# Electronic Supplementary Material (ESI) for Molecular Systems Design & Engineering.
# 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_AIcouma_two_auto
_database_code_depnum_ccdc_archive 'CCDC 2219768'
loop_
_audit_author_name
_audit_author_address
'Ayano Ikemura'
;Gifu University
Japan
;
_audit_update_record             
;
2022-11-15 deposited with the CCDC.	2024-02-21 downloaded from the CCDC.
;
_audit_creation_date             2022-11-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_publ_section_exptl              
;
Any special experimental details
;
_chemical_name_common            ?
_chemical_name_systematic        7-(benzyloxy)-2H-chromen-2-one
_chemical_formula_moiety         'C16 H12 O3'
_chemical_formula_sum            'C16 H12 O3'
_chemical_formula_weight         252.26
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H12O3
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'
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   4.4183(2)
_cell_length_b                   10.1778(4)
_cell_length_c                   13.9165(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.256(4)
_cell_angle_gamma                90
_cell_volume                     625.32(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2153
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.2830
_cell_measurement_theta_min      3.1530
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.754
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3182
_diffrn_reflns_point_group_measured_fraction_full 0.841
_diffrn_reflns_point_group_measured_fraction_max 0.824
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.751
_diffrn_reflns_theta_min         3.178
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     81.00 114.00   0.50    0.20    --   97.43  50.00   0.00   66
  2  ω    121.00 164.00   0.50    0.20    --   97.43  50.00   0.00   86
  3  ω     93.00 163.00   0.50    0.20    --   97.43  33.00 -90.00  140
  4  ω     48.00  99.00   0.50    0.20    --   97.43 -96.00  90.00  102
  5  ω     58.00  86.00   0.50    0.20    --   44.40-128.00 -84.00   56
  6  ω     24.00  52.00   0.50    0.20    --   44.40-128.00 -84.00   56
  7  ω     69.00 106.00   0.50    0.20    --   97.43-117.00-150.00   74
  8  ω     29.00 104.00   0.50    0.20    --   97.43 -77.00-120.00  150
  9  ω     31.00  65.00   0.50    0.20    --   97.43 -59.00-120.00   68
 10  ω     34.00  63.00   0.50    0.20    --   97.43 -59.00 -60.00   58
 11  ω      4.00  35.00   0.50    0.20    --   44.40 -32.00-120.00   62
 12  ω     31.00  56.00   0.50    0.20    --   97.43 -50.00  30.00   50
 13  ω     32.00  57.00   0.50    0.20    --   97.43 -50.00 120.00   50
 14  ω     31.00  56.00   0.50    0.20    --   97.43 -50.00 150.00   50
 15  ω     99.00 125.00   0.50    0.20    --   97.43 128.00  -9.00   52
 16  ω     69.00 101.00   0.50    0.20    --   44.40 142.00 160.00   64
 17  ω     72.00 124.00   0.50    0.20    --   97.43 142.00 160.00  104
 18  ω    -32.00  -7.00   0.50    0.20    --  -42.84  32.00-120.00   50
 19  ω    -67.00 -33.00   0.50    0.20    --  -95.86  59.00-180.00   68
 20  ω     -5.00  23.00   0.50    0.20    --  -42.84  32.00-120.00   56
 21  ω    -57.00 -32.00   0.50    0.20    --  -95.86  50.00 120.00   50
 22  ω   -124.00 -69.00   0.50    0.20    --  -95.86 142.00 160.00  110
 23  ω    -84.00 -59.00   0.50    0.20    --  -42.84 142.00 160.00   50
 24  ω    -75.00 -33.00   0.50    0.20    --  -42.84 128.00  -9.00   84
 25  ω   -114.00 -60.00   0.50    0.20    --  -95.86 128.00  -9.00  108
 26  ω    -99.00 -49.00   0.50    0.20    --  -42.84 -32.00 150.00  100
 27  ω   -126.00 -97.00   0.50    0.20    --  -95.86 -33.00 120.00   58
 28  ω   -160.00-131.00   0.50    0.20    --  -95.86 -33.00 120.00   58
 29  ω   -106.00 -67.00   0.50    0.20    --  -42.84 -43.00  60.00   78
 30  ω    -54.00 -29.00   0.50    0.20    --  -42.84 -43.00  60.00   50
 31  ω   -114.00 -83.00   0.50    0.20    --  -95.86 -17.00 -90.00   62
 32  ω   -144.00-119.00   0.50    0.20    --  -95.86 -33.00-150.00   50
 33  ω   -110.00 -85.00   0.50    0.20    --  -42.84-138.00-150.00   50
 34  ω    -93.00 -68.00   0.50    0.20    --  -42.84-142.00 104.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2549645000
_diffrn_orient_matrix_UB_12      -0.1027717000
_diffrn_orient_matrix_UB_13      0.0114667000
_diffrn_orient_matrix_UB_21      0.2375955000
_diffrn_orient_matrix_UB_22      0.1108652000
_diffrn_orient_matrix_UB_23      0.0028392000
_diffrn_orient_matrix_UB_31      -0.0188936000
_diffrn_orient_matrix_UB_32      0.0078851000
_diffrn_orient_matrix_UB_33      0.1101215000
_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         0.572
_reflns_Friedel_fraction_full    0.663
_reflns_Friedel_fraction_max     0.637
_reflns_number_gt                1790
_reflns_number_total             1957
_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 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 
;
 Flack x determined using 597 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(2)
_refine_ls_extinction_coef       0.026(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         1957
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0512
_refine_ls_restrained_S_all      1.043
_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)+(0.1140P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1600
_refine_ls_wR_factor_ref         0.1600
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
1.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C14(H14), C5(H5), C4(H4), C7(H7), C16(H16), C17(H17), C8(H8),
 C18(H18), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O10 O 0.1728(6) 0.3153(2) 0.45222(17) 0.0584(7) Uani 1 1 d . . . . .
O11 O 0.7277(6) 0.5176(3) 0.20519(19) 0.0625(7) Uani 1 1 d . . . . .
O19 O -0.1002(8) 0.2297(4) 0.5661(2) 0.0820(9) Uani 1 1 d . . . . .
C2 C 0.4410(7) 0.4194(4) 0.3322(3) 0.0497(7) Uani 1 1 d . . . . .
H2 H 0.369886 0.500052 0.353272 0.060 Uiso 1 1 calc R U . . .
C3 C 0.6318(7) 0.4120(4) 0.2554(2) 0.0512(8) Uani 1 1 d . . . . .
C13 C 0.7243(7) 0.7415(4) 0.1578(2) 0.0559(8) Uani 1 1 d . . . . .
C1 C 0.3599(7) 0.3040(3) 0.3766(2) 0.0478(7) Uani 1 1 d . . . . .
C14 C 0.9224(9) 0.8378(4) 0.1900(3) 0.0636(9) Uani 1 1 d . . . . .
H14 H 0.985026 0.840926 0.254586 0.076 Uiso 1 1 calc R U . . .
C9 C 0.0693(9) 0.2082(4) 0.5016(3) 0.0616(9) Uani 1 1 d . . . . .
C6 C 0.4627(8) 0.1809(3) 0.3479(3) 0.0526(8) Uani 1 1 d . . . . .
C5 C 0.6531(9) 0.1777(4) 0.2702(3) 0.0624(9) Uani 1 1 d . . . . .
H5 H 0.723895 0.097285 0.248670 0.075 Uiso 1 1 calc R U . . .
C4 C 0.7372(8) 0.2903(4) 0.2251(3) 0.0602(9) Uani 1 1 d . . . . .
H4 H 0.865715 0.285793 0.173895 0.072 Uiso 1 1 calc R U . . .
C12 C 0.6027(10) 0.6430(4) 0.2276(3) 0.0654(10) Uani 1 1 d . . . . .
H12A H 0.660810 0.667553 0.293077 0.078 Uiso 1 1 calc R U . . .
H12B H 0.383401 0.639845 0.221484 0.078 Uiso 1 1 calc R U . . .
C7 C 0.3627(9) 0.0689(4) 0.3989(3) 0.0618(9) Uani 1 1 d . . . . .
H7 H 0.428541 -0.014207 0.381358 0.074 Uiso 1 1 calc R U . . .
C16 C 0.9365(11) 0.9260(5) 0.0309(4) 0.0820(14) Uani 1 1 d . . . . .
H16 H 1.006655 0.988113 -0.011923 0.098 Uiso 1 1 calc R U . . .
C17 C 0.7425(10) 0.8308(6) -0.0006(3) 0.0828(14) Uani 1 1 d . . . . .
H17 H 0.682096 0.827697 -0.065318 0.099 Uiso 1 1 calc R U . . .
C8 C 0.1747(9) 0.0810(4) 0.4720(3) 0.0659(10) Uani 1 1 d . . . . .
H8 H 0.111698 0.006189 0.503929 0.079 Uiso 1 1 calc R U . . .
C18 C 0.6327(9) 0.7382(5) 0.0619(3) 0.0737(11) Uani 1 1 d . . . . .
H18 H 0.497892 0.674011 0.039434 0.088 Uiso 1 1 calc R U . . .
C15 C 1.0289(10) 0.9305(4) 0.1258(4) 0.0781(12) Uani 1 1 d . . . . .
H15 H 1.162966 0.995445 0.147507 0.094 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
O10 C1 1.369(4) . ?
O10 C9 1.376(4) . ?
O11 C3 1.359(4) . ?
O11 C12 1.429(5) . ?
O19 C9 1.211(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.390(5) . ?
C2 C1 1.381(5) . ?
C3 C4 1.394(5) . ?
C13 C14 1.377(6) . ?
C13 C12 1.509(5) . ?
C13 C18 1.380(6) . ?
C1 C6 1.396(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.395(6) . ?
C9 C8 1.442(6) . ?
C6 C5 1.397(5) . ?
C6 C7 1.422(5) . ?
C5 H5 0.9300 . ?
C5 C4 1.365(6) . ?
C4 H4 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C7 H7 0.9300 . ?
C7 C8 1.344(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.355(8) . ?
C16 C15 1.368(7) . ?
C17 H17 0.9300 . ?
C17 C18 1.384(7) . ?
C8 H8 0.9300 . ?
C18 H18 0.9300 . ?
C15 H15 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
C1 O10 C9 122.7(3) . . ?
C3 O11 C12 117.6(2) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C1 C2 C3 118.3(3) . . ?
O11 C3 C2 124.3(3) . . ?
O11 C3 C4 115.7(3) . . ?
C2 C3 C4 120.0(3) . . ?
C14 C13 C12 120.1(3) . . ?
C14 C13 C18 119.4(4) . . ?
C18 C13 C12 120.5(4) . . ?
O10 C1 C2 116.6(3) . . ?
O10 C1 C6 120.5(3) . . ?
C2 C1 C6 122.9(3) . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 119.9(4) . . ?
C15 C14 H14 120.0 . . ?
O10 C9 C8 116.8(3) . . ?
O19 C9 O10 117.0(4) . . ?
O19 C9 C8 126.2(4) . . ?
C1 C6 C5 117.0(3) . . ?
C1 C6 C7 117.8(3) . . ?
C5 C6 C7 125.2(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 H5 119.3 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.5(3) . . ?
