Cocrystal of phloretin with isoniazid: preparation, characterization, and evaluation
Lu, Zhongyu; Chen, Hankun; Mo, Jiaxin; Yuan, Xiaohong; Wang, Dawei; Zheng, Xianhui; Zhu, Wei; RSC Advances 13 (2023) 10914–10922; doi:10.1039/D3RA00750B

data_7246575
_publ_section_title
;
 Cocrystal of phloretin with isoniazid: preparation, characterization, and
 evaluation
;
_journal_issue                   16
_journal_name_full               'RSC Advances'
_journal_page_first              10914
_journal_page_last               10922
_journal_paper_doi               10.1039/D3RA00750B
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C15 H14 O5, C6 H7 N3 O'
_chemical_formula_sum            'C21 H21 N3 O6'
_chemical_formula_weight         411.41
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-06-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-02-02 deposited with the CCDC.	2023-03-14 downloaded from the CCDC.
;
_cell_angle_alpha                92.308(3)
_cell_angle_beta                 91.398(3)
_cell_angle_gamma                107.015(3)
_cell_formula_units_Z            4
_cell_length_a                   9.8309(4)
_cell_length_b                   9.8954(4)
_cell_length_c                   20.6193(7)
_cell_measurement_reflns_used    12093
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.9310
_cell_measurement_theta_min      4.2860
_cell_volume                     1915.13(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.940
_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     -1.00  24.00   1.00    4.00    --   38.00  95.00-112.32   25
  2  \w   -114.00 -13.00   1.00    4.00    --  -41.14 -57.00 -60.00  101
  3  \w    -91.00  -5.00   1.00    4.00    --  -41.14 125.00  60.00   86
  4  \w   -110.00 -14.00   1.00    4.00    --  -41.14 -57.00  60.00   96
  5  \w    -73.00  32.00   1.00    4.00    --  -41.14  77.00-150.00  105
  6  \w   -114.00 -13.00   1.00    4.00    --  -41.14 -57.00-180.00  101
  7  \w     24.00  78.00   1.00    4.00    --   41.14-125.00   0.00   54
  8  \w      6.00  32.00   1.00    4.00    --   42.00  90.00  91.75   26
  9  \w     11.00  38.00   1.00    4.00    --   46.00  84.00-164.09   27
 10  \w     17.00  45.00   1.00    4.00    --   46.00  79.00 -74.55   28
 11  \w     17.00  42.00   1.00    4.00    --   50.00  80.00  -2.06   25
 12  \w     17.00  42.00   1.00    4.00    --   50.00  79.00  94.31   25
 13  \w     17.00  42.00   1.00    4.00    --   50.00  80.00  31.90   25
 14  \w     87.00 114.00   1.00    4.00    --   66.00  77.00 -29.74   27
 15  \w     34.00  61.00   1.00    4.00    --   66.00  75.00 101.73   27
 16  \w     33.00  59.00   1.00    4.00    --   66.00  77.00-128.05   26
 17  \w     33.00  61.00   1.00    4.00    --   66.00  77.00 163.08   28
 18  \w     80.00 105.00   1.00    4.00    --   66.00  77.00-128.05   25
 19  \w     36.00  63.00   1.00    4.00    --   66.00  76.00   3.02   27
 20  \w     83.00 135.00   1.00    4.00    --   66.00  75.00 101.73   52
 21  \w     34.00  62.00   1.00    4.00    --   66.00  77.00 -29.74   28
 22  \w     37.00  73.00   1.00    4.00    --   70.00  77.00 135.19   36
 23  \w     37.00  65.00   1.00    4.00    --   70.00  77.00-119.88   28
 24  \w     93.00 120.00   1.00    4.00    --   70.00  77.00  54.96   27
 25  \w     38.00  64.00   1.00    4.00    --   70.00  75.00-161.65   26
 26  \w     95.00 122.00   1.00    4.00    --   70.00  75.00-161.65   27
 27  \w     38.00  81.00   1.00    4.00    --   70.00  77.00  54.96   43
 28  \w     37.00  71.00   1.00    4.00    --   70.00  77.00  30.57   34
 29  \w     37.00  80.00   1.00    4.00    --   70.00  77.00 -77.11   43
 30  \w     65.00  94.00   1.00   16.00    --   94.00  62.00 -59.75   29
 31  \w     68.00 170.00   1.00   16.00    --   98.00  64.00 164.13  102
 32  \w     75.00 146.00   1.00   16.00    --  107.79  77.00 -60.00   71
