# Supplementary Information (SI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cute2pcm
_database_code_depnum_ccdc_archive 'CCDC 2489251'
loop_
_audit_author_name
_audit_author_address
'Jan Kotek'
;Faculty of Science, Charles University, Prague
Czech Republic
;
_audit_update_record             
;
2025-09-18 deposited with the CCDC.	2025-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H32 Cu N4 O8 P2, 2(H2 O)'
_chemical_formula_sum            'C16 H36 Cu N4 O10 P2'
_chemical_formula_weight         569.97

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'
Cu Cu 0.3201 1.2651 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1026(7)
_cell_length_b                   8.8622(7)
_cell_length_c                   9.2776(8)
_cell_angle_alpha                71.336(3)
_cell_angle_beta                 65.675(3)
_cell_angle_gamma                79.661(3)
_cell_volume                     574.25(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8775
_cell_measurement_theta_min      2.5055
_cell_measurement_theta_max      27.5024

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_F_000             299
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.216
_exptl_crystal_size_mid          0.189
_exptl_crystal_size_min          0.179
_exptl_absorpt_coefficient_mu    1.151
_shelx_estimated_absorpt_T_min   0.789
_shelx_estimated_absorpt_T_max   0.820
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.62
_exptl_absorpt_correction_T_max  0.82
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 7.391
_diffrn_reflns_number            8746
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.429
_diffrn_reflns_theta_max         27.502
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2627
_reflns_number_gt                2417
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service vV6.2.15'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0973P)²+0.5569P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2627
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1418
_refine_ls_wR_factor_gt          0.1350
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Cu1 Cu 0.5000 0.5000 0.5000 0.01899(17) Uani 1 2 d S . P . .
N1 N 0.6635(3) 0.5704(3) 0.2483(3) 0.0218(4) Uani 1 1 d . . . . .
C2 C 0.7954(3) 0.6718(3) 0.2444(3) 0.0258(5) Uani 1 1 d . . . . .
H21 H 0.8626 0.7326 0.1297 0.031 Uiso 1 1 calc R U . . .
H22H H 0.8841 0.6036 0.2888 0.031 Uiso 1 1 calc R U . . .
C3 C 0.6914(4) 0.7860(3) 0.3478(4) 0.0281(6) Uani 1 1 d . . . . .
H31 H 0.7767 0.8504 0.3516 0.034 Uiso 1 1 calc R U . . .
H32 H 0.6086 0.8593 0.2992 0.034 Uiso 1 1 calc R U . . .
N4 N 0.5861(3) 0.6906(3) 0.5158(3) 0.0247(5) Uani 1 1 d . . . . .
H41 H 0.655(5) 0.655(5) 0.563(5) 0.032(9) Uiso 1 1 d . . . . .
C5 C 0.4462(4) 0.7901(3) 0.6135(4) 0.0286(6) Uani 1 1 d . . . . .
H51 H 0.3552 0.8343 0.5629 0.034 Uiso 1 1 calc R U . . .
H52 H 0.5037 0.8806 0.6118 0.034 Uiso 1 1 calc R U . . .
C6 C 0.3521(4) 0.6948(3) 0.7898(4) 0.0296(6) Uani 1 1 d . . . . .
H61 H 0.4456 0.6429 0.8355 0.036 Uiso 1 1 calc R U . . .
H62 H 0.2761 0.7695 0.8544 0.036 Uiso 1 1 calc R U . . .
C7 C 0.2345(4) 0.5685(3) 0.8129(3) 0.0273(5) Uani 1 1 d . . . . .
H71 H 0.1599 0.5295 0.9316 0.033 Uiso 1 1 calc R U . . .
H72 H 0.1507 0.6178 0.7553 0.033 Uiso 1 1 calc R U . . .
C8 C 0.5644(3) 0.6682(3) 0.1408(3) 0.0241(5) Uani 1 1 d . . . . .
H81 H 0.6058 0.6295 0.0418 0.029 Uiso 1 1 calc R U . . .
H82 H 0.5983 0.7802 0.1037 0.029 Uiso 1 1 calc R U . . .
P1 P 0.31669(8) 0.66464(8) 0.23816(8) 0.02088(19) Uani 1 1 d . . . . .
O11 O 0.2644(2) 0.6523(2) 0.4176(2) 0.0252(4) Uani 1 1 d . . . . .
O12 O 0.2515(3) 0.5421(2) 0.1971(2) 0.0267(4) Uani 1 1 d . . . . .
C9 C 0.2419(4) 0.8613(3) 0.1375(3) 0.0241(5) Uani 1 1 d . . . . .
H91 H 0.3208 0.8894 0.0192 0.029 Uiso 1 1 calc R U . . .
H92 H 0.1166 0.8571 0.1466 0.029 Uiso 1 1 calc R U . . .
C10 C 0.2461(4) 0.9894(3) 0.2095(3) 0.0248(5) Uani 1 1 d . . . . .
O101 O 0.0850(3) 1.0555(3) 0.2767(3) 0.0345(5) Uani 1 1 d . . . . .
H101 H 0.1043 1.1301 0.3196 0.041 Uiso 1 1 d R U . . .
O102 O 0.3853(3) 1.0294(2) 0.2031(3) 0.0304(4) Uani 1 1 d . . . . .
O1W O 0.0846(3) 1.2787(2) 0.3987(2) 0.0282(4) Uani 1 1 d . . . . .
H11W H 0.1240 1.3680 0.3273 0.039(10) Uiso 1 1 d R . . . .
H12W H -0.0249 1.2980 0.4541 0.045(11) Uiso 1 1 d R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Cu1 N4 2.006(2) 2_666 ?
Cu1 N4 2.006(2) . ?
Cu1 N1 2.101(2) 2_666 ?
Cu1 N1 2.101(2) . ?
Cu1 O11 2.3802(18) 2_666 ?
Cu1 O11 2.3803(18) . ?
N1 C7 1.489(3) 2_666 ?
N1 C2 1.499(3) . ?
N1 C8 1.499(3) . ?
C2 C3 1.517(4) . ?
C2 H21 0.9900 . ?
C2 H22H 0.9900 . ?
C3 N4 1.481(4) . ?
C3 H31 0.9900 . ?
C3 H32 0.9900 . ?
N4 C5 1.480(3) . ?
N4 H41 0.80(4) . ?
C5 C6 1.513(4) . ?
C5 H51 0.9900 . ?
C5 H52 0.9900 . ?
C6 C7 1.505(4) . ?
C6 H61 0.9900 . ?
C6 H62 0.9900 . ?
C7 N1 1.489(3) 2_666 ?
C7 H71 0.9900 . ?
C7 H72 0.9900 . ?
C8 P1 1.832(3) . ?
C8 H81 0.9900 . ?
C8 H82 0.9900 . ?
P1 O12 1.4970(19) . ?
P1 O11 1.5110(19) . ?
P1 C9 1.823(3) . ?
C9 C10 1.501(4) . ?
C9 H91 0.9900 . ?
C9 H92 0.9900 . ?
C10 O102 1.215(3) . ?
C10 O101 1.313(3) . ?
O101 H101 0.9365 . ?
O1W H11W 0.8651 . ?
O1W H12W 0.8408 . ?

