Syntheses, crystal structures, Hirshfeld surface analyses and crystal voids of 1-(4-bromophenyl)-2,2-dichloroethan-1-one and 2,2-dibromo-1-(p-tolyl)ethan-1-one
Gurbanov, Atash V.; Guseinov, Firudin I.; Samigullina, Aida I.; Hökelek, Tuncer; Hasanov, Khudayar I.; Javadzade, Tahir A.; Belay, Alebel N.; Acta Crystallographica Section E Crystallographic Communications 81 (2025) –; doi:10.1107/S205698902500012X

data_2023349
_publ_section_title
;
 Syntheses, crystal structures, Hirshfeld surface analyses and crystal
 voids of 1-(4-bromophenyl)-2,2-dichloroethan-1-one and
 2,2-dibromo-1-(p-tolyl)ethan-1-one
;
_journal_coeditor_code           NX2018
_journal_issue                   2
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S205698902500012X
_journal_volume                  81
_journal_year                    2025
_chemical_formula_iupac          'C9 H8 Br2 O'
_chemical_formula_moiety         'C9 H8 Br2 O'
_chemical_formula_sum            'C9 H8 Br2 O'
_chemical_formula_weight         291.97
_chemical_name_common
;
2,2-Dibromo-1-(<i>p</i>-tolyl)ethan-1-one
;
_chemical_name_systematic
;
2,2-Dibromo-1-(4-methylphenyl)ethan-1-one
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.5200(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.62430(10)
_cell_length_b                   9.95740(10)
_cell_length_c                   14.3804(2)
_cell_measurement_reflns_used    8712
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      80.1840
_cell_measurement_theta_min      4.3970
_cell_volume                     947.63(2)
_computing_cell_refinement
;
CrysAlisPro 1.171.43.117a (Rigaku OD, 2024)
;
_computing_data_collection
;
CrysAlis PRO (Rikagu OD, 2024)
;
_computing_data_reduction
;
CrysAlisPro 1.171.43.117a (Rigaku OD, 2024)
;
_computing_molecular_graphics
;
Olex2 1.3 (Dolomanov et al., 2009)
;
_computing_publication_material
;
Olex2 1.3 (Dolomanov et al., 2009)
;
_computing_structure_refinement
;
<i>SHELXL2018/3</i> (Sheldrick, 2015b)
;
_computing_structure_solution
;
<i>SHELXT2018/2</i> (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.621
_diffrn_reflns_theta_min         5.405
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    10.434
_exptl_absorpt_correction_T_max  0.680
_exptl_absorpt_correction_T_min  0.198
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlisPr; Rigaku OD, 2024)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.047
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.613
_refine_diff_density_min         -0.513
_refine_ls_extinction_coef       0.00143(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
<i>SHELXL2018/3</i> (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         2075
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0268
_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/[\s^2^(Fo^2^)+(0.0353P)^2^+1.8407P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0701
_refine_ls_wR_factor_ref         0.0705
_reflns_number_gt                2046
_reflns_number_total             2075
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            nx2018.cif
_cod_data_source_block           II
_cod_database_code               2023349
_shelx_estimated_absorpt_t_min   0.207
_shelx_estimated_absorpt_t_max   0.367
_shelx_hkl_checksum              24932
_shelx_res_checksum              28516