# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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_shs_6457_rola_auto
_database_code_depnum_ccdc_archive 'CCDC 2426155'
loop_
_audit_author_name
_audit_author_address
'Sergiu Shova'
;Institute of Macromolecular Chemistry, Iasi
Romania
;
_audit_update_record             
;
2025-02-22 deposited with the CCDC.	2025-08-18 downloaded from the CCDC.
;
_audit_creation_date             2024-10-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(C4 H5 F3 N4), H2 O'
_chemical_formula_sum            'C12 H17 F9 N12 O'
_chemical_formula_weight         516.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         C4H4N4F3O2
_chemical_oxdiff_usercomment     AV_F2
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'
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6652(5)
_cell_length_b                   11.6950(6)
_cell_length_c                   11.7268(6)
_cell_angle_alpha                65.612(5)
_cell_angle_beta                 80.451(4)
_cell_angle_gamma                89.034(4)
_cell_volume                     1065.58(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3527
_cell_measurement_temperature    180.05(10)
_cell_measurement_theta_max      25.9630
_cell_measurement_theta_min      1.9190
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.128a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0612
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.855
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12423
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.855
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.359
_diffrn_reflns_theta_min         1.915
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      180.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1593
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.855
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -84.00 -59.00   1.00   30.00    --  -15.29 172.00 -40.00   25
  2  ω    -51.00 -26.00   1.00   30.00    --  -15.29 115.00 177.00   25
  3  ω      3.00  28.00   1.00   30.00    --   17.63-115.00  88.00   25
  4  ω     45.00  71.00   1.00   30.00    --   17.63-172.00 -53.00   26
  5  ω    -31.00   3.00   1.00   30.00    --  -15.29 -77.00 -60.00   34
  6  ω    -34.00  54.00   1.00   30.00    --  -15.29  38.00 -30.00   88
  7  ω    -80.00 -12.00   1.00   30.00    --  -15.29 -57.00-150.00   68
  8  ω      1.00  80.00   1.00   30.00    --   17.63  38.00  60.00   79
  9  ω     39.00  72.00   1.00   30.00    --   17.63 178.00-120.00   33
 10  ω    -20.00  54.00   1.00   30.00    --   17.63 -99.00  90.00   74
 11  ω     -9.00  30.00   1.00   30.00    --   17.63  77.00-180.00   39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0378295000
_diffrn_orient_matrix_UB_12      0.0447518000
_diffrn_orient_matrix_UB_13      0.0196375000
_diffrn_orient_matrix_UB_21      -0.0259070000
_diffrn_orient_matrix_UB_22      -0.0482248000
_diffrn_orient_matrix_UB_23      0.0614863000
_diffrn_orient_matrix_UB_31      0.0693585000
_diffrn_orient_matrix_UB_32      0.0109932000
_diffrn_orient_matrix_UB_33      0.0195665000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3453
_reflns_number_total             5011
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.128a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.128a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.128a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         5011
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0988
_refine_ls_R_factor_gt           0.0614
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0467P)²+0.9538P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1195
_refine_ls_wR_factor_ref         0.1368
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4A(H4AD,H4AE), C4B(H4BD,H4BE), C4C(H4CD,H4CE)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
F3A F 0.3765(2) 0.52579(15) -0.65010(16) 0.0518(5) Uani 1 1 d . . . . .
F2A F 0.1406(2) 0.47437(17) -0.5537(2) 0.0589(6) Uani 1 1 d . . . . .
F1A F 0.3175(2) 0.48365(16) -0.45140(17) 0.0532(5) Uani 1 1 d . . . . .
N4A N 0.3762(2) -0.0947(2) -0.3000(2) 0.0193(4) Uani 1 1 d . . . . .
H4AA H 0.439(3) -0.073(2) -0.252(2) 0.023 Uiso 1 1 d . U . . .
H4AB H 0.445(3) -0.095(2) -0.367(3) 0.023 Uiso 1 1 d . U . . .
H4AC H 0.331(3) -0.172(3) -0.250(3) 0.023 Uiso 1 1 d . U . . .
N1A N 0.2407(2) 0.22082(19) -0.40496(19) 0.0231(5) Uani 1 1 d . . . . .
N2A N 0.4152(2) 0.27874(18) -0.58539(19) 0.0219(4) Uani 1 1 d . . . . .