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
N4 Cu1 N4 180.00(13) 2_666 . ?
N4 Cu1 N1 86.06(9) 2_666 2_666 ?
N4 Cu1 N1 93.94(9) . 2_666 ?
N4 Cu1 N1 93.94(9) 2_666 . ?
N4 Cu1 N1 86.06(9) . . ?
N1 Cu1 N1 180.00(9) 2_666 . ?
N4 Cu1 O11 93.10(8) 2_666 2_666 ?
N4 Cu1 O11 86.90(8) . 2_666 ?
N1 Cu1 O11 84.69(7) 2_666 2_666 ?
N1 Cu1 O11 95.31(7) . 2_666 ?
N4 Cu1 O11 86.90(8) 2_666 . ?
N4 Cu1 O11 93.10(8) . . ?
N1 Cu1 O11 95.31(7) 2_666 . ?
N1 Cu1 O11 84.69(7) . . ?
O11 Cu1 O11 180.0 2_666 . ?
C7 N1 C2 108.8(2) 2_666 . ?
C7 N1 C8 110.3(2) 2_666 . ?
C2 N1 C8 109.0(2) . . ?
C7 N1 Cu1 111.68(16) 2_666 . ?
C2 N1 Cu1 102.24(15) . . ?
C8 N1 Cu1 114.46(15) . . ?
N1 C2 C3 108.8(2) . . ?
N1 C2 H21 109.9 . . ?
C3 C2 H21 109.9 . . ?
N1 C2 H22H 109.9 . . ?
C3 C2 H22H 109.9 . . ?
H21 C2 H22H 108.3 . . ?
N4 C3 C2 108.1(2) . . ?
N4 C3 H31 110.1 . . ?
C2 C3 H31 110.1 . . ?
N4 C3 H32 110.1 . . ?
C2 C3 H32 110.1 . . ?
H31 C3 H32 108.4 . . ?
C5 N4 C3 111.9(2) . . ?
C5 N4 Cu1 116.43(18) . . ?
C3 N4 Cu1 108.84(17) . . ?
C5 N4 H41 106(3) . . ?
C3 N4 H41 108(3) . . ?
Cu1 N4 H41 105(3) . . ?
N4 C5 C6 111.5(2) . . ?
N4 C5 H51 109.3 . . ?
C6 C5 H51 109.3 . . ?
N4 C5 H52 109.3 . . ?
C6 C5 H52 109.3 . . ?
H51 C5 H52 108.0 . . ?
C7 C6 C5 115.1(2) . . ?
C7 C6 H61 108.5 . . ?
C5 C6 H61 108.5 . . ?
C7 C6 H62 108.5 . . ?
C5 C6 H62 108.5 . . ?
H61 C6 H62 107.5 . . ?
N1 C7 C6 114.4(2) 2_666 . ?
N1 C7 H71 108.7 2_666 . ?
C6 C7 H71 108.7 . . ?
N1 C7 H72 108.7 2_666 . ?
C6 C7 H72 108.7 . . ?
H71 C7 H72 107.6 . . ?
N1 C8 P1 115.02(17) . . ?
N1 C8 H81 108.5 . . ?
P1 C8 H81 108.5 . . ?
N1 C8 H82 108.5 . . ?
P1 C8 H82 108.5 . . ?
H81 C8 H82 107.5 . . ?
O12 P1 O11 117.95(11) . . ?
O12 P1 C9 108.24(11) . . ?
O11 P1 C9 109.08(12) . . ?
O12 P1 C8 110.35(12) . . ?
O11 P1 C8 107.16(11) . . ?
C9 P1 C8 103.03(12) . . ?
P1 O11 Cu1 107.92(10) . . ?
C10 C9 P1 113.14(18) . . ?
C10 C9 H91 109.0 . . ?
P1 C9 H91 109.0 . . ?
C10 C9 H92 109.0 . . ?
P1 C9 H92 109.0 . . ?
H91 C9 H92 107.8 . . ?
O102 C10 O101 123.7(3) . . ?
O102 C10 C9 123.1(2) . . ?
O101 C10 C9 113.2(2) . . ?
C10 O101 H101 105.4 . . ?
H11W O1W H12W 106.0 . . ?

