# Supplementary Information (SI) for Green 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_w12
_database_code_depnum_ccdc_archive 'CCDC 2451747'
loop_
_audit_author_name
_audit_author_address
'bin wang' 'Guizhou University'
_audit_update_record             
;
2025-05-16 deposited with the CCDC.	2025-11-07 downloaded from the CCDC.
;
_audit_creation_date             2024-10-31
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H17 F6 N O'
_chemical_formula_sum            'C21 H17 F6 N O'
_chemical_formula_weight         413.36
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.1569(2)
_cell_length_b                   22.3534(4)
_cell_length_c                   9.6077(2)
_cell_angle_alpha                90
_cell_angle_beta                 109.638(2)
_cell_angle_gamma                90
_cell_volume                     1852.19(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4616
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.9750
_cell_measurement_theta_min      3.9120
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.158
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.23124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6944
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.224
_diffrn_reflns_theta_min         3.955
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     13.00  86.00   1.00    1.00    --   40.73  57.00  90.00   73
  2  ω     79.00 161.00   1.00    1.00    --  108.20  61.00   0.00   82
  3  ω    108.00 135.00   1.00    1.00    --  108.20 -30.00   0.00   27
  4  ω    113.00 141.00   1.00    1.00    --  108.20 -77.00-150.00   28
  5  ω     37.00 101.00   1.00    1.00    --  108.20 -94.00-150.00   64
  6  ω     25.00  96.00   1.00    1.00    --   40.73-125.00-150.00   71
  7  ω     32.00  71.00   1.00    1.00    --  108.20 -30.00   0.00   39
  8  ω     48.00 120.00   1.00    1.00    --  108.20-125.00 120.00   72
  9  ω    -61.00  34.00   1.00    1.00    --  -40.73  38.00-120.00   95
 10  ω     97.00 148.00   1.00    1.00    --  108.20 125.00   0.00   51
 11  ω     96.00 148.00   1.00    1.00    --  108.20 125.00 -60.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0452963000
_diffrn_orient_matrix_UB_12      0.0610051000
_diffrn_orient_matrix_UB_13      0.0482221000
_diffrn_orient_matrix_UB_21      -0.1326142000
_diffrn_orient_matrix_UB_22      -0.0301427000
_diffrn_orient_matrix_UB_23      0.0389473000
_diffrn_orient_matrix_UB_31      0.1107106000
_diffrn_orient_matrix_UB_32      -0.0110395000
_diffrn_orient_matrix_UB_33      0.1585230000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3254
_reflns_number_total             3645
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.0086(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3645
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0472
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0847P)²+0.3240P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1317
_refine_ls_wR_factor_ref         0.1366
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C16(H16), C17(H17), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 0.49267(14) 0.97325(4) 0.31527(14) 0.0488(3) Uani 1 1 d . . . . .
F2 F 0.35726(13) 0.90460(5) 0.17683(13) 0.0506(3) Uani 1 1 d . . . . .
F3 F 0.59304(14) 0.91763(5) 0.19096(13) 0.0509(3) Uani 1 1 d . . . . .
F4 F 0.52922(14) 0.58803(5) -0.40126(12) 0.0469(3) Uani 1 1 d . . . . .
F5 F 0.36765(14) 0.52568(6) -0.36886(12) 0.0507(3) Uani 1 1 d . . . . .
F6 F 0.60610(14) 0.50063(5) -0.31587(12) 0.0504(3) Uani 1 1 d . . . . .
O1 O 0.52315(14) 0.79510(5) 0.22637(12) 0.0326(3) Uani 1 1 d . . . . .
H1 H 0.539346 0.758280 0.221795 0.049 Uiso 1 1 calc R U . . .
N1 N 0.63730(14) 0.69021(5) 0.31635(13) 0.0245(3) Uani 1 1 d . . . . .
C1 C 0.62547(18) 0.85420(7) 0.66009(18) 0.0307(4) Uani 1 1 d . . . . .
C2 C 0.6541(2) 0.87497(9) 0.8064(2) 0.0385(4) Uani 1 1 d . . . . .
H2 H 0.648998 0.916573 0.824430 0.046 Uiso 1 1 calc R U . . .
C3 C 0.6888(2) 0.83568(10) 0.92125(19) 0.0432(5) Uani 1 1 d . . . . .
H3 H 0.706145 0.849852 1.018720 0.052 Uiso 1 1 calc R U . . .
C4 C 0.6989(2) 0.77422(10) 0.89566(19) 0.0410(4) Uani 1 1 d . . . . .
H4 H 0.722902 0.747137 0.976436 0.049 Uiso 1 1 calc R U . . .
C5 C 0.67484(19) 0.75261(8) 0.75606(18) 0.0342(4) Uani 1 1 d . . . . .
H5 H 0.682950 0.710876 0.741413 0.041 Uiso 1 1 calc R U . . .
C6 C 0.63780(17) 0.79216(7) 0.63299(17) 0.0270(3) Uani 1 1 d . . . . .
C7 C 0.60783(17) 0.77153(7) 0.48500(16) 0.0251(3) Uani 1 1 d . . . . .
C8 C 0.58125(18) 0.89393(7) 0.53915(18) 0.0316(4) Uani 1 1 d . . . . .
H8 H 0.573625 0.935477 0.556318 0.038 Uiso 1 1 calc R U . . .
C9 C 0.54915(17) 0.87383(7) 0.39775(17) 0.0281(3) Uani 1 1 d . . . . .
C10 C 0.56123(17) 0.81176(7) 0.36946(16) 0.0262(3) Uani 1 1 d . . . . .
C11 C 0.4982(2) 0.91654(7) 0.2708(2) 0.0340(4) Uani 1 1 d . . . . .
C12 C 0.61430(18) 0.70509(7) 0.45797(16) 0.0275(3) Uani 1 1 d . . . . .
H12A H 0.700124 0.687378 0.540101 0.033 Uiso 1 1 calc R U . . .
H12B H 0.516470 0.686524 0.458895 0.033 Uiso 1 1 calc R U . . .
C13 C 0.79881(19) 0.70117(8) 0.32804(19) 0.0348(4) Uani 1 1 d . . . . .
H13A H 0.867837 0.677989 0.410608 0.052 Uiso 1 1 calc R U . . .
H13B H 0.822190 0.743872 0.345293 0.052 Uiso 1 1 calc R U . . .
H13C H 0.814382 0.688995 0.236048 0.052 Uiso 1 1 calc R U . . .
C14 C 0.5970(2) 0.62660(7) 0.28418(17) 0.0299(3) Uani 1 1 d . . . . .
H14A H 0.496091 0.618629 0.297411 0.036 Uiso 1 1 calc R U . . .
H14B H 0.676216 0.601571 0.356092 0.036 Uiso 1 1 calc R U . . .
C15 C 0.58660(18) 0.60871(6) 0.12999(16) 0.0268(3) Uani 1 1 d . . . . .
C16 C 0.4772(2) 0.63497(7) 0.00932(19) 0.0344(4) Uani 1 1 d . . . . .
H16 H 0.415257 0.666745 0.024372 0.041 Uiso 1 1 calc R U . . .
