# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_158s
_database_code_depnum_ccdc_archive 'CCDC 2403749'
loop_
_audit_author_name
_audit_author_address
'Galina Romanenko'
;International Tomography Center
Russia
;
_audit_update_record             
;
2024-11-19 deposited with the CCDC.	2025-01-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H2 F5 N7 O'
_chemical_formula_weight         331.19

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'

_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                   6.2914(17)
_cell_length_b                   28.492(7)
_cell_length_c                   7.258(2)
_cell_angle_alpha                90
_cell_angle_beta                 114.975(16)
_cell_angle_gamma                90
_cell_volume                     1179.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    747
_cell_measurement_theta_min      3.41
_cell_measurement_theta_max      19.06

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.865
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    0.184
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4138
_exptl_absorpt_correction_T_max  0.4479
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5120
_diffrn_reflns_av_unetI/netI     0.1325
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.860
_diffrn_reflns_theta_max         28.428
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.783
_diffrn_reflns_point_group_measured_fraction_full 0.861
_reflns_number_total             2333
_reflns_number_gt                995
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.613
_reflns_Friedel_fraction_max     0.599
_reflns_Friedel_fraction_full    0.734

_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. Completness statistics refer to single and 
 composite reflections containing twin component 1 only. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component inversion twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0065P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.2(12)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2333
_refine_ls_number_parameters     209
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1310
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0514
_refine_ls_wR_factor_gt          0.0383
_refine_ls_goodness_of_fit_ref   0.738
_refine_ls_restrained_S_all      0.738
_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
O1 O 1.0377(7) 0.14808(15) 0.4347(7) 0.0568(13) Uani 1 1 d . . . . .
N2 N 1.1308(8) 0.19264(17) 0.4343(8) 0.0447(13) Uani 1 1 d . . . . .
C3 C 0.9717(10) 0.2214(2) 0.4320(9) 0.0411(17) Uani 1 1 d . . . . .
N4 N 0.9813(7) 0.26900(16) 0.4316(7) 0.0500(15) Uani 1 1 d . . . . .
H4A H 1.097518 0.284151 0.427601 0.060 Uiso 1 1 calc R U . . .
C5 C 0.7870(10) 0.2914(2) 0.4383(10) 0.0387(16) Uani 1 1 d . . . . .
N6 N 0.7555(7) 0.33690(17) 0.4469(8) 0.0487(15) Uani 1 1 d . . . . .
N7 N 0.5409(8) 0.33887(18) 0.4495(8) 0.0467(15) Uani 1 1 d . . . . .
N8 N 0.4385(7) 0.29664(16) 0.4450(7) 0.0388(13) Uani 1 1 d . . . . .
C9 C 0.5972(9) 0.26700(19) 0.4377(9) 0.0354(15) Uani 1 1 d . . . . .
N10 N 0.5824(7) 0.21897(15) 0.4312(7) 0.0438(14) Uani 1 1 d . . . . .
H10A H 0.461652 0.204089 0.427184 0.053 Uiso 1 1 calc R U . . .
C11 C 0.7757(10) 0.1965(2) 0.4315(10) 0.0418(17) Uani 1 1 d . . . . .
N12 N 0.8131(8) 0.15133(18) 0.4335(8) 0.0564(15) Uani 1 1 d . . . . .
C13 C 0.4372(11) 0.3808(2) 0.4720(10) 0.0418(16) Uani 1 1 d . . . . .
C14 C 0.5680(10) 0.4144(2) 0.6143(10) 0.056(2) Uani 1 1 d . . . . .
F15 F 0.7942(5) 0.40711(12) 0.7348(6) 0.0770(12) Uani 1 1 d . . . . .
C16 C 0.4602(13) 0.4541(3) 0.6441(12) 0.073(2) Uani 1 1 d . . . . .
F17 F 0.5851(7) 0.48535(15) 0.7848(7) 0.1176(19) Uani 1 1 d . . . . .
C18 C 0.2289(12) 0.4609(3) 0.5312(12) 0.079(3) Uani 1 1 d . . . . .
F19 F 0.1242(7) 0.50040(14) 0.5566(7) 0.131(2) Uani 1 1 d . . . . .
C20 C 0.0986(10) 0.4289(2) 0.3864(11) 0.060(2) Uani 1 1 d . . . . .
F21 F -0.1335(5) 0.43598(12) 0.2753(6) 0.0876(14) Uani 1 1 d . . . . .
C22 C 0.2018(9) 0.3899(2) 0.3591(9) 0.0471(17) Uani 1 1 d . . . . .
F23 F 0.0720(6) 0.35839(11) 0.2185(5) 0.0566(9) 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 N2 1.399(5) . ?
O1 N12 1.412(6) . ?
N2 C3 1.288(7) . ?
C3 N4 1.359(6) . ?
C3 C11 1.421(8) . ?
N4 C5 1.398(7) . ?
C5 N6 1.316(6) . ?
C5 C9 1.380(7) . ?
N6 N7 1.359(6) . ?
N7 N8 1.358(6) . ?
N7 C13 1.403(7) . ?
N8 C9 1.325(6) . ?
C9 N10 1.371(6) . ?
N10 C11 1.373(7) . ?
C11 N12 1.307(6) . ?
C13 C22 1.381(6) . ?
C13 C14 1.395(7) . ?
C14 F15 1.335(6) . ?
C14 C16 1.382(9) . ?
C16 F17 1.333(6) . ?
C16 C18 1.349(8) . ?
C18 F19 1.356(7) . ?
C18 C20 1.371(8) . ?
C20 C22 1.343(8) . ?
C20 F21 1.353(6) . ?
C22 F23 1.345(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
N2 O1 N12 111.1(4) . . ?
C3 N2 O1 104.6(5) . . ?
N2 C3 N4 126.9(6) . . ?
N2 C3 C11 110.6(6) . . ?
N4 C3 C11 122.5(5) . . ?
C3 N4 C5 114.6(5) . . ?
N6 C5 C9 110.4(5) . . ?
N6 C5 N4 127.0(5) . . ?
C9 C5 N4 122.5(5) . . ?
C5 N6 N7 102.2(5) . . ?
N8 N7 N6 115.2(4) . . ?
N8 N7 C13 121.2(5) . . ?
N6 N7 C13 123.4(5) . . ?
C9 N8 N7 102.0(4) . . ?
N8 C9 N10 126.6(5) . . ?
N8 C9 C5 110.1(5) . . ?
N10 C9 C5 123.3(5) . . ?
C9 N10 C11 114.8(5) . . ?
N12 C11 N10 127.9(6) . . ?
N12 C11 C3 109.8(5) . . ?
N10 C11 C3 122.3(6) . . ?
C11 N12 O1 103.9(5) . . ?
C22 C13 C14 117.4(6) . . ?
C22 C13 N7 121.7(6) . . ?
C14 C13 N7 120.9(6) . . ?
F15 C14 C16 118.9(6) . . ?
F15 C14 C13 120.7(6) . . ?
C16 C14 C13 120.2(6) . . ?
F17 C16 C18 120.4(7) . . ?
F17 C16 C14 119.8(6) . . ?
C18 C16 C14 119.8(7) . . ?
C16 C18 F19 119.8(7) . . ?
C16 C18 C20 120.9(7) . . ?
F19 C18 C20 119.3(7) . . ?
C22 C20 F21 120.2(6) . . ?
C22 C20 C18 119.6(6) . . ?
F21 C20 C18 120.2(6) . . ?
C20 C22 F23 119.2(5) . . ?
C20 C22 C13 122.1(6) . . ?
F23 C22 C13 118.7(6) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N4 H4A N8 0.86 2.13 2.944(6) 159.0 1_655 yes
N4 H4A F23 0.86 2.57 3.154(6) 126.3 1_655 yes
N10 H10A N2 0.86 2.13 2.948(7) 159.1 1_455 yes
N10 H10A F23 0.86 2.62 3.054(6) 112.2 4 yes

