#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:01:59 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301802 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/81/2108101.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# 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_2108101
loop_
_publ_author_name
'Bulut, Aysun'
'Wörle, Michael'
'Zorlu, Yunus'
'Kirpi, Erdogan'
'Kurt, Huseyin'
'Zubieta, Jon'
'Grabowsky, Simon'
'Beckmann, Jens'
'Yücesan, Gündoğ'
_publ_section_title
;
 A potential Cu/V-organophosphonate platform for tailored void spaces
 via terpyridine mold casting
;
_journal_coeditor_code           RM5002
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              296
_journal_page_last               303
_journal_paper_doi               10.1107/S2052520617000245
_journal_volume                  73
_journal_year                    2017
_chemical_formula_moiety         'C25 H24 O12 P4, 2(C H4 O)'
_chemical_formula_sum            'C27 H32 O14 P4'
_chemical_formula_weight         704.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 127.610(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   29.093(3)
_cell_length_b                   7.2893(8)
_cell_length_c                   18.672(2)
_cell_measurement_temperature    296.(2)
_cell_volume                     3136.8(6)
_computing_cell_refinement       'APEX2 v2014.11-0 (Bruker AXS)'
_computing_data_collection
'Bruker Instrument Service v2013.12.0.0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material
'PLATON V1.16 (Spek, 2009), SHELXTL V6.14 (Bruker AXS)'
_computing_structure_refinement  'SHELXTL V6.14 (Bruker AXS)'
_computing_structure_solution    'SHELXTL V6.14 (Bruker AXS)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
'Bruker APEX II QUAZAR three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer QUAZAR mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14601
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    0.309
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.108
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.474
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         2772
_refine_ls_number_restraints     102
_refine_ls_restrained_S_all      1.165
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0535
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0601P)²+9.8652P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1317
_refine_ls_wR_factor_ref         0.1410
_reflns_number_gt                2215
_reflns_number_total             2772
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            rm5002sup1.cif
_cod_data_source_block           I
_cod_database_code               2108101
loop_
_space_group_symop_operation_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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.5 0.7543(6) 0.75 0.0201(9) Uani d 1.0 . .
C C2 0.45843(13) 0.6248(4) 0.67007(19) 0.0215(6) Uani d 1.0 . .
C C3 0.48080(14) 0.5023(4) 0.6411(2) 0.0294(7) Uani d 1.0 . .
H H3 0.5205 0.5005 0.6702 0.035 Uiso calc 1.0 . .
C C4 0.44510(14) 0.3832(5) 0.5700(2) 0.0331(8) Uani d 1.0 . .
H H4 0.461 0.3044 0.5512 0.04 Uiso calc 1.0 . .
C C5 0.38592(14) 0.3801(4) 0.5265(2) 0.0275(7) Uani d 1.0 . .
C C6 0.36439(14) 0.4946(5) 0.5582(2) 0.0361(8) Uani d 1.0 . .
H H6 0.325 0.4908 0.5316 0.043 Uiso calc 1.0 . .
C C7 0.39999(14) 0.6155(5) 0.6287(2) 0.0340(8) Uani d 1.0 . .
H H7 0.3841 0.6916 0.6484 0.041 Uiso calc 1.0 . .
C C8 0.46641(13) 0.8852(4) 0.7691(2) 0.0223(7) Uani d 1.0 . .
C C9 0.47309(14) 0.8897(5) 0.8493(2) 0.0303(8) Uani d 1.0 . .
H H9 0.4991 0.8099 0.8959 0.036 Uiso calc 1.0 . .
C C10 0.44141(14) 1.0117(5) 0.8608(2) 0.0319(8) Uani d 1.0 . .
H H10 0.4462 1.0115 0.9148 0.038 Uiso calc 1.0 . .
C C11 0.40288(13) 1.1335(4) 0.7932(2) 0.0262(7) Uani d 1.0 . .
C C12 0.39721(15) 1.1327(5) 0.7139(2) 0.0332(8) Uani d 1.0 . .
H H12 0.3719 1.2147 0.6679 0.04 Uiso calc 1.0 . .
