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_4035409
_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         'C17 H18 N2 O3, H2 O'
_chemical_formula_sum            'C17 H20 N2 O4'
_chemical_formula_weight         316.35
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P -2ac -2n'
_space_group_name_H-M_alt        'P n 21 a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-07-20
_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                   13.6553(3)
_cell_length_b                   20.2125(5)
_cell_length_c                   11.5578(3)
_cell_measurement_reflns_used    16300
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.8870
_cell_measurement_theta_min      3.2690
_cell_volume                     3190.04(13)
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
_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 0.996
_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   -104.00 -79.00   0.50    0.20    --  -41.22-155.00-162.00   50
  2  \w    -61.00 -30.00   0.50    0.20    --  -41.22 -17.00  72.00   62
  3  \w    -37.00 -12.00   0.50    0.20    --  -41.22  17.00-118.00   50
  4  \w    -70.00 -45.00   0.50    0.20    --  -41.22 112.00  -8.00   50
  5  \w    -46.00 -21.00   0.50    0.20    --  -41.22 120.00  78.00   50
  6  \w     41.00  68.00   0.50    0.20    --   41.22-120.00  -5.00   54
  7  \w     15.00  78.00   0.50    0.20    --   41.22-112.00-101.00  126
  8  \w      6.00  31.00   0.50    0.20    --   41.22 -17.00  72.00   50
  9  \w     44.00  70.00   0.50    0.20    --   41.22  17.00-118.00   52
 10  \w     63.00  88.00   0.50    0.20    --   41.22 155.00-124.00   50
 11  \w     94.00 124.00   0.50    0.31    --  101.00  17.00-118.00   60
 12  \w     35.00  76.00   0.50    0.31    --  101.00 -17.00  72.00   82
 13  \w     73.00 103.00   0.50    0.31    --  101.00-120.00  -5.00   60
 14  \w     81.00 106.00   0.50    0.31    --  101.00 155.00-124.00   50
 15  \w     76.00 113.00   0.50    0.31    --  101.00-112.00-101.00   74
 16  \w    104.00 132.00   0.50    0.31    --  101.00 120.00  78.00   56
 17  \w     63.00  88.00   0.50    0.31    --  101.00-155.00-162.00   50
 18  \w     95.00 135.00   0.50    0.31    --  101.00 112.00  -8.00   80
 19  \w    -55.00  21.00   0.50    0.20    --  -41.22  54.00-150.00  152
 20  \w      9.00  65.00   0.50    0.20    --   41.22 -77.00-150.00  112
 21  \w     50.00 105.00   0.50    0.20    --   41.22  32.00-150.00  110
 22  \w    -11.00  26.00   0.50    0.20    --   41.22 -32.00-120.00   74
 23  \w    -23.00   2.00   0.50    0.20    --   41.22 -32.00   0.00   50
 24  \w     73.00 113.00   0.50    0.31    --  101.00-111.00  60.00   80
 25  \w     89.00 147.00   0.50    0.31    --  101.00  17.00   0.00  116
 26  \w     38.00  64.00   0.50    0.31    --  101.00-111.00  60.00   52
 27  \w     79.00 128.00   0.50    0.31    --  101.00  77.00 -90.00   98
 28  \w    112.00 157.00   0.50    0.31    --  101.00  33.00-180.00   90
 29  \w     38.00 115.00   0.50    0.31    --  101.00 -50.00 -90.00  154
 30  \w     37.00  82.00   0.50    0.31    --  101.00 -33.00-180.00   90
 31  \w     80.00 106.00   0.50    0.31    --  101.00 -33.00-180.00   52
 32  \w     25.00  50.00   0.50    0.20    --   41.22 -32.00-180.00   50
 33  \w    109.00 156.00   0.50    0.31    --  101.00  42.00 150.00   94
 34  \w    117.00 143.00   0.50    0.31    --  101.00  77.00 -30.00   52
 35  \w    122.00 157.00   0.50    0.31    --  101.00  59.00  30.00   70
 36  \w     89.00 115.00   0.50    0.31    --  101.00-111.00-180.00   52
 37  \w     76.00 105.00   0.50    0.31    --  101.00  77.00 -30.00   58
 38  \w     86.00 115.00   0.50    0.31    --  101.00  59.00  30.00   58
 39  \w     46.00  72.00   0.50    0.31    --  101.00 178.00  60.00   52
 40  \w     83.00 118.00   0.50    0.31    --  101.00 178.00  60.00   70
 41  \w     65.00 105.00   0.50    0.31    --  101.00 -59.00 -30.00   80
 42  \w     86.00 116.00   0.50    0.31    --  101.00  59.00 -90.00   60
 43  \w     86.00 122.00   0.50    0.31    --  101.00 -68.00-180.00   72
