# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_2bisAP-alpha_340000kPa
_database_code_depnum_ccdc_archive 'CCDC 2039408'
loop_
_audit_author_name
_audit_author_address
'Daniel Tchon'
;Faculty of Chemistry, University of Warsaw
Poland
;
_audit_update_record             
;
2020-10-19 deposited with the CCDC.	2021-01-21 downloaded from the CCDC.
;
_audit_creation_date             2019-08-06
_audit_creation_method           
;
Olex2 1.2
(compiled May 29 2018 13:30:08 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            1,1'-Pyrene-1,8-diyldiethanone
_chemical_name_systematic        1,8-Diacetylpyrene
_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 0.0015 0.0009 '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 0.0056 0.0036 '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                   8.109(3)
_cell_length_b                   22.807(5)
_cell_length_c                   7.27(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.12(11)
_cell_angle_gamma                90
_cell_volume                     1343(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1070
_cell_measurement_temperature    295
_cell_measurement_theta_max      21.8560
_cell_measurement_theta_min      2.0930
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.058
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            'clear greenish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             600
_exptl_crystal_preparation       
'Mounted in a Diamond-Anvil Cell using parabar oil as pressure medium.,Luminescent'
_exptl_crystal_pressure_history  
'Pressurized to 0.34 GPa and left to stabilize over 24 hours.'
_exptl_crystal_recrystallization_method 'from acetonitrile at room temperature'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
High-pressure measurement at 0.34 GPa in a Merill-Basset Diamond Anvil Cell with
effective opening angle of 30 deg. and parabar 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  0.0605
_diffrn_reflns_av_unetI/netI     0.0636
_diffrn_reflns_Laue_measured_fraction_full 0.297
_diffrn_reflns_Laue_measured_fraction_max 0.277
_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       4
_diffrn_reflns_limit_l_min       -3
_diffrn_reflns_number            4077
_diffrn_reflns_point_group_measured_fraction_full 0.297
_diffrn_reflns_point_group_measured_fraction_max 0.277
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         21.062
_diffrn_reflns_theta_min         2.106
_diffrn_ambient_temperature      295
_diffrn_ambient_pressure         340000
_diffrn_ambient_environment      'Diamond Anvil Cell filled with parabar oil'
_diffrn_crystal_treatment        
'Pressurized slowly in parabar oil as a hydrostatic medium.'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0128
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.297
_diffrn_measured_fraction_theta_max 0.277
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -58.00  -5.00   1.00  135.00    --  -18.73  53.00 162.00   53
  1  ω    -58.00  -5.00   1.00  135.0000  --  -18.73  53.00 162.00   53
  2  ω    -23.00  11.00   1.00  135.0000  --  -18.73  53.00 -17.00   34
  3  ω    -61.00 -27.00   1.00  135.0000  --  -18.73 135.00 -57.00   34 
  4  ω     -6.00  20.00   1.00  135.0000  --  -18.73  57.00 150.00   26 
  5  ω     17.00  56.00   1.00  135.0000  --  -18.73-135.00-123.00   39 
  6  ω    -63.00 -37.00   1.00  135.0000  --   18.80 160.00 -90.00   26 
  7  ω     25.00  51.00   1.00  135.0000  --   18.80  19.00-180.00   26 
  8  ω    -42.00  -3.00   1.00  135.0000  --   18.80  19.00-180.00   39 
  9  ω    -35.00  28.00   1.00  135.0000  --   18.80  39.00 -12.00   63 
 10  ω    -17.00   9.00   1.00  135.0000  --   18.80 -57.00-150.00   26 
 11  ω    -73.00   5.00   1.00  135.0000  --  -18.73  97.00 -35.00   78 
 12  ω    -35.00   2.00   1.00  135.0000  --   18.80  97.00 -35.00   37 
 13  ω    -27.00   2.00   1.00  135.0000  --   18.80  81.00 151.00   29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 
'Diamond Anvil Cell, effective opening angle of 30 deg.'
_diffrn_orient_matrix_UB_11      -0.0195096000
_diffrn_orient_matrix_UB_12      0.0020779000
_diffrn_orient_matrix_UB_13      -0.0748004000
_diffrn_orient_matrix_UB_21      0.0253526000
_diffrn_orient_matrix_UB_22      0.0227843000
_diffrn_orient_matrix_UB_23      -0.0003067000
_diffrn_orient_matrix_UB_31      0.0612384000
_diffrn_orient_matrix_UB_32      -0.0087733000
_diffrn_orient_matrix_UB_33      -0.0187067000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56087
_diffrn_source                   'SuperNova (Ag) X-ray Source'
_diffrn_special_details          
'High Pressure experiment in a Diamond Anvil Cell, opening angle 30 degrees.'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                611
_reflns_number_total             821
_reflns_odcompleteness_completeness 27.45
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     21.01
_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 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_computing_data_collection       
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.175
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         821
_refine_ls_number_restraints     165
_refine_ls_R_factor_all          0.1399
_refine_ls_R_factor_gt           0.0971
_refine_ls_restrained_S_all      1.064
_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)+(0.0839P)²+1.8475P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2045
_refine_ls_wR_factor_ref         0.2272
_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. Uiso/Uaniso restraints and constraints
Uanis(C16) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.05
3. Rigid body (RIGU) restrains
 C3, C2, C1, C14, C13, C12, C11, C15, C17, C4, C5, C6, C7, C8, C9, C10, C16, C19
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C14(H14), C13(H13), C11(H11), C4(H4), C8(H8), C7(H7), C10(H10)
4.b Fitted hexagon refined as free rotating group:
 C1(C14,C13,C12,C15,C2), C5(C16,C9,C8,C7,C6)
4.c Idealised Me refined as rotating group:
 C18(H18B,H18A,H18C), C20(H20B,H20A,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5962(7) 0.2480(2) -0.061(2) 0.068(13) Uani 1 1 d . . . . .
O2 O 0.5767(7) 0.52180(19) 0.251(2) 0.103(13) Uani 1 1 d . . . . .
C3 C 0.7133(10) 0.3579(3) 0.086(3) 0.042(7) Uani 1 1 d . U . . .
H3 H 0.6171 0.3405 0.0363 0.051 Uiso 1 1 calc R . . . .
C1 C 0.8614(5) 0.26164(17) 0.0964(16) 0.039(7) Uani 1 1 d . U . . .
C14 C 1.0077(6) 0.23029(13) 0.1232(18) 0.048(8) Uani 1 1 d G U . . .
H14 H 1.0084 0.1899 0.1048 0.058 Uiso 1 1 calc R . . . .
C13 C 1.1532(5) 0.25924(15) 0.1776(17) 0.047(8) Uani 1 1 d G U . . .
H13 H 1.2511 0.2383 0.1955 0.057 Uiso 1 1 calc R . . . .
C12 C 1.1523(5) 0.31954(17) 0.2052(15) 0.038(7) Uani 1 1 d G U . . .
C15 C 1.0059(5) 0.35090(12) 0.1783(16) 0.030(7) Uani 1 1 d G U . . .
C2 C 0.8605(4) 0.32195(15) 0.1240(16) 0.030(7) Uani 1 1 d G U . . .
C11 C 1.3034(10) 0.3495(3) 0.274(3) 0.042(7) Uani 1 1 d . U . . .
H11 H 1.3990 0.3281 0.3018 0.050 Uiso 1 1 calc R . . . .
C17 C 0.7103(11) 0.2266(3) 0.027(3) 0.044(8) Uani 1 1 d . U . . .
C18 C 0.7060(13) 0.1620(3) 0.088(3) 0.070(19) Uani 1 1 d . . . . .
H18B H 0.5948 0.1476 0.0737 0.106 Uiso 1 1 calc GR . . . .
H18A H 0.7448 0.1590 0.2143 0.106 Uiso 1 1 calc GR . . . .
H18C H 0.7757 0.1392 0.0127 0.106 Uiso 1 1 calc GR . . . .
C4 C 0.7152(10) 0.4157(3) 0.122(3) 0.039(7) Uani 1 1 d . U . . .
H4 H 0.6180 0.4369 0.1004 0.046 Uiso 1 1 calc R . . . .
C5 C 0.8600(5) 0.44638(16) 0.1912(16) 0.035(7) Uani 1 1 d . U . . .
C16 C 1.0048(5) 0.41381(12) 0.2105(17) 0.027(6) Uani 1 1 d G U . . .
C9 C 1.1534(5) 0.44139(15) 0.2606(17) 0.041(7) Uani 1 1 d G U . . .
C8 C 1.1571(5) 0.50154(18) 0.2915(16) 0.046(8) Uani 1 1 d G U . . .
H8 H 1.2565 0.5200 0.3250 0.056 Uiso 1 1 calc R . . . .
C7 C 1.0123(5) 0.53410(13) 0.2722(17) 0.035(8) Uani 1 1 d G U . . .
H7 H 1.0149 0.5743 0.2928 0.042 Uiso 1 1 calc R . . . .
C6 C 0.8638(5) 0.50652(14) 0.2220(17) 0.032(8) Uani 1 1 d G U . . .
C10 C 1.3036(10) 0.4070(3) 0.296(3) 0.037(7) Uani 1 1 d . U . . .
H10 H 1.4011 0.4259 0.3343 0.045 Uiso 1 1 calc R . . . .
C19 C 0.7085(10) 0.5424(3) 0.231(3) 0.056(12) Uani 1 1 d . U . . .
C20 C 0.7225(15) 0.6085(3) 0.213(3) 0.056(18) Uani 1 1 d . . . . .
H20B H 0.6182 0.6243 0.1680 0.083 Uiso 1 1 calc GR . . . .
H20A H 0.8054 0.6178 0.1283 0.083 Uiso 1 1 calc GR . . . .
H20C H 0.7526 0.6251 0.3312 0.083 Uiso 1 1 calc GR . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.048(4) 0.047(3) 0.11(4) 0.001(6) -0.011(12) -0.002(3)
O2 0.035(4) 0.047(3) 0.23(4) -0.013(5) 0.033(13) -0.004(2)
C3 0.024(4) 0.043(3) 0.06(2) -0.003(5) -0.003(7) -0.001(2)
C1 0.034(4) 0.040(3) 0.04(2) -0.002(5) 0.001(7) -0.001(2)
C14 0.040(4) 0.044(3) 0.06(2) 0.001(6) 0.001(7) 0.000(3)
C13 0.033(4) 0.041(3) 0.07(2) 0.003(5) 0.000(7) 0.009(2)
C12 0.026(3) 0.044(3) 0.04(2) 0.009(5) -0.002(6) 0.004(2)
C15 0.024(3) 0.038(3) 0.03(2) 0.005(4) 0.000(6) -0.002(2)
C2 0.028(3) 0.040(3) 0.02(2) 0.001(4) 0.003(6) -0.002(2)
C11 0.029(4) 0.057(3) 0.04(2) 0.006(5) 0.002(7) 0.001(3)
C17 0.037(4) 0.041(4) 0.05(2) -0.018(7) 0.006(8) -0.002(3)
C18 0.064(7) 0.037(4) 0.11(6) -0.014(7) 0.032(19) -0.015(4)
C4 0.026(4) 0.043(3) 0.05(2) 0.005(5) -0.009(7) 0.003(3)
C5 0.026(3) 0.039(3) 0.04(2) 0.004(4) -0.004(6) -0.002(2)
C16 0.025(3) 0.041(3) 0.016(17) 0.006(4) 0.002(6) -0.001(2)
C9 0.026(4) 0.046(3) 0.05(2) 0.002(5) -0.004(6) -0.005(2)
C8 0.030(4) 0.046(3) 0.06(3) 0.005(5) -0.006(7) -0.009(3)
C7 0.033(4) 0.039(3) 0.03(3) 0.006(5) -0.001(7) -0.005(3)
C6 0.032(4) 0.038(3) 0.03(2) 0.005(5) 0.000(7) -0.002(2)
C10 0.025(4) 0.053(3) 0.03(2) 0.007(5) -0.001(7) -0.005(3)
C19 0.041(4) 0.033(3) 0.09(4) 0.002(6) 0.002(10) 0.003(3)
C20 0.049(7) 0.044(4) 0.07(5) 0.005(8) 0.010(18) 0.006(4)

_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 1.199(18) . ?
O2 C19 1.185(7) . ?
C3 C2 1.462(10) . ?
C3 C4 1.344(10) . ?
C1 C14 1.3900 . ?
C1 C2 1.3900 . ?
C1 C17 1.526(13) . ?
C14 C13 1.3900 . ?
C13 C12 1.3900 . ?
C12 C15 1.3900 . ?
C12 C11 1.467(14) . ?
C15 C2 1.3900 . ?
C15 C16 1.454(4) . ?
C11 C10 1.320(9) . ?
C17 C18 1.537(12) . ?
C4 C5 1.435(13) . ?
C5 C16 1.3900 . ?
C5 C6 1.3900 . ?
C16 C9 1.3900 . ?
C9 C8 1.3900 . ?
C9 C10 1.460(11) . ?
C8 C7 1.3900 . ?
C7 C6 1.3900 . ?
C6 C19 1.505(7) . ?
C19 C20 1.518(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 C3 C2 120.9(11) . . ?
C14 C1 C2 120.0 . . ?
C14 C1 C17 116.1(4) . . ?
C2 C1 C17 123.8(4) . . ?
C1 C14 C13 120.0 . . ?
C12 C13 C14 120.0 . . ?
C13 C12 C15 120.0 . . ?
C13 C12 C11 120.0(4) . . ?
C15 C12 C11 119.9(4) . . ?
C12 C15 C16 119.9(4) . . ?
C2 C15 C12 120.0 . . ?
C2 C15 C16 120.1(3) . . ?
C1 C2 C3 122.6(5) . . ?
C15 C2 C3 117.3(4) . . ?
C15 C2 C1 120.0 . . ?
C10 C11 C12 120.0(9) . . ?
O1 C17 C1 123.0(7) . . ?
O1 C17 C18 120.9(10) . . ?
C1 C17 C18 115.9(13) . . ?
C3 C4 C5 123.1(8) . . ?
C16 C5 C4 116.5(4) . . ?
C16 C5 C6 120.0 . . ?
C6 C5 C4 123.2(4) . . ?
C5 C16 C15 121.6(4) . . ?
C9 C16 C15 118.4(4) . . ?
C9 C16 C5 120.0 . . ?
C16 C9 C8 120.0 . . ?
C16 C9 C10 120.4(5) . . ?
C8 C9 C10 119.4(5) . . ?
C9 C8 C7 120.0 . . ?
C6 C7 C8 120.0 . . ?
C5 C6 C19 122.1(4) . . ?
C7 C6 C5 120.0 . . ?
C7 C6 C19 117.3(5) . . ?
C11 C10 C9 121.1(10) . . ?
O2 C19 C6 123.5(5) . . ?
O2 C19 C20 118.4(6) . . ?
C6 C19 C20 118.0(6) . . ?

_iucr_refine_instructions_details 
;
TITL v1_abs in P21/c #14
REM reset to P21/c #14
CELL 0.56087 8.108813 22.806588 7.274526 90 93.1212 90
ZERR 4 0.003052 0.004774 0.020414 0 0.1117 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H O
UNIT 80 56 8
RIGU C3 C2 C1 C14 C13 C12 C11 C15 C17 C4 C5 C6 C7 C8 C9 C10 C16 C19
ISOR 0.02 0.05 C16
 
L.S. 4
PLAN  2
BOND
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%./v1_abs.hkl">
REM </olex2.extras>
 
WGHT    0.083900    1.847500
FVAR       2.18699
O1    3    0.596241    0.247968   -0.060824    11.00000    0.04772    0.04716 =
         0.10863    0.00133   -0.01061   -0.00202
O2    3    0.576691    0.521803    0.251376    11.00000    0.03490    0.04696 =
         0.22920   -0.01349    0.03267   -0.00416
C3    1    0.713297    0.357896    0.085917    11.00000    0.02425    0.04335 =
         0.05920   -0.00283   -0.00326   -0.00066
AFIX  43
H3    2    0.617102    0.340529    0.036310    11.00000   -1.20000
AFIX  66
C1    1    0.861416    0.261642    0.096391    11.00000    0.03361    0.04041 =
         0.04138   -0.00235    0.00105   -0.00147
C14    1    1.007744    0.230287    0.123202    11.00000    0.03996    0.04410 =
         0.06007    0.00093    0.00103    0.00000
AFIX  43
H14    2    1.008353    0.189939    0.104754    11.00000   -1.20000
AFIX  65
C13    1    1.153161    0.259238    0.177584    11.00000    0.03339    0.04120 =
         0.06673    0.00325    0.00043    0.00910
AFIX  43
H13    2    1.251064    0.238260    0.195522    11.00000   -1.20000
AFIX  65
C12    1    1.152252    0.319544    0.205157    11.00000    0.02625    0.04389 =
         0.04296    0.00928   -0.00152    0.00391
C15    1    1.005925    0.350899    0.178347    11.00000    0.02381    0.03830 =
         0.02636    0.00451    0.00044   -0.00200
C2    1    0.860506    0.321949    0.123965    11.00000    0.02807    0.03982 =
         0.02188    0.00076    0.00325   -0.00233
AFIX   0
C11    1    1.303357    0.349524    0.273810    11.00000    0.02869    0.05741 =
         0.03867    0.00581    0.00164    0.00096
AFIX  43
H11    2    1.398953    0.328059    0.301836    11.00000   -1.20000
AFIX   0
C17    1    0.710294    0.226565    0.027001    11.00000    0.03714    0.04103 =
         0.05299   -0.01837    0.00626   -0.00189
C18   1    0.705998    0.162030    0.087597    11.00000    0.06368    0.03743 =
         0.11330   -0.01366    0.03191   -0.01538
AFIX 137
H18B  2    0.594786    0.147617    0.073660    11.00000   -1.50000
H18A  2    0.744785    0.158977    0.214290    11.00000   -1.50000
H18C  2    0.775741    0.139195    0.012681    11.00000   -1.50000
AFIX   0
C4   1    0.715194    0.415730    0.121714    11.00000    0.02598    0.04297 =
         0.04575    0.00549   -0.00912    0.00264
AFIX  43
H4   2    0.617977    0.436884    0.100416    11.00000   -1.20000
AFIX  66
C5   1    0.860000    0.446378    0.191194    11.00000    0.02611    0.03878 =
         0.03899    0.00434   -0.00447   -0.00215
C16   1    1.004802    0.413812    0.210491    11.00000    0.02511    0.04054 =
         0.01644    0.00615    0.00157   -0.00095
C9   1    1.153369    0.441391    0.260630    11.00000    0.02640    0.04616 =
         0.05064    0.00165   -0.00398   -0.00512
C8   1    1.157133    0.501536    0.291472    11.00000    0.02984    0.04615 =
         0.06224    0.00505   -0.00626   -0.00895
AFIX  43
H8   2    1.256534    0.519988    0.325018    11.00000   -1.20000
AFIX  65
C7   1    1.012331    0.534102    0.272175    11.00000    0.03350    0.03906 =
         0.03102    0.00579   -0.00131   -0.00481
AFIX  43
H7   2    1.014850    0.574344    0.292810    11.00000   -1.20000
AFIX  65
C6   1    0.863764    0.506524    0.222036    11.00000    0.03237    0.03768 =
         0.02536    0.00468   -0.00020   -0.00166
AFIX   0
C10   1    1.303623    0.406991    0.295808    11.00000    0.02487    0.05326 =
         0.03369    0.00747   -0.00087   -0.00484
AFIX  43
H10   2    1.401128    0.425866    0.334347    11.00000   -1.20000
AFIX   0
C19   1    0.708550    0.542381    0.230652    11.00000    0.04064    0.03317 =
         0.09467    0.00234    0.00175    0.00250
C20   1    0.722457    0.608475    0.212877    11.00000    0.04874    0.04446 =
         0.07422    0.00498    0.00954    0.00561
AFIX 137
H20B  2    0.618157    0.624262    0.167956    11.00000   -1.50000
H20A  2    0.805392    0.617834    0.128279    11.00000   -1.50000
H20C  2    0.752619    0.625139    0.331150    11.00000   -1.50000
AFIX   0
HKLF 4
 
REM  v1_abs in P21/c #14
REM R1 =  0.0971 for     611 Fo > 4sig(Fo)  and  0.1399 for all     821 data
REM    177 parameters refined using    165 restraints
 
END  
     
WGHT      0.0841      1.8497 

REM Highest difference peak  0.159,  deepest hole -0.128,  1-sigma level  0.034
Q1    1   0.8212  0.5190  0.2390  11.00000  0.05    0.16
Q2    1   1.0957  0.5214  0.3235  11.00000  0.05    0.12

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0971 for 611 Fo > 4sig(Fo) and 0.1399 for all 4126 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.16, deepest hole -0.13
  REM Mean Shift 0, Max Shift -0.001.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.1399
  REM R1_gt = 0.0971
  REM wR_ref = 0.2272
  REM GOOF = 1.175
  REM Shift_max = -0.001
  REM Shift_mean = 0
  REM Reflections_all = 4126
  REM Reflections_gt = 611
  REM Parameters = n/a
  REM Hole = -0.13
  REM Peak = 0.16
  REM Flack = n/a

  
;
_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT029_2bisAP-alpha_340000kPa 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.297 Why?  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
;
_vrf_PLAT088_2bisAP-alpha_340000kPa 
;
PROBLEM: Poor Data / Parameter Ratio ....................       4.64 Note  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
;
_vrf_PLAT149_2bisAP-alpha_340000kPa 
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.11 Degree
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC, and in 
particular affected the beta angle due to crystal orientation.
;
_vrf_PLAT911_2bisAP-alpha_340000kPa 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L= 0.600           995 Report
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
;
_vrf_PLAT148_2bisAP-alpha_340000kPa 
;
PROBLEM: s.u. on the      c    - Axis is (Too) Large ....      0.020 Ang.  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC, and in 
particular affected the c direction due to crystal orientation.
;
_vrf_PLAT242_2bisAP-alpha_340000kPa 
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of         C17 Check 
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC, 
resulting in a less precise model.
;
_vrf_PLAT340_2bisAP-alpha_340000kPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0093 Ang.  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC, 
resulting in a less precise model.
;
_vrf_PLAT369_2bisAP-alpha_340000kPa 
;
PROBLEM: Long   C(sp2)-C(sp2) Bond  C1       - C17       .       1.53 Ang.  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC, 
resulting in a less precise model.
;
_vrf_PLAT906_2bisAP-alpha_340000kPa 
;
PROBLEM: Large K Value in the Analysis of Variance ......     37.290 Check 
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. Highest resolution data might be affected 
by gasket shadowing and therefore very week.
;
_vrf_PLAT913_2bisAP-alpha_340000kPa 
;
PROBLEM: Missing # of Very Strong Reflections in FCF ....          7 Note  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC, and in 
particular affected the c direction due to crystal orientation.
;
# 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_2bisAP-beta_1290000kPa
_database_code_depnum_ccdc_archive 'CCDC 2039411'
loop_
_audit_author_name
_audit_author_address
'Daniel Tchon'
;Faculty of Chemistry, University of Warsaw
Poland
;
_audit_update_record             
;
2020-10-19 deposited with the CCDC.	2021-01-21 downloaded from the CCDC.
;
_audit_creation_date             2020-03-20
_audit_creation_method           
;
Olex2 1.2
(compiled May 29 2018 13:30:08 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            1,1'-Pyrene-1,8-diyldiethanone
_chemical_name_systematic        1,8-Diacetylpyrene
_chemical_formula_moiety         'C20 H14 O2'
_chemical_formula_sum            'C20 H14 O2'
_chemical_formula_weight         286.31
_chemical_absolute_configuration ad
_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      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   4.5691(17)
_cell_length_b                   34.74(9)
_cell_length_c                   15.984(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2537(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    264
_cell_measurement_temperature    291.3(3)
_cell_measurement_theta_max      26.3980
_cell_measurement_theta_min      2.8040
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80931
_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 dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1200
_exptl_crystal_preparation       
'Mounted in a Diamond-Anvil Cell using parabar oil as pressure medium.,Luminescent'
_exptl_crystal_pressure_history  
'Pressurized to 1.29 GPa and left to stabilize over 24 hours.'
_exptl_crystal_recrystallization_method 'from chloroform at room temperature'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
High-pressure measurement at 1.29 GPa in a Merill-Basset Diamond Anvil Cell with
effective opening angle of 50 deg. and parabar 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  0.1272
_diffrn_reflns_av_unetI/netI     0.1364
_diffrn_reflns_Laue_measured_fraction_full 0.495
_diffrn_reflns_Laue_measured_fraction_max 0.493
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            1540
_diffrn_reflns_point_group_measured_fraction_full 0.463
_diffrn_reflns_point_group_measured_fraction_max 0.458
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.631
_diffrn_reflns_theta_min         2.805
_diffrn_ambient_temperature      291.3(3)
_diffrn_ambient_pressure         1290000
_diffrn_ambient_environment      'Diamond Anvil Cell filled with parabar oil'
_diffrn_crystal_treatment        
'Pressurized slowly in parabar oil as a hydrostatic medium.'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4391
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.495
_diffrn_measured_fraction_theta_max 0.493
_diffrn_measurement_details      
'List of Runs (angles in degrees, time in seconds): # Type Start End Width tₑₓₚ ω θ κ φ Frames -------------------------------------------------------------------------- 1 ω -25.00 0.00 1.00 130.00 -- 9.85 -37.00-120.00 25 2 ω -35.00 -9.00 1.00 130.00 -- 9.85 -19.00-120.00 26 3 ω -26.00 7.00 1.00 130.00 -- 9.85 19.00 30.00 33 4 ω 4.00 30.00 1.00 130.00 -- 9.85 56.00 161.00 26 5 ω -13.00 19.00 1.00 130.00 -- 9.85 -81.00-151.00 32 6 ω -20.00 5.00 1.00 130.00 -- 9.85 26.00 -7.00 25 7 ω -52.00 -26.00 1.00 130.00 -- -11.72 19.00 30.00 26 8 ω -65.00 -39.00 1.00 130.00 -- -11.72 134.00 123.00 26'
_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_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0011593000
_diffrn_orient_matrix_UB_12      -0.0205085000
_diffrn_orient_matrix_UB_13      0.0015724000
_diffrn_orient_matrix_UB_21      0.1108171000
_diffrn_orient_matrix_UB_22      0.0003305000
_diffrn_orient_matrix_UB_23      0.0308121000
_diffrn_orient_matrix_UB_31      -0.1080203000
_diffrn_orient_matrix_UB_32      0.0005454000
_diffrn_orient_matrix_UB_33      0.0317912000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\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         0.792
_reflns_Friedel_fraction_full    0.428
_reflns_Friedel_fraction_max     0.420
_reflns_number_gt                244
_reflns_number_total             552
_reflns_odcompleteness_completeness 47.17
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.63
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details .
_refine_ls_abs_structure_Flack   .
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         552
_refine_ls_number_restraints     79
_refine_ls_R_factor_all          0.1685
_refine_ls_R_factor_gt           0.0580
_refine_ls_restrained_S_all      0.940
_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)+(0.0543P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.1735
_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
 O1, C15, C2, C12, C1, C3, C13, C11, C14, C17, C18
 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:
 C13(H13), C3(H3), C11(H11), C14(H14)
3.b Idealised Me refined as rotating group:
 C18(H18C,H18B,H18A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C15 C 0.398(2) 0.4866(8) 0.4075(7) 0.040(6) Uani 1 1 d . U . . .
C2 C 0.291(3) 0.4690(7) 0.3315(7) 0.046(6) Uani 1 1 d . U . . .
C12 C 0.287(3) 0.4696(9) 0.4853(8) 0.048(6) Uani 1 1 d . U . . .
C1 C 0.086(2) 0.4392(9) 0.3344(9) 0.044(5) Uani 1 1 d . U . . .
C13 C 0.081(3) 0.4409(10) 0.4860(8) 0.054(7) Uani 1 1 d . U . . .
H13 H 0.0091 0.4318 0.5368 0.065 Uiso 1 1 calc R . . . .
C3 C 0.405(3) 0.4843(9) 0.2560(6) 0.047(8) Uani 1 1 d . U . . .
H3 H 0.3529 0.4731 0.2053 0.057 Uiso 1 1 calc R . . . .
C11 C 0.398(3) 0.4850(10) 0.5606(7) 0.051(9) Uani 1 1 d . U . . .
H11 H 0.3339 0.4750 0.6114 0.061 Uiso 1 1 calc R . . . .
C14 C -0.023(3) 0.4251(8) 0.4114(9) 0.058(6) Uani 1 1 d . U . . .
H14 H -0.1621 0.4056 0.4122 0.069 Uiso 1 1 calc R . . . .
C17 C -0.020(3) 0.4172(10) 0.2582(10) 0.057(7) Uani 1 1 d . U . . .
C18 C -0.268(3) 0.3885(10) 0.2663(10) 0.066(8) Uani 1 1 d . U . . .
H18C H -0.1949 0.3649 0.2898 0.100 Uiso 1 1 calc GR . . . .
H18B H -0.3497 0.3834 0.2120 0.100 Uiso 1 1 calc GR . . . .
H18A H -0.4172 0.3988 0.3022 0.100 Uiso 1 1 calc GR . . . .
O1 O 0.101(2) 0.4214(7) 0.1894(6) 0.074(9) Uani 1 1 d . U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C15 0.034(7) 0.051(17) 0.036(4) 0.002(6) 0.001(5) 0.011(9)
C2 0.044(8) 0.056(17) 0.038(5) 0.003(7) -0.001(5) -0.004(9)
C12 0.047(8) 0.057(19) 0.039(5) 0.006(7) 0.005(5) 0.008(9)
C1 0.036(6) 0.043(17) 0.051(5) 0.000(7) -0.001(5) 0.009(8)
C13 0.055(8) 0.05(2) 0.053(7) 0.002(8) 0.009(6) 0.011(9)
C3 0.063(10) 0.05(3) 0.032(6) -0.002(8) -0.002(6) -0.003(10)
C11 0.067(11) 0.05(3) 0.036(6) 0.007(7) 0.009(6) 0.013(11)
C14 0.046(7) 0.062(19) 0.064(6) 0.004(8) 0.007(6) -0.003(9)
C17 0.051(7) 0.05(2) 0.066(6) -0.005(8) -0.012(6) 0.003(9)
C18 0.056(7) 0.05(2) 0.092(11) -0.011(11) -0.010(8) 0.003(11)
O1 0.094(7) 0.07(3) 0.059(5) -0.008(7) -0.011(5) -0.014(10)

_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
C15 C15 1.32(4) 2_665 ?
C15 C2 1.446(19) . ?
C15 C12 1.47(2) . ?
C2 C1 1.40(3) . ?
C2 C3 1.42(2) . ?
C12 C13 1.37(3) . ?
C12 C11 1.41(2) . ?
C1 C14 1.41(2) . ?
C1 C17 1.52(3) . ?
C13 C14 1.40(3) . ?
C3 C3 1.39(5) 2_665 ?
C11 C11 1.40(5) 2_665 ?
C17 C18 1.52(4) . ?
C17 O1 1.240(19) . ?

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
C15 C15 C2 122.6(8) 2_665 . ?
C15 C15 C12 122.0(11) 2_665 . ?
C2 C15 C12 115.2(16) . . ?
C1 C2 C15 120.9(14) . . ?
C1 C2 C3 123.6(14) . . ?
C3 C2 C15 115.6(16) . . ?
C13 C12 C15 122.5(15) . . ?
C13 C12 C11 120.9(15) . . ?
C11 C12 C15 116.5(19) . . ?
C2 C1 C14 121.4(17) . . ?
C2 C1 C17 124.1(14) . . ?
C14 C1 C17 114.3(18) . . ?
C12 C13 C14 120.7(17) . . ?
C3 C3 C2 121.5(12) 2_665 . ?
C11 C11 C12 121.4(12) 2_665 . ?
C13 C14 C1 119(2) . . ?
C1 C17 C18 120.2(15) . . ?
O1 C17 C1 120.8(19) . . ?
O1 C17 C18 119.0(19) . . ?

_iucr_refine_instructions_details 
;
TITL p2_v1 in Fdd2 #43
REM reset to Fdd2 #43
CELL 0.71073 4.569052 34.744728 15.983655 90 90 90
ZERR 8 0.001669 0.094628 0.005398 0 0 0
LATT -4
SYMM -X,-Y,+Z
SYMM 0.25-X,0.25+Y,0.25+Z
SYMM 0.25+X,0.25-Y,0.25+Z
SFAC C H O
UNIT 160 112 16
RIGU O1 C15 C2 C12 C1 C3 C13 C11 C14 C17 C18
 
L.S. 4
PLAN  2
SIZE 0.06 0.18 0.24
BOND
fmap 2
ACTA
REM <olex2.extras>
REM <HklSrc "%./p2_v1.hkl">
REM </olex2.extras>
 
WGHT    0.054300
FVAR       0.56499
C15    1    0.398304    0.486566    0.407536    11.00000    0.03423    0.05054 =
         0.03641    0.00213    0.00093    0.01083
C2    1    0.290715    0.468999    0.331494    11.00000    0.04379    0.05641 =
         0.03845    0.00287   -0.00072   -0.00353
C12    1    0.287207    0.469608    0.485265    11.00000    0.04704    0.05668 =
         0.03926    0.00606    0.00530    0.00801
C1    1    0.086038    0.439185    0.334363    11.00000    0.03639    0.04335 =
         0.05134   -0.00035   -0.00089    0.00899
C13    1    0.080641    0.440875    0.486025    11.00000    0.05461    0.05445 =
         0.05273    0.00229    0.00921    0.01081
AFIX  43
H13    2    0.009094    0.431830    0.536824    11.00000   -1.20000
AFIX   0
C3    1    0.405355    0.484288    0.255962    11.00000    0.06273    0.04682 =
         0.03211   -0.00229   -0.00192   -0.00332
AFIX  43
H3    2    0.352889    0.473070    0.205309    11.00000   -1.20000
AFIX   0
C11    1    0.398007    0.485006    0.560614    11.00000    0.06679    0.05020 =
         0.03619    0.00654    0.00857    0.01255
AFIX  43
H11    2    0.333907    0.474981    0.611356    11.00000   -1.20000
AFIX   0
C14    1   -0.022933    0.425121    0.411382    11.00000    0.04644    0.06225 =
         0.06428    0.00415    0.00666   -0.00275
AFIX  43
H14    2   -0.162075    0.405589    0.412245    11.00000   -1.20000
AFIX   0
C17    1   -0.019991    0.417215    0.258231    11.00000    0.05121    0.05452 =
         0.06612   -0.00477   -0.01167    0.00263
C18   1   -0.268233    0.388457    0.266298    11.00000    0.05588    0.05132 =
         0.09215   -0.01076   -0.00995    0.00293
AFIX 137
H18C  2   -0.194941    0.364928    0.289802    11.00000   -1.50000
H18B  2   -0.349693    0.383412    0.212032    11.00000   -1.50000
H18A  2   -0.417153    0.398833    0.302165    11.00000   -1.50000
AFIX   0
O1   3    0.100984    0.421371    0.189358    11.00000    0.09397    0.06930 =
         0.05863   -0.00781   -0.01107   -0.01383
HKLF 4
 
REM  p2_v1 in Fdd2 #43
REM R1 =  0.0580 for     244 Fo > 4sig(Fo)  and  0.1685 for all     552 data
REM    101 parameters refined using     79 restraints
 
END  
     
WGHT      0.0543      0.0000 

REM Highest difference peak  0.137,  deepest hole -0.154,  1-sigma level  0.040
Q1    1   0.6344  0.4672  0.5496  11.00000  0.05    0.14
Q2    1  -0.4591  0.4139  0.2822  11.00000  0.05    0.12

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0580 for 244 Fo > 4sig(Fo) and 0.1685 for all 1632 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.14, deepest hole -0.15
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.1685
  REM R1_gt = 0.0580
  REM wR_ref = 0.1735
  REM GOOF = 0.987
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 1632
  REM Reflections_gt = 244
  REM Parameters = n/a
  REM Hole = -0.15
  REM Peak = 0.14
  REM Flack = -3.7(10)

  
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
'Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling'
_oxdiff_exptl_absorpt_empirical_full_max 2.177
_oxdiff_exptl_absorpt_empirical_full_min 0.731

# start Validation Reply Form
_vrf_PLAT340_2bisAP-beta_1290000kPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02923 Ang. 
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 50 degrees on a very thin plate. This limited the number
of reflections that could be collected, as most of them were obscured by the
DAC, which together with weak scattering negatively affected the precision.
;
_vrf_PLAT911_2bisAP-beta_1290000kPa 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L= 0.600            55 Report
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 50 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
;
_vrf_PLAT915_2bisAP-beta_1290000kPa 
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         42 % 
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 50 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
Moreover, high Friedel pair coverage was unnecessary, as space group information
was determined using complete dataset gathered on this sample before experiment. 
;
_vrf_RINTA01_2bisAP-beta_1290000kPa 
;
PROBLEM: The value of Rint is greater than 0.12
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 50 degrees. This limited the number of reflections
that could be collected, as most of them were obscured by the DAC.
This, and relatively weak scattering, affected the precission of the final
intensities.
;
_vrf_PLAT029_2bisAP-beta_1290000kPa 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.495 Why?  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 50 degrees on a very thin plate. This limited the number
of reflections that could be collected, as most of them were obscured
by the DAC.
;
_vrf_PLAT089_2bisAP-beta_1290000kPa 
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       3.05 Note  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 50 degrees on a very thin plate. This limited the number
of reflections that could be collected, as most of them were obscured
by the DAC.
;
_vrf_PLAT026_2bisAP-beta_1290000kPa 
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        44% Check 
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 50 degrees on a very thin plate. This limited the number
of reflections that could be collected, as most of them were obscured
by the DAC.
;
_vrf_PLAT148_2bisAP-beta_1290000kPa 
;
PROBLEM: s.u. on the      b    - Axis is (Too) Large ....     0.0900 Ang.  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 50 degrees on a very thin plate. This limited the number
of reflections that could be collected, as most of them were obscured
by the DAC. b direction, perpendicular to the plate large face was particularly
affected due to crystal orientation.
;
_vrf_PLAT905_2bisAP-beta_1290000kPa 
;
PROBLEM: Negative K value in the Analysis of Variance ...     -1.907 Report
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 50 degrees. This limited the number of reflections
that could be collected, as most of them were obscured by the DAC.
This, and relatively weak scattering, affected the precission of the final
intensities.
;
_vrf_PLAT978_2bisAP-beta_1290000kPa 
;
PROBLEM: Number C-C Bonds with Positive Residual Density.          0 Info  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 50 degrees. This limited the number of reflections
that could be collected, as most of them were obscured by the DAC.
This, and relatively weak scattering, affected the precission of the final
model.
;
# 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_2bisAP-beta_1000000kPa
_database_code_depnum_ccdc_archive 'CCDC 2039412'
loop_
_audit_author_name
_audit_author_address
'Daniel Tchon'
;Faculty of Chemistry, University of Warsaw
Poland
;
_audit_update_record             
;
2020-10-19 deposited with the CCDC.	2021-01-21 downloaded from the CCDC.
;
_audit_creation_date             2019-08-06
_audit_creation_method           
;
Olex2 1.2
(compiled May 29 2018 13:30:08 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            1,1'-Pyrene-1,8-diyldiethanone
_chemical_name_systematic        1,8-Diacetylpyrene
_chemical_formula_moiety         'C20 H14 O2'
_chemical_formula_sum            'C20 H14 O2'
_chemical_formula_weight         286.31
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   4.5674(17)
_cell_length_b                   35.23(9)
_cell_length_c                   16.111(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2592(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    401
_cell_measurement_temperature    290.6(10)
_cell_measurement_theta_max      24.8330
_cell_measurement_theta_min      2.7690
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65734
_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 dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1200
_exptl_crystal_preparation       
'Mounted in a Diamond-Anvil Cell using parabar oil as pressure medium.,Luminescent'
_exptl_crystal_pressure_history  
'Pressurized to 1.00 GPa and left to stabilize over 24 hours.'
_exptl_crystal_recrystallization_method 'from chloroform at room temperature'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
High-pressure measurement at 1.00 GPa in a Merill-Basset Diamond Anvil Cell with
effective opening angle of 50 deg. and parabar 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  0.0726
_diffrn_reflns_av_unetI/netI     0.0675
_diffrn_reflns_Laue_measured_fraction_full 0.523
_diffrn_reflns_Laue_measured_fraction_max 0.412
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            2279
_diffrn_reflns_point_group_measured_fraction_full 0.499
_diffrn_reflns_point_group_measured_fraction_max 0.382
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.274
_diffrn_reflns_theta_min         2.780
_diffrn_ambient_temperature      290.6(10)
_diffrn_ambient_pressure         1000000
_diffrn_ambient_environment      'Diamond Anvil Cell filled with parabar oil'
_diffrn_crystal_treatment        
'Pressurized slowly in parabar oil as a hydrostatic medium.'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4391
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.523
_diffrn_measured_fraction_theta_max 0.412
_diffrn_measurement_details      
'List of Runs (angles in degrees, time in seconds): # Type Start End Width tₑₓₚ ω θ κ φ Frames -------------------------------------------------------------------------- 1 ω -25.00 0.00 1.00 125.00 -- 9.85 -37.00-120.00 25 2 ω -35.00 -9.00 1.00 125.00 -- 9.85 -19.00-120.00 26 3 ω -26.00 7.00 1.00 125.00 -- 9.85 19.00 30.00 33 4 ω 4.00 30.00 1.00 125.00 -- 9.85 56.00 161.00 26 5 ω -13.00 19.00 1.00 125.00 -- 9.85 -81.00-151.00 32 6 ω -20.00 5.00 1.00 125.00 -- 9.85 26.00 -7.00 25 7 ω -52.00 -26.00 1.00 125.00 -- -11.72 19.00 30.00 26 8 ω -65.00 -39.00 1.00 125.00 -- -11.72 134.00 123.00 26'
_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_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0024230000
_diffrn_orient_matrix_UB_12      0.0200189000
_diffrn_orient_matrix_UB_13      -0.0005080000
_diffrn_orient_matrix_UB_21      0.1157989000
_diffrn_orient_matrix_UB_22      -0.0000829000
_diffrn_orient_matrix_UB_23      0.0295546000
_diffrn_orient_matrix_UB_31      0.1043448000
_diffrn_orient_matrix_UB_32      -0.0003453000
_diffrn_orient_matrix_UB_33      -0.0327935000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\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         0.793
_reflns_Friedel_fraction_full    0.474
_reflns_Friedel_fraction_max     0.350
_reflns_number_gt                471
_reflns_number_total             683
_reflns_odcompleteness_completeness 49.31
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXD (Sheldrick, 2008)'
_refine_diff_density_max         0.091
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details .
_refine_ls_abs_structure_Flack   .
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         683
_refine_ls_number_restraints     79
_refine_ls_R_factor_all          0.0981
_refine_ls_R_factor_gt           0.0612
_refine_ls_restrained_S_all      1.078
_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)+(0.0434P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1241
_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
 C2, O1, C17, C1, C18, C14, C3, C15, C13, C12, C11
 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:
 C3(H3), C14(H14), C13(H13), C11(H11)
3.b Idealised Me refined as rotating group:
 C18(H18B,H18A,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1079(11) 0.4214(3) 0.2912(3) 0.066(4) Uani 1 1 d . U . . .
C3 C 0.4058(13) 0.4853(4) 0.3571(3) 0.036(4) Uani 1 1 d . U . . .
H3 H 0.3456 0.4754 0.3063 0.043 Uiso 1 1 calc R . . . .
C2 C 0.2924(12) 0.4683(3) 0.4323(3) 0.033(3) Uani 1 1 d . U . . .
C1 C 0.0926(12) 0.4387(4) 0.4348(4) 0.038(3) Uani 1 1 d . U . . .
C14 C -0.0089(14) 0.4254(4) 0.5119(4) 0.049(4) Uani 1 1 d . U . . .
H14 H -0.1428 0.4055 0.5137 0.058 Uiso 1 1 calc R . . . .
C13 C 0.0897(14) 0.4418(4) 0.5861(4) 0.047(4) Uani 1 1 d . U . . .
H13 H 0.0136 0.4334 0.6364 0.056 Uiso 1 1 calc R . . . .
C12 C 0.2930(13) 0.4696(4) 0.5858(3) 0.041(4) Uani 1 1 d . U . . .
C15 C 0.3970(11) 0.4851(4) 0.5081(3) 0.031(3) Uani 1 1 d . U . . .
C11 C 0.4034(14) 0.4867(4) 0.6618(3) 0.043(5) Uani 1 1 d . U . . .
H11 H 0.3313 0.4781 0.7124 0.052 Uiso 1 1 calc R . . . .
C17 C -0.0075(14) 0.4183(4) 0.3589(5) 0.046(4) Uani 1 1 d . U . . .
C18 C -0.2551(14) 0.3894(4) 0.3669(5) 0.055(5) Uani 1 1 d . U . . .
H18B H -0.3260 0.3829 0.3127 0.083 Uiso 1 1 calc GR . . . .
H18A H -0.4117 0.4002 0.3989 0.083 Uiso 1 1 calc GR . . . .
H18C H -0.1834 0.3671 0.3942 0.083 Uiso 1 1 calc GR . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.100(4) 0.050(14) 0.047(3) -0.005(3) -0.007(2) -0.019(5)
C3 0.046(4) 0.033(14) 0.028(2) 0.005(4) -0.005(2) 0.001(5)
C2 0.038(4) 0.029(10) 0.031(3) 0.007(4) -0.001(3) 0.011(4)
C1 0.036(3) 0.033(10) 0.045(3) -0.001(4) 0.001(3) 0.003(4)
C14 0.046(4) 0.042(13) 0.058(3) 0.007(5) 0.004(3) 0.004(4)
C13 0.048(4) 0.051(13) 0.042(3) 0.010(5) 0.009(3) 0.011(5)
C12 0.040(4) 0.049(12) 0.034(3) 0.005(4) 0.006(3) 0.011(4)
C15 0.037(3) 0.029(11) 0.029(2) 0.000(4) 0.004(2) 0.014(4)
C11 0.062(5) 0.044(16) 0.024(3) 0.007(4) 0.004(2) 0.017(5)
C17 0.045(3) 0.034(13) 0.058(3) -0.004(4) -0.012(3) 0.013(5)
C18 0.045(3) 0.030(14) 0.091(5) -0.019(6) -0.004(3) 0.008(5)

_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 1.216(9) . ?
C3 C3 1.35(2) 2_665 ?
C3 C2 1.448(10) . ?
C2 C1 1.386(15) . ?
C2 C15 1.440(9) . ?
C1 C14 1.405(11) . ?
C1 C17 1.490(12) . ?
C14 C13 1.403(13) . ?
C13 C12 1.349(16) . ?
C12 C15 1.445(11) . ?
C12 C11 1.455(12) . ?
C15 C15 1.41(2) 2_665 ?
C11 C11 1.29(2) 2_665 ?
C17 C18 1.527(17) . ?