_refine_diff_density_max         0.157
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.040



####################################################################### 
# 
# 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_5211
_database_code_depnum_ccdc_archive 'CCDC 2403750'
loop_
_audit_author_name
_audit_author_address
'Galina Romanenko'
;International Tomography Center
Russia
;
_audit_update_record             
;
2024-11-19 deposited with the CCDC.	2025-01-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H41 N8 O'
_chemical_formula_weight         481.67

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.5924(4)
_cell_length_b                   17.8690(7)
_cell_length_c                   18.4283(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.076(3)
_cell_angle_gamma                90
_cell_volume                     2827.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3049
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      18.77

_exptl_crystal_description       cube
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.131
_exptl_crystal_F_000             1044
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22641
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.588
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5550
_reflns_number_gt                2283
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1258P)²+0.0209P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5550
_refine_ls_number_parameters     310
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.1514
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.2326
_refine_ls_wR_factor_gt          0.1654
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_restrained_S_all      0.947
_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
O1 O 0.4391(3) 0.76481(15) 1.01764(14) 0.1188(8) Uani 1 1 d . U . . .
N2 N 0.3373(3) 0.82591(17) 1.02039(16) 0.1114(9) Uani 1 1 d . U . . .
C3 C 0.2793(4) 0.83163(19) 0.95366(19) 0.0887(8) Uani 1 1 d . U . . .
N4 N 0.1738(3) 0.88334(15) 0.93114(16) 0.0960(8) Uani 1 1 d . . . . .
C5 C 0.1423(3) 0.87344(16) 0.86052(18) 0.0791(8) Uani 1 1 d . . . . .
N6 N 0.0442(3) 0.91516(13) 0.82000(15) 0.0883(7) Uani 1 1 d . . . . .
N7 N 0.0528(3) 0.88450(12) 0.75361(14) 0.0840(7) Uani 1 1 d . . . . .
C8 C -0.0259(3) 0.91569(16) 0.69241(19) 0.0893(9) Uani 1 1 d . . . . .
C9 C -0.1156(4) 0.9790(2) 0.7013(2) 0.1235(13) Uani 1 1 d . . . . .
H9A H -0.130209 0.998918 0.747136 0.148 Uiso 1 1 calc R U . . .
C10 C -0.1831(5) 1.0121(2) 0.6397(3) 0.1553(17) Uani 1 1 d . . . . .
H10A H -0.240602 1.055761 0.644447 0.186 Uiso 1 1 calc R U . . .
C11 C -0.1672(5) 0.9820(2) 0.5725(3) 0.1486(16) Uani 1 1 d . . . . .
H11A H -0.213261 1.004999 0.531915 0.178 Uiso 1 1 calc R U . . .
C12 C -0.0832(5) 0.9180(2) 0.5652(2) 0.1329(13) Uani 1 1 d . . . . .
H12A H -0.073191 0.896774 0.519586 0.160 Uiso 1 1 calc R U . . .
C13 C -0.0131(4) 0.88467(18) 0.6254(2) 0.1076(10) Uani 1 1 d . . . . .
H13A H 0.043285 0.840695 0.620210 0.129 Uiso 1 1 calc R U . . .
N14 N 0.1492(3) 0.82496(12) 0.74765(14) 0.0891(7) Uani 1 1 d . . . . .
C15 C 0.2069(3) 0.81677(15) 0.81579(17) 0.0785(8) Uani 1 1 d . . . . .
