#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/13/2231306.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_2231306
loop_
_publ_author_name
'Pourayoubi, Mehrdad'
'Fadaei, Hassan'
'Parvez, Masood'
_publ_section_title
;
 N,N'-Bis(2-chlorobenzyl)-N''-(2,2,2-trichloroacetyl)phosphoric
 triamide
;
_journal_coeditor_code           SJ5176
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2046
_journal_paper_doi               10.1107/S1600536811027681
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H15 Cl5 N3 O2 P'
_chemical_formula_moiety         'C16 H15 Cl5 N3 O2 P'
_chemical_formula_sum            'C16 H15 Cl5 N3 O2 P'
_chemical_formula_weight         489.53
_chemical_name_systematic
;
N,N'-Bis(2-chlorobenzyl)-N''-(2,2,2-
trichloroacetyl)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                75.8920(13)
_cell_angle_beta                 72.2250(15)
_cell_angle_gamma                69.6050(15)
_cell_formula_units_Z            2
_cell_length_a                   9.9789(2)
_cell_length_b                   10.6058(3)
_cell_length_c                   10.8386(3)
_cell_measurement_reflns_used    4567
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.0
_cell_volume                     1011.66(5)
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'enCIFer (Allen et al., 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type
'Nonius KappaCCD diffractometer with APEXII CCD detector'
_diffrn_measurement_method       'ω and φ'
_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  0.0201
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8947
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.62
_diffrn_reflns_theta_min         2.00
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.814
_exptl_absorpt_correction_T_max  0.9086
_exptl_absorpt_correction_T_min  0.8673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1997)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.420
_refine_diff_density_min         -0.680
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4638
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0525
_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)+(0.0430P)²+2.0234P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1224
_refine_ls_wR_factor_ref         0.1292
_reflns_number_gt                4083
_reflns_number_total             4638
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5176.cif
_cod_data_source_block           I
_cod_original_cell_volume        1011.66(4)
_cod_database_code               2231306
_cod_database_fobs_code          2231306
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.58102(9) -0.04802(11) 1.36183(8) 0.0547(3) Uani d . 1 1 . .
Cl Cl2 0.87488(8) -0.22348(7) 1.35952(8) 0.03998(19) Uani d . 1 1 . .
Cl Cl3 0.68228(12) -0.30242(9) 1.26210(11) 0.0590(3) Uani d . 1 1 . .
P P1 0.72798(7) 0.04068(7) 0.90391(6) 0.02507(16) Uani d . 1 1 . .
O O1 0.9079(2) -0.0722(2) 1.1030(2) 0.0386(5) Uani d . 1 1 A .
O O2 0.60042(19) 0.0572(2) 0.85370(18) 0.0317(4) Uani d . 1 1 A .
N N1 0.6903(2) -0.0446(2) 1.0605(2) 0.0262(4) Uani d . 1 1 A .
H H1 0.6044 -0.0605 1.0925 0.031 Uiso calc R 1 1 . .
C C1 0.7866(3) -0.0882(3) 1.1360(3) 0.0259(5) Uani d . 1 1 . .
C C2 0.7338(3) -0.1636(3) 1.2751(3) 0.0301(5) Uani d . 1 1 A .
