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_1571714
_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         'C160 H170 N14 Ni3'
_chemical_formula_sum            'C160 H170 N14 Ni3'
_chemical_formula_weight         2465.22
_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     iterative
_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                72.6545(16)
_cell_angle_beta                 80.455(2)
_cell_angle_gamma                79.266(2)
_cell_formula_units_Z            1
_cell_length_a                   12.1732(4)
_cell_length_b                   15.6437(3)
_cell_length_c                   24.1466(4)
_cell_measurement_reflns_used    24972
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      72.4550
_cell_measurement_theta_min      4.1660
_cell_volume                     4282.49(18)
_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    'olex2.solve (Bourhis et al., 2015)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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      9.00  97.00   1.00    2.00    --   34.23  77.00-120.00   88
  2  \w     64.00  93.00   1.00    2.00    --   34.23  38.00-120.00   29
  3  \w     66.00 105.00   1.00    2.00    --   34.23  19.00-150.00   39
  4  \w     56.00  98.00   1.00    2.00    --   34.23   0.00 -90.00   42
  5  \w     47.00  97.00   1.00    2.00    --   34.23  77.00   0.00   50
  6  \w     61.00 102.00   1.00    2.00    --   34.23  77.00  30.00   41
  7  \w     68.00 100.00   1.00    2.00    --   34.23  77.00 120.00   32
  8  \w     50.00 102.00   1.00    2.00    --   34.23  77.00  90.00   52
  9  \w    113.00 175.00   1.00    8.00    --  107.46  77.00 -30.00   62
 10  \w    133.00 169.00   1.00    8.00    --  107.46  61.00-120.00   36
 11  \w    148.00 173.00   1.00    8.00    --  107.46  77.00-180.00   25
 12  \w    129.00 163.00   1.00    8.00    --  107.46  61.00-180.00   34
 13  \w    120.00 173.00   1.00    8.00    --  107.46  77.00-150.00   53
 14  \w    123.00 160.00   1.00    8.00    --  107.46  77.00 -60.00   37
 15  \w    114.00 172.00   1.00    8.00    --  107.46  77.00   0.00   58
 16  \w    129.00 170.00   1.00    8.00    --  107.46  61.00  90.00   41
 17  \w    123.00 175.00   1.00    8.00    --  107.46  77.00 150.00   52
 18  \w    122.00 174.00   1.00    8.00    --  107.46  77.00  60.00   52
 19  \w    116.00 175.00   1.00    8.00    --  107.46  77.00  30.00   59
 20  \w     89.00 115.00   1.00    8.00    --  107.46  61.00 -90.00   26
 21  \w     89.00 115.00   1.00    8.00    --  107.46  61.00 -60.00   26
 22  \w     89.00 132.00   1.00    8.00    --  107.46  61.00 -30.00   43
 23  \w     86.00 113.00   1.00    8.00    --  107.46  30.00  30.00   27
 24  \w     89.00 116.00   1.00    8.00    --  107.46  61.00   0.00   27
 25  \w     89.00 115.00   1.00    8.00    --  107.46  61.00  30.00   26
 26  \w     89.00 115.00   1.00    8.00    --  107.46  61.00  60.00   26
 27  \w     87.00 115.00   1.00    8.00    --  107.46  30.00  90.00   28
 28  \w     89.00 115.00   1.00    8.00    --  107.46  61.00  90.00   26
 29  \w     89.00 116.00   1.00    8.00    --  107.46  61.00 120.00   27
 30  \w     90.00 115.00   1.00    8.00    --  107.46  61.00 150.00   25
 31  \w     86.00 117.00   1.00    8.00    --  107.46  30.00 150.00   31
 32  \w     86.00 114.00   1.00    8.00    --  107.46  30.00 120.00   28
 33  \w     81.00 175.00   1.00    8.00    --  107.46  77.00 120.00   94
 34  \w     86.00 121.00   1.00    8.00    --  107.46  30.00 -60.00   35
 35  \w     89.00 115.00   1.00    8.00    --  107.46  61.00-120.00   26
 36  \w     89.00 116.00   1.00    8.00    --  107.46  61.00-150.00   27
 37  \w     89.00 116.00   1.00    8.00    --  107.46  61.00-180.00   27
 38  \w     81.00 107.00   1.00    8.00    --  107.46  77.00-120.00   26
 39  \w     81.00 174.00   1.00    8.00    --  107.46  77.00 -90.00   93
 40  \w     86.00 115.00   1.00    8.00    --  107.46  30.00-120.00   29
 41  \w     81.00 107.00   1.00    8.00    --  107.46  77.00-180.00   26
 42  \w     81.00 107.00   1.00    8.00    --  107.46  77.00-150.00   26
 43  \w     86.00 116.00   1.00    8.00    --  107.46  30.00-150.00   30
 44  \w     86.00 119.00   1.00    8.00    --  107.46  30.00-180.00   33
 45  \w     86.00 112.00   1.00    8.00    --  107.46  30.00 -90.00   26
 46  \w     81.00 107.00   1.00    8.00    --  107.46  77.00 -30.00   26