C C13 0.42871(15) 1.0111(5) 0.7024(2) 0.0319(8) Uani d 1.0 . .
H H13 0.4246 1.0136 0.6489 0.038 Uiso calc 1.0 . .
C C14 0.2250(2) 0.2780(7) 0.8758(4) 0.0695(14) Uani d 1.0 . .
H H14A 0.2607 0.261 0.9354 0.104 Uiso calc 1.0 . .
H H14B 0.2049 0.163 0.8533 0.104 Uiso calc 1.0 . .
H H14C 0.2011 0.365 0.8781 0.104 Uiso calc 1.0 . .
O O7 0.23750(14) 0.3461(5) 0.8163(2) 0.0682(9) Uani d 1.0 . .
H H7A 0.2123 0.3109 0.7646 0.102 Uiso calc 1.0 . .
P P1 0.33894(4) 0.23837(12) 0.42935(6) 0.0332(3) Uani d 1.0 . .
P P2 0.36115(4) 1.29093(13) 0.80635(6) 0.0308(3) Uani d 1.0 . .
O O1 0.3493(2) 0.0381(5) 0.4614(3) 0.0378(9) Uani d 0.766(9) A 1
H H1 0.3283 -0.0295 0.4178 0.057 Uiso calc 0.766(9) A 1
O O2 0.27663(14) 0.2975(7) 0.3880(3) 0.0420(9) Uani d 0.766(9) A 1
H H2 0.2725 0.4064 0.3743 0.063 Uiso calc 0.766(9) A 1
O O3 0.35320(19) 0.2664(7) 0.3648(3) 0.0363(9) Uani d 0.766(9) A 1
O O2A 0.2824(5) 0.224(2) 0.4158(9) 0.0384(17) Uani d 0.234(9) A 2
H H2A 0.2627 0.1416 0.3801 0.058 Uiso calc 0.234(9) A 2
O O1A 0.3729(6) 0.0457(15) 0.4733(9) 0.0370(18) Uani d 0.234(9) A 2
H H1A 0.3569 -0.0351 0.4348 0.055 Uiso calc 0.234(9) A 2
O O3A 0.3369(7) 0.280(3) 0.3496(9) 0.0349(18) Uani d 0.234(9) A 2
O O4 0.33591(14) 1.2024(4) 0.8455(2) 0.0384(7) Uani d 0.868(3) B 3
O O5 0.31416(11) 1.3798(4) 0.71242(18) 0.0354(7) Uani d 0.868(3) B 3
H H5 0.2916 1.3004 0.6771 0.053 Uiso calc 0.868(3) B 3
O O6 0.40348(12) 1.4518(4) 0.8630(2) 0.0374(7) Uani d 0.868(3) B 3
H H6A 0.3862 1.532 0.8689 0.056 Uiso calc 0.868(3) B 3
O O4A 0.3663(9) 1.230(2) 0.8915(11) 0.0302(18) Uani d 0.132(3) B 4
O O6A 0.3825(8) 1.4765(18) 0.8126(14) 0.0311(19) Uani d 0.132(3) B 4
H H6A1 0.3641 1.5502 0.8193 0.047 Uiso calc 0.132(3) B 4
O O5A 0.2990(5) 1.226(2) 0.7360(11) 0.0364(19) Uani d 0.132(3) B 4
H H5A 0.2984 1.1462 0.7044 0.055 Uiso calc 0.132(3) B 4
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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C2 C1 C2 2_656 . 104.5(3)
C2 C1 C8 2_656 2_656 111.49(15)
C2 C1 C8 . 2_656 112.66(15)
C2 C1 C8 2_656 . 112.66(15)
C2 C1 C8 . . 111.49(15)
C8 C1 C8 2_656 . 104.2(3)
C7 C2 C3 . . 117.4(3)
C7 C2 C1 . . 123.0(3)
