Bisoxazoline-Lewis Acid-Catalyzed Direct-Electron Demand oxo-Hetero-Diels-Alder Reactions of N-Oxy-pyridine Aldehyde and Ketone Derivatives
Aitor Landa; Bo Richter; Rasmus Lyng Johansen; Anna Minkkilä; Karl Anker Jørgensen; Journal of Organic Chemistry 72 (2007) 240–245; doi:10.1021/jo062012u

data_4022652
_publ_contact_author             'Overgaard, Jacob'
_publ_contact_author_email       jacobo@chem.au.dk
_publ_section_title
;
 Bisoxazoline-Lewis Acid-Catalyzed Direct-Electron Demand
 oxo-Hetero-Diels-Alder Reactions of N-Oxy-pyridine Aldehyde
 and Ketone Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              240
_journal_page_last               245
_journal_paper_doi               10.1021/jo062012u
_journal_volume                  72
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C10 H8 Br1 N1 O3'
_chemical_formula_sum            'C10 H8 Br N O3'
_chemical_formula_weight         270.08
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2006-03-07T08:53:44-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 98.2920(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.14540(10)
_cell_length_b                   6.91760(10)
_cell_length_c                   10.0029(2)
_cell_measurement_reflns_used    4996
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.5
_cell_measurement_theta_min      2.88
_cell_measurement_wavelength     0.71073
_cell_volume                     489.265(14)
_computing_cell_refinement       'Saint+ (Bruker-Nonius, 2006)'
_computing_data_collection       'Apex2 (Bruker-Nonius, 2006)'
_computing_data_reduction        'Saint+ (Bruker-Nonius, 2006)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 83.33
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD-based diffractometer'
_diffrn_measurement_method       '\f-scans and \w-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10810
_diffrn_reflns_theta_full        33.09
_diffrn_reflns_theta_max         33.09
_diffrn_reflns_theta_min         2.06
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Siemens K FFMO 2K 90'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.185
_exptl_absorpt_correction_T_max  0.715
_exptl_absorpt_correction_T_min  0.499
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS (Sheldrick, 1996).
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.833
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 1698 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.003(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         3692
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0274
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0203P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0494
_refine_ls_wR_factor_ref         0.0508
_reflns_Friedel_coverage         0.852
_reflns_number_gt                3328
_reflns_number_total             3692
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo062012urom20060929_035552.cif
_cod_data_source_block           06jo0012_white_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4022652