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
C3 C3 C2 123.2(5) 2_665 . ?
C1 C2 C3 124.9(6) . . ?
C1 C2 C15 120.2(6) . . ?
C15 C2 C3 114.9(8) . . ?
C2 C1 C14 119.6(8) . . ?
C2 C1 C17 122.7(7) . . ?
C14 C1 C17 117.6(10) . . ?
C13 C14 C1 120.7(10) . . ?
C12 C13 C14 121.1(8) . . ?
C13 C12 C15 120.2(7) . . ?
C13 C12 C11 122.4(7) . . ?
C15 C12 C11 117.3(10) . . ?
C2 C15 C12 118.0(8) . . ?
C15 C15 C2 121.9(5) 2_665 . ?
C15 C15 C12 120.0(6) 2_665 . ?
C11 C11 C12 122.6(5) 2_665 . ?
O1 C17 C1 124.1(9) . . ?
O1 C17 C18 117.2(8) . . ?
C1 C17 C18 118.6(7) . . ?

_iucr_refine_instructions_details 
;
TITL p1_v2 in Fdd2 #43
REM Best SHELXD solution FINAL CC 78.48
REM Fragments: 20
REM reset to Fdd2 #43
CELL 0.71073 4.567374 35.230464 16.110961 90 90 90
ZERR 8 0.001652 0.089438 0.006137 0 0 0
LATT -4
SYMM -X,-Y,+Z
SYMM 0.25-X,0.25+Y,0.25+Z
SYMM 0.25+X,0.25-Y,0.25+Z
SFAC C H O
UNIT 160 112 16
RIGU C2 O1 C17 C1 C18 C14 C3 C15 C13 C12 C11
 
L.S. 4 0 0
PLAN  2
SIZE 0.28 0.18 0.07
fmap 2
ACTA
OMIT 0 12 -20
REM <olex2.extras>
REM <HklSrc "%./p1_v2.hkl">
REM </olex2.extras>
 
WGHT    0.043400
FVAR       0.84795
O1    3    0.107912    0.421414    0.291153    11.00000    0.09978    0.05027 =
         0.04729   -0.00506   -0.00668   -0.01926
C3    1    0.405801    0.485296    0.357065    11.00000    0.04650    0.03338 =
         0.02821    0.00505   -0.00502    0.00074
AFIX  43
H3    2    0.345623    0.475449    0.306296    11.00000   -1.20000
AFIX   0
C2    1    0.292434    0.468269    0.432269    11.00000    0.03819    0.02915 =
         0.03059    0.00662   -0.00080    0.01088
C1    1    0.092637    0.438696    0.434798    11.00000    0.03591    0.03315 =
         0.04507   -0.00105    0.00098    0.00269
C14    1   -0.008885    0.425422    0.511864    11.00000    0.04582    0.04171 =
         0.05818    0.00709    0.00373    0.00414
AFIX  43
H14    2   -0.142760    0.405549    0.513663    11.00000   -1.20000
AFIX   0
C13    1    0.089703    0.441849    0.586112    11.00000    0.04804    0.05054 =
         0.04181    0.01003    0.00896    0.01082
AFIX  43
H13    2    0.013609    0.433449    0.636405    11.00000   -1.20000
AFIX   0
C12    1    0.293048    0.469628    0.585772    11.00000    0.04036    0.04852 =
         0.03442    0.00526    0.00564    0.01063
C15    1    0.397017    0.485122    0.508109    11.00000    0.03656    0.02857 =
         0.02869    0.00027    0.00361    0.01435
C11    1    0.403411    0.486737    0.661813    11.00000    0.06179    0.04411 =
         0.02441    0.00739    0.00387    0.01692
AFIX  43
H11    2    0.331287    0.478132    0.712410    11.00000   -1.20000
AFIX   0
C17    1   -0.007536    0.418348    0.358857    11.00000    0.04489    0.03404 =
         0.05758   -0.00361   -0.01239    0.01275
C18   1   -0.255145    0.389442    0.366916    11.00000    0.04484    0.03022 =
         0.09086   -0.01911   -0.00368    0.00837
AFIX 137
H18B  2   -0.326001    0.382859    0.312695    11.00000   -1.50000
H18A  2   -0.411704    0.400225    0.398926    11.00000   -1.50000
H18C  2   -0.183360    0.367074    0.394191    11.00000   -1.50000
AFIX   0
HKLF 4
 
REM  p1_v2 in Fdd2 #43
REM R1 =  0.0612 for     471 Fo > 4sig(Fo)  and  0.0981 for all     683 data
REM    101 parameters refined using     79 restraints
 
END  
     
WGHT      0.0434      0.0000 

REM Highest difference peak  0.091,  deepest hole -0.120,  1-sigma level  0.030
Q1    1   0.1418  0.5163  0.6997  11.00000  0.05    0.09
Q2    1   0.1988  0.5111  0.5089  11.00000  0.05    0.09

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0612 for 471 Fo > 4sig(Fo) and 0.0981 for all 2389 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.09, deepest hole -0.12
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0981
  REM R1_gt = 0.0612
  REM wR_ref = 0.1241
  REM GOOF = 1.105
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 2389
  REM Reflections_gt = 471
  REM Parameters = n/a
  REM Hole = -0.12
  REM Peak = 0.09
  REM Flack = -4.1(10)

  
;
_olex2_exptl_crystal_mounting_method 
'in Diamond Anvill Cell, opening angle 50 degrees, in Pratone N oil'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_diffrn_reflns_filtered   443
_oxdiff_exptl_absorpt_empirical_details 
'Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling'
_oxdiff_exptl_absorpt_empirical_full_max 2.430
_oxdiff_exptl_absorpt_empirical_full_min 0.563

# start Validation Reply Form
_vrf_PLAT029_2bisAP-beta_1000000kPa 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.523 Why?  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 50 degrees on a very thin plate. This limited the number 
of reflections that could be collected, as most of them were obscured 
by the DAC.
;
_vrf_PLAT340_2bisAP-beta_1000000kPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01338 Ang. 
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 50 degrees on a very thin plate. This limited the number
of reflections that could be collected, as most of them were obscured by the
DAC, which together with weak scattering negatively affected the precision.
;
_vrf_PLAT911_2bisAP-beta_1000000kPa 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L= 0.600            55 Report
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 50 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
;
_vrf_PLAT915_2bisAP-beta_1000000kPa 
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         35 % 
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 50 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
Moreover, high Friedel pair coverage was unnecessary, as space group information
was determined using complete dataset gathered on this sample before experiment. 
;
_vrf_PLAT089_2bisAP-beta_1000000kPa 
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       3.77 Note  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 50 degrees on a very thin plate. This limited the number 
of reflections that could be collected, as most of them were obscured 
by the DAC.
;
_vrf_PLAT148_2bisAP-beta_1000000kPa 
;
PROBLEM: s.u. on the      b    - Axis is (Too) Large ....     0.0900 Ang.  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 50 degrees on a very thin plate. This limited the number 
of reflections that could be collected, as most of them were obscured 
by the DAC. b direction was particularly affected due to crystal orientation.
;
_vrf_PLAT906_2bisAP-beta_1000000kPa 
;
PROBLEM: Large K Value in the Analysis of Variance ......      7.641 Check 
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 50 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
This, and relatively weak scattering, affected the precission of the final 
model.
;
_vrf_PLAT978_2bisAP-beta_1000000kPa 
;
PROBLEM: Number C-C Bonds with Positive Residual Density.          0 Info  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 50 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
This, and relatively weak scattering, affected the precission of the final 
model.
;
# 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_2bisAP-beta_1640000kPa
_database_code_depnum_ccdc_archive 'CCDC 2039415'
loop_
_audit_author_name
_audit_author_address
'Daniel Tchon'
;Faculty of Chemistry, University of Warsaw
Poland
;
_audit_update_record             
;
2020-10-19 deposited with the CCDC.	2021-01-21 downloaded from the CCDC.
;
_audit_creation_date             2020-09-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.01.31 svn.r88ba2a3 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            1,1'-Pyrene-1,8-diyldiethanone
_chemical_name_systematic        1,8-Diacetylpyrene
_chemical_formula_moiety         'C20 H14 O2'
_chemical_formula_sum            'C20 H14 O2'
_chemical_formula_weight         286.31
_chemical_absolute_configuration ?
_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 0.0015 0.0009 '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 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   4.464(8)
_cell_length_b                   34.87(11)
_cell_length_c                   15.923(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2479(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    168
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.1240
_cell_measurement_theta_min      2.2070
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.063
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78945
_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_absorpt_special_details   ?
_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    1.534
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1200
_exptl_crystal_preparation       
'Mounted in a Diamond-Anvil Cell using parabar oil as pressure medium.,Luminescent'
_exptl_crystal_pressure_history  
'Pressurized to 1.64 GPa and left to stabilize over 24 hours.'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
High-pressure measurement at 1.64 GPa in a Merill-Basset Diamond Anvil Cell with
effective opening angle of 30 deg. and parabar 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  0.0775
_diffrn_reflns_av_unetI/netI     0.1278
_diffrn_reflns_Laue_measured_fraction_full 0.505
_diffrn_reflns_Laue_measured_fraction_max 0.506
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            713
_diffrn_reflns_point_group_measured_fraction_full 0.413
_diffrn_reflns_point_group_measured_fraction_max 0.413
_diffrn_reflns_theta_full        18.123
_diffrn_reflns_theta_max         18.123
_diffrn_reflns_theta_min         2.219
_diffrn_ambient_temperature      293(2)
_diffrn_ambient_pressure         1640000
_diffrn_ambient_environment      'Diamond Anvil Cell filled with parabar oil'
_diffrn_crystal_treatment        
'Pressurized slowly in parabar oil as a hydrostatic medium.'
_diffrn_detector_area_resol_mean 16.0128
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.505
_diffrn_measured_fraction_theta_max 0.506
_diffrn_measurement_details      
'#__ type_ start__ end____ width___ exp.time_ 1 omega -26.00 46.00 1.0000 180.0000 omega____ theta____ kappa____ phi______ frames - -19.9892 -39.0000 12.0000 72 #__ type_ start__ end____ width___ exp.time_ 2 omega -28.00 -2.00 1.0000 180.0000 omega____ theta____ kappa____ phi______ frames - -19.9892 -81.0000 -151.0000 26 #__ type_ start__ end____ width___ exp.time_ 3 omega -4.00 22.00 1.0000 180.0000 omega____ theta____ kappa____ phi______ frames - -19.9892 38.0000 120.0000 26 #__ type_ start__ end____ width___ exp.time_ 4 omega 17.00 64.00 1.0000 180.0000 omega____ theta____ kappa____ phi______ frames - -19.9892 -135.0000 -123.0000 47 #__ type_ start__ end____ width___ exp.time_ 5 omega -84.00 -59.00 1.0000 180.0000 omega____ theta____ kappa____ phi______ frames - -19.9892 97.0000 143.0000 25 #__ type_ start__ end____ width___ exp.time_ 6 omega -35.00 -10.00 1.0000 180.0000 omega____ theta____ kappa____ phi______ frames - -19.9892 97.0000 143.0000 25 #__ type_ start__ end____ width___ exp.time_ 7 omega 5.00 31.00 1.0000 180.0000 omega____ theta____ kappa____ phi______ frames - -19.9892 38.0000 -30.0000 26 #__ type_ start__ end____ width___ exp.time_ 8 omega -54.00 18.00 1.0000 180.0000 omega____ theta____ kappa____ phi______ frames - -19.9892 39.0000 -12.0000 72 #__ type_ start__ end____ width___ exp.time_ 9 omega -5.00 25.00 1.0000 180.0000 omega____ theta____ kappa____ phi______ frames - 19.9892 -67.0000 23.0000 30 #__ type_ start__ end____ width___ exp.time_ 10 omega -43.00 -30.00 1.0000 180.0000 omega____ theta____ kappa____ phi______ frames - 19.9892 135.0000 -57.0000 13'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 
'Diamond Anvil Cell, effective opening angle of 30 deg.'
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56087
_diffrn_source                   'SuperNova (Ag) X-ray Source'
_reflns_Friedel_coverage         0.564
_reflns_Friedel_fraction_full    0.312
_reflns_Friedel_fraction_max     0.311
_reflns_number_gt                222
_reflns_number_total             366
_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 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_computing_data_collection       
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details .
_refine_ls_abs_structure_Flack   .
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     89
_refine_ls_number_reflns         366
_refine_ls_number_restraints     145
_refine_ls_R_factor_all          0.1475
_refine_ls_R_factor_gt           0.0865
_refine_ls_restrained_S_all      0.941
_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)+(0.0518P)²+19.7312P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1594
_refine_ls_wR_factor_ref         0.1988
_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. Uiso/Uaniso restraints and constraints
O1 \\sim C3 \\sim C2 \\sim C1 \\sim C14 \\sim C13 \\sim C12 \\sim C11 \\sim C15
\\sim C17 \\sim C18: within 1.7A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 1.7A
C2 \\sim C3: within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.04 within 1.7A
3. Rigid body (RIGU) restrains
 C3, C2, C1, C14, C13, C12, C11, C15, C17, C18, O1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C14(H14), C13(H13), C11(H11)
4.b Fitted hexagon refined as free rotating group:
 C2(C1,C14,C13,C12,C15)
4.c Idealised Me refined as rotating group:
 C18(H18C,H18B,H18A)
;
_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 -0.343(5) -0.6719(7) -0.2906(8) 0.067(6) Uani 1 1 d . U . . .
C3 C -0.655(7) -0.7336(11) -0.3560(8) 0.034(6) Uani 1 1 d . U . . .
H3 H -0.604392 -0.721863 -0.305456 0.040 Uiso 1 1 calc R U . . .
C2 C -0.540(4) -0.7187(5) -0.4328(7) 0.033(5) Uani 1 1 d G U . . .
C1 C -0.330(4) -0.6893(5) -0.4342(8) 0.052(6) Uani 1 1 d G U . . .
C14 C -0.226(4) -0.6752(5) -0.5105(11) 0.062(7) Uani 1 1 d G U . . .
H14 H -0.085129 -0.655558 -0.511405 0.074 Uiso 1 1 calc R U . . .
C13 C -0.331(4) -0.6907(5) -0.5854(8) 0.060(7) Uani 1 1 d G U . . .
H13 H -0.260994 -0.681293 -0.636389 0.073 Uiso 1 1 calc R U . . .
C12 C -0.541(4) -0.7201(6) -0.5840(7) 0.053(6) Uani 1 1 d G U . . .
C15 C -0.646(5) -0.7341(6) -0.5077(9) 0.037(4) Uani 1 1 d G U . . .
C11 C -0.660(8) -0.7346(13) -0.6630(9) 0.052(8) Uani 1 1 d . U . . .
H11 H -0.612526 -0.722432 -0.713258 0.063 Uiso 1 1 calc R U . . .
C17 C -0.224(6) -0.6670(10) -0.3575(15) 0.055(7) Uani 1 1 d . U . . .
C18 C 0.018(6) -0.6404(10) -0.3689(17) 0.058(7) Uani 1 1 d . U . . .
H18C H 0.172903 -0.645662 -0.328698 0.087 Uiso 1 1 calc R U . . .
H18B H -0.053944 -0.614702 -0.361125 0.087 Uiso 1 1 calc R U . . .
H18A H 0.097538 -0.643035 -0.424682 0.087 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.10(2) 0.04(2) 0.058(8) -0.005(9) 0.002(9) 0.003(11)
C3 0.027(17) 0.04(2) 0.036(8) -0.013(11) -0.003(11) 0.010(8)
C2 0.025(13) 0.035(15) 0.037(7) -0.009(9) 0.004(9) 0.022(7)
C1 0.050(14) 0.056(15) 0.050(8) 0.000(11) 0.000(10) -0.001(9)
C14 0.070(18) 0.06(2) 0.060(9) 0.015(12) 0.003(12) -0.002(9)
C13 0.078(19) 0.06(2) 0.044(9) 0.017(13) 0.012(12) 0.000(10)
C12 0.073(17) 0.045(19) 0.041(7) 0.005(10) 0.010(9) 0.009(10)
C15 0.044(14) 0.033(16) 0.033(6) -0.002(10) 0.006(10) 0.016(7)
C11 0.09(2) 0.04(3) 0.027(8) 0.015(13) 0.010(12) 0.017(11)
C17 0.053(19) 0.048(19) 0.065(9) -0.001(12) -0.006(11) 0.000(11)
C18 0.03(2) 0.03(2) 0.107(16) -0.006(17) -0.015(13) 0.014(11)

_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 1.20(3) . ?
C3 C3 1.43(5) 14_335 ?
C3 H3 0.9300 . ?
C3 C2 1.42(2) . ?
C2 C1 1.3900 . ?
C2 C15 1.3900 . ?
C1 C14 1.3900 . ?
C1 C17 1.52(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.3900 . ?
C13 H13 0.9300 . ?
C13 C12 1.3900 . ?
C12 C15 1.3900 . ?
C12 C11 1.46(2) . ?
C15 C15 1.45(2) 14_335 ?
C11 C11 1.34(7) 14_335 ?
C11 H11 0.9300 . ?
C17 C18 1.43(4) . ?
C18 H18C 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18A 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
C3 C3 H3 119.8 14_335 . ?
C2 C3 C3 120.5(13) . 14_335 ?
C2 C3 H3 119.8 . . ?
C1 C2 C3 121.7(14) . . ?
C1 C2 C15 120.0 . . ?
C15 C2 C3 118.3(14) . . ?
C2 C1 C14 120.0 . . ?
C2 C1 C17 125.0(15) . . ?
C14 C1 C17 114.6(15) . . ?
C1 C14 H14 120.0 . . ?
C13 C14 C1 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C13 H13 120.0 . . ?
C12 C13 C14 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C12 C15 120.0 . . ?
C13 C12 C11 119.2(16) . . ?
C15 C12 C11 120.7(16) . . ?
C2 C15 C15 120.92(13) . 14_335 ?
C12 C15 C2 120.00(11) . . ?
C12 C15 C15 119.0(2) . 14_335 ?
C12 C11 H11 120.1 . . ?
C11 C11 C12 119.7(16) 14_335 . ?
C11 C11 H11 120.1 14_335 . ?
O1 C17 C1 120(2) . . ?
O1 C17 C18 123(3) . . ?
C18 C17 C1 118(2) . . ?
C17 C18 H18C 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18A 109.5 . . ?
H18C C18 H18B 109.5 . . ?
H18C C18 H18A 109.5 . . ?
H18B C18 H18A 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
C3 C3 C2 C1 -173(4) 14_335 . . . ?
C3 C3 C2 C15 7(5) 14_335 . . . ?
C3 C2 C1 C14 -179(2) . . . . ?
C3 C2 C1 C17 -7(3) . . . . ?
C3 C2 C15 C12 179(2) . . . . ?
C3 C2 C15 C15 -3(4) . . . 14_335 ?
C2 C1 C14 C13 0.0 . . . . ?
C2 C1 C17 O1 -7(4) . . . . ?
C2 C1 C17 C18 173(3) . . . . ?
C1 C2 C15 C12 0.0 . . . . ?
C1 C2 C15 C15 177(5) . . . 14_335 ?
C1 C14 C13 C12 0.0 . . . . ?
C14 C1 C17 O1 166(3) . . . . ?
C14 C1 C17 C18 -14(4) . . . . ?
C14 C13 C12 C15 0.0 . . . . ?
C14 C13 C12 C11 177(3) . . . . ?
C13 C12 C15 C2 0.0 . . . . ?
C13 C12 C15 C15 -177(5) . . . 14_335 ?
C13 C12 C11 C11 173(5) . . . 14_335 ?
C15 C2 C1 C14 0.0 . . . . ?
C15 C2 C1 C17 173(2) . . . . ?
C15 C12 C11 C11 -10(7) . . . 14_335 ?
C11 C12 C15 C2 -177(3) . . . . ?
C11 C12 C15 C15 6(4) . . . 14_335 ?
C17 C1 C14 C13 -173(2) . . . . ?

loop_
_diffrn_refln_index_h
_diffrn_refln_index_k
_diffrn_refln_index_l
_diffrn_refln_intensity_net
_diffrn_refln_intensity_u
_diffrn_refln_scale_group_code
0 0 -8 42.21 10.46 8
0 0 -6 10.33 3.71 8
0 0 -2 7.33 4.99 9
0 0 4 6064.58 202.09 1
0 0 4 6622.77 240.95 4
0 0 6 15.46 5.51 4
0 0 6 4.61 13.21 1
0 0 8 22.15 5.81 4
0 0 8 20.81 8.01 1
0 0 10 61.75 42.48 4
0 0 12 3039.89 308.74 4
0 0 12 2458.53 230.48 1
0 0 12 2568.66 294.69 10
0 0 16 52.1 42.35 10
0 0 16 34.1 34.78 4
0 2 -10 66.49 22.57 8
0 2 -8 24.93 22.14 8
0 2 -6 133.97 37.9 9
0 2 -6 248.21 40.46 8
0 2 -4 10.64 7.65 7
0 -2 -4 9.6 11.5 6
0 2 -4 7.5 10.64 9
0 -2 -2 5198.68 183.08 6
0 2 -2 4978.83 166.12 5
0 2 2 4917.47 149.48 4
0 2 2 5017.62 150.52 1
0 -2 2 4957.05 157.79 10
0 2 4 8.41 13 1
0 2 6 186.49 45.22 1
0 -2 6 182.62 55.48 10
0 2 6 152.43 49.66 4
0 -2 6 175.81 45.73 4
0 2 8 5.21 14.13 4
0 -2 8 39.4 32.41 4
0 -2 10 69.38 33.66 4
0 -2 10 112.5 67.55 10
0 2 10 62.28 42.62 1
0 2 10 88.11 39.45 4
0 -2 12 3.02 35.66 10
0 2 12 38.71 15.76 4
0 -2 12 54.77 46.84 4
0 -2 14 2520.68 305.02 4
0 2 14 2189.63 285.95 10
0 2 14 2710.23 312.34 4
0 2 16 13.35 42.2 10
0 -2 16 65.29 61.14 4
0 4 -14 76.65 40.22 5
0 4 -8 278.22 65.59 9
0 4 -8 305.33 58 8
0 4 -6 5.54 12.26 8
0 4 -6 19.55 18.8 9
0 -4 -4 1186 126.34 6
0 4 -4 1095.67 83.15 7
0 4 4 1100.15 96.24 1
0 4 4 1175.95 104.34 4
0 -4 6 2.17 15.39 10
0 4 6 6.73 8.93 4
0 -4 8 232.86 74.7 10
0 4 8 225.04 61.54 4
0 4 8 293.69 62.36 1
0 -4 10 57.67 31.2 10
0 4 12 1265.44 188.27 4
0 4 12 953.17 157.58 1
0 -4 12 1130.73 181.6 4
0 -4 14 9.66 11.26 4
0 4 14 26.76 75.18 4
0 -4 16 84.7 64.15 4
0 4 16 8.93 88.04 10
0 4 16 180.72 93.67 4
0 6 -14 89.81 78.3 5
0 6 -12 2.38 20.78 5
0 6 -12 18.37 46.32 9
0 6 -10 331.21 71.59 8
0 6 -10 246.12 64.92 9
0 6 -10 224.28 89.79 5
0 -6 -8 22.94 32.4 6
0 6 -8 16.09 21.87 9
0 6 -8 8.74 14.13 7
0 -6 -6 1113.26 146.23 6
0 -6 -4 2.15 10.02 6
0 6 6 1103.93 120.94 4
0 6 6 884.37 110.75 1
0 6 10 396.6 96.34 4
0 6 10 296.13 75.59 1
0 -6 14 58.35 48.24 4
0 6 14 62.04 46.26 4
0 -6 16 3.85 12.35 4
0 -8 -8 1207.06 177.23 6
0 -8 -6 20.81 16.25 6
0 8 6 2.52 18.3 1
0 8 8 1066.14 143 4
0 8 8 1011.92 130.93 1
0 8 10 25.54 22.27 1
0 -8 12 26.76 55.3 4
0 8 14 14.98 50.49 1
0 8 14 39.19 24.35 4
0 -10 -10 336.35 113.43 6
0 -10 -8 30.96 40.42 6
0 10 10 323.73 90.68 1
0 10 10 26.07 21.53 4
0 10 12 16.83 51.46 1
0 10 14 68.3 66.71 1
0 10 16 82.32 70.62 4
0 -12 -12 86.9 69.6 6
0 12 10 2.2 27.76 1
0 12 12 94.36 48.17 1
0 12 14 95.13 62.18 1
1 -1 -17 27.83 19.19 5
1 -1 -15 38.8 52.04 5
1 -1 -13 139.86 67.15 5
1 1 -13 131.01 55.62 9
1 1 -13 113.42 59.87 5
1 -1 -11 39.32 23.84 9
-1 -1 -9 67.49 42.37 6
1 1 -9 32.52 32.47 9
1 1 -9 24.53 14.61 5
-1 1 -9 19.56 22.03 8
1 -1 -9 12.59 34.23 9
-1 1 -7 1593.04 172 6
-1 -1 -7 1497.71 180.04 6
1 -1 -7 1554.39 194.86 5
1 -1 -7 1406.31 163.28 9
-1 1 -5 207.75 53.88 6
1 -1 -5 131.9 41.12 9
-1 -1 -5 31.32 18.15 6
-1 1 -5 118.97 37.11 8
1 -1 -5 146.46 52.72 5
-1 1 -3 764.08 88.54 8
1 -1 5 153.84 47.25 4
1 1 5 53.19 29.69 4
-1 1 5 137.11 41.28 1
1 -1 7 1382.25 87.29 1
1 -1 7 1553.19 168.13 4
1 1 7 1629.42 168.71 4
-1 1 9 33.99 30.63 1
1 -1 9 35.58 14.71 1
1 1 9 56.89 35.17 4
1 1 9 65.25 24.79 1
1 -1 9 95.68 57.5 4
1 -1 11 107.58 66.39 4
1 1 11 54.43 24.36 4
-1 1 11 26.59 14.84 4
1 1 13 298.96 85.67 4
-1 1 13 62.11 37.4 4
1 -1 13 217.03 97.93 4
1 -1 15 59.2 50.7 4
-1 -1 15 3.61 64.65 4
1 1 17 189.39 81.17 4
1 -1 17 29.26 31.65 10
1 -3 -17 108.68 52.65 5
-1 -3 -9 217.88 84.6 6
1 -3 -9 46.54 27.09 9
-1 3 -9 125.19 53.67 8
-1 3 -7 2379.94 187.62 8
1 -3 -7 2191.07 208.34 9
-1 -3 -7 722.85 122 6
-1 3 -5 1622.71 148.86 8
1 -3 -5 1601.46 150.57 9
-1 3 -3 146.65 46.58 8
-1 3 -3 105.94 26.87 6
1 -3 -3 130.47 40.53 5
1 -3 -3 115.54 35.48 9
1 -3 -1 1384.1 136.29 3
-1 3 -1 1327.66 115.38 8
1 -3 -1 1351.98 95.26 9
-1 3 1 1313.4 111.69 1
-1 3 1 1359.98 108.75 8
-1 3 3 129.86 41.11 1
1 -3 3 122.2 33.16 4
-1 3 5 1448.38 156.49 1
1 -3 5 1662.4 152.67 4
-1 3 7 2323.53 191.8 4
-1 3 7 2311.39 209.23 1
1 -3 7 3014.89 245.89 4
-1 3 7 2644.18 211.25 10
1 -3 9 85.72 21.16 1
1 3 9 93.84 33.36 1
-1 3 9 159.27 59.18 4
1 -3 9 173.51 62.77 4
-1 3 9 30.62 20.15 1
-1 3 9 147.58 61.17 10
-1 3 11 96.88 43.69 4
-1 3 11 21.84 46.59 10
1 3 11 48.26 52.7 4
-1 3 11 73.68 66.48 1
-1 3 13 210.8 75.83 10
1 -3 13 213.55 84.58 4
-1 3 13 552.75 139.73 4
-1 3 13 306.27 115.51 1
1 3 13 248.72 95.01 4
1 -3 15 196.41 91.29 4
-1 3 15 20.93 30.7 4
1 3 17 27.78 22.82 4
1 -3 17 56.71 50.88 4
-1 5 -11 76.41 43.63 8
-1 -5 -9 34.81 41.86 6
-1 5 -7 1002.75 130.2 8
-1 5 -5 1097.63 126.66 8
1 -5 -5 1135.33 129.47 9
-1 5 -3 474.93 77.99 8
1 -5 -3 627.35 104.63 3
1 -5 -3 547.21 76.87 9
-1 5 -1 11376.6 361.87 8
1 -5 1 11606.2 204.88 4
-1 5 1 11013.6 325.1 8
-1 5 3 488.12 51.69 4
1 -5 3 557 71.06 4
-1 5 3 467.12 58.9 8
-1 5 3 470.8 83.12 1
-1 5 5 1082.93 106.16 4
1 -5 5 1259.29 136.15 4
-1 5 5 1126.81 107.86 10
-1 5 5 1032.54 133.66 1
-1 5 7 939.7 121.65 4
1 -5 7 1247.05 159.28 4
-1 5 7 1020.89 147.55 1
-1 5 7 1070.88 129.42 10
-1 5 9 26.99 36.09 10
1 -5 9 25.3 15.47 4
1 5 11 35.46 23.72 4
-1 5 11 103.31 27.68 4
-1 5 11 111.71 59.32 10
-1 5 11 51.69 44.68 1
-1 5 13 819.07 154.92 10
1 5 13 773.73 157.67 4
-1 5 13 742.08 158.7 1
1 -5 13 892.7 220.16 10
-1 5 13 1076 189.61 4
-1 5 15 31.78 44.35 10
1 5 15 39.73 25.42 4
-1 5 15 10.06 27.62 4
1 -5 17 54.5 13.6 10
-1 5 17 93.77 69.34 10
-1 5 17 2.01 39.03 4
-1 -7 -13 67.51 61.31 6
-1 7 -11 109.92 32.23 8
-1 7 -9 170.95 58.83 8
-1 7 -7 123.01 49.69 8
1 -7 -5 396.49 96.48 3
-1 7 -5 419.37 80.36 8
-1 7 -3 1711.51 158.07 8
-1 7 -3 1806.06 87.62 1
-1 7 -1 12240 397.44 8
1 -7 1 12297 210.06 4
-1 7 1 12175.5 366.88 8
1 -7 3 1770.57 120.04 4
1 -7 3 1661.14 126.76 10
-1 7 3 1656.83 97.06 4
-1 7 3 1789.01 162.89 1
-1 7 3 1774.16 125.8 8
-1 7 5 477.7 89.78 1
1 -7 5 457.32 82.9 10
-1 7 5 447.89 74.98 4
-1 7 5 445.51 55.25 8
1 -7 5 413.62 74.91 4
-1 7 7 118.76 51.89 4
1 -7 7 36.08 22.89 10
1 -7 7 93.74 41.29 4
-1 7 7 33.12 17.28 1
1 -7 9 143.51 54.26 10
-1 7 9 236.42 68.6 10
1 -7 9 174.24 63.26 4
-1 7 9 161.79 62.95 1
-1 7 9 185.15 58.2 4
-1 7 11 97.28 43.16 4
-1 7 11 38.83 51.31 10
1 -7 11 192.68 88.78 10
-1 7 13 1475.58 215.31 4
-1 7 13 982.07 174.48 1
-1 7 13 1358.66 208.17 10
1 -7 13 1138.73 209.41 4
1 -7 13 1120.47 209.58 10
1 7 15 17.16 25.92 4
-1 7 15 45.77 32.22 10
1 -7 15 143.16 89.23 4
-1 7 15 94.24 71.91 4
1 -7 15 268.24 109.44 10
-1 7 17 79.85 80.29 10
-1 7 17 87.57 77.09 4
-1 9 -13 402.26 124.31 5
-1 9 -11 42.83 9.33 5
-1 9 -11 195.14 58.36 8
-1 9 -9 135.02 65.6 5
-1 9 -9 117.93 52.57 8
-1 9 -7 43.02 19.54 9
1 -9 -7 72.62 70.69 3
-1 9 -7 84.47 35.37 8
-1 9 -5 133.05 26.86 9
-1 9 -5 171.03 52.14 8
1 -9 -3 60.95 27.29 6
-1 9 -3 83.51 22.43 1
-1 9 -3 36.25 13.78 8
-1 9 -3 89.06 42.35 7
-1 9 -1 7963.46 338.24 7
1 -9 -1 7917.13 251.47 6
-1 9 -1 8105.19 264.34 1
-1 9 -1 7854 345.48 8
-1 9 1 7746.3 295.67 1
-1 9 1 7767.89 318.13 7
-1 9 1 8083.25 326.08 8
-1 9 3 65.37 27.84 8
-1 9 3 114.39 42.32 1
-1 9 3 72.92 34.65 7
-1 9 5 173.52 44.25 4
-1 9 5 187.71 41.35 7
1 -9 5 126.18 37.84 10
-1 9 5 204.91 42.22 8
-1 9 5 153.12 47.29 1
-1 9 7 93.65 43.48 4
-1 9 7 138.05 32.79 7
-1 9 7 65 18.23 1
1 -9 7 109.54 53.51 10
1 -9 7 52.52 33.2 4
-1 9 9 209.15 69.8 1
1 -9 9 184.4 71.74 10
-1 9 9 148.93 62.26 4
1 -9 9 103.87 38.03 4
1 -9 11 129.63 59.76 4
-1 9 11 112.58 44 1
1 -9 11 132.13 61.75 10
-1 9 11 4.8 32.3 4
-1 9 13 404.93 123.71 1
1 -9 13 318.62 98.45 4
1 -9 13 284.23 99.59 10
-1 9 13 397.95 121.12 10
-1 9 13 179.64 68.71 4
-1 9 15 153.3 100.26 4
1 -9 15 114.09 73.1 10
-1 9 15 17.74 88.02 10
1 -9 15 56.44 46.34 4
-1 11 -11 164.48 71.52 8
-1 11 -9 168.12 46.3 9
-1 11 -7 6.72 8.22 9
-1 11 -5 67.23 39.29 7
1 -11 -5 91.6 38.09 6
-1 11 -5 109.88 39.34 8
-1 11 -3 260.97 75.29 8
1 -11 -3 289.74 67.28 6
-1 11 -3 337.43 76.27 7
-1 11 -1 2198.16 156.93 1
-1 11 -1 1899.23 182.61 8
-1 11 -1 1921.16 179.24 7
-1 11 1 2062.82 178.33 7
-1 11 1 2001.3 163 1
-1 11 1 1831.67 165.65 8
-1 11 3 265.62 70.79 1
-1 11 3 309.68 63.27 7
-1 11 3 259.24 57.47 8
-1 11 5 152.99 38.83 7
-1 11 5 145.45 39.1 8
-1 11 5 97.4 45.91 1
-1 11 7 23.15 27.65 4
-1 11 9 157.86 55.63 4
-1 11 9 252.81 78.54 1
1 -11 9 150.31 68.85 4
-1 11 11 297.2 85.53 4
-1 11 11 216.89 61.59 1
1 -11 11 161.27 60.74 4
-1 11 13 172.77 87.85 4
1 -11 13 178.6 74.26 4
-1 11 13 95.68 45.42 1
-1 11 15 97.7 33.64 4
1 -11 15 166.37 102.59 4
-1 13 -11 145.14 72.11 8
-1 13 -7 39.93 19.02 7
1 -13 -7 144.09 68.08 6
-1 13 -7 112.7 49.67 8
-1 13 -5 303.24 79.43 7
1 -13 -5 276.42 80.03 6
-1 13 -5 301.84 90.84 8
-1 13 -3 125.82 49.51 7
1 -13 -3 72.62 32.7 6
-1 13 -3 155.33 60.13 8
-1 13 -1 676.78 110.33 7
-1 13 -1 849.57 126.91 8
-1 13 1 780.63 110.55 1
-1 13 1 880.38 122.82 8
-1 13 3 121.07 36.1 8
-1 13 3 192.47 63.96 1
-1 13 5 288.28 58.94 8
-1 13 5 257.52 71.45 1
-1 13 7 74.51 35.85 7
-1 13 7 59.28 23.07 8
-1 13 7 149.16 62.63 1
-1 13 9 103.59 52.24 1
-1 13 9 1.64 10.05 4
-1 13 11 5.54 39.32 1
1 -13 11 19.92 42.05 4
-1 13 13 287.48 85.62 4
-1 13 13 345.05 114.23 1
1 -13 13 259.9 84.03 4
-1 13 15 31.05 56.11 1
1 -15 -9 99.68 66.92 6
1 -15 -7 517.21 126.85 6
1 -15 -5 41.46 38.6 6
-1 15 3 84.13 31.82 1
-1 15 5 258.82 69.35 8
-1 15 5 256.57 78.89 1
-1 15 7 410.63 72.15 8
-1 15 7 386.91 103.94 1
-1 15 9 20.44 31.2 1
-1 15 11 219.28 83.64 1
-1 15 13 169.63 110.41 1
-1 15 15 65.33 76.74 1
1 -17 -9 31.76 61.81 6
-1 17 7 109.07 44.69 1
-1 17 11 150.59 86.21 1
-1 17 13 37.88 59.28 1
1 -19 -11 7.26 38.43 6
-1 19 13 35.16 40.01 1
2 0 14 28.34 39.74 4
2 0 16 32.59 47.07 4
-2 2 -8 239.58 63.15 6
2 -2 10 21.16 18.17 4
2 -2 12 80.38 55.88 4
-2 4 -10 111.86 61.82 8
-2 4 -8 336.12 87.46 8
-2 4 -8 448.01 97.78 6
-2 4 -6 750.36 135.27 8
-2 4 -6 807.98 114.28 6
-2 4 -4 117.94 59.02 8
2 -4 8 317.24 90.2 4
2 -4 10 57.92 33.17 4
2 -4 12 151.95 83.98 4
2 -4 14 29.73 40.7 4
2 -6 -14 76.14 59.56 5
-2 6 -12 36.56 53.03 8
2 -6 -12 84.14 38.49 5
-2 6 -10 66.68 58.28 8
2 -6 -10 30.15 40.53 5
-2 6 -8 31.96 30.01 8
2 -6 -8 55.31 16.38 5
2 -6 -8 29.96 25.93 9
2 -6 -6 577.26 116.54 9
-2 6 -6 598.4 128.13 8
-2 6 -4 144.53 34.36 6
2 -6 -4 124.98 46.03 9
2 -6 0 2405 231.39 3
2 -6 0 1343.48 113.4 9
2 -6 2 71.53 32.2 3
-2 6 4 108.84 57.05 1
2 -6 6 524.54 89.15 4
-2 6 6 551.74 130.02 1
-2 6 8 1.99 17.54 4
-2 6 10 31.95 40.12 1
-2 6 10 45.31 28.08 4
-2 6 12 93.09 82.73 1
-2 6 14 68.56 12.64 4
2 -8 -14 92.79 61.93 5
2 -8 -12 20.83 26.78 5
-2 8 -12 12.25 46.48 8
2 -8 -10 34.84 65.23 5
2 -8 -8 83.54 46.37 5
-2 8 -8 12.97 41.1 8
2 -8 -6 80.9 56.18 5
-2 8 -6 38.95 9.18 8
2 -8 -4 19.77 26.67 9
-2 8 -4 80.91 39.91 8
2 -8 -2 589.96 127.77 3
2 -8 -2 496.57 84.27 9
-2 8 -2 419.42 95.92 8
2 -8 0 3408.52 178.75 9
-2 8 0 3501.61 237.91 1
-2 8 0 3278.55 262.92 8
-2 8 2 488.34 96.34 8
2 -8 2 387.79 45.65 9
-2 8 2 549.84 105.27 1
2 -8 4 29.65 18.49 4
-2 8 4 1.09 22.47 1
2 -8 6 78.3 40.57 4
-2 8 6 25.84 22.23 4
-2 8 6 4.69 40.61 1
2 -8 8 82.05 45.6 4
-2 8 8 155.24 78.19 1
-2 8 8 55.43 26.75 4
2 -8 10 9.08 21.21 4
-2 8 10 20.24 54.53 1
2 -8 12 136.2 86.7 4
-2 8 12 117.15 62.18 1
-2 8 12 29.19 44.86 4
2 -8 14 19.29 45.4 4
-2 8 14 182.8 95.98 1
2 -8 14 174.21 97.98 10
-2 10 -12 27.43 52.43 8
-2 10 -10 118.57 71.98 8
-2 10 -8 56.58 57.56 8
-2 10 -6 183.1 71.66 8
2 -10 -4 9.74 5.74 3
-2 10 -4 20.23 14.66 8
-2 10 -2 33.3 23.28 1
-2 10 -2 45.06 33.06 8
-2 10 0 17.95 28.81 8
-2 10 2 50.78 22.91 8
-2 10 4 43.97 30.38 8
2 -10 4 23.43 21.25 4
-2 10 4 10.72 5.4 4
-2 10 6 257.34 81.36 1
-2 10 6 286.38 56.07 4
2 -10 6 234.14 64.26 4
-2 10 8 3.16 42.79 1
-2 10 8 56.37 22.59 4
2 -10 8 55.79 37.03 4
-2 10 10 10.13 59.59 1
2 -10 10 29.25 46.66 4
2 -10 12 72.47 68.11 10
-2 10 14 378.79 145.19 1
2 -10 14 214.44 93.96 10
2 -10 14 138.83 60.37 4
-2 12 -12 372 124.85 8
-2 12 -8 87.61 31.9 8
2 -12 -6 74.66 16.64 3
-2 12 -6 171.42 80.24 8
-2 12 -4 76.61 30.19 1
-2 12 -4 44.73 41.51 8
-2 12 -2 587.95 112.4 8
-2 12 -2 509.98 86.66 1
-2 12 0 5206.22 312.53 1
-2 12 0 5351.03 352.85 8
2 -12 2 405.36 53.41 4
-2 12 2 466.39 105.52 1
-2 12 2 483.43 101.97 8
2 -12 4 76.77 34.37 10
-2 12 4 123.9 65.57 1
2 -12 4 61.2 26.71 4
-2 12 4 80.5 47.05 8
-2 12 6 139.66 49.14 8
2 -12 6 44.94 44.47 10
2 -12 6 127.87 56.29 4
-2 12 6 154.96 77.37 1
-2 12 8 71.44 46.79 1
2 -12 8 43.8 5.1 10
2 -12 8 23.47 25.6 4
2 -12 10 21.73 31.09 10
-2 12 12 569.3 135.52 1
2 -12 12 309.12 109.95 10
2 -12 12 395.03 109.08 4
2 -12 14 187.44 100.05 10
-2 12 14 283.27 109.12 1
2 -12 14 35.21 47.17 4
2 -14 -8 32.96 20.91 3
2 -14 -6 345.99 137.53 3
-2 14 -6 273.62 86.33 8
-2 14 -4 113.16 37.75 1
-2 14 -4 92.95 20.4 8
-2 14 -2 743.61 111.15 1
-2 14 -2 584.31 123.92 8
-2 14 0 5745.03 340.75 1
-2 14 0 5268.85 363.82 8
-2 14 2 762.05 136.17 1
2 -14 2 582.87 65.42 4
-2 14 2 656.3 119.17 8
-2 14 4 239.63 89.92 1
2 -14 4 180.67 49.32 4
-2 14 4 169.53 61.48 8
-2 14 6 248.76 85.4 1
2 -14 6 96.21 42.16 4
-2 14 6 192.16 57.4 8
2 -14 8 14.82 32.45 10
-2 14 8 72.76 74.42 1
2 -14 8 35.95 25.51 4
2 -14 10 51.3 14 10
2 -14 10 61.03 47.57 4
-2 14 10 88.74 81.2 1
-2 14 12 231.31 110.13 1
2 -14 12 211.01 101.52 10
2 -14 12 274.92 96.11 4
-2 14 14 197.35 67.69 1
2 -14 14 333.53 124.21 4
-2 16 -12 276.46 108.86 8
-2 16 -10 8.94 23.75 8
2 -16 -8 283.36 108.75 3
-2 16 -8 195.16 87.68 8
-2 16 -6 515.24 127.25 8
-2 16 -4 334.46 65.47 1
-2 16 -4 261.99 96.3 8
-2 16 -2 527.93 94.39 1
-2 16 -2 527.56 123.04 8
-2 16 0 1266.17 164.83 1
-2 16 0 1250.89 184.15 8
-2 16 2 597.56 126.46 1
-2 16 2 684.85 131.93 8
-2 16 4 368.96 113.67 1
2 -16 4 203.12 50.15 4
-2 16 4 363.37 100.18 8
-2 16 6 458.17 120.36 1
2 -16 6 343.73 78.98 4
-2 16 6 342.13 82.45 8
-2 16 8 365.8 122.89 1
2 -16 8 293.16 80.27 4
-2 16 10 39.68 31.41 1
2 -16 10 5.32 18.93 4
2 -16 12 339.23 105.25 4
-2 16 12 368.57 141.74 1
-2 16 14 44.59 60.55 1
2 -16 14 11.27 53.6 4
-2 18 -12 112.76 43.93 8
-2 18 -8 510.68 147.4 8
-2 18 -6 734.46 169.85 8
-2 18 -4 164.78 62.98 8
-2 18 -2 127.09 53.62 8
-2 18 -2 13.08 12.3 1
-2 18 2 41.67 27.3 8
-2 18 2 58.02 51.38 1
-2 18 4 256.55 90.15 1
-2 18 4 89.15 49.05 8
-2 18 6 1312.31 222.11 1
-2 18 6 1054.65 155.66 8
-2 18 8 417.32 120.66 1
2 -18 8 414.95 92.04 4
2 -18 10 12.03 21.06 4
2 -18 12 218.89 69.67 4
-2 18 12 157.24 33.87 1
-2 20 -10 22.75 57.72 8
-2 20 -8 210.37 70.62 8
-2 20 -6 378.28 142.72 8
-2 20 -4 46.1 27.85 8
-2 20 -2 139.76 75.14 8
-2 20 -2 83.57 43.18 1
-2 20 0 153.07 89.25 8
-2 20 2 90.38 71 8
-2 20 2 211.05 80.36 1
-2 20 4 131.89 78.64 7
-2 20 4 28.95 56.37 8
-2 20 4 117.43 55.16 1
-2 20 6 480.73 134.29 1
-2 20 6 402.75 92.36 7
-2 20 8 394.82 138.54 1
-2 20 12 153.01 104.41 1
-2 22 -6 631.38 151.67 8
-2 22 -4 258.76 107.71 8
-2 22 -2 246.02 76.95 8
-2 22 2 115.3 75.65 7
-2 22 2 179.79 55.32 8
-2 22 2 268.11 84.66 1
-2 22 4 204.66 76.7 7
-2 22 4 160.77 63.86 8
-2 22 4 182.69 75.73 1
-2 22 6 671.83 141.76 7
-2 22 6 782.52 170.86 1
-2 22 8 132.54 71.65 1
-2 22 10 13.15 29.14 1
-2 22 12 243.72 118.78 1
-2 24 4 47.84 49.05 8
-2 24 6 48.39 51.4 1
-2 24 8 50.53 47.66 1
-3 9 -9 126.37 92.23 8
-3 9 -7 473.62 121.09 8
-3 9 -5 42.41 46.73 8
-3 9 -3 22.51 33.56 8
-3 9 -1 60.89 43.95 8
-3 11 -13 170.01 89.79 8
-3 11 -11 108.33 80.02 8
-3 11 -7 1324.37 220.3 8
-3 11 -5 431.55 118.38 8
3 -11 -5 394.74 103.55 9
-3 11 -3 185.04 96.92 8
-3 11 -1 60.29 58.89 8
-3 11 1 12.39 49.67 8
3 -11 1 100.01 56.66 3
3 -11 3 101.37 73.74 3
-3 11 3 102.25 59.89 1
-3 11 5 309.86 95.93 1
-3 11 7 1143.93 205.43 1
-3 11 9 105.87 56.71 1
-3 11 11 264.01 111.2 1
3 -11 13 14.3 32.27 10
-3 13 -7 385.45 133.06 8
-3 13 -5 255.76 62.87 8
-3 13 1 175.08 84.53 8
3 -13 1 76.61 57.26 3
-3 13 1 86.49 53.82 1
-3 13 3 22.37 25.54 8
-3 13 5 199.18 86.42 1
-3 13 7 656.27 169.39 1
-3 13 11 106.44 82.61 1
-3 15 -11 66.48 96.45 8
-3 15 -7 48.34 71.54 8
3 -15 -5 507.6 152.85 3
-3 15 -5 479.46 119.61 8
-3 15 -3 110.36 75.71 8
3 -15 -1 13.71 65.41 3
-3 15 -1 24.76 19.85 8
-3 15 1 41.37 19.49 8
-3 15 3 140.6 42.14 8
-3 15 3 93.96 7.81 1
-3 15 5 343.31 100.22 8
-3 15 5 611.76 161.47 1
-3 15 9 93.42 85.53 1
-3 15 11 69 72.54 1
-3 17 -9 163 97.72 8
-3 17 -5 133.65 66.51 8
-3 17 -1 255.78 90.19 1
-3 17 -1 281.63 101.03 8
-3 17 1 173.31 78.19 1
-3 17 1 211.98 76.8 8
-3 17 3 3.85 55.57 8
-3 17 5 173.9 77.39 1
-3 17 9 131.23 107.33 1
-3 17 11 122.93 64.94 1
-3 19 -11 90.37 61.46 8
-3 19 -5 98 49.82 8
-3 19 -1 475.09 114.36 1
-3 19 -1 562.83 146.84 8
-3 19 1 516.96 129.07 1
-3 19 1 388.98 119.4 8
-3 19 3 107.78 43.87 1
-3 19 3 82.35 72.31 8
-3 19 9 12.72 44.69 1
-3 21 -7 114.23 77.43 8
-3 21 -5 88.9 70.4 8
-3 21 -1 723.73 158.14 8
-3 21 1 708.32 148.58 1
-3 21 1 820.45 177.89 8
-3 21 3 124.37 59.14 1
-3 21 5 112.21 70.75 1
-3 21 7 19.57 35.67 1
-3 23 -3 94.75 28.66 8
-3 23 -1 439.47 126.65 8
-3 23 1 303.36 108.67 1
-3 23 1 391.8 128.21 8
-3 23 3 41.13 64.86 8
-3 23 9 191.89 122.04 1
-3 25 -1 30.72 57.72 8
-3 25 1 100.06 49.58 1
-3 25 1 57.11 61.75 8
-3 25 3 40.16 16.95 1
-3 25 3 83.96 72.54 8
-3 25 5 95.57 51.04 1
-3 27 -1 21.6 17.67 8
-3 27 1 16.05 10.76 1
-3 27 1 89.5 62.42 8
-3 27 3 89.68 82.34 1
-3 27 3 224.61 92.7 8
-3 29 -1 113.17 84.19 8
-3 29 1 79.82 72.31 8
-3 29 3 23.65 75.23 1
-4 14 -8 241.75 119.97 8
-4 14 -4 120.1 62.94 8
-4 16 -6 52 108.73 8
-4 16 -4 36.48 47.2 8
-4 16 -2 6.95 42.78 8
-4 16 0 80.26 62.26 8
-4 18 -4 23.62 43.31 8
-4 18 -2 87.89 83 8
-4 18 0 20.33 71.15 8
-4 18 2 50.58 87.83 8
-4 18 4 82.77 72.16 1
-4 18 6 36.94 81.72 1
-4 20 0 37.19 35.09 8
4 -20 0 49 44.04 3
-4 20 2 46.07 27.38 8
-4 20 2 118.24 85.36 1
-4 20 4 123.72 62.96 1
-4 20 4 67.42 83.45 8
4 -22 -2 102.71 82.85 3
-4 22 -2 116.04 98.54 8
4 -22 0 188.13 101.75 3

