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_1571715
_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, C H4 O, 5.5(C8 H10)'
_chemical_formula_sum            'C205 H229 N14 Ni3 O'
_chemical_formula_weight         3081.14
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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                 91.719(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   33.0120(7)
_cell_length_b                   17.7275(3)
_cell_length_c                   30.1749(5)
_cell_measurement_reflns_used    24670
_cell_measurement_temperature    99.9(5)
_cell_measurement_theta_max      71.7860
_cell_measurement_theta_min      3.8950
_cell_volume                     17651.0(6)
_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      99.9(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0697
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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     19.00 102.00   1.00    3.50    --   34.73  57.00  30.00   83
  2  \w     36.00  63.00   1.00   15.00    --  105.88 -30.00 -30.00   27
  3  \w     43.00 121.00   1.00   15.00    --  105.88 -61.00   0.00   78
  4  \w     88.00 127.00   1.00   15.00    --  105.88 -30.00 -30.00   39
  5  \w     95.00 174.00   1.00   15.00    --  105.88  45.00  60.00   79
  6  \w    104.00 138.00   1.00   15.00    --  105.88 111.00   0.00   34
  7  \w     68.00 175.00   1.00   15.00    --  105.88  15.00   0.00  107
  8  \w     81.00 109.00   1.00   15.00    --  105.88 -94.00 150.00   28
  9  \w     75.00 116.00   1.00   15.00    --  105.88-111.00  60.00   41
 10  \w     61.00  98.00   1.00   15.00    --  105.88 -94.00 120.00   37
 11  \w     54.00  80.00   1.00   15.00    --  105.88 -94.00 150.00   26
 12  \w     42.00  78.00   1.00   15.00    --  105.88 -61.00 150.00   36
 13  \w     44.00 114.00   1.00   15.00    --  105.88 -45.00 150.00   70
 14  \w     42.00  84.00   1.00   15.00    --  105.88 -94.00   0.00   42
 15  \w     37.00 108.00   1.00   15.00    --  105.88 -94.00 -60.00   71
 16  \w     62.00 107.00   1.00   15.00    --  105.88 -94.00-120.00   45
 17  \w     46.00  87.00   1.00    3.50    --   34.73-125.00 -30.00   41
 18  \w     36.00 122.00   1.00   15.00    --  105.88 -30.00-120.00   86
 19  \w     30.00 103.00   1.00    3.50    --   34.73  38.00-180.00   73
 20  \w     29.00 102.00   1.00    3.50    --   34.73  57.00-120.00   73
 21  \w     36.00 118.00   1.00   15.00    --  105.88 -30.00  60.00   82
 22  \w     26.00  81.00   1.00    3.50    --   34.73-125.00 120.00   55
 23  \w    -33.00   9.00   1.00    3.50    --   34.73 -57.00  90.00   42
 24  \w    -27.00   8.00   1.00    3.50    --  -34.73  57.00 -90.00   35
 25  \w    -39.00   3.00   1.00    3.50    --  -34.73  38.00-120.00   42
 26  \w      5.00  54.00   1.00    3.50    --   34.73 -38.00-120.00   49
 27  \w     28.00  70.00   1.00    3.50    --   34.73 -99.00-180.00   42
 28  \w   -105.00 -17.00   1.00    3.50    --  -34.73 -19.00  60.00   88
;
_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      0.0386555000
_diffrn_orient_matrix_UB_12      -0.0239989000
_diffrn_orient_matrix_UB_13      0.0261752000
_diffrn_orient_matrix_UB_21      -0.0204945000
_diffrn_orient_matrix_UB_22      0.0191999000
_diffrn_orient_matrix_UB_23      0.0438125000
_diffrn_orient_matrix_UB_31      -0.0162316000
_diffrn_orient_matrix_UB_32      -0.0812662000
_diffrn_orient_matrix_UB_33      0.0026468000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0777
_diffrn_reflns_av_unetI/netI     0.0746
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            117754
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.600
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         3.660
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.806
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82025
_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            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.159
_exptl_crystal_description       plank
_exptl_crystal_F_000             6596
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.911
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2124
_refine_ls_number_reflns         31164
_refine_ls_number_restraints     301
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0613
_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^)+(0.0637P)^2^+18.3390P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1478
_refine_ls_wR_factor_ref         0.1625
_reflns_Friedel_coverage         0.000
_reflns_number_gt                23622
_reflns_number_total             31164
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc01450b2.cif
_cod_data_source_block           3a
_cod_depositor_comments
'Adding full bibliography for 1571710--1571717.cif.'
