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_4126007
_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         'C26 H21 B F2 N2 O4, C H4 O'
_chemical_formula_sum            'C27 H25 B F2 N2 O5'
_chemical_formula_weight         506.30
_chemical_name_common            BAD2-TE
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -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                80.269(2)
_cell_angle_beta                 83.793(2)
_cell_angle_gamma                70.715(2)
_cell_formula_units_Z            2
_cell_length_a                   6.3949(3)
_cell_length_b                   9.4233(5)
_cell_length_c                   20.1050(10)
_cell_measurement_reflns_used    9648
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.679
_cell_measurement_theta_min      2.663
_cell_volume                     1125.33(10)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'APEX 3 (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      99.99
_diffrn_detector                 'Bruker D8 Quest ECO'
_diffrn_detector_area_resol_mean 5.12
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device       'DUO Kappa diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST Eco'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            24467
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.695
_diffrn_reflns_theta_min         2.662
_diffrn_source                   'standard sealed x-ray tube'
_diffrn_source_target            Mok\a
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0609 before and 0.0531 after correction.
The Ratio of minimum to maximum transmission is 0.9486.
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    1.494
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_recrystallization_method
'The material was recrystallised from methanol by slow evaporation'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     425
_refine_ls_number_reflns         5164
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0481
_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^)+(0.0448P)^2^+0.9471P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1164
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3827
_reflns_number_total             5164
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b00551_si_005.cif
_cod_data_source_block           kjf126a
_cod_depositor_comments
'Adding full bibliography for 4126005--4126007.cif.'
_cod_database_code               4126007
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O36-H36
 0.89 with sigma of 0.01
3. Others
 Sof(H29D)=Sof(H29E)=Sof(H29F)=1-FVAR(1)
 Sof(H29A)=Sof(H29B)=Sof(H29C)=FVAR(1)
4.a Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C37(H37A,H37B,H37C)
;
_shelx_res_checksum              98666
_shelx_hkl_checksum              70803
_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'