#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:52:29 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179676 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/28/4512828.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4512828
loop_
_publ_author_name
'Andrzejewski, Michał'
'Marciniak, Jędrzej'
'Rajewski, Kacper W.'
'Katrusiak, Andrzej'
_publ_section_title
;
 Halogen and Hydrogen Bond Architectures in Switchable Chains of Di- and
 Trihaloimidazoles
;
_journal_issue                   4
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1658
_journal_paper_doi               10.1021/cg501561w
_journal_volume                  15
_journal_year                    2015
_chemical_formula_moiety         'C3 H2 Br2 N2'
_chemical_formula_sum            'C3 H2 Br2 N2'
_chemical_formula_weight         225.89
_chemical_name_common            dibromoimidazole
_chemical_name_systematic
;
 4,5-dibromo-1H-imidazole
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_Hall           'P 4abw 2nw'
_space_group_name_H-M_alt        'P 41 21 2'
_symmetry_space_group_name_Hall  'P 4abw 2nw'
_symmetry_space_group_name_H-M   'P 41 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-10-21
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.8566(4)
_cell_length_b                   6.8566(4)
_cell_length_c                   25.535(2)
_cell_measurement_temperature    296(2)
_cell_volume                     1200.48(14)
_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_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1342
_diffrn_reflns_av_unetI/netI     0.1396
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            7301
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_min         3.076
_exptl_absorpt_coefficient_mu    13.378
_exptl_absorpt_correction_T_max  0.512
_exptl_absorpt_correction_T_min  0.126
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.500
_exptl_crystal_description       sphere
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.699
_refine_diff_density_min         -0.627
_refine_diff_density_rms         0.146
_refine_ls_abs_structure_details
;
 Flack x determined using 107 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.02(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.888
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     64
_refine_ls_number_reflns         1303
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      0.886
_refine_ls_R_factor_all          0.2279
_refine_ls_R_factor_gt           0.0766
_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/[σ²(Fo²)+(0.0929P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1659
_refine_ls_wR_factor_ref         0.2121
_reflns_Friedel_coverage         0.538
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                467
_reflns_number_total             1303
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg501561w_si_002.cif
_cod_data_source_block           dibromoimidazole
_cod_depositor_comments
'Adding full bibliography for 4512828--4512833.cif.'
_cod_original_cell_volume        1200.51(17)
_cod_database_code               4512828
#BEGIN Tags that were not found in dictionaries:
_shelxl_version_number           2013-4
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 N3-C2
 1.33 with sigma of 0.01
 C5-C4
 1.38 with sigma of 0.01
 N1-C2
 1.34 with sigma of 0.005
 N1-C5 \\sim C4-N3
 with sigma of 0.01
3. Rigid body (RIGU) restrains
 C5, C4, N3
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), N1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+1/2, x+1/2, z+1/4'
'-x, -y, z+1/2'
'y+1/2, -x+1/2, z+3/4'
'x+1/2, -y+1/2, -z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
Br2 Br 0.3250(4) 0.6044(4) 0.65733(9) 0.1037(11) Uani 1 1 d .
Br1 Br 0.7108(4) 0.2214(4) 0.66224(9) 0.1028(11) Uani 1 1 d .
C2 C 0.266(2) 0.174(3) 0.7557(7) 0.082(6) Uani 1 1 d D
H2 H 0.1958 0.1099 0.7817 0.099 Uiso 1 1 calc R
N1 N 0.210(2) 0.340(2) 0.7331(6) 0.081(5) Uani 1 1 d D
H1 H 0.1052 0.4037 0.7402 0.097 Uiso 1 1 calc R
N3 N 0.434(2) 0.112(2) 0.7366(5) 0.068(5) Uani 1 1 d D
C5 C 0.344(2) 0.392(2) 0.6974(6) 0.061(5) Uani 1 1 d D
C4 C 0.485(2) 0.249(3) 0.7010(6) 0.062(5) Uani 1 1 d D
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br2 0.101(2) 0.0847(19) 0.125(2) 0.0307(15) -0.0061(16) 0.0250(14)
Br1 0.0839(19) 0.107(2) 0.118(2) 0.0030(16) 0.0199(15) 0.0195(14)
C2 0.067(17) 0.104(19) 0.076(14) 0.012(14) 0.010(12) 0.031(12)
N1 0.061(11) 0.096(15) 0.087(13) -0.003(10) -0.008(10) 0.035(10)
N3 0.067(11) 0.086(11) 0.052(10) -0.009(7) 0.008(8) 0.029(9)
C5 0.054(12) 0.076(11) 0.053(11) -0.016(9) -0.001(9) 0.018(8)
C4 0.060(10) 0.080(12) 0.045(9) -0.024(8) 0.003(9) 0.019(8)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N3 C2 N1 111.4(15)
C2 N1 C5 109.0(14)
C2 N3 C4 104.5(13)
N1 C5 Br2 123.9(13)
N1 C5 C4 104.2(14)
C4 C5 Br2 131.9(14)
N3 C4 Br1 120.3(12)
N3 C4 C5 111.0(14)
C5 C4 Br1 128.7(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br2 C5 1.784(16)
Br1 C4 1.849(15)
C2 N1 1.335(6)
C2 N3 1.321(11)
N1 C5 1.340(15)
N3 C4 1.353(15)
C5 C4 1.380(11)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
Br2 C5 C4 Br1 -2(3)
Br2 C5 C4 N3 -178.5(14)
C2 N1 C5 Br2 179.2(14)
C2 N1 C5 C4 -1(2)
C2 N3 C4 Br1 -178.6(13)
C2 N3 C4 C5 -2(2)
N1 C2 N3 C4 1(2)
N1 C5 C4 Br1 178.3(13)
N1 C5 C4 N3 2(2)
N3 C2 N1 C5 0(2)
