Synthesis of Carbazole-Based Selenaporphyrin via Annulation.
Masuda, Motoki; Maeda, Chihiro; Yoshioka, Naoki; Organic letters 15 (2013) 578–581; doi:10.1021/ol303392g

data_1508890
_publ_section_title
;
 Synthesis of Carbazole-Based Selenaporphyrin via Annulation.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              578
_journal_page_last               581
_journal_paper_doi               10.1021/ol303392g
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C50 H50 N2 Se2'
_chemical_formula_weight         836.84
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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
_cell_angle_alpha                90.204(4)
_cell_angle_beta                 104.566(3)
_cell_angle_gamma                111.507(2)
_cell_formula_units_Z            2
_cell_length_a                   10.1478(8)
_cell_length_b                   12.6951(12)
_cell_length_c                   16.6983(12)
_cell_measurement_reflns_used    9894
_cell_measurement_temperature    90.(2)
_cell_measurement_theta_max      66.7330
_cell_measurement_theta_min      3.7637
_cell_volume                     1926.1(3)
_computing_cell_refinement       'SAINT V8.18C (Bruker AXS Inc.)'
_computing_data_reduction        'SAINT V8.18C (Bruker AXS Inc.)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.946
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_sigmaI/netI    0.0525
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15836
_diffrn_reflns_theta_full        66.79
_diffrn_reflns_theta_max         66.79
_diffrn_reflns_theta_min         4.42
_exptl_absorpt_coefficient_mu    2.687
_exptl_absorpt_correction_T_max  0.69
_exptl_absorpt_correction_T_min  0.44
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            prism
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       yellow
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_refine_diff_density_max         2.093
_refine_diff_density_min         -1.916
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.253
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     481
_refine_ls_number_reflns         6463
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.253
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0709
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2163
_refine_ls_wR_factor_ref         0.2730
_reflns_number_gt                5714
_reflns_number_total             6463
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol303392g_si_003.cif
_cod_data_source_block           I
_cod_database_code               1508890