# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_120-9
_database_code_depnum_ccdc_archive 'CCDC 2279970'
loop_
_audit_author_name
_audit_author_address
'Zhi Zhou'
;Guangzhou Medical University
China
;
_audit_update_record             
;
2023-07-07 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;
_audit_creation_date             2023-04-24
_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 Br F2 N2 O'
_chemical_formula_sum            'C21 H17 Br F2 N2 O'
_chemical_formula_weight         431.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   9.5594(7)
_cell_length_b                   19.9216(15)
_cell_length_c                   10.3113(8)
_cell_angle_alpha                90
_cell_angle_beta                 110.294(9)
_cell_angle_gamma                90
_cell_volume                     1841.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3205
_cell_measurement_temperature    220.03(10)
_cell_measurement_theta_max      26.3590
_cell_measurement_theta_min      2.9160
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.265
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67432
_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            'light colourless'
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_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  0.0368
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8451
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.045
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      220.03(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 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -84.00 -49.00   1.00    5.00    --  -11.27 -57.00 -90.00   35
  2  ω    -33.00  32.00   1.00    5.00    --   11.90 -38.00 120.00   65
  3  ω    -20.00  84.00   1.00    5.00    --   11.90  77.00  60.00  104
;
_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      0.0611620000
_diffrn_orient_matrix_UB_12      -0.0003240000
_diffrn_orient_matrix_UB_13      0.0632803000
_diffrn_orient_matrix_UB_21      0.0052708000
_diffrn_orient_matrix_UB_22      -0.0353916000
_diffrn_orient_matrix_UB_23      -0.0048499000
_diffrn_orient_matrix_UB_31      0.0498448000
_diffrn_orient_matrix_UB_32      0.0041191000
_diffrn_orient_matrix_UB_33      -0.0367325000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2550
_reflns_number_total             3249
_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         0.624
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.034
_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)+(0.0391P)²+0.3064P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0795
_refine_ls_wR_factor_ref         0.0874
_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
2.a Ternary CH refined with riding coordinates:
 C7(H7), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C11(H11), C12(H12), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_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
Br1 Br 0.35171(3) 0.54045(2) 0.21010(3) 0.03971(13) Uani 1 1 d . . . . .
F1 F 0.5015(2) 0.63622(10) 0.56608(15) 0.0447(5) Uani 1 1 d . . . . .
F2 F 0.7186(2) 0.58645(9) 0.64587(15) 0.0458(5) Uani 1 1 d . . . . .
O1 O 0.6112(3) 0.77752(11) 0.6915(2) 0.0505(6) Uani 1 1 d . . . . .
N1 N 0.5514(2) 0.74864(11) 0.3374(2) 0.0250(5) Uani 1 1 d . . . . .
N2 N 0.6228(3) 0.75264(12) 0.4842(2) 0.0280(6) Uani 1 1 d . . . . .
C1 C 0.5553(3) 0.69910(15) 0.0809(3) 0.0263(7) Uani 1 1 d . . . . .
C2 C 0.5369(3) 0.67969(17) -0.0543(3) 0.0352(8) Uani 1 1 d . . . . .
H2 H 0.573533 0.707748 -0.109879 0.042 Uiso 1 1 calc R U . . .
C3 C 0.4665(3) 0.62058(17) -0.1079(3) 0.0389(8) Uani 1 1 d . . . . .
H3 H 0.455767 0.608068 -0.199790 0.047 Uiso 1 1 calc R U . . .
C4 C 0.4112(3) 0.57912(16) -0.0297(3) 0.0356(8) Uani 1 1 d . . . . .
H4 H 0.363004 0.538113 -0.066529 0.043 Uiso 1 1 calc R U . . .
C5 C 0.4276(3) 0.59870(15) 0.1036(3) 0.0282(7) Uani 1 1 d . . . . .
C6 C 0.4995(3) 0.65761(14) 0.1616(2) 0.0224(6) Uani 1 1 d . . . . .
C7 C 0.5220(3) 0.67620(14) 0.3090(2) 0.0212(6) Uani 1 1 d . . . . .
H7 H 0.429250 0.664320 0.327816 0.025 Uiso 1 1 calc R U . . .
C8 C 0.6576(3) 0.64010(14) 0.4200(2) 0.0225(6) Uani 1 1 d . . . . .
C9 C 0.6381(3) 0.63320(16) 0.5555(3) 0.0326(7) Uani 1 1 d . . . . .
C10 C 0.7146(3) 0.69389(14) 0.5345(3) 0.0270(7) Uani 1 1 d . . . . .
H10 H 0.824197 0.699168 0.584694 0.032 Uiso 1 1 calc R U . . .
C11 C 0.6325(3) 0.76008(15) 0.1431(3) 0.0314(7) Uani 1 1 d . . . . .
H11 H 0.682570 0.785782 0.095016 0.038 Uiso 1 1 calc R U . . .
C12 C 0.6343(3) 0.78058(15) 0.2662(3) 0.0288(7) Uani 1 1 d . . . . .
H12 H 0.693983 0.818247 0.307814 0.035 Uiso 1 1 calc R U . . .
C13 C 0.5554(3) 0.78412(16) 0.5670(3) 0.0346(7) Uani 1 1 d . . . . .
C14 C 0.4204(4) 0.82691(18) 0.4954(3) 0.0431(8) Uani 1 1 d . . . . .
H14A H 0.362750 0.833198 0.557872 0.052 Uiso 1 1 calc R U . . .
H14B H 0.355616 0.803297 0.411636 0.052 Uiso 1 1 calc R U . . .
C15 C 0.4621(4) 0.89481(19) 0.4546(3) 0.0565(10) Uani 1 1 d . . . . .
H15A H 0.506852 0.889149 0.382989 0.085 Uiso 1 1 calc R U . . .
H15B H 0.534037 0.916558 0.535691 0.085 Uiso 1 1 calc R U . . .
H15C H 0.372547 0.922757 0.418756 0.085 Uiso 1 1 calc R U . . .
C16 C 0.7628(3) 0.59635(15) 0.3814(2) 0.0264(7) Uani 1 1 d . . . . .
C17 C 0.7495(4) 0.52685(15) 0.3790(3) 0.0350(8) Uani 1 1 d . . . . .
H17 H 0.671907 0.506123 0.402338 0.042 Uiso 1 1 calc R U . . .
C18 C 0.8511(4) 0.48761(18) 0.3420(3) 0.0471(9) Uani 1 1 d . . . . .
H18 H 0.841541 0.440113 0.339195 0.057 Uiso 1 1 calc R U . . .
C19 C 0.9638(4) 0.5170(2) 0.3098(3) 0.0495(10) Uani 1 1 d . . . . .
H19 H 1.031859 0.489796 0.284526 0.059 Uiso 1 1 calc R U . . .
C20 C 0.9796(4) 0.5851(2) 0.3135(3) 0.0456(9) Uani 1 1 d . . . . .
H20 H 1.058981 0.605230 0.291917 0.055 Uiso 1 1 calc R U . . .
C21 C 0.8795(3) 0.62479(17) 0.3489(3) 0.0350(7) Uani 1 1 d . . . . .
H21 H 0.890605 0.672210 0.351081 0.042 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
Br1 C5 1.905(3) . ?
F1 C9 1.349(3) . ?
F2 C9 1.353(3) . ?
O1 C13 1.215(3) . ?
N1 N2 1.431(3) . ?
N1 C7 1.480(3) . ?
N1 C12 1.405(3) . ?
N2 C10 1.447(4) . ?
N2 C13 1.385(4) . ?
