#------------------------------------------------------------------------------
#$Date: 2025-08-23 00:12:46 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/93/7239304.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_7239304
loop_
_publ_author_name
'Dobrzyńska, Danuta'
'Kubiak, Joanna'
'Janczak, Jan'
'Zoń, Jerzy'
_publ_section_title
;
 Supramolecular networks formation in crystals of
 3-carboxybenzylphosphonic acid, its complexes and salts: from
 coordination bonds to weak intermolecular interactions
;
_journal_issue                   45
_journal_name_full               'RSC Advances'
_journal_page_first              23119
_journal_paper_doi               10.1039/c3ra44614j
_journal_volume                  3
_journal_year                    2013
_chemical_formula_moiety         'C8 H8 O5 P, 0.5(C10 H10 N2)'
_chemical_formula_sum            'C13 H13 N O5 P'
_chemical_formula_weight         294.21
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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                90.00
_cell_angle_beta                 115.94(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.908(4)
_cell_length_b                   4.7119(9)
_cell_length_c                   17.201(3)
_cell_measurement_reflns_used    1220
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.55
_cell_measurement_theta_min      2.63
_cell_volume                     1305.2(5)
_computing_cell_refinement
;
Oxford Diffraction Poland, CrysAlis Red, Version 171.32.6, 2008
;
_computing_data_collection
;
Oxford Diffraction Poland, CrysAlis CCD, Version 171.32.6, 2008
;
_computing_data_reduction
;
Oxford Diffraction Poland, CrysAlis Red, Version 171.32.6, 2008
;
_computing_molecular_graphics
;
Brandenburg & Putz, DIAMOND Version 3.0, Crystal Impact GbR,
Bonn, Germany, (2006)
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean '1024x1024 with blocks 2x2'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'KUMA KM-4 with area CCD detector'
_diffrn_measurement_method       ω-scan
_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  0.0857
_diffrn_reflns_av_sigmaI/netI    0.1876
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16768
_diffrn_reflns_theta_full        28.55
_diffrn_reflns_theta_max         28.55
_diffrn_reflns_theta_min         2.63
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  0.9333
_exptl_absorpt_correction_T_min  0.8952
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
Oxford Diffraction Poland, CrysAlis Red, Version 171.32.6, 2008
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_meas      1.49
_exptl_crystal_density_method    floatation
_exptl_crystal_description       parellelepiped
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3293
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1461
_refine_ls_R_factor_gt           0.0495
_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)+(0.0120P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0533
_refine_ls_wR_factor_ref         0.0589
_reflns_number_gt                1926
_reflns_number_total             3293
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c3ra44614j.txt
_cod_data_source_block           COMP5
_cod_original_cell_volume        1305.2(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7239304
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_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
_atom_site_refinement_flags
P1 P 0.19985(4) 0.52494(14) 0.35740(4) 0.03667(18) Uani 1 1 d .
O1 O 0.21123(9) 0.7864(3) 0.41170(9) 0.0400(4) Uani 1 1 d .
O2 O 0.14465(8) 0.5749(3) 0.26247(8) 0.0453(5) Uani 1 1 d .
O3 O 0.15991(11) 0.2887(3) 0.39088(11) 0.0505(5) Uani 1 1 d .
H3O H 0.1789(15) 0.121(5) 0.3956(15) 0.076 Uiso 1 1 d .
C1 C 0.29811(12) 0.3853(5) 0.37236(13) 0.0394(6) Uani 1 1 d .
H1A H 0.3317 0.3498 0.4335 0.059 Uiso 1 1 calc R
H1B H 0.2892 0.2049 0.3424 0.059 Uiso 1 1 calc R
C2 C 0.34517(15) 0.5791(5) 0.34000(15) 0.0366(6) Uani 1 1 d .
C3 C 0.32217(13) 0.6078(5) 0.25285(15) 0.0393(7) Uani 1 1 d .
H3 H 0.2766 0.5066 0.2138 0.047 Uiso 1 1 calc R
C4 C 0.36531(15) 0.7847(5) 0.22151(16) 0.0390(6) Uani 1 1 d .
C5 C 0.43310(15) 0.9315(5) 0.28039(17) 0.0505(7) Uani 1 1 d .
H5 H 0.4629 1.0503 0.2610 0.061 Uiso 1 1 calc R
C6 C 0.45684(15) 0.9031(6) 0.36764(18) 0.0615(9) Uani 1 1 d .
H6 H 0.5026 1.0033 0.4068 0.074 Uiso 1 1 calc R
C7 C 0.41361(15) 0.7279(5) 0.39746(15) 0.0487(7) Uani 1 1 d .
H7 H 0.4305 0.7095 0.4566 0.058 Uiso 1 1 calc R
C8 C 0.34184(18) 0.8129(6) 0.12760(18) 0.0530(8) Uani 1 1 d .
O4 O 0.38215(12) 0.9299(5) 0.09785(11) 0.0929(8) Uani 1 1 d .
