Polymorphism and distinct physicochemical properties of the phloretin–nicotinamide cocrystal
Aitipamula, Srinivasulu; Shan, Loke Pei; Gupta, Krishna M.; CrystEngComm 24 (2022) 560–570; doi:10.1039/D1CE01352A

data_7243994
_publ_section_title
;
 Polymorphism and distinct physicochemical properties of the
 phloretin--nicotinamide cocrystal
;
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              560
_journal_page_last               570
_journal_paper_doi               10.1039/D1CE01352A
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C15 H14 O5, C6 H6 N2 O'
_chemical_formula_sum            'C21 H20 N2 O6'
_chemical_formula_weight         396.39
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_audit_update_record
;
2021-10-06 deposited with the CCDC.	2021-11-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.945(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.51190(10)
_cell_length_b                   7.5163(2)
_cell_length_c                   17.4195(3)
_cell_measurement_reflns_used    8750
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.3270
_cell_measurement_theta_min      5.1750
_cell_volume                     962.24(3)
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2945
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.980
_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    -60.00  47.00   1.00    4.05    --  -36.88  57.00-120.00  107
  2  \w   -122.00 -80.00   1.00    4.05    --  -36.88 -99.00-150.00   42
  3  \w   -118.00 -93.00   1.00    4.05    --  -36.88-125.00 150.00   25
  4  \w     80.00 111.00   1.00    4.05    --   36.88  38.00   0.00   31
  5  \w      0.00  73.00   1.00    4.05    --   36.88  38.00   0.00   73
  6  \w     80.00 128.00   1.00    4.05    --   36.88  77.00-180.00   48
  7  \w     27.00  67.00   1.00    4.05    --   36.88-125.00   0.00   40
  8  \w      0.00  47.00   1.00    4.05    --   36.88  77.00 120.00   47
  9  \w     40.00 108.00   1.00    4.05    --   36.88  57.00 120.00   68
 10  \w     11.00 107.00   1.00    4.05    --   36.88  77.00   0.00   96
 11  \w     -2.00  70.00   1.00    4.05    --   36.88  77.00 -60.00   72
 12  \w     35.00  98.00   1.00    4.05    --   36.88  77.00-150.00   63
 13  \w     12.00  75.00   1.00    4.05    --   36.88  77.00-180.00   63
 14  \w    -30.00  74.00   1.00    4.05    --   36.88 -38.00  60.00  104
 15  \w      3.00  31.00   1.00    4.05    --   36.88  57.00 120.00   28
 16  \w     23.00  62.00   1.00    4.05    --   36.88-125.00  90.00   39
 17  \w     54.00  93.00   1.00    4.05    --   36.88-125.00 120.00   39
 18  \w     98.00 123.00   1.00    4.05    --   36.88  77.00 120.00   25
 19  \w     42.00  78.00   1.00    4.05    --   36.88-125.00 -60.00   36
 20  \w     74.00 128.00   1.00   12.19    --  109.17  61.00  90.00   54
 21  \w     83.00 149.00   1.00   12.19    --  109.17 178.00 -60.00   66
 22  \w     70.00  97.00   1.00   12.19    --  109.17  77.00 -60.00   27
 23  \w     70.00  96.00   1.00   12.19    --  109.17  77.00  90.00   26
 24  \w    110.00 172.00   1.00   12.19    --  109.17  77.00  30.00   62
 25  \w     36.00  90.00   1.00   12.19    --  109.17 -94.00 -60.00   54
 26  \w     74.00 101.00   1.00   12.19    --  109.17  61.00  60.00   27
 27  \w    124.00 176.00   1.00   12.19    --  109.17  61.00  60.00   52
 28  \w     70.00 175.00   1.00   12.19    --  109.17  77.00-180.00  105
 29  \w     70.00 104.00   1.00   12.19    --  109.17  77.00-150.00   34
 30  \w    116.00 174.00   1.00   12.19    --  109.17  77.00-150.00   58
 31  \w     70.00 102.00   1.00   12.19    --  109.17  77.00   0.00   32
 32  \w     70.00 107.00   1.00   12.19    --  109.17  77.00  30.00   37
 33  \w     70.00  96.00   1.00   12.19    --  109.17  77.00 120.00   26
 34  \w     74.00 100.00   1.00   12.19    --  109.17  61.00  30.00   26
 35  \w     70.00  96.00   1.00   12.19    --  109.17  77.00 -30.00   26
 36  \w     72.00  98.00   1.00   12.19    --  109.17  61.00-150.00   26
