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#$Date: 2016-03-21 03:56:42 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178451 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/72/4027260.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4027260
loop_
_publ_author_name
'Marcelo Siqueira Valle'
'Mauricio Frota Saraiva'
'Pascal Retailleau'
'Mauro V. de Almeida'
'Robert H. Dodd'
_publ_contact_author_address
;Centre de recherche de Gif-sur-Yvette
Institut de Chimie des Substances Naturelles
UPR 2301, CNRS
Avenue de la Terrasse
91198 Gif-sur-Yvette
France
;
_publ_contact_author_email       robert.dodd@icsn.cnrs-gif.fr
_publ_contact_author_fax         '+33 1 69 07 72 47 '
_publ_contact_author_name        'Robert H. Dodd'
_publ_contact_author_phone       '+33 1 69 82 45 94'
_publ_section_title
;
 Rhodium-Catalyzed Intramolecular Formation of N-Sulfamoyl
 2,3-Aziridino-γ-lactones and Their Use for the Enantiospecific Synthesis
 of α,β-Diamino Acid Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5592
_journal_page_last               5599
_journal_paper_doi               10.1021/jo300468j
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C5 H5 N O5 S'
_chemical_formula_sum            'C5 H5 N O5 S'
_chemical_formula_weight         191.16
_chemical_name_common            aziridino-γ-lactone
_chemical_name_systematic
; 
(2aS,2a1R,5aS)-tetrahydro-2H-1,4-dioxa-3-thia-2b-
azacyclopropa[hi]inden-2-one 3,3-dioxide
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.465(4)
_cell_length_b                   6.493(4)
_cell_length_c                   17.064(8)
_cell_measurement_reflns_used    953
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      0.998
_cell_volume                     716.3(7)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'PLATON (Spek, 1980-2004)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.042
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5167
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.39
_exptl_absorpt_coefficient_mu    0.433
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Scalepack
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.773
_exptl_crystal_description       plate
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.091
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881; 641 Friedel pairs coverage= 0.97'
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_coef       0.071(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1618
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0647
_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/[σ²(Fo²)+(0.0000P)²+2.7207P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1538
_refine_ls_wR_factor_ref         0.1553
_reflns_number_gt                1527
_reflns_number_total             1620
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300468j_si_002_2.cif
_cod_data_source_block           compound_6
_cod_database_code               4027260
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S -0.0420(2) 0.4185(3) 0.38586(8) 0.0415(4) Uani 1 1 d .
O1 O -0.1289(7) 0.2177(8) 0.3931(3) 0.0665(15) Uani 1 1 d .
O2 O -0.1667(7) 0.5906(9) 0.4020(3) 0.0673(15) Uani 1 1 d .
O3 O 0.0374(6) 0.4461(6) 0.29994(19) 0.0422(10) Uani 1 1 d .
O4 O 0.4072(6) 0.6196(6) 0.3136(2) 0.0476(11) Uani 1 1 d .
O5 O 0.3573(10) 0.9032(7) 0.3821(4) 0.095(2) Uani 1 1 d .
N2 N 0.1622(6) 0.4187(8) 0.4424(2) 0.0356(10) Uani 1 1 d .
C1 C 0.2177(9) 0.3249(9) 0.2782(3) 0.0400(13) Uani 1 1 d .
H1A H 0.2480 0.3426 0.2229 0.045 Uiso 1 1 calc R
H1B H 0.1925 0.1799 0.2880 0.045 Uiso 1 1 calc R
C2 C 0.3967(8) 0.3999(9) 0.3272(3) 0.0365(11) Uani 1 1 d .
H2 H 0.5250 0.3343 0.3095 0.041 Uiso 1 1 calc R
C3 C 0.3694(8) 0.3673(8) 0.4135(3) 0.0323(11) Uani 1 1 d .
H1 H 0.4565 0.2686 0.4417 0.036 Uiso 1 1 calc R
C4 C 0.3276(8) 0.5715(10) 0.4465(3) 0.0411(12) Uani 1 1 d .
