# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2025

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

data_exp_7897_auto
_database_code_depnum_ccdc_archive 'CCDC 2445379'
loop_
_audit_author_name
_audit_author_address
'Lin Wei'
;WuYi University
China
;
_audit_update_record             
;
2025-04-21 deposited with the CCDC.	2025-10-21 downloaded from the CCDC.
;
_audit_creation_date             2025-04-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
3-(1-fluoro-2-(naphthalen-2-yl)-2-oxoethyl)-2-methoxy-3,4-dihydroisoquinolin-1(2H)-one
_chemical_formula_moiety         'C22 H18 F N O3'
_chemical_formula_sum            'C22 H18 F N O3'
_chemical_formula_weight         363.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.0201(3)
_cell_length_b                   7.3436(2)
_cell_length_c                   21.6386(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.376(2)
_cell_angle_gamma                90
_cell_volume                     1746.05(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6370
_cell_measurement_temperature    213(20)
_cell_measurement_theta_max      77.3430
_cell_measurement_theta_min      4.3440
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.853
_exptl_absorpt_coefficient_mu    0.818
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             760
_exptl_crystal_preparation       no
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            11495
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.632
_diffrn_reflns_theta_min         4.098
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      213(20)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     59.00  98.00   0.50    1.34    --  108.07 -99.00  90.00   78
  2  ω     76.00 102.00   0.50    1.34    --  108.07 -99.00  60.00   52
  3  ω     48.00 106.00   0.50    1.34    --  108.07 -99.00   0.00  116
  4  ω     57.00 102.00   0.50    1.34    --  108.07 -99.00-120.00   90
  5  ω     58.00  83.00   0.50    1.34    --  108.07 -77.00-150.00   50
  6  ω     38.00  65.00   0.50    1.34    --  108.07 -57.00-120.00   54
  7  ω     38.00  63.00   0.50    1.34    --  108.07 -57.00 -60.00   50
  8  ω     36.00  64.00   0.50    1.34    --  108.07 -57.00 -90.00   56
  9  ω     36.00  66.00   0.50    1.34    --  108.07 -57.00  30.00   60
 10  ω     36.00  62.00   0.50    1.34    --  108.07 -57.00  90.00   52
 11  ω     40.00  66.00   0.50    1.34    --  108.07 -57.00 120.00   52
 12  ω     37.00  65.00   0.50    1.34    --  108.07 -57.00 150.00   56
 13  ω    -11.00  26.00   0.50    0.34    --   50.36 -18.00 105.00   74
 14  ω     -2.00  26.00   0.50    0.34    --   50.36 -19.00   0.00   56
 15  ω     83.00 108.00   0.50    0.34    --   50.36  18.00 -86.00   50
 16  ω    107.00 178.00   0.50    1.34    --  108.07  38.00-180.00  142
 17  ω    101.00 169.00   0.50    1.34    --  108.07  18.00 -86.00  136
 18  ω    -50.00 -19.00   0.50    1.34    --  -90.00  57.00-180.00   62
 19  ω    -53.00 -18.00   0.50    1.34    --  -90.00  57.00-120.00   70
 20  ω    -24.00  23.00   0.50    0.34    --  -50.36  18.00 -86.00   94
 21  ω    -26.00  21.00   0.50    0.34    --  -50.36  19.00 -30.00   94
 22  ω    -24.00  13.00   0.50    0.34    --  -50.36  19.00  60.00   74
 23  ω   -105.00 -43.00   0.50    0.34    --  -50.36 -18.00 105.00  124
 24  ω   -134.00 -90.00   0.50    1.34    --  -90.00 -18.00 105.00   88
 25  ω    -71.00 -31.00   0.50    1.34    --  -90.00 125.00 -30.00   80
 26  ω   -109.00 -84.00   0.50    1.34    --  -90.00 -38.00-150.00   50
;
_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      -0.1140603000
_diffrn_orient_matrix_UB_12      0.0517496000
_diffrn_orient_matrix_UB_13      0.0330809000
_diffrn_orient_matrix_UB_21      0.0774095000
_diffrn_orient_matrix_UB_22      0.0088239000
_diffrn_orient_matrix_UB_23      0.0622751000
_diffrn_orient_matrix_UB_31      0.0256435000
_diffrn_orient_matrix_UB_32      0.2031313000
_diffrn_orient_matrix_UB_33      -0.0111404000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2967
_reflns_number_total             3518
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3518
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      1.053
_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)+(0.0559P)²+0.4179P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1090
_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:
 C9(H9), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C3(H3), C21(H21), C22(H22), C6(H6), C5(H5), C16(H16), C4(H4),
 C19(H19), C18(H18), C17(H17)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.91861(7) 0.15361(12) 0.38752(4) 0.0407(2) Uani 1 1 d . . . . .
O2 O 0.65614(8) 0.27442(13) 0.26942(4) 0.0330(2) Uani 1 1 d . . . . .
O1 O 0.82929(9) 0.31834(15) 0.19075(4) 0.0388(3) Uani 1 1 d . . . . .
