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_1571711
_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     dual
_audit_creation_date             2024-05-05
_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                73.5180(12)
_cell_angle_beta                 89.4513(11)
_cell_angle_gamma                80.3482(12)
_cell_formula_units_Z            1
_cell_length_a                   11.99689(17)
_cell_length_b                   15.9669(2)
_cell_length_c                   23.9854(3)
_cell_measurement_reflns_used    37246
_cell_measurement_temperature    101(2)
_cell_measurement_theta_max      72.1130
_cell_measurement_theta_min      3.9210
_cell_volume                     4339.81(10)
_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 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      101(2)
_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    -48.00  24.00   1.00    3.00    --  -35.42  57.00  60.00   72
  2  \w     10.00  87.00   1.00    3.00    --   35.42  77.00 150.00   77
  3  \w     57.00  96.00   1.00    3.00    --   35.42  38.00  60.00   39
  4  \w     53.00  79.00   1.00    3.00    --   35.42  77.00   0.00   26
  5  \w     63.00  96.00   1.00    3.00    --   35.42  77.00 -60.00   33
  6  \w     58.00  84.00   1.00    3.00    --   35.42  77.00 -90.00   26
  7  \w     58.00 100.00   1.00    3.00    --   35.42  57.00-120.00   42
  8  \w    123.00 166.00   1.00    9.00    --  105.82  77.00-180.00   43
  9  \w    124.00 169.00   1.00    9.00    --  105.82  77.00 -90.00   45
 10  \w    123.00 171.00   1.00    9.00    --  105.82  77.00 -30.00   48
 11  \w    133.00 166.00   1.00    9.00    --  105.82  61.00   0.00   33
 12  \w    122.00 172.00   1.00    9.00    --  105.82  77.00  90.00   50
 13  \w    132.00 167.00   1.00    9.00    --  105.82  61.00 120.00   35
 14  \w    113.00 165.00   1.00    9.00    --  105.82  77.00  30.00   52
 15  \w    123.00 167.00   1.00    9.00    --  105.82  77.00 -60.00   44
 16  \w    121.00 170.00   1.00    9.00    --  105.82  77.00-120.00   49
 17  \w    112.00 171.00   1.00    9.00    --  105.82  77.00-150.00   59
 18  \w     87.00 122.00   1.00    9.00    --  105.82  30.00-180.00   35
 19  \w     87.00 113.00   1.00    9.00    --  105.82  30.00-150.00   26
 20  \w     89.00 116.00   1.00    9.00    --  105.82  61.00-120.00   27
 21  \w     89.00 115.00   1.00    9.00    --  105.82  61.00-150.00   26
 22  \w     87.00 114.00   1.00    9.00    --  105.82  30.00-120.00   27
 23  \w     89.00 114.00   1.00    9.00    --  105.82  61.00 -90.00   25
 24  \w     89.00 114.00   1.00    9.00    --  105.82  61.00 -60.00   25
 25  \w     89.00 123.00   1.00    9.00    --  105.82  61.00 -30.00   34
 26  \w     88.00 128.00   1.00    9.00    --  105.82  30.00 -30.00   40
 27  \w     87.00 124.00   1.00    9.00    --  105.82  30.00 -60.00   37
 28  \w     89.00 114.00   1.00    9.00    --  105.82  61.00   0.00   25
 29  \w     88.00 117.00   1.00    9.00    --  105.82  30.00  30.00   29
 30  \w     89.00 115.00   1.00    9.00    --  105.82  61.00  60.00   26