O5 O 0.26951(12) 0.6941(4) 0.07931(10) 0.0655(6) Uani 1 1 d .
H5O H 0.2582(16) 0.690(6) 0.0259(17) 0.098 Uiso 1 1 d .
N1 N 0.09114(13) -0.0056(4) 0.16223(11) 0.0396(5) Uani 1 1 d .
H1N H 0.1137(12) -0.150(3) 0.1989(10) 0.047 Uiso 1 1 d .
C9 C 0.01775(15) 0.1012(5) 0.14687(15) 0.0512(8) Uani 1 1 d .
H9 H -0.0090 0.0407 0.1797 0.061 Uiso 1 1 calc R
C10 C -0.01959(14) 0.2998(5) 0.08333(14) 0.0453(7) Uani 1 1 d .
H10 H -0.0717 0.3701 0.0727 0.054 Uiso 1 1 calc R
C11 C 0.01981(14) 0.3958(4) 0.03506(12) 0.0312(6) Uani 1 1 d .
C12 C 0.09648(14) 0.2825(5) 0.05375(14) 0.0435(7) Uani 1 1 d .
H12 H 0.1254 0.3415 0.0230 0.052 Uiso 1 1 calc R
C13 C 0.13033(15) 0.0841(5) 0.11724(15) 0.0500(8) Uani 1 1 d .
H13 H 0.1824 0.0099 0.1292 0.060 Uiso 1 1 calc R
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_3
O1 P1 O2 112.94(9) .
O1 P1 O3 108.30(9) .
O2 P1 O3 108.69(10) .
O1 P1 C1 110.74(10) .
O2 P1 C1 110.48(10) .
O3 P1 C1 105.36(10) .
P1 O3 H3O 117.9(17) .
C2 C1 P1 113.47(15) .
C2 C1 H1A 108.9 .
P1 C1 H1A 108.9 .
C2 C1 H1B 108.9 .
P1 C1 H1B 108.9 .
H1A C1 H1B 107.7 .
C3 C2 C7 118.6(2) .
C3 C2 C1 120.9(2) .
C7 C2 C1 120.6(2) .
C2 C3 C4 121.8(2) .
C2 C3 H3 119.1 .
C4 C3 H3 119.1 .
C5 C4 C3 118.3(2) .
C5 C4 C8 119.5(2) .
C3 C4 C8 122.2(2) .
C6 C5 C4 120.3(2) .
C6 C5 H5 119.8 .
C4 C5 H5 119.8 .
C7 C6 C5 120.6(2) .
C7 C6 H6 119.7 .
C5 C6 H6 119.7 .
C6 C7 C2 120.4(2) .
C6 C7 H7 119.8 .
C2 C7 H7 119.8 .
O4 C8 O5 122.7(3) .
O4 C8 C4 125.0(3) .
O5 C8 C4 112.3(2) .
C8 O5 H5O 113.2(19) .
C13 N1 C9 119.8(2) .
C13 N1 H1N 117.7(14) .
C9 N1 H1N 122.2(14) .
N1 C9 C10 121.0(2) .
N1 C9 H9 119.5 .
C10 C9 H9 119.5 .
C9 C10 C11 120.3(2) .
C9 C10 H10 119.9 .
C11 C10 H10 119.9 .
C12 C11 C10 117.0(2) .
C12 C11 C11 121.6(3) 3_565
C10 C11 C11 121.4(3) 3_565
C13 C12 C11 120.2(2) .
C13 C12 H12 119.9 .
C11 C12 H12 119.9 .
N1 C13 C12 121.7(2) .
N1 C13 H13 119.2 .
C12 C13 H13 119.2 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 O1 1.5051(14) .
P1 O2 1.5122(14) .
P1 O3 1.5629(16) .
P1 C1 1.789(2) .
O3 H3O 0.85(2) .
C1 C2 1.505(3) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C2 C3 1.377(3) .
C2 C7 1.382(3) .
C3 C4 1.395(3) .
C3 H3 0.9300 .
C4 C5 1.379(3) .
C4 C8 1.486(3) .
C5 C6 1.376(3) .
C5 H5 0.9300 .
C6 C7 1.375(3) .
C6 H6 0.9300 .
C7 H7 0.9300 .
C8 O4 1.188(3) .
C8 O5 1.319(3) .
O5 H5O 0.85(3) .
N1 C13 1.321(3) .
N1 C9 1.322(3) .
N1 H1N 0.89(2) .
C9 C10 1.370(3) .
C9 H9 0.9300 .
C10 C11 1.380(3) .
C10 H10 0.9300 .
C11 C12 1.374(3) .
C11 C11 1.474(4) 3_565
C12 C13 1.362(3) .
C12 H12 0.9300 .
C13 H13 0.9300 .
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
O3 H3O O1 0.85(2) 1.66(2) 2.507(2) 174(2) 1_545
N1 H1N O2 0.89(2) 1.63(2) 2.520(2) 174(2) 1_545
O5 H5O O1 0.85(3) 1.77(3) 2.603(2) 166(3) 4_575
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168340826