 47  \w     81.00 107.00   1.00    8.00    --  107.46  77.00   0.00   26
 48  \w     81.00 107.00   1.00    8.00    --  107.46  77.00  30.00   26
 49  \w     81.00 108.00   1.00    8.00    --  107.46  77.00  60.00   27
 50  \w     81.00 107.00   1.00    8.00    --  107.46  77.00  90.00   26
 51  \w     86.00 113.00   1.00    8.00    --  107.46  30.00  60.00   27
 52  \w     86.00 112.00   1.00    8.00    --  107.46  30.00   0.00   26
 53  \w     86.00 119.00   1.00    8.00    --  107.46  30.00 -30.00   33
 54  \w     81.00 107.00   1.00    8.00    --  107.46  77.00 -60.00   26
 55  \w     47.00 102.00   1.00    2.00    --   34.23  77.00 -60.00   55
 56  \w     16.00  57.00   1.00    2.00    --   34.23  38.00-120.00   41
 57  \w     17.00  86.00   1.00    2.00    --   34.23  57.00 -60.00   69
 58  \w     17.00  64.00   1.00    2.00    --   34.23  57.00   0.00   47
 59  \w     19.00  79.00   1.00    2.00    --   34.23  57.00  90.00   60
 60  \w     13.00  64.00   1.00    2.00    --   34.23  77.00 120.00   51
 61  \w      7.00  34.00   1.00    2.00    --   34.23  77.00  90.00   27
 62  \w      8.00  60.00   1.00    2.00    --   34.23  77.00  30.00   52
 63  \w      7.00  34.00   1.00    2.00    --   34.23  77.00 -60.00   27
 64  \w      8.00  35.00   1.00    2.00    --   34.23  77.00   0.00   27
 65  \w    -27.00  28.00   1.00    2.00    --   34.23   0.00 -90.00   55
 66  \w     11.00  45.00   1.00    2.00    --   34.23  19.00-150.00   34
 67  \w      7.00  71.00   1.00    2.00    --   34.23  77.00-180.00   64
 68  \w     28.00  53.00   1.00    2.00    --   34.23 -38.00   0.00   25
 69  \w      1.00  71.00   1.00    2.00    --   34.23 -99.00  90.00   70
 70  \w     23.00  84.00   1.00    2.00    --   34.23-125.00  30.00   61
 71  \w     23.00  88.00   1.00    2.00    --   34.23-125.00 -60.00   65
 72  \w     24.00  81.00   1.00    2.00    --   34.23-125.00-150.00   57
 73  \w     38.00  94.00   1.00    8.00    --  107.46 -94.00-180.00   56
 74  \w    105.00 134.00   1.00    8.00    --  107.46 -77.00 -90.00   29
 75  \w     56.00 115.00   1.00    8.00    --  107.46-111.00 -90.00   59
 76  \w     43.00  81.00   1.00    8.00    --  107.46 -77.00 -90.00   38
 77  \w     39.00 106.00   1.00    8.00    --  107.46 -94.00 -30.00   67
 78  \w     53.00 106.00   1.00    8.00    --  107.46-111.00  90.00   53
 79  \w     38.00 107.00   1.00    8.00    --  107.46 -94.00 120.00   69
 80  \w     81.00 107.00   1.00    8.00    --  107.46  77.00 150.00   26
 81  \w    -19.00  53.00   1.00    2.00    --   34.23 -38.00  60.00   72
 82  \w    -32.00  45.00   1.00    2.00    --   34.23 -77.00 -90.00   77
 83  \w    -31.00  14.00   1.00    2.00    --   34.23 -38.00   0.00   45
 84  \w    -35.00  42.00   1.00    2.00    --   34.23 -38.00 150.00   77
;
_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      -0.0127362000
_diffrn_orient_matrix_UB_12      0.0485821000
_diffrn_orient_matrix_UB_13      -0.0647378000
_diffrn_orient_matrix_UB_21      -0.0547753000
_diffrn_orient_matrix_UB_22      0.0874414000
_diffrn_orient_matrix_UB_23      0.0165509000
_diffrn_orient_matrix_UB_31      0.1168820000
_diffrn_orient_matrix_UB_32      0.0294532000
_diffrn_orient_matrix_UB_33      -0.0080823000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            61516
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.598
_diffrn_reflns_theta_max         66.598
_diffrn_reflns_theta_min         4.975
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.728
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68204
_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            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    0.956
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.832
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     882
_refine_ls_number_reflns         15113
_refine_ls_number_restraints     102
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0604
_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^)+(0.0682P)^2^+5.8186P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1527
_refine_ls_wR_factor_ref         0.1605
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12632
_reflns_number_total             15113
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc01450b2.cif
_cod_data_source_block           3b
_cod_depositor_comments
'Adding full bibliography for 1571710--1571717.cif.'