C5 C4 H4 119.8 . . ?
O11 C12 C13 107.6(3) . . ?
O11 C12 H12A 110.2 . . ?
O11 C12 H12B 110.2 . . ?
C13 C12 H12A 110.2 . . ?
C13 C12 H12B 110.2 . . ?
H12A C12 H12B 108.5 . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.2(4) . . ?
C8 C7 H7 119.4 . . ?
C17 C16 H16 120.1 . . ?
C17 C16 C15 119.8(4) . . ?
C15 C16 H16 120.1 . . ?
C16 C17 H17 119.4 . . ?
C16 C17 C18 121.1(4) . . ?
C18 C17 H17 119.4 . . ?
C9 C8 H8 119.5 . . ?
C7 C8 C9 121.0(4) . . ?
C7 C8 H8 119.5 . . ?
C13 C18 C17 119.6(4) . . ?
C13 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.1(4) . . ?
C16 C15 H15 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O10 C1 C6 C5 -179.9(3) . . . . ?
O10 C1 C6 C7 1.0(4) . . . . ?
O10 C9 C8 C7 -0.6(6) . . . . ?
O11 C3 C4 C5 -179.6(3) . . . . ?
O19 C9 C8 C7 179.8(4) . . . . ?
C2 C3 C4 C5 0.4(5) . . . . ?
C2 C1 C6 C5 -0.7(5) . . . . ?
C2 C1 C6 C7 -179.8(3) . . . . ?
C3 O11 C12 C13 -175.6(3) . . . . ?
C3 C2 C1 O10 179.7(3) . . . . ?
C3 C2 C1 C6 0.4(5) . . . . ?
C13 C14 C15 C16 0.1(6) . . . . ?
C1 O10 C9 O19 -178.5(3) . . . . ?
C1 O10 C9 C8 1.9(5) . . . . ?
C1 C2 C3 O11 179.7(3) . . . . ?
C1 C2 C3 C4 -0.3(5) . . . . ?
C1 C6 C5 C4 0.8(5) . . . . ?
C1 C6 C7 C8 0.2(5) . . . . ?
C14 C13 C12 O11 -111.9(4) . . . . ?
C14 C13 C18 C17 0.4(6) . . . . ?
C9 O10 C1 C2 178.6(3) . . . . ?
C9 O10 C1 C6 -2.1(4) . . . . ?
C6 C5 C4 C3 -0.6(6) . . . . ?
C6 C7 C8 C9 -0.4(6) . . . . ?
C5 C6 C7 C8 -178.8(4) . . . . ?
C12 O11 C3 C2 -5.8(5) . . . . ?
C12 O11 C3 C4 174.2(3) . . . . ?
C12 C13 C14 C15 -178.6(3) . . . . ?
C12 C13 C18 C17 178.9(4) . . . . ?
C7 C6 C5 C4 179.8(3) . . . . ?
C16 C17 C18 C13 -0.7(7) . . . . ?
C17 C16 C15 C14 -0.4(7) . . . . ?
C18 C13 C14 C15 -0.1(5) . . . . ?
C18 C13 C12 O11 69.7(4) . . . . ?
C15 C16 C17 C18 0.7(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.397
_oxdiff_exptl_absorpt_empirical_full_min 0.457
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane, chloroform'
####################################################################### 
# 
# 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_5a
_database_code_depnum_ccdc_archive 'CCDC 2312834'
loop_
_audit_author_name
_audit_author_address
'Ayano Ikemura'
;Gifu University
Japan
;
_audit_update_record             
;
2023-12-08 deposited with the CCDC.	2024-02-21 downloaded from the CCDC.
;
_audit_creation_date             2023-11-29
_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            5a
_chemical_name_systematic        
7-(hydroxy)-3-(trifluoromethyl)-2H-chromen-2-one
_chemical_formula_moiety         'C10 H5 F3 O3'
_chemical_formula_sum            'C10 H5 F3 O3'
_chemical_formula_weight         230.14
_chemical_melting_point          453
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'
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                   8.6323(4)
_cell_length_b                   7.1785(3)
_cell_length_c                   14.9074(7)
_cell_angle_alpha                90
_cell_angle_beta                 103.982(5)
_cell_angle_gamma                90
_cell_volume                     896.40(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2333
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.2020
_cell_measurement_theta_min      5.2650
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.476
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59240
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0831
_diffrn_reflns_av_unetI/netI     0.1027
_diffrn_reflns_Laue_measured_fraction_full 0.999
_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       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4318
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.492
_diffrn_reflns_theta_min         5.281
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_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    -26.00   3.00   0.50    0.20    --  -44.09  32.00 150.00   58
  2  ω    -61.00  -3.00   0.50    0.20    --  -44.09  54.00 120.00  116
  3  ω    -14.00  11.00   0.50    0.20    --  -44.09  21.00   0.00   50
  4  ω    -37.00  21.00   0.50    0.20    --  -44.09  34.00 -48.00  116
  5  ω     -5.00  26.00   0.50    0.20    --  -44.09  11.00-150.00   62
  6  ω     62.00 108.00   0.50    0.38    --   97.43-117.00 -90.00   92
  7  ω     39.00  64.00   0.50    0.38    --   97.43-117.00  60.00   50
  8  ω     72.00 104.00   0.50    0.38    --   97.43-117.00  60.00   64
  9  ω     37.00  90.00   0.50    0.38    --   97.43-117.00 120.00  106
 10  ω     39.00  70.00   0.50    0.38    --   97.43 -68.00  30.00   62
 11  ω     31.00  56.00   0.50    0.38    --   97.43 -50.00 150.00   50
 12  ω     41.00  66.00   0.50    0.38    --   97.43 -59.00 -30.00   50
 13  ω     31.00  56.00   0.50    0.38    --   97.43 -50.00 -30.00   50
 14  ω     39.00  64.00   0.50    0.38    --   97.43 -59.00 -60.00   50
 15  ω     31.00  57.00   0.50    0.38    --   97.43 -50.00 -90.00   52
 16  ω     39.00  64.00   0.50    0.38    --   97.43 -59.00-120.00   50
 17  ω     54.00 109.00   0.50    0.20    --   45.96  34.00 -48.00  110
 18  ω    139.00 164.00   0.50    0.38    --   97.43  50.00 -90.00   50
 19  ω    129.00 156.00   0.50    0.38    --   97.43  68.00 -60.00   54
 20  ω     85.00 121.00   0.50    0.38    --   97.43  50.00 -90.00   72
 21  ω     79.00 104.00   0.50    0.38    --   97.43  68.00 -60.00   50
 22  ω     96.00 141.00   0.50    0.38    --   97.43  34.00 -48.00   90
 23  ω    133.00 159.00   0.50    0.38    --   97.43  42.00   0.00   52
 24  ω     88.00 130.00   0.50    0.38    --   97.43  42.00   0.00   84
 25  ω     85.00 156.00   0.50    0.38    --   97.43  59.00  30.00  142
 26  ω     65.00  99.00   0.50    0.20    --   45.96 138.00   0.00   68
 27  ω     65.00 109.00   0.50    0.20    --   45.96 138.00 150.00   88
 28  ω    -19.00  39.00   0.50    0.20    --   45.96 -34.00 153.00  116
 29  ω    -83.00 -45.00   0.50    0.20    --  -44.09 -34.00 153.00   76
 30  ω   -162.00 -73.00   0.50    0.38    --  -95.55 -68.00  90.00  178
 31  ω   -119.00 -92.00   0.50    0.38    --  -95.55 -34.00 153.00   54
 32  ω   -106.00 -80.00   0.50    0.20    --  -44.09-138.00-120.00   52
 33  ω    -58.00 -31.00   0.50    0.38    --  -95.55  59.00-150.00   54
 34  ω    -55.00 -29.00   0.50    0.38    --  -95.55  50.00-120.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1364
_reflns_number_total             1676
_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 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_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         0.257
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1676
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0591
_refine_ls_restrained_S_all      1.038
_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)+(0.1237P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1663
_refine_ls_wR_factor_ref         0.1786
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C4(H4), C5(H5)
2.b Idealised tetrahedral OH refined as rotating group:
 O15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
F12 F 0.49518(15) 0.1401(2) 0.73965(10) 0.0633(5) Uani 1 1 d . . . . .
F13 F 0.28675(17) -0.02051(19) 0.68084(10) 0.0618(5) Uani 1 1 d . . . . .
O10 O 0.17125(16) 0.5522(2) 0.61770(9) 0.0442(4) Uani 1 1 d . . . . .
O16 O 0.20960(18) 0.3609(2) 0.73668(10) 0.0505(4) Uani 1 1 d . . . . .
F14 F 0.47317(18) 0.0039(2) 0.60862(11) 0.0695(5) Uani 1 1 d . . . . .
O15 O 0.0887(2) 0.9918(2) 0.37819(12) 0.0586(5) Uani 1 1 d . . . . .
H15 H 0.104139 1.008258 0.326616 0.088 Uiso 1 1 calc R U . . .
C9 C 0.2305(2) 0.3898(3) 0.66042(14) 0.0414(5) Uani 1 1 d . . . . .
C6 C 0.2557(2) 0.4743(3) 0.47971(15) 0.0454(5) Uani 1 1 d . . . . .
C8 C 0.3146(2) 0.2678(3) 0.61033(14) 0.0446(5) Uani 1 1 d . . . . .
C1 C 0.1840(2) 0.5983(3) 0.53011(13) 0.0401(5) Uani 1 1 d . . . . .
C3 C 0.1397(2) 0.8195(3) 0.40872(15) 0.0443(5) Uani 1 1 d . . . . .
C2 C 0.1244(2) 0.7685(3) 0.49556(14) 0.0455(5) Uani 1 1 d . . . . .
H2 H 0.075191 0.847221 0.529789 0.055 Uiso 1 1 calc R U . . .
C7 C 0.3227(3) 0.3083(3) 0.52374(16) 0.0492(5) Uani 1 1 d . . . . .
H7 H 0.373214 0.225729 0.492045 0.059 Uiso 1 1 calc R U . . .
C4 C 0.2055(3) 0.6969(3) 0.35472(16) 0.0516(6) Uani 1 1 d . . . . .
H4 H 0.210591 0.730511 0.295255 0.062 Uiso 1 1 calc R U . . .
C11 C 0.3912(3) 0.0998(3) 0.65992(16) 0.0501(6) Uani 1 1 d . . . . .
C5 C 0.2618(3) 0.5281(3) 0.38989(16) 0.0547(6) Uani 1 1 d . . . . .
H5 H 0.305179 0.446906 0.353865 0.066 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
F12 C11 1.337(3) . ?
F13 C11 1.339(3) . ?
O10 C9 1.367(3) . ?
O10 C1 1.377(2) . ?
O16 C9 1.211(2) . ?
F14 C11 1.349(3) . ?
O15 H15 0.8200 . ?
O15 C3 1.354(3) . ?
C9 C8 1.454(3) . ?
C6 C1 1.402(3) . ?
C6 C7 1.415(3) . ?
C6 C5 1.407(3) . ?
C8 C7 1.341(3) . ?
C8 C11 1.484(3) . ?
C1 C2 1.376(3) . ?
C3 C2 1.382(3) . ?
C3 C4 1.403(3) . ?