_refine_diff_density_max         1.734
_refine_diff_density_min         -1.033
_refine_diff_density_rms         0.142

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_dotptfe
_database_code_depnum_ccdc_archive 'CCDC 2489253'
loop_
_audit_author_name
_audit_author_address
'Jan Kotek'
;Faculty of Science, Charles University, Prague
Czech Republic
;
_audit_update_record             
;
2025-11-10 deposited with the CCDC.	2025-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H15 F9 N O6 P3'
_chemical_formula_sum            'C9 H15 F9 N O6 P3'
_chemical_formula_weight         497.13

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9880(2)
_cell_length_b                   9.1058(2)
_cell_length_c                   13.0820(3)
_cell_angle_alpha                77.8110(10)
_cell_angle_beta                 74.4370(10)
_cell_angle_gamma                61.3910(10)
_cell_volume                     901.15(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6976
_cell_measurement_theta_min      2.7275
_cell_measurement_theta_max      27.4980

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.832
_exptl_crystal_F_000             500
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.393
_exptl_crystal_size_mid          0.285
_exptl_crystal_size_min          0.098
_exptl_absorpt_coefficient_mu    0.449
_shelx_estimated_absorpt_T_min   0.843
_shelx_estimated_absorpt_T_max   0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            13164
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.624
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             4095
_reflns_number_gt                3542
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service v2015.3.1.0'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0574P)²+0.5867P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4095
_refine_ls_number_parameters     287
_refine_ls_number_restraints     90
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.1024
_refine_ls_wR_factor_gt          0.0975
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.19930(18) 0.69011(17) 0.86737(12) 0.0150(3) Uani 1 1 d . . . . .
C1 C 0.3479(2) 0.5470(2) 0.90748(14) 0.0169(3) Uani 1 1 d . . . . .
H11 H 0.306815 0.507262 0.980859 0.020 Uiso 1 1 calc R U . . .
H12 H 0.431276 0.586659 0.911182 0.020 Uiso 1 1 calc R U . . .
P1 P 0.45851(6) 0.37240(5) 0.82713(4) 0.01614(12) Uani 1 1 d . . . . .
O11 O 0.61812(17) 0.26072(16) 0.87959(11) 0.0247(3) Uani 1 1 d . . . . .
H11O H 0.682064 0.161369 0.858733 0.030 Uiso 1 1 d R U . . .
O12 O 0.35185(18) 0.29225(17) 0.82014(11) 0.0244(3) Uani 1 1 d . . . . .
C2 C 0.5259(2) 0.4608(2) 0.69581(15) 0.0233(4) Uani 1 1 d . . . . .
H21 H 0.421843 0.534427 0.664588 0.028 Uiso 1 1 calc R U . . .
H22 H 0.575613 0.532755 0.704413 0.028 Uiso 1 1 calc R U . . .
C3 C 0.6542(3) 0.3383(3) 0.61818(18) 0.0353(5) Uani 1 1 d . . . . .
F31 F 0.6843(2) 0.4148(2) 0.52134(11) 0.0484(4) Uani 1 1 d . . . . .
F32 F 0.80801(19) 0.2501(2) 0.64737(13) 0.0600(5) Uani 1 1 d . . . . .
F33 F 0.6059(3) 0.2279(3) 0.60682(15) 0.0763(7) Uani 1 1 d . . . . .
C11 C 0.1628(2) 0.8436(2) 0.91061(15) 0.0175(3) Uani 1 1 d . . . . .
H111 H 0.179179 0.814796 0.985426 0.021 Uiso 1 1 calc R U . . .
H112 H 0.040371 0.925345 0.910880 0.021 Uiso 1 1 calc R U . . .
P2 P 0.29767(6) 0.94139(6) 0.83651(4) 0.01695(12) Uani 1 1 d . . . . .