_iucr_refine_instructions_details 
;
TITL p1_v2_abs in Fdd2 #43
    2bisap-beta_1.64gpa.res
    created by SHELXL-2016/6 at 15:09:02 on 14-Sep-2020
REM reset to Fdd2 #43
CELL 0.56087 4.46449 34.867694 15.923362 90 90 90
ZERR 8 0.008109 0.110189 0.006726 0 0 0
LATT -4
SYMM -X,-Y,+Z
SYMM 0.25-X,0.25+Y,0.25+Z
SYMM 0.25+X,0.25-Y,0.25+Z
SFAC C H O
UNIT 160 112 16
SIMU 0.02 0.04 1.7 O1 > C12 C11 C15 C17 C18
SIMU 0.02 0.04 1.7 C2 C3
RIGU C3 C2 C1 C14 C13 C12 C11 C15 C17 C18 O1

L.S. 4
PLAN  5
CONF
BOND
fmap 2
acta
MORE -1
BOND $H
OMIT 1 7 -13
REM <olex2.extras>
REM <HklSrc "%./2bisAP-beta_1.64GPa.hkl">
REM </olex2.extras>

WGHT    0.051800   19.731201
FVAR       0.43058
O1    3   -0.343072   -0.671942   -0.290600    11.00000    0.10274    0.04188 =
         0.05774   -0.00502    0.00168    0.00261
C3    1   -0.654512   -0.733595   -0.355990    11.00000    0.02712    0.03766 =
         0.03588   -0.01331   -0.00338    0.01042
AFIX  43
H3    2   -0.604392   -0.721863   -0.305456    11.00000   -1.20000
AFIX  66
C2    1   -0.540152   -0.718689   -0.432788    11.00000    0.02503    0.03531 =
         0.03730   -0.00917    0.00357    0.02196
C1    1   -0.330194   -0.689260   -0.434187    11.00000    0.05035    0.05554 =
         0.05010    0.00037   -0.00024   -0.00124
C14   1   -0.225605   -0.675249   -0.510469    11.00000    0.06973    0.05598 =
         0.06013    0.01454    0.00333   -0.00231
AFIX  43
H14   2   -0.085129   -0.655558   -0.511405    11.00000   -1.20000
AFIX  65
C13   1   -0.330973   -0.690667   -0.585351    11.00000    0.07790    0.05938 =
         0.04421    0.01731    0.01241    0.00037
AFIX  43
H13   2   -0.260994   -0.681293   -0.636389    11.00000   -1.20000
AFIX  65
C12   1   -0.540931   -0.720097   -0.583953    11.00000    0.07279    0.04486 =
         0.04054    0.00503    0.00979    0.00871
C15   1   -0.645522   -0.734108   -0.507672    11.00000    0.04445    0.03286 =
         0.03334   -0.00187    0.00637    0.01572
AFIX   0
C11   1   -0.660369   -0.734560   -0.663000    11.00000    0.08749    0.04245 =
         0.02717    0.01533    0.01028    0.01656
AFIX  43
H11   2   -0.612526   -0.722432   -0.713258    11.00000   -1.20000
AFIX   0
C17   1   -0.223804   -0.666961   -0.357497    11.00000    0.05254    0.04770 =
         0.06535   -0.00148   -0.00622    0.00001
C18   1    0.018194   -0.640392   -0.368948    11.00000    0.03267    0.03341 =
         0.10728   -0.00599   -0.01518    0.01400
AFIX 137
H18C  2    0.172903   -0.645662   -0.328698    11.00000   -1.50000
H18B  2   -0.053944   -0.614702   -0.361125    11.00000   -1.50000
H18A  2    0.097538   -0.643035   -0.424682    11.00000   -1.50000
AFIX   0
HKLF 4




REM  p1_v2_abs in Fdd2 #43
REM R1 =  0.0865 for     222 Fo > 4sig(Fo)  and  0.1475 for all     366 data
REM     89 parameters refined using    145 restraints

END  
     
WGHT      0.0518     19.7288 

REM Highest difference peak  0.171,  deepest hole -0.173,  1-sigma level  0.050
Q1    1  -0.1218 -0.5834 -1.3788  11.00000  0.05    0.17
Q2    1  -0.8412 -0.7208 -1.5122  11.00000  0.05    0.17
Q3    1   0.1480 -0.5902 -1.3280  11.00000  0.05    0.15
Q4    1  -0.4498 -0.7095 -1.3368  11.00000  0.05    0.15
Q5    1  -0.3582 -0.7275 -1.7214  11.00000  0.05    0.14

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0865 for 222 Fo > 4sig(Fo) and 0.1475 for all 757 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.17, deepest hole -0.17
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.1475
  REM R1_gt = 0.0865
  REM wR_ref = 0.1988
  REM GOOF = 1.119
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 757
  REM Reflections_gt = 222
  REM Parameters = n/a
  REM Hole = -0.17
  REM Peak = 0.17
  REM Flack = -0.1(10)

  
;
_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_THETM01_2bisAP-beta_1640000kPa 
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
;
_vrf_PLAT089_2bisAP-beta_1640000kPa 
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       2.63 Note  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
In particular this affected the c direction due to crystal orientation.
;
_vrf_PLAT340_2bisAP-beta_1640000kPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.03077 Ang. 
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees on a very thin plate. This limited the number
of reflections that could be collected, as most of them were obscured by the
DAC, which together with weak scattering negatively affected the precision.
;
_vrf_PLAT911_2bisAP-beta_1640000kPa 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L= 0.555           190 Report
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
;
_vrf_PLAT412_2bisAP-beta_1640000kPa 
;
PROBLEM: Short Intra XH3 .. XHn     H14      ..H18A     .       1.66 Ang.  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
This, and relatively weak scattering, affected the precission of the final 
model. Specifically, H atoms were generated in idealized positions, as they
could not be located from the Fourier map.
;
_vrf_PLAT148_2bisAP-beta_1640000kPa 
;
PROBLEM: s.u. on the      a    - Axis is (Too) Large ....      0.008 Ang.  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
This, and relatively weak scattering, affected the precission of the final 
model.
;
_vrf_PLAT213_2bisAP-beta_1640000kPa 
;
PROBLEM: Atom C2              has ADP max/min Ratio .....        3.3 oblate
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
This, and relatively weak scattering, affected the precission of the final 
model.
;
_vrf_PLAT413_2bisAP-beta_1640000kPa 
;
PROBLEM: Short Inter XH3 .. XHn     H14      ..H18B     .       2.14 Ang.  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
This, and relatively weak scattering, affected the precission of the final 
model. Specifically, H atoms were generated in idealized positions, as they
could not be located from the Fourier map.
;
_vrf_PLAT906_2bisAP-beta_1640000kPa 
;
PROBLEM: Large K Value in the Analysis of Variance ......     10.987 Check 
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
This, and relatively weak scattering, affected the precission of the final 
model.
;
# 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_2bisAP-beta_720000kPa
_database_code_depnum_ccdc_archive 'CCDC 2039410'
loop_
_audit_author_name
_audit_author_address
'Daniel Tchon'
;Faculty of Chemistry, University of Warsaw
Poland
;
_audit_update_record             
;
2020-10-19 deposited with the CCDC.	2021-01-21 downloaded from the CCDC.
;
_audit_creation_date             2020-03-20
_audit_creation_method           
;
Olex2 1.2
(compiled May 29 2018 13:30:08 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            1,1'-Pyrene-1,8-diyldiethanone
_chemical_name_systematic        1,8-Diacetylpyrene
_chemical_formula_moiety         'C20 H14 O2'
_chemical_formula_sum            'C20 H14 O2'
_chemical_formula_weight         286.31
_chemical_absolute_configuration ad
_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      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   4.5651(17)
_cell_length_b                   35.55(9)
_cell_length_c                   16.071(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2608(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    278
_cell_measurement_temperature    284(11)
_cell_measurement_theta_max      21.0780
_cell_measurement_theta_min      2.7520
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79464
_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 dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1200
_exptl_crystal_preparation       
'Mounted in a Diamond-Anvil Cell using parabar oil as pressure medium.,Luminescent'
_exptl_crystal_pressure_history  
'Pressurized to 0.72 GPa and left to stabilize over 24 hours.'
_exptl_crystal_recrystallization_method 'from chloroform at room temperature'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_exptl_special_details_exptl_special_details 
;
High-pressure measurement at 0.72 GPa in a Merill-Basset Diamond Anvil Cell with
effective opening angle of 50 deg. and parabar 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  0.1286
_diffrn_reflns_av_unetI/netI     0.1141
_diffrn_reflns_Laue_measured_fraction_full 0.535
_diffrn_reflns_Laue_measured_fraction_max 0.535
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            2321
_diffrn_reflns_point_group_measured_fraction_full 0.528
_diffrn_reflns_point_group_measured_fraction_max 0.528
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.332
_diffrn_reflns_theta_min         2.782
_diffrn_ambient_temperature      284(11)
_diffrn_ambient_pressure         720000
_diffrn_ambient_environment      'Diamond Anvil Cell filled with parabar oil'
_diffrn_crystal_treatment        
'Pressurized slowly in parabar oil as a hydrostatic medium.'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4391
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.535
_diffrn_measured_fraction_theta_max 0.535
_diffrn_measurement_details      
'List of Runs (angles in degrees, time in seconds): # Type Start End Width tₑₓₚ ω θ κ φ Frames -------------------------------------------------------------------------- 1 ω -25.00 0.00 1.00 130.00 -- 9.85 -37.00-120.00 25 2 ω -35.00 -9.00 1.00 130.00 -- 9.85 -19.00-120.00 26 3 ω -26.00 7.00 1.00 130.00 -- 9.85 19.00 30.00 33 4 ω 4.00 30.00 1.00 130.00 -- 9.85 56.00 161.00 26 5 ω -13.00 19.00 1.00 130.00 -- 9.85 -81.00-151.00 32 6 ω -20.00 5.00 1.00 130.00 -- 9.85 26.00 -7.00 25 7 ω -52.00 -26.00 1.00 130.00 -- -11.72 19.00 30.00 26 8 ω -65.00 -39.00 1.00 130.00 -- -11.72 134.00 123.00 26'
_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_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0011072000
_diffrn_orient_matrix_UB_12      -0.0199830000
_diffrn_orient_matrix_UB_13      0.0015945000
_diffrn_orient_matrix_UB_21      0.1112260000
_diffrn_orient_matrix_UB_22      0.0003733000
_diffrn_orient_matrix_UB_23      0.0307383000
_diffrn_orient_matrix_UB_31      -0.1082657000
_diffrn_orient_matrix_UB_32      0.0005452000
_diffrn_orient_matrix_UB_33      0.0315834000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\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         0.901
_reflns_Friedel_fraction_full    0.520
_reflns_Friedel_fraction_max     0.519
_reflns_number_gt                293
_reflns_number_total             631
_reflns_odcompleteness_completeness 52.02
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details .
_refine_ls_abs_structure_Flack   .
_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         631
_refine_ls_number_restraints     79
_refine_ls_R_factor_all          0.1706
_refine_ls_R_factor_gt           0.0675
_refine_ls_restrained_S_all      1.025
_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)+(0.0804P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1511
_refine_ls_wR_factor_ref         0.2116
_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
 C1, C15, C2, C12, C3, C13, C11, C14, C17, C18, O1
 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:
 C13(H13), C3(H3), C11(H11), C14(H14)
3.b Idealised Me refined as rotating group:
 C18(H18A,H18C,H18B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C15 C 0.600(2) 0.4865(8) 0.3425(7) 0.048(6) Uani 1 1 d . U . . .
C2 C 0.709(3) 0.4690(8) 0.4184(7) 0.055(6) Uani 1 1 d . U . . .
C12 C 0.708(3) 0.4697(9) 0.2648(7) 0.051(7) Uani 1 1 d . U . . .
C1 C 0.905(3) 0.4378(9) 0.4163(9) 0.058(6) Uani 1 1 d . U . . .
C13 C 0.909(3) 0.4423(9) 0.2656(7) 0.056(7) Uani 1 1 d . U . . .
H13 H 0.9877 0.4347 0.2151 0.067 Uiso 1 1 calc R . . . .
C3 C 0.593(3) 0.4850(9) 0.4939(6) 0.058(7) Uani 1 1 d . U . . .
H3 H 0.6472 0.4744 0.5446 0.070 Uiso 1 1 calc R . . . .
C11 C 0.594(3) 0.4863(9) 0.1898(6) 0.053(8) Uani 1 1 d . U . . .
H11 H 0.6582 0.4769 0.1389 0.064 Uiso 1 1 calc R . . . .
C14 C 1.007(3) 0.4244(9) 0.3387(9) 0.064(7) Uani 1 1 d . U . . .
H14 H 1.1366 0.4042 0.3360 0.077 Uiso 1 1 calc R . . . .
C17 C 1.012(3) 0.4175(10) 0.4911(9) 0.068(7) Uani 1 1 d . U . . .
C18 C 1.254(3) 0.3885(10) 0.4829(11) 0.082(8) Uani 1 1 d . U . . .
H18A H 1.4113 0.3987 0.4505 0.122 Uiso 1 1 calc GR . . . .
H18C H 1.1783 0.3664 0.4559 0.122 Uiso 1 1 calc GR . . . .
H18B H 1.3248 0.3819 0.5372 0.122 Uiso 1 1 calc GR . . . .
O1 O 0.890(2) 0.4217(7) 0.5591(6) 0.094(9) Uani 1 1 d . U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C15 0.041(7) 0.064(18) 0.038(4) -0.006(6) -0.002(5) -0.008(9)
C2 0.048(8) 0.076(17) 0.040(5) 0.000(7) -0.003(5) -0.002(8)
C12 0.055(8) 0.06(2) 0.040(5) 0.000(7) 0.009(5) -0.014(9)
C1 0.045(6) 0.079(17) 0.051(5) 0.003(7) 0.000(5) 0.000(8)
C13 0.064(9) 0.06(2) 0.044(6) -0.007(8) 0.005(6) -0.011(9)
C3 0.054(9) 0.09(2) 0.034(5) -0.005(8) -0.006(5) 0.004(10)
C11 0.075(11) 0.05(3) 0.034(5) -0.006(7) 0.007(5) -0.012(11)
C14 0.053(8) 0.074(19) 0.066(6) 0.002(8) 0.004(6) -0.003(8)
C17 0.057(8) 0.08(2) 0.069(6) 0.005(8) -0.012(6) -0.012(9)
C18 0.059(8) 0.09(2) 0.097(11) 0.023(12) 0.001(7) -0.005(11)
O1 0.103(7) 0.12(3) 0.057(5) 0.011(7) -0.007(5) 0.016(10)

_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
C15 C15 1.33(4) 2_665 ?
C15 C2 1.46(2) . ?
C15 C12 1.47(2) . ?
C2 C1 1.43(4) . ?
C2 C3 1.44(2) . ?
C12 C13 1.34(3) . ?
C12 C11 1.44(3) . ?
C1 C14 1.41(2) . ?
C1 C17 1.48(3) . ?
C13 C14 1.41(3) . ?
C3 C3 1.37(5) 2_665 ?
C11 C11 1.30(5) 2_665 ?
C17 C18 1.52(4) . ?
C17 O1 1.235(19) . ?

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
C15 C15 C2 123.0(9) 2_665 . ?
C15 C15 C12 121.7(11) 2_665 . ?
C2 C15 C12 115.1(17) . . ?
C1 C2 C15 121.8(14) . . ?
C1 C2 C3 123.8(15) . . ?
C3 C2 C15 114.3(17) . . ?
C13 C12 C15 121.1(16) . . ?
C13 C12 C11 123.7(14) . . ?
C11 C12 C15 115(2) . . ?
C2 C1 C17 124.4(16) . . ?
C14 C1 C2 119.4(17) . . ?
C14 C1 C17 116(2) . . ?
C12 C13 C14 123.9(16) . . ?
C3 C3 C2 122.5(12) 2_665 . ?
C11 C11 C12 123.1(12) 2_665 . ?
C13 C14 C1 118(2) . . ?
C1 C17 C18 120.0(16) . . ?
O1 C17 C1 121(2) . . ?
O1 C17 C18 119.1(19) . . ?

_iucr_refine_instructions_details 
;
TITL p1_v1_abs in Fdd2 #43
REM reset to Fdd2 #43
CELL 0.71073 4.5651 35.545356 16.070894 90 90 90
ZERR 8 0.001739 0.087608 0.005164 0 0 0
LATT -4
SYMM -X,-Y,+Z
SYMM 0.25-X,0.25+Y,0.25+Z
SYMM 0.25+X,0.25-Y,0.25+Z
SFAC C H O
UNIT 160 112 16
RIGU C1 C15 C2 C12 C3 C13 C11 C14 C17 C18 O1
 
L.S. 4
PLAN  5
SIZE 0.06 0.18 0.24
BOND
fmap 2
ACTA
REM <olex2.extras>
REM <HklSrc "%./p1_v1_abs.hkl">
REM </olex2.extras>
 
WGHT    0.080400
FVAR       0.60782
C15    1    0.600448    0.486537    0.342488    11.00000    0.04109    0.06435 =
         0.03772   -0.00588   -0.00208   -0.00847
C2    1    0.708573    0.468961    0.418386    11.00000    0.04826    0.07650 =
         0.03981   -0.00022   -0.00348   -0.00155
C12    1    0.708135    0.469698    0.264792    11.00000    0.05490    0.05824 =
         0.04011    0.00008    0.00871   -0.01381
C1    1    0.904909    0.437775    0.416321    11.00000    0.04542    0.07857 =
         0.05134    0.00265    0.00047   -0.00036
C13    1    0.908567    0.442327    0.265639    11.00000    0.06355    0.05967 =
         0.04433   -0.00664    0.00483   -0.01069
AFIX  43
H13    2    0.987700    0.434664    0.215081    11.00000   -1.20000
AFIX   0
C3    1    0.593024    0.484967    0.493908    11.00000    0.05445    0.08731 =
         0.03352   -0.00499   -0.00612    0.00384
AFIX  43
H3    2    0.647217    0.474418    0.544578    11.00000   -1.20000
AFIX   0
C11    1    0.594190    0.486268    0.189802    11.00000    0.07539    0.05039 =
         0.03372   -0.00600    0.00714   -0.01173
AFIX  43
H11    2    0.658215    0.476901    0.138922    11.00000   -1.20000
AFIX   0
C14    1    1.007327    0.424352    0.338736    11.00000    0.05331    0.07354 =
         0.06561    0.00207    0.00386   -0.00315
AFIX  43
H14    2    1.136611    0.404171    0.335966    11.00000   -1.20000
AFIX   0
C17    1    1.011985    0.417523    0.491102    11.00000    0.05743    0.07922 =
         0.06868    0.00548   -0.01160   -0.01177
C18   1    1.253818    0.388458    0.482942    11.00000    0.05938    0.08815 =
         0.09706    0.02314    0.00072   -0.00512
AFIX 137
H18A  2    1.411336    0.398712    0.450509    11.00000   -1.50000
H18C  2    1.178259    0.366414    0.455912    11.00000   -1.50000
H18B  2    1.324829    0.381862    0.537243    11.00000   -1.50000
AFIX   0
O1   3    0.890173    0.421736    0.559070    11.00000    0.10296    0.12199 =
         0.05700    0.01136   -0.00669    0.01604
HKLF 4
 
REM  p1_v1_abs in Fdd2 #43
REM R1 =  0.0675 for     293 Fo > 4sig(Fo)  and  0.1706 for all     631 data
REM    101 parameters refined using     79 restraints
 
END  
     
WGHT      0.0804      0.0000 

REM Highest difference peak  0.166,  deepest hole -0.176,  1-sigma level  0.046
Q1    1   0.6307  0.4863  0.6385  11.00000  0.05    0.17
Q2    1   1.3474  0.4362  0.3427  11.00000  0.05    0.15
Q3    1   1.5687  0.4185  0.3800  11.00000  0.05    0.15
Q4    1   1.0999  0.3973  0.2580  11.00000  0.05    0.14
Q5    1   1.3466  0.4318  0.4952  11.00000  0.05    0.14

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0675 for 293 Fo > 4sig(Fo) and 0.1706 for all 2469 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.17, deepest hole -0.18
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.1706
  REM R1_gt = 0.0675
  REM wR_ref = 0.2116
  REM GOOF = 1.070
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 2469
  REM Reflections_gt = 293
  REM Parameters = n/a
  REM Hole = -0.18
  REM Peak = 0.17
  REM Flack = -0.2(10)

  
;
_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 1.488
_oxdiff_exptl_absorpt_empirical_full_min 0.808

# start Validation Reply Form
_vrf_RINTA01_2bisAP-beta_720000kPa 
;
PROBLEM: The value of Rint is greater than 0.12
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 50 degrees. This limited the number of reflections
that could be collected, as most of them were obscured by the DAC.
This, and relatively weak scattering, affected the precission of the final
intensities.
;
_vrf_PLAT029_2bisAP-beta_720000kPa 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.535 Why?  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 50 degrees on a very thin plate. This limited the number
of reflections that could be collected, as most of them were obscured
by the DAC.
;
_vrf_PLAT340_2bisAP-beta_720000kPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............       0.03 Ang.  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 50 degrees on a very thin plate. This limited the number
of reflections that could be collected, as most of them were obscured by the
DAC, which together with weak scattering negatively affected the precision.
;
_vrf_PLAT911_2bisAP-beta_720000kPa 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L= 0.600            61 Report
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 50 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
;
_vrf_PLAT915_2bisAP-beta_720000kPa 
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         52 % 
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 50 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
Moreover, high Friedel pair coverage was unnecessary, as space group information
was determined using complete dataset gathered on this sample before experiment. 
;
_vrf_PLAT089_2bisAP-beta_720000kPa 
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       3.29 Note  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 50 degrees on a very thin plate. This limited the number
of reflections that could be collected, as most of them were obscured
by the DAC.
;
_vrf_PLAT026_2bisAP-beta_720000kPa 
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        46% Check 
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 50 degrees on a very thin plate. This limited the number
of reflections that could be collected, as most of them were obscured
by the DAC.
;
_vrf_PLAT148_2bisAP-beta_720000kPa 
;
PROBLEM: s.u. on the      b    - Axis is (Too) Large ....     0.0900 Ang.  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 50 degrees on a very thin plate. This limited the number
of reflections that could be collected, as most of them were obscured
by the DAC. b direction, perpendicular to the plate large face was particularly
affected due to crystal orientation.
;
_vrf_PLAT978_2bisAP-beta_720000kPa 
;
PROBLEM: Number C-C Bonds with Positive Residual Density.          0 Info  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 50 degrees. This limited the number of reflections
that could be collected, as most of them were obscured by the DAC.
This, and relatively weak scattering, affected the precission of the final
model.
;
# 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_2bisAP-beta_1570000kPa
_database_code_depnum_ccdc_archive 'CCDC 2039414'
loop_
_audit_author_name
_audit_author_address
'Daniel Tchon'
;Faculty of Chemistry, University of Warsaw
Poland
;
_audit_update_record             
;
2020-10-19 deposited with the CCDC.	2021-01-21 downloaded from the CCDC.
;
_audit_creation_date             2019-08-06
_audit_creation_method           
;
Olex2 1.2
(compiled May 29 2018 13:30:08 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            1,1'-Pyrene-1,8-diyldiethanone
_chemical_name_systematic        1,8-Diacetylpyrene
_chemical_formula_moiety         'C20 H14 O2'
_chemical_formula_sum            'C20 H14 O2'
_chemical_formula_weight         286.31
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H12 O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   4.5836(11)
_cell_length_b                   34.10(6)
_cell_length_c                   16.062(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2511(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    447
_cell_measurement_temperature    291.3(3)
_cell_measurement_theta_max      24.7740
_cell_measurement_theta_min      2.7970
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79559
_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 dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1200
_exptl_crystal_preparation       
'Mounted in a Diamond-Anvil Cell using parabar oil as pressure medium.,Luminescent'
_exptl_crystal_pressure_history  
'Pressurized to 1.57 GPa and left to stabilize over 24 hours.'
_exptl_crystal_recrystallization_method 'from chloroform at room temperature'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
High-pressure measurement at 1.57 GPa in a Merill-Basset Diamond Anvil Cell with
effective opening angle of 50 deg. and parabar 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  0.0528
_diffrn_reflns_av_unetI/netI     0.0620
_diffrn_reflns_Laue_measured_fraction_full 0.514
_diffrn_reflns_Laue_measured_fraction_max 0.416
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            2015
_diffrn_reflns_point_group_measured_fraction_full 0.490
_diffrn_reflns_point_group_measured_fraction_max 0.385
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.194
_diffrn_reflns_theta_min         2.804
_diffrn_ambient_temperature      291.3(3)
_diffrn_ambient_pressure         1570000
_diffrn_ambient_environment      'Diamond Anvil Cell filled with parabar oil'
_diffrn_crystal_treatment        
'Pressurized slowly in parabar oil as a hydrostatic medium.'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4391
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.514
_diffrn_measured_fraction_theta_max 0.416
_diffrn_measurement_details      
'List of Runs (angles in degrees, time in seconds): # Type Start End Width tₑₓₚ ω θ κ φ Frames -------------------------------------------------------------------------- 1 ω -25.00 0.00 1.00 130.00 -- 9.85 -37.00-120.00 25 2 ω -35.00 -9.00 1.00 130.00 -- 9.85 -19.00-120.00 26 3 ω -26.00 7.00 1.00 130.00 -- 9.85 19.00 30.00 33 4 ω 4.00 30.00 1.00 130.00 -- 9.85 56.00 161.00 26 5 ω -13.00 19.00 1.00 130.00 -- 9.85 -81.00-151.00 32 6 ω -20.00 5.00 1.00 130.00 -- 9.85 26.00 -7.00 25 7 ω -52.00 -26.00 1.00 130.00 -- -11.72 19.00 30.00 26 8 ω -65.00 -39.00 1.00 130.00 -- -11.72 134.00 123.00 26'
_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_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0027734000
_diffrn_orient_matrix_UB_12      -0.0206846000
_diffrn_orient_matrix_UB_13      0.0004062000
_diffrn_orient_matrix_UB_21      0.1153138000
_diffrn_orient_matrix_UB_22      0.0002091000
_diffrn_orient_matrix_UB_23      -0.0297363000
_diffrn_orient_matrix_UB_31      0.1036019000
_diffrn_orient_matrix_UB_32      0.0003590000
_diffrn_orient_matrix_UB_33      0.0328764000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\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         0.791
_reflns_Friedel_fraction_full    0.464
_reflns_Friedel_fraction_max     0.352
_reflns_number_gt                454
_reflns_number_total             659
_reflns_odcompleteness_completeness 48.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXD (Sheldrick, 2008)'
_refine_diff_density_max         0.103
_refine_diff_density_min         -0.105
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details .
_refine_ls_abs_structure_Flack   .
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         659
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0518
_refine_ls_restrained_S_all      1.040
_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)+(0.0366P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.1012
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C14(H14), C13(H13), C11(H11)
2.b Idealised Me refined as rotating group:
 C18(H18B,H18A,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.9047(10) 0.4200(3) 0.4592(2) 0.066(4) Uani 1 1 d . . . . .
C3 C 0.5962(11) 0.4856(3) 0.3931(3) 0.045(5) Uani 1 1 d . . . . .
H3 H 0.6605 0.4760 0.4441 0.054 Uiso 1 1 calc R . . . .
C2 C 0.7127(10) 0.4683(3) 0.3178(3) 0.042(6) Uani 1 1 d . . . . .
C1 C 0.9183(10) 0.4382(4) 0.3157(3) 0.043(5) Uani 1 1 d . . . . .
C14 C 1.0252(11) 0.4252(4) 0.2384(4) 0.051(6) Uani 1 1 d . . . . .
H14 H 1.1655 0.4055 0.2368 0.061 Uiso 1 1 calc R . . . .
C13 C 0.9239(12) 0.4414(4) 0.1639(3) 0.055(6) Uani 1 1 d . . . . .
H13 H 1.0006 0.4327 0.1136 0.066 Uiso 1 1 calc R . . . .
C12 C 0.7147(10) 0.4697(4) 0.1641(3) 0.045(6) Uani 1 1 d . . . . .
C15 C 0.6059(9) 0.4850(3) 0.2418(3) 0.042(4) Uani 1 1 d . . . . .
C11 C 0.6011(12) 0.4859(4) 0.0874(3) 0.046(6) Uani 1 1 d . . . . .
H11 H 0.6706 0.4764 0.0369 0.056 Uiso 1 1 calc R . . . .
C17 C 1.0235(12) 0.4178(4) 0.3914(4) 0.055(6) Uani 1 1 d . . . . .
C18 C 1.2711(11) 0.3875(4) 0.3821(5) 0.056(7) Uani 1 1 d . . . . .
H18B H 1.3384 0.3797 0.4363 0.084 Uiso 1 1 calc GR . . . .
H18A H 1.4295 0.3989 0.3515 0.084 Uiso 1 1 calc GR . . . .
H18C H 1.1994 0.3649 0.3529 0.084 Uiso 1 1 calc GR . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.082(3) 0.061(14) 0.054(3) 0.001(3) -0.010(2) 0.014(4)
C3 0.041(3) 0.064(16) 0.029(2) -0.002(4) -0.001(2) -0.001(4)
C2 0.031(3) 0.060(19) 0.036(3) 0.000(4) 0.000(2) -0.001(4)
C1 0.033(3) 0.055(17) 0.042(3) 0.011(5) 0.000(2) -0.011(4)
C14 0.037(3) 0.05(2) 0.063(4) -0.005(6) 0.004(3) 0.003(4)
C13 0.048(3) 0.07(2) 0.045(3) -0.006(5) 0.012(3) -0.011(4)
C12 0.036(3) 0.059(19) 0.038(3) -0.006(4) 0.004(3) -0.014(4)
C15 0.033(2) 0.060(14) 0.033(2) -0.004(4) 0.002(3) -0.012(4)
C11 0.060(4) 0.05(2) 0.027(2) -0.003(4) 0.003(2) -0.021(6)
C17 0.043(3) 0.06(2) 0.061(4) 0.004(5) -0.008(3) 0.001(4)
C18 0.043(3) 0.03(2) 0.092(5) 0.017(6) -0.004(3) 0.005(4)

_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 1.220(8) . ?
C3 C3 1.319(17) 2_665 ?
C3 C2 1.448(9) . ?
C2 C1 1.394(14) . ?
C2 C15 1.433(8) . ?
C1 C14 1.406(9) . ?
C1 C17 1.482(11) . ?
C14 C13 1.396(11) . ?
C13 C12 1.360(13) . ?
C12 C15 1.442(9) . ?
C12 C11 1.446(10) . ?
C15 C15 1.412(18) 2_665 ?
C11 C11 1.34(2) 2_665 ?
C17 C18 1.543(14) . ?

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
C3 C3 C2 123.4(4) 2_665 . ?
C1 C2 C3 124.8(5) . . ?
C1 C2 C15 120.1(6) . . ?
C15 C2 C3 115.1(7) . . ?
C2 C1 C14 119.3(7) . . ?
C2 C1 C17 123.0(6) . . ?
C14 C1 C17 117.7(8) . . ?
C13 C14 C1 121.0(8) . . ?
C12 C13 C14 120.9(7) . . ?
C13 C12 C15 120.1(6) . . ?
C13 C12 C11 121.6(5) . . ?
C15 C12 C11 118.3(8) . . ?
C2 C15 C12 118.4(7) . . ?
C15 C15 C2 121.5(4) 2_665 . ?
C15 C15 C12 120.0(5) 2_665 . ?
C11 C11 C12 121.7(5) 2_665 . ?
O1 C17 C1 124.0(7) . . ?
O1 C17 C18 117.1(8) . . ?
C1 C17 C18 118.3(7) . . ?

