Unusually Reactive Cyclic Anhydride Expands the Scope of the Castagnoli-Cushman Reaction.
Chizhova, Maria; Khoroshilova, Olesya; Dar'in, Dmitry; Krasavin, Mikhail; The Journal of organic chemistry 83 (2018) 12722–12733; doi:10.1021/acs.joc.8b02164

data_4035410
_publ_section_title
;
 Unusually Reactive Cyclic Anhydride Expands the Scope of the
 Castagnoli-Cushman Reaction.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12722
_journal_page_last               12733
_journal_paper_doi               10.1021/acs.joc.8b02164
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C20 H24 N2 O5'
_chemical_formula_sum            'C20 H24 N2 O5'
_chemical_formula_weight         372.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.6882(3)
_cell_length_b                   10.5838(3)
_cell_length_c                   30.9945(11)
_cell_measurement_reflns_used    9433
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.8810
_cell_measurement_theta_min      2.9010
_cell_volume                     3834.2(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.990
_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    -68.00 -43.00   0.50    0.25    --  -41.35 122.00 154.00   50
  2  \w    -92.00 -65.00   0.50    0.25    --  -41.35-151.00 -88.00   54
  3  \w    -54.00 -12.00   0.50    0.25    --  -41.35  18.00 -47.00   84
  4  \w    -94.00 -69.00   0.50    0.25    --  -41.35 -18.00 144.00   50
  5  \w     56.00  82.00   0.50    0.25    --   41.35  18.00 -47.00   52
  6  \w    -16.00  10.00   0.50    0.25    --   41.35 -18.00 144.00   52
  7  \w      3.00  28.00   0.50    0.25    --   41.35-109.00 -25.00   50
  8  \w      1.00  69.00   0.50    0.25    --   41.35-122.00  72.00  136
  9  \w     55.00  80.00   0.50    0.25    --   41.35-109.00 -25.00   50
 10  \w     18.00  44.00   0.50    0.25    --   41.35 -18.00 144.00   52
 11  \w     36.00 113.00   0.50    1.02    --  101.00-109.00 -25.00  154
 12  \w    115.00 141.00   0.50    1.02    --  101.00  18.00 -47.00   52
 13  \w     74.00  99.00   0.50    1.02    --  101.00-122.00  72.00   50
 14  \w     47.00  73.00   0.50    1.02    --  101.00 -18.00 144.00   52
 15  \w     95.00 121.00   0.50    1.02    --  101.00 122.00 154.00   52
 16  \w     98.00 123.00   0.50    1.02    --  101.00 109.00  69.00   50
 17  \w    126.00 153.00   0.50    1.02    --  101.00 122.00 154.00   54
 18  \w    -45.00 -20.00   0.50    0.25    --  -41.35 109.00  69.00   50
 19  \w   -103.00 -63.00   0.50    0.25    --  -41.35 -43.00-120.00   80
 20  \w   -105.00 -37.00   0.50    0.25    --  -41.35 -32.00 -60.00  136
 21  \w   -103.00 -78.00   0.50    0.25    --  -41.35 151.00 -44.00   50
 22  \w    -53.00 -28.00   0.50    0.25    --  -41.35 -43.00-120.00   50
 23  \w     62.00  99.00   0.50    0.25    --   41.35  32.00-150.00   74
 24  \w     33.00  64.00   0.50    0.25    --   41.35-138.00  60.00   62
 25  \w     92.00 156.00   0.50    1.02    --  101.00  33.00 -90.00  128
 26  \w     40.00 112.00   0.50    1.02    --  101.00 -42.00   0.00  144
 27  \w     67.00 114.00   0.50    1.02    --  101.00-111.00 150.00   94
 28  \w     89.00 124.00   0.50    1.02    --  101.00  42.00 150.00   70
 29  \w     89.00 154.00   0.50    1.02    --  101.00  42.00   0.00  130
 30  \w     34.00 105.00   0.50    1.02    --  101.00 -25.00 -30.00  142
 31  \w     83.00 108.00   0.50    1.02    --  101.00 151.00 -44.00   50
 32  \w     66.00  92.00   0.50    1.02    --  101.00 -25.00 150.00   52
 33  \w    -48.00 -12.00   0.50    0.25    --  -41.35  43.00  30.00   72
 34  \w     31.00  65.00   0.50    0.25    --   41.35  43.00 120.00   68
 35  \w     91.00 110.50   0.50    1.02    --  101.00 -68.00 -30.00   39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0518521000
_diffrn_orient_matrix_UB_12      -0.0238560000
_diffrn_orient_matrix_UB_13      0.0449692000
_diffrn_orient_matrix_UB_21      -0.1204067000
_diffrn_orient_matrix_UB_22      -0.0258872000
_diffrn_orient_matrix_UB_23      0.0181386000
_diffrn_orient_matrix_UB_31      0.0133207000
_diffrn_orient_matrix_UB_32      -0.1412913000
_diffrn_orient_matrix_UB_33      -0.0109389000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            16960
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.970
_diffrn_reflns_theta_min         2.851
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.768
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79154
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35a (Rigaku Oxford Diffraction, 2017)
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    1.290
_exptl_crystal_description       plate
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3733
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0433
_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^)+(0.0469P)^2^+2.3986P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1099
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3288
_reflns_number_total             3733
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02164_si_003.cif
_cod_data_source_block           cme181
_cod_database_code               4035410
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C20 H24 N2 O5'
_shelx_estimated_absorpt_t_max   0.927
_shelx_estimated_absorpt_t_min   0.825
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.55
_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 Ternary CH refined with riding coordinates:
 C6(H6), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C14(H14), C2(H2), C13(H13), C4(H4), C3(H3)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C11(H11A,H11B,H11C)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_shelx_res_checksum              64079
_shelx_hkl_checksum              43234
_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 1.332
_oxdiff_exptl_absorpt_empirical_full_min 0.701