O3 O 0.85737(9) 0.26969(17) 0.49588(5) 0.0451(3) Uani 1 1 d . . . . .
N1 N 0.76617(10) 0.36314(17) 0.28683(5) 0.0314(3) Uani 1 1 d . . . . .
C2 C 0.97542(12) 0.42150(18) 0.27031(6) 0.0288(3) Uani 1 1 d . . . . .
C1 C 0.85200(12) 0.36299(18) 0.24512(6) 0.0293(3) Uani 1 1 d . . . . .
C13 C 0.64421(12) 0.24595(19) 0.47267(6) 0.0303(3) Uani 1 1 d . . . . .
C7 C 0.99461(12) 0.49635(19) 0.32949(6) 0.0299(3) Uani 1 1 d . . . . .
C9 C 0.78380(12) 0.39432(19) 0.35347(6) 0.0289(3) Uani 1 1 d . . . . .
H9 H 0.708745 0.452755 0.366278 0.035 Uiso 1 1 calc R U . . .
C15 C 0.42763(12) 0.20322(19) 0.44692(6) 0.0320(3) Uani 1 1 d . . . . .
C11 C 0.79935(12) 0.2148(2) 0.38946(6) 0.0314(3) Uani 1 1 d . . . . .
H11 H 0.742501 0.122551 0.370539 0.038 Uiso 1 1 calc R U . . .
C14 C 0.54919(12) 0.2065(2) 0.42992(6) 0.0322(3) Uani 1 1 d . . . . .
H14 H 0.565141 0.181176 0.388736 0.039 Uiso 1 1 calc R U . . .
C20 C 0.40458(13) 0.23856(19) 0.50926(6) 0.0329(3) Uani 1 1 d . . . . .
C12 C 0.77370(12) 0.24421(19) 0.45722(6) 0.0324(3) Uani 1 1 d . . . . .
C8 C 0.88762(12) 0.5295(2) 0.36713(6) 0.0313(3) Uani 1 1 d . . . . .
H8A H 0.856971 0.653036 0.358792 0.038 Uiso 1 1 calc R U . . .
H8B H 0.914922 0.522378 0.411234 0.038 Uiso 1 1 calc R U . . .
C3 C 1.07253(13) 0.4013(2) 0.23333(7) 0.0363(3) Uani 1 1 d . . . . .
H3 H 1.059340 0.351159 0.193414 0.044 Uiso 1 1 calc R U . . .
C21 C 0.50354(15) 0.2825(2) 0.55210(7) 0.0396(3) Uani 1 1 d . . . . .
H21 H 0.489080 0.309428 0.593364 0.048 Uiso 1 1 calc R U . . .
C22 C 0.61955(14) 0.2864(2) 0.53446(6) 0.0378(3) Uani 1 1 d . . . . .
H22 H 0.684024 0.316247 0.563658 0.045 Uiso 1 1 calc R U . . .
C6 C 1.11088(13) 0.5507(2) 0.35067(7) 0.0377(3) Uani 1 1 d . . . . .
H6 H 1.124482 0.602347 0.390350 0.045 Uiso 1 1 calc R U . . .
C5 C 1.20734(13) 0.5294(2) 0.31363(7) 0.0431(4) Uani 1 1 d . . . . .
H5 H 1.285982 0.565931 0.328449 0.052 Uiso 1 1 calc R U . . .
C16 C 0.32832(14) 0.1627(2) 0.40393(8) 0.0441(4) Uani 1 1 d . . . . .
H16 H 0.342306 0.140119 0.362302 0.053 Uiso 1 1 calc R U . . .
C4 C 1.18832(14) 0.4547(2) 0.25511(7) 0.0426(4) Uani 1 1 d . . . . .
H4 H 1.253857 0.440229 0.230170 0.051 Uiso 1 1 calc R U . . .
C19 C 0.28318(14) 0.2287(2) 0.52653(8) 0.0424(4) Uani 1 1 d . . . . .
H19 H 0.267052 0.249924 0.567951 0.051 Uiso 1 1 calc R U . . .
C10 C 0.56389(14) 0.4045(2) 0.25047(8) 0.0439(4) Uani 1 1 d . . . . .
H10A H 0.585106 0.464817 0.212895 0.066 Uiso 1 1 calc R U . . .
H10B H 0.557626 0.494176 0.282993 0.066 Uiso 1 1 calc R U . . .
H10C H 0.486448 0.342687 0.242690 0.066 Uiso 1 1 calc R U . . .
C18 C 0.18963(15) 0.1889(2) 0.48385(9) 0.0476(4) Uani 1 1 d . . . . .
H18 H 0.109534 0.183598 0.495889 0.057 Uiso 1 1 calc R U . . .
C17 C 0.21264(15) 0.1558(3) 0.42190(9) 0.0505(4) Uani 1 1 d . . . . .
H17 H 0.147717 0.128673 0.392633 0.061 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C11 1.3926(15) . ?
O2 N1 1.4025(14) . ?
O2 C10 1.4321(18) . ?
O1 C1 1.2284(16) . ?
O3 C12 1.2113(17) . ?