N N2 0.8865(2) -0.0463(3) 0.8250(2) 0.0352(6) Uani d . 1 1 A 1
H H2 0.9630 -0.0151 0.8031 0.042 Uiso calc PR 0.8823(17) 1 B 1
C C3 0.9024(3) -0.1740(3) 0.7909(3) 0.0335(7) Uani d P 0.8823(17) 1 A 1
H H3A 0.8074 -0.1713 0.7779 0.040 Uiso calc PR 0.8823(17) 1 B 1
H H3B 0.9247 -0.2470 0.8649 0.040 Uiso calc PR 0.8823(17) 1 B 1
C C4 1.0236(2) -0.2094(2) 0.66667(18) 0.0269(7) Uani d PG 0.8823(17) 1 A 1
C C5 1.0496(2) -0.3322(2) 0.6261(2) 0.0362(7) Uani d PG 0.8823(17) 1 A 1
C C6 1.1578(3) -0.3675(2) 0.5135(2) 0.0476(10) Uani d PG 0.8823(17) 1 A 1
H H6 1.1755 -0.4515 0.4858 0.057 Uiso calc PR 0.8823(17) 1 B 1
C C7 1.2401(3) -0.2800(3) 0.4415(2) 0.0501(11) Uani d PG 0.8823(17) 1 A 1
H H7 1.3141 -0.3041 0.3645 0.060 Uiso calc PR 0.8823(17) 1 B 1
C C8 1.2141(2) -0.1572(2) 0.4820(2) 0.0467(9) Uani d PG 0.8823(17) 1 A 1
H H8 1.2704 -0.0973 0.4328 0.056 Uiso calc PR 0.8823(17) 1 B 1
C C9 1.1059(2) -0.12185(18) 0.5946(2) 0.0342(7) Uani d PG 0.8823(17) 1 A 1
H H9 1.0882 -0.0379 0.6223 0.041 Uiso calc PR 0.8823(17) 1 B 1
Cl Cl4 0.94994(12) -0.44175(10) 0.71412(13) 0.0605(3) Uani d P 0.8823(17) 1 A 1
H H2' 0.9162 -0.1096 0.8886 0.042 Uiso calc PR 0.1177(17) 1 B 2
C C3' 0.993(3) -0.079(2) 0.730(2) 0.0335(7) Uani d P 0.1177(17) 1 A 2
H H3'1 1.0801 -0.0997 0.7645 0.040 Uiso calc PR 0.1177(17) 1 B 2
H H3'2 0.9892 0.0079 0.6686 0.040 Uiso calc PR 0.1177(17) 1 B 2
C C4' 1.036(2) -0.1806(18) 0.6432(18) 0.0269(7) Uani d PG 0.1177(17) 1 A 2
C C5' 1.148(2) -0.1813(19) 0.529(2) 0.0362(7) Uani d PG 0.1177(17) 1 A 2
C C6' 1.199(2) -0.289(2) 0.4586(18) 0.0476(10) Uani d PG 0.1177(17) 1 A 2
H H6' 1.2753 -0.2892 0.3808 0.057 Uiso calc PR 0.1177(17) 1 B 2
C C7' 1.137(2) -0.395(2) 0.501(2) 0.0501(11) Uani d PG 0.1177(17) 1 A 2
H H7' 1.1711 -0.4687 0.4529 0.060 Uiso calc PR 0.1177(17) 1 B 2
C C8' 1.024(2) -0.3946(17) 0.6152(19) 0.0467(9) Uani d PG 0.1177(17) 1 A 2
H H8' 0.9819 -0.4675 0.6445 0.056 Uiso calc PR 0.1177(17) 1 B 2
C C9' 0.9738(19) -0.287(2) 0.6861(15) 0.0342(7) Uani d PG 0.1177(17) 1 A 2
H H9' 0.8970 -0.2867 0.7638 0.041 Uiso calc PR 0.1177(17) 1 B 2
Cl Cl4' 1.2278(9) -0.0556(8) 0.4817(10) 0.0605(3) Uani d P 0.1177(17) 1 A 2
N N3 0.7555(2) 0.1823(2) 0.9050(2) 0.0309(5) Uani d . 1 1 A .
H H3 0.8465 0.1849 0.8889 0.037 Uiso calc R 1 1 . .
C C10 0.6334(3) 0.3062(3) 0.9322(3) 0.0356(6) Uani d . 1 1 . .
H H10A 0.5478 0.3027 0.9065 0.043 Uiso calc R 1 1 A .
H H10B 0.6632 0.3860 0.8773 0.043 Uiso calc R 1 1 . .
C C11 0.5868(3) 0.3256(3) 1.0740(3) 0.0322(6) Uani d . 1 1 A .
C C12 0.6657(4) 0.3724(3) 1.1291(3) 0.0409(7) Uani d . 1 1 . .
C C13 0.6224(5) 0.3866(4) 1.2614(4) 0.0529(9) Uani d . 1 1 A .
H H13 0.6780 0.4188 1.2971 0.064 Uiso calc R 1 1 . .
C C14 0.4988(5) 0.3535(4) 1.3393(4) 0.0584(10) Uani d . 1 1 . .
H H14 0.4689 0.3624 1.4296 0.070 Uiso calc R 1 1 A .
C C15 0.4189(4) 0.3081(4) 1.2880(4) 0.0559(9) Uani d . 1 1 A .
H H15 0.3331 0.2856 1.3424 0.067 Uiso calc R 1 1 . .
