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#$Date: 2025-08-23 00:12:46 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/93/7239305.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_7239305
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           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 96.14(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.995(5)
_cell_length_b                   11.763(2)
_cell_length_c                   9.2980(19)
_cell_measurement_reflns_used    1282
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.04
_cell_measurement_theta_min      2.87
_cell_volume                     2500.6(9)
_computing_cell_refinement
;
CrysAlis Red, Version 171.32.6, Oxford Diffraction Poland, 2008
;
_computing_data_collection
;
CrysAlis CCD, Version 171.32.6, Oxford Diffraction Poland, 2008
;
_computing_data_reduction
;
CrysAlis Red, Version 171.32.6, Oxford Diffraction Poland, 2008
;
_computing_molecular_graphics
;
Brandenburg & Putz (2006). Diamond 3.0. Crystal and Molecular
Structure Visualisation, University of Bonn, Germany
;
_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 0.962
_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  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0166
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16883
_diffrn_reflns_theta_full        28.35
_diffrn_reflns_theta_max         29.04
_diffrn_reflns_theta_min         2.87
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  0.9558
_exptl_absorpt_correction_T_min  0.9208
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
CrysAlis Red, Version 171.32.6, Oxford Diffraction Poland, 2008
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_density_meas      1.56
_exptl_crystal_density_method    floatation
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0030(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3221
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0318
_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)+(0.0488P)²+1.8994P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0913
_reflns_number_gt                2597
_reflns_number_total             3221
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c3ra44614j.txt
_cod_data_source_block           COMP6
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7239305
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
C1 C 0.23576(6) 0.03715(12) 0.80415(14) 0.0276(3) Uani 1 1 d .
C2 C 0.26456(6) -0.05024(11) 0.88450(14) 0.0250(3) Uani 1 1 d .
H2 H 0.2523 -0.1251 0.8694 0.030 Uiso 1 1 calc R
C3 C 0.31136(6) -0.02603(11) 0.98675(14) 0.0251(3) Uani 1 1 d .
C4 C 0.32989(7) 0.08592(12) 1.00938(17) 0.0343(3) Uani 1 1 d .
H4 H 0.3614 0.1021 1.0777 0.041 Uiso 1 1 calc R
C5 C 0.30168(7) 0.17237(13) 0.9308(2) 0.0438(4) Uani 1 1 d .
H5 H 0.3141 0.2471 0.9455 0.053 Uiso 1 1 calc R
C6 C 0.25499(7) 0.14806(13) 0.83020(18) 0.0383(4) Uani 1 1 d .
H6 H 0.2358 0.2072 0.7784 0.046 Uiso 1 1 calc R
C7 C 0.18638(6) 0.01451(14) 0.68813(15) 0.0331(3) Uani 1 1 d .
H7A H 0.1979 -0.0484 0.6299 0.050 Uiso 1 1 calc R
H7B H 0.1823 0.0808 0.6258 0.050 Uiso 1 1 calc R
P1 P 0.115027(15) -0.01815(3) 0.74237(3) 0.02305(11) Uani 1 1 d .
O1 O 0.11245(5) -0.13389(8) 0.80689(12) 0.0371(3) Uani 1 1 d .
O2 O 0.07283(4) 0.00156(8) 0.60755(10) 0.0275(2) Uani 1 1 d .
O3 O 0.10308(5) 0.07667(8) 0.85622(11) 0.0310(2) Uani 1 1 d .
H3O H 0.0933(8) 0.0500(17) 0.932(2) 0.046 Uiso 1 1 d .
C8 C 0.34413(6) -0.11616(11) 1.07354(14) 0.0266(3) Uani 1 1 d .
O4 O 0.38460(5) -0.09384(9) 1.16354(12) 0.0393(3) Uani 1 1 d .
O5 O 0.32681(5) -0.22091(9) 1.04161(12) 0.0365(3) Uani 1 1 d .
H5O H 0.3480(9) -0.2695(18) 1.098(2) 0.055 Uiso 1 1 d .
C9 C 0.00671(5) 0.43861(10) 0.51419(14) 0.0217(3) Uani 1 1 d .
C10 C 0.04862(6) 0.40534(11) 0.62591(15) 0.0282(3) Uani 1 1 d .
H10 H 0.0681 0.4597 0.6858 0.034 Uiso 1 1 calc R
C11 C 0.06105(6) 0.29189(12) 0.64712(15) 0.0315(3) Uani 1 1 d .
