Fine-tuned organic photoredox catalysts for fragmentation-alkynylation cascades of cyclic oxime ethers.
Le Vaillant, Franck; Garreau, Marion; Nicolai, Stefano; Gryn'ova, Ganna; Corminboeuf, Clemence; Waser, Jerome; Chemical science 9 (2018) 5883–5889; doi:10.1039/c8sc01818a

data_1549490
_publ_section_title
;
 Fine-tuned organic photoredox catalysts for fragmentation-alkynylation
 cascades of cyclic oxime ethers.
;
_journal_issue                   27
_journal_name_full               'Chemical science'
_journal_page_first              5883
_journal_page_last               5889
_journal_paper_doi               10.1039/c8sc01818a
_journal_volume                  9
_journal_year                    2018
_chemical_formula_moiety         'C56 H24 Cl8 N6'
_chemical_formula_sum            'C56 H24 Cl8 N6'
_chemical_formula_weight         1064.41
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2018-04-18 deposited with the CCDC.
2018-05-29 downloaded from the CCDC.
;
_cell_angle_alpha                81.806(3)
_cell_angle_beta                 74.263(3)
_cell_angle_gamma                87.206(3)
_cell_formula_units_Z            2
_cell_length_a                   12.4209(5)
_cell_length_b                   13.6925(5)
_cell_length_c                   15.8890(6)
_cell_measurement_reflns_used    8105
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      75.4470
_cell_measurement_theta_min      2.8800
_cell_volume                     2574.30(18)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Mercury 3.10 (CCDC, 2017)'
_computing_publication_material  'CIFTab (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.964
_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    128.00 155.00   1.00   16.00    --  112.00  77.00 150.00   27
  2  \w     84.00 111.00   1.00   16.00    --  112.00  77.00 150.00   27
  3  \w     87.00 178.00   1.00   16.00    --  112.00  45.00 -30.00   91
  4  \w    140.00 174.00   1.00   16.00    --  112.00  61.00 -90.00   34
  5  \w     91.00 116.00   1.00    4.00    --   40.66  77.00 -90.00   25
  6  \w     84.00 119.00   1.00   16.00    --  112.00  61.00 -90.00   35
  7  \w     70.00 177.00   1.00   16.00    --  112.00  15.00 -90.00  107
  8  \w     82.00 120.00   1.00   16.00    --  112.00-125.00 -60.00   38
  9  \w     64.00 136.00   1.00   16.00    --  112.00 -45.00 -90.00   72
 10  \w     59.00  85.00   1.00    4.00    --   40.66-125.00 -60.00   26
 11  \w     38.00  64.00   1.00   16.00    --  112.00 -94.00-150.00   26
 12  \w     52.00 136.00   1.00   16.00    --  112.00 -61.00-180.00   84
 13  \w     52.00 116.00   1.00   16.00    --  112.00 -45.00   0.00   64
 14  \w     91.00 118.00   1.00   16.00    --  112.00-125.00 120.00   27
 15  \w     55.00 106.00   1.00   16.00    --  112.00 -94.00  60.00   51
 16  \w     42.00 109.00   1.00   16.00    --  112.00 -94.00 150.00   67
 17  \w     39.00  66.00   1.00   16.00    --  112.00-125.00 120.00   27
 18  \w      9.00  79.00   1.00    4.00    --   40.66 -99.00 120.00   70
 19  \w     32.00 108.00   1.00   16.00    --  112.00 -94.00 -30.00   76
 20  \w    -69.00  32.00   1.00    4.00    --  -40.66  57.00  60.00  101
 21  \w    -65.00  29.00   1.00    4.00    --  -40.66  38.00 -30.00   94
 22  \w   -108.00 -16.00   1.00    4.00    --  -40.66 -38.00 150.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_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  0.0259
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18608
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.194
_diffrn_reflns_theta_min         2.916
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.351
_exptl_absorpt_correction_T_max  0.908
_exptl_absorpt_correction_T_min  0.347
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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 intense yellow'
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1076
_exptl_crystal_size_max          0.284
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.154
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.657
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     631
_refine_ls_number_reflns         10389
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0442
_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^)+(0.0617P)^2^+1.3324P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1203
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8906
_reflns_number_total             10389
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc01818a2.cif
_cod_data_source_block           flv-8-189b
_cod_depositor_comments          'Adding full bibliography for 1549490.cif.'
_cod_original_cell_volume        2574.29(17)
_cod_database_code               1549490
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.371
_shelx_estimated_absorpt_t_max   0.554
_shelx_res_checksum              74271
_shelx_fab_checksum              49628