Preparation and characterization for multicomponent crystals of the antidiabetic drug gliquidone based on crystal engineering
Jia, Lina; Yu, Yang; Wang, Mengwei; Ouyang, Hanzhi; Gong, Junbo; CrystEngComm 21 (2019) 1617–; doi:10.1039/C8CE01848K

data_7232235
_publ_section_title
;
 Preparation and characterization for multicomponent crystals of the
 antidiabetic drug gliquidone based on crystal engineering
;
_journal_issue                   10
_journal_name_full               CrystEngComm
_journal_page_first              1617
_journal_paper_doi               10.1039/C8CE01848K
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C27 H32 N3 O6 S, C2 H6 O, C2 H6 N'
_chemical_formula_sum            'C31 H44 N4 O7 S'
_chemical_formula_weight         616.76
_chemical_name_systematic        gliquidone
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2018-12-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-12-24 deposited with the CCDC.
2019-01-25 downloaded from the CCDC.
;
_cell_angle_alpha                88.7720(10)
_cell_angle_beta                 84.4160(10)
_cell_angle_gamma                78.1010(10)
_cell_formula_units_Z            2
_cell_length_a                   6.38180(10)
_cell_length_b                   11.7984(2)
_cell_length_c                   22.1415(3)
_cell_measurement_reflns_used    20715
_cell_measurement_temperature    159.99(10)
_cell_measurement_theta_max      74.4650
_cell_measurement_theta_min      1.9750
_cell_volume                     1623.58(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (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      159.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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     49.00  75.00   0.50    0.33    --   46.12  38.00 -30.00   52
  2  \w     88.00 116.00   0.50    0.33    --   46.12  38.00 -30.00   56
  3  \w     68.00 117.00   0.50    1.31    --  101.75 -20.00-128.39   98
  4  \w     77.00 118.00   0.50    1.31    --  101.75 -61.00-150.00   82
  5  \w     79.00 104.00   0.50    1.31    --  101.75 -94.00-180.00   50
  6  \w     79.00 113.00   0.50    1.31    --  101.75-125.00-150.00   68
  7  \w     66.00 108.00   0.50    1.31    --  101.75 -94.00-120.00   84
  8  \w     58.00 107.00   0.50    1.31    --  101.75 -94.00 -30.00   98
  9  \w     86.00 117.00   0.50    1.31    --  101.75-125.00  30.00   62
 10  \w     81.00 117.00   0.50    1.31    --  101.75-125.00  90.00   72
 11  \w     92.00 117.00   0.50    1.31    --  101.75-125.00 120.00   50
 12  \w     75.00 106.00   0.50    1.31    --  101.75 -94.00 150.00   62
 13  \w     80.00 114.00   0.50    1.31    --  101.75 -45.00  90.00   68
 14  \w     91.00 120.00   0.50    1.31    --  101.75 -15.00 150.00   58
 15  \w     87.00 131.00   0.50    1.31    --  101.75  30.00  90.00   88
 16  \w    140.00 165.00   0.50    1.31    --  101.75  30.00  90.00   50
 17  \w    122.00 148.00   0.50    1.31    --  101.75  61.00  90.00   52
 18  \w    102.00 144.00   0.50    1.31    --  101.75  77.00  90.00   84
 19  \w    100.00 126.00   0.50    1.31    --  101.75  45.00  90.00   52
 20  \w     90.00 166.00   0.50    1.31    --  101.75  45.00  30.00  152
 21  \w    138.00 174.00   0.50    1.31    --  101.75  45.00   0.00   72
 22  \w    104.00 129.00   0.50    1.31    --  101.75  86.00-156.00   50
 23  \w    103.00 152.00   0.50    1.31    --  101.75  61.00-180.00   98
 24  \w    125.00 150.00   0.50    1.31    --  101.75  30.00-180.00   50
 25  \w     88.00 116.00   0.50    1.31    --  101.75  45.00 -30.00   56
 26  \w     60.00  88.00   0.50    1.31    --  101.75 -34.00 -20.82   56
 27  \w     66.00 104.00   0.50    1.31    --  101.75 -45.00 -30.00   76
 28  \w     81.00 107.00   0.50    1.31    --  101.75 -94.00   0.00   52
 29  \w     65.00 115.00   0.50    1.31    --  101.75-125.00  60.00  100
 30  \w     55.00  80.00   0.50    1.31    --  101.75 -86.00  85.00   50
 31  \w     36.00  70.00   0.50    1.31    --  101.75 -94.00 150.00   68
