Incorporation of the 1,5-Naphthalene Subunit into Heteroporphyrin Structure: Toward Helical Aceneporphyrinoids
Bartosz Szyszko; Ewa Pacholska-Dudziak; Lechosław Latos-Grażyński; Journal of Organic Chemistry 78 (2013) 5090–5095; doi:10.1021/jo4006624

data_4028252
_publ_section_title
;
 Incorporation of the 1,5-Naphthalene Subunit into Heteroporphyrin
 Structure: Toward Helical Aceneporphyrinoids
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5090
_journal_page_last               5095
_journal_paper_doi               10.1021/jo4006624
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C52 H36 N2 S'
_chemical_formula_sum            'C52 H36 N2 S'
_chemical_formula_weight         720.89
_chemical_name_common            22-thia-1,5-naphthiporphyrin
_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                84.56(3)
_cell_angle_beta                 69.02(3)
_cell_angle_gamma                68.47(3)
_cell_formula_units_Z            2
_cell_length_a                   10.894(2)
_cell_length_b                   13.964(3)
_cell_length_c                   14.328(3)
_cell_measurement_reflns_used    5659
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.7857
_cell_measurement_theta_min      3.0052
_cell_volume                     1891.5(9)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_data_collection       'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3359
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.904
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       '\f and \w'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_sigmaI/netI    0.0871
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16990
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         28.87
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_description       plates
_exptl_crystal_F_000             756
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.884
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.938
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     498
_refine_ls_number_reflns         8979
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.938
_refine_ls_R_factor_all          0.1211
_refine_ls_R_factor_gt           0.0611
_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^)+(0.0942P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1494
_refine_ls_wR_factor_ref         0.1728
_reflns_number_gt                4962
_reflns_number_total             8979
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4006624_5-S.cif
_cod_data_source_block           15tianaf
_cod_original_cell_volume        1891.5(7)
_cod_database_code               4028252