 31  \w    116.00 172.00   1.00    9.00    --  105.82  77.00  60.00   56
 32  \w    123.00 172.00   1.00    9.00    --  105.82  77.00 150.00   49
 33  \w     89.00 114.00   1.00    9.00    --  105.82  61.00 150.00   25
 34  \w     89.00 115.00   1.00    9.00    --  105.82  61.00 120.00   26
 35  \w     89.00 114.00   1.00    9.00    --  105.82  61.00  90.00   25
 36  \w     87.00 151.00   1.00    9.00    --  105.82  30.00  60.00   64
 37  \w     87.00 115.00   1.00    9.00    --  105.82  30.00 120.00   28
 38  \w     88.00 115.00   1.00    9.00    --  105.82  30.00 150.00   27
 39  \w     81.00 106.00   1.00    9.00    --  105.82  77.00 150.00   25
 40  \w     81.00 106.00   1.00    9.00    --  105.82  77.00 120.00   25
 41  \w     81.00 107.00   1.00    9.00    --  105.82  77.00  90.00   26
 42  \w     81.00 107.00   1.00    9.00    --  105.82  77.00  60.00   26
 43  \w     89.00 115.00   1.00    9.00    --  105.82  61.00  30.00   26
 44  \w     87.00 118.00   1.00    9.00    --  105.82  30.00  90.00   31
 45  \w     81.00 107.00   1.00    9.00    --  105.82  77.00  30.00   26
 46  \w     81.00 106.00   1.00    9.00    --  105.82  77.00   0.00   25
 47  \w     81.00 106.00   1.00    9.00    --  105.82  77.00 -30.00   25
 48  \w     81.00 107.00   1.00    9.00    --  105.82  77.00 -60.00   26
 49  \w     81.00 106.00   1.00    9.00    --  105.82  77.00 -90.00   25
 50  \w     81.00 107.00   1.00    9.00    --  105.82  77.00-120.00   26
 51  \w     81.00 106.00   1.00    9.00    --  105.82  77.00-150.00   25
 52  \w     89.00 114.00   1.00    9.00    --  105.82  61.00-180.00   25
 53  \w     81.00 107.00   1.00    9.00    --  105.82  77.00-180.00   26
 54  \w     87.00 113.00   1.00    9.00    --  105.82  30.00 -90.00   26
 55  \w     39.00 131.00   1.00    9.00    --  105.82 -77.00-120.00   92
 56  \w     84.00 109.00   1.00    9.00    --  105.82 -94.00-120.00   25
 57  \w     49.00 114.00   1.00    9.00    --  105.82-111.00-150.00   65
 58  \w     37.00  71.00   1.00    9.00    --  105.82 -94.00-120.00   34
 59  \w     37.00 107.00   1.00    9.00    --  105.82 -94.00   0.00   70
 60  \w     43.00 131.00   1.00    9.00    --  105.82 -77.00  30.00   88
 61  \w     39.00  70.00   1.00    3.00    --   35.42 -99.00 120.00   31
 62  \w      3.00  66.00   1.00    3.00    --   35.42 -99.00   0.00   63
 63  \w     27.00  88.00   1.00    3.00    --   35.42-125.00 -60.00   61
 64  \w    -24.00  21.00   1.00    3.00    --   35.42 -77.00 -60.00   45
 65  \w    -46.00  33.00   1.00    3.00    --  -35.42  38.00-150.00   79
 66  \w    -30.00  30.00   1.00    3.00    --  -35.42  57.00-120.00   60
 67  \w      3.00  28.00   1.00    3.00    --   35.42  91.00-153.71   25
 68  \w     21.00  54.00   1.00    3.00    --   35.42  57.00-120.00   33
 69  \w     14.00  51.00   1.00    3.00    --   35.42  77.00 -60.00   37
 70  \w     11.00  46.00   1.00    3.00    --   35.42  77.00   0.00   35
 71  \w     18.00  46.00   1.00    3.00    --   35.42  38.00  60.00   28
 72  \w     22.00  85.00   1.00    3.00    --   35.42  57.00 120.00   63