N3A N 0.4041(2) 0.14987(19) -0.52714(19) 0.0234(5) Uani 1 1 d . . . . .
C4A C 0.2451(3) -0.0113(2) -0.3327(3) 0.0298(6) Uani 1 1 d . . . . .
H4AD H 0.182861 -0.011605 -0.253776 0.036 Uiso 1 1 calc R U . . .
H4AE H 0.175682 -0.044742 -0.372307 0.036 Uiso 1 1 calc R U . . .
C1A C 0.2889(3) 0.4492(2) -0.5411(3) 0.0314(6) Uani 1 1 d . . . . .
C2A C 0.3168(3) 0.3152(2) -0.5102(2) 0.0217(5) Uani 1 1 d . . . . .
C3A C 0.2998(3) 0.1207(2) -0.4217(2) 0.0218(5) Uani 1 1 d . . . . .
F2B F 0.0884(3) 0.20910(19) 0.3139(2) 0.0771(8) Uani 1 1 d . . . . .
F1B F 0.1694(2) 0.39925(19) 0.21007(18) 0.0599(6) Uani 1 1 d . . . . .
F3B F -0.0606(3) 0.3538(3) 0.3140(2) 0.0815(8) Uani 1 1 d . . . . .
N3B N -0.1670(2) 0.3061(2) 0.0109(2) 0.0265(5) Uani 1 1 d . . . . .
N4B N 0.0634(3) 0.1972(2) -0.1702(2) 0.0202(4) Uani 1 1 d . . . . .
H4BA H 0.130(3) 0.162(2) -0.115(3) 0.024 Uiso 1 1 d . U . . .
H4BB H 0.115(3) 0.209(2) -0.256(3) 0.024 Uiso 1 1 d . U . . .
H4BC H -0.028(3) 0.147(2) -0.144(2) 0.024 Uiso 1 1 d . U . . .
N2B N -0.1616(2) 0.3060(2) 0.1276(2) 0.0244(5) Uani 1 1 d . . . . .
N1B N 0.0853(2) 0.33175(19) 0.02235(19) 0.0235(5) Uani 1 1 d . . . . .
C4B C 0.0272(3) 0.3243(2) -0.1760(2) 0.0281(6) Uani 1 1 d . . . . .
H4BD H 0.120699 0.382628 -0.221172 0.034 Uiso 1 1 calc R U . . .
H4BE H -0.058811 0.356477 -0.224875 0.034 Uiso 1 1 calc R U . . .
C2B C -0.0107(3) 0.3214(2) 0.1284(2) 0.0217(5) Uani 1 1 d . . . . .
C1B C 0.0465(3) 0.3204(3) 0.2414(3) 0.0331(6) Uani 1 1 d . . . . .
C3B C -0.0193(3) 0.3212(2) -0.0473(2) 0.0215(5) Uani 1 1 d . . . . .
F1C F 0.2633(3) -0.09777(19) 0.41720(17) 0.0654(6) Uani 1 1 d . . . . .
F2C F 0.3998(3) -0.21388(17) 0.34892(18) 0.0605(6) Uani 1 1 d . . . . .
F3C F 0.1548(3) -0.2193(2) 0.35247(18) 0.0742(8) Uani 1 1 d . . . . .
N3C N 0.2669(2) 0.07250(19) 0.0085(2) 0.0248(5) Uani 1 1 d . . . . .
N1C N 0.4139(2) 0.05114(19) 0.1557(2) 0.0244(5) Uani 1 1 d . . . . .
N2C N 0.2088(2) -0.03262(19) 0.1157(2) 0.0255(5) Uani 1 1 d . . . . .
N4C N 0.4211(3) 0.3437(2) -0.0190(2) 0.0231(5) Uani 1 1 d . . . . .
H4CA H 0.456(3) 0.341(2) 0.052(3) 0.028 Uiso 1 1 d . U . . .
H4CB H 0.312(3) 0.341(2) -0.001(3) 0.028 Uiso 1 1 d . U . . .
H4CC H 0.451(3) 0.422(3) -0.084(3) 0.028 Uiso 1 1 d . U . . .
C2C C 0.2993(3) -0.0402(2) 0.1986(2) 0.0249(6) Uani 1 1 d . . . . .
