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_4507330
_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         'C35 H38 Cl2 N8 O4, C2 H3 O2'
_chemical_formula_sum            'C37 H41 Cl2 N8 O6'
_chemical_formula_weight         764.68
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 104.370(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   30.2048(10)
_cell_length_b                   5.7706(2)
_cell_length_c                   21.9711(10)
_cell_measurement_reflns_used    2482
_cell_measurement_temperature    273(1)
_cell_measurement_theta_max      76.8505
_cell_measurement_theta_min      3.0181
_cell_volume                     3709.7(3)
_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
;
XL, 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(1)
_diffrn_detector_area_resol_mean 10.3953
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
  1 omega -108.00  -16.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -45.0000  120.0000 92

  2 omega -112.00  -23.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -30.0000   30.0000 89

  3 omega   41.00   94.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000   90.0000 53

  4 omega   41.00   99.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000  -90.0000 58

  5 omega   90.00  178.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   45.0000   30.0000 88

  6 omega   38.00  115.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -111.0000 -150.0000 77

  7 omega   39.00   90.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000 -150.0000 51

  8 omega   47.00  137.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -61.0000    0.0000 90
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0135544000
_diffrn_orient_matrix_UB_12      0.0641557000
_diffrn_orient_matrix_UB_13      0.0610398000
_diffrn_orient_matrix_UB_21      -0.0507478000
_diffrn_orient_matrix_UB_22      -0.0367488000
_diffrn_orient_matrix_UB_23      -0.0333665000
_diffrn_orient_matrix_UB_31      0.0039459000
_diffrn_orient_matrix_UB_32      -0.2562714000
_diffrn_orient_matrix_UB_33      0.0201005000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_unetI/netI     0.0562
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12843
_diffrn_reflns_theta_full        70.00
_diffrn_reflns_theta_max         70.00
_diffrn_reflns_theta_min         3.02
_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    2.053
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.646
_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    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1604
_exptl_crystal_size_max          0.3511
_exptl_crystal_size_mid          0.1937
_exptl_crystal_size_min          0.0164
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.00031(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     537
_refine_ls_number_reflns         6966
_refine_ls_number_restraints     191
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0964
_refine_ls_R_factor_gt           0.0579
_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^)+(0.0751P)^2^+0.1445P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1445
_refine_ls_wR_factor_ref         0.1815
_reflns_number_gt                4218
_reflns_number_total             6966
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg3015282_si_002.cif
_cod_data_source_block           C2-K273_itraconazole-cocrystal
_cod_database_code               4507330
_reflns_odcompleteness_completeness 99.41
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13