#------------------------------------------------------------------------------
#$Date: 2021-10-16 05:10:36 +0300 (Sat, 16 Oct 2021) $
#$Revision: 269978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/49/1564944.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1564944
loop_
_publ_author_name
'Tchoń, D.'
'Makal, A.'
_publ_section_title
;
 Maximizing completeness in single-crystal high-pressure diffraction
 experiments: phase transitions in 2{^i̧rc}AP
;
_journal_issue                   6
_journal_name_full               IUCrJ
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2052252521009532
_journal_volume                  8
_journal_year                    2021
_chemical_formula_moiety         'C20 H14 O2'
_chemical_formula_sum            'C20 H14 O2'
_chemical_formula_weight         286.333
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_Int_Tables_number      62
_audit_creation_date             2021-06-15
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2021.06.11 svn.re2ff6fc for OlexSys, GUI svn.r6348)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.15(1)
_cell_length_b                   16.17(3)
_cell_length_c                   11.288(9)
_cell_measurement_reflns_used    170
_cell_measurement_temperature    295.4(6)
_cell_measurement_theta_max      26.6510
_cell_measurement_theta_min      3.6030
_cell_volume                     1305(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement
'olex2.refine 1.5-alpha (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      'Diamond Anvil Cell filled with parabar oil'
_diffrn_ambient_pressure         520500
_diffrn_ambient_temperature      295.4(6)
_diffrn_crystal_treatment
'Pressurized slowly in parabar oil as a hydrostatic medium.'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9182
_diffrn_measured_fraction_theta_max 0.8061
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -37.00  33.00   1.00   80.00    --    6.97 -53.00-162.00   70
  2  ω    -46.00  35.00   1.00   80.00    --    6.97 -26.00   7.00   81
  3  ω    -53.00  50.00   1.00   80.00    --    6.97  13.00  -3.00  103
  4  ω    -20.00   6.00   1.00   80.00    --    6.97 -19.00-180.00   26
  5  ω     19.00  44.00   1.00   80.00    --    6.97 -19.00-180.00   25
  6  ω    -30.00  -4.00   1.00   80.00    --    6.97  19.00-180.00   26
  7  ω     -8.00  24.00   1.00   80.00    --    6.97  81.00 -29.00   32
  8  ω    -19.00   7.00   1.00   80.00    --   -8.77 -97.00-143.00   26
  9  ω    -35.00 -12.00   1.00   80.00    --   -8.77  57.00 -60.00   23
 10  ω    -35.00 -12.00   1.00  320.00    --   -8.77  57.00 120.00   23
 11  ω    -69.00 -30.00   1.00  320.00    --   -8.77 135.00 123.00   39
 12  ω    -19.00  17.00   1.00  320.00    --   -8.77 -97.00  35.00   36
 13  ω      5.00  31.00   1.00  320.00    --   -8.77 -99.00  60.00   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 55 degrees'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0719
_diffrn_reflns_av_unetI/netI     0.0727
_diffrn_reflns_Laue_measured_fraction_full 0.9182
_diffrn_reflns_Laue_measured_fraction_max 0.8061
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            1411
_diffrn_reflns_point_group_measured_fraction_full 0.9182
_diffrn_reflns_point_group_measured_fraction_max 0.8061
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         28.74
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
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_primary    yellow
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_description       block
_exptl_crystal_F_000             600.297
_exptl_crystal_preparation
'Mounted in a Diamond-Anvil Cell using parabar oil as pressure medium.'
_exptl_crystal_pressure_history
'Pressurized to 0.5 GPa and left to stabilize over 24 hours.'
