#------------------------------------------------------------------------------
#$Date: 2024-12-06 22:51:08 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296710 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/91/7249113.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7249113
loop_
_publ_author_name
'Hoser, Anna'
'Zwolenik, Aleksandra'
'Makal, Anna'
_publ_section_title
;
 On the importance of low-frequency modes in predicting pressure-induced
 phase transitions.
;
_journal_issue                   31
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              20745
_journal_page_last               20749
_journal_paper_doi               10.1039/d4cp02368d
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C20 H14 O2'
_chemical_formula_sum            'C20 H14 O2'
_chemical_formula_weight         286.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-01-27
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2023.11.24 svn.r209d9fb for OlexSys, GUI svn.r6869)
;
_audit_update_record
;
2024-02-13 deposited with the CCDC.	2024-07-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.8945(19)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.2316(2)
_cell_length_b                   7.44094(15)
_cell_length_c                   10.0891(2)
_cell_measurement_reflns_used    2775
_cell_measurement_temperature    280.10(10)
_cell_measurement_theta_max      76.3550
_cell_measurement_theta_min      7.0480
_cell_volume                     684.70(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.43d (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43d (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43d (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      280.10(10)
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -91.00 -53.00   0.50    0.40    --    0.00-178.00-150.00   76
  2  ω    -35.00  33.00   0.50    0.40    --    0.00  57.00  90.00  136
  3  ω     48.00  80.00   0.50    0.40    --    0.00  57.00  90.00   64
  4  ω      0.00  25.00   0.50    0.40    --    0.00 -99.00  90.00   50
  5  ω     22.00  49.00   0.50    0.40    --    0.00 -99.00 -90.00   54
  6  ω     27.00  67.00   0.50    1.40    --   66.49  45.00-180.00   80
  7  ω    -26.00   3.00   0.50    1.40    --   66.49 -15.00-150.00   58
  8  ω     -7.00 110.00   0.50    1.40    --   66.49 -45.00-150.00  234
  9  ω     49.00  92.00   0.50    1.40    --   66.49-125.00  30.00   86
 10  ω     16.00 155.00   0.50    1.40    --   66.49 -15.00-150.00  278
 11  ω     34.00 102.00   0.50    1.40    --   66.49-125.00 120.00  136
 12  ω     98.00 129.00   0.50    1.40    --   66.49  45.00-180.00   62
 13  ω    -16.00  49.00   0.50    1.40    --   66.49 -77.00  90.00  130
 14  ω    114.00 145.00   0.50    1.40    --   66.49 125.00 120.00   62
 15  ω     96.00 122.00   0.50    1.40    --   66.49 125.00-180.00   52
 16  ω     97.00 133.00   0.50    1.40    --   66.49 125.00 -60.00   72
 17  ω     69.00 109.00   0.50    1.40    --   66.49 -77.00  90.00   80
 18  ω     43.00  69.00   0.50    1.40    --  121.75 -91.00  90.00   52
 19  ω     33.00 102.00   0.50    1.40    --  121.75 -91.00  60.00  138
 20  ω     32.00 104.00   0.50    1.40    --  121.75 -91.00-150.00  144
 21  ω     76.00 101.00   0.50    1.40    --  121.75-111.00  30.00   50
 22  ω    132.00 164.00   0.50    1.40    --  121.75 111.00 -90.00   64
 23  ω     82.00 174.00   0.50    1.40    --  121.75  77.00  60.00  184
 24  ω    105.00 150.00   0.50    1.40    --  121.75 111.00   0.00   90
 25  ω     76.00 103.00   0.50    1.40    --  121.75-111.00 150.00   54
