#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/93/4509326.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_4509326
loop_
_publ_author_name
'Chen, Shuo-ping'
'Pan, Ling-ling'
'Yuan, Yi-xuan'
'Shi, Xi-xi'
'Yuan, Liang-jie'
_publ_section_title
;
 A Novel Supramolecular Resin Based On an Organic Acid−Base
 Compound
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2668
_journal_paper_doi               10.1021/cg801233x
_journal_volume                  9
_journal_year                    2009
_chemical_formula_sum            'C4 H23 N3 O9 P2'
_chemical_formula_weight         319.19
_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                97.626(4)
_cell_angle_beta                 99.857(5)
_cell_angle_gamma                101.154(4)
_cell_formula_units_Z            2
_cell_length_a                   5.6469(16)
_cell_length_b                   9.008(3)
_cell_length_c                   13.229(4)
_cell_measurement_temperature    273(2)
_cell_volume                     640.8(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  '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  0.0158
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3615
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    0.384
_exptl_absorpt_correction_T_max  0.9033
_exptl_absorpt_correction_T_min  0.8281
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.654
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.066(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2443
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.163
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0284
_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)+(0.0435P)²+0.2629P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0847
_reflns_number_gt                2361
_reflns_number_total             2443
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg801233xsup2.cif
_cod_data_source_block           80410csp_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4509326
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
_atom_site_refinement_flags
C1 C 0.3543(3) 0.45225(16) 0.28987(11) 0.0142(3) Uani 1 1 d .
C2 C 0.2494(3) 0.45447(19) 0.17589(12) 0.0216(3) Uani 1 1 d .
H2A H 0.1287 0.3611 0.1470 0.032 Uiso 1 1 calc R
H2B H 0.3800 0.4631 0.1377 0.032 Uiso 1 1 calc R
H2C H 0.1734 0.5406 0.1714 0.032 Uiso 1 1 calc R
C3 C 0.1061(3) 0.96042(19) 0.49874(13) 0.0220(3) Uani 1 1 d .
H3D H 0.2572 1.0285 0.5387 0.026 Uiso 1 1 calc R
H3E H 0.0767 0.8689 0.5301 0.026 Uiso 1 1 calc R
C4 C 0.1243(3) 0.9805(2) 0.00874(14) 0.0282(4) Uani 1 1 d .
H4A H 0.1352 0.9074 -0.0502 0.034 Uiso 1 1 calc R
H4B H 0.2514 1.0725 0.0147 0.034 Uiso 1 1 calc R
H6 H 0.536(6) 0.307(4) 0.452(2) 0.064(10) Uiso 1 1 d .
H1W1 H 0.695(5) 1.0352(11) 0.2184(19) 0.060(8) Uiso 1 1 d D
H2W1 H 0.612(4) 0.895(2) 0.2398(16) 0.051(7) Uiso 1 1 d D
H1W2 H 0.784(4) 0.643(3) 0.1529(9) 0.039(6) Uiso 1 1 d D
H2W2 H 0.666(4) 0.668(4) 0.0619(19) 0.094(12) Uiso 1 1 d D
H1W3 H 0.721(7) 0.4086(17) 0.031(2) 0.106(14) Uiso 1 1 d D
H2W3 H 0.645(5) 0.299(3) 0.0863(11) 0.055(8) Uiso 1 1 d D
N1 N 0.1406(2) 0.44337(14) 0.34633(10) 0.0175(3) Uani 1 1 d .
H1A H 0.0755 0.5251 0.3405 0.026 Uiso 1 1 calc R
H1B H 0.1946 0.4415 0.4133 0.026 Uiso 1 1 calc R
H1C H 0.0263 0.3584 0.3182 0.026 Uiso 1 1 calc R
N2 N 0.1329(2) 0.91772(15) 0.38992(11) 0.0213(3) Uani 1 1 d .
