Visible-light-induced α-oxyamination of 1,3-dicarbonyls with TEMPO via a photo(electro)catalytic process applying a DSSC anode or in a DSSC system
Gong, Ming; Kim, Jung Keun; Zhao, Xiuli; Li, Yabo; Zhang, Jianye; Huang, Mengmeng; Wu, Yangjie; Green Chemistry 21 (2019) 3615–; doi:10.1039/C9GC01154D

data_7232836
_publ_section_title
;
 Visible-light-induced \a-oxyamination of 1,3-dicarbonyls with TEMPO via a
 photo(electro)catalytic process applying a DSSC anode or in a DSSC system
;
_journal_issue                   13
_journal_name_full               'Green Chemistry'
_journal_page_first              3615
_journal_paper_doi               10.1039/C9GC01154D
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C24 H29 N O3'
_chemical_formula_sum            'C24 H29 N O3'
_chemical_formula_weight         379.48
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-01-23
_audit_creation_method
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Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
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_audit_update_record
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2019-01-24 deposited with the CCDC.    2019-05-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.353(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3821(5)
_cell_length_b                   8.3089(4)
_cell_length_c                   21.5533(8)
_cell_measurement_reflns_used    1947
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.4010
_cell_measurement_theta_min      3.6950
_cell_volume                     2138.30(16)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega -108.00  -32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  -60.0000 76

  2 omega   -4.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000    0.0000 76

  3 omega   57.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   90.0000 25

  4 omega   58.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000 -120.0000 46

  5 omega    0.00   48.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000 -120.0000 48

  6 omega   20.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  120.0000 86

  7 omega    5.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000 -120.0000 71

  8 omega   57.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -150.0000 26

  9 omega  115.00  147.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   90.0000 32

 10 omega   37.00  152.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000  -90.0000 115

 11 omega   42.00   86.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 44

 12 omega   92.00  171.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  120.0000 79

 13 omega   39.00   99.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 60

 14 omega   52.00   77.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 25

 15 omega   42.00   99.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 57

 16 omega   59.00   91.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 32

 17 omega   37.00   62.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0872047000
_diffrn_orient_matrix_UB_12      -0.1166141000
_diffrn_orient_matrix_UB_13      0.0406127000
_diffrn_orient_matrix_UB_21      0.0270748000
_diffrn_orient_matrix_UB_22      -0.0619205000
_diffrn_orient_matrix_UB_23      -0.0616223000
_diffrn_orient_matrix_UB_31      0.0911266000
_diffrn_orient_matrix_UB_32      0.1300725000
_diffrn_orient_matrix_UB_33      0.0071857000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7740
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.072
_diffrn_reflns_theta_max         67.072
_diffrn_reflns_theta_min         3.702
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.610
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92351
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_description       prism
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0052(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3806
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0479
_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^)+(0.0604P)^2^+0.2134P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.1402
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2772
_reflns_number_total             3806
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9gc01154d2.cif
_cod_data_source_block           20190124
_cod_depositor_comments          'Adding full bibliography for 7232836.cif.'
_cod_original_cell_volume        2138.31(16)
_cod_database_code               7232836
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C28H31ON6
_shelx_estimated_absorpt_t_max   0.942
_shelx_estimated_absorpt_t_min   0.898
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C)
;
_olex2_submission_special_instructions 'No special instructions were received'