 44  \w     37.00  64.00   0.50    0.31    --  101.00 -68.00-180.00   54
 45  \w     58.00  84.00   0.50    0.31    --  101.00 154.00-124.00   52
 46  \w   -108.00 -82.00   0.50    0.20    --  -41.22 -11.00  30.00   52
 47  \w    -66.00 -22.00   0.50    0.20    --  -41.22 -11.00  30.00   88
 48  \w      1.00  44.00   0.50    0.20    --   41.22 -32.00 -90.00   86
 49  \w     22.00 101.00   0.50    0.20    --   41.22  65.00  60.00  158
 50  \w     69.00 103.00   0.50    0.20    --   41.22  54.00-120.00   68
 51  \w    -14.00  47.00   0.50    0.20    --   41.22 -43.00  30.00  122
 52  \w     67.00  93.00   0.50    0.20    --   41.22-154.00-163.00   52
 53  \w     10.00  37.00   0.50    0.20    --   41.22 -77.00   0.00   54
 54  \w    -19.00   8.00   0.50    0.20    --   41.22 -77.00   0.00   54
 55  \w    -20.00  57.00   0.50    0.20    --   41.22 -77.00  30.00  154
 56  \w     58.00  98.00   0.50    0.20    --   41.22  43.00 -30.00   80
 57  \w     95.00 121.00   0.50    0.31    --  101.00  33.00-120.00   52
 58  \w     79.00 128.00   0.50    0.31    --  101.00 -87.00-120.00   98
 59  \w    124.00 156.00   0.50    0.31    --  101.00  33.00-120.00   64
 60  \w     67.00 115.00   0.50    0.31    --  101.00-111.00  30.00   96
 61  \w     38.00 104.00   0.50    0.31    --  101.00 -87.00 120.00  132
 62  \w     42.00  68.00   0.50    0.31    --  101.00 -87.00-120.00   52
;
_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      0.0238170000
_diffrn_orient_matrix_UB_12      -0.0613008000
_diffrn_orient_matrix_UB_13      0.0741437000
_diffrn_orient_matrix_UB_21      -0.0098110000
_diffrn_orient_matrix_UB_22      -0.0443110000
_diffrn_orient_matrix_UB_23      -0.1077907000
_diffrn_orient_matrix_UB_31      0.1098137000
_diffrn_orient_matrix_UB_32      0.0093077000
_diffrn_orient_matrix_UB_33      -0.0257376000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            26781
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.938
_diffrn_reflns_theta_min         4.375
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.778
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78123
_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    1.317
_exptl_crystal_description       prism
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.718
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     428
_refine_ls_number_reflns         6162
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0567
_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^)+(0.1137P)^2^+0.5199P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1457
_refine_ls_wR_factor_ref         0.1507
_reflns_Friedel_coverage         0.942
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                5880
_reflns_number_total             6162
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02164_si_002.cif
_cod_data_source_block           cme202_prism
_cod_original_cell_volume        3190.03(14)
_cod_database_code               4035409
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C17 H18 N2 O3'
_shelx_estimated_absorpt_t_max   0.847
_shelx_estimated_absorpt_t_min   0.817
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.93
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.7(3)
 0.3(3)
2. 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, All O(H,H) groups
3.a Free rotating group:
 O2S(H2SA,H2SB), O1S(H1SA,H1SB)
3.b Ternary CH refined with riding coordinates:
 C7A(H7A), C6A(H6A), C6(H6), C7(H7)
3.c Secondary CH2 refined with riding coordinates:
 C8A(H8AA,H8AB), C8(H8A,H8B)
3.d Aromatic/amide H refined with riding coordinates:
 C12(H12), C3A(H3AA), C13A(H13A), C16(H16), C4A(H4A), C4(H4), C12A(H12A),
 C2A(H2A), C15A(H15A), C13(H13), C15(H15), C2(H2), C16A(H16A), C3(H3B)
3.e Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C17(H17D,H17E,H17F), C17A(H17A,H17B,H17C), C9A(H9AA,H9AB,H9AC)
3.f Idealised tetrahedral OH refined as rotating group:
 O3A(H3A), O3(H3)
;
_shelx_res_checksum              51610
_shelx_hkl_checksum              55398
_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 2.492
_oxdiff_exptl_absorpt_empirical_full_min 0.792