# Supplementary Information (SI) for RSC Medicinal 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_8a_prime
_database_code_depnum_ccdc_archive 'CCDC 2468967'
loop_
_audit_author_name
_audit_author_address
'Filipe Almeida Paz'
;University of Aveiro CICECO Aveiro Institute of Materials
Portugal
;
_audit_update_record             
;
2025-07-01 deposited with the CCDC.	2025-10-24 downloaded from the CCDC.
;
#==============================================================================

#=============================================================================
_audit_creation_method           'SHELXL-2019/3, manual editing plus enCIFer'
_audit_creation_date             '1 July 2025'
_shelx_SHELXL_version_number     2019/3
#=============================================================================

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H19 Cl F3 N O'
_chemical_formula_sum            'C23 H19 Cl F3 N O'
_chemical_formula_weight         417.84

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'
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'

#=============================================================================
# CRYSTAL DATA
#=============================================================================

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   11.45488(17)
_cell_length_b                   17.2029(3)
_cell_length_c                   9.67733(13)
_cell_angle_alpha                90
_cell_angle_beta                 97.5738(13)
_cell_angle_gamma                90
_cell_volume                     1890.35(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    17240
_cell_measurement_theta_min      2.1130
_cell_measurement_theta_max      25.4240
_cell_oxdiff_length_a            11.45610(16)
_cell_oxdiff_length_b            17.2000(3)
_cell_oxdiff_length_c            9.67827(12)
_cell_oxdiff_angle_alpha         90.0175(11)
_cell_oxdiff_angle_beta          97.5891(11)
_cell_oxdiff_angle_gamma         89.9794(12)
_cell_oxdiff_volume              1890.35(5)
_cell_oxdiff_measurement_reflns_used 17240

#=============================================================================
# EXPERIMENTAL DATA
#============================================================================= 

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.246
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_T_min  0.94027
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.915
_oxdiff_exptl_absorpt_empirical_full_max 1.147
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      149.99(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix3000
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            22476
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.589
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             3385
_reflns_number_gt                3059
_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.
;

_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0610926000
_diffrn_orient_matrix_UB_12      -0.0063126000
_diffrn_orient_matrix_UB_13      -0.0198749000
_diffrn_orient_matrix_UB_21      -0.0114950000
_diffrn_orient_matrix_UB_22      0.0132118000
_diffrn_orient_matrix_UB_23      0.0663139000
_diffrn_orient_matrix_UB_31      -0.0060856000
_diffrn_orient_matrix_UB_32      0.0385514000
_diffrn_orient_matrix_UB_33      -0.0259599000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00  32.00   0.50   30.00    --   16.65 -26.00-146.00  194
  2  ω    -65.00  32.00   0.50   30.00    --   16.65 -26.00-146.00  194
  3  ω    -32.00  65.00   0.50   30.00    --  -17.28  26.00  16.00  194
  4  ω    -99.00  26.00   0.50   30.00    --  -17.28 -26.00-146.00  250
  5  ω     16.00  93.00   0.50   30.00    --   16.65  15.00-180.00  154
  6  ω    -69.00  22.00   0.50   30.00    --   16.65 -15.00 120.00  182
  7  ω     19.00  69.00   0.50   30.00    --   16.65  26.00  16.00  100
  8  ω     13.00  74.00   0.50   30.00    --   16.65-125.00  60.00  122
  9  ω    -24.00  39.00   0.50   30.00    --   16.65  15.00-180.00  126
 10  ω    -59.00 -10.00   0.50   30.00    --   16.65 -45.00 120.00   98
 11  ω     -1.00  49.00   0.50   30.00    --   16.65 -45.00 120.00  100
 12  ω     14.00  74.00   0.50   30.00    --   16.65-125.00-120.00  120
 13  ω    -61.00  48.00   0.50   30.00    --   16.65 -45.00-150.00  218
 14  ω    -26.00  19.00   0.50   30.00    --  -17.28 -95.00-180.00   90
 15  ω    -53.00 -19.00   0.50   30.00    --  -17.28 125.00-180.00   68
 16  ω    -19.00  15.00   0.50   30.00    --  -17.28 -95.00 -30.00   68
 17  ω     -7.00  21.00   0.50   30.00    --  -17.28 -95.00  90.00   56
 18  ω    -13.00  25.00   0.50   30.00    --  -17.28 -95.00-120.00   76
;
_diffrn_measurement_method       'ω scans'
_diffrn_oxdiff_digest_frames     
;
01e26d9334202c19a697357b9eb1bfcd9b000250a69
;
_diffrn_oxdiff_digest_hkl        
;
434ca5323bd2a2decbc1495127636a4a3f9965
;

_computing_data_collection       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_structure_solution    'SHELXT 2014/5'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    DIAMOND
_computing_publication_material  SHELXL-2019/3


#=============================================================================
# REFINEMENT DATA
#=============================================================================

_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)+(0.0354P)²+1.1666P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3385
_refine_ls_number_parameters     266
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0851
_refine_ls_wR_factor_gt          0.0830
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

#=============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
#=============================================================================

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
Cl1 Cl 0.13248(4) 0.51374(2) 0.31131(5) 0.03350(13) Uani 1 1 d . . . . .
F1 F 0.93158(9) 0.21957(6) 0.53046(13) 0.0459(3) Uani 1 1 d . . . . .
F2 F 0.98383(9) 0.31639(7) 0.66272(11) 0.0435(3) Uani 1 1 d . . . . .
F3 F 0.93534(9) 0.33352(7) 0.44287(12) 0.0455(3) Uani 1 1 d . . . . .
O1 O 0.35288(10) 0.22123(6) 0.52038(12) 0.0267(3) Uani 1 1 d . . . . .
H1 H 0.327996 0.184343 0.467679 0.040 Uiso 1 1 calc R U . . .
N1 N 0.25694(11) 0.40785(8) 0.83653(13) 0.0206(3) Uani 1 1 d D . . . .
H1X H 0.2260(16) 0.3885(11) 0.7545(16) 0.031 Uiso 1 1 d D U . . .
C11 C 0.43136(13) 0.35797(9) 0.66758(15) 0.0179(3) Uani 1 1 d . . . . .
H11 H 0.408391 0.317977 0.733962 0.021 Uiso 1 1 calc R U . . .
C12 C 0.33530(12) 0.35838(9) 0.54071(15) 0.0176(3) Uani 1 1 d . . . . .
C13 C 0.28173(13) 0.42704(9) 0.48931(15) 0.0192(3) Uani 1 1 d . . . . .
H13 H 0.304205 0.474988 0.533774 0.023 Uiso 1 1 calc R U . . .
C14 C 0.19588(13) 0.42623(9) 0.37388(16) 0.0200(3) Uani 1 1 d . . . . .
C15 C 0.16065(13) 0.35792(9) 0.30670(16) 0.0223(3) Uani 1 1 d . . . . .
H15 H 0.101524 0.357960 0.228019 0.027 Uiso 1 1 calc R U . . .
C16 C 0.21322(13) 0.28935(9) 0.35631(16) 0.0230(3) Uani 1 1 d . . . . .
H16 H 0.189921 0.241803 0.310899 0.028 Uiso 1 1 calc R U . . .
C17 C 0.29981(13) 0.28873(9) 0.47179(16) 0.0198(3) Uani 1 1 d . . . . .
C18 C 0.55116(13) 0.33430(9) 0.62905(15) 0.0185(3) Uani 1 1 d . . . . .
C19 C 0.58683(14) 0.35540(9) 0.50241(15) 0.0218(3) Uani 1 1 d . . . . .
H19 H 0.531875 0.378978 0.432826 0.026 Uiso 1 1 calc R U . . .
C20 C 0.70153(14) 0.34256(9) 0.47600(16) 0.0230(3) Uani 1 1 d . . . . .
H20 H 0.724990 0.358149 0.389592 0.028 Uiso 1 1 calc R U . . .
C21 C 0.78164(13) 0.30697(9) 0.57598(16) 0.0223(3) Uani 1 1 d . . . . .
C22 C 0.74613(14) 0.28367(10) 0.70121(17) 0.0272(4) Uani 1 1 d . . . . .
H22 H 0.800260 0.258185 0.769236 0.033 Uiso 1 1 calc R U . . .
C23 C 0.63192(14) 0.29749(10) 0.72727(16) 0.0248(4) Uani 1 1 d . . . . .
H23 H 0.608520 0.281572 0.813523 0.030 Uiso 1 1 calc R U . . .
C24 C 0.90692(14) 0.29459(10) 0.55298(18) 0.0286(4) Uani 1 1 d . . . . .
C25 C 0.16139(14) 0.43598(10) 0.91290(19) 0.0286(4) Uani 1 1 d . . . . .
H25A H 0.181256 0.422953 1.012884 0.034 Uiso 1 1 calc R U . . .
H25B H 0.087642 0.408368 0.877572 0.034 Uiso 1 1 calc R U . . .
C26 C 0.35101(13) 0.46043(9) 0.82206(15) 0.0175(3) Uani 1 1 d . . . . .
C27 C 0.44111(13) 0.43613(8) 0.74544(14) 0.0174(3) Uani 1 1 d . . . . .
C28 C 0.53657(13) 0.48546(9) 0.74009(15) 0.0196(3) Uani 1 1 d . . . . .
H28 H 0.598386 0.469691 0.689813 0.023 Uiso 1 1 calc R U . . .
C29 C 0.54379(13) 0.55725(9) 0.80644(15) 0.0209(3) Uani 1 1 d . . . . .
H29 H 0.610915 0.589369 0.803751 0.025 Uiso 1 1 calc R U . . .
C30 C 0.45271(13) 0.58159(9) 0.87633(15) 0.0205(3) Uani 1 1 d . . . . .
H30 H 0.456647 0.631279 0.919513 0.025 Uiso 1 1 calc R U . . .
C31 C 0.35524(13) 0.53433(9) 0.88439(15) 0.0188(3) Uani 1 1 d . . . . .
C32 C 0.25389(14) 0.56410(10) 0.95427(17) 0.0246(4) Uani 1 1 d . . . . .
H32A H 0.244475 0.620656 0.937399 0.030 Uiso 1 1 calc R U . . .
H32B H 0.271090 0.555755 1.056144 0.030 Uiso 1 1 calc R U . . .
C33 C 0.14050(15) 0.52275(10) 0.89882(19) 0.0298(4) Uani 1 1 d . . . . .
H33A H 0.076635 0.538588 0.952550 0.036 Uiso 1 1 calc R U . . .
H33B H 0.116838 0.536528 0.799766 0.036 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
Cl1 C14 1.7448(15) . ?
F1 C24 1.345(2) . ?
F2 C24 1.3409(19) . ?
F3 C24 1.335(2) . ?
O1 C17 1.3651(18) . ?
O1 H1 0.8400 . ?
N1 C26 1.4279(19) . ?
N1 C25 1.480(2) . ?
N1 H1X 0.890(14) . ?
C11 C18 1.524(2) . ?
C11 C12 1.537(2) . ?
C11 C27 1.538(2) . ?
C11 H11 1.0000 . ?
C12 C13 1.392(2) . ?
C12 C17 1.405(2) . ?
C13 C14 1.388(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.377(2) . ?
C15 C16 1.381(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.393(2) . ?
C16 H16 0.9500 . ?
C18 C23 1.389(2) . ?
C18 C19 1.390(2) . ?
C19 C20 1.389(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.385(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.387(2) . ?
C21 C24 1.496(2) . ?
C22 C23 1.385(2) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C25 C33 1.515(2) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C31 1.405(2) . ?
C26 C27 1.411(2) . ?
C27 C28 1.391(2) . ?
C28 C29 1.389(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.381(2) . ?
C29 H29 0.9500 . ?
C30 C31 1.392(2) . ?
C30 H30 0.9500 . ?
C31 C32 1.508(2) . ?
C32 C33 1.516(2) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?

