# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_test1
_database_code_depnum_ccdc_archive 'CCDC 2330494'
loop_
_audit_author_name
_audit_author_address
'Jie Li'
;College of Chemistry, Chemical Engineering and Materials Science, Soochow University
China
;
_audit_update_record             
;
2024-02-02 deposited with the CCDC.	2024-09-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        
1-(4-chlorobenzyl)-3,3-difluoro-3a-(4-fluorobenzyl)octahydro-1H-indole-2-carbonitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H22 Cl F3 N2'
_chemical_formula_sum            'C23 H22 Cl F3 N2'
_chemical_formula_weight         418.87

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'
F F 0.0171 0.0103 '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'

_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                   16.175(2)
_cell_length_b                   8.8838(10)
_cell_length_c                   16.016(3)
_cell_angle_alpha                90
_cell_angle_beta                 118.393(19)
_cell_angle_gamma                90
_cell_volume                     2024.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    3629
_cell_measurement_theta_min      2.5600
_cell_measurement_theta_max      26.4070

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.227
_shelx_estimated_absorpt_T_min   0.876
_shelx_estimated_absorpt_T_max   0.935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.50267
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4471
_diffrn_reflns_number            10642
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.544
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4103
_reflns_number_gt                2714
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;
_computing_publication_material  
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0575P)²+0.1367P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4103
_refine_ls_number_parameters     278
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1324
_refine_ls_wR_factor_gt          0.1094
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.76390(9) 0.35353(15) 0.32173(11) 0.0631(4) Uani 1 1 d . . . . .
N1 N 0.67994(10) 0.0317(2) 0.32123(12) 0.0418(4) Uani 1 1 d . . . . .
C1 C 0.57769(14) 0.0124(3) 0.27535(16) 0.0509(6) Uani 1 1 d . . . . .
H1A H 0.5569(4) -0.0471(10) 0.2156(10) 0.061 Uiso 1 1 calc R U . . .
H1B H 0.5469(5) 0.1136(17) 0.2575(4) 0.061 Uiso 1 1 calc R U . . .
Cl1 Cl 0.44368(4) -0.31859(7) 0.51738(5) 0.0605(2) Uani 1 1 d . . . . .
F2 F 0.87022(9) 0.26477(18) 0.45681(10) 0.0647(4) Uani 1 1 d . . . . .
N2 N 0.76682(14) 0.0820(3) 0.56220(16) 0.0624(6) Uani 1 1 d . . . . .
C2 C 0.54559(13) -0.0671(3) 0.33860(15) 0.0414(5) Uani 1 1 d . . . . .
F3 F 1.21132(9) 0.46749(18) 0.47592(11) 0.0699(4) Uani 1 1 d . . . . .
C3 C 0.59738(15) -0.1848(3) 0.39670(16) 0.0459(6) Uani 1 1 d . . . . .
H3 H 0.6581(14) -0.2146(7) 0.39877(16) 0.055 Uiso 1 1 calc R U . . .
C4 C 0.56675(15) -0.2617(3) 0.45182(17) 0.0469(6) Uani 1 1 d . . . . .
H4 H 0.6031(10) -0.343(2) 0.4918(11) 0.056 Uiso 1 1 calc R U . . .
C5 C 0.48300(14) -0.2198(3) 0.44864(16) 0.0436(5) Uani 1 1 d . . . . .
C6 C 0.42996(15) -0.1041(3) 0.39190(17) 0.0488(6) Uani 1 1 d . . . . .
H6 H 0.3732(14) -0.0768(7) 0.39018(17) 0.059 Uiso 1 1 calc R U . . .
C7 C 0.46185(14) -0.0283(3) 0.33707(17) 0.0472(6) Uani 1 1 d . . . . .
H7 H 0.4261(9) 0.051(2) 0.2982(10) 0.057 Uiso 1 1 calc R U . . .
C8 C 0.72092(14) 0.0417(3) 0.25555(15) 0.0407(5) Uani 1 1 d . . . . .
H8 H 0.6857(9) 0.1118(18) 0.2064(12) 0.049 Uiso 1 1 calc R U . . .
C17 C 0.86392(14) 0.1742(3) 0.26041(16) 0.0438(5) Uani 1 1 d . . . . .
H17A H 0.87185(18) 0.0950(13) 0.2242(6) 0.053 Uiso 1 1 calc R U . . .
H17B H 0.8203(7) 0.2451(11) 0.2163(7) 0.053 Uiso 1 1 calc R U . . .
C18 C 0.95745(14) 0.2524(3) 0.31676(15) 0.0404(5) Uani 1 1 d . . . . .
C9 C 0.72161(16) -0.1096(3) 0.21176(18) 0.0527(6) Uani 1 1 d . . . . .
H9A H 0.6576(11) -0.1496(7) 0.1798(6) 0.063 Uiso 1 1 calc R U . . .
H9B H 0.7420(3) -0.0950(4) 0.1638(8) 0.063 Uiso 1 1 calc R U . . .
C10 C 0.78565(18) -0.2239(3) 0.2840(2) 0.0626(7) Uani 1 1 d . . . . .
H10A H 0.78816(18) -0.3138(18) 0.2516(6) 0.075 Uiso 1 1 calc R U . . .
H10B H 0.7604(5) -0.2506(6) 0.3257(8) 0.075 Uiso 1 1 calc R U . . .
C11 C 0.88435(17) -0.1613(3) 0.34223(19) 0.0564(7) Uani 1 1 d . . . . .
H11A H 0.9136(6) -0.1441(4) 0.2996(8) 0.068 Uiso 1 1 calc R U . . .
H11B H 0.9243(8) -0.2370(14) 0.3923(9) 0.068 Uiso 1 1 calc R U . . .
C12 C 0.88268(14) -0.0137(3) 0.38974(15) 0.0434(5) Uani 1 1 d . . . . .
H12A H 0.9472(10) 0.0257(7) 0.4246(6) 0.052 Uiso 1 1 calc R U . . .
H12B H 0.8604(3) -0.0334(4) 0.4362(7) 0.052 Uiso 1 1 calc R U . . .
C13 C 0.81975(13) 0.1061(2) 0.31943(14) 0.0366(5) Uani 1 1 d . . . . .
C14 C 0.79557(14) 0.2231(3) 0.37328(16) 0.0454(6) Uani 1 1 d . . . . .
C16 C 0.74417(15) 0.1140(3) 0.48550(18) 0.0483(6) Uani 1 1 d . . . . .
C19 C 0.96144(16) 0.4046(3) 0.33448(18) 0.0519(6) Uani 1 1 d . . . . .
H19 H 0.9068(15) 0.4582(15) 0.3104(7) 0.062 Uiso 1 1 calc R U . . .
C20 C 1.04585(16) 0.4788(3) 0.38769(19) 0.0557(7) Uani 1 1 d . . . . .
H20 H 1.04728(16) 0.582(3) 0.3990(4) 0.067 Uiso 1 1 calc R U . . .
C15 C 0.71444(15) 0.1592(3) 0.38627(16) 0.0443(5) Uani 1 1 d . . . . .
H15 H 0.6656(12) 0.2337(18) 0.3671(5) 0.053 Uiso 1 1 calc R U . . .
C22 C 1.12764(16) 0.2473(3) 0.40592(17) 0.0493(6) Uani 1 1 d . . . . .
H22 H 1.1862(15) 0.1925(14) 0.4304(6) 0.059 Uiso 1 1 calc R U . . .
C23 C 1.04219(14) 0.1751(3) 0.35243(16) 0.0456(6) Uani 1 1 d . . . . .
H23 H 1.04166(15) 0.072(3) 0.3401(4) 0.055 Uiso 1 1 calc R U . . .
C21 C 1.12672(15) 0.3970(3) 0.42298(16) 0.0496(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
F1 C14 1.373(3) . ?
N1 C15 1.458(3) . ?
N1 C1 1.466(2) . ?
N1 C8 1.489(2) . ?
C1 C2 1.515(3) . ?
C1 H1A 1.002(16) . ?
C1 H1B 1.002(16) . ?
Cl1 C5 1.747(2) . ?
F2 C14 1.360(2) . ?
N2 C16 1.139(3) . ?
C2 C3 1.385(3) . ?
C2 C7 1.387(3) . ?
F3 C21 1.371(3) . ?
C3 C4 1.381(3) . ?
C3 H3 1.00(2) . ?
C4 C5 1.382(3) . ?
C4 H4 0.96(2) . ?
C5 C6 1.370(3) . ?
C6 C7 1.386(3) . ?
C6 H6 0.94(2) . ?
C7 H7 0.93(2) . ?
C8 C9 1.518(3) . ?
C8 C13 1.541(3) . ?
C8 H8 0.95(2) . ?
C17 C18 1.513(3) . ?
C17 C13 1.553(3) . ?
C17 H17A 0.958(15) . ?
C17 H17B 0.958(15) . ?
C18 C19 1.376(3) . ?
C18 C23 1.390(3) . ?
C9 C10 1.518(4) . ?
C9 H9A 0.978(15) . ?
C9 H9B 0.978(15) . ?
C10 C11 1.520(4) . ?
C10 H10A 0.964(18) . ?
C10 H10B 0.964(18) . ?
C11 C12 1.523(3) . ?
C11 H11A 1.010(18) . ?
C11 H11B 1.010(18) . ?
C12 C13 1.532(3) . ?
C12 H12A 0.985(15) . ?
C12 H12B 0.985(15) . ?
C13 C14 1.516(3) . ?
C14 C15 1.532(3) . ?
C16 C15 1.480(3) . ?
C19 C20 1.385(3) . ?
C19 H19 0.91(2) . ?
C20 C21 1.362(3) . ?
C20 H20 0.93(3) . ?
C15 H15 0.96(2) . ?
C22 C21 1.359(3) . ?
C22 C23 1.389(3) . ?
C22 H22 0.97(2) . ?
C23 H23 0.94(2) . ?