O21 O 0.24689(18) 1.07873(17) 0.90961(11) 0.0260(3) Uani 1 1 d . . . . .
H21O H 0.301342 1.141430 0.883451 0.031 Uiso 1 1 d R U . . .
O22 O 0.48455(16) 0.82016(17) 0.81258(11) 0.0224(3) Uani 1 1 d . . . . .
C12 C 0.2228(3) 1.0595(2) 0.71520(17) 0.0264(4) Uani 1 1 d . . . . .
H121 H 0.094940 1.115409 0.732119 0.032 Uiso 1 1 calc R U . . .
H122 H 0.260484 1.149373 0.695460 0.032 Uiso 1 1 calc R U . . .
C13 C 0.2776(3) 0.9687(3) 0.61905(17) 0.0292(4) Uani 1 1 d . . . . .
F131 F 0.2160(2) 0.85640(18) 0.63326(11) 0.0432(4) Uani 1 1 d . . . . .
F132 F 0.44821(18) 0.8837(2) 0.58910(11) 0.0477(4) Uani 1 1 d . . . . .
F133 F 0.2200(2) 1.07574(19) 0.53496(11) 0.0457(4) Uani 1 1 d . . . . .
C21 C 0.0472(2) 0.6577(2) 0.89938(14) 0.0162(3) Uani 1 1 d . . . . .
H211 H 0.005961 0.663787 0.977265 0.019 Uiso 1 1 calc R U . . .
H212 H 0.083433 0.541462 0.885263 0.019 Uiso 1 1 calc R U . . .
P3 P -0.13207(6) 0.79894(6) 0.83386(4) 0.01668(12) Uani 1 1 d D . . . .
O31 O -0.27657(17) 0.75542(18) 0.90511(11) 0.0259(3) Uani 1 1 d . . . . .
H31O H -0.378121 0.794125 0.872912 0.031 Uiso 1 1 d R U . . .
O32 O -0.16430(17) 0.97745(16) 0.82177(11) 0.0241(3) Uani 1 1 d . . . . .
C22A C -0.1097(4) 0.7524(3) 0.70132(18) 0.0224(5) Uani 0.836(4) 1 d D . P A 1
H221 H -0.221776 0.824220 0.678410 0.027 Uiso 0.836(4) 1 calc R U P A 1
H222 H -0.023922 0.786708 0.652745 0.027 Uiso 0.836(4) 1 calc R U P A 1
C22B C -0.0412(18) 0.7084(16) 0.7061(8) 0.0224(5) Uani 0.164(4) 1 d D . P A 2
H223 H -0.096645 0.798688 0.651784 0.027 Uiso 0.164(4) 1 calc R U P A 2
H224 H 0.082551 0.682292 0.688935 0.027 Uiso 0.164(4) 1 calc R U P A 2
C23A C -0.0568(4) 0.5745(4) 0.6853(2) 0.0290(5) Uani 0.836(4) 1 d D . P A 1
F231 F 0.1133(2) 0.4805(2) 0.67716(17) 0.0459(5) Uani 0.836(4) 1 d D U P A 1
F232 F -0.1306(4) 0.4975(3) 0.76516(17) 0.0498(6) Uani 0.836(4) 1 d D U P A 1
F233 F -0.0967(3) 0.5657(3) 0.59723(16) 0.0574(7) Uani 0.836(4) 1 d D U P A 1
C23B C -0.0505(11) 0.5560(13) 0.6890(7) 0.0290(5) Uani 0.164(4) 1 d D . P A 2
F234 F 0.0673(13) 0.4719(12) 0.6084(8) 0.052(3) Uani 0.164(4) 1 d D U P A 2
F235 F -0.0249(16) 0.4425(12) 0.7741(8) 0.045(2) Uani 0.164(4) 1 d D U P A 2
F236 F -0.2067(12) 0.5973(12) 0.6725(10) 0.055(3) Uani 0.164(4) 1 d D U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 C21 1.470(2) . ?
N1 C11 1.475(2) . ?
N1 C1 1.476(2) . ?
C1 P1 1.8036(18) . ?
C1 H11 0.9900 . ?
C1 H12 0.9900 . ?
P1 O12 1.4850(14) . ?
P1 O11 1.5491(13) . ?
P1 C2 1.8140(19) . ?
O11 H11O 0.8634 . ?
C2 C3 1.491(3) . ?
C2 H21 0.9900 . ?
C2 H22 0.9900 . ?
C3 F33 1.317(3) . ?
C3 F31 1.337(3) . ?
C3 F32 1.339(3) . ?
C11 P2 1.7999(18) . ?
C11 H111 0.9900 . ?
C11 H112 0.9900 . ?
P2 O22 1.4920(13) . ?
P2 O21 1.5527(14) . ?
P2 C12 1.813(2) . ?
O21 H21O 0.8819 . ?
C12 C13 1.492(3) . ?
C12 H121 0.9900 . ?
C12 H122 0.9900 . ?
C13 F132 1.332(3) . ?
C13 F131 1.339(3) . ?
C13 F133 1.340(2) . ?
C21 P3 1.8099(17) . ?
C21 H211 0.9900 . ?
C21 H212 0.9900 . ?
P3 O32 1.4886(14) . ?
P3 O31 1.5492(14) . ?
P3 C22A 1.808(2) . ?
P3 C22B 1.829(8) . ?
O31 H31O 0.9850 . ?
C22A C23A 1.499(3) . ?
C22A H221 0.9900 . ?
C22A H222 0.9900 . ?
C22B C23B 1.495(9) . ?
C22B H223 0.9900 . ?
C22B H224 0.9900 . ?
C23A F233 1.323(3) . ?
C23A F231 1.334(3) . ?
C23A F232 1.337(3) . ?
C23B F236 1.335(6) . ?
C23B F234 1.335(6) . ?
C23B F235 1.336(6) . ?

