Bridged eosin Y: A visible and near-infrared photoredox catalyst
Tanioka, Masaru; Kuromiya, Ayako; Ueda, Rina; Obata, Tohru; Muranaka, Atsuya; Uchiyama, Masanobu; Kamino, Shinichiro; Chemical Communications  (2022) –; doi:10.1039/D2CC02907C

data_7130227
_publ_section_title
;
 Bridged eosin Y: A visible and near-infrared photoredox catalyst
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02907C
_journal_year                    2022
_chemical_formula_moiety         'C20 H7 Br3 O5'
_chemical_formula_sum            'C20 H7 Br3 O5'
_chemical_formula_weight         566.99
_chemical_name_common            'bridged eosin Y'
_chemical_name_systematic        'bridged eosin Y'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-10-30
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2022-04-07 deposited with the CCDC.	2022-06-15 downloaded from the CCDC.
;
_cell_angle_alpha                68.286(5)
_cell_angle_beta                 76.020(4)
_cell_angle_gamma                83.671(4)
_cell_formula_units_Z            2
_cell_length_a                   7.9825(4)
_cell_length_b                   9.6307(5)
_cell_length_c                   12.1546(6)
_cell_measurement_reflns_used    4026
_cell_measurement_temperature    103.15
_cell_measurement_theta_max      68.0090
_cell_measurement_theta_min      4.9440
_cell_volume                     842.17(8)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      103.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.986
_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     -9.00  42.00   0.50    0.24    --   41.13 -37.00  60.00  102
  2  \w     12.00  62.00   0.50    0.24    --   41.13 -63.00 120.00  100
  3  \w     41.00  72.00   0.50    0.24    --   41.13-104.00  90.00   62
  4  \w     31.00  57.00   0.50    0.95    --   95.43 -50.00 120.00   52
  5  \w     72.00 101.00   0.50    0.95    --   95.43 -77.00  90.00   58
  6  \w     38.00  68.00   0.50    0.24    --   41.13 -91.00 -30.00   60
  7  \w     39.00  76.00   0.50    0.95    --   95.43 -80.00-137.00   74
  8  \w     41.00  67.00   0.50    0.95    --   95.43 -59.00-120.00   52
  9  \w     29.00  55.00   0.50    0.95    --   95.43 -50.00-150.00   52
 10  \w     29.00  54.00   0.50    0.95    --   95.43 -50.00 -90.00   50
 11  \w     36.00  94.00   0.50    0.95    --   95.43-117.00 -60.00  116
 12  \w     69.00  94.00   0.50    0.24    --   41.13-138.00-150.00   50
 13  \w     21.00  46.00   0.50    0.24    --   41.13-138.00-150.00   50
 14  \w    -26.00  33.00   0.50    0.24    --   41.13 -91.00 -30.00  118
 15  \w     30.00  73.00   0.50    0.95    --   95.43 -77.00  60.00   86
 16  \w     11.00  37.00   0.50    0.24    --   41.13-104.00  90.00   52
 17  \w    -20.00  29.00   0.50    0.24    --  -41.44  12.00  90.00   98
 18  \w    -18.00  12.00   0.50    0.24    --  -41.44  80.00 -13.00   60
 19  \w    -51.00 -26.00   0.50    0.24    --  -41.44  80.00 -13.00   50
 20  \w    -66.00 -41.00   0.50    0.95    --  -95.75  59.00 -30.00   50
 21  \w    -57.00 -32.00   0.50    0.95    --  -95.75  50.00   0.00   50
 22  \w    -61.00 -35.00   0.50    0.95    --  -95.75 117.00  60.00   52
 23  \w    -57.00 -31.00   0.50    0.95    --  -95.75  50.00 120.00   52
 24  \w    -22.00  13.00   0.50    0.24    --  -41.44  37.00 120.00   70
 25  \w     49.00  87.00   0.50    0.24    --   41.13  80.00 -13.00   76
 26  \w     79.00 142.00   0.50    0.95    --   95.43  42.00 -30.00  126
 27  \w    128.00 161.00   0.50    0.95    --   95.43  68.00  60.00   66
 28  \w    123.00 148.00   0.50    0.95    --   95.43  77.00 120.00   50
 29  \w     94.00 120.00   0.50    0.95    --   95.43  68.00  60.00   52
 30  \w     82.00 117.00   0.50    0.95    --   95.43  80.00 -13.00   70
 31  \w     69.00 106.00   0.50    0.95    --   95.43  77.00 120.00   74
 32  \w    -28.00  39.00   0.50    0.24    --   41.13 -80.00-137.00  134
