Synthesis of NiII porphyrin—NiII 5,15-diazaporphyrin hybrid tapes
Wang, Lina; Liao, Zian; Lin, Peng; Jia, Yingying; Liu, Le; Xu, Ling; Zhou, Mingbo; Yin, Bangshao; Rao, Yutao; Nakai, Akito; Tanaka, Takayuki; Shimizu, Daiki; Osuka, Atsuhiro; Song, Jianxin; Chemical Science 15 (2024) 10207–10213; doi:10.1039/D4SC01450B

data_1571713
_publ_section_title
;
 Synthesis of NiII porphyrin---NiII 5,15-diazaporphyrin hybrid tapes
;
_journal_issue                   26
_journal_name_full               'Chemical Science'
_journal_page_first              10207
_journal_page_last               10213
_journal_paper_doi               10.1039/D4SC01450B
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'F6 Sb, C98 H97 N10 Ni2, 5(C6 H5 Cl)'
_chemical_formula_sum            'C128 H122 Cl5 F6 N10 Ni2 Sb'
_chemical_formula_weight         2330.77
_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             2024-05-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-05-08 deposited with the CCDC.	2024-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                80.695(2)
_cell_angle_beta                 71.430(2)
_cell_angle_gamma                72.720(2)
_cell_formula_units_Z            2
_cell_length_a                   16.6924(4)
_cell_length_b                   19.0219(5)
_cell_length_c                   21.9272(6)
_cell_measurement_reflns_used    14346
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      72.0700
_cell_measurement_theta_min      3.0920
_cell_volume                     6284.6(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0697
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -27.00  32.00   1.00    1.00    --   35.17 -57.00  30.00   59
  2  \w     37.00  72.00   1.00    1.00    --   35.17 -99.00 120.00   35
  3  \w     29.00  87.00   1.00    1.00    --   35.17-125.00  60.00   58
  4  \w     32.00  59.00   1.00    1.00    --   35.17-125.00   0.00   27
  5  \w     24.00  87.00   1.00    1.00    --   35.17-125.00 -90.00   63
  6  \w     52.00 113.00   1.00    4.00    --  105.82 -77.00-180.00   61
  7  \w     62.00 115.00   1.00    4.00    --  105.82-111.00-180.00   53
  8  \w     58.00 109.00   1.00    4.00    --  105.82 -94.00 -60.00   51
  9  \w     60.00 130.00   1.00    4.00    --  105.82 -77.00   0.00   70
 10  \w     89.00 114.00   1.00    4.00    --  105.82-111.00  90.00   25
 11  \w     49.00 120.00   1.00    4.00    --  105.82 -30.00 150.00   71
 12  \w     39.00 121.00   1.00    4.00    --  105.82 -45.00  90.00   82
 13  \w     39.00 101.00   1.00    1.00    --   35.17  57.00 -60.00   62
 14  \w     51.00  92.00   1.00    1.00    --   35.17  57.00-180.00   41
 15  \w     41.00 121.00   1.00    4.00    --  105.82 -45.00-120.00   80
 16  \w    127.00 165.00   1.00    4.00    --  105.82  61.00-150.00   38
 17  \w     95.00 172.00   1.00    4.00    --  105.82  77.00-120.00   77
 18  \w    134.00 169.00   1.00    4.00    --  105.82 111.00 120.00   35
 19  \w     39.00 117.00   1.00    4.00    --  105.82 -45.00 -30.00   78
 20  \w     36.00 174.00   1.00    4.00    --  105.82   0.00-150.00  138
 21  \w     18.00  96.00   1.00    1.00    --   35.17  38.00 150.00   78
 22  \w   -104.00  34.00   1.00    1.00    --  -35.17   0.00 120.00  138
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0197208000
_diffrn_orient_matrix_UB_12      0.0324792000
_diffrn_orient_matrix_UB_13      -0.0705970000
_diffrn_orient_matrix_UB_21      0.0597243000
_diffrn_orient_matrix_UB_22      -0.0758233000
_diffrn_orient_matrix_UB_23      -0.0221161000
_diffrn_orient_matrix_UB_31      -0.0788954000
_diffrn_orient_matrix_UB_32      -0.0207284000
_diffrn_orient_matrix_UB_33      -0.0071115000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0711
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            41474
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.600
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         2.439
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.485
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_description       block
_exptl_crystal_F_000             2412
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         3.853
_refine_diff_density_min         -2.760
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1462
_refine_ls_number_reflns         22203
_refine_ls_number_restraints     542
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.1193
_refine_ls_R_factor_gt           0.1035
_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^)+(0.1570P)^2^+24.9407P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2774
_refine_ls_wR_factor_ref         0.2938
_reflns_Friedel_coverage         0.000
_reflns_number_gt                17861
_reflns_number_total             22203
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc01450b2.cif
_cod_data_source_block           15
_cod_depositor_comments
'Adding full bibliography for 1571710--1571717.cif.'
