#------------------------------------------------------------------------------
#$Date: 2019-11-23 11:35:32 +0200 (Sat, 23 Nov 2019) $
#$Revision: 233108 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/85/4348570.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4348570
loop_
_publ_author_name
'Chen, Yuxiang'
'Fang, Wenjuan'
'Wang, Kang'
'Liu, Wei'
'Jiang, Jianzhuang'
_publ_section_title
;
 Nonperipheral Tetrakis(dibutylamino)phthalocyanines. New Types of
 1,8,15,22-Tetrakis(substituted)phthalocyanine Isomers.
;
_journal_issue                   18
_journal_name_full               'Inorganic chemistry'
_journal_page_first              9289
_journal_page_last               9296
_journal_paper_doi               10.1021/acs.inorgchem.6b01371
_journal_volume                  55
_journal_year                    2016
_chemical_formula_sum            'C64 H84 N12 Ni'
_chemical_formula_weight         1080.14
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.4140(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.2314(2)
_cell_length_b                   15.5267(2)
_cell_length_c                   15.3175(2)
_cell_measurement_reflns_used    4196
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      67.1836
_cell_measurement_theta_min      2.8850
_cell_volume                     2906.42(7)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0137
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8662
_diffrn_reflns_theta_full        65.00
_diffrn_reflns_theta_max         65.00
_diffrn_reflns_theta_min         3.62
_exptl_absorpt_coefficient_mu    0.870
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91652
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1160
_refine_diff_density_max         0.718
_refine_diff_density_min         -0.613
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         4921
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.117
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0625
_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)+(0.0916P)²+2.3330P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1676
_refine_ls_wR_factor_ref         0.1719
_reflns_number_gt                4387
_reflns_number_total             4921
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic6b01371_si_004.cif
_cod_data_source_block           ni
_cod_database_code               4348570
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
H2 H 0.4444(19) 0.1673(7) 0.3656(18) 0.041(9) Uiso 1 1 d D . .
H1 H 0.459(3) 0.233(2) 0.2844(12) 0.063(10) Uiso 1 1 d D . .
Ni1 Ni 1.0000 0.0000 0.5000 0.0396(2) Uani 1 2 d S . .
N2 N 0.87885(18) 0.01106(16) 0.41833(14) 0.0417(5) Uani 1 1 d . . .
N3 N 0.96947(17) 0.11107(16) 0.54493(14) 0.0420(5) Uani 1 1 d . . .
N6 N 0.88655(18) -0.12574(17) 0.34338(14) 0.0457(6) Uani 1 1 d . . .
C4 C 0.8453(2) -0.0489(2) 0.35765(17) 0.0443(7) Uani 1 1 d . . .
C5 C 0.8835(2) 0.1633(2) 0.51940(17) 0.0424(6) Uani 1 1 d . . .
N5 N 0.60398(19) 0.1884(2) 0.33997(17) 0.0574(7) Uani 1 1 d . B .
C7 C 0.8064(2) 0.0793(2) 0.40994(17) 0.0424(6) Uani 1 1 d . . .
C8 C 0.9788(2) 0.2377(2) 0.62641(17) 0.0445(6) Uani 1 1 d . . .
C9 C 0.7246(2) 0.0623(2) 0.34020(17) 0.0468(7) Uani 1 1 d . . .
N4 N 1.0987(2) 0.30492(19) 0.73946(16) 0.0559(7) Uani 1 1 d . . .
C11 C 0.6540(3) 0.3132(2) 0.2442(2) 0.0586(8) Uani 1 1 d . . .
H11A H 0.6468 0.2756 0.1938 0.070 Uiso 1 1 calc R . .
H11B H 0.5845 0.3422 0.2505 0.070 Uiso 1 1 calc R . .
C12 C 0.6853(2) -0.0601(2) 0.24315(19) 0.0530(7) Uani 1 1 d . . .
H12 H 0.7040 -0.1137 0.2213 0.064 Uiso 1 1 calc R . .
C13 C 0.8853(2) 0.2418(2) 0.57109(17) 0.0438(6) Uani 1 1 d . . .
