#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/11/7151182.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_7151182
loop_
_publ_author_name
'Curtis, Kim L.'
'Evinson, Emma L.'
'Handa, Sandeep'
'Singh, Kuldip'
_publ_section_title
;
 Asymmetric synthesis of
 3-amino-4-hydroxy-2-(hydroxymethyl)pyrrolidines as potential
 glycosidase inhibitors.
;
_journal_issue                   21
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3544
_journal_page_last               3553
_journal_paper_doi               10.1039/b711994a
_journal_volume                  5
_journal_year                    2007
_chemical_absolute_configuration syn
_chemical_formula_sum            'C13 H16 N2 O5 S'
_chemical_formula_weight         312.34
_chemical_melting_point          438.0(10)
_chemical_name_common
;(2R,3R,4S)-1-(Toluene-4-sulfonyl)-2-(carbamoyloxymethyl) -3,4-
epoxypyrrolidine
;
_chemical_name_systematic
;
(2R,3R,4S)-1-(Toluene-4-sulfonyl)-2-(carbamoyloxymethyl)
-3,4-epoxypyrrolidine
;
_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   geom
_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            8
_cell_length_a                   7.7577(8)
_cell_length_b                   17.7377(19)
_cell_length_c                   20.872(2)
_cell_measurement_reflns_used    3646
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.30
_cell_measurement_theta_min      2.26
_cell_volume                     2872.1(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0491
_diffrn_reflns_av_sigmaI/netI    0.0608
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20984
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.51
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_correction_T_min  0.848
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
absorption correction was based on 7737 reflections (SADABS); Rint 0.060 before
correction and 0.035 after.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.12(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.914
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5053
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.914
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0384
_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)+(0.0253P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0673
_refine_ls_wR_factor_ref         0.0699
_reflns_number_gt                4153
_reflns_number_total             5053
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b711994a.txt
_cod_data_source_block           04002
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '437-439K' was changed to '438.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        2872.0(5)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7151182
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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 0.66690(9) 0.12295(4) 0.18951(3) 0.03023(18) Uani 1 1 d . . .
O1 O 0.2276(2) 0.18653(11) 0.22753(8) 0.0419(5) Uani 1 1 d . . .
O2 O 0.3562(2) 0.16997(10) 0.02957(8) 0.0325(5) Uani 1 1 d . . .
O3 O 0.0687(3) 0.16670(12) 0.01106(11) 0.0504(6) Uani 1 1 d . . .
O4 O 0.7032(3) 0.05712(10) 0.15254(8) 0.0382(5) Uani 1 1 d . . .
O5 O 0.7983(2) 0.17839(10) 0.19929(9) 0.0401(5) Uani 1 1 d . . .
N1 N 0.5101(3) 0.16551(12) 0.15235(10) 0.0244(6) Uani 1 1 d . . .
N2 N 0.2348(3) 0.26484(13) -0.02127(11) 0.0464(7) Uani 1 1 d . . .
H2A H 0.3470 0.2866 -0.0244 0.056 Uiso 1 1 d R . .
H2B H 0.1568 0.2933 -0.0372 0.056 Uiso 1 1 d R . .
C1 C 0.4650(3) 0.24443(14) 0.16903(13) 0.0317(7) Uani 1 1 d . . .
H1A H 0.4936 0.2792 0.1335 0.038 Uiso 1 1 calc R . .
H1B H 0.5266 0.2609 0.2081 0.038 Uiso 1 1 calc R . .
C2 C 0.2749(4) 0.24181(16) 0.18018(13) 0.0368(8) Uani 1 1 d . . .
H2 H 0.2029 0.2880 0.1739 0.044 Uiso 1 1 calc R . .
C3 C 0.2101(4) 0.16806(16) 0.16089(12) 0.0323(7) Uani 1 1 d . . .
H3 H 0.0930 0.1633 0.1413 0.039 Uiso 1 1 calc R . .
