Crystal structure and Hirshfeld surface analysis of (<i>E</i>)-2-(4-bromophenyl)-1-[2,2-dibromo-1-(4-nitrophenyl)ethenyl]diazene
Akkurt, Mehmet; Yıldırım, Sema Öztürk; Shikhaliyev, Namiq Q.; Mammadova, Naila A.; Niyazova, Ayten A.; Khrustalev, Victor N.; Bhattarai, Ajaya; Acta Crystallographica Section E 78 (2022) –; doi:10.1107/S205698902200620X

data_2244117
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 (<i>E</i>)-2-(4-bromophenyl)-1-[2,2-dibromo-1-(4-nitrophenyl)ethenyl]diazene
;
_journal_coeditor_code           YK2170
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S205698902200620X
_journal_volume                  78
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_iupac          'C14 H8 Br3 N3 O2'
_chemical_formula_moiety         'C14 H8 Br3 N3 O2'
_chemical_formula_sum            'C14 H8 Br3 N3 O2'
_chemical_formula_weight         489.96
_chemical_name_systematic
;
(<i>E</i>)-2-(4-Bromophenyl)-1-[2,2-dibromo-1-(4-nitrophenyl)ethenyl]diazene
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8678(5)
_cell_length_b                   13.5442(5)
_cell_length_c                   8.3017(3)
_cell_measurement_reflns_used    9976
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      34.81
_cell_measurement_theta_min      2.88
_cell_volume                     1559.29(10)
_computing_cell_refinement
;
SAINT (Bruker, 2018)
;
_computing_data_collection
;
<i>APEX3</i> (Bruker, 2018)
;
_computing_data_reduction
;
SAINT (Bruker, 2018)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 QUEST, Photon III detector'
_diffrn_measurement_method       '\f and \w shutterless scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            75835
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         35.973
_diffrn_reflns_theta_min         2.878
_diffrn_source                   'fine-focus sealed X-Ray tube'
_exptl_absorpt_coefficient_mu    7.770
_exptl_absorpt_correction_T_max  0.1101
_exptl_absorpt_correction_T_min  0.0441
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause <i>et al.</i>,  2015)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.087
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.405
_refine_diff_density_min         -0.968
_refine_ls_abs_structure_details
;
Flack parameter determined using 2437 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>,  2013).
;
_refine_ls_abs_structure_Flack   0.003(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         7370
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0333
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0438P)^2^+0.8309P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0769
_refine_ls_wR_factor_ref         0.0847
_reflns_number_gt                5962
_reflns_number_total             7370
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            yk2170sup1.cif
_cod_data_source_block           I
_cod_database_code               2244117
_shelx_estimated_absorpt_t_min   0.197
_shelx_estimated_absorpt_t_max   0.575
_shelx_hkl_checksum              29246
_shelx_res_checksum              35517
_cod_database_fobs_code 2244117