#------------------------------------------------------------------------------
#$Date: 2024-03-27 02:09:49 +0200 (Wed, 27 Mar 2024) $
#$Revision: 290659 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/55/7715525.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_7715525
loop_
_publ_author_name
'Koucký, Filip'
'Dobrovolná, Tereza'
'Kotek, Jan'
'Cisarova, Ivana'
'Havlickova, Jana'
'Liška, Alan'
'Kubicek, Vojtech'
'Hermann, Petr'
_publ_section_title
;
 Transition Metal Complexes of the (2,2,2-Trifluoroethyl)phosphinate NOTA
 Analogue as Potential Contrast Agents for 19F Magnetic Resonance Imaging
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D4DT00507D
_journal_year                    2024
_chemical_formula_moiety         'C2 H3 F3 O2 P, H4 N'
_chemical_formula_sum            'C2 H7 F3 N O2 P'
_chemical_formula_weight         165.06
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2024-01-20 deposited with the CCDC.	2024-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.3490(4)
_cell_length_b                   11.7365(6)
_cell_length_c                   15.2447(8)
_cell_measurement_reflns_used    9832
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      72.0772
_cell_measurement_theta_min      3.7662
_cell_volume                     1314.88(12)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 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 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            24949
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.128
_diffrn_reflns_theta_min         5.805
_diffrn_source                   'microfocus sealed tube'
_exptl_absorpt_coefficient_mu    3.857
_exptl_absorpt_correction_T_max  0.60
_exptl_absorpt_correction_T_min  0.50
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_description       prism
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.222
_exptl_crystal_size_min          0.146
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1287
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0259
_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)+(0.0364P)²+0.9615P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0759
_refine_ls_wR_factor_ref         0.0759
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1283
_reflns_number_total             1287
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt00507d2.cif
_cod_data_source_block           tfepin
_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 
;
_cod_database_code               7715525
_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   0.438
_shelx_estimated_absorpt_t_max   0.603
_shelx_res_file
;

TITL cu_fk_tfepin_kotek_0m_a.res in Pbca
    tfepin.res
    created by SHELXL-2017/1 at 11:27:03 on 05-Jan-2024
REM Old TITL cu_fk_tfepin_kotek_0m in P2(1)2(1)2(1)
REM SHELXT solution in Pbca: R1 0.120, Rweak 0.002, Alpha 0.031
REM <I/s>   3.776 for  233 systematic absences,  Orientation as input
REM Formula found by SHELXT:  C2 F3 N O2 P
CELL  1.54178   7.3490  11.7365  15.2447   90.000   90.000   90.000
ZERR    8.000   0.0004   0.0006   0.0008    0.000    0.000    0.000
LATT  1
SYMM 1/2-X, -Y, 1/2+Z
SYMM -X, 1/2+Y, 1/2-Z
SYMM 1/2+X, 1/2-Y, -Z
SFAC C H F N O P
UNIT 16 56 24 8 16 8
TEMP -153.150
SIZE 0.146 0.222 0.256
L.S. 8
BOND $H
ACTA
LIST 4
HTAB
FMAP 2
PLAN -10
WGHT    0.036400    0.961500
FVAR       0.64908
P1    6    0.411065    0.592381    0.369543    11.00000    0.01776    0.01523 =
         0.02040    0.00057    0.00020   -0.00051
H1P   2    0.465581    0.591730    0.448688    11.00000    0.02848
O1    5    0.438510    0.708607    0.331239    11.00000    0.02053    0.01856 =
         0.03426    0.00499   -0.00229   -0.00400
O2    5    0.490473    0.492337    0.321868    11.00000    0.02008    0.02018 =
         0.03537   -0.00460    0.00192    0.00138
C1    1    0.167755    0.563190    0.378336    11.00000    0.02138    0.02315 =
         0.02708    0.00221    0.00512   -0.00193
AFIX  23
H11   2    0.116194    0.560709    0.318371    11.00000   -1.20000
H12   2    0.152268    0.486482    0.404296    11.00000   -1.20000
AFIX   0
C2    1    0.058998    0.645642    0.431163    11.00000    0.03213    0.03229 =
         0.03261    0.00643    0.01165    0.00514
F1    3    0.056303    0.750510    0.396992    11.00000    0.04932    0.03066 =
         0.05371    0.00966    0.02002    0.01568
F2    3    0.121084    0.655335    0.513403    11.00000    0.06797    0.05636 =
         0.02864   -0.00647    0.01101    0.01722
F3    3   -0.116321    0.613159    0.438248    11.00000    0.03057    0.05778 =
         0.07285    0.00882    0.02553    0.00623
REM ---------------------------------------------------------------------------
N1A   4    0.725110    0.844207    0.278078    11.00000    0.01689    0.01750 =
         0.02927   -0.00013    0.00048   -0.00200
H1A   2    0.653432    0.804084    0.309152    11.00000    0.03647
H2A   2    0.659126    0.890708    0.244642    11.00000    0.03447
H3A   2    0.788279    0.800677    0.242425    11.00000    0.03424
H4A   2    0.804945    0.886649    0.309756    11.00000    0.03580

