#------------------------------------------------------------------------------
#$Date: 2016-03-24 13:52:29 +0100 (jue 24 de mar de 2016) $
#$Revision: 179676 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/28/4512831.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_4512831
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 H Br3 N2'
_chemical_formula_sum            'C3 H Br3 N2'
_chemical_formula_weight         304.79
_chemical_name_common            tribromoimidazole
_chemical_name_systematic
;
 2,4,5-tribromo-1H-imidazole
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           40
_space_group_name_Hall           'A 2 -2a'
_space_group_name_H-M_alt        'A m a 2'
_symmetry_space_group_name_Hall  'A 2 -2a'
_symmetry_space_group_name_H-M   'A m a 2'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1305(5)
_cell_length_b                   16.7094(10)
_cell_length_c                   4.0483(2)
_cell_measurement_reflns_used    830
_cell_measurement_temperature    296.00(10)
_cell_measurement_theta_max      28.8992
_cell_measurement_theta_min      3.1542
_cell_volume                     685.27(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_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      296.00(10)
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0191109000
_diffrn_orient_matrix_UB_12      0.0336009000
_diffrn_orient_matrix_UB_13      0.0958633000
_diffrn_orient_matrix_UB_21      0.0026022000
_diffrn_orient_matrix_UB_22      -0.0244880000
_diffrn_orient_matrix_UB_23      0.1429838000
_diffrn_orient_matrix_UB_31      0.0672896000
_diffrn_orient_matrix_UB_32      -0.0086011000
_diffrn_orient_matrix_UB_33      -0.0326663000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_av_unetI/netI     0.0629
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            3381
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_min         3.161
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    17.555
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80042
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
colorless
;
_exptl_crystal_density_diffrn    2.954
_exptl_crystal_description
;
;
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.619
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.128
_refine_ls_abs_structure_details
;
 Flack x determined using 190 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     40
_refine_ls_number_reflns         775
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0401
_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)+(0.0080P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0417
_refine_ls_wR_factor_ref         0.0470
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                539
_reflns_number_total             775
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg501561w_si_002.cif
_cod_data_source_block           tribromoimidazole
_cod_depositor_comments
'Adding full bibliography for 4512828--4512833.cif.'
_cod_original_cell_volume        685.27(7)
_cod_database_code               4512831
#BEGIN Tags that were not found in dictionaries:
_reflns_odcompleteness_completeness 94.33
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.90
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
2. Others
 Fixed Sof: H1(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 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'
'-x, -y, z'
'-x+1/2, y, z'
'x+1/2, -y, z'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, 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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Br2 Br 0.57029(8) -0.17119(5) 0.86821(17) 0.0527(3) Uani 1 1 d . . .
Br1 Br 0.7500 0.11873(9) 0.3236(5) 0.0552(4) Uani 1 2 d S T P
N1 N 0.6410(6) -0.0223(5) 0.5805(17) 0.0332(17) Uani 1 1 d . . .
H1 H 0.5606 -0.0075 0.5502 0.040 Uiso 0.5 1 calc R . .
C2 C 0.7500 0.0182(8) 0.506(3) 0.035(3) Uani 1 2 d S T P
C5 C 0.6843(7) -0.0932(6) 0.7171(19) 0.035(3) Uani 1 1 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 0.0443(5) 0.0492(6) 0.0646(6) 0.0044(9) 0.0040(9) -0.0147(5)
Br1 0.0489(8) 0.0453(9) 0.0716(10) 0.0163(13) 0.000 0.000
N1 0.022(4) 0.037(5) 0.040(4) -0.003(4) -0.004(4) 0.002(4)
C2 0.034(8) 0.031(9) 0.039(8) -0.005(6) 0.000 0.000
C5 0.033(5) 0.033(6) 0.040(6) -0.005(4) -0.005(4) 0.000(4)
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 N1 H1 127.3 . .
C2 N1 C5 105.3(8) . .
C5 N1 H1 127.3 . .
N1 C2 Br1 123.9(6) 3_655 .
N1 C2 Br1 123.9(6) . .
N1 C2 N1 112.2(12) . 3_655
N1 C5 Br2 122.7(6) . .
C5 C5 Br2 128.7(3) 3_655 .
C5 C5 N1 108.6(4) 3_655 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br2 C5 1.846(8) .
Br1 C2 1.834(13) .
N1 H1 0.8600 .
N1 C2 1.331(9) .
N1 C5 1.379(10) .
C2 N1 1.331(9) 3_655
C5 C5 1.330(15) 3_655
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
_geom_torsion_site_symmetry_4
C2 N1 C5 Br2 179.3(6) .
C2 N1 C5 C5 -0.5(8) 3_655
C5 N1 C2 Br1 -178.6(7) .
C5 N1 C2 N1 0.9(13) 3_655