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
C17 O1 H1 109.5 . . ?
C26 N1 C25 117.33(13) . . ?
C26 N1 H1X 111.5(12) . . ?
C25 N1 H1X 109.5(12) . . ?
C18 C11 C12 112.26(12) . . ?
C18 C11 C27 110.11(12) . . ?
C12 C11 C27 112.67(12) . . ?
C18 C11 H11 107.2 . . ?
C12 C11 H11 107.2 . . ?
C27 C11 H11 107.2 . . ?
C13 C12 C17 117.88(13) . . ?
C13 C12 C11 121.64(13) . . ?
C17 C12 C11 120.48(13) . . ?
C14 C13 C12 120.74(14) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 121.40(14) . . ?
C15 C14 Cl1 119.32(12) . . ?
C13 C14 Cl1 119.28(12) . . ?
C14 C15 C16 118.51(14) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
C15 C16 C17 121.14(14) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
O1 C17 C16 121.37(14) . . ?
O1 C17 C12 118.30(13) . . ?
C16 C17 C12 120.33(14) . . ?
C23 C18 C19 118.41(14) . . ?
C23 C18 C11 119.63(13) . . ?
C19 C18 C11 121.65(13) . . ?
C20 C19 C18 121.05(14) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C21 C20 C19 119.83(14) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C22 119.62(14) . . ?
C20 C21 C24 121.27(14) . . ?
C22 C21 C24 119.09(14) . . ?
C23 C22 C21 120.15(15) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C18 120.90(15) . . ?
C22 C23 H23 119.5 . . ?
C18 C23 H23 119.5 . . ?
F3 C24 F2 106.74(14) . . ?
F3 C24 F1 105.88(14) . . ?
F2 C24 F1 105.47(14) . . ?
F3 C24 C21 112.76(14) . . ?
F2 C24 C21 112.66(14) . . ?
F1 C24 C21 112.75(14) . . ?
N1 C25 C33 113.30(13) . . ?
N1 C25 H25A 108.9 . . ?
C33 C25 H25A 108.9 . . ?
N1 C25 H25B 108.9 . . ?
C33 C25 H25B 108.9 . . ?
H25A C25 H25B 107.7 . . ?
C31 C26 C27 120.48(14) . . ?
C31 C26 N1 120.98(13) . . ?
C27 C26 N1 118.53(13) . . ?
C28 C27 C26 118.16(14) . . ?
C28 C27 C11 121.46(13) . . ?
C26 C27 C11 120.36(13) . . ?
C29 C28 C27 121.63(14) . . ?
C29 C28 H28 119.2 . . ?
C27 C28 H28 119.2 . . ?
C30 C29 C28 119.54(14) . . ?
C30 C29 H29 120.2 . . ?
C28 C29 H29 120.2 . . ?
C29 C30 C31 120.92(14) . . ?
C29 C30 H30 119.5 . . ?
C31 C30 H30 119.5 . . ?
C30 C31 C26 119.15(14) . . ?
C30 C31 C32 119.83(14) . . ?
C26 C31 C32 120.98(13) . . ?
C31 C32 C33 110.86(13) . . ?
C31 C32 H32A 109.5 . . ?
C33 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
C33 C32 H32B 109.5 . . ?
H32A C32 H32B 108.1 . . ?
C25 C33 C32 108.23(14) . . ?
C25 C33 H33A 110.1 . . ?
C32 C33 H33A 110.1 . . ?
C25 C33 H33B 110.1 . . ?
C32 C33 H33B 110.1 . . ?
H33A C33 H33B 108.4 . . ?

