#------------------------------------------------------------------------------
#$Date: 2023-07-05 02:11:22 +0300 (Wed, 05 Jul 2023) $
#$Revision: 284796 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/33/7713393.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_7713393
loop_
_publ_author_name
'Koucký, Filip'
'Kotek, Jan'
'Císařová, Ivana'
'Havlíčková, Jana'
'Kubíček, Vojtěch'
'Hermann, Petr'
_publ_section_title
;
 Transition metal complexes of cyclam with two
 2,2,2-trifluoroethylphosphinate pendant arms as probes for ¹⁹F
 magnetic resonance imaging.
;
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_paper_doi               10.1039/d3dt01420g
_journal_year                    2023
_chemical_formula_moiety         'C30 H44 F6 N4 O4 P2, 6(H2 O)'
_chemical_formula_sum            'C30 H56 F6 N4 O10 P2'
_chemical_formula_weight         808.72
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2023-05-10 deposited with the CCDC.	2023-06-16 downloaded from the CCDC.
;
_cell_angle_alpha                63.6730(10)
_cell_angle_beta                 70.0310(10)
_cell_angle_gamma                76.3980(10)
_cell_formula_units_Z            1
_cell_length_a                   8.9086(3)
_cell_length_b                   10.8155(4)
_cell_length_c                   11.9920(4)
_cell_measurement_reflns_used    7892
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5542
_cell_measurement_theta_min      2.4446
_cell_volume                     968.51(6)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v2015.3.1.0'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 758)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0226
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14239
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         1.969
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       prism
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.570
_exptl_crystal_size_mid          0.323
_exptl_crystal_size_min          0.192
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4447
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0339
_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)+(0.0485P)²+0.2990P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.0930
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3810
_reflns_number_total             4447
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3dt01420g2.cif
_cod_data_source_block           pf2b2cam
_cod_database_code               7713393
_shelx_shelxl_version_number     2014/7
_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   0.896
_shelx_estimated_absorpt_t_max   0.963
loop_
_space_group_symop_operation_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_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
N1 N -0.02163(12) 0.25232(10) 0.43726(10) 0.0171(2) Uani 1 1 d . . . . .
C2 C -0.18335(14) 0.24759(13) 0.52409(12) 0.0199(3) Uani 1 1 d . . . . .
H21 H -0.2411 0.1855 0.5160 0.024 Uiso 1 1 calc R U . . .
H22 H -0.2412 0.3416 0.4966 0.024 Uiso 1 1 calc R U . . .
C3 C -0.18757(15) 0.19721(13) 0.66541(13) 0.0214(3) Uani 1 1 d . . . . .
H31 H -0.1683 0.2750 0.6796 0.026 Uiso 1 1 calc R U . . .
H32 H -0.2964 0.1707 0.7198 0.026 Uiso 1 1 calc R U . . .
N4 N -0.06743(13) 0.07652(10) 0.70933(10) 0.0176(2) Uani 1 1 d . . . . .
H41 H 0.033(2) 0.0994(16) 0.6605(16) 0.028(4) Uiso 1 1 d . . . . .
C5 C -0.09217(15) -0.04961(12) 0.69724(12) 0.0199(3) Uani 1 1 d . . . . .
H51 H -0.1122 -0.0214 0.6125 0.024 Uiso 1 1 calc R U . . .
H52 H -0.1881 -0.0911 0.7657 0.024 Uiso 1 1 calc R U . . .
C6 C 0.05236(15) -0.15754(13) 0.70875(13) 0.0206(3) Uani 1 1 d . . . . .
H61 H 0.0718 -0.1873 0.7939 0.025 Uiso 1 1 calc R U . . .
H62 H 0.1488 -0.1163 0.6408 0.025 Uiso 1 1 calc R U . . .
C7 C 0.02419(16) -0.28298(12) 0.69456(12) 0.0198(3) Uani 1 1 d . . . . .
H71 H 0.1101 -0.3583 0.7182 0.024 Uiso 1 1 calc R U . . .
H72 H -0.0794 -0.3165 0.7557 0.024 Uiso 1 1 calc R U . . .
C8 C 0.07552(15) 0.34663(12) 0.43571(13) 0.0191(2) Uani 1 1 d . . . . .
H81 H 0.0264 0.3728 0.5108 0.023 Uiso 1 1 calc R U . . .
H82 H 0.0859 0.4319 0.3553 0.023 Uiso 1 1 calc R U . . .
P1 P 0.27070(4) 0.24760(3) 0.44423(3) 0.01708(10) Uani 1 1 d . . . . .
O11 O 0.24162(10) 0.12668(9) 0.57398(9) 0.0210(2) Uani 1 1 d . . . . .
O12 O 0.34941(11) 0.21911(9) 0.32520(9) 0.0224(2) Uani 1 1 d . . . . .
C9 C 0.39031(16) 0.35646(14) 0.45447(13) 0.0235(3) Uani 1 1 d . . . . .
H91 H 0.3193 0.4048 0.5099 0.028 Uiso 1 1 calc R U . . .
H92 H 0.4729 0.2954 0.4982 0.028 Uiso 1 1 calc R U . . .
