#------------------------------------------------------------------------------
#$Date: 2019-11-23 11:35:03 +0200 (Sat, 23 Nov 2019) $
#$Revision: 233106 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/85/4348569.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_4348569
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            'C68 H100 Mg N12 O4'
_chemical_formula_weight         1173.91
_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                 95.710(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   16.6724(4)
_cell_length_b                   9.2766(2)
_cell_length_c                   21.1588(5)
_cell_measurement_reflns_used    4502
_cell_measurement_temperature    150
_cell_measurement_theta_max      67.0879
_cell_measurement_theta_min      3.2207
_cell_volume                     3256.25(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_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  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0330
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10124
_diffrn_reflns_theta_full        65.00
_diffrn_reflns_theta_max         65.00
_diffrn_reflns_theta_min         4.20
_exptl_absorpt_coefficient_mu    0.681
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71874
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blok
_exptl_crystal_F_000             1272
_refine_diff_density_max         0.781
_refine_diff_density_min         -0.917
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         5503
_refine_ls_number_restraints     169
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0713
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1248P)²+3.0527P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1977
_refine_ls_wR_factor_ref         0.2039
_reflns_number_gt                4873
_reflns_number_total             5503
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic6b01371_si_003.cif
_cod_data_source_block           6565
_cod_database_code               4348569
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
Mg1 Mg 1.0000 0.5000 0.5000 0.0263(3) Uani 1 2 d S
N2 N 1.00531(12) 0.3638(2) 0.42648(10) 0.0246(5) Uani 1 1 d .
N4 N 0.88105(12) 0.4664(2) 0.49990(10) 0.0242(5) Uani 1 1 d .
N3 N 0.86683(12) 0.2849(2) 0.41676(10) 0.0252(5) Uani 1 1 d .
C4 C 0.83998(15) 0.3689(3) 0.46189(12) 0.0252(5) Uani 1 1 d U
C5 C 0.69342(16) 0.2764(3) 0.45353(13) 0.0321(5) Uani 1 1 d U
H5 H 0.7001 0.2063 0.4230 0.039 Uiso 1 1 calc R
C6 C 1.05270(15) 0.2165(3) 0.35128(12) 0.0245(5) Uani 1 1 d U
N1 N 0.84897(13) 0.0532(2) 0.31163(10) 0.0290(5) Uani 1 1 d .
C8 C 0.94184(15) 0.2841(3) 0.40022(11) 0.0241(5) Uani 1 1 d U
N5 N 0.65867(15) 0.6138(3) 0.58449(13) 0.0409(6) Uani 1 1 d .
C10 C 0.96986(15) 0.1906(3) 0.35069(11) 0.0243(5) Uani 1 1 d U
C11 C 1.07352(15) 0.3272(3) 0.39997(11) 0.0235(5) Uani 1 1 d U
C12 C 0.93180(16) 0.0837(3) 0.31016(11) 0.0260(5) Uani 1 1 d U
C13 C 0.83018(15) 0.5302(3) 0.53850(12) 0.0244(5) Uani 1 1 d U
