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_7130229
_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         'C22 H13 N O2'
_chemical_formula_sum            'C22 H13 N O2'
_chemical_formula_weight         323.33
_chemical_name_common            1-(4-nitrophenyl)pyrene
_chemical_name_systematic        1-(4-nitrophenyl)pyrene
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-02-16
_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                 97.696(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6037(4)
_cell_length_b                   11.9960(5)
_cell_length_c                   13.4769(5)
_cell_measurement_reflns_used    3726
_cell_measurement_temperature    103.15
_cell_measurement_theta_max      68.2740
_cell_measurement_theta_min      3.3220
_cell_volume                     1538.63(11)
_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 2018/2 (Sheldrick, 2018)'
_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 0.995
_diffrn_measured_fraction_theta_max 0.989
_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    -16.00  28.00   0.50    1.66    --  -41.44  21.00 -90.00   88
  2  \w    -17.00  20.00   0.50    1.66    --  -41.44  87.00-178.00   74
  3  \w    -24.00   3.00   0.50    1.66    --  -41.44  11.00-180.00   54
  4  \w      6.00  32.00   0.50    1.66    --  -41.44  11.00-180.00   52
  5  \w    -21.00   5.00   0.50    1.66    --   41.75 -21.00 -60.00   52
  6  \w    -26.00  18.00   0.50    1.66    --   41.75 -11.00 -90.00   88
  7  \w    -26.00  23.00   0.50    1.66    --   41.75 -11.00-180.00   98
  8  \w     29.00  54.00   0.50    6.66    --   95.75 -50.00 -90.00   50
  9  \w     46.00  79.00   0.50    6.66    --   95.75 -68.00 -60.00   66
 10  \w     29.00  55.00   0.50    6.66    --   95.75 -50.00 -30.00   52
 11  \w     40.00  83.00   0.50    6.66    --   95.75 -87.00  64.00   86
 12  \w     31.00  56.00   0.50    6.66    --   95.75 -50.00  60.00   50
 13  \w     28.00  53.00   0.50    6.66    --   95.75 -59.00  60.00   50
 14  \w     19.00  72.00   0.50    1.66    --   41.75 -87.00  64.00  106
 15  \w    -26.00  -1.00   0.50    1.66    --   41.75 -87.00  64.00   50
 16  \w    -33.00  18.00   0.50    1.66    --  -41.44  32.00 120.00  102
 17  \w    -57.00 -32.00   0.50    6.66    --  -95.43  50.00  30.00   50
 18  \w    -57.00 -32.00   0.50    6.66    --  -95.43  50.00   0.00   50
 19  \w   -106.00 -27.00   0.50    6.66    --  -95.43  77.00  30.00  158
 20  \w    -83.00 -29.00   0.50    6.66    --  -95.43  68.00 150.00  108
 21  \w   -144.00-118.00   0.50    6.66    --  -95.43 -87.00  64.00   52
 22  \w   -148.00 -89.00   0.50    6.66    --  -95.43 -86.00  30.00  118
 23  \w   -102.00 -77.00   0.50    1.66    --  -41.44-138.00 -30.00   50
 24  \w   -159.00 -77.00   0.50    6.66    --  -95.43 -68.00-120.00  164
 25  \w    -57.00 -31.00   0.50    6.66    --  -95.43  50.00-180.00   52
 26  \w    -52.00 -27.00   0.50    6.66    --  -95.43  59.00-180.00   50
 27  \w    -68.00 -25.00   0.50    6.66    --  -95.43  87.00-178.00   86
 28  \w    -52.00 -27.00   0.50    1.66    --  -41.44  87.00-178.00   50
 29  \w     81.00 107.00   0.50    1.66    --   41.75 138.00 -60.00   52
 30  \w     64.00  89.00   0.50    1.66    --   41.75 138.00-150.00   50
 31  \w    124.00 155.00   0.50    6.66    --   95.75  87.00-178.00   62
 32  \w     79.00 104.00   0.50    6.66    --   95.75  87.00-178.00   50
 33  \w    -20.00   6.00   0.50    1.66    --   41.75 -11.00-120.00   52
 34  \w     79.00 162.00   0.50    6.66    --   95.75  68.00 120.00  166
 35  \w    -79.00 -48.00   0.50    6.66    --  -95.43  68.00-180.00   62
 36  \w   -107.00 -72.00   0.50    6.66    --  -95.43  87.00-178.00   70
 37  \w   -160.00 -86.00   0.50    6.66    --  -95.43 -33.00 150.00  148
;
_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      -0.1382838000
_diffrn_orient_matrix_UB_12      0.0634805000
_diffrn_orient_matrix_UB_13      -0.0320925000
_diffrn_orient_matrix_UB_21      -0.0831196000
_diffrn_orient_matrix_UB_22      -0.0964342000
_diffrn_orient_matrix_UB_23      0.0395392000
_diffrn_orient_matrix_UB_31      0.0130821000
_diffrn_orient_matrix_UB_32      0.0563285000
_diffrn_orient_matrix_UB_33      0.1034683000
_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  0.0184
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7975
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.171
_diffrn_reflns_theta_min         4.956
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.719
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.722
_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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.216
_exptl_crystal_size_mid          0.099
_exptl_crystal_size_min          0.071
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2792
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0499
_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^)+(0.0882P)^2^+0.3592P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1442
_refine_ls_wR_factor_ref         0.1513
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2356
_reflns_number_total             2792
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02907c2.cif
_cod_data_source_block           exp_98
_cod_database_code               7130229
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C88 H52 N4 O8 '
_reflns_odcompleteness_completeness 99.97
_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:
 C004(H004), C007(H007), C009(H009), C00D(H00D), C00F(H00F), C00G(H00G),
 C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O),
 C00P(H00P)
;
_shelx_res_checksum              62279
_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 1.362
_oxdiff_exptl_absorpt_empirical_full_min 0.697