C17 C 0.4565(2) 0.61585(7) -0.13256(18) 0.0354(4) Uani 1 1 d . . . . .
H17 H 0.382143 0.634819 -0.214446 0.042 Uiso 1 1 calc R U . . .
C18 C 0.54527(18) 0.56852(7) -0.15527(17) 0.0285(3) Uani 1 1 d . . . . .
C19 C 0.6778(2) 0.56294(8) 0.10581(18) 0.0350(4) Uani 1 1 d . . . . .
H19 H 0.755507 0.545280 0.187443 0.042 Uiso 1 1 calc R U . . .
C20 C 0.6566(2) 0.54262(8) -0.03664(19) 0.0355(4) Uani 1 1 d . . . . .
H20 H 0.718841 0.510972 -0.051860 0.043 Uiso 1 1 calc R U . . .
C21 C 0.5130(2) 0.54587(7) -0.30914(18) 0.0337(4) 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
F1 C11 1.3441(18) . ?
F2 C11 1.330(2) . ?
F3 C11 1.338(2) . ?
F4 C21 1.3348(19) . ?
F5 C21 1.338(2) . ?
F6 C21 1.338(2) . ?
O1 H1 0.8400 . ?
O1 C10 1.3520(18) . ?
N1 C12 1.4829(18) . ?
N1 C13 1.4657(19) . ?
N1 C14 1.4753(18) . ?
C1 C2 1.419(2) . ?
C1 C6 1.422(2) . ?
C1 C8 1.409(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.361(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.404(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.372(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.423(2) . ?
C6 C7 1.431(2) . ?
C7 C10 1.380(2) . ?
C7 C12 1.512(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.366(2) . ?
C9 C10 1.425(2) . ?
C9 C11 1.495(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.506(2) . ?
C15 C16 1.383(2) . ?
C15 C19 1.388(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.380(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.395(2) . ?
C18 C20 1.376(2) . ?
C18 C21 1.495(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.392(2) . ?
C20 H20 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
C10 O1 H1 109.5 . . ?
C13 N1 C12 110.06(12) . . ?
C13 N1 C14 110.63(12) . . ?
C14 N1 C12 107.79(11) . . ?
C2 C1 C6 120.05(16) . . ?
C8 C1 C2 121.13(15) . . ?
C8 C1 C6 118.81(14) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.46(17) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.03(16) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.16(18) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.57(17) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 117.72(14) . . ?
C1 C6 C7 119.71(14) . . ?
C5 C6 C7 122.53(14) . . ?
C6 C7 C12 118.80(13) . . ?
C10 C7 C6 119.56(14) . . ?
C10 C7 C12 121.41(13) . . ?
C1 C8 H8 119.4 . . ?
C9 C8 C1 121.26(14) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 C10 120.35(14) . . ?
C8 C9 C11 120.36(14) . . ?
C10 C9 C11 119.28(14) . . ?
O1 C10 C7 122.87(13) . . ?
O1 C10 C9 116.88(13) . . ?
C7 C10 C9 120.25(14) . . ?
F1 C11 C9 112.19(14) . . ?
F2 C11 F1 105.87(13) . . ?
F2 C11 F3 106.45(15) . . ?
F2 C11 C9 113.04(13) . . ?
F3 C11 F1 105.43(14) . . ?
F3 C11 C9 113.24(14) . . ?
N1 C12 C7 113.81(12) . . ?
N1 C12 H12A 108.8 . . ?
N1 C12 H12B 108.8 . . ?
C7 C12 H12A 108.8 . . ?
C7 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 H14A 109.0 . . ?
N1 C14 H14B 109.0 . . ?
N1 C14 C15 112.99(12) . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C16 C15 C14 120.02(14) . . ?
C16 C15 C19 118.65(14) . . ?
C19 C15 C14 121.17(14) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.15(14) . . ?
C17 C16 H16 119.4 . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.71(15) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C21 118.65(15) . . ?
C20 C18 C17 119.87(14) . . ?
C20 C18 C21 121.45(14) . . ?
C15 C19 H19 119.6 . . ?
C15 C19 C20 120.80(15) . . ?
C20 C19 H19 119.6 . . ?
C18 C20 C19 119.77(15) . . ?
C18 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
F4 C21 F5 105.67(14) . . ?
F4 C21 F6 106.67(13) . . ?
F4 C21 C18 112.80(13) . . ?
F5 C21 C18 112.06(13) . . ?
F6 C21 F5 106.40(14) . . ?
F6 C21 C18 112.72(14) . . ?

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 C14 C15 C16 -62.40(19) . . . . ?
N1 C14 C15 C19 122.28(16) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
C1 C6 C7 C10 -2.6(2) . . . . ?
C1 C6 C7 C12 -177.18(13) . . . . ?
C1 C8 C9 C10 -0.6(2) . . . . ?
C1 C8 C9 C11 178.29(14) . . . . ?
C2 C1 C6 C5 1.8(2) . . . . ?
C2 C1 C6 C7 179.61(14) . . . . ?
C2 C1 C8 C9 -178.03(15) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 C1 -0.6(2) . . . . ?
C4 C5 C6 C7 -178.36(15) . . . . ?
C5 C6 C7 C10 175.17(14) . . . . ?
C5 C6 C7 C12 0.6(2) . . . . ?
C6 C1 C2 C3 -2.0(2) . . . . ?
C6 C1 C8 C9 0.6(2) . . . . ?
C6 C7 C10 O1 -176.48(13) . . . . ?
C6 C7 C10 C9 2.6(2) . . . . ?
C6 C7 C12 N1 -159.43(13) . . . . ?
C8 C1 C2 C3 176.55(16) . . . . ?
C8 C1 C6 C5 -176.84(14) . . . . ?
C8 C1 C6 C7 1.0(2) . . . . ?
C8 C9 C10 O1 178.09(14) . . . . ?
C8 C9 C10 C7 -1.0(2) . . . . ?
C8 C9 C11 F1 1.1(2) . . . . ?
C8 C9 C11 F2 -118.49(16) . . . . ?
C8 C9 C11 F3 120.34(16) . . . . ?
C10 C7 C12 N1 26.1(2) . . . . ?
C10 C9 C11 F1 -179.97(14) . . . . ?
C10 C9 C11 F2 60.41(19) . . . . ?
C10 C9 C11 F3 -60.8(2) . . . . ?
C11 C9 C10 O1 -0.8(2) . . . . ?
C11 C9 C10 C7 -179.90(14) . . . . ?
C12 N1 C14 C15 169.25(13) . . . . ?
C12 C7 C10 O1 -2.0(2) . . . . ?
C12 C7 C10 C9 177.03(13) . . . . ?
C13 N1 C12 C7 75.23(16) . . . . ?
C13 N1 C14 C15 -70.38(17) . . . . ?
C14 N1 C12 C7 -164.03(13) . . . . ?
C14 C15 C16 C17 -174.47(15) . . . . ?
C14 C15 C19 C20 173.50(15) . . . . ?
C15 C16 C17 C18 1.1(3) . . . . ?
