#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/92/2229235.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_2229235
loop_
_publ_author_name
'Pourayoubi, Mehrdad'
'Padělková, Zdeňka'
'Rostami Chaijan, Mahnaz'
'R°užička, Aleš'
_publ_section_title
;
 N,N',N'',N'''-Tetrakis(2-methylphenyl)oxybis(phosphonic
 diamide): a redetermination at 150K with Mo Kα radiation
;
_journal_coeditor_code           SJ5092
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o450
_journal_page_last               o451
_journal_paper_doi               10.1107/S1600536811002091
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C28 H32 N4 O3 P2'
_chemical_formula_moiety         'C28 H32 N4 O3 P2'
_chemical_formula_sum            'C28 H32 N4 O3 P2'
_chemical_formula_weight         534.52
_chemical_name_common
;
N,N',N'',N'''-Tetrakis(2-
methylphenyl)oxybis(phosphonic diamide)
;
_chemical_name_systematic
;
N-{[bis(2-methylanilino)phosphoryloxy](2-
methylanilino)phosphoryl]}-2-methylaniline
;
_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           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 118.915(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2621(6)
_cell_length_b                   15.7029(11)
_cell_length_c                   13.8401(8)
_cell_measurement_temperature    150.0(10)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1
_cell_volume                     2713.2(3)
_computing_cell_refinement
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_data_collection
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_data_reduction
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150.0(10)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker--Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_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  0.0469
_diffrn_reflns_av_sigmaI/netI    0.0444
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19090
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.63
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
Gaussian integration (Coppens & Hamilton, 1970)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.505
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         6133
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.176
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0535
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0260P)²+3.5968P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1211
_reflns_number_gt                4719
_reflns_number_total             6133
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5092.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229235
_cod_database_fobs_code          2229235
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_disorder_assembly
_atom_site_disorder_group
P P1 0.71234(5) 0.23508(4) 0.23550(5) 0.01571(14) Uani d . 1 . .
P P2 0.81104(5) 0.21568(4) 0.47636(5) 0.01629(14) Uani d . 1 . .
O O3 0.71315(13) 0.18618(12) 0.47678(13) 0.0220(4) Uani d . 1 . .
O O2 0.77228(13) 0.18044(11) 0.19840(14) 0.0222(4) Uani d . 1 . .
N N111 0.67768(15) 0.32469(13) 0.16770(15) 0.0171(4) Uani d . 1 . .
H H111 0.7047 0.3375 0.1258 0.021 Uiso d R 1 . .
N N112 0.60850(15) 0.19217(13) 0.23720(15) 0.0181(4) Uani d . 1 . .
H H112 0.6126 0.1794 0.2995 0.022 Uiso d R 1 . .
O O1 0.78382(12) 0.26154(11) 0.36239(12) 0.0195(4) Uani d . 1 . .
N N113 0.87451(15) 0.28468(13) 0.57247(15) 0.0183(4) Uani d . 1 . .
H H113 0.8426 0.3037 0.6073 0.022 Uiso d R 1 . .
N N114 0.89635(16) 0.14390(13) 0.48176(16) 0.0207(4) Uani d . 1 . .
H H114 0.9035 0.1363 0.4242 0.025 Uiso d R 1 . .
C C15 0.97931(18) 0.31677(16) 0.6050(2) 0.0192(5) Uani d . 1 . .
C C8 0.51193(18) 0.17513(15) 0.13812(18) 0.0171(5) Uani d . 1 . .
C C14 0.4100(2) 0.25236(18) 0.2194(2) 0.0263(6) Uani d . 1 . .
H H14A 0.3375 0.2691 0.1963 0.032 Uiso d R 1 . .
H H14B 0.4543 0.3021 0.2366 0.032 Uiso d R 1 . .
H H14C 0.4356 0.2169 0.2837 0.032 Uiso d R 1 . .
C C10 0.3220(2) 0.18702(18) 0.0296(2) 0.0268(6) Uani d . 1 . .
H H10 0.2563 0.2049 0.0211 0.032 Uiso d R 1 . .
C C27 0.9154(2) 0.06277(17) 0.6406(2) 0.0259(6) Uani d . 1 . .
H H27 0.8443 0.0744 0.6200 0.031 Uiso d R 1 . .
C C23 1.0662(2) 0.07556(16) 0.6064(2) 0.0231(5) Uani d . 1 . .
C C1 0.60452(19) 0.38319(15) 0.1753(2) 0.0193(5) Uani d . 1 . .
