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_4508144
_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, C4 H4 O4'
_chemical_formula_sum            'C30 H32 Cl2 N4 O8'
_chemical_formula_weight         647.50
_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             2013-04-22
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                96.238(4)
_cell_angle_beta                 98.973(4)
_cell_angle_gamma                105.330(5)
_cell_formula_units_Z            2
_cell_length_a                   10.5094(6)
_cell_length_b                   11.7425(6)
_cell_length_c                   13.4568(5)
_cell_measurement_reflns_used    6497
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.9810
_cell_measurement_theta_min      3.3641
_cell_volume                     1562.26(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 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details
;
  1 omega  -72.00    6.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -77.0000 -180.0000 78

  2 omega  -31.00   60.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   38.0000  -30.0000 91

  3 omega  -93.00  -15.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -56.8839  125.0000    0.0000 78

  4 omega  -76.00   16.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -56.8839   45.0000  -30.0000 92

  5 omega -123.00  -76.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -56.8839  -45.0000  150.0000 47

  6 omega  -89.00  -11.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -56.8839  125.0000   90.0000 78

  7 omega -129.00   24.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -56.8839    0.0000  -30.0000 153

  8 omega  -49.00  -23.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -56.8839  -45.0000  150.0000 26

  9 omega  -90.00  -54.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -56.8839  125.0000 -150.0000 36

 10 omega  -63.00  -10.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000   50.0000  150.0000 53

 11 omega  -80.00    3.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000   77.0000    0.0000 83

 12 omega  -83.00  -50.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000   50.0000  -90.0000 33

 13 omega  -49.00  -22.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000   50.0000  -90.0000 27

 14 omega   40.00   77.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677  -50.0000 -150.0000 37

 15 omega  118.00  170.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677  112.0000   60.0000 52

 16 omega   56.00   85.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677  -97.0000    2.0000 29

 17 omega   81.00  167.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677   77.0000  150.0000 86

 18 omega   65.00   98.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677 -104.0000 -136.0000 33

 19 omega   95.00  124.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677 -131.0000   34.0000 29

 20 omega   99.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677   50.0000   60.0000 76

 21 omega   40.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677  -50.0000   30.0000 39

 22 omega  148.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677   50.0000 -120.0000 29

 23 omega   86.00  125.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677   50.0000 -120.0000 39

 24 omega   39.00  156.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677  -91.0000   43.0000 117

 25 omega  102.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677  112.0000   90.0000 76

 26 omega   78.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677   77.0000  120.0000 97

 27 omega   84.00  170.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677   77.0000 -180.0000 86

 28 omega   43.00   68.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677  -50.0000   90.0000 25

 29 omega   43.00   70.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677  -50.0000 -180.0000 27

 30 omega   78.00  129.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677   77.0000   90.0000 51

 31 omega   41.00   76.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677  -50.0000  150.0000 35

 32 omega   53.00   92.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677    0.0000  -60.0000 39

 33 omega   59.00  106.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677  -95.0000 -114.0000 47

 34 omega  149.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677  112.0000  -60.0000 27

 35 omega   89.00  114.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677 -108.0000  149.0000 25

 36 omega   36.00   70.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.7677 -108.0000  149.0000 34
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1356662000
_diffrn_orient_matrix_UB_12      0.0131781000
_diffrn_orient_matrix_UB_13      -0.0342667000
_diffrn_orient_matrix_UB_21      0.0239766000
_diffrn_orient_matrix_UB_22      0.1363040000
_diffrn_orient_matrix_UB_23      0.0097231000
_diffrn_orient_matrix_UB_31      0.0708050000
_diffrn_orient_matrix_UB_32      0.0149348000
_diffrn_orient_matrix_UB_33      0.1118265000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10197
_diffrn_reflns_theta_full        71.12
_diffrn_reflns_theta_max         71.12
_diffrn_reflns_theta_min         3.37
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    2.346
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60803
_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    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.710
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.699
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         5896
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.700
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0710
_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          0.2215
_refine_ls_wR_factor_ref         0.2332
_reflns_number_gt                5120
_reflns_number_total             5896
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg400638g_si_001.cif
_cod_data_source_block           Keto-2
_cod_original_cell_volume        1562.27(13)
_cod_database_code               4508144
_chemical_oxdiff_formula         'c26 h28 cl2 n4 o4'
_reflns_odcompleteness_completeness 99.35
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97