C14 C 0.75615(15) 0.3663(3) 0.47635(12) 0.0278(5) Uani 1 1 d U
C15 C 1.10112(16) 0.1390(3) 0.31344(12) 0.0266(5) Uani 1 1 d U
H15 H 1.1562 0.1564 0.3146 0.032 Uiso 1 1 calc R
C16 C 1.06344(16) 0.0344(3) 0.27376(12) 0.0290(5) Uani 1 1 d U
H16 H 1.0940 -0.0193 0.2478 0.035 Uiso 1 1 calc R
C17 C 0.74830(15) 0.4727(3) 0.52240(12) 0.0275(5) Uani 1 1 d U
C44 C 0.98086(16) 0.0084(3) 0.27201(12) 0.0283(5) Uani 1 1 d U
H44 H 0.9578 -0.0616 0.2445 0.034 Uiso 1 1 calc R
C18 C 0.67218(16) 0.4999(3) 0.54409(14) 0.0318(5) Uani 1 1 d U
C19 C 0.82181(18) -0.0905(3) 0.28789(14) 0.0344(6) Uani 1 1 d U
H19A H 0.8620 -0.1620 0.3023 0.041 Uiso 1 1 calc R
H19B H 0.8167 -0.0901 0.2418 0.041 Uiso 1 1 calc R
C20 C 0.61012(16) 0.4049(3) 0.52194(14) 0.0358(6) Uani 1 1 d U
H20 H 0.5599 0.4152 0.5370 0.043 Uiso 1 1 calc R
C21 C 0.62055(16) 0.2958(3) 0.47825(14) 0.0361(6) Uani 1 1 d U
H21 H 0.5777 0.2348 0.4655 0.043 Uiso 1 1 calc R
C22 C 0.79130(19) 0.2007(3) 0.21731(14) 0.0396(6) Uani 1 1 d U
H22A H 0.7734 0.1144 0.1941 0.048 Uiso 1 1 calc R
H22B H 0.8449 0.2242 0.2063 0.048 Uiso 1 1 calc R
C23 C 0.74117(19) -0.1318(3) 0.31102(15) 0.0401(6) Uani 1 1 d U
H23A H 0.7426 -0.1105 0.3560 0.048 Uiso 1 1 calc R
H23B H 0.6989 -0.0737 0.2889 0.048 Uiso 1 1 calc R
C24 C 0.5848(2) 0.6149(4) 0.61587(18) 0.0545(8) Uani 1 1 d U
H24A H 0.5392 0.6031 0.5841 0.065 Uiso 1 1 calc R
H24B H 0.5796 0.7081 0.6358 0.065 Uiso 1 1 calc R
C25 C 0.7209(2) -0.2907(3) 0.30037(17) 0.0453(7) Uani 1 1 d U
H25A H 0.6646 -0.3058 0.3064 0.054 Uiso 1 1 calc R
H25B H 0.7281 -0.3156 0.2568 0.054 Uiso 1 1 calc R
C26 C 0.7344(2) 0.3240(3) 0.19758(16) 0.0470(7) Uani 1 1 d U
H26A H 0.6803 0.2977 0.2066 0.056 Uiso 1 1 calc R
H26B H 0.7505 0.4082 0.2229 0.056 Uiso 1 1 calc R
C30 C 0.5816(3) 0.4985(5) 0.6655(2) 0.0657(8) Uani 1 1 d U
H30A H 0.6274 0.5093 0.6973 0.079 Uiso 1 1 calc R
H30B H 0.5858 0.4050 0.6456 0.079 Uiso 1 1 calc R
C32 C 0.5042(3) 0.5043(6) 0.6980(3) 0.0821(10) Uani 1 1 d U
H32A H 0.4962 0.6020 0.7125 0.099 Uiso 1 1 calc R
H32B H 0.4591 0.4804 0.6672 0.099 Uiso 1 1 calc R
C33 C 0.7329(3) 0.3622(4) 0.12824(19) 0.0758(14) Uani 1 1 d U
H33A H 0.7856 0.3933 0.1194 0.114 Uiso 1 1 calc R
H33B H 0.6948 0.4385 0.1183 0.114 Uiso 1 1 calc R
H33C H 0.7174 0.2791 0.1028 0.114 Uiso 1 1 calc R
C35 C 0.5046(5) 0.4041(9) 0.7531(3) 0.137(3) Uani 1 1 d U
H35A H 0.4988 0.3067 0.7379 0.205 Uiso 1 1 calc R
H35B H 0.4606 0.4273 0.7773 0.205 Uiso 1 1 calc R
H35C H 0.5546 0.4136 0.7795 0.205 Uiso 1 1 calc R
C42 C 0.7720(2) -0.3904(4) 0.34438(18) 0.0513(8) Uani 1 1 d U
H42A H 0.8271 -0.3851 0.3350 0.077 Uiso 1 1 calc R
H42B H 0.7529 -0.4876 0.3384 0.077 Uiso 1 1 calc R
H42C H 0.7685 -0.3618 0.3876 0.077 Uiso 1 1 calc R
C45 C 0.79499(17) 0.1710(3) 0.28787(14) 0.0344(6) Uani 1 1 d U
H45A H 0.8120 0.2585 0.3104 0.041 Uiso 1 1 calc R
H45B H 0.7410 0.1487 0.2982 0.041 Uiso 1 1 calc R
O1 O 0.97773(13) 0.6843(2) 0.43499(10) 0.0360(5) Uani 1 1 d .