H2D H -0.0016 0.8499 0.3545 0.032 Uiso 1 1 calc R
H2E H 0.2638 0.8764 0.3895 0.032 Uiso 1 1 calc R
H2F H 0.1527 1.0012 0.3603 0.032 Uiso 1 1 calc R
N3 N 0.1636(3) 0.91395(17) 0.10476(11) 0.0260(3) Uani 1 1 d .
H3A H 0.1610 0.9829 0.1591 0.039 Uiso 1 1 calc R
H3B H 0.3090 0.8879 0.1133 0.039 Uiso 1 1 calc R
H3C H 0.0446 0.8309 0.0997 0.039 Uiso 1 1 calc R
O1 O 0.6491(2) 0.63603(14) 0.46436(9) 0.0250(3) Uani 1 1 d .
O2 O 0.4554(2) 0.76128(12) 0.32298(9) 0.0225(3) Uani 1 1 d .
O3 O 0.8040(2) 0.63241(13) 0.29661(9) 0.0202(3) Uani 1 1 d .
O4 O 0.6445(2) 0.25851(13) 0.22688(9) 0.0254(3) Uani 1 1 d .
O5 O 0.2353(2) 0.14905(13) 0.27576(10) 0.0261(3) Uani 1 1 d .
O6 O 0.6119(3) 0.28901(15) 0.41193(10) 0.0285(3) Uani 1 1 d .
O1W O 0.6833(3) 0.94076(15) 0.19754(11) 0.0343(3) Uani 1 1 d D
O2W O 0.7968(2) 0.64484(15) 0.09012(10) 0.0285(3) Uani 1 1 d D
O3W O 0.6496(3) 0.31690(16) 0.02598(10) 0.0331(3) Uani 1 1 d D
P1 P 0.58302(7) 0.63345(4) 0.34771(3) 0.01480(15) Uani 1 1 d .
P2 P 0.46735(7) 0.27381(4) 0.29820(3) 0.01657(15) Uani 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
N1 C1 C2 106.80(12) . .
N1 C1 P2 107.03(9) . .
C2 C1 P2 108.78(10) . .
N1 C1 P1 108.17(9) . .
C2 C1 P1 110.03(10) . .
P2 C1 P1 115.65(8) . .
C1 C2 H2A 109.5 . .
C1 C2 H2B 109.5 . .
H2A C2 H2B 109.5 . .
C1 C2 H2C 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
N2 C3 C3 110.17(17) . 2_576
N2 C3 H3D 109.6 . .
C3 C3 H3D 109.6 2_576 .
N2 C3 H3E 109.6 . .
C3 C3 H3E 109.6 2_576 .
H3D C3 H3E 108.1 . .
N3 C4 C4 110.03(18) . 2_575
N3 C4 H4A 109.7 . .
C4 C4 H4A 109.7 2_575 .
N3 C4 H4B 109.7 . .
C4 C4 H4B 109.7 2_575 .
H4A C4 H4B 108.2 . .
C1 N1 H1A 109.5 . .
C1 N1 H1B 109.5 . .
H1A N1 H1B 109.5 . .
C1 N1 H1C 109.5 . .
H1A N1 H1C 109.5 . .
H1B N1 H1C 109.5 . .
C3 N2 H2D 109.5 . .
C3 N2 H2E 109.5 . .
H2D N2 H2E 109.5 . .
C3 N2 H2F 109.5 . .
H2D N2 H2F 109.5 . .
H2E N2 H2F 109.5 . .
C4 N3 H3A 109.5 . .
C4 N3 H3B 109.5 . .
H3A N3 H3B 109.5 . .
C4 N3 H3C 109.5 . .
H3A N3 H3C 109.5 . .
H3B N3 H3C 109.5 . .
P2 O6 H6 112(2) . .
H1W1 O1W H2W1 104.9(14) . .
H1W2 O2W H2W2 105.0(15) . .
H1W3 O3W H2W3 107.7(16) . .
O2 P1 O3 112.48(6) . .
O2 P1 O1 111.68(7) . .
O3 P1 O1 112.01(7) . .
O2 P1 C1 105.70(7) . .
O3 P1 C1 106.96(7) . .
O1 P1 C1 107.57(7) . .