N16 N 0.3097(3) 0.76423(13) 0.83748(15) 0.0955(7) Uani 1 1 d . . . . .
C17 C 0.3455(4) 0.77438(17) 0.9089(2) 0.0903(8) Uani 1 1 d . U . . .
N18 N 0.4441(3) 0.73317(16) 0.94778(19) 0.1150(9) Uani 1 1 d . U . . .
N1 N 0.1299(2) 0.16086(11) 0.88887(11) 0.0757(6) Uani 1 1 d . . . . .
C111 C 0.1584(3) 0.23777(14) 0.91985(16) 0.0828(8) Uani 1 1 d . . . . .
H11B H 0.158017 0.273185 0.879950 0.099 Uiso 1 1 calc R U . . .
H11C H 0.261801 0.238563 0.942759 0.099 Uiso 1 1 calc R U . . .
C112 C 0.0449(4) 0.26462(15) 0.97413(17) 0.0980(9) Uani 1 1 d . . . . .
H11D H 0.047498 0.231343 1.015738 0.118 Uiso 1 1 calc R U . . .
H11E H -0.059621 0.263722 0.952418 0.118 Uiso 1 1 calc R U . . .
C113 C 0.0846(4) 0.3436(2) 0.9989(2) 0.1209(12) Uani 1 1 d . . . . .
H11F H 0.187957 0.343410 1.021881 0.145 Uiso 1 1 calc R U . A 1
H11G H 0.087770 0.375692 0.956497 0.145 Uiso 1 1 calc R U . A 1
C114 C -0.0218(6) 0.3750(3) 1.0484(3) 0.1365(18) Uani 0.816(5) 1 d . . P B 1
H11H H 0.011023 0.424669 1.061396 0.205 Uiso 0.816(5) 1 calc R U P B 1
H11I H -0.124130 0.376784 1.025723 0.205 Uiso 0.816(5) 1 calc R U P B 1
H11J H -0.023798 0.344455 1.091202 0.205 Uiso 0.816(5) 1 calc R U P B 1
C11X C 0.027(2) 0.3981(13) 0.9594(13) 0.1365(18) Uani 0.184(5) 1 d . . P B 2
H11X H 0.059804 0.445118 0.980076 0.205 Uiso 0.184(5) 1 calc R U P B 2
H11Y H 0.064046 0.394105 0.910966 0.205 Uiso 0.184(5) 1 calc R U P B 2
H11Z H -0.084387 0.395273 0.957976 0.205 Uiso 0.184(5) 1 calc R U P B 2
C121 C -0.0307(3) 0.15584(15) 0.85226(15) 0.0849(8) Uani 1 1 d . . . . .
H12B H -0.043836 0.105877 0.832400 0.102 Uiso 1 1 calc R U . . .
H12C H -0.107547 0.162193 0.889065 0.102 Uiso 1 1 calc R U . . .
C122 C -0.0655(3) 0.2117(2) 0.79213(17) 0.1069(10) Uani 1 1 d . . . . .
H12D H -0.051563 0.262044 0.810920 0.128 Uiso 1 1 calc R U . . .
H12E H 0.007237 0.204490 0.753704 0.128 Uiso 1 1 calc R U . . .
C123 C -0.2296(3) 0.2029(2) 0.76150(19) 0.1158(11) Uani 1 1 d . . . . .
H12F H -0.245380 0.151509 0.746065 0.139 Uiso 1 1 calc R U . . .
H12G H -0.302091 0.213324 0.799385 0.139 Uiso 1 1 calc R U . . .
C124 C -0.2644(5) 0.2538(2) 0.6986(2) 0.1509(15) Uani 1 1 d . . . . .
H12H H -0.369804 0.246129 0.681088 0.226 Uiso 1 1 calc R U . . .
H12I H -0.251225 0.304854 0.713774 0.226 Uiso 1 1 calc R U . . .
H12J H -0.194515 0.243040 0.660455 0.226 Uiso 1 1 calc R U . . .
C131 C 0.2568(3) 0.14798(15) 0.83486(15) 0.0860(8) Uani 1 1 d . . . . .
H13B H 0.252159 0.188421 0.799734 0.103 Uiso 1 1 calc R U . . .
H13C H 0.356773 0.151294 0.860820 0.103 Uiso 1 1 calc R U . . .
C132 C 0.2511(4) 0.07517(17) 0.79408(17) 0.1063(10) Uani 1 1 d . . . . .
H13D H 0.150365 0.070118 0.769098 0.128 Uiso 1 1 calc R U . . .
H13E H 0.262933 0.034087 0.828236 0.128 Uiso 1 1 calc R U . . .
C133 C 0.3776(4) 0.0705(2) 0.73943(19) 0.1178(11) Uani 1 1 d . . . . .
H13F H 0.363317 0.110645 0.704397 0.141 Uiso 1 1 calc R U . . .
H13G H 0.477925 0.077700 0.764316 0.141 Uiso 1 1 calc R U . . .
C134 C 0.3785(5) -0.0028(3) 0.6999(3) 0.180(2) Uani 1 1 d . . . . .
H13H H 0.460756 -0.002776 0.666020 0.271 Uiso 1 1 calc R U . . .
H13I H 0.395010 -0.042706 0.734185 0.271 Uiso 1 1 calc R U . . .
