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_1571716
_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 H164 N14 Ni3'
_chemical_formula_sum            'C160 H164 N14 Ni3'
_chemical_formula_weight         2459.17
_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                104.436(2)
_cell_angle_beta                 95.669(2)
_cell_angle_gamma                104.971(3)
_cell_formula_units_Z            3
_cell_length_a                   19.5178(5)
_cell_length_b                   27.7250(9)
_cell_length_c                   28.7677(6)
_cell_measurement_reflns_used    13251
_cell_measurement_temperature    100.27(10)
_cell_measurement_theta_max      71.8900
_cell_measurement_theta_min      4.3180
_cell_volume                     14340.6(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.8a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.8a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.8a (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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.27(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0697
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_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     23.00  88.00   1.00    2.50    --   34.73-125.00 -30.00   65
  2  \w    -33.00  61.00   1.00    2.50    --   34.73 -77.00   0.00   94
  3  \w     24.00  88.00   1.00    2.50    --   34.73-125.00 -90.00   64
  4  \w      8.00 102.00   1.00    2.50    --   34.73  77.00 120.00   94
  5  \w    -29.00  99.00   1.00    2.50    --   34.73   0.00 -30.00  128
  6  \w     56.00 109.00   1.00   10.00    --  107.46 -94.00 -60.00   53
  7  \w     92.00 176.00   1.00   10.00    --  107.46  45.00 120.00   84
  8  \w     42.00 102.00   1.00   10.00    --  107.46 -61.00 -90.00   60
  9  \w     89.00 173.00   1.00   10.00    --  107.46  61.00   0.00   84
 10  \w     44.00 109.00   1.00   10.00    --  107.46 -94.00-180.00   65
 11  \w     42.00 103.00   1.00   10.00    --  107.46 -61.00  60.00   61
 12  \w     90.00 126.00   1.00   10.00    --  107.46 -30.00-180.00   36
 13  \w     41.00 114.00   1.00   10.00    --  107.46 -61.00-180.00   73
 14  \w     64.00 115.00   1.00   10.00    --  107.46-111.00  60.00   51
 15  \w     46.00  74.00   1.00   10.00    --  107.46 -30.00-180.00   28
 16  \w     39.00 125.00   1.00   10.00    --  107.46 -45.00 -30.00   86
 17  \w     49.00 129.00   1.00   10.00    --  107.46 -30.00  60.00   80
 18  \w     90.00 176.00   1.00   10.00    --  107.46  45.00  60.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0296525000
_diffrn_orient_matrix_UB_12      -0.0563391000
_diffrn_orient_matrix_UB_13      0.0023714000
_diffrn_orient_matrix_UB_21      -0.0333257000
_diffrn_orient_matrix_UB_22      -0.0173781000
_diffrn_orient_matrix_UB_23      -0.0545002000
_diffrn_orient_matrix_UB_31      0.0699655000
_diffrn_orient_matrix_UB_32      -0.0112543000
_diffrn_orient_matrix_UB_33      -0.0133379000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0761
_diffrn_reflns_av_unetI/netI     0.1492
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            82935
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.080
_diffrn_reflns_theta_max         67.080
_diffrn_reflns_theta_min         4.329
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.653
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.8a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark brown'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    0.854
_exptl_crystal_description       needle
_exptl_crystal_F_000             3918
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.020
_refine_diff_density_min         -0.648
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2449
_refine_ls_number_reflns         50539
_refine_ls_number_restraints     195
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.1492
_refine_ls_R_factor_gt           0.0983
_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^)+(0.1449P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2607
_refine_ls_wR_factor_ref         0.3045
_reflns_Friedel_coverage         0.000
_reflns_number_gt                26920
_reflns_number_total             50539
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc01450b2.cif
_cod_data_source_block           6
_cod_depositor_comments
'Adding full bibliography for 1571710--1571717.cif.'