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
C21 N1 C11 110.31(13) . . ?
C21 N1 C1 110.17(13) . . ?
C11 N1 C1 108.97(13) . . ?
N1 C1 P1 114.11(12) . . ?
N1 C1 H11 108.7 . . ?
P1 C1 H11 108.7 . . ?
N1 C1 H12 108.7 . . ?
P1 C1 H12 108.7 . . ?
H11 C1 H12 107.6 . . ?
O12 P1 O11 116.55(8) . . ?
O12 P1 C1 114.83(8) . . ?
O11 P1 C1 100.71(8) . . ?
O12 P1 C2 109.88(9) . . ?
O11 P1 C2 109.43(9) . . ?
C1 P1 C2 104.50(9) . . ?
P1 O11 H11O 115.9 . . ?
C3 C2 P1 116.37(14) . . ?
C3 C2 H21 108.2 . . ?
P1 C2 H21 108.2 . . ?
C3 C2 H22 108.2 . . ?
P1 C2 H22 108.2 . . ?
H21 C2 H22 107.3 . . ?
F33 C3 F31 107.2(2) . . ?
F33 C3 F32 106.6(2) . . ?
F31 C3 F32 105.66(19) . . ?
F33 C3 C2 113.1(2) . . ?
F31 C3 C2 111.93(18) . . ?
F32 C3 C2 111.9(2) . . ?
N1 C11 P2 113.52(12) . . ?
N1 C11 H111 108.9 . . ?
P2 C11 H111 108.9 . . ?
N1 C11 H112 108.9 . . ?
P2 C11 H112 108.9 . . ?
H111 C11 H112 107.7 . . ?
O22 P2 O21 116.55(8) . . ?
O22 P2 C11 113.25(8) . . ?
O21 P2 C11 100.69(8) . . ?
O22 P2 C12 110.78(9) . . ?
O21 P2 C12 104.05(9) . . ?
C11 P2 C12 110.80(9) . . ?
P2 O21 H21O 112.5 . . ?
C13 C12 P2 118.85(14) . . ?
C13 C12 H121 107.6 . . ?
P2 C12 H121 107.6 . . ?
C13 C12 H122 107.6 . . ?
P2 C12 H122 107.6 . . ?
H121 C12 H122 107.0 . . ?
F132 C13 F131 105.83(18) . . ?
F132 C13 F133 106.55(18) . . ?
F131 C13 F133 106.39(18) . . ?
F132 C13 C12 113.83(19) . . ?
F131 C13 C12 112.60(18) . . ?
F133 C13 C12 111.13(18) . . ?
N1 C21 P3 115.62(12) . . ?
N1 C21 H211 108.4 . . ?
P3 C21 H211 108.4 . . ?
N1 C21 H212 108.4 . . ?
P3 C21 H212 108.4 . . ?
H211 C21 H212 107.4 . . ?
O32 P3 O31 117.24(8) . . ?
O32 P3 C22A 105.35(10) . . ?
O31 P3 C22A 105.90(10) . . ?
O32 P3 C21 113.14(8) . . ?
O31 P3 C21 100.48(8) . . ?
C22A P3 C21 114.90(11) . . ?
O32 P3 C22B 111.9(4) . . ?
O31 P3 C22B 114.4(4) . . ?
C21 P3 C22B 97.4(5) . . ?
P3 O31 H31O 114.4 . . ?
C23A C22A P3 118.00(18) . . ?
C23A C22A H221 107.8 . . ?
P3 C22A H221 107.8 . . ?
C23A C22A H222 107.8 . . ?
P3 C22A H222 107.8 . . ?
H221 C22A H222 107.1 . . ?
C23B C22B P3 122.2(8) . . ?
C23B C22B H223 106.8 . . ?
P3 C22B H223 106.8 . . ?
C23B C22B H224 106.8 . . ?
P3 C22B H224 106.8 . . ?
H223 C22B H224 106.6 . . ?
F233 C23A F231 107.1(2) . . ?
F233 C23A F232 106.6(3) . . ?
F231 C23A F232 106.0(2) . . ?
F233 C23A C22A 111.6(2) . . ?
F231 C23A C22A 111.4(2) . . ?
F232 C23A C22A 113.5(2) . . ?
F236 C23B F234 108.1(9) . . ?
F236 C23B F235 106.7(10) . . ?
F234 C23B F235 104.5(9) . . ?
F236 C23B C22B 110.4(9) . . ?
F234 C23B C22B 115.0(8) . . ?
F235 C23B C22B 111.7(9) . . ?

_refine_diff_density_max         0.725
_refine_diff_density_min         -0.617
_refine_diff_density_rms         0.070

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_morphtfe
_database_code_depnum_ccdc_archive 'CCDC 2489252'
loop_
_audit_author_name
_audit_author_address
'Jan Kotek'
;Faculty of Science, Charles University, Prague
Czech Republic
;
_audit_update_record             
;
2025-11-10 deposited with the CCDC.	2025-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H11 F3 N O, Cl'
_chemical_formula_sum            'C6 H11 Cl F3 N O'
_chemical_formula_weight         205.61

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'
Cl Cl 0.1484 0.1585 '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'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9673(7)
_cell_length_b                   8.4006(8)
_cell_length_c                   8.7777(9)
_cell_angle_alpha                61.809(3)
_cell_angle_beta                 83.564(3)
_cell_angle_gamma                84.306(3)
_cell_volume                     449.33(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9345
_cell_measurement_theta_min      2.7545
_cell_measurement_theta_max      29.9943

