Radical addition of nitrones to acrylates mediated by SmI2: asymmetric synthesis of ?-amino acids employing carbohydrate-based chiral auxiliariesElectronic Supplementary Information (ESI) available: crystallographic data of 2b and 4a, experimental procedure and spectral data. See http://www.rsc.org/suppdata/cc/b4/b405141f/
Johannesen, Sine A.; Albu, Silvia; Hazell, Rita G.; Skrydstrup, Troels; Chemical Communications  (2004) 1962–1963; doi:10.1039/b405141f

data_7111316
_publ_section_title
;
 Radical addition of nitrones to acrylates mediated by SmI2: asymmetric
 synthesis of ?-amino acids employing carbohydrate-based chiral
 auxiliariesElectronic Supplementary Information (ESI) available:
 crystallographic data of 2b and 4a, experimental procedure and spectral
 data. See http://www.rsc.org/suppdata/cc/b4/b405141f/
;
_journal_issue                   17
_journal_name_full               'Chemical Communications'
_journal_page_first              1962
_journal_page_last               1963
_journal_paper_doi               10.1039/b405141f
_journal_year                    2004
_chemical_formula_moiety         'C23 H41 N O8'
_chemical_formula_sum            'C23 H41 N O8'
_chemical_formula_weight         459.57
_chemical_name_systematic
;
(R)-N-(3-buthoxycarbonyl-1-isopropyl)-2,3:5,6-bis-O-
isopropylidene-D-mannose-imine N-oxide
;
_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_type_scat_source           IntTabIV
_cell_angle_alpha                90.000
_cell_angle_beta                 90.000
_cell_angle_gamma                90.000
_cell_formula_units_Z            4
_cell_length_a                   6.540(7)
_cell_length_b                   19.97(2)
_cell_length_c                   20.00(2)
_cell_measurement_reflns_used    4994
_cell_measurement_temperature    120
_cell_measurement_theta_max      26.61
_cell_measurement_theta_min      2.88
_cell_volume                     2612(5)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics
;
ORTEP-III (Burnett & Johnson,  1996), KRYSTAL
;
_computing_publication_material  KRYSTAL
_computing_structure_refinement  'modified ORFLS(1962), KRYSTAL'
_computing_structure_solution
;
SIR97 (Altomare et al., 1997 ), KRYSTAL
;
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Siemens SMART CCD diffractometer'
_diffrn_measurement_method       '\w rotation scans with narrow frames'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'x-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.19
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            45712
_diffrn_reflns_reduction_process 45712
_diffrn_reflns_theta_full        26.61
_diffrn_reflns_theta_max         26.61
_diffrn_reflns_theta_min         2.88
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.28(6)
_refine_diff_density_min         -0.24(6)
_refine_ls_extinction_coef       524(48)
_refine_ls_extinction_method
;
Type 1 Lorentzian isotropic ( Becker and Coppens, 1974)
;
_refine_ls_goodness_of_fit_ref   1.235
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     290
_refine_ls_number_reflns         1922
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.049
_refine_ls_shift/su_max          0.00019
_refine_ls_shift/su_mean         0.00003
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
w= 1/{[\s~cs~(F^2^)+B+(1+A)F^2^]^1/2^- |F|}^2^
where A = 0.03   and B = 0.0
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.047
_reflns_number_gt                1922
_reflns_number_total             3145
_reflns_threshold_expression     I>3\s(I)
_cod_data_source_file            b405141fsup1.cif
_cod_data_source_block           sine2b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

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
'_geom_hbond_atom_site_label_H' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_contact_atom_site_label_a' replaced with
'_geom_hbond_atom_site_label_A' as specified in the replacement file
'/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
'_geom_hbond_distance_HA' as specified in the replacement file
'/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      'P21 21 21'
_cod_database_code               7111316