_iucr_refine_instructions_details 
;
TITL p3_v1 in Fdd2 #43
REM Best SHELXD solution FINAL CC 76.03
REM Fragments: 18
REM reset to Fdd2 #43
CELL 0.71073 4.583586 34.102004 16.061832 90 90 90
ZERR 8 0.001099 0.056517 0.0043 0 0 0
LATT -4
SYMM -X,-Y,+Z
SYMM 0.25-X,0.25+Y,0.25+Z
SYMM 0.25+X,0.25-Y,0.25+Z
SFAC C H O
UNIT 160 112 16
 
L.S. 4 0 0
PLAN  2
fmap 2
ACTA
REM <olex2.extras>
REM <HklSrc "%./p3_v1.hkl">
REM </olex2.extras>
 
WGHT    0.036600
FVAR       1.01446
O1    3    0.904701    0.419983    0.459250    11.00000    0.08219    0.06054 =
         0.05407    0.00056   -0.00992    0.01427
C3    1    0.596249    0.485619    0.393110    11.00000    0.04098    0.06427 =
         0.02945   -0.00171   -0.00072   -0.00128
AFIX  43
H3    2    0.660464    0.475986    0.444085    11.00000   -1.20000
AFIX   0
C2    1    0.712699    0.468276    0.317822    11.00000    0.03146    0.05983 =
         0.03615    0.00044   -0.00024   -0.00055
C1    1    0.918310    0.438181    0.315667    11.00000    0.03345    0.05484 =
         0.04175    0.01051   -0.00046   -0.01143
C14    1    1.025168    0.425202    0.238394    11.00000    0.03707    0.05170 =
         0.06290   -0.00522    0.00426    0.00259
AFIX  43
H14    2    1.165493    0.405518    0.236829    11.00000   -1.20000
AFIX   0
C13    1    0.923949    0.441396    0.163947    11.00000    0.04801    0.07325 =
         0.04498   -0.00589    0.01221   -0.01086
AFIX  43
H13    2    1.000603    0.432720    0.113601    11.00000   -1.20000
AFIX   0
C12    1    0.714747    0.469690    0.164070    11.00000    0.03644    0.05932 =
         0.03812   -0.00617    0.00396   -0.01445
C15    1    0.605942    0.484966    0.241793    11.00000    0.03250    0.06047 =
         0.03255   -0.00386    0.00178   -0.01159
C11    1    0.601087    0.485899    0.087437    11.00000    0.05956    0.05255 =
         0.02667   -0.00280    0.00341   -0.02106
AFIX  43
H11    2    0.670557    0.476442    0.036876    11.00000   -1.20000
AFIX   0
C17    1    1.023515    0.417814    0.391444    11.00000    0.04294    0.06003 =
         0.06079    0.00379   -0.00781    0.00090
C18   1    1.271085    0.387476    0.382139    11.00000    0.04316    0.03313 =
         0.09180    0.01746   -0.00356    0.00535
AFIX 137
H18B  2    1.338446    0.379728    0.436289    11.00000   -1.50000
H18A  2    1.429459    0.398915    0.351483    11.00000   -1.50000
H18C  2    1.199393    0.364906    0.352855    11.00000   -1.50000
AFIX   0
HKLF 4
 
REM  p3_v1 in Fdd2 #43
REM R1 =  0.0518 for     454 Fo > 4sig(Fo)  and  0.0871 for all     659 data
REM    101 parameters refined using      1 restraints
 
END  
     
WGHT      0.0367      0.0000 

REM Highest difference peak  0.103,  deepest hole -0.105,  1-sigma level  0.028
Q1    1   0.7542  0.4867  0.4707  11.00000  0.05    0.10
Q2    1   0.9068  0.4149  0.2793  11.00000  0.05    0.10

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0518 for 454 Fo > 4sig(Fo) and 0.0871 for all 2114 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.10, deepest hole -0.10
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0871
  REM R1_gt = 0.0518
  REM wR_ref = 0.1012
  REM GOOF = 1.041
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 2114
  REM Reflections_gt = 454
  REM Parameters = n/a
  REM Hole = -0.10
  REM Peak = 0.10
  REM Flack = -2.2(10)

  
;
_olex2_exptl_crystal_mounting_method 
'in a DAC, opening angle 50 degrees, in Paratone N oil'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_diffrn_reflns_filtered   339
_oxdiff_exptl_absorpt_empirical_details 
'Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling'
_oxdiff_exptl_absorpt_empirical_full_max 1.991
_oxdiff_exptl_absorpt_empirical_full_min 0.672

# start Validation Reply Form
_vrf_PLAT029_2bisAP-beta_1570000kPa 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.514 Why?  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 50 degrees on a very thin plate. This limited the number 
of reflections that could be collected, as most of them were obscured 
by the DAC.
;
_vrf_PLAT340_2bisAP-beta_1570000kPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01169 Ang. 
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 50 degrees on a very thin plate. This limited the number
of reflections that could be collected, as most of them were obscured by the
DAC, which together with weak scattering negatively affected the precision.
;
_vrf_PLAT911_2bisAP-beta_1570000kPa 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L= 0.600            66 Report
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 50 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
;
_vrf_PLAT915_2bisAP-beta_1570000kPa 
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         35 % 
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 50 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
Moreover, high Friedel pair coverage was unnecessary, as space group information
was determined using complete dataset gathered on this sample before experiment. 
;
_vrf_PLAT089_2bisAP-beta_1570000kPa 
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       3.64 Note  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 50 degrees on a very thin plate. This limited the number 
of reflections that could be collected, as most of them were obscured 
by the DAC.
;
_vrf_PLAT148_2bisAP-beta_1570000kPa 
;
PROBLEM: s.u. on the      b    - Axis is (Too) Large ....     0.0600 Ang.  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 50 degrees on a very thin plate. This limited the number 
of reflections that could be collected, as most of them were obscured 
by the DAC. b direction was particularly affected due to crystal orientation.
;
_vrf_PLAT906_2bisAP-beta_1570000kPa 
;
PROBLEM: Large K Value in the Analysis of Variance ......      5.496 Check 
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 50 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
This, and relatively weak scattering, affected the precission of the final 
model.
;
_vrf_PLAT978_2bisAP-beta_1570000kPa 
;
PROBLEM: Number C-C Bonds with Positive Residual Density.          0 Info  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 50 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
This, and relatively weak scattering, affected the precission of the final 
model.
;
# 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_2bisAP-delta_2120000kPa
_database_code_depnum_ccdc_archive 'CCDC 2039417'
loop_
_audit_author_name
_audit_author_address
'Daniel Tchon'
;Faculty of Chemistry, University of Warsaw
Poland
;
_audit_update_record             
;
2020-10-19 deposited with the CCDC.	2021-01-21 downloaded from the CCDC.
;
_audit_creation_date             2020-04-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            1,1'-Pyrene-1,8-diyldiethanone
_chemical_name_systematic        1,8-Diacetylpyrene
_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 0.0015 0.0009 '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 0.0056 0.0036 '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                   8.2093(19)
_cell_length_b                   21.333(7)
_cell_length_c                   6.973(8)
_cell_angle_alpha                90
_cell_angle_beta                 99.07(5)
_cell_angle_gamma                90
_cell_volume                     1205.8(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    771
_cell_measurement_temperature    296.2(4)
_cell_measurement_theta_max      18.0450
_cell_measurement_theta_min      2.1060
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81465
_exptl_absorpt_correction_type   multi-scan
_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)
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    1.577
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_preparation       
'Mounted in a Diamond-Anvil Cell using parabar oil as pressure medium.,Luminescent'
_exptl_crystal_pressure_history  
'Pressurized to 2.12 GPa and left to stabilize over 24 hours.'
_exptl_crystal_recrystallization_method 'from acetonitrile at room temperature'
_exptl_crystal_size_max          0.175
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.075
_exptl_special_details           
;
High-pressure measurement at 2.12 GPa in a Merill-Basset Diamond Anvil Cell with
effective opening angle of 33 deg. and parabar 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  0.1138
_diffrn_reflns_av_unetI/netI     0.1515
_diffrn_reflns_Laue_measured_fraction_full 0.483
_diffrn_reflns_Laue_measured_fraction_max 0.483
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            4747
_diffrn_reflns_point_group_measured_fraction_full 0.483
_diffrn_reflns_point_group_measured_fraction_max 0.483
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         19.744
_diffrn_reflns_theta_min         2.121
_diffrn_ambient_temperature      296.2(4)
_diffrn_ambient_pressure         2120000
_diffrn_ambient_environment      'Diamond Anvil Cell filled with parabar oil'
_diffrn_crystal_treatment        
'Pressurized slowly in parabar oil as a hydrostatic medium.'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0064
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.483
_diffrn_measured_fraction_theta_max 0.483
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -12.00   52.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -       13.5545  -67.0000   23.0000 64

#__ type_ start__ end____ width___ exp.time_
  2 omega  -18.00   51.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -       13.5545  -53.0000 -162.0000 69

#__ type_ start__ end____ width___ exp.time_
  3 omega  -26.00   -1.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -       13.5545   53.0000  162.0000 25

#__ type_ start__ end____ width___ exp.time_
  4 omega  -36.00    0.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -       13.5545   39.0000  -12.0000 36

#__ type_ start__ end____ width___ exp.time_
  5 omega  -45.00    5.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.8670   67.0000  157.0000 50

#__ type_ start__ end____ width___ exp.time_
  6 omega  -51.00    4.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.8670   67.0000  -23.0000 55

#__ type_ start__ end____ width___ exp.time_
  7 omega  -23.00   39.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.8670  -39.0000   12.0000 62

#__ type_ start__ end____ width___ exp.time_
  8 omega  -24.00   41.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.8670  -39.0000 -167.0000 65

#__ type_ start__ end____ width___ exp.time_
  9 omega    8.00   46.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.8670 -114.0000 -135.0000 38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 
'Diamond Anvil Cell, effective opening angle of 33 deg.'
_diffrn_orient_matrix_UB_11      0.0095641000
_diffrn_orient_matrix_UB_12      -0.0109904000
_diffrn_orient_matrix_UB_13      0.0736113000
_diffrn_orient_matrix_UB_21      -0.0639619000
_diffrn_orient_matrix_UB_22      0.0070398000
_diffrn_orient_matrix_UB_23      0.0095293000
_diffrn_orient_matrix_UB_31      -0.0243895000
_diffrn_orient_matrix_UB_32      -0.0227783000
_diffrn_orient_matrix_UB_33      -0.0325058000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56087
_diffrn_source                   'SuperNova (Ag) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                536
_reflns_number_total             1064
_reflns_odcompleteness_completeness 47.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     19.69
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         1064
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1819
_refine_ls_R_factor_gt           0.0794
_refine_ls_restrained_S_all      1.045
_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)+(0.0799P)²+0.7392P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1542
_refine_ls_wR_factor_ref         0.1974
_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. Uiso/Uaniso restraints and constraints
Uanis(C9) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.005
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C11(H11), C8(H8), C13(H13), C10(H10), C3(H3), C7(H7), C14(H14)
3.b Idealised Me refined as rotating group:
 C20(H20B,H20A,H20C), C18(H18B,H18A,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
O2 O 0.0747(5) 0.5365(2) 0.7986(11) 0.051(3) Uani 1 1 d . . . . .
O1 O 0.0531(6) 0.2573(2) 0.3519(12) 0.052(3) Uani 1 1 d . . . . .
C4 C 0.1951(8) 0.4347(3) 0.5905(16) 0.036(4) Uani 1 1 d . . . . .
H4 H 0.096789 0.456979 0.581784 0.044 Uiso 1 1 calc R . . . .
C11 C 0.7918(8) 0.3654(3) 0.6730(16) 0.025(4) Uani 1 1 d . . . . .
H11 H 0.889894 0.343476 0.674289 0.030 Uiso 1 1 calc R . . . .
C8 C 0.6557(8) 0.5202(3) 0.8064(16) 0.030(4) Uani 1 1 d . . . . .
H8 H 0.756744 0.539493 0.848006 0.036 Uiso 1 1 calc R . . . .
C13 C 0.6357(8) 0.2716(3) 0.5456(15) 0.028(4) Uani 1 1 d . . . . .
H13 H 0.733405 0.250106 0.539446 0.033 Uiso 1 1 calc R . . . .
C9 C 0.6521(7) 0.4590(3) 0.7408(16) 0.024(2) Uani 1 1 d . U . . .
C20 C 0.2228(8) 0.6313(3) 0.8208(16) 0.035(4) Uani 1 1 d . . . . .
H20B H 0.116245 0.650411 0.787562 0.053 Uiso 1 1 calc GR . . . .
H20A H 0.296540 0.648252 0.739990 0.053 Uiso 1 1 calc GR . . . .
H20C H 0.265383 0.639685 0.954549 0.053 Uiso 1 1 calc GR . . . .
C10 C 0.8000(8) 0.4242(3) 0.7315(16) 0.027(4) Uani 1 1 d . . . . .
H10 H 0.902199 0.443226 0.766883 0.033 Uiso 1 1 calc R . . . .
C2 C 0.3368(7) 0.3366(3) 0.5368(15) 0.025(4) Uani 1 1 d . . . . .
C6 C 0.3550(8) 0.5267(3) 0.7494(16) 0.024(4) Uani 1 1 d . . . . .
C19 C 0.2078(8) 0.5622(3) 0.7900(16) 0.032(4) Uani 1 1 d . . . . .
C3 C 0.1904(8) 0.3751(3) 0.5259(15) 0.023(4) Uani 1 1 d . . . . .
H3 H 0.089164 0.358092 0.472119 0.028 Uiso 1 1 calc R . . . .
C5 C 0.3457(8) 0.4651(3) 0.6722(16) 0.027(4) Uani 1 1 d . . . . .
C16 C 0.4954(8) 0.4313(3) 0.6750(15) 0.024(4) Uani 1 1 d . . . . .
C17 C 0.1788(9) 0.2349(3) 0.4388(18) 0.035(4) Uani 1 1 d . . . . .
C18 C 0.1868(8) 0.1671(3) 0.4956(16) 0.043(5) Uani 1 1 d . . . . .
H18B H 0.080120 0.148317 0.459578 0.064 Uiso 1 1 calc GR . . . .
H18A H 0.220135 0.163592 0.633435 0.064 Uiso 1 1 calc GR . . . .
H18C H 0.265415 0.145913 0.430054 0.064 Uiso 1 1 calc GR . . . .
C7 C 0.5102(8) 0.5536(3) 0.8113(15) 0.027(4) Uani 1 1 d . . . . .
H7 H 0.516393 0.594612 0.856702 0.032 Uiso 1 1 calc R . . . .
C1 C 0.3353(8) 0.2723(3) 0.4900(15) 0.025(4) Uani 1 1 d . . . . .
C12 C 0.6403(7) 0.3337(3) 0.6078(16) 0.033(4) Uani 1 1 d . . . . .
C15 C 0.4881(7) 0.3679(3) 0.6055(16) 0.026(4) Uani 1 1 d . . . . .
C14 C 0.4862(8) 0.2420(3) 0.4932(16) 0.028(4) Uani 1 1 d . . . . .
H14 H 0.485948 0.199924 0.458249 0.033 Uiso 1 1 calc R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O2 0.030(3) 0.040(4) 0.086(11) -0.011(3) 0.014(4) -0.008(2)
O1 0.037(3) 0.042(4) 0.071(12) 0.008(3) -0.013(5) 0.002(2)
C4 0.017(4) 0.033(5) 0.056(16) 0.003(4) -0.004(6) 0.004(3)
C11 0.022(4) 0.037(5) 0.017(15) -0.001(4) 0.008(5) 0.003(3)
C8 0.020(4) 0.034(5) 0.031(16) 0.005(4) -0.011(5) -0.010(3)
C13 0.031(5) 0.025(4) 0.026(14) 0.008(4) 0.001(6) 0.002(3)
C9 0.021(3) 0.027(3) 0.022(6) -0.001(3) 0.001(4) -0.004(3)
C20 0.035(4) 0.031(5) 0.041(15) -0.009(4) 0.007(6) 0.003(3)
C10 0.019(4) 0.038(5) 0.024(16) 0.015(4) 0.000(6) -0.003(3)
C2 0.022(4) 0.027(4) 0.026(14) 0.001(4) 0.006(5) -0.002(3)
C6 0.031(4) 0.028(5) 0.013(15) 0.004(4) 0.009(6) 0.001(3)
C19 0.019(4) 0.032(5) 0.040(15) 0.009(4) -0.009(5) -0.001(3)
C3 0.019(4) 0.035(5) 0.013(15) -0.001(4) -0.005(5) 0.000(3)
C5 0.026(4) 0.033(5) 0.022(15) -0.005(4) 0.001(6) 0.002(3)
C16 0.028(4) 0.020(4) 0.027(14) 0.002(3) 0.016(6) 0.000(3)
C17 0.031(5) 0.029(5) 0.044(15) -0.003(4) 0.003(7) -0.005(4)
C18 0.037(5) 0.027(5) 0.059(17) -0.002(4) -0.007(6) -0.001(3)
C7 0.030(4) 0.024(5) 0.027(14) -0.002(4) 0.006(6) -0.005(3)
C1 0.036(5) 0.023(4) 0.016(14) -0.001(3) 0.002(6) -0.007(3)
C12 0.014(4) 0.036(5) 0.049(15) -0.002(4) 0.003(6) 0.000(3)
C15 0.022(4) 0.031(5) 0.025(15) 0.001(4) 0.004(5) -0.001(3)
C14 0.035(5) 0.020(5) 0.028(14) 0.005(3) 0.003(6) 0.001(3)

_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
O2 C19 1.232(6) . ?
O1 C17 1.210(9) . ?
C4 H4 0.9300 . ?
C4 C3 1.347(9) . ?
C4 C5 1.432(10) . ?
C11 H11 0.9300 . ?
C11 C10 1.317(9) . ?
C11 C12 1.426(9) . ?
C8 H8 0.9300 . ?
C8 C9 1.383(9) . ?
C8 C7 1.395(8) . ?
C13 H13 0.9300 . ?
C13 C12 1.393(9) . ?
C13 C14 1.377(9) . ?
C9 C10 1.433(8) . ?
C9 C16 1.424(9) . ?
C20 H20B 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20C 0.9600 . ?
C20 C19 1.491(8) . ?
C10 H10 0.9300 . ?
C2 C3 1.448(8) . ?
C2 C1 1.410(8) . ?
C2 C15 1.426(9) . ?
C6 C19 1.490(9) . ?
C6 C5 1.418(9) . ?
C6 C7 1.401(9) . ?
C3 H3 0.9300 . ?
C5 C16 1.422(8) . ?
C16 C15 1.434(9) . ?
C17 C18 1.498(9) . ?
C17 C1 1.506(9) . ?
C18 H18B 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18C 0.9600 . ?
C7 H7 0.9300 . ?
C1 C14 1.395(8) . ?
C12 C15 1.445(8) . ?
C14 H14 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C4 H4 118.7 . . ?
C3 C4 C5 122.5(6) . . ?
C5 C4 H4 118.7 . . ?
C10 C11 H11 118.3 . . ?
C10 C11 C12 123.3(6) . . ?
C12 C11 H11 118.3 . . ?
C9 C8 H8 119.5 . . ?
C9 C8 C7 121.0(6) . . ?
C7 C8 H8 119.5 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C14 C13 C12 119.8(7) . . ?
C8 C9 C10 122.0(6) . . ?
C8 C9 C16 118.0(6) . . ?
C16 C9 C10 119.9(6) . . ?
H20B C20 H20A 109.5 . . ?
H20B C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20C 109.5 . . ?
C11 C10 C9 120.3(6) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C1 C2 C3 124.3(6) . . ?
C1 C2 C15 120.6(6) . . ?
C15 C2 C3 115.1(6) . . ?
C5 C6 C19 123.1(6) . . ?
C7 C6 C19 117.3(6) . . ?
C7 C6 C5 119.2(6) . . ?
O2 C19 C20 119.1(6) . . ?
O2 C19 C6 122.4(6) . . ?
C6 C19 C20 118.6(6) . . ?
C4 C3 C2 122.6(7) . . ?
C4 C3 H3 118.7 . . ?
C2 C3 H3 118.7 . . ?
C6 C5 C4 124.2(6) . . ?
C6 C5 C16 118.0(6) . . ?
C16 C5 C4 117.8(6) . . ?
C9 C16 C15 119.2(5) . . ?
C5 C16 C9 121.9(6) . . ?
C5 C16 C15 118.9(6) . . ?
O1 C17 C18 120.8(7) . . ?
O1 C17 C1 122.5(7) . . ?
C18 C17 C1 116.6(7) . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18B C18 H18A 109.5 . . ?
H18B C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
C8 C7 C6 121.7(7) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C2 C1 C17 123.1(6) . . ?
C14 C1 C2 118.1(6) . . ?
C14 C1 C17 118.8(6) . . ?
C11 C12 C15 118.2(6) . . ?
C13 C12 C11 122.0(6) . . ?
C13 C12 C15 119.8(6) . . ?
C2 C15 C16 122.9(6) . . ?
C2 C15 C12 118.2(6) . . ?
C16 C15 C12 118.9(6) . . ?
C13 C14 C1 123.0(7) . . ?
C13 C14 H14 118.5 . . ?
C1 C14 H14 118.5 . . ?

_iucr_refine_instructions_details 
;
TITL exp_303__reject_lims_3d_oa33_res83_hp_smart3__rint40_res83_out_a.res in P2(
 exp_303__reject_lims_3d_oa33_res83_hp_smart3__rint40_res83_out.res created by SHELXL-2016/4 at 13:52:36 on 21-Apr-2020
REM Old TITL exp_303__reject_lims_3D_oa33_Res83_HP_smart3__Rint40_Res83_out in
REM P2(1
REM SHELXT solution in P2(1)/c
REM R1 0.253, Rweak 0.048, Alpha 0.114, Orientation as input
REM Formula found by SHELXT:
CELL 0.56087 8.2093 21.33256 6.97264 90 99.0693 90
ZERR 4 0.0019 0.00707 0.00824 0 0.0468 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H O
UNIT 80 56 8
ISOR 0.005 0.005 C9

L.S. 40 0 0
PLAN  20
BOND H
list 4
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc
REM  "%.\\exp_303__reject_lims_3D_oa33_Res83_HP_smart3__Rint40_Res83_out.hkl">
REM </olex2.extras>

WGHT    0.079900    0.739200
FVAR       1.04664
O2    3    0.074671    0.536537    0.798553    11.00000    0.03018    0.03954 =
         0.08563   -0.01098    0.01389   -0.00788
O1    3    0.053132    0.257321    0.351933    11.00000    0.03720    0.04222 =
         0.07066    0.00780   -0.01265    0.00176
C4    1    0.195092    0.434722    0.590511    11.00000    0.01728    0.03306 =
         0.05553    0.00260   -0.00370    0.00399
AFIX  43
H4    2    0.096789    0.456979    0.581784    11.00000   -1.20000
AFIX   0
C11   1    0.791826    0.365412    0.673003    11.00000    0.02163    0.03701 =
         0.01684   -0.00076    0.00834    0.00266
AFIX  43
H11   2    0.889894    0.343476    0.674289    11.00000   -1.20000
AFIX   0
C8   1    0.655718    0.520231    0.806437    11.00000    0.02036    0.03360 =
         0.03065    0.00533   -0.01063   -0.01013
AFIX  43
H8   2    0.756744    0.539493    0.848006    11.00000   -1.20000
AFIX   0
C13    1    0.635739    0.271558    0.545581    11.00000    0.03133    0.02480 =
         0.02558    0.00833    0.00052    0.00167
AFIX  43
H13    2    0.733405    0.250106    0.539446    11.00000   -1.20000
AFIX   0
C9   1    0.652075    0.458992    0.740786    11.00000    0.02097    0.02744 =
         0.02229   -0.00055    0.00119   -0.00379
C20   1    0.222828    0.631295    0.820757    11.00000    0.03487    0.03120 =
         0.04054   -0.00898    0.00737    0.00342
AFIX 137
H20B  2    0.116245    0.650411    0.787562    11.00000   -1.50000
H20A  2    0.296540    0.648252    0.739990    11.00000   -1.50000
H20C  2    0.265383    0.639685    0.954549    11.00000   -1.50000
AFIX   0
C10   1    0.799958    0.424197    0.731465    11.00000    0.01894    0.03783 =
         0.02354    0.01529    0.00000   -0.00282
AFIX  43
H10   2    0.902199    0.443226    0.766883    11.00000   -1.20000
AFIX   0
C2    1    0.336761    0.336599    0.536766    11.00000    0.02174    0.02727 =
         0.02635    0.00092    0.00555   -0.00224
C6    1    0.355010    0.526732    0.749413    11.00000    0.03112    0.02800 =
         0.01333    0.00411    0.00907    0.00101
C19   1    0.207786    0.562221    0.789952    11.00000    0.01936    0.03236 =
         0.04000    0.00907   -0.00905   -0.00125
C3    1    0.190379    0.375139    0.525857    11.00000    0.01874    0.03518 =
         0.01349   -0.00079   -0.00530   -0.00040
AFIX  43
H3    2    0.089164    0.358092    0.472119    11.00000   -1.20000
AFIX   0
C5    1    0.345698    0.465091    0.672161    11.00000    0.02563    0.03350 =
         0.02162   -0.00493    0.00111    0.00193
C16   1    0.495421    0.431302    0.675049    11.00000    0.02848    0.02014 =
         0.02727    0.00223    0.01554   -0.00039
C17   1    0.178825    0.234896    0.438773    11.00000    0.03060    0.02869 =
         0.04429   -0.00264    0.00320   -0.00550
C18   1    0.186844    0.167088    0.495562    11.00000    0.03686    0.02674 =
         0.05918   -0.00178   -0.00739   -0.00062
AFIX 137
H18B  2    0.080120    0.148317    0.459578    11.00000   -1.50000
H18A  2    0.220135    0.163592    0.633435    11.00000   -1.50000
H18C  2    0.265415    0.145913    0.430054    11.00000   -1.50000
AFIX   0
C7   1    0.510230    0.553556    0.811276    11.00000    0.03005    0.02379 =
         0.02711   -0.00207    0.00585   -0.00486
AFIX  43
H7   2    0.516393    0.594612    0.856702    11.00000   -1.20000
AFIX   0
C1    1    0.335252    0.272266    0.490015    11.00000    0.03600    0.02268 =
         0.01612   -0.00050    0.00218   -0.00718
C12    1    0.640320    0.333687    0.607838    11.00000    0.01371    0.03574 =
         0.04854   -0.00164    0.00345   -0.00039
C15   1    0.488135    0.367943    0.605526    11.00000    0.02249    0.03123 =
         0.02471    0.00096    0.00394   -0.00088
C14    1    0.486250    0.242004    0.493164    11.00000    0.03455    0.02032 =
         0.02819    0.00462    0.00332    0.00090
AFIX  43
H14    2    0.485948    0.199924    0.458249    11.00000   -1.20000
AFIX   0
HKLF 4




REM  exp_303__reject_lims_3d_oa33_res83_hp_smart3__rint40_res83_out_a.res in P2(
REM R1 =  0.0794 for     536 Fo > 4sig(Fo)  and  0.1819 for all    1064 data
REM    201 parameters refined using      6 restraints

END  
     
WGHT      0.0794      0.7557 

REM Highest difference peak  0.189,  deepest hole -0.200,  1-sigma level  0.048
Q1    1   0.4777  0.1781  0.5936  11.00000  0.05    0.19
Q2    1   0.4922  0.4016  0.4431  11.00000  0.05    0.19
Q3    1  -0.0457  0.6806  0.8015  11.00000  0.05    0.17
Q4    1   0.0178  0.2856  0.4414  11.00000  0.05    0.16
Q5    1   0.2319  0.6544  0.9821  11.00000  0.05    0.16
Q6    1   0.2485  0.4168  0.4107  11.00000  0.05    0.15
Q7    1   0.2247  0.1398  0.3223  11.00000  0.05    0.15
Q8    1   0.0756  0.2394  0.4799  11.00000  0.05    0.14
Q9    1  -0.0323  0.5383  0.8970  11.00000  0.05    0.14
Q10   1   0.0421  0.4985  0.5510  11.00000  0.05    0.14
Q11   1   0.1814  0.3996  0.3345  11.00000  0.05    0.14
Q12   1   0.5224  0.5996  0.8157  11.00000  0.05    0.14
Q13   1   0.0386  0.2254  0.4116  11.00000  0.05    0.13
Q14   1   0.8060  0.5607  0.9766  11.00000  0.05    0.13
Q15   1   0.4784  0.2013  0.7214  11.00000  0.05    0.13
Q16   1  -0.0559  0.4751  0.5952  11.00000  0.05    0.13
Q17   1   0.1990  0.1144  0.7673  11.00000  0.05    0.13
Q18   1   0.9342  0.4636  0.6881  11.00000  0.05    0.13
Q19   1   0.5146  0.3984  0.7685  11.00000  0.05    0.13
Q20   1   0.3762  0.6995  0.6641  11.00000  0.05    0.13

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0794 for 536 Fo > 4sig(Fo) and 0.1819 for all 4818 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.19, deepest hole -0.20
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.1819
  REM R1_gt = 0.0794
  REM wR_ref = 0.1974
  REM GOOF = 1.047
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 4818
  REM Reflections_gt = 536
  REM Parameters = n/a
  REM Hole = -0.20
  REM Peak = 0.19
  REM Flack = n/a

  
;
_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT029_2bisAP-delta_2120000kPa 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.483 Why?  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 33 degrees on a very thin plate. This limited the number
of reflections that could be collected, as most of them were obscured
by the DAC.
;
_vrf_PLAT088_2bisAP-delta_2120000kPa 
;
PROBLEM: Poor Data / Parameter Ratio ....................       5.29 Note  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 33 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
;
_vrf_PLAT911_2bisAP-delta_2120000kPa 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L= 0.600           774 Report
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 33 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
;
_vrf_PLAT148_2bisAP-delta_2120000kPa 
;
PROBLEM: s.u. on the      c    - Axis is (Too) Large ....      0.008 Ang.  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 33 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC, and in 
particular affected the c direction due to crystal orientation.
;
_vrf_PLAT340_2bisAP-delta_2120000kPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00987 Ang.  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 33 degrees on a very thin plate. This limited the number
of reflections that could be collected, as most of them were obscured by the
DAC, which together with weak scattering negatively affected the precision.
;
# 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_2bisAP-beta_2030000kPa
_database_code_depnum_ccdc_archive 'CCDC 2039422'
loop_
_audit_author_name
_audit_author_address
'Daniel Tchon'
;Faculty of Chemistry, University of Warsaw
Poland
;
_audit_update_record             
;
2020-10-19 deposited with the CCDC.	2021-01-21 downloaded from the CCDC.
;
_audit_creation_date             2019-08-06
_audit_creation_method           
;
Olex2 1.2
(compiled May 29 2018 13:30:08 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            1,1'-Pyrene-1,8-diyldiethanone
_chemical_name_systematic        1,8-Diacetylpyrene
_chemical_formula_moiety         'C20 H14 O2'
_chemical_formula_sum            'C20 H14 O2'
_chemical_formula_weight         286.31
_chemical_absolute_configuration ?
_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      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   4.545(3)
_cell_length_b                   34.45(15)
_cell_length_c                   16.010(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2506(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    185
_cell_measurement_temperature    291.2(4)
_cell_measurement_theta_max      20.0000
_cell_measurement_theta_min      2.8100
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56306
_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 light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1200
_exptl_crystal_preparation       
'Mounted in a Diamond-Anvil Cell using parabar oil as pressure medium.,Luminescent'
_exptl_crystal_pressure_history  
'Pressurized to 2.03 GPa and left to stabilize over 24 hours.'
_exptl_crystal_recrystallization_method 'from chloroform at room temperature'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
High-pressure measurement at 2.03 GPa in a Merill-Basset Diamond Anvil Cell with
effective opening angle of 48 deg. and parabar 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  0.1851
_diffrn_reflns_av_unetI/netI     0.1144
_diffrn_reflns_Laue_measured_fraction_full 0.345
_diffrn_reflns_Laue_measured_fraction_max 0.516
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            1248
_diffrn_reflns_point_group_measured_fraction_full 0.332
_diffrn_reflns_point_group_measured_fraction_max 0.499
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         21.910
_diffrn_reflns_theta_min         2.806
_diffrn_ambient_temperature      291.2(4)
_diffrn_ambient_pressure         2030000
_diffrn_ambient_environment      'Diamond Anvil Cell filled with parabar oil'
_diffrn_crystal_treatment        
'Pressurized slowly in parabar oil as a hydrostatic medium.'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4391
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.345
_diffrn_measured_fraction_theta_max 0.516
_diffrn_measurement_details      
'List of Runs (angles in degrees, time in seconds): # Type Start End Width tₑₓₚ ω θ κ φ Frames -------------------------------------------------------------------------- 1 ω -25.00 0.00 1.00 130.00 -- 9.85 -37.00-120.00 25 2 ω -35.00 -9.00 1.00 130.00 -- 9.85 -19.00-120.00 26 3 ω -26.00 7.00 1.00 130.00 -- 9.85 19.00 30.00 33 4 ω 4.00 30.00 1.00 130.00 -- 9.85 56.00 161.00 26 5 ω -13.00 19.00 1.00 130.00 -- 9.85 -81.00-151.00 32 6 ω -20.00 5.00 1.00 130.00 -- 9.85 26.00 -7.00 25 7 ω -52.00 -26.00 1.00 130.00 -- -11.72 19.00 30.00 26 8 ω -65.00 -39.00 1.00 130.00 -- -11.72 134.00 123.00 26'
_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 48 deg.'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0032781729
_diffrn_orient_matrix_UB_12      -0.0205398947
_diffrn_orient_matrix_UB_13      0.0001311787
_diffrn_orient_matrix_UB_21      -0.1163759983
_diffrn_orient_matrix_UB_22      0.0003230270
_diffrn_orient_matrix_UB_23      0.0297570292
_diffrn_orient_matrix_UB_31      -0.1041474991
_diffrn_orient_matrix_UB_32      0.0002604192
_diffrn_orient_matrix_UB_33      -0.0329092377
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\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         0.850
_reflns_Friedel_fraction_full    0.318
_reflns_Friedel_fraction_max     0.481
_reflns_number_gt                214
_reflns_number_total             381
_reflns_odcompleteness_completeness 47.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     23.48
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXD (Sheldrick, 2008)'
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details .
_refine_ls_abs_structure_Flack   .
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.227
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         381
_refine_ls_number_restraints     79
_refine_ls_R_factor_all          0.1471
_refine_ls_R_factor_gt           0.0981
_refine_ls_restrained_S_all      1.140
_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)+(0.1000P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2193
_refine_ls_wR_factor_ref         0.2618
_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
 C3, O1, C17, C1, C18, C2, C14, C15, C13, C12, C11
 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:
 C3(H3), C14(H14), C13(H13), C11(H11)
3.b Idealised Me refined as rotating group:
 C18(H18B,H18A,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.091(5) 0.4187(14) 0.2897(9) 0.127(14) Uani 1 1 d . U . . .
C3 C 0.402(4) 0.4874(17) 0.3553(8) 0.098(14) Uani 1 1 d . U . . .
H3 H 0.3211 0.4807 0.3039 0.117 Uiso 1 1 calc R . . . .
C2 C 0.281(4) 0.4663(13) 0.4331(11) 0.088(11) Uani 1 1 d . U . . .
C1 C 0.073(4) 0.4398(15) 0.4348(12) 0.096(11) Uani 1 1 d . U . . .
C14 C -0.036(5) 0.4249(19) 0.5136(15) 0.115(14) Uani 1 1 d . U . . .
H14 H -0.1779 0.4055 0.5152 0.138 Uiso 1 1 calc R . . . .
C13 C 0.078(6) 0.4403(17) 0.5862(13) 0.106(13) Uani 1 1 d . U . . .
H13 H 0.0107 0.4307 0.6371 0.127 Uiso 1 1 calc R . . . .
C12 C 0.282(5) 0.4687(17) 0.5863(11) 0.104(13) Uani 1 1 d . U . . .
C15 C 0.393(4) 0.4848(15) 0.5082(11) 0.087(12) Uani 1 1 d . U . . .
C11 C 0.398(5) 0.4870(17) 0.6629(10) 0.107(15) Uani 1 1 d . U . . .
H11 H 0.3192 0.4794 0.7139 0.128 Uiso 1 1 calc R . . . .
C17 C -0.035(5) 0.4158(18) 0.3594(15) 0.098(12) Uani 1 1 d . U . . .
C18 C -0.279(5) 0.385(2) 0.3671(17) 0.105(14) Uani 1 1 d . U . . .
H18B H -0.3260 0.3754 0.3127 0.157 Uiso 1 1 calc GR . . . .
H18A H -0.4508 0.3972 0.3911 0.157 Uiso 1 1 calc GR . . . .
H18C H -0.2135 0.3645 0.4022 0.157 Uiso 1 1 calc GR . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.132(14) 0.20(5) 0.048(8) -0.005(11) -0.012(7) -0.029(18)
C3 0.068(16) 0.20(4) 0.029(9) -0.002(14) -0.001(8) -0.01(2)
C2 0.047(12) 0.18(3) 0.040(8) -0.002(11) -0.001(8) 0.001(14)
C1 0.056(11) 0.19(3) 0.047(8) -0.007(12) 0.003(8) -0.006(14)
C14 0.073(14) 0.21(4) 0.060(10) -0.003(14) 0.008(9) -0.012(19)
C13 0.062(13) 0.20(4) 0.051(10) -0.010(13) 0.019(10) 0.006(17)
C12 0.065(15) 0.20(4) 0.041(9) 0.005(11) 0.000(8) 0.005(17)
C15 0.054(12) 0.18(3) 0.033(7) -0.005(10) 0.000(7) 0.013(15)
C11 0.073(16) 0.22(5) 0.029(8) 0.006(13) 0.011(8) 0.00(2)
C17 0.073(13) 0.17(3) 0.053(9) -0.001(13) -0.018(9) -0.002(17)
C18 0.070(13) 0.16(4) 0.081(15) -0.016(18) -0.003(12) -0.001(18)

_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 1.26(3) . ?
C3 C3 1.24(8) 2_665 ?
C3 C2 1.54(4) . ?
C2 C1 1.31(5) . ?
C2 C15 1.45(4) . ?
C1 C14 1.45(4) . ?
C1 C17 1.54(5) . ?
C14 C13 1.38(5) . ?
C13 C12 1.35(6) . ?
C12 C15 1.46(4) . ?
C12 C11 1.48(4) . ?
C15 C15 1.43(8) 2_665 ?
C11 C11 1.29(8) 2_665 ?
C17 C18 1.53(6) . ?

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
C3 C3 C2 125.7(13) 2_665 . ?
C1 C2 C3 127(2) . . ?
C1 C2 C15 123(2) . . ?
C15 C2 C3 110(3) . . ?
C2 C1 C14 121(3) . . ?
C2 C1 C17 126(2) . . ?
C14 C1 C17 113(3) . . ?
C13 C14 C1 118(4) . . ?
C12 C13 C14 123(3) . . ?
C13 C12 C15 121(3) . . ?
C13 C12 C11 124(2) . . ?
C15 C12 C11 115(4) . . ?
C2 C15 C12 115(3) . . ?
C15 C15 C2 124.1(17) 2_665 . ?
C15 C15 C12 121(2) 2_665 . ?
C11 C11 C12 123.6(18) 2_665 . ?
O1 C17 C1 121(3) . . ?
O1 C17 C18 117(3) . . ?
C18 C17 C1 122(2) . . ?

_iucr_refine_instructions_details 
;
TITL p4_v3_abs in Fdd2 #43
REM Best SHELXD solution FINAL CC 74.16
REM Fragments: 18
REM reset to Fdd2 #43
CELL 0.71073 4.544704 34.445369 16.010379 90 90 90
ZERR 8 0.003245 0.146127 0.007829 0 0 0
LATT -4
SYMM -X,-Y,+Z
SYMM 0.25-X,0.25+Y,0.25+Z
SYMM 0.25+X,0.25-Y,0.25+Z
SFAC C H O
UNIT 160 112 16
RIGU C3 O1 C17 C1 C18 C2 C14 C15 C13 C12 C11
 
L.S. 4 0 0
PLAN  2
fmap 2
acta
SHEL 100 0.95
REM <olex2.extras>
REM <HklSrc "%./p4_v3_abs.hkl">
REM </olex2.extras>
 
WGHT    0.100000
FVAR       0.96428
O1    3    0.090732    0.418745    0.289739    11.00000    0.13210    0.20068 =
         0.04811   -0.00501   -0.01221   -0.02884
C3    1    0.401976    0.487419    0.355279    11.00000    0.06753    0.19685 =
         0.02884   -0.00164   -0.00130   -0.00726
AFIX  43
H3    2    0.321132    0.480729    0.303895    11.00000   -1.20000
AFIX   0
C2    1    0.280835    0.466291    0.433078    11.00000    0.04678    0.17770 =
         0.03961   -0.00228   -0.00061    0.00135
C1    1    0.072710    0.439815    0.434782    11.00000    0.05555    0.18552 =
         0.04681   -0.00663    0.00331   -0.00611
C14    1   -0.035793    0.424902    0.513634    11.00000    0.07283    0.21086 =
         0.06045   -0.00294    0.00841   -0.01234
AFIX  43
H14    2   -0.177929    0.405492    0.515183    11.00000   -1.20000
AFIX   0
C13    1    0.077595    0.440296    0.586181    11.00000    0.06234    0.20392 =
         0.05120   -0.00978    0.01894    0.00633
AFIX  43
H13    2    0.010737    0.430735    0.637082    11.00000   -1.20000
AFIX   0
C12    1    0.281826    0.468697    0.586298    11.00000    0.06525    0.20463 =
         0.04070    0.00513    0.00004    0.00492
C15    1    0.392756    0.484822    0.508181    11.00000    0.05355    0.17552 =
         0.03260   -0.00541    0.00007    0.01289
C11    1    0.397907    0.487038    0.662865    11.00000    0.07345    0.21694 =
         0.02921    0.00625    0.01057   -0.00485
AFIX  43
H11    2    0.319196    0.479446    0.713934    11.00000   -1.20000
AFIX   0
C17    1   -0.034595    0.415788    0.359416    11.00000    0.07283    0.16769 =
         0.05331   -0.00096   -0.01776   -0.00188
C18   1   -0.279037    0.385391    0.367055    11.00000    0.07031    0.16256 =
         0.08124   -0.01564   -0.00294   -0.00094
AFIX 137
H18B  2   -0.326026    0.375428    0.312668    11.00000   -1.50000
H18A  2   -0.450822    0.397155    0.391074    11.00000   -1.50000
H18C  2   -0.213492    0.364536    0.402212    11.00000   -1.50000
AFIX   0
HKLF 4
 
REM  p4_v3_abs in Fdd2 #43
REM R1 =  0.0981 for     214 Fo > 4sig(Fo)  and  0.1471 for all     381 data
REM    101 parameters refined using     79 restraints
 
END  
     
WGHT      0.1860      0.0000 

REM Highest difference peak  0.168,  deepest hole -0.176,  1-sigma level  0.054
Q1    1   0.5903  0.4766  0.5863  11.00000  0.05    0.17
Q2    1   0.3759  0.4331  0.5806  11.00000  0.05    0.16

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0981 for 214 Fo > 4sig(Fo) and 0.1471 for all 1539 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.17, deepest hole -0.18
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.1471
  REM R1_gt = 0.0981
  REM wR_ref = 0.2618
  REM GOOF = 1.227
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 1539
  REM Reflections_gt = 214
  REM Parameters = n/a
  REM Hole = -0.18
  REM Peak = 0.17
  REM Flack = -10.2(10)

  
;
_olex2_exptl_crystal_mounting_method 
'in a DAC, opening angle of 48, in Paratone N oil'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
'Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling'
_oxdiff_exptl_absorpt_empirical_full_max 1.593
_oxdiff_exptl_absorpt_empirical_full_min 0.685