 73  \w     10.00  69.00   1.00    3.00    --   35.42  77.00  30.00   59
 74  \w     11.00  42.00   1.00    3.00    --   35.42  77.00 -90.00   31
 75  \w      2.00  27.00   1.00    3.00    --   35.42  92.00  83.58   25
 76  \w    -53.00  19.00   1.00    3.00    --  -35.42  38.00 150.00   72
 77  \w    -82.00 -19.00   1.00    3.00    --  -35.42 -40.00  46.62   63
 78  \w   -104.00 -12.00   1.00    3.00    --  -35.42 -19.00 120.00   92
;
_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      -0.0694836000
_diffrn_orient_matrix_UB_12      0.0938485000
_diffrn_orient_matrix_UB_13      -0.0106795000
_diffrn_orient_matrix_UB_21      -0.0054473000
_diffrn_orient_matrix_UB_22      -0.0143071000
_diffrn_orient_matrix_UB_23      0.0661788000
_diffrn_orient_matrix_UB_31      0.1101669000
_diffrn_orient_matrix_UB_32      0.0376926000
_diffrn_orient_matrix_UB_33      -0.0002755000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            61951
_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         3.740
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.719
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48665
_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            'metallic greenish black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    0.943
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.719
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     931
_refine_ls_number_reflns         15306
_refine_ls_number_restraints     272
_refine_ls_restrained_S_all      1.145
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0625
_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^)+(0.0658P)^2^+7.6211P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1625
_refine_ls_wR_factor_ref         0.1652
_reflns_Friedel_coverage         0.000
_reflns_number_gt                14209
_reflns_number_total             15306
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc01450b2.cif
_cod_data_source_block           5b
_cod_depositor_comments
'Adding full bibliography for 1571710--1571717.cif.'
_cod_original_cell_volume        4339.82(11)
_cod_database_code               1571711
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C100 H100 Ni3 N10'
_shelx_estimated_absorpt_t_max   0.965
_shelx_estimated_absorpt_t_min   0.813
_reflns_odcompleteness_completeness 99.92
_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
 C60-C59 = C59-C61 = C62-C59 = C59A-C62A = C59A-C61A = C59A-C60A
 1.5 with sigma of 0.02
 C60-C61
 2.5 with sigma of 0.1
 C62-C61
 2.5 with sigma of 0.1
 C60-C62
 2.5 with sigma of 0.1
 C60A-C61A
 2.5 with sigma of 0.1
 C61A-C62A
 2.5 with sigma of 0.1
 C60A-C62A
 2.5 with sigma of 0.1
 C47-C45 = C46-C45 = C45-C46A = C48A-C45 = C48-C45 = C47A-C45
 1.5 with sigma of 0.02
 C47-C46
 2.5 with sigma of 0.1
 C46-C48
 2.5 with sigma of 0.1
 C47-C48
 2.5 with sigma of 0.1
 C47A-C46A
 2.5 with sigma of 0.1
 C46A-C48A
 2.5 with sigma of 0.1
 C48A-C47A
 2.5 with sigma of 0.1
3. Rigid bond restraints
