Imidazoporphyrins as supramolecular tectons: synthesis and self-assembly of zinc 2-(4-pyridyl)-1H-imidazo[4,5-b]porphyrinate
Abdulaeva, Inna A.; Birin, Kirill P.; Sinelshchikova, Anna A.; Grigoriev, Mikhail S.; Lyssenko, Konstantin A.; Gorbunova, Yulia G.; Tsivadze, Aslan Yu.; Bessmertnykh-Lemeune, Alla; CrystEngComm 21 (2019) 1488–; doi:10.1039/C8CE01992D

data_7232236
_publ_section_title
;
 Imidazoporphyrins as supramolecular tectons: synthesis and self-assembly
 of zinc 2-(4-pyridyl)-1H-imidazo[4,5-b]porphyrinate
;
_journal_issue                   9
_journal_name_full               CrystEngComm
_journal_page_first              1488
_journal_paper_doi               10.1039/C8CE01992D
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C62 H55 N7 Zn, 2(C7 H8)'
_chemical_formula_sum            'C76 H71 N7 Zn'
_chemical_formula_weight         1147.76
_chemical_name_systematic
'5,10,15,20-Tetramesityl-2-(4-pyridyl)-1H-imidazo[4,5-b]porphyrinato zinc(II)'
_chemical_properties_physical    Light-sensitive
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-10-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-10-03 deposited with the CCDC.
2019-01-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.952(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1788(9)
_cell_length_b                   21.4947(16)
_cell_length_c                   22.2362(18)
_cell_measurement_reflns_used    4686
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.65
_cell_measurement_theta_min      3.00
_cell_volume                     6025.3(8)
_computing_cell_refinement       'SAINT-Plus (Bruker, 1998)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1998)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0876
_diffrn_reflns_av_unetI/netI     0.1004
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            48812
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.974
_diffrn_reflns_theta_min         4.095
_exptl_absorpt_coefficient_mu    0.459
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_description       fragment
_exptl_crystal_F_000             2424
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: toluene/methanol; toluene/ethylacetate'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.210
_refine_diff_density_min         -0.709
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     771
_refine_ls_number_reflns         14387
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1195
_refine_ls_R_factor_gt           0.0599
_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^)+(0.0694P)^2^+3.4351P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1342
_refine_ls_wR_factor_ref         0.1594
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8746
_reflns_number_total             14387
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce01992d2.cif
_cod_data_source_block           PyPorZn
_cod_depositor_comments          'Adding full bibliography for 7232236.cif.'
_cod_database_code               7232236
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C8S) \\sim Ueq, Uanis(C9S) \\sim Ueq, Uanis(C10S) \\sim Ueq, Uanis(C11S)
\\sim Ueq, Uanis(C12S) \\sim Ueq, Uanis(C13S) \\sim Ueq, Uanis(C14S) \\sim Ueq:
with sigma of 0.006 and sigma for terminal atoms of 0.012
3.a Aromatic/amide H refined with riding coordinates:
 N6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C17(H17), C18(H18), C23(H23),
 C24(H24), C25(H25), C26(H26), C30(H30), C33(H33), C39(H39), C42(H42), C48(H48),
  C51(H51), C57(H57), C60(H60), C1S(H1S), C2S(H2S), C3S(H3S), C4S(H4S),
 C5S(H5S), C8S(H8S), C9S(H9S), C10S(H10S), C11S(H11S), C12S(H12S)
3.b Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C32(H32A,H32B,H32C), C35(H35A,H35B,H35C), C38(H38A,H38B,
 H38C), C41(H41A,H41B,H41C), C44(H44A,H44B,H44C), C47(H47A,H47B,H47C), C50(H50A,
 H50B,H50C), C53(H53A,H53B,H53C), C56(H56A,H56B,H56C), C59(H59A,H59B,H59C),
 C62(H62A,H62B,H62C), C7S(H7SA,H7SB,H7SC), C14S(H14A,H14B,H14C)
;
_shelx_res_checksum              3980
_shelx_hkl_checksum              14238
_olex2_submission_special_instructions 'No special instructions were received'