#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:24:23 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301857 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/07/7110701.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7110701
loop_
_publ_author_name
'Bonomo, Lucia'
'Solari, Euro'
'Scopelliti, Rosario'
'Floriani, Carlo'
'Latronico, Mario'
_publ_section_title
;
 Porphodimethene--porphyrinogen relationship: the generation of
 unprecedented forms of porphyrinogen†
;
_journal_issue                   21
_journal_name_full               'Chemical Communications'
_journal_page_first              2227
_journal_paper_doi               10.1039/a906817a
_journal_year                    1999
_chemical_formula_moiety         '(C32 H36 N4 Ni), 2(C12 H30 Li O6)'
_chemical_formula_sum            'C56 H96 Li2 N4 Ni O12'
_chemical_formula_weight         1089.96
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 103.49(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.269(3)
_cell_length_b                   19.417(4)
_cell_length_c                   26.192(5)
_cell_measurement_reflns_used    '54 spots from the first image'
_cell_measurement_temperature    143(2)
_cell_volume                     6067(2)
_computing_cell_refinement       'marresearch, marHKL 1.9.1'
_computing_data_collection       'marresearch, mar345 1.2.11'
_computing_data_reduction        'marresearch, marHKL'
_computing_molecular_graphics    'Bruker, SHELXTL 5.1'
_computing_publication_material  'Bruker, SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      143(2)
_diffrn_measurement_device_type  'mar345 IPDS'
_diffrn_measurement_method       'phi scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0642
_diffrn_reflns_av_sigmaI/netI    0.0771
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            10943
_diffrn_reflns_theta_max         24.38
_diffrn_reflns_theta_min         1.60
_exptl_absorpt_coefficient_mu    0.379
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             2360
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       0.0031(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         3664
_refine_ls_number_restraints     34
_refine_ls_restrained_S_all      0.963
_refine_ls_R_factor_all          0.1180
_refine_ls_R_factor_gt           0.0689
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1415P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1844
_refine_ls_wR_factor_ref         0.2153
_reflns_number_gt                2120
_reflns_number_total             3664
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            906817asup1.cif
_cod_data_source_block           3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7110701
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.0000 0.29217(5) 0.2500 0.0580(5) Uani 1 2 d S . .
N1 N -0.1579(4) 0.2913(2) 0.22707(17) 0.0632(12) Uani 1 1 d . . .
C1 C -0.2330(5) 0.3182(3) 0.2529(2) 0.0683(16) Uani 1 1 d . . .
C2 C -0.3410(5) 0.3030(3) 0.2250(3) 0.0828(19) Uani 1 1 d . . .
H2 H -0.4089 0.3161 0.2338 0.080 Uiso 1 1 calc R . .
C3 C -0.3304(6) 0.2650(4) 0.1816(3) 0.0837(19) Uani 1 1 d . . .
H3 H -0.3901 0.2457 0.1558 0.080 Uiso 1 1 calc R . .
C4 C -0.2190(5) 0.2601(3) 0.1824(2) 0.0687(16) Uani 1 1 d . . .
C5 C -0.1639(6) 0.2234(3) 0.1451(2) 0.0777(19) Uani 1 1 d . . .
N2 N 0.0117(4) 0.2919(2) 0.17955(17) 0.0628(12) Uani 1 1 d . . .
C6 C -0.0646(6) 0.2639(3) 0.1377(2) 0.0727(17) Uani 1 1 d . . .
C7 C -0.0285(7) 0.2761(4) 0.0932(3) 0.094(2) Uani 1 1 d . . .
H7 H -0.0660 0.2626 0.0587 0.080 Uiso 1 1 calc R . .
C8 C 0.0733(7) 0.3119(4) 0.1070(3) 0.094(2) Uani 1 1 d . . .
H8 H 0.1181 0.3266 0.0840 0.080 Uiso 1 1 calc R . .
C9 C 0.0958(6) 0.3217(3) 0.1611(2) 0.0715(17) Uani 1 1 d . . .
C10 C 0.1925(6) 0.3546(4) 0.1967(3) 0.086(2) Uani 1 1 d . . .
C11 C 0.2585(10) 0.3980(5) 0.1797(4) 0.161(4) Uani 1 1 d DU . .
