Diastereoselective Multicomponent Cascade Reaction Leading to [3.2.0]-Heterobicyclic Compounds
Kerti Ausmees; Kadri Kriis; Tõnis Pehk; Franz Werner; Ivar Järving; Margus Lopp; Tõnis Kanger; Journal of Organic Chemistry 77 (2012) 10680–10687; doi:10.1021/jo3019413

data_4027760
_publ_section_title
;
 Diastereoselective Multicomponent Cascade Reaction Leading to
 [3.2.0]-Heterobicyclic Compounds
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10680
_journal_page_last               10687
_journal_paper_doi               10.1021/jo3019413
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety
;
(C17 H24 Br N O2)
;
_chemical_formula_sum            'C17 H24 Br N O2'
_chemical_formula_weight         354.28
_chemical_melting_point          367
_chemical_name_common            'KA254, A enantiomer'
_chemical_name_systematic
; 
[(1R,2S,5R,6S,7R)-2-(4-bromophenyl)-7-(diethylamino)-3-
oxabicyclo[3.2.0]heptan-6-yl]methanol
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.853(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.9677(9)
_cell_length_b                   5.2389(7)
_cell_length_c                   17.839(2)
_cell_measurement_reflns_used    2324
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.8034
_cell_measurement_theta_min      2.6364
_cell_volume                     835.09(17)
_computing_cell_refinement       'APEX2 (Bruker, 2011); SAINT (Bruker, 2009)'
_computing_data_collection       'GIS (Bruker)'
_computing_data_reduction        'SAINT (Bruker, 2009);XPREP (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker SMART X2S diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  'doubly curved silicon crystal'
_diffrn_radiation_source         'XOS X-beam microfocus source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_sigmaI/netI    0.0765
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5287
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.15
_exptl_absorpt_coefficient_mu    2.466
_exptl_absorpt_correction_T_max  0.5250
_exptl_absorpt_correction_T_min  0.4388
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Sheldrick, G. M. (2008) SADABS. University of G\"ottingen, Germany.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.004(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.902
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2875
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.902
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0332
_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^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0751
_refine_ls_wR_factor_ref         0.0804
_reflns_number_gt                2430
_reflns_number_total             2876
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3019413_FW38.cif
_cod_data_source_block           fw38final
_cod_original_cell_volume        835.10(17)
_cod_database_code               4027760