A structural and computational comparison of close contacts and related intermolecular energies of interaction in the structures of 1,3-diiodo-5-nitrobenzene, 1,3-dibromo-5-nitrobenzene, and 1,3-dichloro-5-nitrobenzene
Bosch, Eric; Bowling, Nathan P.; Speetzen, Erin D.; Acta Crystallographica Section C 78 (2022) 552–558; doi:10.1107/S2053229622009275

data_2022676
_publ_section_title
;
 A structural and computational comparison of close contacts and related
 intermolecular energies of interaction in the structures of
 1,3-diiodo-5-nitrobenzene, 1,3-dibromo-5-nitrobenzene, and
 1,3-dichloro-5-nitrobenzene
;
_journal_coeditor_code           DV3019
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              552
_journal_page_last               558
_journal_paper_doi               10.1107/S2053229622009275
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C6 H3 Br2 N O2'
_chemical_formula_sum            'C6 H3 Br2 N O2'
_chemical_formula_weight         280.91
_chemical_name_systematic
;
1,3-Dibromo-5-nitrobenzene
;
_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           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 96.486(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   3.9721(7)
_cell_length_b                   14.164(2)
_cell_length_c                   6.7971(11)
_cell_measurement_reflns_used    2304
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.05
_cell_measurement_theta_min      2.88
_cell_volume                     379.96(11)
_computing_cell_refinement
;
SMART (Bruker, 2014)
;
_computing_data_collection
;
SMART (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_molecular_graphics
;
X-SEED (Barbour, 2020)
;
_computing_publication_material
;
X-SEED (Barbour, 2020)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3660
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-I CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4446
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.137
_diffrn_reflns_theta_min         2.876
_exptl_absorpt_coefficient_mu    10.609
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.3431
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.455
_exptl_crystal_description       'cut plate'
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.039
_refine_diff_density_min         -0.521
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     55
_refine_ls_number_reflns         874
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0291
_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^)+(0.0519P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0780
_refine_ls_wR_factor_ref         0.0812
_reflns_number_gt                764
_reflns_number_total             874
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            dv3019sup1.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 2022675--2022677.cif.'
_cod_original_cell_volume        379.97(11)
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               2022676
_cod_database_fobs_code          2022676
_shelx_hkl_checksum              26258
_shelx_res_checksum              79844