C C2 0.5062(2) 0.40163(16) 0.0836(2) 0.0226(5) Uani d . 1 . .
C C9 0.41430(19) 0.20379(16) 0.12797(19) 0.0206(5) Uani d . 1 . .
C C24 1.1247(2) 0.02480(17) 0.6984(2) 0.0294(6) Uani d . 1 . .
H H24 1.1947 0.0104 0.7174 0.035 Uiso d R 1 . .
C C21 1.0415(2) 0.25452(19) 0.7949(2) 0.0297(6) Uani d . 1 . .
H H21A 1.1022 0.2605 0.8673 0.036 Uiso d R 1 . .
H H21B 1.0307 0.1954 0.7750 0.036 Uiso d R 1 . .
H H21C 0.9789 0.2768 0.7950 0.036 Uiso d R 1 . .
C C16 1.06130(19) 0.30251(16) 0.7133(2) 0.0219(5) Uani d . 1 . .
C C6 0.6332(2) 0.42124(17) 0.2774(2) 0.0267(6) Uani d . 1 . .
H H6 0.7003 0.4104 0.3374 0.032 Uiso d R 1 . .
C C22 0.9598(2) 0.09322(16) 0.5770(2) 0.0214(5) Uani d . 1 . .
C C11 0.3249(2) 0.1444(2) -0.0562(2) 0.0326(7) Uani d . 1 . .
H H11 0.2619 0.1348 -0.1218 0.039 Uiso d R 1 . .
C C12 0.4213(2) 0.11623(19) -0.0450(2) 0.0305(6) Uani d . 1 . .
H H12 0.4234 0.0873 -0.1025 0.037 Uiso d R 1 . .
C C3 0.4368(2) 0.45692(18) 0.0985(2) 0.0309(6) Uani d . 1 . .
H H3 0.3708 0.4705 0.0386 0.037 Uiso d R 1 . .
C C13 0.5154(2) 0.13111(17) 0.0530(2) 0.0241(5) Uani d . 1 . .
H H13 0.5806 0.1117 0.0615 0.029 Uiso d R 1 . .
C C25 1.0816(2) -0.00486(18) 0.7628(2) 0.0327(6) Uani d . 1 . .
H H25 1.1228 -0.0381 0.8247 0.039 Uiso d R 1 . .
C C19 1.1003(2) 0.39397(19) 0.5620(3) 0.0331(6) Uani d . 1 . .
H H19 1.1132 0.4239 0.5116 0.040 Uiso d R 1 . .
C C7 0.4739(2) 0.36301(18) -0.0263(2) 0.0264(6) Uani d . 1 . .
H H7A 0.5312 0.3690 -0.0435 0.032 Uiso d R 1 . .
H H7B 0.4112 0.3914 -0.0816 0.032 Uiso d R 1 . .
H H7C 0.4585 0.3037 -0.0247 0.032 Uiso d R 1 . .
C C20 0.9989(2) 0.36202(18) 0.5309(2) 0.0261(6) Uani d . 1 . .
H H20 0.9437 0.3714 0.4595 0.031 Uiso d R 1 . .
C C26 0.9776(2) 0.01502(17) 0.7348(2) 0.0300(6) Uani d . 1 . .
H H26 0.9489 -0.0035 0.7788 0.036 Uiso d R 1 . .
C C28 1.1164(2) 0.11288(19) 0.5422(2) 0.0308(6) Uani d . 1 . .
H H28A 1.1902 0.0960 0.5754 0.037 Uiso d R 1 . .
H H28B 1.1120 0.1739 0.5429 0.037 Uiso d R 1 . .
H H28C 1.0791 0.0928 0.4674 0.037 Uiso d R 1 . .
C C18 1.1820(2) 0.3807(2) 0.6680(3) 0.0354(7) Uani d . 1 . .
H H18 1.2501 0.4021 0.6897 0.043 Uiso d R 1 . .
C C5 0.5626(3) 0.47486(18) 0.2898(3) 0.0347(7) Uani d . 1 . .
H H5 0.5812 0.4991 0.3581 0.042 Uiso d R 1 . .
C C17 1.1622(2) 0.33534(19) 0.7422(2) 0.0314(6) Uani d . 1 . .
H H17 1.2181 0.3266 0.8133 0.038 Uiso d R 1 . .
C C4 0.4648(2) 0.49159(18) 0.2005(3) 0.0344(7) Uani d . 1 . .
