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_4035411
_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 H15 Cl N2 O3'
_chemical_formula_sum            'C20 H15 Cl N2 O3'
_chemical_formula_weight         366.79
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/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                 105.9237(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.6801(3)
_cell_length_b                   8.66090(13)
_cell_length_c                   10.87942(17)
_cell_measurement_reflns_used    10770
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.5860
_cell_measurement_theta_min      2.4650
_cell_volume                     1692.60(5)
_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 0.993
_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     -3.00  24.00   0.50    0.30    --  -41.22  79.00  12.00   54
  2  \w    -33.00  -6.00   0.50    0.30    --  -41.22  79.00  12.00   54
  3  \w     31.00  71.00   0.50    0.30    --   41.22 -93.00 150.00   80
  4  \w     27.00  57.00   0.50    0.30    --   41.22 -53.00  14.00   60
  5  \w    -22.00   7.00   0.50    0.30    --   41.22 -93.00 150.00   58
  6  \w      9.00  36.00   0.50    0.30    --   41.22 -79.00-111.00   54
  7  \w    -23.00   6.00   0.50    0.30    --   41.22 -79.00-111.00   58
  8  \w    119.00 156.00   0.50    1.22    --  100.29  53.00 159.00   74
  9  \w     85.00 156.00   0.50    1.22    --  100.29  79.00  12.00  142
 10  \w     61.00  99.00   0.50    1.22    --  100.29 -79.00-111.00   76
 11  \w     41.00 128.00   0.50    1.22    --  100.29 -93.00 150.00  174
 12  \w     78.00 118.00   0.50    1.22    --  100.29 -53.00  14.00   80
 13  \w     38.00  64.00   0.50    1.22    --  100.29 -53.00  14.00   52
 14  \w    -52.00 -27.00   0.50    0.30    --  -41.22 -53.00  14.00   50
 15  \w     -8.00  21.00   0.50    0.30    --  -41.22  93.00 -97.00   58
 16  \w    -52.00 -25.00   0.50    0.30    --  -41.22  53.00 159.00   54
 17  \w     44.00  87.00   0.50    0.30    --   41.22  43.00 120.00   86
 18  \w     47.00 105.00   0.50    0.30    --   41.22  32.00-150.00  116
 19  \w     40.00  65.00   0.50    0.30    --   41.22  53.00 159.00   50
 20  \w     93.00 147.00   0.50    1.22    --  100.29  25.00 150.00  108
 21  \w    121.00 148.00   0.50    1.22    --  100.29  96.00  30.00   54
 22  \w     41.00 107.00   0.50    1.22    --  100.29 -42.00-120.00  132
 23  \w     89.00 114.00   0.50    1.22    --  100.29  96.00  30.00   50
 24  \w    104.00 157.00   0.50    1.22    --  100.29  25.00  90.00  106
 25  \w     88.00 113.00   0.50    1.22    --  100.29  42.00 -60.00   50
 26  \w    124.00 150.00   0.50    1.22    --  100.29 117.00-150.00   52
 27  \w     -7.00  20.00   0.50    0.30    --   41.22 -11.00 150.00   54
 28  \w     40.00  65.00   0.50    0.30    --   41.22 -11.00 150.00   50
 29  \w    132.00 157.00   0.50    1.22    --  100.29  68.00  90.00   50
 30  \w     89.00 124.00   0.50    1.22    --  100.29  50.00-150.00   70
 31  \w     82.00 110.00   0.50    1.22    --  100.29  68.00  60.00   56
 32  \w    131.00 157.00   0.50    1.22    --  100.29  68.00  60.00   52
 33  \w     54.00 109.00   0.50    1.22    --  100.29 -96.00-120.00  110
 34  \w     37.00  89.00   0.50    1.22    --  100.29 -25.00 -90.00  104
 35  \w    127.00 154.00   0.50    1.22    --  100.29  50.00-150.00   54
 36  \w    100.00 127.00   0.50    1.22    --  100.29  50.00 120.00   54
 37  \w    132.00 157.00   0.50    1.22    --  100.29  50.00 120.00   50
 38  \w    107.00 134.00   0.50    1.22    --  100.29  25.00 -90.00   54
 39  \w     80.00 114.00   0.50    1.22    --  100.29  68.00  90.00   68
 40  \w     36.00  62.00   0.50    1.22    --  100.29 -79.00-111.00   52
 41  \w    -66.00  -7.00   0.50    0.30    --  -41.22  77.00   0.00  118
 42  \w    -19.00  10.00   0.50    0.30    --   41.22 -54.00 -90.00   58
 43  \w     17.00  46.00   0.50    0.30    --   41.22 -54.00 -90.00   58
 44  \w     55.00 107.00   0.50    0.30    --   41.22  32.00  60.00  104
 45  \w     52.00  79.00   0.50    1.22    --  100.29 -87.00 -30.00   54