C3 C2 C1 . . 119.4(2)
C4 C3 C2 . . 121.3(3)
C4 C3 H3 . . 119.3
C2 C3 H3 . . 119.3
C3 C4 C5 . . 120.6(3)
C3 C4 H4 . . 119.7
C5 C4 H4 . . 119.7
C6 C5 C4 . . 117.9(3)
C6 C5 P1 . . 121.3(2)
C4 C5 P1 . . 120.7(2)
C5 C6 C7 . . 121.5(3)
C5 C6 H6 . . 119.2
C7 C6 H6 . . 119.2
C2 C7 C6 . . 121.1(3)
C2 C7 H7 . . 119.5
C6 C7 H7 . . 119.5
C9 C8 C13 . . 117.8(3)
C9 C8 C1 . . 124.6(3)
C13 C8 C1 . . 117.6(2)
C8 C9 C10 . . 120.8(3)
C8 C9 H9 . . 119.6
C10 C9 H9 . . 119.6
C11 C10 C9 . . 121.1(3)
C11 C10 H10 . . 119.5
C9 C10 H10 . . 119.5
C10 C11 C12 . . 118.2(3)
C10 C11 P2 . . 121.8(2)
C12 C11 P2 . . 120.0(2)
C13 C12 C11 . . 120.7(3)
C13 C12 H12 . . 119.6
C11 C12 H12 . . 119.6
C12 C13 C8 . . 121.3(3)
C12 C13 H13 . . 119.3
C8 C13 H13 . . 119.3
O7 C14 H14A . . 109.5
O7 C14 H14B . . 109.5
H14A C14 H14B . . 109.5
O7 C14 H14C . . 109.5
H14A C14 H14C . . 109.5
H14B C14 H14C . . 109.5
C14 O7 H7A . . 109.5
O3A P1 O2A . . 118.3(7)
O3 P1 O2 . . 112.1(2)
O3 P1 O1 . . 110.9(3)
O2 P1 O1 . . 110.6(2)
O3A P1 O1A . . 108.9(9)
O2A P1 O1A . . 106.9(7)
O3A P1 C5 . . 116.0(7)
O3 P1 C5 . . 108.6(2)
O2A P1 C5 . . 106.8(5)
O2 P1 C5 . . 106.52(17)
O1 P1 C5 . . 107.85(19)
O1A P1 C5 . . 97.7(5)
O6A P2 O5A . . 125.4(10)
O4 P2 O6 . . 114.97(18)
O4 P2 O5 . . 112.42(17)
O6 P2 O5 . . 103.79(17)
O6A P2 O4A . . 114.1(10)
O5A P2 O4A . . 96.6(10)
O6A P2 C11 . . 108.2(7)
O4 P2 C11 . . 111.96(16)
O5A P2 C11 . . 103.2(7)
O6 P2 C11 . . 104.74(15)
O5 P2 C11 . . 108.29(15)
O4A P2 C11 . . 107.6(6)
P1 O1 H1 . . 109.5
P1 O2 H2 . . 109.5
P1 O2A H2A . . 109.5
P1 O1A H1A . . 109.5
P2 O5 H5 . . 109.5
P2 O6 H6A . . 109.5
P2 O6A H6A1 . . 109.5
P2 O5A H5A . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 2_656 1.542(4)
C1 C2 . 1.542(4)
C1 C8 2_656 1.555(4)
C1 C8 . 1.555(4)
C2 C7 . 1.374(4)
C2 C3 . 1.394(4)
C3 C4 . 1.383(5)
C3 H3 . 0.93
C4 C5 . 1.385(5)
C4 H4 . 0.93
C5 C6 . 1.374(5)
C5 P1 . 1.789(3)
C6 C7 . 1.385(5)
C6 H6 . 0.93
C7 H7 . 0.93
C8 C9 . 1.388(4)
C8 C13 . 1.389(4)
C9 C10 . 1.389(4)
C9 H9 . 0.93
C10 C11 . 1.382(4)
C10 H10 . 0.93
C11 C12 . 1.388(4)
C11 P2 . 1.792(3)
C12 C13 . 1.383(5)
C12 H12 . 0.93
C13 H13 . 0.93
C14 O7 . 1.451(5)
C14 H14A . 0.96
C14 H14B . 0.96