_cod_original_cell_volume        4282.51(18)
_cod_database_code               1571714
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C100 N10 H150 Ni3'
_shelx_estimated_absorpt_t_max   0.931
_shelx_estimated_absorpt_t_min   0.868
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Rigid bond restraints
 C64, C65, C66, C67, C65A, C66A, C67A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C50, C51, C52, C53, C51A, C52A, C53A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C65A) \\sim Ueq, Uanis(C65) \\sim Ueq, Uanis(C66A) \\sim Ueq, Uanis(C66)
\\sim Ueq, Uanis(C67A) \\sim Ueq, Uanis(C67) \\sim Ueq, Uanis(C64) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C52A) \\sim Ueq, Uanis(C53) \\sim Ueq, Uanis(C53A) \\sim Ueq, Uanis(C51)
\\sim Ueq, Uanis(C51A) \\sim Ueq, Uanis(C52) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
4. Others
 Sof(C65A)=Sof(H65D)=Sof(H65E)=Sof(H65F)=Sof(C66A)=Sof(H66D)=Sof(H66E)=
 Sof(H66F)=Sof(C67A)=Sof(H67D)=Sof(H67E)=Sof(H67F)=1-FVAR(1)
 Sof(C65)=Sof(H65A)=Sof(H65B)=Sof(H65C)=Sof(C66)=Sof(H66A)=Sof(H66B)=Sof(H66C)=
 Sof(C67)=Sof(H67A)=Sof(H67B)=Sof(H67C)=FVAR(1)
 Sof(C51A)=Sof(H51D)=Sof(H51E)=Sof(H51F)=Sof(C52A)=Sof(H52D)=Sof(H52E)=
 Sof(H52F)=Sof(C53A)=Sof(H53D)=Sof(H53E)=Sof(H53F)=1-FVAR(2)
 Sof(C51)=Sof(H51A)=Sof(H51B)=Sof(H51C)=Sof(C52)=Sof(H52A)=Sof(H52B)=Sof(H52C)=
 Sof(C53)=Sof(H53A)=Sof(H53B)=Sof(H53C)=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8), C12(H12), C13(H13), C17(H17), C18(H18),
 C23(H23), C27(H27), C28(H28), C31(H31), C33(H33), C35(H35), C45(H45), C47(H47),
  C49(H49), C59(H59), C61(H61), C63(H63), C74(H74), C76(H76)
5.b Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C39(H39A,H39B,H39C), C41(H41A,H41B,
 H41C), C42(H42A,H42B,H42C), C43(H43A,H43B,H43C), C55(H55A,H55B,H55C), C56(H56A,
 H56B,H56C), C57(H57A,H57B,H57C), C69(H69A,H69B,H69C), C70(H70A,H70B,H70C),
 C71(H71A,H71B,H71C), C78(H78A,H78B,H78C), C79(H79A,H79B,H79C), C80(H80A,H80B,
 H80C), C51(H51A,H51B,H51C), C52(H52A,H52B,H52C), C53(H53A,H53B,H53C), C65(H65A,
 H65B,H65C), C66(H66A,H66B,H66C), C67(H67A,H67B,H67C), C51A(H51D,H51E,H51F),
 C52A(H52D,H52E,H52F), C53A(H53D,H53E,H53F), C65A(H65D,H65E,H65F), C66A(H66D,
 H66E,H66F), C67A(H67D,H67E,H67F)
;
_shelx_res_checksum              8670
_shelx_fab_checksum              23418
_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 2.329
_oxdiff_exptl_absorpt_empirical_full_min 0.501