C15 C19 C20 C18 0.7(3) . . . . ?
C16 C15 C19 C20 -1.9(3) . . . . ?
C16 C17 C18 C20 -2.3(3) . . . . ?
C16 C17 C18 C21 175.81(15) . . . . ?
C17 C18 C20 C19 1.4(3) . . . . ?
C17 C18 C21 F4 59.0(2) . . . . ?
C17 C18 C21 F5 -60.1(2) . . . . ?
C17 C18 C21 F6 179.87(15) . . . . ?
C19 C15 C16 C17 1.0(3) . . . . ?
C20 C18 C21 F4 -122.94(17) . . . . ?
C20 C18 C21 F5 117.95(18) . . . . ?
C20 C18 C21 F6 -2.1(2) . . . . ?
C21 C18 C20 C19 -176.66(15) . . . . ?

_olex2_date_sample_data_collection 2024-10-30
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.166
_oxdiff_exptl_absorpt_empirical_full_min 0.490
####################################################################### 
# 
# 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_38
_database_code_depnum_ccdc_archive 'CCDC 2451748'
loop_
_audit_author_name
_audit_author_address
'bin wang' 'Guizhou University'
_audit_update_record             
;
2025-05-16 deposited with the CCDC.	2025-11-07 downloaded from the CCDC.
;
_audit_creation_date             2024-12-06
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H20 F3 N O'
_chemical_formula_sum            'C21 H20 F3 N O'
_chemical_formula_weight         359.38
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.5424(5)
_cell_length_b                   19.5291(8)
_cell_length_c                   10.0245(5)
_cell_angle_alpha                90
_cell_angle_beta                 111.692(5)
_cell_angle_gamma                90
_cell_volume                     1735.82(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2391
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.4960
_cell_measurement_theta_min      4.5100
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.892
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6793
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.665
_diffrn_reflns_theta_min         4.528
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -12.00  29.00   1.00    3.00    --  -41.11  38.00 -60.00   41
  2  ω    -65.00 -26.00   1.00    3.00    --  -41.11  38.00 -60.00   39
  3  ω   -117.00 -31.00   1.00    3.00    --  -41.11 -77.00 120.00   86
  4  ω      1.00  81.00   1.00    3.00    --   41.11 -99.00-120.00   80
  5  ω     33.00 108.00   1.00    6.00    --  107.58 -94.00 -30.00   75
  6  ω     78.00 109.00   1.00    6.00    --  107.58-125.00 120.00   31
  7  ω     38.00  64.00   1.00    6.00    --  107.58 -30.00 150.00   26
  8  ω     35.00 135.00   1.00    6.00    --  107.58 -61.00 150.00  100
  9  ω    108.00 136.00   1.00    6.00    --  107.58 -30.00 150.00   28
 10  ω    100.00 129.00   1.00    6.00    --  107.58 125.00  60.00   29
 11  ω     94.00 169.00   1.00    6.00    --  107.58 125.00 -90.00   75
 12  ω     92.00 155.00   1.00    6.00    --  107.58  45.00-120.00   63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0413027000
_diffrn_orient_matrix_UB_12      0.0631094000
_diffrn_orient_matrix_UB_13      -0.0701413000
_diffrn_orient_matrix_UB_21      -0.0361097000
_diffrn_orient_matrix_UB_22      0.0470349000
_diffrn_orient_matrix_UB_23      0.1064556000
_diffrn_orient_matrix_UB_31      0.1648433000
_diffrn_orient_matrix_UB_32      -0.0054894000
_diffrn_orient_matrix_UB_33      0.1053706000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2708
_reflns_number_total             3408
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3408
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0552
_refine_ls_restrained_S_all      1.022
_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)+(0.0937P)²+0.0881P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1601
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C10(H10), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C21(H21A,H21B,H21C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 0.76592(17) 0.51017(6) 0.87434(14) 0.0420(4) Uani 1 1 d . . . . .
F2 F 0.68300(17) 0.43456(7) 0.98191(15) 0.0475(4) Uani 1 1 d . . . . .
F3 F 0.91102(15) 0.42881(7) 0.99126(14) 0.0458(4) Uani 1 1 d . . . . .
O1 O 0.75233(16) 0.30141(7) 0.91479(14) 0.0292(3) Uani 1 1 d . . . . .
H1 H 0.725136 0.260275 0.909666 0.044 Uiso 1 1 calc R U . . .
N1 N 0.61831(17) 0.19119(8) 0.80202(16) 0.0225(3) Uani 1 1 d . . . . .
C1 C 0.6400(2) 0.39055(10) 0.5119(2) 0.0247(4) Uani 1 1 d . . . . .
C2 C 0.6094(2) 0.42213(11) 0.3765(2) 0.0303(4) Uani 1 1 d . . . . .
H2 H 0.614791 0.470532 0.370198 0.036 Uiso 1 1 calc R U . . .
C3 C 0.5723(2) 0.38306(12) 0.2550(2) 0.0312(5) Uani 1 1 d . . . . .
H3 H 0.551963 0.404630 0.164850 0.037 Uiso 1 1 calc R U . . .
C4 C 0.5638(2) 0.31109(11) 0.2621(2) 0.0281(4) Uani 1 1 d . . . . .
C5 C 0.5912(2) 0.27968(10) 0.3918(2) 0.0254(4) Uani 1 1 d . . . . .
H5 H 0.583705 0.231248 0.395163 0.030 Uiso 1 1 calc R U . . .
C6 C 0.63085(19) 0.31812(10) 0.52213(19) 0.0222(4) Uani 1 1 d . . . . .
C7 C 0.66316(19) 0.28689(9) 0.65894(19) 0.0221(4) Uani 1 1 d . . . . .
C8 C 0.7114(2) 0.32768(10) 0.78122(19) 0.0228(4) Uani 1 1 d . . . . .
C9 C 0.7185(2) 0.40014(10) 0.7699(2) 0.0246(4) Uani 1 1 d . . . . .
C10 C 0.6823(2) 0.43051(10) 0.6384(2) 0.0259(4) Uani 1 1 d . . . . .
H10 H 0.685511 0.478973 0.631920 0.031 Uiso 1 1 calc R U . . .
C11 C 0.7683(2) 0.44287(10) 0.9034(2) 0.0309(4) Uani 1 1 d . . . . .
C12 C 0.6527(2) 0.20972(10) 0.6739(2) 0.0266(4) Uani 1 1 d . . . . .
H12A H 0.572906 0.191298 0.586881 0.032 Uiso 1 1 calc R U . . .
H12B H 0.749597 0.188456 0.681579 0.032 Uiso 1 1 calc R U . . .
C13 C 0.4575(2) 0.20197(10) 0.7745(2) 0.0274(4) Uani 1 1 d . . . . .
H13A H 0.431327 0.249976 0.748789 0.041 Uiso 1 1 calc R U . . .
H13B H 0.437488 0.190707 0.861065 0.041 Uiso 1 1 calc R U . . .
H13C H 0.396574 0.172399 0.695329 0.041 Uiso 1 1 calc R U . . .
C14 C 0.6634(2) 0.11998(10) 0.8483(2) 0.0273(4) Uani 1 1 d . . . . .
