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

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

data_x-1335_auto
_database_code_depnum_ccdc_archive 'CCDC 2349492'
loop_
_audit_author_name
_audit_author_address
'Haruhiko Fukaya'
;Tokyo University of Pharmacy and Life Sciences
Japan
;
_audit_update_record             
;
2024-04-19 deposited with the CCDC.	2024-12-11 downloaded from the CCDC.
;
_audit_creation_date             2024-04-10
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H19 F2 N O'
_chemical_formula_sum            'C23 H19 F2 N O'
_chemical_formula_weight         363.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H19 F2 N O'
_chemical_oxdiff_usercomment     5aI
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.4568(2)
_cell_length_b                   16.4098(2)
_cell_length_c                   8.25210(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.7070(10)
_cell_angle_gamma                90
_cell_volume                     1816.11(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13500
_cell_measurement_temperature    119.9(5)
_cell_measurement_theta_max      77.1010
_cell_measurement_theta_min      4.2320
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.912
_exptl_absorpt_coefficient_mu    0.783
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68509
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.84a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane and ethylacetate'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.041
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            31987
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.725
_diffrn_reflns_theta_min         3.295
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      119.9(5)
_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 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -68.00  31.00   0.50    0.23    --  -43.07  68.00  59.00  198
  2  ω   -117.00 -18.00   0.50    0.23    --  -43.07 -68.00 -74.00  198
  3  ω    -77.00 -30.00   0.50    0.90    -- -104.50  68.00  59.00   94
  4  ω     88.00 178.00   0.50    0.90    --  113.00  68.00  59.00  180
  5  ω     39.00  87.00   0.50    0.90    --  113.00 -68.00 -74.00   96
  6  ω    -39.00  34.00   0.50    0.23    --  -43.07  38.00-150.00  146
  7  ω    -25.00  38.00   0.50    0.23    --  -43.07  19.00  60.00  126
  8  ω    -66.00 -30.00   0.50    0.90    -- -104.50  61.00 -90.00   72
  9  ω   -174.00 -79.00   0.50    0.90    -- -104.50 -68.00 -74.00  190
 10  ω    -66.00 -30.00   0.50    0.90    -- -104.50  61.00 -60.00   72
 11  ω     89.00 178.00   0.50    0.90    --  113.00  30.00 120.00  178
 12  ω     90.00 178.00   0.50    0.90    --  113.00  95.00 135.61  176
 13  ω     89.00 178.00   0.50    0.90    --  113.00  30.00 150.00  178
 14  ω     39.00  76.00   0.50    0.90    --  113.00 -61.00  60.00   74
 15  ω     39.00  76.00   0.50    0.90    --  113.00 -61.00 -30.00   74
 16  ω     39.00 106.00   0.50    0.90    --  113.00 -77.00  60.00  134
 17  ω     91.00 178.00   0.50    0.90    --  113.00  45.00  90.00  174
 18  ω     89.00 178.00   0.50    0.90    --  113.00  30.00-180.00  178
 19  ω     38.00 106.00   0.50    0.90    --  113.00 -95.00  60.00  136
 20  ω     40.00 108.00   0.50    0.90    --  113.00-110.00 -68.53  136
 21  ω     41.00 112.00   0.50    0.90    --  113.00-125.00-180.00  142
 22  ω     91.00 178.00   0.50    0.90    --  113.00  45.00 -30.00  174
 23  ω     39.00 106.00   0.50    0.90    --  113.00 -77.00  90.00  134
 24  ω     41.00 112.00   0.50    0.90    --  113.00-125.00 -30.00  142
 25  ω     39.00 106.00   0.50    0.90    --  113.00 -77.00 -90.00  134
 26  ω     39.00 106.00   0.50    0.90    --  113.00 -77.00   0.00  134
 27  ω     92.00 178.00   0.50    0.90    --  113.00  51.00  -8.97  172
 28  ω     39.00 106.00   0.50    0.90    --  113.00 -77.00-180.00  134
 29  ω     39.00 106.00   0.50    0.90    --  113.00 -77.00 -30.00  134
 30  ω     41.00 112.00   0.50    0.90    --  113.00-125.00 -60.00  142
 31  ω     39.00  76.00   0.50    0.90    --  113.00 -61.00 120.00   74
 32  ω     38.00 106.00   0.50    0.90    --  113.00 -95.00  30.00  136
 33  ω     38.00 106.00   0.50    0.90    --  113.00 -95.00-150.00  136
 34  ω     38.00 106.00   0.50    0.90    --  113.00 -95.00 -90.00  136
 35  ω     41.00 112.00   0.50    0.90    --  113.00-125.00-120.00  142
 36  ω     39.00  76.00   0.50    0.90    --  113.00 -61.00  90.00   74
 37  ω   -117.00 -14.00   0.50    0.23    --  -43.07 -77.00-180.00  206
 38  ω   -117.00 -14.00   0.50    0.23    --  -43.07 -77.00  90.00  206
 39  ω    -39.00  34.00   0.50    0.23    --  -43.07  38.00 -60.00  146
 40  ω    -39.00  34.00   0.50    0.23    --  -43.07  38.00 150.00  146
 41  ω   -117.00 -20.00   0.50    0.23    --  -43.07 -57.00   0.00  194
 42  ω     63.00 130.00   0.50    0.90    --  113.00  15.00 -90.00  134
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0120160000
_diffrn_orient_matrix_UB_12      0.0717633000
_diffrn_orient_matrix_UB_13      -0.1171631000
_diffrn_orient_matrix_UB_21      0.1141753000
_diffrn_orient_matrix_UB_22      -0.0095551000
_diffrn_orient_matrix_UB_23      0.0230425000
_diffrn_orient_matrix_UB_31      -0.0037256000
_diffrn_orient_matrix_UB_32      -0.0597664000
_diffrn_orient_matrix_UB_33      -0.1443328000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3677
_reflns_number_total             3869
_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 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3869
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0450
_refine_ls_restrained_S_all      1.086
_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)+(0.0419P)²+0.8909P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1079
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
2.b Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C)
;
_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
C1 C 0.32789(10) 0.41680(8) 0.73589(17) 0.0263(3) Uani 1 1 d . . . . .
C2 C 0.29991(11) 0.33603(9) 0.76662(18) 0.0285(3) Uani 1 1 d . . . . .
C3 C 0.36882(12) 0.28640(9) 0.85613(19) 0.0315(3) Uani 1 1 d . . . . .
H3 H 0.349596 0.232378 0.880679 0.038 Uiso 1 1 calc R U . . .
C4 C 0.46381(11) 0.31220(9) 0.91078(18) 0.0304(3) Uani 1 1 d . . . . .
C5 C 0.49248(11) 0.39034(9) 0.86879(18) 0.0305(3) Uani 1 1 d . . . . .
H5 H 0.558500 0.408522 0.898471 0.037 Uiso 1 1 calc R U . . .
C6 C 0.42521(11) 0.44175(9) 0.78391(18) 0.0291(3) Uani 1 1 d . . . . .
H6 H 0.445670 0.495232 0.757692 0.035 Uiso 1 1 calc R U . . .
C7 C 0.17032(11) 0.60077(9) 0.66917(16) 0.0272(3) Uani 1 1 d . . . . .
C10 C 0.25558(10) 0.47602(8) 0.64690(17) 0.0258(3) Uani 1 1 d . . . . .
C11 C 0.27489(11) 0.56724(9) 0.68149(17) 0.0279(3) Uani 1 1 d . . . . .
C12 C 0.14270(11) 0.68651(9) 0.64059(17) 0.0281(3) Uani 1 1 d . . . . .
C13 C 0.05258(12) 0.70547(9) 0.5525(2) 0.0341(3) Uani 1 1 d . . . . .
H13 H 0.009315 0.663104 0.511847 0.041 Uiso 1 1 calc R U . . .
C14 C 0.02652(13) 0.78608(10) 0.5245(2) 0.0391(4) Uani 1 1 d . . . . .
H14 H -0.034722 0.798946 0.464420 0.047 Uiso 1 1 calc R U . . .
C15 C 0.08924(13) 0.84824(10) 0.5836(2) 0.0395(4) Uani 1 1 d . . . . .
H15 H 0.070729 0.903476 0.564336 0.047 Uiso 1 1 calc R U . . .
C16 C 0.17897(13) 0.82986(10) 0.6707(2) 0.0381(4) Uani 1 1 d . . . . .
H16 H 0.221841 0.872478 0.711380 0.046 Uiso 1 1 calc R U . . .
C17 C 0.20604(12) 0.74922(9) 0.69850(19) 0.0342(3) Uani 1 1 d . . . . .
H17 H 0.267856 0.736632 0.757095 0.041 Uiso 1 1 calc R U . . .
C18 C 0.24449(11) 0.46153(8) 0.46195(17) 0.0271(3) Uani 1 1 d . . . . .