C14 C 1.0024(2) 0.3038(2) 0.68747(18) 0.0470(7) Uani 1 1 d . . .
C15 C 1.0276(2) 0.1548(2) 0.61072(17) 0.0431(6) Uani 1 1 d . . .
C16 C 0.5655(2) 0.0634(3) 0.2453(2) 0.0575(8) Uani 1 1 d . . .
H16 H 0.5012 0.0893 0.2239 0.069 Uiso 1 1 calc R . .
C17 C 0.6804(3) 0.2593(2) 0.3258(2) 0.0594(9) Uani 1 1 d . . .
H17A H 0.7533 0.2355 0.3217 0.071 Uiso 1 1 calc R . .
H17B H 0.6812 0.2968 0.3764 0.071 Uiso 1 1 calc R . .
C18 C 0.8096(2) 0.3081(2) 0.57472(18) 0.0466(7) Uani 1 1 d . . .
H18 H 0.7480 0.3102 0.5371 0.056 Uiso 1 1 calc R . .
C19 C 0.5923(2) -0.0168(2) 0.2136(2) 0.0573(8) Uani 1 1 d . . .
H19 H 0.5464 -0.0424 0.1711 0.069 Uiso 1 1 calc R . .
C20 C 0.8303(3) 0.3711(2) 0.63706(19) 0.0514(7) Uani 1 1 d . . .
H20 H 0.7804 0.4157 0.6427 0.062 Uiso 1 1 calc R . .
C21 C 0.7495(2) -0.0186(2) 0.30785(18) 0.0468(7) Uani 1 1 d . . .
C22 C 0.9242(3) 0.3690(2) 0.69158(19) 0.0513(7) Uani 1 1 d . . .
H22 H 0.9353 0.4129 0.7324 0.062 Uiso 1 1 calc R . .
C23 C 0.6307(2) 0.1078(2) 0.30829(19) 0.0506(7) Uani 1 1 d . . .
C24 C 1.0173(3) 0.1806(3) 0.8743(2) 0.0641(9) Uani 1 1 d . . .
H24A H 1.0147 0.1644 0.8131 0.077 Uiso 1 1 calc R . .
H24B H 0.9480 0.2075 0.8863 0.077 Uiso 1 1 calc R . .
C25 C 0.4891(3) 0.2140(3) 0.3408(2) 0.0702(11) Uani 1 1 d D . .
C26 C 1.0964(3) 0.3260(2) 0.8326(2) 0.0650(9) Uani 1 1 d . . .
H26A H 1.0281 0.3550 0.8440 0.078 Uiso 1 1 calc R . .
H26B H 1.1559 0.3652 0.8480 0.078 Uiso 1 1 calc R . .
C27 C 0.7413(3) 0.3794(3) 0.2290(2) 0.0694(10) Uani 1 1 d . . .
H27A H 0.8087 0.3502 0.2156 0.083 Uiso 1 1 calc R . .
H27B H 0.7550 0.4124 0.2821 0.083 Uiso 1 1 calc R . .
C28 C 0.7094(4) 0.4405(3) 0.1549(3) 0.0792(11) Uani 1 1 d . . .
H28A H 0.6975 0.4083 0.1018 0.119 Uiso 1 1 calc R . .
H28B H 0.7671 0.4815 0.1476 0.119 Uiso 1 1 calc R . .
H28C H 0.6434 0.4703 0.1683 0.119 Uiso 1 1 calc R . .
C29 C 1.2015(3) 0.3045(3) 0.6959(3) 0.0779(11) Uani 1 1 d U . .
H29A H 1.1994 0.2595 0.6520 0.093 Uiso 1 1 calc R . .
H29B H 1.2602 0.2910 0.7383 0.093 Uiso 1 1 calc R . .
C30 C 1.1070(3) 0.2453(3) 0.8897(2) 0.0664(9) Uani 1 1 d . . .
H30A H 1.1765 0.2179 0.8793 0.080 Uiso 1 1 calc R . .
H30B H 1.1083 0.2627 0.9506 0.080 Uiso 1 1 calc R . .
C31 C 1.0300(4) 0.1008(3) 0.9287(3) 0.0829(12) Uani 1 1 d . . .