C1 C2 1.398(4) . ?
C1 C6 1.403(4) . ?
C1 C11 1.450(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.374(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(4) . ?
C5 C6 1.387(4) . ?
C6 C7 1.505(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.574(4) . ?
C8 C9 1.478(4) . ?
C8 C10 1.547(4) . ?
C8 C16 1.486(4) . ?
C9 C10 1.467(4) . ?
C10 H10 1.0000 . ?
C11 H11 0.9500 . ?
C11 C12 1.328(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.509(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.511(5) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.390(4) . ?
C16 C21 1.392(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.399(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.364(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.365(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.384(4) . ?
C21 H21 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
N2 N1 C7 104.58(19) . . ?
C12 N1 N2 112.2(2) . . ?
C12 N1 C7 116.2(2) . . ?
N1 N2 C10 110.0(2) . . ?
C13 N2 N1 121.6(2) . . ?
C13 N2 C10 120.0(2) . . ?
C2 C1 C6 119.1(3) . . ?
C2 C1 C11 122.8(3) . . ?
C6 C1 C11 118.1(2) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.9(3) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.7(3) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.8 . . ?
C3 C4 C5 118.5(3) . . ?
C5 C4 H4 120.8 . . ?
C4 C5 Br1 117.8(2) . . ?
C4 C5 C6 122.3(3) . . ?
C6 C5 Br1 119.88(19) . . ?
C1 C6 C7 120.2(2) . . ?
C5 C6 C1 118.5(2) . . ?
C5 C6 C7 121.3(2) . . ?
N1 C7 C6 113.0(2) . . ?
N1 C7 H7 108.2 . . ?
N1 C7 C8 104.5(2) . . ?
C6 C7 H7 108.2 . . ?
C6 C7 C8 114.5(2) . . ?
C8 C7 H7 108.2 . . ?
C9 C8 C7 112.9(2) . . ?
C9 C8 C10 57.98(18) . . ?
C9 C8 C16 121.2(2) . . ?
C10 C8 C7 102.8(2) . . ?
C16 C8 C7 122.4(2) . . ?
C16 C8 C10 121.2(2) . . ?
F1 C9 F2 108.0(2) . . ?
F1 C9 C8 121.0(2) . . ?
F1 C9 C10 121.4(3) . . ?
F2 C9 C8 119.2(3) . . ?
F2 C9 C10 118.4(2) . . ?
C10 C9 C8 63.37(19) . . ?
N2 C10 C8 106.1(2) . . ?
N2 C10 C9 116.6(2) . . ?
N2 C10 H10 119.8 . . ?
C8 C10 H10 119.8 . . ?
C9 C10 C8 58.65(18) . . ?
C9 C10 H10 119.8 . . ?
C1 C11 H11 119.4 . . ?
C12 C11 C1 121.1(3) . . ?
C12 C11 H11 119.4 . . ?
N1 C12 H12 118.8 . . ?
C11 C12 N1 122.5(3) . . ?
C11 C12 H12 118.8 . . ?
O1 C13 N2 118.3(3) . . ?
O1 C13 C14 124.4(3) . . ?
N2 C13 C14 117.2(2) . . ?
C13 C14 H14A 109.2 . . ?
C13 C14 H14B 109.2 . . ?
C13 C14 C15 112.2(3) . . ?
H14A C14 H14B 107.9 . . ?
C15 C14 H14A 109.2 . . ?
C15 C14 H14B 109.2 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C8 121.5(3) . . ?
C17 C16 C21 118.5(3) . . ?
C21 C16 C8 120.0(3) . . ?
C16 C17 H17 120.2 . . ?
C16 C17 C18 119.6(3) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.5(3) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.6(3) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 120.2 . . ?
C19 C20 C21 119.7(3) . . ?
C21 C20 H20 120.2 . . ?
C16 C21 H21 119.5 . . ?
C20 C21 C16 121.1(3) . . ?
C20 C21 H21 119.5 . . ?

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
Br1 C5 C6 C1 179.44(19) . . . . ?
Br1 C5 C6 C7 1.2(4) . . . . ?
F1 C9 C10 N2 -18.3(3) . . . . ?
F1 C9 C10 C8 -111.6(3) . . . . ?
F2 C9 C10 N2 -156.3(2) . . . . ?
F2 C9 C10 C8 110.4(3) . . . . ?
O1 C13 C14 C15 98.7(4) . . . . ?
N1 N2 C10 C8 -19.1(3) . . . . ?
N1 N2 C10 C9 -81.6(3) . . . . ?
N1 N2 C13 O1 169.5(3) . . . . ?
N1 N2 C13 C14 -13.0(4) . . . . ?
N1 C7 C8 C9 82.5(3) . . . . ?
N1 C7 C8 C10 22.1(2) . . . . ?
N1 C7 C8 C16 -118.6(3) . . . . ?
N2 N1 C7 C6 -159.1(2) . . . . ?
N2 N1 C7 C8 -33.9(2) . . . . ?
N2 N1 C12 C11 148.9(3) . . . . ?
N2 C13 C14 C15 -78.6(3) . . . . ?
C1 C2 C3 C4 0.5(5) . . . . ?
C1 C6 C7 N1 21.8(3) . . . . ?
C1 C6 C7 C8 -97.7(3) . . . . ?
C1 C11 C12 N1 -6.1(4) . . . . ?
C2 C1 C6 C5 -0.2(4) . . . . ?
C2 C1 C6 C7 178.1(2) . . . . ?
C2 C1 C11 C12 172.8(3) . . . . ?
C2 C3 C4 C5 0.3(5) . . . . ?
C3 C4 C5 Br1 -179.6(2) . . . . ?
C3 C4 C5 C6 -1.1(4) . . . . ?
C4 C5 C6 C1 1.0(4) . . . . ?
C4 C5 C6 C7 -177.2(2) . . . . ?
C5 C6 C7 N1 -160.0(2) . . . . ?
C5 C6 C7 C8 80.5(3) . . . . ?
C6 C1 C2 C3 -0.6(4) . . . . ?
C6 C1 C11 C12 -8.4(4) . . . . ?
C6 C7 C8 C9 -153.3(2) . . . . ?
C6 C7 C8 C10 146.3(2) . . . . ?
C6 C7 C8 C16 5.5(4) . . . . ?
C7 N1 N2 C10 34.0(3) . . . . ?
C7 N1 N2 C13 -114.0(3) . . . . ?
C7 N1 C12 C11 28.7(4) . . . . ?
C7 C8 C9 F1 21.1(4) . . . . ?
C7 C8 C9 F2 159.6(2) . . . . ?
C7 C8 C9 C10 -91.2(2) . . . . ?
C7 C8 C10 N2 -2.6(3) . . . . ?
C7 C8 C10 C9 109.1(2) . . . . ?
C7 C8 C16 C17 -99.2(3) . . . . ?
C7 C8 C16 C21 82.0(3) . . . . ?
C8 C9 C10 N2 93.3(2) . . . . ?
C8 C16 C17 C18 180.0(2) . . . . ?
C8 C16 C21 C20 179.6(2) . . . . ?
C9 C8 C10 N2 -111.7(3) . . . . ?
C9 C8 C16 C17 57.9(4) . . . . ?
C9 C8 C16 C21 -120.9(3) . . . . ?
C10 N2 C13 O1 24.7(4) . . . . ?
C10 N2 C13 C14 -157.9(3) . . . . ?
C10 C8 C9 F1 112.3(3) . . . . ?
C10 C8 C9 F2 -109.2(3) . . . . ?
C10 C8 C16 C17 127.0(3) . . . . ?