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
C18 C11 C12 C13 -113.11(15) . . . . ?
C27 C11 C12 C13 11.89(19) . . . . ?
C18 C11 C12 C17 66.15(18) . . . . ?
C27 C11 C12 C17 -168.85(13) . . . . ?
C17 C12 C13 C14 0.2(2) . . . . ?
C11 C12 C13 C14 179.44(13) . . . . ?
C12 C13 C14 C15 0.2(2) . . . . ?
C12 C13 C14 Cl1 -179.08(11) . . . . ?
C13 C14 C15 C16 -0.3(2) . . . . ?
Cl1 C14 C15 C16 178.93(12) . . . . ?
C14 C15 C16 C17 0.1(2) . . . . ?
C15 C16 C17 O1 -179.33(14) . . . . ?
C15 C16 C17 C12 0.2(2) . . . . ?
C13 C12 C17 O1 179.20(13) . . . . ?
C11 C12 C17 O1 -0.1(2) . . . . ?
C13 C12 C17 C16 -0.3(2) . . . . ?
C11 C12 C17 C16 -179.61(13) . . . . ?
C12 C11 C18 C23 -151.03(14) . . . . ?
C27 C11 C18 C23 82.57(17) . . . . ?
C12 C11 C18 C19 35.50(19) . . . . ?
C27 C11 C18 C19 -90.89(16) . . . . ?
C23 C18 C19 C20 -2.2(2) . . . . ?
C11 C18 C19 C20 171.34(14) . . . . ?
C18 C19 C20 C21 1.1(2) . . . . ?
C19 C20 C21 C22 0.7(2) . . . . ?
C19 C20 C21 C24 -177.96(15) . . . . ?
C20 C21 C22 C23 -1.4(2) . . . . ?
C24 C21 C22 C23 177.27(15) . . . . ?
C21 C22 C23 C18 0.3(3) . . . . ?
C19 C18 C23 C22 1.5(2) . . . . ?
C11 C18 C23 C22 -172.21(15) . . . . ?
C20 C21 C24 F3 11.8(2) . . . . ?
C22 C21 C24 F3 -166.85(15) . . . . ?
C20 C21 C24 F2 132.72(16) . . . . ?
C22 C21 C24 F2 -45.9(2) . . . . ?
C20 C21 C24 F1 -108.04(18) . . . . ?
C22 C21 C24 F1 73.3(2) . . . . ?
C26 N1 C25 C33 30.6(2) . . . . ?
C25 N1 C26 C31 3.3(2) . . . . ?
C25 N1 C26 C27 -177.76(13) . . . . ?
C31 C26 C27 C28 3.4(2) . . . . ?
N1 C26 C27 C28 -175.54(13) . . . . ?
C31 C26 C27 C11 -175.09(12) . . . . ?
N1 C26 C27 C11 5.9(2) . . . . ?
C18 C11 C27 C28 17.64(18) . . . . ?
C12 C11 C27 C28 -108.52(15) . . . . ?
C18 C11 C27 C26 -163.87(13) . . . . ?
C12 C11 C27 C26 69.97(17) . . . . ?
C26 C27 C28 C29 -0.7(2) . . . . ?
C11 C27 C28 C29 177.82(13) . . . . ?
C27 C28 C29 C30 -1.9(2) . . . . ?
C28 C29 C30 C31 1.7(2) . . . . ?
C29 C30 C31 C26 1.0(2) . . . . ?
C29 C30 C31 C32 -176.53(14) . . . . ?
C27 C26 C31 C30 -3.6(2) . . . . ?
N1 C26 C31 C30 175.36(13) . . . . ?
C27 C26 C31 C32 173.88(13) . . . . ?
N1 C26 C31 C32 -7.2(2) . . . . ?
C30 C31 C32 C33 154.83(14) . . . . ?
C26 C31 C32 C33 -22.6(2) . . . . ?
N1 C25 C33 C32 -59.03(18) . . . . ?
C31 C32 C33 C25 53.53(18) . . . . ?

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
O1 H1 N1 0.84 2.13 2.9644(17) 177.3 4_565 yes
C16 H16 N1 0.95 2.69 3.438(2) 136.3 4_565 yes

_refine_diff_density_max         0.444
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.042



####################################################################### 
# 
# 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_8f_prime
_database_code_depnum_ccdc_archive 'CCDC 2468968'
loop_
_audit_author_name
_audit_author_address
'Filipe Almeida Paz'
;University of Aveiro CICECO Aveiro Institute of Materials
Portugal
;
_audit_update_record             
;
2025-07-01 deposited with the CCDC.	2025-10-24 downloaded from the CCDC.
;
#==============================================================================

#=============================================================================
_audit_creation_method           'SHELXL-2019/3, manual editing plus enCIFer'
_audit_creation_date             '1 July 2025'
_shelx_SHELXL_version_number     2019/3
#=============================================================================

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H20 F3 N O'
_chemical_formula_sum            'C23 H20 F3 N O'
_chemical_formula_weight         383.40

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'


#=============================================================================
# CRYSTAL DATA
#=============================================================================

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   11.1723(2)
_cell_length_b                   16.3213(4)
_cell_length_c                   10.3436(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.802(2)
_cell_angle_gamma                90
_cell_volume                     1863.91(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    19213
_cell_measurement_theta_min      1.8520
_cell_measurement_theta_max      28.0330
_cell_oxdiff_length_a            11.17335(18)
_cell_oxdiff_length_b            16.3227(3)
_cell_oxdiff_length_c            10.34195(18)
_cell_oxdiff_angle_alpha         90.0188(15)
_cell_oxdiff_angle_beta          98.8098(14)
_cell_oxdiff_angle_gamma         89.9703(15)
_cell_oxdiff_volume              1863.91(6)
_cell_oxdiff_measurement_reflns_used 19213

#=============================================================================
# EXPERIMENTAL DATA
#============================================================================= 

_exptl_crystal_description       Plate
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_T_min  0.71685
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.734
_oxdiff_exptl_absorpt_empirical_full_max 1.538
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      150.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix3000
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            30525
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.844
_diffrn_reflns_theta_max         28.214
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4445
_reflns_number_gt                3556
_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.
;

_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0598200000
_diffrn_orient_matrix_UB_12      -0.0076341000
_diffrn_orient_matrix_UB_13      -0.0317897000
_diffrn_orient_matrix_UB_21      0.0213879000
_diffrn_orient_matrix_UB_22      -0.0333502000
_diffrn_orient_matrix_UB_23      -0.0340671000
_diffrn_orient_matrix_UB_31      -0.0095303000
_diffrn_orient_matrix_UB_32      -0.0267918000
_diffrn_orient_matrix_UB_33      0.0514363000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -88.00  11.00   0.50   30.00    --  -17.97 -70.00-167.00  198
  2  ω    -47.00  53.00   0.50   30.00    --  -17.97  70.00 -36.00  200
  3  ω      8.00  46.00   0.50   30.00    --  -17.97  70.00 -36.00   76
  4  ω    -86.00 -34.00   0.50   30.00    --  -17.97 -70.00-167.00  104
  5  ω     12.00  65.00   0.50   30.00    --   17.27-125.00-120.00  106
  6  ω     -6.00  87.00   0.50   30.00    --   17.27  45.00  90.00  186
  7  ω     -4.00  23.00   0.50   30.00    --   17.27 -15.00 -90.00   54
  8  ω    -56.00 -13.00   0.50   30.00    --   17.27 -15.00 -90.00   86
  9  ω    -13.00  31.00   0.50   30.00    --   17.27  77.00 150.00   88
 10  ω     41.00  89.00   0.50   30.00    --   17.27  77.00 150.00   96
 11  ω    -33.00  -7.00   0.50   30.00    --   17.27 -70.00-167.00   52
 12  ω     -8.00  39.00   0.50   30.00    --   17.27  70.00 -36.00   94
 13  ω     22.00  50.00   0.50   30.00    --   17.27-125.00  90.00   56
 14  ω    -30.00  17.00   0.50   30.00    --  -17.97 -95.00 -30.00   94
 15  ω     22.00  61.00   0.50   30.00    --  -17.97  15.00 -30.00   78
 16  ω    -28.00  19.00   0.50   30.00    --  -17.97 -95.00-150.00   94
 17  ω    -30.00  17.00   0.50   30.00    --  -17.97 -95.00  90.00   94
 18  ω    -67.00 -13.00   0.50   30.00    --  -17.97 125.00 -90.00  108
 19  ω    -21.00  13.00   0.50   30.00    --  -17.97  15.00 -30.00   68
 20  ω    -15.00  19.00   0.50   30.00    --  -17.97 -95.00 150.00   68
 21  ω    -48.00  55.00   0.50   30.00    --  -17.97  77.00   0.00  206
 22  ω    -70.00 -14.00   0.50   30.00    --  -17.97 125.00  90.00  112
;
_diffrn_measurement_method       'ω scans'
_diffrn_oxdiff_digest_frames     
;
014e780cd8a8dfec0409ff7d3840addc1d00025a2ae
;
_diffrn_oxdiff_digest_hkl        
;
43d42eb339638d04ff1ca3c0ad81439da9c2d4
;

_computing_data_collection       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_structure_solution    'SHELXT 2014/5'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    DIAMOND
_computing_publication_material  SHELXL-2019/3


#=============================================================================
# REFINEMENT DATA
#=============================================================================

_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)+(0.1054P)²+1.1702P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4445
_refine_ls_number_parameters     266
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0663
_refine_ls_wR_factor_ref         0.2031
_refine_ls_wR_factor_gt          0.1903
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000


#=============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
#=============================================================================