H14A H 0.762356 0.110393 0.841402 0.033 Uiso 1 1 calc R U . . .
H14B H 0.588624 0.088045 0.783202 0.033 Uiso 1 1 calc R U . . .
C15 C 0.6742(2) 0.10777(9) 1.0003(2) 0.0243(4) Uani 1 1 d . . . . .
C16 C 0.5547(2) 0.08115(11) 1.0318(2) 0.0341(5) Uani 1 1 d . . . . .
H16 H 0.462648 0.070090 0.956072 0.041 Uiso 1 1 calc R U . . .
C17 C 0.5692(3) 0.07066(13) 1.1732(3) 0.0429(6) Uani 1 1 d . . . . .
H17 H 0.486956 0.052334 1.193332 0.052 Uiso 1 1 calc R U . . .
C18 C 0.7023(3) 0.08659(12) 1.2852(2) 0.0384(5) Uani 1 1 d . . . . .
H18 H 0.711431 0.079423 1.381822 0.046 Uiso 1 1 calc R U . . .
C19 C 0.8216(2) 0.11299(11) 1.2551(2) 0.0354(5) Uani 1 1 d . . . . .
H19 H 0.913521 0.124060 1.331071 0.042 Uiso 1 1 calc R U . . .
C20 C 0.8067(2) 0.12326(10) 1.1142(2) 0.0277(4) Uani 1 1 d . . . . .
H20 H 0.889487 0.141434 1.094651 0.033 Uiso 1 1 calc R U . . .
C21 C 0.5252(2) 0.26935(12) 0.1263(2) 0.0350(5) Uani 1 1 d . . . . .
H21A H 0.525310 0.220578 0.149309 0.052 Uiso 1 1 calc R U . . .
H21B H 0.600147 0.277937 0.082810 0.052 Uiso 1 1 calc R U . . .
H21C H 0.424976 0.282477 0.058616 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
F1 C11 1.345(2) . ?
F2 C11 1.335(2) . ?
F3 C11 1.349(3) . ?
O1 H1 0.8400 . ?
O1 C8 1.350(2) . ?
N1 C12 1.483(2) . ?
N1 C13 1.470(2) . ?
N1 C14 1.479(2) . ?
C1 C2 1.420(3) . ?
C1 C6 1.423(3) . ?
C1 C10 1.415(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.368(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.411(3) . ?
C4 C5 1.372(3) . ?
C4 C21 1.511(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.431(3) . ?
C6 C7 1.427(2) . ?
C7 C8 1.390(3) . ?
C7 C12 1.521(3) . ?
C8 C9 1.423(3) . ?
C9 C10 1.368(3) . ?
C9 C11 1.498(3) . ?
C10 H10 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.508(3) . ?
C15 C16 1.391(3) . ?
C15 C20 1.388(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.387(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.384(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.381(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.382(3) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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
C8 O1 H1 109.5 . . ?
C13 N1 C12 110.64(14) . . ?
C13 N1 C14 110.85(15) . . ?
C14 N1 C12 111.68(14) . . ?
C2 C1 C6 120.29(17) . . ?
C10 C1 C2 120.47(18) . . ?
C10 C1 C6 119.23(17) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.19(19) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.75(18) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C21 119.41(18) . . ?
C5 C4 C3 119.92(18) . . ?
C5 C4 C21 120.67(19) . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.58(18) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C5 117.26(17) . . ?
C1 C6 C7 119.81(16) . . ?
C7 C6 C5 122.92(17) . . ?
C6 C7 C12 121.32(16) . . ?
C8 C7 C6 119.09(17) . . ?
C8 C7 C12 119.54(17) . . ?
O1 C8 C7 122.48(17) . . ?
O1 C8 C9 116.90(16) . . ?
C7 C8 C9 120.62(17) . . ?
C8 C9 C11 119.41(17) . . ?
C10 C9 C8 120.36(17) . . ?
C10 C9 C11 120.22(17) . . ?
C1 C10 H10 119.6 . . ?
C9 C10 C1 120.75(17) . . ?
C9 C10 H10 119.6 . . ?
F1 C11 F3 105.80(16) . . ?
F1 C11 C9 112.11(17) . . ?
F2 C11 F1 106.36(17) . . ?
F2 C11 F3 106.20(17) . . ?
F2 C11 C9 113.46(16) . . ?
F3 C11 C9 112.35(17) . . ?
N1 C12 C7 111.77(15) . . ?
N1 C12 H12A 109.3 . . ?
N1 C12 H12B 109.3 . . ?
C7 C12 H12A 109.3 . . ?
C7 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 H14A 109.3 . . ?
N1 C14 H14B 109.3 . . ?
N1 C14 C15 111.67(15) . . ?
H14A C14 H14B 107.9 . . ?
C15 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
C16 C15 C14 122.20(18) . . ?
C20 C15 C14 119.86(17) . . ?
C20 C15 C16 117.94(19) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.43(19) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.7(2) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 120.3 . . ?
C19 C18 C17 119.3(2) . . ?
C19 C18 H18 120.3 . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.8(2) . . ?
C20 C19 H19 120.1 . . ?
C15 C20 H20 119.1 . . ?
C19 C20 C15 121.83(18) . . ?
C19 C20 H20 119.1 . . ?
C4 C21 H21A 109.5 . . ?
C4 C21 H21B 109.5 . . ?
C4 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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
O1 C8 C9 C10 178.45(16) . . . . ?
O1 C8 C9 C11 -0.6(3) . . . . ?
N1 C14 C15 C16 94.2(2) . . . . ?
N1 C14 C15 C20 -85.7(2) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C1 C6 C7 C8 -3.6(2) . . . . ?
C1 C6 C7 C12 179.27(16) . . . . ?
C2 C1 C6 C5 0.5(2) . . . . ?
C2 C1 C6 C7 179.44(16) . . . . ?
C2 C1 C10 C9 -177.03(17) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C2 C3 C4 C21 -178.92(18) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C4 C5 C6 C7 -178.62(16) . . . . ?
C5 C6 C7 C8 175.33(16) . . . . ?
C5 C6 C7 C12 -1.8(3) . . . . ?
C6 C1 C2 C3 -0.6(3) . . . . ?
C6 C1 C10 C9 2.0(3) . . . . ?
C6 C7 C8 O1 -176.13(15) . . . . ?
C6 C7 C8 C9 4.4(3) . . . . ?
C6 C7 C12 N1 -152.78(16) . . . . ?
C7 C8 C9 C10 -2.0(3) . . . . ?
C7 C8 C9 C11 178.89(17) . . . . ?
C8 C7 C12 N1 30.1(2) . . . . ?
C8 C9 C10 C1 -1.2(3) . . . . ?
C8 C9 C11 F1 -178.74(17) . . . . ?
C8 C9 C11 F2 -58.2(2) . . . . ?
C8 C9 C11 F3 62.3(2) . . . . ?
C10 C1 C2 C3 178.39(18) . . . . ?
C10 C1 C6 C5 -178.54(16) . . . . ?
C10 C1 C6 C7 0.4(3) . . . . ?