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
C15 N1 C1 113.98(17) . . ?
C15 N1 C8 108.12(16) . . ?
C1 N1 C8 115.34(16) . . ?
N1 C1 C2 112.53(17) . . ?
N1 C1 H1A 109.1 . . ?
C2 C1 H1A 109.1 . . ?
N1 C1 H1B 109.1 . . ?
C2 C1 H1B 109.1 . . ?
H1A C1 H1B 107.8 . . ?
C3 C2 C7 118.2(2) . . ?
C3 C2 C1 120.73(18) . . ?
C7 C2 C1 121.0(2) . . ?
C4 C3 C2 121.1(2) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 119.1(2) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 121.3(2) . . ?
C6 C5 Cl1 119.61(16) . . ?
C4 C5 Cl1 119.04(18) . . ?
C5 C6 C7 118.7(2) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C6 C7 C2 121.5(2) . . ?
C6 C7 H7 119.2 . . ?
C2 C7 H7 119.2 . . ?
N1 C8 C9 112.19(18) . . ?
N1 C8 C13 102.87(16) . . ?
C9 C8 C13 113.72(17) . . ?
N1 C8 H8 109.3 . . ?
C9 C8 H8 109.3 . . ?
C13 C8 H8 109.3 . . ?
C18 C17 C13 115.78(17) . . ?
C18 C17 H17A 108.3 . . ?
C13 C17 H17A 108.3 . . ?
C18 C17 H17B 108.3 . . ?
C13 C17 H17B 108.3 . . ?
H17A C17 H17B 107.4 . . ?
C19 C18 C23 117.4(2) . . ?
C19 C18 C17 120.64(19) . . ?
C23 C18 C17 121.9(2) . . ?
C10 C9 C8 113.1(2) . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 C11 111.1(2) . . ?
C9 C10 H10A 109.4 . . ?
C11 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
C11 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C10 C11 C12 111.00(19) . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 C13 113.24(19) . . ?
C11 C12 H12A 108.9 . . ?
C13 C12 H12A 108.9 . . ?
C11 C12 H12B 108.9 . . ?
C13 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 C12 108.62(17) . . ?
C14 C13 C8 99.53(15) . . ?
C12 C13 C8 110.30(18) . . ?
C14 C13 C17 113.38(18) . . ?
C12 C13 C17 112.39(16) . . ?
C8 C13 C17 111.89(16) . . ?
F2 C14 F1 105.37(19) . . ?
F2 C14 C13 113.44(17) . . ?
F1 C14 C13 111.10(18) . . ?
F2 C14 C15 112.61(19) . . ?
F1 C14 C15 107.20(16) . . ?
C13 C14 C15 107.02(18) . . ?
N2 C16 C15 178.7(3) . . ?
C18 C19 C20 122.0(2) . . ?
C18 C19 H19 119.0 . . ?
C20 C19 H19 119.0 . . ?
C21 C20 C19 118.2(2) . . ?
C21 C20 H20 120.9 . . ?
C19 C20 H20 120.9 . . ?
N1 C15 C16 112.01(19) . . ?
N1 C15 C14 104.61(17) . . ?
C16 C15 C14 112.61(19) . . ?
N1 C15 H15 109.2 . . ?
C16 C15 H15 109.2 . . ?
C14 C15 H15 109.2 . . ?
C21 C22 C23 118.2(2) . . ?
C21 C22 H22 120.9 . . ?
C23 C22 H22 120.9 . . ?
C22 C23 C18 121.5(2) . . ?
C22 C23 H23 119.2 . . ?
C18 C23 H23 119.2 . . ?
C22 C21 C20 122.6(2) . . ?
C22 C21 F3 117.9(2) . . ?
C20 C21 F3 119.5(2) . . ?

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
C15 N1 C1 C2 -80.8(2) . . . . ?
C8 N1 C1 C2 153.24(19) . . . . ?
N1 C1 C2 C3 -38.5(3) . . . . ?
N1 C1 C2 C7 144.2(2) . . . . ?
C7 C2 C3 C4 -0.1(3) . . . . ?
C1 C2 C3 C4 -177.5(2) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C3 C4 C5 Cl1 179.26(17) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
Cl1 C5 C6 C7 -179.24(18) . . . . ?
C5 C6 C7 C2 0.0(3) . . . . ?
C3 C2 C7 C6 0.1(3) . . . . ?
C1 C2 C7 C6 177.5(2) . . . . ?
C15 N1 C8 C9 157.93(18) . . . . ?
C1 N1 C8 C9 -73.2(2) . . . . ?
C15 N1 C8 C13 35.3(2) . . . . ?
C1 N1 C8 C13 164.25(18) . . . . ?
C13 C17 C18 C19 -91.9(3) . . . . ?
C13 C17 C18 C23 88.2(3) . . . . ?
N1 C8 C9 C10 -65.4(2) . . . . ?
C13 C8 C9 C10 50.8(2) . . . . ?
C8 C9 C10 C11 -53.4(3) . . . . ?
C9 C10 C11 C12 55.6(3) . . . . ?
C10 C11 C12 C13 -56.4(3) . . . . ?
C11 C12 C13 C14 160.23(18) . . . . ?
C11 C12 C13 C8 52.1(2) . . . . ?
C11 C12 C13 C17 -73.5(2) . . . . ?
N1 C8 C13 C14 -41.5(2) . . . . ?
C9 C8 C13 C14 -163.06(19) . . . . ?
N1 C8 C13 C12 72.5(2) . . . . ?
C9 C8 C13 C12 -49.0(2) . . . . ?
N1 C8 C13 C17 -161.56(17) . . . . ?
C9 C8 C13 C17 76.9(2) . . . . ?
C18 C17 C13 C14 63.3(2) . . . . ?
C18 C17 C13 C12 -60.4(3) . . . . ?
C18 C17 C13 C8 174.88(18) . . . . ?
C12 C13 C14 F2 43.6(2) . . . . ?
C8 C13 C14 F2 158.89(18) . . . . ?
C17 C13 C14 F2 -82.1(2) . . . . ?
C12 C13 C14 F1 162.05(16) . . . . ?
C8 C13 C14 F1 -82.63(19) . . . . ?
C17 C13 C14 F1 36.3(2) . . . . ?
C12 C13 C14 C15 -81.2(2) . . . . ?
C8 C13 C14 C15 34.1(2) . . . . ?
C17 C13 C14 C15 153.06(18) . . . . ?
C23 C18 C19 C20 -1.6(3) . . . . ?
C17 C18 C19 C20 178.5(2) . . . . ?
C18 C19 C20 C21 0.0(4) . . . . ?
C1 N1 C15 C16 94.5(2) . . . . ?
C8 N1 C15 C16 -135.78(18) . . . . ?
C1 N1 C15 C14 -143.19(18) . . . . ?
C8 N1 C15 C14 -13.5(2) . . . . ?
F2 C14 C15 N1 -139.23(18) . . . . ?
F1 C14 C15 N1 105.35(19) . . . . ?
C13 C14 C15 N1 -13.9(2) . . . . ?
F2 C14 C15 C16 -17.4(3) . . . . ?
F1 C14 C15 C16 -132.8(2) . . . . ?
C13 C14 C15 C16 108.0(2) . . . . ?
C21 C22 C23 C18 0.1(3) . . . . ?
C19 C18 C23 C22 1.6(3) . . . . ?
C17 C18 C23 C22 -178.53(19) . . . . ?
C23 C22 C21 C20 -1.8(4) . . . . ?
C23 C22 C21 F3 179.93(18) . . . . ?
C19 C20 C21 C22 1.7(4) . . . . ?
C19 C20 C21 F3 -180.0(2) . . . . ?

