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_4021642
_publ_contact_author_address
;
Research School of Chemistry,
Australian National University,
Canberra, ACT 0200, Australia
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_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_formula_moiety         'C14 H16 N2 O2 '
_chemical_formula_sum            'C14 H16 N2 O2'
_chemical_formula_weight         244.29
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_audit_creation_date             2001-03-02
_audit_creation_method           'by teXsan v1.8'
_audit_update_record
;
2001-03-02 - Report on C14 H16 N2 O2
             by Anthony C. Willis
             for Connie K. Y. Lee and Christopher J. Easton
2001-03-02 - passes checkcif tests with minor warnings
             *  the crystal is of VERY poor quality and data are weak.   
             * range in absorption transmission coeffs larger than expected: 
               sortav absorption also compensating for shortcomings in the
               quality of the crystal etc..  
;
_cell_angle_alpha                90
_cell_angle_beta                 101.967(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.7154(4)
_cell_length_b                   28.899(2)
_cell_length_c                   7.9525(6)
_cell_measurement_reflns_used    55683
_cell_measurement_temperature    200.0
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      2.26
_cell_volume                     1285.0(2)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       KappaCCD
_computing_data_reduction        'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_publication_material  'teXsan (MSC, 1992-1997)'
_computing_structure_refinement  'teXsan (MSC, 1992-1997)'
_computing_structure_solution
;
SIR92 (Altomare, et. al. 1994)
;
_diffrn_ambient_temperature      200.0
_diffrn_measured_fraction_theta_full .99
_diffrn_measured_fraction_theta_max .99
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ' \f and \w scans with CCD '
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      -0.08016
_diffrn_orient_matrix_UB_12      0.15270
_diffrn_orient_matrix_UB_13      0.04738
_diffrn_orient_matrix_UB_21      0.02121
_diffrn_orient_matrix_UB_22      0.01762
_diffrn_orient_matrix_UB_23      -0.02090
_diffrn_orient_matrix_UB_31      -0.09376
_diffrn_orient_matrix_UB_32      0.00913
_diffrn_orient_matrix_UB_33      -0.08745
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.052
_diffrn_reflns_av_sigmaI/netI    0.100
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10519
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.62
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  .999
_exptl_absorpt_correction_T_min  0.834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995) inplemented in maXus (2000)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_meas      ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             520.00
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.29
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.689
_refine_ls_goodness_of_fit_ref   1.898
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     169
_refine_ls_number_reflns         1275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1643
_refine_ls_R_factor_gt           0.0729
_refine_ls_shift/su_max          0.0170
_refine_ls_shift/su_mean         0.0060
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[\s^2^(Fo) + 0.00040|Fo|^2^]'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.0807
_refine_ls_wR_factor_ref         0.0672
_reflns_number_gt                1275
_reflns_number_total             2190
_reflns_threshold_expression     I>2.00\s(I)
_cod_data_source_file            jo0602569si20060207_060959.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
data name '_geom_bond_atom_site_label_D' replaced with
'_geom_hbond_atom_site_label_D' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_bond_atom_site_label_H' replaced with
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'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_bond_atom_site_label_A' replaced with
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'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_bond_distance_DH' replaced with '_geom_hbond_distance_DH'
as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_contact_distance_HA' replaced with
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'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_contact_distance_DA' replaced with
'_geom_hbond_distance_DA' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_angle_DHA' replaced with '_geom_hbond_angle_DHA' as
specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_contact_site_symmetry_A' replaced with
'_geom_hbond_site_symmetry_A' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 5005 2017-03-03 11:38:54Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/a     '
_cod_original_formula_sum        'C14 H16 N2 O2 '
_cod_database_code               4021642