# Supplementary Information (SI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_2papa_1p8gpa
_database_code_depnum_ccdc_archive 'CCDC 2332696'
loop_
_audit_author_name
_audit_author_address
'Anna Makal'
;University of Warsaw, Chemistry Department
Poland
;
_audit_update_record             
;
2024-02-13 deposited with the CCDC.	2024-07-24 downloaded from the CCDC.
;
_audit_creation_date             2024-01-27
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2023.11.24 svn.r209d9fb for OlexSys, GUI svn.r6869)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H14 O2'
_chemical_formula_sum            'C20 H14 O2'
_chemical_formula_weight         286.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.03(4)
_cell_length_b                   7.104(4)
_cell_length_c                   9.88(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.4(5)
_cell_angle_gamma                90
_cell_volume                     621(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    490
_cell_measurement_temperature    290.4(4)
_cell_measurement_theta_max      26.3800
_cell_measurement_theta_min      2.7510
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.94197
_exptl_absorpt_correction_T_min  0.94197
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Spherical absorption correction
using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             300
_exptl_crystal_preparation       
'Mounted in a Diamond-Anvil Cell using paratone oil as pressure medium.,Luminescent'
_exptl_crystal_pressure_history  'Pressurized to 1.76 GPa.'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.09
_exptl_crystal_size_rad          0.400
_exptl_special_details           
;
High-pressure measurement at 1.76(10) GPa in a Merill-Basset Diamond Anvil Cell with effective opening angle of 40 deg. and paratone oil used as a pressure medium. Pressure determined by monitoring the shift of the ruby R1-fluorescence line.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1797
_diffrn_reflns_av_unetI/netI     0.1416
_diffrn_reflns_Laue_measured_fraction_full 0.381
_diffrn_reflns_Laue_measured_fraction_max 0.370
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2014
_diffrn_reflns_point_group_measured_fraction_full 0.381
_diffrn_reflns_point_group_measured_fraction_max 0.370
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.237
_diffrn_reflns_theta_min         2.794
_diffrn_ambient_temperature      290.15
_diffrn_ambient_pressure         1760000
_diffrn_crystal_treatment        
'pressurized slowly/rapidly in paratone oil as a hydrostatic medium'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.381
_diffrn_measured_fraction_theta_max 0.370
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -15.00  23.00   1.00  120.00    --    9.85  39.00 -12.00   38
  2  ω     -3.00  35.00   1.00  120.00    --    9.85   0.00   0.00   38
  3  ω    -20.00   9.00   1.00  120.00    --    9.85  67.00 157.00   29
  4  ω      1.00  28.00   1.00  120.00    --    9.85 -26.00-172.00   27
  5  ω    -15.00  35.00   1.00  120.00    --    9.85 -26.00   7.00   50
  6  ω     22.00  59.00   1.00  120.00    --    9.85-114.00  45.00   37
  7  ω    -40.00 -15.00   1.00  120.00    --    9.85 114.00 135.00   25
  8  ω    -31.00  -5.00   1.00  120.00    --    9.85   0.00-150.00   26
  9  ω    -36.00 -10.00   1.00  120.00    --  -11.80  39.00 -12.00   26
 10  ω    -61.00 -36.00   1.00  120.00    --  -11.80 114.00 -45.00   25
 11  ω    -19.00   6.00   1.00  120.00    --  -11.80 -39.00-167.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 
'Diamond Anvil Cell, effective opening angle of 40 deg.'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                195
_reflns_number_total             462
_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-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       0.02(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         462
_refine_ls_number_restraints     78
_refine_ls_R_factor_all          0.2367
_refine_ls_R_factor_gt           0.1269
_refine_ls_restrained_S_all      1.049
_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)+(0.2000P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3051
_refine_ls_wR_factor_ref         0.3888
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C14(H14)
3.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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
O1 O 0.642(3) 0.337(2) 0.069(3) 0.075(11) Uani 1 1 d . U . . .
C17 C 0.745(5) 0.395(3) 0.157(5) 0.057(11) Uani 1 1 d . U . . .
C18 C 0.901(3) 0.452(2) 0.125(3) 0.069(14) Uani 1 1 d . U . . .
H18A H 0.9799 0.3375 0.1517 0.104 Uiso 1 1 calc R U . . .
H18B H 0.9427 0.5758 0.1849 0.104 Uiso 1 1 calc R U . . .
H18C H 0.8879 0.4839 0.0160 0.104 Uiso 1 1 calc R U . . .
C1 C 0.710(4) 0.407(2) 0.291(4) 0.053(11) Uani 1 1 d . U . . .
C2 C 0.586(4) 0.469(2) 0.340(4) 0.056(12) Uani 1 1 d . U . . .
C10 C 0.440(4) 0.513(2) 0.234(4) 0.060(12) Uani 1 1 d . U . . .
H10 H 0.4394 0.4941 0.1253 0.072 Uiso 1 1 calc R U . . .
C11 C 0.680(4) 0.4299(18) 0.728(3) 0.097(15) Uani 1 1 d . U . . .
H11 H 0.7737 0.3831 0.8054 0.116 Uiso 1 1 calc R U . . .
C12 C 0.693(5) 0.426(3) 0.584(5) 0.069(13) Uani 1 1 d . U . . .
C13 C 0.838(4) 0.3737(19) 0.549(3) 0.065(11) Uani 1 1 d . U . . .
H13 H 0.9340 0.3331 0.6274 0.078 Uiso 1 1 calc R U . . .
C14 C 0.846(4) 0.380(2) 0.409(4) 0.051(12) Uani 1 1 d . U . . .
H14 H 0.9552 0.3638 0.3828 0.062 Uiso 1 1 calc R U . . .
C15 C 0.567(5) 0.469(2) 0.477(4) 0.062(12) Uani 1 1 d . 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
O1 C17 1.22(6) . ?
C17 C18 1.56(3) . ?
C17 C1 1.42(4) . ?
C18 H18A 1.0831 . ?
C18 H18B 1.0831 . ?
C18 H18C 1.0831 . ?
C1 C2 1.37(3) . ?
C1 C14 1.53(6) . ?
C2 C10 1.54(6) . ?
C2 C15 1.40(5) . ?
C10 H10 1.0770 . ?
C10 C11 1.28(3) 3_666 ?
C11 C10 1.28(3) 3_666 ?
C11 H11 1.0770 . ?
C11 C12 1.45(4) . ?
C12 C13 1.47(3) . ?
C12 C15 1.42(7) . ?
C13 H13 1.0770 . ?
C13 C14 1.40(4) . ?
C14 H14 1.0770 . ?
C15 C15 1.43(4) 3_666 ?

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
O1 C17 C18 123(3) . . ?
O1 C17 C1 114(3) . . ?
C1 C17 C18 123(4) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C1 C14 114(3) . . ?
C2 C1 C17 134(5) . . ?
C2 C1 C14 111(3) . . ?
C1 C2 C10 118(3) . . ?
C1 C2 C15 127(5) . . ?
C15 C2 C10 114(2) . . ?
C2 C10 H10 119.4 . . ?
C11 C10 C2 121(3) 3_666 . ?
C11 C10 H10 119.4 3_666 . ?
C10 C11 H11 118.8 3_666 . ?
C10 C11 C12 122(4) 3_666 . ?
C12 C11 H11 118.8 . . ?
C11 C12 C13 119(4) . . ?
C15 C12 C11 121(2) . . ?
C15 C12 C13 121(3) . . ?
C12 C13 H13 121.9 . . ?
C14 C13 C12 116(4) . . ?
C14 C13 H13 121.9 . . ?
C1 C14 H14 117.6 . . ?
C13 C14 C1 125(2) . . ?
C13 C14 H14 117.6 . . ?
C2 C15 C12 119(3) . . ?
C2 C15 C15 125(6) . 3_666 ?
C12 C15 C15 116(4) . 3_666 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C17 C1 C2 -43(4) . . . . ?
O1 C17 C1 C14 150(3) . . . . ?
C17 C1 C2 C10 10(4) . . . . ?
C17 C1 C2 C15 179(2) . . . . ?
C17 C1 C14 C13 -175.7(13) . . . . ?
C18 C17 C1 C2 137(4) . . . . ?
C18 C17 C1 C14 -30(3) . . . . ?
C1 C2 C10 C11 179.7(14) . . . 3_666 ?
C1 C2 C15 C12 9(4) . . . . ?
C1 C2 C15 C15 -178(3) . . . 3_666 ?
C2 C1 C14 C13 14(3) . . . . ?
C10 C2 C15 C12 178(2) . . . . ?
C10 C2 C15 C15 -9(4) . . . 3_666 ?
C10 C11 C12 C13 174.7(18) 3_666 . . . ?
C10 C11 C12 C15 -6(4) 3_666 . . . ?
C11 C12 C13 C14 -177.5(16) . . . . ?
C11 C12 C15 C2 178.0(14) . . . . ?
C11 C12 C15 C15 5(4) . . . 3_666 ?
C12 C13 C14 C1 -9(3) . . . . ?
C13 C12 C15 C2 -3(4) . . . . ?
C13 C12 C15 C15 -175.9(14) . . . 3_666 ?
C14 C1 C2 C10 177.5(16) . . . . ?
C14 C1 C2 C15 -14(3) . . . . ?
C15 C2 C10 C11 10(3) . . . 3_666 ?
C15 C12 C13 C14 3(3) . . . . ?


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

# start Validation Reply Form
_vrf_PLAT029_2papa_1p8gpa        
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.381 Why?  
RESPONSE: High-pressure measurement at 0.51(10) GPa in a Merill-Basset 
Diamond Anvil Cell with effective opening angle of 40 deg. 
and paratone oil used as a pressure medium. The setup significantly 
reduced the number of collectable reflections.
;
_vrf_PLAT031_2papa_1p8gpa        
;
PROBLEM: Refined Extinction Parameter Within Range of ...      0.667 Sigma 
RESPONSE: High-pressure measurement at 0.51(10) GPa in a Merill-Basset 
Diamond Anvil Cell with effective opening angle of 40 deg. 
and paratone oil used as a pressure medium. The setup significantly 
reduced the number of collectable reflections and affected the intensities
of others. Extinction parameters corrects for insufficient absorption corr.
;
_vrf_PLAT088_2papa_1p8gpa        
;
PROBLEM: Poor Data / Parameter Ratio ....................       4.53 Note  
RESPONSE: High-pressure measurement at 0.51(10) GPa in a Merill-Basset 
Diamond Anvil Cell with effective opening angle of 40 deg. 
and paratone oil used as a pressure medium. The setup significantly 
reduced the number of collectable reflections, especially in some directions.
;
_vrf_PLAT340_2papa_1p8gpa        
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.055 Ang.  
RESPONSE: High-pressure measurement at 0.51(10) GPa in a Merill-Basset 
Diamond Anvil Cell with effective opening angle of 40 deg. 
and paratone oil used as a pressure medium. The setup significantly 
reduced the number of collectable reflections, especially in some directions.
;
_vrf_PLAT084_2papa_1p8gpa        
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.39 Report
RESPONSE: High-pressure measurement at 0.51(10) GPa in a Merill-Basset 
Diamond Anvil Cell with effective opening angle of 40 deg. 
and paratone oil used as a pressure medium. The setup significantly 
reduced the number of collectable reflections, especially in some directions.
;
_vrf_PLAT149_2papa_1p8gpa        
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.50 Degree
RESPONSE: High-pressure measurement at 0.51(10) GPa in a Merill-Basset 
Diamond Anvil Cell with effective opening angle of 40 deg. 
and paratone oil used as a pressure medium. The setup significantly 
reduced the number of collectable reflections, especially in some directions.
;
_vrf_PLAT911_2papa_1p8gpa        
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        650 Report
RESPONSE: High-pressure measurement at 0.51(10) GPa in a Merill-Basset 
Diamond Anvil Cell with effective opening angle of 40 deg. 
and paratone oil used as a pressure medium. The setup significantly 
reduced the number of collectable reflections, especially in some directions.
;
# end Validation Reply Form
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_2papa_0p5gpa
_database_code_depnum_ccdc_archive 'CCDC 2332700'
loop_
_audit_author_name
_audit_author_address
'Anna Makal'
;University of Warsaw, Chemistry Department
Poland
;
_audit_update_record             
;
2024-02-13 deposited with the CCDC.	2024-07-24 downloaded from the CCDC.
;
_audit_creation_date             2024-01-27
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2023.11.24 svn.r209d9fb for OlexSys, GUI svn.r6869)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H14 O2'
_chemical_formula_sum            'C20 H14 O2'
_chemical_formula_weight         286.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.16(4)
_cell_length_b                   7.308(4)
_cell_length_c                   10.05(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.1(4)
_cell_angle_gamma                90
_cell_volume                     662(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    459
_cell_measurement_temperature    290.7(7)
_cell_measurement_theta_max      23.1100
_cell_measurement_theta_min      2.7690
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.89437
_exptl_absorpt_correction_T_min  0.89437
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Spherical absorption correction
using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             300
_exptl_crystal_preparation       
'Mounted in a Diamond-Anvil Cell using paratone oil as pressure medium.'
_exptl_crystal_pressure_history  'Pressurized to 0.56 GPa.'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.09
_exptl_crystal_size_rad          0.400
_exptl_special_details           
;
High-pressure measurement at 0.56(10) GPa in a Merill-Basset Diamond Anvil Cell with effective opening angle of 40 deg. and paratone oil used as a pressure medium. Pressure determined by monitoring the shift of the ruby R1-fluorescence line.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1386
_diffrn_reflns_av_unetI/netI     0.1142
_diffrn_reflns_Laue_measured_fraction_full 0.324
_diffrn_reflns_Laue_measured_fraction_max 0.311
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            1922
_diffrn_reflns_point_group_measured_fraction_full 0.324
_diffrn_reflns_point_group_measured_fraction_max 0.311
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.196
_diffrn_reflns_theta_min         2.778
_diffrn_ambient_temperature      291.15
_diffrn_ambient_pressure         560000
_diffrn_crystal_treatment        
'pressurized slowly/rapidly in paratone oil as a hydrostatic medium'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.324
_diffrn_measured_fraction_theta_max 0.311
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -15.00  23.00   1.00  120.00    --    9.85  39.00 -12.00   38
  2  ω     -3.00  35.00   1.00  120.00    --    9.85   0.00   0.00   38
  3  ω    -20.00   9.00   1.00  120.00    --    9.85  67.00 157.00   29
  4  ω      1.00  28.00   1.00  120.00    --    9.85 -26.00-172.00   27
  5  ω    -15.00  35.00   1.00  120.00    --    9.85 -26.00   7.00   50
  6  ω     22.00  59.00   1.00  120.00    --    9.85-114.00  45.00   37
  7  ω    -40.00 -15.00   1.00  120.00    --    9.85 114.00 135.00   25
  8  ω    -31.00  -5.00   1.00  120.00    --    9.85   0.00-150.00   26
  9  ω    -36.00 -10.00   1.00  120.00    --  -11.80  39.00 -12.00   26
 10  ω    -61.00 -51.00   1.00  120.00    --  -11.80 114.00 -45.00   10
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 
'Diamond Anvil Cell, effective opening angle of 40 deg.'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                200
_reflns_number_total             414
_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-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.028(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         414
_refine_ls_number_restraints     78
_refine_ls_R_factor_all          0.1404
_refine_ls_R_factor_gt           0.0544
_refine_ls_restrained_S_all      0.950
_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)+(0.0660P)²+0.0988P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1206
_refine_ls_wR_factor_ref         0.1705
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C14(H14)
3.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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
O1 O 0.639(2) 0.3388(11) 0.0700(18) 0.064(6) Uani 1 1 d . U . . .
C17 C 0.740(3) 0.3972(13) 0.159(3) 0.044(7) Uani 1 1 d . U . . .
C18 C 0.8794(19) 0.4484(9) 0.1114(18) 0.054(8) Uani 1 1 d . U . . .
H18A H 0.9221 0.3309 0.0649 0.081 Uiso 1 1 calc R U . . .
H18B H 0.9607 0.4937 0.1965 0.081 Uiso 1 1 calc R U . . .
H18C H 0.8570 0.5580 0.0381 0.081 Uiso 1 1 calc R U . . .
C1 C 0.717(3) 0.4147(14) 0.302(2) 0.042(7) Uani 1 1 d . U . . .
C2 C 0.584(3) 0.4636(11) 0.342(2) 0.038(7) Uani 1 1 d . U . . .
C10 C 0.455(2) 0.5162(12) 0.244(2) 0.043(7) Uani 1 1 d . U . . .
H10 H 0.4623 0.5124 0.1382 0.052 Uiso 1 1 calc R U . . .
C11 C 0.6746(19) 0.4303(9) 0.7211(16) 0.049(8) Uani 1 1 d . U . . .
H11 H 0.7666 0.3930 0.7985 0.059 Uiso 1 1 calc R U . . .
C12 C 0.691(3) 0.4226(12) 0.578(2) 0.043(7) Uani 1 1 d . U . . .
C13 C 0.8254(18) 0.3744(9) 0.5389(16) 0.045(7) Uani 1 1 d . U . . .
H13 H 0.9207 0.3381 0.6131 0.054 Uiso 1 1 calc R U . . .
C14 C 0.833(3) 0.3744(13) 0.399(2) 0.040(7) Uani 1 1 d . U . . .
H14 H 0.9374 0.3403 0.3695 0.049 Uiso 1 1 calc R U . . .
C15 C 0.573(2) 0.4732(12) 0.485(2) 0.035(7) Uani 1 1 d . 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
O1 C17 1.24(4) . ?
C17 C18 1.484(18) . ?
C17 C1 1.49(3) . ?
C18 H18A 1.0831 . ?
C18 H18B 1.0831 . ?
C18 H18C 1.0831 . ?
C1 C2 1.40(2) . ?
C1 C14 1.34(5) . ?
C2 C10 1.45(4) . ?
C2 C15 1.46(3) . ?
C10 H10 1.0770 . ?
C10 C11 1.349(16) 3_666 ?
C11 C10 1.349(16) 3_666 ?
C11 H11 1.0770 . ?
C11 C12 1.47(2) . ?
C12 C13 1.402(17) . ?
C12 C15 1.35(4) . ?
C13 H13 1.0770 . ?
C13 C14 1.42(2) . ?
C14 H14 1.0770 . ?
C15 C15 1.47(3) 3_666 ?

