Intramolecular Oxidative C-H Coupling for Medium-Ring Synthesis
Didier G. Pintori; Michael F. Greaney; Journal of the American Chemical Society 133 (2011) 1209–1211; doi:10.1021/ja1090854

data_4105587
_publ_contact_author_email       fraser.white@ed.ac.uk
_publ_contact_author_name        'Fraser J. White'
_publ_section_title
;
 Intramolecular Oxidative C-H Coupling for Medium-Ring Synthesis
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1209
_journal_page_last               1211
_journal_paper_doi               10.1021/ja1090854
_journal_volume                  133
_journal_year                    2011
_chemical_compound_source        'Didier Pintori'
_chemical_formula_moiety         'C18 H15 N O'
_chemical_formula_sum            'C18 H15 N O'
_chemical_formula_weight         261.31
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.858(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6927(5)
_cell_length_b                   14.1460(7)
_cell_length_c                   11.0283(6)
_cell_measurement_reflns_used    7345
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.4735
_cell_measurement_theta_min      2.3688
_cell_volume                     1327.18(13)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_data_collection
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_data_reduction
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_molecular_graphics    Shelxp
_computing_publication_material  'Platon, encifer'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'Shelxs Sheldrick'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3147
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_details
;
  1 omega   -1.00  110.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       21.2429   38.0000  120.0000 111

  2 omega    2.00  119.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       21.2429   77.0000  -30.0000 117

  3 omega -122.00  -55.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.3054  179.0000  120.0000 67

  4 omega  -46.00   24.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.3054  -79.0000  127.0000 70

  5 omega  -28.00   78.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       21.2429   38.0000  -30.0000 106

  6 omega  -73.00   71.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       21.2429  -38.0000    0.0000 144

;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14551
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         28.54
_diffrn_reflns_theta_min         2.37
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.99000
_exptl_absorpt_correction_T_min  0.84263
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_recrystallization_method
'slow evaporation of hexane/CHCl3/Et2O solution'
_exptl_crystal_size_max          0.2843
_exptl_crystal_size_mid          0.2353
_exptl_crystal_size_min          0.1732
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3140
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0393
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0529P)^2^+0.3200P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1032
_reflns_number_gt                2340
_reflns_number_total             3140
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja1090854_si_002.cif
_cod_data_source_block           mg0004
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4105587