H11 H 0.2470 0.3997 0.1425 0.080 Uiso 1 1 calc R A 1
C12A C 0.3451(9) 0.4433(6) 0.2075(6) 0.172(6) Uani 0.789(12) 1 d PDU B 1
H12A H 0.3548 0.4366 0.2454 0.080 Uiso 0.789(12) 1 calc PR B 1
H12B H 0.3239 0.4911 0.1984 0.080 Uiso 0.789(12) 1 calc PR B 1
H12C H 0.4157 0.4328 0.1976 0.080 Uiso 0.789(12) 1 calc PR B 1
C12B C 0.230(4) 0.432(2) 0.1292(13) 0.136(15) Uani 0.211(12) 1 d PDU B 2
H12D H 0.2863 0.4202 0.1093 0.080 Uiso 0.211(12) 1 calc PR B 2
H12E H 0.2295 0.4819 0.1343 0.080 Uiso 0.211(12) 1 calc PR B 2
H12F H 0.1562 0.4166 0.1097 0.080 Uiso 0.211(12) 1 calc PR B 2
C13 C -0.2478(6) 0.2117(4) 0.0918(3) 0.101(2) Uani 1 1 d . . .
H13A H -0.2087 0.1861 0.0686 0.080 Uiso 1 1 calc R . .
H13B H -0.3089 0.1818 0.0979 0.080 Uiso 1 1 calc R . .
C14 C -0.3004(6) 0.2753(4) 0.0627(3) 0.114(3) Uani 1 1 d . . .
H14A H -0.3441 0.2997 0.0839 0.080 Uiso 1 1 calc R . .
H14B H -0.3498 0.2617 0.0291 0.080 Uiso 1 1 calc R . .
H14C H -0.2413 0.3057 0.0561 0.080 Uiso 1 1 calc R . .
C15 C -0.1271(7) 0.1506(4) 0.1700(3) 0.105(3) Uani 1 1 d . . .
H15A H -0.0780 0.1583 0.2053 0.080 Uiso 1 1 calc R . .
H15B H -0.1951 0.1267 0.1750 0.080 Uiso 1 1 calc R . .
C16 C -0.0701(8) 0.1051(5) 0.1422(4) 0.153(4) Uani 1 1 d . . .
H16A H -0.1233 0.0870 0.1113 0.080 Uiso 1 1 calc R . .
H16B H -0.0376 0.0669 0.1652 0.080 Uiso 1 1 calc R . .
H16C H -0.0102 0.1302 0.1311 0.080 Uiso 1 1 calc R . .
Li1 Li 0.3010(9) 0.0673(5) 0.1003(4) 0.080(3) Uani 1 1 d . . .
C17 C 0.2318(6) 0.1344(4) 0.2000(3) 0.104(2) Uani 1 1 d . . .
H17A H 0.2957 0.1216 0.2285 0.080 Uiso 1 1 calc R . .
H17B H 0.1746 0.0982 0.1955 0.080 Uiso 1 1 calc R . .
H17C H 0.2000 0.1780 0.2086 0.080 Uiso 1 1 calc R . .
O1 O 0.2680(3) 0.1421(2) 0.15262(16) 0.0800(12) Uani 1 1 d . . .
C18 C 0.3407(6) 0.1997(4) 0.1555(3) 0.088(2) Uani 1 1 d . . .
H18A H 0.4148 0.1888 0.1785 0.080 Uiso 1 1 calc R . .
H18B H 0.3091 0.2397 0.1705 0.080 Uiso 1 1 calc R . .
C19 C 0.3530(5) 0.2163(3) 0.1021(3) 0.0805(18) Uani 1 1 d . . .
H19A H 0.2811 0.2335 0.0804 0.080 Uiso 1 1 calc R . .
H19B H 0.4105 0.2525 0.1038 0.080 Uiso 1 1 calc R . .
O2 O 0.3854(3) 0.1560(2) 0.07964(17) 0.0840(13) Uani 1 1 d . . .
C20 C 0.4050(7) 0.1691(4) 0.0295(3) 0.108(2) Uani 1 1 d . . .
H20A H 0.3400 0.1927 0.0077 0.080 Uiso 1 1 calc R . .
H20B H 0.4172 0.1254 0.0129 0.080 Uiso 1 1 calc R . .
H20C H 0.4716 0.1982 0.0331 0.080 Uiso 1 1 calc R . .
C21 C 0.0834(6) 0.1384(4) 0.0336(3) 0.104(2) Uani 1 1 d . . .
H21A H 0.1070 0.1739 0.0119 0.080 Uiso 1 1 calc R . .
H21B H 0.0867 0.1569 0.0687 0.080 Uiso 1 1 calc R . .
H21C H 0.0065 0.1241 0.0174 0.080 Uiso 1 1 calc R . .
