One-Pot Access to 1,7a-Dihydro-1,3a-ethano-indene and 1,8a-Dihydro-1,3a-ethano-azulene Skeletons by a Sequential Gold(I)-Catalyzed Propargyl Claisen Rearrangement/Nazarov Cyclization/[4+2] Cycloaddition Reaction.
Rinaldi, Antonia; Langé, Vittoria; Scarpi, Dina; Occhiato, Ernesto G.; The Journal of organic chemistry 85 (2020) 5078–5086; doi:10.1021/acs.joc.0c00088

data_4038127
_publ_section_title
;
 One-Pot Access to 1,7a-Dihydro-1,3a-ethano-indene and
 1,8a-Dihydro-1,3a-ethano-azulene Skeletons by a Sequential
 Gold(I)-Catalyzed Propargyl Claisen Rearrangement/Nazarov
 Cyclization/[4+2] Cycloaddition Reaction.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5078
_journal_page_last               5086
_journal_paper_doi               10.1021/acs.joc.0c00088
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C17 H21 N O3'
_chemical_formula_sum            'C17 H21 N O3'
_chemical_formula_weight         287.35
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date
;
'Thu Dec 06 17:28:40 2018'
;
_audit_creation_method
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_cell_angle_alpha                94.799(7)
_cell_angle_beta                 97.856(7)
_cell_angle_gamma                97.882(8)
_cell_formula_units_Z            2
_cell_length_a                   8.3484(9)
_cell_length_b                   8.5960(8)
_cell_length_c                   10.5662(8)
_cell_measurement_reflns_used    1700
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.5160
_cell_measurement_theta_min      5.1950
_cell_volume                     739.98(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
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_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012'
_computing_publication_material  'WinGX publication routines'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SIR2004 J.Appl.Cryst.38,381-388'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1241
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.9734
_diffrn_measured_fraction_theta_max 0.9027
_diffrn_measurement_details
;
  1 omega   20.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       45.9074   77.0000 -120.0000 89

  2 omega   27.00   66.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       97.3169  -30.0000   30.0000 39

  3 omega   36.00  125.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       97.3169  -77.0000  -30.0000 89

  4 omega   43.00   77.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       97.3169  -45.0000  150.0000 34

  5 omega   28.00   55.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       97.3169  -30.0000   60.0000 27

  6 omega   22.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       97.3169  -94.0000  -90.0000 87

  7 omega  -25.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       45.9074  -77.0000  120.0000 99

  8 omega  -63.00  -36.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   30.0000  -30.0000 27

  9 omega  -69.00  -33.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   30.0000    0.0000 36

 10 omega  -65.00  -21.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   30.0000   30.0000 44

 11 omega  -65.00  -19.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   30.0000  120.0000 46

 12 omega -116.00  -20.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  125.0000  120.0000 96

 13 omega   87.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       45.9074  125.0000  120.0000 27

 14 omega  -52.00  -19.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   30.0000 -180.0000 33

 15 omega  -50.00  -18.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  125.0000 -180.0000 32

 16 omega  -95.00  -68.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   61.0000 -180.0000 27

 17 omega  -97.00  -72.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  125.0000 -180.0000 25

 18 omega -146.00  -78.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -61.0000   30.0000 68

 19 omega  -98.00  -73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -45.9074 -125.0000 -180.0000 25

;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0991
_diffrn_reflns_av_unetI/netI     0.1034
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4262
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         61.165
_diffrn_reflns_theta_min         5.223
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.710
_exptl_absorpt_correction_T_max  0.9970
_exptl_absorpt_correction_T_min  0.9617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2223
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.1385
_refine_ls_R_factor_gt           0.0928
_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^)+(0.1810P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2293
_refine_ls_wR_factor_ref         0.3109
_reflns_number_gt                1370
_reflns_number_total             2223
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00088_si_002.cif
_cod_data_source_block           exp-333
_cod_depositor_comments          'Adding full bibliography for 4038127.cif.'
_cod_database_code               4038127
_shelxl_version_number           2014/6
_shelx_res_checksum              63629
_shelx_hkl_checksum              76514