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#$Date: 2025-04-05 07:13:47 +0300 (Sat, 05 Apr 2025) $
#$Revision: 299145 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/02/7160229.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_7160229
loop_
_publ_author_name
'Urbanovský, Peter'
'David, Tomáš'
'Hlinová, Veronika'
'Kubíček, Vojtěch'
'Pietzsch, Hans-Jürgen'
'Hermann, Petr'
_publ_section_title
;
 Cross-bridged cyclam derivatives with bis(phosphinate) and
 phosphinate-phosphonate pendant arms (cb-BPC) as chelators for copper
 radioisotopes.
;
_journal_issue                   3
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              699
_journal_page_last               720
_journal_paper_doi               10.1039/d4ob01473a
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C8 H11 N O6 P2'
_chemical_formula_sum            'C8 H11 N O6 P2'
_chemical_formula_weight         279.12
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2024-03-18 deposited with the CCDC.	2024-11-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.7720(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.3534(4)
_cell_length_b                   8.1042(2)
_cell_length_c                   10.3592(2)
_cell_measurement_reflns_used    9905
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.4914
_cell_measurement_theta_min      2.9406
_cell_volume                     1120.52(5)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.15'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_unetI/netI     0.0118
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            20659
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.941
_diffrn_source                   'microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.405
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.622
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.118
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2559
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0248
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0355P)²+0.6389P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0701
_refine_ls_wR_factor_ref         0.0711
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2458
_reflns_number_total             2559
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01473a2.cif
_cod_data_source_block           pno2ppinb
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7160229.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7160229
_shelx_shelxl_version_number     2017/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.787
_shelx_estimated_absorpt_t_max   0.954
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.55272(2) 0.73621(4) 0.57944(3) 0.01646(9) Uani 1 1 d . . . . .
H1 H 0.545231 0.749122 0.444126 0.020 Uiso 1 1 d R U . . .
O11 O 0.61833(7) 0.58065(12) 0.59907(9) 0.0232(2) Uani 1 1 d . . . . .
H11O H 0.6265(18) 0.553(3) 0.680(2) 0.063(7) Uiso 1 1 d . . . . .
O12 O 0.59259(7) 0.89304(12) 0.63677(9) 0.0232(2) Uani 1 1 d . . . . .
C1 C 0.43180(9) 0.68931(15) 0.64155(12) 0.0180(2) Uani 1 1 d . . . . .
H11 H 0.438901 0.678459 0.736578 0.022 Uiso 1 1 calc R U . . .
H12 H 0.410009 0.580820 0.606892 0.022 Uiso 1 1 calc R U . . .
P2 P 0.33484(2) 0.83749(4) 0.60497(3) 0.01583(9) Uani 1 1 d . . . . .
O21 O 0.33077(7) 0.85571(11) 0.45554(8) 0.02055(19) Uani 1 1 d . . . . .
H21O H 0.3558(16) 0.943(3) 0.432(2) 0.046(6) Uiso 1 1 d . . . . .
O22 O 0.35221(7) 0.99876(11) 0.67291(9) 0.02186(19) Uani 1 1 d . . . . .
C2 C 0.21928(9) 0.74547(15) 0.65254(12) 0.0189(2) Uani 1 1 d . . . . .
H21 H 0.224659 0.722066 0.746296 0.023 Uiso 1 1 calc R U . . .
H22 H 0.165129 0.827682 0.639048 0.023 Uiso 1 1 calc R U . . .
C3 C 0.18824(9) 0.58848(15) 0.58379(11) 0.0167(2) Uani 1 1 d . . . . .
C4 C 0.13259(9) 0.59579(15) 0.46717(11) 0.0179(2) Uani 1 1 d . . . . .
H41 H 0.117694 0.699868 0.428990 0.021 Uiso 1 1 calc R U . . .
C5 C 0.09900(9) 0.45246(15) 0.40689(12) 0.0186(2) Uani 1 1 d . . . . .
H51 H 0.060791 0.456965 0.328079 0.022 Uiso 1 1 calc R U . . .
C6 C 0.12255(9) 0.30253(15) 0.46447(12) 0.0181(2) Uani 1 1 d . . . . .