C19 C 0.32925(12) 0.45163(9) 0.37742(19) 0.0323(3) Uani 1 1 d . . . . .
H19 H 0.393612 0.453543 0.433954 0.039 Uiso 1 1 calc R U . . .
C20 C 0.31944(13) 0.43894(10) 0.2103(2) 0.0389(4) Uani 1 1 d . . . . .
H20 H 0.377274 0.432352 0.152888 0.047 Uiso 1 1 calc R U . . .
C21 C 0.22571(14) 0.43585(10) 0.12689(19) 0.0397(4) Uani 1 1 d . . . . .
H21 H 0.219324 0.427305 0.012650 0.048 Uiso 1 1 calc R U . . .
C22 C 0.14186(13) 0.44523(9) 0.21055(19) 0.0348(3) Uani 1 1 d . . . . .
H22 H 0.077591 0.442720 0.153791 0.042 Uiso 1 1 calc R U . . .
C23 C 0.15089(11) 0.45834(8) 0.37739(18) 0.0289(3) Uani 1 1 d . . . . .
H23 H 0.092774 0.465156 0.434025 0.035 Uiso 1 1 calc R U . . .
C26 C 0.20043(12) 0.29978(9) 0.7072(2) 0.0367(4) Uani 1 1 d . . . . .
H26A H 0.148657 0.320823 0.772910 0.055 Uiso 1 1 calc R U . . .
H26B H 0.203645 0.240311 0.717107 0.055 Uiso 1 1 calc R U . . .
H26C H 0.184386 0.314687 0.593062 0.055 Uiso 1 1 calc R U . . .
C27 C 0.53405(13) 0.25729(10) 1.0123(2) 0.0393(4) Uani 1 1 d . . . . .
H27A H 0.600917 0.261004 0.973955 0.059 Uiso 1 1 calc R U . . .
H27B H 0.510350 0.200894 1.002529 0.059 Uiso 1 1 calc R U . . .
H27C H 0.536490 0.274308 1.126409 0.059 Uiso 1 1 calc R U . . .
F24 F 0.33653(6) 0.60265(5) 0.58086(12) 0.0353(2) Uani 1 1 d . . . . .
F25 F 0.31602(7) 0.58209(5) 0.83636(11) 0.0367(2) Uani 1 1 d . . . . .
N8 N 0.10717(9) 0.54454(7) 0.69266(15) 0.0292(3) Uani 1 1 d . . . . .
O9 O 0.15740(7) 0.46828(6) 0.70914(12) 0.0275(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.407(2) . ?
C1 C6 1.398(2) . ?
C1 C10 1.5209(19) . ?
C2 C3 1.399(2) . ?
C2 C26 1.509(2) . ?
C3 C4 1.386(2) . ?
C4 C5 1.391(2) . ?
C4 C27 1.509(2) . ?
C5 C6 1.385(2) . ?
C7 C11 1.507(2) . ?
C7 C12 1.4693(19) . ?
C7 N8 1.2799(19) . ?
C10 C11 1.5420(19) . ?
C10 C18 1.5397(19) . ?
C10 O9 1.4617(17) . ?
C11 F24 1.3521(17) . ?
C11 F25 1.3722(16) . ?
C12 C13 1.397(2) . ?
C12 C17 1.395(2) . ?
C13 C14 1.383(2) . ?
C14 C15 1.387(2) . ?
C15 C16 1.387(2) . ?
C16 C17 1.387(2) . ?
C18 C19 1.395(2) . ?
C18 C23 1.390(2) . ?
C19 C20 1.390(2) . ?
C20 C21 1.387(3) . ?
C21 C22 1.379(2) . ?
C22 C23 1.389(2) . ?
N8 O9 1.4234(15) . ?

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
C2 C1 C10 121.26(12) . . ?
C6 C1 C2 118.90(13) . . ?
C6 C1 C10 119.81(12) . . ?
C1 C2 C26 123.79(13) . . ?
C3 C2 C1 117.91(13) . . ?
C3 C2 C26 118.30(13) . . ?
C4 C3 C2 123.21(14) . . ?
C3 C4 C5 117.88(13) . . ?
C3 C4 C27 121.13(14) . . ?
C5 C4 C27 120.99(14) . . ?
C6 C5 C4 120.29(14) . . ?
C5 C6 C1 121.55(14) . . ?
C12 C7 C11 125.67(13) . . ?
N8 C7 C11 110.76(12) . . ?
N8 C7 C12 123.53(13) . . ?
C1 C10 C11 116.06(11) . . ?
C1 C10 C18 112.71(11) . . ?
C18 C10 C11 109.54(11) . . ?
O9 C10 C1 109.62(11) . . ?
O9 C10 C11 99.37(10) . . ?
O9 C10 C18 108.54(11) . . ?
C7 C11 C10 101.52(11) . . ?
F24 C11 C7 114.73(12) . . ?
F24 C11 C10 113.96(12) . . ?
F24 C11 F25 105.95(11) . . ?
F25 C11 C7 107.52(11) . . ?
F25 C11 C10 113.19(11) . . ?
C13 C12 C7 119.62(13) . . ?
C17 C12 C7 120.79(13) . . ?
C17 C12 C13 119.59(13) . . ?
C14 C13 C12 119.82(14) . . ?
C13 C14 C15 120.41(15) . . ?
C14 C15 C16 120.09(15) . . ?
C17 C16 C15 119.92(15) . . ?
C16 C17 C12 120.17(14) . . ?
C19 C18 C10 119.81(13) . . ?
C23 C18 C10 120.90(13) . . ?
C23 C18 C19 119.29(14) . . ?
C20 C19 C18 119.91(15) . . ?
C21 C20 C19 120.41(15) . . ?
C22 C21 C20 119.70(15) . . ?
C21 C22 C23 120.33(15) . . ?
C22 C23 C18 120.36(14) . . ?
C7 N8 O9 109.41(11) . . ?
N8 O9 C10 109.02(10) . . ?


_olex2_exptl_crystal_mounting_method 
;
The crystal was mounted on a MiTeGEN Dual Thickness MicroLoops in  perfluoropolyether oil
;
_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 1.602
_oxdiff_exptl_absorpt_empirical_full_min 0.680
####################################################################### 
# 
# 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_x-1339_auto
_database_code_depnum_ccdc_archive 'CCDC 2349494'
loop_
_audit_author_name
_audit_author_address
'Haruhiko Fukaya'
;Tokyo University of Pharmacy and Life Sciences
Japan
;
_audit_update_record             
;
2024-04-19 deposited with the CCDC.	2024-12-11 downloaded from the CCDC.