O3 O 0.1560(4) 0.0807(3) 0.0375(2) 0.1022(15) Uani 1 1 d . . .
C22 C 0.1585(8) 0.0538(5) -0.0122(4) 0.146(4) Uani 1 1 d . . .
H22A H 0.1894 0.0885 -0.0327 0.080 Uiso 1 1 calc R . .
H22B H 0.0818 0.0419 -0.0319 0.080 Uiso 1 1 calc R . .
C23 C 0.2299(11) -0.0082(6) -0.0042(4) 0.170(4) Uani 1 1 d . . .
H23A H 0.1932 -0.0448 0.0122 0.080 Uiso 1 1 calc R . .
H23B H 0.2387 -0.0254 -0.0386 0.080 Uiso 1 1 calc R . .
O4 O 0.3320(5) 0.0057(3) 0.0270(3) 0.1186(17) Uani 1 1 d . . .
C24 C 0.4069(8) -0.0499(5) 0.0300(4) 0.154(4) Uani 1 1 d . . .
H24A H 0.3778 -0.0898 0.0456 0.080 Uiso 1 1 calc R . .
H24B H 0.4802 -0.0369 0.0519 0.080 Uiso 1 1 calc R . .
H24C H 0.4149 -0.0618 -0.0053 0.080 Uiso 1 1 calc R . .
C25 C 0.1197(7) -0.0383(5) 0.1202(4) 0.141(3) Uani 1 1 d . . .
H25A H 0.1131 -0.0761 0.1441 0.080 Uiso 1 1 calc R . .
H25B H 0.0965 -0.0543 0.0838 0.080 Uiso 1 1 calc R . .
H25C H 0.0716 0.0000 0.1256 0.080 Uiso 1 1 calc R . .
O5 O 0.2296(4) -0.0163(2) 0.13023(19) 0.0958(14) Uani 1 1 d . . .
C26 C 0.3067(8) -0.0563(5) 0.1621(4) 0.133(3) Uani 1 1 d . . .
H26A H 0.2824 -0.0630 0.1953 0.080 Uiso 1 1 calc R . .
H26B H 0.3059 -0.1020 0.1453 0.080 Uiso 1 1 calc R . .
C27 C 0.4135(9) -0.0335(5) 0.1745(4) 0.142(3) Uani 1 1 d . . .
H27A H 0.4620 -0.0716 0.1678 0.080 Uiso 1 1 calc R . .
H27B H 0.4339 -0.0244 0.2127 0.080 Uiso 1 1 calc R . .
O6 O 0.4410(4) 0.0248(3) 0.1493(2) 0.1050(15) Uani 1 1 d . . .
C28 C 0.5478(8) 0.0497(5) 0.1593(5) 0.198(6) Uani 1 1 d . . .
H28A H 0.5599 0.0810 0.1895 0.080 Uiso 1 1 calc R . .
H28B H 0.5593 0.0748 0.1285 0.080 Uiso 1 1 calc R . .
H28C H 0.6010 0.0114 0.1671 0.080 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Li Li -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N2 Ni1 N2 179.7(3) . 2
N2 Ni1 N1 89.71(19) . .
N2 Ni1 N1 90.28(19) 2 .
N2 Ni1 N1 90.28(19) . 2
N2 Ni1 N1 89.71(19) 2 2
N1 Ni1 N1 178.9(3) . 2
N2 Ni1 H15A 72.4 . .
N2 Ni1 H15A 107.3 2 .
N1 Ni1 H15A 69.4 . .
N1 Ni1 H15A 109.6 2 .
N2 Ni1 H15A 107.3 . 2
N2 Ni1 H15A 72.4 2 2
N1 Ni1 H15A 109.6 . 2
N1 Ni1 H15A 69.4 2 2
H15A Ni1 H15A 54.1 . 2
C1 N1 C4 107.0(5) . .
C1 N1 Ni1 126.7(4) . .
C4 N1 Ni1 126.2(4) . .
N1 C1 C2 109.1(6) . .
N1 C1 C10 120.0(6) . 2
C2 C1 C10 130.8(6) . 2
C3 C2 C1 106.5(6) . .
C4 C3 C2 108.0(6) . .
C3 C4 N1 109.3(6) . .
C3 C4 C5 128.8(6) . .
N1 C4 C5 121.8(5) . .
C4 C5 C6 109.8(5) . .
C4 C5 C13 110.7(6) . .
C6 C5 C13 110.5(6) . .
C4 C5 C15 106.6(5) . .
C6 C5 C15 111.2(5) . .
