Comprehensive Structural Insights into Nitro-Substituted Azines as Potential Antioxidant Additives for Biodiesel
Junior, Ronaldo Gonçalves de Freitas; Duarte, Vitor; Almeida, Leonardo R.; Santana Wenceslau, Patricia Rafaella; Aquino, Gilberto Benedito; Valverde, Clodoaldo; Napolitano, Hamilton; CrystEngComm  (2025) –; doi:10.1039/D5CE00915D

data_7251386
_publ_section_title
;
 Comprehensive Structural Insights into Nitro-Substituted Azines as
 Potential Antioxidant Additives for Biodiesel
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D5CE00915D
_journal_year                    2025
_chemical_formula_moiety         'C16 H14 N4 O4'
_chemical_formula_sum            'C16 H14 N4 O4'
_chemical_formula_weight         326.31
_chemical_name_common            Azines
_chemical_name_systematic
(1E,2E)-bis[1-(4-nitrophenyl)-ethylidene]-hydrazine
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2025-01-02
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-09-02 deposited with the CCDC.	2025-11-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.680(5)
_cell_length_b                   11.488(8)
_cell_length_c                   20.223(11)
_cell_measurement_reflns_used    48866
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      60
_cell_measurement_theta_min      2
_cell_volume                     2946(3)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.803
_diffrn_measurement_device_type  'Pilatus 2M detector'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.67019
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.803
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            48828
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.803
_diffrn_reflns_theta_full        23.710
_diffrn_reflns_theta_max         30.032
_diffrn_reflns_theta_min         1.899
_exptl_absorpt_coefficient_mu    0.096
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_refine_diff_density_max         0.500
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       0.025(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         4136
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0434
_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^)+(0.0786P)^2^+0.4931P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1259
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3926
_reflns_number_total             4136
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00915d2.cif
_cod_data_source_block           cps4615-1-08_0001_run0_hkl4_sg60
_cod_database_code               7251386
_shelx_shelxl_version_number     2019/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C12(H12), C3(H3), C2(H2), C13(H13), C15(H15)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C)
;
_shelx_res_checksum              77983
_olex2_submission_special_instructions 'No special instructions were received'