;
_audit_creation_date             2024-04-18
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
fukayah@toyaku.ac.jp
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H19 F2 N O'
_chemical_formula_sum            'C23 H19 F2 N O'
_chemical_formula_weight         363.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H19 F2 N O'
_chemical_oxdiff_usercomment     5aH
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   17.3894(2)
_cell_length_b                   6.21370(10)
_cell_length_c                   16.7372(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.2100(10)
_cell_angle_gamma                90
_cell_volume                     1797.88(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    19760
_cell_measurement_temperature    120.0(4)
_cell_measurement_theta_max      76.6980
_cell_measurement_theta_min      2.5370
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.791
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79248
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.84a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane and ethylacetate'
_exptl_crystal_size_max          0.096
_exptl_crystal_size_mid          0.083
_exptl_crystal_size_min          0.051
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            40254
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.006
_diffrn_reflns_theta_min         2.556
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.0(4)
_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 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      6.00  34.00   0.50    0.10    --   43.16  94.00-119.85   56
  2  ω     21.00 117.00   0.50    0.10    --   43.16  57.00-150.00  192
  3  ω     21.00 117.00   0.50    0.10    --   43.16  57.00 -60.00  192
  4  ω      6.00  34.00   0.50    0.10    --   43.16  94.00  11.65   56
  5  ω      9.00  42.00   0.50    0.10    --   43.16  89.00 130.21   66
  6  ω    -31.00 123.00   0.50    0.10    --   43.16   8.00-124.00  308
  7  ω     38.00 106.00   0.50    0.39    --  113.00 -95.00   0.00  136
  8  ω     19.00  95.00   0.50    0.10    --   43.16-125.00 -60.00  152
  9  ω     19.00  95.00   0.50    0.10    --   43.16-125.00-150.00  152
 10  ω     41.00 112.00   0.50    0.39    --  113.00-125.00 -30.00  142
 11  ω     41.00 112.00   0.50    0.39    --  113.00-125.00   0.00  142
 12  ω     41.00 112.00   0.50    0.39    --  113.00-125.00  60.00  142
 13  ω     41.00 112.00   0.50    0.39    --  113.00-125.00 150.00  142
 14  ω     41.00 112.00   0.50    0.39    --  113.00-125.00  90.00  142
 15  ω     41.00 112.00   0.50    0.39    --  113.00-125.00-150.00  142
 16  ω     39.00 109.00   0.50    0.39    --  113.00 -78.00-125.72  140
 17  ω     39.00  76.00   0.50    0.39    --  113.00 -61.00-150.00   74
 18  ω     39.00 106.00   0.50    0.39    --  113.00 -77.00 -60.00  134
 19  ω     39.00  76.00   0.50    0.39    --  113.00 -61.00   0.00   74
 20  ω     39.00  76.00   0.50    0.39    --  113.00 -61.00 -30.00   74
 21  ω     39.00  76.00   0.50    0.39    --  113.00 -61.00-120.00   74
 22  ω     39.00 106.00   0.50    0.39    --  113.00 -77.00  30.00  134
 23  ω     39.00  76.00   0.50    0.39    --  113.00 -61.00  60.00   74
 24  ω     39.00  76.00   0.50    0.39    --  113.00 -61.00 120.00   74
 25  ω     39.00  76.00   0.50    0.39    --  113.00 -61.00 150.00   74
 26  ω    -36.00  35.00   0.50    0.10    --   43.16 -19.00  60.00  142
 27  ω     37.00 178.00   0.50    0.39    --  113.00   8.00-124.00  282
 28  ω     90.00 178.00   0.50    0.39    --  113.00  61.00-150.00  176
 29  ω     91.00 178.00   0.50    0.39    --  113.00  45.00-120.00  174
 30  ω     91.00 178.00   0.50    0.39    --  113.00  45.00 -90.00  174
 31  ω     63.00 178.00   0.50    0.39    --  113.00  15.00   0.00  230
 32  ω     63.00 178.00   0.50    0.39    --  113.00  15.00 120.00  230
 33  ω     63.00 178.00   0.50    0.39    --  113.00  15.00 150.00  230
 34  ω     91.00 178.00   0.50    0.39    --  113.00  45.00 120.00  174
 35  ω     86.00 178.00   0.50    0.39    --  113.00  83.00 157.40  184
 36  ω     86.00 178.00   0.50    0.39    --  113.00  90.00  57.81  184
 37  ω     80.00 178.00   0.50    0.39    --  113.00 125.00 -30.00  196
 38  ω     90.00 178.00   0.50    0.39    --  113.00  95.00 -52.27  176
 39  ω     80.00 178.00   0.50    0.39    --  113.00 125.00-180.00  196
 40  ω   -123.00  33.00   0.50    0.10    --  -43.16  -8.00  60.00  312
 41  ω   -120.00 -20.00   0.50    0.10    --  -43.16 -38.00 -30.00  200
 42  ω   -174.00 -81.00   0.50    0.39    -- -104.50 -77.00   0.00  186
 43  ω   -174.00 -75.00   0.50    0.39    -- -104.50 -77.00  30.00  198
 44  ω   -117.00 -14.00   0.50    0.10    --  -43.16 -77.00  90.00  206
 45  ω   -174.00 -75.00   0.50    0.39    -- -104.50 -77.00  67.24  198
 46  ω   -174.00 -28.00   0.50    0.39    -- -104.50  -8.00  60.00  292
 47  ω    -66.00 -30.00   0.50    0.39    -- -104.50  61.00 120.00   72
 48  ω    -96.00 -30.00   0.50    0.39    -- -104.50  77.00  60.00  132
 49  ω    -66.00 -30.00   0.50    0.39    -- -104.50  61.00   0.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0130187000
_diffrn_orient_matrix_UB_12      0.0228639000
_diffrn_orient_matrix_UB_13      -0.0892020000
_diffrn_orient_matrix_UB_21      -0.0879479000
_diffrn_orient_matrix_UB_22      -0.0137651000
_diffrn_orient_matrix_UB_23      -0.0238312000
_diffrn_orient_matrix_UB_31      -0.0061316000
_diffrn_orient_matrix_UB_32      0.2464903000
_diffrn_orient_matrix_UB_33      0.0068573000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3612
_reflns_number_total             3825
_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 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3825
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.078
_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)+(0.0345P)²+0.7896P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0912
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
2.b Idealised Me refined as rotating group:
 C26(H26C,H26A,H26B), C27(H27A,H27C,H27B)
;
_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
C1 C 0.63408(7) 0.4822(2) 0.66624(7) 0.0230(2) Uani 1 1 d . . . . .
C2 C 0.60980(7) 0.6813(2) 0.69189(7) 0.0271(3) Uani 1 1 d . . . . .
H2 H 0.646168 0.779990 0.717638 0.032 Uiso 1 1 calc R U . . .
C3 C 0.53157(8) 0.7349(2) 0.67946(7) 0.0289(3) Uani 1 1 d . . . . .
H3 H 0.515122 0.870232 0.697831 0.035 Uiso 1 1 calc R U . . .
C4 C 0.47704(7) 0.5961(2) 0.64099(7) 0.0279(3) Uani 1 1 d . . . . .
C5 C 0.50165(7) 0.3961(2) 0.61380(7) 0.0271(3) Uani 1 1 d . . . . .
C6 C 0.57964(7) 0.3422(2) 0.62713(7) 0.0253(2) Uani 1 1 d . . . . .
H6 H 0.596259 0.206684 0.609132 0.030 Uiso 1 1 calc R U . . .
C7 C 0.82877(7) 0.33069(19) 0.76024(7) 0.0228(2) Uani 1 1 d . . . . .
N8 N 0.79814(6) 0.15168(17) 0.73536(6) 0.0266(2) Uani 1 1 d . . . . .
O9 O 0.72499(5) 0.18969(13) 0.69213(5) 0.02515(19) Uani 1 1 d . . . . .
C10 C 0.71862(7) 0.41776(18) 0.67188(7) 0.0217(2) Uani 1 1 d . . . . .
C11 C 0.77376(7) 0.51475(19) 0.74022(7) 0.0227(2) Uani 1 1 d . . . . .
C12 C 0.90516(7) 0.3430(2) 0.80705(7) 0.0243(2) Uani 1 1 d . . . . .
C13 C 0.95448(8) 0.1643(2) 0.81106(7) 0.0297(3) Uani 1 1 d . . . . .
H13 H 0.939571 0.037349 0.781786 0.036 Uiso 1 1 calc R U . . .
C14 C 1.02532(8) 0.1736(3) 0.85805(8) 0.0365(3) Uani 1 1 d . . . . .
H14 H 1.058606 0.051995 0.861436 0.044 Uiso 1 1 calc R U . . .
C15 C 1.04768(8) 0.3600(3) 0.90010(8) 0.0374(3) Uani 1 1 d . . . . .
H15 H 1.096133 0.365302 0.932251 0.045 Uiso 1 1 calc R U . . .
C16 C 0.99963(8) 0.5381(2) 0.89532(8) 0.0341(3) Uani 1 1 d . . . . .
H16 H 1.015358 0.665753 0.923759 0.041 Uiso 1 1 calc R U . . .
C17 C 0.92849(7) 0.5304(2) 0.84903(7) 0.0282(3) Uani 1 1 d . . . . .
H17 H 0.895573 0.652768 0.845874 0.034 Uiso 1 1 calc R U . . .
C18 C 0.75133(7) 0.45423(19) 0.59115(7) 0.0225(2) Uani 1 1 d . . . . .
C19 C 0.78990(7) 0.2907(2) 0.55495(7) 0.0284(3) Uani 1 1 d . . . . .
H19 H 0.797600 0.155060 0.580737 0.034 Uiso 1 1 calc R U . . .
C20 C 0.81714(8) 0.3264(2) 0.48094(8) 0.0348(3) Uani 1 1 d . . . . .
H20 H 0.843544 0.214716 0.456354 0.042 Uiso 1 1 calc R U . . .
C21 C 0.80608(8) 0.5229(2) 0.44295(8) 0.0336(3) Uani 1 1 d . . . . .
H21 H 0.824232 0.545530 0.392079 0.040 Uiso 1 1 calc R U . . .
C22 C 0.76844(7) 0.6873(2) 0.47910(7) 0.0302(3) Uani 1 1 d . . . . .
H22 H 0.761288 0.823105 0.453265 0.036 Uiso 1 1 calc R U . . .
C23 C 0.74122(7) 0.6533(2) 0.55310(7) 0.0252(2) Uani 1 1 d . . . . .
H23 H 0.715609 0.766257 0.577878 0.030 Uiso 1 1 calc R U . . .
F24 F 0.80748(4) 0.69973(11) 0.72015(4) 0.02811(17) Uani 1 1 d . . . . .
F25 F 0.73780(4) 0.56121(13) 0.80726(4) 0.03043(18) Uani 1 1 d . . . . .