C10 C8 C16 C21 -51.9(3) . . . . ?
C11 C1 C2 C3 178.2(3) . . . . ?
C11 C1 C6 C5 -179.0(2) . . . . ?
C11 C1 C6 C7 -0.8(4) . . . . ?
C12 N1 N2 C10 -92.8(3) . . . . ?
C12 N1 N2 C13 119.3(3) . . . . ?
C12 N1 C7 C6 -34.8(3) . . . . ?
C12 N1 C7 C8 90.3(2) . . . . ?
C13 N2 C10 C8 129.5(3) . . . . ?
C13 N2 C10 C9 66.9(3) . . . . ?
C16 C8 C9 F1 -138.1(3) . . . . ?
C16 C8 C9 F2 0.4(4) . . . . ?
C16 C8 C9 C10 109.7(3) . . . . ?
C16 C8 C10 N2 138.7(2) . . . . ?
C16 C8 C10 C9 -109.6(3) . . . . ?
C16 C17 C18 C19 0.7(4) . . . . ?
C17 C16 C21 C20 0.7(4) . . . . ?
C17 C18 C19 C20 0.2(5) . . . . ?
C18 C19 C20 C21 -0.7(4) . . . . ?
C19 C20 C21 C16 0.2(4) . . . . ?
C21 C16 C17 C18 -1.1(4) . . . . ?

_olex2_date_sample_data_collection 2023-04-23
_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 1.219
_oxdiff_exptl_absorpt_empirical_full_min 0.784
####################################################################### 
# 
# 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_244
_database_code_depnum_ccdc_archive 'CCDC 2279971'
loop_
_audit_author_name
_audit_author_address
'Zhi Zhou'
;Guangzhou Medical University
China
;
_audit_update_record             
;
2023-07-07 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;
_audit_creation_date             2023-03-30
_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         'C17 H15 F N2 O2'
_chemical_formula_sum            'C17 H15 F N2 O2'
_chemical_formula_weight         298.31
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8203(5)
_cell_length_b                   9.1068(6)
_cell_length_c                   10.6468(6)
_cell_angle_alpha                67.050(6)
_cell_angle_beta                 88.220(4)
_cell_angle_gamma                71.172(5)
_cell_volume                     740.95(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3642
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.7350
_cell_measurement_theta_min      5.5820
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.807
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36697
_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            'light colourless'
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4658
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.778
_diffrn_reflns_theta_min         4.537
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      3.00  77.00   1.00    1.00    --   40.73 -99.00 -90.00   74
  2  ω     80.00 122.00   1.00    1.00    --  107.58-125.00 -30.00   42
  3  ω    100.00 126.00   1.00    1.00    --  107.58 -45.00  60.00   26
  4  ω     63.00 118.00   1.00    1.00    --  107.58 -61.00 150.00   55
  5  ω     51.00 108.00   1.00    1.00    --  107.58 -94.00 150.00   57
  6  ω     50.00  81.00   1.00    1.00    --   40.73-125.00  60.00   31
  7  ω     35.00  81.00   1.00    1.00    --  107.58 -45.00  60.00   46
  8  ω     27.00 106.00   1.00    1.00    --  107.58 -94.00  60.00   79
  9  ω     31.00  95.00   1.00    1.00    --  107.58 -30.00-120.00   64
 10  ω     83.00 173.00   1.00    1.00    --  107.58  30.00-180.00   90
 11  ω     93.00 167.00   1.00    1.00    --  107.58  45.00 -90.00   74
 12  ω    150.00 176.00   1.00    1.00    --  107.58 102.00  63.00   26
 13  ω    114.00 178.00   1.00    1.00    --  107.58 125.00 120.00   64
 14  ω     79.00 177.00   1.00    1.00    --  107.58  61.00-150.00   98
 15  ω      2.00  58.00   1.00    1.00    --   40.73 -99.00-180.00   56
 16  ω   -115.00 -16.00   1.00    1.00    --  -40.73 -37.00  30.00   99
 17  ω   -115.00 -17.00   1.00    1.00    --  -40.73 -37.00 -60.00   98
;
_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      0.0367046000
_diffrn_orient_matrix_UB_12      0.0874228000
_diffrn_orient_matrix_UB_13      -0.1478291000
_diffrn_orient_matrix_UB_21      -0.1684671000
_diffrn_orient_matrix_UB_22      0.1361700000
_diffrn_orient_matrix_UB_23      -0.0325529000
_diffrn_orient_matrix_UB_31      0.0687932000
_diffrn_orient_matrix_UB_32      0.1090937000
_diffrn_orient_matrix_UB_33      0.0455397000
_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                2684
_reflns_number_total             2887
_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         0.388
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       0.064(5)
_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   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2887
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0581
_refine_ls_restrained_S_all      1.082
_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)+(0.0971P)²+0.2843P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1552
_refine_ls_wR_factor_ref         0.1585
_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
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C6(H6), C14(H14), C15(H15), C16(H16), C17(H17)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.64793(12) 0.25794(13) 0.33836(10) 0.0315(3) Uani 1 1 d . . . . .
O1 O 0.29177(14) 0.56074(16) 0.35275(13) 0.0298(3) Uani 1 1 d . . . . .
O2 O 0.3782(3) 0.6931(2) -0.05154(15) 0.0640(6) Uani 1 1 d . . . . .
N1 N 0.37272(17) 0.3458(2) 0.68659(15) 0.0279(4) Uani 1 1 d . . . . .
N2 N 0.42065(18) 0.52196(18) 0.17137(14) 0.0257(4) Uani 1 1 d . . . . .
H2 H 0.490(3) 0.449(3) 0.144(2) 0.039(6) Uiso 1 1 d . . . . .
C1 C 0.64586(19) 0.0699(2) 0.62222(17) 0.0236(4) Uani 1 1 d . . . . .
C2 C 0.6112(2) -0.0614(2) 0.72672(19) 0.0295(4) Uani 1 1 d . . . . .
H2A H 0.504572 -0.053785 0.739376 0.035 Uiso 1 1 calc R U . . .
C3 C 0.7351(3) -0.2040(2) 0.8122(2) 0.0386(5) Uani 1 1 d . . . . .
H3 H 0.710994 -0.291852 0.881011 0.046 Uiso 1 1 calc R U . . .
C4 C 0.8943(3) -0.2156(3) 0.7954(2) 0.0415(5) Uani 1 1 d . . . . .
H4 H 0.977013 -0.311063 0.852738 0.050 Uiso 1 1 calc R U . . .
C5 C 0.9297(2) -0.0850(3) 0.6931(2) 0.0387(5) Uani 1 1 d . . . . .
H5 H 1.036539 -0.092304 0.682225 0.046 Uiso 1 1 calc R U . . .
C6 C 0.8068(2) 0.0570(2) 0.60650(18) 0.0292(4) Uani 1 1 d . . . . .
H6 H 0.831818 0.144131 0.537585 0.035 Uiso 1 1 calc R U . . .
C7 C 0.51229(18) 0.2242(2) 0.53383(16) 0.0219(4) Uani 1 1 d . . . . .
C8 C 0.51912(19) 0.3134(2) 0.40215(17) 0.0239(4) Uani 1 1 d . . . . .
C9 C 0.39868(19) 0.4780(2) 0.30903(17) 0.0232(4) Uani 1 1 d . . . . .
C10 C 0.3506(2) 0.6783(2) 0.06440(18) 0.0314(4) Uani 1 1 d . . . . .
C11 C 0.2503(2) 0.8260(2) 0.09321(18) 0.0296(4) Uani 1 1 d . . . . .
