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_7130230
_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         'C26 H15 N O2'
_chemical_formula_sum            'C26 H15 N O2'
_chemical_formula_weight         373.39
_chemical_name_common            1-(4-nitrophenyl)perylene
_chemical_name_systematic        1-(4-nitrophenyl)perylene
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-04-13
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_audit_update_record
;
2022-04-07 deposited with the CCDC.	2022-06-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   12.1091(2)
_cell_length_b                   13.4501(2)
_cell_length_c                   43.2055(9)
_cell_measurement_reflns_used    13433
_cell_measurement_temperature    103.15
_cell_measurement_theta_max      67.8910
_cell_measurement_theta_min      4.0980
_cell_volume                     7036.8(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (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 0.998
_diffrn_measured_fraction_theta_max 0.994
_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    -35.00  23.00   0.50    2.80    --   40.52 -12.00 -30.00  116
  2  \w     45.00  71.00   0.50    2.80    --   40.52  52.00 -68.00   52
  3  \w    128.00 160.00   0.50   11.20    --   96.04  52.00 -68.00   64
  4  \w    139.00 164.00   0.50   11.20    --   96.04 114.00   6.00   50
  5  \w     85.00 118.00   0.50   11.20    --   96.04  70.00 124.00   66
  6  \w     80.00 161.00   0.50   11.20    --   96.04 144.00 -30.00  162
  7  \w     82.00 119.00   0.50   11.20    --   96.04  52.00 -68.00   74
  8  \w     52.00  77.00   0.50   11.20    --   96.04 -70.00  -6.00   50
  9  \w     44.00  84.00   0.50    2.80    --   40.52-114.00 -84.00   80
 10  \w     52.00  77.00   0.50    2.80    --   40.52-171.00 134.00   50
 11  \w    -23.00  59.00   0.50    2.80    --   40.52 -70.00  -6.00  164
 12  \w     90.00 115.00   0.50   11.20    --   96.04-171.00 134.00   50
 13  \w     33.00  63.00   0.50   11.20    --   96.04 -59.00 150.00   60
 14  \w     28.00  53.00   0.50   11.20    --   96.04 -52.00 145.00   50
 15  \w     -4.00  60.00   0.50    2.80    --   40.52 -52.00 145.00  128
 16  \w    -24.00  41.00   0.50    2.80    --   40.52 -37.00  60.00  130
 17  \w     50.00  87.00   0.50    2.80    --   40.52  70.00 124.00   74
 18  \w    -24.00  28.00   0.50    2.80    --  -40.83  12.00 -60.00  104
 19  \w    -35.00  -2.00   0.50    2.80    --   40.52 -12.00  30.00   66
 20  \w    -20.00  23.00   0.50    2.80    --   40.52 -12.00 150.00   86
 21  \w    -44.00 -19.00   0.50    2.80    --  -40.83  70.00 124.00   50
 22  \w    -56.00 -31.00   0.50    2.80    --  -40.83 114.00   6.00   50
 23  \w    -57.00 -32.00   0.50   11.20    --  -96.35  52.00 -68.00   50
 24  \w    -57.00 -32.00   0.50   11.20    --  -96.35  50.00 -30.00   50
 25  \w    -68.00 -31.00   0.50   11.20    --  -96.35  59.00 -30.00   74
 26  \w    -56.00 -30.00   0.50   11.20    --  -96.35  50.00  60.00   52
 27  \w    -57.00 -31.00   0.50   11.20    --  -96.35  50.00  90.00   52
 28  \w    -56.00 -30.00   0.50   11.20    --  -96.35  50.00 120.00   52
 29  \w    -83.00 -29.00   0.50   11.20    --  -96.35  68.00 150.00  108
 30  \w    -76.00 -51.00   0.50    2.80    --  -40.83 171.00 148.00   50
 31  \w   -110.00 -29.00   0.50   11.20    --  -96.35 117.00 120.00  162
 32  \w    -46.00 -21.00   0.50    2.80    --  -40.83 -52.00 145.00   50
 33  \w    -72.00 -47.00   0.50    2.80    --  -40.83 -70.00  -6.00   50
 34  \w   -103.00 -78.00   0.50   11.20    --  -96.35-117.00-120.00   50
 35  \w   -130.00 -92.00   0.50   11.20    --  -96.35-114.00 -84.00   76
 36  \w   -124.00 -74.00   0.50   11.20    --  -96.35 -70.00  -6.00  100
 37  \w   -102.00 -77.00   0.50    2.80    --  -40.83-171.00 134.00   50
 38  \w   -165.00 -72.00   0.50   11.20    --  -96.35 -17.00   0.00  186
 39  \w   -126.00 -86.00   0.50   11.20    --  -96.35 -42.00-150.00   80
 40  \w   -161.00-135.00   0.50   11.20    --  -96.35 -42.00-150.00   52
 41  \w   -163.00-117.00   0.50   11.20    --  -96.35-117.00-120.00   92
;
_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      0.0626249000
_diffrn_orient_matrix_UB_12      0.0471094000
_diffrn_orient_matrix_UB_13      -0.0273346000
_diffrn_orient_matrix_UB_21      0.0506000000
_diffrn_orient_matrix_UB_22      0.0776194000
_diffrn_orient_matrix_UB_23      0.0220680000
_diffrn_orient_matrix_UB_31      0.0985339000
_diffrn_orient_matrix_UB_32      -0.0698380000
_diffrn_orient_matrix_UB_33      0.0060477000
_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  0.0432
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_number            37300
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.408
_diffrn_reflns_theta_min         4.093
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.711
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.728
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.80a (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            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_description       block
_exptl_crystal_F_000             3104
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.189
_exptl_crystal_size_min          0.041
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.00016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     524
_refine_ls_number_reflns         6425
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.156
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0583
_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^)+(0.0443P)^2^+7.5344P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1379
_refine_ls_wR_factor_ref         0.1410
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5840
_reflns_number_total             6425
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02907c2.cif
_cod_data_source_block           exp_133
_cod_depositor_comments
;

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C52 H30 N2 O4'
_cod_original_formula_weight         746.78
_cod_original_formula_moiety         '2(C26 H15 N O2)'
_cod_original_formula_units_Z            8
_cod_database_code               7130230
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C52(H52), C36(H36), C13(H13), C54(H54), C31(H31), C15(H15),
 C32(H32), C34(H34), C23(H23), C24(H24), C53(H53), C6(H6), C7(H7), C29(H29),
 C41(H41), C16(H16), C35(H35), C5(H5), C27(H27), C3(H3), C25(H25), C56(H56),
 C2(H2), C42(H42), C44(H44), C58(H58), C45(H45), C28(H28), C57(H57)
;
_shelx_res_checksum              54751
_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 1.469
_oxdiff_exptl_absorpt_empirical_full_min 0.752