# start Validation Reply Form
_vrf_THETM01_2bisAP-beta_2030000kPa 
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 48 degrees on a crystal that was beginning to crack. 
This resulted in low diffracted intensities, low available data resolution 
and consequently low number of reflections and high Rint value.
;
_vrf_PLAT089_2bisAP-beta_2030000kPa 
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       2.04 Note  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 48 degrees on a crystal that was beginning to crack. 
This resulted in low diffracted intensities, low available data resolution 
and consequently low number of reflections and high Rint value.
The final model is therefore of rather low precission.
;
_vrf_PLAT340_2bisAP-beta_2030000kPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.05154 Ang.  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 48 degrees on a crystal that was beginning to crack. 
This resulted in low diffracted intensities, low available data resolution 
and consequently low number of reflections and high Rint value.
The final model is therefore of rather low precission.
;
_vrf_RINTA01_2bisAP-beta_2030000kPa 
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 48 degrees on a very thin plate. This resulted in low 
diffracted intensities, low available data resolution and high Rint value.
;
_vrf_PLAT020_2bisAP-beta_2030000kPa 
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.185 Report
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 48 degrees on a very thin plate. This resulted in low 
diffracted intensities, low available data resolution and high Rint value.
;
_vrf_PLAT250_2bisAP-beta_2030000kPa 
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        4.1 Note  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell with
opening angle of 48 degrees on a very thin plate. This limited the number of
reflections that could be collected, as most of them were obscured by the DAC,
resulting in an elongation of average U(i,j) tensor due to Fourier cutoff.
;
_vrf_PLAT911_2bisAP-beta_2030000kPa 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L= 0.525            48 Report
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 48 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
;
_vrf_PLAT915_2bisAP-beta_2030000kPa 
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         48 % 
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 48 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
Moreover, high Friedel pair coverage was unnecessary, as space group information
was determined using complete dataset gathered on this sample before experiment. 
;
_vrf_PLAT018_2bisAP-beta_2030000kPa 
;
PROBLEM: _diffrn_measured_fraction_theta_max .NE. *_full           ! Check 
RESPONSE: A discrepancy between what olex2 and shelx report.
;
_vrf_PLAT084_2bisAP-beta_2030000kPa 
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.26 Report
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 48 degrees on a crystal that was beginning to crack. 
This resulted in low diffracted intensities, low available data resolution 
and consequently low number of reflections and high Rint value.
The final model is therefore of rather low precission.
;
_vrf_PLAT148_2bisAP-beta_2030000kPa 
;
PROBLEM: s.u. on the      b    - Axis is (Too) Large ....     0.1500 Ang.  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 48 degrees on a crystal that was beginning to crack. 
This resulted in low diffracted intensities, low available data resolution 
and consequently low number of reflections and high Rint value.
The b direction was particularly affected.
;
_vrf_PLAT260_2bisAP-beta_2030000kPa 
;
PROBLEM: Large Average Ueq of Residue Including        O1      0.103 Check 
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 48 degrees on a crystal that was beginning to crack. 
This resulted in low diffracted intensities, low available data resolution 
and consequently low number of reflections and high Rint value.
The b direction was particularly affected, hence ADP-s are elongated in that
direction.
;
_vrf_PLAT369_2bisAP-beta_2030000kPa 
;
PROBLEM: Long   C(sp2)-C(sp2) Bond  C3       - C2       .       1.54 Ang.  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 48 degrees on a crystal that was beginning to crack. 
This resulted in low diffracted intensities, low available data resolution 
and consequently low number of reflections and high Rint value.
The final model is therefore of rather low precission.
;
_vrf_PLAT411_2bisAP-beta_2030000kPa 
;
PROBLEM: Short Inter H...H Contact  H3       ..H11       .       2.09 Ang.  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 48 degrees on a crystal that was beginning to crack. 
This resulted in low diffracted intensities, low available data resolution 
and consequently low number of reflections and high Rint value.
The final model is therefore of rather low precission.
H atoms were added in idealized positions as locating them from the Fourier
map was impossible.
;
_vrf_PLAT978_2bisAP-beta_2030000kPa 
;
PROBLEM: Number C-C Bonds with Positive Residual Density.          0 Info  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 48 degrees on a crystal that was beginning to crack. 
This resulted in low diffracted intensities, low available data resolution 
and consequently low number of reflections and high Rint value.
The final model is therefore of rather low precission.
;
# 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_2bisAP-delta_980000kPa
_database_code_depnum_ccdc_archive 'CCDC 2039423'
loop_
_audit_author_name
_audit_author_address
'Daniel Tchon'
;Faculty of Chemistry, University of Warsaw
Poland
;
_audit_update_record             
;
2020-10-19 deposited with the CCDC.	2021-01-21 downloaded from the CCDC.
;
_audit_creation_date             2020-03-20
_audit_creation_method           
;
Olex2 1.2
(compiled May 29 2018 13:30:08 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            1,1'-Pyrene-1,8-diyldiethanone
_chemical_name_systematic        1,8-Diacetylpyrene
_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 0.0015 0.0009 '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 0.0056 0.0036 '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                   8.250(2)
_cell_length_b                   21.62(10)
_cell_length_c                   7.166(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.87(3)
_cell_angle_gamma                90
_cell_volume                     1263(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    542
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15.4870
_cell_measurement_theta_min      2.0710
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.061
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82644
_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    1.506
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_preparation       
'Mounted in a Diamond-Anvil Cell using silicone oil as pressure medium.,Luminescent'
_exptl_crystal_pressure_history  
'Pressurized to 0.98 GPa and left to stabilize over 24 hours.'
_exptl_crystal_recrystallization_method 'from acetonitrile at room temperature'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
High-pressure measurement at 0.98 GPa in a Merill-Basset Diamond Anvil Cell with
effective opening angle of 30 deg. and silicone 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  0.0741
_diffrn_reflns_av_unetI/netI     0.1067
_diffrn_reflns_Laue_measured_fraction_full 0.243
_diffrn_reflns_Laue_measured_fraction_max 0.225
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2063
_diffrn_reflns_point_group_measured_fraction_full 0.243
_diffrn_reflns_point_group_measured_fraction_max 0.225
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         20.505
_diffrn_reflns_theta_min         2.107
_diffrn_ambient_temperature      293(2)
_diffrn_ambient_pressure         980000
_diffrn_ambient_environment      'Diamond Anvil Cell filled with silicone oil'
_diffrn_crystal_treatment        
'Pressurized slowly in silicone oil as a hydrostatic medium.'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0064
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.243
_diffrn_measured_fraction_theta_max 0.225
_diffrn_measurement_details      
'List of Runs (angles in degrees, time in seconds): # Type Start End Width tₑₓₚ ω θ κ φ Frames -------------------------------------------------------------------------- 1 ω -43.00 2.00 1.00 100.00 -- 11.07 38.00-180.00 45 2 ω -18.00 47.00 1.00 100.00 -- 11.07 -53.00 17.00 65 3 ω 7.00 55.00 1.00 100.00 -- 11.07 -81.00-151.00 48 4 ω -33.00 24.00 1.00 100.00 -- 11.07 13.00 -3.00 57 5 ω -15.00 10.00 1.00 100.00 -- 11.07 -19.00-180.00 25'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 
'Diamond Anvil Cell, effective opening angle of 30 deg.'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0012743000
_diffrn_orient_matrix_UB_12      0.0260495000
_diffrn_orient_matrix_UB_13      0.0009810000
_diffrn_orient_matrix_UB_21      -0.0630805000
_diffrn_orient_matrix_UB_22      0.0005389000
_diffrn_orient_matrix_UB_23      -0.0411723000
_diffrn_orient_matrix_UB_31      -0.0264035000
_diffrn_orient_matrix_UB_32      -0.0000527000
_diffrn_orient_matrix_UB_33      0.0670948000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56087
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Ag) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                350
_reflns_number_total             579
_reflns_odcompleteness_completeness 23.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     20.46
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.089
_refine_diff_density_min         -0.098
_refine_diff_density_rms         0.025
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.201
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         579
_refine_ls_number_restraints     189
_refine_ls_R_factor_all          0.1413
_refine_ls_R_factor_gt           0.0659
_refine_ls_restrained_S_all      1.000
_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)+(0.0471P)²+0.4000P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1149
_refine_ls_wR_factor_ref         0.1409
_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
 C17, C2, C1, C15, C3, C14, C12, C16, C4, C13, O1, C18, C11, C9, C5, C10, C8,
 C6, C7, C19, O2, C20
 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:
 C14(H14), C13(H13), C8(H8), C7(H7), C4(H4), C3(H3), C11(H11), C10(H10)
3.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.1618(12) 0.6650(18) 0.4575(16) 0.045(9) Uani 1 1 d . U . . .
C1 C 0.1593(12) 0.7270(18) 0.5088(16) 0.050(9) Uani 1 1 d . U . . .
C14 C 0.0110(8) 0.7585(12) 0.5011(10) 0.057(9) Uani 1 1 d . U . . .
H14 H 0.0099 0.8004 0.5301 0.069 Uiso 1 1 calc R . . . .
C13 C -0.1355(14) 0.726(2) 0.4496(17) 0.059(9) Uani 1 1 d . U . . .
H13 H -0.2335 0.7465 0.4590 0.071 Uiso 1 1 calc R . . . .
C12 C -0.1414(12) 0.670(2) 0.3887(17) 0.049(9) Uani 1 1 d . U . . .
C15 C 0.0091(11) 0.629(2) 0.3913(16) 0.049(8) Uani 1 1 d . U . . .
C16 C 0.0048(11) 0.5728(18) 0.3265(15) 0.047(8) Uani 1 1 d . U . . .
C9 C -0.1481(11) 0.5421(18) 0.2647(14) 0.047(9) Uani 1 1 d . U . . .
C8 C -0.1512(12) 0.4838(19) 0.1965(16) 0.052(9) Uani 1 1 d . U . . .
H8 H -0.2528 0.4664 0.1513 0.063 Uiso 1 1 calc R . . . .
C7 C -0.0067(7) 0.4468(12) 0.1895(10) 0.057(9) Uani 1 1 d . U . . .
H7 H -0.0123 0.4059 0.1484 0.068 Uiso 1 1 calc R . . . .
C6 C 0.1451(11) 0.4774(19) 0.2502(14) 0.053(9) Uani 1 1 d . U . . .
C5 C 0.1518(10) 0.5350(17) 0.3242(15) 0.047(8) Uani 1 1 d . U . . .
C4 C 0.3021(13) 0.5660(19) 0.4070(19) 0.057(9) Uani 1 1 d . U . . .
H4 H 0.4002 0.5441 0.4205 0.068 Uiso 1 1 calc R . . . .
O1 O 0.4378(6) 0.7428(9) 0.6497(8) 0.070(10) Uani 1 1 d . U . . .
C17 C 0.3142(13) 0.763(2) 0.5600(17) 0.056(9) Uani 1 1 d . U . . .
C3 C 0.3049(12) 0.628(2) 0.4672(18) 0.050(9) Uani 1 1 d . U . . .
H3 H 0.4055 0.6452 0.5161 0.060 Uiso 1 1 calc R . . . .
C11 C -0.2932(12) 0.6294(18) 0.3274(15) 0.042(9) Uani 1 1 d . U . . .
H11 H -0.3934 0.6460 0.3467 0.050 Uiso 1 1 calc R . . . .
C10 C -0.2970(14) 0.581(2) 0.2597(16) 0.055(9) Uani 1 1 d . U . . .
H10 H -0.3970 0.5654 0.2000 0.066 Uiso 1 1 calc R . . . .
C18 C 0.3099(11) 0.8326(18) 0.5023(18) 0.058(10) Uani 1 1 d . U . . .
H18A H 0.2589 0.8367 0.3732 0.087 Uiso 1 1 calc GR . . . .
H18B H 0.4199 0.8484 0.5160 0.087 Uiso 1 1 calc GR . . . .
H18C H 0.2484 0.8556 0.5822 0.087 Uiso 1 1 calc GR . . . .
O2 O 0.4229(6) 0.4680(9) 0.2083(7) 0.079(10) Uani 1 1 d . U . . .
C19 C 0.2937(14) 0.4380(18) 0.2177(16) 0.052(9) Uani 1 1 d . U . . .
C20 C 0.2793(15) 0.368(2) 0.187(2) 0.071(10) Uani 1 1 d . U . . .
H20A H 0.2013 0.3516 0.2607 0.106 Uiso 1 1 calc GR . . . .
H20B H 0.3844 0.3492 0.2264 0.106 Uiso 1 1 calc GR . . . .
H20C H 0.2433 0.3596 0.0561 0.106 Uiso 1 1 calc GR . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C2 0.029(4) 0.09(3) 0.021(5) 0.006(7) 0.007(3) 0.001(6)
C1 0.034(4) 0.09(3) 0.030(6) 0.003(7) 0.007(4) 0.001(6)
C14 0.034(4) 0.09(3) 0.049(5) 0.006(8) 0.007(3) 0.006(7)
C13 0.042(5) 0.10(3) 0.040(7) 0.000(8) 0.011(4) -0.002(7)
C12 0.030(4) 0.09(3) 0.025(6) 0.006(7) 0.009(3) 0.000(6)
C15 0.031(4) 0.09(3) 0.026(6) 0.004(6) 0.010(3) -0.002(6)
C16 0.029(4) 0.09(3) 0.023(6) 0.006(7) 0.006(3) -0.001(6)
C9 0.028(4) 0.09(3) 0.022(6) 0.006(7) 0.001(3) 0.000(6)
C8 0.030(4) 0.09(3) 0.034(7) 0.001(8) 0.005(4) -0.001(7)
C7 0.032(3) 0.09(3) 0.046(5) 0.001(8) 0.003(3) -0.004(6)
C6 0.038(4) 0.09(3) 0.032(7) 0.005(7) 0.007(4) -0.005(6)
C5 0.025(4) 0.09(3) 0.027(6) 0.004(7) 0.003(3) -0.005(6)
C4 0.031(4) 0.09(3) 0.051(7) -0.003(8) -0.002(4) -0.002(7)
O1 0.043(3) 0.08(3) 0.075(4) 0.004(7) -0.014(3) -0.006(6)
C17 0.046(5) 0.09(3) 0.036(6) 0.000(9) 0.010(4) -0.001(7)
C3 0.027(4) 0.08(3) 0.040(7) 0.002(8) 0.006(4) -0.003(7)
C11 0.024(4) 0.09(3) 0.010(6) 0.010(7) 0.009(3) 0.000(7)
C10 0.040(5) 0.10(3) 0.027(8) 0.001(8) -0.002(4) 0.006(7)
C18 0.038(5) 0.09(3) 0.048(7) -0.001(9) 0.002(4) -0.003(9)
O2 0.040(3) 0.12(3) 0.080(4) 0.002(8) 0.013(3) -0.013(6)
C19 0.033(4) 0.10(3) 0.021(5) 0.000(9) -0.002(4) -0.002(8)
C20 0.051(6) 0.10(3) 0.062(8) -0.004(10) 0.014(5) -0.007(10)

_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
C2 C1 1.39(6) . ?
C2 C15 1.49(3) . ?
C2 C3 1.42(4) . ?
C1 C14 1.39(2) . ?
C1 C17 1.49(3) . ?
C14 C13 1.39(2) . ?
C13 C12 1.30(7) . ?
C12 C15 1.51(4) . ?
C12 C11 1.53(3) . ?
C15 C16 1.31(6) . ?
C16 C9 1.43(3) . ?
C16 C5 1.47(3) . ?
C9 C8 1.35(6) . ?
C9 C10 1.48(3) . ?
C8 C7 1.44(3) . ?
C7 C6 1.42(2) . ?
C6 C5 1.35(6) . ?
C6 C19 1.54(4) . ?
C5 C4 1.45(3) . ?
C4 C3 1.40(7) . ?
O1 C17 1.201(18) . ?
C17 C18 1.56(6) . ?
C11 C10 1.16(6) . ?
O2 C19 1.26(2) . ?
C19 C20 1.53(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 C2 C15 122.5(19) . . ?
C1 C2 C3 125(2) . . ?
C3 C2 C15 112(3) . . ?
C2 C1 C14 120.6(17) . . ?
C2 C1 C17 121(2) . . ?
C14 C1 C17 118(3) . . ?
C13 C14 C1 119(2) . . ?
C12 C13 C14 123.0(19) . . ?
C13 C12 C15 123.4(18) . . ?
C13 C12 C11 128.1(19) . . ?
C15 C12 C11 108(3) . . ?
C2 C15 C12 111(3) . . ?
C16 C15 C2 125.0(19) . . ?
C16 C15 C12 123.8(17) . . ?
C15 C16 C9 121(2) . . ?
C15 C16 C5 123.3(15) . . ?
C9 C16 C5 115(3) . . ?
C16 C9 C10 116(3) . . ?
C8 C9 C16 121(2) . . ?
C8 C9 C10 123.2(17) . . ?
C9 C8 C7 124.1(14) . . ?
C6 C7 C8 115(2) . . ?
C7 C6 C19 112(3) . . ?
C5 C6 C7 121.9(16) . . ?
C5 C6 C19 125.7(17) . . ?
C6 C5 C16 122.3(15) . . ?
C6 C5 C4 124(2) . . ?
C4 C5 C16 113(3) . . ?
C3 C4 C5 123(2) . . ?
C1 C17 C18 117.1(19) . . ?
O1 C17 C1 124(3) . . ?
O1 C17 C18 119(2) . . ?
C4 C3 C2 123.4(19) . . ?
C10 C11 C12 127.1(18) . . ?
C11 C10 C9 122.3(18) . . ?
O2 C19 C6 115(3) . . ?
O2 C19 C20 123.3(19) . . ?
C20 C19 C6 121.5(19) . . ?

_iucr_refine_instructions_details 
;
TITL f9spektro in P21/c #14
REM reset to P21/c #14
CELL 0.56087 8.249635 21.621 7.165503 90 98.8737 90
ZERR 4 0.002411 0.096143 0.002276 0 0.025 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H O
UNIT 80 56 8
RIGU C17 C2 C1 C15 C3 C14 C12 C16 C4 C13 O1 C18 C11 C9 C5 C10 C8 C6 C7 C19 =
 O2 C20
 
L.S. 4
PLAN  2
SIZE 0.11 0.2 0.28
BOND
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%./f9spektro.hkl">
REM </olex2.extras>
 
WGHT    0.047100    0.400000
FVAR       2.70488
C2    1    0.161795    0.664978    0.457538    11.00000    0.02857    0.08547 =
         0.02105    0.00646    0.00709    0.00075
C1    1    0.159281    0.727028    0.508805    11.00000    0.03406    0.08610 =
         0.02958    0.00294    0.00717    0.00087
C14    1    0.011017    0.758498    0.501127    11.00000    0.03390    0.08842 =
         0.04930    0.00614    0.00688    0.00559
AFIX  43
H14    2    0.009873    0.800410    0.530080    11.00000   -1.20000
AFIX   0
C13   1   -0.135458    0.726425    0.449562    11.00000    0.04213    0.09676 =
         0.04021    0.00047    0.01088   -0.00156
AFIX  43
H13   2   -0.233541    0.746516    0.459007    11.00000   -1.20000
AFIX   0
C12   1   -0.141356    0.669570    0.388707    11.00000    0.02998    0.09489 =
         0.02461    0.00601    0.00924   -0.00006
C15    1    0.009131    0.629288    0.391338    11.00000    0.03115    0.09164 =
         0.02572    0.00441    0.00998   -0.00245
C16    1    0.004760    0.572789    0.326533    11.00000    0.02869    0.09131 =
         0.02259    0.00642    0.00581   -0.00148
C9    1   -0.148063    0.542126    0.264706    11.00000    0.02810    0.09064 =
         0.02191    0.00621    0.00108   -0.00009
C8   1   -0.151162    0.483778    0.196502    11.00000    0.02995    0.09287 =
         0.03390    0.00130    0.00456   -0.00120
AFIX  43
H8   2   -0.252753    0.466397    0.151251    11.00000   -1.20000
AFIX   0
C7    1   -0.006677    0.446792    0.189541    11.00000    0.03207    0.09059 =
         0.04598    0.00088    0.00326   -0.00429
AFIX  43
H7    2   -0.012270    0.405939    0.148432    11.00000   -1.20000
AFIX   0
C6    1    0.145119    0.477406    0.250211    11.00000    0.03765    0.09007 =
         0.03194    0.00487    0.00739   -0.00547
C5   1    0.151843    0.534974    0.324221    11.00000    0.02542    0.08871 =
         0.02711    0.00410    0.00307   -0.00533
C4    1    0.302083    0.565993    0.406964    11.00000    0.03135    0.08570 =
         0.05065   -0.00273   -0.00239   -0.00158
AFIX  43
H4    2    0.400170    0.544058    0.420451    11.00000   -1.20000
AFIX   0
O1   3    0.437751    0.742826    0.649684    11.00000    0.04350    0.08331 =
         0.07520    0.00393   -0.01410   -0.00643
C17   1    0.314167    0.763152    0.559988    11.00000    0.04598    0.08785 =
         0.03636    0.00015    0.00953   -0.00085
C3   1    0.304864    0.627690    0.467223    11.00000    0.02708    0.08390 =
         0.03968    0.00218    0.00608   -0.00343
AFIX  43
H3   2    0.405499    0.645164    0.516092    11.00000   -1.20000
AFIX   0
C11   1   -0.293230    0.629441    0.327423    11.00000    0.02443    0.09272 =
         0.01005    0.00973    0.00920    0.00012
AFIX  43
H11   2   -0.393361    0.645995    0.346746    11.00000   -1.20000
AFIX   0
C10   1   -0.296990    0.580765    0.259689    11.00000    0.03961    0.09749 =
         0.02695    0.00123   -0.00179    0.00600
AFIX  43
H10   2   -0.396964    0.565371    0.200043    11.00000   -1.20000
AFIX   0
C18   1    0.309950    0.832622    0.502319    11.00000    0.03841    0.08647 =
         0.04809   -0.00059    0.00246   -0.00334
AFIX 137
H18A  2    0.258870    0.836714    0.373161    11.00000   -1.50000
H18B  2    0.419935    0.848387    0.516033    11.00000   -1.50000
H18C  2    0.248443    0.855603    0.582202    11.00000   -1.50000
AFIX   0
O2    3    0.422927    0.468006    0.208319    11.00000    0.03998    0.11764 =
         0.08011    0.00164    0.01339   -0.01337
C19   1    0.293708    0.438032    0.217665    11.00000    0.03306    0.09864 =
         0.02115   -0.00021   -0.00177   -0.00211
C20   1    0.279332    0.368084    0.187407    11.00000    0.05113    0.10080 =
         0.06234   -0.00360    0.01368   -0.00693
AFIX 137
H20A  2    0.201321    0.351598    0.260733    11.00000   -1.50000
H20B  2    0.384356    0.349158    0.226448    11.00000   -1.50000
H20C  2    0.243297    0.359601    0.056051    11.00000   -1.50000
AFIX   0
HKLF 4
 
REM  f9spektro in P21/c #14
REM R1 =  0.0659 for     350 Fo > 4sig(Fo)  and  0.1413 for all     579 data
REM    201 parameters refined using    189 restraints
 
END  
     
WGHT      0.0471      0.4000 

REM Highest difference peak  0.089,  deepest hole -0.098,  1-sigma level  0.025
Q1    1   0.1463  0.5698  0.1287  11.00000  0.05    0.09
Q2    1   0.5520  0.4639  0.0896  11.00000  0.05    0.09

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0659 for 350 Fo > 4sig(Fo) and 0.1413 for all 2162 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.09, deepest hole -0.10
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.1413
  REM R1_gt = 0.0659
  REM wR_ref = 0.1409
  REM GOOF = 1.201
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 2162
  REM Reflections_gt = 350
  REM Parameters = n/a
  REM Hole = -0.10
  REM Peak = 0.09
  REM Flack = n/a

  
;
_olex2_date_sample_data_collection 2020-02-19
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_diffrn_reflns_filtered   460
_oxdiff_exptl_absorpt_empirical_details 
'Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling'
_oxdiff_exptl_absorpt_empirical_full_max 2.096
_oxdiff_exptl_absorpt_empirical_full_min 0.657


# start Validation Reply Form
_vrf_PLAT029_2bisAP-delta_980000kPa 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.243 Why?  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected. Also, scattering power of the sample with Ag Ka radiation
was weak.
;
_vrf_PLAT213_2bisAP-delta_980000kPa 
;
PROBLEM: Atom C11             has ADP max/min Ratio .....        4.2 prolat
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees on a very thin plate. This limited the number
of reflections that could be collected, as most of them were obscured by the
DAC, which together with weak scattering negatively affected the precision.
;
_vrf_PLAT340_2bisAP-delta_980000kPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.04174 Ang.  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees on a very thin plate. This limited the number
of reflections that could be collected, as most of them were obscured by the
DAC, which together with weak scattering negatively affected the precision.
;
_vrf_PLAT911_2bisAP-delta_980000kPa 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L= 0.600           150 Report
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
;
_vrf_PLAT088_2bisAP-delta_980000kPa 
;
PROBLEM: Poor Data / Parameter Ratio ....................       2.88 Note  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
;
_vrf_PLAT148_2bisAP-delta_980000kPa 
;
PROBLEM: s.u. on the      b    - Axis is (Too) Large ....     0.1000 Ang.  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC, and in 
particular affected the b direction due to crystal orientation.
;
_vrf_PLAT242_2bisAP-delta_980000kPa 
;
PROBLEM: Low    MainMol Ueq as Compared to Neighbors of        C19 Check   
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC, and 
resulted in lower accuracy of the model.
;
_vrf_PLAT250_2bisAP-delta_980000kPa 
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.7 Note  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC, and in 
particular affected the b direction due to crystal orientation. As a result,
all ADP-s are artificially elongated in one direction.
;
_vrf_PLAT368_2bisAP-delta_980000kPa 
;
PROBLEM: Short  C(sp2)-C(sp2) Bond  C11      - C10      .       1.15 Ang.  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC, 
resulting in a less precise model.
;
_vrf_PLAT369_2bisAP-delta_980000kPa 
;
PROBLEM: Long   C(sp2)-C(sp2) Bond  C6       - C19      .       1.54 Ang.  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC, 
resulting in a less precise model.
;
_vrf_PLAT906_2bisAP-delta_980000kPa 
;
PROBLEM: Large K Value in the Analysis of Variance ......     67.847 Check 
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. Highest resolution data might be affected 
by gasket shadowing and therefore very week.
;
_vrf_PLAT978_2bisAP-delta_980000kPa 
;
PROBLEM: Number C-C Bonds with Positive Residual Density.          0 Info  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. Highest resolution data were affected 
by gasket shadowing and therefore very week, so fine features of electron density
could not be discerned.
;
# 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_2bisAP-gamma_840000kPa
_database_code_depnum_ccdc_archive 'CCDC 2039418'
loop_
_audit_author_name
_audit_author_address
'Daniel Tchon'
;Faculty of Chemistry, University of Warsaw
Poland
;
_audit_update_record             
;
2020-10-19 deposited with the CCDC.	2021-01-21 downloaded from the CCDC.
;
_audit_creation_date             2020-03-20
_audit_creation_method           
;
Olex2 1.2
(compiled May 29 2018 13:30:08 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            1,1'-Pyrene-1,8-diyldiethanone
_chemical_name_systematic        1,8-Diacetylpyrene
_chemical_formula_moiety         'C20 H14 O2'
_chemical_formula_sum            'C20 H14 O2'
_chemical_formula_weight         286.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 '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 0.0056 0.0036 '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                   8.072(3)
_cell_length_b                   22.714(12)
_cell_length_c                   7.106(11)
_cell_angle_alpha                90
_cell_angle_beta                 92.98(7)
_cell_angle_gamma                90
_cell_volume                     1301(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    148
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15.8720
_cell_measurement_theta_min      2.1270
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.060
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.06509
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.46 (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    1.462
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_preparation       
'Mounted in a Diamond-Anvil Cell using silicone oil as pressure medium.,Luminescent'
_exptl_crystal_pressure_history  
'Pressurized to 0.84 GPa and left to stabilize over 24 hours.'
_exptl_crystal_recrystallization_method 'from acetonitrile at room temperature'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
High-pressure measurement at 0.84 GPa in a Merill-Basset Diamond Anvil Cell with
effective opening angle of 30 deg. and silicone 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  0.0906
_diffrn_reflns_av_unetI/netI     0.1451
_diffrn_reflns_Laue_measured_fraction_full 0.225
_diffrn_reflns_Laue_measured_fraction_max 0.289
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            861
_diffrn_reflns_point_group_measured_fraction_full 0.225
_diffrn_reflns_point_group_measured_fraction_max 0.289
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         18.082
_diffrn_reflns_theta_min         1.994
_diffrn_ambient_temperature      293(2)
_diffrn_ambient_pressure         840000
_diffrn_ambient_environment      'Diamond Anvil Cell filled with silicone oil'
_diffrn_crystal_treatment        
'Pressurized slowly in silicone oil as a hydrostatic medium.'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0064
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.225
_diffrn_measured_fraction_theta_max 0.289
_diffrn_measurement_details      
'List of Runs (angles in degrees, time in seconds): # Type Start End Width tₑₓₚ ω θ κ φ Frames -------------------------------------------------------------------------- 1 ω 11.00 38.00 0.30 100.00 -- 10.64 -67.00-157.00 90 2 ω -17.00 16.00 0.30 100.00 -- 10.64 13.00 176.00 110 3 ω -41.00 -13.70 0.30 100.00 -- -10.96 67.00 157.00 91'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 
'Diamond Anvil Cell, effective opening angle of 30 deg.'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0048957000
_diffrn_orient_matrix_UB_12      0.0143658000
_diffrn_orient_matrix_UB_13      0.0636060000
_diffrn_orient_matrix_UB_21      -0.0504838000
_diffrn_orient_matrix_UB_22      0.0144854000
_diffrn_orient_matrix_UB_23      -0.0311685000
_diffrn_orient_matrix_UB_31      -0.0475680000
_diffrn_orient_matrix_UB_32      -0.0138147000
_diffrn_orient_matrix_UB_33      0.0341268000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56087
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Ag) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                271
_reflns_number_total             533
_reflns_odcompleteness_completeness 27.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     18.11
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.193
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         533
_refine_ls_number_restraints     291
_refine_ls_R_factor_all          0.2024
_refine_ls_R_factor_gt           0.1208
_refine_ls_restrained_S_all      0.908
_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          0.2866
_refine_ls_wR_factor_ref         0.3526
_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. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C4) \\sim
Ueq, Uanis(C5) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C7) \\sim Ueq,
Uanis(C8) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C15)
\\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq,
Uanis(C11) \\sim Ueq, Uanis(C10) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.05
Uanis(C20) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
3. Rigid body (RIGU) restrains
 C19, O1, C17, C1, C18, C14, C2, C13, C3, C15, C12, C4, C16, C11, C5, C9, C10,
 C6, C8, C7, O2, C20
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C14(H14), C13(H13), C11(H11), C4(H4), C8(H8), C7(H7), C10(H10)
4.b Idealised Me refined as rotating group:
 C18(H18B,H18A,H18C), C20(H20B,H20A,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4493(9) 0.7668(4) 0.790(2) 0.048(7) Uani 1 1 d . U . . .
O2 O 0.4424(9) 0.4821(4) 0.768(2) 0.080(8) Uani 1 1 d . U . . .
C3 C 0.3060(15) 0.6558(6) 0.854(4) 0.031(4) Uani 1 1 d . U . . .
H3 H 0.4030 0.6757 0.8908 0.037 Uiso 1 1 calc R . . . .
C1 C 0.1575(15) 0.7501(7) 0.779(3) 0.036(4) Uani 1 1 d . U . . .
C14 C 0.0079(15) 0.7773(7) 0.741(4) 0.045(5) Uani 1 1 d . U . . .
H14 H 0.0086 0.8182 0.7413 0.054 Uiso 1 1 calc R . . . .
C13 C -0.1376(16) 0.7516(7) 0.705(4) 0.039(5) Uani 1 1 d . U . . .
H13 H -0.2342 0.7730 0.6785 0.047 Uiso 1 1 calc R . . . .
C12 C -0.1361(15) 0.6903(8) 0.710(3) 0.041(5) Uani 1 1 d . U . . .
C15 C 0.0090(14) 0.6556(6) 0.750(3) 0.034(5) Uani 1 1 d . U . . .
C2 C 0.1576(15) 0.6889(8) 0.796(3) 0.044(5) Uani 1 1 d . U . . .
C11 C -0.2894(16) 0.6571(6) 0.665(4) 0.041(5) Uani 1 1 d . U . . .
H11 H -0.3878 0.6776 0.6402 0.049 Uiso 1 1 calc R . . . .
C17 C 0.3148(17) 0.7886(8) 0.817(4) 0.046(6) Uani 1 1 d . U . . .
C18 C 0.3045(19) 0.8517(6) 0.847(4) 0.065(10) Uani 1 1 d . U . . .
H18B H 0.4126 0.8668 0.8830 0.097 Uiso 1 1 calc GR . . . .
H18A H 0.2299 0.8597 0.9443 0.097 Uiso 1 1 calc GR . . . .
H18C H 0.2643 0.8704 0.7319 0.097 Uiso 1 1 calc GR . . . .
C4 C 0.3041(16) 0.5954(6) 0.856(4) 0.040(5) Uani 1 1 d . U . . .
H4 H 0.3989 0.5753 0.8994 0.048 Uiso 1 1 calc R . . . .
C5 C 0.1602(13) 0.5624(7) 0.793(3) 0.030(4) Uani 1 1 d . U . . .
C16 C 0.0085(15) 0.5912(6) 0.755(3) 0.034(5) Uani 1 1 d . U . . .
C9 C -0.1449(14) 0.5629(7) 0.710(3) 0.039(5) Uani 1 1 d . U . . .
C8 C -0.1457(15) 0.5014(7) 0.706(4) 0.043(5) Uani 1 1 d . U . . .
H8 H -0.2437 0.4814 0.6743 0.052 Uiso 1 1 calc R . . . .
C7 C 0.0006(14) 0.4698(7) 0.748(3) 0.036(5) Uani 1 1 d . U . . .
H7 H -0.0032 0.4290 0.7527 0.043 Uiso 1 1 calc R . . . .
C6 C 0.1505(15) 0.4983(7) 0.783(4) 0.037(4) Uani 1 1 d . U . . .
C10 C -0.2916(16) 0.5990(6) 0.659(4) 0.042(5) Uani 1 1 d . U . . .
H10 H -0.3900 0.5801 0.6217 0.050 Uiso 1 1 calc R . . . .
C19 C 0.3053(16) 0.4618(6) 0.790(4) 0.047(6) Uani 1 1 d . U . . .
C20 C 0.2883(18) 0.3968(5) 0.846(4) 0.037(5) Uani 1 1 d . U . . .
H20B H 0.2540 0.3741 0.7365 0.055 Uiso 1 1 calc GR . . . .
H20A H 0.2069 0.3932 0.9389 0.055 Uiso 1 1 calc GR . . . .
H20C H 0.3932 0.3825 0.8965 0.055 Uiso 1 1 calc GR . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.044(4) 0.052(6) 0.05(2) -0.005(5) 0.007(4) -0.001(3)
O2 0.040(4) 0.047(5) 0.16(2) 0.005(6) 0.013(5) 0.000(3)
C3 0.034(3) 0.042(4) 0.016(11) -0.004(3) 0.010(4) -0.003(2)
C1 0.039(3) 0.043(3) 0.026(12) -0.004(3) 0.008(4) -0.0013(19)
C14 0.040(3) 0.044(4) 0.050(13) -0.001(3) 0.004(4) -0.002(2)
C13 0.039(3) 0.043(4) 0.037(12) -0.002(3) 0.007(4) -0.001(2)
C12 0.036(3) 0.043(3) 0.044(13) -0.002(3) 0.002(4) -0.001(2)
C15 0.036(3) 0.042(3) 0.026(12) -0.003(2) 0.006(4) -0.0009(18)
C2 0.038(3) 0.044(3) 0.049(12) -0.003(3) 0.000(4) -0.0019(19)
C11 0.036(4) 0.043(4) 0.043(12) 0.000(3) 0.002(4) 0.000(2)
C17 0.042(3) 0.048(4) 0.049(17) -0.008(4) 0.006(4) -0.004(2)
C18 0.040(6) 0.050(4) 0.10(3) -0.017(6) 0.005(7) -0.004(3)
C4 0.037(4) 0.043(4) 0.041(11) -0.003(3) 0.000(4) -0.002(2)
C5 0.034(3) 0.041(3) 0.017(11) -0.002(3) 0.007(4) -0.0017(18)
C16 0.035(3) 0.042(3) 0.027(12) -0.003(2) 0.005(4) -0.0009(17)
C9 0.036(3) 0.042(3) 0.039(12) -0.001(3) 0.001(4) -0.0015(19)
C8 0.039(4) 0.043(4) 0.048(13) -0.001(3) -0.002(4) -0.002(2)
C7 0.037(3) 0.042(4) 0.029(13) -0.001(3) 0.003(4) -0.002(2)
C6 0.037(3) 0.042(3) 0.033(12) -0.003(3) 0.003(4) -0.0016(18)
C10 0.036(4) 0.043(4) 0.045(12) 0.000(3) 0.000(4) -0.001(2)
C19 0.038(3) 0.043(4) 0.059(18) -0.008(4) 0.000(4) -0.001(2)
C20 0.032(5) 0.042(4) 0.036(12) -0.012(5) -0.015(6) -0.004(3)

_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 1.217(14) . ?
O2 C19 1.216(14) . ?
C3 C2 1.46(2) . ?
C3 C4 1.370(16) . ?
C1 C14 1.37(2) . ?
C1 C2 1.395(18) . ?
C1 C17 1.55(2) . ?
C14 C13 1.32(2) . ?
C13 C12 1.393(17) . ?
C12 C15 1.43(2) . ?
C12 C11 1.47(2) . ?
C15 C2 1.44(2) . ?
C15 C16 1.46(2) . ?
C11 C10 1.320(17) . ?
C17 C18 1.452(17) . ?
C4 C5 1.43(2) . ?
C5 C16 1.40(2) . ?
C5 C6 1.461(19) . ?
C16 C9 1.42(2) . ?
C9 C8 1.397(19) . ?
C9 C10 1.47(2) . ?
C8 C7 1.40(2) . ?
C7 C6 1.38(2) . ?
C6 C19 1.498(18) . ?
C19 C20 1.536(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 C3 C2 120.7(13) . . ?
C14 C1 C2 117.5(12) . . ?
C14 C1 C17 119.0(16) . . ?
C2 C1 C17 123.3(13) . . ?
C13 C14 C1 127.1(17) . . ?
C14 C13 C12 115.4(13) . . ?
C13 C12 C15 124.2(12) . . ?
C13 C12 C11 120.1(13) . . ?
C15 C12 C11 115.7(15) . . ?
C12 C15 C2 114.9(14) . . ?
C12 C15 C16 123.5(12) . . ?
C2 C15 C16 121.5(12) . . ?
C1 C2 C3 122.5(12) . . ?
C1 C2 C15 120.4(13) . . ?
C15 C2 C3 117.1(15) . . ?
C10 C11 C12 122.0(13) . . ?
O1 C17 C1 118.2(15) . . ?
O1 C17 C18 118.8(13) . . ?
C18 C17 C1 121.9(13) . . ?
C3 C4 C5 122.0(13) . . ?
C4 C5 C6 125.3(13) . . ?
C16 C5 C4 120.1(14) . . ?
C16 C5 C6 114.3(11) . . ?
C5 C16 C15 117.8(12) . . ?
C5 C16 C9 125.2(14) . . ?
C9 C16 C15 116.9(13) . . ?
C16 C9 C10 119.1(14) . . ?
C8 C9 C16 117.5(12) . . ?
C8 C9 C10 123.3(13) . . ?
C9 C8 C7 120.3(12) . . ?
C6 C7 C8 121.3(17) . . ?
C5 C6 C19 120.5(11) . . ?
C7 C6 C5 121.3(12) . . ?
C7 C6 C19 117.9(15) . . ?
C11 C10 C9 122.7(13) . . ?
O2 C19 C6 123.2(13) . . ?
O2 C19 C20 119.5(12) . . ?
C6 C19 C20 117.0(11) . . ?

_iucr_refine_instructions_details 
;
TITL 2APb_spektro in P21/c #14
REM reset to P21/c #14
CELL 0.56087 8.071746 22.713697 7.106232 90 92.9811 90
ZERR 4 0.003045 0.011808 0.010921 0 0.0705 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H O
UNIT 80 56 8
RIGU 0.001 0.001 C19 O1 C17 C1 C18 C14 C2 C13 C3 C15 C12 C4 C16 C11 C5 C9 C10 =
 C6 C8 C7 O2 C20
ISOR 0.01 0.05 C1 C2 C3 C4 C5 C6 C7 C8 C9 C16 C15 C12 C13 C14 C11 C10
ISOR 0.005 0.01 C20
 
L.S. 4
PLAN  2
SIZE 0.11 0.21 0.24
BOND
fmap 2
acta
OMIT 3 18 2
REM <olex2.extras>
REM <HklSrc "%./2APb_spektro.hkl">
REM </olex2.extras>
 
WGHT    0.200000
FVAR       0.88140
O1    3    0.449293    0.766833    0.790315    11.00000    0.04373    0.05215 =
         0.04842   -0.00467    0.00744   -0.00143
O2    3    0.442401    0.482076    0.767723    11.00000    0.03962    0.04730 =
         0.15502    0.00529    0.01343   -0.00002
C3    1    0.305981    0.655759    0.854479    11.00000    0.03435    0.04227 =
         0.01618   -0.00353    0.01044   -0.00276
AFIX  43
H3    2    0.403029    0.675725    0.890805    11.00000   -1.20000
AFIX   0
C1    1    0.157485    0.750127    0.779355    11.00000    0.03935    0.04346 =
         0.02646   -0.00418    0.00759   -0.00128
C14    1    0.007884    0.777278    0.741490    11.00000    0.04037    0.04431 =
         0.05044   -0.00084    0.00428   -0.00160
AFIX  43
H14    2    0.008566    0.818221    0.741264    11.00000   -1.20000
AFIX   0
C13    1   -0.137607    0.751602    0.705169    11.00000    0.03888    0.04347 =
         0.03659   -0.00185    0.00745   -0.00084
AFIX  43
H13    2   -0.234154    0.773038    0.678513    11.00000   -1.20000
AFIX   0
C12    1   -0.136099    0.690287    0.709634    11.00000    0.03612    0.04345 =
         0.04394   -0.00174    0.00215   -0.00063
C15    1    0.009019    0.655637    0.750354    11.00000    0.03586    0.04209 =
         0.02573   -0.00287    0.00607   -0.00094
C2    1    0.157617    0.688923    0.796408    11.00000    0.03805    0.04381 =
         0.04900   -0.00274    0.00047   -0.00190
C11    1   -0.289392    0.657054    0.665118    11.00000    0.03621    0.04288 =
         0.04341   -0.00022    0.00162   -0.00047
AFIX  43
H11    2   -0.387810    0.677566    0.640182    11.00000   -1.20000
AFIX   0
C17    1    0.314769    0.788583    0.816940    11.00000    0.04211    0.04806 =
         0.04872   -0.00753    0.00641   -0.00412
C18   1    0.304525    0.851711    0.846546    11.00000    0.03995    0.04990 =
         0.10461   -0.01737    0.00473   -0.00403
AFIX 137
H18B  2    0.412598    0.866782    0.882952    11.00000   -1.50000
H18A  2    0.229909    0.859668    0.944310    11.00000   -1.50000
H18C  2    0.264298    0.870414    0.731946    11.00000   -1.50000
AFIX   0
C4   1    0.304077    0.595440    0.856153    11.00000    0.03664    0.04276 =
         0.04148   -0.00343    0.00020   -0.00236
AFIX  43
H4   2    0.398917    0.575310    0.899355    11.00000   -1.20000
AFIX   0
C5   1    0.160208    0.562424    0.793278    11.00000    0.03359    0.04136 =
         0.01712   -0.00222    0.00712   -0.00166
C16   1    0.008549    0.591201    0.754549    11.00000    0.03472    0.04204 =
         0.02663   -0.00301    0.00471   -0.00090
C9   1   -0.144871    0.562918    0.710341    11.00000    0.03560    0.04220 =
         0.03944   -0.00103    0.00104   -0.00149
C8   1   -0.145681    0.501446    0.705612    11.00000    0.03871    0.04253 =
         0.04837   -0.00108   -0.00153   -0.00185
AFIX  43
H8   2   -0.243732    0.481404    0.674261    11.00000   -1.20000
AFIX   0
C7   1    0.000650    0.469845    0.747915    11.00000    0.03708    0.04174 =
         0.02877   -0.00057    0.00280   -0.00219
AFIX  43
H7   2   -0.003166    0.428953    0.752741    11.00000   -1.20000
AFIX   0
C6   1    0.150548    0.498271    0.782609    11.00000    0.03699    0.04189 =
         0.03319   -0.00294    0.00307   -0.00159
C10   1   -0.291576    0.598981    0.659467    11.00000    0.03596    0.04304 =
         0.04543   -0.00014    0.00016   -0.00120
AFIX  43
H10   2   -0.390014    0.580104    0.621735    11.00000   -1.20000
AFIX   0
C19   1    0.305322    0.461753    0.789727    11.00000    0.03779    0.04265 =
         0.05935   -0.00777    0.00025   -0.00063
C20   1    0.288268    0.396797    0.845647    11.00000    0.03152    0.04155 =
         0.03565   -0.01213   -0.01466   -0.00352
AFIX 137
H20B  2    0.254013    0.374077    0.736543    11.00000   -1.50000
H20A  2    0.206939    0.393228    0.938868    11.00000   -1.50000
H20C  2    0.393196    0.382490    0.896481    11.00000   -1.50000
AFIX   0
HKLF 4
 
REM  2APb_spektro in P21/c #14
REM R1 =  0.1208 for     271 Fo > 4sig(Fo)  and  0.2024 for all     533 data
REM    201 parameters refined using    291 restraints
 
END  
     
WGHT      0.2000      0.0000 

REM Highest difference peak  0.318,  deepest hole -0.277,  1-sigma level  0.073
Q1    1  -0.0196  0.6234  0.6263  11.00000  0.05    0.32
Q2    1   0.0367  0.6268  0.8744  11.00000  0.05    0.29

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.1208 for 271 Fo > 4sig(Fo) and 0.2024 for all 867 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.32, deepest hole -0.28
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.2024
  REM R1_gt = 0.1208
  REM wR_ref = 0.3526
  REM GOOF = 1.193
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 867
  REM Reflections_gt = 271
  REM Parameters = n/a
  REM Hole = -0.28
  REM Peak = 0.32
  REM Flack = n/a

  
;
_olex2_date_sample_data_collection 2020-03-12
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_diffrn_reflns_filtered   401
_oxdiff_exptl_absorpt_empirical_details 
'Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling'
_oxdiff_exptl_absorpt_empirical_full_max 5.138
_oxdiff_exptl_absorpt_empirical_full_min 0.300


