Synthesis and reactivity of the apically functionalized (pseudo)macrobicyclic iron(ii) tris-dioximates and their hybrid phthalocyaninatoclathrochelate derivatives comprising reactive and vector terminal groups
Chuprin, Alexander S.; Dudkin, Semyon V.; Belova, Svetlana A.; Lebed, Ekaterina G.; Dorovatovskii, Pavel V.; Vologzhanina, Anna V.; Voloshin, Yan Z.; New Journal of Chemistry 46 (2022) 10863–10877; doi:10.1039/D2NJ01560A

data_7061483
_publ_section_title
;
 Synthesis and reactivity of the apically functionalized
 (pseudo)macrobicyclic iron(ii) tris-dioximates and their hybrid
 phthalocyaninatoclathrochelate derivatives comprising reactive and vector
 terminal groups
;
_journal_issue                   22
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              10863
_journal_page_last               10877
_journal_paper_doi               10.1039/D2NJ01560A
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C59 H51 B Fe Hf N14 O8, 1.5(C6 H6)'
_chemical_formula_sum            'C68 H60 B Fe Hf N14 O8'
_chemical_formula_weight         1446.45
_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
_audit_creation_date             2019-04-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-03-28 deposited with the CCDC.	2022-05-05 downloaded from the CCDC.
;
_cell_angle_alpha                101.2950(10)
_cell_angle_beta                 103.7350(10)
_cell_angle_gamma                95.3410(10)
_cell_formula_units_Z            2
_cell_length_a                   11.8206(2)
_cell_length_b                   12.7249(3)
_cell_length_c                   23.8173(5)
_cell_measurement_reflns_used    9697
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      72.12
_cell_measurement_theta_min      3.92
_cell_volume                     3375.82(12)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.965
_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       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            53357
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.199
_diffrn_reflns_theta_min         3.581
_exptl_absorpt_coefficient_mu    5.039
_exptl_absorpt_correction_T_max  0.3526
_exptl_absorpt_correction_T_min  0.1916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0999 before and 0.0444 after correction. The Ratio of minimum to maximum transmission is 0.5434. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            bronze
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_description       prism
_exptl_crystal_F_000             1466
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: benzene : iso-octane'
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         3.558
_refine_diff_density_min         -1.590
_refine_diff_density_rms         0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     807
_refine_ls_number_reflns         12875
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.117
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0437
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0646P)^2^+10.1910P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.1221
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12314
_reflns_number_total             12875
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj01560a2.cif
_cod_data_source_block           ac42_sq
_cod_depositor_comments
'Adding full bibliography for 7061481--7061484.cif.'
_cod_database_code               7061483
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.633
_shelx_estimated_absorpt_t_min   0.264
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C12S) \\sim Ueq: with sigma of 0.003 and sigma for terminal atoms of 0.003
Uanis(C59) \\sim Ueq, Uanis(C57) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.005
Uanis(C7S) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.005
Uiso(C10) = Uiso(C10A) = Uiso(C11) = Uiso(C11A)
Uiso(C4) = Uiso(C4A) = Uiso(C5) = Uiso(C5A)
Uiso(C17) = Uiso(C17A) = Uiso(C16) = Uiso(C16A)
Uanis(C12S) = Uanis(C7S) = Uanis(C8S) = Uanis(C10S) = Uanis(C11S) = Uanis(C9S)
3. Others
 Fixed Sof: H9AA(0.5) H9AB(0.5) H9BC(0.5) H9BD(0.5) H3AA(0.5) H3AB(0.5)
 H3BC(0.5) H3BD(0.5) H12A(0.5) H12B(0.5) H12C(0.5) H12D(0.5) H15A(0.5)
 H15B(0.5) H15C(0.5) H15D(0.5) H6AA(0.5) H6AB(0.5) H6BC(0.5) H6BD(0.5)
 H18A(0.5) H18B(0.5) H18C(0.5) H18D(0.5) C4(0.5) H4A(0.5) H4B(0.5) C10(0.5)
 H10A(0.5) H10B(0.5) C17(0.5) H17A(0.5) H17B(0.5) C11(0.5) H11A(0.5) H11B(0.5)
 C16(0.5) H16A(0.5) H16B(0.5) H58A(0.5) H58(0.5) C5(0.5) H5A(0.5) H5B(0.5)
 C12S(0.5) H12S(0.5) C7S(0.5) H7S(0.5) C8S(0.5) H8S(0.5) C9S(0.5) H9S(0.5)
 C10S(0.5) H10S(0.5) C11S(0.5) H11S(0.5) C5A(0.5) H5AA(0.5) H5AB(0.5) O8B(0.5)
 H59D(0.5) H59E(0.5) H59F(0.5) H59A(0.5) H59B(0.5) H59C(0.5) O8A(0.5) C17A(0.5)
 H17C(0.5) H17D(0.5) C16A(0.5) H16C(0.5) H16D(0.5) C11A(0.5) H11C(0.5)
 H11D(0.5) C10A(0.5) H10C(0.5) H10D(0.5) C4A(0.5) H4AA(0.5) H4AB(0.5)
4.a Ternary CH refined with riding coordinates:
 C58(H58A), C58(H58)
4.b Secondary CH2 refined with riding coordinates:
 C9(H9AA,H9AB), C9(H9BC,H9BD), C3(H3AA,H3AB), C3(H3BC,H3BD), C12(H12A,H12B),
 C12(H12C,H12D), C15(H15A,H15B), C15(H15C,H15D), C6(H6AA,H6AB), C6(H6BC,H6BD),
 C18(H18A,H18B), C18(H18C,H18D), C4(H4A,H4B), C10(H10A,H10B), C17(H17A,H17B),
 C11(H11A,H11B), C16(H16A,H16B), C5(H5A,H5B), C5A(H5AA,H5AB), C17A(H17C,H17D),
 C16A(H16C,H16D), C11A(H11C,H11D), C10A(H10C,H10D), C4A(H4AA,H4AB)
4.c Aromatic/amide H refined with riding coordinates:
 C24(H24), C32(H32), C29(H29), C30(H30), C52(H52), C21(H21), C40(H40),
 C37(H37), C22(H22), C45(H45), C23(H23), C56(H56), C31(H31), C46(H46), C6S(H6S),
  C5S(H5S), C4S(H4S), C3S(H3S), C2S(H2S), C1S(H1S), C53(H53), C38(H38),
 C48(H48), C47(H47), C39(H39), C55(H55), C12S(H12S), C7S(H7S), C8S(H8S),
 C9S(H9S), C10S(H10S), C11S(H11S)
4.d Fitted hexagon refined as free rotating group:
 C6S(C5S,C4S,C3S,C2S,C1S), C12S(C7S,C8S,C9S,C10S,C11S)
4.e Idealised Me refined as rotating group:
 C57(H57A,H57B,H57C), C59(H59D,H59E,H59F), C59(H59A,H59B,H59C)
;
_shelx_res_checksum              6692
_shelx_fab_checksum              57937
_olex2_submission_special_instructions 'No special instructions were received'