C26 C 0.44508(8) 0.2423(2) 0.56984(9) 0.0367(3) Uani 1 1 d . . . . .
H26C H 0.471736 0.108246 0.558931 0.055 Uiso 1 1 calc R U . . .
H26A H 0.423374 0.307196 0.518974 0.055 Uiso 1 1 calc R U . . .
H26B H 0.403286 0.211323 0.603000 0.055 Uiso 1 1 calc R U . . .
C27 C 0.39274(8) 0.6590(3) 0.62861(9) 0.0376(3) Uani 1 1 d . . . . .
H27A H 0.375292 0.662335 0.570951 0.056 Uiso 1 1 calc R U . . .
H27C H 0.386161 0.801749 0.651780 0.056 Uiso 1 1 calc R U . . .
H27B H 0.362045 0.553615 0.655054 0.056 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
C1 C2 1.3907(17) . ?
C1 C6 1.3951(17) . ?
C1 C10 1.5165(16) . ?
C2 H2 0.9500 . ?
C2 C3 1.3940(18) . ?
C3 H3 0.9500 . ?
C3 C4 1.3878(19) . ?
C4 C5 1.4058(18) . ?
C4 C27 1.5096(18) . ?
C5 C6 1.3913(17) . ?
C5 C26 1.5052(18) . ?
C6 H6 0.9500 . ?
C7 N8 1.2831(16) . ?
C7 C11 1.5053(16) . ?
C7 C12 1.4695(16) . ?
N8 O9 1.4136(13) . ?
O9 C10 1.4585(14) . ?
C10 C11 1.5342(16) . ?
C10 C18 1.5385(15) . ?
C11 F24 1.3493(13) . ?
C11 F25 1.3730(13) . ?
C12 C13 1.4003(17) . ?
C12 C17 1.3968(18) . ?
C13 H13 0.9500 . ?
C13 C14 1.3891(19) . ?
C14 H14 0.9500 . ?
C14 C15 1.389(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.383(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.3877(18) . ?
C17 H17 0.9500 . ?
C18 C19 1.3916(17) . ?
C18 C23 1.3939(17) . ?
C19 H19 0.9500 . ?
C19 C20 1.3911(18) . ?
C20 H20 0.9500 . ?
C20 C21 1.381(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.387(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.3891(17) . ?
C23 H23 0.9500 . ?
C26 H26C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27C 0.9800 . ?
C27 H27B 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
C2 C1 C6 119.09(11) . . ?
C2 C1 C10 122.71(11) . . ?
C6 C1 C10 117.95(11) . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.37(12) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.1 . . ?
C4 C3 C2 121.84(12) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 C5 118.88(11) . . ?
C3 C4 C27 120.48(12) . . ?
C5 C4 C27 120.63(12) . . ?
C4 C5 C26 120.90(12) . . ?
C6 C5 C4 119.10(12) . . ?
C6 C5 C26 119.99(12) . . ?
C1 C6 H6 119.1 . . ?
C5 C6 C1 121.71(12) . . ?
C5 C6 H6 119.1 . . ?
N8 C7 C11 110.79(10) . . ?
N8 C7 C12 122.54(11) . . ?
C12 C7 C11 126.52(11) . . ?
C7 N8 O9 109.89(10) . . ?
N8 O9 C10 108.84(8) . . ?
C1 C10 C11 117.79(10) . . ?
C1 C10 C18 110.76(9) . . ?
O9 C10 C1 108.64(9) . . ?
O9 C10 C11 100.53(9) . . ?
O9 C10 C18 108.73(9) . . ?
C11 C10 C18 109.65(9) . . ?
C7 C11 C10 101.44(9) . . ?
F24 C11 C7 114.82(10) . . ?
F24 C11 C10 113.73(9) . . ?
F24 C11 F25 105.84(9) . . ?
F25 C11 C7 108.20(9) . . ?
F25 C11 C10 112.88(9) . . ?
C13 C12 C7 119.86(11) . . ?
C17 C12 C7 120.55(11) . . ?
C17 C12 C13 119.58(12) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.68(13) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.27(13) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.22(13) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.06(14) . . ?
C17 C16 H16 120.0 . . ?
C12 C17 H17 119.9 . . ?
C16 C17 C12 120.17(13) . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C10 121.08(11) . . ?
C19 C18 C23 119.47(11) . . ?
C23 C18 C10 119.45(10) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.87(12) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.47(12) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 119.96(12) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 119.96(12) . . ?
C23 C22 H22 120.0 . . ?
C18 C23 H23 119.9 . . ?
C22 C23 C18 120.26(12) . . ?
C22 C23 H23 119.9 . . ?
C5 C26 H26C 109.5 . . ?
C5 C26 H26A 109.5 . . ?
C5 C26 H26B 109.5 . . ?
H26C C26 H26A 109.5 . . ?
H26C C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C4 C27 H27A 109.5 . . ?
C4 C27 H27C 109.5 . . ?
C4 C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27C C27 H27B 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
C1 C2 C3 C4 -0.98(19) . . . . ?
C1 C10 C11 C7 144.99(10) . . . . ?
C1 C10 C11 F24 -91.17(12) . . . . ?
C1 C10 C11 F25 29.43(14) . . . . ?
C1 C10 C18 C19 -127.91(12) . . . . ?
C1 C10 C18 C23 51.18(14) . . . . ?
C2 C1 C6 C5 -0.59(18) . . . . ?
C2 C1 C10 O9 143.18(11) . . . . ?
C2 C1 C10 C11 29.87(16) . . . . ?
C2 C1 C10 C18 -97.45(13) . . . . ?
C2 C3 C4 C5 -0.08(19) . . . . ?
C2 C3 C4 C27 179.91(12) . . . . ?
C3 C4 C5 C6 0.79(17) . . . . ?
C3 C4 C5 C26 -178.40(12) . . . . ?
C4 C5 C6 C1 -0.47(18) . . . . ?
C6 C1 C2 C3 1.30(17) . . . . ?
C6 C1 C10 O9 -42.65(13) . . . . ?
C6 C1 C10 C11 -155.97(10) . . . . ?
C6 C1 C10 C18 76.72(13) . . . . ?
C7 N8 O9 C10 15.34(12) . . . . ?
C7 C12 C13 C14 -177.35(11) . . . . ?
C7 C12 C17 C16 177.77(11) . . . . ?
N8 C7 C11 C10 -20.74(12) . . . . ?
N8 C7 C11 F24 -143.83(10) . . . . ?
N8 C7 C11 F25 98.22(11) . . . . ?
N8 C7 C12 C13 14.09(17) . . . . ?
N8 C7 C12 C17 -164.61(11) . . . . ?
N8 O9 C10 C1 -151.12(9) . . . . ?
N8 O9 C10 C11 -26.84(11) . . . . ?
N8 O9 C10 C18 88.25(10) . . . . ?
O9 C10 C11 C7 27.25(10) . . . . ?
O9 C10 C11 F24 151.08(9) . . . . ?
O9 C10 C11 F25 -88.31(11) . . . . ?
O9 C10 C18 C19 -8.59(15) . . . . ?
O9 C10 C18 C23 170.49(10) . . . . ?
C10 C1 C2 C3 175.40(11) . . . . ?
C10 C1 C6 C5 -174.97(11) . . . . ?
C10 C18 C19 C20 178.34(11) . . . . ?
C10 C18 C23 C22 -178.18(11) . . . . ?
C11 C7 N8 O9 4.34(13) . . . . ?
C11 C7 C12 C13 -170.83(11) . . . . ?
C11 C7 C12 C17 10.47(17) . . . . ?
C11 C10 C18 C19 100.43(13) . . . . ?
C11 C10 C18 C23 -80.49(13) . . . . ?
C12 C7 N8 O9 -179.90(9) . . . . ?
C12 C7 C11 C10 163.71(10) . . . . ?
C12 C7 C11 F24 40.61(15) . . . . ?
C12 C7 C11 F25 -77.34(13) . . . . ?
C12 C13 C14 C15 -0.82(19) . . . . ?
C13 C12 C17 C16 -0.93(18) . . . . ?
C13 C14 C15 C16 -0.2(2) . . . . ?
C14 C15 C16 C17 0.6(2) . . . . ?
C15 C16 C17 C12 -0.06(19) . . . . ?
C17 C12 C13 C14 1.36(18) . . . . ?
C18 C10 C11 C7 -87.16(11) . . . . ?
C18 C10 C11 F24 36.68(13) . . . . ?
C18 C10 C11 F25 157.29(9) . . . . ?
C18 C19 C20 C21 -0.1(2) . . . . ?
C19 C18 C23 C22 0.92(18) . . . . ?
C19 C20 C21 C22 0.8(2) . . . . ?
C20 C21 C22 C23 -0.66(19) . . . . ?
C21 C22 C23 C18 -0.21(18) . . . . ?
