Cocrystals of zonisamide: physicochemical characterization and sustained release solid forms
Aitipamula, Srinivasulu; Cadden, Joseph; Chow, Pui Shan; CrystEngComm 20 (2018) 2923–; doi:10.1039/C8CE00084K

data_7230482
_publ_section_title
;
 Cocrystals of zonisamide: physicochemical characterization and sustained
 release solid forms
;
_journal_issue                   21
_journal_name_full               CrystEngComm
_journal_page_first              2923
_journal_paper_doi               10.1039/C8CE00084K
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C8 H8 N2 O3 S, C8 H10 N4 O2'
_chemical_formula_sum            'C16 H18 N6 O5 S'
_chemical_formula_weight         406.42
_chemical_melting_point          452
_chemical_name_systematic        Zonisamide:Caffeine
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-03-22
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2018-03-26 deposited with the CCDC.
2018-04-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.8550(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.59020(10)
_cell_length_b                   13.30840(10)
_cell_length_c                   14.24360(10)
_cell_measurement_reflns_used    22621
_cell_measurement_temperature    297.3(4)
_cell_measurement_theta_max      67.0200
_cell_measurement_theta_min      4.5800
_cell_volume                     1816.96(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.3(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2945
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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    -26.00   8.00   0.25    2.50    --   40.62 -22.00  54.00  136
  2  \w     50.00  76.00   0.25    2.50    --   40.62  57.00 -60.00  104
  3  \w     24.00 118.00   0.25    2.50    --   40.62  22.00-139.00  376
  4  \w     72.00 119.00   0.25    5.00    --  106.56  22.00-139.00  188
  5  \w    116.00 177.00   0.25    5.00    --  106.56  77.00-180.00  244
  6  \w    111.00 146.00   0.25    5.00    --  106.56  61.00 -60.00  140
  7  \w    102.00 170.00   0.25    5.00    --  106.56 125.00  60.00  272
  8  \w    118.00 144.00   0.25    5.00    --  106.56  77.00 150.00  104
  9  \w     77.00 103.00   0.25    5.00    --  106.56  61.00 120.00  104
 10  \w     77.00 138.00   0.25    5.00    --  106.56  61.00  90.00  244
 11  \w     78.00 119.00   0.25    5.00    --  106.56  61.00  30.00  164
 12  \w     74.00 176.00   0.25    5.00    --  106.56  77.00 120.00  408
 13  \w     77.00 133.00   0.25    5.00    --  106.56  61.00  60.00  224
 14  \w     77.00 168.00   0.25    5.00    --  106.56  61.00 -30.00  364
 15  \w     77.00 103.00   0.25    5.00    --  106.56  61.00 -90.00  104
 16  \w     78.00 103.00   0.25    5.00    --  106.56  61.00-120.00  100
 17  \w     78.00 103.00   0.25    5.00    --  106.56  61.00-150.00  100
 18  \w     77.00 104.00   0.25    5.00    --  106.56  61.00-180.00  108
 19  \w     74.00 178.00   0.25    5.00    --  106.56  77.00-120.00  416
 20  \w     74.00 100.00   0.25    5.00    --  106.56  77.00-180.00  104
 21  \w     74.00 148.00   0.25    5.00    --  106.56  77.00-150.00  296
 22  \w     78.00 105.00   0.25    5.00    --  106.56  61.00 -60.00  108
 23  \w     77.00 104.00   0.25    5.00    --  106.56  61.00   0.00  108
 24  \w     74.00 100.00   0.25    5.00    --  106.56  77.00  30.00  104
 25  \w     75.00 169.00   0.25    5.00    --  106.56  77.00   0.00  376
 26  \w     74.00  99.00   0.25    5.00    --  106.56  77.00  90.00  100
 27  \w     74.00 157.00   0.25    5.00    --  106.56  77.00  60.00  332
 28  \w     74.00 100.00   0.25    5.00    --  106.56  77.00 150.00  104
 29  \w     52.00  86.00   0.25    5.00    --  106.56 -22.00  54.00  136
 30  \w     35.00 135.00   0.25    5.00    --  106.56 -61.00 120.00  400
 31  \w     60.00 121.00   0.25    5.00    --  106.56-125.00  30.00  244
 32  \w     31.00 109.00   0.25    5.00    --  106.56 -94.00  90.00  312
 33  \w     33.00 122.00   0.25    5.00    --  106.56-125.00 -60.00  356
