Crystal structure and Hirshfeld surface analysis of 1-[2-(2-chloroethoxy)ethyl]-2-methyl-4-nitro-1H-imidazole
Mohan Kumar, Thaluru M.; Bhavya, Papegowda; Bhaskar, Besagarahally L.; Shankara Prasad, Holehundi J.; Yathirajan, Hemmige S.; Parkin, Sean; Acta Crystallographica Section E Crystallographic Communications 81 (2025) –; doi:10.1107/S2056989025005493

data_2023529
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 1-[2-(2-chloroethoxy)ethyl]-2-methyl-4-nitro-1H-imidazole
;
_journal_coeditor_code           NX2027
_journal_issue                   7
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S2056989025005493
_journal_volume                  81
_journal_year                    2025
_chemical_formula_iupac          'C8 H12 Cl N3 O3'
_chemical_formula_moiety         'C8 H12 Cl N3 O3'
_chemical_formula_sum            'C8 H12 Cl N3 O3'
_chemical_formula_weight         233.66
_chemical_name_systematic
;
1-[2-(2-Chloroethoxy)ethyl]-2-methyl-4-nitro-1<i>H</i>-imidazole
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL-2019/3 and CIFFIX'
_cell_angle_alpha                98.662(2)
_cell_angle_beta                 93.164(2)
_cell_angle_gamma                103.444(2)
_cell_formula_units_Z            4
_cell_length_a                   8.5810(4)
_cell_length_b                   11.1448(7)
_cell_length_c                   11.5757(5)
_cell_measurement_reflns_used    9978
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      2.71
_cell_volume                     1059.71(10)
_computing_cell_refinement
;
<i>APEX5</i> (Bruker, 2023)
;
_computing_data_collection
;
<i>APEX5</i> (Bruker, 2023)
;
_computing_data_reduction
;
<i>APEX5</i> (Bruker, 2023)
;
_computing_molecular_graphics
;
<i>Mercury</i> (Macrae <i>et al.</i>, 2020) and
<i>Overlay.py</i> (Parkin, 2025)
;
_computing_publication_material
;
<i>SHELX</i> (Sheldrick, 2008) and <i>publCIF</i> (Westrip 2010)
;
_computing_structure_refinement
;
<i>SHELXL2019/3</i> (Sheldrick, 2015b)
;
_computing_structure_solution
;
<i>SHELXT</i> (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector_area_resol_mean 7.41
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture dual source'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            34130
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.561
_diffrn_reflns_theta_min         1.906
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    0.352
_exptl_absorpt_correction_T_max  0.959
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>SADABS</i>; Krause <i>et al</i>., 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_description       'solvent-rounded block'
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.353
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         4879
_refine_ls_number_restraints     416
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0306
_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^)+(0.0258P)^2^+0.4798P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0722
_refine_ls_wR_factor_ref         0.0758
_reflns_number_gt                4337
_reflns_number_total             4879
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            nx2027.cif
_cod_data_source_block           I
_cod_database_code               2023529
_shelx_estimated_absorpt_t_min   0.917
_shelx_estimated_absorpt_t_max   0.956
_shelx_hkl_checksum              2772
_shelx_res_checksum              20290