C1C C 0.2760(4) -0.1416(3) 0.3290(3) 0.0382(7) Uani 1 1 d . . . . .
C4C C 0.4764(3) 0.2389(2) -0.0537(2) 0.0240(5) Uani 1 1 d . . . . .
H4CD H 0.461196 0.257866 -0.141384 0.029 Uiso 1 1 calc R U . . .
H4CE H 0.589668 0.230086 -0.050676 0.029 Uiso 1 1 calc R U . . .
C3C C 0.3872(3) 0.1190(2) 0.0366(2) 0.0213(5) Uani 1 1 d . . . . .
O1W O 0.5413(2) 0.39833(16) -0.83454(17) 0.0240(4) Uani 1 1 d . . . . .
H1WA H 0.503(3) 0.363(3) -0.751(3) 0.036 Uiso 1 1 d . U . . .
H1WB H 0.637(4) 0.385(3) -0.842(3) 0.036 Uiso 1 1 d . 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
F3A C1A 1.329(3) . ?
F2A C1A 1.332(3) . ?
F1A C1A 1.331(3) . ?
N4A H4AA 0.95(3) . ?
N4A H4AB 0.90(3) . ?
N4A H4AC 0.90(3) . ?
N4A C4A 1.479(3) . ?
N1A C2A 1.344(3) . ?
N1A C3A 1.345(3) . ?
N2A N3A 1.371(3) . ?
N2A C2A 1.317(3) . ?
N3A C3A 1.324(3) . ?
C4A H4AD 0.9900 . ?
C4A H4AE 0.9900 . ?
C4A C3A 1.492(3) . ?
C1A C2A 1.480(4) . ?
F2B C1B 1.312(3) . ?
F1B C1B 1.320(3) . ?
F3B C1B 1.318(3) . ?
N3B N2B 1.376(3) . ?
N3B C3B 1.324(3) . ?
N4B H4BA 0.90(3) . ?
N4B H4BB 0.98(3) . ?
N4B H4BC 0.93(3) . ?
N4B C4B 1.489(3) . ?
N2B C2B 1.325(3) . ?
N1B C2B 1.338(3) . ?
N1B C3B 1.356(3) . ?
C4B H4BD 0.9900 . ?
C4B H4BE 0.9900 . ?
C4B C3B 1.481(3) . ?
C2B C1B 1.486(4) . ?
F1C C1C 1.320(3) . ?
F2C C1C 1.346(4) . ?
F3C C1C 1.316(3) . ?
N3C N2C 1.371(3) . ?
N3C C3C 1.331(3) . ?
N1C C2C 1.344(3) . ?
N1C C3C 1.349(3) . ?
N2C C2C 1.322(3) . ?
N4C H4CA 0.93(3) . ?
N4C H4CB 0.93(3) . ?
N4C H4CC 0.92(3) . ?
N4C C4C 1.492(3) . ?
C2C C1C 1.481(4) . ?
C4C H4CD 0.9900 . ?
C4C H4CE 0.9900 . ?
C4C C3C 1.491(3) . ?
O1W H1WA 0.90(3) . ?
O1W H1WB 0.84(3) . ?

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
H4AA N4A H4AB 105(2) . . ?
H4AA N4A H4AC 107(2) . . ?
H4AB N4A H4AC 111(2) . . ?
C4A N4A H4AA 112.6(16) . . ?
C4A N4A H4AB 115.3(16) . . ?
C4A N4A H4AC 105.6(16) . . ?
C2A N1A C3A 100.7(2) . . ?
C2A N2A N3A 105.30(19) . . ?
C3A N3A N2A 105.39(19) . . ?
N4A C4A H4AD 109.1 . . ?
N4A C4A H4AE 109.1 . . ?
N4A C4A C3A 112.6(2) . . ?
H4AD C4A H4AE 107.8 . . ?
C3A C4A H4AD 109.1 . . ?
C3A C4A H4AE 109.1 . . ?
F3A C1A F2A 106.2(2) . . ?
F3A C1A F1A 107.4(2) . . ?
F3A C1A C2A 112.2(2) . . ?
F2A C1A C2A 111.9(2) . . ?
F1A C1A F2A 106.0(2) . . ?
F1A C1A C2A 112.6(2) . . ?
N1A C2A C1A 122.7(2) . . ?
N2A C2A N1A 114.5(2) . . ?