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_F_000             212
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.333
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.194
_exptl_absorpt_coefficient_mu    0.428
_shelx_estimated_absorpt_T_min   0.871
_shelx_estimated_absorpt_T_max   0.922
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.92
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            48200
_diffrn_reflns_av_unetI/netI     0.0100
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.640
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             2604
_reflns_number_gt                2557
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service vV6.2.16'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0273P)²+0.1142P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2604
_refine_ls_number_parameters     144
_refine_ls_number_restraints     50
_refine_ls_R_factor_all          0.0219
_refine_ls_R_factor_gt           0.0216
_refine_ls_wR_factor_ref         0.0603
_refine_ls_wR_factor_gt          0.0601
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
O1 O 0.79846(10) 0.12868(8) 0.43812(8) 0.02558(13) Uani 1 1 d . . . . .
C2 C 0.73443(13) -0.01183(11) 0.60237(11) 0.02409(16) Uani 1 1 d . . . . .
H2A H 0.781095 -0.130457 0.610098 0.029 Uiso 1 1 calc R U . . .
H2B H 0.591277 -0.007734 0.614090 0.029 Uiso 1 1 calc R U . . .
C3 C 0.80825(11) 0.00704(9) 0.74874(10) 0.01805(14) Uani 1 1 d . . . . .
H3A H 0.760371 -0.091016 0.861545 0.022 Uiso 1 1 calc R U . . .
H3B H 0.951394 -0.003581 0.741228 0.022 Uiso 1 1 calc R U . . .
N4 N 0.73926(8) 0.18861(8) 0.73711(7) 0.01337(11) Uani 1 1 d . . . . .
H4 H 0.6101(18) 0.1916(16) 0.7497(16) 0.028(3) Uiso 1 1 d . . . . .
C5 C 0.79858(11) 0.33522(9) 0.55948(9) 0.01696(13) Uani 1 1 d . . . . .
H5A H 0.941323 0.338619 0.543751 0.020 Uiso 1 1 calc R U . . .
H5B H 0.744554 0.454019 0.546820 0.020 Uiso 1 1 calc R U . . .
C6 C 0.72498(12) 0.29925(11) 0.42309(10) 0.02174(15) Uani 1 1 d . . . . .
H6A H 0.581874 0.301805 0.435958 0.026 Uiso 1 1 calc R U . . .
H6B H 0.764645 0.395977 0.306431 0.026 Uiso 1 1 calc R U . . .
C7 C 0.81696(10) 0.20409(10) 0.88049(9) 0.01616(13) Uani 1 1 d D . . . .
H7A1 H 0.959995 0.196777 0.865839 0.019 Uiso 0.590(14) 1 calc R U P A 1
H7A2 H 0.777148 0.099209 0.991570 0.019 Uiso 0.590(14) 1 calc R U P A 1
H7B1 H 0.958218 0.217616 0.855360 0.019 Uiso 0.410(14) 1 calc R U P A 2
H7B2 H 0.796454 0.089940 0.988907 0.019 Uiso 0.410(14) 1 calc R U P A 2
C8A C 0.7532(8) 0.3742(5) 0.8923(7) 0.0244(4) Uani 0.590(14) 1 d D . P A 1
F83A F 0.5631(6) 0.4077(8) 0.8909(7) 0.0466(9) Uani 0.590(14) 1 d D U P A 1
F82A F 0.8342(9) 0.5214(4) 0.7649(3) 0.0405(7) Uani 0.590(14) 1 d D U P A 1
F81A F 0.8022(16) 0.3550(16) 1.0433(12) 0.0390(13) Uani 0.590(14) 1 d D U P A 1
C8B C 0.7284(10) 0.3591(8) 0.9103(11) 0.0244(4) Uani 0.410(14) 1 d D . P A 2
F81B F 0.821(2) 0.364(2) 1.0333(17) 0.0343(13) Uani 0.410(14) 1 d D U P A 2
F82B F 0.7471(17) 0.5223(5) 0.7752(5) 0.0461(13) Uani 0.410(14) 1 d D U P A 2
F83B F 0.5409(5) 0.3434(12) 0.9594(14) 0.0527(13) Uani 0.410(14) 1 d D U P A 2
Cl1 Cl 0.30261(2) 0.20299(2) 0.74503(2) 0.02333(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O1 C2 1.4224(10) . ?
O1 C6 1.4226(10) . ?
C2 C3 1.5157(11) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 N4 1.5121(9) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
N4 C7 1.4884(9) . ?
N4 C5 1.5037(9) . ?
N4 H4 0.894(13) . ?
C5 C6 1.5158(10) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8A 1.502(4) . ?
C7 C8B 1.508(6) . ?
C7 H7A1 0.9900 . ?
C7 H7A2 0.9900 . ?
C7 H7B1 0.9900 . ?
C7 H7B2 0.9900 . ?
C8A F83A 1.326(4) . ?
C8A F81A 1.337(5) . ?
C8A F82A 1.337(4) . ?
C8B F83B 1.328(6) . ?
C8B F82B 1.330(6) . ?
C8B F81B 1.338(6) . ?

