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_4508145
_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 H5 O4'
_chemical_formula_sum            'C30 H33 Cl2 N4 O8'
_chemical_formula_weight         648.50
_chemical_name_systematic
;
 ? 
;
_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             2013-04-19
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                95.287(6)
_cell_angle_beta                 99.302(7)
_cell_angle_gamma                104.429(7)
_cell_formula_units_Z            2
_cell_length_a                   10.5261(8)
_cell_length_b                   11.7297(9)
_cell_length_c                   13.4580(11)
_cell_measurement_reflns_used    4015
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8971
_cell_measurement_theta_min      3.3574
_cell_volume                     1572.7(2)
_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
;
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
;
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 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details
;
  1 omega  -39.00   34.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -77.0000 -150.0000 73

  2 omega    1.00   74.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000  -60.0000 73

  3 omega  -74.00  -44.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -77.0000 -150.0000 30

  4 omega    4.00   31.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000    0.0000 27

  5 omega  -96.00  -18.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -      -56.8839  125.0000   60.0000 78

  6 omega  -70.00    7.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -      -56.8839   77.0000  -30.0000 77

  7 omega  -15.00   18.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -      -56.8839   45.0000   90.0000 33

  8 omega -138.00    2.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -      -56.8839    0.0000   90.0000 140

  9 omega  -67.00  -20.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -      -56.8839   45.0000   90.0000 47

 10 omega   22.00   50.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -       56.8839   45.0000 -150.0000 28

 11 omega   52.00   87.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -       56.8839   45.0000 -150.0000 35

 12 omega  -45.00   15.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -      -64.5000   25.0000  -90.0000 60

 13 omega  -37.00   -4.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -      -64.5000   77.0000   60.0000 33

 14 omega  -95.00  -38.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -      -64.5000   77.0000   60.0000 57

 15 omega  -27.00    0.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -      -64.5000  112.0000 -120.0000 27

 16 omega  -89.00  -52.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -      -64.5000  112.0000 -120.0000 37

 17 omega  -97.00    4.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -      -64.5000   72.0000 -100.0000 101

 18 omega   84.00  119.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -      113.7677   50.0000    0.0000 35

 19 omega   44.00   71.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -      113.7677  -50.0000   90.0000 27

 20 omega  135.00  168.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -      113.7677   50.0000 -120.0000 33

 21 omega  124.00  150.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -      113.7677  -25.0000  -30.0000 26

 22 omega   52.00   82.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -      113.7677  -50.0000 -150.0000 30

 23 omega   85.00  127.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -      113.7677   50.0000 -120.0000 42

 24 omega   53.00   78.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -      113.7677  -50.0000 -120.0000 25

 25 omega   86.00  157.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -      113.7677  -91.0000 -158.0000 71

 26 omega   40.00   76.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -      113.7677  -50.0000 -180.0000 36

 27 omega  130.00  174.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -      113.7677  -25.0000   30.0000 44

 28 omega   54.00  166.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -      113.7677   25.0000  -30.0000 112

 29 omega  112.00  141.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -      113.7677  112.0000  -90.0000 29

 30 omega  147.00  174.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -      113.7677  112.0000  -90.0000 27

 31 omega  148.00  176.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -      113.7677  112.0000    0.0000 28

 32 omega  111.00  166.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -      113.7677  112.0000 -120.0000 55

 33 omega  101.00  159.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -      113.7677  112.0000 -150.0000 58

 34 omega  114.00  161.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -      113.7677  112.0000  150.0000 47

 35 omega   46.00   73.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -      113.7677  -50.0000  -90.0000 27

 36 omega   40.00   74.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -      113.7677  -50.0000  120.0000 34

 37 omega  101.00  178.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -      113.7677  112.0000 -180.0000 77

 38 omega  144.00  170.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -      113.7677   50.0000    0.0000 26

 39 omega   50.00  120.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -      113.7677 -124.0000   46.0000 70

 40 omega   38.00  120.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -      113.7677 -132.0000 -112.0000 82

 41 omega   72.00  110.00   1.0000    2.0300
omega____ theta____ kappa____ phi______ frames
    -      113.7677  -99.0000   83.0000 38
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0582998000
_diffrn_orient_matrix_UB_12      0.0389825000
_diffrn_orient_matrix_UB_13      0.0912379000
_diffrn_orient_matrix_UB_21      -0.1133173000
_diffrn_orient_matrix_UB_22      -0.1163738000
_diffrn_orient_matrix_UB_23      -0.0246453000
_diffrn_orient_matrix_UB_31      0.0864121000
_diffrn_orient_matrix_UB_32      -0.0607382000
_diffrn_orient_matrix_UB_33      0.0691877000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10236
_diffrn_reflns_theta_full        71.03
_diffrn_reflns_theta_max         71.03
_diffrn_reflns_theta_min         3.36
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    2.330
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64697
_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            yellow
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             678
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.622
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.437
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     407
_refine_ls_number_reflns         5930
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.437
_refine_ls_R_factor_all          0.0931
_refine_ls_R_factor_gt           0.0749
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_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          0.2136
_refine_ls_wR_factor_ref         0.2341
_reflns_number_gt                4407
_reflns_number_total             5930
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg400638g_si_001.cif
_cod_data_source_block           Keto-3
_cod_original_cell_volume        1572.8(2)
_cod_database_code               4508145
_chemical_oxdiff_formula         'c26 h28 cl2 n4'
_reflns_odcompleteness_completeness 99.41
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97