N1 C1 1.3563(17) . ?
N1 C9 1.4582(16) . ?
C2 C1 1.4896(18) . ?
C2 C7 1.3947(18) . ?
C2 C3 1.3922(19) . ?
C13 C14 1.374(2) . ?
C13 C12 1.4904(19) . ?
C13 C22 1.4159(19) . ?
C7 C8 1.5031(18) . ?
C7 C6 1.3863(19) . ?
C9 H9 0.9900 . ?
C9 C11 1.5339(19) . ?
C9 C8 1.5264(19) . ?
C15 C14 1.4163(19) . ?
C15 C20 1.4155(19) . ?
C15 C16 1.413(2) . ?
C11 H11 0.9900 . ?
C11 C12 1.5296(19) . ?
C14 H14 0.9400 . ?
C20 C21 1.414(2) . ?
C20 C19 1.418(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C3 H3 0.9400 . ?
C3 C4 1.383(2) . ?
C21 H21 0.9400 . ?
C21 C22 1.362(2) . ?
C22 H22 0.9400 . ?
C6 H6 0.9400 . ?
C6 C5 1.388(2) . ?
C5 H5 0.9400 . ?
C5 C4 1.381(2) . ?
C16 H16 0.9400 . ?
C16 C17 1.362(2) . ?
C4 H4 0.9400 . ?
C19 H19 0.9400 . ?
C19 C18 1.362(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
C18 H18 0.9400 . ?
C18 C17 1.404(3) . ?
C17 H17 0.9400 . ?

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
N1 O2 C10 110.32(11) . . ?
O2 N1 C9 112.69(10) . . ?
C1 N1 O2 116.96(10) . . ?
C1 N1 C9 127.67(11) . . ?
C7 C2 C1 121.33(12) . . ?
C3 C2 C1 118.64(12) . . ?
C3 C2 C7 120.03(12) . . ?
O1 C1 N1 122.42(12) . . ?
O1 C1 C2 122.76(12) . . ?
N1 C1 C2 114.82(11) . . ?
C14 C13 C12 122.72(12) . . ?
C14 C13 C22 119.25(13) . . ?
C22 C13 C12 118.01(12) . . ?
C2 C7 C8 119.41(12) . . ?
C6 C7 C2 119.25(12) . . ?
C6 C7 C8 121.18(12) . . ?
N1 C9 H9 107.1 . . ?
N1 C9 C11 111.61(11) . . ?
N1 C9 C8 109.56(10) . . ?
C11 C9 H9 107.1 . . ?
C8 C9 H9 107.1 . . ?
C8 C9 C11 114.05(11) . . ?
C20 C15 C14 119.11(13) . . ?
C16 C15 C14 122.20(13) . . ?
C16 C15 C20 118.68(13) . . ?
F1 C11 C9 109.34(10) . . ?
F1 C11 H11 109.6 . . ?
F1 C11 C12 108.56(11) . . ?
C9 C11 H11 109.6 . . ?
C12 C11 C9 110.10(11) . . ?
C12 C11 H11 109.6 . . ?
C13 C14 C15 121.06(13) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C15 C20 C19 118.89(14) . . ?
C21 C20 C15 118.76(13) . . ?
C21 C20 C19 122.35(13) . . ?
O3 C12 C13 122.35(13) . . ?
O3 C12 C11 119.81(12) . . ?
C13 C12 C11 117.81(11) . . ?
C7 C8 C9 113.40(11) . . ?
C7 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
C9 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.24(13) . . ?
C4 C3 H3 119.9 . . ?
C20 C21 H21 119.5 . . ?
C22 C21 C20 120.98(13) . . ?
C22 C21 H21 119.5 . . ?
C13 C22 H22 119.6 . . ?
C21 C22 C13 120.80(14) . . ?
C21 C22 H22 119.6 . . ?
C7 C6 H6 119.8 . . ?
C7 C6 C5 120.38(13) . . ?
C5 C6 H6 119.8 . . ?
C6 C5 H5 119.8 . . ?
C4 C5 C6 120.33(14) . . ?
C4 C5 H5 119.8 . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 120.97(15) . . ?
C17 C16 H16 119.5 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.77(13) . . ?
C5 C4 H4 120.1 . . ?
C20 C19 H19 119.6 . . ?
C18 C19 C20 120.85(15) . . ?
C18 C19 H19 119.6 . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C19 C18 H18 119.9 . . ?
C19 C18 C17 120.12(15) . . ?
C17 C18 H18 119.9 . . ?
C16 C17 C18 120.49(16) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?

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 C11 C12 O3 22.85(18) . . . . ?
F1 C11 C12 C13 -159.03(11) . . . . ?
O2 N1 C1 O1 13.03(19) . . . . ?
O2 N1 C1 C2 -167.12(11) . . . . ?
O2 N1 C9 C11 66.35(14) . . . . ?
O2 N1 C9 C8 -166.35(10) . . . . ?
N1 C9 C11 F1 80.31(13) . . . . ?
N1 C9 C11 C12 -160.50(10) . . . . ?
N1 C9 C8 C7 -41.93(16) . . . . ?
