#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/61/2226151.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2226151
loop_
_publ_author_name
'Garden, Simon J.'
'Gama, Paola E.'
'Tiekink, Edward R. T.'
'Wardell, James L.'
'Wardell, Solange M. S. V.'
'Howie, R. Alan'
_publ_section_title
;
 1,3-Bis(4-bromophenyl)imidazolium chloride dihydrate
;
_journal_coeditor_code           HB5456
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1438
_journal_page_last               o1439
_journal_paper_doi               10.1107/S1600536810018581
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H11 Br2 N2 +, Cl -, 2H2 O'
_chemical_formula_moiety         'C15 H11 Br2 N2 +, Cl -, 2(H2 O)'
_chemical_formula_sum            'C15 H15 Br2 Cl N2 O2'
_chemical_formula_weight         450.56
_chemical_name_systematic
;
1,3-Bis(4-bromophenyl)imidazolium chloride dihydrate
;
_space_group_IT_number           94
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4n 2n'
_symmetry_space_group_name_H-M   'P 42 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.8377(7)
_cell_length_b                   17.8377(7)
_cell_length_c                   5.12700(10)
_cell_measurement_reflns_used    2084
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.9
_cell_volume                     1631.33(10)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  '10 cm confocal mirrors'
_diffrn_radiation_source         'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.048
_diffrn_reflns_av_sigmaI/netI    0.028
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            13675
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         3.2
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.140
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.665
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.835
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.40
_refine_diff_density_min         -0.69
_refine_ls_abs_structure_details 'Flack (1983), 742 Friedel pairs'
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     108
_refine_ls_number_reflns         1885
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.040
_refine_ls_R_factor_gt           0.032
_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/[σ²(Fo²)+(0.0285P)²+2.7306P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.071
_refine_ls_wR_factor_ref         0.075
_reflns_number_gt                1654
_reflns_number_total             1885
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5456.cif
_cod_data_source_block           I
_cod_database_code               2226151
_cod_database_fobs_code          2226151
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'y, x, -z'
'-y, -x, -z'
'-y+1/2, x+1/2, z+1/2'
'y+1/2, -x+1/2, z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.100493(18) 0.463088(18) 0.00124(12) 0.02761(11) Uani d . 1 . .
Cl Cl1 0.13502(7) 0.13502(7) 0.5000 0.0552(4) Uani d S 1 . .
O O1 0.20493(17) 0.20493(17) 1.0000 0.0681(15) Uani d SD 1 . .
H H1O 0.186(5) 0.181(5) 1.125(8) 0.102 Uiso d D 1 . .
O O2 0.0584(3) 0.0584(3) 1.0000 0.0794(16) Uani d SD 1 . .
H H2O 0.067(5) 0.087(4) 0.867(10) 0.119 Uiso d D 1 . .
N N1 0.32639(19) 0.38584(18) 0.8472(7) 0.0274(7) Uani d . 1 . .
C C1 0.32553(19) 0.32553(19) 1.0000 0.0270(9) Uani d S 1 . .
H H1 0.2879 0.2879 1.0000 0.032 Uiso calc SR 1 . .
C C2 0.3893(3) 0.4253(3) 0.9090(14) 0.083(3) Uani d . 1 . .
H H2 0.4044 0.4714 0.8322 0.100 Uiso calc R 1 . .
C C3 0.2714(2) 0.4041(2) 0.6525(7) 0.0252(8) Uani d . 1 . .
C C4 0.2720(2) 0.4748(2) 0.5411(11) 0.0382(13) Uani d . 1 . .
H H4 0.3075 0.5111 0.5974 0.046 Uiso calc R 1 . .
C C5 0.2207(3) 0.4925(3) 0.3464(9) 0.0369(10) Uani d . 1 . .
H H5 0.2209 0.5408 0.2685 0.044 Uiso calc R 1 . .
C C6 0.1696(2) 0.4391(2) 0.2680(7) 0.0267(9) Uani d . 1 . .
C C7 0.1683(2) 0.3694(2) 0.3799(8) 0.0265(9) Uani d . 1 . .
H H7 0.1325 0.3334 0.3241 0.032 Uiso calc R 1 . .
C C8 0.2194(2) 0.3512(2) 0.5749(8) 0.0289(10) Uani d . 1 . .