H11A H 0.308287 0.834379 0.164659 0.036 Uiso 1 1 calc R U . . .
H11B H 0.151539 0.807804 0.126723 0.036 Uiso 1 1 calc R U . . .
C12 C 0.2087(3) 0.9907(3) -0.0331(2) 0.0429(5) Uani 1 1 d . . . . .
H12A H 0.157609 0.980313 -0.106086 0.064 Uiso 1 1 calc R U . . .
H12B H 0.305438 1.015222 -0.060962 0.064 Uiso 1 1 calc R U . . .
H12C H 0.136731 1.080783 -0.012398 0.064 Uiso 1 1 calc R U . . .
C13 C 0.36177(19) 0.2776(2) 0.59811(16) 0.0217(4) Uani 1 1 d . . . . .
C14 C 0.2227(2) 0.2541(2) 0.56625(18) 0.0263(4) Uani 1 1 d . . . . .
H14 H 0.221582 0.201907 0.506795 0.032 Uiso 1 1 calc R U . . .
C15 C 0.0852(2) 0.3101(2) 0.62497(19) 0.0293(4) Uani 1 1 d . . . . .
H15 H -0.009962 0.295568 0.606151 0.035 Uiso 1 1 calc R U . . .
C16 C 0.0925(2) 0.3877(2) 0.71180(19) 0.0302(4) Uani 1 1 d . . . . .
H16 H 0.001361 0.430543 0.750010 0.036 Uiso 1 1 calc R U . . .
C17 C 0.2380(2) 0.4004(2) 0.74075(19) 0.0314(4) Uani 1 1 d . . . . .
H17 H 0.242698 0.449836 0.801558 0.038 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 C8 1.3625(18) . ?
O1 C9 1.209(2) . ?
O2 C10 1.214(2) . ?
N1 C13 1.335(2) . ?
N1 C17 1.339(2) . ?
N2 H2 0.88(3) . ?
N2 C9 1.386(2) . ?
N2 C10 1.385(2) . ?
C1 C2 1.393(2) . ?
C1 C6 1.397(2) . ?
C1 C7 1.489(2) . ?
C2 H2A 0.9300 . ?
C2 C3 1.390(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.387(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.329(2) . ?
C7 C13 1.501(2) . ?
C8 C9 1.496(2) . ?
C10 C11 1.491(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.515(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.385(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.387(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.379(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.379(3) . ?
C17 H17 0.9300 . ?

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
C13 N1 C17 116.71(14) . . ?
C9 N2 H2 120.5(15) . . ?
C10 N2 H2 112.2(16) . . ?
C10 N2 C9 127.13(15) . . ?
C2 C1 C6 118.85(16) . . ?
C2 C1 C7 119.93(15) . . ?
C6 C1 C7 121.16(15) . . ?
C1 C2 H2A 119.8 . . ?
C3 C2 C1 120.39(17) . . ?
C3 C2 H2A 119.8 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.25(19) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.73(18) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.41(18) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.36(18) . . ?
C5 C6 H6 119.8 . . ?
C1 C7 C13 117.35(13) . . ?
C8 C7 C1 123.47(14) . . ?
C8 C7 C13 119.17(14) . . ?
F1 C8 C9 112.57(13) . . ?
C7 C8 F1 120.10(15) . . ?
C7 C8 C9 127.32(15) . . ?
O1 C9 N2 124.57(15) . . ?
O1 C9 C8 121.69(15) . . ?
N2 C9 C8 113.73(14) . . ?
O2 C10 N2 118.52(17) . . ?
O2 C10 C11 121.29(17) . . ?
N2 C10 C11 120.12(15) . . ?
C10 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
C10 C11 C12 112.07(15) . . ?
H11A C11 H11B 107.9 . . ?
C12 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C7 115.91(14) . . ?
N1 C13 C14 123.54(15) . . ?
C14 C13 C7 120.55(14) . . ?
C13 C14 H14 120.7 . . ?
C13 C14 C15 118.54(15) . . ?
C15 C14 H14 120.7 . . ?
C14 C15 H15 120.7 . . ?
C16 C15 C14 118.63(15) . . ?
C16 C15 H15 120.7 . . ?
C15 C16 H16 120.7 . . ?
C15 C16 C17 118.53(16) . . ?
C17 C16 H16 120.7 . . ?
N1 C17 C16 123.95(16) . . ?
N1 C17 H17 118.0 . . ?
C16 C17 H17 118.0 . . ?

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
F1 C8 C9 O1 -167.00(14) . . . . ?
F1 C8 C9 N2 14.22(19) . . . . ?
O2 C10 C11 C12 -6.9(3) . . . . ?
N1 C13 C14 C15 2.6(3) . . . . ?
N2 C10 C11 C12 170.11(18) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C1 C7 C8 F1 5.2(2) . . . . ?
C1 C7 C8 C9 -173.69(14) . . . . ?
C1 C7 C13 N1 72.82(19) . . . . ?
C1 C7 C13 C14 -106.52(17) . . . . ?
C2 C1 C6 C5 0.5(3) . . . . ?
C2 C1 C7 C8 -146.99(17) . . . . ?
C2 C1 C7 C13 31.8(2) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C6 C1 C2 C3 -1.0(3) . . . . ?
C6 C1 C7 C8 35.9(2) . . . . ?
C6 C1 C7 C13 -145.33(15) . . . . ?
C7 C1 C2 C3 -178.24(15) . . . . ?
C7 C1 C6 C5 177.62(15) . . . . ?
C7 C8 C9 O1 11.9(3) . . . . ?
C7 C8 C9 N2 -166.85(16) . . . . ?
C7 C13 C14 C15 -178.09(15) . . . . ?
C8 C7 C13 N1 -108.33(18) . . . . ?
C8 C7 C13 C14 72.3(2) . . . . ?
C9 N2 C10 O2 -177.1(2) . . . . ?
C9 N2 C10 C11 5.9(3) . . . . ?
C10 N2 C9 O1 14.7(3) . . . . ?
C10 N2 C9 C8 -166.55(16) . . . . ?
C13 N1 C17 C16 1.0(3) . . . . ?
C13 C7 C8 F1 -173.60(13) . . . . ?
C13 C7 C8 C9 7.5(3) . . . . ?
C13 C14 C15 C16 0.4(3) . . . . ?
C14 C15 C16 C17 -2.5(3) . . . . ?
C15 C16 C17 N1 1.9(3) . . . . ?
C17 N1 C13 C7 177.42(15) . . . . ?