_exptl_crystal_size_max          0.205
_exptl_crystal_size_mid          0.152
_exptl_crystal_size_min          0.118
_refine_diff_density_max         0.3988
_refine_diff_density_min         -0.3837
_refine_diff_density_rms         0.0951
_refine_ls_d_res_high            0.7390
_refine_ls_d_res_low             9.2559
_refine_ls_extinction_coef       0.0075(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   0.9283
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     173
_refine_ls_number_reflns         1409
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.9283
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0341
_refine_ls_shift/su_max          -0.0004
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0031P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0487
_refine_ls_wR_factor_ref         0.0602
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              21
_reflns_limit_k_min              -21
_reflns_limit_l_max              12
_reflns_limit_l_min              -13
_reflns_number_gt                845
_reflns_number_total             1409
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            fc5056.cif
_cod_data_source_block           2oAPal_5kbar
_cod_database_code               1564944
_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
;
_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
;
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z+1/2
3 -x,y+1/2,-z
4 -x+1/2,-y,z+1/2
5 -x,-y,-z
6 -x-1/2,y-1/2,z-1/2
7 x,-y-1/2,z
8 x-1/2,y,-z-1/2
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
O1 O 0.48195(14) 0.53844(4) 0.77605(7) 0.0527(4) Uani 1.000000 1 . . .
C1 C 0.58150(17) 0.67496(5) 0.74280(9) 0.0270(3) Uani 1.000000 1 . . .
C2 C 0.60748(17) 0.67375(5) 0.61754(9) 0.0264(3) Uani 1.000000 1 . . .
C3 C 0.6239(2) 0.59900(7) 0.55040(13) 0.0327(4) Uani 1.000000 1 . . .
H3 H 0.6136(19) 0.5434(6) 0.5963(11) 0.057(4) Uani 1.000000 1 . . .
C4 C 0.6507(2) 0.60005(7) 0.43089(12) 0.0346(4) Uani 1.000000 1 . . .
H4 H 0.6604(18) 0.5445(7) 0.3819(11) 0.058(4) Uani 1.000000 1 . . .
C5 C 0.66706(18) 0.67512(6) 0.36664(10) 0.0314(3) Uani 1.000000 1 . . .
C6 C 0.6948(2) 0.67626(8) 0.24312(12) 0.0400(4) Uani 1.000000 1 . . .
H6 H 0.7065(19) 0.6195(7) 0.1968(9) 0.066(5) Uani 1.000000 1 . . .
C7 C 0.7085(3) 0.75 0.18222(17) 0.0430(6) Uani 1.000000 2 S T P
H7 H 0.732(3) 0.75 0.0864(17) 0.083(8) Uani 1.000000 2 S T P
C14 C 0.5740(3) 0.75 0.80156(15) 0.0279(5) Uani 1.000000 2 S T P
H14 H 0.555(2) 0.75 0.8955(13) 0.044(6) Uani 1.000000 2 S T P
C15 C 0.6230(2) 0.75 0.55602(13) 0.0247(4) Uani 1.000000 2 S T P
C16 C 0.6538(2) 0.75 0.43011(13) 0.0270(4) Uani 1.000000 2 S T P
C17 C 0.55536(18) 0.59944(6) 0.81610(10) 0.0321(4) Uani 1.000000 1 . . .
C18 C 0.6179(3) 0.60176(10) 0.94416(17) 0.0382(4) Uani 1.000000 1 . . .
H18a H 0.741(3) 0.6291(13) 0.9526(15) 0.085(7) Uani 1.000000 1 . . .
H18b H 0.522(3) 0.6386(11) 0.9949(12) 0.080(6) Uani 1.000000 1 . . .
H18c H 0.613(3) 0.5416(9) 0.9810(12) 0.096(6) Uani 1.000000 1 . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0396
-7 -15 -7 0.0974
0 1 0 0.0781
0 1 -1 0.0525
10 -3 3 0.0916
9 -2 6 0.0881
0 -1 -1 0.0708
-1 -1 1 0.0580
0 -1 1 0.0674
0 1 1 0.0592
-1 1 1 0.0425
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
C14 C1 C2 119.49(10) . . ?
C17 C1 C2 123.83(9) . . ?
C17 C1 C14 116.66(10) . . ?
C3 C2 C1 123.17(10) . . ?
