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#$Date: 2025-08-20 19:06:18 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301834 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/13/4121398.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_4121398
loop_
_publ_author_name
'Andrew R. Jupp'
'Jose M. Goicoechea'
_publ_contact_author
;
 Dr. J. M. Goicoechea           
 Chemistry Research Laboratory
 University of Oxford
 Mansfield Road
 Oxford
 OX1 3TA
 UK
;
_publ_contact_author_email       jose.goicoechea@chem.ox.ac.uk
_publ_contact_author_fax         '+44 1865 272690'
_publ_contact_author_phone       '+44 1865 275961'
_publ_section_title
;
 Phosphinecarboxamide: A Phosphorus-Containing Analogue of Urea and Stable
 Primary Phosphine
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              19131
_journal_page_last               19134
_journal_paper_doi               10.1021/ja4115693
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         '0.5(C12 H24 O6), C H4 N O P'
_chemical_formula_sum            'C7 H16 N O4 P'
_chemical_formula_weight         209.18
_chemical_name_systematic
;
 PH2C(O)NH2*0.5(18-crown-6)
;
_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                105.9590(10)
_cell_angle_beta                 114.847(2)
_cell_angle_gamma                96.5740(10)
_cell_formula_units_Z            2
_cell_length_a                   8.4093(2)
_cell_length_b                   8.6581(3)
_cell_length_c                   8.7267(3)
_cell_measurement_reflns_used    3955
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      5.097
_cell_volume                     534.73(3)
_computing_cell_refinement
;
KappaCCD software "DENZO" (Otwinowski & Minor, 1996)
;
_computing_data_collection
;
KappaCCD software "Collect" (Nonius, 2000)
;
_computing_data_reduction
;
KappaCCD software "DENZO" (Otwinowski & Minor, 1996)
;
_computing_molecular_graphics    'WinGX (Farrugia, 2005)'
_computing_publication_material  'XCIF (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '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  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6640
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         5.10
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_T_max  0.9440
_exptl_absorpt_correction_T_min  0.9395
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       block
_exptl_crystal_F_000             224
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2418
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0321
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0354P)²+0.1120P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0781
_refine_ls_wR_factor_ref         0.0821
_reflns_number_gt                2030
_reflns_number_total             2418
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ja4115693_si_002.cif
_cod_data_source_block           2*0.5(18-crown-6)
_cod_database_code               4121398
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
P1 P 0.72503(5) 0.38605(4) 0.94600(5) 0.02729(12) Uani 1 1 d
H1 H 0.783(2) 0.282(2) 1.018(2) 0.045(5) Uiso 1 1 d
H2 H 0.669(2) 0.455(2) 1.059(2) 0.046(5) Uiso 1 1 d
C1 C 0.49671(16) 0.24905(15) 0.76638(16) 0.0204(3) Uani 1 1 d
O1 O 0.36828(12) 0.31190(11) 0.72163(12) 0.0275(2) Uani 1 1 d
N1 N 0.48541(17) 0.08993(14) 0.68909(16) 0.0269(3) Uani 1 1 d
H3 H 0.579(2) 0.053(2) 0.713(2) 0.039(5) Uiso 1 1 d
H4 H 0.383(2) 0.026(2) 0.594(2) 0.036(4) Uiso 1 1 d
O101 O 0.21007(12) 0.08550(10) 0.24767(12) 0.0243(2) Uani 1 1 d
O102 O 0.13295(12) -0.14434(11) 0.40511(12) 0.0262(2) Uani 1 1 d
O103 O 0.41287(12) -0.28735(11) 0.57272(12) 0.0246(2) Uani 1 1 d
C101 C 0.04778(18) 0.05103(18) 0.2622(2) 0.0281(3) Uani 1 1 d
H5 H 0.064(2) 0.1237(19) 0.380(2) 0.028(4) Uiso 1 1 d
H6 H -0.057(2) 0.065(2) 0.164(2) 0.037(4) Uiso 1 1 d
C102 C 0.00023(18) -0.12635(17) 0.24763(18) 0.0274(3) Uani 1 1 d
H7 H -0.118(2) -0.156(2) 0.236(2) 0.035(4) Uiso 1 1 d
H8 H 0.000(2) -0.204(2) 0.136(2) 0.034(4) Uiso 1 1 d
C103 C 0.09878(18) -0.30920(16) 0.40506(19) 0.0257(3) Uani 1 1 d
H9 H -0.023(2) -0.3423(19) 0.396(2) 0.035(4) Uiso 1 1 d
H10 H 0.099(2) -0.3895(19) 0.300(2) 0.029(4) Uiso 1 1 d
C104 C 0.24471(18) -0.31427(17) 0.57629(19) 0.0268(3) Uani 1 1 d
H11 H 0.2507(19) -0.2298(19) 0.681(2) 0.026(4) Uiso 1 1 d
H12 H 0.211(2) -0.424(2) 0.582(2) 0.038(4) Uiso 1 1 d
C105 C 0.55757(19) -0.29177(18) 0.73093(19) 0.0297(3) Uani 1 1 d
H13 H 0.568(2) -0.2078(19) 0.840(2) 0.030(4) Uiso 1 1 d
H14 H 0.533(2) -0.398(2) 0.738(2) 0.039(4) Uiso 1 1 d
C106 C 0.73048(19) -0.25828(16) 0.71977(19) 0.0281(3) Uani 1 1 d
H15 H 0.825(2) -0.289(2) 0.809(2) 0.041(4) Uiso 1 1 d
H16 H 0.714(2) -0.3240(19) 0.601(2) 0.029(4) Uiso 1 1 d
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 P1 H1 98.4(8) . .
