Strain-promoted oxidative annulation of arynes and cyclooctynes with benzamides: palladium-catalyzed C-h/n-h activation for the synthesis of N-heterocycles.
Peng, Xianglong; Wang, Weiguo; Jiang, Chao; Sun, Di; Xu, Zhenghu; Tung, Chen-Ho; Organic letters 16 (2014) 5354–5357; doi:10.1021/ol5025426

data_1517891
_publ_section_title
;
 Strain-promoted oxidative annulation of arynes and cyclooctynes with
 benzamides: palladium-catalyzed C-h/n-h activation for the synthesis of
 N-heterocycles.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5354
_journal_page_last               5357
_journal_paper_doi               10.1021/ol5025426
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C18 H21 N O4'
_chemical_formula_sum            'C18 H21 N O4'
_chemical_formula_weight         315.36
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-06-19
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.06 svn.r2239, GUI svn.r4109)
;
_cell_angle_alpha                98.405(4)
_cell_angle_beta                 95.963(4)
_cell_angle_gamma                104.965(4)
_cell_formula_units_Z            2
_cell_length_a                   5.7842(15)
_cell_length_b                   9.566(3)
_cell_length_c                   15.111(4)
_cell_measurement_reflns_used    1149
_cell_measurement_temperature    298(2)
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_cell_measurement_theta_min      4.481
_cell_volume                     790.3(4)
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
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_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
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_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
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_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3922
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_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.41
_diffrn_source                   'fine-focus sealed tube'
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_exptl_absorpt_correction_T_max  0.9926
_exptl_absorpt_correction_T_min  0.9861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2733
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0452
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0716P)^2^+0.0436P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1184
_refine_ls_wR_factor_ref         0.1354
_reflns_number_gt                1911
_reflns_number_total             2733
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5025426_si_002.cif
_cod_data_source_block           test
_cod_depositor_comments          'Adding full bibliography for 1517891.cif.'
_cod_original_cell_volume        790.2(3)
_cod_database_code               1517891