#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:30:38 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178902 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/31/4113199.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_4113199
loop_
_publ_author_name
'Maximilian N. Kopylovich'
'Vadim Yu. Kukushkin'
'Matti Haukka'
'Konstantin V. Luzyanin'
'Armando J. L. Pombeiro'
_publ_section_title
;
 An Efficient Synthesis of Phthalocyanines Based on an Unprecedented
 Double-Addition of Oximes to Phthalonitriles
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15040
_journal_page_last               15041
_journal_paper_doi               10.1021/ja046759i
_journal_volume                  126
_journal_year                    2004
_chemical_formula_sum            'C30 H34 Cl12 N8 Ni O4'
_chemical_formula_weight         1054.76
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                106.522(4)
_cell_angle_beta                 109.206(4)
_cell_angle_gamma                110.491(4)
_cell_formula_units_Z            1
_cell_length_a                   10.4825(8)
_cell_length_b                   11.3345(9)
_cell_length_c                   11.5961(8)
_cell_measurement_temperature    100(2)
_cell_volume                     1087.37(16)
_computing_cell_refinement       'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP in SHELXTL v.6.14 (Bruker AXS, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_sigmaI/netI    0.0461
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11577
_diffrn_reflns_theta_full        25.33
_diffrn_reflns_theta_max         25.33
_diffrn_reflns_theta_min         4.12
_exptl_absorpt_coefficient_mu    1.229
_exptl_absorpt_correction_T_max  0.79337
_exptl_absorpt_correction_T_min  0.65224
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Xprep in Shelxtl v.6.14 (Bruker AXS, 2003)'
_exptl_crystal_colour            block
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_description       colorless
_exptl_crystal_F_000             534
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3895
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0406
_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)+(0.0352P)²+1.8372P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.1063
_reflns_number_gt                3134
_reflns_number_total             3895
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja046759isi20040602_104139_3.cif
_cod_data_source_block           structure_3
_cod_original_cell_volume        1087.37(14)
_cod_database_code               4113199
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.6736(4) 0.1299(4) -0.1538(4) 0.0238(8) Uani 1 1 d .
C2 C 0.8224(4) 0.2274(4) -0.0248(4) 0.0301(9) Uani 1 1 d .
H2A H 0.8067 0.2234 0.0531 0.045 Uiso 1 1 calc R
H2B H 0.8587 0.3239 -0.0144 0.045 Uiso 1 1 calc R
H2C H 0.8999 0.1991 -0.0280 0.045 Uiso 1 1 calc R
C4 C 0.6659(4) 0.1242(4) -0.2864(4) 0.0315(9) Uani 1 1 d .
H4A H 0.6385 0.0290 -0.3470 0.047 Uiso 1 1 calc R
H4B H 0.7670 0.1923 -0.2693 0.047 Uiso 1 1 calc R
H4C H 0.5872 0.1476 -0.3298 0.047 Uiso 1 1 calc R
C5 C 0.5628(4) 0.3147(4) 0.1477(4) 0.0222(8) Uani 1 1 d .
C6 C 0.4587(5) 0.3048(4) 0.0179(4) 0.0284(9) Uani 1 1 d .
H6A H 0.4191 0.2133 -0.0578 0.043 Uiso 1 1 calc R
H6B H 0.5165 0.3808 0.0007 0.043 Uiso 1 1 calc R
H6C H 0.3717 0.3139 0.0253 0.043 Uiso 1 1 calc R
C8 C 0.6353(5) 0.4457(4) 0.2781(4) 0.0299(9) Uani 1 1 d .
H8A H 0.6010 0.4213 0.3413 0.045 Uiso 1 1 calc R
H8B H 0.6038 0.5126 0.2583 0.045 Uiso 1 1 calc R
H8C H 0.7484 0.4889 0.3201 0.045 Uiso 1 1 calc R
C9 C 0.7041(4) 0.1188(4) 0.2707(3) 0.0198(7) Uani 1 1 d .
C10 C 0.8522(4) 0.1591(3) 0.3895(3) 0.0186(7) Uani 1 1 d .
C11 C 0.8998(4) 0.2163(4) 0.5282(3) 0.0207(7) Uani 1 1 d .
H11 H 0.8412 0.2465 0.5641 0.025 Uiso 1 1 calc R
C12 C 1.0373(4) 0.2274(4) 0.6125(3) 0.0228(8) Uani 1 1 d .