C C16 0.4620(4) 0.2945(3) 1.1571(3) 0.0437(7) Uani d . 1 1 . .
H H16 0.4047 0.2629 1.1228 0.052 Uiso calc R 1 1 A .
Cl Cl5 0.82320(12) 0.41376(12) 1.03083(12) 0.0672(3) Uani d . 1 1 A .
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
O2 P1 N2 116.10(12)
O2 P1 N3 114.51(12)
N2 P1 N3 103.26(13)
O2 P1 N1 104.46(11)
N2 P1 N1 108.13(13)
N3 P1 N1 110.31(11)
C1 N1 P1 122.56(18)
C1 N1 H1 118.7
P1 N1 H1 118.7
O1 C1 N1 124.8(2)
O1 C1 C2 119.8(2)
N1 C1 C2 115.5(2)
C1 C2 Cl1 108.21(18)
C1 C2 Cl2 110.50(18)
Cl1 C2 Cl2 109.24(16)
C1 C2 Cl3 109.63(19)
Cl1 C2 Cl3 109.77(15)
Cl2 C2 Cl3 109.47(15)
C3 N2 P1 120.0(2)
C3 N2 H2 120.0
P1 N2 H2 120.0
N2 C3 C4 113.7(2)
N2 C3 H3A 108.8
C4 C3 H3A 108.8
N2 C3 H3B 108.8
C4 C3 H3B 108.8
H3A C3 H3B 107.7
C5 C4 C9 120.0
C5 C4 C3 118.28(18)
C9 C4 C3 121.71(18)
C4 C5 C6 120.0
C4 C5 Cl4 120.65(14)
C6 C5 Cl4 119.35(14)
C7 C6 C5 120.0
C7 C6 H6 120.0
C5 C6 H6 120.0
C6 C7 C8 120.0
C6 C7 H7 120.0
C8 C7 H7 120.0
C9 C8 C7 120.0
C9 C8 H8 120.0
C7 C8 H8 120.0
C8 C9 C4 120.0
C8 C9 H9 120.0
C4 C9 H9 120.0
C4' C3' H3'1 103.9
C4' C3' H3'2 103.9
H3'1 C3' H3'2 105.4
C5' C4' C9' 120.0
C5' C4' C3' 121.6(16)
C9' C4' C3' 118.0(16)
C4' C5' C6' 120.0
C4' C5' Cl4' 119.8(12)
C6' C5' Cl4' 120.1(12)
C5' C6' C7' 120.0
C5' C6' H6' 120.0
C7' C6' H6' 120.0
C8' C7' C6' 120.0
C8' C7' H7' 120.0
C6' C7' H7' 120.0
C7' C8' C9' 120.0
C7' C8' H8' 120.0
C9' C8' H8' 120.0
C8' C9' C4' 120.0
C8' C9' H9' 120.0
C4' C9' H9' 120.0
C10 N3 P1 122.06(19)
C10 N3 H3 119.0
P1 N3 H3 119.0
N3 C10 C11 113.5(2)
N3 C10 H10A 108.9
C11 C10 H10A 108.9
N3 C10 H10B 108.9
C11 C10 H10B 108.9
H10A C10 H10B 107.7
C12 C11 C16 116.5(3)
C12 C11 C10 122.8(3)
C16 C11 C10 120.7(3)
C11 C12 C13 121.7(3)
C11 C12 Cl5 119.1(3)
C13 C12 Cl5 119.1(3)
C14 C13 C12 119.3(3)
C14 C13 H13 120.3
C12 C13 H13 120.3
C15 C14 C13 120.3(4)
C15 C14 H14 119.9
C13 C14 H14 119.9
C14 C15 C16 120.1(4)
C14 C15 H15 119.9
C16 C15 H15 119.9
C15 C16 C11 121.9(3)
C15 C16 H16 119.0
C11 C16 H16 119.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C2 1.759(3)
Cl2 C2 1.761(3)
Cl3 C2 1.768(3)
P1 O2 1.4724(18)
P1 N2 1.621(2)
P1 N3 1.622(2)
P1 N1 1.715(2)
O1 C1 1.212(3)
N1 C1 1.339(3)
N1 H1 0.8800
C1 C2 1.553(4)