_cod_database_code               1571713
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C100 H100 N8 Ni2 Sb F6'
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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. Restrained distances
 C1F-C125
 1.5 with sigma of 0.02
 C128-C125
 1.5 with sigma of 0.02
 C127-C125
 1.5 with sigma of 0.02
 C1E-C125
 1.5 with sigma of 0.02
 C125-C1D
 1.5 with sigma of 0.02
 C126-C125
 1.5 with sigma of 0.02
 C125-C103
 1.5 with sigma of 0.02
 C1F-C1E
 2.5 with sigma of 0.02
 C126-C1E
 2.5 with sigma of 0.02
 C1F-C126
 2.5 with sigma of 0.02
 C1D-C128
 2.5 with sigma of 0.02
 C127-C128
 2.5 with sigma of 0.02
 C1D-C127
 2.5 with sigma of 0.02
 C128-C103
 2.5 with sigma of 0.02
 C126-C103
 2.5 with sigma of 0.02
 C1D-C103
 2.5 with sigma of 0.02
 C1E-C103
 2.5 with sigma of 0.02
 C127-C103
 2.5 with sigma of 0.02
 C1F-C103
 2.5 with sigma of 0.02
 Sb1-F1A \\sim Sb1-F2 \\sim Sb1-F6 \\sim Sb1-F1 \\sim Sb1-F2A \\sim Sb1-F5A
\\sim Sb1-F5 \\sim Sb1-F6A ~
 Sb1-F4 \\sim Sb1-F4A \\sim Sb1-F3 \\sim Sb1-F3A
 with sigma of 0.02
3. Restrained planarity
 Cl3, C4, C1C, C1B, C1A, C6, C5
 with sigma of 0.1
4. Rigid bond restraints
 Sb1, F4A, F1A, F2A, F3A, F5A, F6A, F1, F4, F2, F5, F6, F3
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C23, Cl3, C4, C5, C6, C1B, C1C, C1A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 Cl3, C4, C5, C6, C1A, C1B, C1C
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C3, C2, C1, C122, C123, C124
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C15, C16, C17, C18, C13, C14, Cl5, C24, C19, C20, C21, C22, C23, Cl4, C28,
 C29, C30, C25, C26, C27, Cl1, C7, C12, C11, C10, C9, C8, Cl2, C127, C128, C126
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C1F, C128, C126, C125, C1D, C1E, C127
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
Uanis(F4) \\sim Ueq, Uanis(F6A) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F4A)
\\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F1A) \\sim Ueq, Uanis(F1) \\sim Ueq,
Uanis(F5A) \\sim Ueq, Uanis(F2A) \\sim Ueq, Uanis(F5) \\sim Ueq, Uanis(F6)
\\sim Ueq, Uanis(F3A) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(Cl3) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C6) \\sim
Ueq, Uanis(C1A) \\sim Ueq, Uanis(C1B) \\sim Ueq, Uanis(C1C) \\sim Ueq: with
sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C3) \\sim Ueq, Uanis(C123) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C124)
\\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C122) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C7) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C10) \\sim
Ueq, Uanis(C12) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(Cl2) \\sim Ueq,
Uanis(C29) \\sim Ueq, Uanis(C30) \\sim Ueq, Uanis(C25) \\sim Ueq, Uanis(C26)
\\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(C28) \\sim Ueq, Uanis(Cl1) \\sim Ueq,
Uanis(C18) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C15)
\\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(Cl5) \\sim Ueq,
Uanis(C127) \\sim Ueq, Uanis(C126) \\sim Ueq, Uanis(C128) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(C1D) \\sim Ueq, Uanis(C1E) \\sim Ueq, Uanis(C1F) \\sim Ueq, Uanis(C126)
\\sim Ueq, Uanis(C128) \\sim Ueq, Uanis(C127) \\sim Ueq, Uanis(C125) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C29) \\sim Ueq, Uanis(C30) \\sim Ueq, Uanis(C25) \\sim Ueq, Uanis(C26)
