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_4507329
_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                 105.111(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   30.181(3)
_cell_length_b                   5.7140(6)
_cell_length_c                   21.6818(18)
_cell_measurement_reflns_used    3154
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      76.9290
_cell_measurement_theta_min      2.8996
_cell_volume                     3609.8(6)
_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      123.01(10)
_diffrn_detector_area_resol_mean 10.3953
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
  1 omega -116.00  -28.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -19.0000  -90.0000 44

  2 omega  -38.00   18.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   37.0000   60.0000 28

  3 omega  -30.00   24.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   30.0000  -60.0000 27

  4 omega   65.00   93.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       43.8187  169.0000 -162.0000 14

  5 omega   88.00  174.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000   90.0000 43

  6 omega   38.00   82.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000    0.0000 22

  7 omega   46.00   98.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000   60.0000 26

  8 omega   91.00  177.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   45.0000 -180.0000 43

  9 omega  109.00  173.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  111.0000   30.0000 32

 10 omega   37.00  103.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000  -30.0000 33
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0514449000
_diffrn_orient_matrix_UB_12      -0.0070088000
_diffrn_orient_matrix_UB_13      -0.0351463000
_diffrn_orient_matrix_UB_21      -0.0085253000
_diffrn_orient_matrix_UB_22      -0.1729513000
_diffrn_orient_matrix_UB_23      0.0502227000
_diffrn_orient_matrix_UB_31      -0.0089148000
_diffrn_orient_matrix_UB_32      0.2062748000
_diffrn_orient_matrix_UB_33      0.0408153000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12636
_diffrn_reflns_theta_full        68.00
_diffrn_reflns_theta_max         69.98
_diffrn_reflns_theta_min         3.03
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.110
_exptl_absorpt_correction_T_max  0.843
_exptl_absorpt_correction_T_min  0.613
_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    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1604
_exptl_crystal_size_max          0.3834
_exptl_crystal_size_mid          0.1639
_exptl_crystal_size_min          0.091
_refine_diff_density_max         0.781
_refine_diff_density_min         -0.720
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.00080(12)
_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   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     546
_refine_ls_number_reflns         6773
_refine_ls_number_restraints     141
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0612
_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^)+(0.0656P)^2^+2.5571P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1491
_refine_ls_wR_factor_ref         0.1611
_reflns_number_gt                5400
_reflns_number_total             6773
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg3015282_si_002.cif
_cod_data_source_block           C2-K123_itraconazole-cocrystal
_cod_original_cell_volume        3609.9(6)
_cod_database_code               4507329
_chemical_oxdiff_formula         'C37 H41 Cl2 N8 O6'
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.79