 46  \w     35.00  62.00   0.50    1.22    --  100.29   0.00-180.00   54
 47  \w     94.00 119.00   0.50    1.22    --  100.29 -59.00 -30.00   50
 48  \w    116.00 143.00   0.50    1.22    --  100.29   0.00-180.00   54
 49  \w     44.00  72.00   0.50    1.22    --  100.29 -59.00 -30.00   56
 50  \w     96.00 124.00   0.50    1.22    --  100.29 -79.00-111.00   56
 51  \w      0.00  25.00   0.50    0.30    --  -41.22  32.00 150.00   50
 52  \w    -49.00 -22.00   0.50    0.30    --  -41.22  32.00 150.00   54
 53  \w     65.00 107.00   0.50    0.30    --   41.22  32.00 150.00   84
 54  \w    -21.00  17.00   0.50    0.30    --   41.22 -54.00-180.00   76
 55  \w    -11.00  18.00   0.50    0.30    --   41.22 -54.00  30.00   58
 56  \w     32.00  65.00   0.50    0.30    --   41.22  21.00   0.00   66
 57  \w     34.00  59.00   0.50    0.30    --   41.22 -54.00-180.00   50
 58  \w    -15.00  12.00   0.50    0.30    --   41.22 -32.00 -60.00   54
 59  \w     67.00 111.00   0.50    0.30    --   41.22  21.00   0.00   88
 60  \w     99.00 156.00   0.50    1.22    --  100.29  17.00 -30.00  114
 61  \w    132.00 157.00   0.50    1.22    --  100.29  68.00   0.00   50
 62  \w     85.00 114.00   0.50    1.22    --  100.29  68.00   0.00   58
 63  \w     80.00 107.00   0.50    1.22    --  100.29  68.00 120.00   54
 64  \w     83.00 110.00   0.50    1.22    --  100.29  59.00   0.00   54
 65  \w    127.00 154.00   0.50    1.22    --  100.29  77.00 -30.00   54
 66  \w     77.00 104.00   0.50    1.22    --  100.29 -50.00 120.00   54
 67  \w     84.00 109.00   0.50    1.22    --  100.29 -96.00 -60.00   50
 68  \w     34.00  69.00   0.50    1.22    --  100.29 -17.00  30.00   70
 69  \w     81.00 119.00   0.50    1.22    --  100.29  68.00  30.00   76
 70  \w     86.00 121.00   0.50    1.22    --  100.29  77.00 -30.00   70
 71  \w     89.00 114.00   0.50    1.22    --  100.29 -17.00  30.00   50
 72  \w    131.00 157.00   0.50    1.22    --  100.29  50.00  90.00   52
 73  \w     86.00 113.00   0.50    1.22    --  100.29  50.00  90.00   54
 74  \w     85.00 110.00   0.50    1.22    --  100.29  50.00 120.00   50
 75  \w     83.00 110.00   0.50    1.22    --  100.29-117.00-120.00   54
 76  \w     52.00  60.50   0.50    1.22    --  100.29 -33.00-180.00   17
;
_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      -0.0491013000
_diffrn_orient_matrix_UB_12      -0.0055458000
_diffrn_orient_matrix_UB_13      0.0928443000
_diffrn_orient_matrix_UB_21      0.0547075000
_diffrn_orient_matrix_UB_22      -0.1145549000
_diffrn_orient_matrix_UB_23      0.0855338000
_diffrn_orient_matrix_UB_31      0.0441507000
_diffrn_orient_matrix_UB_32      0.1359881000
_diffrn_orient_matrix_UB_33      0.0758526000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15551
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.632
_diffrn_reflns_theta_min         2.460
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.199
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53318
_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    1.439
_exptl_crystal_description       plate
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3291
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0386
_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^)+(0.0667P)^2^+0.6374P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1054
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3151
_reflns_number_total             3291
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02164_si_006.cif
_cod_data_source_block           cme135
_cod_database_code               4035411
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C20 Cl N2 O3'
_reflns_odcompleteness_completeness 99.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  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), C14(H14), C17(H17), C16(H16), C2(H2), C19(H19), C3(H3A), C10(H10),
 C13(H13), C11(H11), C12(H12), C4(H4)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              75508
_shelx_hkl_checksum              73240
_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 1.795
_oxdiff_exptl_absorpt_empirical_full_min 0.480