Copper-catalyzed coupling of oxime acetates with aldehydes: a new strategy for synthesis of pyridines.
Ren, Zhi-Hui; Zhang, Zhi-Yuan; Yang, Bing-Qin; Wang, Yao-Yu; Guan, Zheng-Hui; Organic letters 13 (2011) 5394–5397; doi:10.1021/ol202290y

data_1502513
_publ_section_title
;
 Copper-catalyzed coupling of oxime acetates with aldehydes: a new
 strategy for synthesis of pyridines.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5394
_journal_page_last               5397
_journal_paper_doi               10.1021/ol202290y
_journal_volume                  13
_journal_year                    2011
_chemical_formula_sum            'C23 H17 N'
_chemical_formula_weight         307.38
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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            4
_cell_length_a                   7.468(3)
_cell_length_b                   19.561(8)
_cell_length_c                   11.277(4)
_cell_measurement_reflns_used    461
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.14
_cell_measurement_theta_min      2.70
_cell_volume                     1647.4(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0830
_diffrn_reflns_av_sigmaI/netI    0.0840
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7867
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.9915
_exptl_absorpt_correction_T_min  0.9858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.122
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   10(8)
_refine_ls_extinction_coef       0.0044(11)
_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   0.890
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2900
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.890
_refine_ls_R_factor_all          0.1543
_refine_ls_R_factor_gt           0.0553
_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^)+(0.0659P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1658
_reflns_number_gt                1170
_reflns_number_total             2900
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol202290y_si_002.cif
_cod_data_source_block           xb4076
_cod_original_cell_volume        1647.3(11)
_cod_original_sg_symbol_H-M      Pna2(1)
_cod_database_code               1502513