H13J H 0.280384 -0.009756 0.674256 0.271 Uiso 1 1 calc R U . . .
C141 C 0.1339(3) 0.10142(14) 0.94849(14) 0.0849(8) Uani 1 1 d . . . . .
H14A H 0.043687 0.108586 0.977893 0.102 Uiso 1 1 calc R U . . .
H14B H 0.123531 0.052687 0.925643 0.102 Uiso 1 1 calc R U . . .
C142 C 0.2764(4) 0.10038(16) 0.99801(16) 0.0948(9) Uiso 1 1 d . . . . .
H14C H 0.287902 0.148371 1.022222 0.114 Uiso 1 1 calc R U . . .
H14D H 0.367960 0.092005 0.969825 0.114 Uiso 1 1 calc R U . . .
C144 C 0.3973(4) 0.0368(2) 1.1077(2) 0.1453(14) Uani 1 1 d . . . . .
H14E H 0.382790 -0.002967 1.141784 0.218 Uiso 1 1 calc R U . . .
H14F H 0.491747 0.028625 1.082626 0.218 Uiso 1 1 calc R U . . .
H14G H 0.403751 0.083689 1.133146 0.218 Uiso 1 1 calc R U . . .
C143 C 0.2630(4) 0.03870(17) 1.05429(17) 0.1071(10) Uiso 1 1 d . . . . .
H14H H 0.167797 0.045852 1.080128 0.129 Uiso 1 1 calc R U . . .
H14I H 0.255769 -0.009198 1.029622 0.129 Uiso 1 1 calc 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
O1 N2 1.401(3) . ?
O1 N18 1.408(3) . ?
N2 C3 1.314(4) . ?
C3 N4 1.349(4) . ?
C3 C17 1.444(4) . ?
N4 C5 1.331(3) . ?
C5 N6 1.333(3) . ?
C5 C15 1.431(4) . ?
N6 N7 1.345(3) . ?
N7 N14 1.355(3) . ?
N7 C8 1.409(3) . ?
C8 C13 1.362(4) . ?
C8 C9 1.382(4) . ?
C9 C10 1.387(5) . ?
C10 C11 1.361(5) . ?
C11 C12 1.361(5) . ?
C12 C13 1.378(4) . ?
N14 C15 1.342(3) . ?
C15 N16 1.340(3) . ?
N16 C17 1.353(4) . ?
C17 N18 1.316(4) . ?
N1 C111 1.505(3) . ?
N1 C121 1.517(3) . ?
N1 C141 1.528(3) . ?
N1 C131 1.520(3) . ?
C111 C112 1.501(4) . ?
C112 C113 1.519(4) . ?
C113 C11X 1.30(2) . ?
C113 C114 1.429(5) . ?
C121 C122 1.513(4) . ?
C122 C123 1.508(4) . ?
C123 C124 1.495(4) . ?
C131 C132 1.503(4) . ?
C132 C133 1.511(4) . ?
C133 C134 1.498(5) . ?
C141 C142 1.501(4) . ?
C142 C143 1.521(4) . ?
C144 C143 1.489(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
N2 O1 N18 112.7(2) . . ?
C3 N2 O1 104.0(3) . . ?
N2 C3 N4 124.7(3) . . ?
N2 C3 C17 109.6(3) . . ?
N4 C3 C17 125.7(3) . . ?
C5 N4 C3 108.7(3) . . ?
N4 C5 N6 125.1(3) . . ?
N4 C5 C15 126.0(3) . . ?
N6 C5 C15 108.9(3) . . ?
C5 N6 N7 103.1(2) . . ?
N6 N7 N14 116.6(2) . . ?
N6 N7 C8 121.8(2) . . ?
N14 N7 C8 121.5(2) . . ?
C13 C8 C9 120.3(3) . . ?
C13 C8 N7 120.8(3) . . ?
C9 C8 N7 118.9(3) . . ?
C10 C9 C8 118.1(3) . . ?
C11 C10 C9 121.5(4) . . ?
C10 C11 C12 119.5(4) . . ?
C11 C12 C13 120.1(4) . . ?
C8 C13 C12 120.4(3) . . ?
C15 N14 N7 102.5(2) . . ?
N14 C15 N16 125.0(3) . . ?
N14 C15 C5 108.9(3) . . ?
N16 C15 C5 126.1(3) . . ?
C15 N16 C17 108.7(3) . . ?
N18 C17 N16 125.1(3) . . ?
N18 C17 C3 110.1(3) . . ?
N16 C17 C3 124.8(3) . . ?
C17 N18 O1 103.5(3) . . ?
C111 N1 C121 110.82(19) . . ?
C111 N1 C141 111.28(19) . . ?
C121 N1 C141 105.95(19) . . ?
C111 N1 C131 106.03(18) . . ?
C121 N1 C131 111.3(2) . . ?
C141 N1 C131 111.6(2) . . ?
N1 C111 C112 116.4(2) . . ?
C111 C112 C113 110.7(3) . . ?
C11X C113 C112 116.8(10) . . ?
C114 C113 C112 114.5(3) . . ?
C122 C121 N1 116.1(2) . . ?
C123 C122 C121 111.3(3) . . ?
C124 C123 C122 112.7(3) . . ?
C132 C131 N1 116.6(2) . . ?
C131 C132 C133 111.8(2) . . ?
C134 C133 C132 112.9(3) . . ?
C142 C141 N1 116.3(2) . . ?
C141 C142 C143 110.1(2) . . ?
C144 C143 C142 113.0(3) . . ?

