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_4021647
_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 ad
_chemical_compound_source
;
?
;
_chemical_formula_moiety         ' C39 H60 N2 O5 S '
_chemical_formula_sum            'C39 H60 N2 O5 S'
_chemical_formula_weight         668.98
_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             05-10-01
_audit_creation_method           CRYSTALS_ver_12-03-99
_audit_update_record
;
2005-01-13 - Report on  C39 H60 N2 O5 S 
             by Anthony C. Willis
             for Connie Lee and Chris Easton
2005-01-14 - 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                   12.76750(10)
_cell_length_b                   15.20140(10)
_cell_length_c                   19.6121(2)
_cell_measurement_reflns_used    50173
_cell_measurement_temperature    200
_cell_measurement_theta_max      27
_cell_measurement_theta_min      3
_cell_volume                     3806.39(6)
_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
; 
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
;
_computing_publication_material
; 
 CRYSTALS (Watkin et al 2003) 
;
_computing_structure_refinement
; 
 CRYSTALS (Watkin et al 2003) 
;
_computing_structure_solution
; 
 SIR92 (Altomare et al, 1994) 
;
_diffrn_ambient_temperature      200
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
; 
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  0.08
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            70300
_diffrn_reflns_theta_full        27.112
_diffrn_reflns_theta_max         27.1
_diffrn_reflns_theta_min         2.619
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.957
_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    1.167
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ' plate '
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.26
_refine_ls_abs_structure_details 'Flack, 3731 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.06(5)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1260
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     425
_refine_ls_number_reflns         5042
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0276
_refine_ls_shift/su_max          0.000608
_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: 
 0.664 0.190 0.627 0.0337 0.159 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0385
_refine_ls_wR_factor_gt          0.0307
_refine_ls_wR_factor_ref         0.0307
_reflns_limit_h_max              16
_reflns_limit_h_min              -16
_reflns_limit_k_max              19
_reflns_limit_k_min              0
_reflns_limit_l_max              25
_reflns_limit_l_min              0
_reflns_number_gt                5042
_reflns_number_total             8395
_reflns_threshold_expression     I>3.00u(I)
_cod_data_source_file            jo0602569si20060207_061214.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 
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        ' C39 H60 N2 O5 S '
_cod_database_code               4021647