C1 P1 H2 95.1(8) . .
H1 P1 H2 95.6(10) . .
O1 C1 N1 124.12(12) . .
O1 C1 P1 118.50(9) . .
N1 C1 P1 117.32(9) . .
C1 N1 H3 122.0(12) . .
C1 N1 H4 118.9(10) . .
H3 N1 H4 117.6(16) . .
C101 O101 C106 111.07(10) . 2_656
C103 O102 C102 112.75(10) . .
C105 O103 C104 111.79(10) . .
O101 C101 C102 109.83(10) . .
O101 C101 H5 110.9(9) . .
C102 C101 H5 108.2(9) . .
O101 C101 H6 112.0(10) . .
C102 C101 H6 106.5(10) . .
H5 C101 H6 109.3(12) . .
O102 C102 C101 108.39(11) . .
O102 C102 H7 110.6(10) . .
C101 C102 H7 110.6(10) . .
O102 C102 H8 109.6(9) . .
C101 C102 H8 110.0(9) . .
H7 C102 H8 107.7(13) . .
O102 C103 C104 108.45(10) . .
O102 C103 H9 110.1(9) . .
C104 C103 H9 110.5(9) . .
O102 C103 H10 110.6(9) . .
C104 C103 H10 109.6(8) . .
H9 C103 H10 107.6(12) . .
O103 C104 C103 108.75(11) . .
O103 C104 H11 111.1(9) . .
C103 C104 H11 109.9(8) . .
O103 C104 H12 111.2(9) . .
C103 C104 H12 107.7(10) . .
H11 C104 H12 108.2(13) . .
O103 C105 C106 108.78(11) . .
O103 C105 H13 110.2(9) . .
C106 C105 H13 110.3(9) . .
O103 C105 H14 108.8(10) . .
C106 C105 H14 110.2(10) . .
H13 C105 H14 108.5(13) . .
O101 C106 C105 109.96(11) 2_656 .
O101 C106 H15 109.3(10) 2_656 .
C105 C106 H15 110.3(10) . .
O101 C106 H16 108.9(9) 2_656 .
C105 C106 H16 111.0(9) . .
H15 C106 H16 107.2(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 C1 1.8647(13) .
P1 H1 1.266(17) .
P1 H2 1.295(16) .
C1 O1 1.2297(15) .
C1 N1 1.3293(16) .
N1 H3 0.848(18) .
N1 H4 0.878(18) .
O101 C101 1.4283(16) .
O101 C106 1.4298(15) 2_656
O102 C103 1.4233(15) .
O102 C102 1.4237(16) .
O103 C105 1.4200(16) .
O103 C104 1.4215(15) .
C101 C102 1.498(2) .
C101 H5 0.989(15) .
C101 H6 0.982(17) .
C102 H7 0.952(17) .
C102 H8 1.017(16) .
C103 C104 1.4993(19) .
C103 H9 0.995(16) .
C103 H10 0.991(15) .
C104 H11 0.976(15) .
C104 H12 0.978(18) .
C105 C106 1.499(2) .
C105 H13 0.986(15) .
C105 H14 0.946(18) .
C106 O101 1.4298(15) 2_656
C106 H15 0.975(18) .
C106 H16 0.978(15) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H4 O102 0.878(18) 2.089(19) 2.9541(15) 167.9(15) .
N1 H3 O101 0.848(18) 2.215(18) 3.0550(15) 170.4(16) 2_656
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139122938