C13 C5 C15 108.0(5) . .
C9 N2 C6 108.3(5) . .
C9 N2 Ni1 125.6(4) . .
C6 N2 Ni1 126.1(4) . .
C7 C6 N2 108.5(6) . .
C7 C6 C5 129.7(7) . .
N2 C6 C5 121.7(5) . .
C6 C7 C8 108.3(6) . .
C9 C8 C7 106.4(6) . .
N2 C9 C8 108.4(6) . .
N2 C9 C10 121.6(6) . .
C8 C9 C10 130.0(7) . .
C11 C10 C9 122.2(8) . .
C11 C10 C1 120.2(8) . 2
C9 C10 C1 114.3(6) . 2
C10 C11 C12A 131.2(11) . .
C10 C11 C12B 125(2) . .
C12A C11 C12B 100(2) . .
C14 C13 C5 116.8(6) . .
C16 C15 C5 118.1(7) . .
O6 Li1 O5 79.4(4) . .
O6 Li1 O1 97.4(5) . .
O5 Li1 O1 97.5(5) . .
O6 Li1 O3 161.9(6) . .
O5 Li1 O3 92.1(5) . .
O1 Li1 O3 99.5(4) . .
O6 Li1 O2 95.6(5) . .
O5 Li1 O2 172.6(6) . .
O1 Li1 O2 77.7(4) . .
O3 Li1 O2 94.2(4) . .
O6 Li1 O4 92.0(4) . .
O5 Li1 O4 94.2(5) . .
O1 Li1 O4 166.1(6) . .
O3 Li1 O4 72.6(4) . .
O2 Li1 O4 91.4(4) . .
C17 O1 C18 111.0(5) . .
C17 O1 Li1 130.1(5) . .
C18 O1 Li1 111.4(5) . .
O1 C18 C19 108.9(5) . .
O2 C19 C18 108.4(5) . .
C19 O2 C20 111.4(5) . .
C19 O2 Li1 111.3(5) . .
C20 O2 Li1 125.2(5) . .
C22 O3 C21 111.9(6) . .
C22 O3 Li1 118.1(5) . .
C21 O3 Li1 123.2(5) . .
O3 C22 C23 108.1(8) . .
O4 C23 C22 111.0(9) . .
C23 O4 C24 112.4(8) . .
C23 O4 Li1 106.8(6) . .
C24 O4 Li1 124.6(6) . .
C26 O5 C25 116.9(6) . .
C26 O5 Li1 112.6(6) . .
C25 O5 Li1 130.3(6) . .
C27 C26 O5 117.5(7) . .
C26 C27 O6 118.8(7) . .
C28 O6 C27 121.7(7) . .
C28 O6 Li1 127.0(6) . .
C27 O6 Li1 111.2(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 N2 1.884(4) .
Ni1 N2 1.884(4) 2
Ni1 N1 1.889(4) .
Ni1 N1 1.889(5) 2
Ni1 H15A 2.9193 .
Ni1 H15A 2.9193 2
N1 C1 1.369(7) .
N1 C4 1.373(7) .
C1 C2 1.388(8) .
C1 C10 1.477(9) 2
C2 C3 1.388(9) .
C3 C4 1.364(8) .
C4 C5 1.494(8) .
C5 C6 1.500(9) .
C5 C13 1.546(8) .
C5 C15 1.577(9) .
N2 C9 1.366(8) .
N2 C6 1.377(7) .
C6 C7 1.360(9) .
C7 C8 1.402(10) .
C8 C9 1.392(8) .
C9 C10 1.473(9) .
C10 C11 1.316(11) .
C10 C1 1.477(9) 2
C11 C12A 1.439(14) .
C11 C12B 1.45(2) .
C13 C14 1.515(9) .
C15 C16 1.428(10) .
Li1 O6 2.062(11) .
Li1 O5 2.083(11) .
Li1 O1 2.101(11) .
Li1 O3 2.138(11) .
Li1 O2 2.143(11) .
Li1 O4 2.367(12) .
C17 O1 1.420(7) .
O1 C18 1.420(7) .
C18 C19 1.476(8) .
C19 O2 1.407(7) .
O2 C20 1.412(7) .
C21 O3 1.419(7) .
O3 C22 1.410(9) .
C22 C23 1.475(12) .
C23 O4 1.354(11) .
O4 C24 1.408(8) .
C25 O5 1.379(8) .
O5 C26 1.351(8) .
C26 C27 1.349(10) .
C27 O6 1.391(9) .
O6 C28 1.363(9) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139183819
