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_4025983
_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 calculation and graphics software, see: Spek (2003), Farrugia (1999),
Macrae <i>et al.</i> (2006).

For H-bonding motifs see: Bernstein <i>et al.</i> (1995).

For absolute configuration literature, see: Hooft <i>et al.</i> (2009).
;
_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         'C15 H21 N O5'
_chemical_formula_sum            'C15 H21 N O5'
_chemical_formula_weight         295.33
_chemical_name_systematic
;
3-(2,2-Dimethyl-propoxycarbonylamino)-2-hydroxy-3-phenyl-propionic acid methyl
ester
;
_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
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.2982(3)
_cell_length_b                   10.8741(6)
_cell_length_c                   26.5635(19)
_cell_measurement_reflns_used    4640
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      71.9
_cell_measurement_theta_min      6.7
_cell_volume                     1530.41(16)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0475
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13212
_diffrn_reflns_theta_full        46.37
_diffrn_reflns_theta_max         46.37
_diffrn_reflns_theta_min         6.67
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.799
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.721
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR, Higashi (1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.110
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 'Flack(1983), 501 Bijvoet pairs'
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_coef       0.0043(6)
_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   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         1311
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0306
_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^)+(0.0595P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0770
_refine_ls_wR_factor_ref         0.0789
_reflns_number_gt                1242
_reflns_number_total             1311
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1018816_si_003.cif
_cod_data_source_block           compound_23a
_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 (4 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               4025983