Design of a new nitronyl-nitroxide biradical and its complexes: synthesis, crystal structures and magnetic properties
Spinu, Cristian Andrei; Novitchi, Ghenadie; Hillebrand, Mihaela; Mocanu, Teodora; Ionita, Gabriela; Hanganu, Anamaria; Tecuceanu, Victoriţa; Andruh, Marius; CrystEngComm 27 (2025) 6462–6472; doi:10.1039/D5CE00795J

data_7250846
_publ_section_title
;
 Design of a new nitronyl-nitroxide biradical and its complexes:
 synthesis, crystal structures and magnetic properties
;
_journal_issue                   39
_journal_name_full               CrystEngComm
_journal_page_first              6462
_journal_page_last               6472
_journal_paper_doi               10.1039/D5CE00795J
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C17 H14 N2 O8'
_chemical_formula_sum            'C17 H14 N2 O8'
_chemical_formula_weight         374.30
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-08-04
_audit_creation_method
;
Olex2 1.5-ac6-016
(compiled 2024.01.13 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6897)
;
_audit_update_record
;
2025-08-04 deposited with the CCDC.	2025-09-09 downloaded from the CCDC.
;
_cell_angle_alpha                101.627(12)
_cell_angle_beta                 93.540(10)
_cell_angle_gamma                90.027(11)
_cell_formula_units_Z            2
_cell_length_a                   8.4632(10)
_cell_length_b                   9.8218(14)
_cell_length_c                   10.1702(14)
_cell_measurement_reflns_used    2740
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.2710
_cell_measurement_theta_min      2.1520
_cell_volume                     826.39(19)
_computing_cell_refinement       'CrysAlisPro 1.171.42.76a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.76a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.76a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac6-016 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-016 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -16.00  48.00   0.50    3.65    --   -4.97  37.00  90.00  128
  2  \w    -17.00  62.00   0.50    3.65    --   -4.97  37.00 -30.00  158
  3  \w    -11.00  65.00   0.50    3.65    --   -4.97  19.00-150.00  152
  4  \w    -15.00  27.00   0.50    3.65    --   -4.97 -99.00-150.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0084405000
_diffrn_orient_matrix_UB_12      0.0624499000
_diffrn_orient_matrix_UB_13      -0.0239631000
_diffrn_orient_matrix_UB_21      -0.0002055000
_diffrn_orient_matrix_UB_22      -0.0388237000
_diffrn_orient_matrix_UB_23      -0.0668582000
_diffrn_orient_matrix_UB_31      -0.0835509000
_diffrn_orient_matrix_UB_32      0.0054278000
_diffrn_orient_matrix_UB_33      -0.0067829000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6030
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.048
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.76a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         2883
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.1059
_refine_ls_R_factor_gt           0.0789
_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^)+(0.1576P)^2^+0.1326P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2409
_refine_ls_wR_factor_ref         0.2659
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1866
_reflns_number_total             2883
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00795j2.cif
_cod_data_source_block           cs382
_cod_depositor_comments
'Adding full bibliography for 7250845--7250847.cif.'
_cod_database_code               7250846
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C10 H10 N4 O5'
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.945
_olex2_refinement_description
;
1. Restrained distances
 O6B-C17
 1.234 with sigma of 0.002
2. Uiso/Uaniso restraints and constraints
C12 \\sim C17: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 1.7A
C17 \\sim O6B: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 1.7A
Uanis(O6B) = Uanis(O6A)
3. Rigid body (RIGU) restrains
 O6A, O6B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Sof(H17A)=Sof(O6B)=1-FVAR(1)
 Sof(O6A)=Sof(H17)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C13(H13), C15(H15), C5(H5A), C7(H7), C17(H17), C17(H17A)
5.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
5.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O5(H5)
;
_shelx_res_checksum              6966
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.221
_oxdiff_exptl_absorpt_empirical_full_min 0.372