 32  \w     41.00  67.00   0.50    1.31    --  101.75 -45.00  90.00   52
 33  \w     52.00  78.00   0.50    1.31    --  101.75 -15.00  90.00   52
 34  \w     84.00 164.00   0.50    1.31    --  101.75  15.00 150.00  160
 35  \w     84.00 116.00   0.50    1.31    --  101.75  61.00  90.00   64
 36  \w     87.00 113.00   0.50    1.31    --  101.75  30.00 150.00   52
 37  \w     84.00 163.00   0.50    1.31    --  101.75  61.00 150.00  158
 38  \w     63.00  89.00   0.50    1.31    --  101.75 -61.00 -60.00   52
 39  \w     45.00  71.00   0.50    1.31    --  101.75 -45.00-120.00   52
 40  \w     31.00 119.00   0.50    1.31    --  101.75 -62.00 -35.13  176
 41  \w     63.00  89.00   0.50    1.31    --  101.75 -94.00-150.00   52
 42  \w     59.00  95.00   0.50    1.31    --  101.75-125.00-120.00   72
 43  \w     46.00  95.00   0.50    1.31    --  101.75-125.00 -30.00   98
 44  \w     32.00  72.00   0.50    1.31    --  101.75 -30.00  30.00   80
 45  \w     30.00  98.00   0.50    1.31    --  101.75 -77.00 -30.00  136
 46  \w     28.00  64.00   0.50    1.31    --  101.75 -20.00-128.39   72
 47  \w     36.00  62.00   0.50    1.31    --  101.75 -61.00 -90.00   52
 48  \w     30.00  58.00   0.50    1.31    --  101.75 -45.00 -30.00   56
 49  \w     34.00 117.00   0.50    1.31    --  101.75-125.00 -90.00  166
 50  \w     29.00  61.00   0.50    1.31    --  101.75 -94.00-180.00   64
 51  \w     33.00 114.00   0.50    1.31    --  101.75-125.00-180.00  162
 52  \w     31.00 108.00   0.50    1.31    --  101.75 -45.00-180.00  154
 53  \w     30.00  56.00   0.50    1.31    --  101.75-125.00-150.00   52
 54  \w     -8.00  78.00   0.50    0.33    --   46.12 -99.00 -60.00  172
 55  \w     27.00  86.00   0.50    1.31    --  101.75 -30.00-150.00  118
 56  \w    -26.00  74.00   0.50    0.33    --   46.12 -86.00  85.00  200
 57  \w     33.00  61.00   0.50    1.31    --  101.75 -15.00 150.00   56
 58  \w    -74.00  27.00   0.50    0.33    --  -46.12  86.00-156.00  202
 59  \w    -61.00  28.00   0.50    0.33    --  -46.12  38.00 120.00  178
 60  \w   -113.00 -73.00   0.50    0.33    --  -46.12-125.00 -30.00   80
 61  \w   -117.00 -87.00   0.50    0.33    --  -46.12-125.00-150.00   60
 62  \w   -158.00 -99.00   0.50    1.31    -- -100.00 -86.00  85.00  118
 63  \w   -128.00 -27.00   0.50    1.31    -- -100.00  86.00-156.00  202
 64  \w   -127.00 -89.00   0.50    1.31    -- -100.00 139.00-143.68   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0046583000
_diffrn_orient_matrix_UB_12      -0.0917324000
_diffrn_orient_matrix_UB_13      0.0504152000
_diffrn_orient_matrix_UB_21      0.1848872000
_diffrn_orient_matrix_UB_22      -0.0832543000
_diffrn_orient_matrix_UB_23      -0.0362667000
_diffrn_orient_matrix_UB_31      0.1649516000
_diffrn_orient_matrix_UB_32      0.0496040000
_diffrn_orient_matrix_UB_33      0.0321002000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            34065
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.668
_diffrn_reflns_theta_min         2.005
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.306
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45g (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    1.262
_exptl_crystal_description       needle
_exptl_crystal_F_000             660
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.0015(3)
_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   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     503
_refine_ls_number_reflns         6603
_refine_ls_number_restraints     451
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0468
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0665P)^2^+0.7213P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1272
_refine_ls_wR_factor_ref         0.1302
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6018
_reflns_number_total             6603
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce01848k2.cif
_cod_data_source_block           god-b05
_cod_depositor_comments
'Adding full bibliography for 7232232--7232235.cif.'
