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_1571710
_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      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                90
_cell_angle_beta                 108.649(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.2235(11)
_cell_length_b                   30.1037(7)
_cell_length_c                   27.7552(7)
_cell_measurement_reflns_used    14364
_cell_measurement_temperature    171(2)
_cell_measurement_theta_max      72.3910
_cell_measurement_theta_min      3.8150
_cell_volume                     16010.2(11)
_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      171(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    -81.00 -54.00   1.00    7.50    --  -34.73 -57.00-150.00   27
  2  \w    -52.00 -25.00   1.00    7.50    --  -34.73  77.00-150.00   27
  3  \w    -99.00 -40.00   1.00    7.50    --  -34.73 -57.00  60.00   59
  4  \w     -5.00  33.00   1.00    7.50    --  -34.73  77.00-150.00   38
  5  \w    -29.00  48.00   1.00    7.50    --   34.73 -57.00 -60.00   77
  6  \w     54.00  88.00   1.00    7.50    --   34.73-125.00  90.00   34
  7  \w     24.00  82.00   1.00    7.50    --   34.73-125.00-120.00   58
  8  \w    -29.00 104.00   1.00    7.50    --   34.73   0.00  90.00  133
  9  \w      1.00  74.00   1.00    7.50    --   34.73 -99.00 -90.00   73
 10  \w    -33.00  50.00   1.00    7.50    --   34.73 -57.00  90.00   83
 11  \w      6.00  49.00   1.00    7.50    --   34.73 -99.00  60.00   43
 12  \w     39.00 117.00   1.00   30.00    --  107.46 -45.00 120.00   78
 13  \w     40.00 123.00   1.00   30.00    --  107.46 -45.00 -60.00   83
 14  \w     42.00  97.00   1.00   30.00    --  107.46 -61.00-120.00   55
 15  \w     41.00  66.00   1.00   30.00    --  107.46 -45.00  30.00   25
 16  \w     62.00  96.00   1.00   30.00    --  107.46 -94.00 -30.00   34
 17  \w     43.00  91.00   1.00   30.00    --  107.46 -94.00-180.00   48
 18  \w     43.00  99.00   1.00   30.00    --  107.46 -30.00-180.00   56
 19  \w     46.00 113.00   1.00   30.00    --  107.46-111.00 -90.00   67
 20  \w     84.00 173.00   1.00   30.00    --  107.46  77.00  90.00   89
 21  \w    112.00 174.00   1.00   30.00    --  107.46  45.00  60.00   62
 22  \w     46.00 105.00   1.00   30.00    --  107.46 -61.00  30.00   59
 23  \w     88.00 124.00   1.00   30.00    --  107.46 -45.00  30.00   36
 24  \w     69.00 107.00   1.00   30.00    --  107.46 -94.00 120.00   38
 25  \w     72.00 177.00   1.00   30.00    --  107.46   0.00-150.00  105
 26  \w     37.00 112.00   1.00   30.00    --  107.46-111.00  60.00   75
;
_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      -0.0696515000
_diffrn_orient_matrix_UB_12      0.0250238000
_diffrn_orient_matrix_UB_13      -0.0105081000
_diffrn_orient_matrix_UB_21      -0.0058978000
_diffrn_orient_matrix_UB_22      -0.0168452000
_diffrn_orient_matrix_UB_23      0.0508768000
_diffrn_orient_matrix_UB_31      0.0396999000
_diffrn_orient_matrix_UB_32      0.0413581000
_diffrn_orient_matrix_UB_33      0.0270523000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0970
_diffrn_reflns_av_unetI/netI     0.0963
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            105696
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.601
_diffrn_reflns_theta_max         66.601
_diffrn_reflns_theta_min         3.575
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.779
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46636
_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            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.023
_exptl_crystal_description       needle
_exptl_crystal_F_000             5248
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.734
_refine_diff_density_min         -0.593
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1724
_refine_ls_number_reflns         28255
_refine_ls_number_restraints     321
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.1710
_refine_ls_R_factor_gt           0.1127
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3239
_refine_ls_wR_factor_ref         0.3921
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12329
_reflns_number_total             28255
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc01450b2.cif
_cod_data_source_block           5a
_cod_depositor_comments
'Adding full bibliography for 1571710--1571717.cif.'
