Regioselective De Novo Synthesis of Cyanohydroxypyridines with a Concerted Cycloaddition Mechanism
Jin-Yong Lu; John A. Keith; Wei-Zheng Shen; Markus Schürmann; Hans Preut; Timo Jacob; Hans-Dieter Arndt; Journal of the American Chemical Society 130 (2008) 13219–13221; doi:10.1021/ja804078v

data_4108428
_publ_contact_author_address
;       Fachbereich Chemie
    Universit\"at Dortmund
    Otto-Hahn-Str. 6
    44221 Dortmund
    Germany
;
_publ_contact_author_email       markus.schuermann@tu-dortmund
_publ_contact_author_name        'Dr. Markus Sch\"urmann'
_publ_contact_author_phone       49-231-755-3841
_publ_section_title
;
 Regioselective De Novo Synthesis of Cyanohydroxypyridines with a
 Concerted Cycloaddition Mechanism
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13219
_journal_page_last               13221
_journal_paper_doi               10.1021/ja804078v
_journal_volume                  130
_journal_year                    2008
_chemical_formula_moiety         'C16 H11 F3 N2 O3'
_chemical_formula_sum            'C16 H11 F3 N2 O3'
_chemical_formula_weight         336.27
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 96.257(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.1687(16)
_cell_length_b                   6.9866(9)
_cell_length_c                   31.257(3)
_cell_measurement_reflns_used    40932
_cell_measurement_temperature    173(1)
_cell_measurement_theta_max      25.37
_cell_measurement_theta_min      2.56
_cell_volume                     3075.7(6)
_computing_cell_refinement
; 
DENZO & SCALEPACK (Otwinowski & Minor, 1997)
;
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction
; 
DENZO & SCALEPACK (Otwinowski & Minor, 1997)
;
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 1991)'
_computing_publication_material
;
SHELXL-97, PLATON (Spek, 2003)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(1)
_diffrn_detector_area_resol_mean '19 vertical, 18 horizontal'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method
;
682 frames via \w-rotation (\D\w=1\%) and two times 115 s per frame
(seven sets at different \k-angles)
;
_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  0.051
_diffrn_reflns_av_sigmaI/netI    0.3584
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            40932
_diffrn_reflns_theta_full        25.37
_diffrn_reflns_theta_max         25.37
_diffrn_reflns_theta_min         2.56
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_description       needle
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.915
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     465
_refine_ls_number_reflns         5622
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.915
_refine_ls_R_factor_all          0.1941
_refine_ls_R_factor_gt           0.0406
_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 
 [1.0exp(4.90(sin\q/\l)^2^)]/[\s^2^(Fo^2^)] 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0658
_refine_ls_wR_factor_ref         0.0831
_reflns_number_gt                1491
_reflns_number_total             5622
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ja804078v_si_001.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4108428