#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/88/2228803.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_2228803
loop_
_publ_author_name
'Pourayoubi, Mehrdad'
'Zargaran, Poorya'
'Rheingold, Arnold L.'
'Golen, James A.'
_publ_section_title
;
 Diphenyl (2-chlorobenzylamido)phosphate
;
_journal_coeditor_code           LH5173
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5
_journal_paper_doi               10.1107/S160053681004955X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C19 H17 Cl N O3 P'
_chemical_formula_moiety         'C19 H17 Cl N O3 P'
_chemical_formula_sum            'C19 H17 Cl N O3 P'
_chemical_formula_weight         373.76
_chemical_name_systematic
;
Diphenyl (2-chlorobenzylamido)phosphate
;
_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                107.6090(10)
_cell_angle_beta                 93.8820(10)
_cell_angle_gamma                110.0360(10)
_cell_formula_units_Z            2
_cell_length_a                   8.6178(5)
_cell_length_b                   9.5901(6)
_cell_length_c                   12.1543(7)
_cell_measurement_reflns_used    9988
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.97
_cell_measurement_theta_min      2.41
_cell_volume                     882.86(9)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_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      100(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_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  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13560
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.97
_diffrn_reflns_theta_min         2.41
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.325
_exptl_absorpt_correction_T_max  0.9232
_exptl_absorpt_correction_T_min  0.8810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.438
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3982
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0329
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0396P)²+0.4993P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0855
_reflns_number_gt                3681
_reflns_number_total             3982
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5173.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     ' -P 1 '
_cod_database_code               2228803
_cod_database_fobs_code          2228803
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
Cl Cl1 1.12274(4) 0.65811(4) 0.77058(3) 0.02847(10) Uani d . 1 . .
P P1 0.49017(4) 0.15695(4) 0.67814(3) 0.01573(9) Uani d . 1 . .
O O1 0.35884(12) 0.01133(11) 0.59500(8) 0.0201(2) Uani d . 1 . .
O O2 0.44078(12) 0.30686(11) 0.72227(8) 0.01837(19) Uani d . 1 . .
O O3 0.53917(12) 0.14595(11) 0.80359(8) 0.0184(2) Uani d . 1 . .
N N1 0.65627(15) 0.21809(13) 0.62570(10) 0.0194(2) Uani d . 1 . .
C C1 0.97088(17) 0.61883(16) 0.65109(11) 0.0190(3) Uani d . 1 . .
C C2 1.00000(19) 0.72582(16) 0.59229(13) 0.0244(3) Uani d . 1 . .
H H2A 1.1015 0.8170 0.6159 0.029 Uiso calc R 1 . .
C C3 0.8788(2) 0.69789(18) 0.49836(13) 0.0276(3) Uani d . 1 . .
H H3A 0.8965 0.7708 0.4577 0.033 Uiso calc R 1 . .
C C4 0.7317(2) 0.56346(18) 0.46398(13) 0.0262(3) Uani d . 1 . .
H H4A 0.6485 0.5443 0.3999 0.031 Uiso calc R 1 . .
C C5 0.70658(17) 0.45701(16) 0.52345(12) 0.0207(3) Uani d . 1 . .
H H5A 0.6058 0.3650 0.4989 0.025 Uiso calc R 1 . .
C C6 0.82539(16) 0.48181(15) 0.61804(11) 0.0167(2) Uani d . 1 . .
C C7 0.80201(17) 0.36547(15) 0.68278(11) 0.0188(3) Uani d . 1 . .
H H7A 0.9043 0.3410 0.6882 0.023 Uiso calc R 1 . .
H H7B 0.7890 0.4157 0.7639 0.023 Uiso calc R 1 . .
C C8 0.32185(16) 0.31673(15) 0.79467(11) 0.0170(3) Uani d . 1 . .
C C9 0.35893(18) 0.46128(16) 0.88220(12) 0.0206(3) Uani d . 1 . .
H H9A 0.4608 0.5481 0.8920 0.025 Uiso calc R 1 . .
C C10 0.24451(19) 0.47717(17) 0.95549(12) 0.0232(3) Uani d . 1 . .
H H10A 0.2686 0.5755 1.0163 0.028 Uiso calc R 1 . .
C C11 0.09537(19) 0.35066(17) 0.94059(13) 0.0235(3) Uani d . 1 . .
H H11A 0.0181 0.3619 0.9915 0.028 Uiso calc R 1 . .
C C12 0.05959(18) 0.20772(17) 0.85097(13) 0.0241(3) Uani d . 1 . .
H H12A -0.0430 0.1213 0.8402 0.029 Uiso calc R 1 . .
C C13 0.17259(18) 0.18976(16) 0.77676(12) 0.0215(3) Uani d . 1 . .
H H13A 0.1478 0.0921 0.7149 0.026 Uiso calc R 1 . .