N2 C3 1.434(4)
N2 H2 0.8800
C3 C4 1.534(3)
C3 H3A 0.9900
C3 H3B 0.9900
C4 C5 1.3900
C4 C9 1.3900
C5 C6 1.3900
C5 Cl4 1.713(2)
C6 C7 1.3900
C6 H6 0.9500
C7 C8 1.3900
C7 H7 0.9500
C8 C9 1.3900
C8 H8 0.9500
C9 H9 0.9500
C3' C4' 1.47(3)
C3' H3'1 0.9900
C3' H3'2 0.9900
C4' C5' 1.3900
C4' C9' 1.3900
C5' C6' 1.3900
C5' Cl4' 1.682(17)
C6' C7' 1.3900
C6' H6' 0.9500
C7' C8' 1.3900
C7' H7' 0.9500
C8' C9' 1.3900
C8' H8' 0.9500
C9' H9' 0.9500
N3 C10 1.467(4)
N3 H3 0.8800
C10 C11 1.507(4)
C10 H10A 0.9900
C10 H10B 0.9900
C11 C12 1.388(4)
C11 C16 1.389(4)
C12 C13 1.395(5)
C12 Cl5 1.740(4)
C13 C14 1.371(6)
C13 H13 0.9500
C14 C15 1.359(6)
C14 H14 0.9500
C15 C16 1.380(5)
C15 H15 0.9500
C16 H16 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
N1 H1 O2 2_657 0.88 1.94 2.804(3) 168.2
N2 H2 O1 2_757 0.88 2.38 3.106(3) 140.5
N2' H2' O1 . 0.88 2.42 3.025(3) 125.9
N3 H3 O1 2_757 0.88 2.34 3.129(3) 149.1
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
O2 P1 N1 C1 174.8(2)
N2 P1 N1 C1 50.6(2)
N3 P1 N1 C1 -61.6(2)
P1 N1 C1 O1 0.2(4)
P1 N1 C1 C2 -179.98(18)
O1 C1 C2 Cl1 116.0(3)
N1 C1 C2 Cl1 -63.9(3)
O1 C1 C2 Cl2 -3.6(3)
N1 C1 C2 Cl2 176.56(19)
O1 C1 C2 Cl3 -124.3(2)
N1 C1 C2 Cl3 55.8(3)
O2 P1 N2 C3 -47.0(3)
N3 P1 N2 C3 -173.2(2)
N1 P1 N2 C3 69.9(3)
P1 N2 C3 C4 151.5(2)
N2 C3 C4 C5 179.0(2)
N2 C3 C4 C9 -1.5(4)
C9 C4 C5 C6 0.0
C3 C4 C5 C6 179.5(2)
C9 C4 C5 Cl4 179.67(18)
C3 C4 C5 Cl4 -0.8(2)
C4 C5 C6 C7 0.0
Cl4 C5 C6 C7 -179.67(18)
C5 C6 C7 C8 0.0
C6 C7 C8 C9 0.0
C7 C8 C9 C4 0.0
C5 C4 C9 C8 0.0
C3 C4 C9 C8 -179.5(3)
C9' C4' C5' C6' 0.0
C3' C4' C5' C6' 172(2)
C9' C4' C5' Cl4' -177.3(15)
C3' C4' C5' Cl4' -5(2)
C4' C5' C6' C7' 0.0
Cl4' C5' C6' C7' 177.2(16)
C5' C6' C7' C8' 0.0
C6' C7' C8' C9' 0.0
C7' C8' C9' C4' 0.0
C5' C4' C9' C8' 0.0
C3' C4' C9' C8' -172(2)
O2 P1 N3 C10 34.9(2)
N2 P1 N3 C10 162.0(2)
N1 P1 N3 C10 -82.6(2)
P1 N3 C10 C11 94.5(3)
N3 C10 C11 C12 77.3(3)
N3 C10 C11 C16 -101.5(3)
C16 C11 C12 C13 0.4(4)
C10 C11 C12 C13 -178.5(3)
C16 C11 C12 Cl5 -179.9(2)
C10 C11 C12 Cl5 1.2(4)
C11 C12 C13 C14 0.0(5)
Cl5 C12 C13 C14 -179.7(3)
C12 C13 C14 C15 -0.3(5)
C13 C14 C15 C16 0.2(6)
C14 C15 C16 C11 0.2(5)
C12 C11 C16 C15 -0.5(5)
C10 C11 C16 C15 178.4(3)
