Enhanced Hypsochromic Shifts, Quantum Yield, and π-π Interactions in a meso,β-Heteroaryl-Fused BODIPY.
Zhao, Ning; Xuan, Sunting; Fronczek, Frank R.; Smith, Kevin M.; Vicente, M Graça H; The Journal of organic chemistry 82 (2017) 3880–3885; doi:10.1021/acs.joc.6b02981

data_4032382
_publ_section_title
;
 Enhanced Hypsochromic Shifts, Quantum Yield, and \p-\p Interactions in a
 meso,\b-Heteroaryl-Fused BODIPY.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3880
_journal_page_last               3885
_journal_paper_doi               10.1021/acs.joc.6b02981
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C15 H5 B Br2 Cl4 F2 N2 O'
_chemical_formula_sum            'C15 H5 B Br2 Cl4 F2 N2 O'
_chemical_formula_weight         579.64
_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                115.154(2)
_cell_angle_beta                 111.867(2)
_cell_angle_gamma                93.784(2)
_cell_formula_units_Z            2
_cell_length_a                   10.0033(9)
_cell_length_b                   10.2945(9)
_cell_length_c                   10.8914(10)
_cell_measurement_reflns_used    5368
_cell_measurement_temperature    90.0(5)
_cell_measurement_theta_max      30.43
_cell_measurement_theta_min      2.75
_cell_volume                     907.97(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90.0(5)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.903
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10782
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         30.50
_diffrn_reflns_theta_min         2.27
_exptl_absorpt_coefficient_mu    5.081
_exptl_absorpt_correction_T_max  0.6866
_exptl_absorpt_correction_T_min  0.5672
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.120
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.161
_refine_diff_density_min         -0.722
_refine_diff_density_rms         0.117
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         5019
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0277
_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^)+(0.0464P)^2^+0.1870P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0704
_refine_ls_wR_factor_ref         0.0746
_reflns_number_gt                4262
_reflns_number_total             5019
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo6b02981_si_001.cif
_cod_data_source_block           NZhao61
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4032381--4032382.cif.
;
_cod_original_sg_symbol_Hall     '-P 1 '
_cod_original_sg_symbol_H-M      'P -1   '
_cod_database_code               4032382