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
O1 C17 C18 115.5(18) . . ?
O1 C17 C1 120.4(16) . . ?
C18 C17 C1 124(3) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2 C1 C17 125(3) . . ?
C14 C1 C17 117.1(16) . . ?
C14 C1 C2 117.8(18) . . ?
C1 C2 C10 121.6(18) . . ?
C1 C2 C15 120(2) . . ?
C10 C2 C15 117.9(12) . . ?
C2 C10 H10 118.4 . . ?
C11 C10 C2 123.2(17) 3_666 . ?
C11 C10 H10 118.4 3_666 . ?
C10 C11 H11 119.7 3_666 . ?
C10 C11 C12 121(2) 3_666 . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 122(2) . . ?
C15 C12 C11 117.3(12) . . ?
C15 C12 C13 120.6(17) . . ?
C12 C13 H13 120.7 . . ?
C12 C13 C14 119(2) . . ?
C14 C13 H13 120.7 . . ?
C1 C14 C13 123.4(13) . . ?
C1 C14 H14 118.3 . . ?
C13 C14 H14 118.3 . . ?
C2 C15 C15 116(3) . 3_666 ?
C12 C15 C2 119.0(13) . . ?
C12 C15 C15 125(2) . 3_666 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C17 C1 C2 -35(2) . . . . ?
O1 C17 C1 C14 143(3) . . . . ?
C17 C1 C2 C10 -5(2) . . . . ?
C17 C1 C2 C15 178.8(9) . . . . ?
C17 C1 C14 C13 -176.2(7) . . . . ?
C18 C17 C1 C2 144.1(19) . . . . ?
C18 C17 C1 C14 -38.3(17) . . . . ?
C1 C2 C10 C11 -177.8(9) . . . 3_666 ?
C1 C2 C15 C12 -4(2) . . . . ?
C1 C2 C15 C15 179.7(12) . . . 3_666 ?
C2 C1 C14 C13 2(3) . . . . ?
C10 C2 C15 C12 179.2(14) . . . . ?
C10 C2 C15 C15 3(2) . . . 3_666 ?
C10 C11 C12 C13 177.5(8) 3_666 . . . ?
C10 C11 C12 C15 1(2) 3_666 . . . ?
C11 C12 C13 C14 -178.5(9) . . . . ?
C11 C12 C15 C2 -178.7(7) . . . . ?
C11 C12 C15 C15 -3(3) . . . 3_666 ?
C12 C13 C14 C1 -1(2) . . . . ?
C13 C12 C15 C2 5(2) . . . . ?
C13 C12 C15 C15 -179.8(10) . . . 3_666 ?
C14 C1 C2 C10 177.6(14) . . . . ?
C14 C1 C2 C15 1(2) . . . . ?
C15 C2 C10 C11 -1(2) . . . 3_666 ?
C15 C12 C13 C14 -2(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
;

# start Validation Reply Form
_vrf_PLAT029_2papa_0p5gpa        
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.324 Why?  
RESPONSE: High-pressure measurement at 0.51(10) GPa in a Merill-Basset 
Diamond Anvil Cell with effective opening angle of 40 deg. 
and paratone oil used as a pressure medium. The setup significantly 
reduced the number of collectable reflections.
;
_vrf_PLAT088_2papa_0p5gpa        
;
PROBLEM: Poor Data / Parameter Ratio ....................       4.06 Note  
RESPONSE: High-pressure measurement at 0.51(10) GPa in a Merill-Basset 
Diamond Anvil Cell with effective opening angle of 40 deg. 
and paratone oil used as a pressure medium. The setup significantly 
reduced the number of collectable reflections.
;
_vrf_PLAT031_2papa_0p5gpa        
;
PROBLEM: Refined Extinction Parameter Within Range of ...      2.154 Sigma 
RESPONSE: High-pressure measurement at 0.51(10) GPa in a Merill-Basset 
Diamond Anvil Cell with effective opening angle of 40 deg. 
and paratone oil used as a pressure medium. The setup significantly 
reduced the number of collectable reflections and affected the intensities
of others. Extinction parameters corrects for insufficient absorption corr.
;
_vrf_PLAT149_2papa_0p5gpa        
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.40 Degree
RESPONSE: High-pressure measurement at 0.51(10) GPa in a Merill-Basset 
Diamond Anvil Cell with effective opening angle of 40 deg. 
and paratone oil used as a pressure medium. The setup significantly 
reduced the number of collectable reflections, especially in some directions.
;
_vrf_PLAT340_2papa_0p5gpa        
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.03167 Ang.  
RESPONSE: High-pressure measurement at 0.51(10) GPa in a Merill-Basset 
Diamond Anvil Cell with effective opening angle of 40 deg. 
and paratone oil used as a pressure medium. The setup significantly 
reduced the number of collectable reflections, especially in some directions.
;
_vrf_PLAT911_2papa_0p5gpa        
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        749 Report
RESPONSE: High-pressure measurement at 0.51(10) GPa in a Merill-Basset 
Diamond Anvil Cell with effective opening angle of 40 deg. 
and paratone oil used as a pressure medium. The setup significantly 
reduced the number of collectable reflections, especially in some directions.
;
# end Validation Reply Form


####################################################################### 
# 
# 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_2papb_0p5gpa
_database_code_depnum_ccdc_archive 'CCDC 2332697'
loop_
_audit_author_name
_audit_author_address
'Anna Makal'
;University of Warsaw, Chemistry Department
Poland
;
_audit_update_record             
;
2024-02-13 deposited with the CCDC.	2024-07-24 downloaded from the CCDC.
;
_audit_creation_date             2024-01-25
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2023.11.24 svn.r209d9fb for OlexSys, GUI svn.r6869)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C10 H7 O)'
_chemical_formula_sum            'C20 H14 O2'
_chemical_formula_weight         286.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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                   8.017(3)
_cell_length_b                   23.00(3)
_cell_length_c                   7.369(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.75(3)
_cell_angle_gamma                90
_cell_volume                     1352.1(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    688
_cell_measurement_temperature    287(7)
_cell_measurement_theta_max      31.4710
_cell_measurement_theta_min      2.6420
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.23391
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43d (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_preparation       
'Mounted in a Diamond-Anvil Cell using paratone oil as pressure medium.'
_exptl_crystal_pressure_history  'Pressurized to 0.51 GPa.'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
High-pressure measurement at 0.51(10) GPa in a Merill-Basset Diamond Anvil Cell with effective opening angle of 40 deg. and paratone oil used as a pressure medium. Pressure determined by monitoring the shift of the ruby R1-fluorescence line.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_av_unetI/netI     0.2123
_diffrn_reflns_Laue_measured_fraction_full 0.566
_diffrn_reflns_Laue_measured_fraction_max 0.389
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4593
_diffrn_reflns_point_group_measured_fraction_full 0.566
_diffrn_reflns_point_group_measured_fraction_max 0.389
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.729
_diffrn_reflns_theta_min         2.703
_diffrn_ambient_temperature      287.15
_diffrn_ambient_pressure         510000
_diffrn_crystal_treatment        
'pressurized slowly/rapidly in paratone oil as a hydrostatic medium'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.566
_diffrn_measured_fraction_theta_max 0.389
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  41.00   1.00   60.00    --   18.10  26.00 172.00   55
  2  ω    -15.00  21.00   1.00   60.00    --   18.10  81.00 -29.00   36
  3  ω    -14.00  48.00   1.00   60.00    --   18.10 -97.00  35.00   62
  4  ω    -19.00   9.00   1.00   60.00    --   18.10 -53.00  17.00   28
  5  ω     55.00  95.00   1.00   60.00    --   18.10-178.00  90.00   40
  6  ω    -43.00   6.00   1.00   60.00    --   18.10  13.00  -3.00   49
  7  ω    -75.00 -49.00   1.00   60.00    --  -19.97 134.00 -57.00   26
  8  ω    -20.00   5.00   1.00   60.00    --  -19.97 -39.00-167.00   25
  9  ω      8.00  33.00   1.00   60.00    --  -19.97-134.00-123.00   25
 10  ω    -15.00   8.00   1.00   60.00    --  -19.97 -57.00  30.00   23
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 
'Diamond Anvil Cell, effective opening angle of 40 deg.'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                812
_reflns_number_total             1938
_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 1.171.39.43d (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43d (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43d (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         1938
_refine_ls_number_restraints     108
_refine_ls_R_factor_all          0.3215
_refine_ls_R_factor_gt           0.1480
_refine_ls_restrained_S_all      1.130
_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)+(0.0189P)²+2.1477P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1628
_refine_ls_wR_factor_ref         0.2140
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 C1B, C2B, C3B, C4B, C5B, C6B, C7B, C8B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1A, C2A, C3A, C4A, C5A, C6A, C7A, C8A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C5A(H5A), C6A(H6A), C7A(H7A), C1B(H1B), C5B(H5B), C6B(H6B), C7B(H7B)
3.b Idealised Me refined as rotating group:
 C10A(H10A,H10B,H10C), C10B(H10D,H10E,H10F)
;
_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
O1A O 0.5948(8) 0.2938(5) 0.5061(11) 0.122(4) Uani 1 1 d . . . . .
C1A C 0.4040(7) 0.3948(5) 0.5407(7) 0.034(3) Uani 1 1 d . U . . .
H1A H 0.3931 0.3546 0.5466 0.040 Uiso 1 1 calc R U . . .
C2A C 0.5580(8) 0.4212(4) 0.4822(7) 0.032(2) Uani 1 1 d . U . . .
C3A C 0.5659(7) 0.4816(5) 0.4740(8) 0.036(2) Uani 1 1 d . U . . .
C4A C 0.7120(8) 0.5114(5) 0.4170(8) 0.036(2) Uani 1 1 d . U . . .
C5A C 0.7149(10) 0.5717(6) 0.4164(9) 0.053(3) Uani 1 1 d . U . . .
H5A H 0.8111 0.5896 0.3822 0.064 Uiso 1 1 calc R U . . .
C6A C 0.8424(9) 0.4758(5) 0.3661(9) 0.047(3) Uani 1 1 d . U . . .
H6A H 0.9367 0.4929 0.3248 0.056 Uiso 1 1 calc R U . . .
C7A C 0.8335(8) 0.4174(5) 0.3760(9) 0.044(3) Uani 1 1 d . U . . .
H7A H 0.9248 0.3961 0.3442 0.053 Uiso 1 1 calc R U . . .
C8A C 0.6950(8) 0.3861(5) 0.4316(9) 0.041(2) Uani 1 1 d . U . . .
C9A C 0.6980(11) 0.3228(6) 0.4463(11) 0.057(4) Uani 1 1 d . . . . .
C10A C 0.8425(11) 0.2895(6) 0.3789(13) 0.100(5) Uani 1 1 d . . . . .
H10A H 0.9393 0.2928 0.4661 0.149 Uiso 1 1 calc R U . . .
H10B H 0.8675 0.3051 0.2640 0.149 Uiso 1 1 calc R U . . .
H10C H 0.8122 0.2492 0.3640 0.149 Uiso 1 1 calc R U . . .
O1B O 0.0800(6) 0.1493(4) 0.5077(8) 0.084(3) Uani 1 1 d . . . . .
C1B C 0.2185(7) 0.0327(5) 0.5915(8) 0.030(2) Uani 1 1 d . U . . .
H1B H 0.1246 0.0529 0.6213 0.036 Uiso 1 1 calc R U . . .
C2B C 0.3595(7) 0.0654(5) 0.5378(8) 0.030(2) Uani 1 1 d . U . . .
C3B C 0.5026(8) 0.0303(3) 0.4961(9) 0.027(2) Uani 1 1 d . U . . .
C4B C 0.6448(7) 0.0613(5) 0.4448(8) 0.027(2) Uani 1 1 d . U . . .
C5B C 0.7827(7) 0.0246(5) 0.4001(8) 0.030(2) Uani 1 1 d . U . . .
H5B H 0.8775 0.0427 0.3633 0.036 Uiso 1 1 calc R U . . .
C6B C 0.6505(8) 0.1206(5) 0.4395(8) 0.035(2) Uani 1 1 d . U . . .
H6B H 0.7460 0.1391 0.4064 0.042 Uiso 1 1 calc R U . . .
C7B C 0.5148(7) 0.1536(4) 0.4832(8) 0.038(2) Uani 1 1 d . U . . .
H7B H 0.5210 0.1940 0.4829 0.045 Uiso 1 1 calc R U . . .
C8B C 0.3691(8) 0.1259(5) 0.5277(8) 0.033(2) Uani 1 1 d . U . . .
C9B C 0.2225(9) 0.1642(5) 0.5601(10) 0.046(4) Uani 1 1 d . . . . .
C10B C 0.2562(8) 0.2214(5) 0.6539(10) 0.052(4) Uani 1 1 d . . . . .
H10D H 0.2884 0.2495 0.5675 0.079 Uiso 1 1 calc R U . . .
H10E H 0.3451 0.2170 0.7503 0.079 Uiso 1 1 calc R U . . .
H10F H 0.1567 0.2345 0.7039 0.079 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
O1A C9A 1.182(12) . ?
C1A H1A 0.9300 . ?
C1A C2A 1.478(9) . ?
C1A C5A 1.289(11) 3_666 ?
C2A C3A 1.394(12) . ?
C2A C8A 1.441(11) . ?
C3A C3A 1.434(16) 3_666 ?
C3A C4A 1.455(10) . ?
C4A C5A 1.388(13) . ?
C4A C6A 1.409(12) . ?
C5A C1A 1.289(11) 3_666 ?
C5A H5A 0.9300 . ?
C6A H6A 0.9300 . ?
C6A C7A 1.347(13) . ?
C7A H7A 0.9300 . ?
C7A C8A 1.418(11) . ?
C8A C9A 1.460(15) . ?
C9A C10A 1.514(13) . ?
C10A H10A 0.9600 . ?
C10A H10B 0.9600 . ?
C10A H10C 0.9600 . ?
O1B C9B 1.218(8) . ?
C1B H1B 0.9300 . ?
C1B C2B 1.447(10) . ?
C1B C5B 1.319(11) 3_656 ?
C2B C3B 1.461(11) . ?
C2B C8B 1.396(12) . ?
C3B C3B 1.395(16) 3_656 ?
C3B C4B 1.428(9) . ?
C4B C5B 1.454(11) . ?
C4B C6B 1.366(12) . ?
C5B C1B 1.319(11) 3_656 ?
C5B H5B 0.9300 . ?
C6B H6B 0.9300 . ?
C6B C7B 1.390(10) . ?
C7B H7B 0.9300 . ?
C7B C8B 1.398(9) . ?
C8B C9B 1.506(11) . ?
C9B C10B 1.500(14) . ?
C10B H10D 0.9600 . ?
C10B H10E 0.9600 . ?
C10B H10F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2A C1A H1A 120.4 . . ?
C5A C1A H1A 120.4 3_666 . ?
C5A C1A C2A 119.1(11) 3_666 . ?
C3A C2A C1A 117.7(7) . . ?
C3A C2A C8A 120.5(7) . . ?
C8A C2A C1A 121.8(9) . . ?
C2A C3A C3A 122.6(10) . 3_666 ?
C2A C3A C4A 121.6(8) . . ?
C3A C3A C4A 115.8(12) 3_666 . ?
C5A C4A C3A 119.1(8) . . ?
C5A C4A C6A 124.6(9) . . ?
C6A C4A C3A 116.3(10) . . ?
C1A C5A C4A 125.6(10) 3_666 . ?
C1A C5A H5A 117.2 3_666 . ?
C4A C5A H5A 117.2 . . ?
C4A C6A H6A 119.3 . . ?
C7A C6A C4A 121.4(8) . . ?
C7A C6A H6A 119.3 . . ?
C6A C7A H7A 117.7 . . ?
C6A C7A C8A 124.7(9) . . ?
C8A C7A H7A 117.7 . . ?
C2A C8A C9A 123.1(8) . . ?
C7A C8A C2A 115.5(11) . . ?
C7A C8A C9A 121.3(9) . . ?
O1A C9A C8A 125.7(11) . . ?
O1A C9A C10A 115.0(14) . . ?
C8A C9A C10A 119.3(9) . . ?
C9A C10A H10A 109.5 . . ?
C9A C10A H10B 109.5 . . ?
C9A C10A H10C 109.5 . . ?
H10A C10A H10B 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
C2B C1B H1B 118.6 . . ?
C5B C1B H1B 118.6 3_656 . ?
C5B C1B C2B 122.9(8) 3_656 . ?
C1B C2B C3B 114.9(9) . . ?
C8B C2B C1B 125.6(8) . . ?
C8B C2B C3B 119.5(7) . . ?
C3B C3B C2B 121.1(8) 3_656 . ?
C3B C3B C4B 122.6(8) 3_656 . ?
C4B C3B C2B 116.3(7) . . ?
C3B C4B C5B 114.5(9) . . ?
C6B C4B C3B 122.4(7) . . ?
C6B C4B C5B 123.0(7) . . ?
C1B C5B C4B 124.0(7) 3_656 . ?
C1B C5B H5B 118.0 3_656 . ?
C4B C5B H5B 118.0 . . ?
C4B C6B H6B 119.7 . . ?
C4B C6B C7B 120.7(8) . . ?
C7B C6B H6B 119.7 . . ?
C6B C7B H7B 120.1 . . ?
C6B C7B C8B 119.8(9) . . ?
C8B C7B H7B 120.1 . . ?
C2B C8B C7B 121.2(7) . . ?
C2B C8B C9B 121.7(8) . . ?
C7B C8B C9B 117.1(10) . . ?
O1B C9B C8B 120.6(10) . . ?
O1B C9B C10B 120.8(8) . . ?
C10B C9B C8B 118.6(7) . . ?
C9B C10B H10D 109.5 . . ?
C9B C10B H10E 109.5 . . ?
C9B C10B H10F 109.5 . . ?
H10D C10B H10E 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1A C2A C3A C3A 2.3(11) . . . 3_666 ?
C1A C2A C3A C4A -179.6(5) . . . . ?
C1A C2A C8A C7A 179.2(5) . . . . ?
C1A C2A C8A C9A -4.5(10) . . . . ?
C2A C3A C4A C5A -178.1(6) . . . . ?
C2A C3A C4A C6A 1.6(9) . . . . ?
C2A C8A C9A O1A -3.0(14) . . . . ?
C2A C8A C9A C10A 176.3(7) . . . . ?
C3A C2A C8A C7A 0.4(9) . . . . ?
C3A C2A C8A C9A 176.7(7) . . . . ?
C3A C3A C4A C5A 0.0(10) 3_666 . . . ?
C3A C3A C4A C6A 179.8(7) 3_666 . . . ?
C3A C4A C5A C1A -1.5(11) . . . 3_666 ?
C3A C4A C6A C7A -2.1(10) . . . . ?
C4A C6A C7A C8A 1.9(12) . . . . ?
C5A C1A C2A C3A -0.8(9) 3_666 . . . ?
C5A C1A C2A C8A -179.6(6) 3_666 . . . ?
C5A C4A C6A C7A 177.6(7) . . . . ?
C6A C4A C5A C1A 178.7(6) . . . 3_666 ?
C6A C7A C8A C2A -0.9(10) . . . . ?
C6A C7A C8A C9A -177.3(8) . . . . ?
C7A C8A C9A O1A 173.1(8) . . . . ?
C7A C8A C9A C10A -7.6(12) . . . . ?
C8A C2A C3A C3A -178.9(7) . . . 3_666 ?
C8A C2A C3A C4A -0.8(9) . . . . ?
C1B C2B C3B C3B 1.7(10) . . . 3_656 ?
C1B C2B C3B C4B -179.3(5) . . . . ?
C1B C2B C8B C7B 176.7(5) . . . . ?
C1B C2B C8B C9B -4.7(11) . . . . ?
C2B C3B C4B C5B -178.5(6) . . . . ?
C2B C3B C4B C6B 1.9(9) . . . . ?
C2B C8B C9B O1B -37.1(11) . . . . ?
C2B C8B C9B C10B 144.5(8) . . . . ?
C3B C2B C8B C7B -1.7(10) . . . . ?
C3B C2B C8B C9B 176.9(6) . . . . ?
C3B C3B C4B C5B 0.5(10) 3_656 . . . ?
C3B C3B C4B C6B -179.1(8) 3_656 . . . ?
C3B C4B C5B C1B -1.3(9) . . . 3_656 ?
C3B C4B C6B C7B -0.6(10) . . . . ?
C4B C6B C7B C8B -1.9(9) . . . . ?
C5B C1B C2B C3B -0.9(9) 3_656 . . . ?
C5B C1B C2B C8B -179.4(7) 3_656 . . . ?
C5B C4B C6B C7B 179.9(5) . . . . ?
C6B C4B C5B C1B 178.3(6) . . . 3_656 ?
C6B C7B C8B C2B 3.1(9) . . . . ?
C6B C7B C8B C9B -175.6(6) . . . . ?
C7B C8B C9B O1B 141.6(8) . . . . ?
C7B C8B C9B C10B -36.8(10) . . . . ?
C8B C2B C3B C3B -179.7(7) . . . 3_656 ?
C8B C2B C3B C4B -0.7(9) . . . . ?


