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_4113198
_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            'C32 H44 Cl2 N8 Ni O4'
_chemical_formula_weight         734.36
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 95.820(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.6235(11)
_cell_length_b                   9.2927(6)
_cell_length_c                   17.5169(15)
_cell_measurement_temperature    120(2)
_cell_volume                     1720.4(3)
_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      120(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0477
_diffrn_reflns_av_sigmaI/netI    0.0473
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10468
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.48
_exptl_absorpt_coefficient_mu    0.768
_exptl_absorpt_correction_T_max  0.9001
_exptl_absorpt_correction_T_min  0.8335
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v.2.10 (Sheldrick, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_description       block
_exptl_crystal_F_000             772
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         1.287
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.112
_refine_ls_extinction_coef       0.0086(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3000
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0516
_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^)+(0.0729P)^2^+4.1583P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1335
_refine_ls_wR_factor_ref         0.1519
_reflns_number_gt                2246
_reflns_number_total             3000
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja046759isi20040602_104139_2.cif
_cod_data_source_block           structure_2
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4113198