C4 C 0.3539(3) 0.12071(15) 0.13745(11) 0.0268(6) Uani 1 1 d . . .
H4 H 0.3569 0.0728 0.1627 0.032 Uiso 1 1 calc R . .
C5 C 0.3430(4) 0.10194(14) 0.06714(11) 0.0319(7) Uani 1 1 d . . .
H5A H 0.4375 0.0670 0.0555 0.038 Uiso 1 1 calc R . .
H5B H 0.2321 0.0766 0.0580 0.038 Uiso 1 1 calc R . .
C6 C 0.2056(4) 0.19861(17) 0.00627(14) 0.0372(7) Uani 1 1 d . . .
C7 C 0.5903(3) 0.09412(15) 0.26466(13) 0.0283(7) Uani 1 1 d . . .
C8 C 0.5265(4) 0.02152(15) 0.27250(14) 0.0309(7) Uani 1 1 d . . .
H8 H 0.5283 -0.0135 0.2381 0.037 Uiso 1 1 calc R . .
C9 C 0.4601(4) 0.00132(15) 0.33168(14) 0.0355(8) Uani 1 1 d . . .
H9 H 0.4170 -0.0484 0.3373 0.043 Uiso 1 1 calc R . .
C10 C 0.4544(4) 0.05047(17) 0.38257(14) 0.0352(8) Uani 1 1 d . . .
C11 C 0.5215(4) 0.12244(17) 0.37307(14) 0.0350(7) Uani 1 1 d . . .
H11 H 0.5208 0.1574 0.4076 0.042 Uiso 1 1 calc R . .
C12 C 0.5888(3) 0.14405(14) 0.31504(14) 0.0319(7) Uani 1 1 d . . .
H12 H 0.6341 0.1934 0.3097 0.038 Uiso 1 1 calc R . .
C13 C 0.3811(4) 0.02813(18) 0.44588(14) 0.0536(10) Uani 1 1 d . . .
H13A H 0.3846 0.0713 0.4752 0.080 Uiso 1 1 d R . .
H13B H 0.4491 -0.0134 0.4638 0.080 Uiso 1 1 d R . .
H13C H 0.2614 0.0117 0.4402 0.080 Uiso 1 1 d R . .
S2 S 1.16841(9) 0.88523(4) 0.17313(3) 0.03044(18) Uani 1 1 d . . .
O6 O 0.7138(2) 0.87713(10) 0.20884(8) 0.0347(5) Uani 1 1 d . . .
O7 O 0.8529(2) 0.72761(10) 0.06683(8) 0.0377(5) Uani 1 1 d . . .
O8 O 1.0546(3) 0.66160(12) 0.01401(10) 0.0554(7) Uani 1 1 d . . .
O9 O 1.2867(2) 0.82354(10) 0.18095(9) 0.0355(5) Uani 1 1 d . . .
O10 O 1.2215(2) 0.94932(10) 0.13669(9) 0.0390(5) Uani 1 1 d . . .
N3 N 1.0010(3) 0.85005(12) 0.13702(10) 0.0262(6) Uani 1 1 d . . .
N4 N 0.8320(3) 0.71791(13) -0.03757(11) 0.0461(7) Uani 1 1 d . . .
H4A H 0.8579 0.6960 -0.0809 0.055 Uiso 1 1 d R . .
H4B H 0.7472 0.7555 -0.0324 0.055 Uiso 1 1 d R . .
C14 C 0.8703(3) 0.90178(14) 0.10928(13) 0.0315(7) Uani 1 1 d . . .
H14A H 0.8640 0.8959 0.0622 0.038 Uiso 1 1 calc R . .
H14B H 0.8983 0.9549 0.1194 0.038 Uiso 1 1 calc R . .
C15 C 0.7046(4) 0.87909(15) 0.13989(12) 0.0308(7) Uani 1 1 d . . .
H15 H 0.5925 0.8898 0.1180 0.037 Uiso 1 1 calc R . .