_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
;
####################################################################### 
# 
# 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_2papa_rt
_database_code_depnum_ccdc_archive 'CCDC 2332701'
loop_
_audit_author_name
_audit_author_address
'Anna Makal'
;University of Warsaw, Chemistry Department
Poland
;
_audit_update_record             
;
2024-02-13 deposited with the CCDC.	2024-07-24 downloaded from the CCDC.
;
_audit_creation_date             2024-01-27
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2023.11.24 svn.r209d9fb for OlexSys, GUI svn.r6869)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 O2'
_chemical_formula_sum            'C20 H14 O2'
_chemical_formula_weight         286.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.2316(2)
_cell_length_b                   7.44094(15)
_cell_length_c                   10.0891(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.8945(19)
_cell_angle_gamma                90
_cell_volume                     684.71(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2775
_cell_measurement_temperature    280.10(10)
_cell_measurement_theta_max      76.3550
_cell_measurement_theta_min      7.0480
_shelx_estimated_absorpt_T_max   0.884
_shelx_estimated_absorpt_T_min   0.806
_exptl_absorpt_coefficient_mu    0.705
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79246
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43d (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5826
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.510
_diffrn_reflns_theta_min         6.049
_diffrn_ambient_temperature      280.10(10)
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -91.00 -53.00   0.50    0.40    --    0.00-178.00-150.00   76
  2  ω    -35.00  33.00   0.50    0.40    --    0.00  57.00  90.00  136
  3  ω     48.00  80.00   0.50    0.40    --    0.00  57.00  90.00   64
  4  ω      0.00  25.00   0.50    0.40    --    0.00 -99.00  90.00   50
  5  ω     22.00  49.00   0.50    0.40    --    0.00 -99.00 -90.00   54
  6  ω     27.00  67.00   0.50    1.40    --   66.49  45.00-180.00   80
  7  ω    -26.00   3.00   0.50    1.40    --   66.49 -15.00-150.00   58
  8  ω     -7.00 110.00   0.50    1.40    --   66.49 -45.00-150.00  234
  9  ω     49.00  92.00   0.50    1.40    --   66.49-125.00  30.00   86
 10  ω     16.00 155.00   0.50    1.40    --   66.49 -15.00-150.00  278
 11  ω     34.00 102.00   0.50    1.40    --   66.49-125.00 120.00  136
 12  ω     98.00 129.00   0.50    1.40    --   66.49  45.00-180.00   62
 13  ω    -16.00  49.00   0.50    1.40    --   66.49 -77.00  90.00  130
 14  ω    114.00 145.00   0.50    1.40    --   66.49 125.00 120.00   62
 15  ω     96.00 122.00   0.50    1.40    --   66.49 125.00-180.00   52
 16  ω     97.00 133.00   0.50    1.40    --   66.49 125.00 -60.00   72
 17  ω     69.00 109.00   0.50    1.40    --   66.49 -77.00  90.00   80
 18  ω     43.00  69.00   0.50    1.40    --  121.75 -91.00  90.00   52
 19  ω     33.00 102.00   0.50    1.40    --  121.75 -91.00  60.00  138
 20  ω     32.00 104.00   0.50    1.40    --  121.75 -91.00-150.00  144
 21  ω     76.00 101.00   0.50    1.40    --  121.75-111.00  30.00   50
 22  ω    132.00 164.00   0.50    1.40    --  121.75 111.00 -90.00   64
 23  ω     82.00 174.00   0.50    1.40    --  121.75  77.00  60.00  184
 24  ω    105.00 150.00   0.50    1.40    --  121.75 111.00   0.00   90
 25  ω     76.00 103.00   0.50    1.40    --  121.75-111.00 150.00   54
 26  ω     78.00 104.00   0.50    1.40    --  121.75 -91.00 -90.00   52
 27  ω     65.00  91.00   0.50    1.40    --  121.75 178.00 -30.00   52
 28  ω     64.00 117.00   0.50    1.40    --  121.75 178.00  60.00  106
 29  ω     71.00 140.00   0.50    1.40    --  121.75  38.00-180.00  138
 30  ω     72.00 101.00   0.50    1.40    --  121.75 -91.00  90.00   58
 31  ω     39.00  74.00   0.50    1.40    --  121.75 -91.00 -90.00   70
 32  ω     93.00 141.00   0.50    1.40    --  121.75  63.00 -60.00   96
 33  ω     79.00 178.00   0.50    1.40    --  121.75  38.00   0.00  198
 34  ω     68.00 159.00   0.50    1.40    --  121.75 -50.00 -90.00  182
 35  ω     72.00 108.00   0.50    1.40    --  121.75-111.00-180.00   72
 36  ω     86.00 156.00   0.50    1.40    --  121.75  63.00-180.00  140
 37  ω     45.00  71.00   0.50    1.40    --  121.75-111.00 -90.00   52
 38  ω     80.00 105.00   0.50    1.40    --  121.75-111.00 -90.00   50
 39  ω     63.00 106.00   0.50    1.40    --  121.75-111.00-150.00   86
 40  ω     62.00 108.00   0.50    1.40    --  121.75-111.00 -30.00   92
 41  ω    108.00 166.00   0.50    1.40    --  121.75 111.00-120.00  116
 42  ω     80.00 107.00   0.50    1.40    --  121.75-103.00  29.27   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, HyPix'
_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                1292
_reflns_number_total             1450
_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 1.171.39.43d (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43d (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43d (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1450
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.099
_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)+(0.0833P)²+0.1385P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1430
_refine_ls_wR_factor_ref         0.1462
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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
O1 O 0.63814(12) 0.33977(19) 0.07319(11) 0.0554(4) Uani 1 1 d . . . . .
C17 C 0.73489(16) 0.3975(2) 0.15757(14) 0.0401(4) Uani 1 1 d . . . . .
C18 C 0.87984(18) 0.4524(2) 0.11874(17) 0.0494(4) Uani 1 1 d . . . . .
H18A H 0.9629 0.3547 0.1569 0.074 Uiso 1 1 calc R U . . .
H18B H 0.9110 0.5832 0.1610 0.074 Uiso 1 1 calc R U . . .
H18C H 0.8698 0.4588 0.0105 0.074 Uiso 1 1 calc R U . . .
C1 C 0.71523(15) 0.41463(19) 0.30192(14) 0.0365(3) Uani 1 1 d . . . . .
C2 C 0.57901(14) 0.46566(18) 0.33923(13) 0.0339(3) Uani 1 1 d . . . . .
C10 C 0.45410(15) 0.5192(2) 0.24384(14) 0.0390(4) Uani 1 1 d . . . . .
H10 H 0.4612 0.5170 0.1383 0.047 Uiso 1 1 calc R U . . .
C11 C 0.67204(15) 0.4277(2) 0.71538(14) 0.0411(4) Uani 1 1 d . . . . .
H11 H 0.7628 0.3871 0.7896 0.049 Uiso 1 1 calc R U . . .
C12 C 0.68851(14) 0.42389(19) 0.57666(14) 0.0363(3) Uani 1 1 d . . . . .
C13 C 0.82066(15) 0.3739(2) 0.53517(15) 0.0410(4) Uani 1 1 d . . . . .
H13 H 0.9129 0.3360 0.6087 0.049 Uiso 1 1 calc R U . . .
C14 C 0.83361(15) 0.3728(2) 0.40085(15) 0.0401(4) Uani 1 1 d . . . . .
H14 H 0.9376 0.3390 0.3715 0.048 Uiso 1 1 calc R U . . .
C15 C 0.56713(14) 0.47256(17) 0.47892(13) 0.0328(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C17 1.2132(18) . ?
C17 C18 1.508(2) . ?
C17 C1 1.5006(19) . ?
C18 H18A 1.0831 . ?
C18 H18B 1.0831 . ?
C18 H18C 1.0831 . ?
C1 C2 1.4190(19) . ?
C1 C14 1.396(2) . ?
C2 C10 1.4393(19) . ?
C2 C15 1.4313(18) . ?
C10 H10 1.0770 . ?
C10 C11 1.353(2) 3_666 ?
C11 C10 1.353(2) 3_666 ?
C11 H11 1.0770 . ?
C11 C12 1.4313(19) . ?
C12 C13 1.3999(19) . ?
C12 C15 1.4204(18) . ?
C13 H13 1.0770 . ?
C13 C14 1.379(2) . ?
C14 H14 1.0770 . ?
C15 C15 1.431(3) 3_666 ?

