Triplet quenching pathway control with molecular dyads enables the identification of a highly oxidizing annihilator class.
Bertrams, Maria-Sophie; Hermainski, Katharina; Mörsdorf, Jean-Marc; Ballmann, Joachim; Kerzig, Christoph; Chemical science 14 (2023) 8583–8591; doi:10.1039/d3sc01725g

data_1569549
_publ_section_title
;
 Triplet quenching pathway control with molecular dyads enables the
 identification of a highly oxidizing annihilator class.
;
_journal_issue                   32
_journal_name_full               'Chemical science'
_journal_page_first              8583
_journal_page_last               8591
_journal_paper_doi               10.1039/d3sc01725g
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C26 H34 F2 P2, 4(C H4 O), 2(Cl)'
_chemical_formula_sum            'C30 H50 Cl2 F2 O4 P2'
_chemical_formula_weight         645.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-11-23
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-12-06 deposited with the CCDC.	2023-07-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.5657(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.68726(3)
_cell_length_b                   16.93199(8)
_cell_length_c                   13.38321(7)
_cell_measurement_reflns_used    60640
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      70.9470
_cell_measurement_theta_min      4.2050
_cell_volume                     1736.439(14)
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      120(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9621
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -26.00  72.00   1.00    2.00    --    0.00  38.00 150.00   98
  2  \w    -30.00  70.00   1.00    2.00    --    0.00  77.00-120.00  100
  3  \w    -30.00  70.00   1.00    2.00    --    0.00  77.00  30.00  100
  4  \w    -37.00   1.00   1.00    2.00    --   18.00 122.00 137.93   38
  5  \w    -29.00   1.00   1.00    2.00    --   26.00 121.00 -93.11   30
  6  \w     -2.00  24.00   1.00    4.00    --   38.00  96.00  40.28   26
  7  \w      0.00  28.00   1.00    4.00    --   38.00  92.00 151.31   28
  8  \w      6.00  34.00   1.00    4.00    --   42.00  87.00-162.33   28
  9  \w      5.00  33.00   1.00    4.00    --   42.00  89.00  41.48   28
 10  \w     12.00  38.00   1.00    4.00    --   46.00  84.00-145.82   26
 11  \w     14.00  45.00   1.00    4.00    --   46.00  81.00  46.17   31
 12  \w     12.00  38.00   1.00    4.00    --   46.00  84.00 -45.14   26
 13  \w     18.00  45.00   1.00    4.00    --   50.00  81.00 -99.09   27
 14  \w     18.00  45.00   1.00    4.00    --   50.00  81.00 140.76   27
 15  \w     18.00  45.00   1.00    4.00    --   50.00  81.00 108.87   27
 16  \w     23.00 111.00   1.00    4.00    --   54.00-125.00  30.00   88
 17  \w    -15.00  75.00   1.00    4.00    --   54.00 -57.00  90.00   90
 18  \w     24.00 124.00   1.00    4.00    --   54.00  77.00 -30.00  100
 19  \w     23.00 111.00   1.00    4.00    --   54.00-125.00  60.00   88
 20  \w    -15.00  75.00   1.00    4.00    --   54.00 -57.00-150.00   90
 21  \w     24.00 124.00   1.00    4.00    --   54.00  77.00  30.00  100
 22  \w     24.00 124.00   1.00    4.00    --   54.00  77.00-150.00  100
 23  \w     24.00 124.00   1.00    4.00    --   54.00  77.00 -60.00  100
 24  \w     24.00 124.00   1.00    4.00    --   54.00  77.00   0.00  100
 25  \w     24.00 124.00   1.00    4.00    --   54.00  77.00  60.00  100