C2 H2 0.9300 . ?
C7 H7 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.363(3) . ?
C5 H5 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
C9 O10 C1 122.69(15) . . ?
C3 O15 H15 109.5 . . ?
O10 C9 C8 116.85(17) . . ?
O16 C9 O10 117.31(17) . . ?
O16 C9 C8 125.83(19) . . ?
C1 C6 C7 118.04(19) . . ?
C1 C6 C5 117.3(2) . . ?
C5 C6 C7 124.58(18) . . ?
C9 C8 C11 116.84(18) . . ?
C7 C8 C9 120.79(19) . . ?
C7 C8 C11 122.36(18) . . ?
O10 C1 C6 120.15(19) . . ?
C2 C1 O10 117.40(17) . . ?
C2 C1 C6 122.45(18) . . ?
O15 C3 C2 117.39(18) . . ?
O15 C3 C4 121.63(19) . . ?
C2 C3 C4 121.0(2) . . ?
C1 C2 C3 118.31(18) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.26(19) . . ?
C8 C7 H7 119.4 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.6(2) . . ?
C5 C4 H4 120.2 . . ?
F12 C11 F13 106.13(18) . . ?
F12 C11 F14 106.45(18) . . ?
F12 C11 C8 112.93(19) . . ?
F13 C11 F14 106.16(19) . . ?
F13 C11 C8 113.33(17) . . ?
F14 C11 C8 111.33(18) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 C6 121.21(19) . . ?
C4 C5 H5 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O10 C9 C8 C7 -4.6(3) . . . . ?
O10 C9 C8 C11 174.76(17) . . . . ?
O10 C1 C2 C3 178.36(17) . . . . ?
O16 C9 C8 C7 176.0(2) . . . . ?
O16 C9 C8 C11 -4.6(3) . . . . ?
O15 C3 C2 C1 -176.30(17) . . . . ?
O15 C3 C4 C5 177.1(2) . . . . ?
C9 O10 C1 C6 2.0(3) . . . . ?
C9 O10 C1 C2 -177.86(16) . . . . ?
C9 C8 C7 C6 2.7(3) . . . . ?
C9 C8 C11 F12 -56.6(2) . . . . ?
C9 C8 C11 F13 64.1(2) . . . . ?
C9 C8 C11 F14 -176.32(18) . . . . ?
C6 C1 C2 C3 -1.5(3) . . . . ?
C1 O10 C9 O16 -178.32(16) . . . . ?
C1 O10 C9 C8 2.3(3) . . . . ?
C1 C6 C7 C8 1.6(3) . . . . ?
C1 C6 C5 C4 2.3(3) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C2 C3 C4 C5 -3.0(3) . . . . ?
C7 C6 C1 O10 -4.0(3) . . . . ?
C7 C6 C1 C2 175.84(19) . . . . ?
C7 C6 C5 C4 -174.8(2) . . . . ?
C7 C8 C11 F12 122.7(2) . . . . ?
C7 C8 C11 F13 -116.6(2) . . . . ?
C7 C8 C11 F14 3.0(3) . . . . ?
C4 C3 C2 C1 3.8(3) . . . . ?
C11 C8 C7 C6 -176.67(19) . . . . ?
C5 C6 C1 O10 178.66(18) . . . . ?
C5 C6 C1 C2 -1.5(3) . . . . ?
C5 C6 C7 C8 178.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2315002'
loop_
_audit_author_name
_audit_author_address
'Ayano Ikemura'
;Gifu University
Japan
;
_audit_update_record             
;
2023-12-18 deposited with the CCDC.	2024-02-21 downloaded from the CCDC.
;
_audit_creation_date             2023-12-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            1
_chemical_name_systematic        7-(hydroxy)-2H-chromen-2-one
_chemical_formula_moiety         'C9 H6 O3'
_chemical_formula_sum            'C9 H6 O3'
_chemical_formula_weight         162.14
_chemical_melting_point          503.5
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   3.8515(4)
_cell_length_b                   11.0399(13)
_cell_length_c                   16.7731(13)
_cell_angle_alpha                90
_cell_angle_beta                 90.489(8)
_cell_angle_gamma                90
_cell_volume                     713.17(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3072
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      30.2340
_cell_measurement_theta_min      2.1620
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44450
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.213
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.105
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6911
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.209
_diffrn_ambient_temperature      173.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -105.00  75.00   0.50   60.00    --  -15.00  45.00  90.00  360
  2  ω   -105.00  75.00   0.50   60.00    --  -15.00  45.00   0.00  360
  3  ω   -105.00  -1.00   0.50   60.00    --  -15.00  45.00 270.00  208
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0306066000
_diffrn_orient_matrix_UB_12      -0.0129723000
_diffrn_orient_matrix_UB_13      -0.0407413000
_diffrn_orient_matrix_UB_21      -0.1791987000
_diffrn_orient_matrix_UB_22      0.0077826000
_diffrn_orient_matrix_UB_23      -0.0085459000
_diffrn_orient_matrix_UB_31      0.0284592000
_diffrn_orient_matrix_UB_32      0.0625046000
_diffrn_orient_matrix_UB_33      -0.0074088000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1073
_reflns_number_total             1453
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_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         0.331
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1453
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0570
_refine_ls_restrained_S_all      1.026
_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)+(0.1127P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1544
_refine_ls_wR_factor_ref         0.1696
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C12(H12), C9(H9), C8(H8), C11(H11)
2.b Idealised tetrahedral OH refined as rotating group:
 O7(H7)
;
_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
O3 O 0.8359(3) 0.19618(11) 0.72568(7) 0.0377(4) Uani 1 1 d . . . . .
O1 O 1.0841(4) 0.20139(12) 0.84453(7) 0.0503(5) Uani 1 1 d . . . . .
O7 O 0.3666(4) 0.16355(13) 0.46645(8) 0.0528(5) Uani 1 1 d . . . . .
H7 H 0.260444 0.204273 0.431664 0.079 Uiso 1 1 calc R U . . .
C10 C 0.5550(4) 0.37190(16) 0.66849(10) 0.0337(5) Uani 1 1 d . . . . .
C4 C 0.6596(4) 0.24993(17) 0.66292(9) 0.0325(5) Uani 1 1 d . . . . .
C5 C 0.5953(5) 0.17992(16) 0.59602(10) 0.0359(5) Uani 1 1 d . . . . .
H5 H 0.666778 0.097614 0.594053 0.043 Uiso 1 1 calc R U . . .
C2 C 0.9182(5) 0.25775(18) 0.79419(10) 0.0374(5) Uani 1 1 d . . . . .
C12 C 0.8074(5) 0.38237(16) 0.80037(10) 0.0389(5) Uani 1 1 d . . . . .
H12 H 0.856750 0.426850 0.847605 0.047 Uiso 1 1 calc R U . . .
C6 C 0.4236(5) 0.23304(18) 0.53176(10) 0.0396(5) Uani 1 1 d . . . . .
C9 C 0.3796(5) 0.42188(17) 0.60225(11) 0.0403(5) Uani 1 1 d . . . . .
H9 H 0.303145 0.503626 0.604264 0.048 Uiso 1 1 calc R U . . .
C8 C 0.3174(5) 0.35484(18) 0.53501(10) 0.0413(5) Uani 1 1 d . . . . .
H8 H 0.202524 0.390554 0.490525 0.050 Uiso 1 1 calc R U . . .
C11 C 0.6358(5) 0.43582(16) 0.74014(11) 0.0386(5) Uani 1 1 d . . . . .
H11 H 0.566431 0.518016 0.745282 0.046 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
O3 C4 1.3817(19) . ?
O3 C2 1.370(2) . ?
O1 C2 1.224(2) . ?
O7 H7 0.8400 . ?
O7 C6 1.354(2) . ?
C10 C4 1.409(3) . ?
C10 C9 1.408(2) . ?
C10 C11 1.426(2) . ?
C4 C5 1.383(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(2) . ?
C2 C12 1.444(3) . ?
C12 H12 0.9500 . ?
C12 C11 1.340(2) . ?
C6 C8 1.407(3) . ?
C9 H9 0.9500 . ?
C9 C8 1.368(2) . ?
C8 H8 0.9500 . ?
C11 H11 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O3 C4 122.33(14) . . ?
C6 O7 H7 109.5 . . ?
C4 C10 C11 117.93(15) . . ?
C9 C10 C4 117.25(15) . . ?
C9 C10 C11 124.82(16) . . ?
O3 C4 C10 119.93(14) . . ?
O3 C4 C5 117.49(16) . . ?
C5 C4 C10 122.59(15) . . ?
C4 C5 H5 120.8 . . ?
C4 C5 C6 118.30(17) . . ?
C6 C5 H5 120.8 . . ?
O3 C2 C12 117.80(15) . . ?
O1 C2 O3 116.24(17) . . ?
O1 C2 C12 125.96(16) . . ?
C2 C12 H12 119.7 . . ?
C11 C12 C2 120.65(16) . . ?
C11 C12 H12 119.7 . . ?
O7 C6 C5 117.47(17) . . ?
O7 C6 C8 121.87(16) . . ?
C5 C6 C8 120.66(16) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 C10 121.18(17) . . ?
C8 C9 H9 119.4 . . ?
C6 C8 H8 120.0 . . ?
C9 C8 C6 120.01(16) . . ?
C9 C8 H8 120.0 . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.35(17) . . ?
C12 C11 H11 119.3 . . ?

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
O3 C4 C5 C6 -178.92(14) . . . . ?
O3 C2 C12 C11 -1.2(3) . . . . ?
O1 C2 C12 C11 177.89(18) . . . . ?
O7 C6 C8 C9 179.90(17) . . . . ?
C10 C4 C5 C6 0.6(3) . . . . ?
C10 C9 C8 C6 1.2(3) . . . . ?
C4 O3 C2 O1 -177.83(15) . . . . ?
C4 O3 C2 C12 1.4(3) . . . . ?
C4 C10 C9 C8 -0.7(3) . . . . ?
C4 C10 C11 C12 0.4(3) . . . . ?
C4 C5 C6 O7 179.24(16) . . . . ?
C4 C5 C6 C8 -0.2(3) . . . . ?
C5 C6 C8 C9 -0.7(3) . . . . ?
C2 O3 C4 C10 -0.7(3) . . . . ?
C2 O3 C4 C5 178.89(16) . . . . ?
C2 C12 C11 C10 0.4(3) . . . . ?
C9 C10 C4 O3 179.34(14) . . . . ?
C9 C10 C4 C5 -0.2(3) . . . . ?
C9 C10 C11 C12 -179.18(17) . . . . ?
C11 C10 C4 O3 -0.2(2) . . . . ?
C11 C10 C4 C5 -179.78(16) . . . . ?
C11 C10 C9 C8 178.83(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.812
_oxdiff_exptl_absorpt_empirical_full_min 0.287
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone, chloroform'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_AIcouma_foura_auto
_database_code_depnum_ccdc_archive 'CCDC 2219769'
loop_
_audit_author_name
_audit_author_address
'Ayano Ikemura'
;Gifu University
Japan
;
_audit_update_record             
;
2022-11-15 deposited with the CCDC.	2024-02-21 downloaded from the CCDC.