# start Validation Reply Form
_vrf_THETM01_2bisAP-gamma_840000kPa 
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees on a very thin plate. This resulted in low 
diffracted intensities, low available data resolution and high Rint value.
;
_vrf_PLAT149_2bisAP-gamma_840000kPa 
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.07 Degree
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC, and in 
particular affected the beta angle due to crystal orientation.
;
_vrf_PLAT340_2bisAP-gamma_840000kPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01961 Ang.  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees on a very thin plate. This limited the number
of reflections that could be collected, as most of them were obscured by the
DAC, which together with weak scattering negatively affected the precision.
;
_vrf_PLAT088_2bisAP-gamma_840000kPa 
;
PROBLEM: Poor Data / Parameter Ratio ....................       2.65 Note  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
;
_vrf_PLAT911_2bisAP-gamma_840000kPa 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L= 0.553           871 Report
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
;
_vrf_PLAT018_2bisAP-gamma_840000kPa 
;
PROBLEM: _diffrn_measured_fraction_theta_max .NE. *_full           ! Check 
RESPONSE: A discrepancy between what olex2 and shelx report.
;
_vrf_PLAT082_2bisAP-gamma_840000kPa 
;
PROBLEM: High R1 Value ..................................       0.12 Report
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC, and 
affected the fit of the final model.
;
_vrf_PLAT084_2bisAP-gamma_840000kPa 
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.35 Report
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC, and 
affected the fit of the final model.
;
_vrf_PLAT148_2bisAP-gamma_840000kPa 
;
PROBLEM: s.u. on the      c    - Axis is (Too) Large ....      0.011 Ang.  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC, and in 
particular affected the c direction due to crystal orientation.
;
_vrf_PLAT369_2bisAP-gamma_840000kPa 
;
PROBLEM: Long   C(sp2)-C(sp2) Bond  C1       - C17       .       1.55 Ang.  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC, 
resulting in a less precise model.
;
_vrf_PLAT906_2bisAP-gamma_840000kPa 
;
PROBLEM: Large K Value in the Analysis of Variance ......     42.791 Check 
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. Highest resolution data might be affected 
by gasket shadowing and therefore very week.
;
_vrf_PLAT913_2bisAP-gamma_840000kPa 
;
PROBLEM: Missing # of Very Strong Reflections in FCF ....          4 Note  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. Highest resolution data might be affected 
by gasket shadowing and therefore very week.
;
# 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_2bisAP-gamma_1160000kPa
_database_code_depnum_ccdc_archive 'CCDC 2039420'
loop_
_audit_author_name
_audit_author_address
'Daniel Tchon'
;Faculty of Chemistry, University of Warsaw
Poland
;
_audit_update_record             
;
2020-10-19 deposited with the CCDC.	2021-01-21 downloaded from the CCDC.
;
_audit_creation_date             2019-08-06
_audit_creation_method           
;
Olex2 1.2
(compiled May 29 2018 13:30:08 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            1,1'-Pyrene-1,8-diyldiethanone
_chemical_name_systematic        1,8-Diacetylpyrene
_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 0.0015 0.0009 '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 0.0056 0.0036 '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                   7.997(3)
_cell_length_b                   22.591(8)
_cell_length_c                   6.94(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.73(14)
_cell_angle_gamma                90
_cell_volume                     1253(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    331
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.0780
_cell_measurement_theta_min      2.0150
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.00708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            'clear greenish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             600
_exptl_crystal_preparation       
'Mounted in a Diamond-Anvil Cell using parabar oil as pressure medium.,Luminescent'
_exptl_crystal_pressure_history  
'Pressurized to 1.16 GPa and left to stabilize over 24 hours.'
_exptl_crystal_recrystallization_method 'from acetonitrile at room temperature'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
High-pressure measurement at 1.16 GPa in a Merill-Basset Diamond Anvil Cell with
effective opening angle of 30 deg. and parabar 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  0.0396
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_Laue_measured_fraction_full 0.246
_diffrn_reflns_Laue_measured_fraction_max 0.221
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_limit_l_min       -3
_diffrn_reflns_number            1454
_diffrn_reflns_point_group_measured_fraction_full 0.246
_diffrn_reflns_point_group_measured_fraction_max 0.221
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         21.033
_diffrn_reflns_theta_min         2.012
_diffrn_ambient_temperature      293(2)
_diffrn_ambient_pressure         1160000
_diffrn_ambient_environment      'Diamond Anvil Cell filled with parabar oil'
_diffrn_crystal_treatment        
'Pressurized slowly in parabar oil as a hydrostatic medium.'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0128
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.246
_diffrn_measured_fraction_theta_max 0.221
_diffrn_measurement_details      
'#__ type_ start__ end____ width___ exp.time_ 1 omega -58.00 -5.00 1.0000 150.0000 omega____ theta____ kappa____ phi______ frames - -18.7267 53.0000 162.0000 53 #__ type_ start__ end____ width___ exp.time_ 2 omega -23.00 11.00 1.0000 150.0000 omega____ theta____ kappa____ phi______ frames - -18.7267 53.0000 -17.0000 34 #__ type_ start__ end____ width___ exp.time_ 3 omega -61.00 -27.00 1.0000 150.0000 omega____ theta____ kappa____ phi______ frames - -18.7267 135.0000 -57.0000 34 #__ type_ start__ end____ width___ exp.time_ 4 omega -6.00 20.00 1.0000 150.0000 omega____ theta____ kappa____ phi______ frames - -18.7267 57.0000 150.0000 26 #__ type_ start__ end____ width___ exp.time_ 5 omega 17.00 56.00 1.0000 150.0000 omega____ theta____ kappa____ phi______ frames - -18.7267 -135.0000 -123.0000 39 #__ type_ start__ end____ width___ exp.time_ 6 omega -63.00 -37.00 1.0000 150.0000 omega____ theta____ kappa____ phi______ frames - 18.8049 160.0000 -90.0000 26 #__ type_ start__ end____ width___ exp.time_ 7 omega 25.00 51.00 1.0000 150.0000 omega____ theta____ kappa____ phi______ frames - 18.8049 19.0000 -180.0000 26 #__ type_ start__ end____ width___ exp.time_ 8 omega -42.00 -40.00 1.0000 150.0000 omega____ theta____ kappa____ phi______ frames - 18.8049 19.0000 -180.0000 2'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 
'Diamond Anvil Cell, effective opening angle of 30 deg.'
_diffrn_orient_matrix_UB_11      0.0172948000
_diffrn_orient_matrix_UB_12      0.0018019000
_diffrn_orient_matrix_UB_13      0.0784740000
_diffrn_orient_matrix_UB_21      -0.0261351000
_diffrn_orient_matrix_UB_22      0.0230340000
_diffrn_orient_matrix_UB_23      0.0006315000
_diffrn_orient_matrix_UB_31      -0.0626903000
_diffrn_orient_matrix_UB_32      -0.0090627000
_diffrn_orient_matrix_UB_33      0.0174370000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56087
_diffrn_source                   'SuperNova (Ag) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                380
_reflns_number_total             607
_reflns_odcompleteness_completeness 22.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     20.46
_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 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_computing_data_collection       
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         607
_refine_ls_number_restraints     208
_refine_ls_R_factor_all          0.1441
_refine_ls_R_factor_gt           0.0975
_refine_ls_restrained_S_all      0.966
_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)+(0.1776P)²+0.9122P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2547
_refine_ls_wR_factor_ref         0.2964
_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. Restrained planarity
 C3, C2, C1, C14, C13, C12, C11, C10, C9, C8, C7, C6, C5, C4, C15, C16
 with sigma of 0.05
3. Uiso/Uaniso restraints and constraints
O1 \\sim C17: within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 C6, O1, C17, C1, C18, C14, C2, C13, C3, C15, C12, C4, C16, C11, C5, C9, C10,
 C8, C7, C19, O2, C20
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Me refined with riding coordinates:
 C18(H18C,H18A,H18B), C20(H20C,H20A,H20B)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C14(H14), C13(H13), C11(H11), C4(H4), C8(H8), C7(H7), C10(H10)
5.c Fitted hexagon refined as free rotating group:
 C1(C14,C13,C12,C15,C2), C5(C16,C9,C8,C7,C6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5457(7) 0.2331(2) 0.207(2) 0.036(11) Uani 1 1 d . U . . .
O2 O 0.5580(8) 0.5187(2) 0.228(3) 0.082(15) Uani 1 1 d . U . . .
C3 C 0.7006(10) 0.3453(3) 0.162(2) 0.037(11) Uani 1 1 d . U . . .
H3 H 0.5990 0.3258 0.1400 0.044 Uiso 1 1 calc R . . . .
C1 C 0.8400(5) 0.24931(18) 0.207(2) 0.028(11) Uani 1 1 d . U . . .
C14 C 0.9883(6) 0.21870(14) 0.248(2) 0.020(11) Uani 1 1 d G U . . .
H14 H 0.9884 0.1775 0.2490 0.024 Uiso 1 1 calc R . . . .
C13 C 1.1363(5) 0.24961(19) 0.287(2) 0.029(11) Uani 1 1 d G U . . .
H13 H 1.2355 0.2291 0.3139 0.035 Uiso 1 1 calc R . . . .
C12 C 1.1362(5) 0.31114(19) 0.2845(18) 0.044(11) Uani 1 1 d G U . . .
C15 C 0.9879(6) 0.34175(14) 0.2435(14) 0.039(10) Uani 1 1 d G U . . .
C2 C 0.8399(5) 0.31084(19) 0.2047(16) 0.033(11) Uani 1 1 d G U . . .
C11 C 1.2905(12) 0.3434(4) 0.342(4) 0.039(11) Uani 1 1 d . U . . .
H11 H 1.3865 0.3228 0.3823 0.047 Uiso 1 1 calc R . . . .
C17 C 0.6828(12) 0.2127(3) 0.180(4) 0.038(11) Uani 1 1 d . U . . .
C18 C 0.6989(13) 0.1472(3) 0.136(4) 0.073(17) Uani 1 1 d . U . . .
H18C H 0.6618 0.1245 0.2424 0.110 Uiso 1 1 calc R . . . .
H18A H 0.8138 0.1380 0.1150 0.110 Uiso 1 1 calc R . . . .
H18B H 0.6313 0.1378 0.0220 0.110 Uiso 1 1 calc R . . . .
C4 C 0.6990(11) 0.4047(3) 0.149(3) 0.035(11) Uani 1 1 d . U . . .
H4 H 0.6026 0.4239 0.1021 0.042 Uiso 1 1 calc R . . . .
C5 C 0.8455(5) 0.4390(2) 0.2077(19) 0.034(10) Uani 1 1 d . U . . .
C16 C 0.9914(6) 0.40678(15) 0.245(2) 0.043(10) Uani 1 1 d G U . . .
C9 C 1.1417(5) 0.4360(2) 0.2868(19) 0.033(11) Uani 1 1 d G U . . .
C8 C 1.1461(5) 0.4975(2) 0.291(2) 0.050(12) Uani 1 1 d G U . . .
H8 H 1.2466 0.5171 0.3185 0.060 Uiso 1 1 calc R . . . .
C7 C 1.0001(6) 0.52978(15) 0.253(2) 0.087(14) Uani 1 1 d G U . . .
H7 H 1.0030 0.5709 0.2558 0.105 Uiso 1 1 calc R . . . .
C6 C 0.8498(5) 0.50052(19) 0.212(2) 0.063(12) Uani 1 1 d G U . . .
C10 C 1.2923(12) 0.4020(4) 0.336(3) 0.035(11) Uani 1 1 d . U . . .
H10 H 1.3923 0.4219 0.3640 0.042 Uiso 1 1 calc R . . . .
C19 C 0.6935(12) 0.5394(3) 0.195(4) 0.052(13) Uani 1 1 d . U . . .
C20 C 0.7072(14) 0.6035(3) 0.150(4) 0.040(16) Uani 1 1 d . U . . .
H20C H 0.5974 0.6197 0.1249 0.060 Uiso 1 1 calc R . . . .
H20A H 0.7722 0.6085 0.0385 0.060 Uiso 1 1 calc R . . . .
H20B H 0.7610 0.6237 0.2578 0.060 Uiso 1 1 calc R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.023(3) 0.040(3) 0.05(3) 0.005(6) -0.003(9) 0.001(3)
O2 0.030(4) 0.035(4) 0.18(5) 0.008(6) 0.030(12) 0.001(2)
C3 0.027(5) 0.025(4) 0.06(4) 0.006(6) 0.003(9) -0.002(3)
C1 0.026(4) 0.024(4) 0.03(3) 0.012(5) 0.003(8) 0.003(2)
C14 0.023(4) 0.023(4) 0.01(4) 0.004(6) 0.004(8) 0.009(3)
C13 0.025(4) 0.029(4) 0.03(3) -0.001(6) 0.004(8) 0.006(3)
C12 0.024(4) 0.030(4) 0.08(3) -0.002(6) 0.002(8) 0.005(2)
C15 0.024(4) 0.022(4) 0.07(3) -0.004(5) 0.005(8) 0.002(2)
C2 0.026(4) 0.027(4) 0.05(3) 0.010(5) 0.003(8) 0.001(2)
C11 0.021(4) 0.037(4) 0.06(3) -0.014(6) 0.013(9) 0.001(3)
C17 0.026(4) 0.031(4) 0.06(3) 0.011(7) -0.001(8) -0.002(3)
C18 0.037(6) 0.040(5) 0.15(5) -0.004(9) 0.038(16) -0.010(4)
C4 0.022(4) 0.025(4) 0.06(3) 0.001(6) 0.015(9) 0.002(3)
C5 0.018(4) 0.020(4) 0.06(3) 0.003(5) 0.012(8) 0.000(2)
C16 0.018(4) 0.022(4) 0.09(3) -0.002(5) 0.005(8) 0.002(2)
C9 0.017(4) 0.028(4) 0.06(3) -0.013(5) 0.015(8) -0.002(2)
C8 0.028(4) 0.032(4) 0.09(4) -0.014(6) 0.020(9) -0.003(3)
C7 0.030(4) 0.029(5) 0.20(4) -0.011(8) 0.003(9) -0.006(3)
C6 0.028(4) 0.019(4) 0.14(4) 0.001(6) 0.010(9) -0.004(3)
C10 0.023(4) 0.037(4) 0.05(3) -0.016(6) 0.016(9) -0.001(3)
C19 0.025(4) 0.027(4) 0.11(4) 0.009(8) 0.016(10) 0.000(3)
C20 0.037(6) 0.029(4) 0.06(5) -0.007(8) 0.015(14) -0.004(4)

_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 1.212(8) . ?
O2 C19 1.212(8) . ?
C3 C2 1.380(9) . ?
C3 C4 1.344(11) . ?
C1 C14 1.3900 . ?
C1 C2 1.3900 . ?
C1 C17 1.509(11) . ?
C14 C13 1.3900 . ?
C13 C12 1.3900 . ?
C12 C15 1.3900 . ?
C12 C11 1.472(14) . ?
C15 C2 1.3900 . ?
C15 C16 1.469(5) . ?
C11 C10 1.324(11) . ?
C17 C18 1.517(13) . ?
C4 C5 1.447(13) . ?
C5 C16 1.3900 . ?
C5 C6 1.3900 . ?
C16 C9 1.3900 . ?
C9 C8 1.3900 . ?
C9 C10 1.455(13) . ?
C8 C7 1.3900 . ?
C7 C6 1.3900 . ?
C6 C19 1.528(11) . ?
C19 C20 1.486(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 C3 C2 125.6(8) . . ?
C14 C1 C2 120.0 . . ?
C14 C1 C17 116.7(5) . . ?
C2 C1 C17 123.1(4) . . ?
C1 C14 C13 120.0 . . ?
C12 C13 C14 120.0 . . ?
C13 C12 C11 119.5(5) . . ?
C15 C12 C13 120.0 . . ?
C15 C12 C11 120.3(5) . . ?
C12 C15 C2 120.0 . . ?
C12 C15 C16 118.7(4) . . ?
C2 C15 C16 121.3(4) . . ?
C3 C2 C1 124.6(4) . . ?
C3 C2 C15 115.4(4) . . ?
C15 C2 C1 120.0 . . ?
C10 C11 C12 119.8(11) . . ?
O1 C17 C1 121.8(9) . . ?
O1 C17 C18 119.3(8) . . ?
C1 C17 C18 118.7(7) . . ?
C3 C4 C5 120.7(10) . . ?
C16 C5 C4 115.7(5) . . ?
C16 C5 C6 120.0 . . ?
C6 C5 C4 124.1(5) . . ?
C5 C16 C15 120.5(4) . . ?
C5 C16 C9 120.0 . . ?
C9 C16 C15 119.5(4) . . ?
C16 C9 C10 119.7(5) . . ?
C8 C9 C16 120.0 . . ?
C8 C9 C10 120.3(5) . . ?
C9 C8 C7 120.0 . . ?
C6 C7 C8 120.0 . . ?
C5 C6 C19 123.7(5) . . ?
C7 C6 C5 120.0 . . ?
C7 C6 C19 116.0(5) . . ?
C11 C10 C9 121.7(10) . . ?
O2 C19 C6 119.9(8) . . ?
O2 C19 C20 119.5(8) . . ?
C20 C19 C6 120.5(6) . . ?

_iucr_refine_instructions_details 
;
TITL v1_abs in P21/c #14
REM reset to P21/c #14
CELL 0.56087 7.996935 22.591205 6.944198 90 92.7319 90
ZERR 4 0.002934 0.007823 0.032736 0 0.1442 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H O
UNIT 80 56 8
FLAT 0.05 C3 C2 C1 C14 C13 C12 C11 C10 C9 C8 C7 C6 C5 C4 C15 C16
SIMU 0.01 0.02 1.7 O1 C17
RIGU C6 O1 C17 C1 C18 C14 C2 C13 C3 C15 C12 C4 C16 C11 C5 C9 C10 C8 C7 C19 =
 O2 C20
 
L.S. 4
PLAN  20
BOND
fmap 2
acta
OMIT -1 12 2
REM <olex2.extras>
REM <HklSrc "%./v1_abs.hkl">
REM </olex2.extras>
 
WGHT    0.177600    0.912200
FVAR       2.07935
O1    3    0.545726    0.233147    0.206884    11.00000    0.02342    0.03970 =
         0.04507    0.00460   -0.00292    0.00066
O2    3    0.557951    0.518666    0.227853    11.00000    0.03016    0.03504 =
         0.18355    0.00836    0.03006    0.00052
C3    1    0.700566    0.345341    0.161896    11.00000    0.02668    0.02526 =
         0.05942    0.00589    0.00328   -0.00215
AFIX  43
H3    2    0.599038    0.325824    0.140040    11.00000   -1.20000
AFIX  66
C1    1    0.840041    0.249312    0.206729    11.00000    0.02573    0.02375 =
         0.03476    0.01155    0.00337    0.00295
C14    1    0.988274    0.218699    0.247642    11.00000    0.02329    0.02340 =
         0.01434    0.00428    0.00369    0.00910
AFIX  43
H14    2    0.988385    0.177535    0.249015    11.00000   -1.20000
AFIX  65
C13    1    1.136340    0.249612    0.286503    11.00000    0.02536    0.02937 =
         0.03189   -0.00069    0.00436    0.00559
AFIX  43
H13    2    1.235518    0.229129    0.313877    11.00000   -1.20000
AFIX  65
C12    1    1.136175    0.311136    0.284451    11.00000    0.02421    0.02998 =
         0.07796   -0.00232    0.00200    0.00458
C15    1    0.987943    0.341750    0.243538    11.00000    0.02395    0.02186 =
         0.07050   -0.00407    0.00482    0.00181
C2    1    0.839876    0.310838    0.204677    11.00000    0.02621    0.02659 =
         0.04772    0.00980    0.00305    0.00124
AFIX   0
C11    1    1.290510    0.343433    0.341929    11.00000    0.02144    0.03658 =
         0.06001   -0.01404    0.01346    0.00067
AFIX  43
H11    2    1.386455    0.322753    0.382259    11.00000   -1.20000
AFIX   0
C17    1    0.682751    0.212700    0.180081    11.00000    0.02591    0.03096 =
         0.05754    0.01111   -0.00052   -0.00203
C18   1    0.698873    0.147247    0.135808    11.00000    0.03730    0.03972 =
         0.14569   -0.00408    0.03829   -0.01014
AFIX  33
H18C  2    0.661781    0.124489    0.242443    11.00000   -1.50000
H18A  2    0.813789    0.138024    0.114950    11.00000   -1.50000
H18B  2    0.631250    0.137809    0.022014    11.00000   -1.50000
AFIX   0
C4   1    0.698965    0.404709    0.149093    11.00000    0.02197    0.02496 =
         0.06032    0.00113    0.01498    0.00171
AFIX  43
H4   2    0.602636    0.423942    0.102059    11.00000   -1.20000
AFIX  66
C5   1    0.845452    0.439017    0.207680    11.00000    0.01842    0.02032 =
         0.06493    0.00320    0.01157    0.00038
C16   1    0.991429    0.406782    0.245246    11.00000    0.01804    0.02249 =
         0.08829   -0.00163    0.00534    0.00184
C9   1    1.141741    0.436045    0.286784    11.00000    0.01698    0.02802 =
         0.05630   -0.01312    0.01490   -0.00156
C8   1    1.146078    0.497543    0.290756    11.00000    0.02780    0.03176 =
         0.09279   -0.01397    0.01952   -0.00280
AFIX  43
H8   2    1.246647    0.517122    0.318548    11.00000   -1.20000
AFIX  65
C7   1    1.000102    0.529779    0.253191    11.00000    0.02990    0.02931 =
         0.20210   -0.01069    0.00286   -0.00610
AFIX  43
H7   2    1.003004    0.570925    0.255849    11.00000   -1.20000
AFIX  65
C6   1    0.849788    0.500516    0.211653    11.00000    0.02837    0.01861 =
         0.14250    0.00140    0.01011   -0.00410
AFIX   0
C10   1    1.292269    0.402006    0.336017    11.00000    0.02278    0.03680 =
         0.04641   -0.01601    0.01554   -0.00134
AFIX  43
H10   2    1.392278    0.421911    0.364050    11.00000   -1.20000
AFIX   0
C19   1    0.693511    0.539433    0.195404    11.00000    0.02488    0.02698 =
         0.10541    0.00868    0.01573    0.00034
C20   1    0.707216    0.603498    0.150145    11.00000    0.03688    0.02943 =
         0.05515   -0.00664    0.01517   -0.00445
AFIX  33
H20C  2    0.597351    0.619675    0.124851    11.00000   -1.50000
H20A  2    0.772180    0.608491    0.038544    11.00000   -1.50000
H20B  2    0.760969    0.623712    0.257807    11.00000   -1.50000
AFIX   0
HKLF 4
 
REM  v1_abs in P21/c #14
REM R1 =  0.0975 for     380 Fo > 4sig(Fo)  and  0.1441 for all     607 data
REM    175 parameters refined using    208 restraints
 
END  
     
WGHT      0.1776      0.9165 

REM Highest difference peak  0.271,  deepest hole -0.211,  1-sigma level  0.059
Q1    1   0.8301  0.5120  0.1978  11.00000  0.05    0.24
Q2    1   0.6734  0.3478  0.0299  11.00000  0.05    0.20
Q3    1   1.1707  0.3106  0.3612  11.00000  0.05    0.19
Q4    1   1.1686  0.5031  0.3868  11.00000  0.05    0.18
Q5    1   1.2961  0.5289  0.2913  11.00000  0.05    0.17
Q6    1   0.4692  0.2286  0.3394  11.00000  0.05    0.16
Q7    1   1.1705  0.2486  0.4052  11.00000  0.05    0.16
Q8    1   0.8526  0.6222  0.3128  11.00000  0.05    0.16
Q9    1   1.1528  0.2998  0.1878  11.00000  0.05    0.16
Q10   1   1.1463  0.2913  0.1089  11.00000  0.05    0.15
Q11   1   1.4350  0.3086  0.3815  11.00000  0.05    0.15
Q12   1   1.1659  0.2418  0.3063  11.00000  0.05    0.15
Q13   1   1.1559  0.2387  0.2440  11.00000  0.05    0.15
Q14   1   0.8349  0.4378  0.1348  11.00000  0.05    0.15
Q15   1   1.1493  0.2390  0.4862  11.00000  0.05    0.14
Q16   1   1.4309  0.3199  0.2623  11.00000  0.05    0.14
Q17   1   0.6750  0.4086  0.0832  11.00000  0.05    0.14
Q18   1   1.3235  0.4007  0.4536  11.00000  0.05    0.14
Q19   1   0.5380  0.5195  0.1734  11.00000  0.05    0.14
Q20   1   0.4489  0.5121  0.3393  11.00000  0.05    0.13

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0975 for 380 Fo > 4sig(Fo) and 0.1441 for all 1477 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.27, deepest hole -0.21
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.1441
  REM R1_gt = 0.0975
  REM wR_ref = 0.2964
  REM GOOF = 1.124
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 1477
  REM Reflections_gt = 380
  REM Parameters = n/a
  REM Hole = -0.21
  REM Peak = 0.27
  REM Flack = n/a

  
;
_olex2_exptl_crystal_mounting_method 
'in a Diamond Anvil Cell, opening angle 30 degrees, in Paratone oil'
_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT029_2bisAP-gamma_1160000kPa 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.246 Why?  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC, and in 
particular affected the c direction due to crystal orientation.
;
_vrf_PLAT088_2bisAP-gamma_1160000kPa 
;
PROBLEM: Poor Data / Parameter Ratio ....................       3.47 Note  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC, and in 
particular affected the c direction due to crystal orientation.
;
_vrf_PLAT911_2bisAP-gamma_1160000kPa 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L= 0.600           770 Report
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
;
_vrf_PLAT149_2bisAP-gamma_1160000kPa 
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.14 Degree
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC, and in 
particular affected the beta angle due to crystal orientation.
;
_vrf_PLAT340_2bisAP-gamma_1160000kPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01061 Ang.  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections
that could be collected, as most of them were obscured by the DAC,
which together with weak scattering negatively affected the precision.
;
_vrf_PLAT084_2bisAP-gamma_1160000kPa 
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.30 Report
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
In particular affected the c direction due to crystal orientation.
Additionally, the structure was determined just after a pressure-induced 
phase transition took place, resulting in an even less precise model.
;
_vrf_PLAT148_2bisAP-gamma_1160000kPa 
;
PROBLEM: s.u. on the      c    - Axis is (Too) Large ....      0.030 Ang.  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
In particular affected the c direction due to crystal orientation.
;
_vrf_PLAT220_2bisAP-gamma_1160000kPa 
;
PROBLEM: Non-Solvent  Resd 1  C   Ueq(max)/Ueq(min) Range        4.5 Ratio 
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
In particular affected the c direction due to crystal orientation.
Additionally, the structure was determined just after a pressure-induced 
phase transition took place, resulting in an even less precise model.
;
_vrf_PLAT222_2bisAP-gamma_1160000kPa 
;
PROBLEM: Non-Solv.  Resd 1  H   Uiso(max)/Uiso(min) Range        4.6 Ratio 
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
In particular affected the c direction due to crystal orientation.
Additionally, the structure was determined just after a pressure-induced 
phase transition took place, resulting in an even less precise model.
;
_vrf_PLAT241_2bisAP-gamma_1160000kPa 
;
PROBLEM: High   'MainMol' Ueq as Compared to Neighbors of         C7 Check 
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
In particular affected the c direction due to crystal orientation.
Additionally, the structure was determined just after a pressure-induced 
phase transition took place, resulting in an even less precise model.
;
_vrf_PLAT250_2bisAP-gamma_1160000kPa 
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        3.4 Note  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
In particular affected the c direction due to crystal orientation.
Additionally, the structure was determined just after a pressure-induced 
phase transition took place, resulting in an even less precise model.
;
_vrf_PLAT369_2bisAP-gamma_1160000kPa 
;
PROBLEM: Long   C(sp2)-C(sp2) Bond  C6        - C19      .       1.53 Ang.  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
In particular affected the c direction due to crystal orientation.
Additionally, the structure was determined just after a pressure-induced 
phase transition took place, resulting in an even less precise model.
;
_vrf_PLAT412_2bisAP-gamma_1160000kPa 
;
PROBLEM: Short Intra XH3 .. XHn     H14       ..H18A     .       1.87 Ang.  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
In particular affected the c direction due to crystal orientation.
Additionally, the structure was determined just after a pressure-induced 
phase transition took place, resulting in an even less precise model.
;
_vrf_PLAT906_2bisAP-gamma_1160000kPa 
;
PROBLEM: Large K Value in the Analysis of Variance ......     40.773 Check 
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
In particular affected the c direction due to crystal orientation.
Additionally, the structure was determined just after a pressure-induced 
phase transition took place, resulting in an even less precise model.
;
_vrf_PLAT978_2bisAP-gamma_1160000kPa 
;
PROBLEM: Number C-C Bonds with Positive Residual Density.          0 Info  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
In particular affected the c direction due to crystal orientation.
Additionally, the structure was determined just after a pressure-induced 
phase transition took place, resulting in an even less precise model.
;
# 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_2bisAP-beta_1870000kPa
_database_code_depnum_ccdc_archive 'CCDC 2039419'
loop_
_audit_author_name
_audit_author_address
'Daniel Tchon'
;Faculty of Chemistry, University of Warsaw
Poland
;
_audit_update_record             
;
2020-10-19 deposited with the CCDC.	2021-01-21 downloaded from the CCDC.
;
_audit_creation_date             2019-08-06
_audit_creation_method           
;
Olex2 1.2
(compiled May 29 2018 13:30:08 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            1,1'-Pyrene-1,8-diyldiethanone
_chemical_name_systematic        1,8-Diacetylpyrene
_chemical_formula_moiety         'C20 H14 O2'
_chemical_formula_sum            'C20 H14 O2'
_chemical_formula_weight         286.31
_chemical_absolute_configuration ad
_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      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   4.5345(14)
_cell_length_b                   34.26(7)
_cell_length_c                   16.040(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2492(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    489
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.2900
_cell_measurement_theta_min      2.6530
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37716
_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 dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1200
_exptl_crystal_preparation       
'Mounted in a Diamond-Anvil Cell using parabar oil as pressure medium.,Luminescent'
_exptl_crystal_pressure_history  
'Pressurized to 1.87 GPa and left to stabilize over 24 hours.'
_exptl_crystal_recrystallization_method 'from chloroform at room temperature'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
High-pressure measurement at 1.87 GPa in a Merill-Basset Diamond Anvil Cell with
effective opening angle of 45 deg. and parabar 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  0.1406
_diffrn_reflns_av_unetI/netI     0.1308
_diffrn_reflns_Laue_measured_fraction_full 0.474
_diffrn_reflns_Laue_measured_fraction_max 0.522
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            2008
_diffrn_reflns_point_group_measured_fraction_full 0.442
_diffrn_reflns_point_group_measured_fraction_max 0.486
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.401
_diffrn_reflns_theta_min         2.804
_diffrn_ambient_temperature      293(2)
_diffrn_ambient_pressure         1870000
_diffrn_ambient_environment      'Diamond Anvil Cell filled with parabar oil'
_diffrn_crystal_treatment        
'Pressurized slowly in parabar oil as a hydrostatic medium.'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.474
_diffrn_measured_fraction_theta_max 0.522
_diffrn_measurement_details      
'List of Runs (angles in degrees, time in seconds): # Type Start End Width tₑₓₚ ω θ κ φ Frames -------------------------------------------------------------------------- 1 ω -12.00 13.00 1.00 60.00 -- 18.26 67.00 157.00 25 2 ω -10.00 15.00 1.00 60.00 -- 18.26 57.00 150.00 25 3 ω 15.00 44.00 1.00 60.00 -- 18.26 -57.00-180.00 29 4 ω -7.00 21.00 1.00 60.00 -- 18.26 81.00 -29.00 28 5 ω -24.00 35.00 1.00 60.00 -- 18.26 -39.00 12.00 59 6 ω 31.00 58.00 1.00 60.00 -- 18.26 -99.00-180.00 27 7 ω -34.00 -7.00 1.00 60.00 -- 18.26 13.00 176.00 27 8 ω -8.00 20.00 1.00 60.00 -- 18.26 53.00 162.00 28 9 ω -6.00 19.00 1.00 60.00 -- 18.26 37.00 150.00 25 10 ω -13.00 17.00 1.00 60.00 -- 18.26 26.00 172.00 30 11 ω -108.00 -57.00 1.00 60.00 -- -20.13-178.00 -90.00 51 12 ω -6.00 21.00 1.00 60.00 -- -20.13 -19.00-180.00 27 13 ω -15.00 8.00 1.00 60.00 -- -20.13 -57.00-150.00 23 14 ω -81.00 -56.00 1.00 60.00 -- -20.13 134.00 123.00 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 45 deg.'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0116630425
_diffrn_orient_matrix_UB_12      -0.0204257910
_diffrn_orient_matrix_UB_13      -0.0039475414
_diffrn_orient_matrix_UB_21      -0.0439276529
_diffrn_orient_matrix_UB_22      -0.0022357442
_diffrn_orient_matrix_UB_23      0.0423382985
_diffrn_orient_matrix_UB_31      -0.1503916057
_diffrn_orient_matrix_UB_32      -0.0008843156
_diffrn_orient_matrix_UB_33      -0.0125141940
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\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         0.792
_reflns_Friedel_fraction_full    0.407
_reflns_Friedel_fraction_max     0.447
_reflns_number_gt                327
_reflns_number_total             500
_reflns_odcompleteness_completeness 50.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.35
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXD (Sheldrick, 2008)'
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details .
_refine_ls_abs_structure_Flack   .
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         500
_refine_ls_number_restraints     85
_refine_ls_R_factor_all          0.1373
_refine_ls_R_factor_gt           0.0897
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1218P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1972
_refine_ls_wR_factor_ref         0.2351
_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. Uiso/Uaniso restraints and constraints
Uanis(C18) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Rigid body (RIGU) restrains
 C3, O1, C17, C1, C18, C2, C14, C15, C13, C12, C11
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.003
4.a Me refined with riding coordinates:
 C18(H18B,H18A,H18C)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C14(H14), C13(H13), C11(H11)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.091(3) 0.4203(8) 0.2904(6) 0.066(8) Uani 1 1 d . U . . .
C3 C 0.406(2) 0.4850(9) 0.3562(6) 0.032(7) Uani 1 1 d . U . . .
H3 H 0.3480 0.4747 0.3051 0.039 Uiso 1 1 calc R . . . .
C2 C 0.284(2) 0.4671(7) 0.4335(7) 0.029(5) Uani 1 1 d . U . . .
C1 C 0.076(2) 0.4386(9) 0.4338(8) 0.035(5) Uani 1 1 d . U . . .
C14 C -0.028(3) 0.4255(10) 0.5135(8) 0.046(6) Uani 1 1 d . U . . .
H14 H -0.1680 0.4056 0.5157 0.055 Uiso 1 1 calc R . . . .
C13 C 0.074(3) 0.4418(10) 0.5875(9) 0.048(7) Uani 1 1 d . U . . .
H13 H 0.0008 0.4331 0.6384 0.058 Uiso 1 1 calc R . . . .
C12 C 0.286(3) 0.4709(10) 0.5851(7) 0.042(7) Uani 1 1 d . U . . .
C15 C 0.393(2) 0.4854(8) 0.5081(7) 0.030(6) Uani 1 1 d . U . . .
C11 C 0.404(3) 0.4857(10) 0.6621(7) 0.039(8) Uani 1 1 d . U . . .
H11 H 0.3432 0.4749 0.7124 0.047 Uiso 1 1 calc R . . . .
C17 C -0.027(3) 0.4180(10) 0.3579(9) 0.042(6) Uani 1 1 d . U . . .
C18 C -0.277(3) 0.3888(10) 0.3668(10) 0.044(6) Uani 1 1 d . U . . .
H18B H -0.3814 0.3869 0.3149 0.066 Uiso 1 1 calc R . . . .
H18A H -0.4091 0.3974 0.4098 0.066 Uiso 1 1 calc R . . . .
H18C H -0.1975 0.3637 0.3813 0.066 Uiso 1 1 calc R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.079(7) 0.07(3) 0.048(5) 0.005(7) -0.006(4) -0.016(9)
C3 0.035(7) 0.03(2) 0.032(5) 0.000(7) -0.001(4) 0.004(9)
C2 0.020(5) 0.029(15) 0.038(5) 0.006(5) -0.003(4) 0.016(6)
C1 0.021(5) 0.031(15) 0.053(5) 0.010(6) -0.005(4) 0.013(7)
C14 0.048(7) 0.031(18) 0.059(5) 0.010(7) 0.006(5) 0.009(9)
C13 0.056(8) 0.04(2) 0.051(6) 0.011(7) 0.010(6) 0.003(10)
C12 0.052(8) 0.04(2) 0.034(5) 0.008(6) 0.013(4) 0.005(8)
C15 0.031(6) 0.031(17) 0.028(4) 0.009(5) 0.001(4) 0.007(8)
C11 0.057(9) 0.03(3) 0.031(5) 0.013(7) 0.011(5) 0.010(11)
C17 0.039(6) 0.034(18) 0.053(5) 0.011(6) -0.012(5) 0.014(8)
C18 0.031(5) 0.027(18) 0.075(9) -0.007(9) 0.009(5) 0.019(8)

_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 1.21(2) . ?
C3 C3 1.34(5) 2_665 ?
C3 C2 1.49(2) . ?
C2 C1 1.36(3) . ?
C2 C15 1.44(2) . ?
C1 C14 1.43(2) . ?
C1 C17 1.48(3) . ?
C14 C13 1.39(3) . ?
C13 C12 1.38(3) . ?
C12 C15 1.42(2) . ?
C12 C11 1.44(2) . ?
C15 C15 1.39(5) 2_665 ?
C11 C11 1.31(5) 2_665 ?
C17 C18 1.52(4) . ?

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
C3 C3 C2 123.6(10) 2_665 . ?
C1 C2 C3 123.9(13) . . ?
C1 C2 C15 123.2(14) . . ?
C15 C2 C3 112.7(17) . . ?
C2 C1 C14 117.2(17) . . ?
C2 C1 C17 123.9(13) . . ?
C14 C1 C17 119(2) . . ?
C13 C14 C1 122(2) . . ?
C12 C13 C14 119.7(17) . . ?
C13 C12 C15 121.0(16) . . ?
C13 C12 C11 119.2(15) . . ?
C15 C12 C11 120(2) . . ?
C12 C15 C2 117.0(19) . . ?
C15 C15 C2 123.5(10) 2_665 . ?
C15 C15 C12 119.4(13) 2_665 . ?
C11 C11 C12 120.7(14) 2_665 . ?
O1 C17 C1 124.3(19) . . ?
O1 C17 C18 117.2(19) . . ?
C1 C17 C18 118.2(15) . . ?