N6 N 0.08219(8) 0.15123(13) 0.40521(11) 0.0225(2) Uani 1 1 d . . . . .
O61 O 0.01925(8) 0.16460(12) 0.31706(10) 0.0286(2) Uani 1 1 d . . . . .
O62 O 0.11284(9) 0.01758(12) 0.44629(12) 0.0369(3) Uani 1 1 d . . . . .
C7 C 0.18006(9) 0.29016(16) 0.57775(13) 0.0206(2) Uani 1 1 d . . . . .
H71 H 0.196757 0.185585 0.613836 0.025 Uiso 1 1 calc R U . . .
C8 C 0.21254(9) 0.43505(16) 0.63691(12) 0.0198(2) Uani 1 1 d . . . . .
H81 H 0.251909 0.429587 0.714764 0.024 Uiso 1 1 calc R U . . .
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
_geom_angle_publ_flag
O12 P1 O11 116.63(6) . . ?
O12 P1 C1 110.53(6) . . ?
O11 P1 C1 107.00(6) . . ?
O12 P1 H1 110.3 . . ?
O11 P1 H1 102.4 . . ?
C1 P1 H1 109.6 . . ?
P1 O11 H11O 112.8(16) . . ?
P1 C1 P2 115.62(7) . . ?
P1 C1 H11 108.4 . . ?
P2 C1 H11 108.4 . . ?
P1 C1 H12 108.4 . . ?
P2 C1 H12 108.4 . . ?
H11 C1 H12 107.4 . . ?
O22 P2 O21 112.64(5) . . ?
O22 P2 C2 110.78(6) . . ?
O21 P2 C2 107.98(6) . . ?
O22 P2 C1 112.55(6) . . ?
O21 P2 C1 106.04(6) . . ?
C2 P2 C1 106.50(6) . . ?
P2 O21 H21O 112.3(14) . . ?
C3 C2 P2 116.49(9) . . ?
C3 C2 H21 108.2 . . ?
P2 C2 H21 108.2 . . ?
C3 C2 H22 108.2 . . ?
P2 C2 H22 108.2 . . ?
H21 C2 H22 107.3 . . ?
C8 C3 C4 119.30(11) . . ?
C8 C3 C2 120.55(10) . . ?
C4 C3 C2 120.14(11) . . ?
C5 C4 C3 120.58(11) . . ?
C5 C4 H41 119.7 . . ?
C3 C4 H41 119.7 . . ?
C6 C5 C4 118.35(11) . . ?
C6 C5 H51 120.8 . . ?
C4 C5 H51 120.8 . . ?
C5 C6 C7 122.71(11) . . ?
C5 C6 N6 118.53(11) . . ?
C7 C6 N6 118.74(11) . . ?
O61 N6 O62 123.28(11) . . ?
O61 N6 C6 118.18(11) . . ?
O62 N6 C6 118.54(11) . . ?
C6 C7 C8 118.04(11) . . ?
C6 C7 H71 121.0 . . ?
C8 C7 H71 121.0 . . ?
C7 C8 C3 120.97(11) . . ?
C7 C8 H81 119.5 . . ?
C3 C8 H81 119.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O12 1.4941(9) . ?
P1 O11 1.5450(10) . ?
P1 C1 1.7973(12) . ?
P1 H1 1.4062 . ?
O11 H11O 0.87(2) . ?
C1 P2 1.7976(12) . ?
C1 H11 0.9900 . ?
C1 H12 0.9900 . ?
P2 O22 1.4991(9) . ?
P2 O21 1.5543(9) . ?
P2 C2 1.7964(13) . ?
O21 H21O 0.82(2) . ?
C2 C3 1.5099(16) . ?
C2 H21 0.9900 . ?
C2 H22 0.9900 . ?
C3 C8 1.3940(17) . ?
C3 C4 1.3999(16) . ?
C4 C5 1.3867(17) . ?
C4 H41 0.9500 . ?
C5 C6 1.3854(17) . ?
C5 H51 0.9500 . ?
C6 C7 1.3862(17) . ?
C6 N6 1.4664(15) . ?
N6 O61 1.2266(15) . ?
N6 O62 1.2292(15) . ?
C7 C8 1.3878(18) . ?
C7 H71 0.9500 . ?
C8 H81 0.9500 . ?
