Crystal structure, Hirshfeld surface analysis and DFT study of <i>N</i>-(2-nitro-phen-yl)male-imide.
Montoya-Garcia, Maribel; Cortes-Hernandez, Héctor; D'Vries, Richard; Valencia-Sanchez, Hoover; Acta crystallographica. Section E, Crystallographic communications 80 (2024) 256–261; doi:10.1107/S2056989024000926

data_2023023
_publ_section_title
;
 Crystal structure, Hirshfeld surface analysis and DFT study of
 <i>N</i>-(2-nitro-phen-yl)male-imide.
;
_journal_coeditor_code           VU2003
_journal_issue                   'Pt 3'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              256
_journal_page_last               261
_journal_paper_doi               10.1107/S2056989024000926
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          'C10 H6 N2 O4'
_chemical_formula_moiety         'C10 H6 N2 O4'
_chemical_formula_sum            'C10 H6 N2 O4'
_chemical_formula_weight         218.17
_chemical_name_common
;
<i>N</i>-(2-Nitrophenyl)maleimide
;
_chemical_name_systematic
;
1-(2-Nitrophenyl)pyrrole-2,5-dione
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.969(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.331(5)
_cell_length_b                   7.769(5)
_cell_length_c                   17.558(5)
_cell_measurement_reflns_used    2214
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4914
_cell_measurement_theta_min      3.6101
_cell_volume                     1953.7(15)
_computing_cell_refinement
;
CrysAlisPro (Agilent, 2012)
;
_computing_data_collection
;
CrysAlisPro (Agilent, 2012)
;
_computing_data_reduction
;
CrysAlisPro (Agilent, 2012)
;
_computing_molecular_graphics
;
Olex2 1.3 (Dolomanov <i>et al.</i>,  2009)
;
_computing_publication_material
;
Olex2 1.3 (Dolomanov <i>et al.</i>,  2009)
;
_computing_structure_refinement
;
<i>SHELXL2016/6</i> (Sheldrick, 2015b)
;
_computing_structure_solution
;
<i>SHELXT2014/5</i> (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.877
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8808
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.968
_diffrn_reflns_theta_min         3.610
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
(CrysAlisPro;  Agilent, 2012)
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.5963
_exptl_crystal_size_mid          0.5082
_exptl_crystal_size_min          0.3633
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.194
_refine_ls_extinction_coef       0.0083(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
<i>SHELXL2016/6</i> (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4548
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0479
_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^)+(0.0388P)^2^+0.6076P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1215
_reflns_number_gt                2815
_reflns_number_total             5183
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            vu2003sup1.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2023023.cif.'
_cod_database_code               2023023
_cod_database_fobs_code          2023023
_shelx_res_checksum              64526