N2A C2A C1A 122.7(2) . . ?
N1A C3A C4A 122.6(2) . . ?
N3A C3A N1A 114.1(2) . . ?
N3A C3A C4A 123.2(2) . . ?
C3B N3B N2B 105.59(19) . . ?
H4BA N4B H4BB 109(2) . . ?
H4BA N4B H4BC 109(2) . . ?
H4BB N4B H4BC 112(2) . . ?
C4B N4B H4BA 109.7(16) . . ?
C4B N4B H4BB 107.3(15) . . ?
C4B N4B H4BC 109.9(16) . . ?
C2B N2B N3B 105.0(2) . . ?
C2B N1B C3B 100.82(19) . . ?
N4B C4B H4BD 109.3 . . ?
N4B C4B H4BE 109.3 . . ?
H4BD C4B H4BE 108.0 . . ?
C3B C4B N4B 111.6(2) . . ?
C3B C4B H4BD 109.3 . . ?
C3B C4B H4BE 109.3 . . ?
N2B C2B N1B 114.8(2) . . ?
N2B C2B C1B 122.1(2) . . ?
N1B C2B C1B 123.0(2) . . ?
F2B C1B F1B 106.6(2) . . ?
F2B C1B F3B 106.8(3) . . ?
F2B C1B C2B 112.4(2) . . ?
F1B C1B C2B 112.4(2) . . ?
F3B C1B F1B 105.9(2) . . ?
F3B C1B C2B 112.2(2) . . ?
N3B C3B N1B 113.8(2) . . ?
N3B C3B C4B 123.0(2) . . ?
N1B C3B C4B 123.2(2) . . ?
C3C N3C N2C 105.95(19) . . ?
C2C N1C C3C 100.77(19) . . ?
C2C N2C N3C 104.81(19) . . ?
H4CA N4C H4CB 106(2) . . ?
H4CA N4C H4CC 108(2) . . ?
H4CB N4C H4CC 106(2) . . ?
C4C N4C H4CA 112.7(17) . . ?
C4C N4C H4CB 111.4(17) . . ?
C4C N4C H4CC 112.6(17) . . ?
N1C C2C C1C 122.6(2) . . ?
N2C C2C N1C 114.9(2) . . ?
N2C C2C C1C 122.5(2) . . ?
F1C C1C F2C 104.0(2) . . ?
F1C C1C C2C 112.6(2) . . ?
F2C C1C C2C 111.8(3) . . ?
F3C C1C F1C 109.8(3) . . ?
F3C C1C F2C 105.4(2) . . ?
F3C C1C C2C 112.7(2) . . ?
N4C C4C H4CD 109.7 . . ?
N4C C4C H4CE 109.7 . . ?
H4CD C4C H4CE 108.2 . . ?
C3C C4C N4C 109.9(2) . . ?
C3C C4C H4CD 109.7 . . ?
C3C C4C H4CE 109.7 . . ?
N3C C3C N1C 113.5(2) . . ?
N3C C3C C4C 122.4(2) . . ?
N1C C3C C4C 124.0(2) . . ?
H1WA O1W H1WB 106(3) . . ?

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
N4A H4AA N1C 0.95(3) 1.92(3) 2.863(3) 171(2) 2_655 yes
N4A H4AB N3A 0.90(3) 1.94(3) 2.812(3) 162(2) 2_654 yes
N4A H4AC N2B 0.90(3) 2.05(3) 2.904(3) 158(2) 2 yes
N4A H4AC O1W 0.90(3) 2.70(3) 3.357(3) 130(2) 2_654 yes
N4B H4BA N3C 0.90(3) 1.97(3) 2.872(3) 176(2) . yes
N4B H4BB N1A 0.98(3) 1.85(3) 2.828(3) 171(2) . yes
N4B H4BC N2C 0.93(3) 1.97(3) 2.883(3) 169(2) 2 yes
N4C H4CA O1W 0.93(3) 1.96(3) 2.843(3) 160(2) 1_556 yes
N4C H4CB N1B 0.93(3) 1.94(3) 2.865(3) 174(2) . yes
N4C H4CC O1W 0.92(3) 1.92(3) 2.780(3) 155(2) 2_664 yes
C4C H4CE N3B 0.99 2.62 3.477(3) 145.1 1_655 yes
O1W H1WA N2A 0.90(3) 1.81(3) 2.703(3) 173(3) . yes
O1W H1WB N2B 0.84(3) 2.01(3) 2.813(3) 161(3) 1_654 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F3A C1A C2A N1A -179.6(2) . . . . ?
