#------------------------------------------------------------------------------
#$Date: 2022-01-07 01:12:38 +0200 (Fri, 07 Jan 2022) $
#$Revision: 271912 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/39/2243993.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_2243993
loop_
_publ_author_name
'Konovalova, Irina S.'
'Shishkina, Svitlana V.'
'Kobzev, Dmytro'
'Semenova, Olha'
'Tatarets, Anatoliy'
_publ_section_title
;
 Crystal structures and Hirshfeld analysis of 4,6-dibromoindolenine and
 its quaternized salt
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1203
_journal_page_last               1207
_journal_paper_doi               10.1107/S2056989021011385
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C12 H14 Br2 N +, I -'
_chemical_formula_moiety         'C12 H14 Br2 N +, I -'
_chemical_formula_sum            'C12 H14 Br2 I N'
_chemical_formula_weight         458.96
_chemical_name_systematic
;
4,6-Dibromo-2,3,3-trimethyl-3H-indol-1-ium iodide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.755(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.3507(6)
_cell_length_b                   7.3719(5)
_cell_length_c                   11.7180(8)
_cell_measurement_reflns_used    1781
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.6260
_cell_measurement_theta_min      3.7560
_cell_volume                     720.53(9)
_computing_data_collection       'CrysAlisPro (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2018)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL2016/6 (Sheldrick, 2015a)'
_computing_structure_solution    'SHELXT2014/5 (Sheldrick, 2015b)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1827
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0833
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4499
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.930
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    7.743
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2018)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.115
_exptl_crystal_description       needle
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.855
_refine_diff_density_min         -0.914
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     97
_refine_ls_number_reflns         1374
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0457
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0732P)²+0.1443P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1155
_refine_ls_wR_factor_ref         0.1209
_reflns_number_gt                1242
_reflns_number_total             1374
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            zn2011sup1.cif
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      P21/m
_cod_database_code               2243993
_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.
;
_shelx_estimated_absorpt_t_min   0.148
_shelx_estimated_absorpt_t_max   0.511
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I I1 0.70649(6) 0.750000 0.12215(4) 0.0481(3) Uani d 1 . .
Br Br1 0.57546(9) 0.250000 0.65282(7) 0.0477(3) Uani d 1 . .
Br Br2 1.19756(8) 0.250000 0.49523(7) 0.0455(3) Uani d 1 . .
N N1 0.7083(7) 0.250000 0.2129(5) 0.0333(13) Uani d 1 . .
C C1 0.7464(7) 0.250000 0.3305(5) 0.0310(15) Uani d 1 . .
C C2 0.6429(8) 0.250000 0.4171(6) 0.0339(15) Uani d 1 . .
H H2 0.532393 0.250000 0.402939 0.041 Uiso calc 1 . .
C C3 0.7113(9) 0.250000 0.5275(6) 0.0361(16) Uani d 1 . .
C C4 0.8733(8) 0.250000 0.5472(6) 0.0334(15) Uani d 1 . .
H H4 0.915491 0.250000 0.622086 0.040 Uiso calc 1 . .
C C5 0.9763(8) 0.250000 0.4585(6) 0.0321(14) Uani d 1 . .
C C6 0.9130(8) 0.250000 0.3468(6) 0.0317(15) Uani d 1 . .
C C7 0.9823(9) 0.250000 0.2291(6) 0.0328(15) Uani d 1 . .
C C8 0.8337(9) 0.250000 0.1513(6) 0.0347(16) Uani d 1 . .
C C9 1.0830(6) 0.4194(8) 0.2084(5) 0.0446(12) Uani d 1 . .
H H9A 1.017880 0.525689 0.215897 0.067 Uiso calc 1 . .
H H9B 1.122463 0.414922 0.132876 0.067 Uiso calc 1 . .
H H9C 1.171753 0.423837 0.263544 0.067 Uiso calc 1 . .
C C10 0.8300(11) 0.250000 0.0265(7) 0.0483(19) Uani d 1 . .
H H10A 0.929629 0.203613 0.001073 0.073 Uiso calc 0.5 A -1
H H10B 0.814457 0.371640 -0.001140 0.073 Uiso calc 0.5 A -1
H H10C 0.743463 0.174747 -0.002504 0.073 Uiso calc 0.5 A -1
C C11 0.5431(10) 0.250000 0.1659(8) 0.051(2) Uani d 1 . .
H H11A 0.541464 0.284350 0.086856 0.077 Uiso calc 0.5 B -1
H H11B 0.480906 0.334906 0.207372 0.077 Uiso calc 0.5 B -1
H H11C 0.498349 0.130744 0.172659 0.077 Uiso calc 0.5 B -1
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'
I I -0.4742 1.8119 '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'
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 C11 . . 122.5(6) ?
C8 N1 C1 . . 113.3(6) ?
C8 N1 C11 . . 124.2(7) ?
C2 C1 N1 . . 127.6(6) ?
C2 C1 C6 . . 124.1(6) ?
C6 C1 N1 . . 108.3(6) ?
C1 C2 H2 . . 121.7 ?
C1 C2 C3 . . 116.5(6) ?
C3 C2 H2 . . 121.7 ?
C2 C3 Br1 . . 119.1(5) ?
