Enantioselective palladium(II)-catalyzed formal [3,3]-sigmatropic rearrangement of 2-allyloxypyridines and related heterocycles.
Rodrigues, Alessandro; Lee, Ernest E.; Batey, Robert A.; Organic letters 12 (2010) 260–263; doi:10.1021/ol9025759

data_1503365
_publ_section_title
;
 Enantioselective palladium(II)-catalyzed formal [3,3]-sigmatropic
 rearrangement of 2-allyloxypyridines and related heterocycles.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              260
_journal_page_last               263
_journal_paper_doi               10.1021/ol9025759
_journal_volume                  12
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C9 H11 N O2'
_chemical_formula_sum            'C9 H11 N O2'
_chemical_formula_weight         165.19
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 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
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2691(1)
_cell_length_b                   8.1601(1)
_cell_length_c                   14.8411(2)
_cell_measurement_reflns_used    9495
_cell_measurement_temperature    150
_cell_measurement_theta_max      67.36
_cell_measurement_theta_min      5.96
_cell_volume                     880.32(2)
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006b)'
_computing_data_collection       'APEX2 v2.1-0 (Bruker AXS, 2006a)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006b)'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.881
_diffrn_measurement_device_type  'Bruker Microstar'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_av_sigmaI/netI    0.0177
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13854
_diffrn_reflns_theta_full        67.89
_diffrn_reflns_theta_max         67.89
_diffrn_reflns_theta_min         5.96
_diffrn_standards_decay_%        3.20
_diffrn_standards_interval_time  900
_diffrn_standards_number         108
_exptl_absorpt_coefficient_mu    0.726
_exptl_absorpt_correction_T_max  0.9436
_exptl_absorpt_correction_T_min  0.7739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.103
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 'Flack H D (1983), 452 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1401
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0266
_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^)+(0.0511P)^2^+0.0611P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0716
_refine_ls_wR_factor_ref         0.0724
_reflns_number_gt                1376
_reflns_number_total             1401
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol9025759_si_002.cif
_cod_data_source_block           lough8
_cod_depositor_comments
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The following automatic conversions were performed:

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

'_geom_bond_publ_flag'
value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26 (12
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.2 from 2011-04-26 (15 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               1503365