Dimerization and Isomerization Reactions of α-Lithiated Terminal Aziridines
David M. Hodgson; Philip G. Humphreys; Steven M. Miles; Christopher A. J. Brierley; John G. Ward; Journal of Organic Chemistry 72 (2007) 10009–10021; doi:10.1021/jo701901t

data_4023127
_publ_contact_author_address
;Department of Chemistry 
University of Oxford
Chemistry Research Laboratory
Mansfield Road
Oxford
OX1 3TA
United Kingdom
;
_publ_contact_author_email       david.hodgson@chem.ox.ac.uk
_publ_contact_author_name        'Prof. David M. Hodgson'
_publ_contact_author_phone       '01865 275697'
_publ_section_title
;
 Dimerization and Isomerization Reactions of
 \a-Lithiated Terminal Aziridines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10009
_journal_page_last               10021
_journal_paper_doi               10.1021/jo701901t
_journal_volume                  72
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C12 H23 N O2 S'
_chemical_formula_sum            'C12 H23 N O2 S'
_chemical_formula_weight         245.39
_chemical_melting_point          373
_space_group_IT_number           33
_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
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.0101(6)
_cell_length_b                   6.2216(2)
_cell_length_c                   9.5931(3)
_cell_measurement_reflns_used    8342
_cell_measurement_temperature    150
_cell_measurement_theta_max      28
_cell_measurement_theta_min      5
_cell_volume                     1313.66(7)
_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_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.034
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8342
_diffrn_reflns_theta_full        27.462
_diffrn_reflns_theta_max         27.462
_diffrn_reflns_theta_min         5.384
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 Denzo/Scalepack (Otwinowski & Minor, 1996) 
;
_exptl_crystal_colour            ' colourless '
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_description       ' prism '
_exptl_crystal_F_000             536
_exptl_crystal_recrystallization_method
'Slow evaporation from petroleum ether / diethyl ether mixture'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_crystal_thermal_history
; 
The material was crystallised at ambient temperature. A suitable crystal 
was cooled rapidly to 150K for single-crystal X-ray diffraction analysis. 
;
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.24
_refine_ls_abs_structure_details 'Flack, 1219 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.43(7)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1147
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2286
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0300
_refine_ls_shift/su_max          0.001363
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 0.320 0.0346 0.0674 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0458
_refine_ls_wR_factor_gt          0.0309
_refine_ls_wR_factor_ref         0.0309
_reflns_limit_h_max              28
_reflns_limit_h_min              0
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              12
_reflns_limit_l_min              -12
_reflns_number_gt                2286
_reflns_number_total             2973
_reflns_threshold_expression     I>3.00u(I)
_cod_data_source_file            jo701901t-File009.cif
_cod_data_source_block           arc1118
_cod_database_code               4023127