C10 C9 C11 F1 2.2(3) . . . . ?
C10 C9 C11 F2 122.7(2) . . . . ?
C10 C9 C11 F3 -116.8(2) . . . . ?
C11 C9 C10 C1 177.84(17) . . . . ?
C12 N1 C14 C15 162.34(15) . . . . ?
C12 C7 C8 O1 1.1(3) . . . . ?
C12 C7 C8 C9 -178.40(16) . . . . ?
C13 N1 C12 C7 77.42(19) . . . . ?
C13 N1 C14 C15 -73.79(19) . . . . ?
C14 N1 C12 C7 -158.59(15) . . . . ?
C14 C15 C16 C17 179.98(19) . . . . ?
C14 C15 C20 C19 179.91(18) . . . . ?
C15 C16 C17 C18 0.2(4) . . . . ?
C16 C15 C20 C19 -0.1(3) . . . . ?
C16 C17 C18 C19 -0.2(4) . . . . ?
C17 C18 C19 C20 0.1(3) . . . . ?
C18 C19 C20 C15 0.0(3) . . . . ?
C20 C15 C16 C17 0.0(3) . . . . ?
C21 C4 C5 C6 178.77(17) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.551
_oxdiff_exptl_absorpt_empirical_full_min 0.667
####################################################################### 
# 
# 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_l114
_database_code_depnum_ccdc_archive 'CCDC 2451749'
loop_
_audit_author_name
_audit_author_address
'bin wang' 'Guizhou University'
_audit_update_record             
;
2025-05-16 deposited with the CCDC.	2025-11-07 downloaded from the CCDC.
;
_audit_creation_date             2025-03-31
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H14 F3 N O2'
_chemical_formula_sum            'C15 H14 F3 N O2'
_chemical_formula_weight         297.27
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N F S Cl'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   5.49673(14)
_cell_length_b                   20.9321(5)
_cell_length_c                   23.4394(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.345(2)
_cell_angle_gamma                90
_cell_volume                     2694.63(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    13510
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      72.6330
_cell_measurement_theta_min      4.2070
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52550
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.121a (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_density_diffrn    1.466
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            22600
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.859
_diffrn_reflns_theta_min         3.775
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     36.00  78.00   0.50    0.05    --   61.98-126.00 -90.00   84
  2  ω     24.00  75.00   0.50    0.05    --   61.98-126.00-120.00  102
  3  ω     62.00  88.00   0.50    0.05    --   71.30-126.00 -90.00   52
  4  ω     24.00  49.00   0.50    0.05    --   61.98-126.00 -60.00   50
  5  ω     24.00  77.00   0.50    0.05    --   61.98-126.00 -30.00  106
  6  ω     61.00  91.00   0.50    0.05    --   74.09-126.00 -30.00   60
  7  ω     36.00  89.00   0.50    0.05    --   74.09-126.00   0.00  106
  8  ω     36.00  91.00   0.50    0.05    --   74.09-126.00 -60.00  110
  9  ω     59.00  85.00   0.50    0.05    --   71.30-126.00 -60.00   52
 10  ω     43.00  69.00   0.50    0.05    --   74.09-126.00 -90.00   52
 11  ω     54.00  91.00   0.50    0.05    --   74.09-126.00-120.00   74
 12  ω     35.00  60.00   0.50    0.05    --   71.30-120.00-172.00   50
 13  ω     38.00  64.00   0.50    0.05    --   74.09-120.00-172.00   52
 14  ω     25.00  69.00   0.50    0.05    --   61.98-120.00-172.00   88
 15  ω     37.00  91.00   0.50    0.05    --   74.09-126.00-150.00  108
 16  ω     62.00  87.00   0.50    0.05    --   75.65-118.00 -49.86   50
 17  ω     68.00 108.00   0.50    0.05    --   74.09  15.00 -90.00   80
 18  ω     57.00  93.00   0.50    0.05    --   61.98  15.00-180.00   72
 19  ω     57.00  91.00   0.50    0.05    --   61.98  15.00 -90.00   68
 20  ω     62.00  92.00   0.50    0.05    --   61.98  15.00-120.00   60
 21  ω     71.00  99.00   0.50    0.05    --   61.98  15.00 -60.00   56
 22  ω     72.00 101.00   0.50    0.05    --   74.09  15.00-120.00   58
 23  ω     81.00 108.00   0.50    0.05    --   74.09  15.00-180.00   54
 24  ω     54.00  79.00   0.50    0.05    --   61.98  15.00 -30.00   50
 25  ω     55.00  95.00   0.50    0.05    --   61.98  15.00   0.00   80
 26  ω     73.00 113.00   0.50    0.05    --   74.09  15.00 -30.00   80
 27  ω     54.00 100.00   0.50    0.05    --   61.98  15.00 120.00   92
 28  ω     71.00  97.00   0.50    0.05    --   74.09  15.00 150.00   52
 29  ω     74.00 113.00   0.50    0.05    --   74.09  15.00 120.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1231696000
_diffrn_orient_matrix_UB_12      -0.0474673000
_diffrn_orient_matrix_UB_13      0.0422835000
_diffrn_orient_matrix_UB_21      -0.1387965000
_diffrn_orient_matrix_UB_22      -0.0555175000
_diffrn_orient_matrix_UB_23      -0.0296587000
_diffrn_orient_matrix_UB_31      0.2105328000
_diffrn_orient_matrix_UB_32      -0.0088195000
_diffrn_orient_matrix_UB_33      -0.0407192000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4525
_reflns_number_total             5116
_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 1.171.43.121a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.121a 64-bit (release 24-04-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         5116
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0490
_refine_ls_restrained_S_all      1.362
_refine_ls_shift/su_max          0.089
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0737P)²+1.5896P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1381
_refine_ls_wR_factor_ref         0.1421
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O3-H3
 0.86 with sigma of 0.01
 O5-C13 = O5-H5A
 1.38 with sigma of 0.01
3. Others
 Sof(H13A)=Sof(O5)=Sof(H5A)=1-FVAR(1)
 Sof(O2)=Sof(H2)=Sof(H13)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C13(H13), C13(H13A), C16(H16)
4.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C14(H14A,H14B), C17(H17A,H17B), C18(H18A,H18B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C4(H4), C5(H5), C7(H7), C10(H10), C21(H21), C23(H23), C25(H25),
 C27(H27), C28(H28)
4.d Tetrahedral OH refined with riding coordinates:
 O5(H5A)
4.e Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C30(H30A,H30B,H30C)
4.f Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.6954(2) 0.23080(6) 0.39326(6) 0.0457(3) Uani 1 1 d . . . . .
F2 F 0.9892(3) 0.26759(6) 0.44790(5) 0.0474(3) Uani 1 1 d . . . . .
F3 F 1.0676(3) 0.20752(6) 0.37667(6) 0.0511(4) Uani 1 1 d . . . . .
O1 O 1.2083(3) 0.50957(7) 0.15792(6) 0.0373(3) Uani 1 1 d . . . . .