_refine_diff_density_max         0.148
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.027



####################################################################### 
# 
# 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_174x
_database_code_depnum_ccdc_archive 'CCDC 2403751'
loop_
_audit_author_name
_audit_author_address
'Galina Romanenko'
;International Tomography Center
Russia
;
_audit_update_record             
;
2024-11-19 deposited with the CCDC.	2025-01-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8.67 H12 F1.67 N2.67 O0.33'
_chemical_formula_weight         190.54

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.4306(6)
_cell_length_b                   20.1188(12)
_cell_length_c                   14.4748(9)
_cell_angle_alpha                90
_cell_angle_beta                 99.556(4)
_cell_angle_gamma                90
_cell_volume                     2995.4(3)
_cell_formula_units_Z            12
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1536
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      13.26

_exptl_crystal_description       plate
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_F_000             1204
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.005
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21301
_diffrn_reflns_av_unetI/netI     0.0726
_diffrn_reflns_av_R_equivalents  0.0694
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.024
_diffrn_reflns_theta_max         23.255
_diffrn_reflns_theta_full        23.255
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4305
_reflns_number_gt                1504
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1542P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.004(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4305
_refine_ls_number_parameters     371
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.2075
_refine_ls_R_factor_gt           0.0773
_refine_ls_wR_factor_ref         0.3094
_refine_ls_wR_factor_gt          0.2248
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.002
_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 0.1702(4) 0.1121(2) 0.6282(3) 0.0989(13) Uani 1 1 d . . . . .
C11 C 0.1788(6) 0.1861(3) 0.6090(4) 0.1098(18) Uani 1 1 d D . . . .
H11A H 0.165465 0.209957 0.664894 0.132 Uiso 1 1 calc R U . . .
H11B H 0.266275 0.195838 0.598573 0.132 Uiso 1 1 calc R U . . .
C12 C 0.0856(6) 0.2126(3) 0.5281(5) 0.123(2) Uani 1 1 d D . . . .
H12A H -0.002848 0.211589 0.540839 0.148 Uiso 1 1 calc R U . A 1
H12B H 0.089770 0.187361 0.471631 0.148 Uiso 1 1 calc R U . A 1
C13 C 0.131(2) 0.2839(9) 0.519(3) 0.135(6) Uani 0.5 1 d D . P B 1
H13A H 0.221067 0.283644 0.508630 0.162 Uiso 0.5 1 calc R U P B 1
H13B H 0.127766 0.307848 0.576469 0.162 Uiso 0.5 1 calc R U P B 1
C14 C 0.0459(16) 0.3193(7) 0.4366(12) 0.169(4) Uani 0.5 1 d D . P B 1
H14A H 0.076227 0.363996 0.431849 0.253 Uiso 0.5 1 calc R U P B 1
H14B H 0.050589 0.295877 0.379452 0.253 Uiso 0.5 1 calc R U P B 1