HKLF 4




REM  cu_fk_tfepin_kotek_0m_a.res in Pbca
REM R1 =  0.0259 for    1283 Fo > 4sig(Fo)  and  0.0259 for all    1287 data
REM    102 parameters refined using      0 restraints

END

WGHT      0.0364      0.9616

REM Instructions for potential hydrogen bonds
EQIV $1 x-1/2, y, -z+1/2
HTAB C1 O2_$1
HTAB N1A O1
EQIV $2 -x+1, y+1/2, -z+1/2
HTAB N1A O2_$2
EQIV $3 x+1/2, y, -z+1/2
HTAB N1A O1_$3
EQIV $4 -x+3/2, y+1/2, z
HTAB N1A O2_$4

REM Highest difference peak  0.284,  deepest hole -0.230,  1-sigma level  0.050
Q1    1   0.2732  0.5770  0.3786  11.00000  0.05    0.28
Q2    1   0.1215  0.6031  0.4033  11.00000  0.05    0.28
Q3    1   0.4353  0.6576  0.3501  11.00000  0.05    0.28
Q4    1   0.4435  0.5330  0.3408  11.00000  0.05    0.25
Q5    1   0.4968  0.4581  0.3429  11.00000  0.05    0.21
Q6    1   0.4631  0.4813  0.2944  11.00000  0.05    0.18
Q7    1   0.4648  0.7004  0.3007  11.00000  0.05    0.17
Q8    1   0.4580  0.6018  0.4144  11.00000  0.05    0.17
Q9    1   0.1551  0.5264  0.3981  11.00000  0.05    0.14
Q10   1   0.1534  0.7644  0.4361  11.00000  0.05    0.12
;
_shelx_res_checksum              74760
loop_
_space_group_symop_operation_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'
'-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_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 0.41107(5) 0.59238(3) 0.36954(2) 0.01779(15) Uani 1 1 d . . . . .
H1P H 0.466(3) 0.5917(16) 0.4487(13) 0.028(5) Uiso 1 1 d . . . . .
O1 O 0.43851(14) 0.70861(9) 0.33124(7) 0.0244(3) Uani 1 1 d . . . . .
O2 O 0.49047(15) 0.49234(9) 0.32187(7) 0.0252(3) Uani 1 1 d . . . . .
C1 C 0.1678(2) 0.56319(14) 0.37834(10) 0.0239(3) Uani 1 1 d . . . . .
H11 H 0.116194 0.560709 0.318371 0.029 Uiso 1 1 calc R U . . .
H12 H 0.152268 0.486482 0.404296 0.029 Uiso 1 1 calc R U . . .
C2 C 0.0590(3) 0.64564(15) 0.43116(12) 0.0323(4) Uani 1 1 d . . . . .
F1 F 0.05630(16) 0.75051(9) 0.39699(8) 0.0446(3) Uani 1 1 d . . . . .
F2 F 0.12108(19) 0.65534(11) 0.51340(7) 0.0510(4) Uani 1 1 d . . . . .
