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#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/84/2228487.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_2228487
loop_
_publ_author_name
'Pourayoubi, Mehrdad'
'Zargaran, Poorya'
'Ghammamy, Shahriar'
'Eshtiagh-Hosseini, Hossein'
_publ_section_title
;
 Diphenyl (p-tolylamido)phosphate
;
_journal_coeditor_code           NG5073
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3357
_journal_paper_doi               10.1107/S1600536810049354
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C19 H18 N O3 P'
_chemical_formula_moiety         'C19 H18 N O3 P'
_chemical_formula_sum            'C19 H18 N O3 P'
_chemical_formula_weight         339.31
_chemical_name_systematic
;
Diphenyl (p-tolylamido)phosphate
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.337(2)
_cell_angle_beta                 109.303(2)
_cell_angle_gamma                117.827(2)
_cell_formula_units_Z            2
_cell_length_a                   9.7406(10)
_cell_length_b                   9.9653(10)
_cell_length_c                   11.1788(12)
_cell_measurement_reflns_used    948
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29
_cell_measurement_theta_min      3
_cell_volume                     858.93(16)
_computing_cell_refinement       'SAINT-Plus (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1998)'
_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      120(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0203
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8165
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.565
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3744
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0453
_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)+(0.0100P)²+1.4000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.0988
_reflns_number_gt                3232
_reflns_number_total             3744
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng5073.cif
_cod_data_source_block           I
_cod_original_cell_volume        858.93(15)
_cod_database_code               2228487
_cod_database_fobs_code          2228487
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 0.30226(6) 0.32453(5) 0.30029(5) 0.01976(12) Uani d . 1 . .
O O1 0.26650(17) 0.38136(15) 0.40642(13) 0.0232(3) Uani d . 1 . .
O O2 0.16664(16) 0.14657(15) 0.20459(12) 0.0212(3) Uani d . 1 . .
O O3 0.28250(16) 0.40203(15) 0.18341(13) 0.0216(3) Uani d . 1 . .
N N1 0.4912(2) 0.34721(19) 0.36132(15) 0.0214(3) Uani d . 1 . .
H H1 0.5535 0.4125 0.4324 0.026 Uiso d R 1 . .
C C1 0.1005(2) 0.0096(2) 0.24317(19) 0.0203(4) Uani d . 1 . .
C C2 -0.0075(2) -0.1338(2) 0.1388(2) 0.0235(4) Uani d . 1 . .
H H2A -0.0313 -0.1345 0.0492 0.028 Uiso calc R 1 . .
C C3 -0.0801(3) -0.2761(2) 0.1673(2) 0.0296(4) Uani d . 1 . .
H H3A -0.1534 -0.3750 0.0968 0.036 Uiso calc R 1 . .
C C4 -0.0461(3) -0.2743(3) 0.2985(2) 0.0319(5) Uani d . 1 . .
H H4A -0.0961 -0.3719 0.3179 0.038 Uiso calc R 1 . .
C C5 0.0611(3) -0.1297(3) 0.4011(2) 0.0325(5) Uani d . 1 . .
H H5A 0.0837 -0.1289 0.4907 0.039 Uiso calc R 1 . .
C C6 0.1362(3) 0.0147(2) 0.3750(2) 0.0276(4) Uani d . 1 . .
H H6A 0.2097 0.1137 0.4454 0.033 Uiso calc R 1 . .
C C7 0.3697(2) 0.5708(2) 0.22208(19) 0.0227(4) Uani d . 1 . .
C C8 0.2885(3) 0.6432(2) 0.2520(2) 0.0300(4) Uani d . 1 . .
H H8A 0.1772 0.5812 0.2487 0.036 Uiso calc R 1 . .
C C9 0.3736(3) 0.8088(3) 0.2869(2) 0.0347(5) Uani d . 1 . .
H H9A 0.3204 0.8612 0.3081 0.042 Uiso calc R 1 . .
C C10 0.5357(3) 0.8980(2) 0.2909(2) 0.0335(5) Uani d . 1 . .
H H10A 0.5929 1.0112 0.3143 0.040 Uiso calc R 1 . .
C C11 0.6148(3) 0.8228(3) 0.2610(2) 0.0327(5) Uani d . 1 . .
H H11A 0.7263 0.8845 0.2646 0.039 Uiso calc R 1 . .
C C12 0.5309(3) 0.6567(2) 0.2257(2) 0.0272(4) Uani d . 1 . .
H H12A 0.5838 0.6039 0.2046 0.033 Uiso calc R 1 . .
C C13 0.5718(2) 0.3089(2) 0.29081(18) 0.0204(4) Uani d . 1 . .