C16 C 0.7308(3) 0.80796(15) 0.17288(12) 0.0294(7) Uani 1 1 d . . .
H16 H 0.6367 0.7694 0.1739 0.035 Uiso 1 1 calc R . .
C17 C 0.9165(3) 0.78358(14) 0.16675(13) 0.0250(7) Uani 1 1 d . . .
H17 H 0.9662 0.7745 0.2103 0.030 Uiso 1 1 calc R . .
C18 C 0.9347(4) 0.71380(15) 0.12655(12) 0.0305(7) Uani 1 1 d . . .
H18A H 1.0581 0.7020 0.1198 0.037 Uiso 1 1 calc R . .
H18B H 0.8798 0.6704 0.1483 0.037 Uiso 1 1 calc R . .
C19 C 0.9238(4) 0.69876(16) 0.01357(15) 0.0337(7) Uani 1 1 d . . .
C20 C 1.1050(3) 0.91457(14) 0.25016(13) 0.0269(7) Uani 1 1 d . . .
C21 C 1.1121(3) 0.86487(15) 0.30068(13) 0.0303(7) Uani 1 1 d . . .
H21 H 1.1632 0.8166 0.2954 0.036 Uiso 1 1 calc R . .
C22 C 1.0446(4) 0.88568(17) 0.35886(13) 0.0346(7) Uani 1 1 d . . .
H22 H 1.0495 0.8512 0.3937 0.042 Uiso 1 1 calc R . .
C23 C 0.9693(4) 0.95576(17) 0.36801(14) 0.0360(8) Uani 1 1 d . . .
C24 C 0.9702(4) 1.00498(16) 0.31696(15) 0.0374(8) Uani 1 1 d . . .
H24 H 0.9239 1.0541 0.3227 0.045 Uiso 1 1 calc R . .
C25 C 1.0349(4) 0.98583(15) 0.25842(15) 0.0335(8) Uani 1 1 d . . .
H25 H 1.0319 1.0207 0.2239 0.040 Uiso 1 1 calc R . .
C26 C 0.8855(4) 0.97633(19) 0.43102(14) 0.0578(10) Uani 1 1 d . . .
H26A H 0.9435 1.0205 0.4492 0.087 Uiso 1 1 d R . .
H26B H 0.8953 0.9339 0.4608 0.087 Uiso 1 1 d R . .
H26C H 0.7635 0.9880 0.4239 0.087 Uiso 1 1 d 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 O5 119.92(12) . . ?
O4 S1 N1 105.61(11) . . ?
O5 S1 N1 106.35(11) . . ?
O4 S1 C7 108.16(12) . . ?
O5 S1 C7 108.31(12) . . ?
N1 S1 C7 107.95(12) . . ?
C3 O1 C2 60.95(16) . . ?
C6 O2 C5 116.4(2) . . ?
C4 N1 C1 111.2(2) . . ?
C4 N1 S1 117.53(16) . . ?
C1 N1 S1 120.11(18) . . ?
N1 C1 C2 103.9(2) . . ?
O1 C2 C3 59.37(17) . . ?
O1 C2 C1 112.3(2) . . ?
C3 C2 C1 109.0(2) . . ?
O1 C3 C2 59.68(17) . . ?
O1 C3 C4 112.3(2) . . ?
C2 C3 C4 109.9(2) . . ?
C3 C4 N1 104.04(19) . . ?
C3 C4 C5 113.9(2) . . ?
N1 C4 C5 111.6(2) . . ?
O2 C5 C4 109.9(2) . . ?
O3 C6 N2 126.9(3) . . ?
O3 C6 O2 123.3(3) . . ?
N2 C6 O2 109.8(3) . . ?
C12 C7 C8 120.3(3) . . ?
C12 C7 S1 120.0(2) . . ?
C8 C7 S1 119.8(2) . . ?
C9 C8 C7 118.5(3) . . ?