H H4 0.4168 0.5270 0.2087 0.041 Uiso d 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'
O O 0.0106 0.0060 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 1 0 0.134
-1 0 0 0.117
0 -1 0 0.125
1 0 0 0.189
0 0 -1 0.082
0 0 1 0.106
0 1 0 0.173
0 -1 -1 0.082
0 1 -1 0.110
0 1 1 0.146
1 1 -1 0.110
-1 -1 1 0.154
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 O1 . . 111.45(10) ?
O2 P1 N111 . . 111.65(10) ?
O1 P1 N111 . . 105.22(10) ?
O2 P1 N112 . . 116.62(11) ?
O1 P1 N112 . . 101.05(9) ?
N111 P1 N112 . . 109.81(10) ?
O3 P2 O1 . . 111.48(9) ?
O3 P2 N113 . . 111.30(10) ?
O1 P2 N113 . . 106.40(10) ?
O3 P2 N114 . . 117.97(11) ?
O1 P2 N114 . . 100.12(10) ?
N113 P2 N114 . . 108.51(11) ?
C1 N111 P1 . . 122.72(15) ?
C1 N111 H111 . . 118.7 ?
P1 N111 H111 . . 118.6 ?
C8 N112 P1 . . 121.64(15) ?
C8 N112 H112 . . 119.2 ?
P1 N112 H112 . . 119.2 ?
P1 O1 P2 . . 133.31(11) ?
C15 N113 P2 . . 125.59(16) ?
C15 N113 H113 . . 117.2 ?
P2 N113 H113 . . 117.2 ?
C22 N114 P2 . . 123.54(17) ?
C22 N114 H114 . . 118.2 ?
P2 N114 H114 . . 118.3 ?
C20 C15 C16 . . 120.8(2) ?
C20 C15 N113 . . 120.2(2) ?
C16 C15 N113 . . 119.0(2) ?
C13 C8 C9 . . 121.0(2) ?
C13 C8 N112 . . 119.8(2) ?
C9 C8 N112 . . 119.2(2) ?
C9 C14 H14A . . 109.5 ?
C9 C14 H14B . . 109.4 ?
H14A C14 H14B . . 109.5 ?
C9 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C11 C10 C9 . . 121.8(2) ?
C11 C10 H10 . . 119.1 ?
C9 C10 H10 . . 119.1 ?
C26 C27 C22 . . 119.9(3) ?
C26 C27 H27 . . 120.1 ?
C22 C27 H27 . . 120.0 ?
C24 C23 C22 . . 117.9(2) ?
C24 C23 C28 . . 121.3(2) ?
C22 C23 C28 . . 120.8(2) ?
C2 C1 C6 . . 120.3(2) ?
C2 C1 N111 . . 121.0(2) ?
C6 C1 N111 . . 118.7(2) ?
C1 C2 C3 . . 117.8(2) ?
C1 C2 C7 . . 121.6(2) ?
C3 C2 C7 . . 120.6(2) ?
C10 C9 C8 . . 117.5(2) ?
C10 C9 C14 . . 121.1(2) ?
C8 C9 C14 . . 121.3(2) ?
C25 C24 C23 . . 121.8(3) ?
C25 C24 H24 . . 119.2 ?
C23 C24 H24 . . 119.0 ?
C16 C21 H21A . . 109.5 ?
C16 C21 H21B . . 109.4 ?
H21A C21 H21B . . 109.5 ?
C16 C21 H21C . . 109.4 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C17 C16 C15 . . 117.3(2) ?
C17 C16 C21 . . 121.1(2) ?
C15 C16 C21 . . 121.6(2) ?
C5 C6 C1 . . 120.6(3) ?
C5 C6 H6 . . 119.7 ?
C1 C6 H6 . . 119.7 ?
C27 C22 C23 . . 120.6(2) ?
C27 C22 N114 . . 119.8(2) ?
C23 C22 N114 . . 119.6(2) ?
C12 C11 C10 . . 120.1(2) ?
C12 C11 H11 . . 119.9 ?
C10 C11 H11 . . 120.0 ?
C11 C12 C13 . . 119.7(3) ?
C11 C12 H12 . . 120.2 ?
C13 C12 H12 . . 120.2 ?
C4 C3 C2 . . 121.2(3) ?
C4 C3 H3 . . 119.3 ?
C2 C3 H3 . . 119.5 ?
C8 C13 C12 . . 119.9(2) ?
C8 C13 H13 . . 120.0 ?
C12 C13 H13 . . 120.1 ?
C26 C25 C24 . . 119.7(3) ?
C26 C25 H25 . . 120.2 ?
