Halogen and Hydrogen Bond Architectures in Switchable Chains of Di- and Trihaloimidazoles
Andrzejewski, Michał; Marciniak, Jędrzej; Rajewski, Kacper W.; Katrusiak, Andrzej; Crystal Growth & Design 15 (2015) 1658–; doi:10.1021/cg501561w

data_4512832
_publ_section_title
;
 Halogen and Hydrogen Bond Architectures in Switchable Chains of Di- and
 Trihaloimidazoles
;
_journal_issue                   4
_journal_name_full               'Crystal Growth &amp; Design'
_journal_page_first              1658
_journal_paper_doi               10.1021/cg501561w
_journal_volume                  15
_journal_year                    2015
_chemical_formula_moiety         'C3 H I3 N2'
_chemical_formula_sum            'C3 H I3 N2'
_chemical_formula_weight         445.76
_chemical_name_common            triiodoimidazole
_chemical_name_systematic
;
2,4,5-triiodo-1H-imidazole
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yab'
_space_group_name_H-M_alt        'P 1 21/a 1'
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-10-20
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90
_cell_angle_beta                 108.219(4)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   9.4587(4)
_cell_length_b                   22.0806(7)
_cell_length_c                   14.0805(5)
_cell_measurement_reflns_used    4392
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.9890
_cell_measurement_theta_min      3.2660
_cell_volume                     2793.34(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 16.2413
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_details
;
  1 omega  -72.00  -23.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -        1.1719   19.0000  -30.0000 49

  2 omega   13.00   89.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -        1.1719   19.0000  -30.0000 76

  3 omega -109.00  -76.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.2292 -125.0000  -60.0000 33

  4 omega -119.00  -94.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.2292 -125.0000   60.0000 25

  5 omega -115.00  -74.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.2292 -125.0000 -150.0000 41

  6 omega -111.00  -81.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.2292 -125.0000  150.0000 30

  7 omega  -22.00   32.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.2292  -99.0000 -150.0000 54

  8 omega  -60.00   98.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       32.5729   19.0000  -90.0000 158

  9 omega  -49.00   89.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -        1.1719   57.0000  120.0000 138

 10 omega -102.00  -35.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -        1.1719 -178.0000 -180.0000 67

 11 omega -118.00   20.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.2292  -57.0000    0.0000 138

 12 omega -127.00  -79.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.2292  -99.0000    0.0000 48

 13 omega -118.00  -10.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.2292  -57.0000   90.0000 108

 14 omega   -3.00  110.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       32.5729 -125.0000  -60.0000 113
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0257996000
_diffrn_orient_matrix_UB_12      0.0203622000
_diffrn_orient_matrix_UB_13      0.0407478000
_diffrn_orient_matrix_UB_21      0.0282794000
_diffrn_orient_matrix_UB_22      0.0193825000
_diffrn_orient_matrix_UB_23      -0.0299455000
_diffrn_orient_matrix_UB_31      -0.0690396000
_diffrn_orient_matrix_UB_32      0.0155413000
_diffrn_orient_matrix_UB_33      -0.0159937000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0946
_diffrn_reflns_av_unetI/netI     0.1492
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            28491
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.601
_diffrn_reflns_theta_min         3.562
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    9.994
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96509
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    3.180
_exptl_crystal_description
;
;
_exptl_crystal_F_000             2304
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         2.142
_refine_diff_density_min         -1.487
_refine_diff_density_rms         0.193
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         6078
_refine_ls_number_restraints     77
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.2209
_refine_ls_R_factor_gt           0.0710
_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^)+(0.0630P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1983
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2177
_reflns_number_total             6078
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cg501561w_si_002.cif
_cod_data_source_block           triiodoimidazole
_cod_depositor_comments
'Adding full bibliography for 4512828--4512833.cif.'
_cod_original_cell_volume        2793.33(18)
_cod_database_code               4512832
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
2. Restrained distances
 I3C-C5C = C2C-I1C = C4C-I2C = I3B-C5B = C4B-I2B = I3A-C5A = C4A-I2A = I1A-C2A
 2.07 with sigma of 0.01
 C2C-N3C \\sim C2B-N3B \\sim C2A-N3A
 with sigma of 0.004
 N1C-C2C \\sim N1B-C2B \\sim N1A-C2A
 with sigma of 0.004
 C5C-C4C \\sim C5B-C4B \\sim C5A-C4A
 with sigma of 0.001
 C5C-C2C \\sim C2B-C5B \\sim C5A-C2A
 with sigma of 0.001
 C4A-N3A \\sim N3B-C4B \\sim N3C-C4C
 with sigma of 0.001
 C5A-N1A \\sim C5B-N1B \\sim C5C-N1C
 with sigma of 0.001
 N3A-C4A \\sim C5A-N1A \\sim N3B-C4B \\sim C5B-N1B \\sim N3C-C4C \\sim C5C-N1C
 with sigma of 0.05
3. Rigid bond restraints
 I1B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
N3B \\sim N1B \\sim C2B \\sim C4B \\sim C5B: within 1.7A with sigma of 0.04 and
sigma for terminal atoms of 0.08
I1B: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
Uanis(I2C) \\sim Ueq: with sigma of 0.004 and sigma for terminal atoms of 0.008
5.a Aromatic/amide H refined with riding coordinates:
 N3C(H3C), N3B(H3B), N3A(H3A)
;
_olex2_submission_special_instructions 'No special instructions were received'