Highly Efficient and Enantioselective Biotransformations of Racemic Azetidine-2-carbonitriles and Their Synthetic Applications
Dong-Hui Leng; De-Xiang Wang; Jie Pan; Zhi-Tang Huang; Mei-Xiang Wang; Journal of Organic Chemistry 74 (2009) 6077–6082; doi:10.1021/jo9011656

data_4024777
_publ_section_title
;
Highly Efficient and Enantioselective Biotransformations of Racemic
Azetidine-2-carbonitriles and Their Synthetic Applications
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6077
_journal_page_last               6082
_journal_paper_doi               10.1021/jo9011656
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C11 H13 Br N2 O'
_chemical_formula_sum            'C11 H13 Br N2 O'
_chemical_formula_weight         269.14
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.177(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.3048(6)
_cell_length_b                   8.2600(6)
_cell_length_c                   9.2431(8)
_cell_measurement_reflns_used    1319
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.8
_cell_volume                     557.30(8)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalClear
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_sigmaI/netI    0.0776
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7075
_diffrn_reflns_theta_full        27.85
_diffrn_reflns_theta_max         27.85
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    3.663
_exptl_absorpt_correction_T_max  0.7582
_exptl_absorpt_correction_T_min  0.6676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.870
_refine_diff_density_min         -0.726
_refine_diff_density_rms         0.091
_refine_ls_abs_structure_details
'Flack H D (1983), 1225 Friedel Pairs, Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.022(8)
_refine_ls_extinction_coef       0.0200(10)
_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   0.928
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2638
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.928
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0326
_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          0.0432
_refine_ls_wR_factor_ref         0.0467
_reflns_number_gt                2079
_reflns_number_total             2638
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9011656_si_001.cif
_cod_data_source_block           shelxl
_cod_database_code               4024777