Interplay between the crystal stability and the energy of the molecular conformation
Dyk, Konrad; Baran, Łukasz; Rżysko, Wojciech; Stankevič, Marek; Kamiński, Daniel M.; CrystEngComm 23 (2021) 2683–2694; doi:10.1039/D0CE01673J

data_7242309
_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, C3 H6 O, 1.25(H2 O)'
_chemical_formula_sum            'C27 H26.5 O6.25'
_chemical_formula_weight         450.98
_chemical_melting_point          523
_chemical_name_common            BHDB
_chemical_name_systematic
5,5?-bis(4-hydroxyphenyl)-2,2?-dihydroxy-1,1?-biphenyl
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc27614n
_audit_creation_date             2021-02-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6257)
;
_audit_update_record
;
2021-02-17 deposited with the CCDC.	2021-02-19 downloaded from the CCDC.
;
_cell_angle_alpha                80.520(4)
_cell_angle_beta                 82.650(5)
_cell_angle_gamma                83.754(5)
_cell_formula_units_Z            2
_cell_length_a                   10.4718(6)
_cell_length_b                   10.6341(5)
_cell_length_c                   11.1086(6)
_cell_measurement_reflns_used    3307
_cell_measurement_temperature    293.0
_cell_measurement_theta_max      74.6370
_cell_measurement_theta_min      4.0370
_cell_volume                     1205.24(11)
_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    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2763
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -24.00  63.00   1.00    7.15    --   40.94 -37.00 -30.00   87
  2  \w     42.00 140.00   1.00   28.61    --  112.00 -61.00  90.00   98
  3  \w     85.00 114.00   1.00   28.61    --  112.00-111.00  60.00   29
  4  \w     90.00 141.00   1.00   28.61    --  112.00 -61.00 -30.00   51
  5  \w     83.00 108.00   1.00   28.61    --  112.00 -94.00 -60.00   25
  6  \w     57.00 140.00   1.00   28.61    --  112.00 -77.00-150.00   83
  7  \w     79.00 115.00   1.00   28.61    --  112.00-111.00-180.00   36
  8  \w     40.00  68.00   1.00   28.61    --  112.00 -61.00 -30.00   28
  9  \w     58.00 109.00   1.00   28.61    --  112.00 -94.00  30.00   51
 10  \w     36.00  65.00   1.00   28.61    --  112.00-111.00  60.00   29
 11  \w     32.00  91.00   1.00    7.15    --   40.94-132.00 166.00   59
 12  \w    -23.00 110.00   1.00    7.15    --   40.94   0.00   0.00  133
 13  \w     93.00 158.00   1.00   28.61    --  112.00  61.00 -30.00   65
 14  \w    115.00 156.00   1.00   28.61    --  112.00  45.00 -60.00   41
 15  \w    125.00 158.00   1.00   28.61    --  112.00  45.00-180.00   33
 16  \w     90.00 125.00   1.00   28.61    --  112.00  30.00-180.00   35
 17  \w     82.00 142.00   1.00   28.61    --  112.00 111.00-180.00   60
 18  \w     85.00 154.00   1.00   28.61    --  112.00 111.00  30.00   69
 19  \w     65.00 142.00   1.00   28.61    --  112.00 137.00  53.00   77
 20  \w    -53.00  -3.00   1.00    7.15    --  -40.94 125.00 150.00   50
 21  \w    -92.00 -28.00   1.00    7.15    --  -40.94 125.00-120.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0628294000
_diffrn_orient_matrix_UB_12      -0.0463242000
_diffrn_orient_matrix_UB_13      0.1306736000
_diffrn_orient_matrix_UB_21      0.1128073000
_diffrn_orient_matrix_UB_22      0.0441498000
_diffrn_orient_matrix_UB_23      0.0541539000
_diffrn_orient_matrix_UB_31      -0.0742176000
_diffrn_orient_matrix_UB_32      0.1328624000
_diffrn_orient_matrix_UB_33      0.0035463000
_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  0.0672
_diffrn_reflns_av_unetI/netI     0.0808
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8362
_diffrn_reflns_point_group_measured_fraction_full 0.592
_diffrn_reflns_point_group_measured_fraction_max 0.568
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.116
_diffrn_reflns_theta_min         4.060
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.721
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36139
_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            'dull yellow'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_description       plate
_exptl_crystal_F_000             477
_exptl_crystal_preparation       'solvent mixture aceton+water'
_exptl_crystal_recrystallization_method 'low temperature solvent evaporation'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.3(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     625
_refine_ls_number_reflns         5726
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0802
_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/[\s^2^(Fo^2^)+(0.1140P)^2^+0.2220P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2037
_refine_ls_wR_factor_ref         0.2485
_reflns_Friedel_coverage         0.181
_reflns_Friedel_fraction_full    0.187
_reflns_Friedel_fraction_max     0.174
_reflns_number_gt                4325
_reflns_number_total             5726
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce01673j1.cif
_cod_data_source_block           22942
_cod_depositor_comments
'Adding full bibliography for 7242306--7242309.cif.'
_cod_original_formula_sum        'C27 H26.50 O6.25'
_cod_database_code               7242309
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.965
_shelx_estimated_absorpt_t_min   0.761
_reflns_odcompleteness_completeness 99.76
_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 C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 H1O7-H3O'_$2 = H3O'_$2-H2O7
 2.4 with sigma of 0.02
 H1O'-H2O5
 2.3 with sigma of 0.04
3. Others
 Fixed Sof: O6(0.5) H1O6(0.5) H2O6(0.5)
4.a Free rotating group:
 O5(H1O5,H2O5), O6(H1O6,H2O6), O7(H2O7,H1O7)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C4(H4A), C5(H5), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14),
 C16(H16), C17(H17), C20(H20), C21(H21), C23(H23), C24(H24), C2'(H2'A),
 C4'(H4'A), C5'(H5'), C8'(H8'), C9'(H9'), C11'(H11'), C12'(H12'), C14'(H14'),
 C16'(H16'), C17'(H17'), C20'(H20'), C21'(H21'), C23'(H23'), C24'(H24')
4.c Idealised Me refined as rotating group:
 C1AC(H1AA,H1AB,H1AC), C3AC(H3AA,H3AB,H3AC), C4AC(H4AA,H4AB,H4AC), C6AC(H6AA,
 H6AB,H6AC)
4.d Idealised tetrahedral OH refined as rotating group:
 O1(H1O), O2(H2O), O3(H3O), O4(H4O), O1'(H1O'), O2'(H2O'), O3'(H3O'), O4'(H4O')
;
_shelx_res_checksum              3004
_olex2_exptl_crystal_mounting_method 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 2.263
_oxdiff_exptl_absorpt_empirical_full_min 0.238