F3A C1A C2A N2A -1.5(4) . . . . ?
F2A C1A C2A N1A -60.3(3) . . . . ?
F2A C1A C2A N2A 117.8(3) . . . . ?
F1A C1A C2A N1A 59.0(3) . . . . ?
F1A C1A C2A N2A -122.9(3) . . . . ?
N4A C4A C3A N1A -135.1(2) . . . . ?
N4A C4A C3A N3A 48.7(3) . . . . ?
N2A N3A C3A N1A -0.2(3) . . . . ?
N2A N3A C3A C4A 176.4(2) . . . . ?
N3A N2A C2A N1A 0.5(3) . . . . ?
N3A N2A C2A C1A -177.8(2) . . . . ?
C2A N1A C3A N3A 0.5(3) . . . . ?
C2A N1A C3A C4A -176.1(2) . . . . ?
C2A N2A N3A C3A -0.2(2) . . . . ?
C3A N1A C2A N2A -0.6(3) . . . . ?
C3A N1A C2A C1A 177.7(2) . . . . ?
N3B N2B C2B N1B -0.1(3) . . . . ?
N3B N2B C2B C1B -177.0(2) . . . . ?
N4B C4B C3B N3B -92.5(3) . . . . ?
N4B C4B C3B N1B 86.5(3) . . . . ?
N2B N3B C3B N1B -0.3(3) . . . . ?
N2B N3B C3B C4B 178.9(2) . . . . ?
N2B C2B C1B F2B 94.6(3) . . . . ?
N2B C2B C1B F1B -145.1(3) . . . . ?
N2B C2B C1B F3B -25.8(4) . . . . ?
N1B C2B C1B F2B -82.0(3) . . . . ?
N1B C2B C1B F1B 38.3(4) . . . . ?
N1B C2B C1B F3B 157.6(3) . . . . ?
C2B N1B C3B N3B 0.2(3) . . . . ?
C2B N1B C3B C4B -178.9(2) . . . . ?
C3B N3B N2B C2B 0.2(3) . . . . ?
C3B N1B C2B N2B -0.1(3) . . . . ?
C3B N1B C2B C1B 176.8(2) . . . . ?
N3C N2C C2C N1C -0.3(3) . . . . ?
N3C N2C C2C C1C 179.7(3) . . . . ?
N1C C2C C1C F1C 53.6(4) . . . . ?
N1C C2C C1C F2C -63.1(3) . . . . ?
N1C C2C C1C F3C 178.4(3) . . . . ?
N2C N3C C3C N1C 0.4(3) . . . . ?
N2C N3C C3C C4C -176.3(2) . . . . ?
N2C C2C C1C F1C -126.4(3) . . . . ?
N2C C2C C1C F2C 116.9(3) . . . . ?
N2C C2C C1C F3C -1.6(4) . . . . ?
N4C C4C C3C N3C 99.4(3) . . . . ?
N4C C4C C3C N1C -76.9(3) . . . . ?
C2C N1C C3C N3C -0.5(3) . . . . ?
C2C N1C C3C C4C 176.1(2) . . . . ?
C3C N3C N2C C2C -0.1(3) . . . . ?
C3C N1C C2C N2C 0.5(3) . . . . ?
C3C N1C C2C C1C -179.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.020
_oxdiff_exptl_absorpt_empirical_full_min 0.980
####################################################################### 
# 
# 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_shi_3577_rola
_database_code_depnum_ccdc_archive 'CCDC 2426156'
loop_
_audit_author_name
_audit_author_address
'Sergiu Shova'
;Institute of Macromolecular Chemistry, Iasi
Romania
;
_audit_update_record             
;
2025-02-22 deposited with the CCDC.	2025-08-18 downloaded from the CCDC.
;
_audit_creation_date             2024-05-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H13 F3 N4 O2'
_chemical_formula_sum            'C9 H13 F3 N4 O2'
_chemical_formula_weight         266.23
_chemical_melting_point          ?