 26  \w     25.00 124.00   1.00    4.00    --   54.00  75.00  86.52   99
 27  \w     28.00 128.00   1.00    4.00    --   58.00  77.00   0.94  100
 28  \w     30.00 127.00   1.00    4.00    --   58.00  73.00  41.68   97
 29  \w     29.00 128.00   1.00    4.00    --   58.00  75.00 166.12   99
 30  \w     29.00 128.00   1.00    4.00    --   58.00  75.00 -89.51   99
 31  \w     32.00 127.00   1.00    4.00    --   58.00  70.00 112.52   95
 32  \w     34.00 131.00   1.00    4.00    --   62.00  73.00-140.93   97
 33  \w     34.00 132.00   1.00    4.00    --   62.00  74.00 -86.24   98
 34  \w     32.00 132.00   1.00    4.00    --   62.00  77.00 -60.02  100
 35  \w     33.00 132.00   1.00    4.00    --   62.00  75.00-163.18   99
 36  \w     37.00 136.00   1.00    4.00    --   66.00  76.00 105.44   99
 37  \w     37.00 136.00   1.00    4.00    --   66.00  76.00  77.91   99
 38  \w     36.00 136.00   1.00    4.00    --   66.00  77.00-123.17  100
 39  \w     38.00 135.00   1.00    4.00    --   66.00  73.00 129.59   97
 40  \w     43.00 133.00   1.00    4.00    --   66.00  64.00 -88.95   90
 41  \w     43.00 134.00   1.00    4.00    --   66.00  66.00  72.06   91
 42  \w     38.00 135.00   1.00    4.00    --   66.00  73.00 -24.55   97
 43  \w     41.00 140.00   1.00    4.00    --   70.00  76.00  61.18   99
 44  \w     42.00 140.00   1.00    4.00    --   70.00  74.00 -53.98   98
 45  \w     40.00 140.00   1.00    4.00    --   70.00  77.00-171.54  100
 46  \w     43.00 139.00   1.00    4.00    --   70.00  71.00  29.47   96
 47  \w     41.00 140.00   1.00    4.00    --   70.00  75.00-133.85   99
 48  \w     48.00 143.00   1.00    4.00    --   74.00  70.00 133.43   95
 49  \w     44.00 144.00   1.00    4.00    --   74.00  77.00  13.35  100
 50  \w     47.00 143.00   1.00    4.00    --   74.00  72.00 -19.16   96
 51  \w     45.00 144.00   1.00    4.00    --   74.00  76.00-161.41   99
 52  \w     57.00 147.00   1.00    4.00    --   78.00  54.00 -35.36   90
 53  \w     54.00 146.00   1.00    4.00    --   78.00  68.00  90.07   92
 54  \w     58.00 153.00   1.00    8.00    --   82.00  44.00-126.47   95
 55  \w     61.00 151.00   1.00    8.00    --   82.00  54.00 -29.44   90
 56  \w     52.00 152.00   1.00    8.00    --   82.00  77.00 -96.21  100
 57  \w     52.00 152.00   1.00    8.00    --   82.00  77.00  42.64  100
 58  \w     56.00 156.00   1.00    8.00    --   86.00  77.00 140.73  100
 59  \w     65.00 156.00   1.00    8.00    --   86.00  53.00-100.29   91
 60  \w     73.00 163.00   1.00    8.00    --   94.00  57.00 109.91   90
 61  \w     65.00 164.00   1.00    8.00    --   94.00  76.00-151.00   99
 62  \w     77.00 168.00   1.00    8.00    --   98.00  53.00 -74.25   91
 63  \w     69.00 168.00   1.00    8.00    --   98.00  76.00  14.67   99
 64  \w     69.00 168.00   1.00    8.00    --   98.00  75.00 100.96   99
 65  \w     74.00 172.00   1.00    8.00    --  102.00  74.00 -39.65   98
 66  \w     85.00 175.00   1.00    8.00    --  108.00  64.00 120.00   90
 67  \w    100.00 178.00   1.00    8.00    --  108.00 111.00 -90.00   78
 68  \w     83.00 176.00   1.00    8.00    --  108.00  69.00  46.00   93
 69  \w     36.00 113.00   1.00    8.00    --  108.00-111.00  30.00   77
 70  \w     36.00 109.00   1.00    8.00    --  108.00 -92.00 120.00   73
 71  \w     82.00 178.00   1.00    8.00    --  108.00  38.00  30.00   96
 72  \w     36.00 109.00   1.00    8.00    --  108.00 -92.00-150.00   73