H14C H -0.042557 0.320041 0.447179 0.253 Uiso 0.5 1 calc R U P B 1
C13X C 0.079(2) 0.2874(9) 0.515(3) 0.135(6) Uani 0.5 1 d D . P B 2
H13X H 0.059751 0.309358 0.570523 0.162 Uiso 0.5 1 calc R U P B 2
H13Y H 0.012374 0.299249 0.462083 0.162 Uiso 0.5 1 calc R U P B 2
C14X C 0.2134(17) 0.3065(8) 0.4958(12) 0.169(4) Uani 0.5 1 d D . P B 2
H14X H 0.216965 0.353660 0.486455 0.253 Uiso 0.5 1 calc R U P B 2
H14Y H 0.277514 0.293962 0.548410 0.253 Uiso 0.5 1 calc R U P B 2
H14Z H 0.230464 0.283922 0.440717 0.253 Uiso 0.5 1 calc R U P B 2
C21 C 0.1778(6) 0.0711(3) 0.5425(4) 0.1093(17) Uani 1 1 d D . . . .
H21A H 0.174426 0.024470 0.558973 0.131 Uiso 1 1 calc R U . . .
H21B H 0.102058 0.080551 0.495796 0.131 Uiso 1 1 calc R U . . .
C22 C 0.2964(7) 0.0826(3) 0.5002(5) 0.137(2) Uani 1 1 d D . . . .
H22A H 0.373264 0.069116 0.543358 0.164 Uiso 1 1 calc R U . . .
H22B H 0.304458 0.129445 0.486053 0.164 Uiso 1 1 calc R U . . .
C23 C 0.2830(8) 0.0415(4) 0.4104(6) 0.172(3) Uani 1 1 d D . . . .
H23A H 0.282196 -0.005267 0.426337 0.206 Uiso 1 1 calc R U . . .
H23B H 0.200723 0.051966 0.371277 0.206 Uiso 1 1 calc R U . . .
C24 C 0.3899(10) 0.0541(5) 0.3569(7) 0.229(4) Uani 1 1 d D . . . .
H24A H 0.377331 0.027263 0.301252 0.344 Uiso 1 1 calc R U . . .
H24B H 0.390043 0.100207 0.339771 0.344 Uiso 1 1 calc R U . . .
H24C H 0.471503 0.042983 0.394823 0.344 Uiso 1 1 calc R U . . .
C31 C 0.2804(5) 0.0977(3) 0.7084(4) 0.1092(18) Uani 1 1 d D . . . .
H31A H 0.361668 0.110036 0.688731 0.131 Uiso 1 1 calc R U . . .
H31B H 0.269643 0.125939 0.760812 0.131 Uiso 1 1 calc R U . . .
C32 C 0.2915(6) 0.0273(3) 0.7419(4) 0.130(2) Uani 1 1 d D . . . .
H32A H 0.308718 -0.001453 0.691608 0.155 Uiso 1 1 calc R U . . .
H32B H 0.210128 0.013502 0.760041 0.155 Uiso 1 1 calc R U . . .
C33 C 0.4007(7) 0.0208(4) 0.8251(5) 0.159(3) Uani 1 1 d D . . . .
H33A H 0.480995 0.036055 0.806582 0.191 Uiso 1 1 calc R U . . .
H33B H 0.382230 0.049709 0.874898 0.191 Uiso 1 1 calc R U . . .
C34 C 0.4200(9) -0.0478(5) 0.8620(7) 0.225(4) Uani 1 1 d D . . . .
H34A H 0.490099 -0.048288 0.914150 0.337 Uiso 1 1 calc R U . . .
H34B H 0.341776 -0.062930 0.882032 0.337 Uiso 1 1 calc R U . . .
H34C H 0.440638 -0.076598 0.813649 0.337 Uiso 1 1 calc R U . . .
C41 C 0.0383(6) 0.0931(3) 0.6561(5) 0.124(2) Uani 1 1 d D . . . .
H41A H -0.030176 0.103684 0.604266 0.149 Uiso 1 1 calc R U . . .
H41B H 0.036925 0.045448 0.665736 0.149 Uiso 1 1 calc R U . . .
C42 C 0.0078(7) 0.1273(4) 0.7437(6) 0.158(3) Uani 1 1 d D . . . .
H42A H 0.071405 0.114472 0.797433 0.190 Uiso 1 1 calc R U . . .
H42B H 0.011918 0.175104 0.736430 0.190 Uiso 1 1 calc R U . . .
C43 C -0.1276(9) 0.1072(6) 0.7594(7) 0.216(4) Uani 1 1 d D . . . .
H43A H -0.190254 0.124132 0.707637 0.259 Uiso 1 1 calc R U . C 1
H43B H -0.133285 0.059091 0.757583 0.259 Uiso 1 1 calc R U . C 1
C44 C -0.165(2) 0.1301(11) 0.8463(14) 0.238(7) Uani 0.5 1 d D . P D 1
H44A H -0.251339 0.114985 0.849730 0.357 Uiso 0.5 1 calc R U P D 1