 33  \w    -18.00  26.00   0.50    0.24    --   41.13 -25.00-150.00   88
 34  \w     82.00 163.00   0.50    0.95    --   95.43  33.00-180.00  162
 35  \w    -57.00 -32.00   0.50    0.95    --  -95.75  50.00-180.00   50
 36  \w    -83.00 -29.00   0.50    0.95    --  -95.75  68.00-180.00  108
 37  \w    -97.00 -30.00   0.50    0.95    --  -95.75 117.00 -30.00  134
 38  \w    -97.00 -65.00   0.50    0.95    --  -95.75 117.00  60.00   64
 39  \w    -92.00 -67.00   0.50    0.95    --  -95.75  80.00 -13.00   50
 40  \w   -104.00 -32.00   0.50    0.95    --  -95.75 117.00 -60.00  144
 41  \w   -125.00 -35.00   0.50    0.95    --  -95.75 141.00 -30.15  180
 42  \w   -106.00 -29.00   0.50    0.95    --  -95.75 117.00 150.00  154
 43  \w   -125.00 -27.00   0.50    0.95    --  -95.75 145.00 150.00  196
 44  \w    -96.00 -71.00   0.50    0.95    --  -95.75 -17.00 120.00   50
 45  \w   -110.00 -79.00   0.50    0.95    --  -95.75 -42.00  90.00   62
 46  \w    -56.00 -29.00   0.50    0.24    --  -41.44 -50.00 120.00   54
 47  \w   -104.00 -76.00   0.50    0.24    --  -41.44 -50.00 120.00   56
 48  \w    -96.00 -71.00   0.50    0.24    --  -41.44-138.00 120.00   50
 49  \w   -156.00-113.00   0.50    0.95    --  -95.75 -42.00  90.00   86
 50  \w   -161.00-116.00   0.50    0.95    --  -95.75 -17.00 120.00   90
 51  \w   -145.00 -84.00   0.50    0.95    --  -95.75 -96.00 -90.00  122
 52  \w   -112.00 -84.00   0.50    0.95    --  -95.75 -80.00-137.00   56
 53  \w   -110.00 -73.00   0.50    0.24    --  -41.44 -80.00-137.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1740421000
_diffrn_orient_matrix_UB_12      -0.0753729000
_diffrn_orient_matrix_UB_13      0.0297260000
_diffrn_orient_matrix_UB_21      -0.0449559000
_diffrn_orient_matrix_UB_22      0.1169180000
_diffrn_orient_matrix_UB_23      -0.1163081000
_diffrn_orient_matrix_UB_31      0.0852317000
_diffrn_orient_matrix_UB_32      -0.1015431000
_diffrn_orient_matrix_UB_33      -0.0715902000
_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  0.0353
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6805
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.408
_diffrn_reflns_theta_min         4.011
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    9.196
_exptl_absorpt_correction_T_max  0.895
_exptl_absorpt_correction_T_min  0.447
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (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            'metallic dark black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    2.236
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CHCl3/Et2O'
_exptl_crystal_size_max          0.129
_exptl_crystal_size_mid          0.099
_exptl_crystal_size_min          0.033
_refine_diff_density_max         0.685
_refine_diff_density_min         -1.012
_refine_diff_density_rms         0.132
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3051
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0376
_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^)+(0.0651P)^2^+0.2908P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1055
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2788
_reflns_number_total             3051
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02907c2.cif
_cod_data_source_block           bey_1030
_cod_database_code               7130227
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C40 H10 Br6 O10 '
_diffrn_oxdiff_digest_frames
;
014c042441cbf784b05a58b8aa6e2b3b76042949a36
;
_diffrn_oxdiff_digest_hkl
;
01907412a1eb38ad94eff3f063f7698015342f
;
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C16(H16), C15(H15), C17(H17), C5(H5A)
2.b Idealised tetrahedral OH refined as rotating group:
 O5(H5), O2(H2)
;
_shelx_res_checksum              98746
_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 1.530
_oxdiff_exptl_absorpt_empirical_full_min 0.769