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_4035408
_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         'C22 H20 N2 O5'
_chemical_formula_sum            'C22 H20 N2 O5'
_chemical_formula_weight         392.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_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                 94.769(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.6608(6)
_cell_length_b                   10.8233(5)
_cell_length_c                   27.9283(11)
_cell_measurement_reflns_used    7125
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.8380
_cell_measurement_theta_min      3.0740
_cell_volume                     3813.8(3)
_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 0.997
_diffrn_measured_fraction_theta_max 0.988
_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    -40.00   1.00   0.50    1.85    --  -41.22 105.00-160.00   82
  2  \w     -8.00  42.00   0.50    1.85    --   41.22-105.00  98.00  100
  3  \w     86.00 133.00   0.50    4.00    --  101.00 105.00-160.00   94
  4  \w     43.00  69.00   0.50    4.00    --  101.00-105.00  98.00   52
  5  \w   -106.00 -32.00   0.50    1.85    --  -41.22 -32.00 120.00  148
  6  \w   -107.00 -32.00   0.50    1.85    --  -41.22 -32.00  60.00  150
  7  \w     29.00  72.00   0.50    1.85    --   41.22  43.00-120.00   86
  8  \w    -32.00  24.00   0.50    1.85    --   41.22 -11.00-150.00  112
  9  \w     77.00 102.00   0.50    1.85    --   41.22  43.00-120.00   50
 10  \w    -17.00  19.00   0.50    1.85    --   41.22 -54.00 -90.00   72
 11  \w     57.00  94.00   0.50    1.85    --   41.22-138.00 120.00   74
 12  \w     23.00  50.00   0.50    1.85    --   41.22 -54.00 -90.00   54
 13  \w     30.00  65.00   0.50    1.85    --   41.22 -11.00-150.00   70
 14  \w     72.00  97.00   0.50    1.85    --   41.22-138.00-180.00   50
 15  \w     14.00  62.00   0.50    1.85    --   41.22 -65.00 150.00   96
 16  \w     19.00  54.00   0.50    1.85    --   41.22-138.00-180.00   70
 17  \w     83.00 156.00   0.50    4.00    --  101.00  77.00 -60.00  146
 18  \w     57.00 120.00   0.50    4.00    --  101.00 -77.00 120.00  126
 19  \w     58.00 106.00   0.50    4.00    --  101.00 -42.00 120.00   96
 20  \w     35.00 114.00   0.50    4.00    --  101.00-111.00  90.00  158
 21  \w     92.00 157.00   0.50    4.00    --  101.00  25.00-150.00  130
 22  \w    125.00 157.00   0.50    4.00    --  101.00  25.00 150.00   64
 23  \w     45.00 116.00   0.50    4.00    --  101.00 -50.00 120.00  142
 24  \w    129.00 154.00   0.50    4.00    --  101.00  42.00-120.00   50
 25  \w     73.00 155.00   0.50    4.00    --  101.00 133.00-120.00  164
 26  \w     76.00 102.00   0.50    4.00    --  101.00-111.00 150.00   52
 27  \w    129.00 155.00   0.50    4.00    --  101.00  93.00-120.00   52
 28  \w    101.00 153.00   0.50    4.00    --  101.00 111.00 -90.00  104
 29  \w     93.00 123.00   0.50    4.00    --  101.00  25.00-120.00   60
 30  \w     89.00 114.00   0.50    4.00    --  101.00-111.00-180.00   50
 31  \w     81.00 142.00   0.50    4.00    --  101.00 111.00  60.00  122
 32  \w    -70.00 -40.00   0.50    1.85    --  -41.22 105.00-160.00   60
 33  \w   -107.00 -53.00   0.50    1.85    --  -41.22 -32.00   0.00  108
;
_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      0.0425194000
_diffrn_orient_matrix_UB_12      -0.1176364000
_diffrn_orient_matrix_UB_13      -0.0227958000
_diffrn_orient_matrix_UB_21      0.0999173000
_diffrn_orient_matrix_UB_22      0.0709577000
_diffrn_orient_matrix_UB_23      -0.0119999000
_diffrn_orient_matrix_UB_31      0.0558575000
_diffrn_orient_matrix_UB_32      -0.0372702000
_diffrn_orient_matrix_UB_33      0.0489890000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            10468
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.052
_diffrn_reflns_theta_min         3.176
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.809
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62556
_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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_description       prism
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3719
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0355
_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^)+(0.0440P)^2^+3.0931P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0928
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3323
_reflns_number_total             3719
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02164_si_004.cif
_cod_data_source_block           cme920
_cod_database_code               4035408
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C22 H20 N2 O5'
_shelx_estimated_absorpt_t_max   0.909
_shelx_estimated_absorpt_t_min   0.836
_reflns_odcompleteness_completeness 99.29
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.55
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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 Aromatic/amide H refined with riding coordinates:
 C20(H20), C4(H4), C19(H19), C3(H3), C2(H2), C9(H9), C16(H16), C17(H17),
 C13(H13), C10(H10), C12(H12)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C21(H21A,H21B,H21C)
2.d Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_shelx_res_checksum              23232
_shelx_hkl_checksum              41187
_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 2.218
_oxdiff_exptl_absorpt_empirical_full_min 0.671