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_4508143
_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 H29 Cl2 N4 O4, C2 H O4'
_chemical_formula_sum            'C28 H30 Cl2 N4 O8'
_chemical_formula_weight         621.46
_chemical_name_systematic
;
 ? 
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-04-09
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.6413(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.51506(16)
_cell_length_b                   13.3330(2)
_cell_length_c                   20.3036(3)
_cell_measurement_reflns_used    10066
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.0410
_cell_measurement_theta_min      3.9570
_cell_volume                     2827.41(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_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 0.9985
_diffrn_measured_fraction_theta_max 0.9985
_diffrn_measurement_details
;
  1 omega  -75.00  -47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  -90.0000 28

  2 omega  -63.00   18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000 -150.0000 81

  3 omega -130.00  -81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -56.3168  -95.0000   60.0000 49

  4 omega  -78.00    4.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -56.3168   61.0000   60.0000 82

  5 omega -126.00  -79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -56.3168 -126.0000 -180.0000 47

  6 omega -127.00  -80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -56.3168  -95.0000 -150.0000 47

  7 omega  -42.00   14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -56.3168   30.0000 -180.0000 56

  8 omega -125.00  -81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -56.3168  -95.0000  -60.0000 44

  9 omega   46.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.6336  -50.0000  -90.0000 41

 10 omega   58.00  139.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.6336  -64.0000  -60.0000 81

 11 omega   45.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.6336  -25.0000    0.0000 47

 12 omega   40.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.6336  -25.0000  -60.0000 34

 13 omega  120.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.6336   81.0000   52.0000 57

 14 omega  100.00  139.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.6336   50.0000 -180.0000 39

 15 omega   54.00   80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.6336  -38.0000 -180.0000 26

 16 omega  152.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.6336   50.0000 -180.0000 26

 17 omega   62.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.6336  -38.0000   90.0000 31

 18 omega   41.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.6336  -38.0000   60.0000 52

 19 omega  147.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.6336  -12.0000 -150.0000 31

 20 omega   69.00  125.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.6336  -12.0000 -150.0000 56

 21 omega  -76.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -19.0000    0.0000 142

 22 omega  -73.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000  -60.0000 104

 23 omega -129.00  -23.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -56.3168  -77.0000  150.0000 106

 24 omega -126.00  -31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -56.3168  -61.0000   90.0000 95

 25 omega   24.00  117.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.3168 -126.0000  -90.0000 93

 26 omega   23.00  129.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.3168   77.0000   30.0000 106

 27 omega   31.00  126.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.3168   61.0000 -150.0000 95

 28 omega   31.00  126.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.3168   61.0000  -30.0000 95

 29 omega -137.00  -38.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000  -77.0000  -90.0000 99

 30 omega   81.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.6336   38.0000  150.0000 97

 31 omega   39.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.6336 -112.0000  120.0000 77

 32 omega   68.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.6336   25.0000   90.0000 110
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0304237000
_diffrn_orient_matrix_UB_12      0.0988943000
_diffrn_orient_matrix_UB_13      0.0341671000
_diffrn_orient_matrix_UB_21      -0.1176699000
_diffrn_orient_matrix_UB_22      0.0154148000
_diffrn_orient_matrix_UB_23      -0.0516485000
_diffrn_orient_matrix_UB_31      -0.0835317000
_diffrn_orient_matrix_UB_32      -0.0578105000
_diffrn_orient_matrix_UB_33      0.0447030000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21015
_diffrn_reflns_theta_full        71.82
_diffrn_reflns_theta_max         71.82
_diffrn_reflns_theta_min         3.97
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    2.566
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         5429
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0435
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0537P)^2^+1.4708P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1171
_reflns_number_gt                4748
_reflns_number_total             5429
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg400638g_si_001.cif
_cod_data_source_block           Keto-1
_cod_original_cell_volume        2827.40(8)
_cod_database_code               4508143
_chemical_oxdiff_formula         'c28 h30 cl2 n4 o8'
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97