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_1508585
_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         'C21 H13 N'
_chemical_formula_sum            'C21 H13 N'
_chemical_formula_weight         279.32
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           78
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_symmetry_space_group_name_Hall  'P 4cw'
_symmetry_space_group_name_H-M   'P 43'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.1152(2)
_cell_length_b                   9.1152(2)
_cell_length_c                   36.0783(11)
_cell_measurement_reflns_used    9900
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      29.82
_cell_measurement_theta_min      2.50
_cell_volume                     2997.63(13)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0508
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_number            41476
_diffrn_reflns_theta_full        30.54
_diffrn_reflns_theta_max         30.54
_diffrn_reflns_theta_min         2.26
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.9732
_exptl_absorpt_correction_T_min  0.9718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     476
_refine_ls_number_reflns         4617
_refine_ls_number_restraints     563
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0542
_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^)+(0.0849P)^2^+0.0399P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1367
_reflns_number_gt                4021
_reflns_number_total             4617
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             1507891
_cod_data_source_file            ol301583y_si_002.cif
_cod_data_source_block           (+)-1q
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal'
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      P4(3)
_cod_database_code               1508585