C24 C25 H25 . . 120.1 ?
C18 C19 C20 . . 119.5(3) ?
C18 C19 H19 . . 120.2 ?
C20 C19 H19 . . 120.3 ?
C2 C7 H7A . . 109.5 ?
C2 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C2 C7 H7C . . 109.4 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C15 C20 C19 . . 120.6(3) ?
C15 C20 H20 . . 119.8 ?
C19 C20 H20 . . 119.5 ?
C25 C26 C27 . . 120.0(3) ?
C25 C26 H26 . . 120.0 ?
C27 C26 H26 . . 120.0 ?
C23 C28 H28A . . 109.6 ?
C23 C28 H28B . . 109.3 ?
H28A C28 H28B . . 109.5 ?
C23 C28 H28C . . 109.5 ?
H28A C28 H28C . . 109.5 ?
H28B C28 H28C . . 109.5 ?
C19 C18 C17 . . 119.8(3) ?
C19 C18 H18 . . 120.0 ?
C17 C18 H18 . . 120.1 ?
C4 C5 C6 . . 119.2(3) ?
C4 C5 H5 . . 120.3 ?
C6 C5 H5 . . 120.5 ?
C18 C17 C16 . . 122.0(3) ?
C18 C17 H17 . . 118.8 ?
C16 C17 H17 . . 119.2 ?
C5 C4 C3 . . 120.8(3) ?
C5 C4 H4 . . 119.5 ?
C3 C4 H4 . . 119.6 ?
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 . 1.4681(17) ?
P1 O1 . 1.6014(16) ?
P1 N111 . 1.630(2) ?
P1 N112 . 1.6376(19) ?
P2 O3 . 1.4736(17) ?
P2 O1 . 1.6017(16) ?
P2 N113 . 1.612(2) ?
P2 N114 . 1.634(2) ?
N111 C1 . 1.432(3) ?
N111 H111 . 0.8600 ?
N112 C8 . 1.422(3) ?
N112 H112 . 0.8599 ?
N113 C15 . 1.428(3) ?
N113 H113 . 0.8600 ?
N114 C22 . 1.427(3) ?
N114 H114 . 0.8600 ?
C15 C20 . 1.383(4) ?
C15 C16 . 1.403(3) ?
C8 C13 . 1.387(3) ?
C8 C9 . 1.404(3) ?
C14 C9 . 1.504(3) ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9599 ?
C10 C11 . 1.382(4) ?
C10 C9 . 1.387(3) ?
C10 H10 . 0.9300 ?
C27 C26 . 1.389(4) ?
C27 C22 . 1.393(4) ?
C27 H27 . 0.9300 ?
C23 C24 . 1.388(4) ?
C23 C22 . 1.396(3) ?
C23 C28 . 1.504(4) ?
C1 C2 . 1.393(3) ?
C1 C6 . 1.401(3) ?
C2 C3 . 1.404(4) ?
C2 C7 . 1.489(4) ?
C24 C25 . 1.385(4) ?
C24 H24 . 0.9300 ?
C21 C16 . 1.494(4) ?
C21 H21A . 0.9601 ?
C21 H21B . 0.9599 ?
C21 H21C . 0.9601 ?
C16 C17 . 1.392(4) ?
C6 C5 . 1.385(4) ?
C6 H6 . 0.9300 ?
C11 C12 . 1.379(4) ?
C11 H11 . 0.9299 ?
C12 C13 . 1.391(4) ?
C12 H12 . 0.9300 ?
C3 C4 . 1.380(4) ?
C3 H3 . 0.9299 ?
C13 H13 . 0.9300 ?
C25 C26 . 1.375(4) ?
C25 H25 . 0.9300 ?
C19 C18 . 1.379(4) ?
C19 C20 . 1.388(4) ?
C19 H19 . 0.9300 ?
C7 H7A . 0.9601 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9601 ?
C20 H20 . 0.9301 ?
C26 H26 . 0.9300 ?
C28 H28A . 0.9601 ?
C28 H28B . 0.9600 ?
C28 H28C . 0.9600 ?
C18 C17 . 1.386(4) ?
C18 H18 . 0.9300 ?
C5 C4 . 1.369(4) ?
C5 H5 . 0.9300 ?
C17 H17 . 0.9300 ?
C4 H4 . 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
N111 H111 O3 4_565 0.86 2.16 2.926(2) 149
N112 H112 O3 . 0.86 2.16 2.906(2) 144
N113 H113 O2 4_566 0.86 1.97 2.814(2) 167
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656494
