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_2022675
_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 I2 N O2'
_chemical_formula_sum            'C6 H3 I2 N O2'
_chemical_formula_weight         374.89
_chemical_name_systematic
;
1,3-Diiodo-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                 96.506(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.1810(5)
_cell_length_b                   15.0336(17)
_cell_length_c                   6.7970(8)
_cell_measurement_reflns_used    4388
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.20
_cell_measurement_theta_min      2.71
_cell_volume                     424.48(9)
_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 0.999
_diffrn_measured_fraction_theta_max 0.998
_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  0.0190
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5377
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.198
_diffrn_reflns_theta_min         2.710
_exptl_absorpt_coefficient_mu    7.358
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.4056
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.933
_exptl_crystal_description       trapezoidal
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.770
_refine_diff_density_min         -0.751
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.345
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     55
_refine_ls_number_reflns         982
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.345
_refine_ls_R_factor_all          0.0196
_refine_ls_R_factor_gt           0.0191
_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^)+1.4021P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0402
_refine_ls_wR_factor_ref         0.0404
_reflns_number_gt                974
_reflns_number_total             982
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            dv3019sup1.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 2022675--2022677.cif.'
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               2022675
_cod_database_fobs_code          2022675
_shelx_hkl_checksum              31028
_shelx_res_checksum              36604