Regioselective Reduction of 3-Methoxymaleimides: An Efficient Method for the Synthesis of Methyl 5-Hydroxytetramates
Fatiah Issa; Joshua Fischer; Peter Turner; Mark J. Coster; Journal of Organic Chemistry 71 (2006) 4703–4705; doi:10.1021/jo0605750

data_4021751
_publ_section_title
;
 Regioselective Reduction of 3-Methoxymaleimides:
 An Efficient Method for the Synthesis of Methyl 5-Hydroxytetramates
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4703
_journal_page_last               4705
_journal_paper_doi               10.1021/jo0605750
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C12 H13 N O3'
_chemical_formula_weight         219.23
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      33
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.6992(3)
_cell_length_b                   6.3159(2)
_cell_length_c                   39.6797(15)
_cell_measurement_reflns_used    8777
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      3.08
_cell_volume                     2180.13(13)
_computing_cell_refinement       'SAINT (Bruker-Nonius,2003)'
_computing_data_collection       'APEX (Bruker-Nonius,2003)'
_computing_data_reduction        'SAINT and XPREP (Bruker-Nonius 2003)'
_computing_molecular_graphics
;
  xtal 3.6 (Hall,du Boulay, D.J. & Olthof-Hazekamp, R. 1999)
  ORTEPII  (Johnson,C.K., 1976). 
  WinGX (Farrugia, 1999)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, et. al. 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_crystal_treatment
;
attached with Exxon Paratone N, to a short length 
of fibre supported on a thin piece of copper wire 
inserted in a copper mounting pin.  The crystal was 
quenched in a cold nitrogen gas stream from an 
Oxford Cryosystems Cryostream. 
;
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_device_type  APEXII-FR591
_diffrn_measurement_method       \w+\f
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0946
_diffrn_reflns_av_sigmaI/netI    0.0836
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            30509
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         30.46
_diffrn_reflns_theta_min         3.08
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.472
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.117
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'could not be reliably determined'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.184
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3092
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.184
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.02P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0678
_refine_ls_wR_factor_ref         0.0689
_reflns_number_gt                3707
_reflns_number_total             5902
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0605750si20060315_081557.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_Hall     'P 2c -2n    '
_cod_original_sg_symbol_H-M      'P n a 21    '
_cod_database_code               4021751