Mechanochemistry and cocrystallization of 3-iodoethynylbenzoic acid with nitrogen-containing heterocycles: concurrent halogen and hydrogen bonding
Szell, Patrick M. J.; Dragon, Julien; Zablotny, Scott; Harrigan, Stephen R.; Gabidullin, Bulat; Bryce, David L.; New Journal of Chemistry 42 (2018) 10493–; doi:10.1039/C8NJ00437D

data_7057167
_publ_section_title
;
 Mechanochemistry and cocrystallization of 3-iodoethynylbenzoic acid with
 nitrogen-containing heterocycles: concurrent halogen and hydrogen bonding
;
_journal_issue                   13
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              10493
_journal_paper_doi               10.1039/C8NJ00437D
_journal_volume                  42
_journal_year                    2018
_chemical_formula_moiety         'C9 H5 I1 O2, C6 H12 N4'
_chemical_formula_sum            'C15 H17 I N4 O2'
_chemical_formula_weight         412.23
_chemical_melting_point          459
_chemical_name_common            '(3-iodoethynylbenzoic acid)(urotropin)'
_chemical_name_systematic
'(3-iodoethynylbenzoic acid)(hexamethylenetetramine)'
_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   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-01-18 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.304(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.465(5)
_cell_length_b                   16.493(5)
_cell_length_c                   6.958(2)
_cell_measurement_reflns_used    1993
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      17.66
_cell_measurement_theta_min      2.86
_cell_volume                     1627.8(9)
_computing_cell_refinement       'APEX II (Bruker, 2009)'
_computing_data_collection       'APEX II (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'XT (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.2066
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            28340
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_min         1.436
_exptl_absorpt_coefficient_mu    1.980
_exptl_absorpt_correction_T_max  0.745684
_exptl_absorpt_correction_T_min  0.599917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS v.2012/1 (Bruker,2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_description       plate
_exptl_crystal_F_000             816
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetonitrile'
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.154
_refine_diff_density_max         2.072
_refine_diff_density_min         -0.598
_refine_diff_density_rms         0.156
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         28340
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.1813
_refine_ls_R_factor_gt           0.0845
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0372P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1783
_refine_ls_wR_factor_ref         0.2343
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13424
_reflns_number_total             28340
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8nj00437d2.cif
_cod_data_source_block           shelx_CCDC4
_cod_depositor_comments
'Adding full bibliography for 7057163--7057168.cif.'
_cod_original_cell_volume        1627.7(9)
_cod_database_code               7057167
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.631
_shelx_estimated_absorpt_t_max   0.750
_exptl_absorpt_special_details
;
    15845 data (   3716 unique ) involve domain  1 only,  mean I/sigma   2.2
    15717 data (   3685 unique ) involve domain  2 only,  mean I/sigma   1.3
     3740 data (   1362 unique ) involve   2 domains,  mean I/sigma   1.8
;
_shelx_res_checksum              89282