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_4315729
_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         'C13 H9 B F2 N2 O'
_chemical_formula_sum            'C13 H9 B F2 N2 O'
_chemical_formula_weight         258.03
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 113.720(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   17.064(5)
_cell_length_b                   9.872(5)
_cell_length_c                   7.399(5)
_cell_measurement_temperature    293(2)
_cell_volume                     1141.1(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.920
_diffrn_measured_fraction_theta_max 0.920
_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  0.0503
_diffrn_reflns_av_sigmaI/netI    0.0792
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6003
_diffrn_reflns_theta_full        25.85
_diffrn_reflns_theta_max         25.85
_diffrn_reflns_theta_min         2.44
_exptl_absorpt_coefficient_mu    0.118
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.6(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1807
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0558
_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^)+(0.0694P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1314
_reflns_number_gt                1344
_reflns_number_total             1807
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ic902467h_si_004.cif
_cod_data_source_block           2009_09_24b_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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               4315729