 26  ω     78.00 104.00   0.50    1.40    --  121.75 -91.00 -90.00   52
 27  ω     65.00  91.00   0.50    1.40    --  121.75 178.00 -30.00   52
 28  ω     64.00 117.00   0.50    1.40    --  121.75 178.00  60.00  106
 29  ω     71.00 140.00   0.50    1.40    --  121.75  38.00-180.00  138
 30  ω     72.00 101.00   0.50    1.40    --  121.75 -91.00  90.00   58
 31  ω     39.00  74.00   0.50    1.40    --  121.75 -91.00 -90.00   70
 32  ω     93.00 141.00   0.50    1.40    --  121.75  63.00 -60.00   96
 33  ω     79.00 178.00   0.50    1.40    --  121.75  38.00   0.00  198
 34  ω     68.00 159.00   0.50    1.40    --  121.75 -50.00 -90.00  182
 35  ω     72.00 108.00   0.50    1.40    --  121.75-111.00-180.00   72
 36  ω     86.00 156.00   0.50    1.40    --  121.75  63.00-180.00  140
 37  ω     45.00  71.00   0.50    1.40    --  121.75-111.00 -90.00   52
 38  ω     80.00 105.00   0.50    1.40    --  121.75-111.00 -90.00   50
 39  ω     63.00 106.00   0.50    1.40    --  121.75-111.00-150.00   86
 40  ω     62.00 108.00   0.50    1.40    --  121.75-111.00 -30.00   92
 41  ω    108.00 166.00   0.50    1.40    --  121.75 111.00-120.00  116
 42  ω     80.00 107.00   0.50    1.40    --  121.75-103.00  29.27   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5826
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.510
_diffrn_reflns_theta_min         6.049
_exptl_absorpt_coefficient_mu    0.705
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79246
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.43d (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1450
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0467
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0833P)²+0.1385P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1430
_refine_ls_wR_factor_ref         0.1462
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1292
_reflns_number_total             1450
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cp02368d2.cif
_cod_data_source_block           2papa_rt
_cod_depositor_comments
'Adding full bibliography for 7249110--7249118.cif.'
_cod_original_cell_volume        684.71(2)
_cod_database_code               7249113
_shelxl_version_number           2013-2
_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.
;
_shelx_estimated_absorpt_t_max   0.884
_shelx_estimated_absorpt_t_min   0.806
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.63814(12) 0.33977(19) 0.07319(11) 0.0554(4) Uani 1 1 d . . . . .
C17 C 0.73489(16) 0.3975(2) 0.15757(14) 0.0401(4) Uani 1 1 d . . . . .
C18 C 0.87984(18) 0.4524(2) 0.11874(17) 0.0494(4) Uani 1 1 d . . . . .
H18A H 0.9629 0.3547 0.1569 0.074 Uiso 1 1 calc R U . . .
H18B H 0.9110 0.5832 0.1610 0.074 Uiso 1 1 calc R U . . .
H18C H 0.8698 0.4588 0.0105 0.074 Uiso 1 1 calc R U . . .
C1 C 0.71523(15) 0.41463(19) 0.30192(14) 0.0365(3) Uani 1 1 d . . . . .
C2 C 0.57901(14) 0.46566(18) 0.33923(13) 0.0339(3) Uani 1 1 d . . . . .
C10 C 0.45410(15) 0.5192(2) 0.24384(14) 0.0390(4) Uani 1 1 d . . . . .
H10 H 0.4612 0.5170 0.1383 0.047 Uiso 1 1 calc R U . . .
C11 C 0.67204(15) 0.4277(2) 0.71538(14) 0.0411(4) Uani 1 1 d . . . . .
H11 H 0.7628 0.3871 0.7896 0.049 Uiso 1 1 calc R U . . .
C12 C 0.68851(14) 0.42389(19) 0.57666(14) 0.0363(3) Uani 1 1 d . . . . .
C13 C 0.82066(15) 0.3739(2) 0.53517(15) 0.0410(4) Uani 1 1 d . . . . .
H13 H 0.9129 0.3360 0.6087 0.049 Uiso 1 1 calc R U . . .
C14 C 0.83361(15) 0.3728(2) 0.40085(15) 0.0401(4) Uani 1 1 d . . . . .
H14 H 0.9376 0.3390 0.3715 0.048 Uiso 1 1 calc R U . . .
