#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:38:45 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178435 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/56/4025622.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_4025622
loop_
_publ_author_name
'Bing Wang'
_publ_section_title
;
 Practical Enantiospecific Synthesis of an Orthogonally Protected
 1,4-trans-1,5-cis- 4,5-Diamino-2-cyclopenten-1-ol Derivative
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6012
_journal_page_last               6015
_journal_paper_doi               10.1021/jo1009118
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H25 N O4 S'
_chemical_formula_sum            'C13 H25 N O4 S'
_chemical_formula_weight         291.41
_chemical_name_systematic
; 
 ? 
;
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.9800(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.6663(5)
_cell_length_b                   8.5121(5)
_cell_length_c                   9.8764(6)
_cell_measurement_temperature    173(2)
_cell_volume                     785.02(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0192
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9120
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.873092
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.531
_exptl_crystal_size_mid          0.368
_exptl_crystal_size_min          0.131
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2478
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0435
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0362P)²+0.9382P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1043
_reflns_number_gt                2433
_reflns_number_total             2478
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1009118_si_003.cif
_cod_data_source_block           DS-6
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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               4025622
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.94384(7) 0.24678(9) 0.31156(7) 0.02582(18) Uani 1 1 d . . .
O1 O 0.5887(3) 0.7765(4) 0.1255(3) 0.0696(11) Uani 1 1 d . . .
O2 O 0.5346(2) 0.6242(3) 0.2927(3) 0.0425(6) Uani 1 1 d . . .
O3 O 0.9708(2) 0.7810(3) 0.2790(3) 0.0428(7) Uani 1 1 d . . .
H3B H 0.9878 0.7450 0.3609 0.064 Uiso 1 1 calc R . .
O4 O 1.0092(2) 0.1711(3) 0.4507(2) 0.0333(5) Uani 1 1 d . . .
N1 N 0.8783(3) 0.4208(3) 0.3345(3) 0.0261(6) Uani 1 1 d . . .
H1A H 0.9338 0.5036 0.3576 0.031 Uiso 1 1 calc R . .
C1 C 0.4761(3) 0.7061(4) 0.1670(3) 0.0308(8) Uani 1 1 d . . .
C2 C 0.7210(3) 0.7015(4) 0.1924(3) 0.0328(8) Uani 1 1 d . . .
H2A H 0.7515 0.6299 0.1253 0.039 Uiso 1 1 calc R . .
C3 C 0.6849(3) 0.6059(4) 0.3116(3) 0.0280(7) Uani 1 1 d . . .
H3A H 0.7359 0.6537 0.4034 0.034 Uiso 1 1 calc R . .
C4 C 0.3726(7) 0.8259(7) 0.1904(6) 0.0844(18) Uani 1 1 d . . .
H4A H 0.4223 0.9008 0.2618 0.127 Uiso 1 1 calc R . .
H4B H 0.2961 0.7739 0.2222 0.127 Uiso 1 1 calc R . .
H4C H 0.3311 0.8819 0.1026 0.127 Uiso 1 1 calc R . .
C5 C 0.4071(7) 0.5877(7) 0.0565(5) 0.0826(18) Uani 1 1 d . . .
H5A H 0.4799 0.5139 0.0422 0.124 Uiso 1 1 calc R . .
H5B H 0.3639 0.6423 -0.0317 0.124 Uiso 1 1 calc R . .
H5C H 0.3328 0.5300 0.0871 0.124 Uiso 1 1 calc R . .
C6 C 0.5806(4) 0.2263(6) 0.3984(5) 0.0546(11) Uani 1 1 d . . .
H6A H 0.5407 0.1928 0.3047 0.082 Uiso 1 1 calc R . .
H6B H 0.5538 0.1756 0.4735 0.082 Uiso 1 1 calc R . .
C7 C 0.6724(3) 0.3422(4) 0.4241(4) 0.0335(8) Uani 1 1 d . . .
H7A H 0.7101 0.3725 0.5191 0.040 Uiso 1 1 calc R . .
C8 C 0.7223(3) 0.4305(4) 0.3144(3) 0.0258(6) Uani 1 1 d . . .
H8A H 0.6746 0.3845 0.2208 0.031 Uiso 1 1 calc R . .
C9 C 0.8286(4) 0.8339(4) 0.2371(4) 0.0355(8) Uani 1 1 d . . .
H9A H 0.8187 0.9081 0.1580 0.043 Uiso 1 1 calc R . .
H9B H 0.8062 0.8918 0.3158 0.043 Uiso 1 1 calc R . .
C10 C 1.0968(3) 0.3096(4) 0.2450(3) 0.0318(7) Uani 1 1 d . . .
C11 C 1.1725(4) 0.1566(5) 0.2275(4) 0.0479(10) Uani 1 1 d . . .
H11A H 1.2562 0.1797 0.1921 0.072 Uiso 1 1 calc R . .
H11B H 1.1065 0.0884 0.1608 0.072 Uiso 1 1 calc R . .
H11C H 1.2036 0.1033 0.3183 0.072 Uiso 1 1 calc R . .
C12 C 1.0329(4) 0.3879(6) 0.1037(4) 0.0518(11) Uani 1 1 d . . .
H12A H 1.1103 0.4238 0.0638 0.078 Uiso 1 1 calc R . .
H12B H 0.9745 0.4781 0.1166 0.078 Uiso 1 1 calc R . .
H12C H 0.9728 0.3122 0.0399 0.078 Uiso 1 1 calc R . .
C13 C 1.1952(3) 0.4190(4) 0.3475(4) 0.0369(8) Uani 1 1 d . . .
H13A H 1.2752 0.4505 0.3096 0.055 Uiso 1 1 calc R . .
