#------------------------------------------------------------------------------
#$Date: 2021-06-05 21:13:40 +0300 (Sat, 05 Jun 2021) $
#$Revision: 265972 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/23/7242307.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_7242307
loop_
_publ_author_name
'Dyk, Konrad'
'Baran, Łukasz'
'Rżysko, Wojciech'
'Stankevič, Marek'
'Kamiński, Daniel M.'
_publ_section_title
;
 Interplay between the crystal stability and the energy of the molecular
 conformation
;
_journal_issue                   14
_journal_name_full               CrystEngComm
_journal_page_first              2683
_journal_page_last               2694
_journal_paper_doi               10.1039/D0CE01673J
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C24 H18 O4'
_chemical_formula_sum            'C24 H18 O4'
_chemical_formula_weight         370.38
_chemical_melting_point          523
_chemical_name_common            DHBD
_chemical_name_systematic
5,5?-bis(4-hydroxyphenyl)-2,2?-dihydroxy-1,1?-biphenyl
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2781g1
_audit_creation_date             2021-02-16
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-02-16 deposited with the CCDC.	2021-02-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.1304(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.3993(4)
_cell_length_b                   8.82171(15)
_cell_length_c                   9.76280(17)
_cell_measurement_reflns_used    7741
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.7000
_cell_measurement_theta_min      4.3070
_cell_volume                     1749.84(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2763
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  31.00   1.00    3.00    --   40.94 -57.00 -30.00   57
  2  ω      3.00  79.00   1.00    3.00    --   40.94-125.00 -60.00   76
  3  ω     58.00 138.00   1.00   12.00    --  112.00 -45.00 -90.00   80
  4  ω    109.00 140.00   1.00   12.00    --  112.00 -61.00   0.00   31
  5  ω     58.00 116.00   1.00   12.00    --  112.00-111.00  60.00   58
  6  ω     37.00 144.00   1.00   12.00    --  112.00 -77.00  60.00  107
  7  ω     84.00 115.00   1.00   12.00    --  112.00  61.00 -30.00   31
  8  ω    121.00 158.00   1.00   12.00    --  112.00  77.00 -60.00   37
  9  ω    117.00 148.00   1.00   12.00    --  112.00 111.00 -60.00   31
 10  ω    116.00 157.00   1.00   12.00    --  112.00  77.00 -90.00   41
 11  ω    122.00 157.00   1.00   12.00    --  112.00  77.00-120.00   35
 12  ω     85.00 157.00   1.00   12.00    --  112.00  61.00-180.00   72
 13  ω     84.00 110.00   1.00   12.00    --  112.00  61.00 -60.00   26
 14  ω     84.00 152.00   1.00   12.00    --  112.00  61.00   0.00   68
 15  ω    133.00 158.00   1.00   12.00    --  112.00  61.00  60.00   25
 16  ω    131.00 157.00   1.00   12.00    --  112.00  61.00  90.00   26
 17  ω    119.00 144.00   1.00   12.00    --  112.00  77.00 150.00   25
 18  ω     84.00 158.00   1.00   12.00    --  112.00  61.00  30.00   74
 19  ω     85.00 118.00   1.00   12.00    --  112.00  61.00 -90.00   33
 20  ω     83.00 109.00   1.00   12.00    --  112.00  61.00-120.00   26
 21  ω     83.00 111.00   1.00   12.00    --  112.00  61.00-150.00   28
 22  ω     87.00 113.00   1.00   12.00    --  112.00  45.00-180.00   26
 23  ω     79.00 106.00   1.00   12.00    --  112.00  77.00-120.00   27
 24  ω     80.00 156.00   1.00   12.00    --  112.00  77.00-150.00   76
 25  ω     79.00 105.00   1.00   12.00    --  112.00  77.00 -60.00   26
 26  ω     80.00 106.00   1.00   12.00    --  112.00  77.00 -90.00   26
 27  ω     79.00 123.00   1.00   12.00    --  112.00  77.00 -30.00   44
 28  ω     79.00 158.00   1.00   12.00    --  112.00  77.00  60.00   79
 29  ω     80.00 105.00   1.00   12.00    --  112.00  77.00 120.00   25
 30  ω     83.00 158.00   1.00   12.00    --  112.00  61.00 120.00   75
 31  ω     79.00 104.00   1.00   12.00    --  112.00  77.00 150.00   25
 32  ω     83.00 109.00   1.00   12.00    --  112.00  61.00 150.00   26
 33  ω     83.00 110.00   1.00   12.00    --  112.00  61.00  90.00   27
 34  ω     84.00 110.00   1.00   12.00    --  112.00  61.00  60.00   26
 35  ω     79.00 105.00   1.00   12.00    --  112.00  77.00   0.00   26
 36  ω     80.00 106.00   1.00   12.00    --  112.00  77.00  30.00   26
