4-Alkoxycarbonyl- and Aminocarbonyl-Substituted Isoxazoles as Masked Acrylates and Acrylamides in the Asymmetric Synthesis of Δ^2^-Isoxazolines
Connie K. Y. Lee; Anthony J. Herlt; Gregory W. Simpson; Anthony C. Willis; Christopher J. Easton; Journal of Organic Chemistry 71 (2006) 3221–3231; doi:10.1021/jo0602569

data_4021646
_publ_contact_author_address
;
Research School of Chemistry,
Australian National University,
Canberra, ACT 0200, Australia
;
_publ_contact_author_email       ' easton@rsc.anu.edu.au '
_publ_contact_author_fax         ' 61 2 6125 8114 '
_publ_contact_author_name        ' Christopher J. Easton '
_publ_contact_author_phone       ' 61 2 6125 8201 '
_publ_section_title
;
 4-Alkoxycarbonyl- and Aminocarbonyl-Substituted Isoxazoles
 as Masked Acrylates and Acrylamides in the Asymmetric
 Synthesis of \D^2^-Isoxazolines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3221
_journal_page_last               3231
_journal_paper_doi               10.1021/jo0602569
_journal_volume                  71
_journal_year                    2006
_chemical_absolute_configuration syn
_chemical_compound_source
;
?
;
_chemical_formula_moiety         ' C29 H37 N O3 '
_chemical_formula_sum            'C29 H37 N O3'
_chemical_formula_weight         447.62
_chemical_melting_point          ?
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             01-08-11
_audit_creation_method           CRYSTALS_ver_12-03-99
_audit_update_record
;
2001-11-13 - Report on C29 H37 N2 O3
             by Anthony C. Willis
             for Connie K. Y. Lee and Christopher J. Easton
2001-11-13 - passes checkcif tests with minor warnings
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6385(1)
_cell_length_b                   11.8594(1)
_cell_length_c                   29.2414(4)
_cell_measurement_reflns_used    57028
_cell_measurement_temperature    200
_cell_measurement_theta_max      27
_cell_measurement_theta_min      3
_cell_volume                     2648.92(5)
_computing_cell_refinement
; 
 Denzo/Scalepack (Otwinowski & Minor, 1996) 
;
_computing_data_collection
; 
 COLLECT (Nonius BV, 1997) 
;
_computing_data_reduction
; 
 Denzo/Scalepack (Otwinowski & Minor, 1996) 
;
_computing_molecular_graphics
; 
teXsan (MSC, 1992-1997)
;
_computing_publication_material
; 
 CRYSTALS (Watkin et al 2001) 
;
_computing_structure_refinement
; 
 CRYSTALS (Watkin et al 2001) 
;
_computing_structure_solution
; 
 SIR92 (Altomare et al, 1994) 
;
_diffrn_ambient_temperature      200
_diffrn_measured_fraction_theta_full .99
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type
; 
Enraf Nonius Kappa CCD 
;
_diffrn_measurement_method       ' \f and \w scans with CCD '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.044
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            44477
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         4.22
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
via Gaussian method (Coppens, 1970) implemented in maXus (2000)
;
_exptl_crystal_colour            ' colourless '
_exptl_crystal_density_diffrn    1.122
_exptl_crystal_density_meas      ?
_exptl_crystal_description       ' block '
_exptl_crystal_F_000             968.
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.12
_refine_ls_abs_structure_details
;
An attempt to refine a Flack parameter to determine the absolute configuration
gave an inconclusive result.
However the chirality of the (1R,2S)-trans-2-phenyl-1-cyclohexanol synthetic 
precursor is known, so the absolute configuration can be assigned on this 
basis.
;
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0422
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         1939
_refine_ls_R_factor_gt           0.0353
_refine_ls_shift/su_max          0.000205
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Chebychev polynomial with 4 parameters, Carruthers & Watkin , 1979, 
0.685    -.426    0.330    -.306    
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0381
_reflns_limit_h_max              9
_reflns_limit_h_min              0
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              37
_reflns_limit_l_min              0
_reflns_number_gt                1939
_reflns_number_total             3466
_reflns_threshold_expression     >3.00\s(I)
_cod_data_source_file            jo0602569si20060207_061152.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic ' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        ' C29 H37 N O3 '
_cod_database_code               4021646