H13B H 1.2323 0.3647 0.4371 0.055 Uiso 1 1 calc R . .
H13C H 1.1417 0.5124 0.3623 0.055 Uiso 1 1 calc R . .
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'
H H 0.0000 0.0000 '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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 S1 N1 110.21(13) . . ?
O4 S1 C10 105.32(14) . . ?
N1 S1 C10 99.22(14) . . ?
C1 O1 C2 110.2(3) . . ?
C1 O2 C3 109.4(2) . . ?
C9 O3 H3B 109.5 . . ?
C8 N1 S1 116.7(2) . . ?
C8 N1 H1A 121.7 . . ?
S1 N1 H1A 121.7 . . ?
O1 C1 O2 107.8(2) . . ?
O1 C1 C4 111.0(4) . . ?
O2 C1 C4 109.6(3) . . ?
O1 C1 C5 107.9(3) . . ?
O2 C1 C5 108.0(3) . . ?
C4 C1 C5 112.4(4) . . ?
O1 C2 C9 105.5(3) . . ?
O1 C2 C3 103.7(2) . . ?
C9 C2 C3 116.3(3) . . ?
O1 C2 H2A 110.3 . . ?
C9 C2 H2A 110.3 . . ?
C3 C2 H2A 110.3 . . ?
O2 C3 C8 109.7(3) . . ?
O2 C3 C2 105.4(2) . . ?
C8 C3 C2 115.4(3) . . ?
O2 C3 H3A 108.7 . . ?
C8 C3 H3A 108.7 . . ?
C2 C3 H3A 108.7 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C1 C5 H5A 109.5 . . ?
C1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 H6A 120.0 . . ?
C7 C6 H6B 120.0 . . ?
H6A C6 H6B 120.0 . . ?
C6 C7 C8 124.6(3) . . ?
C6 C7 H7A 117.7 . . ?
C8 C7 H7A 117.7 . . ?
N1 C8 C7 112.6(3) . . ?
N1 C8 C3 106.6(2) . . ?
C7 C8 C3 112.5(3) . . ?
N1 C8 H8A 108.3 . . ?
C7 C8 H8A 108.3 . . ?
C3 C8 H8A 108.3 . . ?
O3 C9 C2 113.1(3) . . ?
O3 C9 H9A 109.0 . . ?
C2 C9 H9A 109.0 . . ?
O3 C9 H9B 109.0 . . ?
C2 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C13 C10 C12 112.2(3) . . ?
C13 C10 C11 111.3(3) . . ?
C12 C10 C11 111.2(3) . . ?
C13 C10 S1 111.2(2) . . ?
C12 C10 S1 106.3(2) . . ?
C11 C10 S1 104.2(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O4 1.501(2) . ?
S1 N1 1.650(3) . ?
S1 C10 1.846(3) . ?
O1 C1 1.393(4) . ?
O1 C2 1.429(4) . ?
O2 C1 1.409(4) . ?
O2 C3 1.425(4) . ?
O3 C9 1.403(4) . ?
O3 H3B 0.8400 . ?
N1 C8 1.471(4) . ?
N1 H1A 0.8800 . ?
C1 C4 1.488(5) . ?
C1 C5 1.509(6) . ?
C2 C9 1.520(5) . ?
C2 C3 1.543(4) . ?
C2 H2A 1.0000 . ?
C3 C8 1.534(4) . ?
C3 H3A 1.0000 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.307(5) . ?
C6 H6A 0.9500 . ?
C6 H6B 0.9500 . ?
C7 C8 1.498(4) . ?
C7 H7A 0.9500 . ?
C8 H8A 1.0000 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C13 1.516(5) . ?
C10 C12 1.526(5) . ?
C10 C11 1.526(5) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 S1 N1 C8 -101.5(2) . . . . ?
C10 S1 N1 C8 148.4(2) . . . . ?
C2 O1 C1 O2 19.6(4) . . . . ?
C2 O1 C1 C4 139.7(4) . . . . ?
C2 O1 C1 C5 -96.8(4) . . . . ?
C3 O2 C1 O1 -15.8(4) . . . . ?
C3 O2 C1 C4 -136.8(4) . . . . ?
C3 O2 C1 C5 100.5(4) . . . . ?
C1 O1 C2 C9 -137.7(3) . . . . ?
C1 O1 C2 C3 -15.1(4) . . . . ?
C1 O2 C3 C8 -118.6(3) . . . . ?
C1 O2 C3 C2 6.2(4) . . . . ?
O1 C2 C3 O2 5.2(4) . . . . ?
C9 C2 C3 O2 120.4(3) . . . . ?
O1 C2 C3 C8 126.3(3) . . . . ?
C9 C2 C3 C8 -118.4(3) . . . . ?
S1 N1 C8 C7 67.4(3) . . . . ?
S1 N1 C8 C3 -168.74(19) . . . . ?
C6 C7 C8 N1 -120.5(4) . . . . ?
C6 C7 C8 C3 118.9(4) . . . . ?
O2 C3 C8 N1 -179.8(2) . . . . ?
C2 C3 C8 N1 61.3(3) . . . . ?
O2 C3 C8 C7 -55.9(3) . . . . ?
C2 C3 C8 C7 -174.8(3) . . . . ?
O1 C2 C9 O3 -167.7(3) . . . . ?
C3 C2 C9 O3 78.1(4) . . . . ?
O4 S1 C10 C13 -57.2(3) . . . . ?
N1 S1 C10 C13 56.8(3) . . . . ?
O4 S1 C10 C12 -179.7(3) . . . . ?
N1 S1 C10 C12 -65.7(3) . . . . ?
O4 S1 C10 C11 62.8(3) . . . . ?
N1 S1 C10 C11 176.8(2) . . . . ?
