Syntheses and Reactivity of meso-Unsubstituted Azuliporphyrins Derived from 6-tert-Butyl- and 6-Phenylazulene
Timothy D. Lash; Jessica A. El-Beck; Gregory M. Ferrence; Journal of Organic Chemistry 72 (2007) 8402–8415; doi:10.1021/jo701523s

data_4023033
_publ_contact_author             'Ferrence, Gregory M.'
_publ_contact_author_email       ferrence@ilstu.edu
_publ_section_title
;
 Syntheses and Reactivity of meso-Unsubstituted Azuliporphyrins
 Derived from 6-tert-Butyl- and 6-Phenylazulene
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8402
_journal_page_last               8415
_journal_paper_doi               10.1021/jo701523s
_journal_volume                  72
_journal_year                    2007
_chemical_compound_source        'Lash laboratory'
_chemical_formula_moiety         'C40 H45 N3'
_chemical_formula_sum            'C40 H45 N3'
_chemical_formula_weight         567.79
_chemical_name_systematic
;
 2^3^-<i>tert</i>-butyl-8,12,13,17-tetraethyl-7,18-dimethylazuliporphyrin
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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_date             2007-06-12T20:20:40-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                87.9668(15)
_cell_angle_beta                 74.7962(15)
_cell_angle_gamma                88.7667(16)
_cell_formula_units_Z            2
_cell_length_a                   10.2118(8)
_cell_length_b                   12.0005(10)
_cell_length_c                   13.2831(11)
_cell_measurement_reflns_used    6582
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.771
_cell_measurement_theta_min      2.253
_cell_measurement_wavelength     0.71073
_cell_volume                     1569.7(2)
_computing_cell_refinement       'SAINT+ 6.45 (Bruker, 2003)'
_computing_data_collection       'SMART 5.630 (Bruker, 1997-2002)'
_computing_data_reduction        'SAINT+ 6.45'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2002 (Giacovazzo et al, 2003)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker AXS SMART APEX CCD diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_unetI/netI     0.0911
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16847
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.59
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.07
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS in SAINT+ (Bruker, 2003)'
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         7749
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1256
_refine_ls_R_factor_gt           0.064
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0819P)^2^+0.0982P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1509
_refine_ls_wR_factor_ref         0.1777
_reflns_number_gt                4342
_reflns_number_total             7749
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo701523s-File001.cif
_cod_data_source_block           07mz083m
_cod_database_code               4023033