New Reagent Space and New Scope for the Castagnoli-Cushman Reaction of Oximes and 3-Arylglutaconic anhydrides
Bannykh, Anton; Levashova, Ekaterina; Bakulina, Olga; Krasavin, Mikhail; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01675C

data_7158928
_publ_section_title
;
 New Reagent Space and New Scope for the Castagnoli-Cushman Reaction of
 Oximes and 3-Arylglutaconic anhydrides
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01675C
_journal_year                    2022
_chemical_formula_moiety         'C16 H19 N O4'
_chemical_formula_sum            'C16 H19 N O4'
_chemical_formula_weight         289.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-01-14
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-01-14 deposited with the CCDC.	2022-10-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.914(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.8108(2)
_cell_length_b                   6.5963(2)
_cell_length_c                   13.6805(4)
_cell_measurement_reflns_used    7777
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.9500
_cell_measurement_theta_min      3.2460
_cell_volume                     699.73(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (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      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_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    -26.00  25.00   0.50    0.15    --   47.20 -19.00 -60.00  102
  2  \w     13.00  76.00   0.50    0.15    --   47.20-100.00-151.00  126
  3  \w     58.00 100.00   0.50    0.60    --  107.75-100.00-151.00   84
  4  \w     81.00 106.00   0.50    0.60    --  107.75 -77.00-180.00   50
  5  \w     71.00  99.00   0.50    0.60    --  107.75 -94.00-120.00   56
  6  \w     61.00 104.00   0.50    0.60    --  107.75 -77.00-120.00   86
  7  \w     35.00  73.00   0.50    0.60    --  107.75 -77.00-150.00   76
  8  \w     37.00  71.00   0.50    0.60    --  107.75 -61.00 -90.00   68
  9  \w     40.00  70.00   0.50    0.60    --  107.75 -61.00 -60.00   60
 10  \w     36.00  70.00   0.50    0.60    --  107.75 -61.00   0.00   68
 11  \w     55.00 103.00   0.50    0.60    --  107.75 -77.00  60.00   96
 12  \w     38.00  71.00   0.50    0.60    --  107.75 -61.00  30.00   66
 13  \w    106.00 178.00   0.50    0.60    --  107.75  45.00  90.00  144
 14  \w    147.00 175.00   0.50    0.60    --  107.75  45.00  30.00   56
 15  \w    113.00 139.00   0.50    0.60    --  107.75 100.00 -46.00   52
 16  \w     95.00 143.00   0.50    0.60    --  107.75  45.00  30.00   96
 17  \w     74.00  99.00   0.50    0.15    --   47.20 125.00 -90.00   50
 18  \w     79.00 119.00   0.50    0.15    --   47.20 125.00-120.00   80
 19  \w    104.00 178.00   0.50    0.60    --  107.75  15.00-180.00  148
 20  \w     35.00  61.00   0.50    0.60    --  107.75 -77.00-180.00   52
 21  \w    -71.00 -23.00   0.50    0.15    --  -47.20 100.00 -46.00   96
 22  \w    -12.00  22.00   0.50    0.15    --  -47.20 100.00 -46.00   68
 23  \w    -63.00 -38.00   0.50    0.60    -- -106.00  61.00 -60.00   50
 24  \w    -61.00 -33.00   0.50    0.60    -- -106.00  61.00 -90.00   56
 25  \w    -98.00 -65.00   0.50    0.60    -- -106.00 100.00 -46.00   66
 26  \w    -59.00 -34.00   0.50    0.60    -- -106.00  61.00  90.00   50
 27  \w    -62.00 -37.00   0.50    0.60    -- -106.00  61.00 150.00   50
 28  \w   -165.00-104.00   0.50    0.60    -- -106.00-100.00-151.00  122
 29  \w    101.00 127.00   0.50    0.60    --  107.75 100.00 -46.00   52
 30  \w     88.00 113.00   0.50    0.15    --   47.20 125.00 -90.00   50
 31  \w    -10.00  26.00   0.50    0.15    --   47.20 -19.00-120.00   72
 32  \w    -22.00   4.00   0.50    0.15    --   47.20 -19.00  30.00   52
 33  \w     46.00  95.00   0.50    0.15    --   47.20  57.00  60.00   98
 34  \w   -119.00 -88.00   0.50    0.60    -- -106.00 -68.00 -93.15   62
 35  \w   -121.00 -96.00   0.50    0.60    -- -106.00 138.00-138.62   50