C15 C2 C1 118.90(10) . . ?
C15 C2 C3 117.91(11) . . ?
H3 C3 C2 117.4(6) . . ?
C4 C3 C2 121.67(11) . . ?
C4 C3 H3 120.9(6) . . ?
H4 C4 C3 121.1(7) . . ?
C5 C4 C3 121.89(11) . . ?
C5 C4 H4 117.0(7) . . ?
C6 C5 C4 121.92(10) . . ?
C16 C5 C4 118.00(11) . . ?
C16 C5 C6 120.08(11) . . ?
H6 C6 C5 119.2(6) . . ?
C7 C6 C5 120.96(13) . . ?
C7 C6 H6 119.8(6) . . ?
C6 C7 C6 119.57(19) 7_575 . ?
H7 C7 C6 120.21(10) . 7_575 ?
H7 C7 C6 120.21(10) . . ?
C1 C14 C1 122.52(15) 7_575 . ?
H14 C14 C1 118.70(8) . 7_575 ?
H14 C14 C1 118.70(8) . . ?
C2 C15 C2 120.60(14) 7_575 . ?
C16 C15 C2 119.70(7) . . ?
C16 C15 C2 119.70(7) . 7_575 ?
C5 C16 C5 118.34(14) 7_575 . ?
C15 C16 C5 120.82(7) . . ?
C15 C16 C5 120.82(7) . 7_575 ?
C1 C17 O1 121.21(11) . . ?
C18 C17 O1 120.47(11) . . ?
C18 C17 C1 118.29(11) . . ?
H18a C18 C17 111.5(10) . . ?
H18b C18 C17 109.5(9) . . ?
H18b C18 H18a 105.7(12) . . ?
H18c C18 C17 110.1(8) . . ?
H18c C18 H18a 113.5(13) . . ?
H18c C18 H18b 106.3(11) . . ?
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 1.2054(18) . ?
C1 C2 1.4261(18) . ?
C1 C14 1.384(2) . ?
C1 C17 1.487(2) . ?
C2 C3 1.432(2) . ?
C2 C15 1.420(2) . ?
C3 H3 1.041(12) . ?
C3 C4 1.363(2) . ?
C4 H4 1.058(11) . ?
C4 C5 1.419(2) . ?
C5 C6 1.408(2) . ?
C5 C16 1.410(2) . ?
C6 H6 1.061(11) . ?
C6 C7 1.380(2) . ?
C7 H7 1.094(18) . ?
C14 H14 1.069(14) . ?
C15 C16 1.438(2) . ?
C17 C18 1.513(2) . ?
C18 H18a 0.993(19) . ?
C18 H18b 1.075(16) . ?
C18 H18c 1.058(14) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C17 C1 C2 -30.07(15) . . . . ?
O1 C17 C1 C14 147.97(14) . . . . ?
C1 C2 C3 C4 -179.25(12) . . . . ?
C1 C2 C15 C2 -1.84(7) . . . 7_575 ?
C1 C2 C15 C16 178.52(12) . . . . ?
C1 C14 C1 C2 -3.3(2) . . 7_575 7_575 ?
C1 C14 C1 C17 174.83(16) . . 7_575 7_575 ?
C2 C3 C4 C5 1.08(16) . . . . ?
C2 C15 C2 C3 -179.81(15) . . 7_575 7_575 ?
C2 C15 C16 C5 0.55(17) . . . . ?
C2 C15 C16 C5 179.09(13) . . . 7_575 ?
C3 C4 C5 C6 -179.98(13) . . . . ?
C3 C4 C5 C16 -0.32(17) . . . . ?
C4 C5 C6 C7 179.36(16) . . . . ?
C4 C5 C16 C5 -179.06(15) . . . 7_575 ?
C4 C5 C16 C15 -0.49(15) . . . . ?
C5 C6 C7 C6 -0.04(9) . . . 7_575 ?
C5 C16 C5 C6 -0.60(18) . . 7_575 7_575 ?