 73  \w     85.00 175.00   1.00    8.00    --  108.00  64.00  60.00   90
 74  \w     36.00 109.00   1.00    8.00    --  108.00 -92.00  30.00   73
 75  \w     85.00 175.00   1.00    8.00    --  108.00  64.00 150.00   90
 76  \w     85.00 175.00   1.00    8.00    --  108.00  64.00 -90.00   90
 77  \w     85.00 175.00   1.00    8.00    --  108.00  64.00-180.00   90
 78  \w     85.00 175.00   1.00    8.00    --  108.00  64.00  90.00   90
 79  \w     85.00 175.00   1.00    8.00    --  108.00  64.00   0.00   90
 80  \w     78.00 178.00   1.00    8.00    --  108.00  77.00 -30.00  100
 81  \w     78.00 178.00   1.00    8.00    --  108.00  77.00 120.00  100
 82  \w     85.00 175.00   1.00    8.00    --  108.00  64.00 -60.00   90
 83  \w     78.00 178.00   1.00    8.00    --  108.00  77.00  30.00  100
 84  \w     36.00 113.00   1.00    8.00    --  108.00-111.00 -60.00   77
 85  \w     78.00 178.00   1.00    8.00    --  108.00  77.00-180.00  100
 86  \w     78.00 178.00   1.00    8.00    --  108.00  77.00-120.00  100
 87  \w     78.00 178.00   1.00    8.00    --  108.00  77.00 -60.00  100
 88  \w     78.00 178.00   1.00    8.00    --  108.00  77.00-150.00  100
 89  \w     78.00 178.00   1.00    8.00    --  108.00  77.00 150.00  100
 90  \w     78.00 178.00   1.00    8.00    --  108.00  77.00  60.00  100
 91  \w     78.00 178.00   1.00    8.00    --  108.00  77.00 -90.00  100
 92  \w     41.00 131.00   1.00    8.00    --  108.00 -64.00-150.00   90
 93  \w     36.00 113.00   1.00    8.00    --  108.00-111.00  90.00   77
 94  \f      0.00 120.00   1.00    2.00 -48.23   0.00 -40.00    --   120
 95  \f      0.00 120.00   1.00    2.00  -0.93   0.00  40.00    --   120
 96  \f      0.00 120.00   1.00    2.00  -0.70   0.00 -60.00    --   120
 97  \f      0.00 120.00   1.00    2.00 -46.10   0.00 -60.00    --   120
 98  \f      0.00 120.00   1.00    2.00  48.23   0.00  40.00    --   120
 99  \f      0.00 120.00   1.00    2.00   0.70   0.00  60.00    --   120
100  \f      0.00 120.00   1.00    2.00   0.93   0.00 -40.00    --   120
101  \f      0.00 120.00   1.00    4.00  54.70  54.00  60.00    --   120
102  \f    240.00 360.00   1.00    4.00   5.77  54.00 -40.00    --   120
103  \f      0.00 120.00   1.00    4.00   7.90  54.00 -60.00    --   120
104  \f    240.00 360.00   1.00    4.00  54.93  54.00 -40.00    --   120
105  \f      0.00 120.00   1.00    4.00  53.30  54.00 -60.00    --   120
106  \f    240.00 360.00   1.00    4.00   7.90  54.00 -60.00    --   120
107  \f      0.00 120.00   1.00    4.00 100.10  54.00  60.00    --   120
108  \f      0.00 120.00   1.00    4.00 102.23  54.00  40.00    --   120
109  \w     24.00 124.00   1.00    4.00    --   54.00  77.00  60.00  100
110  \f    120.00 240.00   1.00    4.00   7.90  54.00 -60.00    --   120
111  \f    120.00 240.00   1.00    4.00 102.23  54.00  40.00    --   120
112  \w     24.00 124.00   1.00    4.00    --   54.00  77.00  90.00  100
113  \f      0.00 120.00   1.00    4.00  53.07  54.00  40.00    --   120
114  \f    120.00 240.00   1.00    4.00  54.70  54.00  60.00    --   120
115  \f    120.00 240.00   1.00    4.00 100.10  54.00  60.00    --   120
116  \f    120.00 240.00   1.00    4.00  53.07  54.00  40.00    --   120
117  \f      0.00 120.00   1.00    4.00  54.93  54.00 -40.00    --   120
118  \f    240.00 360.00   1.00    4.00  53.07  54.00  40.00    --   120
119  \f    240.00 360.00   1.00    4.00 102.23  54.00  40.00    --   120