C13 C 1.1240(4) 0.1842(4) 0.5588(4) 0.0209(7) Uani 1 1 d .
C14 C 1.0761(4) 0.1294(4) 0.4195(4) 0.0211(7) Uani 1 1 d .
H14 H 1.1354 0.1014 0.3828 0.025 Uiso 1 1 calc R
C15 C 0.9377(4) 0.1174(3) 0.3363(3) 0.0197(7) Uani 1 1 d .
C16 C 0.8447(4) 0.0526(3) 0.1844(3) 0.0189(7) Uani 1 1 d .
C99 C 0.2769(5) 0.4752(4) 0.3046(4) 0.0314(9) Uani 1 1 d .
H99 H 0.2925 0.3916 0.2960 0.038 Uiso 1 1 calc R
N1 N 0.5568(3) 0.0552(3) -0.1448(3) 0.0207(6) Uani 1 1 d .
N2 N 0.5840(3) 0.2097(3) 0.1430(3) 0.0203(6) Uani 1 1 d .
N3 N 0.8934(3) 0.0011(3) 0.1013(3) 0.0234(7) Uani 1 1 d .
H3A H 0.8236 -0.0450 0.0047 0.035 Uiso 1 1 d .
H3B H 0.9967 0.0244 0.1240 0.035 Uiso 1 1 d .
N4 N 0.7101(3) 0.0496(3) 0.1476(3) 0.0182(6) Uani 1 1 d .
O2 O 0.6944(3) 0.2415(2) 0.2761(2) 0.0214(5) Uani 1 1 d .
O3 O 0.4216(3) -0.0264(2) -0.2781(2) 0.0211(5) Uani 1 1 d .
Cl12 Cl 1.10012(11) 0.29481(11) 0.78733(9) 0.0316(2) Uani 1 1 d .
Cl13 Cl 1.29224(10) 0.19333(9) 0.66410(9) 0.0262(2) Uani 1 1 d .
Cl96 Cl 0.73613(10) -0.15089(9) -0.22295(9) 0.0244(2) Uani 1 1 d .
Cl97 Cl 0.44125(12) 0.62596(10) 0.44823(10) 0.0353(2) Uani 1 1 d .
Cl98 Cl 0.25112(14) 0.49552(12) 0.15363(11) 0.0426(3) Uani 1 1 d .
Cl99 Cl 0.11000(12) 0.44580(11) 0.32530(11) 0.0395(3) Uani 1 1 d .
Ni1 Ni 0.5000 0.0000 0.0000 0.01767(16) Uani 1 2 d S
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'
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'
Cl Cl 0.1484 0.1585 '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
N1 C1 C2 117.5(3) . .
N1 C1 C4 123.1(3) . .
C2 C1 C4 119.4(3) . .
C1 C2 H2A 109.5 . .
C1 C2 H2B 109.5 . .
H2A C2 H2B 109.5 . .
C1 C2 H2C 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
C1 C4 H4A 109.5 . .
C1 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
C1 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
N2 C5 C6 118.2(3) . .
N2 C5 C8 123.0(3) . .
C6 C5 C8 118.8(3) . .
C5 C6 H6A 109.5 . .
C5 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C5 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
C5 C8 H8A 109.5 . .
C5 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C5 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
O3 C9 O2 110.5(3) 2_655 .
O3 C9 N4 111.4(3) 2_655 .
O2 C9 N4 110.4(3) . .
O3 C9 C10 108.5(3) 2_655 .
O2 C9 C10 109.6(3) . .
N4 C9 C10 106.4(3) . .
C15 C10 C11 122.2(3) . .
C15 C10 C9 107.2(3) . .
C11 C10 C9 130.4(3) . .
C10 C11 C12 116.8(3) . .
C10 C11 H11 121.6 . .
C12 C11 H11 121.6 . .
C11 C12 C13 121.2(3) . .
C11 C12 Cl12 118.6(3) . .
C13 C12 Cl12 120.2(3) . .
C14 C13 C12 121.4(3) . .
C14 C13 Cl13 117.7(3) . .
C12 C13 Cl13 120.9(3) . .
C15 C14 C13 116.8(3) . .
C15 C14 H14 121.6 . .
C13 C14 H14 121.6 . .