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'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.894(3)
_cell_length_b                   12.028(3)
_cell_length_c                   9.8863(18)
_cell_angle_alpha                90
_cell_angle_beta                 101.17(2)
_cell_angle_gamma                90
_cell_volume                     1270.9(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    730
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.4210
_cell_measurement_theta_min      1.9040
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.950
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0909
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5253
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.025
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         1.905
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1534
_reflns_number_total             2243
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1151
_refine_ls_R_factor_gt           0.0694
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0425P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1366
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), N4(H4)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
F1 F -0.1815(2) 0.48016(18) 0.3097(2) 0.0679(7) Uani 1 1 d . . . . .
F2 F -0.0294(2) 0.49771(19) 0.2057(2) 0.0727(7) Uani 1 1 d . . . . .
F3 F -0.1560(2) 0.36238(18) 0.1571(2) 0.0701(7) Uani 1 1 d . . . . .
O1 O 0.36633(19) 0.27696(18) 0.72225(18) 0.0326(6) Uani 1 1 d . . . . .
O2 O 0.51059(19) 0.33846(16) 0.59947(19) 0.0324(5) Uani 1 1 d . . . . .
N1 N 0.0775(2) 0.2893(2) 0.3367(2) 0.0255(6) Uani 1 1 d . . . . .
N2 N -0.0272(2) 0.3549(2) 0.4966(2) 0.0333(7) Uani 1 1 d . . . . .
N3 N 0.0660(2) 0.2836(2) 0.5524(2) 0.0309(7) Uani 1 1 d . . . . .
H3 H 0.083089 0.265174 0.638088 0.037 Uiso 1 1 calc R U . . .
N4 N 0.3555(2) 0.23153(19) 0.4996(2) 0.0280(6) Uani 1 1 d . . . . .
H4 H 0.391354 0.234577 0.429500 0.034 Uiso 1 1 calc R U . . .
C1 C -0.0149(3) 0.3546(3) 0.3673(3) 0.0286(7) Uani 1 1 d . . . . .
C2 C 0.1271(3) 0.2461(2) 0.4579(3) 0.0217(7) Uani 1 1 d . . . . .
C3 C -0.0957(3) 0.4233(3) 0.2614(3) 0.0415(9) Uani 1 1 d . . . . .
C4 C 0.2387(3) 0.1714(2) 0.4889(3) 0.0287(7) Uani 1 1 d . . . . .
H4A H 0.238456 0.132702 0.574940 0.034 Uiso 1 1 calc R U . . .
H4B H 0.232945 0.116045 0.416580 0.034 Uiso 1 1 calc R U . . .
C5 C 0.4084(3) 0.2825(2) 0.6171(3) 0.0242(7) Uani 1 1 d . . . . .
C6 C 0.5891(3) 0.4012(3) 0.7137(3) 0.0350(8) Uani 1 1 d . . . . .
C7 C 0.6887(3) 0.4509(3) 0.6442(4) 0.0575(11) Uani 1 1 d . . . . .
H7A H 0.731269 0.392443 0.605805 0.086 Uiso 1 1 calc R U . . .
H7B H 0.747758 0.491508 0.710815 0.086 Uiso 1 1 calc R U . . .
H7C H 0.650274 0.500255 0.572004 0.086 Uiso 1 1 calc R U . . .
C8 C 0.6472(3) 0.3214(3) 0.8258(4) 0.0579(11) Uani 1 1 d . . . . .
H8A H 0.583742 0.293687 0.872149 0.087 Uiso 1 1 calc R U . . .
H8B H 0.710215 0.359343 0.890775 0.087 Uiso 1 1 calc R U . . .
H8C H 0.684509 0.260501 0.785734 0.087 Uiso 1 1 calc R U . . .
C9 C 0.5114(3) 0.4910(3) 0.7642(4) 0.0645(13) Uani 1 1 d . . . . .
H9A H 0.472261 0.536004 0.687741 0.097 Uiso 1 1 calc R U . . .
H9B H 0.564405 0.536674 0.830782 0.097 Uiso 1 1 calc R U . . .
H9C H 0.448185 0.457159 0.806155 0.097 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
F1 C3 1.320(4) . ?
F2 C3 1.334(4) . ?
F3 C3 1.330(4) . ?
O1 C5 1.216(3) . ?
O2 C5 1.340(3) . ?
O2 C6 1.484(3) . ?