C10 C 0.47213(16) 0.46231(14) 0.32913(14) 0.0262(3) Uani 1 1 d . . . . .
F1 F 0.53414(12) 0.55264(10) 0.34724(10) 0.0447(3) Uani 1 1 d . . . . .
F2 F 0.37288(11) 0.53982(9) 0.25535(9) 0.0352(2) Uani 1 1 d . . . . .
F3 F 0.59380(10) 0.40814(10) 0.25738(9) 0.0392(2) Uani 1 1 d . . . . .
C11 C -0.07608(17) 0.04242(13) 0.84794(12) 0.0223(3) Uani 1 1 d . . . . .
H111 H -0.1874 0.0242 0.9017 0.027 Uiso 1 1 calc R U . . .
H112 H -0.0056 -0.0438 0.8793 0.027 Uiso 1 1 calc R U . . .
C12 C -0.02751(16) 0.15476(13) 0.86697(12) 0.0208(3) Uani 1 1 d . . . . .
C13 C 0.13431(17) 0.16505(15) 0.84334(13) 0.0274(3) Uani 1 1 d . . . . .
H131 H 0.2140 0.1059 0.8090 0.033 Uiso 1 1 calc R U . . .
C14 C 0.1796(2) 0.26174(17) 0.86985(15) 0.0376(4) Uani 1 1 d . . . . .
H141 H 0.2901 0.2678 0.8544 0.045 Uiso 1 1 calc R U . . .
C15 C 0.0648(2) 0.34859(16) 0.91842(16) 0.0412(4) Uani 1 1 d . . . . .
H151 H 0.0964 0.4144 0.9363 0.049 Uiso 1 1 calc R U . . .
C16 C -0.0955(2) 0.34050(15) 0.94114(16) 0.0396(4) Uani 1 1 d . . . . .
H161 H -0.1744 0.4015 0.9735 0.047 Uiso 1 1 calc R U . . .
C17 C -0.14216(18) 0.24248(15) 0.91663(14) 0.0286(3) Uani 1 1 d . . . . .
H171 H -0.2529 0.2358 0.9340 0.034 Uiso 1 1 calc R U . . .
O1W O 0.49550(13) -0.03090(11) 0.31930(11) 0.0287(2) Uani 1 1 d . . . . .
H11W H 0.449(3) 0.042(2) 0.331(2) 0.055(6) Uiso 1 1 d . . . . .
H12W H 0.579(3) -0.055(2) 0.3486(19) 0.046(5) Uiso 1 1 d . . . . .
O2W O 0.4190(2) 0.37078(17) 0.05582(14) 0.0539(4) Uani 1 1 d D . . . .
H21W H 0.414(3) 0.333(2) 0.132(2) 0.054(6) Uiso 1 1 d . . . . .
H22W H 0.449(8) 0.316(6) 0.019(6) 0.12(3) Uiso 0.5 1 d D . P A 1
H23W H 0.469(6) 0.435(5) 0.018(5) 0.069(17) Uiso 0.5 1 d . . P B 2
O3W O 0.48709(18) 0.09065(17) 0.05800(14) 0.0449(3) Uani 1 1 d . . . . .
H31W H 0.505(3) 0.048(2) 0.129(2) 0.054(6) Uiso 1 1 d . . . . .
H32W H 0.514(6) 0.043(5) 0.012(5) 0.069(15) Uiso 0.5 1 d . . P C 1
H33W H 0.463(6) 0.170(6) 0.045(5) 0.069(16) Uiso 0.5 1 d . . P D 2
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'
F F 0.0171 0.0103 '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
C2 N1 C7 111.43(10) . 2_556 ?
C2 N1 C8 114.32(10) . . ?
C7 N1 C8 110.91(10) 2_556 . ?
N1 C2 C3 113.78(10) . . ?
N1 C2 H21 108.8 . . ?
C3 C2 H21 108.8 . . ?
N1 C2 H22 108.8 . . ?
C3 C2 H22 108.8 . . ?
H21 C2 H22 107.7 . . ?
N4 C3 C2 114.40(10) . . ?
N4 C3 H31 108.7 . . ?
C2 C3 H31 108.7 . . ?
N4 C3 H32 108.7 . . ?
C2 C3 H32 108.7 . . ?
H31 C3 H32 107.6 . . ?
C3 N4 C5 112.55(9) . . ?
C3 N4 C11 109.34(10) . . ?
C5 N4 C11 110.03(9) . . ?
C3 N4 H41 109.7(10) . . ?
C5 N4 H41 107.5(10) . . ?
C11 N4 H41 107.6(10) . . ?
N4 C5 C6 111.88(10) . . ?
N4 C5 H51 109.2 . . ?
C6 C5 H51 109.2 . . ?
N4 C5 H52 109.2 . . ?
C6 C5 H52 109.2 . . ?
H51 C5 H52 107.9 . . ?
C5 C6 C7 110.54(10) . . ?
C5 C6 H61 109.5 . . ?
C7 C6 H61 109.5 . . ?
C5 C6 H62 109.5 . . ?
C7 C6 H62 109.5 . . ?