 37  ω     79.00 104.00   1.00   12.00    --  112.00  77.00  90.00   25
 38  ω     22.00 111.00   1.00    3.00    --   40.94  37.00  60.00   89
 39  ω     24.00 108.00   1.00    3.00    --   40.94  37.00-120.00   84
 40  ω     80.00 105.00   1.00   12.00    --  112.00  77.00-180.00   25
 41  ω      9.00  58.00   1.00    3.00    --   40.94  77.00-180.00   49
 42  ω      9.00  92.00   1.00    3.00    --   40.94-125.00  90.00   83
 43  ω     29.00 102.00   1.00   12.00    --  112.00 -94.00 -30.00   73
 44  ω     36.00 116.00   1.00   12.00    --  112.00-111.00-120.00   80
 45  ω     29.00  84.00   1.00   12.00    --  112.00 -94.00 -90.00   55
 46  ω    -25.00  64.00   1.00    3.00    --   40.94 -57.00 120.00   89
 47  ω      9.00  57.00   1.00    3.00    --   40.94  77.00   0.00   48
 48  ω      8.00 115.00   1.00    3.00    --   40.94  77.00 -90.00  107
 49  ω      9.00 117.00   1.00    3.00    --   40.94  77.00  90.00  108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0435307000
_diffrn_orient_matrix_UB_12      -0.1214159000
_diffrn_orient_matrix_UB_13      -0.0600214000
_diffrn_orient_matrix_UB_21      -0.0046726000
_diffrn_orient_matrix_UB_22      0.0855494000
_diffrn_orient_matrix_UB_23      -0.1381184000
_diffrn_orient_matrix_UB_31      0.0619177000
_diffrn_orient_matrix_UB_32      0.0918540000
_diffrn_orient_matrix_UB_33      0.0491664000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12203
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.256
_diffrn_reflns_theta_min         4.352
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.774
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59609
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.406
_exptl_crystal_description       plate
_exptl_crystal_F_000             776
_exptl_crystal_preparation       'Evoparoation from acetonitrille'
_exptl_crystal_recrystallization_method 'Crystallization from acetonitrille'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1821
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0392
_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)+(0.0563P)²+0.8901P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1093
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1724
_reflns_number_total             1821
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01673j1.cif
_cod_data_source_block           exp_563
_cod_depositor_comments
'Adding full bibliography for 7242306--7242309.cif.'
_cod_database_code               7242307
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C12H4O2
_chemical_oxdiff_usercomment     2294-5
_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   0.977
_shelx_estimated_absorpt_t_min   0.747
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.01
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C11(H11), C2(H2A), C8(H8), C9(H9), C5(H5), C4(H4)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_olex2_exptl_crystal_mounting_method oil
_olex2_submission_original_sample_id BHDB
_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 1.610
_oxdiff_exptl_absorpt_empirical_full_min 0.550
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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 0.41868(4) 0.86038(12) 0.38101(9) 0.0434(3) Uani 1 1 d . . . . .
H1 H 0.404691 0.903727 0.446757 0.065 Uiso 1 1 calc R U . . .
O2 O 0.86531(4) 0.48689(11) 0.63138(10) 0.0438(3) Uani 1 1 d . . . . .
H2 H 0.883370 0.538622 0.693548 0.066 Uiso 1 1 calc R U . . .
C12 C 0.70802(6) 0.68791(14) 0.64186(11) 0.0333(3) Uani 1 1 d . . . . .
H12 H 0.690448 0.770373 0.685323 0.040 Uiso 1 1 calc R U . . .
C7 C 0.66757(5) 0.60483(14) 0.54621(11) 0.0312(3) Uani 1 1 d . . . . .
C10 C 0.80014(5) 0.52807(14) 0.60919(12) 0.0321(3) Uani 1 1 d . . . . .
C3 C 0.59953(5) 0.65785(14) 0.50468(12) 0.0324(3) Uani 1 1 d . . . . .
C11 C 0.77359(6) 0.65077(14) 0.67371(12) 0.0339(3) Uani 1 1 d . . . . .
H11 H 0.799585 0.707634 0.737800 0.041 Uiso 1 1 calc R U . . .
C2 C 0.57319(5) 0.65354(13) 0.36770(12) 0.0315(3) Uani 1 1 d . . . . .
H2A H 0.596887 0.605496 0.303151 0.038 Uiso 1 1 calc R U . . .
C1 C 0.51253(5) 0.71881(14) 0.32424(11) 0.0303(3) Uani 1 1 d . . . . .
C6 C 0.47727(5) 0.78981(15) 0.42267(12) 0.0331(3) Uani 1 1 d . . . . .
C8 C 0.69512(6) 0.48042(15) 0.48522(14) 0.0388(3) Uani 1 1 d . . . . .
H8 H 0.669073 0.421678 0.422742 0.047 Uiso 1 1 calc R U . . .
