Ketoconazole Salt and Co-crystals with Enhanced Aqueous Solubility
Martin, Flavia A.; Pop, Mihaela M.; Borodi, Gheorghe; Filip, Xenia; Kacso, Irina; Crystal Growth & Design 13 (2013) 4295–; doi:10.1021/cg400638g

data_4508146
_publ_section_title
;
 Ketoconazole Salt and Co-crystals with Enhanced Aqueous Solubility
;
_journal_issue                   10
_journal_name_full               'Crystal Growth &amp; Design'
_journal_page_first              4295
_journal_paper_doi               10.1021/cg400638g
_journal_volume                  13
_journal_year                    2013
_chemical_formula_moiety         'C26 H28 Cl2 N4 O4, C6 H10 O4'
_chemical_formula_sum            'C32 H38 Cl2 N4 O8'
_chemical_formula_weight         677.56
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-03-29
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                92.623(4)
_cell_angle_beta                 93.859(4)
_cell_angle_gamma                103.791(4)
_cell_formula_units_Z            2
_cell_length_a                   5.8721(3)
_cell_length_b                   8.3797(4)
_cell_length_c                   34.4919(14)
_cell_measurement_reflns_used    5174
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8406
_cell_measurement_theta_min      3.8581
_cell_volume                     1641.21(14)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_collection
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.4335
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details
;
  1 omega  -56.00  -17.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  125.0000   58.0000 39

  2 omega    3.00   75.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000  -90.0000 72

  3 omega   28.00   67.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000 -180.0000 39

  4 omega  -91.00   -8.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -56.8839   77.0000    0.0000 83

  5 omega  -84.00  -44.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -56.8839  148.0000 -175.0000 40

  6 omega   26.00  132.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.8839   45.0000  150.0000 106

  7 omega   91.00  131.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.8839 -148.0000  135.0000 40

  8 omega   37.00   88.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.8839 -148.0000  135.0000 51

  9 omega   21.00  132.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.8839   77.0000 -150.0000 111

 10 omega -102.00   -6.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000  -25.0000 -120.0000 96

 11 omega  -79.00   11.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000   77.0000 -180.0000 90

 12 omega  -28.00   14.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000   25.0000   60.0000 42

 13 omega   41.00   76.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677  -50.0000 -180.0000 35

 14 omega  102.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677  112.0000  -60.0000 75

 15 omega  129.00  158.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677  -25.0000   60.0000 29

 16 omega   50.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677  -50.0000  -30.0000 29

 17 omega  127.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677   50.0000   60.0000 51

 18 omega   44.00   71.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677  -50.0000  150.0000 27

 19 omega   89.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677  148.0000    4.0000 26

 20 omega   84.00  119.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677   50.0000   60.0000 35

 21 omega  126.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677  -25.0000  150.0000 49

 22 omega  140.00  173.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677  148.0000    4.0000 33

 23 omega   37.00   67.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677 -125.0000  121.0000 30

 24 omega   51.00  108.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677   25.0000  150.0000 57

 25 omega   80.00  132.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677 -148.0000  135.0000 52

 26 omega   40.00   77.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677  -50.0000  -90.0000 37

 27 omega   62.00  132.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677   25.0000   30.0000 70

 28 omega  153.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677   25.0000   30.0000 25

 29 omega  115.00  174.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677  112.0000  -90.0000 59

 30 omega  104.00  133.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677  112.0000  -30.0000 29

 31 omega  132.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677  112.0000   60.0000 43

 32 omega   49.00  111.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677 -125.0000  160.0000 62

 33 omega  148.00  173.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677  112.0000  -30.0000 25

 34 omega   51.00   78.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677  -50.0000  -60.0000 27

 35 omega   81.00  146.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677  -91.0000  -88.0000 65

 36 omega   37.00   74.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677  -91.0000  -88.0000 37
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0939249000
_diffrn_orient_matrix_UB_12      -0.0159839000
_diffrn_orient_matrix_UB_13      0.0420730000
_diffrn_orient_matrix_UB_21      -0.1473750000
_diffrn_orient_matrix_UB_22      0.1155537000
_diffrn_orient_matrix_UB_23      0.0151418000
_diffrn_orient_matrix_UB_31      -0.2071549000
_diffrn_orient_matrix_UB_32      -0.1495771000
_diffrn_orient_matrix_UB_33      0.0035732000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            9895
_diffrn_reflns_theta_full        70.98
_diffrn_reflns_theta_max         70.98
_diffrn_reflns_theta_min         3.86
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    2.255
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.599
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.318
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     418
_refine_ls_number_reflns         6186
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.318
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0689
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1900
_refine_ls_wR_factor_ref         0.2033
_reflns_number_gt                5163
_reflns_number_total             6186
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg400638g_si_001.cif
_cod_data_source_block           Keto-4
_cod_original_cell_volume        1641.20(13)
_cod_database_code               4508146
_chemical_oxdiff_formula         'c26 h28 cl2 n4 o4'
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97