_refine_diff_density_max         0.164
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.045



####################################################################### 
# 
# 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_test1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2330499'
loop_
_audit_author_name
_audit_author_address
'Jie Li'
;College of Chemistry, Chemical Engineering and Materials Science, Soochow University
China
;
_audit_update_record             
;
2024-02-02 deposited with the CCDC.	2024-09-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        
;
1-(4-chlorobenzyl)-3,3-difluoro-3a-(4-fluorobenzyl)octahydro-1H-indol-2-ol
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H23 Cl F3 N O'
_chemical_formula_sum            'C22 H23 Cl F3 N O'
_chemical_formula_weight         409.86

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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   15.0621(14)
_cell_length_b                   7.4049(8)
_cell_length_c                   18.0353(15)
_cell_angle_alpha                90
_cell_angle_beta                 109.111(9)
_cell_angle_gamma                90
_cell_volume                     1900.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    3538
_cell_measurement_theta_min      2.3480
_cell_measurement_theta_max      30.0090

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.242
_shelx_estimated_absorpt_T_min   0.868
_shelx_estimated_absorpt_T_max   0.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.22044
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4471
_diffrn_reflns_number            9416
_diffrn_reflns_av_unetI/netI     0.0596
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.144
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3876
_reflns_number_gt                2758
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;
_computing_publication_material  
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0527P)²+0.4116P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3876
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.1345
_refine_ls_wR_factor_gt          0.1159
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.05180(11) 0.0905(2) 0.36175(8) 0.0520(5) Uani 1 1 d . . . . .
O1 O -0.02308(11) 0.2567(3) 0.49473(10) 0.0396(5) Uani 1 1 d . . . . .
Cl1 Cl 0.40339(4) -0.31920(11) 0.71109(4) 0.0481(2) Uani 1 1 d . . . . .
N1 N 0.12989(12) 0.3807(3) 0.51703(9) 0.0279(5) Uani 1 1 d . . . . .
C1 C 0.06035(15) 0.2443(4) 0.47808(12) 0.0297(5) Uani 1 1 d . . . . .
H1 H 0.0864(8) 0.133(3) 0.4955(5) 0.036 Uiso 1 1 calc R U . . .
C2 C 0.05298(15) 0.2606(4) 0.39157(12) 0.0307(6) Uani 1 1 d . . . . .
F3 F 0.01447(12) 0.2567(3) 0.00803(8) 0.0684(6) Uani 1 1 d . . . . .
C3 C 0.13565(14) 0.3762(4) 0.38659(11) 0.0270(5) Uani 1 1 d . . . . .
C4 C 0.10194(16) 0.5683(4) 0.35980(12) 0.0316(6) Uani 1 1 d . . . . .
H4A H 0.0700(5) 0.5675(4) 0.3040(9) 0.038 Uiso 1 1 calc R U . . .
H4B H 0.0573(7) 0.6050(7) 0.3848(4) 0.038 Uiso 1 1 calc R U . . .
C5 C 0.18134(17) 0.7057(4) 0.37866(13) 0.0389(6) Uani 1 1 d . . . . .
H5A H 0.1552(5) 0.828(2) 0.3595(4) 0.047 Uiso 1 1 calc R U . . .
H5B H 0.2270(9) 0.6715(7) 0.3510(5) 0.047 Uiso 1 1 calc R U . . .
H100 H -0.051(2) 0.368(5) 0.4816(16) 0.058 Uiso 1 1 d . U . . .
F2 F -0.03241(9) 0.3308(3) 0.34880(8) 0.0502(5) Uani 1 1 d . . . . .
C6 C 0.23208(17) 0.7124(4) 0.46707(13) 0.0397(6) Uani 1 1 d . . . . .
H6A H 0.2840(10) 0.8020(17) 0.4790(3) 0.048 Uiso 1 1 calc R U . . .
H6B H 0.1876(8) 0.7508(9) 0.4943(5) 0.048 Uiso 1 1 calc R U . . .
C7 C 0.27127(16) 0.5277(4) 0.49608(13) 0.0345(6) Uani 1 1 d . . . . .
H7A H 0.2992(5) 0.5321(4) 0.5530(9) 0.041 Uiso 1 1 calc R U . . .
H7B H 0.3212(8) 0.4998(6) 0.4746(3) 0.041 Uiso 1 1 calc R U . . .
C8 C 0.19915(14) 0.3753(4) 0.47453(11) 0.0283(5) Uani 1 1 d . . . . .
H8 H 0.2330(9) 0.258(3) 0.4860(3) 0.034 Uiso 1 1 calc R U . . .
C9 C 0.17021(16) 0.3535(4) 0.60334(12) 0.0316(6) Uani 1 1 d . . . . .
H9A H 0.1178(9) 0.3521(4) 0.6252(4) 0.038 Uiso 1 1 calc R U . . .
H9B H 0.2103(7) 0.4591(18) 0.6262(4) 0.038 Uiso 1 1 calc R U . . .
C10 C 0.22812(15) 0.1835(4) 0.63037(11) 0.0289(5) Uani 1 1 d . . . . .
C11 C 0.32450(16) 0.1840(4) 0.64303(13) 0.0382(6) Uani 1 1 d . . . . .
H11 H 0.3553(10) 0.296(3) 0.6348(3) 0.046 Uiso 1 1 calc R U . . .
C12 C 0.37754(17) 0.0295(4) 0.66691(13) 0.0399(7) Uani 1 1 d . . . . .
H12 H 0.4411(18) 0.0307(4) 0.6741(2) 0.048 Uiso 1 1 calc R U . . .
C13 C 0.33528(16) -0.1251(4) 0.67990(12) 0.0336(6) Uani 1 1 d . . . . .
C14 C 0.24086(16) -0.1293(4) 0.66995(13) 0.0360(6) Uani 1 1 d . . . . .
H14 H 0.2151(9) -0.227(3) 0.6794(3) 0.043 Uiso 1 1 calc R U . . .
C15 C 0.18774(16) 0.0248(4) 0.64468(12) 0.0326(6) Uani 1 1 d . . . . .
H15 H 0.1225(17) 0.0218(4) 0.6370(2) 0.039 Uiso 1 1 calc R U . . .
C16 C 0.19025(15) 0.2885(4) 0.33601(12) 0.0305(6) Uani 1 1 d . . . . .
H16A H 0.2484(11) 0.3533(12) 0.3458(2) 0.037 Uiso 1 1 calc R U . . .
H16B H 0.2060(3) 0.167(2) 0.3543(4) 0.037 Uiso 1 1 calc R U . . .
C17 C 0.14134(14) 0.2817(4) 0.24766(12) 0.0286(6) Uani 1 1 d . . . . .
C18 C 0.14455(16) 0.4279(4) 0.20025(13) 0.0353(6) Uani 1 1 d . . . . .
H18 H 0.1774(10) 0.536(3) 0.2239(7) 0.042 Uiso 1 1 calc R U . . .
C20 C 0.05667(17) 0.2650(5) 0.08734(13) 0.0436(7) Uani 1 1 d . . . . .
C22 C 0.09574(16) 0.1250(4) 0.21193(13) 0.0370(6) Uani 1 1 d . . . . .
H22 H 0.09414(17) 0.023(3) 0.2433(9) 0.044 Uiso 1 1 calc R U . . .
C21 C 0.05237(17) 0.1165(5) 0.13071(14) 0.0438(7) Uani 1 1 d . . . . .
H21 H 0.0206(10) 0.010(3) 0.1063(8) 0.053 Uiso 1 1 calc R U . . .
C19 C 0.10128(17) 0.4217(4) 0.11947(13) 0.0414(7) Uani 1 1 d . . . . .
H19 H 0.10258(18) 0.524(3) 0.0871(10) 0.050 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 C2 1.367(3) . ?
O1 C1 1.387(3) . ?
O1 H100 0.92(3) . ?
Cl1 C13 1.748(3) . ?
N1 C1 1.459(3) . ?
N1 C8 1.483(3) . ?
N1 C9 1.488(2) . ?
C1 C2 1.532(3) . ?
C1 H1 0.93(3) . ?
C2 F2 1.368(3) . ?
C2 C3 1.538(3) . ?
F3 C20 1.363(3) . ?
C3 C4 1.534(3) . ?
C3 C16 1.556(3) . ?
C3 C8 1.561(3) . ?
C4 C5 1.522(4) . ?
C4 H4A 0.963(15) . ?
C4 H4B 0.963(15) . ?
C5 C6 1.527(3) . ?
C5 H5A 1.005(18) . ?
C5 H5B 1.005(18) . ?
C6 C7 1.513(4) . ?
C6 H6A 0.994(18) . ?
C6 H6B 0.994(18) . ?
C7 C8 1.526(3) . ?
C7 H7A 0.974(15) . ?
C7 H7B 0.974(15) . ?
C8 H8 0.99(3) . ?
C9 C10 1.518(3) . ?
C9 H9A 0.992(16) . ?
C9 H9B 0.992(17) . ?
C10 C15 1.386(4) . ?
C10 C11 1.394(3) . ?
C11 C12 1.381(4) . ?
C11 H11 0.99(3) . ?
C12 C13 1.367(4) . ?
C12 H12 0.92(2) . ?
C13 C14 1.374(3) . ?
C14 C15 1.382(4) . ?
C14 H14 0.86(3) . ?
C15 H15 0.95(2) . ?
C16 C17 1.522(3) . ?
C16 H16A 0.963(17) . ?
C16 H16B 0.963(17) . ?
C17 C18 1.390(4) . ?
C17 C22 1.394(4) . ?
C18 C19 1.388(3) . ?
C18 H18 0.96(3) . ?
C20 C21 1.363(4) . ?
C20 C19 1.370(4) . ?
C22 C21 1.396(3) . ?
C22 H22 0.95(3) . ?
C21 H21 0.95(3) . ?
C19 H19 0.96(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H100 111.7(19) . . ?
C1 N1 C8 104.35(17) . . ?
C1 N1 C9 113.12(18) . . ?
C8 N1 C9 114.94(16) . . ?
O1 C1 N1 114.1(2) . . ?
O1 C1 C2 116.52(17) . . ?
N1 C1 C2 103.71(18) . . ?
O1 C1 H1 107.3 . . ?
N1 C1 H1 107.3 . . ?
C2 C1 H1 107.3 . . ?
F1 C2 F2 103.87(17) . . ?
F1 C2 C1 108.4(2) . . ?
F2 C2 C1 110.21(17) . . ?
F1 C2 C3 113.35(18) . . ?
F2 C2 C3 112.6(2) . . ?
C1 C2 C3 108.25(17) . . ?
C4 C3 C2 110.11(18) . . ?
C4 C3 C16 112.72(18) . . ?
C2 C3 C16 113.3(2) . . ?
C4 C3 C8 110.7(2) . . ?
C2 C3 C8 100.17(16) . . ?
C16 C3 C8 109.16(17) . . ?
C5 C4 C3 113.26(19) . . ?
C5 C4 H4A 108.9 . . ?
C3 C4 H4A 108.9 . . ?
C5 C4 H4B 108.9 . . ?
C3 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
C4 C5 C6 110.1(2) . . ?
C4 C5 H5A 109.6 . . ?
C6 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
C6 C5 H5B 109.6 . . ?
H5A C5 H5B 108.2 . . ?
C7 C6 C5 109.7(2) . . ?
C7 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
C7 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
C6 C7 C8 114.6(2) . . ?
C6 C7 H7A 108.6 . . ?
C8 C7 H7A 108.6 . . ?
C6 C7 H7B 108.6 . . ?
C8 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
N1 C8 C7 114.2(2) . . ?
N1 C8 C3 102.95(15) . . ?
C7 C8 C3 113.81(19) . . ?
N1 C8 H8 108.5 . . ?
C7 C8 H8 108.5 . . ?
C3 C8 H8 108.5 . . ?
N1 C9 C10 116.31(19) . . ?
N1 C9 H9A 108.2 . . ?
C10 C9 H9A 108.2 . . ?
N1 C9 H9B 108.2 . . ?
C10 C9 H9B 108.2 . . ?
H9A C9 H9B 107.4 . . ?
C15 C10 C11 118.0(2) . . ?
C15 C10 C9 121.5(2) . . ?
C11 C10 C9 120.6(2) . . ?
C12 C11 C10 120.9(3) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C13 C12 C11 119.5(2) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 121.1(3) . . ?
C12 C13 Cl1 119.12(19) . . ?
C14 C13 Cl1 119.8(2) . . ?
C13 C14 C15 119.2(3) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C14 C15 C10 121.3(2) . . ?
C14 C15 H15 119.4 . . ?
C10 C15 H15 119.4 . . ?
C17 C16 C3 117.40(18) . . ?
C17 C16 H16A 108.0 . . ?
C3 C16 H16A 108.0 . . ?
C17 C16 H16B 108.0 . . ?
C3 C16 H16B 108.0 . . ?
H16A C16 H16B 107.2 . . ?
C18 C17 C22 118.4(2) . . ?
C18 C17 C16 121.0(2) . . ?
C22 C17 C16 120.5(2) . . ?
C19 C18 C17 121.4(3) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C21 C20 F3 118.2(3) . . ?
C21 C20 C19 123.3(2) . . ?
F3 C20 C19 118.5(3) . . ?
C17 C22 C21 120.9(3) . . ?
C17 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C20 C21 C22 118.1(3) . . ?
C20 C21 H21 120.9 . . ?
C22 C21 H21 120.9 . . ?
C20 C19 C18 117.9(3) . . ?
C20 C19 H19 121.0 . . ?
C18 C19 H19 121.0 . . ?