N1 C1 1.356(4) . ?
N1 C2 1.322(3) . ?
N2 N3 1.361(3) . ?
N2 C1 1.311(4) . ?
N3 H3 0.8600 . ?
N3 C2 1.327(3) . ?
N4 H4 0.8600 . ?
N4 C4 1.449(3) . ?
N4 C5 1.342(3) . ?
C1 C3 1.483(4) . ?
C2 C4 1.496(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C6 C7 1.515(4) . ?
C6 C8 1.509(5) . ?
C6 C9 1.516(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

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
C5 O2 C6 121.8(2) . . ?
C2 N1 C1 102.5(2) . . ?
C1 N2 N3 100.6(2) . . ?
N2 N3 H3 124.3 . . ?
C2 N3 N2 111.4(2) . . ?
C2 N3 H3 124.3 . . ?
C4 N4 H4 119.5 . . ?
C5 N4 H4 119.5 . . ?
C5 N4 C4 121.0(2) . . ?
N1 C1 C3 122.0(3) . . ?
N2 C1 N1 116.1(3) . . ?
N2 C1 C3 121.9(3) . . ?
N1 C2 N3 109.4(2) . . ?
N1 C2 C4 126.5(2) . . ?
N3 C2 C4 124.0(2) . . ?
F1 C3 F2 106.2(3) . . ?
F1 C3 F3 106.8(3) . . ?
F1 C3 C1 113.5(3) . . ?
F2 C3 C1 111.7(3) . . ?
F3 C3 F2 106.0(3) . . ?
F3 C3 C1 112.1(3) . . ?
N4 C4 C2 112.5(2) . . ?
N4 C4 H4A 109.1 . . ?
N4 C4 H4B 109.1 . . ?
C2 C4 H4A 109.1 . . ?
C2 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
O1 C5 O2 126.8(3) . . ?
O1 C5 N4 123.0(3) . . ?
O2 C5 N4 110.2(2) . . ?
O2 C6 C7 102.3(2) . . ?
O2 C6 C8 109.5(3) . . ?
O2 C6 C9 109.7(3) . . ?
C7 C6 C9 111.3(3) . . ?
C8 C6 C7 110.4(3) . . ?
C8 C6 C9 113.1(3) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

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
N3 H3 N1 0.86 2.08 2.923(3) 165.8 4_566 yes
N4 H4 O1 0.86 2.02 2.769(3) 145.3 4_565 yes
C8 H8A O1 0.96 2.55 3.079(4) 115.1 . yes
C9 H9C O1 0.96 2.43 3.007(4) 118.5 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C3 F1 179.1(3) . . . . ?
N1 C1 C3 F2 -60.8(4) . . . . ?
N1 C1 C3 F3 58.0(4) . . . . ?
N1 C2 C4 N4 77.7(4) . . . . ?
N2 N3 C2 N1 -0.5(3) . . . . ?
N2 N3 C2 C4 176.5(2) . . . . ?
N2 C1 C3 F1 -2.1(5) . . . . ?
N2 C1 C3 F2 118.0(3) . . . . ?
N2 C1 C3 F3 -123.2(3) . . . . ?
N3 N2 C1 N1 0.1(4) . . . . ?
N3 N2 C1 C3 -178.7(3) . . . . ?
N3 C2 C4 N4 -98.9(3) . . . . ?
C1 N1 C2 N3 0.6(3) . . . . ?
C1 N1 C2 C4 -176.4(3) . . . . ?
C1 N2 N3 C2 0.2(3) . . . . ?
C2 N1 C1 N2 -0.5(4) . . . . ?
C2 N1 C1 C3 178.4(3) . . . . ?
C4 N4 C5 O1 3.8(5) . . . . ?
C4 N4 C5 O2 -175.9(2) . . . . ?
C5 O2 C6 C7 -178.8(3) . . . . ?
C5 O2 C6 C8 64.1(4) . . . . ?
C5 O2 C6 C9 -60.5(4) . . . . ?
C5 N4 C4 C2 82.9(3) . . . . ?
C6 O2 C5 O1 1.4(5) . . . . ?
C6 O2 C5 N4 -178.9(2) . . . . ?

_olex2_date_sample_data_collection 2024-05-18
_olex2_submission_special_instructions 'No special instructions were received'