H4 H 0.3857 0.6052 0.4980 0.046 Uiso 1 1 calc R
C5 C 0.3590(10) 0.7234(9) 0.3797(4) 0.0494(14) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0289(6) 0.0602(9) 0.0354(6) 0.0050(7) 0.0017(6) 0.0036(7)
O1 0.043(2) 0.082(3) 0.075(3) 0.023(3) -0.003(2) -0.026(2)
O2 0.048(2) 0.103(4) 0.052(3) -0.007(3) 0.0043(19) 0.035(3)
O3 0.0366(18) 0.059(3) 0.0306(17) 0.0051(17) -0.0037(16) 0.008(2)
O4 0.060(3) 0.044(2) 0.0385(19) 0.0084(18) 0.0001(19) -0.0210(19)
O5 0.151(6) 0.031(2) 0.104(4) 0.007(3) -0.028(4) -0.013(3)
N2 0.034(2) 0.044(2) 0.029(2) 0.008(2) -0.0002(16) 0.003(2)
C1 0.041(3) 0.043(3) 0.036(3) -0.014(2) -0.004(2) 0.000(2)
C2 0.034(2) 0.037(3) 0.038(3) -0.003(2) 0.004(2) 0.001(2)
C3 0.029(2) 0.029(2) 0.039(3) -0.0027(19) -0.007(2) -0.0023(19)
C4 0.046(3) 0.042(3) 0.035(3) -0.008(2) -0.007(2) 0.003(3)
C5 0.064(4) 0.033(3) 0.052(3) 0.001(3) -0.008(3) -0.009(3)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 S1 O1 119.0(3)
O2 S1 O3 106.3(3)
O1 S1 O3 108.4(3)
O2 S1 N2 110.3(3)
O1 S1 N2 105.5(3)
O3 S1 N2 106.7(2)
C1 O3 S1 116.1(3)
C5 O4 C2 110.3(4)
C4 N2 C3 60.1(3)
C4 N2 S1 128.3(4)
C3 N2 S1 122.7(3)
O3 C1 C2 107.4(4)
O3 C1 H1A 110.2
C2 C1 H1A 110.2
O3 C1 H1B 110.2
C2 C1 H1B 110.2
H1A C1 H1B 108.5
O4 C2 C3 107.6(4)
O4 C2 C1 105.4(4)
C3 C2 C1 114.2(5)
O4 C2 H2 109.8
C3 C2 H2 109.8
C1 C2 H2 109.8
C4 C3 N2 59.8(3)
C4 C3 C2 105.8(4)
N2 C3 C2 113.9(4)
C4 C3 H1 120.6
N2 C3 H1 120.6
C2 C3 H1 120.6
N2 C4 C3 60.1(3)
N2 C4 C5 120.1(5)
C3 C4 C5 105.9(5)
N2 C4 H4 118.4
C3 C4 H4 118.4
C5 C4 H4 118.4
O5 C5 O4 122.0(7)
O5 C5 C4 128.3(7)
O4 C5 C4 109.4(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.406(5)
S1 O1 1.425(5)
S1 O3 1.564(4)
S1 N2 1.635(4)
O3 C1 1.455(7)
O4 C5 1.351(8)
O4 C2 1.447(7)
O5 C5 1.168(7)
N2 C4 1.460(7)
N2 C3 1.466(6)
C1 C2 1.508(7)
C1 H1A 0.9700
C1 H1B 0.9700
C2 C3 1.499(7)
C2 H2 0.9800
C3 C4 1.465(8)
C3 H1 0.9800
C4 C5 1.521(8)
C4 H4 0.9800
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O2 S1 O3 C1 161.3(4)
O1 S1 O3 C1 -69.7(4)
N2 S1 O3 C1 43.6(4)
O2 S1 N2 C4 -62.0(5)
O1 S1 N2 C4 168.3(5)
O3 S1 N2 C4 53.0(5)
O2 S1 N2 C3 -137.7(4)
O1 S1 N2 C3 92.6(5)
O3 S1 N2 C3 -22.6(5)
S1 O3 C1 C2 -65.0(5)
C5 O4 C2 C3 -9.1(6)
C5 O4 C2 C1 113.1(5)
O3 C1 C2 O4 -54.5(5)
O3 C1 C2 C3 63.3(6)
S1 N2 C3 C4 118.8(5)
C4 N2 C3 C2 -94.9(5)
S1 N2 C3 C2 23.9(6)
O4 C2 C3 C4 9.9(6)
C1 C2 C3 C4 -106.7(5)
O4 C2 C3 N2 73.3(5)
C1 C2 C3 N2 -43.3(6)
S1 N2 C4 C3 -109.8(5)
C3 N2 C4 C5 91.8(6)
S1 N2 C4 C5 -18.0(7)
C2 C3 C4 N2 108.9(4)
N2 C3 C4 C5 -116.0(5)
C2 C3 C4 C5 -7.1(6)
C2 O4 C5 O5 -179.9(7)
C2 O4 C5 C4 4.5(6)
N2 C4 C5 O5 122.3(8)
C3 C4 C5 O5 -173.4(7)
N2 C4 C5 O4 -62.4(7)
C3 C4 C5 O4 1.9(6)