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
C8 N1 C1 O1 -164.55(19) . . . . ?
C9 N1 C1 O1 69.8(3) . . . . ?
C8 N1 C1 C2 -36.8(2) . . . . ?
C9 N1 C1 C2 -162.39(18) . . . . ?
O1 C1 C2 F1 -97.4(2) . . . . ?
N1 C1 C2 F1 136.35(19) . . . . ?
O1 C1 C2 F2 15.7(3) . . . . ?
N1 C1 C2 F2 -110.6(2) . . . . ?
O1 C1 C2 C3 139.3(2) . . . . ?
N1 C1 C2 C3 13.0(3) . . . . ?
F1 C2 C3 C4 137.28(19) . . . . ?
F2 C2 C3 C4 19.7(2) . . . . ?
C1 C2 C3 C4 -102.4(2) . . . . ?
F1 C2 C3 C16 10.0(3) . . . . ?
F2 C2 C3 C16 -107.6(2) . . . . ?
C1 C2 C3 C16 130.3(2) . . . . ?
F1 C2 C3 C8 -106.1(2) . . . . ?
F2 C2 C3 C8 136.32(19) . . . . ?
C1 C2 C3 C8 14.2(3) . . . . ?
C2 C3 C4 C5 161.00(18) . . . . ?
C16 C3 C4 C5 -71.4(2) . . . . ?
C8 C3 C4 C5 51.2(2) . . . . ?
C3 C4 C5 C6 -59.7(3) . . . . ?
C4 C5 C6 C7 59.1(3) . . . . ?
C5 C6 C7 C8 -54.2(2) . . . . ?
C1 N1 C8 C7 170.7(2) . . . . ?
C9 N1 C8 C7 -64.8(3) . . . . ?
C1 N1 C8 C3 46.8(2) . . . . ?
C9 N1 C8 C3 171.3(2) . . . . ?
C6 C7 C8 N1 -70.4(2) . . . . ?
C6 C7 C8 C3 47.4(3) . . . . ?
C4 C3 C8 N1 80.0(2) . . . . ?
C2 C3 C8 N1 -36.2(2) . . . . ?
C16 C3 C8 N1 -155.3(2) . . . . ?
C4 C3 C8 C7 -44.2(2) . . . . ?
C2 C3 C8 C7 -160.4(2) . . . . ?
C16 C3 C8 C7 80.5(3) . . . . ?
C1 N1 C9 C10 65.1(2) . . . . ?
C8 N1 C9 C10 -54.6(3) . . . . ?
N1 C9 C10 C15 -91.9(2) . . . . ?
N1 C9 C10 C11 89.4(3) . . . . ?
C15 C10 C11 C12 1.8(3) . . . . ?
C9 C10 C11 C12 -179.4(2) . . . . ?
C10 C11 C12 C13 -1.4(4) . . . . ?
C11 C12 C13 C14 -0.3(4) . . . . ?
C11 C12 C13 Cl1 -179.35(18) . . . . ?
C12 C13 C14 C15 1.5(3) . . . . ?
Cl1 C13 C14 C15 -179.50(17) . . . . ?
C13 C14 C15 C10 -1.0(3) . . . . ?
C11 C10 C15 C14 -0.7(3) . . . . ?
C9 C10 C15 C14 -179.42(19) . . . . ?
C4 C3 C16 C17 -54.7(3) . . . . ?
C2 C3 C16 C17 71.2(3) . . . . ?
C8 C3 C16 C17 -178.1(2) . . . . ?
C3 C16 C17 C18 84.7(3) . . . . ?
C3 C16 C17 C22 -98.2(3) . . . . ?
C22 C17 C18 C19 1.9(3) . . . . ?
C16 C17 C18 C19 179.0(2) . . . . ?
C18 C17 C22 C21 -1.5(3) . . . . ?
C16 C17 C22 C21 -178.7(2) . . . . ?
F3 C20 C21 C22 179.9(2) . . . . ?
C19 C20 C21 C22 0.0(4) . . . . ?
C17 C22 C21 C20 0.6(4) . . . . ?
C21 C20 C19 C18 0.4(4) . . . . ?
F3 C20 C19 C18 -179.5(2) . . . . ?
C17 C18 C19 C20 -1.3(3) . . . . ?