C17 N1 C13 C14 -3.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 11.768
_oxdiff_exptl_absorpt_empirical_full_min 0.530
####################################################################### 
# 
# 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_pdp-31
_database_code_depnum_ccdc_archive 'CCDC 2279973'
loop_
_audit_author_name
_audit_author_address
'Zhi Zhou'
;Guangzhou Medical University
China
;
_audit_update_record             
;
2023-07-07 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;
_audit_creation_date             2022-04-06
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H16 F2 N2 O'
_chemical_formula_sum            'C17 H16 F2 N2 O'
_chemical_formula_weight         302.32
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C272 H256 N32 O48 '
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      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   37.7194(4)
_cell_length_b                   16.9142(2)
_cell_length_c                   9.49011(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6054.64(13)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    8539
_cell_measurement_temperature    294.60(10)
_cell_measurement_theta_max      75.4790
_cell_measurement_theta_min      5.4500
_shelx_estimated_absorpt_T_max   0.928
_shelx_estimated_absorpt_T_min   0.898
_exptl_absorpt_coefficient_mu    0.842
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2528
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10107
_diffrn_reflns_point_group_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.506
_diffrn_reflns_theta_min         4.689
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.60(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     84.00 178.00   0.50    0.80    --  109.26  26.00   7.00  188
  2  ω     80.00 178.00   0.50    0.80    --  109.26  77.00-120.00  196
  3  ω     90.00 118.00   0.50    0.80    --  109.26  30.00-180.00   56
  4  ω    125.00 177.00   0.50    0.80    --  109.26  30.00-180.00  104
  5  ω    -27.00  38.00   0.50    0.27    --  -43.18  19.00 120.00  130
  6  ω    -51.00 -14.00   0.50    0.80    --  -90.25  45.00 120.00   74
  7  ω    -51.00 -14.00   0.50    0.80    --  -90.25  45.00   0.00   74
  8  ω    -51.00 -14.00   0.50    0.80    --  -90.25  45.00  30.00   74
  9  ω    -32.00  36.00   0.50    0.27    --  -43.18  26.00   7.00  136
 10  ω     58.00  94.00   0.50    0.80    --  109.26-103.00  91.00   72
 11  ω     36.00 105.00   0.50    0.80    --  109.26 -94.00  30.00  138
 12  ω    -86.00 -13.00   0.50    0.27    --  -43.18 125.00-180.00  146
 13  ω    -81.00 -15.00   0.50    0.80    --  -90.25 103.00-166.00  132
 14  ω    -82.00 -15.00   0.50    0.80    --  -90.25 112.00  95.00  134
 15  ω    -36.00  32.00   0.50    0.27    --   43.18 -26.00-156.00  136
 16  ω     35.00 106.00   0.50    0.80    --  109.26 -77.00-180.00  142
 17  ω     35.00  71.00   0.50    0.80    --  109.26 -61.00 -90.00   72
 18  ω     35.00  71.00   0.50    0.80    --  109.26 -61.00 -30.00   72
 19  ω     35.00 106.00   0.50    0.80    --  109.26 -77.00 120.00  142
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0039474000
_diffrn_orient_matrix_UB_12      -0.0584249000
_diffrn_orient_matrix_UB_13      -0.1235441000
_diffrn_orient_matrix_UB_21      -0.0137158000
_diffrn_orient_matrix_UB_22      -0.0674732000
_diffrn_orient_matrix_UB_23      0.0943938000
_diffrn_orient_matrix_UB_31      -0.0382741000
_diffrn_orient_matrix_UB_32      0.0181410000
_diffrn_orient_matrix_UB_33      -0.0466123000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.749
_reflns_Friedel_fraction_full    0.887
_reflns_Friedel_fraction_max     0.835
_reflns_number_gt                2752
_reflns_number_total             2875
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 
;
 Flack x determined using 1133 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2875
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0323
_refine_ls_restrained_S_all      1.051
_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)+(0.0554P)²+1.3038P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0871
_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
2.a Ternary CH refined with riding coordinates:
 C8(H8), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_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 0.55008(5) 0.55311(9) 0.81458(16) 0.0768(5) Uani 1 1 d . . . . .
F2 F 0.57846(4) 0.66085(8) 0.75873(17) 0.0675(4) Uani 1 1 d . . . . .
O1 O 0.50994(4) 0.75390(9) 0.6475(2) 0.0581(4) Uani 1 1 d . . . . .
N1 N 0.56935(4) 0.66830(9) 0.40262(18) 0.0412(3) Uani 1 1 d . . . . .
N2 N 0.54113(4) 0.67846(9) 0.50071(19) 0.0435(4) Uani 1 1 d . . . . .
C1 C 0.57138(5) 0.47337(11) 0.5520(2) 0.0415(4) Uani 1 1 d . . . . .
C2 C 0.59114(6) 0.42526(13) 0.6397(3) 0.0561(5) Uani 1 1 d . . . . .
H2 H 0.603852 0.447274 0.713931 0.067 Uiso 1 1 calc R U . . .
C3 C 0.59206(8) 0.34402(14) 0.6173(3) 0.0668(7) Uani 1 1 d . . . . .
H3 H 0.605423 0.311886 0.676482 0.080 Uiso 1 1 calc R U . . .
C4 C 0.57321(7) 0.31099(13) 0.5074(3) 0.0627(6) Uani 1 1 d . . . . .
H4 H 0.573895 0.256655 0.492680 0.075 Uiso 1 1 calc R U . . .
C5 C 0.55354(7) 0.35807(14) 0.4203(3) 0.0607(6) Uani 1 1 d . . . . .
H5 H 0.540734 0.335724 0.346676 0.073 Uiso 1 1 calc R U . . .
C6 C 0.55266(6) 0.43945(12) 0.4418(2) 0.0504(5) Uani 1 1 d . . . . .
H6 H 0.539418 0.471320 0.381788 0.060 Uiso 1 1 calc R U . . .
C7 C 0.57108(5) 0.56114(10) 0.5713(2) 0.0399(4) Uani 1 1 d . . . . .
C8 C 0.53655(5) 0.60837(10) 0.5854(2) 0.0434(4) Uani 1 1 d . . . . .
H8 H 0.513752 0.580563 0.584395 0.052 Uiso 1 1 calc R U . . .
C9 C 0.56058(6) 0.59856(11) 0.7061(2) 0.0508(5) Uani 1 1 d . . . . .
C10 C 0.59483(5) 0.61566(11) 0.4758(2) 0.0409(4) Uani 1 1 d . . . . .
H10 H 0.609920 0.648059 0.536850 0.049 Uiso 1 1 calc R U . . .
C11 C 0.61803(5) 0.57164(12) 0.3747(3) 0.0520(5) Uani 1 1 d . . . . .
H11 H 0.638992 0.549257 0.407426 0.062 Uiso 1 1 calc R U . . .
C12 C 0.60957(6) 0.56370(13) 0.2407(3) 0.0582(6) Uani 1 1 d . . . . .
H12 H 0.624536 0.535852 0.180695 0.070 Uiso 1 1 calc R U . . .
C13 C 0.57728(7) 0.59786(14) 0.1862(3) 0.0594(6) Uani 1 1 d . . . . .
H13 H 0.570141 0.587244 0.094347 0.071 Uiso 1 1 calc R U . . .
C14 C 0.55776(5) 0.64469(12) 0.2683(2) 0.0494(5) Uani 1 1 d . . . . .
H14 H 0.535872 0.662225 0.235814 0.059 Uiso 1 1 calc R U . . .
C15 C 0.52882(5) 0.75063(11) 0.5432(2) 0.0437(4) Uani 1 1 d . . . . .
C16 C 0.53769(6) 0.82014(12) 0.4514(3) 0.0560(5) Uani 1 1 d . . . . .
H16A H 0.562957 0.819999 0.432377 0.067 Uiso 1 1 calc R U . . .
H16B H 0.525430 0.814626 0.362129 0.067 Uiso 1 1 calc R U . . .
C17 C 0.52777(12) 0.89747(16) 0.5164(5) 0.1013(13) Uani 1 1 d . . . . .
H17A H 0.530306 0.938826 0.447847 0.152 Uiso 1 1 calc R U . . .
H17B H 0.543017 0.907974 0.595196 0.152 Uiso 1 1 calc R U . . .
H17C H 0.503601 0.895325 0.547903 0.152 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 C9 1.345(3) . ?
F2 C9 1.347(2) . ?
O1 C15 1.221(3) . ?
N1 N2 1.425(2) . ?
N1 C10 1.483(2) . ?
N1 C14 1.405(3) . ?
