Ferrocene functionalized enantiomerically pure Schiff bases and their Zn(ii) and Pd(ii) complexes: a spectroscopic, crystallographic, electrochemical and computational investigation
Celedón, Salvador; Hamon, Paul; Artigas, Vania; Fuentealba, Mauricio; Kahlal, Samia; Carrillo, David; Saillard, Jean-Yves; Hamon, Jean-René; Manzur, Carolina; New Journal of Chemistry 46 (2022) 3948–3960; doi:10.1039/D1NJ06106B

data_7061266
_publ_section_title
;
 Ferrocene functionalized enantiomerically pure Schiff bases and their
 Zn(ii) and Pd(ii) complexes: a spectroscopic, crystallographic,
 electrochemical and computational investigation
;
_journal_issue                   8
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              3948
_journal_page_last               3960
_journal_paper_doi               10.1039/D1NJ06106B
_journal_volume                  46
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H28 Fe N2 O2, C3 H8 O'
_chemical_formula_sum            'C28 H36 Fe N2 O3'
_chemical_formula_weight         504.44
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-12-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-01-27 deposited with the CCDC.	2022-02-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2197(6)
_cell_length_b                   10.3087(5)
_cell_length_c                   25.1548(12)
_cell_measurement_reflns_used    9553
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.17
_cell_measurement_theta_min      2.55
_cell_volume                     2650.1(2)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_collection       'Apex3 v2017.3-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            88090
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.432
_diffrn_reflns_theta_min         2.135
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.599
_exptl_absorpt_correction_T_max  0.9668
_exptl_absorpt_correction_T_min  0.8480
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0612 before and 0.0558 after correction. The Ratio of minimum to maximum transmission is 0.8771. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       plate
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.388
_exptl_crystal_size_mid          0.201
_exptl_crystal_size_min          0.098
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1899 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         5444
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0378
_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^)+(0.0617P)^2^+0.5146P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1036
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                4801
_reflns_number_total             5444
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj06106b3.cif
_cod_data_source_block           test
_cod_depositor_comments
'Adding full bibliography for 7061265--7061266.cif.'
_cod_database_code               7061266
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Shared sites
{O3, O3A}
{C26, C28A}
{C26A, C28}
3. Restrained distances
 C26-C27 = C27-C28
 1.498 with sigma of 0.01
 C26A-C27A = C27A-C28A
 1.498 with sigma of 0.01
 O3-C27
 1.429 with sigma of 0.01
 O3A-C27A
 1.429 with sigma of 0.01
 C26-C28
 2.435 with sigma of 0.004
 C26A-C28A
 2.435 with sigma of 0.004
 O3-C26
 2.348 with sigma of 0.004
 O3-C28
 2.348 with sigma of 0.004
 O3A-C26A
 2.348 with sigma of 0.004
 O3A-C28A
 2.348 with sigma of 0.004
4. Uiso/Uaniso restraints and constraints
Uanis(C28A) \\sim Ueq, Uanis(C26) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
Uanis(C26A) \\sim Ueq, Uanis(C28) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
Uanis(C27A) = Uanis(C27)
Uanis(C28A) = Uanis(C26)
Uanis(C26) = Uanis(C28A)
Uanis(C26A) = Uanis(C28)
Uanis(O3) = Uanis(O3A)
5. Others
 Sof(C26A)=Sof(H)=Sof(HA)=Sof(HB)=Sof(C27A)=Sof(HC)=Sof(C28A)=Sof(HD)=Sof(HE)=
 Sof(HF)=Sof(O3A)=Sof(HG)=1-FVAR(1)
 Sof(O3)=Sof(H3A)=Sof(C28)=Sof(H28A)=Sof(H28B)=Sof(H28C)=Sof(C27)=Sof(H27)=
 Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(H26C)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C20(H20), C25(H25), C27(H27), C27A(HC)
6.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B)
6.c Me refined with riding coordinates:
 C28(H28A,H28B,H28C), C26(H26A,H26B,H26C), C26A(H,HA,HB), C28A(HD,HE,HF)
6.d Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2C), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8),
 C9(H9), C12(H12), C15(H15), C16(H16), C18(H18), C19(H19)
6.e Tetrahedral OH refined with riding coordinates:
 O3(H3A), O3A(HG)
6.f Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'