 33  \w     75.00 146.00   1.00   16.00    --  107.79  77.00   0.00   71
 34  \w     25.00 105.00   1.00   16.00    --  107.79 -94.00  90.00   80
 35  \w    109.00 170.00   1.00   16.00    --  107.79  77.00  60.00   61
 36  \w     37.00 118.00   1.00   16.00    --  107.79-125.00 -90.00   81
 37  \w     80.00 138.00   1.00   16.00    --  107.79  61.00-150.00   58
 38  \w     75.00 103.00   1.00   16.00    --  107.79  77.00  60.00   28
 39  \w     80.00 174.00   1.00   16.00    --  107.79  61.00 -90.00   94
 40  \w     75.00 101.00   1.00   16.00    --  107.79  77.00-180.00   26
 41  \w     44.00 140.00   1.00   16.00    --  107.79 -77.00 -90.00   96
 42  \w     80.00 107.00   1.00   16.00    --  107.79  61.00-180.00   27
 43  \w     75.00 175.00   1.00   16.00    --  107.79  77.00  30.00  100
 44  \w    119.00 176.00   1.00   16.00    --  107.79  77.00  90.00   57
 45  \w     75.00 102.00   1.00   16.00    --  107.79  77.00  90.00   27
 46  \w     80.00 107.00   1.00   16.00    --  107.79  61.00  90.00   27
 47  \w     72.00 118.00   1.00   16.00    --  107.79-125.00  90.00   46
 48  \w     79.00 140.00   1.00   16.00    --  107.79  61.00 -30.00   61
 49  \w     36.00  65.00   1.00   16.00    --  107.79-125.00  90.00   29
 50  \w     75.00 177.00   1.00   16.00    --  107.79  77.00 120.00  102
 51  \w     75.00 146.00   1.00   16.00    --  107.79  77.00-150.00   71
 52  \w     75.00 154.00   1.00   16.00    --  107.79  77.00 -30.00   79
 53  \w     75.00 132.00   1.00   16.00    --  107.79  77.00-120.00   57
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0179380000
_diffrn_orient_matrix_UB_12      -0.1431420000
_diffrn_orient_matrix_UB_13      -0.0238338000
_diffrn_orient_matrix_UB_21      0.0075266000
_diffrn_orient_matrix_UB_22      -0.0416344000
_diffrn_orient_matrix_UB_23      0.0708952000
_diffrn_orient_matrix_UB_31      -0.1628400000
_diffrn_orient_matrix_UB_32      -0.0659524000
_diffrn_orient_matrix_UB_33      -0.0022009000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            30217
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.702
_diffrn_reflns_theta_min         4.295
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.887
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_description       plate
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       0.0013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     550
_refine_ls_number_reflns         7393
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0878
_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^)+(0.1092P)^2^+6.5036P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2537
_refine_ls_wR_factor_ref         0.2574
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6401
_reflns_number_total             7393
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ra00750b1.cif
_cod_data_source_block           a22062601a0305
_cod_original_cell_volume        1915.13(12)
_cod_database_code               7246575
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         CHON
_chemical_oxdiff_usercomment     GPS/YYS
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.783
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Riding coordinates:
 N1(H1A,H1B), N4(H4A,H4B)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C22(H22A,H22B), C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C5(H5A), C6(H6), C12(H12), C14(H14), C17(H17), C18(H18),
 C20(H20), C21(H21), C27(H27), C29(H29), N2(H2A), C33(H33), C34(H34), C35(H35),
 C36(H36), N5(H5B), C39(H39), C40(H40), C41(H41), C42(H42)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3), O4(H4), O5(H5), O6(H6A), O8(H8), O9(H9), O10(H10)
;
_olex2_date_sample_data_collection 2022-06-26
_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 1.306
_oxdiff_exptl_absorpt_empirical_full_min 0.694