5-Hydroxyalkyl derivatives of <i>tert</i>-butyl 2-oxo-2,5-dihydro-1<i>H</i>-pyrrole-1-carboxylate: diastereoselectivity of the Mukaiyama crossed-aldol-type reaction
Vallat, Olivier; Buciumas, Ana-Maria; Neier, Reinhard; Stoeckli-Evans, Helen; Acta Crystallographica Section C 65 (2009) o171–o175; doi:10.1107/S0108270109008877

data_2017046
_publ_section_title
;
 5-Hydroxyalkyl derivatives of <i>tert</i>-butyl
 2-oxo-2,5-dihydro-1<i>H</i>-pyrrole-1-carboxylate:
 diastereoselectivity of the Mukaiyama crossed-aldol-type reaction
;
_journal_coeditor_code           GA3120
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o171
_journal_page_last               o175
_journal_paper_doi               10.1107/S0108270109008877
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C13 H20 Br N O4'
_chemical_formula_moiety         'C13 H20 Br N O4'
_chemical_formula_sum            'C13 H20 Br N O4'
_chemical_formula_weight         334.21
_chemical_name_systematic
;
<i>tert</i>-butyl
2-(4-bromo-1-hydroxybutyl)-5-oxo-2,5-dihydro-1<i>H</i>-pyrrole-1-carboxylate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                104.176(7)
_cell_angle_beta                 113.759(7)
_cell_angle_gamma                101.367(8)
_cell_formula_units_Z            2
_cell_length_a                   8.8340(9)
_cell_length_b                   9.0750(9)
_cell_length_c                   10.7283(10)
_cell_measurement_reflns_used    12982
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.74
_cell_measurement_theta_min      2.23
_cell_volume                     719.57(14)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2006)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2006)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2006)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and PLATON  (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 0.81\%A
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Stoe IPDS-2'
_diffrn_measurement_method       '\f and \w'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0264
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9956
_diffrn_reflns_theta_full        29.20
_diffrn_reflns_theta_max         29.20
_diffrn_reflns_theta_min         2.22
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.866
_exptl_absorpt_correction_T_max  0.47217
_exptl_absorpt_correction_T_min  0.30730
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(MULscanABS in PLATON; Spek, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.50
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.779
_refine_ls_extinction_coef       0.012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         3862
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0270
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0236P)^2^+0.4857P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0647
_refine_ls_wR_factor_ref         0.0662
_reflns_number_gt                3587
_reflns_number_total             3862
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ga3120.cif
_cod_data_source_block           III
_cod_original_cell_volume        719.57(12)
_cod_database_code               2017046
_cod_database_fobs_code          2017046