C10 C9 C8 122.5(3) . . ?
C9 C10 C11 117.3(3) . . ?
C9 C10 C13 121.9(3) . . ?
C11 C10 C13 120.8(3) . . ?
C12 C11 C10 121.6(3) . . ?
C11 C12 C7 119.9(3) . . ?
O10 S2 O9 118.84(11) . . ?
O10 S2 N3 106.79(12) . . ?
O9 S2 N3 105.67(11) . . ?
O10 S2 C20 109.38(12) . . ?
O9 S2 C20 107.44(12) . . ?
N3 S2 C20 108.30(12) . . ?
C15 O6 C16 60.40(16) . . ?
C19 O7 C18 118.6(2) . . ?
C17 N3 C14 110.6(2) . . ?
C17 N3 S2 117.63(17) . . ?
C14 N3 S2 119.28(17) . . ?
N3 C14 C15 104.8(2) . . ?
O6 C15 C16 59.89(15) . . ?
O6 C15 C14 113.1(2) . . ?
C16 C15 C14 108.5(2) . . ?
O6 C16 C15 59.71(16) . . ?
O6 C16 C17 112.0(2) . . ?
C15 C16 C17 110.0(2) . . ?
N3 C17 C18 112.3(2) . . ?
N3 C17 C16 103.3(2) . . ?
C18 C17 C16 111.9(2) . . ?
O7 C18 C17 107.8(2) . . ?
O8 C19 N4 126.5(3) . . ?
O8 C19 O7 123.1(3) . . ?
N4 C19 O7 110.4(3) . . ?
C21 C20 C25 120.3(3) . . ?
C21 C20 S2 120.0(2) . . ?
C25 C20 S2 119.5(2) . . ?
C22 C21 C20 119.4(3) . . ?
C21 C22 C23 121.6(3) . . ?
C24 C23 C22 117.4(3) . . ?
C24 C23 C26 121.5(3) . . ?
C22 C23 C26 121.1(3) . . ?
C25 C24 C23 122.5(3) . . ?
C24 C25 C20 118.9(3) . . ?
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 1.4276(18) . ?
S1 O5 1.4310(18) . ?
S1 N1 1.628(2) . ?
S1 C7 1.754(3) . ?
O1 C3 1.435(3) . ?
O1 C2 1.440(3) . ?
O2 C6 1.363(3) . ?
O2 C5 1.443(3) . ?
O3 C6 1.208(3) . ?
N1 C4 1.482(3) . ?
N1 C1 1.484(3) . ?
N2 C6 1.327(3) . ?
C1 C2 1.493(4) . ?
C2 C3 1.458(4) . ?
C3 C4 1.479(3) . ?
C4 C5 1.507(3) . ?
C7 C12 1.375(3) . ?
C7 C8 1.390(3) . ?
C8 C9 1.385(4) . ?
C9 C10 1.375(4) . ?
C10 C11 1.393(4) . ?
C10 C13 1.492(4) . ?
C11 C12 1.373(4) . ?
S2 O10 1.4284(18) . ?
S2 O9 1.4372(18) . ?
S2 N3 1.626(2) . ?
S2 C20 1.760(3) . ?
O6 C15 1.441(3) . ?
O6 C16 1.444(3) . ?
O7 C19 1.342(3) . ?
O7 C18 1.420(3) . ?
O8 C19 1.210(3) . ?
N3 C17 1.485(3) . ?
N3 C14 1.485(3) . ?
N4 C19 1.328(3) . ?
C14 C15 1.491(3) . ?
C15 C16 1.452(4) . ?
C16 C17 1.509(4) . ?
C17 C18 1.502(3) . ?
C20 C21 1.375(3) . ?
C20 C25 1.387(3) . ?
C21 C22 1.373(4) . ?
C22 C23 1.387(4) . ?
C23 C24 1.378(4) . ?
C23 C26 1.512(4) . ?
C24 C25 1.364(4) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139190402