_cod_database_code               7232235
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.938
_shelx_estimated_absorpt_t_min   0.828
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C2A-C3A \\sim C3A-C4A \\sim C4A-C5A
 with sigma of 0.02
 C3A-C5A \\sim C2A-C4A
 with sigma of 0.04
 C21-C26A \\sim C21-C26
 with sigma of 0.02
 C22-C23A \\sim C22-C23
 with sigma of 0.02
 C23A-C24A \\sim C23-C24
 with sigma of 0.02
 C26A-C25A \\sim C26-C25
 with sigma of 0.02
 C25A-C24A \\sim C25-C24
 with sigma of 0.02
 C21-C25A \\sim C21-C25
 with sigma of 0.04
 C22-C24A \\sim C22-C24
 with sigma of 0.04
 C23A-C25A \\sim C23-C25
 with sigma of 0.04
 C26A-C24A \\sim C26-C24
 with sigma of 0.04
 C6A-C5A \\sim C4A-C3A \\sim C2A-C1A
 with sigma of 0.02
 C6-C5 \\sim C4-C3 \\sim C2-C1
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C2A \\sim C3A \\sim C4A \\sim C5A: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08
4. Rigid body (RIGU) restrains
 C2A, C3A, C4A, C5A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(H3A)=Sof(C23A)=Sof(H23A)=Sof(C24A)=Sof(H24A)=Sof(C25A)=Sof(C26A)=
 Sof(H26A)=Sof(C6A)=Sof(H6A)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(C2A)=Sof(H2AA)=
 Sof(H2AB)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(C4A)=Sof(H4AA)=Sof(H4AB)=Sof(C5A)=
 Sof(H5AA)=Sof(H5AB)=Sof(O1A)=Sof(C27A)=Sof(H27D)=Sof(H27E)=Sof(H27F)=1-FVAR(1)
 Sof(H3B)=Sof(C23)=Sof(H23)=Sof(C24)=Sof(H24)=Sof(C25)=Sof(C26)=Sof(H26)=
 Sof(C6)=Sof(H6)=Sof(C5)=Sof(H5A)=Sof(H5B)=Sof(C3)=Sof(H3C)=Sof(H3D)=Sof(C1)=
 Sof(H1A)=Sof(H1B)=Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(O1)=
 Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(H27C)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C6(H6), C6A(H6A)
6.b Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C28(H28A,H28B), C15(H15A,H15B), C14(H14A,H14B), C30(H30A,
 H30B), C5(H5A,H5B), C3(H3C,H3D), C1(H1A,H1B), C4(H4A,H4B), C2(H2A,H2B),
 C1A(H1AA,H1AB), C2A(H2AA,H2AB), C3A(H3AA,H3AB), C4A(H4AA,H4AB), C5A(H5AA,H5AB)
6.c Aromatic/amide H refined with riding coordinates:
 N3(H3B), N3(H3A), C9(H9), C23A(H23A), C24A(H24A), C26A(H26A), C23(H23),
 C24(H24), C26(H26), C10(H10), C11(H11), C12(H12)
6.d Fitted hexagon refined as free rotating group:
 C21(C22,C23A,C24A,C25A,C26A)
6.e Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C31(H31A,H31B,H31C), C27(H27A,H27B,
 H27C), C27A(H27D,H27E,H27F)
;
_shelx_res_checksum              44412
_shelx_hkl_checksum              67704
_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 2.266
_oxdiff_exptl_absorpt_empirical_full_min 0.750