Crystallographic, Photophysical, NMR Spectroscopic and Reactivity Manifestations of the "8-Heteroaryl Effect" in 4,4-Difluoro-8-(C4H3X)-4-bora-3a,4a-diaza-s-indacene (X= O, S, Se) (BODIPY) Systems
Kibong Kim; Changbum Jo; Shanmugam Easwaramoorthi; Jooyoung Sung; Dong Ho Kim; David G. Churchill; Inorganic Chemistry 49 (2010) 4881–4894; doi:10.1021/ic902467h

data_4315727
_publ_section_title
;
 Crystallographic, Photophysical, NMR Spectroscopic and Reactivity
 Manifestations of the "8-Heteroaryl Effect" in
 4,4-Difluoro-8-(C4H3X)-4-bora-3a,4a-diaza-s-indacene (X= O, S, Se)
 (BODIPY) Systems
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              4881
_journal_page_last               4894
_journal_paper_doi               10.1021/ic902467h
_journal_volume                  49
_journal_year                    2010
_chemical_formula_moiety         C13H9BF2N2Se
_chemical_formula_sum            'C13 H9 B F2 N2 Se'
_chemical_formula_weight         320.99
_chemical_name_common            2Se-BF2
_chemical_name_systematic
;
 Difluoroboryl-(2-selenyl)dipyrrin
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 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            4
_cell_length_a                   7.29830(10)
_cell_length_b                   10.8015(2)
_cell_length_c                   15.1294(2)
_cell_measurement_temperature    100(2)
_cell_volume                     1192.69(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.866
_diffrn_measured_fraction_theta_max 0.866
_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  0.0207
_diffrn_reflns_av_sigmaI/netI    0.0525
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5987
_diffrn_reflns_theta_full        31.21
_diffrn_reflns_theta_max         31.21
_diffrn_reflns_theta_min         3.10
_exptl_absorpt_coefficient_mu    3.157
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.788
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.685
_refine_diff_density_min         -0.574
_refine_diff_density_rms         0.096
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.030(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3079
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0379
_refine_ls_shift/su_max          0.222
_refine_ls_shift/su_mean         0.022
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0651P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1050
_reflns_number_gt                2805
_reflns_number_total             3079
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ic902467h_si_002.cif
_cod_data_source_block           2009_08_26a_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4315727