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
O1 C17 C18 120.02(13) . . ?
O1 C17 C1 121.65(13) . . ?
C1 C17 C18 118.33(13) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2 C1 C17 121.69(13) . . ?
C14 C1 C17 118.43(12) . . ?
C14 C1 C2 119.85(13) . . ?
C1 C2 C10 123.23(13) . . ?
C1 C2 C15 118.48(12) . . ?
C15 C2 C10 118.23(12) . . ?
C2 C10 H10 119.5 . . ?
C11 C10 C2 121.06(13) 3_666 . ?
C11 C10 H10 119.5 3_666 . ?
C10 C11 H11 119.0 3_666 . ?
C10 C11 C12 122.00(12) 3_666 . ?
C12 C11 H11 119.0 . . ?
C13 C12 C11 121.80(12) . . ?
C13 C12 C15 119.37(13) . . ?
C15 C12 C11 118.82(12) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.49(12) . . ?
C14 C13 H13 119.8 . . ?
C1 C14 H14 119.2 . . ?
C13 C14 C1 121.60(13) . . ?
C13 C14 H14 119.2 . . ?
C12 C15 C2 120.14(12) . . ?
C12 C15 C15 119.54(15) . 3_666 ?
C15 C15 C2 120.32(15) 3_666 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C17 C1 C2 -36.6(2) . . . . ?
O1 C17 C1 C14 141.13(16) . . . . ?
C17 C1 C2 C10 -5.4(2) . . . . ?
C17 C1 C2 C15 177.67(12) . . . . ?
C17 C1 C14 C13 -175.61(13) . . . . ?
C18 C17 C1 C2 143.97(15) . . . . ?
C18 C17 C1 C14 -38.26(19) . . . . ?
C1 C2 C10 C11 -177.85(13) . . . 3_666 ?
C1 C2 C15 C12 -1.85(19) . . . . ?
C1 C2 C15 C15 178.51(14) . . . 3_666 ?
C2 C1 C14 C13 2.2(2) . . . . ?
C10 C2 C15 C12 -178.92(12) . . . . ?
C10 C2 C15 C15 1.4(2) . . . 3_666 ?
C10 C11 C12 C13 178.09(15) 3_666 . . . ?
C10 C11 C12 C15 -1.8(2) 3_666 . . . ?
C11 C12 C13 C14 -179.49(14) . . . . ?
C11 C12 C15 C2 -178.41(12) . . . . ?
C11 C12 C15 C15 1.2(2) . . . 3_666 ?
C12 C13 C14 C1 -2.4(2) . . . . ?
C13 C12 C15 C2 1.7(2) . . . . ?
C13 C12 C15 C15 -178.66(15) . . . 3_666 ?
C14 C1 C2 C10 176.86(13) . . . . ?
C14 C1 C2 C15 -0.1(2) . . . . ?
C15 C2 C10 C11 -0.9(2) . . . 3_666 ?
C15 C12 C13 C14 0.4(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
;
####################################################################### 
# 
# 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_2papb_2p0gpa
_database_code_depnum_ccdc_archive 'CCDC 2332702'
loop_
_audit_author_name
_audit_author_address
'Anna Makal'
;University of Warsaw, Chemistry Department
Poland
;
_audit_update_record             
;
2024-02-13 deposited with the CCDC.	2024-07-24 downloaded from the CCDC.
;
_audit_creation_date             2024-01-25
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2023.11.24 svn.r209d9fb for OlexSys, GUI svn.r6869)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C10 H7 O)'
_chemical_formula_sum            'C20 H14 O2'
_chemical_formula_weight         286.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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                   7.901(2)
_cell_length_b                   22.685(5)
_cell_length_c                   6.897(11)
_cell_angle_alpha                90
_cell_angle_beta                 96.68(5)
_cell_angle_gamma                90
_cell_volume                     1228(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    825
_cell_measurement_temperature    292.3(5)
_cell_measurement_theta_max      29.9840
_cell_measurement_theta_min      2.7450
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.36a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_preparation       
'Mounted in a Diamond-Anvil Cell using paratone oil as pressure medium.'
_exptl_crystal_pressure_history  'Pressurized to 1.98 GPa.'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
High-pressure measurement at 1.98(10) GPa in a DACOne20 Diamond Anvil Cell with effective opening angle of 50 deg. and paratone oil used as a pressure medium. Pressure determined by monitoring the shift of the ruby R1-fluorescence line.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1322
_diffrn_reflns_av_unetI/netI     0.1659
_diffrn_reflns_Laue_measured_fraction_full 0.492
_diffrn_reflns_Laue_measured_fraction_max 0.479
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -3
_diffrn_reflns_number            4771
_diffrn_reflns_point_group_measured_fraction_full 0.492
_diffrn_reflns_point_group_measured_fraction_max 0.479
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.595
_diffrn_ambient_temperature      292.15
_diffrn_ambient_pressure         2000000
_diffrn_crystal_treatment        
'pressurized slowly/rapidly in paratone oil as a hydrostatic medium'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.492
_diffrn_measured_fraction_theta_max 0.479
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -44.00  26.00   0.50   25.00    --    2.10  13.00  -3.00  140
  2  ω    -22.00   4.00   0.50   75.00    --   18.10 -19.00-150.00   52
  3  ω     -7.00  18.00   0.50   75.00    --   18.10  53.00 162.00   50
  4  ω     -7.00  18.00   0.50   75.00    --   18.10  53.00 -17.00   50
  5  ω      6.00  31.00   0.50   75.00    --   18.10  13.00  -3.00   50
  6  ω    -18.00   8.00   0.50   75.00    --  -19.97 -26.00   7.00   52
  7  ω    -10.00  11.00   0.50   75.00    --  -19.97 -70.00-157.00   42
  8  ω    -18.00   7.00   0.50   75.00    --  -19.97 -53.00  17.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 
'Diamond Anvil Cell, effective opening angle of 50 deg.'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                436
_reflns_number_total             1204
_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 1.171.42.36a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.36a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.36a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.011(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         1204
_refine_ls_number_restraints     108
_refine_ls_R_factor_all          0.2403
_refine_ls_R_factor_gt           0.1015
_refine_ls_restrained_S_all      0.995
_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)+(0.1658P)²+0.3370P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2506
_refine_ls_wR_factor_ref         0.3586
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 C1B, C2B, C3B, C4B, C5B, C6B, C7B, C8B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1A, C2A, C3A, C4A, C5A, C6A, C7A, C8A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C5A(H5A), C6A(H6A), C7A(H7A), C1B(H1B), C5B(H5B), C6B(H6B), C7B(H7B)
3.b Idealised Me refined as rotating group:
 C10A(H10A,H10B,H10C), C10B(H10D,H10E,H10F)
;
_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
O1A O 0.6029(9) 0.2917(3) 0.527(2) 0.108(8) Uani 1 1 d . . . . .
C1A C 0.3997(10) 0.3952(3) 0.535(3) 0.042(7) Uani 1 1 d . U . . .
H1A H 0.3862 0.3544 0.5336 0.050 Uiso 1 1 calc R U . . .
C2A C 0.5581(10) 0.4196(3) 0.482(3) 0.048(7) Uani 1 1 d . U . . .
C3A C 0.5696(9) 0.4822(3) 0.479(3) 0.049(7) Uani 1 1 d . U . . .
C4A C 0.7163(11) 0.5103(3) 0.416(3) 0.047(7) Uani 1 1 d . U . . .
C5A C 0.7256(12) 0.5720(3) 0.415(3) 0.061(9) Uani 1 1 d . U . . .
H5A H 0.8224 0.5901 0.3780 0.073 Uiso 1 1 calc R U . . .
C6A C 0.8524(11) 0.4749(3) 0.372(3) 0.049(7) Uani 1 1 d . U . . .
H6A H 0.9515 0.4926 0.3399 0.058 Uiso 1 1 calc R U . . .
C7A C 0.8412(11) 0.4150(4) 0.375(3) 0.058(7) Uani 1 1 d . U . . .
H7A H 0.9304 0.3930 0.3354 0.070 Uiso 1 1 calc R U . . .
C8A C 0.7018(11) 0.3847(3) 0.436(3) 0.047(7) Uani 1 1 d . U . . .
C9A C 0.7073(12) 0.3203(3) 0.453(3) 0.067(10) Uani 1 1 d . . . . .
C10A C 0.8492(13) 0.2879(4) 0.373(4) 0.093(11) Uani 1 1 d . . . . .
H10A H 0.8755 0.2528 0.4485 0.140 Uiso 1 1 calc R U . . .
H10B H 0.9482 0.3126 0.3803 0.140 Uiso 1 1 calc R U . . .
H10C H 0.8148 0.2774 0.2395 0.140 Uiso 1 1 calc R U . . .
O1B O 0.0752(7) 0.1527(2) 0.4981(19) 0.098(7) Uani 1 1 d . . . . .
C1B C 0.2138(10) 0.0347(3) 0.599(3) 0.044(7) Uani 1 1 d . U . . .
H1B H 0.1230 0.0560 0.6380 0.052 Uiso 1 1 calc R U . . .
C2B C 0.3588(9) 0.0663(3) 0.534(3) 0.042(6) Uani 1 1 d . U . . .
C3B C 0.5014(10) 0.0314(3) 0.493(3) 0.051(7) Uani 1 1 d . U . . .
C4B C 0.6490(10) 0.0606(3) 0.438(3) 0.061(7) Uani 1 1 d . U . . .
C5B C 0.7904(9) 0.0254(3) 0.397(3) 0.051(7) Uani 1 1 d . U . . .
H5B H 0.8889 0.0440 0.3675 0.062 Uiso 1 1 calc R U . . .
C6B C 0.6557(10) 0.1214(3) 0.440(3) 0.063(8) Uani 1 1 d . U . . .
H6B H 0.7542 0.1406 0.4122 0.075 Uiso 1 1 calc R U . . .
C7B C 0.5167(10) 0.1542(3) 0.483(3) 0.058(7) Uani 1 1 d . U . . .
H7B H 0.5236 0.1951 0.4818 0.070 Uiso 1 1 calc R U . . .
C8B C 0.3687(10) 0.1280(3) 0.527(3) 0.049(7) Uani 1 1 d . U . . .
C9B C 0.2214(11) 0.1666(3) 0.559(3) 0.088(11) Uani 1 1 d . . . . .
C10B C 0.2560(13) 0.2235(3) 0.659(3) 0.084(13) Uani 1 1 d . . . . .
H10D H 0.1598 0.2491 0.6303 0.126 Uiso 1 1 calc R U . . .
H10E H 0.3549 0.2412 0.6152 0.126 Uiso 1 1 calc R U . . .
H10F H 0.2760 0.2171 0.7978 0.126 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
O1A C9A 1.212(13) . ?
C1A H1A 0.9300 . ?
C1A C2A 1.454(11) . ?
C1A C5A 1.316(12) 3_666 ?
C2A C3A 1.422(10) . ?
C2A C8A 1.449(12) . ?
C3A C3A 1.421(15) 3_666 ?
C3A C4A 1.434(12) . ?
C4A C5A 1.401(10) . ?
C4A C6A 1.404(11) . ?
C5A C1A 1.316(12) 3_666 ?
C5A H5A 0.9300 . ?
C6A H6A 0.9300 . ?
C6A C7A 1.363(10) . ?
C7A H7A 0.9300 . ?
C7A C8A 1.402(13) . ?
C8A C9A 1.466(11) . ?
C9A C10A 1.498(15) . ?
C10A H10A 0.9600 . ?
C10A H10B 0.9600 . ?
C10A H10C 0.9600 . ?
O1B C9B 1.224(12) . ?
C1B H1B 0.9300 . ?
C1B C2B 1.463(12) . ?
C1B C5B 1.364(9) 3_656 ?
C2B C3B 1.432(11) . ?
C2B C8B 1.405(10) . ?
C3B C3B 1.427(14) 3_656 ?
C3B C4B 1.432(13) . ?
C4B C5B 1.427(11) . ?
C4B C6B 1.380(10) . ?
C5B C1B 1.364(9) 3_656 ?
C5B H5B 0.9300 . ?
C6B H6B 0.9300 . ?
C6B C7B 1.387(11) . ?
C7B H7B 0.9300 . ?
C7B C8B 1.376(11) . ?
C8B C9B 1.494(11) . ?
C9B C10B 1.474(17) . ?
C10B H10D 0.9600 . ?
C10B H10E 0.9600 . ?
C10B H10F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2A C1A H1A 118.5 . . ?
C5A C1A H1A 118.5 3_666 . ?
C5A C1A C2A 123.0(7) 3_666 . ?
C3A C2A C1A 116.2(8) . . ?
C3A C2A C8A 119.3(8) . . ?
C8A C2A C1A 124.5(7) . . ?
C2A C3A C4A 120.2(8) . . ?
C3A C3A C2A 120.9(9) 3_666 . ?
C3A C3A C4A 118.6(9) 3_666 . ?
C5A C4A C3A 119.4(9) . . ?
C5A C4A C6A 121.8(9) . . ?
C6A C4A C3A 118.6(7) . . ?
C1A C5A C4A 121.5(10) 3_666 . ?
C1A C5A H5A 119.3 3_666 . ?
C4A C5A H5A 119.3 . . ?
C4A C6A H6A 119.5 . . ?
C7A C6A C4A 120.9(8) . . ?
C7A C6A H6A 119.5 . . ?
C6A C7A H7A 118.4 . . ?
C6A C7A C8A 123.2(10) . . ?
C8A C7A H7A 118.4 . . ?
C2A C8A C9A 122.9(9) . . ?
C7A C8A C2A 117.5(8) . . ?
C7A C8A C9A 119.6(9) . . ?
O1A C9A C8A 123.6(11) . . ?
O1A C9A C10A 117.9(8) . . ?
C8A C9A C10A 118.6(11) . . ?
C9A C10A H10A 109.5 . . ?
C9A C10A H10B 109.5 . . ?
C9A C10A H10C 109.5 . . ?
H10A C10A H10B 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
C2B C1B H1B 119.5 . . ?
C5B C1B H1B 119.5 3_656 . ?
C5B C1B C2B 121.1(9) 3_656 . ?
C3B C2B C1B 116.9(7) . . ?
C8B C2B C1B 123.3(8) . . ?
C8B C2B C3B 119.7(8) . . ?
C3B C3B C2B 121.3(10) 3_656 . ?
C3B C3B C4B 119.9(10) 3_656 . ?
C4B C3B C2B 118.8(7) . . ?
C5B C4B C3B 118.2(7) . . ?
C6B C4B C3B 119.5(8) . . ?
C6B C4B C5B 122.1(8) . . ?
C1B C5B C4B 122.3(8) 3_656 . ?
C1B C5B H5B 118.8 3_656 . ?
C4B C5B H5B 118.8 . . ?
C4B C6B H6B 119.8 . . ?
C4B C6B C7B 120.5(8) . . ?
C7B C6B H6B 119.8 . . ?
C6B C7B H7B 119.0 . . ?
C8B C7B C6B 122.0(7) . . ?
C8B C7B H7B 119.0 . . ?
C2B C8B C9B 122.0(7) . . ?
C7B C8B C2B 119.4(7) . . ?
C7B C8B C9B 118.5(7) . . ?
O1B C9B C8B 121.2(11) . . ?
O1B C9B C10B 120.2(8) . . ?
C10B C9B C8B 118.5(9) . . ?
C9B C10B H10D 109.5 . . ?
C9B C10B H10E 109.5 . . ?
C9B C10B H10F 109.5 . . ?
H10D C10B H10E 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1A C2A C3A C3A -2(3) . . . 3_666 ?
C1A C2A C3A C4A -175.9(14) . . . . ?
C1A C2A C8A C7A 175.9(16) . . . . ?
C1A C2A C8A C9A -5(3) . . . . ?
C2A C3A C4A C5A -179.9(16) . . . . ?
C2A C3A C4A C6A -5(2) . . . . ?
C2A C8A C9A O1A -9(3) . . . . ?
C2A C8A C9A C10A 170.9(16) . . . . ?
C3A C2A C8A C7A -5(3) . . . . ?
C3A C2A C8A C9A 174.2(18) . . . . ?
C3A C3A C4A C5A 6(3) 3_666 . . . ?
C3A C3A C4A C6A -179(2) 3_666 . . . ?
C3A C4A C5A C1A -2(3) . . . 3_666 ?
C3A C4A C6A C7A 4(3) . . . . ?
C4A C6A C7A C8A -5(3) . . . . ?
C5A C1A C2A C3A -2(3) 3_666 . . . ?
C5A C1A C2A C8A 176.8(17) 3_666 . . . ?
C5A C4A C6A C7A 179.6(18) . . . . ?
C6A C4A C5A C1A -177.0(17) . . . 3_666 ?
C6A C7A C8A C2A 5(3) . . . . ?
C6A C7A C8A C9A -174.2(19) . . . . ?
C7A C8A C9A O1A 170.2(17) . . . . ?
C7A C8A C9A C10A -10(3) . . . . ?
C8A C2A C3A C3A 179.0(19) . . . 3_666 ?
C8A C2A C3A C4A 5(3) . . . . ?
C1B C2B C3B C3B 2(3) . . . 3_656 ?
C1B C2B C3B C4B -177.3(15) . . . . ?
C1B C2B C8B C7B 173.7(15) . . . . ?
C1B C2B C8B C9B -8(3) . . . . ?
C2B C3B C4B C5B 179.9(15) . . . . ?
C2B C3B C4B C6B 5(3) . . . . ?
C2B C8B C9B O1B -38(3) . . . . ?
C2B C8B C9B C10B 145.1(17) . . . . ?
C3B C2B C8B C7B -1(3) . . . . ?
C3B C2B C8B C9B 177.1(16) . . . . ?
C3B C3B C4B C5B 0(3) 3_656 . . . ?
C3B C3B C4B C6B -175(2) 3_656 . . . ?
C3B C4B C5B C1B 3(3) . . . 3_656 ?
C3B C4B C6B C7B -4(3) . . . . ?
C4B C6B C7B C8B 1(3) . . . . ?
C5B C1B C2B C3B -6(2) 3_656 . . . ?
C5B C1B C2B C8B 179.6(17) 3_656 . . . ?
C5B C4B C6B C7B -179.0(18) . . . . ?
C6B C4B C5B C1B 177.9(18) . . . 3_656 ?
C6B C7B C8B C2B 2(3) . . . . ?
C6B C7B C8B C9B -176.4(17) . . . . ?
C7B C8B C9B O1B 140.3(17) . . . . ?
C7B C8B C9B C10B -37(2) . . . . ?
C8B C2B C3B C3B 177(2) . . . 3_656 ?
C8B C2B C3B C4B -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
;
####################################################################### 
# 
# 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_2pAPa_100K
_database_code_depnum_ccdc_archive 'CCDC 2332703'
loop_
_audit_author_name
_audit_author_address
'Anna Makal'
;University of Warsaw, Chemistry Department
Poland
;
_audit_update_record             
;
2024-02-13 deposited with the CCDC.	2024-07-24 downloaded from the CCDC.
;
_audit_creation_date             2024-01-25
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2023.11.24 svn.r209d9fb for OlexSys, GUI svn.r6869)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H14 O2'
_chemical_formula_sum            'C20 H14 O2'
_chemical_formula_weight         286.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.2009(4)
_cell_length_b                   7.3090(3)
_cell_length_c                   10.0763(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.993(5)
_cell_angle_gamma                90
_cell_volume                     669.30(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2218
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      71.4490
_cell_measurement_theta_min      7.0800
_shelx_estimated_absorpt_T_max   0.963
_shelx_estimated_absorpt_T_min   0.787
_exptl_absorpt_coefficient_mu    0.722
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.909
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) Numerical absorption correction based on gaussian integration over 			a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.348
_exptl_crystal_size_mid          0.199
_exptl_crystal_size_min          0.0526
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3928
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.613
_diffrn_reflns_theta_min         6.059
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
 #__ type_ start__ end____ width___ exp.time_ 1 omega 56.00 109.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.9624 -125.0000 0.0000 53 #__ type_ start__ end____ width___ exp.time_ 2 omega 84.00 110.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 109.9249 -111.0000 0.0000 26 #__ type_ start__ end____ width___ exp.time_ 3 omega 58.00 147.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 109.9249 -77.0000 -90.0000 89 #__ type_ start__ end____ width___ exp.time_ 4 omega 70.00 175.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 109.9249 37.0000 30.0000 105 #__ type_ start__ end____ width___ exp.time_ 5 omega 116.00 176.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 109.9249 111.0000 -90.0000 60 #__ type_ start__ end____ width___ exp.time_ 6 omega 118.00 143.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.9624 125.0000 -30.0000 25 #__ type_ start__ end____ width___ exp.time_ 7 omega 101.00 176.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 109.9249 111.0000 -60.0000 75 #__ type_ start__ end____ width___ exp.time_ 8 omega 106.00 146.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 109.9249 111.0000 60.0000 40 #__ type_ start__ end____ width___ exp.time_ 9 omega 106.00 155.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 109.9249 111.0000 -30.0000 49 #__ type_ start__ end____ width___ exp.time_ 10 omega 103.00 129.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 109.9249 111.0000 -150.0000 26 #__ type_ start__ end____ width___ exp.time_ 11 omega 80.00 115.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 109.9249 178.0000 -30.0000 35 #__ type_ start__ end____ width___ exp.time_ 12 omega 65.00 166.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 109.9249 37.0000 120.0000 101 #__ type_ start__ end____ width___ exp.time_ 13 omega 80.00 142.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 109.9
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_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                1152
_reflns_number_total             1286
_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, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01)'
_computing_data_collection       
'CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/2 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1286
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0400
_refine_ls_restrained_S_all      1.070
_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)+(0.0607P)²+0.3044P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1129
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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
O1 O 0.63701(10) 0.34002(14) 0.07110(9) 0.0215(3) Uani 1 1 d . . . . .
C17 C 0.73463(14) 0.39850(18) 0.15594(13) 0.0165(3) Uani 1 1 d . . . . .
C18 C 0.88057(15) 0.4546(2) 0.11765(14) 0.0202(3) Uani 1 1 d . . . . .
H18A H 0.9534 0.3635 0.1482 0.030 Uiso 1 1 calc R U . . .
H18B H 0.9103 0.5700 0.1587 0.030 Uiso 1 1 calc R U . . .
H18C H 0.8708 0.4660 0.0217 0.030 Uiso 1 1 calc R U . . .
C1 C 0.71555(14) 0.41505(17) 0.30078(13) 0.0151(3) Uani 1 1 d . . . . .
C2 C 0.57875(14) 0.46606(17) 0.33865(13) 0.0144(3) Uani 1 1 d . . . . .
C10 C 0.45197(15) 0.51973(18) 0.24351(13) 0.0168(3) Uani 1 1 d . . . . .
H10 H 0.4574 0.5175 0.1521 0.020 Uiso 1 1 calc R U . . .
C11 C 0.67383(15) 0.42713(18) 0.71573(13) 0.0176(3) Uani 1 1 d . . . . .
H11 H 0.7527 0.3914 0.7798 0.021 Uiso 1 1 calc R U . . .
C12 C 0.69007(14) 0.42388(17) 0.57644(13) 0.0153(3) Uani 1 1 d . . . . .
C13 C 0.82247(14) 0.37399(18) 0.53436(14) 0.0167(3) Uani 1 1 d . . . . .
H13 H 0.9028 0.3409 0.5978 0.020 Uiso 1 1 calc R U . . .
C14 C 0.83507(14) 0.37335(18) 0.39968(14) 0.0165(3) Uani 1 1 d . . . . .
H14 H 0.9252 0.3445 0.3741 0.020 Uiso 1 1 calc R U . . .
C15 C 0.56743(14) 0.47245(17) 0.47846(13) 0.0141(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C17 1.2166(16) . ?
C17 C18 1.5107(18) . ?
C17 C1 1.5018(18) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C1 C2 1.4210(18) . ?
C1 C14 1.3974(19) . ?
C2 C10 1.4436(18) . ?
C2 C15 1.4295(19) . ?
C10 H10 0.9300 . ?
C10 C11 1.345(2) 3_666 ?
C11 C10 1.345(2) 3_666 ?
C11 H11 0.9300 . ?
C11 C12 1.4347(19) . ?
C12 C13 1.3993(19) . ?
C12 C15 1.4234(19) . ?
C13 H13 0.9300 . ?
C13 C14 1.3800(19) . ?
C14 H14 0.9300 . ?
C15 C15 1.435(3) 3_666 ?