C10 C15 C14 121.6(3) . .
C10 C15 C16 106.5(3) . .
C14 C15 C16 131.7(3) . .
N4 C16 N3 126.2(3) . .
N4 C16 C15 111.4(3) . .
N3 C16 C15 122.3(3) . .
Cl97 C99 Cl99 110.1(2) . .
Cl97 C99 Cl98 110.3(2) . .
Cl99 C99 Cl98 110.1(2) . .
Cl97 C99 H99 108.8 . .
Cl99 C99 H99 108.8 . .
Cl98 C99 H99 108.8 . .
C1 N1 O3 109.7(3) . .
C1 N1 Ni1 140.5(3) . .
O3 N1 Ni1 109.50(18) . .
C5 N2 O2 110.2(3) . .
C5 N2 Ni1 139.2(2) . .
O2 N2 Ni1 110.52(18) . .
C16 N3 H3A 117.2 . .
C16 N3 H3B 126.2 . .
H3A N3 H3B 114.5 . .
C16 N4 C9 108.3(3) . .
C16 N4 Ni1 151.1(2) . .
C9 N4 Ni1 100.5(2) . .
C9 O2 N2 108.9(2) . .
C9 O3 N1 109.8(2) 2_655 .
N4 Ni1 N4 180.0 . 2_655
N4 Ni1 N2 103.13(11) . 2_655
N4 Ni1 N2 76.87(11) 2_655 2_655
N4 Ni1 N2 76.87(11) . .
N4 Ni1 N2 103.13(11) 2_655 .
N2 Ni1 N2 180.0 2_655 .
N4 Ni1 N1 102.74(11) . .
N4 Ni1 N1 77.26(11) 2_655 .
N2 Ni1 N1 84.19(11) 2_655 .
N2 Ni1 N1 95.81(11) . .
N4 Ni1 N1 77.26(11) . 2_655
N4 Ni1 N1 102.74(11) 2_655 2_655
N2 Ni1 N1 95.81(11) 2_655 2_655
N2 Ni1 N1 84.19(11) . 2_655
N1 Ni1 N1 180.0 . 2_655
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.278(5) .
C1 C2 1.486(5) .
C1 C4 1.494(5) .
C2 H2A 0.9800 .
C2 H2B 0.9800 .
C2 H2C 0.9800 .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C5 N2 1.275(5) .
C5 C6 1.485(5) .
C5 C8 1.499(5) .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 O3 1.414(4) 2_655
C9 O2 1.415(4) .
C9 N4 1.455(4) .
C9 C10 1.502(5) .
C10 C15 1.380(5) .
C10 C11 1.381(5) .
C11 C12 1.388(5) .
C11 H11 0.9500 .
C12 C13 1.401(5) .
C12 Cl12 1.737(4) .
C13 C14 1.388(5) .
C13 Cl13 1.731(3) .
C14 C15 1.386(5) .
C14 H14 0.9500 .
C15 C16 1.492(5) .
C16 N4 1.317(4) .
C16 N3 1.321(4) .
C99 Cl97 1.759(4) .
C99 Cl99 1.773(4) .
C99 Cl98 1.775(4) .
C99 H99 1.0000 .
N1 O3 1.443(4) .
N1 Ni1 2.136(3) .
N2 O2 1.438(4) .
N2 Ni1 2.123(3) .
N3 H3A 0.9606 .
N3 H3B 0.9399 .
N4 Ni1 2.050(3) .
O3 C9 1.414(4) 2_655
Ni1 N4 2.050(3) 2_655
Ni1 N2 2.123(3) 2_655
Ni1 N1 2.136(3) 2_655
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3A Cl96 0.96 2.25 3.173(3) 159.6 .
N3 H3B Cl96 0.94 2.31 3.220(3) 161.7 2_755
N3 H3B N3 0.94 3.16 3.737(6) 121.0 2_755
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
O3 C9 C10 C15 121.0(3) 2_655 .
O2 C9 C10 C15 -118.3(3) . .
N4 C9 C10 C15 1.0(4) . .
O3 C9 C10 C11 -53.9(5) 2_655 .
O2 C9 C10 C11 66.8(5) . .
N4 C9 C10 C11 -173.8(3) . .
C15 C10 C11 C12 -1.3(5) . .
C9 C10 C11 C12 172.9(3) . .