C23 C18 C19 C20 -0.75(19) . . . . ?
C26 C5 C6 C1 178.73(12) . . . . ?
C27 C4 C5 C6 -179.19(12) . . . . ?
C27 C4 C5 C26 1.61(18) . . . . ?

_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MiTeGEN Dual Thickness MicroLoops in  perfluoropolyether oil'
_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 0.755
####################################################################### 
# 
# 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_5aj_twin1_hklf4
_database_code_depnum_ccdc_archive 'CCDC 2349493'
loop_
_audit_author_name
_audit_author_address
Haruhiko
;Tokyo University of Pharmacy and Life Sciences
Japan
;
_audit_update_record             
;
2024-04-19 deposited with the CCDC.	2024-12-11 downloaded from the CCDC.
;
_audit_creation_date             2024-04-10
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
fukayah@toyaku.ac.jp
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H16 F2 N2 O'
_chemical_formula_sum            'C20 H16 F2 N2 O'
_chemical_formula_weight         338.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H16 F2 N O'
_chemical_oxdiff_usercomment     5aJ
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                   8.14050(10)
_cell_length_b                   12.07940(10)
_cell_length_c                   17.1421(3)
_cell_angle_alpha                96.3100(10)
_cell_angle_beta                 97.1640(10)
_cell_angle_gamma                93.9910(10)
_cell_volume                     1656.39(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    31356
_cell_measurement_temperature    120.0(5)
_cell_measurement_theta_max      77.1460
_cell_measurement_theta_min      2.6630
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.896
_exptl_absorpt_coefficient_mu    0.834
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.84a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane and ethylacetate'
_exptl_crystal_size_max          0.135
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13056
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.956
_diffrn_reflns_theta_min         2.617
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.0(5)
_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 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00  31.00   0.50    0.17    --  -43.07  82.00  79.00  210
  2  ω    -30.00  74.00   0.50    0.17    --   43.07 -82.00 -42.00  208
  3  ω   -136.00 -30.00   0.50    0.67    -- -104.50  82.00  79.00  212
  4  ω   -174.00 -79.00   0.50    0.67    -- -104.50 -82.00 -42.00  190
  5  ω     39.00 144.00   0.50    0.67    --  113.00 -82.00 -42.00  210
  6  ω     86.00 178.00   0.50    0.67    --  113.00  82.00  79.00  184
  7  ω    -25.00  38.00   0.50    0.17    --  -43.07  19.00-120.00  126
  8  ω    -25.00  38.00   0.50    0.17    --  -43.07  19.00 120.00  126
  9  ω    -25.00  38.00   0.50    0.17    --  -43.07  19.00   0.00  126
 10  ω     12.00 124.00   0.50    0.17    --   43.07  19.00   0.00  224
 11  ω    -30.00  65.00   0.50    0.17    --   43.07 -57.00-180.00  190
 12  ω     19.00  95.00   0.50    0.17    --   43.07-125.00 120.00  152
 13  ω   -123.00 -30.00   0.50    0.67    -- -104.50 140.00 -56.36  186
 14  ω     40.00 107.00   0.50    0.67    --  113.00-109.00 145.85  134
 15  ω     41.00 112.00   0.50    0.67    --  113.00-125.00 -90.00  142
 16  ω     39.00 106.00   0.50    0.67    --  113.00 -77.00 -30.00  134
 17  ω     40.00 108.00   0.50    0.67    --  113.00-108.00 -62.39  136
 18  ω     84.00 178.00   0.50    0.67    --  113.00  77.00-180.00  188
 19  ω     38.00 106.00   0.50    0.67    --  113.00 -95.00  90.00  136
 20  ω     90.00 178.00   0.50    0.67    --  113.00  61.00-150.00  176
 21  ω     91.00 178.00   0.50    0.67    --  113.00  45.00 -60.00  174
 22  ω     89.00 178.00   0.50    0.67    --  113.00  30.00-120.00  178
 23  ω     39.00  76.00   0.50    0.67    --  113.00 -61.00   0.00   74
 24  ω     39.00  76.00   0.50    0.67    --  113.00 -61.00 -30.00   74
 25  ω     90.00 178.00   0.50    0.67    --  113.00  61.00-120.00  176
 26  ω     39.00 106.00   0.50    0.67    --  113.00 -77.00  90.00  134
 27  ω     39.00  76.00   0.50    0.67    --  113.00 -61.00 120.00   74
 28  ω     41.00 112.00   0.50    0.67    --  113.00-125.00 -60.00  142
 29  ω     38.00 106.00   0.50    0.67    --  113.00 -95.00  60.00  136
 30  ω     89.00 178.00   0.50    0.67    --  113.00  30.00  60.00  178
 31  ω     39.00 106.00   0.50    0.67    --  113.00 -77.00 -90.00  134
 32  ω     41.00 110.00   0.50    0.67    --  113.00-123.00-101.27  138
 33  ω     89.00 178.00   0.50    0.67    --  113.00  30.00-180.00  178
 34  ω     90.00 178.00   0.50    0.67    --  113.00  61.00 120.00  176
 35  ω     90.00 178.00   0.50    0.67    --  113.00  57.00 -40.19  176
 36  ω     90.00 178.00   0.50    0.67    --  113.00  61.00 -90.00  176
 37  ω     39.00  76.00   0.50    0.67    --  113.00 -61.00  30.00   74
 38  ω     41.00 112.00   0.50    0.67    --  113.00-125.00 150.00  142
 39  ω     80.00 178.00   0.50    0.67    --  113.00 125.00 -60.00  196
 40  ω     40.00 106.00   0.50    0.67    --  113.00 -93.00 137.99  132
 41  ω     41.00 117.00   0.50    0.67    --  113.00-133.00  76.88  152
 42  ω     39.00 106.00   0.50    0.67    --  113.00 -77.00-120.00  134
 43  ω     91.00 178.00   0.50    0.67    --  113.00  45.00  60.00  174
 44  ω     80.00 178.00   0.50    0.67    --  113.00 125.00  60.00  196
 45  ω     39.00 106.00   0.50    0.67    --  113.00 -77.00-180.00  134
 46  ω     38.00 106.00   0.50    0.67    --  113.00 -95.00 -60.00  136
 47  ω     38.00 106.00   0.50    0.67    --  113.00 -95.00 120.00  136
 48  ω     91.00 178.00   0.50    0.67    --  113.00  45.00  30.00  174
 49  ω     89.00 178.00   0.50    0.67    --  113.00  30.00   0.00  178
 50  ω     41.00 112.00   0.50    0.67    --  113.00-125.00  90.00  142
 51  ω     39.00  76.00   0.50    0.67    --  113.00 -61.00-180.00   74
 52  ω     39.00  76.00   0.50    0.67    --  113.00 -61.00  60.00   74
 53  ω     39.00  76.00   0.50    0.67    --  113.00 -61.00 150.00   74
 54  ω     39.00 121.00   0.50    0.67    --  113.00-138.00-130.24  164
 55  ω     89.00 178.00   0.50    0.67    --  113.00  30.00 120.00  178
 56  ω     39.00 106.00   0.50    0.67    --  113.00 -77.00 150.00  134
 57  ω     38.00 106.00   0.50    0.67    --  113.00 -95.00 -30.00  136
 58  ω     38.00 106.00   0.50    0.67    --  113.00 -95.00   0.00  136
 59  ω     41.00 112.00   0.50    0.67    --  113.00-125.00 -30.00  142
 60  ω     41.00 112.00   0.50    0.67    --  113.00-125.00  60.00  142
 61  ω     41.00 112.00   0.50    0.67    --  113.00-125.00 120.00  142
 62  ω     39.00 113.00   0.50    0.67    --  113.00 -79.00 171.54  148
