The structural landscape of heteroaryl-2-imidazoles: competing halogen- and hydrogen-bond interactions
Aakeröy, Christer B.; Wijethunga, Tharanga K.; Haj, Mohammad Abul; Desper, John; Moore, Curtis; CrystEngComm 16 (2014) 7218–; doi:10.1039/C4CE00803K

data_7217406
_publ_section_title
;
 The structural landscape of heteroaryl-2-imidazoles: competing halogen-
 and hydrogen-bond interactions
;
_journal_issue                   31
_journal_name_full               CrystEngComm
_journal_page_first              7218
_journal_paper_doi               10.1039/C4CE00803K
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety
;
(C8 H7 N3)2 (C6 F3 I3)
;
_chemical_formula_sum            'C22 H14 F3 I3 N6'
_chemical_formula_weight         800.09
_chemical_name_systematic
;
TW-1-57 [2-(3-pyridyl)-imidazole]2,  1,3,5-F3-2,4,6-I3-benzene
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   32.4147(16)
_cell_length_b                   9.9354(5)
_cell_length_c                   7.4776(4)
_cell_measurement_reflns_used    9957
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      32.56
_cell_measurement_theta_min      2.51
_cell_volume                     2408.2(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.902
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            18651
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         32.58
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    3.941
_exptl_absorpt_correction_T_max  0.7979
_exptl_absorpt_correction_T_min  0.4050
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.207
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1496
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.906
_refine_diff_density_min         -0.858
_refine_diff_density_rms         0.139
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         3961
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.157
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0343
_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^)+(0.0200P)^2^+10.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0781
_refine_ls_wR_factor_ref         0.0805
_reflns_number_gt                3361
_reflns_number_total             3961
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             7216662
_cod_data_source_file            c4ce00803k2.cif
_cod_data_source_block           A2D9
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      Pbcn
_cod_database_code               7217406