;
_audit_creation_date             2022-09-22
_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        
7-(benzyloxy)-3-(trifluoromethyl)-2H-chromen-2-one
_chemical_formula_moiety         'C17 H11 F3 O3'
_chemical_formula_sum            'C17 H11 F3 O3'
_chemical_formula_weight         320.26
_chemical_melting_point          438
_chemical_oxdiff_formula         C17H11F3O3
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'
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                   6.6324(3)
_cell_length_b                   10.1334(5)
_cell_length_c                   10.8812(5)
_cell_angle_alpha                97.289(4)
_cell_angle_beta                 91.792(4)
_cell_angle_gamma                104.569(4)
_cell_volume                     700.56(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3725
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.9410
_cell_measurement_theta_min      4.0970
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.125
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36355
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   1.00000
_exptl_transmission_factor_min   0.36355
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6299
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.676
_diffrn_reflns_theta_min         4.105
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     94.00 163.00   0.50    0.68    --   97.43  42.00  60.00  138
  2  ω     94.00 163.00   0.50    0.68    --   97.43  33.00 -60.00  138
  3  ω     85.00 115.00   0.50    0.68    --   97.43  59.00-120.00   60
  4  ω     92.00 163.00   0.50    0.68    --   97.43  33.00-180.00  142
  5  ω    131.00 156.00   0.50    0.68    --   97.43  59.00-120.00   50
  6  ω     85.00 110.00   0.50    0.68    --   97.43   2.00  81.00   50
  7  ω     52.00 117.00   0.50    0.20    --   44.40   2.00  81.00  130
  8  ω    -24.00  34.00   0.50    0.20    --   44.40   2.00  81.00  116
  9  ω     34.00  89.00   0.50    0.20    --   44.40-138.00-120.00  110
 10  ω     41.00  81.00   0.50    0.68    --   97.43-117.00   0.00   80
 11  ω     39.00  64.00   0.50    0.68    --   97.43-117.00  30.00   50
 12  ω     66.00 109.00   0.50    0.68    --   97.43-117.00  30.00   86
 13  ω     57.00 110.00   0.50    0.68    --   97.43-117.00  90.00  106
 14  ω     53.00  85.00   0.50    0.68    --   97.43 -96.00 120.00   64
 15  ω     43.00  89.00   0.50    0.20    --   44.40-138.00  90.00   92
 16  ω     31.00  57.00   0.50    0.68    --   97.43 -96.00  30.00   52
 17  ω     69.00 106.00   0.50    0.68    --   97.43 -96.00  30.00   74
 18  ω     57.00 110.00   0.50    0.68    --   97.43-117.00-180.00  106
 19  ω     27.00 100.00   0.50    0.68    --   97.43 -96.00-150.00  146
 20  ω     50.00 100.00   0.50    0.68    --   97.43 -77.00-150.00  100
 21  ω     54.00  82.00   0.50    0.68    --   97.43 -68.00-120.00   56
 22  ω     15.00  46.00   0.50    0.20    --   44.40 -43.00-120.00   62
 23  ω     31.00  56.00   0.50    0.68    --   97.43 -50.00 -30.00   50
 24  ω     92.00 117.00   0.50    0.68    --   97.43  -2.00 -97.00   50
 25  ω     76.00 108.00   0.50    0.20    --   44.40  -2.00 -97.00   64
 26  ω    -58.00  31.00   0.50    0.20    --  -42.84   2.00  81.00  178
 27  ω    -59.00  -4.00   0.50    0.20    --  -42.84  54.00 -30.00  110
 28  ω    -35.00  21.00   0.50    0.20    --  -42.84  32.00-120.00  112
 29  ω    -99.00 -73.00   0.50    0.20    --  -42.84   2.00  81.00   52
 30  ω    -79.00 -36.00   0.50    0.20    --  -42.84 -21.00  60.00   86
 31  ω   -112.00 -87.00   0.50    0.20    --  -42.84 -21.00  60.00   50
 32  ω    -99.00 -73.00   0.50    0.20    --  -42.84  -2.00 -97.00   52
 33  ω    -62.00 -27.00   0.50    0.68    --  -95.86  96.00   0.00   70
 34  ω    -46.00 -21.00   0.50    0.20    --  -42.84 138.00   0.00   50
 35  ω    -99.00 -54.00   0.50    0.20    --  -42.84 138.00   0.00   90
 36  ω   -126.00 -99.00   0.50    0.68    --  -95.86 143.00-117.48   54
 37  ω    -58.00 -33.00   0.50    0.68    --  -95.86 143.00-117.48   50
 38  ω    -83.00 -58.00   0.50    0.68    --  -95.86  68.00-150.00   50
 39  ω    -56.00 -29.00   0.50    0.68    --  -95.86  50.00-180.00   54
 40  ω    -56.00 -30.00   0.50    0.68    --  -95.86  50.00 -90.00   52
 41  ω    -57.00 -32.00   0.50    0.68    --  -95.86  50.00-120.00   50
 42  ω    -57.00 -32.00   0.50    0.68    --  -95.86  50.00 -60.00   50
 43  ω    -57.00 -30.00   0.50    0.68    --  -95.86  50.00 -30.00   54
 44  ω    -55.00 -29.00   0.50    0.68    --  -95.86  50.00  90.00   52
 45  ω    -77.00 -48.00   0.50    0.68    --  -95.86  68.00 120.00   58
 46  ω    -55.00 -30.00   0.50    0.68    --  -95.86  50.00 120.00   50
 47  ω    -56.00 -29.00   0.50    0.68    --  -95.86  50.00 150.00   54
 48  ω    -94.00 -68.00   0.50    0.68    --  -95.86   2.00  81.00   52
 49  ω   -141.00-115.00   0.50    0.68    --  -95.86   2.00  81.00   52
 50  ω    -57.00 -32.00   0.50    0.68    --  -95.86  50.00-150.00   50
 51  ω   -122.00 -97.00   0.50    0.68    --  -95.86  -2.00 -97.00   50
 52  ω   -119.00 -90.00   0.50    0.68    --  -95.86 -59.00 -30.00   58
 53  ω   -162.00-134.00   0.50    0.68    --  -95.86 -59.00 -30.00   56
 54  ω   -161.00-128.00   0.50    0.68    --  -95.86 -68.00-150.00   66
 55  ω   -115.00 -78.00   0.50    0.68    --  -95.86 -68.00-150.00   74
 56  ω   -110.00 -69.00   0.50    0.20    --  -42.84-138.00-120.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1978495000
_diffrn_orient_matrix_UB_12      0.1193048000
_diffrn_orient_matrix_UB_13      0.0031317000
_diffrn_orient_matrix_UB_21      0.1362559000
_diffrn_orient_matrix_UB_22      -0.1027386000
_diffrn_orient_matrix_UB_23      -0.0002386000
_diffrn_orient_matrix_UB_31      -0.0117280000
_diffrn_orient_matrix_UB_32      -0.0193146000
_diffrn_orient_matrix_UB_33      -0.1430090000
_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                2123
_reflns_number_total             2603
_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 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_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         0.251
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0077(14)
_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   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2603
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0453
_refine_ls_restrained_S_all      1.079
_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)+(0.0818P)²+0.0169P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1337
_refine_ls_wR_factor_ref         0.1405
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
1.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C5(H5), C4(H4), C14(H14), C16(H16), C17(H17), C18(H18),
 C15(H15)
;
_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
O10 O 0.59774(15) 0.43084(11) 0.37055(10) 0.0498(3) Uani 1 1 d . . . . .
F20 F 0.7760(2) 0.58919(14) 0.03517(10) 0.0879(4) Uani 1 1 d . . . . .
O11 O 0.75074(19) 0.10484(14) 0.61309(11) 0.0621(4) Uani 1 1 d . . . . .
O23 O 0.50392(18) 0.56740(14) 0.25077(12) 0.0667(4) Uani 1 1 d . . . . .
F21 F 0.8650(2) 0.75931(11) 0.18035(13) 0.0868(4) Uani 1 1 d . . . . .
F22 F 1.09233(19) 0.65766(16) 0.11175(14) 0.0959(5) Uani 1 1 d . . . . .
C1 C 0.7359(2) 0.36162(15) 0.40849(13) 0.0426(3) Uani 1 1 d . . . . .
C2 C 0.6682(2) 0.27319(16) 0.49440(13) 0.0477(4) Uani 1 1 d . . . . .
H2 H 0.537521 0.264835 0.525882 0.057 Uiso 1 1 calc R U . . .
C6 C 0.9323(2) 0.38045(15) 0.36203(13) 0.0438(3) Uani 1 1 d . . . . .
C9 C 0.6397(2) 0.51726(16) 0.28119(14) 0.0484(4) Uani 1 1 d . . . . .
C13 C 0.5410(3) -0.01111(16) 0.76119(13) 0.0495(4) Uani 1 1 d . . . . .
C8 C 0.8470(2) 0.53930(15) 0.23471(14) 0.0471(4) Uani 1 1 d . . . . .
C7 C 0.9859(2) 0.47450(16) 0.27362(14) 0.0472(4) Uani 1 1 d . . . . .
H7 H 1.117768 0.491008 0.242772 0.057 Uiso 1 1 calc R U . . .
C5 C 1.0632(2) 0.30418(17) 0.40363(14) 0.0524(4) Uani 1 1 d . . . . .
H5 H 1.196126 0.315384 0.374801 0.063 Uiso 1 1 calc R U . . .
C4 C 0.9984(3) 0.21331(18) 0.48613(15) 0.0555(4) Uani 1 1 d . . . . .
H4 H 1.085970 0.161921 0.511666 0.067 Uiso 1 1 calc R U . . .
C3 C 0.7996(2) 0.19769(16) 0.53221(13) 0.0491(4) Uani 1 1 d . . . . .
C12 C 0.5617(2) 0.09508(18) 0.67469(15) 0.0540(4) Uani 1 1 d . . . . .
H12A H 0.443400 0.069323 0.613976 0.065 Uiso 1 1 calc R U . . .
H12B H 0.563367 0.183649 0.721177 0.065 Uiso 1 1 calc R U . . .
C14 C 0.3536(3) -0.05199(19) 0.81512(15) 0.0581(4) Uani 1 1 d . . . . .
H14 H 0.243972 -0.014396 0.796516 0.070 Uiso 1 1 calc R U . . .
C19 C 0.8956(3) 0.63638(19) 0.14030(17) 0.0609(4) Uani 1 1 d . . . . .
C16 C 0.4868(3) -0.20601(19) 0.92452(16) 0.0658(5) Uani 1 1 d . . . . .
H16 H 0.468739 -0.271267 0.978850 0.079 Uiso 1 1 calc R U . . .
C17 C 0.6727(3) -0.1660(2) 0.87119(18) 0.0722(5) Uani 1 1 d . . . . .
H17 H 0.781373 -0.204692 0.889316 0.087 Uiso 1 1 calc R U . . .
C18 C 0.7010(3) -0.0678(2) 0.78995(17) 0.0637(5) Uani 1 1 d . . . . .
H18 H 0.828585 -0.040618 0.755159 0.076 Uiso 1 1 calc R U . . .
C15 C 0.3278(3) -0.1485(2) 0.89666(16) 0.0639(5) Uani 1 1 d . . . . .