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 0.17129(14) 0.72500(9) -0.00922(15) 0.0420(4) Uani 1 1 d . . . . .
H1 H 0.199243 0.687968 0.043258 0.063 Uiso 1 1 calc R U . . .
F1 F -0.4797(7) 0.8082(6) -0.1693(8) 0.084(2) Uiso 0.3 1 d . . P A 1
F2 F -0.4298(7) 0.8579(5) 0.0232(9) 0.082(2) Uiso 0.3 1 d . . P A 1
F3 F -0.4208(4) 0.7346(3) 0.0045(6) 0.0457(11) Uiso 0.3 1 d . . P A 1
F4 F -0.4364(3) 0.7234(2) -0.0521(5) 0.0412(8) Uiso 0.4 1 d . . P A 2
F5 F -0.4156(3) 0.8376(3) 0.0676(4) 0.0432(8) Uiso 0.4 1 d . . P A 2
F6 F -0.4804(3) 0.8406(3) -0.1467(4) 0.0335(7) Uiso 0.4 1 d . . P A 2
F7 F -0.4528(6) 0.7263(4) -0.1250(8) 0.0799(18) Uiso 0.3 1 d . . P A 3
F8 F -0.4764(6) 0.8585(4) -0.1028(8) 0.0639(19) Uiso 0.3 1 d . . P A 3
F9 F -0.4232(6) 0.7950(5) 0.0562(7) 0.0738(17) Uiso 0.3 1 d . . P A 3
N1 N 0.26212(16) 0.90224(11) -0.32706(17) 0.0363(4) Uani 1 1 d D . . . .
H1X H 0.285(2) 0.8753(16) -0.250(2) 0.055 Uiso 1 1 d D U . . .
C1 C 0.16642(18) 0.95942(12) -0.32167(18) 0.0326(4) Uani 1 1 d . . . . .
C2 C 0.07624(18) 0.93971(11) -0.24539(18) 0.0305(4) Uani 1 1 d . . . . .
C3 C -0.01811(19) 0.99493(12) -0.24217(19) 0.0345(4) Uani 1 1 d . . . . .
H3 H -0.079356 0.982554 -0.190799 0.041 Uiso 1 1 calc R U . . .
C4 C -0.0248(2) 1.06780(13) -0.3124(2) 0.0399(5) Uani 1 1 d . . . . .
H4 H -0.089570 1.104946 -0.308456 0.048 Uiso 1 1 calc R U . . .
C5 C 0.0632(2) 1.08574(13) -0.3878(2) 0.0413(5) Uani 1 1 d . . . . .
H5 H 0.058026 1.135326 -0.436433 0.050 Uiso 1 1 calc R U . . .
C6 C 0.1595(2) 1.03256(13) -0.39404(19) 0.0386(5) Uani 1 1 d . . . . .
C7 C 0.2553(2) 1.05355(16) -0.4770(3) 0.0528(6) Uani 1 1 d . . . . .
H7A H 0.310051 1.095710 -0.431636 0.063 Uiso 1 1 calc R U . . .
H7B H 0.215868 1.077054 -0.561094 0.063 Uiso 1 1 calc R U . . .
C8 C 0.3291(2) 0.97959(19) -0.5042(2) 0.0555(7) Uani 1 1 d . . . . .
H8A H 0.400868 0.997374 -0.542484 0.067 Uiso 1 1 calc R U . . .
H8B H 0.279738 0.943204 -0.567916 0.067 Uiso 1 1 calc R U . . .
C9 C 0.3695(2) 0.93348(17) -0.3777(2) 0.0481(6) Uani 1 1 d . . . . .
H9A H 0.422742 0.887291 -0.393853 0.058 Uiso 1 1 calc R U . . .
H9B H 0.415902 0.970485 -0.312634 0.058 Uiso 1 1 calc R U . . .
C11 C 0.08649(17) 0.86084(11) -0.16310(18) 0.0298(4) Uani 1 1 d . . . . .
H11 H 0.111980 0.815956 -0.218803 0.036 Uiso 1 1 calc R U . . .
C12 C -0.03698(17) 0.83760(11) -0.12922(18) 0.0302(4) Uani 1 1 d . . . . .
C13 C -0.1250(2) 0.80530(13) -0.2260(2) 0.0393(5) Uani 1 1 d . . . . .
H13 H -0.104191 0.791872 -0.309167 0.047 Uiso 1 1 calc R U . . .
C14 C -0.2428(2) 0.79252(14) -0.2024(2) 0.0454(5) Uani 1 1 d . . . . .
H14 H -0.302182 0.771006 -0.269346 0.054 Uiso 1 1 calc R U . . .
C15 C -0.27348(19) 0.81127(14) -0.0807(2) 0.0418(5) Uani 1 1 d . . . . .
C16 C -0.1868(2) 0.84041(13) 0.0172(2) 0.0391(5) Uani 1 1 d . . . . .
H16 H -0.207118 0.851677 0.101313 0.047 Uiso 1 1 calc R U . . .
C17 C -0.06908(18) 0.85338(12) -0.00716(19) 0.0344(4) Uani 1 1 d . . . . .
H17 H -0.009607 0.873401 0.061042 0.041 Uiso 1 1 calc R U . . .
C18 C 0.18365(17) 0.86797(12) -0.04206(18) 0.0302(4) Uani 1 1 d . . . . .
C19 C 0.22176(18) 0.79823(12) 0.0321(2) 0.0334(4) Uani 1 1 d . . . . .
C20 C 0.30726(19) 0.80511(14) 0.1445(2) 0.0390(5) Uani 1 1 d . . . . .
H20 H 0.332322 0.757452 0.194056 0.047 Uiso 1 1 calc R U . . .
C21 C 0.3562(2) 0.88009(14) 0.1849(2) 0.0419(5) Uani 1 1 d . . . . .
H21 H 0.414444 0.883976 0.261844 0.050 Uiso 1 1 calc R U . . .
C22 C 0.3201(2) 0.94939(14) 0.1133(2) 0.0432(5) Uani 1 1 d . . . . .
H22 H 0.353221 1.001318 0.140430 0.052 Uiso 1 1 calc R U . . .
C23 C 0.23468(19) 0.94266(13) 0.0007(2) 0.0374(5) Uani 1 1 d . . . . .
H23 H 0.210519 0.990661 -0.048351 0.045 Uiso 1 1 calc R U . . .
C25 C -0.4021(2) 0.80088(16) -0.0580(3) 0.0521(6) 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 C19 1.362(2) . ?
O1 H1 0.8400 . ?
F1 C25 1.337(8) . ?
F2 C25 1.322(8) . ?
F3 C25 1.294(5) . ?
F4 C25 1.326(4) . ?
F5 C25 1.460(5) . ?
F6 C25 1.335(4) . ?
F7 C25 1.471(8) . ?
F8 C25 1.292(7) . ?
F9 C25 1.244(7) . ?
N1 C1 1.427(3) . ?
N1 C9 1.472(3) . ?
N1 H1X 0.915(17) . ?
C1 C6 1.405(3) . ?
C1 C2 1.409(3) . ?
C2 C3 1.391(3) . ?
C2 C11 1.538(3) . ?
C3 C4 1.390(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.510(3) . ?
C7 C8 1.512(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.517(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C11 C12 1.522(3) . ?
C11 C18 1.531(3) . ?
C11 H11 1.0000 . ?
C12 C17 1.388(3) . ?
C12 C13 1.395(3) . ?
C13 C14 1.391(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.375(3) . ?
C15 C25 1.500(3) . ?
C16 C17 1.393(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C23 1.389(3) . ?
C18 C19 1.402(3) . ?
C19 C20 1.391(3) . ?
C20 C21 1.379(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.378(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.392(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?