C47 C 1.0242(2) 0.7190(4) 0.38443(14) 0.0419(7) Uani 1 1 d .
H47A H 1.0702 0.6564 0.3859 0.063 Uiso 1 1 calc R
H47B H 1.0420 0.8173 0.3886 0.063 Uiso 1 1 calc R
H47C H 0.9919 0.7068 0.3446 0.063 Uiso 1 1 calc R
N6 N 0.85138(13) 0.6252(2) 0.58517(10) 0.0253(5) Uani 1 1 d .
O3 O 0.87809(16) 0.9225(2) 0.44183(10) 0.0505(6) Uani 1 1 d .
H3 H 0.8658 0.9819 0.4138 0.076 Uiso 1 1 calc R
C49 C 0.8751(3) 0.9864(4) 0.50076(18) 0.0686(12) Uani 1 1 d .
H49A H 0.9235 1.0407 0.5116 0.103 Uiso 1 1 calc R
H49B H 0.8702 0.9131 0.5322 0.103 Uiso 1 1 calc R
H49C H 0.8293 1.0496 0.4994 0.103 Uiso 1 1 calc R
C50 C 0.6837(2) 0.7597(4) 0.56619(18) 0.0493(7) Uani 1 1 d U
H50A H 0.7334 0.7505 0.5462 0.059 Uiso 1 1 calc R
H50B H 0.6960 0.8154 0.6047 0.059 Uiso 1 1 calc R
C51 C 0.6237(2) 0.8468(4) 0.52132(19) 0.0552(7) Uani 1 1 d U
H51A H 0.5734 0.8561 0.5405 0.066 Uiso 1 1 calc R
H51B H 0.6451 0.9430 0.5165 0.066 Uiso 1 1 calc R
C52 C 0.6069(2) 0.7800(4) 0.4572(2) 0.0590(8) Uani 1 1 d U
H52A H 0.5810 0.6874 0.4614 0.071 Uiso 1 1 calc R
H52B H 0.6575 0.7634 0.4393 0.071 Uiso 1 1 calc R
C53 C 0.5523(3) 0.8766(5) 0.4117(2) 0.0734(12) Uani 1 1 d U
H53A H 0.5020 0.8924 0.4291 0.110 Uiso 1 1 calc R
H53B H 0.5425 0.8301 0.3712 0.110 Uiso 1 1 calc R
H53C H 0.5785 0.9675 0.4066 0.110 Uiso 1 1 calc R
H1Z H 0.949(2) 0.747(5) 0.4366(19) 0.053(12) Uiso 1 1 d .
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'
Mg Mg 0.1719 0.1771 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
N4 Mg1 N4 180.00(12) 3_766 .
N4 Mg1 N2 91.22(8) 3_766 3_766
N4 Mg1 N2 88.78(8) . 3_766
N4 Mg1 N2 88.78(8) 3_766 .
N4 Mg1 N2 91.22(8) . .
N2 Mg1 N2 180.000(1) 3_766 .
N4 Mg1 O1 90.84(8) 3_766 3_766
N4 Mg1 O1 89.16(8) . 3_766
N2 Mg1 O1 91.27(8) 3_766 3_766
N2 Mg1 O1 88.73(8) . 3_766
N4 Mg1 O1 89.16(8) 3_766 .
N4 Mg1 O1 90.84(8) . .
N2 Mg1 O1 88.73(8) 3_766 .
N2 Mg1 O1 91.27(8) . .
O1 Mg1 O1 180.00(8) 3_766 .
C11 N2 C8 110.1(2) . .
C11 N2 Mg1 125.34(17) . .
C8 N2 Mg1 124.29(17) . .
C4 N4 C13 109.7(2) . .
C4 N4 Mg1 123.14(17) . .
C13 N4 Mg1 127.08(17) . .
C8 N3 C4 125.3(2) . .
N3 C4 N4 128.8(2) . .
N3 C4 C14 122.2(2) . .
N4 C4 C14 109.0(2) . .
C21 C5 C14 116.8(3) . .
C15 C6 C10 122.3(2) . .