C14 H14C . 0.96
O7 H7A . 0.82
P1 O3A . 1.484(12)
P1 O3 . 1.508(4)
P1 O2A . 1.509(10)
P1 O2 . 1.536(4)
P1 O1 . 1.536(4)
P1 O1A . 1.622(11)
P2 O6A . 1.463(13)
P2 O4 . 1.465(3)
P2 O5A . 1.524(12)
P2 O6 . 1.556(3)
P2 O5 . 1.561(3)
P2 O4A . 1.568(12)
O1 H1 . 0.82
O2 H2 . 0.82
O2A H2A . 0.82
O1A H1A . 0.82
O5 H5 . 0.82
O6 H6A . 0.82
O6A H6A1 . 0.82
O5A H5A . 0.82
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C14 H14B O5 4_536 0.96 2.29 3.185(6) 154.9
O7 H7A O3 7_556 0.82 2.04 2.861(5) 177.1
O7 H7A O3A 7_556 0.82 1.82 2.635(15) 173.4
O2 H2 O7 6_565 0.82 2.03 2.824(7) 163.3
O5A H5A O7 4_556 0.82 2.35 2.910(17) 126.0
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_site_symmetry_1
_geom_torsion
C2 C1 C2 C7 2_656 115.3(3)
C8 C1 C2 C7 2_656 -123.4(3)
C8 C1 C2 C7 . -6.6(4)
C2 C1 C2 C3 2_656 -60.4(2)
C8 C1 C2 C3 2_656 60.8(4)
C8 C1 C2 C3 . 177.6(3)
C7 C2 C3 C4 . 3.7(5)
C1 C2 C3 C4 . 179.7(3)
C2 C3 C4 C5 . -1.3(5)
C3 C4 C5 C6 . -2.0(5)
C3 C4 C5 P1 . 175.4(3)
C4 C5 C6 C7 . 2.8(5)
P1 C5 C6 C7 . -174.6(3)
C3 C2 C7 C6 . -2.9(5)
C1 C2 C7 C6 . -178.8(3)
C5 C6 C7 C2 . -0.3(6)
C2 C1 C8 C9 2_656 1.0(4)
C2 C1 C8 C9 . 118.1(3)
C8 C1 C8 C9 2_656 -120.0(3)
C2 C1 C8 C13 2_656 178.5(3)
C2 C1 C8 C13 . -64.4(4)
C8 C1 C8 C13 2_656 57.5(2)
C13 C8 C9 C10 . 2.3(5)
C1 C8 C9 C10 . 179.8(3)
C8 C9 C10 C11 . -0.7(5)
C9 C10 C11 C12 . -0.9(5)
C9 C10 C11 P2 . 179.5(3)
C10 C11 C12 C13 . 0.9(5)
P2 C11 C12 C13 . -179.5(3)
C11 C12 C13 C8 . 0.7(5)
C9 C8 C13 C12 . -2.3(5)
C1 C8 C13 C12 . -179.9(3)
C6 C5 P1 O3A . 115.4(8)
C4 C5 P1 O3A . -61.8(8)
C6 C5 P1 O3 . 129.4(3)
C4 C5 P1 O3 . -47.8(4)
C6 C5 P1 O2A . -18.8(8)
C4 C5 P1 O2A . 163.9(8)
C6 C5 P1 O2 . 8.5(4)
C4 C5 P1 O2 . -168.8(3)
C6 C5 P1 O1 . -110.3(3)
C4 C5 P1 O1 . 72.5(4)
C6 C5 P1 O1A . -129.2(6)
C4 C5 P1 O1A . 53.6(6)
C10 C11 P2 O6A . 110.9(9)
C12 C11 P2 O6A . -68.7(9)
C10 C11 P2 O4 . -44.7(3)
C12 C11 P2 O4 . 135.7(3)
C10 C11 P2 O5A . -114.3(8)
C12 C11 P2 O5A . 66.1(8)
C10 C11 P2 O6 . 80.6(3)
C12 C11 P2 O6 . -99.0(3)
C10 C11 P2 O5 . -169.2(3)
C12 C11 P2 O5 . 11.2(3)
C10 C11 P2 O4A . -12.9(9)
C12 C11 P2 O4A . 167.5(8)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139064629