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
C19 O1 H1 109.5 . . ?
C1 N1 C9 116.35(18) . . ?
C1 N1 H1X 113.0(18) . . ?
C9 N1 H1X 110.1(18) . . ?
C6 C1 C2 120.45(19) . . ?
C6 C1 N1 121.02(18) . . ?
C2 C1 N1 118.49(17) . . ?
C3 C2 C1 118.36(18) . . ?
C3 C2 C11 121.44(17) . . ?
C1 C2 C11 120.14(17) . . ?
C4 C3 C2 121.5(2) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C5 C4 C3 119.5(2) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 121.19(19) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 119.0(2) . . ?
C5 C6 C7 120.3(2) . . ?
C1 C6 C7 120.6(2) . . ?
C6 C7 C8 112.3(2) . . ?
C6 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 C9 109.5(2) . . ?
C7 C8 H8A 109.8 . . ?
C9 C8 H8A 109.8 . . ?
C7 C8 H8B 109.8 . . ?
C9 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
N1 C9 C8 109.15(19) . . ?
N1 C9 H9A 109.9 . . ?
C8 C9 H9A 109.9 . . ?
N1 C9 H9B 109.9 . . ?
C8 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
C12 C11 C18 112.63(15) . . ?
C12 C11 C2 110.04(15) . . ?
C18 C11 C2 111.87(15) . . ?
C12 C11 H11 107.3 . . ?
C18 C11 H11 107.3 . . ?
C2 C11 H11 107.3 . . ?
C17 C12 C13 118.11(18) . . ?
C17 C12 C11 122.17(17) . . ?
C13 C12 C11 119.52(17) . . ?
C14 C13 C12 120.8(2) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 119.9(2) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C16 C15 C14 120.0(2) . . ?
C16 C15 C25 120.5(2) . . ?
C14 C15 C25 119.5(2) . . ?
C15 C16 C17 119.9(2) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C12 C17 C16 121.27(19) . . ?
C12 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C23 C18 C19 117.56(18) . . ?
C23 C18 C11 122.16(17) . . ?
C19 C18 C11 120.26(17) . . ?
O1 C19 C20 122.10(18) . . ?
O1 C19 C18 117.65(18) . . ?
C20 C19 C18 120.24(19) . . ?
C21 C20 C19 121.0(2) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C22 C21 C20 119.7(2) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C21 C22 C23 119.4(2) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C18 C23 C22 122.08(19) . . ?
C18 C23 H23 119.0 . . ?
C22 C23 H23 119.0 . . ?
F9 C25 F8 101.0(5) . . ?
F3 C25 F2 101.5(5) . . ?
F4 C25 F6 109.3(3) . . ?
F3 C25 F1 111.9(5) . . ?
F2 C25 F1 107.4(6) . . ?
F4 C25 F5 106.2(3) . . ?
F6 C25 F5 105.4(3) . . ?
F9 C25 F7 105.6(5) . . ?
F8 C25 F7 104.6(5) . . ?
F9 C25 C15 118.9(4) . . ?
F8 C25 C15 116.1(3) . . ?
F3 C25 C15 113.9(3) . . ?
F2 C25 C15 110.1(4) . . ?
F4 C25 C15 114.0(2) . . ?
F6 C25 C15 112.4(2) . . ?
F1 C25 C15 111.5(4) . . ?
F5 C25 C15 109.0(2) . . ?
F7 C25 C15 109.2(3) . . ?

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
C9 N1 C1 C6 17.7(3) . . . . ?
C9 N1 C1 C2 -164.42(18) . . . . ?
C6 C1 C2 C3 -1.0(3) . . . . ?
N1 C1 C2 C3 -178.88(17) . . . . ?
C6 C1 C2 C11 -178.11(17) . . . . ?
N1 C1 C2 C11 4.0(3) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C11 C2 C3 C4 177.38(17) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
C4 C5 C6 C7 -179.8(2) . . . . ?
C2 C1 C6 C5 0.9(3) . . . . ?
N1 C1 C6 C5 178.72(17) . . . . ?
C2 C1 C6 C7 -179.38(18) . . . . ?
N1 C1 C6 C7 -1.6(3) . . . . ?
C5 C6 C7 C8 -162.7(2) . . . . ?
C1 C6 C7 C8 17.6(3) . . . . ?
C6 C7 C8 C9 -47.8(3) . . . . ?
C1 N1 C9 C8 -48.4(3) . . . . ?
C7 C8 C9 N1 63.5(3) . . . . ?
C3 C2 C11 C12 22.7(2) . . . . ?
C1 C2 C11 C12 -160.27(16) . . . . ?
C3 C2 C11 C18 -103.3(2) . . . . ?
C1 C2 C11 C18 73.7(2) . . . . ?
C18 C11 C12 C17 24.1(3) . . . . ?
C2 C11 C12 C17 -101.5(2) . . . . ?
C18 C11 C12 C13 -161.11(18) . . . . ?
C2 C11 C12 C13 73.3(2) . . . . ?
C17 C12 C13 C14 2.6(3) . . . . ?
C11 C12 C13 C14 -172.37(19) . . . . ?
C12 C13 C14 C15 -0.6(3) . . . . ?
C13 C14 C15 C16 -1.7(3) . . . . ?
C13 C14 C15 C25 177.2(2) . . . . ?
C14 C15 C16 C17 1.9(3) . . . . ?
C25 C15 C16 C17 -177.0(2) . . . . ?
C13 C12 C17 C16 -2.4(3) . . . . ?
C11 C12 C17 C16 172.46(18) . . . . ?
C15 C16 C17 C12 0.2(3) . . . . ?
C12 C11 C18 C23 -111.2(2) . . . . ?
C2 C11 C18 C23 13.4(2) . . . . ?
C12 C11 C18 C19 66.9(2) . . . . ?
C2 C11 C18 C19 -168.49(17) . . . . ?
C23 C18 C19 O1 179.60(18) . . . . ?
C11 C18 C19 O1 1.4(3) . . . . ?
C23 C18 C19 C20 0.3(3) . . . . ?
C11 C18 C19 C20 -177.95(18) . . . . ?
O1 C19 C20 C21 -179.4(2) . . . . ?
C18 C19 C20 C21 -0.1(3) . . . . ?
C19 C20 C21 C22 0.0(3) . . . . ?
C20 C21 C22 C23 -0.1(3) . . . . ?
C19 C18 C23 C22 -0.4(3) . . . . ?
C11 C18 C23 C22 177.83(19) . . . . ?
C21 C22 C23 C18 0.3(3) . . . . ?
C16 C15 C25 F9 -21.2(6) . . . . ?
C14 C15 C25 F9 159.9(5) . . . . ?
C16 C15 C25 F8 99.7(5) . . . . ?
C14 C15 C25 F8 -79.2(5) . . . . ?
C16 C15 C25 F3 -80.1(4) . . . . ?
C14 C15 C25 F3 101.0(4) . . . . ?
C16 C15 C25 F2 33.0(5) . . . . ?
C14 C15 C25 F2 -145.9(5) . . . . ?
C16 C15 C25 F4 -109.8(3) . . . . ?
C14 C15 C25 F4 71.4(4) . . . . ?
C16 C15 C25 F6 125.2(3) . . . . ?
C14 C15 C25 F6 -53.7(4) . . . . ?
C16 C15 C25 F1 152.1(5) . . . . ?
C14 C15 C25 F1 -26.8(5) . . . . ?
C16 C15 C25 F5 8.7(4) . . . . ?
C14 C15 C25 F5 -170.2(3) . . . . ?
C16 C15 C25 F7 -142.3(4) . . . . ?
C14 C15 C25 F7 38.8(4) . . . . ?

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
O1 H1 N1 0.84 2.04 2.882(2) 178.2 4_576 yes
C20 H20 F1^a 0.95 2.58 3.375(9) 141.7 4_676 yes

_refine_diff_density_max         0.769
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.067



####################################################################### 
# 
# 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_8a_tripleprime
_database_code_depnum_ccdc_archive 'CCDC 2468969'
loop_
_audit_author_name
_audit_author_address
'Filipe Almeida Paz'
;University of Aveiro CICECO Aveiro Institute of Materials
Portugal
;
_audit_update_record             
;
2025-07-01 deposited with the CCDC.	2025-10-24 downloaded from the CCDC.
;
#==============================================================================

#=============================================================================
_audit_creation_method           'SHELXL-2019/3, manual editing plus enCIFer'
_audit_creation_date             '1 July 2025'
_shelx_SHELXL_version_number     2019/3
#=============================================================================

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H27 Cl F3 N O3'
_chemical_formula_sum            'C37 H27 Cl F3 N O3'
_chemical_formula_weight         626.04

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'
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'


#=============================================================================
# CRYSTAL DATA
#=============================================================================

_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                   7.9684(2)
_cell_length_b                   12.2691(3)
_cell_length_c                   16.0679(4)
_cell_angle_alpha                78.803(2)
_cell_angle_beta                 79.663(2)
_cell_angle_gamma                76.349(2)
_cell_volume                     1482.67(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    21427
_cell_measurement_theta_min      1.9890
_cell_measurement_theta_max      26.1440
_cell_oxdiff_length_a            7.9684(2)
_cell_oxdiff_length_b            12.2691(3)
_cell_oxdiff_length_c            16.0679(4)
_cell_oxdiff_angle_alpha         78.803(2)
_cell_oxdiff_angle_beta          79.663(2)
_cell_oxdiff_angle_gamma         76.349(2)
_cell_oxdiff_volume              1482.67(7)
_cell_oxdiff_measurement_reflns_used 21427

#=============================================================================
# EXPERIMENTAL DATA
#============================================================================= 

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.188
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_T_min  0.98138
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.908
_oxdiff_exptl_absorpt_empirical_full_max 1.157
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      149.99(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix3000
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            31555
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.664
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5416
_reflns_number_gt                4473
_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.
;