 63  ω     39.00 130.00   0.50    0.67    --  113.00-151.00  40.72  182
 64  ω     84.00 178.00   0.50    0.67    --  113.00  77.00  60.00  188
 65  ω     90.00 178.00   0.50    0.67    --  113.00  61.00 150.00  176
 66  ω     14.00 117.00   0.50    0.17    --   43.07  77.00-180.00  206
 67  ω     14.00 117.00   0.50    0.17    --   43.07  77.00   0.00  206
 68  ω     14.00 117.00   0.50    0.17    --   43.07  77.00 -60.00  206
 69  ω     21.00 117.00   0.50    0.17    --   43.07  57.00 150.00  192
 70  ω     21.00 117.00   0.50    0.17    --   43.07  57.00  60.00  192
 71  ω      9.00  42.00   0.50    0.17    --   43.07  89.00  67.39   66
 72  ω     21.00 120.00   0.50    0.17    --   43.07  38.00 150.00  198
 73  ω     14.00 117.00   0.50    0.17    --   43.07  77.00-120.00  206
 74  ω     21.00 120.00   0.50    0.17    --   43.07  38.00  30.00  198
 75  ω     14.00 117.00   0.50    0.17    --   43.07  77.00  60.00  206
 76  ω     21.00 117.00   0.50    0.17    --   43.07  57.00-150.00  192
 77  ω     21.00 117.00   0.50    0.17    --   43.07  57.00 -90.00  192
 78  ω   -174.00 -75.00   0.50    0.67    -- -104.50 -77.00  41.84  198
 79  ω   -174.00 -76.00   0.50    0.67    -- -104.50 -75.00-177.09  196
 80  ω   -174.00 -75.00   0.50    0.67    -- -104.50 -77.00   0.00  198
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0842134000
_diffrn_orient_matrix_UB_12      0.0036962000
_diffrn_orient_matrix_UB_13      -0.0754287000
_diffrn_orient_matrix_UB_21      -0.1073035000
_diffrn_orient_matrix_UB_22      0.0938097000
_diffrn_orient_matrix_UB_23      -0.0244314000
_diffrn_orient_matrix_UB_31      0.1342961000
_diffrn_orient_matrix_UB_32      0.0881407000
_diffrn_orient_matrix_UB_33      0.0451366000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                11518
_reflns_number_total             13056
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     546
_refine_ls_number_reflns         13056
_refine_ls_number_restraints     169
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0486
_refine_ls_restrained_S_all      1.074
_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)+(0.0732P)²+0.6159P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1357
_refine_ls_wR_factor_ref         0.1394
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.6885(9)
 0.3115(9)
2. 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
3. Restrained distances
 C3A-C15A \\sim C3A-C15B
 with sigma of 0.02
 C16A-C18A \\sim C16B-C18B
 with sigma of 0.04
 C15A-C16A \\sim C15B-C16B
 with sigma of 0.02
 C15A-C20A \\sim C15B-C20B
 with sigma of 0.02
 C16A-C17A \\sim C16B-C17B
 with sigma of 0.02
 C17A-C18A \\sim C17B-C18B
 with sigma of 0.02
 C18A-C19A \\sim C18B-C19B
 with sigma of 0.02
 C16A-C20A \\sim C16B-C20B
 with sigma of 0.04
 C19A-C20A \\sim C19B-C20B
 with sigma of 0.02
 C17A-C19A \\sim C17B-C19B
 with sigma of 0.04
 C18A-C20A \\sim C18B-C20B
 with sigma of 0.04
 C3A-C16A \\sim C3A-C16B
 with sigma of 0.04
 C3A-C20A \\sim C3A-C20B
 with sigma of 0.04
 C15A-C17A \\sim C15B-C17B
 with sigma of 0.04
 C15A-C19A \\sim C15B-C19B
 with sigma of 0.04
 C15-C19 \\sim C15-C1C
 with sigma of 0.04
 C15-C20 \\sim C15-C1D
 with sigma of 0.02
 C16-C17 \\sim C21-C1B
 with sigma of 0.02
 C18-C20 \\sim C18-C1D
 with sigma of 0.04
 C17-C18 \\sim C1B-C18
 with sigma of 0.02
 C15-C17 \\sim C15-C1B
 with sigma of 0.04
 C16-C18 \\sim C21-C18
 with sigma of 0.04
 C19-C20 \\sim C1C-C1D
 with sigma of 0.02
 C18-C19 \\sim C18-C1C
 with sigma of 0.02
 C15-C16 \\sim C15-C21
 with sigma of 0.02
4. Rigid body (RIGU) restrains
 C15A, C15B, C16A, C16B, C17A, C17B, C18A, C18B, C19A, C19B, C20A, C20B
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 C1B, C1C, C1D, C15, C16, C17, C18, C19, C20, C21
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
5. Others
 Sof(C15B)=Sof(C16B)=Sof(H16B)=Sof(C17B)=Sof(H17B)=Sof(C18B)=Sof(H18B)=
 Sof(C19B)=Sof(H19B)=Sof(C20B)=Sof(H20B)=1-FVAR(1)
 Sof(C15A)=Sof(C16A)=Sof(H16A)=Sof(C17A)=Sof(H17A)=Sof(C18A)=Sof(H18A)=
 Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20A)=FVAR(1)
 Sof(C1B)=Sof(H1B)=Sof(C1C)=Sof(H1C)=Sof(C1D)=Sof(H1D)=Sof(H18C)=Sof(C21)=
 Sof(H21)=1-FVAR(2)
 Sof(C16)=Sof(H16)=Sof(C17)=Sof(H17)=Sof(H18)=Sof(C19)=Sof(H19)=Sof(C20)=
 Sof(H20)=FVAR(2)
6.a Aromatic/amide H refined with riding coordinates:
 C1B(H1B), C1C(H1C), C1D(H1D), C5(H5), C5A(H5A), C6(H6), C6A(H6A), C7(H7),
 C7A(H7A), C8(H8), C8A(H8A), C9(H9), C9A(H9A), C11(H11), C11A(H11A), C12(H12),
 C12A(H12A), C13(H13), C13A(H13A), C16(H16), C16A(H16A), C16B(H16B), C17(H17),
 C17A(H17A), C17B(H17B), C18(H18), C18(H18C), C18A(H18A), C18B(H18B), C19(H19),
 C19A(H19A), C19B(H19B), C20(H20), C20A(H20A), C20B(H20B), C21(H21)
6.b Idealised Me refined as rotating group:
 C14(H14D,H14E,H14F), C14A(H14A,H14B,H14C)
;
_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
C1 C 0.7754(2) 0.15671(14) 0.20655(11) 0.0208(4) Uani 1 1 d . . . . .
C1A C 0.5536(2) 0.65626(14) 0.23258(11) 0.0209(4) Uani 1 1 d . . . . .
C1B C 0.9176(18) 0.3735(6) 0.5357(4) 0.049(2) Uani 0.50(2) 1 d D . P A 2
H1B H 0.933440 0.451318 0.553220 0.059 Uiso 0.50(2) 1 calc R U P A 2
C1C C 0.883(2) 0.1867(6) 0.5664(3) 0.052(2) Uani 0.50(2) 1 d D . P A 2
H1C H 0.873848 0.135456 0.604308 0.062 Uiso 0.50(2) 1 calc R U P A 2
C1D C 0.8649(19) 0.1472(5) 0.4865(3) 0.0433(19) Uani 0.50(2) 1 d D . P A 2
H1D H 0.845227 0.069175 0.470162 0.052 Uiso 0.50(2) 1 calc R U P A 2
C2 C 0.8273(2) 0.24867(16) 0.27684(11) 0.0247(4) Uani 1 1 d . . . . .
C2A C 0.5483(2) 0.61735(15) 0.31445(11) 0.0246(4) Uani 1 1 d . . . . .
C3 C 0.8592(2) 0.17996(16) 0.34494(12) 0.0251(4) Uani 1 1 d . . . . .
C3A C 0.5530(2) 0.72728(16) 0.36666(11) 0.0242(4) Uani 1 1 d D . . . .
C4 C 0.5869(2) 0.12752(15) 0.19771(10) 0.0199(4) Uani 1 1 d . . . . .
C4A C 0.7344(2) 0.67768(15) 0.21765(10) 0.0206(4) Uani 1 1 d . . . . .
C5 C 0.5201(2) 0.03653(15) 0.23010(12) 0.0240(4) Uani 1 1 d . . . . .
H5 H 0.591393 -0.007588 0.259399 0.029 Uiso 1 1 calc R U . . .
C5A C 0.8163(2) 0.58881(17) 0.18623(12) 0.0278(4) Uani 1 1 d . . . . .
H5A H 0.761144 0.515759 0.175712 0.033 Uiso 1 1 calc R U . . .
C6 C 0.3492(2) 0.01011(16) 0.21967(13) 0.0273(4) Uani 1 1 d . . . . .
H6 H 0.304305 -0.052851 0.241072 0.033 Uiso 1 1 calc R U . . .
C6A C 0.9791(3) 0.60730(19) 0.17030(13) 0.0333(5) Uani 1 1 d . . . . .
H6A H 1.034670 0.546652 0.149059 0.040 Uiso 1 1 calc R U . . .
C7 C 0.2441(2) 0.07505(17) 0.17827(12) 0.0278(4) Uani 1 1 d . . . . .
H7 H 0.127352 0.056881 0.171421 0.033 Uiso 1 1 calc R U . . .
C7A C 1.0604(2) 0.71373(19) 0.18528(13) 0.0310(4) Uani 1 1 d . . . . .
H7A H 1.171093 0.726138 0.174043 0.037 Uiso 1 1 calc R U . . .
C8 C 0.3096(2) 0.16661(17) 0.14686(12) 0.0275(4) Uani 1 1 d . . . . .
H8 H 0.237397 0.211742 0.119004 0.033 Uiso 1 1 calc R U . . .