\\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(Cl1) \\sim Ueq, Uanis(C28) \\sim Ueq,
Uanis(C9) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C12) \\sim
Ueq, Uanis(C11) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(Cl2) \\sim Ueq,
Uanis(C5) \\sim Ueq, Uanis(Cl3) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C1C)
\\sim Ueq, Uanis(C1B) \\sim Ueq, Uanis(C1A) \\sim Ueq, Uanis(C6) \\sim Ueq,
Uanis(C16) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C13)
\\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(Cl5) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C125) \\sim Ueq, Uanis(C128) \\sim Ueq, Uanis(C127) \\sim Ueq,
Uanis(C126) \\sim Ueq, Uanis(C1D) \\sim Ueq, Uanis(C1E) \\sim Ueq, Uanis(C1F)
\\sim Ueq, Uanis(C121) \\sim Ueq, Uanis(C123) \\sim Ueq, Uanis(C124) \\sim Ueq,
Uanis(C122) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3)
\\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
6. Others
 Sof(F4A)=Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(F5A)=Sof(F6A)=1-FVAR(1)
 Sof(F1)=Sof(F4)=Sof(F2)=Sof(F5)=Sof(F6)=Sof(F3)=FVAR(1)
 Sof(C123)=Sof(H12D)=Sof(H12E)=Sof(H12F)=Sof(C124)=Sof(H12G)=Sof(H12H)=
 Sof(H12I)=Sof(C122)=Sof(H12J)=Sof(H12K)=Sof(H12L)=1-FVAR(2)
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(H2C)=Sof(C3)=
 Sof(H3A)=Sof(H3B)=Sof(H3C)=FVAR(2)
 Sof(C126)=Sof(H12S)=Sof(H12T)=Sof(H12U)=Sof(C1E)=Sof(H1EA)=Sof(H1EB)=
 Sof(H1EC)=Sof(C1F)=Sof(H1FA)=Sof(H1FB)=Sof(H1FC)=1-FVAR(3)
 Sof(C128)=Sof(H12M)=Sof(H12N)=Sof(H12O)=Sof(C127)=Sof(H12P)=Sof(H12Q)=
 Sof(H12R)=Sof(C1D)=Sof(H1DA)=Sof(H1DB)=Sof(H1DC)=FVAR(3)
7.a Aromatic/amide H refined with riding coordinates:
 C37(H37), C112(H112), C84(H84), C70(H70), C52(H52), C33(H33), C91(H91),
 C42(H42), C32(H32), C89(H89), C54(H54), C114(H114), C106(H106), C116(H116),
 C46(H46), C88(H88), C63(H63), C79(H79), C47(H47), C74(H74), C75(H75), C80(H80),
  C104(H104), C102(H102), C61(H61), C24(H24), C22(H22), C20(H20), C23(H23),
 C19(H19), C28(H28), C29(H29), C30(H30), C25(H25), C26(H26), C7(H7), C8(H8),
 C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17),
 C5(H5), C6(H6), C1A(H1AA), C1B(H1BA), C1C(H1CA)
7.b Fitted hexagon refined as free rotating group:
 C28(C29,C30,C25,C26,C27), C7(C8,C9,C10,C11,C12), C18(C13,C14,C15,C16,C17),
 C4(C5,C6,C1A,C1B,C1C)
7.c Idealised Me refined as rotating group:
 C56(H56A,H56B,H56C), C64(H64A,H64B,H64C), C51(H51A,H51B,H51C), C57(H57A,H57B,
 H57C), C110(H11A,H11B,H11C), C120(H12A,H12B,H12C), C108(H10A,H10B,H10C),
 C109(H10D,H10E,H10F), C119(H11D,H11E,H11F), C118(H11G,H11H,H11I), C60(H60A,
 H60B,H60C), C66(H66A,H66B,H66C), C95(H95A,H95B,H95C), C98(H98A,H98B,H98C),
 C99(H99A,H99B,H99C), C100(H10G,H10H,H10I), C94(H94A,H94B,H94C), C96(H96A,H96B,
 H96C), C123(H12D,H12E,H12F), C124(H12G,H12H,H12I), C122(H12J,H12K,H12L),
 C128(H12M,H12N,H12O), C127(H12P,H12Q,H12R), C126(H12S,H12T,H12U), C1(H1A,H1B,
 H1C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C1D(H1DA,H1DB,H1DC), C1E(H1EA,H1EB,
 H1EC), C1F(H1FA,H1FB,H1FC)
;
_shelx_res_checksum              37579
_shelx_fab_checksum              16024
_platon_squeeze_void_probe_radius 1.20
_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 1.805
_oxdiff_exptl_absorpt_empirical_full_min 0.635