C9 C 0.76081(6) 0.44247(14) 0.51601(14) 0.0393(3) Uani 1 1 d . . . . .
H9 H 0.778422 0.359192 0.473824 0.047 Uiso 1 1 calc R U . . .
C5 C 0.50189(6) 0.79155(17) 0.55976(12) 0.0408(3) Uani 1 1 d . . . . .
H5 H 0.477735 0.836915 0.625010 0.049 Uiso 1 1 calc R U . . .
C4 C 0.56214(6) 0.72621(17) 0.59992(12) 0.0399(3) Uani 1 1 d . . . . .
H4 H 0.577980 0.727950 0.692238 0.048 Uiso 1 1 calc R U . . .
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
C6 O1 H1 109.5 . . ?
C10 O2 H2 109.5 . . ?
C7 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C11 C12 C7 121.78(11) . . ?
C12 C7 C3 119.91(10) . . ?
C8 C7 C12 117.58(10) . . ?
C8 C7 C3 122.32(10) . . ?
O2 C10 C11 123.05(11) . . ?
O2 C10 C9 117.06(11) . . ?
C9 C10 C11 119.88(11) . . ?
C2 C3 C7 121.52(10) . . ?
C4 C3 C7 120.55(10) . . ?
C4 C3 C2 117.69(10) . . ?
C12 C11 C10 119.42(11) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C3 C2 H2A 118.8 . . ?
C1 C2 C3 122.31(10) . . ?
C1 C2 H2A 118.8 . . ?
C2 C1 C1 120.80(11) . 2_655 ?
C2 C1 C6 118.17(10) . . ?
C6 C1 C1 120.97(11) . 2_655 ?
O1 C6 C1 119.06(10) . . ?
O1 C6 C5 120.67(11) . . ?
C5 C6 C1 120.26(10) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.12(11) . . ?
C9 C8 H8 119.4 . . ?
C10 C9 C8 120.20(11) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C6 C5 H5 119.8 . . ?
C4 C5 C6 120.34(11) . . ?
C4 C5 H5 119.8 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.19(11) . . ?
C5 C4 H4 119.4 . . ?
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 H1 0.8200 . ?
O1 C6 1.3765(13) . ?
O2 H2 0.8200 . ?
O2 C10 1.3766(13) . ?
C12 H12 0.9300 . ?
C12 C7 1.3972(16) . ?
C12 C11 1.3852(16) . ?
C7 C3 1.4862(14) . ?
C7 C8 1.3910(17) . ?
C10 C11 1.3866(17) . ?
C10 C9 1.3824(17) . ?
C3 C2 1.3965(16) . ?
C3 C4 1.3917(17) . ?
C11 H11 0.9300 . ?
C2 H2A 0.9300 . ?
C2 C1 1.3960(15) . ?
C1 C1 1.493(2) 2_655 ?
C1 C6 1.3988(16) . ?
C6 C5 1.3869(16) . ?
C8 H8 0.9300 . ?
C8 C9 1.3879(16) . ?
C9 H9 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.3822(16) . ?
C4 H4 0.9300 . ?
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 C6 C5 C4 -177.16(13) . . . . ?
O2 C10 C11 C12 177.66(11) . . . . ?
O2 C10 C9 C8 -177.92(12) . . . . ?
C12 C7 C3 C2 137.79(12) . . . . ?
C12 C7 C3 C4 -36.38(18) . . . . ?
C12 C7 C8 C9 -1.5(2) . . . . ?
C7 C12 C11 C10 0.07(19) . . . . ?
C7 C3 C2 C1 -172.35(11) . . . . ?
C7 C3 C4 C5 172.52(13) . . . . ?
C7 C8 C9 C10 0.3(2) . . . . ?
C3 C7 C8 C9 173.45(12) . . . . ?
C3 C2 C1 C1 176.89(9) . . . 2_655 ?
C3 C2 C1 C6 -0.40(18) . . . . ?
C11 C12 C7 C3 -173.78(11) . . . . ?
C11 C12 C7 C8 1.25(19) . . . . ?
C11 C10 C9 C8 1.0(2) . . . . ?
C2 C3 C4 C5 -1.9(2) . . . . ?
C2 C1 C6 O1 177.30(11) . . . . ?
C2 C1 C6 C5 -1.36(18) . . . . ?
C1 C1 C6 O1 0.02(16) 2_655 . . . ?
C1 C1 C6 C5 -178.64(11) 2_655 . . . ?
C1 C6 C5 C4 1.5(2) . . . . ?
C6 C5 C4 C3 0.2(2) . . . . ?
C8 C7 C3 C2 -37.00(18) . . . . ?
C8 C7 C3 C4 148.83(13) . . . . ?
C9 C10 C11 C12 -1.23(19) . . . . ?
C4 C3 C2 C1 1.99(19) . . . . ?