C8A C 0.9796(2) 0.80157(18) 0.21661(13) 0.0287(4) Uani 1 1 d . . . . .
H8A H 1.035036 0.874552 0.226774 0.034 Uiso 1 1 calc R U . . .
C9 C 0.4809(2) 0.19289(16) 0.15588(11) 0.0237(4) Uani 1 1 d . . . . .
H9 H 0.525319 0.255166 0.133604 0.028 Uiso 1 1 calc R U . . .
C9A C 0.8170(2) 0.78391(16) 0.23347(12) 0.0244(4) Uani 1 1 d . . . . .
H9A H 0.762880 0.844573 0.255760 0.029 Uiso 1 1 calc R U . . .
C10 C 0.8330(2) 0.17817(16) 0.12959(11) 0.0222(4) Uani 1 1 d . . . . .
C10A C 0.4506(2) 0.58505(15) 0.16431(11) 0.0224(4) Uani 1 1 d . . . . .
C11 C 0.9002(2) 0.27408(17) 0.10451(12) 0.0255(4) Uani 1 1 d . . . . .
H11 H 0.927253 0.344517 0.135683 0.031 Uiso 1 1 calc R U . . .
C11A C 0.3744(2) 0.47810(16) 0.15762(13) 0.0270(4) Uani 1 1 d . . . . .
H11A H 0.370309 0.432093 0.198979 0.032 Uiso 1 1 calc R U . . .
C12 C 0.9215(2) 0.24862(18) 0.02416(12) 0.0292(4) Uani 1 1 d . . . . .
H12 H 0.964883 0.298619 -0.008748 0.035 Uiso 1 1 calc R U . . .
C12A C 0.3037(2) 0.44990(17) 0.07791(13) 0.0295(4) Uani 1 1 d . . . . .
H12A H 0.243741 0.381060 0.055683 0.035 Uiso 1 1 calc R U . . .
C13 C 0.8679(2) 0.13843(19) 0.00274(12) 0.0297(4) Uani 1 1 d . . . . .
H13 H 0.869088 0.098284 -0.048029 0.036 Uiso 1 1 calc R U . . .
C13A C 0.3370(2) 0.53908(17) 0.03852(12) 0.0287(4) Uani 1 1 d . . . . .
H13A H 0.302866 0.543210 -0.016069 0.034 Uiso 1 1 calc R U . . .
C14 C 0.7409(3) -0.01947(17) 0.06344(13) 0.0325(4) Uani 1 1 d . . . . .
H14D H 0.795510 -0.053671 0.107930 0.049 Uiso 1 1 calc R U . . .
H14E H 0.757429 -0.062343 0.013488 0.049 Uiso 1 1 calc R U . . .
H14F H 0.621694 -0.019473 0.067072 0.049 Uiso 1 1 calc R U . . .
C14A C 0.4935(3) 0.72726(17) 0.06758(12) 0.0292(4) Uani 1 1 d . . . . .
H14A H 0.474175 0.789036 0.106523 0.044 Uiso 1 1 calc R U . . .
H14B H 0.437591 0.738066 0.015274 0.044 Uiso 1 1 calc R U . . .
H14C H 0.613111 0.725458 0.065615 0.044 Uiso 1 1 calc R U . . .
C15 C 0.8757(3) 0.22125(19) 0.42972(12) 0.0320(4) Uani 1 1 d D . . . .
C15A C 0.590(6) 0.7444(10) 0.4538(6) 0.0289(17) Uani 0.50(2) 1 d D . P B 1
C15B C 0.588(6) 0.7441(11) 0.4528(7) 0.0296(17) Uani 0.50(2) 1 d D . P B 2
C16 C 0.8380(15) 0.3278(6) 0.4560(3) 0.0378(15) Uani 0.50(2) 1 d D . P A 1
H16 H 0.798774 0.375991 0.418864 0.045 Uiso 0.50(2) 1 calc R U P A 1
C16A C 0.6370(13) 0.6560(5) 0.4956(3) 0.0330(14) Uani 0.50(2) 1 d D . P B 1
H16A H 0.648373 0.585029 0.467919 0.040 Uiso 0.50(2) 1 calc R U P B 1
C16B C 0.5769(17) 0.6577(5) 0.4983(4) 0.0415(18) Uani 0.50(2) 1 d D . P B 2
H16B H 0.545909 0.583588 0.473616 0.050 Uiso 0.50(2) 1 calc R U P B 2
C17 C 0.8576(17) 0.3646(7) 0.5370(4) 0.046(2) Uani 0.50(2) 1 d D . P A 1
H17 H 0.832437 0.438139 0.554561 0.055 Uiso 0.50(2) 1 calc R U P A 1
C17A C 0.6671(15) 0.6723(6) 0.5779(4) 0.0402(17) Uani 0.50(2) 1 d D . P B 1
H17A H 0.691147 0.611119 0.606559 0.048 Uiso 0.50(2) 1 calc R U P B 1
C17B C 0.6112(19) 0.6782(6) 0.5808(4) 0.051(2) Uani 0.50(2) 1 d D . P B 2
H17B H 0.613201 0.617091 0.611197 0.061 Uiso 0.50(2) 1 calc R U P B 2
C18 C 0.9119(4) 0.2968(2) 0.59089(15) 0.0459(5) Uani 1 1 d D . . . .
H18 H 0.922655 0.321891 0.645925 0.055 Uiso 0.50(2) 1 calc R U P A 1
H18C H 0.928797 0.322543 0.645911 0.055 Uiso 0.50(2) 1 calc R U P A 2
C18A C 0.662(2) 0.7742(7) 0.6169(6) 0.0399(17) Uani 0.50(2) 1 d D . P B 1
H18A H 0.651758 0.783191 0.671771 0.048 Uiso 0.50(2) 1 calc R U P B 1
C18B C 0.642(2) 0.7856(8) 0.6187(6) 0.045(2) Uani 0.50(2) 1 d D . P B 2
H18B H 0.693057 0.801587 0.672135 0.054 Uiso 0.50(2) 1 calc R U P B 2
C19 C 0.9528(16) 0.1874(6) 0.5642(4) 0.0474(17) Uani 0.50(2) 1 d D . P A 1
H19 H 0.993435 0.139750 0.601458 0.057 Uiso 0.50(2) 1 calc R U P A 1
C19A C 0.6727(18) 0.8687(5) 0.5744(3) 0.046(2) Uani 0.50(2) 1 d D . P B 1
H19A H 0.702194 0.941417 0.601860 0.055 Uiso 0.50(2) 1 calc R U P B 1
C19B C 0.5961(17) 0.8650(5) 0.5752(3) 0.0445(17) Uani 0.50(2) 1 d D . P B 2
H19B H 0.582551 0.936785 0.601041 0.053 Uiso 0.50(2) 1 calc R U P B 2
C20 C 0.9330(15) 0.1507(5) 0.4839(3) 0.0391(15) Uani 0.50(2) 1 d D . P A 1
H20 H 0.958625 0.077448 0.465989 0.047 Uiso 0.50(2) 1 calc R U P A 1
C20A C 0.6393(17) 0.8535(5) 0.4924(3) 0.0394(17) Uani 0.50(2) 1 d D . P B 1
H20A H 0.649422 0.915032 0.462743 0.047 Uiso 0.50(2) 1 calc R U P B 1
C20B C 0.5669(16) 0.8468(5) 0.4933(3) 0.0385(15) Uani 0.50(2) 1 d D . P B 2
H20B H 0.532038 0.905704 0.464424 0.046 Uiso 0.50(2) 1 calc R U P B 2
C21 C 0.9000(18) 0.3361(5) 0.4549(3) 0.0422(18) Uani 0.50(2) 1 d D . P A 2
H21 H 0.904580 0.388052 0.417313 0.051 Uiso 0.50(2) 1 calc R U P A 2
F1 F 0.71264(16) 0.32326(10) 0.28472(7) 0.0333(3) Uani 1 1 d . . . . .
F1A F 0.67225(17) 0.55272(10) 0.33519(7) 0.0349(3) Uani 1 1 d . . . . .
F2 F 0.97216(16) 0.31023(11) 0.27145(7) 0.0361(3) Uani 1 1 d . . . . .
F2A F 0.40378(17) 0.55561(10) 0.32071(7) 0.0359(3) Uani 1 1 d . . . . .
N1 N 0.8827(2) 0.07870(14) 0.32014(9) 0.0257(3) Uani 1 1 d . . . . .
N1A N 0.5086(2) 0.80521(13) 0.32564(9) 0.0246(3) Uani 1 1 d . . . . .
N2 N 0.8123(2) 0.09522(14) 0.06614(9) 0.0252(3) Uani 1 1 d . . . . .
N2A N 0.4274(2) 0.62170(14) 0.09043(10) 0.0239(3) Uani 1 1 d . . . . .