C2 C7 C8 C9 30.64(18) . . . . ?
C2 C7 C6 C5 -0.6(2) . . . . ?
C2 C3 C4 C5 -0.4(2) . . . . ?
C1 N1 C9 C11 -94.33(16) . . . . ?
C1 N1 C9 C8 32.97(19) . . . . ?
C1 C2 C7 C8 -3.9(2) . . . . ?
C1 C2 C7 C6 -179.27(13) . . . . ?
C1 C2 C3 C4 179.78(14) . . . . ?
C7 C2 C1 O1 170.55(13) . . . . ?
C7 C2 C1 N1 -9.30(19) . . . . ?
C7 C2 C3 C4 0.2(2) . . . . ?
C7 C6 C5 C4 0.4(2) . . . . ?
C9 N1 C1 O1 173.00(13) . . . . ?
C9 N1 C1 C2 -7.1(2) . . . . ?
C9 C11 C12 O3 -96.81(16) . . . . ?
C9 C11 C12 C13 81.31(15) . . . . ?
C15 C20 C21 C22 -1.7(2) . . . . ?
C15 C20 C19 C18 -1.1(2) . . . . ?
C15 C16 C17 C18 0.0(3) . . . . ?
C11 C9 C8 C7 83.99(14) . . . . ?
C14 C13 C12 O3 -176.00(14) . . . . ?
C14 C13 C12 C11 5.9(2) . . . . ?
C14 C13 C22 C21 1.5(2) . . . . ?
C14 C15 C20 C21 2.3(2) . . . . ?
C14 C15 C20 C19 -177.75(13) . . . . ?
C14 C15 C16 C17 178.25(16) . . . . ?
C20 C15 C14 C13 -1.0(2) . . . . ?
C20 C15 C16 C17 -0.6(2) . . . . ?
C20 C21 C22 C13 -0.2(2) . . . . ?
C20 C19 C18 C17 0.4(3) . . . . ?
C12 C13 C14 C15 177.74(13) . . . . ?
C12 C13 C22 C21 -177.20(14) . . . . ?
C8 C7 C6 C5 -175.93(14) . . . . ?
C8 C9 C11 F1 -44.53(15) . . . . ?
C8 C9 C11 C12 74.67(14) . . . . ?
C3 C2 C1 O1 -9.0(2) . . . . ?
C3 C2 C1 N1 171.12(13) . . . . ?
C3 C2 C7 C8 175.72(13) . . . . ?
C3 C2 C7 C6 0.3(2) . . . . ?
C21 C20 C19 C18 178.92(15) . . . . ?
C22 C13 C14 C15 -0.9(2) . . . . ?
C22 C13 C12 O3 2.6(2) . . . . ?
C22 C13 C12 C11 -175.45(13) . . . . ?
C6 C7 C8 C9 -154.03(13) . . . . ?
C6 C5 C4 C3 0.1(3) . . . . ?
C16 C15 C14 C13 -179.87(14) . . . . ?
C16 C15 C20 C21 -178.83(14) . . . . ?
C16 C15 C20 C19 1.2(2) . . . . ?
C19 C20 C21 C22 178.32(15) . . . . ?
C19 C18 C17 C16 0.2(3) . . . . ?
C10 O2 N1 C1 -101.61(14) . . . . ?
C10 O2 N1 C9 95.47(13) . . . . ?

_olex2_exptl_crystal_mounting_method no
_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 1.528
_oxdiff_exptl_absorpt_empirical_full_min 0.775
####################################################################### 
# 
# 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_exp_8121_auto
_database_code_depnum_ccdc_archive 'CCDC 2472711'
loop_
_audit_author_name
_audit_author_address
'Lin Wei'
;WuYi University
China
;
_audit_update_record             
;
2025-07-15 deposited with the CCDC.	2025-10-21 downloaded from the CCDC.
