Copper-catalyzed aerobic spirocyclization of biaryl-N-H-imines via 1,4-aminooxygenation of benzene rings.
Tnay, Ya Lin; Chen, Cheng; Chua, Yi Yuan; Zhang, Line; Chiba, Shunsuke; Organic letters 14 (2012) 3550–3553; doi:10.1021/ol301583y

data_1508588
_publ_contact_author
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Dr Shunsuke Chiba
Division of Chemistry and Biological Chemistry
School of Physical and Mathematical Sciences
Nanyang Technological University
21 Nanyang Link
Singapore 637371
Singapore
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_publ_section_title
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 Copper-catalyzed aerobic spirocyclization of biaryl-N-H-imines via
 1,4-aminooxygenation of benzene rings.
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_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3550
_journal_page_last               3553
_journal_paper_doi               10.1021/ol301583y
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C32 H44 Cu2 O10'
_chemical_formula_sum            'C32 H44 Cu2 O10'
_chemical_formula_weight         715.75
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 96.521(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.9473(8)
_cell_length_b                   18.846(2)
_cell_length_c                   12.6117(13)
_cell_measurement_reflns_used    5072
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      26.62
_cell_measurement_theta_min      2.70
_cell_volume                     1640.6(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_av_sigmaI/netI    0.0820
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            23124
_diffrn_reflns_theta_full        30.55
_diffrn_reflns_theta_max         30.55
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    1.351
_exptl_absorpt_correction_T_max  0.7930
_exptl_absorpt_correction_T_min  0.6420
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             748
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.853
_refine_diff_density_min         -1.277
_refine_diff_density_rms         0.313
_refine_ls_extinction_coef       0.053(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         4969
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0560
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0907P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1324
_refine_ls_wR_factor_ref         0.1549
_reflns_number_gt                3151
_reflns_number_total             4969
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             1507894
_cod_data_source_file            ol301583y_si_005.cif
_cod_data_source_block           Cu2(esp)2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1508588