Alkyl 4-Chlorobenzoyloxycarbamates as Highly Effective Nitrogen Source Reagents for the Base-Free, Intermolecular Aminohydroxylation Reaction
Lawrence Harris; Simon P. H. Mee; Richard H. Furneaux; Graeme J. Gainsford; Andreas Luxenburger; Journal of Organic Chemistry 76 (2011) 358–372; doi:10.1021/jo1018816

data_4025984
_publ_contact_author_address
;Industrial Research Limited
 PO Box 31-310
 Lower Hutt
 New Zealand
;
_publ_contact_author_email       g.gainsford@irl.cri.nz
_publ_contact_author_fax         '64(4)931 0142'
_publ_contact_author_name        'Gainsford, Graeme J.'
_publ_contact_author_phone       '64(4)931 3815'
_publ_section_related_literature
;
For ring conformations see: Cremer & Pople (1975).
For calculation and graphics software, see: Spek (2009),
Farrugia (1997), Macrae <i>et al.</i> (2008).

For h-bonding motifs see: Bernstein <i>et al.</i> (1995).
;
_publ_section_title
;
 Alkyl 4-Chlorobenzoyloxycarbamates as Highly Effective Nitrogen Source
 Reagents for the Base-Free, Intermolecular Aminohydroxylation Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              358
_journal_page_last               372
_journal_paper_doi               10.1021/jo1018816
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C11 H11 N O4'
_chemical_formula_sum            'C11 H11 N O4'
_chemical_formula_weight         221.21
_chemical_name_systematic
;

2-Oxo-4-phenyl-oxazolidine-5-carboxylic acid methyl ester 

;
_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
_audit_update_record
;
2008-09-29 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 108.428(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.2984(3)
_cell_length_b                   5.8941(2)
_cell_length_c                   11.0767(8)
_cell_measurement_reflns_used    4697
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      71.9
_cell_measurement_theta_min      8.03
_cell_volume                     514.00(5)
_computing_cell_refinement
; 
    FSProcess in Process-auto (Rigaku, 1998)
;
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction
; 
    FSProcess in Process-auto (Rigaku, 1998)
;
_computing_molecular_graphics
;
 ORTEP in Wingx (Farrugia, 1999)
;
_computing_publication_material
;
 SHELXL-97 (Sheldrick, 2008); PLATON (Spek, 2003)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      '551 images in steps of 1\%'
_diffrn_measurement_device_details 'Curved image plate'
_diffrn_measurement_device_type
;  
Rigaku Spider 
;
_diffrn_measurement_method       \w-scans
_diffrn_radiation_monochromator
;
Rigaku VariMax-HF Confocal Optical System
;
_diffrn_radiation_source
;
 Rigaku MM007 rotating anode
;
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9452
_diffrn_reflns_theta_full        65.00
_diffrn_reflns_theta_max         65.00
_diffrn_reflns_theta_min         8.03
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.928
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.8482
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR, Higashi (1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_description       needle
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 'Flack (1983), 753 bijvoet pairs'
_refine_ls_abs_structure_Flack   -0.02(19)
_refine_ls_extinction_coef       0.0099(11)
_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   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         1712
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0271
_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^)+(0.0311P)^2^+0.0625P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0629
_refine_ls_wR_factor_ref         0.0658
_reflns_number_gt                1586
_reflns_number_total             1712
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1018816_si_004.cif
_cod_data_source_block           compound_25
_cod_depositor_comments
;
The following automatic conversions were performed:

'_geom_hbond_publ_flag' value 'YES' changed to 'yes' 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 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4025984