_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0077097000
_diffrn_orient_matrix_UB_12      0.0559081000
_diffrn_orient_matrix_UB_13      -0.0233028000
_diffrn_orient_matrix_UB_21      -0.0176055000
_diffrn_orient_matrix_UB_22      0.0221597000
_diffrn_orient_matrix_UB_23      0.0390097000
_diffrn_orient_matrix_UB_31      0.0904967000
_diffrn_orient_matrix_UB_32      -0.0037670000
_diffrn_orient_matrix_UB_33      -0.0009082000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     16.00  65.00   0.50   45.00    --   12.93-132.00  86.00   98
  2  ω     20.00  71.00   0.50   45.00    --   12.93-138.00 -89.00  102
  3  ω    -75.00 -24.00   0.50   45.00    --  -13.67 138.00 -27.00  102
  4  ω    -49.00 -19.00   0.50   45.00    --  -13.67 132.00 156.00   60
  5  ω     22.00  63.00   0.50   45.00    --   12.93-125.00 150.00   82
  6  ω     56.00  82.00   0.50   45.00    --   12.93  38.00 -30.00   52
  7  ω      8.00  82.00   0.50   45.00    --   12.93  57.00  30.00  148
  8  ω     -9.00  36.00   0.50   45.00    --   12.93  38.00 -30.00   90
  9  ω    -55.00  36.00   0.50   45.00    --   12.93 -57.00  90.00  182
 10  ω    -10.00  89.00   0.50   45.00    --   12.93  19.00-150.00  198
 11  ω    -21.00  51.00   0.50   45.00    --   12.93 -99.00 -30.00  144
 12  ω    -23.00  29.00   0.50   45.00    --   12.93 -99.00   0.00  104
 13  ω     13.00  65.00   0.50   45.00    --   12.93-125.00-150.00  104
 14  ω     -3.00  23.00   0.50   45.00    --  -13.67  19.00-120.00   52
 15  ω      7.00  33.00   0.50   45.00    --  -13.67  38.00-120.00   52
 16  ω    -32.00  -6.00   0.50   45.00    --  -13.67  38.00-120.00   52
 17  ω    -85.00 -37.00   0.50   45.00    --  -13.67 -77.00-180.00   96
 18  ω    -32.00  17.00   0.50   45.00    --  -13.67 -77.00-180.00   98
 19  ω    -12.00  21.00   0.50   45.00    --  -13.67 -99.00 -60.00   66
 20  ω     -9.00  24.00   0.50   45.00    --  -13.67 -99.00  90.00   66
 21  ω    -82.00   7.00   0.50   45.00    --  -13.67 -38.00   0.00  178
 22  ω    -27.00  13.00   0.50   45.00    --  -13.67  38.00  90.00   80
 23  ω    -12.00  17.00   0.50   45.00    --  -13.67 -77.00-150.00   58
 24  ω    -23.00  19.00   0.50   45.00    --  -13.67 -99.00 -90.00   84
 25  ω     16.00  55.00   0.50   45.00    --  -13.67  38.00  90.00   78
 26  ω    -83.00  -9.00   0.50   45.00    --  -13.67 -38.00  90.00  148
 27  ω    -82.00 -19.00   0.50   45.00    --  -13.67 -77.00-150.00  126
 28  ω    -56.00  21.00   0.50   45.00    --  -13.67 -19.00-120.00  154
 29  ω    -89.00 -63.00   0.50   45.00    --  -13.67 -19.00-120.00   52
 30  ω    -22.00  16.00   0.50   45.00    --  -13.67 -99.00  60.00   76
 31  ω     24.00  53.00   0.50   45.00    --  -13.67  19.00-120.00   58
 32  ω    -84.00   7.00   0.50   45.00    --  -13.67 -38.00-150.00  182
;
_diffrn_measurement_method       'ω scans'
_diffrn_oxdiff_digest_frames     
;
01d533400a148bcee149703d7582ba005000025e894
;
_diffrn_oxdiff_digest_hkl        
;
43ae84284ba0f2ce48379d0950f689e6b1b775
;


_computing_data_collection       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_structure_solution    'SHELXT 2014/5'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    DIAMOND
_computing_publication_material  SHELXL-2019/3


#=============================================================================
# REFINEMENT DATA
#=============================================================================

_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)+(0.0406P)²+0.6347P] 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         5416
_refine_ls_number_parameters     407
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.1008
_refine_ls_wR_factor_gt          0.0957
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