_refine_diff_density_max         0.310
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.056



####################################################################### 
# 
# 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_test1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2330506'
loop_
_audit_author_name
_audit_author_address
'Jie Li'
;College of Chemistry, Chemical Engineering and Materials Science, Soochow University
China
;
_audit_update_record             
;
2024-02-02 deposited with the CCDC.	2024-09-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        
1-(4-chlorophenyl)-3,3-difluoro-3a-(4-fluorobenzyl)hexahydrocyclopenta[b]pyrrol-2(1H)-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H17 Cl F3 N O'
_chemical_formula_sum            'C20 H17 Cl F3 N O'
_chemical_formula_weight         379.80

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.4827(8)
_cell_length_b                   11.3393(9)
_cell_length_c                   16.2357(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1745.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3253
_cell_measurement_theta_min      2.1770
_cell_measurement_theta_max      28.1690

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.350
_exptl_absorpt_coefficient_mu    0.258
_shelx_estimated_absorpt_T_min   0.820
_shelx_estimated_absorpt_T_max   0.915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.86361
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4471
_diffrn_reflns_number            5950
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.191
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3512
_reflns_number_gt                2835
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.717
_reflns_Friedel_fraction_max     0.962
_reflns_Friedel_fraction_full    0.978

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;
_computing_publication_material  
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0454P)²+0.1498P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.46(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3512
_refine_ls_number_parameters     249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.1001
_refine_ls_wR_factor_gt          0.0899
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.7103(2) 0.94145(17) 0.53983(12) 0.0676(6) Uani 1 1 d . . . . .
C2 C 0.6321(3) 0.8906(3) 0.60165(19) 0.0485(8) Uani 1 1 d . . . . .
F3 F 0.7689(3) 1.3836(2) 0.81718(16) 0.0889(7) Uani 1 1 d . . . . .
C3 C 0.7219(3) 0.8528(3) 0.67392(19) 0.0430(7) Uani 1 1 d . . . . .
C4 C 0.7628(4) 0.7240(3) 0.6492(2) 0.0488(8) Uani 1 1 d . . . . .
H4 H 0.864(3) 0.7191(3) 0.6229(9) 0.059 Uiso 1 1 calc R U . . .
C5 C 0.7518(5) 0.6539(3) 0.7279(2) 0.0723(12) Uani 1 1 d . . . . .
H5A H 0.835(3) 0.6638(4) 0.7614(10) 0.087 Uiso 1 1 calc R U . . .
H5B H 0.7388(6) 0.571(3) 0.7165(4) 0.087 Uiso 1 1 calc R U . . .
C6 C 0.6227(6) 0.7058(4) 0.7703(2) 0.0807(13) Uani 1 1 d . . . . .
H6A H 0.538(3) 0.6730(11) 0.7482(7) 0.097 Uiso 1 1 calc R U . . .
H6B H 0.6254(5) 0.6911(6) 0.8281(19) 0.097 Uiso 1 1 calc R U . . .
C7 C 0.6311(4) 0.8357(3) 0.7528(2) 0.0584(9) Uani 1 1 d . . . . .
H7A H 0.6716(11) 0.8742(11) 0.7963(12) 0.070 Uiso 1 1 calc R U . . .
H7B H 0.543(2) 0.8658(9) 0.7448(3) 0.070 Uiso 1 1 calc R U . . .
C8 C 0.6373(3) 0.5724(3) 0.55987(17) 0.0409(7) Uani 1 1 d . . . . .
C9 C 0.7525(4) 0.5179(3) 0.5250(2) 0.0573(9) Uani 1 1 d . . . . .
H9 H 0.843(4) 0.5583(17) 0.5230(2) 0.069 Uiso 1 1 calc R U . . .
C10 C 0.7388(4) 0.4060(3) 0.4927(2) 0.0584(9) Uani 1 1 d . . . . .
H10 H 0.813(3) 0.3701(17) 0.4705(10) 0.070 Uiso 1 1 calc R U . . .
C11 C 0.6110(4) 0.3504(3) 0.4951(2) 0.0478(7) Uani 1 1 d . . . . .
C12 C 0.4960(4) 0.4032(3) 0.5304(2) 0.0562(9) Uani 1 1 d . . . . .
H12 H 0.404(4) 0.3613(16) 0.5326(3) 0.067 Uiso 1 1 calc R U . . .
C13 C 0.5094(4) 0.5148(3) 0.5627(2) 0.0538(9) Uani 1 1 d . . . . .
H13 H 0.432(3) 0.5514(16) 0.5866(11) 0.065 Uiso 1 1 calc R U . . .
O1 O 0.4702(3) 0.7749(2) 0.51746(16) 0.0663(7) Uani 1 1 d . . . . .
N1 N 0.6508(3) 0.6897(2) 0.59084(15) 0.0439(6) Uani 1 1 d . . . . .
C1 C 0.5693(4) 0.7787(3) 0.56459(19) 0.0471(7) Uani 1 1 d . . . . .
Cl1 Cl 0.59600(11) 0.20899(8) 0.45418(7) 0.0755(3) Uani 1 1 d . . . . .
F2 F 0.5306(2) 0.97104(17) 0.61909(13) 0.0687(6) Uani 1 1 d . . . . .
C15 C 0.8299(3) 1.0504(3) 0.7231(2) 0.0499(8) Uani 1 1 d . . . . .
C16 C 0.7924(4) 1.1437(3) 0.6732(2) 0.0631(10) Uani 1 1 d . . . . .
H16 H 0.7808(7) 1.1306(7) 0.618(2) 0.076 Uiso 1 1 calc R U . . .
C14 C 0.8549(4) 0.9274(3) 0.6881(2) 0.0560(9) Uani 1 1 d . . . . .
H14A H 0.9167(18) 0.8848(12) 0.7254(10) 0.067 Uiso 1 1 calc R U . . .
H14B H 0.9042(14) 0.9353(3) 0.6360(14) 0.067 Uiso 1 1 calc R U . . .
C19 C 0.8247(5) 1.1855(4) 0.8383(3) 0.0698(11) Uani 1 1 d . . . . .
H19 H 0.8344(7) 1.1988(8) 0.891(3) 0.084 Uiso 1 1 calc R U . . .
C17 C 0.7716(5) 1.2562(3) 0.7038(2) 0.0676(11) Uani 1 1 d . . . . .
H17 H 0.7467(13) 1.318(3) 0.6690(17) 0.081 Uiso 1 1 calc R U . . .
C18 C 0.7885(4) 1.2735(3) 0.7863(2) 0.0595(9) Uani 1 1 d . . . . .
C20 C 0.8460(4) 1.0735(3) 0.8060(2) 0.0636(10) Uani 1 1 d . . . . .
H20 H 0.8723(13) 1.011(3) 0.8417(17) 0.076 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 C2 1.375(4) . ?
C2 F2 1.356(4) . ?
C2 C3 1.512(4) . ?
C2 C1 1.525(5) . ?
F3 C18 1.359(4) . ?
C3 C14 1.536(4) . ?
C3 C7 1.555(4) . ?
C3 C4 1.563(4) . ?
C4 N1 1.476(4) . ?
C4 C5 1.508(5) . ?
C4 H4 1.05(4) . ?
C5 C6 1.522(7) . ?
C5 H5A 0.97(3) . ?
C5 H5B 0.97(3) . ?
C6 C7 1.502(5) . ?
C6 H6A 0.95(3) . ?
C6 H6B 0.95(3) . ?
C7 H7A 0.91(2) . ?
C7 H7B 0.91(2) . ?
C8 C9 1.377(5) . ?
C8 C13 1.378(4) . ?
C8 N1 1.427(4) . ?
C9 C10 1.379(5) . ?
C9 H9 0.98(4) . ?
C10 C11 1.366(5) . ?
C10 H10 0.89(4) . ?
C11 C12 1.369(5) . ?
C11 Cl1 1.742(3) . ?
C12 C13 1.376(5) . ?
C12 H12 1.00(4) . ?
C13 H13 0.93(4) . ?
O1 C1 1.213(4) . ?
N1 C1 1.341(4) . ?
C15 C16 1.378(5) . ?
C15 C20 1.379(5) . ?
C15 C14 1.525(5) . ?
C16 C17 1.383(5) . ?
C16 H16 0.92(4) . ?
C14 H14A 0.97(3) . ?
C14 H14B 0.97(3) . ?
C19 C18 1.350(5) . ?
C19 C20 1.389(5) . ?
C19 H19 0.87(4) . ?
C17 C18 1.363(5) . ?
C17 H17 0.94(4) . ?
C20 H20 0.95(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F2 C2 F1 104.7(2) . . ?
F2 C2 C3 115.4(3) . . ?
F1 C2 C3 112.4(3) . . ?
F2 C2 C1 111.4(3) . . ?
F1 C2 C1 105.8(3) . . ?
C3 C2 C1 106.9(2) . . ?
C2 C3 C14 115.0(3) . . ?
C2 C3 C7 111.3(3) . . ?
C14 C3 C7 113.6(3) . . ?
C2 C3 C4 101.9(2) . . ?
C14 C3 C4 110.4(3) . . ?
C7 C3 C4 103.4(3) . . ?
N1 C4 C5 110.8(3) . . ?
N1 C4 C3 103.4(2) . . ?
C5 C4 C3 104.9(3) . . ?
N1 C4 H4 112.4 . . ?
C5 C4 H4 112.4 . . ?
C3 C4 H4 112.4 . . ?
C4 C5 C6 103.6(3) . . ?
C4 C5 H5A 111.0 . . ?
C6 C5 H5A 111.0 . . ?
C4 C5 H5B 111.0 . . ?
C6 C5 H5B 111.0 . . ?
H5A C5 H5B 109.0 . . ?
C7 C6 C5 104.5(3) . . ?
C7 C6 H6A 110.8 . . ?
C5 C6 H6A 110.8 . . ?
C7 C6 H6B 110.8 . . ?
C5 C6 H6B 110.8 . . ?
H6A C6 H6B 108.9 . . ?
C6 C7 C3 107.9(3) . . ?
C6 C7 H7A 110.1 . . ?
C3 C7 H7A 110.1 . . ?
C6 C7 H7B 110.1 . . ?
C3 C7 H7B 110.1 . . ?
H7A C7 H7B 108.4 . . ?
C9 C8 C13 119.9(3) . . ?
C9 C8 N1 119.5(3) . . ?
C13 C8 N1 120.6(3) . . ?
C8 C9 C10 119.7(3) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 119.8(3) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 121.1(3) . . ?
C10 C11 Cl1 119.1(3) . . ?
C12 C11 Cl1 119.8(3) . . ?
C11 C12 C13 119.2(3) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C12 C13 C8 120.3(3) . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?
C1 N1 C8 122.5(3) . . ?
C1 N1 C4 114.8(2) . . ?
C8 N1 C4 122.5(2) . . ?
O1 C1 N1 128.3(3) . . ?
O1 C1 C2 125.5(3) . . ?
N1 C1 C2 106.0(3) . . ?
C16 C15 C20 117.1(3) . . ?
C16 C15 C14 121.5(3) . . ?
C20 C15 C14 121.3(3) . . ?
C15 C16 C17 122.2(4) . . ?
C15 C16 H16 118.9 . . ?
C17 C16 H16 118.9 . . ?
C15 C14 C3 115.6(3) . . ?
C15 C14 H14A 108.4 . . ?
C3 C14 H14A 108.4 . . ?
C15 C14 H14B 108.4 . . ?
C3 C14 H14B 108.4 . . ?
H14A C14 H14B 107.4 . . ?
C18 C19 C20 118.4(4) . . ?
C18 C19 H19 120.8 . . ?
C20 C19 H19 120.8 . . ?
C18 C17 C16 118.0(4) . . ?
C18 C17 H17 121.0 . . ?
C16 C17 H17 121.0 . . ?
C19 C18 F3 118.9(3) . . ?
C19 C18 C17 122.5(4) . . ?
F3 C18 C17 118.6(3) . . ?
C15 C20 C19 121.7(4) . . ?
C15 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?