H44B H -0.105482 0.112539 0.898411 0.357 Uiso 0.5 1 calc R U P D 1
H44C H -0.162592 0.177742 0.848342 0.357 Uiso 0.5 1 calc R U P D 1
C44X C -0.146(2) 0.0622(9) 0.8207(16) 0.238(7) Uani 0.5 1 d D . P D 2
H44X H -0.237598 0.056648 0.820112 0.357 Uiso 0.5 1 calc R U P D 2
H44Y H -0.109173 0.020775 0.805220 0.357 Uiso 0.5 1 calc R U P D 2
H44Z H -0.104946 0.076069 0.881976 0.357 Uiso 0.5 1 calc R U P D 2
O1A O -0.4471(5) 0.1981(4) 1.5281(4) 0.1690(19) Uani 1 1 d . . . . .
N2A N -0.4300(7) 0.2410(3) 1.4560(6) 0.165(2) Uani 1 1 d . . . . .
C3A C -0.3398(7) 0.2134(4) 1.4143(6) 0.125(2) Uani 1 1 d . . . . .
N4A N -0.2908(6) 0.2382(3) 1.3414(5) 0.144(2) Uani 1 1 d . . . . .
C5A C -0.1996(7) 0.1971(3) 1.3186(5) 0.1096(18) Uani 1 1 d . . . . .
N6A N -0.1279(6) 0.2074(3) 1.2507(4) 0.1286(18) Uani 1 1 d . . . . .
N7A N -0.0542(5) 0.1535(3) 1.2565(4) 0.1060(15) Uani 1 1 d . . . . .
C8A C 0.0391(7) 0.1471(4) 1.1977(5) 0.1089(18) Uani 1 1 d . . . . .
F10A F 0.1591(7) 0.2331(4) 1.2699(5) 0.323(5) Uani 1 1 d . . . . .
C10A C 0.1447(10) 0.1867(5) 1.2043(7) 0.171(3) Uani 1 1 d . . . . .
C11A C 0.2299(10) 0.1777(6) 1.1491(9) 0.192(4) Uani 1 1 d . . . . .
F12A F 0.3320(7) 0.2215(4) 1.1538(6) 0.337(5) Uani 1 1 d . . . . .
C13A C 0.2221(10) 0.1346(5) 1.0841(7) 0.140(3) Uani 1 1 d . . . . .
F14A F 0.3074(5) 0.1264(3) 1.0244(4) 0.200(2) Uani 1 1 d . . . . .
C15A C 0.1211(11) 0.0923(5) 1.0751(6) 0.162(3) Uani 1 1 d . . . . .
F16A F 0.1048(6) 0.0472(4) 1.0091(6) 0.302(4) Uani 1 1 d . . . . .
C17A C 0.0285(8) 0.1005(4) 1.1310(7) 0.147(2) Uani 1 1 d . . . . .
F18A F -0.0738(6) 0.0596(3) 1.1234(5) 0.264(3) Uani 1 1 d . . . . .
N19A N -0.0672(5) 0.1085(2) 1.3236(4) 0.1067(15) Uani 1 1 d . . . . .
C20A C -0.1601(6) 0.1357(3) 1.3650(5) 0.0993(17) Uani 1 1 d . . . . .
N21A N -0.2101(5) 0.1092(3) 1.4383(4) 0.1167(16) Uani 1 1 d . . . . .
C22A C -0.2980(7) 0.1510(4) 1.4617(5) 0.119(2) Uani 1 1 d . . . . .
N23A N -0.3643(7) 0.1411(3) 1.5307(5) 0.152(2) 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
N1 C21 1.502(6) . ?
N1 C11 1.520(6) . ?
N1 C31 1.520(6) . ?
N1 C41 1.544(7) . ?
C11 C12 1.491(7) . ?
C12 C13X 1.517(16) . ?
C12 C13 1.524(16) . ?
C13 C14 1.539(19) . ?
C13X C14X 1.524(19) . ?
C21 C22 1.487(7) . ?
C22 C23 1.527(8) . ?
C23 C24 1.481(9) . ?
C31 C32 1.494(7) . ?
C32 C33 1.520(7) . ?
C33 C34 1.482(8) . ?
C41 C42 1.521(8) . ?
C42 C43 1.521(9) . ?
C43 C44X 1.305(15) . ?
C43 C44 1.453(15) . ?
O1A N2A 1.388(7) . ?
O1A N23A 1.432(7) . ?
N2A C3A 1.321(8) . ?
C3A N4A 1.343(8) . ?
C3A C22A 1.462(9) . ?
N4A C5A 1.342(7) . ?
C5A N6A 1.346(7) . ?
C5A C20A 1.434(7) . ?
N6A N7A 1.325(6) . ?
N7A N19A 1.351(6) . ?
N7A C8A 1.401(7) . ?
C8A C17A 1.337(8) . ?
C8A C10A 1.350(10) . ?
F10A C10A 1.322(9) . ?
C10A C11A 1.303(11) . ?
C11A C13A 1.272(11) . ?
C11A F12A 1.374(9) . ?
C13A C15A 1.344(10) . ?
C13A F14A 1.350(8) . ?
C15A F16A 1.309(8) . ?
C15A C17A 1.368(10) . ?
C17A F18A 1.337(8) . ?
N19A C20A 1.338(7) . ?
C20A N21A 1.366(7) . ?
N21A C22A 1.330(8) . ?
C22A N23A 1.321(7) . ?