#=============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
#=============================================================================
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
Cl1 Cl -0.11741(6) 0.38175(4) 0.57707(3) 0.04382(14) Uani 1 1 d . . . . .
O1 O 0.52306(15) 0.17497(9) 0.72996(7) 0.0322(3) Uani 1 1 d . . . . .
O2 O 0.37051(17) 0.08447(13) 0.84318(9) 0.0534(4) Uani 1 1 d . . . . .
O3 O 0.13780(17) 0.43279(11) 1.12123(8) 0.0451(3) Uani 1 1 d . . . . .
N1 N 0.40162(19) 0.31726(12) 1.08438(9) 0.0321(3) Uani 1 1 d . . . . .
C1 C 0.5714(2) 0.25939(15) 1.11285(11) 0.0370(4) Uani 1 1 d . . . . .
H1A H 0.603520 0.181093 1.099365 0.044 Uiso 1 1 calc R U . . .
H1B H 0.562273 0.254714 1.175651 0.044 Uiso 1 1 calc R U . . .
C2 C 0.7107(2) 0.32433(16) 1.06817(11) 0.0361(4) Uani 1 1 d . . . . .
H2A H 0.822324 0.288509 1.090365 0.043 Uiso 1 1 calc R U . . .
H2B H 0.676517 0.403494 1.079833 0.043 Uiso 1 1 calc R U . . .
C3 C 0.7336(2) 0.32414(16) 0.97242(11) 0.0360(4) Uani 1 1 d . . . . .
H3A H 0.800617 0.382209 0.942280 0.043 Uiso 1 1 calc R U . . .
H3B H 0.801393 0.249100 0.959669 0.043 Uiso 1 1 calc R U . . .
C4 C 0.5600(2) 0.34866(13) 0.93942(10) 0.0283(4) Uani 1 1 d . . . . .
C5 C 0.5570(2) 0.37123(13) 0.85136(10) 0.0278(4) Uani 1 1 d . . . . .
H5 H 0.663665 0.374578 0.814443 0.033 Uiso 1 1 calc R U . . .
C6 C 0.4062(2) 0.38903(13) 0.81498(10) 0.0258(3) Uani 1 1 d . . . . .
C7 C 0.2503(2) 0.38497(14) 0.87010(11) 0.0294(4) Uani 1 1 d . . . . .
H7 H 0.144573 0.396445 0.847031 0.035 Uiso 1 1 calc R U . . .
C8 C 0.2481(2) 0.36442(14) 0.95798(11) 0.0311(4) Uani 1 1 d . . . . .
H8 H 0.140613 0.362802 0.994590 0.037 Uiso 1 1 calc R U . . .
C9 C 0.4022(2) 0.34597(13) 0.99365(10) 0.0289(4) Uani 1 1 d . . . . .
C11 C 0.4156(2) 0.41096(13) 0.71785(10) 0.0260(3) Uani 1 1 d . . . . .
H11 H 0.540427 0.383269 0.694723 0.031 Uiso 1 1 calc R U . . .
C12 C 0.3696(2) 0.53610(14) 0.67902(10) 0.0273(4) Uani 1 1 d . . . . .
C13 C 0.2482(2) 0.61640(15) 0.72030(11) 0.0359(4) Uani 1 1 d . . . . .
H13 H 0.192562 0.594791 0.776555 0.043 Uiso 1 1 calc R U . . .
C14 C 0.2073(3) 0.72854(15) 0.67989(13) 0.0409(5) Uani 1 1 d . . . . .
H14 H 0.124294 0.783251 0.708637 0.049 Uiso 1 1 calc R U . . .
C15 C 0.2873(2) 0.76017(15) 0.59807(12) 0.0376(4) Uani 1 1 d . . . . .
C16 C 0.4087(2) 0.68074(16) 0.55623(12) 0.0410(5) Uani 1 1 d . . . . .
H16 H 0.464162 0.702395 0.499944 0.049 Uiso 1 1 calc R U . . .
C17 C 0.4488(2) 0.56977(15) 0.59685(11) 0.0355(4) Uani 1 1 d . . . . .
H17 H 0.532183 0.515405 0.567966 0.043 Uiso 1 1 calc R U . . .
C18 C 0.3114(2) 0.34085(13) 0.68668(10) 0.0268(4) Uani 1 1 d . . . . .
C19 C 0.1607(2) 0.38906(14) 0.64898(10) 0.0294(4) Uani 1 1 d . . . . .
H19 H 0.117970 0.468938 0.642080 0.035 Uiso 1 1 calc R U . . .
C20 C 0.0737(2) 0.32055(15) 0.62170(11) 0.0319(4) Uani 1 1 d . . . . .
C21 C 0.1348(2) 0.20457(15) 0.62772(11) 0.0359(4) Uani 1 1 d . . . . .
H21 H 0.074277 0.159055 0.607562 0.043 Uiso 1 1 calc R U . . .
C22 C 0.2857(2) 0.15597(15) 0.66366(11) 0.0355(4) Uani 1 1 d . . . . .
H22 H 0.331588 0.076608 0.667432 0.043 Uiso 1 1 calc R U . . .
C23 C 0.3689(2) 0.22356(14) 0.69393(11) 0.0300(4) Uani 1 1 d . . . . .
C25 C 0.5065(2) 0.10657(14) 0.80798(11) 0.0336(4) Uani 1 1 d . . . . .
C28 C 0.2435(3) 0.87904(17) 0.55225(15) 0.0502(5) Uani 1 1 d . . . . .
F1 F 0.1341(2) 0.94940(11) 0.60139(11) 0.0888(5) Uani 1 1 d . . . . .
F2 F 0.3797(2) 0.92514(12) 0.52544(13) 0.1041(7) Uani 1 1 d . . . . .
F3 F 0.1641(2) 0.88755(11) 0.48544(10) 0.0806(5) Uani 1 1 d . . . . .
C32 C 0.2611(2) 0.35741(15) 1.14187(11) 0.0348(4) Uani 1 1 d . . . . .
C34 C 0.2576(2) 0.29977(15) 1.23302(11) 0.0354(4) Uani 1 1 d . . . . .
C35 C 0.2161(2) 0.36390(16) 1.29847(12) 0.0383(4) Uani 1 1 d . . . . .
H35 H 0.197276 0.444391 1.285467 0.046 Uiso 1 1 calc R U . . .
C36 C 0.2019(3) 0.31097(18) 1.38294(12) 0.0441(5) Uani 1 1 d . . . . .
H36 H 0.174556 0.355185 1.427860 0.053 Uiso 1 1 calc R U . . .
C37 C 0.2274(3) 0.19413(18) 1.40215(13) 0.0485(5) Uani 1 1 d . . . . .
H37 H 0.217651 0.158063 1.460230 0.058 Uiso 1 1 calc R U . . .
C38 C 0.2667(3) 0.12994(18) 1.33736(13) 0.0530(6) Uani 1 1 d . . . . .
H38 H 0.283214 0.049559 1.350529 0.064 Uiso 1 1 calc R U . . .
C39 C 0.2822(3) 0.18254(16) 1.25322(13) 0.0484(5) Uani 1 1 d . . . . .
H39 H 0.309975 0.137930 1.208530 0.058 Uiso 1 1 calc R U . . .
C40 C 0.6758(2) 0.06292(14) 0.84050(11) 0.0323(4) Uani 1 1 d . . . . .
C41 C 0.6816(3) -0.01923(16) 0.91356(12) 0.0402(4) Uani 1 1 d . . . . .
H41 H 0.577792 -0.043056 0.941714 0.048 Uiso 1 1 calc R U . . .
C42 C 0.8370(3) -0.06644(17) 0.94552(13) 0.0466(5) Uani 1 1 d . . . . .
H42 H 0.840904 -0.123211 0.995034 0.056 Uiso 1 1 calc R U . . .
C43 C 0.9863(3) -0.03034(19) 0.90483(14) 0.0515(5) Uani 1 1 d . . . . .
H43 H 1.093705 -0.062610 0.926372 0.062 Uiso 1 1 calc R U . . .
C44 C 0.9812(3) 0.0517(2) 0.83357(14) 0.0561(6) Uani 1 1 d . . . . .
H44 H 1.084728 0.076800 0.806657 0.067 Uiso 1 1 calc R U . . .
C45 C 0.8259(2) 0.09840(17) 0.80036(13) 0.0431(5) Uani 1 1 d . . . . .
H45 H 0.823279 0.154387 0.750363 0.052 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
Cl1 C20 1.7436(17) . ?
O1 C25 1.370(2) . ?
O1 C23 1.405(2) . ?
O2 C25 1.195(2) . ?
O3 C32 1.225(2) . ?
N1 C32 1.377(2) . ?
N1 C9 1.431(2) . ?
N1 C1 1.478(2) . ?
C1 C2 1.514(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.517(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.513(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.392(2) . ?
C4 C9 1.399(2) . ?
C5 C6 1.383(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.395(2) . ?
C6 C11 1.522(2) . ?
C7 C8 1.383(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.400(2) . ?
C8 H8 0.9500 . ?
C11 C12 1.525(2) . ?
C11 C18 1.528(2) . ?
C11 H11 1.0000 . ?
C12 C13 1.386(2) . ?
C12 C17 1.387(2) . ?
C13 C14 1.392(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.383(3) . ?
C15 C28 1.492(3) . ?
C16 C17 1.381(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C23 1.392(2) . ?
C18 C19 1.395(2) . ?
C19 C20 1.381(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.381(2) . ?
C21 C22 1.383(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.377(2) . ?
C22 H22 0.9500 . ?
C25 C40 1.477(2) . ?
C28 F2 1.307(2) . ?
C28 F3 1.317(2) . ?
C28 F1 1.338(3) . ?
C32 C34 1.496(2) . ?
C34 C35 1.381(3) . ?
C34 C39 1.386(3) . ?
C35 C36 1.384(3) . ?
C35 H35 0.9500 . ?
C36 C37 1.380(3) . ?
C36 H36 0.9500 . ?
C37 C38 1.374(3) . ?
C37 H37 0.9500 . ?
C38 C39 1.378(3) . ?
C38 H38 0.9500 . ?
C39 H39 0.9500 . ?
C40 C45 1.378(3) . ?
C40 C41 1.391(2) . ?
C41 C42 1.381(3) . ?
C41 H41 0.9500 . ?
C42 C43 1.377(3) . ?
C42 H42 0.9500 . ?
C43 C44 1.369(3) . ?
C43 H43 0.9500 . ?
C44 C45 1.388(3) . ?
C44 H44 0.9500 . ?
C45 H45 0.9500 . ?

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
C25 O1 C23 116.61(13) . . ?
C32 N1 C9 122.33(14) . . ?
C32 N1 C1 121.00(14) . . ?
C9 N1 C1 115.77(13) . . ?
N1 C1 C2 109.92(14) . . ?
N1 C1 H1A 109.7 . . ?
C2 C1 H1A 109.7 . . ?
N1 C1 H1B 109.7 . . ?
C2 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
C1 C2 C3 109.63(15) . . ?
C1 C2 H2A 109.7 . . ?
C3 C2 H2A 109.7 . . ?
C1 C2 H2B 109.7 . . ?
C3 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
C4 C3 C2 111.76(15) . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
C5 C4 C9 118.29(15) . . ?
C5 C4 C3 118.89(15) . . ?
C9 C4 C3 122.79(15) . . ?
C6 C5 C4 123.19(15) . . ?
C6 C5 H5 118.4 . . ?
C4 C5 H5 118.4 . . ?
C5 C6 C7 117.69(15) . . ?
C5 C6 C11 119.62(14) . . ?
C7 C6 C11 122.70(14) . . ?
C8 C7 C6 120.68(15) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 120.83(15) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C4 C9 C8 119.33(15) . . ?
C4 C9 N1 119.77(14) . . ?
C8 C9 N1 120.78(15) . . ?
C6 C11 C12 114.42(13) . . ?
C6 C11 C18 112.23(13) . . ?
C12 C11 C18 111.38(13) . . ?
C6 C11 H11 106.0 . . ?
C12 C11 H11 106.0 . . ?
C18 C11 H11 106.0 . . ?
C13 C12 C17 118.66(15) . . ?
C13 C12 C11 123.31(15) . . ?
C17 C12 C11 117.98(15) . . ?
C12 C13 C14 120.43(17) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 119.96(18) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.11(16) . . ?
C14 C15 C28 121.30(19) . . ?
C16 C15 C28 118.58(18) . . ?
C17 C16 C15 119.54(18) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C12 121.30(17) . . ?
C16 C17 H17 119.4 . . ?
C12 C17 H17 119.4 . . ?
C23 C18 C19 117.39(15) . . ?
C23 C18 C11 119.58(14) . . ?
C19 C18 C11 123.02(14) . . ?
C20 C19 C18 119.91(15) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 121.90(16) . . ?
C19 C20 Cl1 119.35(13) . . ?
C21 C20 Cl1 118.75(13) . . ?
C20 C21 C22 118.72(16) . . ?
C20 C21 H21 120.6 . . ?
C22 C21 H21 120.6 . . ?
C23 C22 C21 119.45(16) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C22 C23 C18 122.56(15) . . ?
C22 C23 O1 119.80(15) . . ?
C18 C23 O1 117.56(14) . . ?
O2 C25 O1 122.82(16) . . ?
O2 C25 C40 125.36(16) . . ?
O1 C25 C40 111.80(15) . . ?
F2 C28 F3 107.22(19) . . ?
F2 C28 F1 105.15(19) . . ?
F3 C28 F1 104.52(18) . . ?
F2 C28 C15 113.30(18) . . ?
F3 C28 C15 113.04(17) . . ?
F1 C28 C15 112.89(18) . . ?
O3 C32 N1 123.43(16) . . ?
O3 C32 C34 119.51(16) . . ?
N1 C32 C34 116.96(15) . . ?
C35 C34 C39 119.17(17) . . ?
C35 C34 C32 119.90(16) . . ?
C39 C34 C32 120.74(16) . . ?
C34 C35 C36 120.03(18) . . ?
C34 C35 H35 120.0 . . ?
C36 C35 H35 120.0 . . ?
C37 C36 C35 120.20(18) . . ?
C37 C36 H36 119.9 . . ?
C35 C36 H36 119.9 . . ?
C38 C37 C36 120.05(18) . . ?
C38 C37 H37 120.0 . . ?
C36 C37 H37 120.0 . . ?
C37 C38 C39 119.78(19) . . ?
C37 C38 H38 120.1 . . ?
C39 C38 H38 120.1 . . ?
C38 C39 C34 120.76(18) . . ?
C38 C39 H39 119.6 . . ?
C34 C39 H39 119.6 . . ?
C45 C40 C41 119.67(16) . . ?
C45 C40 C25 122.67(16) . . ?
C41 C40 C25 117.65(16) . . ?
C42 C41 C40 120.53(18) . . ?
C42 C41 H41 119.7 . . ?
C40 C41 H41 119.7 . . ?
C43 C42 C41 119.27(19) . . ?
C43 C42 H42 120.4 . . ?
C41 C42 H42 120.4 . . ?
C44 C43 C42 120.57(19) . . ?
C44 C43 H43 119.7 . . ?
C42 C43 H43 119.7 . . ?
C43 C44 C45 120.5(2) . . ?
C43 C44 H44 119.8 . . ?
C45 C44 H44 119.8 . . ?
C40 C45 C44 119.45(18) . . ?
C40 C45 H45 120.3 . . ?
C44 C45 H45 120.3 . . ?

