A hydrazine-free photoredox catalytic synthesis of azines by reductive activation of readily available oxime esters
Schütte, Jonathan; Corsi, Daria; Haumer, Wolfgang; Schmid, Simon; Žurauskas, Jonas; Barham, Joshua P.; Green Chemistry 26 (2024) 6446–6453; doi:10.1039/D4GC00804A

data_7248394
_publ_section_title
;
 A hydrazine-free photoredox catalytic synthesis of azines by reductive
 activation of readily available oxime esters
;
_journal_issue                   11
_journal_name_full               'Green Chemistry'
_journal_page_first              6446
_journal_page_last               6453
_journal_paper_doi               10.1039/D4GC00804A
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C16 H16 N2'
_chemical_formula_sum            'C16 H16 N2'
_chemical_formula_weight         236.31
_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   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-10
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2022.06.10 svn.r3fa896fb for OlexSys, GUI svn.r6535)
;
_audit_update_record
;
2023-08-13 deposited with the CCDC.	2024-04-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.5220(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.58810(10)
_cell_length_b                   7.38790(10)
_cell_length_c                   14.8464(2)
_cell_measurement_reflns_used    11814
_cell_measurement_temperature    126.06(10)
_cell_measurement_theta_max      73.9120
_cell_measurement_theta_min      3.8610
_cell_volume                     1260.09(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      126.06(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.968
_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     71.00 103.00   0.50    0.10    --   76.31-125.00  60.00   64
  2  \w     35.00  99.00   0.50    0.10    --   71.85-125.00  90.00  128
  3  \w     35.00  61.00   0.50    0.10    --   76.31-125.00  60.00   52
  4  \w     35.00  61.00   0.50    0.10    --   76.31-125.00 120.00   52
  5  \w     78.00 103.00   0.50    0.10    --   76.31-125.00 120.00   50
  6  \w     37.00  63.00   0.50    0.10    --   76.31-125.00  30.00   52
  7  \w     70.00 102.00   0.50    0.10    --   76.31-125.00  30.00   64
  8  \w     78.00 103.00   0.50    0.10    --   76.31-125.00 -30.00   50
  9  \w     45.00  71.00   0.50    0.10    --   76.31-125.00 -30.00   52
 10  \w     32.00  87.00   0.50    0.10    --   71.85-105.00 -55.00  110
 11  \w     66.00  91.00   0.50    0.10    --   76.31-105.00 -55.00   50
 12  \w     29.00  68.00   0.50    0.10    --   64.17 -95.00   0.00   78
 13  \w     27.00  56.00   0.50    0.10    --   64.17 -95.00  30.00   58
 14  \w     26.00  58.00   0.50    0.10    --   64.17 -95.00 -30.00   64
 15  \w     24.00  74.00   0.50    0.10    --   64.17-105.00 -55.00  100
 16  \w     39.00  74.00   0.50    0.10    --   76.31 -95.00 120.00   70
 17  \w     36.00  61.00   0.50    0.10    --   71.85 -95.00 -60.00   50
 18  \w     56.00  83.00   0.50    0.10    --   76.31 -95.00-120.00   54
 19  \w     27.00  53.00   0.50    0.10    --   64.17 -95.00-180.00   52
 20  \w     33.00 101.00   0.50    0.10    --   64.17   0.00 -60.00  136
 21  \w     72.00  97.00   0.50    0.10    --   60.00  71.00  21.55   50
 22  \w     66.00  91.00   0.50    0.10    --   60.00  73.00  10.13   50
 23  \w     59.00  84.00   0.50    0.10    --   52.00  70.00  15.04   50
 24  \w     53.00  78.00   0.50    0.10    --   44.00  63.00  23.05   50
 25  \w     41.00  66.00   0.50    0.10    --   32.00  62.00  40.19   50
 26  \w     67.00  92.00   0.50    0.10    --   60.00  71.00  -7.34   50
 27  \w     38.00 109.00   0.50    0.10    --   71.85   0.00-120.00  142
 28  \w     27.00  53.00   0.50    0.10    --   64.17   0.00-120.00   52
 29  \w     69.00  95.00   0.50    0.10    --   64.17   0.00-120.00   52
 30  \w     72.00 112.00   0.50    0.10    --   76.31  15.00 -90.00   80
 31  \w     41.00  66.00   0.50    0.10    --   76.31   0.00  90.00   50
 32  \w     74.00  99.00   0.50    0.10    --   76.31   0.00  90.00   50
 33  \w    -63.00 -37.00   0.50    0.10    --  -76.25 140.00  27.65   52
 34  \w    -62.00 -35.00   0.50    0.10    --  -65.07 105.00  44.00   54
 35  \w    -86.00 -60.00   0.50    0.10    --  -71.26 105.00  44.00   52
 36  \w   -113.00 -88.00   0.50    0.10    --  -76.25 140.00  27.65   50
 37  \w    -82.00 -38.00   0.50    0.10    --  -71.26   0.00-120.00   88
 38  \w    -93.00 -34.00   0.50    0.10    --  -65.07   0.00-150.00  118
 39  \w   -102.00 -28.00   0.50    0.10    --  -65.07   0.00 -30.00  148
 40  \w    -98.00 -47.00   0.50    0.10    --  -65.07   0.00  90.00  102
 41  \w   -102.00 -72.00   0.50    0.10    --  -68.00 -76.00 -23.81   60
 42  \w   -102.00 -77.00   0.50    0.10    --  -72.00 -75.00   5.72   50
 43  \w   -105.00 -80.00   0.50    0.10    --  -72.00 -66.00   3.78   50
 44  \w   -105.00 -80.00   0.50    0.10    --  -72.00 -66.00 -20.23   50
 45  \w   -118.00 -93.00   0.50    0.10    --  -76.25 -61.00 -10.60   50
 46  \w   -109.00 -42.00   0.50    0.10    --  -71.26 -15.00-150.00  134
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0174900000
_diffrn_orient_matrix_UB_12      -0.2002943000
_diffrn_orient_matrix_UB_13      -0.0236838000
_diffrn_orient_matrix_UB_21      -0.0929485000
_diffrn_orient_matrix_UB_22      0.0184565000
_diffrn_orient_matrix_UB_23      -0.0837391000
_diffrn_orient_matrix_UB_31      0.0950612000
_diffrn_orient_matrix_UB_32      0.0549512000
_diffrn_orient_matrix_UB_33      -0.0581701000
_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  0.0159
_diffrn_reflns_av_unetI/netI     0.0087
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16836
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.812
_diffrn_reflns_theta_min         4.562
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.570
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.462
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_description       prism
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.263
_exptl_crystal_size_mid          0.197
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2468
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0324
_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^)+(0.0538P)^2^+0.2444P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.0938
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2351
_reflns_number_total             2468
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4gc00804a2.cif
_cod_data_source_block           w037
_cod_depositor_comments          'Adding full bibliography for 7248394.cif.'
_cod_database_code               7248394
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C16 H16 N2'
_chemical_oxdiff_usercomment     Corsi_Barham_JS-Model_product
_shelx_estimated_absorpt_t_max   0.959
_shelx_estimated_absorpt_t_min   0.865
_olex2_refinement_description
;
;
_shelx_res_checksum              2083
_olex2_date_sample_data_collection 2023-05-08
_olex2_date_sample_submission    2023-04-28
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 700'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder inert oil'
_olex2_submission_original_sample_id JS-Model-product
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.368
_oxdiff_exptl_absorpt_empirical_full_min 0.831