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
O1 C17 C18 120.26(12) . . ?
O1 C17 C1 121.71(12) . . ?
C1 C17 C18 118.03(11) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2 C1 C17 121.68(12) . . ?
C14 C1 C17 118.49(12) . . ?
C14 C1 C2 119.81(12) . . ?
C1 C2 C10 123.41(12) . . ?
C1 C2 C15 118.51(12) . . ?
C15 C2 C10 118.02(12) . . ?
C2 C10 H10 119.3 . . ?
C11 C10 C2 121.36(12) 3_666 . ?
C11 C10 H10 119.3 3_666 . ?
C10 C11 H11 119.0 3_666 . ?
C10 C11 C12 122.00(12) 3_666 . ?
C12 C11 H11 119.0 . . ?
C13 C12 C11 121.97(12) . . ?
C13 C12 C15 119.22(12) . . ?
C15 C12 C11 118.81(12) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.65(12) . . ?
C14 C13 H13 119.7 . . ?
C1 C14 H14 119.2 . . ?
C13 C14 C1 121.52(12) . . ?
C13 C14 H14 119.2 . . ?
C2 C15 C15 120.47(15) . 3_666 ?
C12 C15 C2 120.23(12) . . ?
C12 C15 C15 119.30(15) . 3_666 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C17 C1 C2 -36.40(19) . . . . ?
O1 C17 C1 C14 141.61(14) . . . . ?
C17 C1 C2 C10 -5.10(19) . . . . ?
C17 C1 C2 C15 177.73(11) . . . . ?
C17 C1 C14 C13 -175.69(12) . . . . ?
C18 C17 C1 C2 144.38(13) . . . . ?
C18 C17 C1 C14 -37.61(17) . . . . ?
C1 C2 C10 C11 -177.73(12) . . . 3_666 ?
C1 C2 C15 C12 -1.62(18) . . . . ?
C1 C2 C15 C15 178.47(14) . . . 3_666 ?
C2 C1 C14 C13 2.36(19) . . . . ?
C10 C2 C15 C12 -178.94(11) . . . . ?
C10 C2 C15 C15 1.1(2) . . . 3_666 ?
C10 C11 C12 C13 177.98(13) 3_666 . . . ?
C10 C11 C12 C15 -2.2(2) 3_666 . . . ?
C11 C12 C13 C14 -179.56(12) . . . . ?
C11 C12 C15 C2 -178.37(11) . . . . ?
C11 C12 C15 C15 1.5(2) . . . 3_666 ?
C12 C13 C14 C1 -2.6(2) . . . . ?
C13 C12 C15 C2 1.45(19) . . . . ?
C13 C12 C15 C15 -178.63(14) . . . 3_666 ?
C14 C1 C2 C10 176.92(12) . . . . ?
C14 C1 C2 C15 -0.25(18) . . . . ?
C15 C2 C10 C11 -0.55(19) . . . 3_666 ?
C15 C12 C13 C14 0.62(19) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2oapb_100k_smart3_abs
_database_code_depnum_ccdc_archive 'CCDC 2332704'
loop_
_audit_author_name
_audit_author_address
'Anna Makal'
;University of Warsaw, Chemistry Department
Poland
;
_audit_update_record             
;
2024-02-13 deposited with the CCDC.	2024-07-24 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT196_2oapb_100k_smart3_abs 
;
PROBLEM: No TEMP record and _measurement_temperature .NE.        293 Degree
RESPONSE: measurement temperature was 100K
;
_vrf_PLAT094_2oapb_100k_smart3_abs 
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       2.43 Report
RESPONSE: Certain bonding density features were visible in the pyrene fragment, hence high residual density peaks in the middle of the bonds.
;
_vrf_PLAT906_2oapb_100k_smart3_abs 
;
PROBLEM: Large K Value in the Analysis of Variance ......      2.688 Check
RESPONSE: This is a result of very low intensities of the data in the highest resolution shell.
;
# Added during the CSD deposition process: Tuesday 13 February 2024 01:00 PM
# end Validation Reply Form

_audit_creation_date             2024-01-17
_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            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 O2'
_chemical_formula_sum            'C20 H14 O2'
_chemical_formula_weight         286.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H14 O2'
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                   7.15110(13)
_cell_length_b                   10.90793(19)
_cell_length_c                   17.7744(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.4944(19)
_cell_angle_gamma                90
_cell_volume                     1353.63(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    19785
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      34.4320
_cell_measurement_theta_min      3.3090
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.836
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43d (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             600
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 3 5 0.0480
-5 0 3 0.0571
-1 2 5 0.0569
-1 5 0 0.0068
1 -5 -1 0.0241
2 -9 -21 0.0669
3 -1 -5 0.0793
6 -6 -20 0.0754
10 1 -9 0.0779
5 3 1 0.0652
0 2 5 0.0607
-2 -4 -5 0.0757
-3 1 5 0.0622
-1 5 4 0.0255
0 -2 5 0.0854
0 2 -24 0.0701

_exptl_crystal_size_max          0.173
_exptl_crystal_size_mid          0.141
_exptl_crystal_size_min          0.036
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
3.0000 3.0000 5.0000 0.1574 0.3024 0.2888
-5.0000 0.0000 3.0000 -0.2175 -0.4389 0.0792
-1.0000 2.0000 5.0000 -0.0287 -0.0608 0.2357
-1.0000 5.0000 -0.0000 -0.2790 0.0602 0.1859
1.0000 -5.0000 -1.0000 0.2555 -0.0532 -0.2186
2.0000 -9.0000 -21.0000 0.0204 0.0542 -1.0209
3.0000 -1.0000 -5.0000 0.0996 0.2568 -0.1901
6.0000 -6.0000 -20.0000 0.1415 0.4681 -0.8592
10.0000 1.0000 -9.0000 0.3203 0.9275 -0.2186
5.0000 3.0000 1.0000 0.1786 0.4975 0.1655
0.0000 2.0000 5.0000 0.0289 0.0228 0.2394
-2.0000 -4.0000 -5.0000 -0.0555 -0.2476 -0.3229
-3.0000 1.0000 5.0000 -0.0996 -0.2568 0.1901
-1.0000 5.0000 4.0000 -0.1850 0.0324 0.3168
0.0000 -2.0000 5.0000 0.2060 -0.0922 0.0877
-0.0000 2.0000 -24.0000 -0.6523 0.2242 -0.7093