O2 O 0.419(3) 0.4328(7) 0.5128(3) 0.0430(19) Uani 0.51(4) 1 d . . P A 1
H2 H 0.500267 0.465905 0.506350 0.064 Uiso 0.51(4) 1 calc R U P A 1
N1 N 0.5766(3) 0.36712(8) 0.39384(7) 0.0300(4) Uani 1 1 d . . . . .
C1 C 0.9743(3) 0.41522(8) 0.27735(8) 0.0260(4) Uani 1 1 d . . . . .
C2 C 0.9920(3) 0.46520(9) 0.23696(8) 0.0275(4) Uani 1 1 d . . . . .
H2A H 0.875814 0.498818 0.235928 0.033 Uiso 1 1 calc R U . . .
C3 C 1.1772(4) 0.46508(9) 0.19926(8) 0.0291(4) Uani 1 1 d . . . . .
C4 C 1.3526(4) 0.41536(9) 0.20013(8) 0.0314(4) Uani 1 1 d . . . . .
H4 H 1.481335 0.416135 0.174305 0.038 Uiso 1 1 calc R U . . .
C5 C 1.3357(3) 0.36642(9) 0.23820(8) 0.0306(4) Uani 1 1 d . . . . .
H5 H 1.453536 0.333207 0.238539 0.037 Uiso 1 1 calc R U . . .
C6 C 1.1456(3) 0.36416(8) 0.27729(8) 0.0275(4) Uani 1 1 d . . . . .
C7 C 1.1200(4) 0.31386(9) 0.31634(8) 0.0305(4) Uani 1 1 d . . . . .
H7 H 1.232576 0.279448 0.316114 0.037 Uiso 1 1 calc R U . . .
C8 C 0.9381(4) 0.31264(9) 0.35481(8) 0.0304(4) Uani 1 1 d . . . . .
C9 C 0.7704(3) 0.36530(9) 0.35726(8) 0.0277(4) Uani 1 1 d . . . . .
C10 C 0.7922(3) 0.41435(9) 0.31825(8) 0.0269(4) Uani 1 1 d . . . . .
H10 H 0.680161 0.448871 0.318961 0.032 Uiso 1 1 calc R U . . .
C11 C 0.9208(4) 0.25533(10) 0.39246(9) 0.0385(5) Uani 1 1 d . . . . .
C12 C 0.5753(4) 0.35160(14) 0.45570(9) 0.0477(6) Uani 1 1 d . . . . .
H12A H 0.726895 0.363614 0.477335 0.057 Uiso 1 1 calc R U . . .
H12B H 0.528248 0.306978 0.463875 0.057 Uiso 1 1 calc R U . . .
C13 C 0.3689(4) 0.39967(11) 0.46061(9) 0.0396(5) Uani 1 1 d D . . . .
H13 H 0.205076 0.378841 0.459309 0.047 Uiso 0.51(4) 1 calc R U P A 1
H13A H 0.210169 0.376543 0.455963 0.047 Uiso 0.49(4) 1 calc R U P A 2
C14 C 0.4369(4) 0.42627(9) 0.40223(8) 0.0334(4) Uani 1 1 d . . . . .
H14A H 0.296467 0.431740 0.374864 0.040 Uiso 1 1 calc R U . . .
H14B H 0.538165 0.465375 0.404555 0.040 Uiso 1 1 calc R U . . .
C15 C 1.0321(5) 0.55966(10) 0.15288(10) 0.0446(5) Uani 1 1 d . . . . .
H15A H 1.071027 0.587668 0.121021 0.067 Uiso 1 1 calc R U . . .
H15B H 1.034532 0.584489 0.188349 0.067 Uiso 1 1 calc R U . . .
H15C H 0.869839 0.541171 0.145831 0.067 Uiso 1 1 calc R U . . .
F4 F 0.5728(3) 0.39587(6) 0.71771(6) 0.0483(3) Uani 1 1 d . . . . .
F5 F 0.2822(2) 0.33936(7) 0.75098(5) 0.0451(3) Uani 1 1 d . . . . .
F6 F 0.6557(3) 0.31287(8) 0.76874(5) 0.0539(4) Uani 1 1 d . . . . .
O3 O -0.0606(5) 0.46882(8) 0.55886(8) 0.0671(7) Uani 1 1 d D . . . .
O4 O 0.6769(3) 0.07254(7) 0.49270(7) 0.0447(4) Uani 1 1 d . . . . .
N2 N 0.1150(3) 0.34222(7) 0.63344(7) 0.0279(3) Uani 1 1 d . . . . .
C16 C -0.0812(4) 0.42201(10) 0.60184(9) 0.0390(5) Uani 1 1 d . . . . .
H16 H -0.235094 0.427680 0.622612 0.047 Uiso 1 1 calc R U . . .
C17 C -0.0502(4) 0.35246(9) 0.58306(8) 0.0304(4) Uani 1 1 d . . . . .
H17A H -0.201903 0.327016 0.583522 0.036 Uiso 1 1 calc R U . . .
H17B H 0.029584 0.347745 0.546180 0.036 Uiso 1 1 calc R U . . .
C18 C 0.1362(4) 0.41217(9) 0.64362(9) 0.0366(5) Uani 1 1 d . . . . .
H18A H 0.289728 0.430997 0.630715 0.044 Uiso 1 1 calc R U . . .
H18B H 0.105141 0.425112 0.683291 0.044 Uiso 1 1 calc R U . . .
C19 C 0.3062(3) 0.29846(8) 0.63129(8) 0.0268(4) Uani 1 1 d . . . . .
C20 C 0.4963(4) 0.29367(9) 0.67526(8) 0.0299(4) Uani 1 1 d . . . . .
C21 C 0.6768(4) 0.24866(10) 0.67099(8) 0.0315(4) Uani 1 1 d . . . . .
H21 H 0.803894 0.247129 0.699665 0.038 Uiso 1 1 calc R U . . .
C22 C 0.6794(3) 0.20471(9) 0.62543(8) 0.0294(4) Uani 1 1 d . . . . .
C23 C 0.3075(3) 0.25477(9) 0.58708(8) 0.0275(4) Uani 1 1 d . . . . .
H23 H 0.181289 0.256827 0.558214 0.033 Uiso 1 1 calc R U . . .
C24 C 0.4878(3) 0.20733(9) 0.58293(8) 0.0280(4) Uani 1 1 d . . . . .
C25 C 0.4827(4) 0.16271(9) 0.53739(9) 0.0316(4) Uani 1 1 d . . . . .
H25 H 0.355024 0.164058 0.508839 0.038 Uiso 1 1 calc R U . . .
C26 C 0.6632(4) 0.11747(9) 0.53473(9) 0.0355(5) Uani 1 1 d . . . . .
C27 C 0.8544(4) 0.11469(10) 0.57709(10) 0.0381(5) Uani 1 1 d . . . . .
H27 H 0.977423 0.083035 0.574787 0.046 Uiso 1 1 calc R U . . .
C28 C 0.8623(4) 0.15718(10) 0.62105(9) 0.0358(5) Uani 1 1 d . . . . .
H28 H 0.991684 0.155068 0.649134 0.043 Uiso 1 1 calc R U . . .
