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_4023126
_publ_contact_author_address
;Department of Chemistry
University of Oxford
Chemistry Research Laboratory
Mansfield Road
Oxford
OX1 3TA
UK
;
_publ_contact_author_email       david.hogson@chem.ac.uk
_publ_contact_author_name        'David M. Hodgson'
_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_compound_source        'synthesis as described'
_chemical_formula_moiety         'C10 H19 N1 O2 S1'
_chemical_formula_sum            'C10 H19 N O2 S'
_chemical_formula_weight         217.33
_chemical_melting_point          374.5(5)
_chemical_name_systematic
N-((1RS,2RS,5SR)-bicyclo[3.1.0]hexan-2-yl)-2-methylpropane-2-sulfonamide
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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
_audit_creation_date             04-06-04
_audit_creation_method           CRYSTALS_ver_12.30
_cell_angle_alpha                90
_cell_angle_beta                 91.4596(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7827(5)
_cell_length_b                   6.0089(2)
_cell_length_c                   16.0233(7)
_cell_measurement_reflns_used    2375
_cell_measurement_temperature    150
_cell_measurement_theta_max      30
_cell_measurement_theta_min      5
_cell_volume                     1134.10(8)
_computing_cell_refinement       'Denzo/Scalepack (Otwinowski & Minor, 1996)'
_computing_data_collection       'COLLECT (Nonius BV, 1997)'
_computing_data_reduction        'Denzo/Scalepack (Otwinowski & Minor, 1996)'
_computing_molecular_graphics    'CAMERON (Watkin et al 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al 2003)'
_computing_structure_solution    'SIR92 (Altomare et al, 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.943
_diffrn_measured_fraction_theta_max 0.874
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.032
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2883
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.941
_diffrn_reflns_theta_min         5.315
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.262
_exptl_absorpt_correction_T_max  0.95
_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    1.273
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_recrystallization_method
'10 mg dissolved in 5 mL petrol/Et2O (7:3) and evaporated to dryness over 48 h'
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0606
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1619
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0575
_refine_ls_shift/su_max          0.000816
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 p=P(6)*max(Fo^2^,0) + (1-P(6))Fc^2^ 
 Method = SHELXL 97 (Sheldrick, 1997) 
 W = 1. / [Sigma^2^(F*)+(P(1)p)^2^+P(2)p+P(4)+P(5)Sin(theta) ] 
 P(i) are: 
 0.110 0.825 0.00 0.00 0.00 0.333 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1666
_refine_ls_wR_factor_gt          0.1636
_refine_ls_wR_factor_ref         0.1666
_reflns_limit_h_max              16
_reflns_limit_h_min              -16
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                1554
_reflns_number_total             2883
_reflns_threshold_expression     I>2.00u(I)
_cod_data_source_file            jo701901t-File008.cif
_cod_data_source_block           CRYSTALS_cif
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '374-375' was changed to '374.5(5)' -
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        'C10 H19 N1 O2 S1'
_cod_database_code               4023126