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            48392
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.567
_diffrn_reflns_theta_min         3.326
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -52.00  43.00   0.50   80.00    --   30.50 -49.00  90.00  190
  2  ω     -9.00 112.00   0.50   80.00    --   30.50  49.00-122.00  242
  3  ω    -75.00 -39.00   0.50   80.00    --  -30.81 -49.00  90.00   72
  4  ω    -12.00 116.00   0.50   80.00    --   30.50  77.00  90.00  256
  5  ω     56.00 114.00   0.50   80.00    --   30.50 178.00  90.00  116
  6  ω    -49.00 -23.00   0.50   80.00    --   30.50  19.00-150.00   52
  7  ω    -12.00  78.00   0.50   80.00    --   30.50  77.00 -60.00  180
  8  ω     -4.00 117.00   0.50   80.00    --   30.50  19.00-150.00  242
  9  ω     -2.00 110.00   0.50   80.00    --   30.50  57.00  60.00  224
 10  ω   -126.00 -61.00   0.50   80.00    --  -30.81 178.00 -90.00  130
 11  ω   -124.00 -63.00   0.50   80.00    --  -30.81-178.00-180.00  122
 12  ω   -116.00   8.00   0.50   80.00    --  -30.81 -38.00 -90.00  248
 13  ω   -118.00  54.00   0.50   80.00    --  -30.81  19.00-150.00  344
 14  ω   -126.00 -73.00   0.50   80.00    --  -30.81-178.00  30.00  106
 15  ω    -22.00  16.00   0.50   80.00    --  -30.81 -99.00 150.00   76
 16  ω    -38.00  43.00   0.50   80.00    --  -30.81  49.00-122.00  162
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0575942284
_diffrn_orient_matrix_UB_12      -0.0442814338
_diffrn_orient_matrix_UB_13      0.0234894896
_diffrn_orient_matrix_UB_21      0.0836230409
_diffrn_orient_matrix_UB_22      0.0287614565
_diffrn_orient_matrix_UB_23      -0.0069440485
_diffrn_orient_matrix_UB_31      0.0037924276
_diffrn_orient_matrix_UB_32      0.0379375689
_diffrn_orient_matrix_UB_33      0.0327143467
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4111
_reflns_number_total             5486
_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 1.171.39.43d (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43d (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43d (Rigaku OD, 2018)'
_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    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         5486
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0440
_refine_ls_restrained_S_all      1.043
_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)+(0.0803P)²+0.0475P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1293
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.24475(10) 0.98448(7) 0.49282(4) 0.01581(14) Uani 1 1 d . . . . .
C2 C 0.21188(11) 0.85691(7) 0.47674(4) 0.01654(14) Uani 1 1 d . . . . .
C3 C 0.22866(11) 1.06901(7) 0.42994(4) 0.01755(15) Uani 1 1 d . . . . .
C4 C 0.31902(11) 0.94302(7) 0.63189(4) 0.01623(14) Uani 1 1 d . . . . .
C5 C 0.29938(10) 1.02865(7) 0.57028(4) 0.01591(14) Uani 1 1 d . . . . .
C6 C 0.28293(11) 0.81934(7) 0.61458(4) 0.01717(14) Uani 1 1 d . . . . .
C7 C 0.23508(11) 0.77387(7) 0.53962(4) 0.01708(14) Uani 1 1 d . . . . .
C8 C 0.26797(11) 1.19569(7) 0.44410(5) 0.01953(15) Uani 1 1 d . . . . .
C9 C 0.17952(11) 1.02675(8) 0.35263(5) 0.02002(16) Uani 1 1 d . . . . .
C10 C 0.31708(12) 1.23734(8) 0.52204(5) 0.02145(16) Uani 1 1 d . . . . .
C11 C 0.15490(12) 0.81825(8) 0.39779(5) 0.02074(16) Uani 1 1 d . . . . .
O12 O 0.47002(9) 1.07299(6) 0.73586(3) 0.02476(14) Uani 1 1 d . . . . .
C13 C 0.33103(12) 1.15849(7) 0.58220(5) 0.01978(15) Uani 1 1 d . . . . .
C14 C 0.14100(12) 0.89921(8) 0.33880(5) 0.02225(17) Uani 1 1 d . . . . .
C15 C 0.17271(12) 1.11012(9) 0.29186(5) 0.02462(18) Uani 1 1 d . . . . .
C16 C 0.26022(12) 1.27623(8) 0.38173(5) 0.02412(17) Uani 1 1 d . . . . .
C17 C 0.38571(11) 0.97683(7) 0.71499(4) 0.01829(15) Uani 1 1 d . . . . .
C18 C 0.22419(11) 0.63729(7) 0.52995(5) 0.02006(16) Uani 1 1 d . . . . .
O19 O 0.25546(11) 0.58620(6) 0.47258(4) 0.03026(16) Uani 1 1 d . . . . .
C20 C 0.21368(12) 1.23319(9) 0.30653(5) 0.02633(19) Uani 1 1 d . . . . .
C21 C 0.17864(14) 0.56170(8) 0.59488(5) 0.02398(17) Uani 1 1 d . . . . .
C22 C 0.34924(14) 0.88761(9) 0.77532(5) 0.02400(17) Uani 1 1 d . . . . .
H6 H 0.3035(17) 0.7585(11) 0.6583(7) 0.027(3) Uiso 1 1 d . . . . .
H20 H 0.2133(19) 1.2907(12) 0.2635(7) 0.040(3) Uiso 1 1 d . . . . .
H11 H 0.1298(18) 0.7303(12) 0.3869(7) 0.036(3) Uiso 1 1 d . . . . .
H15 H 0.1414(18) 1.0776(11) 0.2372(7) 0.028(3) Uiso 1 1 d . . . . .
H10 H 0.3443(18) 1.3253(12) 0.5307(7) 0.035(3) Uiso 1 1 d . . . . .
H22A H 0.429(2) 0.8150(14) 0.7761(8) 0.051(4) Uiso 1 1 d . . . . .
H13 H 0.3672(17) 1.1891(11) 0.6346(7) 0.027(3) Uiso 1 1 d . . . . .
H22B H 0.2134(18) 0.8618(12) 0.7638(7) 0.033(3) Uiso 1 1 d . . . . .
H22C H 0.3794(19) 0.9286(11) 0.8257(7) 0.033(3) Uiso 1 1 d . . . . .
H16 H 0.2958(18) 1.3626(12) 0.3924(7) 0.035(3) Uiso 1 1 d . . . . .
H14 H 0.1041(17) 0.8718(11) 0.2838(7) 0.027(3) Uiso 1 1 d . . . . .
H21A H 0.0736(19) 0.5979(12) 0.6140(7) 0.036(3) Uiso 1 1 d . . . . .
H21B H 0.142(2) 0.4786(13) 0.5749(7) 0.043(4) Uiso 1 1 d . . . . .
H21C H 0.292(2) 0.5545(12) 0.6379(7) 0.038(3) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.4298(11) . ?
C1 C3 1.4342(11) . ?
C1 C5 1.4309(10) . ?
C2 C7 1.4202(11) . ?
C2 C11 1.4372(11) . ?
C3 C8 1.4217(11) . ?
C3 C9 1.4197(11) . ?
C4 C5 1.4230(11) . ?
C4 C6 1.3954(11) . ?
C4 C17 1.4966(11) . ?
C5 C13 1.4427(11) . ?
C6 C7 1.3931(11) . ?
C6 H6 1.008(12) . ?
C7 C18 1.4998(11) . ?
C8 C10 1.4277(12) . ?
C8 C16 1.4062(11) . ?
C9 C14 1.4291(12) . ?
C9 C15 1.4047(12) . ?
C10 C13 1.3590(11) . ?
C10 H10 0.985(13) . ?
C11 C14 1.3581(12) . ?
C11 H11 0.987(13) . ?
O12 C17 1.2266(10) . ?
C13 H13 0.970(11) . ?
C14 H14 1.001(12) . ?
C15 C20 1.3868(14) . ?
C15 H15 1.012(12) . ?
C16 C20 1.3876(13) . ?
C16 H16 0.984(13) . ?
C17 C22 1.5120(12) . ?
C18 O19 1.2243(10) . ?
C18 C21 1.5102(12) . ?
C20 H20 0.989(13) . ?
C21 H21A 0.973(13) . ?
C21 H21B 0.987(14) . ?
C21 H21C 0.991(14) . ?
C22 H22A 0.973(15) . ?
C22 H22B 0.989(13) . ?
C22 H22C 0.983(13) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C3 119.20(7) . . ?
C2 C1 C5 121.27(7) . . ?
C5 C1 C3 119.50(7) . . ?
C1 C2 C11 118.71(7) . . ?
C7 C2 C1 118.50(7) . . ?
C7 C2 C11 122.78(7) . . ?
C8 C3 C1 120.50(7) . . ?
C9 C3 C1 120.46(7) . . ?
C9 C3 C8 119.01(7) . . ?
C5 C4 C17 123.72(7) . . ?
C6 C4 C5 118.82(7) . . ?
C6 C4 C17 117.39(7) . . ?
C1 C5 C13 118.26(7) . . ?
C4 C5 C1 118.71(7) . . ?
C4 C5 C13 123.03(7) . . ?
C4 C6 H6 118.5(7) . . ?
C7 C6 C4 123.41(7) . . ?
C7 C6 H6 117.9(7) . . ?
C2 C7 C18 123.29(7) . . ?
C6 C7 C2 119.23(7) . . ?
C6 C7 C18 117.34(7) . . ?
C3 C8 C10 118.60(7) . . ?
C16 C8 C3 119.68(8) . . ?
C16 C8 C10 121.71(8) . . ?
C3 C9 C14 118.73(7) . . ?
C15 C9 C3 119.63(8) . . ?
C15 C9 C14 121.64(8) . . ?
C8 C10 H10 117.4(7) . . ?
C13 C10 C8 121.53(7) . . ?
C13 C10 H10 121.0(7) . . ?
C2 C11 H11 118.5(7) . . ?
C14 C11 C2 121.40(8) . . ?
C14 C11 H11 120.1(7) . . ?
C5 C13 H13 118.7(7) . . ?
C10 C13 C5 121.55(7) . . ?
C10 C13 H13 119.7(7) . . ?
C9 C14 H14 117.3(7) . . ?
C11 C14 C9 121.40(7) . . ?
C11 C14 H14 121.3(7) . . ?
C9 C15 H15 118.3(7) . . ?
C20 C15 C9 120.76(8) . . ?
C20 C15 H15 120.9(7) . . ?
C8 C16 H16 118.8(7) . . ?
C20 C16 C8 120.56(8) . . ?
C20 C16 H16 120.5(7) . . ?
C4 C17 C22 118.32(7) . . ?
O12 C17 C4 122.69(7) . . ?
O12 C17 C22 118.99(7) . . ?
C7 C18 C21 117.97(7) . . ?
O19 C18 C7 122.23(8) . . ?
O19 C18 C21 119.77(8) . . ?
C15 C20 C16 120.37(8) . . ?
C15 C20 H20 120.2(8) . . ?
C16 C20 H20 119.4(8) . . ?
C18 C21 H21A 110.8(7) . . ?
C18 C21 H21B 108.1(8) . . ?
C18 C21 H21C 110.9(8) . . ?
H21A C21 H21B 109.6(11) . . ?
H21A C21 H21C 109.2(10) . . ?
H21B C21 H21C 108.2(11) . . ?
C17 C22 H22A 110.1(9) . . ?
C17 C22 H22B 110.4(7) . . ?
C17 C22 H22C 108.4(7) . . ?
H22A C22 H22B 108.4(12) . . ?
H22A C22 H22C 110.2(11) . . ?
H22B C22 H22C 109.3(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C7 C6 1.99(11) . . . . ?
C1 C2 C7 C18 -173.59(7) . . . . ?
C1 C2 C11 C14 3.21(12) . . . . ?
C1 C3 C8 C10 -2.17(11) . . . . ?
C1 C3 C8 C16 177.01(7) . . . . ?
C1 C3 C9 C14 1.83(11) . . . . ?
C1 C3 C9 C15 -177.20(7) . . . . ?
C1 C5 C13 C10 -2.49(11) . . . . ?
C2 C1 C3 C8 -177.47(7) . . . . ?
C2 C1 C3 C9 0.39(11) . . . . ?
C2 C1 C5 C4 -0.60(11) . . . . ?
C2 C1 C5 C13 179.72(7) . . . . ?
C2 C7 C18 O19 23.86(12) . . . . ?
C2 C7 C18 C21 -157.99(7) . . . . ?
C2 C11 C14 C9 -0.99(13) . . . . ?
C3 C1 C2 C7 177.78(7) . . . . ?
C3 C1 C2 C11 -2.86(11) . . . . ?
C3 C1 C5 C4 -178.53(7) . . . . ?
C3 C1 C5 C13 1.79(10) . . . . ?
C3 C8 C10 C13 1.53(12) . . . . ?
C3 C8 C16 C20 0.30(12) . . . . ?
C3 C9 C14 C11 -1.56(12) . . . . ?
C3 C9 C15 C20 0.09(12) . . . . ?
C4 C5 C13 C10 177.85(7) . . . . ?
C4 C6 C7 C2 -3.23(12) . . . . ?
C4 C6 C7 C18 172.62(7) . . . . ?
C5 C1 C2 C7 -0.15(11) . . . . ?
C5 C1 C2 C11 179.21(7) . . . . ?
C5 C1 C3 C8 0.50(11) . . . . ?
C5 C1 C3 C9 178.36(7) . . . . ?
C5 C4 C6 C7 2.45(12) . . . . ?
C5 C4 C17 O12 -17.42(12) . . . . ?
C5 C4 C17 C22 163.35(7) . . . . ?
C6 C4 C5 C1 -0.48(11) . . . . ?
C6 C4 C5 C13 179.18(7) . . . . ?
C6 C4 C17 O12 159.59(8) . . . . ?
C6 C4 C17 C22 -19.64(11) . . . . ?
C6 C7 C18 O19 -151.80(8) . . . . ?
C6 C7 C18 C21 26.35(11) . . . . ?
C7 C2 C11 C14 -177.45(7) . . . . ?
C8 C3 C9 C14 179.72(7) . . . . ?
C8 C3 C9 C15 0.69(11) . . . . ?
C8 C10 C13 C5 0.82(12) . . . . ?
C8 C16 C20 C15 0.50(13) . . . . ?
C9 C3 C8 C10 179.94(7) . . . . ?
C9 C3 C8 C16 -0.88(11) . . . . ?
C9 C15 C20 C16 -0.69(13) . . . . ?
C10 C8 C16 C20 179.45(8) . . . . ?
C11 C2 C7 C6 -177.34(7) . . . . ?
C11 C2 C7 C18 7.07(12) . . . . ?
C14 C9 C15 C20 -178.92(8) . . . . ?
C15 C9 C14 C11 177.45(8) . . . . ?
C16 C8 C10 C13 -177.63(8) . . . . ?
C17 C4 C5 C1 176.49(7) . . . . ?
C17 C4 C5 C13 -3.85(12) . . . . ?
C17 C4 C6 C7 -174.71(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 1.258
_oxdiff_exptl_absorpt_empirical_full_min 0.823
####################################################################### 
# 
# 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_2pAPb_100K
_database_code_depnum_ccdc_archive 'CCDC 2332699'
loop_
_audit_author_name
_audit_author_address
'Anna Makal'
;University of Warsaw, Chemistry Department
Poland
;
_audit_update_record             
;
2024-02-13 deposited with the CCDC.	2024-07-24 downloaded from the CCDC.
;
_audit_creation_date             2024-01-25
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2023.11.24 svn.r209d9fb for OlexSys, GUI svn.r6869)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C10 H7 O)'
_chemical_formula_sum            'C20 H14 O2'
_chemical_formula_weight         286.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   8.02950(10)
_cell_length_b                   23.1438(4)
_cell_length_c                   7.45590(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.865(2)
_cell_angle_gamma                90
_cell_volume                     1378.30(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.701
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             600
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            16650
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.170
_diffrn_reflns_theta_min         3.820
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_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                2510
_reflns_number_total             2904
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/2 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.0009(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2904
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.093
_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)+(0.0872P)²+0.2800P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1414
_refine_ls_wR_factor_ref         0.1477
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C5A(H5A), C6A(H6A), C7A(H7A), C1B(H1B), C5B(H5B), C6B(H6B), C7B(H7B)
2.b Idealised Me refined as rotating group:
 C10A(H10A,H10B,H10C), C10B(H10D,H10E,H10F)
;
_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
O1A O 0.57841(16) 0.29405(5) 0.4889(2) 0.0523(4) Uani 1 1 d . . . . .
C1A C 0.39322(16) 0.39784(6) 0.53075(15) 0.0227(3) Uani 1 1 d . . . . .
H1A H 0.3760 0.3517 0.5313 0.027 Uiso 1 1 calc R U . . .
C2A C 0.55046(15) 0.42068(6) 0.47436(15) 0.0211(3) Uani 1 1 d . . . . .
C3A C 0.56578(14) 0.48196(5) 0.47332(15) 0.0212(3) Uani 1 1 d . . . . .
C4A C 0.71212(16) 0.50836(6) 0.41872(16) 0.0235(3) Uani 1 1 d . . . . .
C5A C 0.72673(16) 0.56967(6) 0.41976(17) 0.0263(3) Uani 1 1 d . . . . .
H5A H 0.8383 0.5895 0.3792 0.032 Uiso 1 1 calc R U . . .
C6A C 0.84059(16) 0.47361(6) 0.36435(17) 0.0261(3) Uani 1 1 d . . . . .
H6A H 0.9511 0.4933 0.3209 0.031 Uiso 1 1 calc R U . . .
C7A C 0.82628(16) 0.41430(6) 0.36621(17) 0.0259(3) Uani 1 1 d . . . . .
H7A H 0.9266 0.3885 0.3237 0.031 Uiso 1 1 calc R U . . .
C8A C 0.68499(16) 0.38656(6) 0.42179(16) 0.0227(3) Uani 1 1 d . . . . .
C9A C 0.68447(17) 0.32215(6) 0.42408(18) 0.0281(3) Uani 1 1 d . . . . .
C10A C 0.8230(2) 0.28983(7) 0.3461(3) 0.0453(4) Uani 1 1 d . . . . .
H10A H 0.9391 0.2959 0.4316 0.068 Uiso 1 1 calc R U . . .
H10B H 0.8370 0.3061 0.2123 0.068 Uiso 1 1 calc R U . . .
H10C H 0.7927 0.2442 0.3383 0.068 Uiso 1 1 calc R U . . .
O1B O 0.07045(12) 0.14582(4) 0.50642(18) 0.0406(3) Uani 1 1 d . . . . .
C1B C 0.21601(14) 0.03206(5) 0.59067(16) 0.0208(3) Uani 1 1 d . . . . .
H1B H 0.1076 0.0556 0.6238 0.025 Uiso 1 1 calc R U . . .
C2B C 0.35614(14) 0.06326(5) 0.53298(15) 0.0186(3) Uani 1 1 d . . . . .
C3B C 0.49944(14) 0.03082(5) 0.49333(15) 0.0181(3) Uani 1 1 d . . . . .
C4B C 0.64198(14) 0.05980(5) 0.43893(15) 0.0192(3) Uani 1 1 d . . . . .
C5B C 0.78254(14) 0.02629(5) 0.39586(16) 0.0208(3) Uani 1 1 d . . . . .
H5B H 0.8897 0.0480 0.3517 0.025 Uiso 1 1 calc R U . . .
C6B C 0.64297(15) 0.12003(5) 0.42940(16) 0.0217(3) Uani 1 1 d . . . . .
H6B H 0.7511 0.1420 0.3886 0.026 Uiso 1 1 calc R U . . .
C7B C 0.50582(15) 0.15187(5) 0.47207(17) 0.0219(3) Uani 1 1 d . . . . .
H7B H 0.5105 0.1984 0.4683 0.026 Uiso 1 1 calc R U . . .
C8B C 0.36136(15) 0.12433(5) 0.52002(16) 0.0206(3) Uani 1 1 d . . . . .
C9B C 0.21372(16) 0.16138(5) 0.55018(18) 0.0244(3) Uani 1 1 d . . . . .
C10B C 0.24764(17) 0.21961(6) 0.6365(2) 0.0293(3) Uani 1 1 d . . . . .
H10D H 0.3057 0.2475 0.5443 0.044 Uiso 1 1 calc R U . . .
H10E H 0.3308 0.2145 0.7593 0.044 Uiso 1 1 calc R U . . .
H10F H 0.1308 0.2386 0.6680 0.044 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
O1A C9A 1.2108(18) . ?
C1A H1A 1.0770 . ?
C1A C2A 1.4692(16) . ?
C1A C5A 1.3044(19) 3_666 ?
C2A C3A 1.4238(18) . ?
C2A C8A 1.4250(17) . ?
C3A C3A 1.434(2) 3_666 ?
C3A C4A 1.4203(17) . ?
C4A C5A 1.4239(18) . ?
C4A C6A 1.4001(18) . ?
C5A C1A 1.3044(19) 3_666 ?
C5A H5A 1.0770 . ?
C6A H6A 1.0770 . ?
C6A C7A 1.3777(19) . ?
C7A H7A 1.0770 . ?
C7A C8A 1.4026(17) . ?
C8A C9A 1.4908(19) . ?
C9A C10A 1.5060(19) . ?
C10A H10A 1.0831 . ?
C10A H10B 1.0831 . ?
C10A H10C 1.0831 . ?
O1B C9B 1.2176(17) . ?
C1B H1B 1.0770 . ?
C1B C2B 1.4393(16) . ?
C1B C5B 1.3541(18) 3_656 ?
C2B C3B 1.4299(16) . ?
C2B C8B 1.4177(17) . ?
C3B C3B 1.430(2) 3_656 ?
C3B C4B 1.4209(16) . ?
C4B C5B 1.4326(16) . ?
C4B C6B 1.3960(18) . ?
C5B C1B 1.3541(18) 3_656 ?
C5B H5B 1.0770 . ?
C6B H6B 1.0770 . ?
C6B C7B 1.3887(17) . ?
C7B H7B 1.0770 . ?
C7B C8B 1.4015(16) . ?
C8B C9B 1.4985(16) . ?
C9B C10B 1.5063(18) . ?
C10B H10D 1.0831 . ?
C10B H10E 1.0831 . ?
C10B H10F 1.0831 . ?

