Evidence of Weak Halogen Bonding: New Insights on Itraconazole and its Succinic Acid Cocrystal
Nonappa,; Lahtinen, Manu; Kolehmainen, Erkki; Haarala, Jorma; Shevchenko, Anna; Crystal Growth & Design 13 (2013) 346–; doi:10.1021/cg3015282

data_4507328
_publ_section_title
;
 Evidence of Weak Halogen Bonding: New Insights on Itraconazole and its
 Succinic Acid Cocrystal
;
_journal_issue                   1
_journal_name_full               'Crystal Growth &amp; Design'
_journal_page_first              346
_journal_paper_doi               10.1021/cg3015282
_journal_volume                  13
_journal_year                    2013
_chemical_formula_moiety         '0.5(C70 H76 Cl4 N16 O8)'
_chemical_formula_sum            'C35 H38 Cl2 N8 O4'
_chemical_formula_weight         705.63
_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
_cell_angle_alpha                73.297(6)
_cell_angle_beta                 89.003(5)
_cell_angle_gamma                79.571(5)
_cell_formula_units_Z            4
_cell_length_a                   8.6126(5)
_cell_length_b                   20.1032(13)
_cell_length_c                   21.1211(15)
_cell_measurement_reflns_used    5360
_cell_measurement_temperature    273.00(10)
_cell_measurement_theta_max      77.1182
_cell_measurement_theta_min      3.6282
_cell_volume                     3442.4(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_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      273.00(10)
_diffrn_detector_area_resol_mean 5.1977
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
  1 omega -116.00   -5.00   1.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -19.0000  -30.0000 74

  2 omega  -49.00   32.00   1.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   37.0000  150.0000 54

  3 omega    1.00   82.00   1.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       43.8187  -99.0000 -120.0000 54

  4 omega   14.00   62.00   1.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       43.8187   77.0000    0.0000 32

  5 omega   38.00   77.00   1.5000  125.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000   90.0000 26

  6 omega   38.00  116.00   1.5000  125.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -111.0000  150.0000 52

  7 omega   43.00  140.50   1.5000  125.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -77.0000  -30.0000 65

  8 omega   56.00   98.00   1.5000  125.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000 -120.0000 28

  9 omega   90.00  165.00   1.5000  125.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   30.0000 -150.0000 50

 10 omega   38.00   74.00   1.5000  125.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000    0.0000 24

 11 omega   48.00   99.00   1.5000  125.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000  150.0000 34

 12 omega   39.00  115.50   1.5000  125.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -111.0000  -60.0000 51

 13 omega   38.00   56.00   1.5000  125.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000  -60.0000 12

 14 omega   38.00   90.50   1.5000  125.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000   30.0000 35

 15 omega   49.00  109.00   1.5000  125.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000 -180.0000 40

 16 omega   38.00  150.50   1.5000  125.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -15.0000 -180.0000 75
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0056825000
_diffrn_orient_matrix_UB_12      -0.0680656000
_diffrn_orient_matrix_UB_13      0.0575307000
_diffrn_orient_matrix_UB_21      0.0829743000
_diffrn_orient_matrix_UB_22      -0.0438991000
_diffrn_orient_matrix_UB_23      -0.0440035000
_diffrn_orient_matrix_UB_31      0.1618856000
_diffrn_orient_matrix_UB_32      0.0080701000
_diffrn_orient_matrix_UB_33      0.0236839000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0564
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            22223
_diffrn_reflns_theta_full        69.50
_diffrn_reflns_theta_max         69.50
_diffrn_reflns_theta_min         3.63
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.121
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.722
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1480
_exptl_crystal_size_max          0.192
_exptl_crystal_size_mid          0.1722
_exptl_crystal_size_min          0.0135
_refine_diff_density_max         0.775
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     981
_refine_ls_number_reflns         12703
_refine_ls_number_restraints     223
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0648
_refine_ls_shift/su_max          0.044
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0870P)^2^+1.1936P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1668
_refine_ls_wR_factor_ref         0.1896
_reflns_number_gt                8706
_reflns_number_total             12703
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg3015282_si_002.cif
_cod_data_source_block           C1-K273_itraconazole-neat
_cod_original_cell_volume        3442.5(4)
_cod_database_code               4507328
_reflns_odcompleteness_completeness 97.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98