C C14 0.7373(2) 0.3403(2) 0.36440(19) 0.0216(4) Uani d . 1 . .
H H14A 0.7917 0.3854 0.4590 0.026 Uiso calc R 1 . .
C C15 0.8219(2) 0.3056(2) 0.2994(2) 0.0238(4) Uani d . 1 . .
H H15A 0.9342 0.3281 0.3504 0.029 Uiso calc R 1 . .
C C16 0.7450(2) 0.2383(2) 0.1608(2) 0.0255(4) Uani d . 1 . .
C C17 0.5803(3) 0.2073(3) 0.0896(2) 0.0294(4) Uani d . 1 . .
H H17A 0.5251 0.1608 -0.0049 0.035 Uiso calc R 1 . .
C C18 0.4949(3) 0.2425(3) 0.1528(2) 0.0275(4) Uani d . 1 . .
H H18A 0.3832 0.2212 0.1015 0.033 Uiso calc R 1 . .
C C19 0.8337(3) 0.1978(3) 0.0886(2) 0.0363(5) Uani d . 1 . .
H H19A 0.7571 0.1485 -0.0074 0.054 Uiso calc R 1 . .
H H19B 0.8614 0.1228 0.1227 0.054 Uiso calc R 1 . .
H H19C 0.9401 0.2957 0.1035 0.054 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'
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 P1 O2 . . 117.14(8) ?
O1 P1 O3 . . 114.32(8) ?
O2 P1 O3 . . 94.65(7) ?
O1 P1 N1 . . 111.29(8) ?
O2 P1 N1 . . 107.89(8) ?
O3 P1 N1 . . 110.35(8) ?
C1 O2 P1 . . 126.66(12) ?
C7 O3 P1 . . 116.80(11) ?
C13 N1 P1 . . 127.92(13) ?
C13 N1 H1 . . 115.8 ?
P1 N1 H1 . . 112.7 ?
C6 C1 C2 . . 121.82(18) ?
C6 C1 O2 . . 123.22(16) ?
C2 C1 O2 . . 114.95(16) ?
C3 C2 C1 . . 119.12(18) ?
C3 C2 H2A . . 120.4 ?
C1 C2 H2A . . 120.4 ?
C4 C3 C2 . . 120.23(19) ?
C4 C3 H3A . . 119.9 ?
C2 C3 H3A . . 119.9 ?
C3 C4 C5 . . 119.69(19) ?
C3 C4 H4A . . 120.2 ?
C5 C4 H4A . . 120.2 ?
C6 C5 C4 . . 121.1(2) ?
C6 C5 H5A . . 119.5 ?
C4 C5 H5A . . 119.5 ?
C1 C6 C5 . . 118.05(19) ?
C1 C6 H6A . . 121.0 ?
C5 C6 H6A . . 121.0 ?
C8 C7 C12 . . 122.44(18) ?
C8 C7 O3 . . 118.89(17) ?
C12 C7 O3 . . 118.65(17) ?
C7 C8 C9 . . 118.42(19) ?
C7 C8 H8A . . 120.8 ?
C9 C8 H8A . . 120.8 ?
C10 C9 C8 . . 120.3(2) ?
C10 C9 H9A . . 119.8 ?
C8 C9 H9A . . 119.8 ?
C11 C10 C9 . . 120.22(19) ?
C11 C10 H10A . . 119.9 ?
C9 C10 H10A . . 119.9 ?
C10 C11 C12 . . 120.1(2) ?
C10 C11 H11A . . 119.9 ?
C12 C11 H11A . . 119.9 ?
C7 C12 C11 . . 118.45(19) ?
C7 C12 H12A . . 120.8 ?
C11 C12 H12A . . 120.8 ?
C18 C13 C14 . . 118.81(17) ?
C18 C13 N1 . . 123.00(16) ?
C14 C13 N1 . . 118.18(16) ?
C15 C14 C13 . . 120.21(17) ?
C15 C14 H14A . . 119.9 ?
C13 C14 H14A . . 119.9 ?
C14 C15 C16 . . 121.26(17) ?
C14 C15 H15A . . 119.4 ?
C16 C15 H15A . . 119.4 ?
C17 C16 C15 . . 117.64(18) ?
C17 C16 C19 . . 120.30(19) ?
C15 C16 C19 . . 122.06(18) ?
C18 C17 C16 . . 121.78(19) ?
C18 C17 H17A . . 119.1 ?
C16 C17 H17A . . 119.1 ?
C17 C18 C13 . . 120.29(18) ?
C17 C18 H18A . . 119.9 ?
C13 C18 H18A . . 119.9 ?
C16 C19 H19A . . 109.5 ?