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
C2A C1A H1A 118.2 . . ?
C5A C1A H1A 118.2 3_666 . ?
C5A C1A C2A 123.68(12) 3_666 . ?
C3A C2A C1A 115.92(12) . . ?
C3A C2A C8A 118.83(11) . . ?
C8A C2A C1A 125.25(12) . . ?
C2A C3A C3A 120.79(14) . 3_666 ?
C4A C3A C2A 120.30(12) . . ?
C4A C3A C3A 118.91(15) . 3_666 ?
C3A C4A C5A 119.81(12) . . ?
C6A C4A C3A 119.44(12) . . ?
C6A C4A C5A 120.74(12) . . ?
C1A C5A C4A 120.87(12) 3_666 . ?
C1A C5A H5A 119.6 3_666 . ?
C4A C5A H5A 119.6 . . ?
C4A C6A H6A 119.8 . . ?
C7A C6A C4A 120.30(12) . . ?
C7A C6A H6A 119.8 . . ?
C6A C7A H7A 119.0 . . ?
C6A C7A C8A 122.00(12) . . ?
C8A C7A H7A 119.0 . . ?
C2A C8A C9A 123.22(11) . . ?
C7A C8A C2A 119.10(12) . . ?
C7A C8A C9A 117.67(12) . . ?
O1A C9A C8A 122.99(12) . . ?
O1A C9A C10A 117.71(13) . . ?
C8A C9A C10A 119.29(12) . . ?
C9A C10A H10A 109.5 . . ?
C9A C10A H10B 109.5 . . ?
C9A C10A H10C 109.5 . . ?
H10A C10A H10B 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
C2B C1B H1B 119.3 . . ?
C5B C1B H1B 119.3 3_656 . ?
C5B C1B C2B 121.43(11) 3_656 . ?
C3B C2B C1B 117.94(11) . . ?
C8B C2B C1B 123.37(11) . . ?
C8B C2B C3B 118.65(11) . . ?
C2B C3B C3B 120.59(13) . 3_656 ?
C4B C3B C2B 119.99(11) . . ?
C4B C3B C3B 119.42(13) . 3_656 ?
C3B C4B C5B 118.98(11) . . ?
C6B C4B C3B 119.66(11) . . ?
C6B C4B C5B 121.36(11) . . ?
C1B C5B C4B 121.61(11) 3_656 . ?
C1B C5B H5B 119.2 3_656 . ?
C4B C5B H5B 119.2 . . ?
C4B C6B H6B 119.7 . . ?
C7B C6B C4B 120.62(11) . . ?
C7B C6B H6B 119.7 . . ?
C6B C7B H7B 119.5 . . ?
C6B C7B C8B 120.91(12) . . ?
C8B C7B H7B 119.5 . . ?
C2B C8B C9B 122.07(10) . . ?
C7B C8B C2B 120.11(11) . . ?
C7B C8B C9B 117.79(11) . . ?
O1B C9B C8B 122.06(12) . . ?
O1B C9B C10B 120.24(12) . . ?
C8B C9B C10B 117.70(11) . . ?
C9B C10B H10D 109.5 . . ?
C9B C10B H10E 109.5 . . ?
C9B C10B H10F 109.5 . . ?
H10D C10B H10E 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1A C2A C3A C3A 0.64(19) . . . 3_666 ?
C1A C2A C3A C4A -179.20(10) . . . . ?
C1A C2A C8A C7A 178.25(11) . . . . ?
C1A C2A C8A C9A -2.28(19) . . . . ?
C2A C3A C4A C5A -179.43(11) . . . . ?
C2A C3A C4A C6A 0.58(17) . . . . ?
C2A C8A C9A O1A -8.2(2) . . . . ?
C2A C8A C9A C10A 173.01(13) . . . . ?
C3A C2A C8A C7A -1.65(17) . . . . ?
C3A C2A C8A C9A 177.82(11) . . . . ?
C3A C3A C4A C5A 0.7(2) 3_666 . . . ?
C3A C3A C4A C6A -179.27(13) 3_666 . . . ?
C3A C4A C5A C1A -0.43(19) . . . 3_666 ?
C3A C4A C6A C7A -0.92(18) . . . . ?
C4A C6A C7A C8A -0.06(19) . . . . ?
C5A C1A C2A C3A -0.97(17) 3_666 . . . ?
C5A C1A C2A C8A 179.12(12) 3_666 . . . ?
C5A C4A C6A C7A 179.09(11) . . . . ?
C6A C4A C5A C1A 179.56(11) . . . 3_666 ?
C6A C7A C8A C2A 1.36(18) . . . . ?
C6A C7A C8A C9A -178.14(11) . . . . ?
C7A C8A C9A O1A 171.23(14) . . . . ?
C7A C8A C9A C10A -7.51(19) . . . . ?
C8A C2A C3A C3A -179.45(12) . . . 3_666 ?
C8A C2A C3A C4A 0.71(17) . . . . ?
C1B C2B C3B C3B 1.53(19) . . . 3_656 ?
C1B C2B C3B C4B -178.90(10) . . . . ?
C1B C2B C8B C7B 176.57(11) . . . . ?
C1B C2B C8B C9B -5.53(18) . . . . ?
C2B C3B C4B C5B -178.56(10) . . . . ?
C2B C3B C4B C6B 1.79(17) . . . . ?
C2B C8B C9B O1B -34.48(19) . . . . ?
C2B C8B C9B C10B 145.93(12) . . . . ?
C3B C2B C8B C7B -1.04(17) . . . . ?
C3B C2B C8B C9B 176.87(11) . . . . ?
C3B C3B C4B C5B 1.0(2) 3_656 . . . ?
C3B C3B C4B C6B -178.63(12) 3_656 . . . ?
C3B C4B C5B C1B -1.38(18) . . . 3_656 ?
C3B C4B C6B C7B -0.18(18) . . . . ?
C4B C6B C7B C8B -2.06(18) . . . . ?
C5B C1B C2B C3B -1.21(17) 3_656 . . . ?
C5B C1B C2B C8B -178.83(11) 3_656 . . . ?
C5B C4B C6B C7B -179.83(11) . . . . ?
C6B C4B C5B C1B 178.27(11) . . . 3_656 ?
C6B C7B C8B C2B 2.67(18) . . . . ?
C6B C7B C8B C9B -175.32(11) . . . . ?
C7B C8B C9B O1B 143.48(14) . . . . ?
C7B C8B C9B C10B -36.12(17) . . . . ?
C8B C2B C3B C3B 179.26(12) . . . 3_656 ?
C8B C2B C3B C4B -1.17(17) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2papb_rt
_database_code_depnum_ccdc_archive 'CCDC 2332698'
loop_
_audit_author_name
_audit_author_address
'Anna Makal'
;University of Warsaw, Chemistry Department
Poland
;
_audit_update_record             
;
2024-02-13 deposited with the CCDC.	2024-07-24 downloaded from the CCDC.
;
_audit_creation_date             2024-01-25
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2023.11.24 svn.r209d9fb for OlexSys, GUI svn.r6869)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C10 H7 O)'
_chemical_formula_sum            'C20 H14 O2'
_chemical_formula_weight         286.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   8.12030(10)
_cell_length_b                   23.1408(4)
_cell_length_c                   7.56240(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.1960(10)
_cell_angle_gamma                90
_cell_volume                     1415.21(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4908
_cell_measurement_temperature    280.00(10)
_cell_measurement_theta_max      77.5390
_cell_measurement_theta_min      3.8150
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.683
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.669
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43d (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 3 0 0.0839
-1 2 -5 0.1553
0 -1 5 0.1472
0 -15 0 0.0344
0 15 0 0.0114
0 14 -1 0.0269
5 -3 0 0.1008
5 -4 -3 0.1126
1 -2 5 0.1385