 36  \w   -108.00 -82.00   0.50    0.60    -- -106.00 109.00-174.39   52
 37  \w   -112.00 -87.00   0.50    0.60    -- -106.00 125.00 -60.00   50
 38  \w   -114.00 -88.00   0.50    0.60    -- -106.00-125.00  30.00   52
 39  \w   -159.00-127.00   0.50    0.60    -- -106.00 -83.00 -98.08   64
 40  \w   -158.00-132.00   0.50    0.60    -- -106.00 -68.00 -93.15   52
 41  \w   -121.00 -95.00   0.50    0.60    -- -106.00 -30.00  90.00   52
 42  \w   -117.00 -83.00   0.50    0.60    -- -106.00 -77.00 -60.00   68
 43  \w   -173.00-128.00   0.50    0.60    -- -106.00 -77.00 -60.00   90
 44  \w   -105.00 -80.00   0.50    0.60    -- -106.00 -83.00 -98.08   50
 45  \w   -105.00 -80.00   0.50    0.60    -- -106.00 125.00 -30.00   50
 46  \w   -170.00-144.00   0.50    0.60    -- -106.00 -30.00  90.00   52
 47  \w   -112.00 -75.00   0.50    0.60    -- -106.00 125.00  90.00   74
 48  \w    -67.00 -35.00   0.50    0.60    -- -106.00 125.00 -30.00   64
 49  \w   -171.00-146.00   0.50    0.60    -- -106.00-125.00  30.00   50
 50  \w     74.00  99.00   0.50    0.60    --  107.75 -94.00 -30.00   50
 51  \w     67.00 104.00   0.50    0.60    --  107.75-125.00-150.00   74
 52  \w     36.00  62.00   0.50    0.60    --  107.75-125.00-150.00   52
 53  \w    128.00 174.00   0.50    0.60    --  107.75  45.00  60.00   92
 54  \w     91.00 124.00   0.50    0.60    --  107.75  61.00 -90.00   66
 55  \w     39.00  69.00   0.50    0.60    --  107.75 -61.00-120.00   60
 56  \w     87.00 112.00   0.50    0.60    --  107.75-125.00-120.00   50
 57  \w    144.00 172.00   0.50    0.60    --  107.75  61.00   0.00   56
 58  \w     42.00  67.00   0.50    0.60    --  107.75-125.00-120.00   50
 59  \w     64.00  90.00   0.50    0.60    --  107.75-125.00  30.00   52
 60  \w    100.00 126.00   0.50    0.60    --  107.75  61.00   0.00   52
 61  \w     85.00 125.00   0.50    0.60    --  107.75  77.00 -90.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1290677000
_diffrn_orient_matrix_UB_12      0.0335436000
_diffrn_orient_matrix_UB_13      -0.0929568000
_diffrn_orient_matrix_UB_21      -0.0297498000
_diffrn_orient_matrix_UB_22      0.2191448000
_diffrn_orient_matrix_UB_23      0.0329136000
_diffrn_orient_matrix_UB_31      0.1480684000
_diffrn_orient_matrix_UB_32      0.0734947000
_diffrn_orient_matrix_UB_33      -0.0560717000
_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  0.0386
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9975
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.217
_diffrn_reflns_theta_min         3.254
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.812
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.71a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       prism
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 1254 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2903
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0322
_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^)+(0.0481P)^2^+0.0851P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0840
_reflns_Friedel_coverage         0.816
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                2840
_reflns_number_total             2903
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01675c2.cif
_cod_data_source_block           16854_abb899
_cod_database_code               7158928
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C16 H19 O4 N1'
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00B(H00A,H00B), C00E(H00E,H00F), C00F(H00G,H00H), C00G(H00I,H00J), C00J(H00L,
 H00M)
2.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C00C(H00C), C00D(H00D), C00H(H00K), C00K(H00N)
2.c Idealised Me refined as rotating group:
 C00L(H00O,H00P,H00Q)
2.d Idealised tetrahedral OH refined as rotating group:
 O003(H003)
;
_shelx_res_checksum              3462
_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 1.592
_oxdiff_exptl_absorpt_empirical_full_min 0.717