Dearomatization of electron poor six-membered N-heterocycles through [3 + 2] annulation with aminocyclopropanes
Preindl, Johannes; Chakrabarty, Shyamal; Waser, Jérôme; Chemical Science 8 (2017) 7112–7118; doi:10.1039/C7SC03197A

data_1546842
_publ_section_title
;
 Dearomatization of electron poor six-membered N-heterocycles through [3 +
 2] annulation with aminocyclopropanes
;
_journal_issue                   10
_journal_name_full               'Chemical Science'
_journal_page_first              7112
_journal_page_last               7118
_journal_paper_doi               10.1039/C7SC03197A
_journal_volume                  8
_journal_year                    2017
_chemical_formula_moiety         'C24 H20 N2 O6'
_chemical_formula_sum            'C24 H20 N2 O6'
_chemical_formula_weight         432.42
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2017-06-15 deposited with the CCDC.
2017-08-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   28.9068(4)
_cell_length_b                   7.90250(10)
_cell_length_c                   8.98890(10)
_cell_measurement_reflns_used    24791
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.1130
_cell_measurement_theta_min      4.5600
_cell_volume                     2053.39(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1333
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_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     -9.00  23.00   1.00    1.00    --  -42.20  37.00 -60.00   32
  2  \w    -49.00 -18.00   1.00    1.00    --  -42.20 -37.00 -30.00   31
  3  \w    -60.00 -23.00   1.00    1.00    --  -42.20  37.00 -60.00   37
  4  \w    -71.00  31.00   1.00    1.00    --  -42.20  65.00  28.00  102
  5  \w     -7.00  18.00   1.00    1.00    --   34.00  99.00  82.94   25
  6  \w     17.00  44.00   1.00    1.00    --   50.00  79.00  84.41   27
  7  \w     59.00 108.00   1.00    1.00    --   42.20  65.00  28.00   49
  8  \w    131.00 163.00   1.00    1.46    --   90.00  67.00 -50.91   32
  9  \w    153.00 178.00   1.00    1.46    --  109.26  65.00  28.00   25
 10  \w    121.00 147.00   1.00    1.46    --  109.26  77.00  30.00   26
 11  \w     89.00 178.00   1.00    1.46    --  109.26  77.00 -60.00   89
 12  \w    114.00 147.00   1.00    1.46    --   82.00  60.00-112.18   33
 13  \w    113.00 171.00   1.00    1.46    --  109.26  77.00-180.00   58
 14  \w     93.00 129.00   1.00    1.46    --  109.26 178.00-120.00   36
 15  \w     81.00 169.00   1.00    1.46    --  109.26  74.00-103.13   88
 16  \w     79.00 111.00   1.00    1.46    --  109.26  65.00  28.00   32
 17  \w     80.00 173.00   1.00    1.46    --  109.26  61.00  60.00   93
 18  \w     83.00 176.00   1.00    1.46    --  109.26  61.00  90.00   93
 19  \w     83.00 110.00   1.00    1.46    --  109.26  63.00 -32.54   27
 20  \w     78.00 115.00   1.00    1.46    --  109.26  77.00  30.00   37
 21  \w     81.00 144.00   1.00    1.46    --  109.26  77.00 -30.00   63
 22  \w     77.00 103.00   1.00    1.46    --  109.26  77.00  60.00   26
 23  \w     77.00 162.00   1.00    1.46    --  109.26  77.00 120.00   85
 24  \w     77.00 152.00   1.00    1.46    --  109.26  77.00 150.00   75
 25  \w     64.00  89.00   1.00    1.46    --   94.00  67.00  25.58   25
 26  \w     60.00 125.00   1.00    1.46    --   90.00  67.00 -50.91   65
 27  \w     77.00 119.00   1.00    1.46    --  109.26  77.00-120.00   42
 28  \w     77.00 107.00   1.00    1.46    --  109.26  77.00-180.00   30
 29  \w     77.00 177.00   1.00    1.46    --  109.26  77.00-150.00  100
 30  \w     67.00 114.00   1.00    1.46    --   98.00  75.00 104.33   47
 31  \w     56.00  86.00   1.00    1.46    --   86.00  64.00 179.00   30