O1 O 0.85939(16) 0.06334(11) 0.23602(8) 0.0230(3) Uani 1 1 d . . . . .
O1A O 0.48229(16) 0.76410(10) 0.24393(8) 0.0220(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.542(3) . ?
C1 C4 1.535(2) . ?
C1 C10 1.497(3) . ?
C1 O1 1.463(2) . ?
C1A C2A 1.533(3) . ?
C1A C4A 1.534(2) . ?
C1A C10A 1.499(3) . ?
C1A O1A 1.466(2) . ?
C1B C18 1.398(7) . ?
C1B C21 1.395(7) . ?
C1C C1D 1.387(7) . ?
C1C C18 1.346(7) . ?
C1D C15 1.399(6) . ?
C2 C3 1.512(3) . ?
C2 F1 1.350(2) . ?
C2 F2 1.368(2) . ?
C2A C3A 1.513(3) . ?
C2A F1A 1.355(2) . ?
C2A F2A 1.371(2) . ?
C3 C15 1.470(3) . ?
C3 N1 1.285(3) . ?
C3A C15A 1.475(11) . ?
C3A C15B 1.457(11) . ?
C3A N1A 1.281(3) . ?
C4 C5 1.392(3) . ?
C4 C9 1.396(2) . ?
C4A C5A 1.396(3) . ?
C4A C9A 1.390(3) . ?
C5 C6 1.390(3) . ?
C5A C6A 1.394(3) . ?
C6 C7 1.384(3) . ?
C6A C7A 1.387(3) . ?
C7 C8 1.385(3) . ?
C7A C8A 1.381(3) . ?
C8 C9 1.394(3) . ?
C8A C9A 1.397(3) . ?
C10 C11 1.381(3) . ?
C10 N2 1.381(2) . ?
C10A C11A 1.380(3) . ?
C10A N2A 1.382(2) . ?
C11 C12 1.413(3) . ?
C11A C12A 1.410(3) . ?
C12 C13 1.367(3) . ?
C12A C13A 1.362(3) . ?
C13 N2 1.368(3) . ?
C13A N2A 1.367(3) . ?
C14 N2 1.458(3) . ?
C14A N2A 1.461(2) . ?
C15 C16 1.384(6) . ?
C15 C20 1.389(6) . ?
C15 C21 1.399(6) . ?
C15A C16A 1.399(14) . ?
C15A C20A 1.415(15) . ?
C15B C16B 1.375(15) . ?
C15B C20B 1.386(16) . ?
C16 C17 1.397(7) . ?
C16A C17A 1.391(7) . ?
C16B C17B 1.397(7) . ?
C17 C18 1.354(7) . ?
C17A C18A 1.340(8) . ?
C17B C18B 1.377(10) . ?
C18 C19 1.426(7) . ?
C18A C19A 1.424(10) . ?
C18B C19B 1.324(10) . ?
C19 C20 1.385(7) . ?
C19A C20A 1.387(6) . ?
C19B C20B 1.385(6) . ?
N1 O1 1.421(2) . ?
N1A O1A 1.418(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 C1 C2 109.47(15) . . ?
C10 C1 C2 116.29(15) . . ?
C10 C1 C4 112.03(15) . . ?
O1 C1 C2 100.65(14) . . ?
O1 C1 C4 108.72(14) . . ?
O1 C1 C10 108.89(14) . . ?
C2A C1A C4A 110.10(15) . . ?
C10A C1A C2A 116.33(15) . . ?
C10A C1A C4A 111.90(15) . . ?
O1A C1A C2A 100.70(14) . . ?
O1A C1A C4A 108.49(14) . . ?
O1A C1A C10A 108.51(14) . . ?
C21 C1B C18 120.2(6) . . ?
C18 C1C C1D 120.6(5) . . ?
C1C C1D C15 120.6(5) . . ?
C3 C2 C1 101.52(15) . . ?
F1 C2 C1 112.97(15) . . ?
F1 C2 C3 115.38(16) . . ?
F1 C2 F2 105.74(15) . . ?
F2 C2 C1 113.46(16) . . ?
F2 C2 C3 107.91(15) . . ?
C3A C2A C1A 101.82(15) . . ?
F1A C2A C1A 113.17(15) . . ?
F1A C2A C3A 114.83(16) . . ?
F1A C2A F2A 105.66(15) . . ?
F2A C2A C1A 113.52(16) . . ?
F2A C2A C3A 107.96(15) . . ?
C15 C3 C2 126.36(18) . . ?
N1 C3 C2 111.30(17) . . ?
N1 C3 C15 122.18(18) . . ?
C15A C3A C2A 126.1(5) . . ?
C15B C3A C2A 126.2(5) . . ?
N1A C3A C2A 110.90(17) . . ?
N1A C3A C15A 122.8(6) . . ?
N1A C3A C15B 122.7(6) . . ?
C5 C4 C1 121.19(16) . . ?
C5 C4 C9 119.46(17) . . ?
C9 C4 C1 119.35(16) . . ?
C5A C4A C1A 119.20(16) . . ?
C9A C4A C1A 121.36(16) . . ?
C9A C4A C5A 119.43(17) . . ?
C6 C5 C4 120.15(17) . . ?
C6A C5A C4A 119.99(19) . . ?
C7 C6 C5 120.34(18) . . ?
C7A C6A C5A 120.38(19) . . ?
C6 C7 C8 119.81(18) . . ?
C8A C7A C6A 119.66(18) . . ?
C7 C8 C9 120.36(17) . . ?
C7A C8A C9A 120.49(19) . . ?
C8 C9 C4 119.87(18) . . ?
C4A C9A C8A 120.04(18) . . ?
C11 C10 C1 131.59(17) . . ?
C11 C10 N2 107.62(17) . . ?
N2 C10 C1 120.66(17) . . ?
C11A C10A C1A 131.61(18) . . ?
C11A C10A N2A 107.77(17) . . ?
N2A C10A C1A 120.49(16) . . ?
C10 C11 C12 107.69(18) . . ?
C10A C11A C12A 107.18(18) . . ?
C13 C12 C11 107.02(18) . . ?
C13A C12A C11A 107.70(18) . . ?
C12 C13 N2 109.08(18) . . ?
C12A C13A N2A 108.80(18) . . ?
C1D C15 C3 120.9(3) . . ?
C1D C15 C21 118.8(4) . . ?
C16 C15 C3 121.8(3) . . ?
C16 C15 C20 120.0(4) . . ?
C20 C15 C3 118.2(3) . . ?
C21 C15 C3 120.3(3) . . ?
C16A C15A C3A 120.4(10) . . ?
C16A C15A C20A 116.3(14) . . ?
C20A C15A C3A 119.2(10) . . ?
C16B C15B C3A 122.6(10) . . ?
C16B C15B C20B 113.0(15) . . ?
C20B C15B C3A 119.6(11) . . ?
C15 C16 C17 120.1(5) . . ?
C17A C16A C15A 119.9(7) . . ?
C15B C16B C17B 120.3(7) . . ?
C18 C17 C16 120.8(6) . . ?
C18A C17A C16A 120.2(6) . . ?
C18B C17B C16B 121.2(7) . . ?
C1C C18 C1B 120.3(4) . . ?
C17 C18 C19 119.4(4) . . ?
C17A C18A C19A 118.6(8) . . ?
C19B C18B C17B 115.0(9) . . ?
C20 C19 C18 119.9(5) . . ?
C20A C19A C18A 119.3(6) . . ?
C18B C19B C20B 122.3(6) . . ?
C19 C20 C15 119.8(5) . . ?
C19A C20A C15A 118.7(6) . . ?
C19B C20B C15B 121.1(6) . . ?
C1B C21 C15 119.4(5) . . ?
C3 N1 O1 109.58(15) . . ?
C3A N1A O1A 109.99(15) . . ?
C10 N2 C14 127.60(17) . . ?
C13 N2 C10 108.58(17) . . ?
C13 N2 C14 123.80(17) . . ?
C10A N2A C14A 127.56(16) . . ?
C13A N2A C10A 108.54(17) . . ?
C13A N2A C14A 123.82(17) . . ?
N1 O1 C1 109.35(13) . . ?
N1A O1A C1A 109.11(13) . . ?


_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MiTeGEN Dual Thickness MicroLoops in  perfluoropolyether oil'
_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 1.462
_oxdiff_exptl_absorpt_empirical_full_min 0.745
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.6885(9) 34247 29318 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.3115(9) 33996 29318 nmt -0.9997 0.0003 0.0015 -0.0004 -0.9999 0.0010 0.5664
0.3395 0.9990

_twin_special_details            
;
Component 2 rotated by -179.9757° 
around [0.00 0.00 1.00] (reciprocal) or [0.27 0.16 0.95] (direct)
;
