Crystal structures and stimuli-responsive properties for three novel D–A type salicylhydrazide–viologen compounds with free radical properties under ambient conditions
Xu, Yu-Ru; Zheng, Wen-Hui; Fang, Zong-Bin; Huang, Jian-Cai; Wu, Shu-Ting; CrystEngComm 26 (2024) 1527–1533; doi:10.1039/D3CE01287E

data_7248126
_publ_section_title
;
 Crystal structures and stimuli-responsive properties for three novel D--A
 type salicylhydrazide--viologen compounds with free radical properties
 under ambient conditions
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              1527
_journal_page_last               1533
_journal_paper_doi               10.1039/D3CE01287E
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'F6 P, C19 H17 N4 O3, C3 H7 N O'
_chemical_formula_sum            'C22 H24 F6 N5 O4 P'
_chemical_formula_weight         567.43
_chemical_properties_physical    Light-sensitive
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-07-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-08-05 deposited with the CCDC.	2024-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.036(11)
_cell_length_b                   10.119(5)
_cell_length_c                   22.787(11)
_cell_measurement_reflns_used    7720
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.70
_cell_measurement_theta_min      2.57
_cell_volume                     5081(4)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1638
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            123745
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.126
_diffrn_reflns_theta_min         2.012
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_T_max  0.7410
_exptl_absorpt_correction_T_min  0.7090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1159 before and 0.0702 after correction. The Ratio of minimum to maximum transmission is 0.9568. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear dark orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_description       plate
_exptl_crystal_F_000             2336
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         4516
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1386
_refine_ls_R_factor_gt           0.0581
_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^)+(0.0656P)^2^+4.2225P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1323
_refine_ls_wR_factor_ref         0.1675
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2347
_reflns_number_total             4516
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce01287e2.cif
_cod_data_source_block           p-1
_cod_depositor_comments
'Adding full bibliography for 7248124--7248126.cif.'
_cod_database_code               7248126
_shelxl_version_number           2013-2
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1A), C10(H10), C11(H11), C13(H13), C14(H14), C6(H6), C5(H5),
 C16(H16), C4(H4), C17(H17), C1S(H1S), C19(H19), C18(H18), C3(H3)
2.c Idealised Me refined as rotating group:
 C3S(H3SA,H3SB,H3SC), C2S(H2SA,H2SB,H2SC)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              66519
_shelx_hkl_checksum              22489
_olex2_submission_special_instructions 'No special instructions were received'