Facile Synthesis of Biphenyl-Fused BODIPY and Its Property.
Hayashi, Yosuke; Obata, Naoki; Tamaru, Masatomo; Yamaguchi, Shigeru; Matsuo, Yutaka; Saeki, Akinori; Seki, Shu; Kureishi, Yuka; Saito, Shohei; Yamaguchi, Shigehiro; Shinokubo, Hiroshi; Organic letters 14 (2012) 866–869; doi:10.1021/ol2033916

data_1503602
_publ_section_title
;
 Facile Synthesis of Biphenyl-Fused BODIPY and Its Property.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              866
_journal_page_last               869
_journal_paper_doi               10.1021/ol2033916
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C21.75 H15 B0.5 Cl2 F N'
_chemical_formula_weight         385.65
_chemical_name_systematic
; 
 ? 
;
_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                112.753(2)
_cell_angle_beta                 97.302(2)
_cell_angle_gamma                92.737(2)
_cell_formula_units_Z            4
_cell_length_a                   10.2548(11)
_cell_length_b                   13.2868(15)
_cell_length_c                   14.5076(16)
_cell_measurement_temperature    153(2)
_cell_volume                     1797.9(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0378
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_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            19430
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.54
_exptl_absorpt_coefficient_mu    0.376
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.189
_refine_diff_density_min         -0.859
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     490
_refine_ls_number_reflns         6346
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0974
_refine_ls_R_factor_gt           0.0895
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0778P)^2^+5.5437P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2053
_refine_ls_wR_factor_ref         0.2109
_reflns_number_gt                5781
_reflns_number_total             6346
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol2033916_si_001.cif
_cod_data_source_block           01113yh
_cod_original_formula_sum        'C21.75 H15 B0.50 Cl2 F N'
_cod_database_code               1503602