N2 C8 1.443(2) . ?
N2 C15 1.367(2) . ?
C1 C2 1.382(3) . ?
C1 C6 1.386(3) . ?
C1 C7 1.496(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.391(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.380(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.367(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.392(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.534(3) . ?
C7 C9 1.481(3) . ?
C7 C10 1.573(3) . ?
C8 H8 0.9800 . ?
C8 C9 1.470(3) . ?
C10 H10 0.9800 . ?
C10 C11 1.496(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.318(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.444(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.333(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.501(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.494(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C10 104.53(14) . . ?
C14 N1 N2 113.24(15) . . ?
C14 N1 C10 117.10(15) . . ?
N1 N2 C8 110.76(14) . . ?
C15 N2 N1 123.66(15) . . ?
C15 N2 C8 121.94(17) . . ?
C2 C1 C6 119.03(18) . . ?
C2 C1 C7 120.98(18) . . ?
C6 C1 C7 119.96(17) . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.2(2) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.0(2) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 120.5(2) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C1 C7 C8 122.27(15) . . ?
C1 C7 C10 120.46(16) . . ?
C8 C7 C10 103.20(14) . . ?
C9 C7 C1 122.14(17) . . ?
C9 C7 C8 58.34(14) . . ?
C9 C7 C10 113.55(15) . . ?
N2 C8 C7 106.13(14) . . ?
N2 C8 H8 119.6 . . ?
N2 C8 C9 116.92(16) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 59.02(13) . . ?
C9 C8 H8 119.6 . . ?
F1 C9 F2 108.09(18) . . ?
F1 C9 C7 119.72(17) . . ?
F1 C9 C8 118.66(19) . . ?
F2 C9 C7 121.38(19) . . ?
F2 C9 C8 120.63(17) . . ?
C8 C9 C7 62.64(13) . . ?
N1 C10 C7 104.65(14) . . ?
N1 C10 H10 108.5 . . ?
N1 C10 C11 112.20(17) . . ?
C7 C10 H10 108.5 . . ?
C11 C10 C7 114.24(15) . . ?
C11 C10 H10 108.5 . . ?
C10 C11 H11 119.1 . . ?
C12 C11 C10 121.83(19) . . ?
C12 C11 H11 119.1 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.6(2) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.6(2) . . ?
C14 C13 H13 120.2 . . ?
N1 C14 H14 119.1 . . ?
C13 C14 N1 121.82(19) . . ?
C13 C14 H14 119.1 . . ?
O1 C15 N2 118.54(18) . . ?
O1 C15 C16 124.40(18) . . ?
N2 C15 C16 116.94(18) . . ?
C15 C16 H16A 109.0 . . ?
C15 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C17 C16 C15 113.0(2) . . ?
C17 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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 C15 C16 C17 12.5(4) . . . . ?
N1 N2 C8 C7 18.3(2) . . . . ?
N1 N2 C8 C9 81.3(2) . . . . ?
N1 N2 C15 O1 -165.07(18) . . . . ?
N1 N2 C15 C16 18.9(3) . . . . ?
N1 C10 C11 C12 -18.3(3) . . . . ?
N2 N1 C10 C7 31.94(18) . . . . ?
N2 N1 C10 C11 156.34(15) . . . . ?
N2 N1 C14 C13 -147.5(2) . . . . ?
N2 C8 C9 F1 155.96(17) . . . . ?
N2 C8 C9 F2 18.7(3) . . . . ?
N2 C8 C9 C7 -93.35(17) . . . . ?
N2 C15 C16 C17 -171.6(3) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C1 C7 C8 N2 -137.43(18) . . . . ?
C1 C7 C8 C9 110.5(2) . . . . ?
C1 C7 C9 F1 -1.6(3) . . . . ?
C1 C7 C9 F2 138.44(19) . . . . ?
C1 C7 C9 C8 -110.69(19) . . . . ?
C1 C7 C10 N1 119.87(18) . . . . ?
C1 C7 C10 C11 -3.2(3) . . . . ?
C2 C1 C6 C5 0.5(3) . . . . ?
C2 C1 C7 C8 -127.1(2) . . . . ?
C2 C1 C7 C9 -56.8(3) . . . . ?
C2 C1 C7 C10 99.7(2) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
C4 C5 C6 C1 -0.6(4) . . . . ?
C6 C1 C2 C3 -0.1(3) . . . . ?
C6 C1 C7 C8 55.2(3) . . . . ?
C6 C1 C7 C9 125.6(2) . . . . ?
C6 C1 C7 C10 -78.0(2) . . . . ?
C7 C1 C2 C3 -177.8(2) . . . . ?
C7 C1 C6 C5 178.2(2) . . . . ?
C7 C8 C9 F1 -110.7(2) . . . . ?
C7 C8 C9 F2 112.0(2) . . . . ?
C7 C10 C11 C12 100.6(2) . . . . ?
C8 N2 C15 O1 -8.6(3) . . . . ?
C8 N2 C15 C16 175.35(19) . . . . ?
C8 C7 C9 F1 109.0(2) . . . . ?
C8 C7 C9 F2 -110.9(2) . . . . ?
C8 C7 C10 N1 -20.85(19) . . . . ?
C8 C7 C10 C11 -143.94(18) . . . . ?
C9 C7 C8 N2 112.09(18) . . . . ?
C9 C7 C10 N1 -81.8(2) . . . . ?
C9 C7 C10 C11 155.13(19) . . . . ?
C10 N1 N2 C8 -32.3(2) . . . . ?
C10 N1 N2 C15 126.5(2) . . . . ?
C10 N1 C14 C13 -25.7(3) . . . . ?
C10 C7 C8 N2 2.4(2) . . . . ?
C10 C7 C8 C9 -109.72(17) . . . . ?
C10 C7 C9 F1 -159.58(19) . . . . ?
C10 C7 C9 F2 -19.5(3) . . . . ?
C10 C7 C9 C8 91.37(17) . . . . ?
C10 C11 C12 C13 0.2(4) . . . . ?
C11 C12 C13 C14 7.1(4) . . . . ?
C12 C13 C14 N1 6.3(4) . . . . ?
C14 N1 N2 C8 96.31(19) . . . . ?
C14 N1 N2 C15 -104.9(2) . . . . ?
C14 N1 C10 C7 -94.25(19) . . . . ?
C14 N1 C10 C11 30.1(2) . . . . ?
C15 N2 C8 C7 -140.86(18) . . . . ?
C15 N2 C8 C9 -77.9(2) . . . . ?