 32  \w     50.00  83.00   1.00    1.46    --   82.00  76.00 125.67   33
 33  \w     42.00  69.00   1.00    1.00    --   74.00  77.00  87.25   27
 34  \w     36.00  62.00   1.00    1.00    --   66.00  75.00 127.10   26
 35  \w     37.00  63.00   1.00    1.00    --   70.00  77.00  65.22   26
 36  \w     42.00  68.00   1.00    1.00    --   74.00  74.00  16.43   26
 37  \w     53.00  79.00   1.00    1.46    --   86.00  77.00  14.95   26
 38  \w     38.00  67.00   1.00    1.00    --   70.00  76.00  -5.79   29
 39  \w     43.00  69.00   1.00    1.00    --   74.00  74.00 -34.94   26
 40  \w     53.00  79.00   1.00    1.46    --   82.00  63.00 -83.48   26
 41  \w     54.00  80.00   1.00    1.46    --   82.00  60.00-112.18   26
 42  \w     45.00  74.00   1.00    1.46    --   78.00  77.00-170.38   29
 43  \w     44.00  71.00   1.00    1.00    --   74.00  68.00-101.70   27
 44  \w     37.00  63.00   1.00    1.00    --   70.00  77.00-138.03   26
 45  \w     35.00  60.00   1.00    1.00    --   66.00  76.00-172.27   25
 46  \w     20.00  46.00   1.00    1.00    --   54.00  81.00-178.46   26
 47  \w     37.00  63.00   1.00    1.00    --   70.00  77.00 -69.76   26
 48  \w     20.00  45.00   1.00    1.00    --   54.00  81.00  -7.44   25
 49  \w     21.00  46.00   1.00    1.00    --   54.00  79.00 -55.09   25
 50  \w     13.00  38.00   1.00    1.00    --   42.20  65.00  28.00   25
 51  \w     20.00  46.00   1.00    1.00    --   54.00  81.00  89.05   26
 52  \w     20.00  45.00   1.00    1.00    --   54.00  81.00 151.43   25
 53  \w     57.00 145.00   1.00    1.46    --  109.26 178.00 -60.00   88
 54  \w      9.00  34.00   1.00    1.00    --   42.00  79.00 -67.22   25
 55  \w     39.00 139.00   1.00    1.46    --  109.26 -65.00-107.00  100
 56  \w     61.00 105.00   1.00    1.46    --  109.26-111.00  60.00   44
 57  \w     55.00 114.00   1.00    1.46    --  109.26-111.00 120.00   59
 58  \w     24.00  98.00   1.00    1.00    --   42.20-125.00 150.00   74
 59  \w     34.00 115.00   1.00    1.46    --  109.26-111.00 -90.00   81
 60  \w    -30.00  42.00   1.00    1.00    --   42.20 -65.00-107.00   72
 61  \w   -108.00 -12.00   1.00    1.00    --  -42.20 -65.00-107.00   96
 62  \w   -116.00 -61.00   1.00    1.00    --  -42.20 -37.00 -30.00   55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            35518
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.495
_diffrn_reflns_theta_min         5.797
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.846
_exptl_absorpt_correction_T_max  0.850
_exptl_absorpt_correction_T_min  0.723
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear intense yellow'
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_description       plate
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.509
_exptl_crystal_size_mid          0.409
_exptl_crystal_size_min          0.265
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 1862 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(5)
_refine_ls_extinction_coef       0.0012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         4206
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0236
_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^)+(0.0418P)^2^+0.1851P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0639
_refine_ls_wR_factor_ref         0.0645
_reflns_Friedel_coverage         0.864
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                4111
_reflns_number_total             4206
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc03197a2.cif
_cod_data_source_block           shelx
_cod_database_code               1546842
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              44334