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
F2 C2 C3 C14 -90.0(3) . . . . ?
F1 C2 C3 C14 29.9(4) . . . . ?
C1 C2 C3 C14 145.5(3) . . . . ?
F2 C2 C3 C7 40.9(4) . . . . ?
F1 C2 C3 C7 160.8(2) . . . . ?
C1 C2 C3 C7 -83.5(3) . . . . ?
F2 C2 C3 C4 150.6(3) . . . . ?
F1 C2 C3 C4 -89.5(3) . . . . ?
C1 C2 C3 C4 26.1(3) . . . . ?
C2 C3 C4 N1 -22.9(3) . . . . ?
C14 C3 C4 N1 -145.5(3) . . . . ?
C7 C3 C4 N1 92.6(3) . . . . ?
C2 C3 C4 C5 -139.1(3) . . . . ?
C14 C3 C4 C5 98.3(3) . . . . ?
C7 C3 C4 C5 -23.6(4) . . . . ?
N1 C4 C5 C6 -72.7(4) . . . . ?
C3 C4 C5 C6 38.3(4) . . . . ?
C4 C5 C6 C7 -38.2(4) . . . . ?
C5 C6 C7 C3 23.3(4) . . . . ?
C2 C3 C7 C6 108.6(4) . . . . ?
C14 C3 C7 C6 -119.7(3) . . . . ?
C4 C3 C7 C6 0.0(4) . . . . ?
C13 C8 C9 C10 0.3(5) . . . . ?
N1 C8 C9 C10 -178.1(3) . . . . ?
C8 C9 C10 C11 0.5(6) . . . . ?
C9 C10 C11 C12 -1.2(6) . . . . ?
C9 C10 C11 Cl1 -179.9(3) . . . . ?
C10 C11 C12 C13 1.1(5) . . . . ?
Cl1 C11 C12 C13 179.8(3) . . . . ?
C11 C12 C13 C8 -0.3(5) . . . . ?
C9 C8 C13 C12 -0.4(5) . . . . ?
N1 C8 C13 C12 177.9(3) . . . . ?
C9 C8 N1 C1 123.0(3) . . . . ?
C13 C8 N1 C1 -55.3(4) . . . . ?
C9 C8 N1 C4 -52.0(4) . . . . ?
C13 C8 N1 C4 129.7(3) . . . . ?
C5 C4 N1 C1 124.2(3) . . . . ?
C3 C4 N1 C1 12.2(3) . . . . ?
C5 C4 N1 C8 -60.4(4) . . . . ?
C3 C4 N1 C8 -172.4(3) . . . . ?
C8 N1 C1 O1 5.2(5) . . . . ?
C4 N1 C1 O1 -179.4(3) . . . . ?
C8 N1 C1 C2 -171.1(3) . . . . ?
C4 N1 C1 C2 4.3(4) . . . . ?
F2 C2 C1 O1 36.8(4) . . . . ?
F1 C2 C1 O1 -76.3(4) . . . . ?
C3 C2 C1 O1 163.7(3) . . . . ?
F2 C2 C1 N1 -146.8(3) . . . . ?
F1 C2 C1 N1 100.1(3) . . . . ?
C3 C2 C1 N1 -19.9(3) . . . . ?
C20 C15 C16 C17 0.1(6) . . . . ?
C14 C15 C16 C17 -178.9(4) . . . . ?
C16 C15 C14 C3 -82.2(4) . . . . ?
C20 C15 C14 C3 98.7(4) . . . . ?
C2 C3 C14 C15 72.9(4) . . . . ?
C7 C3 C14 C15 -56.9(4) . . . . ?
C4 C3 C14 C15 -172.5(3) . . . . ?
C15 C16 C17 C18 -0.4(6) . . . . ?
C20 C19 C18 F3 -179.3(4) . . . . ?
C20 C19 C18 C17 0.4(7) . . . . ?
C16 C17 C18 C19 0.1(7) . . . . ?
C16 C17 C18 F3 179.8(4) . . . . ?
C16 C15 C20 C19 0.4(6) . . . . ?
C14 C15 C20 C19 179.4(3) . . . . ?
C18 C19 C20 C15 -0.6(6) . . . . ?

