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_7060176
_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_formula_moiety         'C15 H12 O8, 2.5(C10 H8 N2)'
_chemical_formula_sum            'C40 H32 N5 O8'
_chemical_formula_weight         710.70
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-07-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-08-19 deposited with the CCDC.	2020-12-18 downloaded from the CCDC.
;
_cell_angle_alpha                113.404(6)
_cell_angle_beta                 92.846(5)
_cell_angle_gamma                96.827(6)
_cell_formula_units_Z            2
_cell_length_a                   7.7292(5)
_cell_length_b                   14.6301(10)
_cell_length_c                   16.7639(8)
_cell_measurement_reflns_used    1964
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.2410
_cell_measurement_theta_min      3.1510
_cell_volume                     1717.6(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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     -2.00  80.00   1.00   10.00    --   16.65  37.00 -90.00   82
  2  \w    -16.00  23.00   1.00   10.00    --  -17.43 -99.00-120.00   39
  3  \w    -37.00  45.00   1.00   10.00    --   16.65 -77.00   0.00   82
  4  \w     -2.00  84.00   1.00   10.00    --   16.65  57.00 120.00   86
  5  \w     35.00  65.00   1.00   10.00    --   16.65 178.00   0.00   30
  6  \w    -51.00  35.00   1.00   10.00    --   16.65 -57.00 120.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0905
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12742
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         2.806
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91491
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_description       block
_exptl_crystal_F_000             742
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0054(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     551
_refine_ls_number_reflns         6386
_refine_ls_number_restraints     301
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.1495
_refine_ls_R_factor_gt           0.0702
_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^)+(0.0439P)^2^+0.6926P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1680
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3256
_reflns_number_total             6386
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj04113k2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7060176--7060177.cif.'
_cod_database_code               7060176
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.961
_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. Restrained distances
 O5AA-O4AA
 0.85 with sigma of 0.01
 C37A-N5 \\sim N5-C38
 with sigma of 0.02
 C37A-N5 \\sim N5-C38A
 with sigma of 0.02
 C39A-C40 \\sim C37A-C36A \\sim N5-C37A \\sim N5-C38A \\sim C39A-C38A \\sim
C36A-C40
 with sigma of 0.01
 C7B-C8B \\sim C7A-C8A \\sim C9-C8B \\sim C9-C8A
 with sigma of 0.01
 C7A-C1 \\sim C7B-C1
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C36 \\sim C36A \\sim C37 \\sim C37A \\sim C38 \\sim C38A \\sim C39 \\sim C39A:
within 3.8A with sigma of 0.01 and sigma for terminal atoms of 0.02
O4AA \\sim C8A \\sim C7B \\sim C7A \\sim C8B: within 3.8A with sigma of 0.01
and sigma for terminal atoms of 0.02
Uanis(O4AA) \\sim Ueq, Uanis(C8A) \\sim Ueq, Uanis(C8B) \\sim Ueq, Uanis(C7B)
\\sim Ueq, Uanis(C7A) \\sim Ueq, Uanis(C35) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 C36, C37, C38, C39
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C36A, C37A, C38A, C39A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C36A)=Sof(H36A)=Sof(C37A)=Sof(H37A)=Sof(C38A)=Sof(H38A)=Sof(C39A)=
 Sof(H39A)=1-FVAR(1)
 Sof(C36)=Sof(H36)=Sof(C37)=Sof(H37)=Sof(C38)=Sof(H38)=Sof(C39)=Sof(H39)=FVAR(1)
 Sof(C8B)=Sof(H8B)=Sof(C7B)=Sof(H7B)=Sof(O5AA)=Sof(H5AA)=1-FVAR(2)
 Sof(C8A)=Sof(H8A)=Sof(C7A)=Sof(H7A)=Sof(O4AA)=Sof(H4AA)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C8A(H8A), C7A(H7A), C8B(H8B), C7B(H7B)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C6(H6), C12(H12), C14(H14), C16(H16), C17(H17), C19(H19), C20(H20),
 C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C29(H29), C30(H30),
  C31(H31), C32(H32), C34(H34), C35(H35), C36(H36), C36A(H36A), C37(H37),
 C37A(H37A), C38(H38), C38A(H38A), C39(H39), C39A(H39A)
6.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O3(H3), O7(H7), O8(H8), O4AA(H4AA), O5AA(H5AA)
;
_shelx_res_checksum              12462
_shelx_hkl_checksum              15297
_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
;