H61 C6 H62 108.1 . . ?
N1 C7 C6 112.96(10) 2_556 . ?
N1 C7 H71 109.0 2_556 . ?
C6 C7 H71 109.0 . . ?
N1 C7 H72 109.0 2_556 . ?
C6 C7 H72 109.0 . . ?
H71 C7 H72 107.8 . . ?
N1 C8 P1 104.71(8) . . ?
N1 C8 H81 110.8 . . ?
P1 C8 H81 110.8 . . ?
N1 C8 H82 110.8 . . ?
P1 C8 H82 110.8 . . ?
H81 C8 H82 108.9 . . ?
O12 P1 O11 118.71(5) . . ?
O12 P1 C8 110.23(6) . . ?
O11 P1 C8 105.94(6) . . ?
O12 P1 C9 109.83(6) . . ?
O11 P1 C9 105.29(6) . . ?
C8 P1 C9 106.05(6) . . ?
C10 C9 P1 115.90(9) . . ?
C10 C9 H91 108.3 . . ?
P1 C9 H91 108.3 . . ?
C10 C9 H92 108.3 . . ?
P1 C9 H92 108.3 . . ?
H91 C9 H92 107.4 . . ?
F3 C10 F2 106.64(12) . . ?
F3 C10 F1 106.08(11) . . ?
F2 C10 F1 105.71(11) . . ?
F3 C10 C9 113.41(12) . . ?
F2 C10 C9 112.90(11) . . ?
F1 C10 C9 111.55(11) . . ?
C12 C11 N4 114.23(10) . . ?
C12 C11 H111 108.7 . . ?
N4 C11 H111 108.7 . . ?
C12 C11 H112 108.7 . . ?
N4 C11 H112 108.7 . . ?
H111 C11 H112 107.6 . . ?
C17 C12 C13 119.03(12) . . ?
C17 C12 C11 120.93(12) . . ?
C13 C12 C11 119.88(12) . . ?
C14 C13 C12 120.17(14) . . ?
C14 C13 H131 119.9 . . ?
C12 C13 H131 119.9 . . ?
C15 C14 C13 120.24(15) . . ?
C15 C14 H141 119.9 . . ?
C13 C14 H141 119.9 . . ?
C16 C15 C14 120.25(14) . . ?
C16 C15 H151 119.9 . . ?
C14 C15 H151 119.9 . . ?
C15 C16 C17 119.94(15) . . ?
C15 C16 H161 120.0 . . ?
C17 C16 H161 120.0 . . ?
C12 C17 C16 120.36(14) . . ?
C12 C17 H171 119.8 . . ?
C16 C17 H171 119.8 . . ?
H11W O1W H12W 106.4(19) . . ?
H21W O2W H22W 113(5) . . ?
H21W O2W H23W 114(4) . . ?
H31W O3W H32W 114(4) . . ?
H31W O3W H33W 110(4) . . ?
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
N1 C2 1.4578(16) . ?
N1 C7 1.4715(16) 2_556 ?
N1 C8 1.4756(14) . ?
C2 C3 1.5223(18) . ?
C2 H21 0.9900 . ?
C2 H22 0.9900 . ?
C3 N4 1.4983(16) . ?
C3 H31 0.9900 . ?
C3 H32 0.9900 . ?
N4 C5 1.5064(14) . ?
N4 C11 1.5123(16) . ?
N4 H41 0.907(18) . ?
C5 C6 1.5202(17) . ?
C5 H51 0.9900 . ?
C5 H52 0.9900 . ?
C6 C7 1.5254(16) . ?
C6 H61 0.9900 . ?
C6 H62 0.9900 . ?
C7 N1 1.4714(16) 2_556 ?
C7 H71 0.9900 . ?
C7 H72 0.9900 . ?
C8 P1 1.8246(13) . ?
C8 H81 0.9900 . ?
C8 H82 0.9900 . ?
P1 O12 1.4929(9) . ?
P1 O11 1.5092(9) . ?
P1 C9 1.8288(12) . ?
C9 C10 1.4896(19) . ?
C9 H91 0.9900 . ?
C9 H92 0.9900 . ?
C10 F3 1.3303(17) . ?
C10 F2 1.3398(16) . ?
C10 F1 1.3531(15) . ?
C11 C12 1.5087(17) . ?
C11 H111 0.9900 . ?
C11 H112 0.9900 . ?
C12 C17 1.3886(19) . ?
C12 C13 1.393(2) . ?
C13 C14 1.392(2) . ?
C13 H131 0.9500 . ?
C14 C15 1.376(3) . ?
C14 H141 0.9500 . ?
C15 C16 1.376(3) . ?
C15 H151 0.9500 . ?
C16 C17 1.396(2) . ?
C16 H161 0.9500 . ?
C17 H171 0.9500 . ?
O1W H11W 0.85(2) . ?
O1W H12W 0.87(2) . ?
O2W H21W 0.81(2) . ?
O2W H22W 0.84(2) . ?
O2W H23W 0.78(5) . ?
O3W H31W 0.82(3) . ?
O3W H32W 0.86(5) . ?
O3W H33W 0.79(6) . ?