_exptl_crystal_size_max          0.327
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.046
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0207
_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       29
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            13641
_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         77.708
_diffrn_reflns_theta_min         3.820
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_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    -94.00 -44.00   0.50    0.35    --    0.00-178.00-180.00  100
  2  ω    -43.00  14.00   0.50    0.35    --    0.00  77.00-180.00  114
  3  ω      8.00  51.00   0.50    0.35    --    0.00 -99.00  30.00   86
  4  ω     31.00  81.00   0.50    0.35    --    0.00  77.00-180.00  100
  5  ω      8.00  33.00   0.50    0.35    --    0.00 -99.00-180.00   50
  6  ω    103.00 129.00   0.50    1.35    --   66.54 125.00 150.00   52
  7  ω     64.00  90.00   0.50    1.35    --   66.54  61.00 120.00   52
  8  ω    114.00 148.00   0.50    1.35    --   66.54 125.00-150.00   68
  9  ω    114.00 140.00   0.50    1.35    --   66.54 125.00-180.00   52
 10  ω     26.00 105.00   0.50    1.35    --   66.54 -94.00 150.00  158
 11  ω     34.00 111.00   0.50    1.35    --   66.54-125.00 -30.00  154
 12  ω     37.00  63.00   0.50    1.35    --   66.54  61.00 120.00   52
 13  ω    106.00 132.00   0.50    1.35    --   66.54  61.00 120.00   52
 14  ω    106.00 140.00   0.50    1.35    --   66.54 125.00 120.00   68
 15  ω    -26.00 155.00   0.50    1.35    --   66.54   0.00  30.00  362
 16  ω    102.00 138.00   0.50    1.35    --   66.54 125.00  30.00   72
 17  ω     95.00 120.00   0.50    1.35    --   66.54 125.00  60.00   50
 18  ω    108.00 133.00   0.50    1.35    --   66.54 125.00 -30.00   50
 19  ω    120.00 148.00   0.50    1.35    --   66.54 125.00 -90.00   56
 20  ω    -12.00  13.00   0.50    1.35    --   66.54 -94.00 150.00   50
 21  ω    114.00 158.00   0.50    1.35    --  121.75 -50.00-180.00   88
 22  ω     81.00 107.00   0.50    1.35    --  121.75 -50.00-180.00   52
 23  ω    129.00 161.00   0.50    1.35    --  121.75 -50.00   0.00   64
 24  ω     41.00 119.00   0.50    1.35    --  121.75 -77.00-150.00  156
 25  ω     83.00 108.00   0.50    1.35    --  121.75-111.00 120.00   50
 26  ω     63.00  89.00   0.50    1.35    --  121.75-111.00  60.00   52
 27  ω    133.00 160.00   0.50    1.35    --  121.75 -77.00-150.00   54
 28  ω    120.00 168.00   0.50    1.35    --  121.75 111.00 -90.00   96
 29  ω     82.00 108.00   0.50    1.35    --  121.75-111.00-120.00   52
 30  ω     89.00 121.00   0.50    1.35    --  121.75 -50.00   0.00   64
 31  ω     45.00 108.00   0.50    1.35    --  121.75-111.00  30.00  126
 32  ω     66.00 108.00   0.50    1.35    --  121.75-111.00 -60.00   84
 33  ω     28.00 167.00   0.50    1.35    --  121.75  12.00  90.00  278
 34  ω     43.00 169.00   0.50    1.35    --  121.75 -38.00 150.00  252
 35  ω    105.00 172.00   0.50    1.35    --  121.75 111.00-150.00  134
 36  ω     44.00 107.00   0.50    1.35    --  121.75-111.00   0.00  126
 37  ω     45.00  86.00   0.50    1.35    --  121.75 -50.00   0.00   82
 38  ω     78.00 108.00   0.50    1.35    --  121.75-111.00 150.00   60
 39  ω    120.00 170.00   0.50    1.35    --  121.75  77.00-180.00  100
 40  ω     80.00 106.00   0.50    1.35    --  121.75  77.00-180.00   52
 41  ω    115.00 144.00   0.50    1.35    --  121.75 111.00-120.00   58
 42  ω     65.00 105.00   0.50    1.35    --  121.75-111.00-150.00   80
 43  ω     48.00  73.00   0.50    1.35    --  121.75-111.00 150.00   50
 44  ω     71.00 134.00   0.50    1.35    --  121.75 178.00 -90.00  126
 45  ω     38.00 101.00   0.50    1.35    --  121.75 -91.00  30.00  126
 46  ω     67.00 107.00   0.50    1.35    --  121.75-111.00  90.00   80
 47  ω    121.00 146.00   0.50    1.35    --  121.75 178.00-120.00   50
 48  ω     65.00 100.00   0.50    1.35    --  121.75 178.00-120.00   70
 49  ω     87.00 113.00   0.50    1.35    --  121.75 178.00 -30.00   52
 50  ω     77.00 109.00   0.50    1.35    --  121.75-112.00 -23.60   64
 51  ω     47.00  72.00   0.50    1.35    --  121.75-112.00 -23.60   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, HyPix'
_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                2408
_reflns_number_total             2998
_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 1.171.39.43d (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43d (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43d (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0007(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2998
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0529
_refine_ls_restrained_S_all      1.080
_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)+(0.1035P)²+0.1897P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1740
_refine_ls_wR_factor_ref         0.1839
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C5A(H5A), C6A(H6A), C7A(H7A), C1B(H1B), C5B(H5B), C6B(H6B), C7B(H7B)
2.b Idealised Me refined as rotating group:
 C10A(H10A,H10B,H10C), C10B(H10D,H10E,H10F)
;
_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
O1A O 0.5844(3) 0.29546(7) 0.4858(4) 0.1373(9) Uani 1 1 d . . . . .
C1A C 0.4018(2) 0.39760(7) 0.53906(18) 0.0518(4) Uani 1 1 d . . . . .
H1A H 0.3881 0.3513 0.5434 0.062 Uiso 1 1 calc R U . . .
C2A C 0.55529(18) 0.42105(7) 0.48017(17) 0.0481(4) Uani 1 1 d . . . . .
C3A C 0.56643(16) 0.48235(6) 0.47456(16) 0.0457(4) Uani 1 1 d . . . . .
C4A C 0.70931(18) 0.50946(7) 0.41806(18) 0.0510(4) Uani 1 1 d . . . . .
C5A C 0.7181(2) 0.57085(8) 0.4139(2) 0.0583(4) Uani 1 1 d . . . . .
H5A H 0.8266 0.5914 0.3709 0.070 Uiso 1 1 calc R U . . .
C6A C 0.83854(19) 0.47537(8) 0.3669(2) 0.0583(4) Uani 1 1 d . . . . .
H6A H 0.9465 0.4957 0.3216 0.070 Uiso 1 1 calc R U . . .
C7A C 0.8292(2) 0.41603(8) 0.3737(2) 0.0611(4) Uani 1 1 d . . . . .
H7A H 0.9310 0.3907 0.3343 0.073 Uiso 1 1 calc R U . . .
C8A C 0.69128(19) 0.38776(7) 0.4305(2) 0.0541(4) Uani 1 1 d . . . . .
C9A C 0.6938(2) 0.32357(8) 0.4371(2) 0.0691(5) Uani 1 1 d . . . . .
C10A C 0.8341(4) 0.29122(12) 0.3728(6) 0.1388(14) Uani 1 1 d . . . . .
H10A H 0.9418 0.2959 0.4671 0.208 Uiso 1 1 calc R U . . .
H10B H 0.8612 0.3082 0.2452 0.208 Uiso 1 1 calc R U . . .
H10C H 0.8017 0.2459 0.3591 0.208 Uiso 1 1 calc R U . . .
O1B O 0.08167(16) 0.14728(6) 0.5119(3) 0.1043(7) Uani 1 1 d . . . . .
C1B C 0.21936(16) 0.03250(6) 0.59052(19) 0.0476(3) Uani 1 1 d . . . . .
H1B H 0.1127 0.0562 0.6250 0.057 Uiso 1 1 calc R U . . .
C2B C 0.36003(15) 0.06361(6) 0.53588(16) 0.0420(3) Uani 1 1 d . . . . .
C3B C 0.50069(15) 0.03080(6) 0.49533(15) 0.0397(3) Uani 1 1 d . . . . .
C4B C 0.64368(16) 0.05948(6) 0.44449(17) 0.0431(3) Uani 1 1 d . . . . .
C5B C 0.78137(16) 0.02553(6) 0.40066(19) 0.0479(3) Uani 1 1 d . . . . .
H5B H 0.8890 0.0471 0.3593 0.058 Uiso 1 1 calc R U . . .
C6B C 0.64663(18) 0.11967(7) 0.4384(2) 0.0499(4) Uani 1 1 d . . . . .
H6B H 0.7549 0.1416 0.4001 0.060 Uiso 1 1 calc R U . . .
C7B C 0.51178(18) 0.15152(6) 0.4812(2) 0.0516(4) Uani 1 1 d . . . . .
H7B H 0.5181 0.1980 0.4796 0.062 Uiso 1 1 calc R U . . .
C8B C 0.36730(17) 0.12455(6) 0.52669(19) 0.0476(3) Uani 1 1 d . . . . .
C9B C 0.2221(2) 0.16195(7) 0.5571(2) 0.0606(4) Uani 1 1 d . . . . .
C10B C 0.2552(2) 0.21980(8) 0.6429(3) 0.0735(5) Uani 1 1 d . . . . .
H10D H 0.3133 0.2479 0.5524 0.110 Uiso 1 1 calc R U . . .
H10E H 0.3366 0.2144 0.7634 0.110 Uiso 1 1 calc R U . . .
H10F H 0.1397 0.2388 0.6748 0.110 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
O1A C9A 1.186(2) . ?
C1A H1A 1.0770 . ?
C1A C2A 1.465(2) . ?
C1A C5A 1.292(2) 3_666 ?
C2A C3A 1.422(2) . ?
C2A C8A 1.424(2) . ?
C3A C3A 1.433(3) 3_666 ?
C3A C4A 1.4185(19) . ?
C4A C5A 1.423(2) . ?
C4A C6A 1.395(2) . ?
C5A C1A 1.292(2) 3_666 ?
C5A H5A 1.0770 . ?
C6A H6A 1.0770 . ?
C6A C7A 1.377(2) . ?
C7A H7A 1.0770 . ?
C7A C8A 1.398(2) . ?
C8A C9A 1.486(2) . ?
C9A C10A 1.481(3) . ?
C10A H10A 1.0831 . ?
C10A H10B 1.0831 . ?
C10A H10C 1.0831 . ?
O1B C9B 1.209(2) . ?
C1B H1B 1.0770 . ?
C1B C2B 1.4420(19) . ?
C1B C5B 1.344(2) 3_656 ?
C2B C3B 1.4279(18) . ?
C2B C8B 1.413(2) . ?
C3B C3B 1.427(3) 3_656 ?
C3B C4B 1.4204(18) . ?
C4B C5B 1.4298(19) . ?
C4B C6B 1.394(2) . ?
C5B C1B 1.345(2) 3_656 ?
C5B H5B 1.0770 . ?
C6B H6B 1.0770 . ?
C6B C7B 1.383(2) . ?
C7B H7B 1.0770 . ?
C7B C8B 1.399(2) . ?
C8B C9B 1.497(2) . ?
C9B C10B 1.501(2) . ?
C10B H10D 1.0831 . ?
C10B H10E 1.0831 . ?
C10B H10F 1.0831 . ?

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
C2A C1A H1A 118.1 . . ?
C5A C1A H1A 118.1 3_666 . ?
C5A C1A C2A 123.86(15) 3_666 . ?
C3A C2A C1A 115.89(14) . . ?
C3A C2A C8A 118.60(13) . . ?
C8A C2A C1A 125.51(15) . . ?
C2A C3A C3A 120.59(16) . 3_666 ?
C4A C3A C2A 120.40(15) . . ?
C4A C3A C3A 119.00(17) . 3_666 ?
C3A C4A C5A 119.49(15) . . ?
C6A C4A C3A 119.32(15) . . ?
C6A C4A C5A 121.18(14) . . ?
C1A C5A C4A 121.15(14) 3_666 . ?
C1A C5A H5A 119.4 3_666 . ?
C4A C5A H5A 119.4 . . ?
C4A C6A H6A 119.7 . . ?
C7A C6A C4A 120.55(14) . . ?
C7A C6A H6A 119.7 . . ?
C6A C7A H7A 119.1 . . ?
C6A C7A C8A 121.78(16) . . ?
C8A C7A H7A 119.1 . . ?
C2A C8A C9A 122.71(14) . . ?
C7A C8A C2A 119.33(15) . . ?
C7A C8A C9A 117.97(16) . . ?
O1A C9A C8A 123.38(18) . . ?
O1A C9A C10A 116.4(2) . . ?
C10A C9A C8A 120.18(19) . . ?
C9A C10A H10A 109.5 . . ?
C9A C10A H10B 109.5 . . ?
C9A C10A H10C 109.5 . . ?
H10A C10A H10B 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
C2B C1B H1B 119.3 . . ?
C5B C1B H1B 119.3 3_656 . ?
C5B C1B C2B 121.34(12) 3_656 . ?
C3B C2B C1B 117.77(13) . . ?
C8B C2B C1B 123.37(12) . . ?
C8B C2B C3B 118.83(12) . . ?
C3B C3B C2B 120.69(14) 3_656 . ?
C4B C3B C2B 119.94(13) . . ?
C4B C3B C3B 119.37(14) . 3_656 ?
C3B C4B C5B 118.79(13) . . ?
C6B C4B C3B 119.52(12) . . ?
C6B C4B C5B 121.69(12) . . ?
C1B C5B C4B 122.02(12) 3_656 . ?
C1B C5B H5B 119.0 3_656 . ?
C4B C5B H5B 119.0 . . ?
C4B C6B H6B 119.7 . . ?
C7B C6B C4B 120.58(13) . . ?
C7B C6B H6B 119.7 . . ?
C6B C7B H7B 119.4 . . ?
C6B C7B C8B 121.28(14) . . ?
C8B C7B H7B 119.4 . . ?
C2B C8B C9B 122.17(13) . . ?
C7B C8B C2B 119.80(13) . . ?
C7B C8B C9B 117.98(13) . . ?
O1B C9B C8B 122.00(16) . . ?
O1B C9B C10B 119.99(15) . . ?
C8B C9B C10B 118.00(14) . . ?
C9B C10B H10D 109.5 . . ?
C9B C10B H10E 109.5 . . ?
C9B C10B H10F 109.5 . . ?
H10D C10B H10E 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1A C2A C3A C3A 0.4(2) . . . 3_666 ?
C1A C2A C3A C4A -179.49(11) . . . . ?
C1A C2A C8A C7A 178.85(13) . . . . ?
C1A C2A C8A C9A -1.4(2) . . . . ?
C2A C3A C4A C5A -179.81(12) . . . . ?
C2A C3A C4A C6A 0.4(2) . . . . ?
C2A C8A C9A O1A -0.9(3) . . . . ?
C2A C8A C9A C10A 176.1(2) . . . . ?
C3A C2A C8A C7A -1.6(2) . . . . ?
C3A C2A C8A C9A 178.12(13) . . . . ?
C3A C3A C4A C5A 0.3(2) 3_666 . . . ?
C3A C3A C4A C6A -179.45(14) 3_666 . . . ?
C3A C4A C5A C1A 0.1(2) . . . 3_666 ?
C3A C4A C6A C7A -1.1(2) . . . . ?
C4A C6A C7A C8A 0.4(2) . . . . ?
C5A C1A C2A C3A -0.8(2) 3_666 . . . ?
C5A C1A C2A C8A 178.78(14) 3_666 . . . ?
C5A C4A C6A C7A 179.15(14) . . . . ?
C6A C4A C5A C1A 179.82(14) . . . 3_666 ?
C6A C7A C8A C2A 1.0(2) . . . . ?
C6A C7A C8A C9A -178.75(14) . . . . ?
C7A C8A C9A O1A 178.8(2) . . . . ?
C7A C8A C9A C10A -4.2(3) . . . . ?
C8A C2A C3A C3A -179.22(14) . . . 3_666 ?
C8A C2A C3A C4A 0.9(2) . . . . ?
C1B C2B C3B C3B 1.5(2) . . . 3_656 ?
C1B C2B C3B C4B -178.68(11) . . . . ?
C1B C2B C8B C7B 176.68(12) . . . . ?
C1B C2B C8B C9B -5.8(2) . . . . ?
C2B C3B C4B C5B -178.58(11) . . . . ?
C2B C3B C4B C6B 1.41(19) . . . . ?
C2B C8B C9B O1B -34.6(3) . . . . ?
C2B C8B C9B C10B 146.75(16) . . . . ?
C3B C2B C8B C7B -1.0(2) . . . . ?
C3B C2B C8B C9B 176.47(13) . . . . ?
C3B C3B C4B C5B 1.2(2) 3_656 . . . ?
C3B C3B C4B C6B -178.81(14) 3_656 . . . ?
C3B C4B C5B C1B -1.3(2) . . . 3_656 ?
C3B C4B C6B C7B -0.1(2) . . . . ?
C4B C6B C7B C8B -1.9(2) . . . . ?
C5B C1B C2B C3B -1.5(2) 3_656 . . . ?
C5B C1B C2B C8B -179.19(13) 3_656 . . . ?
C5B C4B C6B C7B 179.92(13) . . . . ?
C6B C4B C5B C1B 178.70(13) . . . 3_656 ?
C6B C7B C8B C2B 2.4(2) . . . . ?
C6B C7B C8B C9B -175.18(14) . . . . ?
C7B C8B C9B O1B 142.94(19) . . . . ?
C7B C8B C9B C10B -35.7(2) . . . . ?
C8B C2B C3B C3B 179.36(13) . . . 3_656 ?
C8B C2B C3B C4B -0.85(19) . . . . ?


_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
;
