Organolithium-Induced Alkylative Ring Opening of Aziridines: Synthesis of Unsaturated Amino Alcohols and Ethers
David M. Hodgson; Bogdan Štefane; Timothy J. Miles; Jason Witherington; Journal of Organic Chemistry 71 (2006) 8510–8515; doi:10.1021/jo0615201

data_4022049
_publ_contact_author_address
;
Faculty of Chemistry and Chemical Technology
University of Ljubljana
A\<sker\<ceva 5, P. O. Box 537
1000 Ljubljana
Slovenia
;
_publ_contact_author_email       bogdan.stefane@fkkt.uni-lj.si
_publ_contact_author_name        'Bogdan \<Stefane'
_publ_section_title
;
 Organolithium-Induced Alkylative Ring Opening of
 Aziridines: Synthesis of Unsaturated Amino Alcohols and Ethers
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8510
_journal_page_last               8515
_journal_paper_doi               10.1021/jo0615201
_journal_volume                  71
_journal_year                    2006
_chemical_compound_source
;
synthesis as described
;
_chemical_formula_moiety         ' C11 H13 N1 O3 S1 '
_chemical_formula_sum            'C11 H13 N O3 S'
_chemical_formula_weight         239.29
_chemical_melting_point          390.4(3)
_chemical_name_systematic
;
6-[(4-Methylphenyl)sulfonyl]-3-oxa-6-azabicyclo[3.1.0]hexane
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 90.5392(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0038(2)
_cell_length_b                   8.1286(2)
_cell_length_c                   23.0641(7)
_cell_measurement_reflns_used    9426
_cell_measurement_temperature    150
_cell_measurement_theta_max      28
_cell_measurement_theta_min      5
_cell_volume                     1125.5
_computing_cell_refinement
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
_computing_data_collection
;
KappaCCD software 'Collect' (Nonius, 2000)
;
_computing_data_reduction
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
_computing_publication_material
;
CRYSTALS (Watkin et al, 2001)
;
_computing_structure_refinement
;
CRYSTALS (Watkin et al, 2001)
;
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1992)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type
;
Nonius KappaCCD
;
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.040
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            9426
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         5.32
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.279
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 Denzo/Scalepack (Otwinowski & Minor, 1996)
;
_exptl_crystal_colour            ' colourless '
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_description       ' fragment '
_exptl_crystal_F_000             504.573
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.43
_refine_diff_density_min         -0.39
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0548
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1724
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.003528
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Chebychev polynomial with 3 parameters (Carruthers & Watkin , 1979)
0.882    0.350    0.501
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0485
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              29
_reflns_limit_l_min              0
_reflns_number_gt                1724
_reflns_number_total             2517
_reflns_threshold_expression     >3.00\s(I)
_cod_data_source_file            jo0615201si20060808_124111_1.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 

The following automatic conversions were performed:

'_chemical_melting_point' value '117-117.5 \%C' was changed to
'390.4(3)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        ' C11 H13 N1 O3 S1 '
_cod_database_code               4022049