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 O1 C6 109.74(6) . . ?
O1 C2 C3 111.18(6) . . ?
O1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
O1 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
N4 C3 C2 109.81(6) . . ?
N4 C3 H3A 109.7 . . ?
C2 C3 H3A 109.7 . . ?
N4 C3 H3B 109.7 . . ?
C2 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C7 N4 C5 113.90(5) . . ?
C7 N4 C3 108.44(5) . . ?
C5 N4 C3 108.97(5) . . ?
C7 N4 H4 109.9(8) . . ?
C5 N4 H4 108.0(8) . . ?
C3 N4 H4 107.5(8) . . ?
N4 C5 C6 109.68(6) . . ?
N4 C5 H5A 109.7 . . ?
C6 C5 H5A 109.7 . . ?
N4 C5 H5B 109.7 . . ?
C6 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
O1 C6 C5 111.35(6) . . ?
O1 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
O1 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
N4 C7 C8A 115.1(2) . . ?
N4 C7 C8B 115.0(4) . . ?
N4 C7 H7A1 108.5 . . ?
C8A C7 H7A1 108.5 . . ?
N4 C7 H7A2 108.5 . . ?
C8A C7 H7A2 108.5 . . ?
H7A1 C7 H7A2 107.5 . . ?
N4 C7 H7B1 108.5 . . ?
C8B C7 H7B1 108.5 . . ?
N4 C7 H7B2 108.5 . . ?
C8B C7 H7B2 108.5 . . ?
H7B1 C7 H7B2 107.5 . . ?
F83A C8A F81A 106.5(6) . . ?
F83A C8A F82A 107.1(3) . . ?
F81A C8A F82A 108.1(6) . . ?
F83A C8A C7 113.1(4) . . ?
F81A C8A C7 108.5(7) . . ?
F82A C8A C7 113.3(3) . . ?
F83B C8B F82B 106.7(5) . . ?
F83B C8B F81B 109.3(9) . . ?
F82B C8B F81B 104.5(9) . . ?
F83B C8B C7 112.5(5) . . ?
F82B C8B C7 115.2(5) . . ?
F81B C8B C7 108.3(10) . . ?

_refine_diff_density_max         0.456
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.036

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_tfepon
_database_code_depnum_ccdc_archive 'CCDC 2489254'
loop_
_audit_author_name
_audit_author_address
'Jan Kotek'
;Faculty of Science, Charles University, Prague
Czech Republic
;
_audit_update_record             
;
2025-09-18 deposited with the CCDC.	2025-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C2 H3 F3 O3 P, H4 N'
_chemical_formula_sum            'C2 H7 F3 N O3 P'
_chemical_formula_weight         181.06

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_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.
;

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'

_cell_length_a                   10.8639(11)
_cell_length_b                   23.001(2)
_cell_length_c                   7.7886(14)
_cell_angle_alpha                90
_cell_angle_beta                 133.943(2)
_cell_angle_gamma                90
_cell_volume                     1401.3(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9893
_cell_measurement_theta_min      3.8436
_cell_measurement_theta_max      68.6085

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.716
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.278
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.086
_exptl_absorpt_coefficient_mu    3.793
_shelx_estimated_absorpt_T_min   0.419
_shelx_estimated_absorpt_T_max   0.736
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.419
_exptl_absorpt_correction_T_max  0.736
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 7.391
_diffrn_reflns_number            9185
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.843
_diffrn_reflns_theta_max         68.761
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_point_group_measured_fraction_full 0.871
_reflns_number_total             2251
_reflns_number_gt                2230
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_max     0.735
_reflns_Friedel_fraction_full    0.749