_cod_database_code               1571716
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C78 H78 Ni2 N8'
_reflns_odcompleteness_completeness 98.74
_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
 C205-C207
 1.5 with sigma of 0.02
 C205-C208
 1.5 with sigma of 0.02
 C206-C205
 1.5 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C103) \\sim Ueq: with sigma of 0.003 and sigma for terminal atoms of 0.006
Uanis(C117) \\sim Ueq, Uanis(C119) \\sim Ueq, Uanis(C118) \\sim Ueq, Uanis(C68)
\\sim Ueq, Uanis(C66) \\sim Ueq, Uanis(C65) \\sim Ueq, Uanis(C67) \\sim Ueq,
Uanis(C156) \\sim Ueq, Uanis(C154) \\sim Ueq, Uanis(C155) \\sim Ueq,
Uanis(C160) \\sim Ueq, Uanis(C157) \\sim Ueq, Uanis(C159) \\sim Ueq,
Uanis(C158) \\sim Ueq, Uanis(C212) \\sim Ueq, Uanis(C211) \\sim Ueq,
Uanis(C209) \\sim Ueq, Uanis(C210) \\sim Ueq, Uanis(C230) \\sim Ueq,
Uanis(C229) \\sim Ueq, Uanis(C231) \\sim Ueq, Uanis(C145) \\sim Ueq,
Uanis(C122) \\sim Ueq, Uanis(C121) \\sim Ueq, Uanis(C123) \\sim Ueq,
Uanis(C120) \\sim Ueq, Uanis(C206) \\sim Ueq, Uanis(C208) \\sim Ueq,
Uanis(C207) \\sim Ueq, Uanis(C81) \\sim Ueq, Uanis(C71) \\sim Ueq: with sigma
of 0.05 and sigma for terminal atoms of 0.01
4.a Me refined with riding coordinates:
 C68(H68A,H68B,H68C), C81(H81A,H81B,H81C), C103(H10A,H10B,H10C), C105(H10G,
 H10H,H10I), C118(H11D,H11E,H11F), C154(H15A,H15B,H15C)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C8(H8), C14(H14), C18(H18), C19(H19), C22(H22), C26(H26),
 C31(H31), C35(H35), C40(H40), C44(H44), C45(H45), C49(H49), C50(H50), C54(H54),
  C60(H60), C62(H62), C64(H64), C74(H74), C76(H76), C78(H78), C89(H89),
 C91(H91), C97(H97), C99(H99), C101(H101), C111(H111), C113(H113), C115(H115),
 C125(H125), C127(H127), C129(H129), C140(H140), C142(H142), C148(H148),
 C150(H150), C152(H152), C163(H163), C164(H164), C168(H168), C171(H171),
 C173(H173), C176(H176), C180(H180), C181(H181), C186(H186), C188(H188),
 C190(H190), C200(H200), C202(H202), C204(H204), C215(H215), C217(H217),
 C223(H223), C225(H225), C227(H227)
4.c Idealised Me refined as rotating group:
 C66(H66A,H66B,H66C), C67(H67A,H67B,H67C), C70(H70A,H70B,H70C), C71(H71A,H71B,
 H71C), C72(H72A,H72B,H72C), C80(H80A,H80B,H80C), C82(H82A,H82B,H82C), C84(H84A,
 H84B,H84C), C85(H85A,H85B,H85C), C86(H86A,H86B,H86C), C93(H93A,H93B,H93C),
 C94(H94A,H94B,H94C), C95(H95A,H95B,H95C), C104(H10D,H10E,H10F), C107(H10J,H10K,
 H10L), C108(H10M,H10N,H10O), C109(H10P,H10Q,H10R), C117(H11A,H11B,H11C),
 C119(H11G,H11H,H11I), C121(H12A,H12B,H12C), C122(H12D,H12E,H12F), C123(H12G,
 H12H,H12I), C131(H13A,H13B,H13C), C132(H13D,H13E,H13F), C133(H13G,H13H,H13I),
 C135(H13J,H13K,H13L), C136(H13M,H13N,H13O), C137(H13P,H13Q,H13R), C144(H14A,
 H14B,H14C), C145(H14D,H14E,H14F), C146(H14G,H14H,H14I), C155(H15D,H15E,H15F),
 C156(H15G,H15H,H15I), C158(H15J,H15K,H15L), C159(H15M,H15N,H15O), C160(H16A,
 H16B,H16C), C192(H19A,H19B,H19C), C193(H19D,H19E,H19F), C194(H19G,H19H,H19I),
 C196(H19J,H19K,H19L), C197(H19M,H19N,H19O), C198(H19P,H19Q,H19R), C206(H20A,
 H20B,H20C), C207(H20D,H20E,H20F), C208(H20G,H20H,H20I), C210(H21A,H21B,H21C),
 C211(H21D,H21E,H21F), C212(H21G,H21H,H21I), C219(H21J,H21K,H21L), C220(H22A,
 H22B,H22C), C221(H22D,H22E,H22F), C229(H22G,H22H,H22I), C230(H23A,H23B,H23C),
 C231(H23D,H23E,H23F), C233(H23G,H23H,H23I), C234(H23J,H23K,H23L), C235(H23M,
 H23N,H23O)
;
_shelx_res_checksum              17308
_shelx_fab_checksum              66325
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.238
_oxdiff_exptl_absorpt_empirical_full_min 0.429