An Efficient Synthesis of Phthalocyanines Based on an Unprecedented Double-Addition of Oximes to Phthalonitriles
Maximilian N. Kopylovich; Vadim Yu. Kukushkin; Matti Haukka; Konstantin V. Luzyanin; Armando J. L. Pombeiro; Journal of the American Chemical Society 126 (2004) 15040–15041; doi:10.1021/ja046759i

data_4113199
_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
_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 \k-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/[\s^2^(Fo^2^)+(0.0352P)^2^+1.8372P] where P=(Fo^2^+2Fc^2^)/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