Highly Diastereoselective Baldwin Rearrangement of Isoxazolines intocis-Acylaziridines
Eric Gayon; Olivier Debleds; Marie Nicouleau; Frederic Lamaty; Arie van der Lee; Emmanuel Vrancken; Jean-Marc Campagne; Journal of Organic Chemistry 75 (2010) 6050–6053; doi:10.1021/jo101273d

data_4025657
_publ_section_title
;
 Highly Diastereoselective Baldwin Rearrangement of Isoxazolines
 intocis-Acylaziridines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6050
_journal_page_last               6053
_journal_paper_doi               10.1021/jo101273d
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C19 H21 N1 O3 S1'
_chemical_formula_sum            'C19 H21 N O3 S'
_chemical_formula_weight         343.45
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             09-06-16
_audit_creation_method           CRYSTALS_ver_12.86
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.2623(10)
_cell_length_b                   11.1128(10)
_cell_length_c                   19.8940(10)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    293
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     3595.2(4)
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measurement_device       Unknown
_diffrn_measurement_device_type  Serial
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.091
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            41166
_diffrn_reflns_theta_full        26.785
_diffrn_reflns_theta_max         29.114
_diffrn_reflns_theta_min         3.020
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  1.0000
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1456
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.50
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9605
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2339
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1007
_refine_ls_R_factor_gt           0.0448
_refine_ls_shift/su_max          0.000257
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 2.00 1.12 1.32 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0803
_refine_ls_wR_factor_gt          0.0522
_refine_ls_wR_factor_ref         0.0522
_reflns_limit_h_max              22
_reflns_limit_h_min              0
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              26
_reflns_limit_l_min              0
_reflns_number_gt                2339
_reflns_number_total             4435
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0448
_oxford_refine_ls_scale          0.4479(10)
_oxford_reflns_number_all        4435
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_oxford_structure_analysis_title 'CF solution in Pbca'
_cod_data_source_file            jo101273d_si_001.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P b c a '
_cod_original_formula_sum        'C19 H21 N1 O3 S1'
_cod_database_code               4025657