 0.8279 0.4239 0.4240 0.051 Uiso calc R 1 . .
N N3 0.8251(4) 0.6669(3) 0.6149(3) 0.0481(8) Uani d . 1 . .
H H3 0.7538 0.6631 0.6405 0.058 Uiso calc R 1 . .
C C1 0.5775(5) 0.3419(5) 0.2368(4) 0.0512(10) Uani d . 1 . .
H H1A 0.6696 0.4058 0.2197 0.061 Uiso calc R 1 . .
C C2 0.6105(4) 0.4020(4) 0.3661(3) 0.0423(8) Uani d . 1 . .
C C3 0.9204(5) 0.8049(5) 0.5877(4) 0.0611(11) Uani d . 1 . .
H H3A 1.0292 0.8142 0.6081 0.073 Uiso calc R 1 . .
H H3B 0.9319 0.8859 0.6395 0.073 Uiso calc R 1 . .
C C4 0.8437(5) 0.8158(4) 0.4545(4) 0.0524(10) Uani d . 1 . .
C C5 0.7214(5) 0.8603(4) 0.4084(4) 0.0560(10) Uani d . 1 . .
C C6 0.6453(6) 0.8610(5) 0.2847(5) 0.0741(14) Uani d . 1 . .
H H6 0.5635 0.8919 0.2570 0.089 Uiso calc R 1 . .
C C7 0.6907(8) 0.8161(6) 0.2034(5) 0.0846(16) Uani d . 1 . .
H H7 0.6393 0.8155 0.1199 0.102 Uiso calc R 1 . .
C C8 0.8110(8) 0.7727(6) 0.2449(5) 0.0837(16) Uani d . 1 . .
H H8 0.8424 0.7428 0.1897 0.100 Uiso calc R 1 . .
C C9 0.8878(6) 0.7724(5) 0.3692(5) 0.0678(12) Uani d . 1 . .
H H9 0.9705 0.7425 0.3960 0.081 Uiso calc R 1 . .
C C10 0.7581(5) 0.4233(5) 0.7789(4) 0.0513(10) Uani d . 1 . .
H H10A 0.6585 0.4211 0.7776 0.062 Uiso calc R 1 . .
H H10B 0.8462 0.5203 0.8215 0.062 Uiso calc R 1 . .
C C11 0.7950(4) 0.3128(4) 0.8509(3) 0.0458(9) Uani d . 1 . .
C C12 0.8030(5) 0.3159(5) 0.9693(4) 0.0571(11) Uani d . 1 . .
C C13 0.8391(6) 0.2189(6) 1.0401(5) 0.0745(14) Uani d . 1 . .
H H13 0.8461 0.2247 1.1196 0.089 Uiso calc R 1 . .
C C14 0.8644(7) 0.1145(7) 0.9923(6) 0.0904(17) Uani d . 1 . .
H H14 0.8875 0.0476 1.0391 0.108 Uiso calc R 1 . .
C C15 0.8562(7) 0.1062(6) 0.8740(6) 0.0893(17) Uani d . 1 . .
H H15 0.8733 0.0343 0.8414 0.107 Uiso calc R 1 . .
C C16 0.8225(6) 0.2060(5) 0.8060(5) 0.0657(12) Uani d . 1 . .
H H16 0.8182 0.2013 0.7273 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'
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
O1 P N1 . . 117.84(17) ?
O1 P N3 . . 110.86(18) ?
N1 P N3 . . 106.48(17) ?
O1 P N2 . . 106.38(15) ?
N1 P N2 . . 103.08(16) ?
N3 P N2 . . 112.03(16) ?
C10 N1 P . . 123.7(3) ?
C10 N1 H1 . . 118.2 ?
P N1 H1 . . 118.2 ?
C2 N2 P . . 126.3(2) ?
C2 N2 H2 . . 116.9 ?
P N2 H2 . . 116.9 ?
C3 N3 P . . 122.2(3) ?
C3 N3 H3 . . 118.9 ?
P N3 H3 . . 118.9 ?
C2 C1 Cl1 . . 111.5(3) ?
C2 C1 Cl2 . . 109.2(3) ?
Cl1 C1 Cl2 . . 111.2(2) ?
C2 C1 H1A . . 108.3 ?
Cl1 C1 H1A . . 108.3 ?
Cl2 C1 H1A . . 108.3 ?
O2 C2 N2 . . 123.9(3) ?
O2 C2 C1 . . 123.1(3) ?
N2 C2 C1 . . 113.0(3) ?
N3 C3 C4 . . 113.0(3) ?
N3 C3 H3A . . 109.0 ?
C4 C3 H3A . . 109.0 ?
N3 C3 H3B . . 109.0 ?
C4 C3 H3B . . 109.0 ?
H3A C3 H3B . . 107.8 ?
C5 C4 C9 . . 116.2(4) ?
C5 C4 C3 . . 123.2(4) ?
C9 C4 C3 . . 120.5(4) ?
C4 C5 C6 . . 122.5(4) ?
C4 C5 Cl3 . . 119.7(4) ?
C6 C5 Cl3 . . 117.8(4) ?
C7 C6 C5 . . 119.7(5) ?
C7 C6 H6 . . 120.1 ?
C5 C6 H6 . . 120.1 ?
C8 C7 C6 . . 119.7(5) ?
C8 C7 H7 . . 120.2 ?
C6 C7 H7 . . 120.2 ?
C7 C8 C9 . . 120.7(5) ?
C7 C8 H8 . . 119.7 ?
C9 C8 H8 . . 119.7 ?