H15 H 0.201226 -0.174546 0.932869 0.077 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
O10 C1 1.3696(17) . ?
O10 C9 1.3784(18) . ?
F20 C19 1.334(2) . ?
O11 C3 1.3562(18) . ?
O11 C12 1.4277(19) . ?
O23 C9 1.1973(19) . ?
F21 C19 1.333(2) . ?
F22 C19 1.321(2) . ?
C1 C2 1.384(2) . ?
C1 C6 1.389(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.381(2) . ?
C6 C7 1.430(2) . ?
C6 C5 1.399(2) . ?
C9 C8 1.453(2) . ?
C13 C12 1.501(2) . ?
C13 C14 1.382(2) . ?
C13 C18 1.373(2) . ?
C8 C7 1.345(2) . ?
C8 C19 1.498(2) . ?
C7 H7 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.369(2) . ?
C4 H4 0.9300 . ?
C4 C3 1.404(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C14 H14 0.9300 . ?
C14 C15 1.385(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.369(3) . ?
C16 C15 1.371(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.395(2) . ?
C18 H18 0.9300 . ?
C15 H15 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
C1 O10 C9 122.75(11) . . ?
C3 O11 C12 118.25(12) . . ?
O10 C1 C2 116.29(12) . . ?
O10 C1 C6 121.00(13) . . ?
C2 C1 C6 122.72(13) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.33(13) . . ?
C3 C2 H2 120.8 . . ?
C1 C6 C7 117.96(13) . . ?
C1 C6 C5 117.61(13) . . ?
C5 C6 C7 124.42(13) . . ?
O10 C9 C8 116.11(12) . . ?
O23 C9 O10 117.17(13) . . ?
O23 C9 C8 126.71(14) . . ?
C14 C13 C12 118.40(14) . . ?
C18 C13 C12 122.79(14) . . ?
C18 C13 C14 118.81(15) . . ?
C9 C8 C19 116.34(13) . . ?
C7 C8 C9 121.54(14) . . ?
C7 C8 C19 122.11(13) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.51(13) . . ?
C8 C7 H7 119.7 . . ?
C6 C5 H5 119.5 . . ?
C4 C5 C6 120.95(13) . . ?
C4 C5 H5 119.5 . . ?
C5 C4 H4 120.0 . . ?
C5 C4 C3 119.99(14) . . ?
C3 C4 H4 120.0 . . ?
O11 C3 C2 124.42(13) . . ?
O11 C3 C4 115.21(13) . . ?
C2 C3 C4 120.37(14) . . ?
O11 C12 C13 109.33(13) . . ?
O11 C12 H12A 109.8 . . ?
O11 C12 H12B 109.8 . . ?
C13 C12 H12A 109.8 . . ?
C13 C12 H12B 109.8 . . ?
H12A C12 H12B 108.3 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.55(17) . . ?
C15 C14 H14 119.7 . . ?
F20 C19 C8 112.05(15) . . ?
F21 C19 F20 106.26(14) . . ?
F21 C19 C8 112.31(14) . . ?
F22 C19 F20 107.54(15) . . ?
F22 C19 F21 106.89(15) . . ?
F22 C19 C8 111.45(14) . . ?
C17 C16 H16 120.5 . . ?
C17 C16 C15 119.03(16) . . ?
C15 C16 H16 120.5 . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.72(18) . . ?
C18 C17 H17 119.6 . . ?
C13 C18 C17 120.24(17) . . ?
C13 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.65(16) . . ?
C16 C15 H15 119.7 . . ?

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
O10 C1 C2 C3 177.85(13) . . . . ?
O10 C1 C6 C7 0.1(2) . . . . ?
O10 C1 C6 C5 -178.87(13) . . . . ?
O10 C9 C8 C7 2.5(2) . . . . ?
O10 C9 C8 C19 -178.27(13) . . . . ?
O23 C9 C8 C7 -178.34(17) . . . . ?
O23 C9 C8 C19 0.9(3) . . . . ?
C1 O10 C9 O23 176.50(13) . . . . ?
C1 O10 C9 C8 -4.3(2) . . . . ?
C1 C2 C3 O11 -178.16(13) . . . . ?
C1 C2 C3 C4 1.4(2) . . . . ?
C1 C6 C7 C8 -1.8(2) . . . . ?
C1 C6 C5 C4 0.7(2) . . . . ?
C2 C1 C6 C7 -179.96(13) . . . . ?
C2 C1 C6 C5 1.0(2) . . . . ?
C6 C1 C2 C3 -2.1(2) . . . . ?
C6 C5 C4 C3 -1.3(3) . . . . ?
C9 O10 C1 C2 -176.87(13) . . . . ?
C9 O10 C1 C6 3.0(2) . . . . ?
C9 C8 C7 C6 0.4(2) . . . . ?
C9 C8 C19 F20 -64.50(19) . . . . ?
C9 C8 C19 F21 55.0(2) . . . . ?
C9 C8 C19 F22 174.93(15) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C7 C6 C5 C4 -178.24(15) . . . . ?
C7 C8 C19 F20 114.73(17) . . . . ?
C7 C8 C19 F21 -125.75(17) . . . . ?
C7 C8 C19 F22 -5.8(2) . . . . ?
C5 C6 C7 C8 177.12(14) . . . . ?
C5 C4 C3 O11 179.84(15) . . . . ?
C5 C4 C3 C2 0.3(3) . . . . ?
C3 O11 C12 C13 -178.82(13) . . . . ?
C12 O11 C3 C2 -7.6(2) . . . . ?
C12 O11 C3 C4 172.85(14) . . . . ?
C12 C13 C14 C15 -179.26(15) . . . . ?
C12 C13 C18 C17 179.89(17) . . . . ?
C14 C13 C12 O11 -169.95(14) . . . . ?
C14 C13 C18 C17 0.7(3) . . . . ?
C19 C8 C7 C6 -178.74(14) . . . . ?
C16 C17 C18 C13 -0.8(3) . . . . ?
C17 C16 C15 C14 0.4(3) . . . . ?
C18 C13 C12 O11 10.9(2) . . . . ?
C18 C13 C14 C15 0.0(3) . . . . ?
C15 C16 C17 C18 0.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.341
_oxdiff_exptl_absorpt_empirical_full_min 0.471
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane, chloroform'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_5b
_database_code_depnum_ccdc_archive 'CCDC 2219770'
loop_
_audit_author_name
_audit_author_address
'Ayano Ikemura'
;Gifu University
Japan
;
_audit_update_record             
;
2023-12-26 deposited with the CCDC.	2024-02-21 downloaded from the CCDC.
;
_audit_creation_date             2023-12-26
_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            5b
_chemical_name_systematic        5b
_chemical_formula_moiety         'C13 H5 F9 O3'
_chemical_formula_sum            'C13 H5 F9 O3'
_chemical_formula_weight         380.17
_chemical_melting_point          436
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0192 0.0096 '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 0.0754 0.0551 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0524 0.0338 '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                   13.9448(2)
_cell_length_b                   5.92150(10)
_cell_length_c                   16.9008(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.068(2)
_cell_angle_gamma                90
_cell_volume                     1341.05(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5539
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.5060
_cell_measurement_theta_min      2.7130
_shelx_estimated_absorpt_T_max   0.908
_shelx_estimated_absorpt_T_min   0.695
_exptl_absorpt_coefficient_mu    1.958
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.883
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6943
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.679
_diffrn_reflns_theta_min         3.649
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     59.00  94.00   0.50    0.28    --   45.09 155.00 -48.00   70
  2  ω     77.00 107.00   0.50    0.28    --   45.09 138.00-120.00   60
  3  ω     83.00 108.00   0.50    1.11    --   97.11 155.00 -48.00   50
  4  ω    128.00 153.00   0.50    1.11    --   97.11  25.00  90.00   50
  5  ω     93.00 119.00   0.50    1.11    --   97.11  25.00  90.00   52
  6  ω    -15.00  10.00   0.50    0.28    --   45.09 -89.00  60.00   50
  7  ω     17.00  74.00   0.50    0.28    --   45.09 -89.00  60.00  114
  8  ω     50.00  75.00   0.50    0.28    --   45.09-120.00  70.00   50
  9  ω    101.00 126.00   0.50    1.11    --   97.11 -87.00  60.00   50
 10  ω     50.00  87.00   0.50    1.11    --   97.11 -87.00  60.00   74
 11  ω     33.00 110.00   0.50    1.11    --   97.11-120.00  70.00  154
 12  ω     63.00 109.00   0.50    1.11    --   97.11-117.00 150.00   92
 13  ω     31.00  56.00   0.50    1.11    --   97.11 -50.00 120.00   50
 14  ω     31.00  63.00   0.50    1.11    --   97.11 -59.00 -30.00   64
 15  ω     -3.00  23.00   0.50    0.28    --   45.09 -21.00 -30.00   52
 16  ω     -9.00  16.00   0.50    0.28    --   45.09 -21.00  30.00   50
 17  ω    -10.00  37.00   0.50    0.28    --   45.09 -32.00 -60.00   94
 18  ω      0.00  25.00   0.50    0.28    --   45.09 -21.00-150.00   50
 19  ω     32.00  81.00   0.50    1.11    --   97.11 -68.00-180.00   98
 20  ω    -28.00  26.00   0.50    0.28    --  -43.84  21.00 -30.00  108
 21  ω    -67.00 -38.00   0.50    1.11    --  -95.86  59.00 120.00   58
 22  ω    -54.00 -29.00   0.50    1.11    --  -95.86  50.00  30.00   50
 23  ω    -55.00 -30.00   0.50    1.11    --  -95.86  50.00 150.00   50
 24  ω    -57.00 -30.00   0.50    1.11    --  -95.86  50.00 -30.00   54
 25  ω    -56.00 -30.00   0.50    1.11    --  -95.86  50.00   0.00   52
 26  ω    -55.00 -29.00   0.50    1.11    --  -95.86  50.00 -60.00   52
 27  ω    -57.00 -31.00   0.50    1.11    --  -95.86  50.00 -90.00   52
 28  ω    -22.00  26.00   0.50    0.28    --  -43.84  21.00 -90.00   96
 29  ω    -78.00 -44.00   0.50    1.11    --  -95.86  68.00-180.00   68
 30  ω    -91.00 -60.00   0.50    0.28    --  -43.84 138.00-150.00   62
 31  ω    -98.00 -69.00   0.50    1.11    --  -95.86 120.00 154.00   58
 32  ω    -66.00 -29.00   0.50    0.28    --  -43.84 120.00 154.00   74
 33  ω   -124.00 -87.00   0.50    1.11    --  -95.86 -25.00 150.00   74
 34  ω   -152.00-127.00   0.50    1.11    --  -95.86 -25.00 150.00   50
 35  ω   -167.00-125.00   0.50    1.11    --  -95.86 -17.00-120.00   84
 36  ω   -112.00 -83.00   0.50    1.11    --  -95.86 -17.00-120.00   58
 37  ω   -108.00 -67.00   0.50    0.28    --  -43.84-155.00 -86.00   82
 38  ω    -94.00 -54.00   0.50    1.11    --  -95.86-155.00 -86.00   80
 39  ω   -126.00-100.00   0.50    1.11    --  -95.86-120.00  70.00   52
 40  ω   -106.00 -68.00   0.50    0.28    --  -43.84-138.00  90.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2244
_reflns_number_total             2493
_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 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_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  (Sheldrick, 2015)'
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0041(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   1.082
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         2493
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0586P)²+0.5113P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1141
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_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
F23 F 0.55072(8) 0.2535(2) 0.73839(7) 0.0568(4) Uani 1 1 d . . . . .