H11 H 0.0890 0.2701 0.7217 0.038 Uiso 1 1 calc R
N1 N 0.03369(5) 0.21246(9) 0.56279(13) 0.0295(3) Uani 1 1 d .
H1N H 0.0450(7) 0.1380(15) 0.5801(18) 0.035 Uiso 1 1 d .
C12 C -0.00687(6) 0.24054(12) 0.45564(17) 0.0330(3) Uani 1 1 d .
H12 H -0.0254 0.1840 0.3977 0.040 Uiso 1 1 calc R
C13 C -0.02160(6) 0.35313(11) 0.42994(15) 0.0300(3) Uani 1 1 d .
H13 H -0.0505 0.3719 0.3561 0.036 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
C6 C1 C2 118.29(13) .
C6 C1 C7 119.52(13) .
C2 C1 C7 122.16(13) .
C3 C2 C1 120.31(12) .
C3 C2 H2 119.8 .
C1 C2 H2 119.8 .
C2 C3 C4 119.99(12) .
C2 C3 C8 122.44(12) .
C4 C3 C8 117.56(12) .
C5 C4 C3 119.99(14) .
C5 C4 H4 120.0 .
C3 C4 H4 120.0 .
C4 C5 C6 119.82(14) .
C4 C5 H5 120.1 .
C6 C5 H5 120.1 .
C5 C6 C1 121.59(13) .
C5 C6 H6 119.2 .
C1 C6 H6 119.2 .
C1 C7 P1 118.39(10) .
C1 C7 H7A 107.7 .
P1 C7 H7A 107.7 .
C1 C7 H7B 107.7 .
P1 C7 H7B 107.7 .
H7A C7 H7B 107.1 .
O1 P1 O2 114.96(6) .
O1 P1 O3 110.93(6) .
O2 P1 O3 107.66(6) .
O1 P1 C7 112.48(7) .
O2 P1 C7 104.83(6) .
O3 P1 C7 105.33(7) .
P1 O3 H3O 112.8(14) .
O4 C8 O5 123.29(12) .
O4 C8 C3 121.82(13) .
O5 C8 C3 114.86(11) .
C8 O5 H5O 109.7(13) .
C13 C9 C10 117.41(11) .
C13 C9 C9 121.55(14) 5_566
C10 C9 C9 121.04(14) 5_566
C11 C10 C9 119.71(12) .
C11 C10 H10 120.1 .
C9 C10 H10 120.1 .
N1 C11 C10 121.21(12) .
N1 C11 H11 119.4 .
C10 C11 H11 119.4 .
C12 N1 C11 120.98(12) .
C12 N1 H1N 121.9(11) .
C11 N1 H1N 117.1(11) .
N1 C12 C13 120.43(13) .
N1 C12 H12 119.8 .
C13 C12 H12 119.8 .
C12 C13 C9 120.25(12) .
C12 C13 H13 119.9 .
C9 C13 H13 119.9 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.391(2) .
C1 C2 1.3956(18) .
C1 C7 1.5039(19) .
C2 C3 1.3872(18) .
C2 H2 0.9300 .
C3 C4 1.3931(19) .
C3 C8 1.4876(18) .
C4 C5 1.374(2) .
C4 H4 0.9300 .
C5 C6 1.376(2) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 P1 1.8087(15) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
P1 O1 1.4915(10) .
P1 O2 1.5186(10) .
P1 O3 1.5819(10) .
O3 H3O 0.83(2) .
C8 O4 1.2118(16) .
C8 O5 1.3191(17) .
O5 H5O 0.88(2) .
C9 C13 1.3925(18) .
C9 C10 1.3953(18) .
C9 C9 1.494(2) 5_566
C10 C11 1.3746(18) .
C10 H10 0.9300 .
C11 N1 1.3335(18) .
C11 H11 0.9300 .
N1 C12 1.3314(19) .
N1 H1N 0.923(18) .
C12 C13 1.3815(19) .
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
N1 H1N O2 0.923(18) 1.736(18) 2.6566(15) 174.5(16) .
O3 H3O O2 0.83(2) 1.85(2) 2.6720(15) 177(2) 6_556
O5 H5O O1 0.88(2) 1.65(2) 2.5360(15) 176(2) 7_547
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168340826