C10 C11 C12 C13 0.8(5) . .
C10 C11 C12 Cl12 -178.6(3) . .
C11 C12 C13 C14 0.3(5) . .
Cl12 C12 C13 C14 179.7(3) . .
C11 C12 C13 Cl13 -178.0(3) . .
Cl12 C12 C13 Cl13 1.4(4) . .
C12 C13 C14 C15 -1.0(5) . .
Cl13 C13 C14 C15 177.3(3) . .
C11 C10 C15 C14 0.6(5) . .
C9 C10 C15 C14 -174.8(3) . .
C11 C10 C15 C16 176.1(3) . .
C9 C10 C15 C16 0.7(4) . .
C13 C14 C15 C10 0.6(5) . .
C13 C14 C15 C16 -173.7(3) . .
C10 C15 C16 N4 -2.5(4) . .
C14 C15 C16 N4 172.4(3) . .
C10 C15 C16 N3 -180.0(3) . .
C14 C15 C16 N3 -5.1(6) . .
C2 C1 N1 O3 176.8(3) . .
C4 C1 N1 O3 -2.6(5) . .
C2 C1 N1 Ni1 -9.5(6) . .
C4 C1 N1 Ni1 171.2(3) . .
C6 C5 N2 O2 176.7(3) . .
C8 C5 N2 O2 -4.6(5) . .
C6 C5 N2 Ni1 -6.1(6) . .
C8 C5 N2 Ni1 172.5(3) . .
N3 C16 N4 C9 -179.5(3) . .
C15 C16 N4 C9 3.2(4) . .
N3 C16 N4 Ni1 -2.6(7) . .
C15 C16 N4 Ni1 -179.9(4) . .
O3 C9 N4 C16 -120.7(3) 2_655 .
O2 C9 N4 C16 116.3(3) . .
C10 C9 N4 C16 -2.6(4) . .
O3 C9 N4 Ni1 60.9(3) 2_655 .
O2 C9 N4 Ni1 -62.2(3) . .
C10 C9 N4 Ni1 178.9(2) . .
O3 C9 O2 N2 -79.7(3) 2_655 .
N4 C9 O2 N2 43.9(3) . .
C10 C9 O2 N2 160.8(3) . .
C5 N2 O2 C9 174.3(3) . .
Ni1 N2 O2 C9 -3.7(3) . .
C1 N1 O3 C9 174.5(3) . 2_655
Ni1 N1 O3 C9 -1.3(3) . 2_655
C16 N4 Ni1 N4 -132(6) . 2_655
C9 N4 Ni1 N4 45(6) . 2_655
C16 N4 Ni1 N2 46.5(5) . 2_655
C9 N4 Ni1 N2 -136.53(19) . 2_655
C16 N4 Ni1 N2 -133.5(5) . .
C9 N4 Ni1 N2 43.47(19) . .
C16 N4 Ni1 N1 -40.4(5) . .
C9 N4 Ni1 N1 136.56(19) . .
C16 N4 Ni1 N1 139.6(5) . 2_655
C9 N4 Ni1 N1 -43.44(19) . 2_655
C5 N2 Ni1 N4 159.1(4) . .
O2 N2 Ni1 N4 -23.77(19) . .
C5 N2 Ni1 N4 -20.9(4) . 2_655
O2 N2 Ni1 N4 156.23(19) . 2_655
C5 N2 Ni1 N2 -80(4) . 2_655
O2 N2 Ni1 N2 97(4) . 2_655
C5 N2 Ni1 N1 57.3(4) . .
O2 N2 Ni1 N1 -125.5(2) . .
C5 N2 Ni1 N1 -122.7(4) . 2_655
O2 N2 Ni1 N1 54.5(2) . 2_655
C1 N1 Ni1 N4 -18.8(4) . .
O3 N1 Ni1 N4 154.90(19) . .
C1 N1 Ni1 N4 161.2(4) . 2_655
O3 N1 Ni1 N4 -25.10(19) . 2_655
C1 N1 Ni1 N2 -121.0(4) . 2_655
O3 N1 Ni1 N2 52.72(19) . 2_655
C1 N1 Ni1 N2 59.0(4) . .
O3 N1 Ni1 N2 -127.28(19) . .
C1 N1 Ni1 N1 165(7) . 2_655
O3 N1 Ni1 N1 -22(7) . 2_655
