Control of triplet state generation in heavy atom-free BODIPY-anthracene dyads by media polarity and structural factors.
Filatov, Mikhail A.; Karuthedath, Safakath; Polestshuk, Pavel M.; Callaghan, Susan; Flanagan, Keith J.; Telitchko, Maxime; Wiesner, Thomas; Laquai, Frédéric; Senge, Mathias O.; Physical chemistry chemical physics : PCCP 20 (2018) 8016–8031; doi:10.1039/c7cp08472b

data_7230131
_publ_section_title
;
 Control of triplet state generation in heavy atom-free BODIPY-anthracene
 dyads by media polarity and structural factors.
;
_journal_issue                   12
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              8016
_journal_page_last               8031
_journal_paper_doi               10.1039/c7cp08472b
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C H Cl3, 2(C12.5 H9.5 B0.5 F N)'
_chemical_formula_sum            'C26 H20 B Cl3 F2 N2'
_chemical_formula_weight         515.60
_chemical_name_systematic
3,5-Dimethyl-8-(anthracen-9-yl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-10-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-11-12 deposited with the CCDC.
2018-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.737(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2315(15)
_cell_length_b                   11.3053(12)
_cell_length_c                   15.4276(16)
_cell_measurement_reflns_used    4339
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.85
_cell_measurement_theta_min      2.23
_cell_volume                     2476.9(5)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'APEX 3 (Bruker, 2016) '
_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      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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Kappa diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            30226
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.490
_diffrn_reflns_theta_min         1.801
_diffrn_source                   'standard sealed X-ray tube'
_diffrn_source_type              'Siemens, KFF Mo 2K -90 C'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.403
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6669
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0581 before and 0.0528 after correction. The Ratio of minimum to maximum transmission is 0.8944. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1056
_exptl_crystal_recrystallization_method
'The material was recrystallised from chloroform by slow evaporation'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         4620
_refine_ls_number_restraints     307
_refine_ls_restrained_S_all      1.580
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0480
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0547P)^2^+2.1573P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1289
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3153
_reflns_number_total             4620
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cp08472b2.cif
_cod_data_source_block           kjf153a
_cod_depositor_comments
'Adding full bibliography for 7230130--7230136.cif.'
_cod_database_code               7230131
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.896
_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
 Cl3-C1X
 1.73 with sigma of 0.01
 Cl3-C1X \\sim Cl1-C1X \\sim Cl2-C1X
 with sigma of 0.02
 Cl3-C1X \\sim Cl9-C1X \\sim Cl12-C1X \\sim Cl6-C1X \\sim Cl1-C1X \\sim Cl7-C1X
\\sim Cl4-C1X \\sim Cl10-
 C1X \\sim Cl2-C1X \\sim Cl11-C1X \\sim Cl5-C1X \\sim Cl8-C1X
 with sigma of 0.02
 Cl3-C1X \\sim Cl9-C3X \\sim Cl12-C4X \\sim Cl6-C2X \\sim Cl1-C1X \\sim Cl7-C3X
\\sim Cl4-C2X \\sim Cl10-
 C4X \\sim Cl11-C4X \\sim Cl2-C1X \\sim Cl5-C2X \\sim Cl8-C3X
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(Cl3) \\sim Ueq, Uanis(Cl9) \\sim Ueq, Uanis(Cl12) \\sim Ueq, Uanis(Cl6)
\\sim Ueq, Uanis(Cl1) \\sim Ueq, Uanis(Cl7) \\sim Ueq, Uanis(Cl4) \\sim Ueq,
Uanis(Cl10) \\sim Ueq, Uanis(Cl2) \\sim Ueq, Uanis(Cl5) \\sim Ueq, Uanis(Cl11)
\\sim Ueq, Uanis(Cl8) \\sim Ueq: with sigma of 0.001 and sigma for terminal
atoms of 0.002
Uanis(C3X) \\sim Ueq, Uanis(C1X) \\sim Ueq, Uanis(C4X) \\sim Ueq, Uanis(C2X)
\\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C1X) \\sim Ueq, Uanis(C4X) \\sim Ueq, Uanis(C2X) \\sim Ueq, Uanis(C3X)
\\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
4. Others
 Fixed Sof: Cl1(0.5) C1X(0.5) H1X(0.5) Cl2(0.5) Cl3(0.5) C4X(0.1) H4X(0.1)
 Cl10(0.1) Cl11(0.1) Cl12(0.1) C2X(0.27) H2X(0.27) Cl4(0.27) Cl5(0.27)
 Cl6(0.27) C3X(0.13) H3X(0.13) Cl7(0.13) Cl8(0.13) Cl9(0.13)
5.a Ternary CH refined with riding coordinates:
 C1X(H1X), C4X(H4X), C2X(H2X), C3X(H3X)
5.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C2(H2), C1(H1), C17(H17), C18(H18), C19(H19), C22(H22), C2(H2),
 C1(H1), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22)
5.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              21742
_shelx_hkl_checksum              18418
_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'