;
_audit_creation_date             2024-04-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C22 H18 F N O3)'
_chemical_formula_sum            'C11 H9 F0.50 N0.50 O1.50'
_chemical_formula_weight         181.69
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.34490(10)
_cell_length_b                   9.46510(10)
_cell_length_c                   25.5608(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.0170(10)
_cell_angle_gamma                90
_cell_volume                     1774.53(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    15619
_cell_measurement_temperature    299.19(10)
_cell_measurement_theta_max      77.7720
_cell_measurement_theta_min      4.9820
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.805
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59485
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             760
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            23690
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.871
_diffrn_reflns_theta_min         3.463
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.19(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     58.00  83.00   0.50    0.27    --  108.07-140.00 112.00   50
  2  ω     62.00  89.00   0.50    0.07    --   50.49-140.00 112.00   54
  3  ω     89.00 115.00   0.50    0.27    --  108.07-130.00 -73.00   52
  4  ω     69.00 112.00   0.50    0.27    --  108.07-125.00 -90.00   86
  5  ω     38.00  73.00   0.50    0.07    --   50.49-130.00 -73.00   70
  6  ω     80.00 105.00   0.50    0.27    --  108.07 -99.00   0.00   50
  7  ω     38.00  84.00   0.50    0.27    --  108.07 -99.00 -30.00   92
  8  ω     53.00 106.00   0.50    0.27    --  108.07 -99.00 -90.00  106
  9  ω     77.00 103.00   0.50    0.27    --  108.07 -99.00-180.00   52
 10  ω     38.00  66.00   0.50    0.27    --  108.07 -99.00   0.00   56
 11  ω     77.00 112.00   0.50    0.27    --  108.07-125.00  30.00   70
 12  ω     38.00  94.00   0.50    0.27    --  108.07 -99.00  90.00  112
 13  ω     39.00  97.00   0.50    0.27    --  108.07 -99.00 120.00  116
 14  ω     38.00 104.00   0.50    0.27    --  108.07 -99.00 150.00  132
 15  ω     36.00  61.00   0.50    0.27    --  108.07 -57.00  90.00   50
 16  ω    -20.00   6.00   0.50    0.07    --   50.49 -19.00  30.00   52
 17  ω     -2.00  23.00   0.50    0.07    --   50.49 -19.00   0.00   50
 18  ω     39.00  65.00   0.50    0.27    --  108.07 -57.00-120.00   52
 19  ω     39.00  64.00   0.50    0.27    --  108.07 -57.00 -30.00   50
 20  ω    103.00 178.00   0.50    0.27    --  108.07  38.00  90.00  150
 21  ω    143.00 168.00   0.50    0.27    --  108.07  57.00 150.00   50
 22  ω    106.00 136.00   0.50    0.27    --  108.07  57.00 150.00   60
 23  ω    128.00 173.00   0.50    0.27    --  108.07 140.00 171.00   90
 24  ω     97.00 123.00   0.50    0.27    --  108.07 140.00 171.00   52
 25  ω    100.00 147.00   0.50    0.27    --  108.07 130.00  -1.00   94
 26  ω    101.00 132.00   0.50    0.27    --  108.07 125.00 -90.00   62
 27  ω    -26.00  23.00   0.50    0.07    --  -50.49  19.00 120.00   98
 28  ω    -83.00 -58.00   0.50    0.27    --  -90.00 140.00 171.00   50
 29  ω    -84.00 -59.00   0.50    0.07    --  -50.49 140.00 171.00   50
 30  ω    -81.00 -43.00   0.50    0.07    --  -50.49 130.00  -1.00   76
 31  ω    -82.00 -51.00   0.50    0.27    --  -90.00 130.00  -1.00   62
 32  ω    -50.00 -19.00   0.50    0.27    --  -90.00  57.00 -30.00   62
 33  ω    -66.00 -21.00   0.50    0.27    --  -90.00 125.00-120.00   90
 34  ω    -64.00 -20.00   0.50    0.27    --  -90.00  57.00-150.00   88
 35  ω   -158.00 -82.00   0.50    0.27    --  -90.00 -19.00 -30.00  152
 36  ω   -161.00 -83.00   0.50    0.27    --  -90.00 -38.00 -90.00  156
 37  ω   -121.00 -32.00   0.50    0.07    --  -50.49 -77.00-180.00  178
 38  ω   -140.00 -69.00   0.50    0.27    --  -90.00 -77.00-150.00  142
 39  ω   -159.00 -89.00   0.50    0.27    --  -90.00 -99.00-120.00  140
 40  ω   -139.00-114.00   0.50    0.27    --  -90.00-130.00 -73.00   50
 41  ω   -119.00 -94.00   0.50    0.07    --  -50.49-125.00 -60.00   50
 42  ω   -114.00 -85.00   0.50    0.07    --  -50.49-125.00 -90.00   58
 43  ω    -97.00 -70.00   0.50    0.07    --  -50.49-130.00 -73.00   54
 44  ω   -119.00 -63.00   0.50    0.07    --  -50.49-140.00 112.00  112
 45  ω   -126.00 -64.00   0.50    0.27    --  -90.00-140.00 112.00  124
;
_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      -0.1151932000
_diffrn_orient_matrix_UB_12      0.0164961000
_diffrn_orient_matrix_UB_13      0.0482743000
_diffrn_orient_matrix_UB_21      -0.1695862000
_diffrn_orient_matrix_UB_22      0.0316651000
_diffrn_orient_matrix_UB_23      -0.0361427000
_diffrn_orient_matrix_UB_31      -0.0457626000
_diffrn_orient_matrix_UB_32      -0.1588108000
_diffrn_orient_matrix_UB_33      -0.0021913000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3285
_reflns_number_total             3679
_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 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0028(4)
_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   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3679
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0449
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0667P)²+0.3903P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1289
_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:
 C006(H006), C009(H009)
2.b Secondary CH2 refined with riding coordinates:
 C00F(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L),
 C00M(H00M), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R)
2.d Idealised Me refined as rotating group:
 C00N(H00C,H00D,H00F)
;
_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
F001 F 0.40152(13) 0.32071(10) 0.80754(3) 0.0587(3) Uani 1 1 d . . . . .
O002 O 0.71626(13) 0.41607(11) 0.70099(4) 0.0463(3) Uani 1 1 d . . . . .