O10 O 0.45866(8) 0.7413(2) 0.55095(7) 0.0389(3) Uani 1 1 d . . . . .
F22 F 0.41426(11) 0.0646(2) 0.68549(7) 0.0613(4) Uani 1 1 d . . . . .
F21 F 0.42160(11) 0.5977(2) 0.77287(8) 0.0653(4) Uani 1 1 d . . . . .
O25 O 0.56437(9) 0.6729(3) 0.67092(8) 0.0483(4) Uani 1 1 d . . . . .
F20 F 0.30363(9) 0.3512(3) 0.73620(7) 0.0679(4) Uani 1 1 d . . . . .
O24 O 0.23625(12) 0.9567(3) 0.30007(9) 0.0571(4) Uani 1 1 d . . . . .
H24 H 0.192(2) 0.917(6) 0.2665(19) 0.083(10) Uiso 1 1 d . . . . .
F18 F 0.52735(10) 0.3462(4) 0.89073(8) 0.0867(6) Uani 1 1 d . . . . .
F19 F 0.43610(19) 0.0500(3) 0.84819(10) 0.1072(7) Uani 1 1 d . . . . .
F15 F 0.36279(15) 0.5565(4) 0.91555(11) 0.0995(6) Uani 1 1 d . . . . .
F17 F 0.41041(16) 0.2567(4) 0.98423(9) 0.1068(7) Uani 1 1 d . . . . .
C1 C 0.37471(11) 0.6932(3) 0.48739(9) 0.0326(4) Uani 1 1 d . . . . .
C9 C 0.48986(12) 0.6102(3) 0.62068(9) 0.0353(4) Uani 1 1 d . . . . .
C6 C 0.32163(12) 0.4949(3) 0.48920(10) 0.0360(4) Uani 1 1 d . . . . .
C8 C 0.43004(12) 0.4115(3) 0.62430(10) 0.0365(4) Uani 1 1 d . . . . .
C2 C 0.34776(13) 0.8471(3) 0.42442(10) 0.0381(4) Uani 1 1 d . . . . .
H2 H 0.3835(15) 0.980(4) 0.4231(12) 0.041(5) Uiso 1 1 d . . . . .
C7 C 0.35169(13) 0.3566(3) 0.56010(11) 0.0402(4) Uani 1 1 d . . . . .
H7 H 0.3149(16) 0.229(4) 0.5650(13) 0.050(6) Uiso 1 1 d . . . . .
F16 F 0.27957(15) 0.2555(5) 0.88289(11) 0.1254(9) Uani 1 1 d . . . . .
C3 C 0.26259(13) 0.8022(3) 0.36007(10) 0.0395(4) Uani 1 1 d . . . . .
C4 C 0.20820(13) 0.6034(4) 0.35931(10) 0.0446(4) Uani 1 1 d . . . . .
H4 H 0.1546(17) 0.575(4) 0.3145(14) 0.057(6) Uiso 1 1 d . . . . .
C11 C 0.45210(14) 0.2756(3) 0.70237(11) 0.0417(4) Uani 1 1 d . . . . .
C5 C 0.23769(14) 0.4523(4) 0.42212(11) 0.0453(4) Uani 1 1 d . . . . .
H5 H 0.2009(18) 0.309(5) 0.4236(15) 0.062(7) Uiso 1 1 d . . . . .
C12 C 0.40302(14) 0.3766(3) 0.76632(11) 0.0426(4) Uani 1 1 d . . . . .
C13 C 0.43498(17) 0.2736(4) 0.85343(12) 0.0543(5) Uani 1 1 d . . . . .
C14 C 0.3699(2) 0.3375(6) 0.91001(14) 0.0702(7) 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
F23 C11 1.347(2) . ?
O10 C1 1.3817(18) . ?
O10 C9 1.377(2) . ?
F22 C11 1.356(2) . ?
F21 C12 1.333(2) . ?
O25 C9 1.204(2) . ?
F20 C12 1.346(2) . ?
O24 H24 0.75(3) . ?
O24 C3 1.339(2) . ?
F18 C13 1.339(3) . ?
F19 C13 1.327(3) . ?
F15 C14 1.305(4) . ?
F17 C14 1.315(3) . ?
C1 C6 1.393(2) . ?
C1 C2 1.372(2) . ?
C9 C8 1.453(2) . ?
C6 C7 1.415(2) . ?
C6 C5 1.409(2) . ?
C8 C7 1.349(2) . ?
C8 C11 1.503(2) . ?
C2 H2 0.93(2) . ?
C2 C3 1.396(2) . ?
C7 H7 0.93(2) . ?
F16 C14 1.308(3) . ?
C3 C4 1.399(3) . ?
C4 H4 0.92(2) . ?
C4 C5 1.362(3) . ?
C11 C12 1.550(3) . ?
C5 H5 0.99(3) . ?
C12 C13 1.541(3) . ?
C13 C14 1.537(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O10 C1 123.24(13) . . ?
C3 O24 H24 111(3) . . ?
O10 C1 C6 119.83(15) . . ?
C2 C1 O10 117.22(15) . . ?
C2 C1 C6 122.95(14) . . ?
O10 C9 C8 116.31(14) . . ?
O25 C9 O10 115.85(16) . . ?
O25 C9 C8 127.83(16) . . ?
C1 C6 C7 118.13(15) . . ?
C1 C6 C5 117.47(16) . . ?
C5 C6 C7 124.29(16) . . ?
C9 C8 C11 119.34(15) . . ?
C7 C8 C9 120.51(16) . . ?
C7 C8 C11 120.03(16) . . ?
C1 C2 H2 123.0(12) . . ?
C1 C2 C3 117.96(16) . . ?
C3 C2 H2 119.1(12) . . ?
C6 C7 H7 120.2(13) . . ?
C8 C7 C6 121.71(17) . . ?
C8 C7 H7 117.9(13) . . ?
O24 C3 C2 117.11(17) . . ?
O24 C3 C4 122.24(16) . . ?
C2 C3 C4 120.65(17) . . ?
C3 C4 H4 118.4(15) . . ?
C5 C4 C3 119.98(16) . . ?
C5 C4 H4 121.5(15) . . ?
F23 C11 F22 107.15(15) . . ?
F23 C11 C8 112.57(15) . . ?
F23 C11 C12 108.35(15) . . ?
F22 C11 C8 109.60(15) . . ?
F22 C11 C12 106.33(15) . . ?
C8 C11 C12 112.51(15) . . ?
C6 C5 H5 116.8(14) . . ?
C4 C5 C6 120.96(17) . . ?
C4 C5 H5 122.2(14) . . ?
F21 C12 F20 107.29(16) . . ?
F21 C12 C11 108.89(15) . . ?
F21 C12 C13 108.13(17) . . ?
F20 C12 C11 107.48(15) . . ?
F20 C12 C13 108.20(16) . . ?
C13 C12 C11 116.51(16) . . ?
F18 C13 C12 108.00(18) . . ?
F18 C13 C14 106.56(18) . . ?
F19 C13 F18 108.9(2) . . ?
F19 C13 C12 109.68(18) . . ?
F19 C13 C14 107.9(2) . . ?
C14 C13 C12 115.62(19) . . ?
F15 C14 F17 108.3(2) . . ?
F15 C14 F16 108.0(3) . . ?
F15 C14 C13 111.0(2) . . ?
F17 C14 C13 109.4(2) . . ?
F16 C14 F17 108.5(2) . . ?
F16 C14 C13 111.6(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F23 C11 C12 F21 77.47(18) . . . . ?
F23 C11 C12 F20 -166.62(15) . . . . ?
F23 C11 C12 C13 -45.1(2) . . . . ?
O10 C1 C6 C7 4.8(2) . . . . ?
O10 C1 C6 C5 -178.88(15) . . . . ?
O10 C1 C2 C3 -179.43(15) . . . . ?
O10 C9 C8 C7 3.3(2) . . . . ?
O10 C9 C8 C11 -172.83(14) . . . . ?
F22 C11 C12 F21 -167.64(14) . . . . ?
F22 C11 C12 F20 -51.72(19) . . . . ?
F22 C11 C12 C13 69.8(2) . . . . ?
F21 C12 C13 F18 -49.2(2) . . . . ?
F21 C12 C13 F19 -167.80(19) . . . . ?
F21 C12 C13 C14 70.0(2) . . . . ?
O25 C9 C8 C7 -175.72(18) . . . . ?
O25 C9 C8 C11 8.2(3) . . . . ?
F20 C12 C13 F18 -165.14(17) . . . . ?
F20 C12 C13 F19 76.3(2) . . . . ?
F20 C12 C13 C14 -45.9(3) . . . . ?
O24 C3 C4 C5 -179.53(18) . . . . ?
F18 C13 C14 F15 65.4(3) . . . . ?
F18 C13 C14 F17 -54.1(3) . . . . ?
F18 C13 C14 F16 -174.1(2) . . . . ?
F19 C13 C14 F15 -177.8(2) . . . . ?
F19 C13 C14 F17 62.7(3) . . . . ?
F19 C13 C14 F16 -57.3(3) . . . . ?
C1 O10 C9 O25 -179.98(15) . . . . ?
C1 O10 C9 C8 0.9(2) . . . . ?
C1 C6 C7 C8 -0.7(3) . . . . ?
C1 C6 C5 C4 -1.9(3) . . . . ?
C1 C2 C3 O24 178.59(16) . . . . ?
C1 C2 C3 C4 -1.5(3) . . . . ?
C9 O10 C1 C6 -5.0(2) . . . . ?
C9 O10 C1 C2 175.12(15) . . . . ?
C9 C8 C7 C6 -3.3(3) . . . . ?
C9 C8 C11 F23 -40.0(2) . . . . ?
C9 C8 C11 F22 -159.15(15) . . . . ?
C9 C8 C11 C12 82.8(2) . . . . ?
C6 C1 C2 C3 0.7(3) . . . . ?
C8 C11 C12 F21 -47.6(2) . . . . ?
C8 C11 C12 F20 68.3(2) . . . . ?
C8 C11 C12 C13 -170.20(16) . . . . ?
C2 C1 C6 C7 -175.30(16) . . . . ?
C2 C1 C6 C5 1.0(3) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C7 C6 C5 C4 174.09(18) . . . . ?
C7 C8 C11 F23 143.90(17) . . . . ?
C7 C8 C11 F22 24.8(2) . . . . ?
C7 C8 C11 C12 -93.3(2) . . . . ?
C3 C4 C5 C6 1.2(3) . . . . ?
C11 C8 C7 C6 172.71(16) . . . . ?
C11 C12 C13 F18 73.7(2) . . . . ?
C11 C12 C13 F19 -44.8(3) . . . . ?
C11 C12 C13 C14 -167.07(19) . . . . ?
C5 C6 C7 C8 -176.74(17) . . . . ?