_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 1.515
_oxdiff_exptl_absorpt_empirical_full_min 0.579
####################################################################### 
# 
# 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_429
_database_code_depnum_ccdc_archive 'CCDC 2279972'
loop_
_audit_author_name
_audit_author_address
'Zhi Zhou'
;Guangzhou Medical University
China
;
_audit_update_record             
;
2023-07-07 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;
_audit_creation_date             2023-04-27
_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         'C24 H21 F N2 O3 S'
_chemical_formula_sum            'C24 H21 F N2 O3 S'
_chemical_formula_weight         436.49
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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                   11.0253(12)
_cell_length_b                   19.0234(19)
_cell_length_c                   11.0800(13)
_cell_angle_alpha                90
_cell_angle_beta                 117.375(15)
_cell_angle_gamma                90
_cell_volume                     2063.7(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5453
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.2470
_cell_measurement_theta_min      2.3110
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22970
_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            'light colourless'
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11871
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.080
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -37.00  65.00   1.00    5.00    --  -11.27  77.00   0.00  102
  2  ω     30.00  57.00   1.00    5.00    --  -11.27  77.00-120.00   27
  3  ω    -15.00  88.00   1.00    5.00    --   11.90  77.00 -90.00  103
  4  ω    -20.00   5.00   1.00    5.00    --   11.90  77.00 150.00   25
;
_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      -0.0356248000
_diffrn_orient_matrix_UB_12      0.0107812000
_diffrn_orient_matrix_UB_13      -0.0688920000
_diffrn_orient_matrix_UB_21      0.0130173000
_diffrn_orient_matrix_UB_22      -0.0331612000
_diffrn_orient_matrix_UB_23      -0.0209462000
_diffrn_orient_matrix_UB_31      -0.0616940000
_diffrn_orient_matrix_UB_32      -0.0132166000
_diffrn_orient_matrix_UB_33      -0.0035454000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3111
_reflns_number_total             3564
_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  (Sheldrick, 2015)'
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3564
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0422
_refine_ls_restrained_S_all      1.073
_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)+(0.0433P)²+1.1412P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.1036
_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
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13),
 C14(H14), C19(H19), C20(H20), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C24(H24A,H24B,H24C)
;
_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
S1 S 0.92247(5) 0.42226(3) 0.78539(5) 0.01952(15) Uani 1 1 d . . . . .
F1 F 0.52280(11) 0.43514(6) 0.60004(11) 0.0256(3) Uani 1 1 d . . . . .
O1 O 0.86184(14) 0.57085(7) 0.80204(15) 0.0264(4) Uani 1 1 d . . . . .
O2 O 0.91569(14) 0.34882(7) 0.80737(14) 0.0260(4) Uani 1 1 d . . . . .
O3 O 1.04752(13) 0.45913(8) 0.85765(14) 0.0273(4) Uani 1 1 d . . . . .
N1 N 0.71558(15) 0.37210(8) 0.93001(15) 0.0165(4) Uani 1 1 d . . . . .
N2 N 0.80541(15) 0.45823(8) 0.82815(16) 0.0177(4) Uani 1 1 d . . . . .
C1 C 0.35793(19) 0.33144(9) 0.67986(19) 0.0171(4) Uani 1 1 d . . . . .
C2 C 0.3020(2) 0.32479(10) 0.5389(2) 0.0224(5) Uani 1 1 d . . . . .
H2 H 0.357500 0.333353 0.495489 0.027 Uiso 1 1 calc R U . . .
C3 C 0.1666(2) 0.30587(11) 0.4617(2) 0.0269(5) Uani 1 1 d . . . . .
H3 H 0.129806 0.301628 0.365835 0.032 Uiso 1 1 calc R U . . .
C4 C 0.0846(2) 0.29312(11) 0.5234(2) 0.0290(5) Uani 1 1 d . . . . .
H4 H -0.007949 0.279463 0.470424 0.035 Uiso 1 1 calc R U . . .
C5 C 0.1381(2) 0.30034(11) 0.6625(2) 0.0261(5) Uani 1 1 d . . . . .
H5 H 0.081792 0.292162 0.705183 0.031 Uiso 1 1 calc R U . . .
C6 C 0.2738(2) 0.31951(10) 0.7404(2) 0.0209(5) Uani 1 1 d . . . . .
H6 H 0.309482 0.324520 0.836025 0.025 Uiso 1 1 calc R U . . .
C7 C 0.50103(19) 0.35417(10) 0.75952(19) 0.0167(4) Uani 1 1 d . . . . .
C8 C 0.57289(19) 0.40122(10) 0.72012(19) 0.0172(4) Uani 1 1 d . . . . .
C9 C 0.70210(19) 0.41322(10) 0.82173(19) 0.0171(4) Uani 1 1 d . . . . .
C10 C 0.59301(19) 0.33561(10) 0.89323(19) 0.0168(4) Uani 1 1 d . . . . .
C11 C 0.5878(2) 0.28957(10) 0.9909(2) 0.0206(5) Uani 1 1 d . . . . .
H11 H 0.507071 0.263374 0.969448 0.025 Uiso 1 1 calc R U . . .
C12 C 0.6974(2) 0.28257(11) 1.1151(2) 0.0240(5) Uani 1 1 d . . . . .
H12 H 0.692782 0.251999 1.180668 0.029 Uiso 1 1 calc R U . . .
C13 C 0.8186(2) 0.32072(11) 1.1472(2) 0.0249(5) Uani 1 1 d . . . . .
H13 H 0.894706 0.315666 1.234426 0.030 Uiso 1 1 calc R U . . .
C14 C 0.8273(2) 0.36423(11) 1.0552(2) 0.0219(5) Uani 1 1 d . . . . .
H14 H 0.909435 0.389072 1.076598 0.026 Uiso 1 1 calc R U . . .
C15 C 0.78909(19) 0.53254(10) 0.82605(19) 0.0195(4) Uani 1 1 d . . . . .
C16 C 0.6747(2) 0.55779(11) 0.8533(2) 0.0226(5) Uani 1 1 d . . . . .
H16A H 0.679613 0.533249 0.934232 0.027 Uiso 1 1 calc R U . . .
H16B H 0.586148 0.545760 0.774870 0.027 Uiso 1 1 calc R U . . .
C17 C 0.6810(2) 0.63630(12) 0.8771(3) 0.0369(6) Uani 1 1 d . . . . .
H17A H 0.675643 0.660798 0.796931 0.055 Uiso 1 1 calc R U . . .
H17B H 0.767256 0.648232 0.956503 0.055 Uiso 1 1 calc R U . . .
H17C H 0.604362 0.650729 0.893139 0.055 Uiso 1 1 calc R U . . .
C18 C 0.85362(19) 0.43833(10) 0.6104(2) 0.0194(4) Uani 1 1 d . . . . .
C19 C 0.8810(2) 0.50082(11) 0.5641(2) 0.0211(5) Uani 1 1 d . . . . .
H19 H 0.940757 0.534502 0.626320 0.025 Uiso 1 1 calc R U . . .
C20 C 0.8202(2) 0.51356(11) 0.4260(2) 0.0230(5) Uani 1 1 d . . . . .
H20 H 0.839137 0.556283 0.393559 0.028 Uiso 1 1 calc R U . . .
C21 C 0.7318(2) 0.46499(11) 0.3336(2) 0.0223(5) Uani 1 1 d . . . . .
C22 C 0.7070(2) 0.40233(11) 0.3828(2) 0.0266(5) Uani 1 1 d . . . . .
H22 H 0.647593 0.368514 0.320573 0.032 Uiso 1 1 calc R U . . .
C23 C 0.7671(2) 0.38832(11) 0.5203(2) 0.0247(5) Uani 1 1 d . . . . .
H23 H 0.749734 0.345250 0.552972 0.030 Uiso 1 1 calc R U . . .
C24 C 0.6662(2) 0.48117(12) 0.1839(2) 0.0285(5) Uani 1 1 d . . . . .
H24A H 0.615764 0.439852 0.132454 0.043 Uiso 1 1 calc R U . . .
H24B H 0.737022 0.493380 0.157368 0.043 Uiso 1 1 calc R U . . .
H24C H 0.603166 0.520810 0.164338 0.043 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
S1 O2 1.4260(15) . ?
S1 O3 1.4207(15) . ?
S1 N2 1.7089(17) . ?
S1 C18 1.754(2) . ?
F1 C8 1.348(2) . ?
O1 C15 1.201(2) . ?
N1 C9 1.382(2) . ?
N1 C10 1.403(2) . ?
N1 C14 1.375(2) . ?