120  \w     24.00 124.00   1.00    4.00    --   54.00  77.00-120.00  100
121  \f    240.00 360.00   1.00    4.00  53.30  54.00 -60.00    --   120
122  \f    240.00 360.00   1.00    4.00  54.70  54.00  60.00    --   120
123  \f    240.00 360.00   1.00    4.00 100.10  54.00  60.00    --   120
124  \f    120.00 240.00   1.00    4.00  54.93  54.00 -40.00    --   120
125  \w     24.00 124.00   1.00    4.00    --   54.00  77.00-150.00  100
126  \w     24.00 124.00   1.00    4.00    --   54.00  77.00-180.00  100
127  \w     24.00 124.00   1.00    4.00    --   54.00  77.00 -90.00  100
128  \w     24.00 124.00   1.00    4.00    --   54.00  77.00 -60.00  100
129  \w     24.00 124.00   1.00    4.00    --   54.00  77.00 -30.00  100
130  \w     24.00 124.00   1.00    4.00    --   54.00  77.00   0.00  100
131  \w     24.00 124.00   1.00    4.00    --   54.00  77.00  30.00  100
132  \f    120.00 240.00   1.00    4.00   5.77  54.00 -40.00    --   120
133  \f      0.00 120.00   1.00    4.00   5.77  54.00 -40.00    --   120
134  \w     24.00 124.00   1.00    4.00    --   54.00  77.00 120.00  100
135  \f    120.00 240.00   1.00    4.00  53.30  54.00 -60.00    --   120
136  \f      0.00  26.00   1.00    8.00 108.93 108.00 -40.00    --    26
137  \f      0.00 120.00   1.00    8.00  59.77 108.00 -40.00    --   120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0006821000
_diffrn_orient_matrix_UB_12      0.0670767000
_diffrn_orient_matrix_UB_13      -0.0777940000
_diffrn_orient_matrix_UB_21      0.1849662000
_diffrn_orient_matrix_UB_22      -0.0238713000
_diffrn_orient_matrix_UB_23      -0.0250369000
_diffrn_orient_matrix_UB_31      -0.0787950000
_diffrn_orient_matrix_UB_32      -0.0566143000
_diffrn_orient_matrix_UB_33      -0.0816221000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0080
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            95360
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.133
_diffrn_reflns_theta_min         4.219
_diffrn_source_type              'Agilent SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.900
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.625
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_description       irregular
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3356
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0269
_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^)+(0.0368P)^2^+0.8550P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0730
_refine_ls_wR_factor_ref         0.0736
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3239
_reflns_number_total             3356
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc01725g2.cif
_cod_data_source_block           ba_para_fluor
_cod_depositor_comments
'Adding full bibliography for 1569549--1569550.cif.'
_cod_original_cell_volume        1736.440(14)
_cod_database_code               1569549
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.760
_shelx_estimated_absorpt_t_min   0.760
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6)
2.c Idealised Me refined as rotating group with stretchable bonds:
 C12(H12A,H12B,H12C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C13(H13A,H13B,
 H13C), C21(H21A,H21B,H21C), C31(H31A,H31B,H31C)
;
_shelx_res_checksum              17283
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.155
_oxdiff_exptl_absorpt_empirical_full_min 0.893