C4 C9 C8 . . 121.3(5) ?
C4 C9 H9 . . 119.3 ?
C8 C9 H9 . . 119.3 ?
N1 C10 C11 . . 114.6(3) ?
N1 C10 H10A . . 108.6 ?
C11 C10 H10A . . 108.6 ?
N1 C10 H10B . . 108.6 ?
C11 C10 H10B . . 108.6 ?
H10A C10 H10B . . 107.6 ?
C16 C11 C12 . . 117.0(4) ?
C16 C11 C10 . . 123.2(4) ?
C12 C11 C10 . . 119.7(4) ?
C13 C12 C11 . . 122.2(5) ?
C13 C12 Cl4 . . 118.4(4) ?
C11 C12 Cl4 . . 119.4(3) ?
C12 C13 C14 . . 119.0(5) ?
C12 C13 H13 . . 120.5 ?
C14 C13 H13 . . 120.5 ?
C15 C14 C13 . . 120.8(5) ?
C15 C14 H14 . . 119.6 ?
C13 C14 H14 . . 119.6 ?
C14 C15 C16 . . 118.9(5) ?
C14 C15 H15 . . 120.6 ?
C16 C15 H15 . . 120.6 ?
C11 C16 C15 . . 122.0(5) ?
C11 C16 H16 . . 119.0 ?
C15 C16 H16 . . 119.0 ?
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
P O1 . 1.471(3) ?
P N1 . 1.616(3) ?
P N3 . 1.619(3) ?
P N2 . 1.682(3) ?
Cl1 C1 . 1.718(4) ?
Cl2 C1 . 1.748(4) ?
Cl3 C5 . 1.741(5) ?
Cl4 C12 . 1.733(5) ?
O2 C2 . 1.208(4) ?
N1 C10 . 1.450(5) ?
N1 H1 . 0.8600 ?
N2 C2 . 1.349(4) ?
N2 H2 . 0.8600 ?
N3 C3 . 1.461(5) ?
N3 H3 . 0.8600 ?
C1 C2 . 1.525(5) ?
C1 H1A . 0.9800 ?
C3 C4 . 1.509(6) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 C5 . 1.381(6) ?
C4 C9 . 1.392(6) ?
C5 C6 . 1.382(7) ?
C6 C7 . 1.367(8) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.354(8) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.388(7) ?
C8 H8 . 0.9300 ?
C9 H9 . 0.9300 ?
C10 C11 . 1.500(5) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C16 . 1.376(6) ?
C11 C12 . 1.394(5) ?
C12 C13 . 1.375(6) ?
C13 C14 . 1.358(8) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.392(8) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.373(7) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
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
N2 H2 O1 2_766 0.86 1.93 2.756(4) 162
N3 H3 O2 2_666 0.86 2.24 3.024(4) 151
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
O1 P N1 C10 . . . . 66.5(4) ?
N3 P N1 C10 . . . . -58.7(3) ?
N2 P N1 C10 . . . . -176.8(3) ?
O1 P N2 C2 . . . . -174.1(3) ?
N1 P N2 C2 . . . . 61.3(4) ?
N3 P N2 C2 . . . . -52.8(4) ?
O1 P N3 C3 . . . . 44.0(3) ?
N1 P N3 C3 . . . . 173.4(3) ?
N2 P N3 C3 . . . . -74.6(3) ?
P N2 C2 O2 . . . . -4.7(6) ?
P N2 C2 C1 . . . . 176.0(3) ?
Cl1 C1 C2 O2 . . . . 17.2(5) ?
Cl2 C1 C2 O2 . . . . -106.1(4) ?
Cl1 C1 C2 N2 . . . . -163.5(3) ?
Cl2 C1 C2 N2 . . . . 73.2(4) ?
P N3 C3 C4 . . . . 87.6(4) ?
N3 C3 C4 C5 . . . . 83.3(5) ?
N3 C3 C4 C9 . . . . -93.0(5) ?
C9 C4 C5 C6 . . . . 0.5(6) ?
C3 C4 C5 C6 . . . . -175.9(4) ?
C9 C4 C5 Cl3 . . . . -179.7(3) ?
C3 C4 C5 Cl3 . . . . 3.9(5) ?
C4 C5 C6 C7 . . . . 0.1(7) ?
Cl3 C5 C6 C7 . . . . -179.6(4) ?
C5 C6 C7 C8 . . . . -0.6(8) ?
C6 C7 C8 C9 . . . . 0.4(8) ?
C5 C4 C9 C8 . . . . -0.7(6) ?
C3 C4 C9 C8 . . . . 175.8(4) ?
C7 C8 C9 C4 . . . . 0.3(8) ?
P N1 C10 C11 . . . . -121.2(3) ?
N1 C10 C11 C16 . . . . 5.6(6) ?
N1 C10 C11 C12 . . . . -174.5(4) ?
C16 C11 C12 C13 . . . . 1.0(6) ?
C10 C11 C12 C13 . . . . -178.9(4) ?
C16 C11 C12 Cl4 . . . . 179.6(3) ?
C10 C11 C12 Cl4 . . . . -0.3(5) ?
C11 C12 C13 C14 . . . . -1.4(7) ?
Cl4 C12 C13 C14 . . . . 179.9(4) ?
C12 C13 C14 C15 . . . . 0.8(9) ?
C13 C14 C15 C16 . . . . 0.2(9) ?
C12 C11 C16 C15 . . . . 0.1(7) ?
C10 C11 C16 C15 . . . . 180.0(5) ?
C14 C15 C16 C11 . . . . -0.7(8) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656461