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service v8.5.5.6'
_computing_cell_refinement       'SAINT V8.41 (Bruker AXS LLC)'
_computing_data_reduction        'SAINT V8.41 (Bruker AXS LLC)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0791P)²+6.5705P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 921 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2251
_refine_ls_number_parameters     181
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1483
_refine_ls_wR_factor_gt          0.1463
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
P1A P 0.4033(2) 0.60724(7) 0.6131(3) 0.0232(4) Uani 1 1 d . . . . .
O1A O 0.5805(7) 0.6050(2) 0.6939(9) 0.0286(12) Uani 1 1 d . . . . .
H1A H 0.582203 0.596840 0.578932 0.034 Uiso 1 1 d R U . . .
O2A O 0.2739(7) 0.5686(2) 0.4025(10) 0.0329(12) Uani 1 1 d . . . . .
O3A O 0.4338(8) 0.5969(3) 0.8310(11) 0.0367(13) Uani 1 1 d . . . . .
C1A C 0.3332(10) 0.6827(3) 0.5270(15) 0.0294(16) Uani 1 1 d . . . . .
H11A H 0.250440 0.690570 0.540170 0.035 Uiso 1 1 calc R U . . .
H12A H 0.433469 0.708162 0.643477 0.035 Uiso 1 1 calc R U . . .
C2A C 0.2532(12) 0.6997(3) 0.2846(17) 0.0369(19) Uani 1 1 d . . . . .
F1A F 0.3462(8) 0.6877(2) 0.2383(10) 0.0475(13) Uani 1 1 d . . . . .
F2A F 0.2198(8) 0.7570(2) 0.2477(12) 0.0513(14) Uani 1 1 d . . . . .
F3A F 0.0972(7) 0.6740(2) 0.1099(9) 0.0475(13) Uani 1 1 d . . . . .
P1B P 0.7530(2) 0.58851(7) 0.4400(3) 0.0220(4) Uani 1 1 d . . . . .
O1B O 0.7251(7) 0.5635(2) 0.2279(9) 0.0292(11) Uani 1 1 d . . . . .
H1B H 0.613855 0.574403 0.075931 0.035 Uiso 1 1 d R U . . .
O2B O 0.5931(7) 0.5835(2) 0.3914(10) 0.0295(12) Uani 1 1 d . . . . .
O3B O 0.9100(6) 0.5597(2) 0.6646(8) 0.0253(11) Uani 1 1 d . . . . .
C1B C 0.7916(11) 0.6665(3) 0.4532(16) 0.0329(17) Uani 1 1 d . . . . .
H11B H 0.682962 0.684916 0.311866 0.039 Uiso 1 1 calc R U . . .
H12B H 0.820448 0.682392 0.595707 0.039 Uiso 1 1 calc R U . . .
C2B C 0.9256(12) 0.6850(4) 0.4623(17) 0.0382(19) Uani 1 1 d . . . . .
F1B F 0.8884(12) 0.6725(3) 0.2629(15) 0.077(2) Uani 1 1 d . . . . .
F2B F 1.0788(8) 0.6613(3) 0.6475(17) 0.087(3) Uani 1 1 d . . . . .
F3B F 0.9535(10) 0.7418(2) 0.4898(12) 0.0594(16) Uani 1 1 d . . . . .
N1 N -0.0774(8) 0.5562(3) 0.0445(11) 0.0251(12) Uani 1 1 d . . . . .
H11N H -0.002093 0.577216 0.124462 0.030 Uiso 1 1 d R U . . .
H12N H -0.090366 0.551726 -0.078770 0.030 Uiso 1 1 d R U . . .
H13N H -0.074074 0.524627 0.071011 0.030 Uiso 1 1 d R U . . .
H14N H -0.149598 0.576449 0.019589 0.030 Uiso 1 1 d R U . . .
N2 N 0.2689(8) 0.5521(3) 0.9553(12) 0.0286(13) Uani 1 1 d . . . . .
H21N H 0.317091 0.570881 0.936349 0.034 Uiso 1 1 d R U . . .
H22N H 0.268049 0.519762 0.949838 0.034 Uiso 1 1 d R U . . .
H23N H 0.324729 0.565833 1.099114 0.034 Uiso 1 1 d R U . . .
H24N H 0.191525 0.565055 0.906394 0.034 Uiso 1 1 d R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
P1A O2A 1.502(6) . ?
P1A O3A 1.505(6) . ?
P1A O1A 1.557(5) . ?
P1A C1A 1.826(8) . ?
O1A H1A 0.9274 . ?
C1A C2A 1.481(12) . ?
C1A H11A 0.9900 . ?
C1A H12A 0.9900 . ?
C2A F1A 1.316(9) . ?
C2A F2A 1.344(10) . ?
C2A F3A 1.368(11) . ?
P1B O2B 1.505(5) . ?
P1B O3B 1.506(5) . ?
P1B O1B 1.567(5) . ?
P1B C1B 1.830(8) . ?
O1B H1B 0.9693 . ?
C1B C2B 1.470(12) . ?
C1B H11B 0.9900 . ?
C1B H12B 0.9900 . ?
C2B F3B 1.324(10) . ?
C2B F1B 1.337(11) . ?
C2B F2B 1.348(11) . ?
N1 H11N 0.7634 . ?
N1 H12N 0.8744 . ?
N1 H13N 0.7497 . ?
N1 H14N 0.8113 . ?
N2 H21N 0.7678 . ?
N2 H22N 0.7453 . ?
N2 H23N 0.8827 . ?
N2 H24N 0.7038 . ?

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
O2A P1A O3A 116.4(3) . . ?
O2A P1A O1A 112.3(3) . . ?
O3A P1A O1A 107.2(3) . . ?
O2A P1A C1A 109.0(4) . . ?
O3A P1A C1A 105.9(4) . . ?
O1A P1A C1A 105.2(3) . . ?
P1A O1A H1A 117.6 . . ?
C2A C1A P1A 116.4(6) . . ?
C2A C1A H11A 108.2 . . ?
P1A C1A H11A 108.2 . . ?
C2A C1A H12A 108.2 . . ?
P1A C1A H12A 108.2 . . ?
H11A C1A H12A 107.3 . . ?
F1A C2A F2A 106.9(6) . . ?
F1A C2A F3A 107.0(7) . . ?
F2A C2A F3A 104.3(7) . . ?
F1A C2A C1A 114.2(7) . . ?
F2A C2A C1A 111.3(7) . . ?
F3A C2A C1A 112.4(6) . . ?
O2B P1B O3B 115.9(3) . . ?
O2B P1B O1B 111.2(3) . . ?
O3B P1B O1B 107.3(3) . . ?
O2B P1B C1B 105.6(3) . . ?
O3B P1B C1B 109.6(4) . . ?
O1B P1B C1B 106.8(3) . . ?
P1B O1B H1B 110.9 . . ?
C2B C1B P1B 117.8(6) . . ?
C2B C1B H11B 107.8 . . ?
P1B C1B H11B 107.8 . . ?
C2B C1B H12B 107.8 . . ?
P1B C1B H12B 107.8 . . ?
H11B C1B H12B 107.2 . . ?
F3B C2B F1B 104.6(7) . . ?
F3B C2B F2B 104.6(8) . . ?
F1B C2B F2B 108.0(9) . . ?
F3B C2B C1B 113.6(7) . . ?
F1B C2B C1B 113.0(8) . . ?
F2B C2B C1B 112.4(7) . . ?
H11N N1 H12N 103.6 . . ?
H11N N1 H13N 124.7 . . ?
H12N N1 H13N 97.3 . . ?
H11N N1 H14N 98.3 . . ?
H12N N1 H14N 114.4 . . ?
H13N N1 H14N 118.4 . . ?
H21N N2 H22N 122.2 . . ?
H21N N2 H23N 94.8 . . ?
H22N N2 H23N 113.5 . . ?
H21N N2 H24N 112.1 . . ?
H22N N2 H24N 115.4 . . ?
H23N N2 H24N 92.7 . . ?

_refine_diff_density_max         0.530
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.092