_iucr_refine_instructions_details 
;
TITL v4_abs1 in Fdd2 #43
REM Best SHELXD solution FINAL CC 74.56
REM Fragments: 20
REM reset to Fdd2 #43
CELL 0.71073 4.534487 34.255602 16.040475 90 90 90
ZERR 8 0.001424 0.074079 0.005061 0 0 0
LATT -4
SYMM -X,-Y,+Z
SYMM 0.25-X,0.25+Y,0.25+Z
SYMM 0.25+X,0.25-Y,0.25+Z
SFAC C H O
UNIT 160 112 16
RIGU 0.003 0.003 C3 O1 C17 C1 C18 C2 C14 C15 C13 C12 C11
ISOR 0.01 0.02 C18
 
L.S. 4
PLAN  2
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%./v4_abs1.hkl">
REM </olex2.extras>
 
WGHT    0.121800
FVAR       0.71152
O1    3    0.090829    0.420343    0.290439    11.00000    0.07865    0.07190 =
         0.04829    0.00475   -0.00594   -0.01618
C3    1    0.405995    0.485003    0.356195    11.00000    0.03466    0.03030 =
         0.03226   -0.00013   -0.00113    0.00394
AFIX  43
H3    2    0.347959    0.474716    0.305109    11.00000   -1.20000
AFIX   0
C2    1    0.284084    0.467106    0.433452    11.00000    0.01961    0.02883 =
         0.03779    0.00614   -0.00285    0.01616
C1    1    0.075799    0.438615    0.433787    11.00000    0.02112    0.03083 =
         0.05349    0.00969   -0.00539    0.01348
C14    1   -0.028415    0.425507    0.513462    11.00000    0.04817    0.03124 =
         0.05902    0.01040    0.00563    0.00932
AFIX  43
H14    2   -0.167990    0.405642    0.515692    11.00000   -1.20000
AFIX   0
C13    1    0.074132    0.441775    0.587517    11.00000    0.05578    0.03873 =
         0.05070    0.01114    0.00979    0.00320
AFIX  43
H13    2    0.000769    0.433126    0.638412    11.00000   -1.20000
AFIX   0
C12    1    0.285719    0.470873    0.585093    11.00000    0.05250    0.03881 =
         0.03399    0.00771    0.01289    0.00507
C15    1    0.393374    0.485351    0.508134    11.00000    0.03102    0.03094 =
         0.02842    0.00916    0.00079    0.00677
C11    1    0.403868    0.485700    0.662106    11.00000    0.05709    0.03032 =
         0.03073    0.01320    0.01133    0.01008
AFIX  43
H11    2    0.343192    0.474880    0.712438    11.00000   -1.20000
AFIX   0
C17    1   -0.027049    0.417987    0.357930    11.00000    0.03912    0.03376 =
         0.05253    0.01136   -0.01162    0.01400
C18   1   -0.276648    0.388829    0.366798    11.00000    0.03126    0.02699 =
         0.07459   -0.00689    0.00917    0.01870
AFIX  33
H18B  2   -0.381373    0.386900    0.314947    11.00000   -1.50000
H18A  2   -0.409128    0.397386    0.409756    11.00000   -1.50000
H18C  2   -0.197481    0.363741    0.381304    11.00000   -1.50000
AFIX   0
HKLF 4
 
REM  v4_abs1 in Fdd2 #43
REM R1 =  0.0897 for     327 Fo > 4sig(Fo)  and  0.1373 for all     500 data
REM    100 parameters refined using     85 restraints
 
END  
     
WGHT      0.1218      0.0000 

REM Highest difference peak  0.187,  deepest hole -0.209,  1-sigma level  0.063
Q1    1   0.0713  0.4891  0.2941  11.00000  0.05    0.19
Q2    1  -0.3276  0.4289  0.5489  11.00000  0.05    0.18

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0897 for 327 Fo > 4sig(Fo) and 0.1373 for all 2104 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.19, deepest hole -0.21
  REM Mean Shift 0.001, Max Shift 0.003.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.1373
  REM R1_gt = 0.0897
  REM wR_ref = 0.2351
  REM GOOF = 1.089
  REM Shift_max = 0.003
  REM Shift_mean = 0.001
  REM Reflections_all = 2104
  REM Reflections_gt = 327
  REM Parameters = n/a
  REM Hole = -0.21
  REM Peak = 0.19
  REM Flack = -1.4(10)

  
;
_olex2_exptl_crystal_mounting_method 
'in Diamond Anvil Cell, opening angle 45 degrees, in Paratone N oil'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_diffrn_reflns_filtered   562
_oxdiff_exptl_absorpt_empirical_details 
'Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling'
_oxdiff_exptl_absorpt_empirical_full_max 2.206
_oxdiff_exptl_absorpt_empirical_full_min 0.616

# start Validation Reply Form
_vrf_RINTA01_2bisAP-beta_1870000kPa 
;
PROBLEM: The value of Rint is greater than 0.12
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 45 degrees on a very thin plate. This resulted in low 
diffracted intensities, low available data resolution and high Rint value.
;
_vrf_PLAT340_2bisAP-beta_1870000kPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02846 Ang. 
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 45 degrees on a very thin plate. This limited the number
of reflections that could be collected, as most of them were obscured by the
DAC, which together with weak scattering negatively affected the precision.
;
_vrf_PLAT911_2bisAP-beta_1870000kPa 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L= 0.581            66 Report
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 45 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
;
_vrf_PLAT915_2bisAP-beta_1870000kPa 
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         45 % 
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 45 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
Moreover, high Friedel pair coverage was unnecessary, as space group information
was determined using complete dataset gathered on this sample before experiment. 
;
_vrf_THETM01_2bisAP-beta_1870000kPa 
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.590
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 45 degrees on a very thin plate. This resulted in low 
diffracted intensities, low available data resolution and high Rint value.
;
_vrf_PLAT089_2bisAP-beta_1870000kPa 
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       2.79 Note  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 45 degrees on a very thin plate. This resulted in low 
diffracted intensities, low available data resolution and high Rint value.
;
_vrf_PLAT018_2bisAP-beta_1870000kPa 
;
PROBLEM: _diffrn_measured_fraction_theta_max .NE. *_full           ! Check 
RESPONSE: A discrepancy between what olex2 and shelx report.
;
_vrf_PLAT020_2bisAP-beta_1870000kPa 
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.141 Report
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 45 degrees on a very thin plate. This resulted in low 
diffracted intensities, low available data resolution and high Rint value.
;
_vrf_PLAT148_2bisAP-beta_1870000kPa 
;
PROBLEM: s.u. on the      b    - Axis is (Too) Large ....     0.0700 Ang.  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 45 degrees on a very thin plate. This limited the number 
of reflections that could be collected, as most of them were obscured 
by the DAC.
;
_vrf_PLAT213_2bisAP-beta_1870000kPa 
;
PROBLEM: Atom C18             has ADP max/min Ratio .....        3.1 oblate
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 45 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
This, and relatively weak scattering, affected the precission of the final 
model.
;
_vrf_PLAT906_2bisAP-beta_1870000kPa 
;
PROBLEM: Large K Value in the Analysis of Variance ......      7.186 Check 
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 45 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
This, and relatively weak scattering, affected the precission of the final 
model.
;
_vrf_PLAT978_2bisAP-beta_1870000kPa 
;
PROBLEM: Number C-C Bonds with Positive Residual Density.          0 Info  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 45 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
This, and relatively weak scattering, affected the precission of the final 
model.
;
# 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_2bisAP-gamma_1650000kPa
_database_code_depnum_ccdc_archive 'CCDC 2039421'
loop_
_audit_author_name
_audit_author_address
'Daniel Tchon'
;Faculty of Chemistry, University of Warsaw
Poland
;
_audit_update_record             
;
2020-10-19 deposited with the CCDC.	2021-01-21 downloaded from the CCDC.
;
_audit_creation_date             2019-08-06
_audit_creation_method           
;
Olex2 1.2
(compiled May 29 2018 13:30:08 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            1,1'-Pyrene-1,8-diyldiethanone
_chemical_name_systematic        1,8-Diacetylpyrene
_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 0.0015 0.0009 '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 0.0056 0.0036 '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                   8.045(4)
_cell_length_b                   22.756(10)
_cell_length_c                   6.80(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.1(2)
_cell_angle_gamma                90
_cell_volume                     1243(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    262
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.7010
_cell_measurement_theta_min      2.0320
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.07587
_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 greenish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             600
_exptl_crystal_preparation       
'Mounted in a Diamond-Anvil Cell using parabar oil as pressure medium.,Luminescent'
_exptl_crystal_pressure_history  
'Pressurized to 1.65 GPa and left to stabilize over 24 hours.'
_exptl_crystal_recrystallization_method 'from acetonitrile at room temperature'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
High-pressure measurement at 1.65 GPa in a Merill-Basset Diamond Anvil Cell with
effective opening angle of 30 deg. and parabar 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  0.0846
_diffrn_reflns_av_unetI/netI     0.1040
_diffrn_reflns_Laue_measured_fraction_full 0.234
_diffrn_reflns_Laue_measured_fraction_max 0.238
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_limit_l_min       -3
_diffrn_reflns_number            1451
_diffrn_reflns_point_group_measured_fraction_full 0.234
_diffrn_reflns_point_group_measured_fraction_max 0.238
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         19.575
_diffrn_reflns_theta_min         2.001
_diffrn_ambient_temperature      293(2)
_diffrn_ambient_pressure         1650000
_diffrn_ambient_environment      'Diamond Anvil Cell filled with parabar oil'
_diffrn_crystal_treatment        
'Pressurized slowly in parabar oil as a hydrostatic medium.'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0128
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.234
_diffrn_measured_fraction_theta_max 0.238
_diffrn_measurement_details      
'List of Runs (angles in degrees, time in seconds): # Type Start End Width tₑₓₚ ω θ κ φ Frames -------------------------------------------------------------------------- 1 ω -58.00 -5.00 1.00 160.00 -- -18.73 53.00 162.00 53 2 ω -23.00 11.00 1.00 160.00 -- -18.73 53.00 -17.00 34 3 ω -61.00 -27.00 1.00 160.00 -- -18.73 135.00 -57.00 34 4 ω -6.00 20.00 1.00 160.00 -- -18.73 57.00 150.00 26 5 ω 17.00 56.00 1.00 160.00 -- -18.73-135.00-123.00 39 6 ω -63.00 -37.00 1.00 160.00 -- 18.80 160.00 -90.00 26 7 ω 25.00 51.00 1.00 160.00 -- 18.80 19.00-180.00 26 8 ω -42.00 -3.00 1.00 160.00 -- 18.80 19.00-180.00 39 9 ω -35.00 -15.00 1.00 160.00 -- 18.80 39.00 -12.00 20'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 
'Diamond Anvil Cell, effective opening angle of 30 deg.'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0173601000
_diffrn_orient_matrix_UB_12      0.0012232000
_diffrn_orient_matrix_UB_13      -0.0789397000
_diffrn_orient_matrix_UB_21      0.0272025000
_diffrn_orient_matrix_UB_22      0.0228914000
_diffrn_orient_matrix_UB_23      -0.0029498000
_diffrn_orient_matrix_UB_31      0.0625244000
_diffrn_orient_matrix_UB_32      -0.0096173000
_diffrn_orient_matrix_UB_33      -0.0166959000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56087
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Ag) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                308
_reflns_number_total             528
_reflns_odcompleteness_completeness 23.06
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     19.69
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.120
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.451
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         528
_refine_ls_number_restraints     353
_refine_ls_R_factor_all          0.2230
_refine_ls_R_factor_gt           0.1558
_refine_ls_restrained_S_all      1.389
_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)+(0.2000P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3561
_refine_ls_wR_factor_ref         0.3986
_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. Restrained distances
 C2-C3 \\sim C5-C4 \\sim C4-C3 \\sim C16-C5 \\sim C15-C2 \\sim C15-C16 \\sim
C16-C9 \\sim C10-C9 \\sim C11-
 C10 \\sim C11-C12 \\sim C15-C12
 with sigma of 0.02
3. Restrained planarity
 C1, C14, C13, C12, C15, C2, C11, C5, C16, C9, C8, C7, C6, C10, C3, C4
 with sigma of 0.05
4. Uiso/Uaniso restraints and constraints
C20 \\sim C19: within 1.7A with sigma of 0.01 and sigma for terminal atoms of
0.02
C4 \\sim C5 \\sim C16 \\sim C9 \\sim C10 \\sim C15: within 1.7A with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(O1) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C8)
\\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C7) \\sim Ueq,
Uanis(C10) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C12) \\sim Ueq, Uanis(C17) \\sim Ueq: with sigma of 0.02 and sigma for
terminal atoms of 0.05
5. Rigid body (RIGU) restrains
 C2, O1, C17, C1, C18, C14, C13, C3, C15, C12, C4, C16, C11, C5, C9, C10, C6,
 C8, C7, C19, O2, C20
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6.a Me refined with riding coordinates:
 C18(H18B,H18C,H18A), C20(H20C,H20A,H20B)
6.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C14(H14), C13(H13), C11(H11), C4(H4), C8(H8), C7(H7), C10(H10)
6.c Fitted hexagon refined as free rotating group:
 C1(C14,C13,C12,C15,C2), C5(C16,C9,C8,C7,C6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5455(13) 0.2326(4) 0.198(5) 0.044(9) Uani 1 1 d . U . . .
O2 O 0.5585(13) 0.5178(4) 0.238(5) 0.03(2) Uani 1 1 d . U . . .
C3 C 0.6971(15) 0.3460(5) 0.154(4) 0.026(6) Uani 1 1 d D U . . .
H3 H 0.5970 0.3273 0.1189 0.031 Uiso 1 1 calc R . . . .
C1 C 0.8419(9) 0.2503(3) 0.200(3) 0.022(11) Uani 1 1 d . U . . .
C14 C 0.9894(10) 0.2197(2) 0.241(3) 0.051(15) Uani 1 1 d G U . . .
H14 H 0.9895 0.1789 0.2399 0.062 Uiso 1 1 calc R . . . .
C13 C 1.1367(9) 0.2503(3) 0.283(3) 0.020(11) Uani 1 1 d G U . . .
H13 H 1.2354 0.2298 0.3106 0.024 Uiso 1 1 calc R . . . .
C12 C 1.1365(9) 0.3113(3) 0.285(3) 0.033(8) Uani 1 1 d DG U . . .
C15 C 0.9891(10) 0.3419(2) 0.244(2) 0.029(6) Uani 1 1 d DG U . . .
C2 C 0.8417(9) 0.3114(3) 0.202(3) 0.048(12) Uani 1 1 d DG U . . .
C11 C 1.2908(15) 0.3427(5) 0.327(4) 0.025(5) Uani 1 1 d D U . . .
H11 H 1.3897 0.3220 0.3482 0.030 Uiso 1 1 calc R . . . .
C17 C 0.6848(19) 0.2135(6) 0.173(7) 0.024(9) Uani 1 1 d . U . . .
C18 C 0.6934(19) 0.1459(5) 0.134(6) 0.019(10) Uani 1 1 d . U . . .
H18B H 0.5836 0.1294 0.1356 0.029 Uiso 1 1 calc R . . . .
H18C H 0.7643 0.1276 0.2343 0.029 Uiso 1 1 calc R . . . .
H18A H 0.7374 0.1391 0.0074 0.029 Uiso 1 1 calc R . . . .
C4 C 0.7026(15) 0.4073(5) 0.159(4) 0.025(5) Uani 1 1 d D U . . .
H4 H 0.6050 0.4279 0.1267 0.031 Uiso 1 1 calc R . . . .
C5 C 0.8485(8) 0.4400(3) 0.211(3) 0.022(5) Uani 1 1 d D U . . .
C16 C 0.9947(10) 0.4083(2) 0.247(3) 0.026(5) Uani 1 1 d DG U . . .
C9 C 1.1441(8) 0.4377(3) 0.288(3) 0.023(5) Uani 1 1 d DG U . . .
C8 C 1.1473(8) 0.4987(3) 0.293(3) 0.027(6) Uani 1 1 d G U . . .
H8 H 1.2472 0.5184 0.3206 0.033 Uiso 1 1 calc R . . . .
C7 C 1.0011(9) 0.5304(2) 0.257(3) 0.017(6) Uani 1 1 d G U . . .
H7 H 1.0033 0.5713 0.2599 0.020 Uiso 1 1 calc R . . . .
C6 C 0.8517(8) 0.5011(3) 0.216(3) 0.058(12) Uani 1 1 d G U . . .
C10 C 1.2924(16) 0.4041(5) 0.334(4) 0.026(5) Uani 1 1 d D U . . .
H10 H 1.3911 0.4236 0.3701 0.032 Uiso 1 1 calc R . . . .
C19 C 0.6912(18) 0.5396(6) 0.204(6) 0.046(14) Uani 1 1 d . U . . .
C20 C 0.717(2) 0.6037(5) 0.168(7) 0.041(15) Uani 1 1 d . U . . .
H20C H 0.6239 0.6190 0.0903 0.062 Uiso 1 1 calc R . . . .
H20A H 0.8170 0.6091 0.0993 0.062 Uiso 1 1 calc R . . . .
H20B H 0.7271 0.6240 0.2921 0.062 Uiso 1 1 calc R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.035(5) 0.049(6) 0.05(3) -0.002(11) 0.008(9) 0.005(5)
O2 0.018(6) 0.027(6) 0.04(7) -0.008(9) -0.008(18) 0.004(4)
C3 0.027(6) 0.030(5) 0.022(14) -0.002(6) 0.005(7) -0.001(4)
C1 0.029(6) 0.022(6) 0.02(3) -0.001(7) 0.001(8) 0.001(4)
C14 0.031(6) 0.018(8) 0.10(5) -0.001(9) -0.016(10) 0.004(4)
C13 0.024(6) 0.025(6) 0.01(4) -0.010(7) 0.006(9) 0.004(4)
C12 0.030(6) 0.027(6) 0.04(2) -0.007(7) 0.000(7) -0.001(4)
C15 0.031(5) 0.021(5) 0.035(17) -0.009(6) -0.001(7) 0.001(3)
C2 0.031(6) 0.025(6) 0.09(4) -0.005(7) -0.012(8) -0.001(4)
C11 0.023(5) 0.032(6) 0.021(14) -0.007(6) 0.008(7) 0.001(4)
C17 0.031(6) 0.020(6) 0.02(2) -0.002(8) 0.001(8) -0.002(4)
C18 0.027(8) 0.022(6) 0.01(3) 0.003(8) 0.007(13) -0.001(5)
C4 0.024(5) 0.029(5) 0.024(12) -0.005(6) 0.009(6) -0.004(4)
C5 0.023(5) 0.021(5) 0.025(13) -0.008(6) 0.011(6) -0.004(3)
C16 0.026(5) 0.021(5) 0.031(14) -0.009(6) 0.006(6) 0.000(3)
C9 0.022(5) 0.025(5) 0.023(14) -0.008(6) 0.011(6) -0.003(3)
C8 0.025(5) 0.028(6) 0.029(14) -0.005(6) 0.007(7) -0.006(4)
C7 0.022(5) 0.018(6) 0.012(14) -0.005(7) 0.012(7) -0.007(4)
C6 0.025(6) 0.020(6) 0.13(4) -0.014(7) -0.005(7) -0.006(4)
C10 0.025(5) 0.030(5) 0.025(12) -0.007(6) 0.008(7) -0.002(4)
C19 0.025(6) 0.029(6) 0.08(4) -0.011(9) 0.004(10) -0.004(4)
C20 0.017(7) 0.027(6) 0.08(4) -0.013(10) 0.010(14) -0.002(5)

_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 1.221(14) . ?
O2 C19 1.211(15) . ?
C3 C2 1.428(13) . ?
C3 C4 1.396(13) . ?
C1 C14 1.3900 . ?
C1 C2 1.3900 . ?
C1 C17 1.519(17) . ?
C14 C13 1.3900 . ?
C13 C12 1.3900 . ?
C12 C15 1.3900 . ?
C12 C11 1.447(13) . ?
C15 C2 1.3900 . ?
C15 C16 1.512(7) . ?
C11 C10 1.398(13) . ?
C17 C18 1.564(19) . ?
C4 C5 1.418(13) . ?
C5 C16 1.3900 . ?
C5 C6 1.3900 . ?
C16 C9 1.3900 . ?
C9 C8 1.3900 . ?
C9 C10 1.436(13) . ?
C8 C7 1.3900 . ?
C7 C6 1.3900 . ?
C6 C19 1.559(16) . ?
C19 C20 1.495(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 C3 C2 121.5(13) . . ?
C14 C1 C2 120.0 . . ?
C14 C1 C17 116.3(8) . . ?
C2 C1 C17 123.5(7) . . ?
C1 C14 C13 120.0 . . ?
C12 C13 C14 120.0 . . ?
C13 C12 C15 120.0 . . ?
C13 C12 C11 119.6(7) . . ?
C15 C12 C11 120.4(7) . . ?
C12 C15 C16 118.2(6) . . ?
C2 C15 C12 120.0 . . ?
C2 C15 C16 121.8(6) . . ?
C1 C2 C3 123.5(8) . . ?
C15 C2 C3 116.5(7) . . ?
C15 C2 C1 120.0 . . ?
C10 C11 C12 120.5(12) . . ?
O1 C17 C1 123.4(14) . . ?
O1 C17 C18 115.0(12) . . ?
C1 C17 C18 121.3(10) . . ?
C3 C4 C5 123.7(13) . . ?
C16 C5 C4 116.9(8) . . ?
C16 C5 C6 120.0 . . ?
C6 C5 C4 123.0(8) . . ?
C5 C16 C15 119.5(6) . . ?
C5 C16 C9 120.0 . . ?
C9 C16 C15 120.5(7) . . ?
C16 C9 C8 120.0 . . ?
C16 C9 C10 119.2(8) . . ?
C8 C9 C10 120.8(8) . . ?
C7 C8 C9 120.0 . . ?
C8 C7 C6 120.0 . . ?
C5 C6 C19 123.2(7) . . ?
C7 C6 C5 120.0 . . ?
C7 C6 C19 116.4(8) . . ?
C11 C10 C9 121.1(13) . . ?
O2 C19 C6 119.7(15) . . ?
O2 C19 C20 124.3(13) . . ?
C20 C19 C6 115.8(10) . . ?

_iucr_refine_instructions_details 
;
TITL p6_v2_abs in P21/c #14
REM reset to P21/c #14
CELL 0.56087 8.044535 22.756495 6.797682 90 93.1431 90
ZERR 4 0.004211 0.010436 0.044133 0 0.2101 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H O
UNIT 80 56 8
SADI C2 C3 C5 C4 C4 C3 C16 C5 C15 C2 C15 C16 C16 C9 C10 C9 C11 C10 C11 C12 =
 C15 C12
FLAT 0.05 C1 C14 C13 C12 C15 C2 C11 C5 C16 C9 C8 C7 C6 C10 C3 C4
SIMU 0.01 0.02 1.7 C20 C19
SIMU 0.01 0.02 1.7 C4 C5 C16 C9 C10 C15
RIGU C2 O1 C17 C1 C18 C14 C13 C3 C15 C12 C4 C16 C11 C5 C9 C10 C6 C8 C7 C19 =
 O2 C20
ISOR 0.01 0.02 O1 C3 C4 C8 C11 C18 C7 C10
ISOR 0.02 0.05 C12 C17
 
L.S. 4
PLAN  2
SIZE 0.32 0.23 0.13
BOND
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%./p6_v2_abs.hkl">
REM </olex2.extras>
 
WGHT    0.200000
FVAR       1.59070
O1    3    0.545542    0.232566    0.198006    11.00000    0.03506    0.04917 =
         0.04990   -0.00167    0.00822    0.00489
O2    3    0.558524    0.517760    0.237941    11.00000    0.01777    0.02684 =
         0.04462   -0.00771   -0.00849    0.00375
C3    1    0.697100    0.346020    0.154079    11.00000    0.02662    0.02995 =
         0.02182   -0.00229    0.00472   -0.00110
AFIX  43
H3    2    0.597040    0.327331    0.118890    11.00000   -1.20000
AFIX  66
C1    1    0.841934    0.250298    0.200198    11.00000    0.02852    0.02241 =
         0.01625   -0.00064    0.00056    0.00132
C14    1    0.989421    0.219739    0.240976    11.00000    0.03103    0.01807 =
         0.10303   -0.00080   -0.01590    0.00369
AFIX  43
H14    2    0.989546    0.178873    0.239907    11.00000   -1.20000
AFIX  65
C13    1    1.136723    0.250259    0.283353    11.00000    0.02447    0.02527 =
         0.00992   -0.00956    0.00605    0.00377
AFIX  43
H13    2    1.235402    0.229813    0.310637    11.00000   -1.20000
AFIX  65
C12    1    1.136538    0.311339    0.284953    11.00000    0.02962    0.02685 =
         0.04243   -0.00731   -0.00025   -0.00065
C15    1    0.989052    0.341898    0.244175    11.00000    0.03108    0.02129 =
         0.03477   -0.00857   -0.00074    0.00085
C2    1    0.841749    0.311379    0.201797    11.00000    0.03142    0.02466 =
         0.08709   -0.00466   -0.01237   -0.00067
AFIX   0
C11    1    1.290825    0.342746    0.326537    11.00000    0.02316    0.03214 =
         0.02122   -0.00745    0.00787    0.00114
AFIX  43
H11    2    1.389665    0.321955    0.348196    11.00000   -1.20000
AFIX   0
C17    1    0.684797    0.213476    0.173454    11.00000    0.03091    0.02010 =
         0.01994   -0.00216    0.00064   -0.00155
C18   1    0.693366    0.145888    0.133867    11.00000    0.02704    0.02161 =
         0.00970    0.00332    0.00650   -0.00149
AFIX  33
H18B  2    0.583623    0.129390    0.135587    11.00000   -1.50000
H18C  2    0.764306    0.127634    0.234301    11.00000   -1.50000
H18A  2    0.737429    0.139142    0.007407    11.00000   -1.50000
AFIX   0
C4   1    0.702582    0.407298    0.159086    11.00000    0.02375    0.02926 =
         0.02435   -0.00501    0.00932   -0.00404
AFIX  43
H4   2    0.604976    0.427851    0.126660    11.00000   -1.20000
AFIX  66
C5   1    0.848493    0.439995    0.210794    11.00000    0.02312    0.02082 =
         0.02452   -0.00801    0.01069   -0.00407
C16   1    0.994657    0.408299    0.247178    11.00000    0.02636    0.02050 =
         0.03066   -0.00908    0.00556   -0.00050
C9   1    1.144052    0.437659    0.288316    11.00000    0.02212    0.02482 =
         0.02350   -0.00770    0.01081   -0.00321
C8   1    1.147283    0.498715    0.293071    11.00000    0.02514    0.02847 =
         0.02866   -0.00481    0.00708   -0.00644
AFIX  43
H8   2    1.247238    0.518358    0.320595    11.00000   -1.20000
AFIX  65
C7   1    1.001119    0.530411    0.256688    11.00000    0.02224    0.01809 =
         0.01198   -0.00521    0.01163   -0.00716
AFIX  43
H7   2    1.003282    0.571261    0.259870    11.00000   -1.20000
AFIX  65
C6   1    0.851724    0.501052    0.215550    11.00000    0.02548    0.01969 =
         0.12704   -0.01380   -0.00541   -0.00645
AFIX   0
C10   1    1.292384    0.404123    0.334390    11.00000    0.02517    0.02959 =
         0.02507   -0.00713    0.00792   -0.00207
AFIX  43
H10   2    1.391143    0.423580    0.370055    11.00000   -1.20000
AFIX   0
C19   1    0.691249    0.539606    0.203982    11.00000    0.02497    0.02894 =
         0.08431   -0.01069    0.00356   -0.00400
C20   1    0.717119    0.603687    0.168232    11.00000    0.01690    0.02712 =
         0.08092   -0.01313    0.00951   -0.00179
AFIX  33
H20C  2    0.623876    0.619048    0.090347    11.00000   -1.50000
H20A  2    0.816995    0.609149    0.099335    11.00000   -1.50000
H20B  2    0.727102    0.624019    0.292057    11.00000   -1.50000
AFIX   0
HKLF 4
 
REM  p6_v2_abs in P21/c #14
REM R1 =  0.1558 for     308 Fo > 4sig(Fo)  and  0.2230 for all     528 data
REM    175 parameters refined using    353 restraints
 
END  
     
WGHT      0.2000      0.0000 

REM Highest difference peak  0.432,  deepest hole -0.400,  1-sigma level  0.120
Q1    1   0.8419  0.2374  0.2393  11.00000  0.05    0.43
Q2    1   0.5565  0.2292  0.2447  11.00000  0.05    0.33

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.1558 for 308 Fo > 4sig(Fo) and 0.2230 for all 1479 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.43, deepest hole -0.40
  REM Mean Shift 0, Max Shift 0.001.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.2230
  REM R1_gt = 0.1558
  REM wR_ref = 0.3986
  REM GOOF = 1.451
  REM Shift_max = 0.001
  REM Shift_mean = 0
  REM Reflections_all = 1479
  REM Reflections_gt = 308
  REM Parameters = n/a
  REM Hole = -0.40
  REM Peak = 0.43
  REM Flack = n/a

  
;
_olex2_exptl_crystal_mounting_method 
'in a Diamond Anvil Cell, opening angle 30 deg, in Paratone oil'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_diffrn_reflns_filtered   367
_oxdiff_exptl_absorpt_empirical_details 
'Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling'
_oxdiff_exptl_absorpt_empirical_full_max 7.142
_oxdiff_exptl_absorpt_empirical_full_min 0.399

# start Validation Reply Form
_vrf_PLAT088_2bisAP-gamma_1650000kPa 
;
PROBLEM: Poor Data / Parameter Ratio ....................       3.02 Note  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
In particular affected the c direction due to crystal orientation.
Additionally, the structure was determined just after a pressure-induced 
phase transition took place, resulting in an even less precise model.
;
_vrf_PLAT911_2bisAP-gamma_1650000kPa 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L= 0.597           787 Report
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
;
_vrf_PLAT082_2bisAP-gamma_1650000kPa 
;
PROBLEM: High R1 Value ..................................       0.16 Report
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC, and 
affected the fit of the final model, worsening the overall statistics.
;
_vrf_PLAT084_2bisAP-gamma_1650000kPa 
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.40 Report
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC, and 
affected the fit of the final model, worsening the overall statistics.
;
_vrf_PLAT149_2bisAP-gamma_1650000kPa 
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.20 Degree
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC, and in 
particular affected the beta angle due to crystal orientation.
;
_vrf_PLAT340_2bisAP-gamma_1650000kPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01565 Ang.  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees on a very thin plate. This limited the number
of reflections that could be collected, as most of them were obscured by the
DAC, which together with weak scattering negatively affected the precision.
;
_vrf_PLAT018_2bisAP-gamma_1650000kPa 
;
PROBLEM: _diffrn_measured_fraction_theta_max .NE. *_full           ! Check 
RESPONSE: A discrepancy between what olex2 and shelx report.
;
_vrf_PLAT148_2bisAP-gamma_1650000kPa 
;
PROBLEM: s.u. on the      c    - Axis is (Too) Large ....      0.040 Ang.  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
In particular affected the c direction due to crystal orientation.
Additionally, the structure was determined just after a pressure-induced 
phase transition took place, resulting in an even less precise model.
;
_vrf_PLAT213_2bisAP-gamma_1650000kPa 
;
PROBLEM: Atom C13              has ADP max/min Ratio .....        3.4 oblate
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
In particular affected the c direction due to crystal orientation.
Additionally, the structure was determined just after a pressure-induced 
phase transition took place, resulting in an even less precise model.
;
_vrf_PLAT220_2bisAP-gamma_1650000kPa 
;
PROBLEM: Non-Solvent  Resd 1  C   Ueq(max)/Ueq(min) Range        3.5 Ratio 
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
In particular affected the c direction due to crystal orientation.
Additionally, the structure was determined just after a pressure-induced 
phase transition took place, resulting in an even less precise model.
;
_vrf_PLAT241_2bisAP-gamma_1650000kPa 
;
PROBLEM: High   'MainMol' Ueq as Compared to Neighbors of         C2 Check 
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
In particular affected the c direction due to crystal orientation.
Additionally, the structure was determined just after a pressure-induced 
phase transition took place, resulting in an even less precise model.
;
_vrf_PLAT242_2bisAP-gamma_1650000kPa 
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of         C1 Check 
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
In particular affected the c direction due to crystal orientation.
Additionally, the structure was determined just after a pressure-induced 
phase transition took place, resulting in an even less precise model.
;
_vrf_PLAT369_2bisAP-gamma_1650000kPa 
;
PROBLEM: Long   C(sp2)-C(sp2) Bond  C6      - C19      .       1.56 Ang.  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
In particular affected the c direction due to crystal orientation.
Additionally, the structure was determined just after a pressure-induced 
phase transition took place, resulting in an even less precise model.
;
_vrf_PLAT906_2bisAP-gamma_1650000kPa 
;
PROBLEM: Large K Value in the Analysis of Variance ......     90.099 Check 
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
In particular affected the c direction due to crystal orientation.
Additionally, the structure was determined just after a pressure-induced 
phase transition took place, resulting in an even less precise model.
;
_vrf_PLAT978_2bisAP-gamma_1650000kPa 
;
PROBLEM: Number C-C Bonds with Positive Residual Density.          0 Info  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 30 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
In particular affected the c direction due to crystal orientation.
Additionally, the structure was determined just after a pressure-induced 
phase transition took place, resulting in an even less precise model.
;
# 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_2bisAP-delta_880000kPa
_database_code_depnum_ccdc_archive 'CCDC 2039416'
loop_
_audit_author_name
_audit_author_address
'Daniel Tchon'
;Faculty of Chemistry, University of Warsaw
Poland
;
_audit_update_record             
;
2020-10-19 deposited with the CCDC.	2021-01-21 downloaded from the CCDC.
;
_audit_creation_date             2020-04-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            1,1'-Pyrene-1,8-diyldiethanone
_chemical_name_systematic        1,8-Diacetylpyrene
_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'
_chemical_oxdiff_usercomment     
'f9lp, p18=0.86GPa, oa=37deg, round Bruker cell, large yellow block'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 '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 0.0056 0.0036 '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                   8.288(2)
_cell_length_b                   21.531(9)
_cell_length_c                   7.213(9)
_cell_angle_alpha                90
_cell_angle_beta                 98.93(5)
_cell_angle_gamma                90
_cell_volume                     1271.6(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1147
_cell_measurement_temperature    296.1(7)
_cell_measurement_theta_max      19.5770
_cell_measurement_theta_min      1.5390
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.061
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.15978
_exptl_absorpt_correction_type   multi-scan
_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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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    1.496
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_preparation       
'Mounted in a Diamond-Anvil Cell using parabar oil as pressure medium.,Luminescent'
_exptl_crystal_pressure_history  
'Pressurized to 0.88 GPa and left to stabilize over 24 hours.'
_exptl_crystal_recrystallization_method 'from acetonitrile at room temperature'
_exptl_crystal_size_max          0.175
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.075
_exptl_special_details           
;
High-pressure measurement at 0.88 GPa in a Merill-Basset Diamond Anvil Cell with
effective opening angle of 33 deg. and parabar 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  0.2050
_diffrn_reflns_av_unetI/netI     0.2061
_diffrn_reflns_Laue_measured_fraction_full 0.513
_diffrn_reflns_Laue_measured_fraction_max 0.510
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            5304
_diffrn_reflns_point_group_measured_fraction_full 0.513
_diffrn_reflns_point_group_measured_fraction_max 0.510
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         19.740
_diffrn_reflns_theta_min         1.963
_diffrn_ambient_temperature      296.1(7)
_diffrn_ambient_pressure         880000
_diffrn_ambient_environment      'Diamond Anvil Cell filled with parabar oil'
_diffrn_crystal_treatment        
'Pressurized slowly in parabar oil as a hydrostatic medium.'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0064
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.513
_diffrn_measured_fraction_theta_max 0.510
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -40.00   24.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -       13.7497   39.0000  167.0000 64

#__ type_ start__ end____ width___ exp.time_
  2 omega  -40.00   24.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -       13.7497   39.0000  -12.0000 64

#__ type_ start__ end____ width___ exp.time_
  3 omega   -8.00   52.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -       13.7497  -67.0000 -157.0000 60

#__ type_ start__ end____ width___ exp.time_
  4 omega  -18.00   53.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -       13.7497  -53.0000   17.0000 71

#__ type_ start__ end____ width___ exp.time_
  5 omega  -18.00   40.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.0622  -39.0000 -167.0000 58

#__ type_ start__ end____ width___ exp.time_
  6 omega  -52.00   13.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.0622   67.0000  157.0000 65

#__ type_ start__ end____ width___ exp.time_
  7 omega  -41.00   32.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.0622   13.0000   -3.0000 73

#__ type_ start__ end____ width___ exp.time_
  8 omega  -90.00  -21.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.0622  135.0000  -57.0000 69

#__ type_ start__ end____ width___ exp.time_
  9 omega  -24.00   40.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.0622  -39.0000   12.0000 64

#__ type_ start__ end____ width___ exp.time_
 10 omega   11.00   49.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.0622 -114.0000 -135.0000 38

#__ type_ start__ end____ width___ exp.time_
 11 omega   37.00   59.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -       13.7497  -99.0000    0.0000 22

#__ type_ start__ end____ width___ exp.time_
 12 omega  -33.00  -13.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.0622   77.0000  120.0000 20

#__ type_ start__ end____ width___ exp.time_
 13 omega   -1.00   40.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.0622  -97.0000   35.0000 41
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 
'Diamond Anvil Cell, effective opening angle of 33 deg.'
_diffrn_orient_matrix_UB_11      0.0080870000
_diffrn_orient_matrix_UB_12      0.0121816000
_diffrn_orient_matrix_UB_13      0.0692071000
_diffrn_orient_matrix_UB_21      -0.0634470000
_diffrn_orient_matrix_UB_22      -0.0067275000
_diffrn_orient_matrix_UB_23      0.0095444000
_diffrn_orient_matrix_UB_31      0.0240206000
_diffrn_orient_matrix_UB_32      -0.0219610000
_diffrn_orient_matrix_UB_33      0.0357442000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56087
_diffrn_source                   'SuperNova (Ag) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                514
_reflns_number_total             1188
_reflns_odcompleteness_completeness 50.21
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     19.69
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         1188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2165
_refine_ls_R_factor_gt           0.0958
_refine_ls_restrained_S_all      1.050
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1922
_refine_ls_wR_factor_ref         0.2589
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C14(H14), C13(H13), C4(H4), C8(H8), C10(H10), C7(H7), C11(H11)
2.b Idealised Me refined as rotating group:
 C18(H18B,H18A,H18C), C20(H20B,H20A,H20C)
;
_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
O2 O 0.0768(6) 0.5340(2) 0.7895(12) 0.066(4) Uani 1 1 d . . . . .
O1 O 0.0636(7) 0.2577(2) 0.3525(13) 0.065(3) Uani 1 1 d . . . . .
C2 C 0.3397(8) 0.3361(3) 0.5399(16) 0.040(4) Uani 1 1 d . . . . .
C15 C 0.4908(8) 0.3657(3) 0.6074(16) 0.037(4) Uani 1 1 d . . . . .
C18 C 0.1902(8) 0.1679(3) 0.4991(18) 0.058(5) Uani 1 1 d . . . . .
H18B H 0.081652 0.151160 0.475704 0.087 Uiso 1 1 calc GR . . . .
H18A H 0.232148 0.164848 0.630552 0.087 Uiso 1 1 calc GR . . . .
H18C H 0.259342 0.144950 0.428623 0.087 Uiso 1 1 calc GR . . . .
C20 C 0.2208(9) 0.6287(3) 0.8117(17) 0.050(4) Uani 1 1 d . . . . .
H20B H 0.115155 0.647574 0.780305 0.075 Uiso 1 1 calc GR . . . .
H20A H 0.293224 0.645367 0.732497 0.075 Uiso 1 1 calc GR . . . .
H20C H 0.263590 0.637241 0.940561 0.075 Uiso 1 1 calc GR . . . .
C12 C 0.6399(8) 0.3340(3) 0.6105(15) 0.039(4) Uani 1 1 d . . . . .
C16 C 0.4946(8) 0.4285(3) 0.6722(15) 0.030(4) Uani 1 1 d . . . . .
C6 C 0.3550(8) 0.5239(3) 0.7498(17) 0.039(4) Uani 1 1 d . . . . .
C19 C 0.2059(8) 0.5600(4) 0.7830(17) 0.044(4) Uani 1 1 d . . . . .
C3 C 0.1941(7) 0.3739(3) 0.5287(15) 0.036(4) Uani 1 1 d . . . . .
H3 H 0.094348 0.357029 0.475606 0.043 Uiso 1 1 calc R . . . .
C5 C 0.3454(7) 0.4627(3) 0.6747(16) 0.038(4) Uani 1 1 d . . . . .
C14 C 0.4899(9) 0.2422(3) 0.5033(17) 0.041(4) Uani 1 1 d . . . . .
H14 H 0.490690 0.199837 0.478472 0.049 Uiso 1 1 calc R . . . .
C9 C 0.6480(8) 0.4583(4) 0.7361(18) 0.047(5) Uani 1 1 d . . . . .
C1 C 0.3388(8) 0.2724(3) 0.4901(16) 0.040(4) Uani 1 1 d . . . . .
C17 C 0.1864(10) 0.2358(4) 0.4396(19) 0.044(4) Uani 1 1 d . . . . .
C13 C 0.6362(9) 0.2720(4) 0.5509(16) 0.040(4) Uani 1 1 d . . . . .
H13 H 0.733277 0.251053 0.543667 0.047 Uiso 1 1 calc R . . . .
C4 C 0.1983(9) 0.4335(4) 0.5934(17) 0.047(4) Uani 1 1 d . . . . .
H4 H 0.101113 0.455729 0.583714 0.057 Uiso 1 1 calc R . . . .
C8 C 0.6523(9) 0.5191(4) 0.8056(19) 0.059(5) Uani 1 1 d . . . . .
H8 H 0.751579 0.538020 0.850574 0.071 Uiso 1 1 calc R . . . .
C10 C 0.7957(8) 0.4226(3) 0.7315(16) 0.044(5) Uani 1 1 d . . . . .
H10 H 0.896376 0.441519 0.769148 0.052 Uiso 1 1 calc R . . . .
C7 C 0.5045(8) 0.5514(4) 0.8066(16) 0.040(4) Uani 1 1 d . . . . .
H7 H 0.508081 0.592454 0.846908 0.048 Uiso 1 1 calc R . . . .
C11 C 0.7919(8) 0.3648(4) 0.6762(17) 0.041(4) Uani 1 1 d . . . . .
H11 H 0.889413 0.343159 0.679364 0.050 Uiso 1 1 calc R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O2 0.046(3) 0.053(5) 0.108(13) -0.014(3) 0.035(5) -0.002(3)
O1 0.040(3) 0.052(5) 0.094(13) -0.001(3) -0.016(5) -0.005(3)
C2 0.036(4) 0.021(5) 0.068(15) -0.001(4) 0.024(5) -0.003(3)
C15 0.037(4) 0.021(5) 0.059(16) 0.001(4) 0.021(5) 0.000(3)
C18 0.043(4) 0.031(7) 0.099(19) 0.006(5) 0.006(6) -0.007(4)
C20 0.055(5) 0.021(6) 0.077(16) -0.011(4) 0.023(6) 0.003(4)
C12 0.037(4) 0.041(6) 0.043(16) 0.006(4) 0.017(6) 0.000(4)
C16 0.034(4) 0.027(6) 0.036(15) 0.003(4) 0.024(5) 0.002(3)
C6 0.039(4) 0.026(6) 0.061(16) 0.001(4) 0.033(6) 0.001(4)
C19 0.033(4) 0.041(7) 0.059(16) 0.004(5) 0.010(5) 0.003(4)
C3 0.018(3) 0.036(6) 0.053(16) 0.006(4) 0.004(5) -0.005(3)
C5 0.028(4) 0.031(6) 0.056(16) 0.004(4) 0.015(5) -0.004(4)
C14 0.045(5) 0.032(6) 0.048(16) -0.004(4) 0.019(6) -0.008(4)
C9 0.034(4) 0.046(7) 0.068(18) -0.001(5) 0.026(6) -0.008(4)
C1 0.038(5) 0.029(6) 0.055(15) -0.005(4) 0.012(6) 0.000(4)
C17 0.043(5) 0.035(6) 0.056(16) -0.002(4) 0.014(7) -0.011(4)
C13 0.045(5) 0.033(6) 0.047(16) 0.004(4) 0.026(6) 0.008(4)
C4 0.039(4) 0.036(7) 0.071(17) 0.000(5) 0.025(6) -0.001(4)
C8 0.044(5) 0.031(7) 0.11(2) -0.005(5) 0.033(7) -0.011(4)
C10 0.027(4) 0.031(7) 0.074(17) 0.002(4) 0.015(6) 0.001(3)
C7 0.042(4) 0.033(6) 0.047(15) -0.002(4) 0.018(5) -0.004(4)
C11 0.033(4) 0.048(7) 0.046(17) 0.000(5) 0.016(5) 0.005(4)

_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
O2 C19 1.214(7) . ?
O1 C17 1.206(10) . ?
C2 C15 1.421(10) . ?
C2 C3 1.447(8) . ?
C2 C1 1.418(10) . ?
C15 C12 1.409(8) . ?
C15 C16 1.429(10) . ?
C18 H18B 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18C 0.9600 . ?
C18 C17 1.523(10) . ?
C20 H20B 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20C 0.9600 . ?
C20 C19 1.497(9) . ?
C12 C13 1.403(10) . ?
C12 C11 1.438(10) . ?
C16 C5 1.442(8) . ?
C16 C9 1.435(9) . ?
C6 C19 1.510(9) . ?
C6 C5 1.423(10) . ?
C6 C7 1.377(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.363(10) . ?
C5 C4 1.415(10) . ?
C14 H14 0.9300 . ?
C14 C1 1.401(9) . ?
C14 C13 1.367(9) . ?
C9 C8 1.400(11) . ?
C9 C10 1.451(9) . ?
C1 C17 1.486(10) . ?
C13 H13 0.9300 . ?
C4 H4 0.9300 . ?
C8 H8 0.9300 . ?
C8 C7 1.409(9) . ?
C10 H10 0.9300 . ?
C10 C11 1.306(10) . ?
C7 H7 0.9300 . ?
C11 H11 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 C2 C3 116.7(7) . . ?
C1 C2 C15 119.3(6) . . ?
C1 C2 C3 124.0(7) . . ?
C2 C15 C16 120.6(6) . . ?
C12 C15 C2 120.9(7) . . ?
C12 C15 C16 118.5(7) . . ?
H18B C18 H18A 109.5 . . ?
H18B C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H20B C20 H20A 109.5 . . ?
H20B C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20C 109.5 . . ?
C15 C12 C11 120.3(7) . . ?
C13 C12 C15 118.6(7) . . ?
C13 C12 C11 121.1(7) . . ?
C15 C16 C5 120.8(6) . . ?
C15 C16 C9 120.2(6) . . ?
C9 C16 C5 119.1(7) . . ?
C5 C6 C19 122.5(6) . . ?
C7 C6 C19 117.0(7) . . ?
C7 C6 C5 120.4(6) . . ?
O2 C19 C20 120.3(7) . . ?
O2 C19 C6 121.2(7) . . ?
C20 C19 C6 118.6(6) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 C2 122.2(7) . . ?
C4 C3 H3 118.9 . . ?
C6 C5 C16 118.7(7) . . ?
C4 C5 C16 117.0(7) . . ?
C4 C5 C6 124.3(6) . . ?
C1 C14 H14 118.4 . . ?
C13 C14 H14 118.4 . . ?
C13 C14 C1 123.2(8) . . ?
C16 C9 C10 117.7(7) . . ?
C8 C9 C16 120.4(6) . . ?
C8 C9 C10 121.9(7) . . ?
C2 C1 C17 123.1(7) . . ?
C14 C1 C2 117.6(7) . . ?
C14 C1 C17 119.2(7) . . ?
O1 C17 C18 120.1(7) . . ?
O1 C17 C1 122.5(8) . . ?
C1 C17 C18 117.4(8) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 119.9(7) . . ?
C14 C13 H13 120.0 . . ?
C3 C4 C5 122.3(7) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C9 C8 H8 120.4 . . ?
C9 C8 C7 119.3(7) . . ?
C7 C8 H8 120.4 . . ?
C9 C10 H10 118.9 . . ?
C11 C10 C9 122.1(7) . . ?
C11 C10 H10 118.9 . . ?
C6 C7 C8 122.0(8) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 H7 119.0 . . ?
C12 C11 H11 119.4 . . ?
C10 C11 C12 121.2(7) . . ?
C10 C11 H11 119.4 . . ?