F3 F -0.11632(16) 0.61316(12) 0.43825(9) 0.0537(4) Uani 1 1 d . . . . .
N1A N 0.72511(18) 0.84421(11) 0.27808(10) 0.0212(3) Uani 1 1 d . . . . .
H1A H 0.653(3) 0.8041(19) 0.3092(14) 0.036(6) Uiso 1 1 d . . . . .
H2A H 0.659(3) 0.8907(19) 0.2446(15) 0.034(5) Uiso 1 1 d . . . . .
H3A H 0.788(3) 0.8007(19) 0.2424(14) 0.034(5) Uiso 1 1 d . . . . .
H4A H 0.805(3) 0.8866(19) 0.3098(14) 0.036(6) Uiso 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
P1 0.0178(2) 0.0152(2) 0.0204(2) 0.00057(13) 0.00020(13) -0.00051(13)
O1 0.0205(5) 0.0186(5) 0.0343(6) 0.0050(4) -0.0023(5) -0.0040(4)
O2 0.0201(5) 0.0202(5) 0.0354(6) -0.0046(4) 0.0019(5) 0.0014(4)
C1 0.0214(8) 0.0231(7) 0.0271(8) 0.0022(6) 0.0051(6) -0.0019(6)
C2 0.0321(9) 0.0323(9) 0.0326(9) 0.0064(7) 0.0116(7) 0.0051(7)
F1 0.0493(7) 0.0307(6) 0.0537(7) 0.0097(5) 0.0200(6) 0.0157(5)
F2 0.0680(9) 0.0564(8) 0.0286(6) -0.0065(5) 0.0110(5) 0.0172(6)
F3 0.0306(6) 0.0578(8) 0.0729(9) 0.0088(7) 0.0255(6) 0.0062(5)
N1A 0.0169(6) 0.0175(6) 0.0293(7) -0.0001(5) 0.0005(6) -0.0020(5)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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
O1 P1 O2 118.16(7) . . ?
O1 P1 C1 109.36(7) . . ?
O2 P1 C1 105.66(7) . . ?
O1 P1 H1P 109.5(9) . . ?
O2 P1 H1P 109.4(9) . . ?
C1 P1 H1P 103.8(10) . . ?
C2 C1 P1 116.28(12) . . ?
C2 C1 H11 108.2 . . ?
P1 C1 H11 108.2 . . ?
C2 C1 H12 108.2 . . ?
P1 C1 H12 108.2 . . ?
H11 C1 H12 107.4 . . ?
F1 C2 F2 106.96(16) . . ?
F1 C2 F3 106.11(15) . . ?
F2 C2 F3 105.94(14) . . ?
F1 C2 C1 113.27(14) . . ?
F2 C2 C1 112.22(15) . . ?
F3 C2 C1 111.84(16) . . ?
H1A N1A H2A 109(2) . . ?
H1A N1A H3A 110.5(19) . . ?
H2A N1A H3A 106.9(19) . . ?
H1A N1A H4A 114(2) . . ?
H2A N1A H4A 108.7(18) . . ?
H3A N1A H4A 108(2) . . ?
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 O1 1.4975(11) . ?
P1 O2 1.4992(11) . ?
P1 C1 1.8255(17) . ?
P1 H1P 1.27(2) . ?
C1 C2 1.491(2) . ?
C1 H11 0.9900 . ?
C1 H12 0.9900 . ?
C2 F1 1.337(2) . ?
C2 F2 1.339(2) . ?
C2 F3 1.348(2) . ?
N1A H1A 0.85(2) . ?
N1A H2A 0.89(2) . ?
N1A H3A 0.88(2) . ?
N1A H4A 0.91(2) . ?
