Ring-opening and -expansion of 2,2'-biaziridine: access to diverse enantiopure linear and bicyclic vicinal diamines.
Bailey, Stephen J.; Wales, Steven M.; Willis, Anthony C.; Keller, Paul A.; Organic letters 16 (2014) 4344–4347; doi:10.1021/ol502164b

data_1517506
_publ_section_title
;
 Ring-opening and -expansion of 2,2'-biaziridine: access to diverse
 enantiopure linear and bicyclic vicinal diamines.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4344
_journal_page_last               4347
_journal_paper_doi               10.1021/ol502164b
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_compound_source        ' from U of Wollongong'
_chemical_formula_moiety         'C18 H20 N2 O4 S2'
_chemical_formula_sum            'C18 H20 N2 O4 S2'
_chemical_formula_weight         392.50
_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
_audit_creation_date             11-07-22
_audit_creation_method           CRYSTALS_ver_14.11
_audit_update_record
;
2011-07-22 - Report on C18 H20 N2 O4 S2
             by Anthony C. Willis
             for Paul Keller

2011-07-22 - passes checkcif tests with minor warnings  
;
_cell_angle_alpha                90
_cell_angle_beta                 91.7472(14)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.5547(2)
_cell_length_b                   13.2602(3)
_cell_length_c                   9.4580(2)
_cell_measurement_reflns_used    15134
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     947.03(4)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
; 
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
;
_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      200
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ' \f and \w scans with CCD '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            19578
_diffrn_reflns_theta_full        27.505
_diffrn_reflns_theta_max         27.505
_diffrn_reflns_theta_min         2.646
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.307
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_correction_T_min  0.882
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
via Gaussian method (Coppens, 1970) implemented in maXus (2000)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.34
_refine_ls_abs_structure_details 'Flack (1983), 2078 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.02(5)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9999
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         4347
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0297
_refine_ls_shift/su_max          0.0055425
_refine_ls_shift/su_mean         0.0005891
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.13P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0767
_refine_ls_wR_factor_gt          0.0747
_refine_ls_wR_factor_ref         0.0767
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              17
_reflns_limit_k_min              -17
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                4046
_reflns_number_total             4349
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.95
_oxford_diffrn_Wilson_scale      0.78
_oxford_refine_ls_r_factor_ref   0.0333
_oxford_refine_ls_scale          1.144(4)
_oxford_reflns_number_all        4347
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title '7211149 wol1105'
_cod_data_source_file            ol502164b_si_007.cif
_cod_data_source_block           wol1105
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_database_code               1517506
_iucr_refine_instruction_details_constraints
;
BLOCK 
CONT SCALE 
CONT S    (    1 ,X'S,U'S)  UNTIL C    (   18 ) 
CONT H    (   11 ,X'S)  UNTIL H    (  183 ) 
CONT ENANTIO 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM            3 H ON SP 3 
DIST 0.96, 0.02 = 
CONT C ( 11) TO H(111) 
CONT C ( 11) TO H(112) 
CONT C ( 11) TO H(113) 
REST 0.111, 0.002 = H(111,U[ISO]) 
REST 0.111, 0.002 = H(112,U[ISO]) 
REST 0.111, 0.002 = H(113,U[ISO]) 
ANGLE 109.54, 2.0 = 
CONT C(8) TO C ( 11) TO H(111) 
CONT C(8) TO C ( 11) TO H(112) 
CONT C(8) TO C ( 11) TO H(113) 
ANGLE 0.0, 2.0 = MEAN H(111) TO C ( 11) TO H(112) 
CONT H(111) TO C ( 11) TO H(113) 
CONT H(112) TO C ( 11) TO H(113) 
REM            3 H ON SP 3 
DIST 0.96, 0.02 = 
CONT C ( 18) TO H(181) 
CONT C ( 18) TO H(182) 
CONT C ( 18) TO H(183) 
REST 0.087, 0.002 = H(181,U[ISO]) 
REST 0.087, 0.002 = H(182,U[ISO]) 
REST 0.087, 0.002 = H(183,U[ISO]) 
ANGLE 109.54, 2.0 = 
CONT C(15) TO C ( 18) TO H(181) 
CONT C(15) TO C ( 18) TO H(182) 
CONT C(15) TO C ( 18) TO H(183) 
ANGLE 0.0, 2.0 = MEAN H(181) TO C ( 18) TO H(182) 
CONT H(181) TO C ( 18) TO H(183) 
CONT H(182) TO C ( 18) TO H(183) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;