Synthesis of 2-Chloro-2-imidoylaziridines via Aza-Darzens-type Reaction of 3,3-Dichloro-1-azaallylic Anions and N-(Arylsulfonyl)imines
Nicola Giubellina; Sven Mangelinckx; Karl W. Törnroos; Norbert De Kimpe; Journal of Organic Chemistry 71 (2006) 5881–5887; doi:10.1021/jo060241a

data_4021833
_publ_section_title
;
 Synthesis of 2-Chloro-2-imidoylaziridines via Aza-Darzens-type
 Reaction of 3,3-Dichloro-1-azaallylic Anions
 and N-(Arylsulfonyl)imines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5881
_journal_page_last               5887
_journal_paper_doi               10.1021/jo060241a
_journal_volume                  71
_journal_year                    2006
_chemical_formula_moiety         'C24 H24 Cl2 N2 O2 S'
_chemical_formula_sum            'C24 H24 Cl2 N2 O2 S'
_chemical_formula_weight         475.41
_chemical_name_systematic
; 
Syn-N-[(cis-1-benzenesulfonyl-2-chloro-3-(4-chlorophenyl)
aziridin-2-yl)phenylmethyl]isopropylamine
;
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           'KWT manual based on SHELXL-97'
_cell_angle_alpha                90.00
_cell_angle_beta                 116.0520(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.9628(5)
_cell_length_b                   11.9516(4)
_cell_length_c                   15.2533(5)
_cell_measurement_reflns_used    14646
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      30.062
_cell_measurement_theta_min      2.261
_cell_volume                     2286.81(13)
_computing_cell_refinement       'SAINT, V6.45A (Bruker AXS, 2003)'
_computing_data_collection       'SMART, V5.054 (Bruker AXS, 1999)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker AXS, 2003)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker-AXS SMART 2K CCD'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0123
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            37813
_diffrn_reflns_theta_full        30.06
_diffrn_reflns_theta_max         30.06
_diffrn_reflns_theta_min         2.26
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  '30 hours'
_diffrn_standards_number         791
_exptl_absorpt_coefficient_mu    0.399
_exptl_absorpt_correction_T_max  0.92652
_exptl_absorpt_correction_T_min  0.81091
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
FACE     0.00 -1.00  1.00     0.106 
FACE     0.00  1.00 -1.00     0.106 
FACE     0.00  1.00  1.00     0.125 
FACE     0.00 -1.00 -1.00     0.125 
FACE    -1.00  1.00  0.00     0.290 
FACE    -1.00  0.00 -1.00     0.220 
FACE    -1.00 -1.00  0.00     0.300 
FACE    -2.00 -1.00  5.00     0.210 
FACE     2.00 -1.00 -1.00     0.290 

Bruker AXS (2003). SHELXTL. Version 6.14. 
Bruker AXS Inc., Madison, Wisconsin, USA. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Complex prism'
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         6698
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0296
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0418P)^2^+0.7940P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0829
_reflns_number_gt                6079
_reflns_number_total             6698
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo060241asi20060206_041937.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.

'_exptl_absorpt_correction_type' value 'Numerical' changed to
'numerical' 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/n'
_cod_database_code               4021833