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_4023124
_publ_contact_author             'David Hodgson'
_publ_contact_author_email       David.Hodgson@chem.ox.ac.uk
_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 syn
_chemical_compound_source
;
synthesis as described
;
_chemical_formula_moiety         ' C24 H46 N2 O4 S2 '
_chemical_formula_sum            'C24 H46 N2 O4 S2'
_chemical_formula_weight         490.77
_chemical_melting_point          481
_chemical_name_systematic
; 
(2E,1S,4S)-N,N'-bis-(tert-butylsulfonyl)-1,4-dicyclohexyl-but-2-ene-1,4-diamine
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 112.6566(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.0205(2)
_cell_length_b                   9.4000(2)
_cell_length_c                   12.7518(3)
_cell_measurement_reflns_used    3151
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     1329.67(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_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.048
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14883
_diffrn_reflns_theta_full        27.481
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         5.103
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  0.95
_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    1.226
_exptl_crystal_description       ' prism '
_exptl_crystal_F_000             536
_exptl_crystal_preparation       acetone
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_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         0.65
_refine_diff_density_min         -0.43
_refine_ls_abs_structure_details 'Flack, 2271 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.04(6)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1186
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4423
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0347
_refine_ls_shift/su_max          0.007558
_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: 
 0.331 0.162 0.149 0.0791 0.0355 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0475
_refine_ls_wR_factor_gt          0.0344
_refine_ls_wR_factor_ref         0.0344
_reflns_limit_h_max              14
_reflns_limit_h_min              -15
_reflns_limit_k_max              12
_reflns_limit_k_min              -10
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                4423
_reflns_number_total             5484
_reflns_threshold_expression     I>3.00u(I)
_cod_data_source_file            jo701901t-File006.cif
_cod_data_source_block           ARC1132
_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 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        ' C24 H46 N2 O4 S2 '
_cod_database_code               4023124