Generation of Triplet Excited States via Photoinduced Electron Transfer in meso-anthra-BODIPY: Fluorogenic Response toward Singlet Oxygen in Solution and in Vitro.
Filatov, Mikhail A.; Karuthedath, Safakath; Polestshuk, Pavel M.; Savoie, Huguette; Flanagan, Keith J.; Sy, Cindy; Sitte, Elisabeth; Telitchko, Maxime; Laquai, Frédéric; Boyle, Ross W.; Senge, Mathias O.; Journal of the American Chemical Society 139 (2017) 6282–6285; doi:10.1021/jacs.7b00551

data_4126005
_publ_section_title
;
 Generation of Triplet Excited States via Photoinduced Electron Transfer
 in meso-anthra-BODIPY: Fluorogenic Response toward Singlet Oxygen in
 Solution and in Vitro.
;
_journal_issue                   18
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6282
_journal_page_last               6285
_journal_paper_doi               10.1021/jacs.7b00551
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         '0.5(C H2 Cl2), C26 H21 B F2 N2 O2'
_chemical_formula_sum            'C26.5 H22 B Cl F2 N2 O2'
_chemical_formula_weight         484.72
_chemical_name_common            BAD2-BA
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-01-03
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.061(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.3115(10)
_cell_length_b                   6.4766(4)
_cell_length_c                   20.9257(12)
_cell_measurement_reflns_used    7402
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.32
_cell_measurement_theta_min      2.70
_cell_volume                     2242.9(2)
_computing_cell_refinement       'SAINT+ Ver. 8.34A (Bruker, 2014)'
_computing_data_collection       'APEX 3 (Bruker, 2015) '
_computing_data_reduction        'SAINT+ Ver. 8.34A (Bruker, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'Kappa diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0916
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            33492
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.390
_diffrn_reflns_theta_max         25.390
_diffrn_reflns_theta_min         2.695
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mok\a
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6672
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0672 before and 0.0590 after correction.
The Ratio of minimum to maximum transmission is 0.8953.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_description       plate
_exptl_crystal_F_000             1004
_exptl_crystal_recrystallization_method
;
The material was recrystallised from a mixture of DCM and 
methanol by slow evaporation'
;
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         4113
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0426
_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^)+(0.0418P)^2^+0.9346P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0976
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2876
_reflns_number_total             4113
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b00551_si_004.cif
_cod_data_source_block           kjf122
_cod_depositor_comments
'Adding full bibliography for 4126005--4126007.cif.'
_cod_original_formula_sum        'C26.50 H22 B Cl F2 N2 O2'
_cod_database_code               4126005
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C34-H34A = C34-H34B
 0.98 with sigma of 0.01
3. Others
 Fixed Sof: C34(0.5) Cl35(0.5) Cl36(0.5) H34A(0.5) H34B(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C8(H8), C4(H4), C3(H3), C27(H27), C26(H26), C25(H25), C24(H24),
 C20(H20), C19(H19), C18(H18), C17(H17)
4.b Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C33(H33A,H33B,H33C)
;
_shelx_res_checksum              38296
_shelx_hkl_checksum              42961
_shelx_shelxl_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN micromount with oil'
_olex2_submission_special_instructions 'No special instructions were received'