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 112.0(4) . . ?
C21 N1 C31 112.8(4) . . ?
C11 N1 C31 105.4(4) . . ?
C21 N1 C41 104.6(4) . . ?
C11 N1 C41 111.8(4) . . ?
C31 N1 C41 110.3(4) . . ?
C12 C11 N1 116.3(5) . . ?
C11 C12 C13X 117.8(13) . . ?
C11 C12 C13 103.5(11) . . ?
C12 C13 C14 110.7(16) . . ?
C12 C13X C14X 104.4(16) . . ?
C22 C21 N1 114.6(5) . . ?
C21 C22 C23 107.5(6) . . ?
C24 C23 C22 112.5(7) . . ?
C32 C31 N1 115.9(4) . . ?
C31 C32 C33 110.3(5) . . ?
C34 C33 C32 113.9(7) . . ?
C42 C41 N1 115.2(5) . . ?
C43 C42 C41 109.4(7) . . ?
C44X C43 C42 122.1(14) . . ?
C44 C43 C42 115.7(13) . . ?
N2A O1A N23A 111.4(5) . . ?
C3A N2A O1A 105.8(6) . . ?
N2A C3A N4A 126.6(9) . . ?
N2A C3A C22A 109.0(7) . . ?
N4A C3A C22A 124.4(7) . . ?
C3A N4A C5A 110.0(6) . . ?
N4A C5A N6A 125.9(7) . . ?
N4A C5A C20A 125.2(7) . . ?
N6A C5A C20A 108.9(6) . . ?
N7A N6A C5A 102.4(5) . . ?
N6A N7A N19A 117.9(5) . . ?
N6A N7A C8A 119.5(6) . . ?
N19A N7A C8A 122.5(6) . . ?
C17A C8A C10A 115.7(8) . . ?
C17A C8A N7A 121.4(7) . . ?
C10A C8A N7A 122.9(8) . . ?
C11A C10A F10A 122.0(10) . . ?
C11A C10A C8A 120.4(9) . . ?
F10A C10A C8A 117.6(9) . . ?
C13A C11A C10A 125.6(9) . . ?
C13A C11A F12A 115.3(11) . . ?
C10A C11A F12A 118.8(11) . . ?
C11A C13A C15A 117.1(9) . . ?
C11A C13A F14A 126.1(11) . . ?
C15A C13A F14A 116.8(10) . . ?
F16A C15A C13A 121.0(10) . . ?
F16A C15A C17A 119.8(11) . . ?
C13A C15A C17A 119.0(9) . . ?
F18A C17A C8A 117.3(8) . . ?
F18A C17A C15A 120.6(10) . . ?
C8A C17A C15A 122.0(8) . . ?
C20A N19A N7A 102.4(5) . . ?
N19A C20A N21A 125.9(6) . . ?
N19A C20A C5A 108.4(6) . . ?
N21A C20A C5A 125.7(7) . . ?
C22A N21A C20A 108.6(6) . . ?
N23A C22A N21A 124.6(9) . . ?
N23A C22A C3A 109.4(7) . . ?
N21A C22A C3A 126.0(7) . . ?
C22A N23A O1A 104.4(6) . . ?

_refine_diff_density_max         0.196
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.040




# start Validation Reply Form
_vrf_THETM01_174x                
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: All the crystals studied give practically no reflections 
at 2theta angles greater than 50 degrees, regardless of the crystal 
size and exposure time
;
_vrf_PLAT026_174x                
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low .. 35% Check
RESPONSE: All the crystals studied give practically no reflections 
at 2theta angles greater than 50 degrees, regardless of the crystal 
size and exposure time
;
_vrf_PLAT031_174x                
;
PROBLEM: Refined Extinction Parameter Within Range of ... 2.000 Sigma
RESPONSE: All the crystals studied give practically no reflections 
at 2theta angles greater than 50 degrees, regardless of the crystal 
size and exposure time
;
_vrf_PLAT334_174x                
;
PROBLEM: Small <C-C> Benzene Dist. C8A -C17A . 1.33 Ang.
RESPONSE: Very short F...F contacts (2.85 A) of F atom at C17A
maybe the reasons of this problem.
;
_vrf_PLAT340_174x                
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.01182 Ang.
RESPONSE: Low reflective crystal
;
# end Validation Reply Form