O003 O 0.96620(13) 0.34045(11) 0.77303(4) 0.0528(3) Uani 1 1 d . . . . .
N004 N 0.70614(14) 0.46142(12) 0.75271(4) 0.0398(3) Uani 1 1 d . . . . .
O005 O 0.40608(18) 0.17822(11) 0.72378(5) 0.0639(3) Uani 1 1 d . . . . .
C006 C 0.52718(16) 0.51653(13) 0.76443(5) 0.0354(3) Uani 1 1 d . . . . .
H006 H 0.493006 0.586487 0.737407 0.042 Uiso 1 1 calc R U . . .
C007 C 0.83516(16) 0.40753(13) 0.78723(5) 0.0393(3) Uani 1 1 d . . . . .
C008 C 0.80683(18) 0.43760(14) 0.84327(6) 0.0421(3) Uani 1 1 d . . . . .
C009 C 0.37885(17) 0.40313(14) 0.76255(5) 0.0395(3) Uani 1 1 d . . . . .
H009 H 0.259906 0.449966 0.762788 0.047 Uiso 1 1 calc R U . . .
C00A C 0.66237(19) 0.52218(14) 0.85804(5) 0.0429(3) Uani 1 1 d . . . . .
C00B C 0.37706(18) 0.30274(14) 0.71605(6) 0.0438(3) Uani 1 1 d . . . . .
C00C C 0.23178(18) 0.52928(15) 0.59703(6) 0.0454(3) Uani 1 1 d . . . . .
C00D C 0.33914(18) 0.35656(15) 0.66178(6) 0.0441(3) Uani 1 1 d . . . . .
C00E C 0.26000(18) 0.48445(15) 0.65021(6) 0.0445(3) Uani 1 1 d . . . . .
H00E H 0.224338 0.542605 0.677156 0.053 Uiso 1 1 calc R U . . .
C00F C 0.5426(2) 0.59438(14) 0.81683(5) 0.0441(3) Uani 1 1 d . . . . .
H00A H 0.590215 0.688391 0.811110 0.053 Uiso 1 1 calc R U . . .
H00B H 0.421518 0.604762 0.829776 0.053 Uiso 1 1 calc R U . . .
C00G C 0.2900(2) 0.44029(18) 0.55667(6) 0.0523(4) Uani 1 1 d . . . . .
C00H C 0.1479(2) 0.65970(17) 0.58393(6) 0.0542(4) Uani 1 1 d . . . . .
H00H H 0.106522 0.717665 0.610179 0.065 Uiso 1 1 calc R U . . .
C00I C 0.3929(2) 0.26781(18) 0.62050(7) 0.0582(4) Uani 1 1 d . . . . .
H00I H 0.444415 0.180105 0.628370 0.070 Uiso 1 1 calc R U . . .
C00J C 0.9282(2) 0.37888(17) 0.88087(7) 0.0560(4) Uani 1 1 d . . . . .
H00J H 1.025063 0.324001 0.870569 0.067 Uiso 1 1 calc R U . . .
C00K C 0.6408(2) 0.54315(19) 0.91118(6) 0.0583(4) Uani 1 1 d . . . . .
H00K H 0.544731 0.598185 0.921946 0.070 Uiso 1 1 calc R U . . .
C00L C 0.1274(3) 0.7008(2) 0.53264(7) 0.0627(4) Uani 1 1 d . . . . .
H00L H 0.071982 0.786864 0.524289 0.075 Uiso 1 1 calc R U . . .
C00M C 0.3700(3) 0.3092(2) 0.56979(7) 0.0642(4) Uani 1 1 d . . . . .
H00M H 0.407676 0.250151 0.543368 0.077 Uiso 1 1 calc R U . . .
C00N C 0.7748(3) 0.5298(2) 0.66911(7) 0.0680(5) Uani 1 1 d . . . . .
H00C H 0.800739 0.494369 0.635102 0.102 Uiso 1 1 calc R U . . .
H00D H 0.882878 0.571635 0.685205 0.102 Uiso 1 1 calc R U . . .
H00F H 0.680232 0.599632 0.665628 0.102 Uiso 1 1 calc R U . . .
C00O C 0.1887(3) 0.6151(2) 0.49261(7) 0.0684(5) Uani 1 1 d . . . . .
H00O H 0.175512 0.645227 0.457991 0.082 Uiso 1 1 calc R U . . .
C00P C 0.9051(3) 0.4019(2) 0.93334(7) 0.0687(5) Uani 1 1 d . . . . .
H00P H 0.986418 0.363082 0.958500 0.082 Uiso 1 1 calc R U . . .
C00Q C 0.2668(3) 0.4890(2) 0.50386(7) 0.0658(5) Uani 1 1 d . . . . .
H00Q H 0.306192 0.432838 0.476809 0.079 Uiso 1 1 calc R U . . .
C00R C 0.7613(3) 0.4826(2) 0.94827(7) 0.0704(5) Uani 1 1 d . . . . .
H00R H 0.744647 0.496804 0.983698 0.084 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
F001 C009 1.3922(15) . ?