_cod_database_code               1571710
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C200 H200 N14 Ni3 Cl'
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.860
_reflns_odcompleteness_completeness 99.92
_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. Restrained distances
 C931-C929
 2.5 with sigma of 0.1
 C931-C129 = C929-C129
 1.5 with sigma of 0.02
 C930-C129
 1.5 with sigma of 0.02
 C930-C931
 2.5 with sigma of 0.02
 C929-C930
 2.5 with sigma of 0.02
3. Rigid bond restraints
 C31, C32, C33, C34, C32A, C33A, C34A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C129, C130, C131, C132, C929, C931
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C59
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C133, C134, C135, C136, C137, C138, C139, C140, C141, C142, C143, C144, C145,
 C146, C157, C158, C159, C160, C958, C959, C960
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C930
 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(C157) \\sim Ueq, Uanis(C159) \\sim Ueq, Uanis(C160) \\sim Ueq,
Uanis(C158) \\sim Ueq, Uanis(C958) \\sim Ueq, Uanis(C959) \\sim Ueq,
Uanis(C960) \\sim Ueq: with sigma of 0 and sigma for terminal atoms of 0.02
Uanis(C31) \\sim Ueq, Uanis(C34) \\sim Ueq, Uanis(C33) \\sim Ueq, Uanis(C32)
\\sim Ueq, Uanis(C33A) \\sim Ueq, Uanis(C32A) \\sim Ueq, Uanis(C34A) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 1
Uanis(C142) \\sim Ueq, Uanis(C140) \\sim Ueq, Uanis(C139) \\sim Ueq,
Uanis(C141) \\sim Ueq, Uanis(C135) \\sim Ueq, Uanis(C136) \\sim Ueq,
Uanis(C134) \\sim Ueq, Uanis(C133) \\sim Ueq, Uanis(C106) \\sim Ueq,
Uanis(C138) \\sim Ueq, Uanis(C137) \\sim Ueq, Uanis(C143) \\sim Ueq,
Uanis(C144) \\sim Ueq, Uanis(C146) \\sim Ueq, Uanis(C145) \\sim Ueq,
Uanis(C131) \\sim Ueq, Uanis(C931) \\sim Ueq, Uanis(C132) \\sim Ueq,
Uanis(C929) \\sim Ueq, Uanis(C130) \\sim Ueq, Uanis(C129) \\sim Ueq,
Uanis(C110) \\sim Ueq, Uanis(C111) \\sim Ueq, Uanis(C109) \\sim Ueq,
Uanis(C108) \\sim Ueq, Uanis(C107) \\sim Ueq, Uanis(C105) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(C930) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Others
 Sof(C958)=Sof(H95A)=Sof(H95B)=Sof(H95C)=Sof(C959)=Sof(H95D)=Sof(H95E)=
 Sof(H95F)=Sof(C960)=Sof(H96D)=Sof(H96E)=Sof(H96F)=1-FVAR(1)
 Sof(C158)=Sof(H15J)=Sof(H15K)=Sof(H15L)=Sof(C159)=Sof(H15M)=Sof(H15N)=
 Sof(H15O)=Sof(C160)=Sof(H16A)=Sof(H16B)=Sof(H16C)=FVAR(1)
 Sof(C929)=Sof(H92A)=Sof(H92B)=Sof(H92C)=Sof(C930)=Sof(H93A)=Sof(H93B)=
 Sof(H93C)=Sof(C931)=Sof(H93D)=Sof(H93E)=Sof(H93F)=1-FVAR(2)
 Sof(C130)=Sof(H13A)=Sof(H13B)=Sof(H13C)=Sof(C131)=Sof(H13D)=Sof(H13E)=
 Sof(H13F)=Sof(C132)=Sof(H13G)=Sof(H13H)=Sof(H13I)=FVAR(2)
 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(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 Me refined with riding coordinates:
 C62(H62A,H62B,H62C), C145(H14M,H14N,H14O), C146(H14P,H14Q,H14R), C929(H92A,
 H92B,H92C), C930(H93A,H93B,H93C)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8), C10(H10), C13(H13), C17(H17), C18(H18),
 C22(H22), C24(H24), C26(H26), C36(H36), C38(H38), C40(H40), C50(H50), C52(H52),
  C54(H54), C65(H65), C69(H69), C73(H73), C74(H74), C78(H78), C79(H79),
 C83(H83), C85(H85), C92(H92), C94(H94), C100(H100), C101(H101), C105(H105),
 C106(H106), C110(H110), C111(H111), C115(H115), C118(H118), C120(H120),
 C122(H122), C124(H124), C134(H134), C136(H136), C138(H138), C148(H148),
 C150(H150), C152(H152)
6.c 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), C46(H46A,H46B,H46C), C47(H47A,
 H47B,H47C), C48(H48A,H48B,H48C), C56(H56A,H56B,H56C), C57(H57A,H57B,H57C),
 C58(H58A,H58B,H58C), C60(H60A,H60B,H60C), C61(H61A,H61B,H61C), C87(H87A,H87B,
 H87C), C88(H88A,H88B,H88C), C89(H89A,H89B,H89C), C96(H96A,H96B,H96C), C97(H97A,
 H97B,H97C), C98(H98A,H98B,H98C), C126(H12A,H12B,H12C), C127(H12D,H12E,H12F),
 C128(H12G,H12H,H12I), C140(H14A,H14B,H14C), C141(H14D,H14E,H14F), C142(H14G,
 H14H,H14I), C144(H14J,H14K,H14L), C154(H15A,H15B,H15C), C155(H15D,H15E,H15F),
 C156(H15G,H15H,H15I), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C34(H34A,H34B,
 H34C), C130(H13A,H13B,H13C), C131(H13D,H13E,H13F), C132(H13G,H13H,H13I),
 C158(H15J,H15K,H15L), C159(H15M,H15N,H15O), C160(H16A,H16B,H16C), C32A(H32D,
 H32E,H32F), C33A(H33D,H33E,H33F), C34A(H34D,H34E,H34F), C931(H93D,H93E,H93F),
 C958(H95A,H95B,H95C), C959(H95D,H95E,H95F), C960(H96D,H96E,H96F)
;
_shelx_res_checksum              97517
_shelx_fab_checksum              95419
_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 2.789
_oxdiff_exptl_absorpt_empirical_full_min 0.249