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
C32 N1 C1 C2 -119.50(17) . . . . ?
C9 N1 C1 C2 49.9(2) . . . . ?
N1 C1 C2 C3 -63.39(19) . . . . ?
C1 C2 C3 C4 44.3(2) . . . . ?
C2 C3 C4 C5 168.86(15) . . . . ?
C2 C3 C4 C9 -13.3(2) . . . . ?
C9 C4 C5 C6 -1.2(2) . . . . ?
C3 C4 C5 C6 176.70(15) . . . . ?
C4 C5 C6 C7 0.6(2) . . . . ?
C4 C5 C6 C11 -178.83(15) . . . . ?
C5 C6 C7 C8 0.3(2) . . . . ?
C11 C6 C7 C8 179.79(15) . . . . ?
C6 C7 C8 C9 -0.7(2) . . . . ?
C5 C4 C9 C8 0.8(2) . . . . ?
C3 C4 C9 C8 -177.01(16) . . . . ?
C5 C4 C9 N1 176.79(14) . . . . ?
C3 C4 C9 N1 -1.0(2) . . . . ?
C7 C8 C9 C4 0.1(2) . . . . ?
C7 C8 C9 N1 -175.81(15) . . . . ?
C32 N1 C9 C4 151.55(16) . . . . ?
C1 N1 C9 C4 -17.7(2) . . . . ?
C32 N1 C9 C8 -32.5(2) . . . . ?
C1 N1 C9 C8 158.20(16) . . . . ?
C5 C6 C11 C12 -97.84(17) . . . . ?
C7 C6 C11 C12 82.73(19) . . . . ?
C5 C6 C11 C18 133.98(15) . . . . ?
C7 C6 C11 C18 -45.5(2) . . . . ?
C6 C11 C12 C13 -32.8(2) . . . . ?
C18 C11 C12 C13 95.85(18) . . . . ?
C6 C11 C12 C17 149.82(15) . . . . ?
C18 C11 C12 C17 -81.56(18) . . . . ?
C17 C12 C13 C14 -0.1(3) . . . . ?
C11 C12 C13 C14 -177.51(16) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C13 C14 C15 C28 178.66(17) . . . . ?
C14 C15 C16 C17 0.2(3) . . . . ?
C28 C15 C16 C17 -178.81(17) . . . . ?
C15 C16 C17 C12 0.0(3) . . . . ?
C13 C12 C17 C16 0.0(3) . . . . ?
C11 C12 C17 C16 177.53(16) . . . . ?
C6 C11 C18 C23 -69.00(19) . . . . ?
C12 C11 C18 C23 161.23(15) . . . . ?
C6 C11 C18 C19 112.40(17) . . . . ?
C12 C11 C18 C19 -17.4(2) . . . . ?
C23 C18 C19 C20 0.9(2) . . . . ?
C11 C18 C19 C20 179.52(15) . . . . ?
C18 C19 C20 C21 -2.4(3) . . . . ?
C18 C19 C20 Cl1 178.45(12) . . . . ?
C19 C20 C21 C22 1.2(3) . . . . ?
Cl1 C20 C21 C22 -179.56(14) . . . . ?
C20 C21 C22 C23 1.3(3) . . . . ?
C21 C22 C23 C18 -2.8(3) . . . . ?
C21 C22 C23 O1 -179.52(15) . . . . ?
C19 C18 C23 C22 1.7(2) . . . . ?
C11 C18 C23 C22 -177.01(16) . . . . ?
C19 C18 C23 O1 178.47(14) . . . . ?
C11 C18 C23 O1 -0.2(2) . . . . ?
C25 O1 C23 C22 -70.4(2) . . . . ?
C25 O1 C23 C18 112.68(17) . . . . ?
C23 O1 C25 O2 3.0(2) . . . . ?
C23 O1 C25 C40 -178.47(14) . . . . ?
C14 C15 C28 F2 124.9(2) . . . . ?
C16 C15 C28 F2 -56.2(3) . . . . ?
C14 C15 C28 F3 -112.9(2) . . . . ?
C16 C15 C28 F3 66.1(3) . . . . ?
C14 C15 C28 F1 5.5(3) . . . . ?
C16 C15 C28 F1 -175.56(18) . . . . ?
C9 N1 C32 O3 -11.1(3) . . . . ?
C1 N1 C32 O3 157.57(18) . . . . ?
C9 N1 C32 C34 165.25(15) . . . . ?
C1 N1 C32 C34 -26.0(2) . . . . ?
O3 C32 C34 C35 -49.0(3) . . . . ?
N1 C32 C34 C35 134.46(18) . . . . ?
O3 C32 C34 C39 125.9(2) . . . . ?
N1 C32 C34 C39 -50.6(3) . . . . ?
C39 C34 C35 C36 0.9(3) . . . . ?
C32 C34 C35 C36 175.89(17) . . . . ?
C34 C35 C36 C37 -0.7(3) . . . . ?
C35 C36 C37 C38 -0.1(3) . . . . ?
C36 C37 C38 C39 0.6(3) . . . . ?
C37 C38 C39 C34 -0.3(3) . . . . ?
C35 C34 C39 C38 -0.4(3) . . . . ?
C32 C34 C39 C38 -175.4(2) . . . . ?
O2 C25 C40 C45 -174.76(19) . . . . ?
O1 C25 C40 C45 6.7(2) . . . . ?
O2 C25 C40 C41 6.8(3) . . . . ?
O1 C25 C40 C41 -171.77(15) . . . . ?
C45 C40 C41 C42 -0.8(3) . . . . ?
C25 C40 C41 C42 177.72(17) . . . . ?
C40 C41 C42 C43 0.8(3) . . . . ?
C41 C42 C43 C44 0.2(3) . . . . ?
C42 C43 C44 C45 -1.1(4) . . . . ?
C41 C40 C45 C44 -0.1(3) . . . . ?
C25 C40 C45 C44 -178.54(19) . . . . ?
C43 C44 C45 C40 1.0(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
C8 H8 O3 0.95 2.35 2.835(2) 111.0 . yes
C21 H21 F1 0.95 2.52 3.241(2) 132.6 1_545 yes

_refine_diff_density_max         0.361
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.038



