The role of 3-OH in the self-assembly of pharmaceutical cocrystals of dihydroflavonol with 4,4′-bipyridine
Liu, Lixin; Liu, Moqi; Zhang, Yunan; Yin, Hemei; Su, Xin; Zhang, Qiang; Feng, Yanru; Guo, Yingxue; Zou, Dongyu; Liu, Yingli; New Journal of Chemistry 45 (2021) 1626–1633; doi:10.1039/D0NJ04113K

data_7060177
_publ_section_title
;
 The role of 3-OH in the self-assembly of pharmaceutical cocrystals of
 dihydroflavonol with 4,4&#x2032;-bipyridine
;
_journal_issue                   3
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1626
_journal_page_last               1633
_journal_paper_doi               10.1039/D0NJ04113K
_journal_volume                  45
_journal_year                    2021
_chemical_absolute_configuration unk
_chemical_formula_moiety         '2(C15 H12 O7), 3(C10 H8 N2)'
_chemical_formula_sum            'C60 H48 N6 O14'
_chemical_formula_weight         1077.04
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-07-19
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-08-19 deposited with the CCDC.	2020-12-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.014(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.6073(4)
_cell_length_b                   8.4846(4)
_cell_length_c                   34.8953(14)
_cell_measurement_reflns_used    3722
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.8800
_cell_measurement_theta_min      3.6510
_cell_volume                     2534.4(2)
_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)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.878
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.878
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            17976
_diffrn_reflns_point_group_measured_fraction_full 0.849
_diffrn_reflns_point_group_measured_fraction_max 0.716
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.909
_diffrn_reflns_theta_min         3.474
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_description       block
_exptl_crystal_F_000             1124
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.8(13)
_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     750
_refine_ls_number_reflns         9567
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0565
_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^)+(0.0550P)^2^+0.1492P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1304
_reflns_Friedel_coverage         0.532
_reflns_Friedel_fraction_full    0.678
_reflns_Friedel_fraction_max     0.532
_reflns_number_gt                6655
_reflns_number_total             9567
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj04113k2.cif
_cod_data_source_block           tmp
_cod_depositor_comments
'Adding full bibliography for 7060176--7060177.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7060177
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.960
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.2(13)
 0.8(13)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
3. Restrained distances
 C24A-C23A \\sim C24B-C23B
 with sigma of 0.01
 C23B-C22 \\sim C23A-C22 \\sim C24A-C23A \\sim C24B-C23B
 with sigma of 0.01
 C24B-C25 \\sim C24A-C25
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
C23B \\sim C23A: within 1.7A with sigma of 0.005 and sigma for terminal atoms
of 0.01 within 1.7A
C24B \\sim C24A: within 1.7A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 1.7A
5. Others
 Sof(H11A)=Sof(C23A)=Sof(H23A)=Sof(C24A)=Sof(H24A)=1-FVAR(1)
 Sof(H11)=Sof(C23B)=Sof(H23B)=Sof(C24B)=Sof(H24B)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8A), C23B(H23B), C24B(H24B), C23A(H23A), C24A(H24A)
6.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C3(H3A), C6(H6A), C14(H14A), C41(H41), C42(H42), C44(H44), C5(H5A),
 C45(H45), C47(H47), C50(H50), C48(H48), C49(H49), C26(H26), C30(H30), C16(H16),
  C27(H27), C18(H18), C32(H32), C40(H40), C35(H35), C38(H38), C34(H34),
 C39(H39), C31(H31), C37(H37), C57(H57), C60(H60), C58(H58), C54(H54), C52(H52),
  C51(H51), C59(H59), C55(H55)
6.c Tetrahedral OH refined with riding coordinates:
 O11(H11), O11(H11A)
6.d Idealised tetrahedral OH refined as rotating group:
 O3(H3), O1(H1), O6(H6), O5(H5), O2(H2), O14(H14), O9(H9), O8(H8), O13(H13)
;
_olex2_submission_special_instructions 'No special instructions were received'