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_4035407
_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         'C19 H16 N2 O3 S'
_chemical_formula_sum            'C19 H16 N2 O3 S'
_chemical_formula_weight         352.40
_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                 94.376(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7036(2)
_cell_length_b                   8.6989(3)
_cell_length_c                   24.4570(9)
_cell_measurement_reflns_used    8384
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.5750
_cell_measurement_theta_min      3.5540
_cell_volume                     1634.16(9)
_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 1.000
_diffrn_measured_fraction_theta_max 0.997
_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    -59.00 -31.00   0.50    0.21    --  -41.35  67.00-157.00   56
  2  \w    -62.00 -24.00   0.50    0.21    --  -41.35 -67.00  68.00   76
  3  \w    -11.00  23.00   0.50    0.21    --  -41.35  67.00-157.00   68
  4  \w   -100.00 -74.00   0.50    0.21    --  -41.35 -67.00  68.00   52
  5  \w     80.00 157.00   0.50    0.85    --  101.00  67.00-157.00  154
  6  \w     57.00 122.00   0.50    0.85    --  101.00 -67.00  68.00  130
  7  \w    -94.00 -67.00   0.50    0.21    --  -41.35 138.00 -90.00   54
  8  \w   -104.00 -27.00   0.50    0.21    --  -41.35 -54.00 -30.00  154
  9  \w    -54.00 -20.00   0.50    0.21    --  -41.35 138.00 -90.00   68
 10  \w     22.00  56.00   0.50    0.21    --   41.35 -54.00 -30.00   68
 11  \w    -23.00  12.00   0.50    0.21    --   41.35 -77.00-150.00   70
 12  \w    -18.00  52.00   0.50    0.21    --   41.35 -43.00  90.00  140
 13  \w     39.00  66.00   0.50    0.21    --   41.35  21.00 -60.00   54
 14  \w     19.00  44.00   0.50    0.21    --   41.35 -67.00  68.00   50
 15  \w     32.00  66.00   0.50    0.21    --   41.35 -77.00-150.00   68
 16  \w     75.00 101.00   0.50    0.21    --   41.35  21.00 -60.00   52
 17  \w    -19.00   7.00   0.50    0.21    --   41.35 -54.00 -30.00   52
 18  \w    -19.00   7.00   0.50    0.21    --   41.35 -67.00  68.00   52
 19  \w     79.00 104.00   0.50    0.21    --   41.35  67.00-157.00   50
 20  \w     88.00 114.00   0.50    0.85    --  101.00  50.00 150.00   52
 21  \w     39.00 113.00   0.50    0.85    --  101.00 -42.00 -90.00  148
 22  \w     88.00 132.00   0.50    0.85    --  101.00  59.00 150.00   88
 23  \w     62.00  88.00   0.50    0.85    --  101.00 -33.00-150.00   52
 24  \w     78.00 157.00   0.50    0.85    --  101.00  77.00 150.00  158
 25  \w    113.00 157.00   0.50    0.85    --  101.00  50.00 -60.00   88
 26  \w    126.00 157.00   0.50    0.85    --  101.00  93.00 -30.00   62
 27  \w     86.00 157.00   0.50    0.85    --  101.00  68.00-180.00  142
 28  \w     90.00 147.00   0.50    0.85    --  101.00  17.00 -60.00  114
 29  \w     81.00 112.00   0.50    0.85    --  101.00-111.00  60.00   62
 30  \w     87.00 112.00   0.50    0.85    --  101.00  93.00 -30.00   50
 31  \w     41.00 114.00   0.50    0.85    --  101.00 -77.00  30.00  146
 32  \w     43.00  99.00   0.50    0.85    --  101.00 -42.00   0.00  112
 33  \w     64.00 110.00   0.50    0.85    --  101.00 -87.00-120.00   92
 34  \w     94.00 119.00   0.50    0.85    --  101.00  67.00-157.00   50
 35  \w    -65.00 -39.00   0.50    0.21    --  -41.35 -54.00   0.00   52
 36  \w    -91.00 -65.00   0.50    0.21    --  -41.35 -32.00 150.00   52
 37  \w   -101.00 -68.00   0.50    0.21    --  -41.35 -54.00   0.00   66
 38  \w     79.00 105.00   0.50    0.21    --   41.35  32.00 150.00   52
 39  \w     26.00  54.00   0.50    0.21    --   41.35  65.00   0.00   56
 40  \w     26.00  57.00   0.50    0.21    --   41.35 -54.00-120.00   62
 41  \w     40.00  66.00   0.50    0.21    --   41.35  43.00 -30.00   52
 42  \w    -19.00   9.00   0.50    0.21    --   41.35 -54.00-120.00   56
 43  \w     76.00 129.00   0.50    0.85    --  101.00  77.00 -30.00  106
 44  \w     81.00 114.00   0.50    0.85    --  101.00  68.00   0.00   66
 45  \w    128.00 156.00   0.50    0.85    --  101.00  17.00 120.00   56
 46  \w     30.00 100.00   0.50    0.85    --  101.00 -17.00  30.00  140
 47  \w     83.00 109.00   0.50    0.85    --  101.00  59.00 -60.00   52
 48  \w     43.00  99.00   0.50    0.85    --  101.00 -42.00  60.00  112
 49  \w     84.00 135.00   0.50    0.85    --  101.00  59.00-120.00  102
 50  \w    125.00 133.00   0.50    0.85    --  101.00  77.00 -60.00   16
;
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_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
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'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1501828000
_diffrn_orient_matrix_UB_12      -0.0975853000
_diffrn_orient_matrix_UB_13      0.0195926000
_diffrn_orient_matrix_UB_21      -0.1316033000
_diffrn_orient_matrix_UB_22      0.0949285000
_diffrn_orient_matrix_UB_23      -0.0366298000
_diffrn_orient_matrix_UB_31      0.0190650000
_diffrn_orient_matrix_UB_32      -0.1132390000
_diffrn_orient_matrix_UB_33      -0.0475944000
_diffrn_radiation_monochromator  mirror
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_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            12169
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.779
_diffrn_reflns_theta_min         3.625
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.945
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39193
_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    1.432
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3197
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0413
_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^)+(0.0607P)^2^+0.7194P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1143
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2882
_reflns_number_total             3197
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02164_si_005.cif
_cod_data_source_block           cme081
_cod_original_cell_volume        1634.17(10)
_cod_database_code               4035407
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C19 N2 O3 S'
_shelx_estimated_absorpt_t_max   0.709
_shelx_estimated_absorpt_t_min   0.652
_reflns_odcompleteness_completeness 99.71
_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:
 C7(H7), C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C11(H11), C10(H10), C14(H14), C2(H2), C3(H3A), C13(H13), C17(H17),
 C19(H19), C18(H18)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              44825
_shelx_hkl_checksum              66920
_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 2.652
_oxdiff_exptl_absorpt_empirical_full_min 0.531