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_4032381
_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         'C27 H15 B Br2 Cl2 F2 N2 O3'
_chemical_formula_sum            'C27 H15 B Br2 Cl2 F2 N2 O3'
_chemical_formula_weight         694.94
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 98.473(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.0387(10)
_cell_length_b                   5.7510(4)
_cell_length_c                   16.2336(11)
_cell_measurement_reflns_used    2082
_cell_measurement_temperature    90.0(5)
_cell_measurement_theta_max      67.23
_cell_measurement_theta_min      3.18
_cell_volume                     1296.34(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90.0(5)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'QUAZAR multilayer optics'
_diffrn_radiation_source         'I\mS microfocus'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_av_unetI/netI     0.0782
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7138
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.199
_diffrn_reflns_theta_min         3.183
_exptl_absorpt_coefficient_mu    6.297
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_correction_T_min  0.542
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.780
_exptl_crystal_description       needle
_exptl_crystal_F_000             684
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_refine_diff_density_max         5.260
_refine_diff_density_min         -1.091
_refine_diff_density_rms         0.265
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.37(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         3433
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.1175
_refine_ls_R_factor_gt           0.1002
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2457
_refine_ls_wR_factor_ref         0.2689
_reflns_Friedel_coverage         0.810
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                2753
_reflns_number_total             3433
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02981_si_002.cif
_cod_data_source_block           NZhao83
_cod_depositor_comments
'Adding full bibliography for 4032381--4032382.cif.'
_cod_database_code               4032381
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.452
_shelx_estimated_absorpt_t_max   0.940
_shelx_res_checksum              75679
_shelx_hkl_checksum              90685