C16 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C16 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 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 O1 . 1.4691(14) ?
P1 O2 . 1.5793(13) ?
P1 O3 . 1.5926(14) ?
P1 N1 . 1.6279(16) ?
O2 C1 . 1.399(2) ?
O3 C7 . 1.414(2) ?
N1 C13 . 1.417(2) ?
N1 H1 . 0.7881 ?
C1 C6 . 1.387(3) ?
C1 C2 . 1.388(3) ?
C2 C3 . 1.387(3) ?
C2 H2A . 0.9500 ?
C3 C4 . 1.390(3) ?
C3 H3A . 0.9500 ?
C4 C5 . 1.386(3) ?
C4 H4A . 0.9500 ?
C5 C6 . 1.393(3) ?
C5 H5A . 0.9500 ?
C6 H6A . 0.9500 ?
C7 C8 . 1.383(3) ?
C7 C12 . 1.377(3) ?
C8 C9 . 1.389(3) ?
C8 H8A . 0.9500 ?
C9 C10 . 1.385(3) ?
C9 H9A . 0.9500 ?
C10 C11 . 1.386(3) ?
C10 H10A . 0.9500 ?
C11 C12 . 1.394(3) ?
C11 H11A . 0.9500 ?
C12 H12A . 0.9500 ?
C13 C18 . 1.388(3) ?
C13 C14 . 1.403(3) ?
C14 C15 . 1.391(3) ?
C14 H14A . 0.9500 ?
C15 C16 . 1.395(3) ?
C15 H15A . 0.9500 ?
C16 C17 . 1.393(3) ?
C16 C19 . 1.509(3) ?
C17 C18 . 1.387(3) ?
C17 H17A . 0.9500 ?
C18 H18A . 0.9500 ?
C19 H19A . 0.9800 ?
C19 H19B . 0.9800 ?
C19 H19C . 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
_geom_hbond_publ_flag
N1 H1 O1 2_666 0.79 2.07 2.840(3) 167 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
O1 P1 O2 C1 . . . . -50.89(16) ?
O3 P1 O2 C1 . . . . -171.29(14) ?
N1 P1 O2 C1 . . . . 75.58(15) ?
O1 P1 O3 C7 . . . . 50.54(15) ?
O2 P1 O3 C7 . . . . 173.16(13) ?
N1 P1 O3 C7 . . . . -75.81(14) ?
O1 P1 N1 C13 . . . . -179.07(15) ?
O2 P1 N1 C13 . . . . 51.11(18) ?
O3 P1 N1 C13 . . . . -51.04(18) ?
P1 O2 C1 C6 . . . . 5.8(3) ?
P1 O2 C1 C2 . . . . -175.33(13) ?
C6 C1 C2 C3 . . . . -0.8(3) ?
O2 C1 C2 C3 . . . . -179.63(17) ?
C1 C2 C3 C4 . . . . 0.6(3) ?
C2 C3 C4 C5 . . . . -0.1(3) ?
C3 C4 C5 C6 . . . . -0.2(3) ?
C2 C1 C6 C5 . . . . 0.4(3) ?
O2 C1 C6 C5 . . . . 179.22(18) ?
C4 C5 C6 C1 . . . . 0.0(3) ?
P1 O3 C7 C8 . . . . -86.63(19) ?
P1 O3 C7 C12 . . . . 94.78(19) ?
C12 C7 C8 C9 . . . . 0.0(3) ?
O3 C7 C8 C9 . . . . -178.54(18) ?
C7 C8 C9 C10 . . . . 0.2(3) ?
C8 C9 C10 C11 . . . . -0.4(3) ?
C9 C10 C11 C12 . . . . 0.5(3) ?
C8 C7 C12 C11 . . . . 0.0(3) ?
O3 C7 C12 C11 . . . . 178.59(17) ?
C10 C11 C12 C7 . . . . -0.3(3) ?
P1 N1 C13 C18 . . . . -0.3(3) ?
P1 N1 C13 C14 . . . . 179.39(14) ?
C18 C13 C14 C15 . . . . 0.1(3) ?
N1 C13 C14 C15 . . . . -179.59(17) ?
C13 C14 C15 C16 . . . . -0.4(3) ?
C14 C15 C16 C17 . . . . 0.1(3) ?
C14 C15 C16 C19 . . . . -179.19(19) ?
C15 C16 C17 C18 . . . . 0.4(3) ?
C19 C16 C17 C18 . . . . 179.8(2) ?
C16 C17 C18 C13 . . . . -0.7(3) ?
C14 C13 C18 C17 . . . . 0.4(3) ?
N1 C13 C18 C17 . . . . -179.86(19) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1555347
2 PubChem 2066074