 37  \w     74.00 176.00   1.00   12.19    --  109.17  61.00 -60.00  102
 38  \w     70.00  99.00   1.00   12.19    --  109.17  77.00  60.00   29
 39  \w     73.00 174.00   1.00   12.19    --  109.17  61.00 150.00  101
 40  \w    108.00 160.00   1.00   12.19    --  109.17  77.00 -90.00   52
 41  \w     70.00 175.00   1.00   12.19    --  109.17  77.00-120.00  105
 42  \w     72.00  97.00   1.00   12.19    --  109.17  61.00 -30.00   25
 43  \w     72.00 149.00   1.00   12.19    --  109.17  61.00 120.00   77
 44  \w     72.00  98.00   1.00   12.19    --  109.17  61.00-180.00   26
 45  \w     75.00 101.00   1.00   12.19    --  109.17  61.00 -90.00   26
 46  \w     70.00  96.00   1.00   12.19    --  109.17  77.00 -90.00   26
 47  \w     73.00  99.00   1.00   12.19    --  109.17  61.00   0.00   26
 48  \w     76.00 108.00   1.00   12.19    --  109.17  61.00-120.00   32
 49  \w    151.00 177.00   1.00   12.19    --  109.17  77.00 150.00   26
 50  \w     75.00 178.00   1.00   12.19    --  109.17  45.00   0.00  103
 51  \w     70.00  95.00   1.00   12.19    --  109.17  77.00 150.00   25
 52  \w     20.00 100.00   1.00   12.19    --  109.17 -94.00   0.00   80
 53  \w    152.00 177.00   1.00   12.19    --  109.17  61.00  90.00   25
 54  \w    153.00 178.00   1.00   12.19    --  109.17  77.00 -60.00   25
 55  \w     62.00 135.00   1.00   12.19    --  109.17 -77.00  30.00   73
 56  \w     40.00  90.00   1.00   12.19    --  109.17 -94.00-120.00   50
;
_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      0.0752556000
_diffrn_orient_matrix_UB_12      0.0068927000
_diffrn_orient_matrix_UB_13      -0.0757887000
_diffrn_orient_matrix_UB_21      -0.1955707000
_diffrn_orient_matrix_UB_22      0.0044090000
_diffrn_orient_matrix_UB_23      -0.0491228000
_diffrn_orient_matrix_UB_31      0.0016855000
_diffrn_orient_matrix_UB_32      0.2048590000
_diffrn_orient_matrix_UB_33      0.0035993000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9930
_diffrn_reflns_point_group_measured_fraction_full 0.894
_diffrn_reflns_point_group_measured_fraction_max 0.872
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.388
_diffrn_reflns_theta_min         2.593
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.846
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.757
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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    1.368
_exptl_crystal_description       needle
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.224
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.074
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.085
_refine_ls_abs_structure_details
;
 Flack x determined using 1212 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         3334
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0438
_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/[\s^2^(Fo^2^)+(0.0788P)^2^+0.0185P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1091
_reflns_Friedel_coverage         0.647
_reflns_Friedel_fraction_full    0.773
_reflns_Friedel_fraction_max     0.746
_reflns_number_gt                3222
_reflns_number_total             3334
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce01352a2.cif
_cod_data_source_block           PHL-NA-FormII
_cod_depositor_comments          'Adding full bibliography for 7243994.cif.'
_cod_database_code               7243994
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C20 H24 N2 O6'
_reflns_odcompleteness_completeness 99.73
_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
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C20(H20), C5(H5A), C17(H17), C11(H11), C12(H12), C19(H19), C15(H15),
 C18(H18), C14(H14)
;
_shelx_res_checksum              44581
_shelx_hkl_checksum              6896
_olex2_date_sample_data_collection 2019-08-14
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 5.647
_oxdiff_exptl_absorpt_empirical_full_min 0.591