_refine_diff_density_max         0.156
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.036



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

data_b230317c1_0m
_database_code_depnum_ccdc_archive 'CCDC 2330508'
loop_
_audit_author_name
_audit_author_address
'Jie Li'
;College of Chemistry, Chemical Engineering and Materials Science, Soochow University
China
;
_audit_update_record             
;
2024-02-02 deposited with the CCDC.	2024-09-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H20 Cl F2 N O S'
_chemical_formula_weight         467.94

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0140 0.0070 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3280 0.5430 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0580 0.0400 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0240 0.0130 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0390 0.0240 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2920 0.4300 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/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                   11.743(3)
_cell_length_b                   16.564(4)
_cell_length_c                   12.926(3)
_cell_angle_alpha                90
_cell_angle_beta                 120.721(17)
_cell_angle_gamma                90
_cell_volume                     2161.4(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.831
_shelx_estimated_absorpt_T_min   0.771
_shelx_estimated_absorpt_T_max   0.838
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     1.34138
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19916
_diffrn_reflns_av_unetI/netI     0.1071
_diffrn_reflns_av_R_equivalents  0.1153
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.809
_diffrn_reflns_theta_max         53.996
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3953
_reflns_number_gt                2214
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1254P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3953
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1409
_refine_ls_R_factor_gt           0.0717
_refine_ls_wR_factor_ref         0.2201
_refine_ls_wR_factor_gt          0.1765
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.23751(14) -0.54174(8) 1.12308(11) 0.0678(5) Uani 1 1 d . . . . .
S1 S -0.57079(11) -0.35663(7) -0.13001(9) 0.0417(4) Uani 1 1 d . . . . .
F1 F -0.0818(2) -0.34202(15) 0.36608(19) 0.0452(7) Uani 1 1 d . . . . .
F2 F 0.0029(3) -0.24669(15) 0.5008(2) 0.0533(7) Uani 1 1 d . . . . .
O1 O 0.1050(3) -0.4221(2) 0.5803(3) 0.0501(9) Uani 1 1 d . . . . .
N1 N -0.0244(3) -0.3719(2) 0.6540(3) 0.0368(9) Uani 1 1 d . . . . .
C1 C 0.0175(4) -0.3788(3) 0.5744(4) 0.0385(11) Uani 1 1 d . . . . .
C2 C -0.0672(4) -0.3189(3) 0.4731(3) 0.0393(11) Uani 1 1 d . . . . .
C3 C -0.1909(4) -0.3077(3) 0.4778(3) 0.0398(11) Uani 1 1 d . . . . .
H3 H -0.2333 -0.2545 0.4424 0.048 Uiso 1 1 calc R U . . .
C4 C -0.1295(4) -0.3077(3) 0.6165(3) 0.0409(11) Uani 1 1 d . . . . .
H4 H -0.0861 -0.2544 0.6498 0.049 Uiso 1 1 calc R U . . .
C5 C -0.2275(5) -0.3253(3) 0.6578(4) 0.0473(13) Uani 1 1 d . . . . .
H5A H -0.1774 -0.3360 0.7454 0.057 Uiso 1 1 calc R U . . .
H5B H -0.2824 -0.2766 0.6441 0.057 Uiso 1 1 calc R U . . .
C6 C -0.3186(4) -0.3965(3) 0.5943(4) 0.0474(12) Uani 1 1 d . . . . .
H6A H -0.3849 -0.4008 0.6196 0.057 Uiso 1 1 calc R U . . .
H6B H -0.2661 -0.4469 0.6177 0.057 Uiso 1 1 calc R U . . .
C7 C -0.3894(4) -0.3862(3) 0.4580(4) 0.0451(12) Uani 1 1 d . . . . .
H7A H -0.4460 -0.3374 0.4344 0.054 Uiso 1 1 calc R U . . .
H7B H -0.4474 -0.4334 0.4187 0.054 Uiso 1 1 calc R U . . .
C8 C -0.2894(4) -0.3781(3) 0.4139(4) 0.0401(11) Uani 1 1 d . . . . .
H8 H -0.2360 -0.4289 0.4374 0.048 Uiso 1 1 calc R U . . .
C9 C -0.4839(4) -0.3701(3) 0.0269(4) 0.0384(11) Uani 1 1 d . . . . .
C10 C -0.3949(4) -0.4315(3) 0.0906(4) 0.0375(11) Uani 1 1 d . . . . .
H10 H -0.3751 -0.4717 0.0497 0.045 Uiso 1 1 calc R U . . .
C11 C -0.3358(4) -0.4332(3) 0.2140(4) 0.0395(11) Uani 1 1 d . . . . .
H11 H -0.2763 -0.4758 0.2576 0.047 Uiso 1 1 calc R U . . .
C12 C -0.3611(4) -0.3731(3) 0.2779(4) 0.0372(11) Uani 1 1 d . . . . .
C13 C -0.4502(4) -0.3121(3) 0.2123(3) 0.0358(10) Uani 1 1 d . . . . .
H13 H -0.4685 -0.2714 0.2535 0.043 Uiso 1 1 calc R U . . .
C14 C -0.5133(4) -0.3091(3) 0.0869(4) 0.0337(10) Uani 1 1 d . . . . .
C15 C -0.6083(4) -0.2512(3) 0.0023(3) 0.0353(10) Uani 1 1 d . . . . .
C16 C -0.6621(4) -0.1824(3) 0.0250(4) 0.0414(11) Uani 1 1 d . . . . .
H16 H -0.6376 -0.1687 0.1051 0.050 Uiso 1 1 calc R U . . .
C17 C -0.7510(5) -0.1349(3) -0.0703(4) 0.0486(13) Uani 1 1 d . . . . .
H17 H -0.7884 -0.0888 -0.0551 0.058 Uiso 1 1 calc R U . . .
C18 C -0.7866(5) -0.1537(3) -0.1886(4) 0.0475(12) Uani 1 1 d . . . . .
H18 H -0.8465 -0.1196 -0.2526 0.057 Uiso 1 1 calc R U . . .
C19 C -0.7359(4) -0.2211(3) -0.2134(4) 0.0431(12) Uani 1 1 d . . . . .
H19 H -0.7610 -0.2342 -0.2938 0.052 Uiso 1 1 calc R U . . .
C20 C -0.6469(4) -0.2696(3) -0.1180(3) 0.0362(10) Uani 1 1 d . . . . .
C21 C 0.0382(4) -0.4128(3) 0.7675(4) 0.0354(10) Uani 1 1 d . . . . .
C22 C 0.0412(4) -0.4959(3) 0.7704(4) 0.0410(11) Uani 1 1 d . . . . .
H22 H 0.0024 -0.5258 0.6974 0.049 Uiso 1 1 calc R U . . .
C23 C 0.1004(4) -0.5357(3) 0.8790(4) 0.0443(12) Uani 1 1 d . . . . .
H23 H 0.1020 -0.5930 0.8814 0.053 Uiso 1 1 calc R U . . .
C24 C 0.1575(4) -0.4917(3) 0.9845(4) 0.0444(12) Uani 1 1 d . . . . .
C25 C 0.1563(5) -0.4084(3) 0.9835(4) 0.0442(12) Uani 1 1 d . . . . .
H25 H 0.1963 -0.3790 1.0569 0.053 Uiso 1 1 calc R U . . .
C26 C 0.0959(4) -0.3680(3) 0.8738(3) 0.0394(11) Uani 1 1 d . . . . .
H26 H 0.0938 -0.3107 0.8713 0.047 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 C24 1.749(4) . ?
S1 C20 1.745(4) . ?
S1 C9 1.758(4) . ?
F1 C2 1.359(4) . ?
F2 C2 1.392(5) . ?
O1 C1 1.223(5) . ?
N1 C1 1.354(5) . ?
N1 C21 1.431(5) . ?
N1 C4 1.509(5) . ?
C1 C2 1.535(6) . ?
C2 C3 1.496(6) . ?
C3 C8 1.551(6) . ?
C3 C4 1.554(5) . ?
C3 H3 1.0000 . ?
C4 C5 1.523(6) . ?
C4 H4 1.0000 . ?
C5 C6 1.520(7) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.526(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.551(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C12 1.514(5) . ?
C8 H8 1.0000 . ?
C9 C10 1.387(6) . ?
C9 C14 1.419(5) . ?
C10 C11 1.377(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.419(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(6) . ?
C13 C14 1.397(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.454(6) . ?
C15 C16 1.404(6) . ?
C15 C20 1.412(5) . ?
C16 C17 1.383(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.399(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.378(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.393(6) . ?
C19 H19 0.9500 . ?
C21 C22 1.378(6) . ?
C21 C26 1.395(5) . ?
C22 C23 1.375(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.381(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.379(7) . ?
C25 C26 1.391(6) . ?
C25 H25 0.9500 . ?
C26 H26 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
C20 S1 C9 91.38(19) . . ?
C1 N1 C21 122.9(4) . . ?
C1 N1 C4 111.7(3) . . ?
C21 N1 C4 124.8(3) . . ?
O1 C1 N1 128.5(4) . . ?
O1 C1 C2 126.1(4) . . ?
N1 C1 C2 105.4(4) . . ?
F1 C2 F2 104.7(3) . . ?
F1 C2 C3 117.1(3) . . ?
F2 C2 C3 110.0(4) . . ?
F1 C2 C1 112.1(4) . . ?
F2 C2 C1 107.2(3) . . ?
C3 C2 C1 105.4(3) . . ?
C2 C3 C8 111.1(3) . . ?
C2 C3 C4 99.1(3) . . ?
C8 C3 C4 113.2(3) . . ?
C2 C3 H3 111.0 . . ?
C8 C3 H3 111.0 . . ?
C4 C3 H3 111.0 . . ?
N1 C4 C5 113.1(3) . . ?
N1 C4 C3 101.1(3) . . ?
C5 C4 C3 114.6(4) . . ?
N1 C4 H4 109.2 . . ?
C5 C4 H4 109.2 . . ?
C3 C4 H4 109.2 . . ?
C6 C5 C4 114.1(4) . . ?
C6 C5 H5A 108.7 . . ?
C4 C5 H5A 108.7 . . ?
C6 C5 H5B 108.7 . . ?
C4 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
C5 C6 C7 110.8(4) . . ?
C5 C6 H6A 109.5 . . ?
C7 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C6 C7 C8 111.5(4) . . ?
C6 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C12 C8 C3 113.5(3) . . ?
C12 C8 C7 110.8(3) . . ?
C3 C8 C7 111.6(3) . . ?
C12 C8 H8 106.9 . . ?
C3 C8 H8 106.9 . . ?
C7 C8 H8 106.9 . . ?
C10 C9 C14 121.1(4) . . ?
C10 C9 S1 126.5(3) . . ?
C14 C9 S1 112.3(3) . . ?
C11 C10 C9 118.9(4) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C10 C11 C12 121.9(4) . . ?
C10 C11 H11 119.0 . . ?
C12 C11 H11 119.0 . . ?
C13 C12 C11 118.1(4) . . ?
C13 C12 C8 123.3(4) . . ?
C11 C12 C8 118.6(4) . . ?
C12 C13 C14 121.5(4) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C13 C14 C9 118.4(4) . . ?
C13 C14 C15 130.1(4) . . ?
C9 C14 C15 111.5(4) . . ?
C16 C15 C20 118.6(4) . . ?
C16 C15 C14 129.2(4) . . ?
C20 C15 C14 112.1(4) . . ?
C17 C16 C15 119.4(4) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C18 121.0(4) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C19 C18 C17 120.7(4) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C20 118.7(4) . . ?
C18 C19 H19 120.7 . . ?
C20 C19 H19 120.7 . . ?
C19 C20 C15 121.6(4) . . ?
C19 C20 S1 125.8(3) . . ?
C15 C20 S1 112.7(3) . . ?
C22 C21 C26 120.8(4) . . ?
C22 C21 N1 119.5(4) . . ?
C26 C21 N1 119.6(4) . . ?
C23 C22 C21 119.9(4) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C23 C24 119.5(4) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
C25 C24 C23 121.4(4) . . ?
C25 C24 Cl1 118.8(4) . . ?
C23 C24 Cl1 119.8(4) . . ?
C24 C25 C26 119.2(4) . . ?
C24 C25 H25 120.4 . . ?
C26 C25 H25 120.4 . . ?
C25 C26 C21 119.1(4) . . ?
C25 C26 H26 120.4 . . ?
C21 C26 H26 120.4 . . ?