C C14 0.60296(16) 0.03684(15) 0.82152(12) 0.0177(3) Uani d . 1 . .
C C15 0.60994(18) -0.08832(16) 0.73025(13) 0.0233(3) Uani d . 1 . .
H H15A 0.5699 -0.1047 0.6508 0.028 Uiso calc R 1 . .
C C16 0.67701(19) -0.18925(17) 0.75786(14) 0.0277(3) Uani d . 1 . .
H H16A 0.6826 -0.2756 0.6965 0.033 Uiso calc R 1 . .
C C17 0.7356(2) -0.16551(18) 0.87353(15) 0.0287(3) Uani d . 1 . .
H H17A 0.7817 -0.2348 0.8913 0.034 Uiso calc R 1 . .
C C18 0.7269(2) -0.03992(19) 0.96360(14) 0.0278(3) Uani d . 1 . .
H H18A 0.7667 -0.0235 1.0431 0.033 Uiso calc R 1 . .
C C19 0.65988(18) 0.06176(16) 0.93767(12) 0.0214(3) Uani d . 1 . .
H H19A 0.6533 0.1475 0.9991 0.026 Uiso calc R 1 . .
H H1N 0.661(2) 0.160(2) 0.5644(18) 0.031(5) Uiso d . 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 P1 O2 . . 116.37(6) ?
O1 P1 O3 . . 113.92(5) ?
O2 P1 O3 . . 98.03(5) ?
O1 P1 N1 . . 113.05(6) ?
O2 P1 N1 . . 104.00(6) ?
O3 P1 N1 . . 110.13(6) ?
C8 O2 P1 . . 123.42(8) ?
C14 O3 P1 . . 124.66(8) ?
C7 N1 P1 . . 125.99(9) ?
C7 N1 H1N . . 117.4(14) ?
P1 N1 H1N . . 116.5(14) ?
C2 C1 C6 . . 122.43(13) ?
C2 C1 Cl1 . . 118.35(11) ?
C6 C1 Cl1 . . 119.22(10) ?
C1 C2 C3 . . 119.07(13) ?
C1 C2 H2A . . 120.5 ?
C3 C2 H2A . . 120.5 ?
C4 C3 C2 . . 119.95(13) ?
C4 C3 H3A . . 120.0 ?
C2 C3 H3A . . 120.0 ?
C3 C4 C5 . . 119.83(14) ?
C3 C4 H4A . . 120.1 ?
C5 C4 H4A . . 120.1 ?
C4 C5 C6 . . 121.60(13) ?
C4 C5 H5A . . 119.2 ?
C6 C5 H5A . . 119.2 ?
C5 C6 C1 . . 117.10(12) ?
C5 C6 C7 . . 122.47(12) ?
C1 C6 C7 . . 120.42(12) ?
N1 C7 C6 . . 113.03(11) ?
N1 C7 H7A . . 109.0 ?
C6 C7 H7A . . 109.0 ?
N1 C7 H7B . . 109.0 ?
C6 C7 H7B . . 109.0 ?
H7A C7 H7B . . 107.8 ?
C9 C8 C13 . . 121.71(13) ?
C9 C8 O2 . . 116.66(12) ?
C13 C8 O2 . . 121.59(12) ?
C8 C9 C10 . . 118.77(13) ?
C8 C9 H9A . . 120.6 ?
C10 C9 H9A . . 120.6 ?
C11 C10 C9 . . 120.55(13) ?
C11 C10 H10A . . 119.7 ?
C9 C10 H10A . . 119.7 ?
C12 C11 C10 . . 119.65(13) ?
C12 C11 H11A . . 120.2 ?
C10 C11 H11A . . 120.2 ?
C11 C12 C13 . . 120.56(14) ?
C11 C12 H12A . . 119.7 ?
C13 C12 H12A . . 119.7 ?
C8 C13 C12 . . 118.73(13) ?
C8 C13 H13A . . 120.6 ?
C12 C13 H13A . . 120.6 ?
C19 C14 C15 . . 121.49(12) ?
C19 C14 O3 . . 115.36(11) ?
C15 C14 O3 . . 123.15(12) ?
C14 C15 C16 . . 118.46(13) ?
C14 C15 H15A . . 120.8 ?
C16 C15 H15A . . 120.8 ?
C17 C16 C15 . . 120.86(14) ?
C17 C16 H16A . . 119.6 ?
C15 C16 H16A . . 119.6 ?
C16 C17 C18 . . 119.76(13) ?
C16 C17 H17A . . 120.1 ?
C18 C17 H17A . . 120.1 ?
C19 C18 C17 . . 120.15(14) ?
C19 C18 H18A . . 119.9 ?
C17 C18 H18A . . 119.9 ?
C14 C19 C18 . . 119.28(13) ?