O002 N004 1.3956(14) . ?
O002 C00N 1.430(2) . ?
O003 C007 1.2240(16) . ?
N004 C006 1.4599(15) . ?
N004 C007 1.3598(17) . ?
O005 C00B 1.2121(17) . ?
C006 H006 0.9800 . ?
C006 C009 1.5284(17) . ?
C006 C00F 1.5277(18) . ?
C007 C008 1.486(2) . ?
C008 C00A 1.397(2) . ?
C008 C00J 1.392(2) . ?
C009 H009 0.9800 . ?
C009 C00B 1.521(2) . ?
C00A C00F 1.5009(19) . ?
C00A C00K 1.390(2) . ?
C00B C00D 1.490(2) . ?
C00C C00E 1.429(2) . ?
C00C C00G 1.415(2) . ?
C00C C00H 1.412(2) . ?
C00D C00E 1.368(2) . ?
C00D C00I 1.421(2) . ?
C00E H00E 0.9300 . ?
C00F H00A 0.9700 . ?
C00F H00B 0.9700 . ?
C00G C00M 1.406(2) . ?
C00G C00Q 1.428(2) . ?
C00H H00H 0.9300 . ?
C00H C00L 1.368(2) . ?
C00I H00I 0.9300 . ?
C00I C00M 1.356(2) . ?
C00J H00J 0.9300 . ?
C00J C00P 1.378(3) . ?
C00K H00K 0.9300 . ?
C00K C00R 1.387(3) . ?
C00L H00L 0.9300 . ?
C00L C00O 1.399(3) . ?
C00M H00M 0.9300 . ?
C00N H00C 0.9600 . ?
C00N H00D 0.9600 . ?
C00N H00F 0.9600 . ?
C00O H00O 0.9300 . ?
C00O C00Q 1.349(3) . ?
C00P H00P 0.9300 . ?
C00P C00R 1.373(3) . ?
C00Q H00Q 0.9300 . ?
C00R H00R 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
N004 O002 C00N 109.93(11) . . ?
O002 N004 C006 113.44(10) . . ?
C007 N004 O002 115.42(10) . . ?
C007 N004 C006 127.23(11) . . ?
N004 C006 H006 107.3 . . ?
N004 C006 C009 112.99(10) . . ?
N004 C006 C00F 109.05(10) . . ?
C009 C006 H006 107.3 . . ?
C00F C006 H006 107.3 . . ?
C00F C006 C009 112.72(11) . . ?
O003 C007 N004 122.28(13) . . ?
O003 C007 C008 122.52(12) . . ?
N004 C007 C008 115.19(11) . . ?
C00A C008 C007 121.15(12) . . ?
C00J C008 C007 118.17(13) . . ?
C00J C008 C00A 120.68(14) . . ?
F001 C009 C006 108.27(10) . . ?
F001 C009 H009 108.4 . . ?
F001 C009 C00B 106.92(11) . . ?
C006 C009 H009 108.4 . . ?
C00B C009 C006 116.11(11) . . ?
C00B C009 H009 108.4 . . ?
C008 C00A C00F 119.79(12) . . ?
C00K C00A C008 118.25(14) . . ?
C00K C00A C00F 121.86(14) . . ?
O005 C00B C009 119.07(13) . . ?
O005 C00B C00D 120.45(14) . . ?
C00D C00B C009 120.49(11) . . ?
C00G C00C C00E 118.86(14) . . ?
C00H C00C C00E 121.66(14) . . ?
C00H C00C C00G 119.48(14) . . ?
C00E C00D C00B 124.06(13) . . ?
C00E C00D C00I 119.60(14) . . ?
C00I C00D C00B 116.33(13) . . ?
C00C C00E H00E 119.8 . . ?
C00D C00E C00C 120.47(13) . . ?
C00D C00E H00E 119.8 . . ?
C006 C00F H00A 108.7 . . ?
C006 C00F H00B 108.7 . . ?
C00A C00F C006 114.16(11) . . ?
C00A C00F H00A 108.7 . . ?
C00A C00F H00B 108.7 . . ?
H00A C00F H00B 107.6 . . ?
C00C C00G C00Q 118.14(16) . . ?
C00M C00G C00C 119.33(15) . . ?
C00M C00G C00Q 122.53(15) . . ?
C00C C00H H00H 120.0 . . ?
C00L C00H C00C 120.04(15) . . ?
C00L C00H H00H 120.0 . . ?
C00D C00I H00I 119.5 . . ?
C00M C00I C00D 120.91(15) . . ?
C00M C00I H00I 119.5 . . ?
C008 C00J H00J 119.9 . . ?
C00P C00J C008 120.11(16) . . ?
C00P C00J H00J 119.9 . . ?
C00A C00K H00K 119.8 . . ?
C00R C00K C00A 120.48(17) . . ?
C00R C00K H00K 119.8 . . ?
C00H C00L H00L 119.6 . . ?
C00H C00L C00O 120.81(17) . . ?
C00O C00L H00L 119.6 . . ?