 C53, C59, C60, C61, C62, C59A, C60A, C61A, C62A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C45, C46, C47, C48, C46A, C47A, C48A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C31, C32, C33, C34, C31A, C32A, C33A, C34A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C79
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C62) \\sim Ueq, Uanis(C59A) \\sim Ueq, Uanis(C61) \\sim Ueq, Uanis(C60)
\\sim Ueq, Uanis(C59) \\sim Ueq, Uanis(C61A) \\sim Ueq, Uanis(C60A) \\sim Ueq,
Uanis(C62A) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C45) \\sim Ueq, Uanis(C46) \\sim Ueq, Uanis(C47) \\sim Ueq, Uanis(C48A)
\\sim Ueq, Uanis(C47A) \\sim Ueq, Uanis(C46A) \\sim Ueq, Uanis(C48) \\sim Ueq:
with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C31) \\sim Ueq, Uanis(C34) \\sim Ueq, Uanis(C32) \\sim Ueq, Uanis(C33)
\\sim Ueq, Uanis(C34A) \\sim Ueq, Uanis(C33A) \\sim Ueq, Uanis(C32A) \\sim Ueq,
Uanis(C31A) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C79) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C49) \\sim Ueq, Uanis(C50) \\sim Ueq, Uanis(C51) \\sim Ueq, Uanis(C52)
\\sim Ueq, Uanis(C53) \\sim Ueq, Uanis(C54) \\sim Ueq, Uanis(C55) \\sim Ueq,
Uanis(C56) \\sim Ueq, Uanis(C57) \\sim Ueq, Uanis(C58) \\sim Ueq: with sigma of
0.002 and sigma for terminal atoms of 0.004
5. Others
 Sof(C59A)=Sof(C60A)=Sof(H60D)=Sof(H60E)=Sof(H60F)=Sof(C61A)=Sof(H61D)=
 Sof(H61E)=Sof(H61F)=Sof(C62A)=Sof(H62D)=Sof(H62E)=Sof(H62F)=1-FVAR(1)
 Sof(C59)=Sof(C60)=Sof(H60A)=Sof(H60B)=Sof(H60C)=Sof(C61)=Sof(H61A)=Sof(H61B)=
 Sof(H61C)=Sof(C62)=Sof(H62A)=Sof(H62B)=Sof(H62C)=FVAR(1)
 Sof(C46A)=Sof(H46D)=Sof(H46E)=Sof(H46F)=Sof(C47A)=Sof(H47D)=Sof(H47E)=
 Sof(H47F)=Sof(C48A)=Sof(H48D)=Sof(H48E)=Sof(H48F)=1-FVAR(2)
 Sof(C46)=Sof(H46A)=Sof(H46B)=Sof(H46C)=Sof(C47)=Sof(H47A)=Sof(H47B)=Sof(H47C)=
 Sof(C48)=Sof(H48A)=Sof(H48B)=Sof(H48C)=FVAR(2)
 Sof(C31A)=Sof(C32A)=Sof(H32D)=Sof(H32E)=Sof(H32F)=Sof(C33A)=Sof(H33D)=
 Sof(H33E)=Sof(H33F)=Sof(C34A)=Sof(H34D)=Sof(H34E)=Sof(H34F)=1-FVAR(3)
 Sof(C31)=Sof(C32)=Sof(H32A)=Sof(H32B)=Sof(H32C)=Sof(C33)=Sof(H33A)=Sof(H33B)=
 Sof(H33C)=Sof(C34)=Sof(H34A)=Sof(H34B)=Sof(H34C)=FVAR(3)
6.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8), C12(H12), C13(H13), C15(H15), C18(H18),
 C22(H22), C24(H24), C26(H26), C36(H36), C38(H38), C40(H40), C50(H50), C52(H52),
  C54(H54), C64(H64), C68(H68), C69(H69), C74(H74), C76(H76)
6.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C42(H42A,H42B,
 H42C), C43(H43A,H43B,H43C), C44(H44A,H44B,H44C), C56(H56A,H56B,H56C), C57(H57A,
 H57B,H57C), C58(H58A,H58B,H58C), C78(H78A,H78B,H78C), C79(H79A,H79B,H79C),
 C80(H80A,H80B,H80C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C34(H34A,H34B,
 H34C), C46(H46A,H46B,H46C), C47(H47A,H47B,H47C), C48(H48A,H48B,H48C), C60(H60A,
 H60B,H60C), C61(H61A,H61B,H61C), C62(H62A,H62B,H62C), C32A(H32D,H32E,H32F),
 C33A(H33D,H33E,H33F), C34A(H34D,H34E,H34F), C46A(H46D,H46E,H46F), C47A(H47D,
 H47E,H47F), C48A(H48D,H48E,H48F), C60A(H60D,H60E,H60F), C61A(H61D,H61E,H61F),
 C62A(H62D,H62E,H62F)
;
_shelx_res_checksum              81134
_shelx_fab_checksum              51600
_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 2.798
_oxdiff_exptl_absorpt_empirical_full_min 0.410