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
C21 N1 C1 O1 4.8(7) . . . . ?
C4 N1 C1 O1 176.5(4) . . . . ?
C21 N1 C1 C2 -174.2(4) . . . . ?
C4 N1 C1 C2 -2.6(5) . . . . ?
O1 C1 C2 F1 28.4(6) . . . . ?
N1 C1 C2 F1 -152.5(3) . . . . ?
O1 C1 C2 F2 -86.0(5) . . . . ?
N1 C1 C2 F2 93.1(4) . . . . ?
O1 C1 C2 C3 156.9(4) . . . . ?
N1 C1 C2 C3 -24.0(4) . . . . ?
F1 C2 C3 C8 44.7(5) . . . . ?
F2 C2 C3 C8 164.1(3) . . . . ?
C1 C2 C3 C8 -80.7(4) . . . . ?
F1 C2 C3 C4 164.1(4) . . . . ?
F2 C2 C3 C4 -76.6(4) . . . . ?
C1 C2 C3 C4 38.7(4) . . . . ?
C1 N1 C4 C5 149.7(4) . . . . ?
C21 N1 C4 C5 -38.8(5) . . . . ?
C1 N1 C4 C3 26.7(4) . . . . ?
C21 N1 C4 C3 -161.8(4) . . . . ?
C2 C3 C4 N1 -38.6(4) . . . . ?
C8 C3 C4 N1 79.1(4) . . . . ?
C2 C3 C4 C5 -160.6(4) . . . . ?
C8 C3 C4 C5 -42.9(5) . . . . ?
N1 C4 C5 C6 -69.1(5) . . . . ?
C3 C4 C5 C6 46.1(5) . . . . ?
C4 C5 C6 C7 -53.5(5) . . . . ?
C5 C6 C7 C8 58.5(5) . . . . ?
C2 C3 C8 C12 -76.0(5) . . . . ?
C4 C3 C8 C12 173.5(3) . . . . ?
C2 C3 C8 C7 158.0(3) . . . . ?
C4 C3 C8 C7 47.5(5) . . . . ?
C6 C7 C8 C12 176.6(4) . . . . ?
C6 C7 C8 C3 -56.0(5) . . . . ?
C20 S1 C9 C10 -179.5(4) . . . . ?
C20 S1 C9 C14 0.2(3) . . . . ?
C14 C9 C10 C11 0.7(6) . . . . ?
S1 C9 C10 C11 -179.7(3) . . . . ?
C9 C10 C11 C12 -1.3(6) . . . . ?
C10 C11 C12 C13 1.1(6) . . . . ?
C10 C11 C12 C8 -178.4(4) . . . . ?
C3 C8 C12 C13 -65.6(5) . . . . ?
C7 C8 C12 C13 60.8(5) . . . . ?
C3 C8 C12 C11 113.9(4) . . . . ?
C7 C8 C12 C11 -119.7(4) . . . . ?
C11 C12 C13 C14 -0.2(6) . . . . ?
C8 C12 C13 C14 179.3(4) . . . . ?
C12 C13 C14 C9 -0.4(6) . . . . ?
C12 C13 C14 C15 -179.9(4) . . . . ?
C10 C9 C14 C13 0.2(6) . . . . ?
S1 C9 C14 C13 -179.5(3) . . . . ?
C10 C9 C14 C15 179.8(4) . . . . ?
S1 C9 C14 C15 0.1(4) . . . . ?
C13 C14 C15 C16 -0.1(7) . . . . ?
C9 C14 C15 C16 -179.6(4) . . . . ?
C13 C14 C15 C20 179.1(4) . . . . ?
C9 C14 C15 C20 -0.4(5) . . . . ?
C20 C15 C16 C17 0.1(6) . . . . ?
C14 C15 C16 C17 179.3(4) . . . . ?
C15 C16 C17 C18 -0.9(7) . . . . ?
C16 C17 C18 C19 1.3(7) . . . . ?
C17 C18 C19 C20 -0.8(7) . . . . ?
C18 C19 C20 C15 0.1(6) . . . . ?
C18 C19 C20 S1 -179.5(3) . . . . ?
C16 C15 C20 C19 0.3(6) . . . . ?
C14 C15 C20 C19 -179.0(4) . . . . ?
C16 C15 C20 S1 179.9(3) . . . . ?
C14 C15 C20 S1 0.6(4) . . . . ?
C9 S1 C20 C19 179.1(4) . . . . ?
C9 S1 C20 C15 -0.4(3) . . . . ?
C1 N1 C21 C22 -61.7(6) . . . . ?
C4 N1 C21 C22 127.7(4) . . . . ?
C1 N1 C21 C26 118.1(5) . . . . ?
C4 N1 C21 C26 -52.5(5) . . . . ?
C26 C21 C22 C23 0.6(6) . . . . ?
N1 C21 C22 C23 -179.5(4) . . . . ?
C21 C22 C23 C24 -0.6(6) . . . . ?
C22 C23 C24 C25 0.1(6) . . . . ?
C22 C23 C24 Cl1 -178.0(3) . . . . ?
C23 C24 C25 C26 0.2(6) . . . . ?
Cl1 C24 C25 C26 178.4(3) . . . . ?
C24 C25 C26 C21 -0.2(6) . . . . ?
C22 C21 C26 C25 -0.3(6) . . . . ?
N1 C21 C26 C25 179.9(4) . . . . ?

_refine_diff_density_max         0.391
_refine_diff_density_min         -0.602
_refine_diff_density_rms         0.093

_shelxl_version_number           2014-3