C00G C00M H00M 119.6 . . ?
C00I C00M C00G 120.81(15) . . ?
C00I C00M H00M 119.6 . . ?
O002 C00N H00C 109.5 . . ?
O002 C00N H00D 109.5 . . ?
O002 C00N H00F 109.5 . . ?
H00C C00N H00D 109.5 . . ?
H00C C00N H00F 109.5 . . ?
H00D C00N H00F 109.5 . . ?
C00L C00O H00O 119.8 . . ?
C00Q C00O C00L 120.49(16) . . ?
C00Q C00O H00O 119.8 . . ?
C00J C00P H00P 120.2 . . ?
C00R C00P C00J 119.62(16) . . ?
C00R C00P H00P 120.2 . . ?
C00G C00Q H00Q 119.5 . . ?
C00O C00Q C00G 121.01(17) . . ?
C00O C00Q H00Q 119.5 . . ?
C00K C00R H00R 119.6 . . ?
C00P C00R C00K 120.84(17) . . ?
C00P C00R H00R 119.6 . . ?

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
F001 C009 C00B O005 -4.85(17) . . . . ?
F001 C009 C00B C00D 174.81(11) . . . . ?
O002 N004 C006 C009 67.16(13) . . . . ?
O002 N004 C006 C00F -166.66(10) . . . . ?
O002 N004 C007 O003 10.07(18) . . . . ?
O002 N004 C007 C008 -170.72(10) . . . . ?
O003 C007 C008 C00A 175.81(12) . . . . ?
O003 C007 C008 C00J -4.3(2) . . . . ?
N004 C006 C009 F001 75.23(13) . . . . ?
N004 C006 C009 C00B -44.98(15) . . . . ?
N004 C006 C00F C00A -40.79(15) . . . . ?
N004 C007 C008 C00A -3.40(18) . . . . ?
N004 C007 C008 C00J 176.47(13) . . . . ?
O005 C00B C00D C00E 162.37(14) . . . . ?
O005 C00B C00D C00I -18.7(2) . . . . ?
C006 N004 C007 O003 166.20(12) . . . . ?
C006 N004 C007 C008 -14.59(18) . . . . ?
C006 C009 C00B O005 116.08(14) . . . . ?
C006 C009 C00B C00D -64.26(16) . . . . ?
C007 N004 C006 C009 -89.37(15) . . . . ?
C007 N004 C006 C00F 36.81(17) . . . . ?
C007 C008 C00A C00F -5.29(19) . . . . ?
C007 C008 C00A C00K 178.35(13) . . . . ?
C007 C008 C00J C00P -178.83(14) . . . . ?
C008 C00A C00F C006 28.73(18) . . . . ?
C008 C00A C00K C00R 0.7(2) . . . . ?
C008 C00J C00P C00R 0.3(3) . . . . ?
C009 C006 C00F C00A 85.55(14) . . . . ?
C009 C00B C00D C00E -17.3(2) . . . . ?
C009 C00B C00D C00I 161.69(13) . . . . ?
C00A C008 C00J C00P 1.0(2) . . . . ?
C00A C00K C00R C00P 0.6(3) . . . . ?
C00B C00D C00E C00C 178.73(12) . . . . ?
C00B C00D C00I C00M -177.76(15) . . . . ?
C00C C00G C00M C00I -0.4(3) . . . . ?
C00C C00G C00Q C00O -1.2(3) . . . . ?
C00C C00H C00L C00O 0.0(3) . . . . ?
C00D C00I C00M C00G -0.9(3) . . . . ?
C00E C00C C00G C00M 1.4(2) . . . . ?
C00E C00C C00G C00Q -177.75(14) . . . . ?
C00E C00C C00H C00L 178.30(15) . . . . ?
C00E C00D C00I C00M 1.3(2) . . . . ?
C00F C006 C009 F001 -48.97(14) . . . . ?
C00F C006 C009 C00B -169.18(11) . . . . ?
C00F C00A C00K C00R -175.56(16) . . . . ?
C00G C00C C00E C00D -1.1(2) . . . . ?
C00G C00C C00H C00L -1.6(2) . . . . ?
C00H C00C C00E C00D 178.99(14) . . . . ?
C00H C00C C00G C00M -178.67(15) . . . . ?
C00H C00C C00G C00Q 2.2(2) . . . . ?
C00H C00L C00O C00Q 1.0(3) . . . . ?
C00I C00D C00E C00C -0.2(2) . . . . ?
C00J C008 C00A C00F 174.84(13) . . . . ?
C00J C008 C00A C00K -1.5(2) . . . . ?
C00J C00P C00R C00K -1.1(3) . . . . ?
C00K C00A C00F C006 -155.04(13) . . . . ?
C00L C00O C00Q C00G -0.4(3) . . . . ?
C00M C00G C00Q C00O 179.69(19) . . . . ?
C00N O002 N004 C006 90.91(14) . . . . ?
C00N O002 N004 C007 -109.65(14) . . . . ?
C00Q C00G C00M C00I 178.72(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.154
_oxdiff_exptl_absorpt_empirical_full_min 0.488
