#------------------------------------------------------------------------------
#$Date: 2022-01-07 01:12:38 +0200 (Fri, 07 Jan 2022) $
#$Revision: 271912 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/39/2243992.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_2243992
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_coeditor_code           ZN2011
_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_absolute_configuration syn
_chemical_formula_iupac          'C11 H11 Br2 N'
_chemical_formula_moiety         'C11 H11 Br2 N'
_chemical_formula_sum            'C11 H11 Br2 N'
_chemical_formula_weight         317.03
_chemical_name_systematic
;
4,6-Dibromo-2,3,3-trimethyl-3H-indole
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7761(5)
_cell_length_b                   11.3876(7)
_cell_length_c                   11.8654(4)
_cell_measurement_reflns_used    2796
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.8590
_cell_measurement_theta_min      3.6160
_cell_volume                     1185.81(11)
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2018)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0809
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8516
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.930
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    6.798
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68169
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2018)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.776
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.545
_refine_ls_abs_structure_details
;
 Flack x determined using 613 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
 (Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack   0.05(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         2086
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0469
_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)+(0.0554P)²+0.2950P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1103
_refine_ls_wR_factor_ref         0.1207
_reflns_number_gt                1789
_reflns_number_total             2086
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            zn2011sup1.cif
_cod_data_source_block           1
_cod_database_code               2243992
_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   0.172
_shelx_estimated_absorpt_t_max   0.235
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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
Br Br1 0.24163(11) 0.35819(9) 0.83683(7) 0.0630(4) Uani d 1 . .
Br Br2 0.73559(14) 0.21032(9) 0.56768(8) 0.0769(4) Uani d 1 . .
N N1 0.5082(8) 0.6304(7) 0.5315(6) 0.0518(18) Uani d 1 . .
C C1 0.4908(9) 0.5231(8) 0.5910(6) 0.0432(19) Uani d 1 . .
C C2 0.3837(10) 0.5003(7) 0.6734(6) 0.047(2) Uani d 1 . .
H H2 0.312700 0.556729 0.694752 0.056 Uiso calc 1 . .
C C3 0.3861(9) 0.3912(8) 0.7227(6) 0.046(2) Uani d 1 . .
C C4 0.4903(9) 0.3063(8) 0.6936(7) 0.052(2) Uani d 1 . .
H H4 0.489872 0.233692 0.729463 0.062 Uiso calc 1 . .
C C5 0.5979(10) 0.3311(8) 0.6085(7) 0.049(2) Uani d 1 . .
C C6 0.5999(9) 0.4389(8) 0.5579(6) 0.046(2) Uani d 1 . .
C C7 0.6962(9) 0.4972(8) 0.4670(6) 0.050(2) Uani d 1 . .
C C8 0.6202(9) 0.6146(8) 0.4635(7) 0.051(2) Uani d 1 . .
C C9 0.6811(15) 0.4323(11) 0.3518(7) 0.077(3) Uani d 1 . .
H H9A 0.719284 0.353684 0.359071 0.116 Uiso calc 1 . .
H H9B 0.738795 0.473434 0.295515 0.116 Uiso calc 1 . .
H H9C 0.575831 0.429848 0.329832 0.116 Uiso calc 1 . .
C C10 0.8638(11) 0.5078(11) 0.5014(10) 0.079(3) Uani d 1 . .
H H10A 0.870442 0.542173 0.575093 0.119 Uiso calc 1 . .
H H10B 0.916473 0.556660 0.448193 0.119 Uiso calc 1 . .
H H10C 0.909473 0.431228 0.502393 0.119 Uiso calc 1 . .
C C11 0.6680(12) 0.7123(9) 0.3846(8) 0.072(3) Uani d 1 . .
H H11A 0.597667 0.776545 0.390964 0.107 Uiso calc 1 . .
H H11B 0.668219 0.683767 0.308475 0.107 Uiso calc 1 . .
H H11C 0.768433 0.738629 0.404338 0.107 Uiso calc 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'
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
C8 N1 C1 . . 105.9(8) ?
C2 C1 N1 . . 126.0(8) ?
C2 C1 C6 . . 122.1(8) ?
C6 C1 N1 . . 111.9(7) ?
C1 C2 H2 . . 121.3 ?
C3 C2 C1 . . 117.5(8) ?
C3 C2 H2 . . 121.3 ?
C2 C3 Br1 . . 118.3(6) ?