C12 C13 C14 F15 -54.6(3) . . . . ?
C12 C13 C14 F17 -174.1(2) . . . . ?
C12 C13 C14 F16 65.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane, chloroform'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_AIcoumarin_six_fourb_auto
_database_code_depnum_ccdc_archive 'CCDC 2219771'
loop_
_audit_author_name
_audit_author_address
'Ayano Ikemura'
;Gifu University
Japan
;
_audit_update_record             
;
2022-11-15 deposited with the CCDC.	2024-02-21 downloaded from the CCDC.
;
_audit_creation_date             2022-09-22
_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        
7-(benzyloxy)-3-(perfluorobutyl)-2H-chromen-2-one
_chemical_formula_moiety         'C20 H11 F9 O3'
_chemical_formula_sum            'C20 H11 F9 O3'
_chemical_formula_weight         470.29
_chemical_melting_point          406
_chemical_oxdiff_formula         C20H11F9O3
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'
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                   7.4736(4)
_cell_length_b                   8.8428(4)
_cell_length_c                   15.7659(7)
_cell_angle_alpha                85.931(4)
_cell_angle_beta                 88.314(4)
_cell_angle_gamma                69.315(5)
_cell_volume                     972.29(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4621
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.9800
_cell_measurement_theta_min      2.8220
_shelx_estimated_absorpt_T_max   1.00000
_shelx_estimated_absorpt_T_min   0.44804
_exptl_absorpt_coefficient_mu    1.481
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   1.00000
_exptl_transmission_factor_min   0.44804
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.918
_diffrn_reflns_theta_min         2.810
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     79.00 115.00   0.50    0.36    --   97.43  77.00-120.00   72
  2  ω    124.00 163.00   0.50    0.36    --   97.43  77.00-120.00   78
  3  ω     87.00 163.00   0.50    0.36    --   97.43  59.00-180.00  152
  4  ω     97.00 149.00   0.50    0.36    --   97.43  33.00 120.00  104
  5  ω     31.00  56.00   0.50    0.36    --   97.43 -50.00 150.00   50
  6  ω     51.00  81.00   0.50    0.36    --   97.43 -68.00  90.00   60
  7  ω     55.00 105.00   0.50    0.36    --   97.43 -77.00  30.00  100
  8  ω     31.00  56.00   0.50    0.36    --   97.43 -50.00 120.00   50
  9  ω     31.00  65.00   0.50    0.36    --   97.43 -59.00 -30.00   68
 10  ω     31.00  56.00   0.50    0.36    --   97.43 -50.00  30.00   50
 11  ω     69.00  95.00   0.50    0.36    --   97.43 -77.00 -60.00   52
 12  ω     31.00  56.00   0.50    0.36    --   97.43 -50.00 -60.00   50
 13  ω     33.00  58.00   0.50    0.36    --   97.43 -59.00-120.00   50
 14  ω     31.00  56.00   0.50    0.36    --   97.43 -50.00-180.00   50
 15  ω     98.00 126.00   0.50    0.36    --   97.43-145.00-150.00   56
 16  ω     35.00  81.00   0.50    0.36    --   97.43-145.00-150.00   92
 17  ω     33.00 108.00   0.50    0.36    --   97.43-117.00 -90.00  150
 18  ω     42.00 104.00   0.50    0.36    --   97.43 -96.00 -60.00  124
 19  ω     48.00 110.00   0.50    0.36    --   97.43-117.00  60.00  124
 20  ω     65.00  99.00   0.50    0.36    --   97.43 -90.00 150.00   68
 21  ω     29.00  54.00   0.50    0.20    --   44.40 -89.00  90.00   50
 22  ω    -16.00  18.00   0.50    0.20    --   44.40 -89.00  90.00   68
 23  ω     -7.00  64.00   0.50    0.20    --   44.40 -90.00 150.00  142
 24  ω     43.00  80.00   0.50    0.20    --   44.40-104.00  30.00   74
 25  ω     -1.00  32.00   0.50    0.20    --   44.40-104.00  30.00   66
 26  ω     74.00 110.00   0.50    0.20    --   44.40 138.00  30.00   72
 27  ω    129.00 161.00   0.50    0.36    --   97.43  90.00 -94.00   64
 28  ω     21.00  46.00   0.50    0.20    --   44.40 -43.00-180.00   50
 29  ω     33.00  58.00   0.50    0.20    --   44.40 -77.00 -30.00   50
 30  ω     -6.00  23.00   0.50    0.20    --   44.40 -77.00 -30.00   58
 31  ω     -3.00  22.00   0.50    0.20    --  -42.84  43.00 -90.00   50
 32  ω     -6.00  31.00   0.50    0.20    --  -42.84  11.00-150.00   74
 33  ω    -48.00  -7.00   0.50    0.20    --  -42.84  43.00 -90.00   82
 34  ω    -40.00  -2.00   0.50    0.20    --  -42.84  43.00 120.00   76
 35  ω    -24.00  24.00   0.50    0.20    --  -42.84  21.00 150.00   96
 36  ω    -33.00   0.00   0.50    0.20    --  -42.84  32.00  60.00   66
 37  ω     -7.00  28.00   0.50    0.20    --  -42.84  11.00   0.00   70
 38  ω    -57.00 -32.00   0.50    0.36    --  -95.86  50.00  90.00   50
 39  ω    -68.00 -29.00   0.50    0.36    --  -95.86  59.00 120.00   78
 40  ω    -56.00 -30.00   0.50    0.36    --  -95.86  50.00  60.00   52
 41  ω    -57.00 -32.00   0.50    0.36    --  -95.86  50.00 -90.00   50
 42  ω    -81.00 -56.00   0.50    0.36    --  -95.86  68.00-120.00   50
 43  ω    -68.00 -43.00   0.50    0.36    --  -95.86  59.00-150.00   50
 44  ω    -90.00 -64.00   0.50    0.36    --  -95.86  90.00 -94.00   52
 45  ω   -109.00 -82.00   0.50    0.36    --  -95.86 117.00 -90.00   54
 46  ω    -76.00 -33.00   0.50    0.36    --  -95.86 117.00 -90.00   86
 47  ω    -66.00 -11.00   0.50    0.20    --  -42.84  90.00 -94.00  110
 48  ω     -1.00  25.00   0.50    0.20    --  -42.84  90.00 -94.00   52
 49  ω    -62.00 -25.00   0.50    0.36    --  -95.86  96.00 -30.00   74
 50  ω   -121.00 -96.00   0.50    0.36    --  -95.86 -17.00-150.00   50
 51  ω   -159.00-118.00   0.50    0.36    --  -95.86 -68.00-180.00   82
 52  ω    -99.00 -74.00   0.50    0.36    --  -95.86 -68.00-180.00   50
 53  ω   -153.00 -86.00   0.50    0.36    --  -95.86 -33.00 -90.00  134
 54  ω   -146.00 -95.00   0.50    0.36    --  -95.86 -42.00   0.00  102
 55  ω   -106.00 -30.00   0.50    0.20    --  -42.84 -43.00  30.00  152
 56  ω   -161.00 -89.00   0.50    0.36    --  -95.86 -50.00  60.00  144
 57  ω   -160.00-134.00   0.50    0.36    --  -95.86 -90.00 150.00   52
 58  ω   -108.00 -67.00   0.50    0.20    --  -42.84-138.00  30.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1277050000
_diffrn_orient_matrix_UB_12      0.0662830000
_diffrn_orient_matrix_UB_13      -0.0789090000
_diffrn_orient_matrix_UB_21      0.1534819000
_diffrn_orient_matrix_UB_22      0.0602083000
_diffrn_orient_matrix_UB_23      -0.0419426000
_diffrn_orient_matrix_UB_31      0.0931891000
_diffrn_orient_matrix_UB_32      -0.1637259000
_diffrn_orient_matrix_UB_33      -0.0401370000
_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                2665
_reflns_number_total             3633
_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 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_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         0.266
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0077(14)
_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   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3633
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0660
_refine_ls_restrained_S_all      1.104
_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)+(0.1115P)²+0.1842P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2043
_refine_ls_wR_factor_ref         0.2202
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
1.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C2(H2), C18(H18), C14(H14), C5(H5), C7(H7), C16(H16), C17(H17),
 C15(H15)
;
_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
O10 O 0.5855(3) 0.57934(18) 0.40092(11) 0.0745(5) Uani 1 1 d . . . . .
F31 F 0.9589(3) 0.3153(2) 0.21776(13) 0.1110(7) Uani 1 1 d . . . . .
F30 F 0.8502(3) 0.5171(2) 0.12478(13) 0.1109(6) Uani 1 1 d . . . . .
F29 F 0.6265(3) 0.2524(2) 0.20462(12) 0.1103(6) Uani 1 1 d . . . . .
F28 F 0.5158(3) 0.4623(2) 0.11782(13) 0.1090(6) Uani 1 1 d . . . . .
O11 O 0.1954(3) 1.10256(19) 0.48374(12) 0.0793(5) Uani 1 1 d . . . . .
O32 O 0.7450(4) 0.3319(2) 0.36528(13) 0.1106(8) Uani 1 1 d . . . . .
F26 F 0.9369(4) 0.1444(4) 0.0904(2) 0.2016(17) Uani 1 1 d . . . . .
C20 C 0.6761(4) 0.3472(3) 0.14567(19) 0.0847(8) Uani 1 1 d . . . . .
F27 F 0.7839(5) 0.3451(4) 0.00485(16) 0.1647(11) Uani 1 1 d . . . . .
C1 C 0.4927(3) 0.7424(2) 0.38106(16) 0.0642(6) Uani 1 1 d . . . . .
C6 C 0.5002(4) 0.8065(3) 0.29909(16) 0.0692(6) Uani 1 1 d . . . . .
C19 C 0.7977(4) 0.4297(3) 0.18828(18) 0.0831(8) Uani 1 1 d . . . . .
C3 C 0.2977(3) 0.9980(3) 0.42784(17) 0.0684(6) Uani 1 1 d . . . . .
C4 C 0.3012(4) 1.0670(3) 0.34524(19) 0.0799(7) Uani 1 1 d . . . . .
H4 H 0.235413 1.176974 0.333214 0.096 Uiso 1 1 calc R U . . .
F23 F 0.6566(9) 0.0302(5) 0.0872(2) 0.239(2) Uani 1 1 d . . . . .
C13 C 0.0528(4) 1.1838(3) 0.61752(19) 0.0742(7) Uani 1 1 d . . . . .
F25 F 0.7220(5) 0.0890(4) -0.0360(2) 0.1970(15) Uani 1 1 d . . . . .
C9 C 0.6801(4) 0.4726(3) 0.34122(17) 0.0782(7) Uani 1 1 d . . . . .
C8 C 0.6920(4) 0.5402(3) 0.25601(17) 0.0739(7) Uani 1 1 d . . . . .
C21 C 0.7665(6) 0.2450(5) 0.0705(2) 0.1085(11) Uani 1 1 d . . . . .
C2 C 0.3950(3) 0.8334(3) 0.44640(16) 0.0660(6) Uani 1 1 d . . . . .
H2 H 0.394053 0.786477 0.501016 0.079 Uiso 1 1 calc R U . . .