C4 C3 Br1 . . 119.6(5) ?
C4 C3 C2 . . 121.3(6) ?
C3 C4 H4 . . 119.3 ?
C3 C4 C5 . . 121.5(6) ?
C5 C4 H4 . . 119.3 ?
C4 C5 Br2 . . 118.0(5) ?
C4 C5 C6 . . 119.1(6) ?
C6 C5 Br2 . . 122.9(5) ?
C1 C6 C7 . . 107.2(6) ?
C5 C6 C1 . . 117.5(6) ?
C5 C6 C7 . . 135.3(6) ?
C6 C7 C9 . 4_565 112.3(4) ?
C6 C7 C9 . . 112.3(4) ?
C8 C7 C6 . . 102.2(5) ?
C8 C7 C9 . . 110.3(4) ?
C8 C7 C9 . 4_565 110.3(4) ?
C9 C7 C9 . 4_565 109.3(6) ?
N1 C8 C7 . . 109.0(6) ?
N1 C8 C10 . . 125.2(7) ?
C10 C8 C7 . . 125.7(6) ?
C7 C9 H9A . . 109.5 ?
C7 C9 H9B . . 109.5 ?
C7 C9 H9C . . 109.5 ?
H9A C9 H9B . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C8 C10 H10A . . 109.5 ?
C8 C10 H10B . . 109.5 ?
C8 C10 H10C . . 109.5 ?
H10A C10 H10B . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
N1 C11 H11A . . 109.5 ?
N1 C11 H11B . . 109.5 ?
N1 C11 H11C . . 109.5 ?
H11A C11 H11B . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
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 C3 . 1.899(7) ?
Br2 C5 . 1.877(7) ?
N1 C1 . 1.399(8) ?
N1 C8 . 1.301(9) ?
N1 C11 . 1.460(10) ?
C1 C2 . 1.364(10) ?
C1 C6 . 1.395(9) ?
C2 H2 . 0.9300 ?
C2 C3 . 1.389(10) ?
C3 C4 . 1.361(10) ?
C4 H4 . 0.9300 ?
C4 C5 . 1.381(10) ?
C5 C6 . 1.387(10) ?
C6 C7 . 1.522(9) ?
C7 C8 . 1.504(10) ?
C7 C9 . 1.532(7) ?
C7 C9 4_565 1.532(7) ?
C8 C10 . 1.461(10) ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
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
C2 H2 Br2 1_455 0.93 3.05 3.8720(10) 149
C5 Br2 Br1 1_655 1.877(7) 3.58 5.3970(10) 162
C3 Br1 I1 3_666 1.899(7) 3.62 5.5140(10) 176
C11 H11A I1 3_665 0.96 3.14 3.8810(10) 135
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
Br1 C3 C4 C5 . . . . 180.000(2) ?
Br2 C5 C6 C1 . . . . 180.0000(10) ?
Br2 C5 C6 C7 . . . . 0.000(2) ?
N1 C1 C2 C3 . . . . 180.0000(10) ?
N1 C1 C6 C5 . . . . 180.0000(10) ?
N1 C1 C6 C7 . . . . 0.0000(10) ?
C1 N1 C8 C7 . . . . 0.0000(10) ?
C1 N1 C8 C10 . . . . 180.000000 ?
C1 C2 C3 Br1 . . . . 180.0000(10) ?
C1 C2 C3 C4 . . . . 0.000(2) ?
C1 C6 C7 C8 . . . . 0.0000(10) ?
C1 C6 C7 C9 . . . 4_565 -118.2(4) ?
C1 C6 C7 C9 . . . . 118.2(4) ?
C2 C1 C6 C5 . . . . 0.0000(10) ?
C2 C1 C6 C7 . . . . 180.0000(10) ?
C2 C3 C4 C5 . . . . 0.000(2) ?
C3 C4 C5 Br2 . . . . 180.0000(10) ?
C3 C4 C5 C6 . . . . 0.000(2) ?
C4 C5 C6 C1 . . . . 0.0000(10) ?
C4 C5 C6 C7 . . . . 180.0000(10) ?
C5 C6 C7 C8 . . . . 180.0000(10) ?
C5 C6 C7 C9 . . . . -61.8(4) ?
C5 C6 C7 C9 . . . 4_565 61.8(4) ?
C6 C1 C2 C3 . . . . 0.0000(10) ?
C6 C7 C8 N1 . . . . 0.0000(10) ?
C6 C7 C8 C10 . . . . 180.0000(10) ?
C8 N1 C1 C2 . . . . 180.0000(10) ?
C8 N1 C1 C6 . . . . 0.0000(10) ?
C9 C7 C8 N1 4_565 . . . 119.6(4) ?
C9 C7 C8 N1 . . . . -119.6(4) ?
C9 C7 C8 C10 4_565 . . . -60.4(4) ?
C9 C7 C8 C10 . . . . 60.4(4) ?
C11 N1 C1 C2 . . . . 0.0000(10) ?
C11 N1 C1 C6 . . . . 180.0000(10) ?
C11 N1 C8 C7 . . . . 180.0000(10) ?
C11 N1 C8 C10 . . . . 0.0000(10) ?

_cod_database_fobs_code 2243993
