Replacing Phenyl Ring with Thiophene: An Approach to Longer Wavelength Aza-dipyrromethene Boron Difluoride (Aza-BODIPY) Dyes
Xinfu Zhang; Haibo Yu; Yi Xiao; Journal of Organic Chemistry 77 (2012) 669–673; doi:10.1021/jo201413b

data_4026821
_publ_section_title
;
 Replacing Phenyl Ring with Thiophene: An Approach to Longer Wavelength
 Aza-dipyrromethene Boron Difluoride (Aza-BODIPY) Dyes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              669
_journal_page_last               673
_journal_paper_doi               10.1021/jo201413b
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C24 H14 B F2 N3 S4'
_chemical_formula_weight         521.43
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.984(11)
_cell_length_b                   16.310(13)
_cell_length_c                   21.560(17)
_cell_measurement_reflns_used    2960
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      23.09
_cell_measurement_theta_min      2.22
_cell_volume                     4566(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0972
_diffrn_reflns_av_sigmaI/netI    0.1250
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19043
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    0.452
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_description       block
_exptl_crystal_F_000             2128
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.680
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.123
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.25(18)
_refine_ls_extinction_coef       0.0027(9)
_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   0.999
_refine_ls_hydrogen_treatment    'riding model'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     612
_refine_ls_number_reflns         6601
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.2149
_refine_ls_R_factor_gt           0.0927
_refine_ls_shift/su_max          0.089
_refine_ls_shift/su_mean         0.014
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1541P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2352
_refine_ls_wR_factor_ref         0.2778
_reflns_number_gt                2949
_reflns_number_total             6601
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201413b_si_003.cif
_cod_data_source_block           b
_cod_depositor_comments
;

2025-10-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C48 H28 B2 F4 N6 S8'
_cod_original_formula_weight         1042.86
_cod_original_formula_units_Z            4
_cod_database_code               4026821