H31A H 1.0972 0.0725 0.9159 0.124 Uiso 1 1 calc R . .
H31B H 0.9696 0.0627 0.9157 0.124 Uiso 1 1 calc R . .
H31C H 1.0311 0.1160 0.9895 0.124 Uiso 1 1 calc R . .
C32 C 1.2275(4) 0.3918(4) 0.6513(3) 0.0986(15) Uani 1 1 d U . .
H32A H 1.1606 0.4128 0.6223 0.118 Uiso 1 1 calc R . .
H32B H 1.2481 0.4329 0.6967 0.118 Uiso 1 1 calc R . .
C33 C 1.3322(5) 0.4791(5) 0.5472(4) 0.139(3) Uani 1 1 d . . .
H33A H 1.2686 0.4966 0.5129 0.208 Uiso 1 1 calc R . .
H33B H 1.3936 0.4748 0.5103 0.208 Uiso 1 1 calc R . .
H33C H 1.3478 0.5209 0.5922 0.208 Uiso 1 1 calc R . .
C34 C 1.3113(4) 0.3915(5) 0.5889(3) 0.131(3) Uani 1 1 d . . .
H34A H 1.2912 0.3508 0.5430 0.157 Uiso 1 1 calc R . .
H34B H 1.3788 0.3715 0.6175 0.157 Uiso 1 1 calc R . .
C36 C 0.4150(5) 0.1243(5) 0.5356(4) 0.145(3) Uani 1 1 d . B .
H36A H 0.3422 0.1283 0.5101 0.217 Uiso 1 1 calc R . .
H36B H 0.4126 0.1291 0.5980 0.217 Uiso 1 1 calc R . .
H36C H 0.4463 0.0698 0.5208 0.217 Uiso 1 1 calc RD . .
C37 C 0.4845(4) 0.1965(5) 0.5009(3) 0.124(2) Uani 1 1 d DU . .
H37A H 0.5546 0.1699 0.4904 0.149 Uiso 1 1 calc R A 1
H37B H 0.4976 0.2348 0.5502 0.149 Uiso 1 1 calc R A 1
N1 N 0.80731(17) 0.15002(17) 0.45731(14) 0.0441(6) Uani 1 1 d . . .
C35A C 0.4615(4) 0.2586(4) 0.4195(4) 0.0596(12) Uani 0.594(6) 1 d P B 1
H35A H 0.3850 0.2751 0.4161 0.072 Uiso 0.594(6) 1 calc PRD B 1
H35B H 0.5053 0.3105 0.4262 0.072 Uiso 0.594(6) 1 calc PR B 1
C35B C 0.4264(6) 0.1704(5) 0.4058(5) 0.0596(12) Uani 0.406(6) 1 d PD B 2
H35C H 0.4285 0.1086 0.3972 0.072 Uiso 0.406(6) 1 calc PRD B 2
H35D H 0.3507 0.1892 0.4023 0.072 Uiso 0.406(6) 1 calc PR B 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 '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
N3 Ni1 N3 180.000(1) . 3_756
N3 Ni1 N2 89.81(9) . .
N3 Ni1 N2 90.19(9) 3_756 .
N3 Ni1 N2 90.19(9) . 3_756
N3 Ni1 N2 89.81(9) 3_756 3_756
N2 Ni1 N2 180.000(1) . 3_756
C4 N2 C7 106.6(2) . .
C4 N2 Ni1 126.00(19) . .
C7 N2 Ni1 127.37(18) . .
C5 N3 C15 106.3(2) . .
C5 N3 Ni1 126.42(18) . .
C15 N3 Ni1 127.27(19) . .
C4 N6 C15 121.6(2) . 3_756
N6 C4 N2 128.6(2) . .
N6 C4 C21 120.9(3) . .
N2 C4 C21 110.4(3) . .
N1 C5 N3 128.5(3) . .
N1 C5 C13 121.2(3) . .
N3 C5 C13 110.3(2) . .
C23 N5 C25 119.3(3) . .
C23 N5 C17 117.7(2) . .
C25 N5 C17 114.6(3) . .