C14 C19 H19A . . 120.4 ?
C18 C19 H19A . . 120.4 ?
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 C1 . 1.7429(14) ?
P1 O1 . 1.4699(10) ?
P1 O2 . 1.5872(9) ?
P1 O3 . 1.5984(9) ?
P1 N1 . 1.6042(12) ?
O2 C8 . 1.4043(15) ?
O3 C14 . 1.4002(15) ?
N1 C7 . 1.4591(17) ?
N1 H1N . 0.80(2) ?
C1 C2 . 1.3850(19) ?
C1 C6 . 1.3942(18) ?
C2 C3 . 1.389(2) ?
C2 H2A . 0.9500 ?
C3 C4 . 1.388(2) ?
C3 H3A . 0.9500 ?
C4 C5 . 1.388(2) ?
C4 H4A . 0.9500 ?
C5 C6 . 1.3910(18) ?
C5 H5A . 0.9500 ?
C6 C7 . 1.5175(17) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C8 C9 . 1.3834(18) ?
C8 C13 . 1.3831(19) ?
C9 C10 . 1.389(2) ?
C9 H9A . 0.9500 ?
C10 C11 . 1.387(2) ?
C10 H10A . 0.9500 ?
C11 C12 . 1.386(2) ?
C11 H11A . 0.9500 ?
C12 C13 . 1.390(2) ?
C12 H12A . 0.9500 ?
C13 H13A . 0.9500 ?
C14 C19 . 1.3829(19) ?
C14 C15 . 1.3884(19) ?
C15 C16 . 1.392(2) ?
C15 H15A . 0.9500 ?
C16 C17 . 1.384(2) ?
C16 H16A . 0.9500 ?
C17 C18 . 1.389(2) ?
C17 H17A . 0.9500 ?
C18 C19 . 1.389(2) ?
C18 H18A . 0.9500 ?
C19 H19A . 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 H1N O1 2_656 0.80(2) 2.08(2) 2.8703(15) 172.2(19)
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 C8 . . . . 67.62(11) ?
O3 P1 O2 C8 . . . . -54.18(10) ?
N1 P1 O2 C8 . . . . -167.34(10) ?
O1 P1 O3 C14 . . . . 59.85(11) ?
O2 P1 O3 C14 . . . . -176.56(10) ?
N1 P1 O3 C14 . . . . -68.38(11) ?
O1 P1 N1 C7 . . . . 174.57(10) ?
O2 P1 N1 C7 . . . . 47.45(12) ?
O3 P1 N1 C7 . . . . -56.72(12) ?
C6 C1 C2 C3 . . . . 1.3(2) ?
Cl1 C1 C2 C3 . . . . -178.73(11) ?
C1 C2 C3 C4 . . . . -0.6(2) ?
C2 C3 C4 C5 . . . . -0.2(2) ?
C3 C4 C5 C6 . . . . 0.4(2) ?
C4 C5 C6 C1 . . . . 0.29(19) ?
C4 C5 C6 C7 . . . . -178.79(12) ?
C2 C1 C6 C5 . . . . -1.16(19) ?
Cl1 C1 C6 C5 . . . . 178.91(10) ?
C2 C1 C6 C7 . . . . 177.94(12) ?
Cl1 C1 C6 C7 . . . . -1.99(17) ?
P1 N1 C7 C6 . . . . -113.96(12) ?
C5 C6 C7 N1 . . . . 8.01(18) ?
C1 C6 C7 N1 . . . . -171.04(11) ?
P1 O2 C8 C9 . . . . 140.36(10) ?
P1 O2 C8 C13 . . . . -41.74(16) ?
C13 C8 C9 C10 . . . . 1.6(2) ?
O2 C8 C9 C10 . . . . 179.53(11) ?
C8 C9 C10 C11 . . . . -0.4(2) ?
C9 C10 C11 C12 . . . . -0.7(2) ?
C10 C11 C12 C13 . . . . 0.6(2) ?
C9 C8 C13 C12 . . . . -1.7(2) ?
O2 C8 C13 C12 . . . . -179.47(12) ?
C11 C12 C13 C8 . . . . 0.5(2) ?
P1 O3 C14 C19 . . . . 171.04(10) ?
P1 O3 C14 C15 . . . . -8.87(18) ?
C19 C14 C15 C16 . . . . -0.4(2) ?
O3 C14 C15 C16 . . . . 179.53(13) ?
C14 C15 C16 C17 . . . . -0.1(2) ?
C15 C16 C17 C18 . . . . 0.4(2) ?
C16 C17 C18 C19 . . . . -0.2(2) ?
C15 C14 C19 C18 . . . . 0.5(2) ?
O3 C14 C19 C18 . . . . -179.36(12) ?
C17 C18 C19 C14 . . . . -0.3(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656427