C15 C 0.56713(14) 0.47256(17) 0.47892(13) 0.0328(3) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C17 C18 120.02(13) . . ?
O1 C17 C1 121.65(13) . . ?
C1 C17 C18 118.33(13) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2 C1 C17 121.69(13) . . ?
C14 C1 C17 118.43(12) . . ?
C14 C1 C2 119.85(13) . . ?
C1 C2 C10 123.23(13) . . ?
C1 C2 C15 118.48(12) . . ?
C15 C2 C10 118.23(12) . . ?
C2 C10 H10 119.5 . . ?
C11 C10 C2 121.06(13) 3_666 . ?
C11 C10 H10 119.5 3_666 . ?
C10 C11 H11 119.0 3_666 . ?
C10 C11 C12 122.00(12) 3_666 . ?
C12 C11 H11 119.0 . . ?
C13 C12 C11 121.80(12) . . ?
C13 C12 C15 119.37(13) . . ?
C15 C12 C11 118.82(12) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.49(12) . . ?
C14 C13 H13 119.8 . . ?
C1 C14 H14 119.2 . . ?
C13 C14 C1 121.60(13) . . ?
C13 C14 H14 119.2 . . ?
C12 C15 C2 120.14(12) . . ?
C12 C15 C15 119.54(15) . 3_666 ?
C15 C15 C2 120.32(15) 3_666 . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C17 1.2132(18) . ?
C17 C18 1.508(2) . ?
C17 C1 1.5006(19) . ?
C18 H18A 1.0831 . ?
C18 H18B 1.0831 . ?
C18 H18C 1.0831 . ?
C1 C2 1.4190(19) . ?
C1 C14 1.396(2) . ?
C2 C10 1.4393(19) . ?
C2 C15 1.4313(18) . ?
C10 H10 1.0770 . ?
C10 C11 1.353(2) 3_666 ?
C11 C10 1.353(2) 3_666 ?
C11 H11 1.0770 . ?
C11 C12 1.4313(19) . ?
C12 C13 1.3999(19) . ?
C12 C15 1.4204(18) . ?
C13 H13 1.0770 . ?
C13 C14 1.379(2) . ?
C14 H14 1.0770 . ?
C15 C15 1.431(3) 3_666 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C17 C1 C2 -36.6(2) . . . . ?
O1 C17 C1 C14 141.13(16) . . . . ?
C17 C1 C2 C10 -5.4(2) . . . . ?
C17 C1 C2 C15 177.67(12) . . . . ?
C17 C1 C14 C13 -175.61(13) . . . . ?
C18 C17 C1 C2 143.97(15) . . . . ?
C18 C17 C1 C14 -38.26(19) . . . . ?
C1 C2 C10 C11 -177.85(13) . . . 3_666 ?
C1 C2 C15 C12 -1.85(19) . . . . ?
C1 C2 C15 C15 178.51(14) . . . 3_666 ?
C2 C1 C14 C13 2.2(2) . . . . ?
C10 C2 C15 C12 -178.92(12) . . . . ?
C10 C2 C15 C15 1.4(2) . . . 3_666 ?
C10 C11 C12 C13 178.09(15) 3_666 . . . ?
C10 C11 C12 C15 -1.8(2) 3_666 . . . ?
C11 C12 C13 C14 -179.49(14) . . . . ?
C11 C12 C15 C2 -178.41(12) . . . . ?
C11 C12 C15 C15 1.2(2) . . . 3_666 ?
C12 C13 C14 C1 -2.4(2) . . . . ?
C13 C12 C15 C2 1.7(2) . . . . ?
C13 C12 C15 C15 -178.66(15) . . . 3_666 ?
C14 C1 C2 C10 176.86(13) . . . . ?
C14 C1 C2 C15 -0.1(2) . . . . ?
C15 C2 C10 C11 -0.9(2) . . . 3_666 ?
C15 C12 C13 C14 0.4(2) . . . . ?