C12 C 0.1760(4) 1.0447(3) 0.56905(18) 0.0739(7) Uani 1 1 d . . . . .
H12A H 0.300833 0.996956 0.595401 0.089 Uiso 1 1 calc R U . . .
H12B H 0.118169 0.962193 0.569388 0.089 Uiso 1 1 calc R U . . .
F24 F 0.4794(5) 0.2340(5) 0.0240(3) 0.2023(17) Uani 1 1 d . . . . .
C18 C -0.0383(4) 1.3375(3) 0.5794(2) 0.0900(8) Uani 1 1 d . . . . .
H18 H -0.023370 1.356988 0.521355 0.108 Uiso 1 1 calc R U . . .
C14 C 0.0249(5) 1.1583(4) 0.7037(2) 0.0935(9) Uani 1 1 d . . . . .
H14 H 0.082686 1.055926 0.730473 0.112 Uiso 1 1 calc R U . . .
C5 C 0.4006(4) 0.9735(3) 0.28272(18) 0.0810(8) Uani 1 1 d . . . . .
H5 H 0.402807 1.020561 0.228221 0.097 Uiso 1 1 calc R U . . .
C22 C 0.6552(8) 0.1504(6) 0.0357(3) 0.1262(14) Uani 1 1 d . . . . .
C7 C 0.6039(4) 0.7009(3) 0.23695(18) 0.0763(7) Uani 1 1 d . . . . .
H7 H 0.611613 0.742976 0.181766 0.092 Uiso 1 1 calc R U . . .
C16 C -0.1765(5) 1.4367(5) 0.7108(3) 0.1067(11) Uani 1 1 d . . . . .
H16 H -0.253016 1.521810 0.741862 0.128 Uiso 1 1 calc R U . . .
C17 C -0.1501(5) 1.4606(4) 0.6268(3) 0.1050(11) Uani 1 1 d . . . . .
H17 H -0.209075 1.563047 0.600289 0.126 Uiso 1 1 calc R U . . .
C15 C -0.0894(6) 1.2854(6) 0.7504(3) 0.1135(12) Uani 1 1 d . . . . .
H15 H -0.106946 1.268080 0.808436 0.136 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
O10 C1 1.378(3) . ?
O10 C9 1.376(3) . ?
F31 C19 1.340(3) . ?
F30 C19 1.354(3) . ?
F29 C20 1.339(3) . ?
F28 C20 1.330(3) . ?
O11 C3 1.339(3) . ?
O11 C12 1.427(3) . ?
O32 C9 1.202(3) . ?
F26 C21 1.302(4) . ?
C20 C19 1.544(5) . ?
C20 C21 1.534(5) . ?
F27 C21 1.347(5) . ?
C1 C6 1.381(3) . ?
C1 C2 1.379(4) . ?
C6 C5 1.408(3) . ?
C6 C7 1.416(4) . ?
C19 C8 1.507(4) . ?
C3 C4 1.402(4) . ?
C3 C2 1.392(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.358(4) . ?
F23 C22 1.288(5) . ?
C13 C12 1.495(4) . ?
C13 C18 1.388(4) . ?
C13 C14 1.383(4) . ?
F25 C22 1.297(5) . ?
C9 C8 1.445(4) . ?
C8 C7 1.354(3) . ?
C21 C22 1.509(6) . ?
C2 H2 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
F24 C22 1.271(5) . ?
C18 H18 0.9300 . ?
C18 C17 1.370(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.393(5) . ?
C5 H5 0.9300 . ?
C7 H7 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.347(5) . ?
C16 C15 1.376(5) . ?
C17 H17 0.9300 . ?
C15 H15 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
C9 O10 C1 122.82(19) . . ?
C3 O11 C12 119.36(18) . . ?
F29 C20 C19 108.7(2) . . ?
F29 C20 C21 108.0(3) . . ?
F28 C20 F29 107.3(3) . . ?
F28 C20 C19 108.0(2) . . ?
F28 C20 C21 107.3(3) . . ?
C21 C20 C19 117.1(3) . . ?
O10 C1 C6 120.1(2) . . ?
O10 C1 C2 116.5(2) . . ?
C2 C1 C6 123.4(2) . . ?
C1 C6 C5 117.3(2) . . ?
C1 C6 C7 118.5(2) . . ?
C5 C6 C7 124.3(2) . . ?
F31 C19 F30 106.6(2) . . ?
F31 C19 C20 108.8(2) . . ?
F31 C19 C8 112.2(2) . . ?
F30 C19 C20 105.6(2) . . ?
F30 C19 C8 109.4(2) . . ?
C8 C19 C20 113.7(2) . . ?
O11 C3 C4 114.5(2) . . ?
O11 C3 C2 125.1(2) . . ?
C2 C3 C4 120.4(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.1(2) . . ?
C5 C4 H4 119.9 . . ?
C18 C13 C12 122.8(3) . . ?
C14 C13 C12 118.9(2) . . ?
C14 C13 C18 118.3(3) . . ?
O10 C9 C8 117.0(2) . . ?
O32 C9 O10 116.6(2) . . ?
O32 C9 C8 126.4(3) . . ?
C9 C8 C19 119.4(2) . . ?
C7 C8 C19 120.5(2) . . ?
C7 C8 C9 120.0(3) . . ?
F26 C21 C20 110.2(3) . . ?
F26 C21 F27 108.0(4) . . ?
F26 C21 C22 108.2(3) . . ?
F27 C21 C20 108.4(3) . . ?
F27 C21 C22 105.1(3) . . ?
C22 C21 C20 116.5(4) . . ?
C1 C2 C3 117.7(2) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
O11 C12 C13 108.7(2) . . ?
O11 C12 H12A 109.9 . . ?
O11 C12 H12B 109.9 . . ?
C13 C12 H12A 109.9 . . ?
C13 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
C13 C18 H18 119.8 . . ?
C17 C18 C13 120.4(3) . . ?
C17 C18 H18 119.8 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.2(3) . . ?
C15 C14 H14 119.9 . . ?
C6 C5 H5 119.5 . . ?
C4 C5 C6 121.1(2) . . ?
C4 C5 H5 119.5 . . ?
F23 C22 F25 106.0(4) . . ?
F23 C22 C21 111.7(4) . . ?
F25 C22 C21 113.4(4) . . ?
F24 C22 F23 105.2(5) . . ?
F24 C22 F25 106.8(4) . . ?
F24 C22 C21 113.1(4) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 C6 121.5(2) . . ?
C8 C7 H7 119.2 . . ?
C17 C16 H16 120.2 . . ?
C17 C16 C15 119.5(3) . . ?
C15 C16 H16 120.2 . . ?
C18 C17 H17 119.2 . . ?
C16 C17 C18 121.5(3) . . ?
C16 C17 H17 119.2 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.1(4) . . ?
C16 C15 H15 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O10 C1 C6 C5 179.3(2) . . . . ?
O10 C1 C6 C7 0.3(3) . . . . ?
O10 C1 C2 C3 -179.1(2) . . . . ?
O10 C9 C8 C19 178.6(2) . . . . ?
O10 C9 C8 C7 -3.3(4) . . . . ?
F31 C19 C8 C9 -40.4(4) . . . . ?
F31 C19 C8 C7 141.5(3) . . . . ?
F30 C19 C8 C9 -158.5(2) . . . . ?
F30 C19 C8 C7 23.5(4) . . . . ?
F29 C20 C19 F31 63.1(3) . . . . ?
F29 C20 C19 F30 177.2(2) . . . . ?
F29 C20 C19 C8 -62.8(3) . . . . ?
F29 C20 C21 F26 -73.4(4) . . . . ?
F29 C20 C21 F27 168.7(3) . . . . ?
F29 C20 C21 C22 50.5(4) . . . . ?
F28 C20 C19 F31 179.2(2) . . . . ?
F28 C20 C19 F30 -66.7(3) . . . . ?
F28 C20 C19 C8 53.3(3) . . . . ?
F28 C20 C21 F26 171.2(3) . . . . ?
F28 C20 C21 F27 53.2(4) . . . . ?
F28 C20 C21 C22 -65.0(4) . . . . ?
O11 C3 C4 C5 179.8(2) . . . . ?
O11 C3 C2 C1 179.6(2) . . . . ?
O32 C9 C8 C19 -1.2(5) . . . . ?
O32 C9 C8 C7 176.8(3) . . . . ?
F26 C21 C22 F23 53.5(5) . . . . ?
F26 C21 C22 F25 -66.2(6) . . . . ?
F26 C21 C22 F24 171.9(4) . . . . ?
C20 C19 C8 C9 83.7(3) . . . . ?
C20 C19 C8 C7 -94.4(3) . . . . ?
C20 C21 C22 F23 -71.4(5) . . . . ?
C20 C21 C22 F25 169.0(4) . . . . ?
C20 C21 C22 F24 47.1(6) . . . . ?
F27 C21 C22 F23 168.6(4) . . . . ?
F27 C21 C22 F25 49.0(5) . . . . ?
F27 C21 C22 F24 -72.9(5) . . . . ?
C1 O10 C9 O32 -175.4(2) . . . . ?
C1 O10 C9 C8 4.7(4) . . . . ?
C1 C6 C5 C4 -0.1(4) . . . . ?
C1 C6 C7 C8 1.0(4) . . . . ?
C6 C1 C2 C3 0.7(4) . . . . ?
C19 C20 C21 F26 49.7(5) . . . . ?
C19 C20 C21 F27 -68.3(4) . . . . ?
C19 C20 C21 C22 173.5(3) . . . . ?
C19 C8 C7 C6 178.6(2) . . . . ?
C3 O11 C12 C13 -178.83(19) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C4 C3 C2 C1 -0.3(3) . . . . ?
C13 C18 C17 C16 -0.6(5) . . . . ?
C13 C14 C15 C16 0.6(5) . . . . ?
C9 O10 C1 C6 -3.3(4) . . . . ?
C9 O10 C1 C2 176.5(2) . . . . ?
C9 C8 C7 C6 0.6(4) . . . . ?
C21 C20 C19 F31 -59.6(3) . . . . ?
C21 C20 C19 F30 54.5(3) . . . . ?
C21 C20 C19 C8 174.5(2) . . . . ?
C2 C1 C6 C5 -0.5(4) . . . . ?
C2 C1 C6 C7 -179.5(2) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C12 O11 C3 C4 177.7(2) . . . . ?
C12 O11 C3 C2 -2.1(4) . . . . ?
C12 C13 C18 C17 179.8(3) . . . . ?
C12 C13 C14 C15 -179.8(3) . . . . ?
C18 C13 C12 O11 5.7(3) . . . . ?
C18 C13 C14 C15 -1.1(4) . . . . ?
C14 C13 C12 O11 -175.6(2) . . . . ?
C14 C13 C18 C17 1.1(4) . . . . ?
C5 C6 C7 C8 -177.9(3) . . . . ?
C7 C6 C5 C4 178.8(3) . . . . ?
C17 C16 C15 C14 -0.1(6) . . . . ?
C15 C16 C17 C18 0.1(6) . . . . ?

_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 1.943
_oxdiff_exptl_absorpt_empirical_full_min 0.485
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane, chloroform'
_exptl_crystal_preparation       Luminescent
