Crystal structures and Hirshfeld analysis of 4,6-dibromoindolenine and its quaternized salt
Konovalova, Irina S.; Shishkina, Svitlana V.; Kobzev, Dmytro; Semenova, Olha; Tatarets, Anatoliy; Acta Crystallographica Section E 77 (2021) 1203–1207; doi:10.1107/S2056989021011385

data_2243992
_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-3<i>H</i>-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    '<i>OLEX2</i> (Dolomanov et al., 2009)'
_computing_publication_material  '<i>OLEX2</i> (Dolomanov et al., 2009)'
_computing_structure_refinement  '<i>SHELXL2016/6</i> (Sheldrick, 2015a)'
_computing_structure_solution    '<i>SHELXT2014/5</i> (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       '\w 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 <i>x</i> determined using 613 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</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/[\s^2^(Fo^2^)+(0.0554P)^2^+0.2950P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(I)'
_cod_data_source_file            zn2011sup1.cif
_cod_data_source_block           1
_cod_database_code               2243992
_shelx_estimated_absorpt_t_min   0.172
_shelx_estimated_absorpt_t_max   0.235
_shelx_hkl_checksum              51009
_shelx_res_checksum              84205
_cod_database_fobs_code 2243992