 34  \w     23.00  71.00   0.25    2.50    --   40.62-125.00  30.00  192
 35  \w     23.00  92.00   0.25    2.50    --   40.62-125.00 -60.00  276
 36  \w     24.00  86.00   0.25    5.00    --  106.56 -94.00  30.00  248
 37  \w      2.00  81.00   0.25    2.50    --   40.62 -99.00  60.00  316
 38  \w     13.00  40.00   0.25    2.50    --   40.62  57.00 -60.00  108
 39  \w      8.00  60.00   0.25    2.50    --   40.62  77.00 -30.00  208
 40  \w     12.00 116.00   0.25    2.50    --   40.62  77.00  30.00  416
 41  \w     74.00 100.00   0.25    5.00    --  106.56  77.00 -90.00  104
 42  \w     74.00 148.00   0.25    5.00    --  106.56  77.00 -60.00  296
 43  \w     74.00 100.00   0.25    5.00    --  106.56  77.00 -30.00  104
 44  \w     10.00  71.00   0.25    2.50    --   40.62  77.00 120.00  244
 45  \w    -46.00  -6.00   0.25    2.50    --  -40.62 -22.00  54.00  160
 46  \w    -67.00  -9.00   0.25    2.50    --  -40.62 -77.00 150.00  232
 47  \w   -120.00 -65.00   0.25    2.50    --  -40.62 -22.00  54.00  220
 48  \w    -73.00  16.00   0.25    2.50    --  -40.62  22.00-139.00  356
 49  \w    -92.00  -9.00   0.25    2.50    --  -40.62 -77.00-120.00  332
 50  \w   -116.00 -88.00   0.25    2.50    --  -40.62 -77.00 150.00  112
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0941641000
_diffrn_orient_matrix_UB_12      0.0898088000
_diffrn_orient_matrix_UB_13      0.0271119000
_diffrn_orient_matrix_UB_21      -0.1201169000
_diffrn_orient_matrix_UB_22      0.0727216000
_diffrn_orient_matrix_UB_23      -0.0258157000
_diffrn_orient_matrix_UB_31      -0.0501458000
_diffrn_orient_matrix_UB_32      -0.0054720000
_diffrn_orient_matrix_UB_33      0.1014965000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0081
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            27367
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.048
_diffrn_reflns_theta_max         67.048
_diffrn_reflns_theta_min         5.647
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.977
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47088
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.486
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_preparation
'Prepared by dissolution of equimolar amounts of Zonisamide and Caffeine in methanol solvent'
_exptl_crystal_recrystallization_method
'Crystallised by slow room temperature evaporation of methanol solvent from a solution containing equimolar amounts of zonisamide and caffeine'
_exptl_crystal_size_max          0.462
_exptl_crystal_size_mid          0.398
_exptl_crystal_size_min          0.164
_refine_diff_density_max         0.919
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.0024(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3217
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0504
_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^)+(0.0840P)^2^+1.2702P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1446
_refine_ls_wR_factor_ref         0.1446
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3205
_reflns_number_total             3217
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce00084k2.cif
_cod_data_source_block           ZNS-CAF
_cod_depositor_comments
'Adding full bibliography for 7230481--7230482.cif.'
_cod_database_code               7230482
_chemical_oxdiff_formula         'C16 H18 N6 O5 S'
_shelx_estimated_absorpt_t_max   0.738
_shelx_estimated_absorpt_t_min   0.462
_reflns_odcompleteness_completeness 99.88
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C4(H4), C3(H3), C13(H13)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              3490
_olex2_date_sample_data_collection 2018-03-14
_olex2_exptl_crystal_mounting_method
'Mounted on a needle tip and secured in place with glue'
_olex2_submission_original_sample_id S17-70-A2
_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 1.831
_oxdiff_exptl_absorpt_empirical_full_min 0.520