O4 P2 O5 116.21(7) . .
O4 P2 O6 107.61(8) . .
O5 P2 O6 111.17(8) . .
O4 P2 C1 110.43(7) . .
O5 P2 C1 104.08(7) . .
O6 P2 C1 106.99(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.5193(18) .
C1 C2 1.527(2) .
C1 P2 1.8502(15) .
C1 P1 1.8526(15) .
C2 H2A 0.9600 .
C2 H2B 0.9600 .
C2 H2C 0.9600 .
C3 N2 1.481(2) .
C3 C3 1.512(3) 2_576
C3 H3D 0.9700 .
C3 H3E 0.9700 .
C4 N3 1.476(2) .
C4 C4 1.499(4) 2_575
C4 H4A 0.9700 .
C4 H4B 0.9700 .
N1 H1A 0.8900 .
N1 H1B 0.8900 .
N1 H1C 0.8900 .
N2 H2D 0.8900 .
N2 H2E 0.8900 .
N2 H2F 0.8900 .
N3 H3A 0.8900 .
N3 H3B 0.8900 .
N3 H3C 0.8900 .
O1 P1 1.5202(12) .
O2 P1 1.5141(12) .
O3 P1 1.5186(12) .
O4 P2 1.5006(12) .
O5 P2 1.5088(12) .
O6 P2 1.5589(13) .
O6 H6 0.75(3) .
O1W H1W1 0.845(10) .
O1W H2W1 0.848(9) .
O2W H1W2 0.847(9) .
O2W H2W2 0.844(10) .
O3W H1W3 0.834(10) .
O3W H2W3 0.839(10) .
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
N3 H3C O2W 0.89 1.94 2.828(2) 177.4 1_455
N3 H3B O3W 0.89 2.50 2.991(2) 115.1 2_665
N3 H3B O1W 0.89 2.14 2.931(2) 147.0 .
N3 H3A O5 0.89 1.93 2.8017(19) 166.5 1_565
N2 H2F O5 0.89 1.89 2.7614(19) 165.4 1_565
N2 H2E O2 0.89 1.88 2.7017(18) 152.5 .
N2 H2D O3 0.89 2.03 2.8468(18) 152.5 1_455
N1 H1C O4 0.89 2.23 3.0165(19) 146.6 1_455
N1 H1B O1 0.89 1.98 2.8249(19) 157.1 2_666
N1 H1A O3 0.89 2.01 2.8400(18) 154.6 1_455
O3W H2W3 O4 0.839(10) 1.942(10) 2.7806(19) 178(3) .
O3W H1W3 O2W 0.834(10) 2.101(18) 2.878(2) 155(3) .
O2W H2W2 O3W 0.844(10) 1.994(11) 2.826(2) 168(3) 2_665
O2W H1W2 O3 0.847(9) 1.902(10) 2.7426(18) 172(2) .
O1W H2W1 O2 0.848(9) 1.928(10) 2.7679(18) 171(2) .
O1W H1W1 O4 0.845(10) 2.077(12) 2.8927(19) 162(3) 1_565
O6 H6 O1 0.75(3) 1.74(3) 2.4948(19) 174(3) 2_666
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
N1 C1 P1 O2 -64.92(11)
C2 C1 P1 O2 51.41(11)
P2 C1 P1 O2 175.12(7)
N1 C1 P1 O3 175.02(9)
C2 C1 P1 O3 -68.66(11)
P2 C1 P1 O3 55.06(10)
N1 C1 P1 O1 54.52(11)
C2 C1 P1 O1 170.84(10)
P2 C1 P1 O1 -65.44(9)
N1 C1 P2 O4 168.80(9)
C2 C1 P2 O4 53.75(12)
P1 C1 P2 O4 -70.62(10)
N1 C1 P2 O5 43.40(11)
C2 C1 P2 O5 -71.65(11)
P1 C1 P2 O5 163.98(8)
N1 C1 P2 O6 -74.36(11)
C2 C1 P2 O6 170.58(10)
P1 C1 P2 O6 46.21(10)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146909