_cod_database_code               1571715
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C100 H100 N12 Ni3'
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.794
_reflns_odcompleteness_completeness 99.93
_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, All O(H) groups
2. Restrained distances
 C945-C143
 1.5 with sigma of 0.02
3. Rigid bond restraints
 C129, C130, C131, C132, C930, C931, C932, C161, C162, C163, C164, C165, C166,
 C167, C168, C177, C178, C179, C180, C181, C182, C183, C184, C193, C194, C195,
 C196, C197, C198, C199, C200
 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(C129) \\sim Ueq, Uanis(C131) \\sim Ueq, Uanis(C132) \\sim Ueq,
Uanis(C130) \\sim Ueq, Uanis(C932) \\sim Ueq, Uanis(C930) \\sim Ueq,
Uanis(C931) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C193) \\sim Ueq, Uanis(C194) \\sim Ueq, Uanis(C195) \\sim Ueq,
Uanis(C196) \\sim Ueq, Uanis(C199) \\sim Ueq, Uanis(C198) \\sim Ueq,
Uanis(C197) \\sim Ueq, Uanis(C200) \\sim Ueq, Uanis(C181) \\sim Ueq,
Uanis(C182) \\sim Ueq, Uanis(C183) \\sim Ueq, Uanis(C178) \\sim Ueq,
Uanis(C179) \\sim Ueq, Uanis(C180) \\sim Ueq, Uanis(C184) \\sim Ueq,
Uanis(C177) \\sim Ueq, Uanis(C168) \\sim Ueq, Uanis(C165) \\sim Ueq,
Uanis(C164) \\sim Ueq, Uanis(C163) \\sim Ueq, Uanis(C162) \\sim Ueq,
Uanis(C167) \\sim Ueq, Uanis(C166) \\sim Ueq, Uanis(C161) \\sim Ueq: with sigma
of 0.005 and sigma for terminal atoms of 0.01
Uanis(O1) \\sim Ueq, Uanis(C205) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(C946) \\sim Ueq, Uanis(C144) \\sim Ueq, Uanis(C944) \\sim Ueq,
Uanis(C145) \\sim Ueq, Uanis(C945) \\sim Ueq, Uanis(C146) \\sim Ueq: with sigma
of 0.002 and sigma for terminal atoms of 0.005
5. Others
 Sof(C930)=Sof(H93A)=Sof(H93B)=Sof(H93C)=Sof(C931)=Sof(H93D)=Sof(H93E)=
 Sof(H93F)=Sof(C932)=Sof(H93G)=Sof(H93H)=Sof(H93I)=1-FVAR(1)
 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(1)
 Sof(C944)=Sof(H94A)=Sof(H94B)=Sof(H94C)=Sof(C945)=Sof(H94D)=Sof(H94E)=
 Sof(H94F)=Sof(C946)=Sof(H94G)=Sof(H94H)=Sof(H94I)=1-FVAR(2)
 Sof(C144)=Sof(H14J)=Sof(H14K)=Sof(H14L)=Sof(C145)=Sof(H14M)=Sof(H14N)=
 Sof(H14O)=Sof(C146)=Sof(H14P)=Sof(H14Q)=Sof(H14R)=FVAR(2)
6.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8), C12(H12), 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), C101(H101), C102(H102), C106(H106),
 C107(H107), C111(H111), C112(H112), C116(H116), C117(H117), C120(H120),
 C122(H122), C124(H124), C134(H134), C136(H136), C138(H138), C148(H148),
 C150(H150), C152(H152), C163(H163), C164(H164), C166(H166), C167(H167),
 C171(H171), C172(H172), C174(H174), C175(H175), C179(H179), C180(H180),
 C182(H182), C183(H183), C187(H187), C188(H188), C190(H190), C191(H191),
 C195(H195), C196(H196), C198(H198), C199(H199), C203(H203), C204(H204)
6.b Tetrahedral OH refined with riding coordinates:
 O1(H1)
6.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C32(H32A,H32B,
 H32C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C), 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), C62(H62A,H62B,H62C), 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), C154(H15A,H15B,H15C), C155(H15D,H15E,H15F), C156(H15G,
 H15H,H15I), C158(H15J,H15K,H15L), C159(H15M,H15N,H15O), C160(H16A,H16B,H16C),
 C130(H13A,H13B,H13C), C131(H13D,H13E,H13F), C132(H13G,H13H,H13I), C144(H14J,
 H14K,H14L), C145(H14M,H14N,H14O), C146(H14P,H14Q,H14R), C930(H93A,H93B,H93C),
 C931(H93D,H93E,H93F), C932(H93G,H93H,H93I), C944(H94A,H94B,H94C), C945(H94D,
 H94E,H94F), C946(H94G,H94H,H94I), C205(H20G,H20H,H20I), C161(H16D,H16E,H16F),
 C168(H16G,H16H,H16I), C169(H16J,H16K,H16L), C176(H17A,H17B,H17C), C177(H17D,
 H17E,H17F), C184(H18A,H18B,H18C), C185(H18D,H18E,H18F), C192(H19A,H19B,H19C),
 C193(H19D,H19E,H19F), C200(H20A,H20B,H20C), C201(H20D,H20E,H20F)
;
_shelx_res_checksum              83301
_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 1.496
_oxdiff_exptl_absorpt_empirical_full_min 0.597