N2 C9 1.400(2) . ?
N2 C15 1.424(3) . ?
C1 C2 1.397(3) . ?
C1 C6 1.391(3) . ?
C1 C7 1.475(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.384(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.381(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.392(3) . ?
C7 C10 1.402(3) . ?
C8 C9 1.369(3) . ?
C10 C11 1.414(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.358(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.414(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.350(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.505(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.513(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.382(3) . ?
C18 C23 1.391(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.380(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.391(3) . ?
C21 C22 1.389(3) . ?
C21 C24 1.505(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.380(3) . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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
O2 S1 N2 103.85(9) . . ?
O2 S1 C18 109.24(9) . . ?
O3 S1 O2 120.06(9) . . ?
O3 S1 N2 107.88(9) . . ?
O3 S1 C18 110.58(9) . . ?
N2 S1 C18 103.80(9) . . ?
C9 N1 C10 108.86(15) . . ?
C14 N1 C9 128.76(17) . . ?
C14 N1 C10 122.37(17) . . ?
C9 N2 S1 116.20(13) . . ?
C9 N2 C15 120.83(16) . . ?
C15 N2 S1 119.92(14) . . ?
C2 C1 C7 119.78(19) . . ?
C6 C1 C2 118.38(18) . . ?
C6 C1 C7 121.76(17) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.60(19) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.3(2) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 H6 119.7 . . ?
C5 C6 C1 120.66(19) . . ?
C5 C6 H6 119.7 . . ?
C8 C7 C1 127.41(17) . . ?
C8 C7 C10 104.70(16) . . ?
C10 C7 C1 127.85(18) . . ?
F1 C8 C7 125.71(16) . . ?
F1 C8 C9 122.08(18) . . ?
C9 C8 C7 112.11(17) . . ?
N1 C9 N2 122.81(16) . . ?
C8 C9 N1 105.99(17) . . ?
C8 C9 N2 131.16(18) . . ?
N1 C10 C11 117.20(16) . . ?
C7 C10 N1 108.33(17) . . ?
C7 C10 C11 134.46(18) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.41(19) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.1(2) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.79(18) . . ?
C14 C13 H13 119.6 . . ?
N1 C14 H14 120.4 . . ?
C13 C14 N1 119.10(18) . . ?
C13 C14 H14 120.4 . . ?
O1 C15 N2 120.94(19) . . ?
O1 C15 C16 123.90(19) . . ?
N2 C15 C16 115.15(17) . . ?
C15 C16 H16A 109.2 . . ?
C15 C16 H16B 109.2 . . ?
C15 C16 C17 111.97(18) . . ?
H16A C16 H16B 107.9 . . ?
C17 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 S1 120.20(15) . . ?
C19 C18 C23 121.11(19) . . ?
C23 C18 S1 118.64(16) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 C18 119.01(19) . . ?
C20 C19 H19 120.5 . . ?
C19 C20 H20 119.4 . . ?
C19 C20 C21 121.2(2) . . ?
C21 C20 H20 119.4 . . ?
C20 C21 C24 119.65(19) . . ?
C22 C21 C20 118.61(19) . . ?
C22 C21 C24 121.74(19) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 C21 121.18(19) . . ?
C23 C22 H22 119.4 . . ?
C18 C23 H23 120.6 . . ?
C22 C23 C18 118.9(2) . . ?
C22 C23 H23 120.6 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
S1 N2 C9 N1 88.6(2) . . . . ?
S1 N2 C9 C8 -94.1(2) . . . . ?
S1 N2 C15 O1 -4.2(2) . . . . ?
S1 N2 C15 C16 174.75(13) . . . . ?
S1 C18 C19 C20 -176.89(15) . . . . ?
S1 C18 C23 C22 176.64(16) . . . . ?
F1 C8 C9 N1 177.43(16) . . . . ?
F1 C8 C9 N2 -0.3(3) . . . . ?
O1 C15 C16 C17 -12.4(3) . . . . ?
O2 S1 N2 C9 -23.11(15) . . . . ?
O2 S1 N2 C15 176.48(14) . . . . ?
O2 S1 C18 C19 -162.42(16) . . . . ?
O2 S1 C18 C23 20.14(19) . . . . ?
O3 S1 N2 C9 -151.54(14) . . . . ?
O3 S1 N2 C15 48.05(16) . . . . ?
O3 S1 C18 C19 -28.18(19) . . . . ?
O3 S1 C18 C23 154.38(16) . . . . ?
N1 C10 C11 C12 0.9(3) . . . . ?
N2 S1 C18 C19 87.29(17) . . . . ?
N2 S1 C18 C23 -90.15(17) . . . . ?
N2 C15 C16 C17 168.66(18) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C1 C7 C8 F1 0.4(3) . . . . ?
C1 C7 C8 C9 176.89(19) . . . . ?
C1 C7 C10 N1 -177.19(18) . . . . ?
C1 C7 C10 C11 4.0(4) . . . . ?
C2 C1 C6 C5 1.0(3) . . . . ?
C2 C1 C7 C8 33.9(3) . . . . ?
C2 C1 C7 C10 -148.9(2) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
C6 C1 C2 C3 -0.9(3) . . . . ?
C6 C1 C7 C8 -142.9(2) . . . . ?
C6 C1 C7 C10 34.3(3) . . . . ?
C7 C1 C2 C3 -177.77(18) . . . . ?
C7 C1 C6 C5 177.89(18) . . . . ?
C7 C8 C9 N1 0.8(2) . . . . ?
C7 C8 C9 N2 -176.9(2) . . . . ?
C7 C10 C11 C12 179.6(2) . . . . ?
C8 C7 C10 N1 0.5(2) . . . . ?
C8 C7 C10 C11 -178.3(2) . . . . ?
C9 N1 C10 C7 0.0(2) . . . . ?
C9 N1 C10 C11 179.01(17) . . . . ?
C9 N1 C14 C13 -179.82(19) . . . . ?
C9 N2 C15 O1 -163.75(18) . . . . ?
C9 N2 C15 C16 15.3(3) . . . . ?
C10 N1 C9 N2 177.48(17) . . . . ?
C10 N1 C9 C8 -0.5(2) . . . . ?
C10 N1 C14 C13 -1.1(3) . . . . ?
C10 C7 C8 F1 -177.29(18) . . . . ?
C10 C7 C8 C9 -0.8(2) . . . . ?
C10 C11 C12 C13 -0.8(3) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C12 C13 C14 N1 1.2(3) . . . . ?
C14 N1 C9 N2 -3.6(3) . . . . ?
C14 N1 C9 C8 178.43(18) . . . . ?
C14 N1 C10 C7 -178.98(17) . . . . ?
C14 N1 C10 C11 0.0(3) . . . . ?
C15 N2 C9 N1 -111.2(2) . . . . ?
C15 N2 C9 C8 66.2(3) . . . . ?
C18 S1 N2 C9 91.10(15) . . . . ?
C18 S1 N2 C15 -69.32(16) . . . . ?
C18 C19 C20 C21 0.4(3) . . . . ?
C19 C18 C23 C22 -0.8(3) . . . . ?
C19 C20 C21 C22 -1.0(3) . . . . ?
C19 C20 C21 C24 179.27(18) . . . . ?
C20 C21 C22 C23 0.7(3) . . . . ?
C21 C22 C23 C18 0.2(3) . . . . ?
C23 C18 C19 C20 0.5(3) . . . . ?
C24 C21 C22 C23 -179.6(2) . . . . ?

_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 2.334
_oxdiff_exptl_absorpt_empirical_full_min 0.445