_iucr_refine_instructions_details 
;
TITL exp_292__reject_lims_3d_oa33_res83_hp_smart3__rint40_res83_out_a.res in P2(
 2''ap-de-9kbar.res created by SHELXL-2016/4 at 11:07:38 on 21-Apr-2020
REM Old TITL exp_292__reject_lims_3D_oa33_Res83_HP_smart3__Rint40_Res83_out in
REM P2(1
REM SHELXT solution in P2(1)/c
REM R1 0.264, Rweak 0.044, Alpha 0.087, Orientation as input
REM Formula found by SHELXT:
CELL 0.56087 8.2885 21.5312 7.2128 90 98.933 90
ZERR 4 0.002 0.0087 0.0088 0 0.049 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H O
UNIT 80 56 8

L.S. 4 0 0
PLAN  20
BOND H
list 4
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%.\\2\'\'AP-de-9kbar.hkl">
REM </olex2.extras>

WGHT    0.100000
FVAR       1.10697
O2    3    0.076817    0.534009    0.789550    11.00000    0.04565    0.05259 =
         0.10834   -0.01410    0.03502   -0.00219
O1    3    0.063594    0.257722    0.352500    11.00000    0.03996    0.05211 =
         0.09449   -0.00083   -0.01645   -0.00493
C2    1    0.339708    0.336150    0.539907    11.00000    0.03563    0.02057 =
         0.06809   -0.00056    0.02411   -0.00259
C15   1    0.490753    0.365688    0.607362    11.00000    0.03666    0.02081 =
         0.05873    0.00065    0.02080   -0.00021
C18   1    0.190239    0.167922    0.499109    11.00000    0.04286    0.03147 =
         0.09883    0.00589    0.00627   -0.00680
AFIX 137
H18B  2    0.081652    0.151160    0.475704    11.00000   -1.50000
H18A  2    0.232148    0.164848    0.630552    11.00000   -1.50000
H18C  2    0.259342    0.144950    0.428623    11.00000   -1.50000
AFIX   0
C20   1    0.220803    0.628699    0.811661    11.00000    0.05549    0.02100 =
         0.07664   -0.01053    0.02254    0.00310
AFIX 137
H20B  2    0.115155    0.647574    0.780305    11.00000   -1.50000
H20A  2    0.293224    0.645367    0.732497    11.00000   -1.50000
H20C  2    0.263590    0.637241    0.940561    11.00000   -1.50000
AFIX   0
C12    1    0.639866    0.334009    0.610476    11.00000    0.03677    0.04111 =
         0.04254    0.00551    0.01707   -0.00042
C16   1    0.494623    0.428491    0.672162    11.00000    0.03369    0.02723 =
         0.03554    0.00303    0.02355    0.00194
C6    1    0.355024    0.523933    0.749751    11.00000    0.03915    0.02554 =
         0.06128    0.00079    0.03333    0.00134
C19   1    0.205895    0.559964    0.783003    11.00000    0.03257    0.04071 =
         0.05881    0.00380    0.00975    0.00313
C3    1    0.194118    0.373949    0.528710    11.00000    0.01845    0.03576 =
         0.05264    0.00603    0.00368   -0.00524
AFIX  43
H3    2    0.094348    0.357029    0.475606    11.00000   -1.20000
AFIX   0
C5    1    0.345370    0.462693    0.674662    11.00000    0.02836    0.03076 =
         0.05599    0.00395    0.01454   -0.00427
C14    1    0.489909    0.242211    0.503301    11.00000    0.04522    0.03178 =
         0.04850   -0.00356    0.01944   -0.00769
AFIX  43
H14    2    0.490690    0.199837    0.478472    11.00000   -1.20000
AFIX   0
C9   1    0.647978    0.458337    0.736085    11.00000    0.03369    0.04582 =
         0.06778   -0.00086    0.02555   -0.00781
C1    1    0.338845    0.272422    0.490135    11.00000    0.03842    0.02918 =
         0.05488   -0.00478    0.01194    0.00025
C17   1    0.186390    0.235819    0.439550    11.00000    0.04291    0.03453 =
         0.05581   -0.00169    0.01365   -0.01100
C13    1    0.636247    0.271952    0.550852    11.00000    0.04457    0.03305 =
         0.04692    0.00384    0.02585    0.00794
AFIX  43
H13    2    0.733277    0.251053    0.543667    11.00000   -1.20000
AFIX   0
C4    1    0.198275    0.433508    0.593360    11.00000    0.03939    0.03647 =
         0.07066   -0.00029    0.02485   -0.00129
AFIX  43
H4    2    0.101113    0.455729    0.583714    11.00000   -1.20000
AFIX   0
C8   1    0.652292    0.519136    0.805589    11.00000    0.04396    0.03096 =
         0.10945   -0.00514    0.03281   -0.01131
AFIX  43
H8   2    0.751579    0.538020    0.850574    11.00000   -1.20000
AFIX   0
C10   1    0.795712    0.422632    0.731495    11.00000    0.02726    0.03134 =
         0.07448    0.00217    0.01464    0.00065
AFIX  43
H10   2    0.896376    0.441519    0.769148    11.00000   -1.20000
AFIX   0
C7   1    0.504518    0.551378    0.806602    11.00000    0.04208    0.03323 =
         0.04697   -0.00164    0.01789   -0.00408
AFIX  43
H7   2    0.508081    0.592454    0.846908    11.00000   -1.20000
AFIX   0
C11   1    0.791932    0.364809    0.676184    11.00000    0.03295    0.04828 =
         0.04602   -0.00037    0.01649    0.00535
AFIX  43
H11   2    0.889413    0.343159    0.679364    11.00000   -1.20000
AFIX   0
HKLF 4




REM  exp_292__reject_lims_3d_oa33_res83_hp_smart3__rint40_res83_out_a.res in P2(
REM R1 =  0.0958 for     514 Fo > 4sig(Fo)  and  0.2165 for all    1188 data
REM    201 parameters refined using      0 restraints

END  
     
WGHT      0.1220      0.0000 

REM Highest difference peak  0.251,  deepest hole -0.238,  1-sigma level  0.064
Q1    1   0.3351  0.5199  0.5374  11.00000  0.05    0.25
Q2    1   0.1086  0.4813  0.3946  11.00000  0.05    0.25
Q3    1   0.5441  0.6034  0.9753  11.00000  0.05    0.24
Q4    1   0.2466  0.1438  0.3330  11.00000  0.05    0.23
Q5    1   0.6930  0.5808  0.9456  11.00000  0.05    0.21
Q6    1   0.3198  0.7031  0.6761  11.00000  0.05    0.21
Q7    1   0.3389  0.1403  0.5629  11.00000  0.05    0.21
Q8    1   0.4578  0.6169  0.6199  11.00000  0.05    0.21
Q9    1   0.9067  0.5017  0.6934  11.00000  0.05    0.21
Q10   1   0.1155  0.1153  0.3551  11.00000  0.05    0.20
Q11   1   0.7851  0.5403  0.8050  11.00000  0.05    0.19
Q12   1   0.5366  0.6148  0.8899  11.00000  0.05    0.19
Q13   1   0.7428  0.4197  0.4983  11.00000  0.05    0.19
Q14   1   0.3814  0.6418  0.8292  11.00000  0.05    0.18
Q15   1   0.0616  0.3361  0.5575  11.00000  0.05    0.18
Q16   1   0.5991  0.5163  0.5558  11.00000  0.05    0.18
Q17   1   0.4025  0.1190  0.4211  11.00000  0.05    0.18
Q18   1   0.5001  0.1636  0.5270  11.00000  0.05    0.18
Q19   1   0.1528  0.1003  0.3991  11.00000  0.05    0.18
Q20   1   0.4845  0.4204  0.4944  11.00000  0.05    0.17

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0958 for 514 Fo > 4sig(Fo) and 0.2165 for all 5365 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.25, deepest hole -0.24
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.2165
  REM R1_gt = 0.0958
  REM wR_ref = 0.2589
  REM GOOF = 1.050
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 5365
  REM Reflections_gt = 514
  REM Parameters = n/a
  REM Hole = -0.24
  REM Peak = 0.25
  REM Flack = n/a

  
;
_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT029_2bisAP-delta_880000kPa 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.513 Why?  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 33 degrees on a very thin plate. This limited the number
of reflections that could be collected, as most of them were obscured
by the DAC.
;
_vrf_PLAT088_2bisAP-delta_880000kPa 
;
PROBLEM: Poor Data / Parameter Ratio ....................       5.91 Note  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 33 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
;
_vrf_RINTA01_2bisAP-delta_880000kPa 
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 33 degrees on a very thin plate. This resulted in low 
diffracted intensities, low available data resolution and high Rint value.
;
_vrf_PLAT020_2bisAP-delta_880000kPa 
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.205 Report
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 33 degrees on a very thin plate. This resulted in low 
diffracted intensities, low available data resolution and high Rint value.
;
_vrf_PLAT340_2bisAP-delta_880000kPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01087 Ang.  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 33 degrees on a very thin plate. This limited the number
of reflections that could be collected, as most of them were obscured by the
DAC, which together with weak scattering negatively affected the precision.
;
_vrf_PLAT911_2bisAP-delta_880000kPa 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L= 0.600           701 Report
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 33 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC.
;
_vrf_PLAT026_2bisAP-delta_880000kPa 
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        43% Check 
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 33 degrees on a very thin plate. This limited the number
of reflections that could be collected, as most of them were obscured
by the DAC.
;
_vrf_PLAT084_2bisAP-delta_880000kPa 
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.26 Report
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 33 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC, and 
affected the fit of the final model, worsening the overall statistics.
;
_vrf_PLAT148_2bisAP-delta_880000kPa 
;
PROBLEM: s.u. on the      c    - Axis is (Too) Large ....      0.009 Ang.  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 33 degrees. This limited the number of reflections 
that could be collected, as most of them were obscured by the DAC, and in 
particular affected the c direction due to crystal orientation.
;
_vrf_PLAT241_2bisAP-delta_880000kPa 
;
PROBLEM: High   'MainMol' Ueq as Compared to Neighbors of         C8 Check 
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell
with opening angle of 33 degrees on a very thin plate. This limited the number
of reflections that could be collected, as most of them were obscured by the
DAC, which together with weak scattering negatively affected the precision.
;
_vrf_PLAT250_2bisAP-delta_880000kPa 
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.1 Note  
RESPONSE: The data were collected at high pressure in a Diamond Anvil Cell with
opening angle of 33 degrees on a very thin plate. This limited the number of
reflections that could be collected, as most of them were obscured by the DAC,
resulting in an elongation of average U(i,j) tensor due to Fourier cutoff.
;
# 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_2bisAP-beta_0kPa
_database_code_depnum_ccdc_archive 'CCDC 2039409'
loop_
_audit_author_name
_audit_author_address
'Daniel Tchon'
;Faculty of Chemistry, University of Warsaw
Poland
;
_audit_update_record             
;
2020-10-19 deposited with the CCDC.	2021-01-21 downloaded from the CCDC.
;
_audit_creation_date             2020-03-24
_audit_creation_method           
;
Olex2 1.2
(compiled May 29 2018 13:30:08 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            1,1'-Pyrene-1,8-diyldiethanone
_chemical_name_systematic        1,8-Diacetylpyrene
_chemical_formula_moiety         'C20 H14 O2'
_chemical_formula_sum            'C20 H14 O2'
_chemical_formula_weight         286.31
_chemical_absolute_configuration ?
_chemical_melting_point          430
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      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   4.69175(9)
_cell_length_b                   35.5546(5)
_cell_length_c                   16.2326(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2707.81(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    15294
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      46.7040
_cell_measurement_theta_min      2.2750
_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  0.827
_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 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       plate
_exptl_crystal_F_000             1200
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.0155
0 -1 0 0.0155
0 -5 2 0.0810
0 5 -2 0.0810
-1 -5 0 0.0394
0 -4 -5 0.1202
0 4 5 0.1202
3 -3 5 0.0907
1 1 0 0.0557
-1 -1 0 0.0497

_exptl_crystal_recrystallization_method 'from chloroform at room temperature'
_exptl_crystal_size_max          0.254
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.031
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       74
_diffrn_reflns_limit_k_min       -69
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            31142
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         48.280
_diffrn_reflns_theta_min         2.759
_diffrn_ambient_temperature      100.00(10)
_diffrn_ambient_pressure         0
_diffrn_ambient_environment      air
_diffrn_detector_area_resol_mean 8.0013
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
'List of Runs (angles in degrees, time in seconds): # Type Start End Width tₑₓₚ ω θ κ φ Frames -------------------------------------------------------------------------- 1 ω -21.00 69.00 1.00 20.00 -- 0.00 57.00 -90.00 90 2 ω -21.00 69.00 1.00 20.00 -- 0.00 57.00 0.00 90 3 ω -76.00 -21.00 1.00 20.00 -- 0.00 160.00 90.00 55 4 ω -20.00 42.00 1.00 20.00 -- 0.00 -99.00 90.00 62 5 ω 21.00 76.00 1.00 20.00 -- 0.00-160.00-180.00 55 6 ω -26.00 72.00 1.00 20.00 -- 0.00 37.00 90.00 98 7 ω -76.00 -21.00 1.00 20.00 -- 0.00 160.00 150.00 55 8 ω -7.00 93.00 1.00 90.00 -- 62.95 -77.00 -30.00 100 9 ω 40.00 134.00 1.00 90.00 -- 62.95 45.00 60.00 94 10 ω -21.00 69.00 1.00 5.00 -- 0.00 57.00 0.00 90 11 ω -76.00 -21.00 1.00 5.00 -- 0.00 160.00 90.00 55 12 ω -20.00 42.00 1.00 5.00 -- 0.00 -99.00 90.00 62 13 ω -9.00 102.00 1.00 90.00 -- 62.95 -94.00 90.00 111 14 ω -8.00 86.00 1.00 90.00 -- 62.95 -45.00 90.00 94 15 ω 2.00 117.00 1.00 90.00 -- 62.95-125.00 -90.00 115 16 ω -10.00 116.00 1.00 90.00 -- 62.95 -15.00 60.00 126 17 ω -7.00 93.00 1.00 90.00 -- 62.95 -77.00 -90.00 100 18 ω 41.00 69.00 1.00 90.00 -- 62.95 61.00-150.00 28'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.946
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                4903
_reflns_number_total             6521
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.297
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.093
_refine_ls_abs_structure_details .
_refine_ls_abs_structure_Flack   .
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         6521
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0691
_refine_ls_restrained_S_all      1.084
_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)+(0.0841P)²+0.1221P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1527
_refine_ls_wR_factor_ref         0.1657
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C11(H11), C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C18(H18B,H18A,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3753(3) 0.07922(3) 0.19242(8) 0.0254(2) Uani 1 1 d . . . . .
C1 C 0.3960(2) 0.06147(3) 0.33406(8) 0.01488(18) Uani 1 1 d . . . . .
C2 C 0.1993(2) 0.03095(3) 0.33157(7) 0.01273(16) Uani 1 1 d . . . . .
C3 C 0.0936(3) 0.01474(3) 0.25673(7) 0.01565(19) Uani 1 1 d . . . . .
H3 H 0.1541 0.0246 0.2066 0.019 Uiso 1 1 calc R . . . .
C11 C 0.0961(3) 0.01401(4) 0.55955(8) 0.0204(2) Uani 1 1 d . . . . .
H11 H 0.1620 0.0235 0.6094 0.025 Uiso 1 1 calc R . . . .
C12 C 0.2011(3) 0.02945(3) 0.48357(7) 0.01533(18) Uani 1 1 d . . . . .
C13 C 0.4018(3) 0.05854(4) 0.48390(9) 0.0192(2) Uani 1 1 d . . . . .
H13 H 0.4724 0.0675 0.5337 0.023 Uiso 1 1 calc R . . . .
C14 C 0.4958(3) 0.07402(3) 0.41069(9) 0.01846(19) Uani 1 1 d . . . . .
H14 H 0.6293 0.0933 0.4123 0.022 Uiso 1 1 calc R . . . .
C15 C 0.1009(2) 0.01515(3) 0.40692(8) 0.01239(14) Uani 1 1 d . . . . .
C17 C 0.4932(3) 0.08229(3) 0.25911(9) 0.0182(2) Uani 1 1 d . . . . .
C18 C 0.7389(3) 0.10953(4) 0.26779(12) 0.0259(3) Uani 1 1 d . . . . .
H18B H 0.8064 0.1165 0.2141 0.039 Uiso 1 1 calc GR . . . .
H18A H 0.8904 0.0978 0.2981 0.039 Uiso 1 1 calc GR . . . .
H18C H 0.6758 0.1316 0.2967 0.039 Uiso 1 1 calc GR . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0357(6) 0.0208(4) 0.0198(4) 0.0029(3) 0.0043(4) -0.0063(4)
C1 0.0148(4) 0.0119(3) 0.0180(5) -0.0007(3) 0.0008(3) 0.0007(3)
C2 0.0146(4) 0.0110(3) 0.0126(4) -0.0003(3) 0.0003(3) 0.0011(3)
C3 0.0204(5) 0.0156(4) 0.0109(4) 0.0000(3) 0.0011(3) -0.0027(3)
C11 0.0284(6) 0.0220(5) 0.0109(4) -0.0017(3) -0.0020(4) 0.0059(4)
C12 0.0186(5) 0.0147(4) 0.0127(4) -0.0022(3) -0.0019(3) 0.0033(3)
C13 0.0214(5) 0.0175(5) 0.0186(5) -0.0051(4) -0.0050(4) 0.0015(4)
C14 0.0179(4) 0.0145(4) 0.0230(5) -0.0030(4) -0.0029(4) -0.0004(3)
C15 0.0142(3) 0.0115(3) 0.0115(3) -0.0008(3) -0.0005(3) 0.0020(2)
C17 0.0176(4) 0.0130(3) 0.0241(5) 0.0020(4) 0.0058(4) 0.0019(3)
C18 0.0177(5) 0.0208(5) 0.0392(8) 0.0082(5) 0.0024(5) -0.0023(4)

_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 1.220(2) . ?
C1 C2 1.4249(15) . ?
C1 C14 1.4019(19) . ?
C1 C17 1.4953(18) . ?
C2 C3 1.4334(17) . ?
C2 C15 1.4230(16) . ?
C3 C3 1.367(2) 2 ?
C11 C11 1.343(3) 2 ?
C11 C12 1.4373(19) . ?
C12 C13 1.3987(18) . ?
C12 C15 1.4240(16) . ?
C13 C14 1.382(2) . ?
C15 C15 1.434(2) 2 ?
C17 C18 1.5122(19) . ?

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 C17 123.46(11) . . ?
C14 C1 C2 118.93(11) . . ?
C14 C1 C17 117.55(11) . . ?
C1 C2 C3 123.67(11) . . ?
C15 C2 C1 119.11(10) . . ?
C15 C2 C3 117.22(10) . . ?
C3 C3 C2 122.04(6) 2 . ?
C11 C11 C12 120.89(8) 2 . ?
C13 C12 C11 120.67(12) . . ?
C13 C12 C15 119.33(12) . . ?
C15 C12 C11 120.01(11) . . ?
C14 C13 C12 120.39(12) . . ?
C13 C14 C1 121.99(10) . . ?
C2 C15 C12 120.18(9) . . ?
C2 C15 C15 120.72(6) . 2 ?
C12 C15 C15 119.09(7) . 2 ?
O1 C17 C1 122.64(12) . . ?
O1 C17 C18 119.03(12) . . ?
C1 C17 C18 118.27(13) . . ?

_iucr_refine_instructions_details 
;
TITL F9o_1 in Fdd2 #43
REM reset to Fdd2 #43
CELL 0.71073 4.691746 35.554621 16.232553 90 90 90
ZERR 8 0.000092 0.000522 0.000311 0 0 0
LATT -4
SYMM -X,-Y,+Z
SYMM 0.25-X,0.25+Y,0.25+Z
SYMM 0.25+X,0.25-Y,0.25+Z
SFAC C H O
UNIT 160 112 16
 
L.S. 4
PLAN  5
BOND
fmap 2
acta
OMIT 0 4 0
REM <olex2.extras>
REM <HklSrc "%./f9o_1.hkl">
REM </olex2.extras>
 
WGHT    0.084100    0.122100
FVAR       1.00875
O1    3    0.375319    0.079221    0.192421    11.00000    0.03569    0.02082 =
         0.01984    0.00290    0.00431   -0.00627
C1    1    0.396024    0.061467    0.334060    11.00000    0.01481    0.01186 =
         0.01797   -0.00072    0.00081    0.00070
C2    1    0.199350    0.030950    0.331573    11.00000    0.01456    0.01099 =
         0.01263   -0.00026    0.00031    0.00105
C3    1    0.093565    0.014742    0.256725    11.00000    0.02043    0.01557 =
         0.01095    0.00000    0.00107   -0.00271
AFIX  43
H3    2    0.154082    0.024583    0.206608    11.00000   -1.20000
AFIX   0
C11   1    0.096062    0.014008    0.559551    11.00000    0.02838    0.02201 =
         0.01093   -0.00175   -0.00200    0.00585
AFIX  43
H11   2    0.161971    0.023538    0.609389    11.00000   -1.20000
AFIX   0
C12   1    0.201137    0.029451    0.483566    11.00000    0.01861    0.01471 =
         0.01267   -0.00218   -0.00194    0.00333
C13   1    0.401812    0.058544    0.483900    11.00000    0.02141    0.01749 =
         0.01857   -0.00505   -0.00498    0.00154
AFIX  43
H13   2    0.472392    0.067528    0.533690    11.00000   -1.20000
AFIX   0
C14   1    0.495807    0.074015    0.410689    11.00000    0.01789    0.01447 =
         0.02301   -0.00296   -0.00290   -0.00039
AFIX  43
H14   2    0.629303    0.093337    0.412297    11.00000   -1.20000
AFIX   0
C15   1    0.100868    0.015150    0.406916    11.00000    0.01422    0.01151 =
         0.01146   -0.00081   -0.00046    0.00197
C17   1    0.493171    0.082287    0.259109    11.00000    0.01761    0.01304 =
         0.02410    0.00197    0.00577    0.00195
C18   1    0.738880    0.109528    0.267789    11.00000    0.01772    0.02082 =
         0.03924    0.00823    0.00241   -0.00230
AFIX 137
H18B  2    0.806370    0.116545    0.214115    11.00000   -1.50000
H18A  2    0.890416    0.097769    0.298053    11.00000   -1.50000
H18C  2    0.675836    0.131562    0.296708    11.00000   -1.50000
AFIX   0
HKLF 4
 
REM  F9o_1 in Fdd2 #43
REM R1 =  0.0691 for    4903 Fo > 4sig(Fo)  and  0.0939 for all    6521 data
REM    101 parameters refined using      1 restraints
 
END  
     
WGHT      0.0841      0.1221 

REM Highest difference peak  1.297,  deepest hole -0.298,  1-sigma level  0.093
Q1    1   0.0000  0.0000  0.5575  10.50000  0.05    1.30
Q2    1   0.0000  0.0000  0.2612  10.50000  0.05    0.93
Q3    1   0.0000  0.0000  0.4079  10.50000  0.05    0.79
Q4    1   0.2996  0.0457  0.3358  11.00000  0.05    0.70
Q5    1   0.1519  0.0246  0.3689  11.00000  0.05    0.65

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0691 for 4903 Fo > 4sig(Fo) and 0.0939 for all 32864 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 1.30, deepest hole -0.30
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0939
  REM R1_gt = 0.0691
  REM wR_ref = 0.1657
  REM GOOF = 1.084
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 32864
  REM Reflections_gt = 4903
  REM Parameters = n/a
  REM Hole = -0.30
  REM Peak = 1.30
  REM Flack = 0.2(5)

  
;
_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_DIFMX02_2bisAP-beta_0kPa    
;
PROBLEM: The maximum difference density is > 0.1*ZMAX*0.75
RESPONSE: The presence of high-resolution diffraction data
revealed high positive residual density on electron-rich double bonds,
which could not be described by a spherical approximation of electron density.
;
_vrf_PLAT097_2bisAP-beta_0kPa    
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       1.30 eA-3  
RESPONSE: The presence of high-resolution diffraction data
revealed high positive residual density on electron-rich double bonds,
which could not be described by a spherical approximation of electron density.
;
_vrf_PLAT094_2bisAP-beta_0kPa    
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       4.35 Report
RESPONSE: The presence of high-resolution diffraction data
revealed high positive residual density on electron-rich double bonds,
which could not be described by a spherical approximation of electron density.
;
# end Validation Reply Form
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2bisAP-alpha_0kPa
_database_code_depnum_ccdc_archive 'CCDC 2039413'
loop_
_audit_author_name
_audit_author_address
'Daniel Tchon'
;Faculty of Chemistry, University of Warsaw
Poland
;
_audit_update_record             
;
2020-10-19 deposited with the CCDC.	2021-01-21 downloaded from the CCDC.
;
_audit_creation_date             2020-03-24
_audit_creation_method           
;
Olex2 1.2
(compiled May 29 2018 13:30:08 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            1,1'-Pyrene-1,8-diyldiethanone
_chemical_name_systematic        1,8-Diacetylpyrene
_chemical_formula_moiety         'C20 H14 O2'
_chemical_formula_sum            'C20 H14 O2'
_chemical_formula_weight         286.31
_chemical_melting_point          435
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                   8.13770(10)
_cell_length_b                   22.9058(3)
_cell_length_c                   7.23590(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.7010(10)
_cell_angle_gamma                90
_cell_volume                     1345.96(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    29567
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      53.3960
_cell_measurement_theta_min      2.6470
_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  0.694
_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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_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
-1 0 0 0.1298
1 0 0 0.1308
0 2 1 0.0663
0 -2 -1 0.0663
0 2 -1 0.0706
0 -2 1 0.0656
0 1 0 0.0938
0 -1 0 0.0948

_exptl_crystal_recrystallization_method 'from acetonitrile at room temperature'
_exptl_crystal_size_max          0.271
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.133
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       51
_diffrn_reflns_limit_k_min       -51
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            115754
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         53.515
_diffrn_reflns_theta_min         1.778
_diffrn_ambient_temperature      100.00(10)
_diffrn_ambient_pressure         0
_diffrn_ambient_environment      air
_diffrn_detector_area_resol_mean 8.0013
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -11.00  79.00   1.00    4.00    --   10.00  57.00   0.00   90
  2  ω    -31.00  59.00   1.00    4.00    --  -10.00  57.00   0.00   90
  3  ω    -99.00  -9.00   1.00   16.00    --  -30.00 -57.00-180.00   90
  4  ω   -100.00 -51.00   1.00   16.00    --  -30.00-159.00 -64.00   49
  5  ω    -51.00  39.00   1.00   16.00    --  -30.00  57.00   0.00   90
  6  ω    -36.00  64.00   1.00   16.00    --   33.82 -77.00 150.00  100
  7  ω     13.00 103.00   1.00   16.00    --   33.82  57.00 -60.00   90
  8  ω      4.00 104.00   1.00   16.00    --   33.82  77.00-180.00  100
  9  ω      4.00 104.00   1.00   16.00    --   33.82  77.00  60.00  100
 10  ω      4.00 104.00   1.00   16.00    --   33.82  77.00 -30.00  100
 11  ω      2.00 114.00   1.00   60.00    --   73.57-118.00  89.00  112
 12  ω      1.00 103.00   1.00   60.00    --   73.57 -30.00-180.00  102
 13  ω      2.00 109.00   1.00   60.00    --   73.57 -94.00 -30.00  107
 14  ω     44.00 146.00   1.00   60.00    --   73.57  30.00   0.00  102
 15  ω     73.00 145.00   1.00   60.00    --   73.57 125.00 150.00   72
 16  ω      2.00 109.00   1.00   60.00    --   73.57 -94.00  90.00  107
 17  ω     52.00 142.00   1.00   60.00    --   73.57  61.00  90.00   90
 18  ω      2.00 109.00   1.00   60.00    --   73.57 -94.00-150.00  107
 19  ω      2.00  97.00   1.00   60.00    --   73.57 -45.00  60.00   95
 20  ω      3.00 104.00   1.00   60.00    --   73.57 -77.00-120.00  101
 21  ω     44.00 144.00   1.00   60.00    --   73.57  77.00  30.00  100
 22  ω     44.00 144.00   1.00   60.00    --   73.57  77.00 -60.00  100
 23  ω     44.00 129.00   1.00   60.00    --   73.57  77.00 -90.00   85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_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                13010
_reflns_number_total             16246
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.679
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         16246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0590
_refine_ls_restrained_S_all      1.136
_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)+(0.0646P)²+0.1982P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1452
_refine_ls_wR_factor_ref         0.1535
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C18(H18B,H18A,H18C), C20(H20B,H20A,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.09826(5) 0.24718(2) 0.43209(7) 0.01767(7) Uani 1 1 d . . . . .
O2 O 0.07424(6) 0.52107(2) 0.75482(9) 0.02428(10) Uani 1 1 d . . . . .
C1 C 0.35994(5) 0.26019(2) 0.59478(6) 0.01091(5) Uani 1 1 d . . . . .
C2 C 0.35665(5) 0.32172(2) 0.61976(6) 0.00957(5) Uani 1 1 d . . . . .
C3 C 0.21050(5) 0.35648(2) 0.58952(6) 0.01120(6) Uani 1 1 d . . . . .
H3 H 0.1129 0.3384 0.5468 0.013 Uiso 1 1 calc R . . . .
C4 C 0.21052(5) 0.41514(2) 0.62156(6) 0.01148(6) Uani 1 1 d . . . . .
H4 H 0.1132 0.4360 0.5995 0.014 Uiso 1 1 calc R . . . .
C5 C 0.35663(5) 0.44559(2) 0.68836(6) 0.00978(5) Uani 1 1 d . . . . .
C6 C 0.36078(5) 0.50652(2) 0.72487(6) 0.01095(5) Uani 1 1 d . . . . .
C7 C 0.51187(6) 0.53353(2) 0.77275(7) 0.01317(6) Uani 1 1 d . . . . .
H7 H 0.5148 0.5738 0.7898 0.016 Uiso 1 1 calc R . . . .
C8 C 0.65734(6) 0.50202(2) 0.79547(7) 0.01320(6) Uani 1 1 d . . . . .
H8 H 0.7559 0.5211 0.8277 0.016 Uiso 1 1 calc R . . . .
C9 C 0.65590(5) 0.44134(2) 0.76992(6) 0.01079(5) Uani 1 1 d . . . . .
C10 C 0.80425(5) 0.40769(2) 0.79969(7) 0.01307(6) Uani 1 1 d . . . . .
H10 H 0.9023 0.4263 0.8371 0.016 Uiso 1 1 calc R . . . .
C11 C 0.80292(5) 0.34891(2) 0.77376(7) 0.01310(6) Uani 1 1 d . . . . .
H11 H 0.8998 0.3278 0.7954 0.016 Uiso 1 1 calc R . . . .
C12 C 0.65398(5) 0.31904(2) 0.71353(6) 0.01086(5) Uani 1 1 d . . . . .
C13 C 0.65321(6) 0.25851(2) 0.68639(7) 0.01351(6) Uani 1 1 d . . . . .
H13 H 0.7504 0.2374 0.7057 0.016 Uiso 1 1 calc R . . . .
C14 C 0.50811(6) 0.22997(2) 0.63082(7) 0.01340(6) Uani 1 1 d . . . . .
H14 H 0.5092 0.1896 0.6171 0.016 Uiso 1 1 calc R . . . .
C15 C 0.50464(5) 0.35106(2) 0.68189(6) 0.00935(5) Uani 1 1 d . . . . .
C16 C 0.50513(5) 0.41282(2) 0.71340(6) 0.00930(5) Uani 1 1 d . . . . .
C17 C 0.21060(6) 0.22580(2) 0.52993(6) 0.01228(6) Uani 1 1 d . . . . .
C18 C 0.20389(7) 0.16214(2) 0.58504(7) 0.01579(7) Uani 1 1 d . . . . .
H18B H 0.0919 0.1487 0.5726 0.024 Uiso 1 1 calc GR . . . .
H18A H 0.2459 0.1578 0.7114 0.024 Uiso 1 1 calc GR . . . .
H18C H 0.2696 0.1395 0.5061 0.024 Uiso 1 1 calc GR . . . .
C19 C 0.20757(6) 0.54257(2) 0.72680(7) 0.01326(6) Uani 1 1 d . . . . .
C20 C 0.22086(7) 0.60790(2) 0.70448(8) 0.01572(7) Uani 1 1 d . . . . .
H20B H 0.1165 0.6233 0.6582 0.024 Uiso 1 1 calc GR . . . .
H20A H 0.3027 0.6166 0.6188 0.024 Uiso 1 1 calc GR . . . .
H20C H 0.2518 0.6253 0.8223 0.024 Uiso 1 1 calc GR . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.01543(14) 0.01488(13) 0.02172(17) -0.00070(11) -0.00640(12) -0.00139(11)
O2 0.01141(14) 0.01537(14) 0.0467(3) -0.00444(16) 0.00687(16) -0.00074(11)
C1 0.01013(13) 0.01091(12) 0.01166(13) -0.00048(10) 0.00036(10) -0.00029(10)
C2 0.00814(11) 0.01054(12) 0.00998(12) -0.00002(9) 0.00019(9) -0.00021(9)
C3 0.00813(12) 0.01158(13) 0.01370(14) -0.00111(10) -0.00079(10) -0.00017(9)
C4 0.00815(12) 0.01155(12) 0.01452(14) -0.00056(11) -0.00095(10) 0.00033(10)
C5 0.00834(11) 0.01026(11) 0.01069(12) 0.00042(9) 0.00034(9) -0.00040(9)
C6 0.00947(12) 0.01049(12) 0.01291(14) 0.00045(10) 0.00075(10) -0.00029(9)
C7 0.01115(14) 0.01123(13) 0.01708(16) -0.00017(11) 0.00052(11) -0.00183(10)
C8 0.00985(13) 0.01287(14) 0.01676(16) -0.00037(12) 0.00002(11) -0.00245(10)
C9 0.00811(12) 0.01249(13) 0.01168(13) 0.00040(10) 0.00004(9) -0.00116(9)
C10 0.00783(12) 0.01577(15) 0.01540(15) 0.00029(12) -0.00082(10) -0.00073(10)
C11 0.00829(12) 0.01544(15) 0.01535(15) 0.00074(12) -0.00083(11) 0.00083(11)
C12 0.00836(12) 0.01234(13) 0.01181(13) 0.00069(10) 0.00008(9) 0.00068(10)
C13 0.01052(14) 0.01283(14) 0.01706(16) 0.00024(12) -0.00002(11) 0.00218(11)
C14 0.01219(15) 0.01159(13) 0.01629(16) -0.00067(11) -0.00001(12) 0.00132(11)
C15 0.00783(11) 0.01047(11) 0.00973(12) 0.00036(9) 0.00046(9) -0.00005(9)
C16 0.00776(11) 0.01047(11) 0.00965(12) 0.00059(9) 0.00032(9) -0.00059(9)
C17 0.01215(14) 0.01195(13) 0.01264(14) -0.00115(11) 0.00005(11) -0.00150(11)
C18 0.01821(18) 0.01321(15) 0.01575(16) 0.00068(12) -0.00045(13) -0.00337(13)
C19 0.01109(14) 0.01167(13) 0.01700(16) -0.00076(12) 0.00081(11) 0.00051(11)
C20 0.01726(18) 0.01207(14) 0.01796(18) 0.00176(13) 0.00218(14) 0.00206(12)

_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 1.2219(6) . ?
O2 C19 1.2203(7) . ?
C1 C2 1.4215(6) . ?
C1 C14 1.4002(6) . ?
C1 C17 1.4980(6) . ?
C2 C3 1.4361(6) . ?
C2 C15 1.4262(6) . ?
C3 C4 1.3636(6) . ?
C4 C5 1.4351(6) . ?
C5 C6 1.4203(6) . ?
C5 C16 1.4243(6) . ?
C6 C7 1.3998(6) . ?
C6 C19 1.4963(6) . ?
C7 C8 1.3872(7) . ?
C8 C9 1.4021(6) . ?
C9 C10 1.4367(6) . ?
C9 C16 1.4263(6) . ?
C10 C11 1.3595(7) . ?
C11 C12 1.4349(6) . ?
C12 C13 1.4001(6) . ?
C12 C15 1.4253(6) . ?
C13 C14 1.3864(7) . ?
C15 C16 1.4329(6) . ?
C17 C18 1.5137(7) . ?
C19 C20 1.5099(7) . ?

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 C17 122.66(4) . . ?
C14 C1 C2 119.31(4) . . ?
C14 C1 C17 118.02(4) . . ?
C1 C2 C3 123.54(4) . . ?
C1 C2 C15 119.00(4) . . ?
C15 C2 C3 117.45(4) . . ?
C4 C3 C2 121.96(4) . . ?
C3 C4 C5 121.82(4) . . ?
C6 C5 C4 123.33(4) . . ?
C6 C5 C16 118.97(4) . . ?
C16 C5 C4 117.67(4) . . ?
C5 C6 C19 122.28(4) . . ?
C7 C6 C5 119.36(4) . . ?
C7 C6 C19 118.22(4) . . ?
C8 C7 C6 121.91(4) . . ?
C7 C8 C9 120.03(4) . . ?
C8 C9 C10 120.81(4) . . ?
C8 C9 C16 119.44(4) . . ?
C16 C9 C10 119.75(4) . . ?
C11 C10 C9 120.77(4) . . ?
C10 C11 C12 120.88(4) . . ?
C13 C12 C11 120.71(4) . . ?
C13 C12 C15 119.41(4) . . ?
C15 C12 C11 119.88(4) . . ?
C14 C13 C12 120.24(4) . . ?
C13 C14 C1 121.86(4) . . ?
C2 C15 C16 120.60(4) . . ?
C12 C15 C2 120.13(4) . . ?
C12 C15 C16 119.27(4) . . ?
C5 C16 C9 120.15(4) . . ?
C5 C16 C15 120.43(4) . . ?
C9 C16 C15 119.43(4) . . ?
O1 C17 C1 122.16(4) . . ?
O1 C17 C18 120.02(4) . . ?
C1 C17 C18 117.80(4) . . ?
O2 C19 C6 121.96(4) . . ?
O2 C19 C20 119.23(5) . . ?
C6 C19 C20 118.72(4) . . ?

_iucr_refine_instructions_details 
;
TITL 500f9a_r1-23_abs_a.res in P2(1)/c
REM Old TITL 500F9a_r1-23_abs in P21/c #14
REM SHELXT solution in P2(1)/c: R1 0.108, Rweak 0.070, Alpha 0.023
REM <I/s> 1.368 for 84 systematic absences, Orientation as input
REM Formula found by SHELXT: C20 O2
CELL 0.71073 8.1377 22.9058 7.2359 90 93.701 90
ZERR 4 0.0001 0.0003 0.0001 0 0.001 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H O
UNIT 80 56 8
 
L.S. 4 0 0
PLAN  8
BOND
list 4
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%./500f9a_r1-23_abs.hkl">
REM </olex2.extras>
 
WGHT    0.064600    0.198200
FVAR       0.99704
O1    3    0.098261    0.247179    0.432092    11.00000    0.01543    0.01488 =
         0.02172   -0.00070   -0.00640   -0.00139
O2    3    0.074236    0.521074    0.754820    11.00000    0.01141    0.01537 =
         0.04670   -0.00444    0.00687   -0.00074
C1    1    0.359938    0.260188    0.594783    11.00000    0.01013    0.01091 =
         0.01166   -0.00048    0.00036   -0.00029
C2    1    0.356647    0.321724    0.619761    11.00000    0.00814    0.01054 =
         0.00998   -0.00002    0.00019   -0.00021
C3    1    0.210501    0.356478    0.589519    11.00000    0.00813    0.01158 =
         0.01370   -0.00111   -0.00079   -0.00017
AFIX  43
H3    2    0.112941    0.338437    0.546810    11.00000   -1.20000
AFIX   0
C4    1    0.210524    0.415141    0.621561    11.00000    0.00815    0.01155 =
         0.01452   -0.00056   -0.00095    0.00033
AFIX  43
H4    2    0.113170    0.435993    0.599516    11.00000   -1.20000
AFIX   0
C5    1    0.356627    0.445595    0.688362    11.00000    0.00834    0.01026 =
         0.01069    0.00042    0.00034   -0.00040
C6    1    0.360784    0.506517    0.724874    11.00000    0.00947    0.01049 =
         0.01291    0.00045    0.00075   -0.00029
C7    1    0.511872    0.533529    0.772749    11.00000    0.01115    0.01123 =
         0.01708   -0.00017    0.00052   -0.00183
AFIX  43
H7    2    0.514808    0.573766    0.789813    11.00000   -1.20000
AFIX   0
C8    1    0.657341    0.502018    0.795474    11.00000    0.00985    0.01287 =
         0.01676   -0.00037    0.00002   -0.00245
AFIX  43
H8    2    0.755859    0.521147    0.827672    11.00000   -1.20000
AFIX   0
C9    1    0.655903    0.441338    0.769919    11.00000    0.00811    0.01249 =
         0.01168    0.00040    0.00004   -0.00116
C10   1    0.804249    0.407691    0.799688    11.00000    0.00783    0.01577 =
         0.01540    0.00029   -0.00082   -0.00073
AFIX  43
H10   2    0.902320    0.426341    0.837125    11.00000   -1.20000
AFIX   0
C11   1    0.802923    0.348906    0.773765    11.00000    0.00829    0.01544 =
         0.01535    0.00074   -0.00083    0.00083
AFIX  43
H11   2    0.899837    0.327769    0.795361    11.00000   -1.20000
AFIX   0
C12   1    0.653978    0.319039    0.713525    11.00000    0.00836    0.01234 =
         0.01181    0.00069    0.00008    0.00068
C13   1    0.653211    0.258514    0.686392    11.00000    0.01052    0.01283 =
         0.01706    0.00024   -0.00002    0.00218
AFIX  43
H13   2    0.750391    0.237385    0.705715    11.00000   -1.20000
AFIX   0
C14   1    0.508115    0.229966    0.630824    11.00000    0.01219    0.01159 =
         0.01629   -0.00067   -0.00001    0.00132
AFIX  43
H14   2    0.509233    0.189601    0.617099    11.00000   -1.20000
AFIX   0
C15   1    0.504636    0.351062    0.681887    11.00000    0.00783    0.01047 =
         0.00973    0.00036    0.00046   -0.00005
C16   1    0.505134    0.412822    0.713398    11.00000    0.00776    0.01047 =
         0.00965    0.00059    0.00032   -0.00059
C17   1    0.210599    0.225800    0.529927    11.00000    0.01215    0.01195 =
         0.01264   -0.00115    0.00005   -0.00150
C18   1    0.203888    0.162136    0.585041    11.00000    0.01821    0.01321 =
         0.01575    0.00068   -0.00045   -0.00337
AFIX 137
H18B  2    0.091934    0.148744    0.572632    11.00000   -1.50000
H18A  2    0.245859    0.157822    0.711363    11.00000   -1.50000
H18C  2    0.269614    0.139466    0.506082    11.00000   -1.50000
AFIX   0
C19   1    0.207569    0.542567    0.726798    11.00000    0.01109    0.01167 =
         0.01700   -0.00076    0.00081    0.00051
C20   1    0.220861    0.607903    0.704485    11.00000    0.01726    0.01207 =
         0.01796    0.00176    0.00218    0.00206
AFIX 137
H20B  2    0.116461    0.623289    0.658156    11.00000   -1.50000
H20A  2    0.302732    0.616647    0.618813    11.00000   -1.50000
H20C  2    0.251841    0.625314    0.822298    11.00000   -1.50000
AFIX   0
HKLF 4
 
REM  500f9a_r1-23_abs_a.res in P2(1)/c
REM R1 =  0.0590 for   13010 Fo > 4sig(Fo)  and  0.0752 for all   16246 data
REM    201 parameters refined using      0 restraints
 
END  
     
WGHT      0.0643      0.1992 

REM Highest difference peak  1.679,  deepest hole -0.335,  1-sigma level  0.079
Q1    1   0.7987  0.3803  0.7823  11.00000  0.05    1.68
Q2    1   0.2210  0.3830  0.5988  11.00000  0.05    0.88
Q3    1   0.6581  0.2840  0.6936  11.00000  0.05    0.69
Q4    1   0.5070  0.3807  0.7015  11.00000  0.05    0.61
Q5    1   0.1580  0.2393  0.4841  11.00000  0.05    0.61
Q6    1   0.5928  0.5189  0.7853  11.00000  0.05    0.58
Q7    1   0.6638  0.4741  0.7795  11.00000  0.05    0.56
Q8    1   0.5773  0.2422  0.6570  11.00000  0.05    0.55

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0590 for 13010 Fo > 4sig(Fo) and 0.0752 for all 116769 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 1.68, deepest hole -0.33
  REM Mean Shift 0, Max Shift -0.001.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0752
  REM R1_gt = 0.0590
  REM wR_ref = 0.1535
  REM GOOF = 1.136
  REM Shift_max = -0.001
  REM Shift_mean = 0
  REM Reflections_all = 116769
  REM Reflections_gt = 13010
  REM Parameters = n/a
  REM Hole = -0.33
  REM Peak = 1.68
  REM Flack = n/a

  
;
_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_DIFMX02_2bisAP-alpha_0kPa   
;
PROBLEM: The maximum difference density is > 0.1*ZMAX*0.75
RESPONSE: The presence of high-resolution diffraction data
revealed high positive residual density on electron-rich double bonds,
which could not be described by a spherical approximation of electron density.
;
_vrf_PLAT097_2bisAP-alpha_0kPa   
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       1.68 eA-3  
RESPONSE: The presence of high-resolution diffraction data
revealed high positive residual density on electron-rich double bonds,
which could not be described by a spherical approximation of electron density.
;
_vrf_PLAT094_2bisAP-alpha_0kPa   
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       5.01 Report
RESPONSE: The presence of high-resolution diffraction data
revealed high positive residual density on electron-rich double bonds,
which could not be described by a spherical approximation of electron density.
;
# end Validation Reply Form
_exptl_crystal_preparation       Luminescent