C29 C 0.5016(4) 0.33483(11) 0.72751(9) 0.0382(5) Uani 1 1 d . . . . .
C30 C 0.4785(5) 0.06972(11) 0.45146(10) 0.0465(5) Uani 1 1 d . . . . .
H30A H 0.503764 0.034169 0.425149 0.070 Uiso 1 1 calc R U . . .
H30B H 0.469508 0.109873 0.429978 0.070 Uiso 1 1 calc R U . . .
H30C H 0.326148 0.063183 0.470965 0.070 Uiso 1 1 calc R U . . .
H3 H 0.0899(19) 0.4675(13) 0.5585(11) 0.033(8) Uiso 1 1 d D . . . .
O5 O 0.347(3) 0.4483(8) 0.5039(7) 0.044(2) Uani 0.49(4) 1 d D . P A 2
H5A H 0.295848 0.482314 0.488607 0.065 Uiso 0.49(4) 1 calc DR U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C11 1.342(3) . ?
F2 C11 1.362(3) . ?
F3 C11 1.347(3) . ?
O1 C3 1.360(2) . ?
O1 C15 1.429(3) . ?
O2 H2 0.8400 . ?
O2 C13 1.424(8) . ?
N1 C9 1.395(3) . ?
N1 C12 1.486(3) . ?
N1 C14 1.474(3) . ?
C1 C2 1.417(3) . ?
C1 C6 1.424(3) . ?
C1 C10 1.414(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.375(3) . ?
C3 C4 1.418(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.364(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.418(3) . ?
C6 C7 1.406(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.373(3) . ?
C8 C9 1.440(3) . ?
C8 C11 1.495(3) . ?
C9 C10 1.383(3) . ?
C10 H10 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.524(4) . ?
C13 H13 1.0000 . ?
C13 H13A 1.0000 . ?
C13 C14 1.538(3) . ?
C13 O5 1.446(7) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
F4 C29 1.359(3) . ?
F5 C29 1.349(3) . ?
F6 C29 1.340(3) . ?
O3 C16 1.413(2) . ?
O3 H3 0.828(10) . ?
O4 C26 1.366(3) . ?
O4 C30 1.429(3) . ?
N2 C17 1.476(2) . ?
N2 C18 1.487(2) . ?
N2 C19 1.396(2) . ?
C16 H16 1.0000 . ?
C16 C17 1.533(3) . ?
C16 C18 1.528(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.441(3) . ?
C19 C23 1.382(3) . ?
C20 C21 1.375(3) . ?
C20 C29 1.497(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.410(3) . ?
C22 C24 1.421(3) . ?
C22 C28 1.421(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.409(3) . ?
C24 C25 1.418(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.375(3) . ?
C26 C27 1.417(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.360(3) . ?
C28 H28 0.9500 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
O5 H5A 0.8400 . ?

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
C3 O1 C15 117.16(15) . . ?
C13 O2 H2 109.5 . . ?
C9 N1 C12 128.88(17) . . ?
C9 N1 C14 121.33(15) . . ?
C14 N1 C12 91.73(16) . . ?
C2 C1 C6 119.33(17) . . ?
C10 C1 C2 122.16(17) . . ?
C10 C1 C6 118.51(17) . . ?
C1 C2 H2A 120.0 . . ?
C3 C2 C1 120.07(17) . . ?
C3 C2 H2A 120.0 . . ?
O1 C3 C2 125.10(17) . . ?
O1 C3 C4 114.04(16) . . ?
C2 C3 C4 120.84(17) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.73(17) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.28(17) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 118.69(17) . . ?
C7 C6 C1 118.51(17) . . ?
C7 C6 C5 122.79(17) . . ?
C6 C7 H7 118.8 . . ?
C8 C7 C6 122.44(18) . . ?
C8 C7 H7 118.8 . . ?
C7 C8 C9 119.76(17) . . ?
C7 C8 C11 117.93(18) . . ?
C9 C8 C11 122.31(18) . . ?
N1 C9 C8 123.49(17) . . ?
C10 C9 N1 118.34(17) . . ?
C10 C9 C8 117.98(17) . . ?
C1 C10 H10 118.6 . . ?
C9 C10 C1 122.71(17) . . ?
C9 C10 H10 118.6 . . ?
F1 C11 F2 106.13(17) . . ?
F1 C11 F3 106.46(16) . . ?
F1 C11 C8 113.38(18) . . ?
F2 C11 C8 112.96(16) . . ?
F3 C11 F2 104.88(17) . . ?
F3 C11 C8 112.38(18) . . ?
N1 C12 H12A 114.0 . . ?
N1 C12 H12B 114.0 . . ?
N1 C12 C13 87.86(16) . . ?
H12A C12 H12B 111.2 . . ?
C13 C12 H12A 114.0 . . ?
C13 C12 H12B 114.0 . . ?
O2 C13 C12 105.5(9) . . ?
O2 C13 H13 112.5 . . ?
O2 C13 C14 122.8(4) . . ?
C12 C13 H13 112.5 . . ?
C12 C13 H13A 108.7 . . ?
C12 C13 C14 87.89(16) . . ?
C14 C13 H13 112.5 . . ?
C14 C13 H13A 108.7 . . ?
O5 C13 C12 126.9(10) . . ?
O5 C13 H13A 108.7 . . ?
O5 C13 C14 113.5(7) . . ?
N1 C14 C13 87.79(15) . . ?
N1 C14 H14A 114.0 . . ?
N1 C14 H14B 114.0 . . ?
C13 C14 H14A 114.0 . . ?
C13 C14 H14B 114.0 . . ?
H14A C14 H14B 111.2 . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
O1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C16 O3 H3 95.4(19) . . ?
C26 O4 C30 116.94(17) . . ?
C17 N2 C18 91.54(14) . . ?
C19 N2 C17 120.38(15) . . ?
C19 N2 C18 126.70(16) . . ?
O3 C16 H16 111.0 . . ?
O3 C16 C17 116.15(17) . . ?
O3 C16 C18 117.8(2) . . ?
C17 C16 H16 111.0 . . ?
C18 C16 H16 111.0 . . ?
C18 C16 C17 87.86(15) . . ?
N2 C17 C16 88.86(15) . . ?
N2 C17 H17A 113.8 . . ?
N2 C17 H17B 113.8 . . ?
C16 C17 H17A 113.8 . . ?
C16 C17 H17B 113.8 . . ?
H17A C17 H17B 111.1 . . ?
N2 C18 C16 88.62(15) . . ?
N2 C18 H18A 113.9 . . ?
N2 C18 H18B 113.9 . . ?
C16 C18 H18A 113.9 . . ?
C16 C18 H18B 113.9 . . ?
H18A C18 H18B 111.1 . . ?
N2 C19 C20 123.00(16) . . ?
C23 C19 N2 119.21(17) . . ?
C23 C19 C20 117.66(17) . . ?
C19 C20 C29 122.31(18) . . ?
C21 C20 C19 120.01(17) . . ?
C21 C20 C29 117.65(18) . . ?
C20 C21 H21 118.9 . . ?
C20 C21 C22 122.14(18) . . ?