C2 C3 C4 . . 122.6(7) ?
C4 C3 Br1 . . 119.1(6) ?
C3 C4 H4 . . 120.5 ?
C3 C4 C5 . . 119.0(8) ?
C5 C4 H4 . . 120.5 ?
C4 C5 Br2 . . 117.7(7) ?
C6 C5 Br2 . . 122.2(6) ?
C6 C5 C4 . . 120.2(8) ?
C1 C6 C7 . . 106.1(7) ?
C5 C6 C1 . . 118.7(7) ?
C5 C6 C7 . . 135.2(8) ?
C6 C7 C9 . . 111.5(8) ?
C6 C7 C10 . . 112.3(8) ?
C8 C7 C6 . . 99.3(7) ?
C8 C7 C9 . . 111.2(8) ?
C8 C7 C10 . . 111.5(8) ?
C10 C7 C9 . . 110.6(7) ?
N1 C8 C7 . . 116.7(8) ?
N1 C8 C11 . . 119.8(9) ?
C7 C8 C11 . . 123.4(8) ?
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 ?
C7 C10 H10A . . 109.5 ?
C7 C10 H10B . . 109.5 ?
C7 C10 H10C . . 109.5 ?
H10A C10 H10B . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C8 C11 H11A . . 109.5 ?
C8 C11 H11B . . 109.5 ?
C8 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 . 1.893(8) ?
Br2 C5 . 1.894(9) ?
N1 C1 . 1.419(11) ?
N1 C8 . 1.284(10) ?
C1 C2 . 1.381(11) ?
C1 C6 . 1.411(11) ?
C2 H2 . 0.9300 ?
C2 C3 . 1.374(11) ?
C3 C4 . 1.375(11) ?
C4 H4 . 0.9300 ?
C4 C5 . 1.412(11) ?
C5 C6 . 1.367(12) ?
C6 C7 . 1.522(11) ?
C7 C8 . 1.494(13) ?
C7 C9 . 1.560(12) ?
C7 C10 . 1.531(13) ?
C8 C11 . 1.514(12) ?
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
C3 Br1 N1 2_565 1.89 3.19 5.2830(10) 166
C3 Br1 C8 2_565 1.89 3.53 5.0460(10) 153
C11 H11C N1 4_566 0.96 2.69 3.6210(10) 164
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 . . . . -180.0(6) ?
Br2 C5 C6 C1 . . . . 178.3(6) ?
Br2 C5 C6 C7 . . . . -1.3(14) ?
N1 C1 C2 C3 . . . . -179.1(7) ?
N1 C1 C6 C5 . . . . 179.6(7) ?
N1 C1 C6 C7 . . . . -0.6(9) ?
C1 N1 C8 C7 . . . . -0.7(10) ?
C1 N1 C8 C11 . . . . 178.8(8) ?
C1 C2 C3 Br1 . . . . 179.5(6) ?
C1 C2 C3 C4 . . . . 0.5(12) ?
C1 C6 C7 C8 . . . . 0.2(8) ?
C1 C6 C7 C9 . . . . -117.1(8) ?
C1 C6 C7 C10 . . . . 118.1(9) ?
C2 C1 C6 C5 . . . . 0.7(12) ?
C2 C1 C6 C7 . . . . -179.6(7) ?
C2 C3 C4 C5 . . . . -1.0(13) ?
C3 C4 C5 Br2 . . . . -178.1(6) ?
C3 C4 C5 C6 . . . . 1.4(13) ?
C4 C5 C6 C1 . . . . -1.2(12) ?
C4 C5 C6 C7 . . . . 179.2(9) ?
C5 C6 C7 C8 . . . . 179.9(9) ?
C5 C6 C7 C9 . . . . 62.6(13) ?
C5 C6 C7 C10 . . . . -62.2(13) ?
C6 C1 C2 C3 . . . . -0.3(12) ?
C6 C7 C8 N1 . . . . 0.3(9) ?
C6 C7 C8 C11 . . . . -179.2(8) ?
C8 N1 C1 C2 . . . . 179.8(8) ?
C8 N1 C1 C6 . . . . 0.8(9) ?
C9 C7 C8 N1 . . . . 117.9(8) ?
C9 C7 C8 C11 . . . . -61.7(11) ?
C10 C7 C8 N1 . . . . -118.2(9) ?
C10 C7 C8 C11 . . . . 62.3(11) ?

_cod_database_fobs_code 2243992