H H8 0.2185 0.3030 0.6536 0.035 Uiso calc R 1 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Br1 0.02725(18) 0.0350(2) 0.02061(17) 0.00424(13) -0.0019(3) 0.0025(3)
Cl1 0.0652(6) 0.0652(6) 0.0352(8) -0.0031(8) 0.0037(10) -0.0037(10)
O1 0.079(2) 0.079(2) 0.046(3) -0.049(3) -0.009(4) 0.009(4)
O2 0.080(2) 0.080(2) 0.078(4) 0.008(3) 0.018(4) -0.018(4)
N1 0.0252(17) 0.0274(18) 0.0296(19) 0.0075(14) -0.0003(15) 0.0059(15)
C1 0.0298(14) 0.0298(14) 0.021(2) 0.0017(19) -0.005(3) 0.005(3)
C2 0.056(3) 0.061(3) 0.132(7) -0.030(3) -0.064(4) 0.064(4)
C3 0.0245(19) 0.030(2) 0.021(2) 0.0066(16) 0.0005(15) 0.0017(16)
C4 0.038(2) 0.033(2) 0.044(4) -0.0073(16) -0.011(2) 0.011(2)
C5 0.038(2) 0.033(2) 0.039(3) -0.0040(19) -0.013(2) 0.014(2)
C6 0.0221(19) 0.036(2) 0.0219(19) 0.0067(16) 0.0002(15) 0.0025(16)
C7 0.0219(19) 0.027(2) 0.030(2) 0.0039(16) 0.0048(17) -0.0021(17)
C8 0.026(2) 0.029(2) 0.032(3) 0.0052(16) 0.0026(15) 0.0037(15)
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
O O 0.0106 0.0060 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C2 . . 106.9(4) ?
C1 N1 C3 . . 125.8(4) ?
C2 N1 C3 . . 127.3(4) ?
N1 C1 N1 . 5_557 109.1(5) ?
N1 C1 H1 . . 125.4 ?
N1 C1 H1 5_557 . 125.4 ?
C2 C2 N1 5_557 . 108.5(3) ?
C2 C2 H2 5_557 . 125.7 ?
N1 C2 H2 . . 125.7 ?
C8 C3 C4 . . 120.6(4) ?
C8 C3 N1 . . 120.2(4) ?
C4 C3 N1 . . 119.2(4) ?
C3 C4 C5 . . 119.9(4) ?
C3 C4 H4 . . 120.1 ?
C5 C4 H4 . . 120.1 ?
C6 C5 C4 . . 119.2(4) ?
C6 C5 H5 . . 120.4 ?
C4 C5 H5 . . 120.4 ?
C7 C6 C5 . . 121.1(4) ?
C7 C6 Br1 . . 119.8(3) ?
C5 C6 Br1 . . 119.1(3) ?
C6 C7 C8 . . 120.2(4) ?
C6 C7 H7 . . 119.9 ?
C8 C7 H7 . . 119.9 ?
C3 C8 C7 . . 119.1(4) ?
C3 C8 H8 . . 120.5 ?
C7 C8 H8 . . 120.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C6 . 1.890(4) ?
O1 H1O . 0.84(6) ?
O2 H2O . 0.87(6) ?
N1 C1 . 1.331(4) ?
N1 C2 . 1.362(6) ?
N1 C3 . 1.437(5) ?
C1 N1 5_557 1.331(4) ?
C1 H1 . 0.9500 ?
C2 C2 5_557 1.303(10) ?
C2 H2 . 0.9500 ?
C3 C8 . 1.383(6) ?
C3 C4 . 1.383(6) ?
C4 C5 . 1.391(6) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.378(6) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.370(6) ?
C7 C8 . 1.391(6) ?
C7 H7 . 0.9500 ?
C8 H8 . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1o Cl1 1_556 0.84(6) 2.28(6) 3.1116(19) 170(8)
O2 H2o Cl1 1_555 0.87(6) 2.40(6) 3.211(3) 157(7)
C1 H1 O1 1_555 0.95 2.09 3.042(5) 180
C2 H2 O2 7_554 0.95 2.40 3.302(7) 159
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C1 N1 . . . 5_557 -0.2(4) ?
C3 N1 C1 N1 . . . 5_557 178.9(4) ?
C1 N1 C2 C2 . . . 5_557 0.7(10) ?
C3 N1 C2 C2 . . . 5_557 -178.4(6) ?
C1 N1 C3 C8 . . . . -12.5(5) ?
C2 N1 C3 C8 . . . . 166.4(5) ?
C1 N1 C3 C4 . . . . 168.5(4) ?
C2 N1 C3 C4 . . . . -12.5(7) ?
C8 C3 C4 C5 . . . . -1.0(7) ?
N1 C3 C4 C5 . . . . 177.9(4) ?
C3 C4 C5 C6 . . . . 0.2(7) ?
C4 C5 C6 C7 . . . . 0.5(7) ?
C4 C5 C6 Br1 . . . . -179.4(4) ?
C5 C6 C7 C8 . . . . -0.4(6) ?
Br1 C6 C7 C8 . . . . 179.5(3) ?
C4 C3 C8 C7 . . . . 1.0(6) ?
N1 C3 C8 C7 . . . . -177.9(3) ?
C6 C7 C8 C3 . . . . -0.3(6) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 57450212
