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#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/49/4504980.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_4504980
loop_
_publ_author_name
'Kong, Deyuan'
'McBee, Jennifer L.'
'Clearfield, Abraham'
_publ_section_title
;
 Crystal Engineered Acid--Base Complexes with 2D and 3D Hydrogen
 Bonding Systems Using a Bisphosphonic Acid as the Building Block
;
_journal_coden_ASTM              CGDEFU
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              643
_journal_page_last               649
_journal_paper_doi               10.1021/cg0497243
_journal_volume                  5
_journal_year                    2005
_chemical_formula_sum            'C2 H11 N O7 P2'
_chemical_formula_weight         223.06
_space_group_IT_number           19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4589(15)
_cell_length_b                   8.1654(16)
_cell_length_c                   13.538(3)
_cell_measurement_temperature    293(2)
_cell_volume                     824.5(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_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  0.0178
_diffrn_reflns_av_sigmaI/netI    0.0224
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4820
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         2.91
_exptl_absorpt_coefficient_mu    0.532
_exptl_absorpt_correction_T_max  0.9244
_exptl_absorpt_correction_T_min  0.7103
_exptl_crystal_density_diffrn    1.797
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.69
_exptl_crystal_size_mid          0.56
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.600
_refine_diff_density_min         -0.577
_refine_diff_density_rms         0.115
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(11)
_refine_ls_extinction_coef       0.162(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1805
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.141
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0317
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0521P)²+0.5583P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.0848
_reflns_number_gt                1803
_reflns_number_total             1805
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg0497243si20040805_031606.cif
_cod_data_source_block           sol1
_cod_original_cell_volume        824.6(3)
_cod_database_code               4504980
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
N1 N 0.7102(3) 0.1922(2) 0.28893(14) 0.0096(4) Uani 1 1 d .
H1F H 0.659(5) 0.244(4) 0.241(2) 0.023(8) Uiso 1 1 d .
P1 P 0.89529(7) 0.02020(7) 0.14389(4) 0.00897(16) Uani 1 1 d .
P2 P 0.37675(7) 0.06795(7) 0.34081(4) 0.00874(17) Uani 1 1 d .
H2A H 1.1280 0.1325 0.1786 0.013 Uiso 1 1 d R
O1 O 0.7643(2) 0.05696(19) 0.06328(11) 0.0123(3) Uani 1 1 d .
O1W O 0.9067(3) 0.3505(2) 0.96776(13) 0.0222(4) Uani 1 1 d .
H1WA H 0.872(4) 0.245(4) 1.003(2) 0.011(6) Uiso 1 1 d .
O2 O 1.0355(2) 0.16360(19) 0.14719(11) 0.0120(3) Uani 1 1 d .
O3 O 0.9848(2) -0.14585(18) 0.13983(11) 0.0120(3) Uani 1 1 d .
O4 O 0.2296(2) 0.12797(19) 0.41635(12) 0.0126(3) Uani 1 1 d .
H4A H 0.1671 0.2025 0.3892 0.019 Uiso 1 1 d R
O5 O 0.3263(2) 0.1147(2) 0.23632(11) 0.0131(3) Uani 1 1 d .
O6 O 0.4122(2) -0.10894(18) 0.35980(11) 0.0119(3) Uani 1 1 d .
C1 C 0.7852(3) 0.0268(2) 0.26408(15) 0.0116(4) Uani 1 1 d .
H1C H 0.6887 -0.0529 0.2649 0.014 Uiso 1 1 calc R
H1D H 0.8708 -0.0045 0.3146 0.014 Uiso 1 1 calc R
C2 C 0.5751(3) 0.1892(3) 0.37100(15) 0.0111(4) Uani 1 1 d .
H2C H 0.6327 0.1306 0.4237 0.013 Uiso 1 1 d R
H2B H 0.5485 0.2953 0.3978 0.013 Uiso 1 1 d R
H1WC H 0.836(4) 0.438(4) 1.008(2) 0.012(7) Uiso 1 1 d .
H1WB H 1.047(7) 0.367(6) 0.977(3) 0.064(14) Uiso 1 1 d .
H1E H 0.812(4) 0.263(4) 0.309(2) 0.012(7) 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
C2 N1 C1 113.67(16)
C2 N1 H1F 106(2)
C1 N1 H1F 116(2)
C2 N1 H1E 108.9(18)
C1 N1 H1E 107.6(17)
H1F N1 H1E 105(3)
O1 P1 O3 116.24(9)
O1 P1 O2 107.84(9)
O3 P1 O2 112.05(9)
O1 P1 C1 110.54(10)
O3 P1 C1 104.93(9)
O2 P1 C1 104.63(9)
O6 P2 O5 116.73(9)
O6 P2 O4 108.21(9)
O5 P2 O4 110.76(9)
O6 P2 C2 110.04(10)
O5 P2 C2 105.92(10)
O4 P2 C2 104.49(9)
H1WA O1W H1WC 102(2)
H1WA O1W H1WB 108(3)
H1WC O1W H1WB 111(3)
P1 O2 H2A 109.4
P2 O4 H4A 108.9
N1 C1 P1 113.23(14)
N1 C1 H1C 108.9
P1 C1 H1C 108.9
N1 C1 H1D 108.9
P1 C1 H1D 108.9
H1C C1 H1D 107.7
N1 C2 P2 112.78(14)
N1 C2 H2C 105.0
P2 C2 H2C 105.0
N1 C2 H2B 113.8
P2 C2 H2B 114.0
H2C C2 H2B 105.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.500(3)
N1 C1 1.501(3)
N1 H1F 0.87(3)
N1 H1E 0.99(3)
P1 O1 1.4954(16)
P1 O3 1.5125(15)
P1 O2 1.5705(16)
P1 C1 1.824(2)
P2 O6 1.4907(16)
P2 O5 1.5127(16)
P2 O4 1.5783(16)
P2 C2 1.827(2)
O1W H1WA 1.01(3)
O1W H1WC 1.04(3)
O1W H1WB 1.06(5)
O2 H2A 0.8498
O4 H4A 0.8501
C1 H1C 0.9700
C1 H1D 0.9700
C2 H2C 0.9600
C2 H2B 0.9599
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
O2 H2A O5 0.85 1.68 2.514(2) 167.0 1_655
O1W H1WA O1 1.01(3) 1.92(3) 2.923(2) 170(3) 1_556
O1W H1WA O2 1.01(3) 2.40(3) 3.025(2) 119(2) 1_556
O1W H1WC O4 1.04(3) 1.92(3) 2.937(3) 164(2) 3_656
O1W H1WC O6 1.04(3) 2.61(3) 3.349(2) 128(2) 3_656
O1W H1WB O1 1.06(5) 1.82(5) 2.804(3) 153(4) 4_556
N1 H1E O3 0.99(3) 1.83(3) 2.802(3) 167(3) 3_755
O4 H4A O3 0.85 1.72 2.559(2) 166.7 3_655
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
C2 N1 C1 P1 162.97(15)
O1 P1 C1 N1 -62.36(17)
O3 P1 C1 N1 171.59(14)
O2 P1 C1 N1 53.48(17)
C1 N1 C2 P2 -62.4(2)
O6 P2 C2 N1 82.84(16)
O5 P2 C2 N1 -44.16(17)
O4 P2 C2 N1 -161.19(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139145682