N1 C7 N2 126.7(2) . .
N1 C7 C9 123.0(3) . .
N2 C7 C9 110.3(2) . .
C13 C8 C14 120.7(3) . .
C13 C8 C15 105.8(2) . .
C14 C8 C15 133.2(3) . .
C21 C9 C23 121.0(3) . .
C21 C9 C7 105.7(2) . .
C23 C9 C7 133.2(3) . .
C14 N4 C29 117.8(3) . .
C14 N4 C26 120.6(3) . .
C29 N4 C26 120.2(3) . .
C27 C11 C17 112.0(3) . .
C19 C12 C21 116.1(3) . .
C18 C13 C8 122.7(3) . .
C18 C13 C5 130.5(2) . .
C8 C13 C5 106.6(2) . .
N4 C14 C22 121.9(3) . .
N4 C14 C8 122.2(3) . .
C22 C14 C8 115.9(3) . .
N6 C15 N3 126.3(3) 3_756 .
N6 C15 C8 122.8(3) 3_756 .
N3 C15 C8 110.8(2) . .
C19 C16 C23 123.2(3) . .
N5 C17 C11 114.8(3) . .
C20 C18 C13 116.7(3) . .
C16 C19 C12 121.8(3) . .
C18 C20 C22 121.4(3) . .
C9 C21 C12 123.1(3) . .
C9 C21 C4 106.9(2) . .
C12 C21 C4 129.9(3) . .
C20 C22 C14 122.6(3) . .
N5 C23 C16 123.2(3) . .
N5 C23 C9 121.9(3) . .
C16 C23 C9 114.8(3) . .
C30 C24 C31 114.2(3) . .
C35A C25 C35B 60.1(4) . .
C35A C25 N5 113.4(3) . .
C35B C25 N5 114.5(4) . .
N4 C26 C30 111.7(3) . .
C11 C27 C28 112.3(3) . .
N4 C29 C32 113.3(4) . .
C24 C30 C26 114.5(3) . .
C34 C32 C29 117.1(6) . .
C32 C34 C33 114.5(6) . .
C36 C37 C35A 129.7(5) . .
C36 C37 C35B 84.3(5) . .
C35A C37 C35B 53.1(4) . .
C7 N1 C5 121.1(2) . .
C25 C35A C37 108.9(5) . .
C25 C35B C37 105.8(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 N3 1.900(2) .
Ni1 N3 1.900(2) 3_756
Ni1 N2 1.906(2) .
Ni1 N2 1.906(2) 3_756
N2 C4 1.367(4) .
N2 C7 1.383(4) .
N3 C5 1.372(4) .
N3 C15 1.386(3) .
N6 C4 1.317(4) .
N6 C15 1.319(4) 3_756
C4 C21 1.450(4) .
C5 N1 1.320(3) .
C5 C13 1.452(4) .
N5 C23 1.386(4) .
N5 C25 1.461(4) .
N5 C17 1.466(5) .
C7 N1 1.316(4) .
C7 C9 1.457(4) .
C8 C13 1.396(4) .
C8 C14 1.410(4) .
C8 C15 1.444(4) .
C9 C21 1.388(4) .
C9 C23 1.418(4) .
N4 C14 1.394(4) .
N4 C29 1.449(5) .
N4 C26 1.466(4) .
C11 C27 1.507(5) .
C11 C17 1.527(5) .
C12 C19 1.381(5) .
C12 C21 1.396(4) .
C13 C18 1.388(4) .
C14 C22 1.396(4) .
C15 N6 1.319(4) 3_756
C16 C19 1.381(5) .
C16 C23 1.406(4) .
C18 C20 1.382(4) .
C20 C22 1.392(4) .
C24 C30 1.499(5) .
C24 C31 1.499(5) .
C25 C35A 1.442(7) .
C25 C35B 1.449(8) .
C26 C30 1.530(5) .
C27 C28 1.518(6) .
C29 C32 1.556(7) .
C32 C34 1.431(7) .
C33 C34 1.528(9) .
C36 C37 1.516(9) .
C37 C35A 1.592(8) .
C37 C35B 1.644(8) .