C22 C21 H21 118.9 . . ?
C21 C22 C24 118.40(17) . . ?
C21 C22 C28 122.72(18) . . ?
C24 C22 C28 118.86(18) . . ?
C19 C23 H23 118.5 . . ?
C19 C23 C24 122.90(18) . . ?
C24 C23 H23 118.5 . . ?
C23 C24 C22 118.81(17) . . ?
C23 C24 C25 121.59(18) . . ?
C25 C24 C22 119.60(17) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 C24 119.71(19) . . ?
C26 C25 H25 120.1 . . ?
O4 C26 C25 124.6(2) . . ?
O4 C26 C27 114.55(18) . . ?
C25 C26 C27 120.83(19) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 C26 120.24(19) . . ?
C28 C27 H27 119.9 . . ?
C22 C28 H28 119.6 . . ?
C27 C28 C22 120.76(19) . . ?
C27 C28 H28 119.6 . . ?
F4 C29 C20 113.53(16) . . ?
F5 C29 F4 105.73(18) . . ?
F5 C29 C20 112.72(17) . . ?
F6 C29 F4 105.46(17) . . ?
F6 C29 F5 106.21(17) . . ?
F6 C29 C20 112.54(18) . . ?
O4 C30 H30A 109.5 . . ?
O4 C30 H30B 109.5 . . ?
O4 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C13 O5 H5A 109.5 . . ?

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
O1 C3 C4 C5 -177.47(17) . . . . ?
O2 C13 C14 N1 123.3(10) . . . . ?
N1 C9 C10 C1 -176.58(17) . . . . ?
N1 C12 C13 O2 -139.6(4) . . . . ?
N1 C12 C13 C14 -16.02(15) . . . . ?
N1 C12 C13 O5 -134.2(7) . . . . ?
C1 C2 C3 O1 178.30(17) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C1 C6 C7 C8 -0.8(3) . . . . ?
C2 C1 C6 C5 2.7(3) . . . . ?
C2 C1 C6 C7 -177.78(16) . . . . ?
C2 C1 C10 C9 178.86(17) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C1 -1.8(3) . . . . ?
C4 C5 C6 C7 178.75(18) . . . . ?
C5 C6 C7 C8 178.71(18) . . . . ?
C6 C1 C2 C3 -1.8(3) . . . . ?
C6 C1 C10 C9 -1.5(3) . . . . ?
C6 C7 C8 C9 -2.1(3) . . . . ?
C6 C7 C8 C11 177.12(17) . . . . ?
C7 C8 C9 N1 178.11(17) . . . . ?
C7 C8 C9 C10 3.1(3) . . . . ?
C7 C8 C11 F1 -130.58(19) . . . . ?
C7 C8 C11 F2 108.6(2) . . . . ?
C7 C8 C11 F3 -9.8(3) . . . . ?
C8 C9 C10 C1 -1.3(3) . . . . ?
C9 N1 C12 C13 150.56(19) . . . . ?
C9 N1 C14 C13 -155.48(17) . . . . ?
C9 C8 C11 F1 48.6(3) . . . . ?
C9 C8 C11 F2 -72.2(2) . . . . ?
C9 C8 C11 F3 169.41(17) . . . . ?
C10 C1 C2 C3 177.82(18) . . . . ?
C10 C1 C6 C5 -176.95(17) . . . . ?
C10 C1 C6 C7 2.6(3) . . . . ?
C11 C8 C9 N1 -1.1(3) . . . . ?
C11 C8 C9 C10 -176.05(17) . . . . ?
C12 N1 C9 C8 46.6(3) . . . . ?
C12 N1 C9 C10 -138.5(2) . . . . ?
C12 N1 C14 C13 -16.58(16) . . . . ?
C12 C13 C14 N1 16.16(16) . . . . ?
C14 N1 C9 C8 168.98(17) . . . . ?
C14 N1 C9 C10 -16.1(3) . . . . ?
C14 N1 C12 C13 16.73(16) . . . . ?
C15 O1 C3 C2 -1.1(3) . . . . ?
C15 O1 C3 C4 177.39(18) . . . . ?
O3 C16 C17 N2 133.3(2) . . . . ?
O3 C16 C18 N2 -131.64(18) . . . . ?
O4 C26 C27 C28 179.53(18) . . . . ?
N2 C19 C20 C21 178.78(16) . . . . ?
N2 C19 C20 C29 1.0(3) . . . . ?
N2 C19 C23 C24 -177.33(16) . . . . ?
C17 N2 C18 C16 13.53(14) . . . . ?
C17 N2 C19 C20 169.62(16) . . . . ?
C17 N2 C19 C23 -14.6(2) . . . . ?
C17 C16 C18 N2 -13.02(14) . . . . ?
C18 N2 C17 C16 -13.49(15) . . . . ?
C18 N2 C19 C20 51.2(3) . . . . ?
C18 N2 C19 C23 -132.98(19) . . . . ?
C18 C16 C17 N2 13.13(14) . . . . ?
C19 N2 C17 C16 -148.63(16) . . . . ?
C19 N2 C18 C16 144.16(18) . . . . ?
C19 C20 C21 C22 -2.2(3) . . . . ?
C19 C20 C29 F4 -75.5(2) . . . . ?
C19 C20 C29 F5 44.7(2) . . . . ?
C19 C20 C29 F6 164.82(17) . . . . ?
C19 C23 C24 C22 -1.1(3) . . . . ?
C19 C23 C24 C25 179.26(17) . . . . ?
C20 C19 C23 C24 -1.3(3) . . . . ?
C20 C21 C22 C24 -0.2(3) . . . . ?
C20 C21 C22 C28 -178.81(17) . . . . ?
C21 C20 C29 F4 106.7(2) . . . . ?
C21 C20 C29 F5 -133.11(18) . . . . ?
C21 C20 C29 F6 -13.0(3) . . . . ?
C21 C22 C24 C23 1.8(3) . . . . ?
C21 C22 C24 C25 -178.48(16) . . . . ?
C21 C22 C28 C27 178.33(18) . . . . ?
C22 C24 C25 C26 -0.1(3) . . . . ?
C23 C19 C20 C21 2.9(3) . . . . ?
C23 C19 C20 C29 -174.88(17) . . . . ?
C23 C24 C25 C26 179.52(17) . . . . ?
C24 C22 C28 C27 -0.2(3) . . . . ?
C24 C25 C26 O4 -179.60(18) . . . . ?
C24 C25 C26 C27 0.2(3) . . . . ?
C25 C26 C27 C28 -0.3(3) . . . . ?
C26 C27 C28 C22 0.3(3) . . . . ?
C28 C22 C24 C23 -179.52(16) . . . . ?
C28 C22 C24 C25 0.2(3) . . . . ?
C29 C20 C21 C22 175.70(17) . . . . ?
C30 O4 C26 C25 -5.2(3) . . . . ?
C30 O4 C26 C27 175.01(18) . . . . ?
O5 C13 C14 N1 145.9(9) . . . . ?

_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 1.784
_oxdiff_exptl_absorpt_empirical_full_min 0.505
