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_7251387
_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         'C15 H13 N3 O2'
_chemical_formula_sum            'C15 H13 N3 O2'
_chemical_formula_weight         267.28
_chemical_name_common            Azines
_chemical_name_systematic
(1E,2E)-1-benzylidene-2-[1-(4-nitrophenyl)-ethylidene]-hydrazine
_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   mixed
_audit_creation_date             2025-01-08
_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                105.669(5)
_cell_angle_beta                 105.283(8)
_cell_angle_gamma                116.786(4)
_cell_formula_units_Z            2
_cell_length_a                   9.3240(17)
_cell_length_b                   9.3840(11)
_cell_length_c                   9.5750(10)
_cell_measurement_reflns_used    32769
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      60
_cell_measurement_theta_min      2
_cell_volume                     643.68(17)
_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)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.841
_diffrn_measurement_device_type  'Pilatus 2M detector'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.67019
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.841
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            32769
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.841
_diffrn_reflns_theta_full        23.710
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_min         2.330
_exptl_absorpt_coefficient_mu    0.084
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.597
_refine_diff_density_rms         0.156
_refine_ls_extinction_coef       0.76(4)
_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   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3767
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0501
_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^)+(0.0807P)^2^+0.1209P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1286
_refine_ls_wR_factor_ref         0.1290
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3707
_reflns_number_total             3767
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00915d2.cif
_cod_data_source_block           cps4614-1-14_merge_a
_cod_original_cell_volume        643.68(16)
_cod_database_code               7251387
_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:
 C3(H3), C9(H9), C2(H2), C15(H15), C12(H12), C11(H11), C14(H14), C13(H13)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_shelx_res_checksum              59978
_olex2_submission_special_instructions 'No special instructions were received'