Synthesis of Unnatural Selenocystines and β-Aminodiselenides via Regioselective Ring-Opening of Sulfamidates Using a Sequential, One-Pot, Multistep Strategy
Nasir Baig Rashid Baig; R. N. Chandrakala; V. Sai Sudhir; Srinivasan Chandrasekaran; Journal of Organic Chemistry 75 (2010) 2910–2921; doi:10.1021/jo1001388

data_4025389
_publ_contact_author_address
; 
 Department of Organic Chemistry
 Indian Institute of Science
 Bangalore, 560 012
 India
;
_publ_contact_author_name
; 
 'Srinivasan Chandrasekaran'
;
_publ_section_title
;
 Synthesis of Unnatural Selenocystines and \b-Aminodiselenides via
 Regioselective Ring-Opening of Sulfamidates Using a Sequential, One-Pot,
 Multistep Strategy
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2910
_journal_page_last               2921
_journal_paper_doi               10.1021/jo1001388
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration unk
_chemical_compound_source        'see text'
_chemical_formula_moiety         'C44 H50 N4 O10 Se2'
_chemical_formula_sum            'C44 H50 N4 O10 Se2'
_chemical_formula_weight         952.80
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             'Dec 20 17:51:27 2009'
_audit_creation_method           SHELXL-97
_audit_update_record
;
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.3000(4)
_cell_length_b                   16.5434(5)
_cell_length_c                   20.9360(8)
_cell_measurement_reflns_used    46013
_cell_measurement_temperature    293
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      1.57
_cell_volume                     4606.5(3)
_computing_cell_refinement       Apex2
_computing_data_collection       'Bruker kappa Apex2'
_computing_data_reduction        SAINT32
_computing_molecular_graphics
'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97  (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Brucker kappa apex2 CCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1346
_diffrn_reflns_av_sigmaI/netI    0.1332
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            46013
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.57
_exptl_absorpt_coefficient_mu    1.663
_exptl_absorpt_correction_T_max  0.8513
_exptl_absorpt_correction_T_min  0.6909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'APEX 2 (Bruker)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1936
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.013(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.729
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     545
_refine_ls_number_reflns         8130
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.729
_refine_ls_R_factor_all          0.1102
_refine_ls_R_factor_gt           0.0336
_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^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0505
_refine_ls_wR_factor_ref         0.0600
_reflns_number_gt                3791
_reflns_number_total             8130
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1001388_si_001.cif
_cod_data_source_block           anb_om
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025389