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_1517508
_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         'C24 H28 N2 O4 S2'
_chemical_formula_sum            'C24 H28 N2 O4 S2'
_chemical_formula_weight         472.63
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             14-03-14
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2014-03-14 - Report on C24 H28 N2 O4 S2
             by Anthony C. Willis
             for Paul Keller

2014-03-14 - passes checkcif tests with minor warnings  
;
_cell_angle_alpha                90
_cell_angle_beta                 127.7224(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.6086(7)
_cell_length_b                   7.9486(1)
_cell_length_c                   15.1824(4)
_cell_measurement_reflns_used    20061
_cell_measurement_temperature    200
_cell_measurement_theta_max      30
_cell_measurement_theta_min      3
_cell_volume                     2349.02(10)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.066
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21013
_diffrn_reflns_theta_full        30.012
_diffrn_reflns_theta_max         30.012
_diffrn_reflns_theta_min         2.683
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_correction_T_min  0.909
_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    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.240
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.32
_refine_ls_abs_structure_details 'Flack (1983), 2958 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.02(5)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9907
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         6608
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.0069959
_refine_ls_shift/su_mean         0.0002539
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.06P)^2^ + 1.05P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0991
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.0991
_reflns_limit_h_max              27
_reflns_limit_h_min              -34
_reflns_limit_k_max              11
_reflns_limit_k_min              -9
_reflns_limit_l_max              21
_reflns_limit_l_min              0
_reflns_number_gt                6134
_reflns_number_total             6611
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.13
_oxford_diffrn_Wilson_scale      1.23
_oxford_refine_ls_r_factor_ref   0.0414
_oxford_refine_ls_scale          0.990(3)
_oxford_reflns_number_all        6608
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'kel1402 At 14:54 on 14/ 3'
_cod_data_source_file            ol502164b_si_006.cif
_cod_data_source_block           kel1402
_cod_original_sg_symbol_Hall     'C 2y '
_cod_original_sg_symbol_H-M      'C 1 2 1 '
_cod_database_code               1517508
_iucr_refine_instruction_details_constraints
;
BLOCK 
CONT SCALE 
CONT N    (    1 ,X'S,U'S)  UNTIL C    (   32 ) 
CONT H    (   21 ,X'S)  UNTIL H    (  323 ) 
CONT ENANTIO 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM            3 H ON SP 3 
DIST 0.96, 0.02 = 
CONT C ( 22) TO H(221) 
CONT C ( 22) TO H(222) 
CONT C ( 22) TO H(223) 
REST 0.105, 0.002 = H(221,U[ISO]) 
REST 0.105, 0.002 = H(222,U[ISO]) 
REST 0.105, 0.002 = H(223,U[ISO]) 
ANGLE 109.54, 2.0 = 
CONT C(19) TO C ( 22) TO H(221) 
CONT C(19) TO C ( 22) TO H(222) 
CONT C(19) TO C ( 22) TO H(223) 
ANGLE 0.0, 2.0 = MEAN H(221) TO C ( 22) TO H(222) 
CONT H(221) TO C ( 22) TO H(223) 
CONT H(222) TO C ( 22) TO H(223) 
REM            3 H ON SP 3 
DIST 0.96, 0.02 = 
CONT C ( 32) TO H(321) 
CONT C ( 32) TO H(322) 
CONT C ( 32) TO H(323) 
REST 0.135, 0.002 = H(321,U[ISO]) 
REST 0.135, 0.002 = H(322,U[ISO]) 
REST 0.135, 0.002 = H(323,U[ISO]) 
ANGLE 109.54, 2.0 = 
CONT C(29) TO C ( 32) TO H(321) 
CONT C(29) TO C ( 32) TO H(322) 
CONT C(29) TO C ( 32) TO H(323) 
ANGLE 0.0, 2.0 = MEAN H(321) TO C ( 32) TO H(322) 
CONT H(321) TO C ( 32) TO H(323) 
CONT H(322) TO C ( 32) TO H(323) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;