C15 C6 C11 130.8(2) . .
C10 C6 C11 106.8(2) . .
C12 N1 C45 114.2(2) . .
C12 N1 C19 116.1(2) . .
C45 N1 C19 113.4(2) . .
N3 C8 N2 127.0(2) . .
N3 C8 C10 124.2(2) . .
N2 C8 C10 108.8(2) . .
C18 N5 C24 118.8(3) . .
C18 N5 C50 117.8(3) . .
C24 N5 C50 112.7(3) . .
C6 C10 C12 120.4(2) . .
C6 C10 C8 105.9(2) . .
C12 C10 C8 133.5(2) . .
N6 C11 N2 128.5(2) 3_766 .
N6 C11 C6 123.1(2) 3_766 .
N2 C11 C6 108.3(2) . .
C44 C12 N1 122.9(2) . .
C44 C12 C10 116.6(2) . .
N1 C12 C10 120.4(2) . .
N6 C13 N4 126.0(2) . .
N6 C13 C17 125.2(2) . .
N4 C13 C17 108.7(2) . .
C5 C14 C17 123.1(2) . .
C5 C14 C4 129.9(2) . .
C17 C14 C4 107.0(2) . .
C16 C15 C6 117.0(2) . .
C15 C16 C44 121.5(2) . .
C14 C17 C18 120.0(2) . .
C14 C17 C13 105.5(2) . .
C18 C17 C13 134.5(2) . .
C12 C44 C16 122.2(2) . .
N5 C18 C20 121.5(3) . .
N5 C18 C17 122.7(2) . .
C20 C18 C17 115.8(3) . .
N1 C19 C23 111.5(2) . .
C21 C20 C18 122.8(3) . .
C5 C21 C20 121.2(3) . .
C45 C22 C26 111.8(3) . .
C25 C23 C19 112.7(3) . .
N5 C24 C30 113.7(3) . .
C42 C25 C23 113.4(3) . .
C33 C26 C22 113.2(3) . .
C24 C30 C32 112.2(4) . .
C35 C32 C30 113.1(5) . .
N1 C45 C22 115.8(2) . .
C47 O1 Mg1 125.18(18) . .
C11 N6 C13 124.2(2) 3_766 .
N5 C50 C51 117.3(3) . .
C52 C51 C50 113.2(3) . .
C51 C52 C53 111.8(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Mg1 N4 2.007(2) 3_766
Mg1 N4 2.007(2) .
Mg1 N2 2.013(2) 3_766
Mg1 N2 2.013(2) .
Mg1 O1 2.203(2) 3_766
Mg1 O1 2.203(2) .
N2 C11 1.360(3) .
N2 C8 1.363(3) .
N4 C4 1.351(3) .
N4 C13 1.369(3) .
N3 C8 1.332(3) .
N3 C4 1.343(3) .
C4 C14 1.460(4) .
C5 C21 1.382(4) .
C5 C14 1.387(4) .
C6 C15 1.392(4) .
C6 C10 1.401(4) .
C6 C11 1.472(3) .
N1 C12 1.413(3) .
N1 C45 1.472(4) .
N1 C19 1.480(3) .
C8 C10 1.472(3) .
N5 C18 1.391(4) .
N5 C24 1.456(4) .
N5 C50 1.480(4) .
C10 C12 1.419(3) .
C11 N6 1.335(3) 3_766
C12 C44 1.393(4) .
C13 N6 1.345(3) .
C13 C17 1.474(4) .
C14 C17 1.402(4) .
C15 C16 1.391(4) .
C16 C44 1.395(4) .
C17 C18 1.414(4) .
C18 C20 1.404(4) .
C19 C23 1.525(4) .
C20 C21 1.393(4) .
C22 C45 1.513(4) .
C22 C26 1.518(4) .
C23 C25 1.524(4) .
C24 C30 1.511(6) .
C25 C42 1.514(5) .
C26 C33 1.507(5) .
C30 C32 1.523(6) .
C32 C35 1.490(8) .
O1 C47 1.419(4) .
N6 C11 1.335(3) 3_766
O3 C49 1.386(4) .
C50 C51 1.539(5) .
C51 C52 1.492(6) .
C52 C53 1.545(6) .
