#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/11/7151184.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_7151184
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            'C12 H16 Br N O4 S'
_chemical_formula_weight         350.23
_chemical_melting_point          439(2)
_chemical_name_common
;(2R,3R,4R)-1-(Toluene-4-sulfonyl)-2-hydroxymethyl-3-bromo-4-
hydroxypyrrolidine
;
_chemical_name_systematic
;
(2R,3R,4R)-1-(Toluene-4-sulfonyl)-2-hydroxymethyl-3-bromo-4-hydroxypyrrolidine
;
_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            4
_cell_length_a                   7.5443(6)
_cell_length_b                   10.6588(9)
_cell_length_c                   17.4366(15)
_cell_measurement_reflns_used    5920
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.37
_cell_measurement_theta_min      2.24
_cell_volume                     1402.1(2)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11010
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    3.089
_exptl_absorpt_correction_T_max  0.87
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
absorption correction based on 8619 reflections (SADABS); Rint 0.032 before
correction and 0.027 after.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.659
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.003(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2752
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0255
_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)+(0.0394P)²+0.0192P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0657
_refine_ls_wR_factor_ref         0.0661
_reflns_number_gt                2592
_reflns_number_total             2752
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b711994a.txt
_cod_data_source_block           04058
_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 '437-441' was changed to '439(2)' -
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_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7151184
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
Br1 Br 0.63334(3) 0.75240(3) 0.222683(13) 0.03602(11) Uani 1 1 d . . .
S1 S 0.09719(8) 0.77799(5) 0.32151(3) 0.01772(13) Uani 1 1 d . . .
N1 N 0.2955(3) 0.77676(18) 0.35848(11) 0.0186(4) Uani 1 1 d . . .
O1 O 0.4526(3) 0.6245(2) 0.48087(10) 0.0329(5) Uani 1 1 d . . .
H1 H 0.3630 0.6389 0.5080 0.049 Uiso 1 1 calc R . .
O2 O 0.6285(3) 0.8390(2) 0.45167(10) 0.0361(5) Uani 1 1 d . . .
H2A H 0.5582 0.7879 0.4721 0.054 Uiso 1 1 calc R . .
O3 O 0.0176(2) 0.66083(16) 0.34249(10) 0.0240(4) Uani 1 1 d . . .
O4 O 0.0181(2) 0.89393(16) 0.34438(10) 0.0245(4) Uani 1 1 d . . .
C1 C 0.4097(3) 0.6658(2) 0.34369(14) 0.0195(5) Uani 1 1 d . . .
H1A H 0.3714 0.6239 0.2951 0.023 Uiso 1 1 calc R . .
C1' C 0.3986(4) 0.5727(2) 0.40979(14) 0.0266(6) Uani 1 1 d . . .
H1'1 H 0.2749 0.5427 0.4145 0.032 Uiso 1 1 calc R . .
H1'2 H 0.4742 0.4993 0.3979 0.032 Uiso 1 1 calc R . .
C2 C 0.5937(3) 0.7243(2) 0.33255(13) 0.0205(5) Uani 1 1 d . . .
H2 H 0.6882 0.6695 0.3548 0.025 Uiso 1 1 calc R . .
C3 C 0.5877(4) 0.8511(3) 0.37308(15) 0.0279(6) Uani 1 1 d . . .
H3 H 0.6727 0.9104 0.3482 0.034 Uiso 1 1 calc R . .
C4 C 0.3987(4) 0.8942(2) 0.35882(16) 0.0288(6) Uani 1 1 d . . .
H4A H 0.3579 0.9510 0.4001 0.035 Uiso 1 1 calc R . .
H4B H 0.3887 0.9382 0.3090 0.035 Uiso 1 1 calc R . .
C5 C 0.1213(3) 0.7781(2) 0.22123(13) 0.0195(5) Uani 1 1 d . . .
C6 C 0.1273(4) 0.6660(2) 0.18099(14) 0.0225(5) Uani 1 1 d . . .
H6 H 0.1160 0.5881 0.2071 0.027 Uiso 1 1 calc R . .
C7 C 0.1501(4) 0.6691(2) 0.10226(16) 0.0280(6) Uani 1 1 d . . .
H7 H 0.1558 0.5924 0.0746 0.034 Uiso 1 1 calc R . .
C8 C 0.1648(3) 0.7812(2) 0.06277(14) 0.0256(6) Uani 1 1 d . . .
C8' C 0.1849(5) 0.7830(3) -0.02344(15) 0.0405(8) Uani 1 1 d . . .
H8'1 H 0.2233 0.7001 -0.0412 0.061 Uiso 1 1 calc R . .
H8'2 H 0.2735 0.8459 -0.0379 0.061 Uiso 1 1 calc R . .
H8'3 H 0.0709 0.8040 -0.0471 0.061 Uiso 1 1 calc R . .
C9 C 0.1559(4) 0.8929(2) 0.10398(15) 0.0255(6) Uani 1 1 d . . .
H9 H 0.1645 0.9706 0.0775 0.031 Uiso 1 1 calc R . .
C10 C 0.1349(3) 0.8930(2) 0.18266(14) 0.0222(5) Uani 1 1 d . . .
H10 H 0.1298 0.9698 0.2102 0.027 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'
Br Br -0.2901 2.4595 '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 O3 120.50(10) . . ?
O4 S1 N1 106.25(11) . . ?
O3 S1 N1 106.07(10) . . ?
O4 S1 C5 108.68(11) . . ?
O3 S1 C5 107.30(11) . . ?
N1 S1 C5 107.38(10) . . ?
C4 N1 C1 111.77(19) . . ?
C4 N1 S1 118.66(17) . . ?
C1 N1 S1 118.03(15) . . ?
N1 C1 C1' 110.82(19) . . ?
N1 C1 C2 102.87(18) . . ?
C1' C1 C2 114.2(2) . . ?
O1 C1' C1 113.1(2) . . ?
C3 C2 C1 105.93(19) . . ?
C3 C2 Br1 108.73(16) . . ?
C1 C2 Br1 108.88(16) . . ?
O2 C3 C4 113.1(2) . . ?
O2 C3 C2 111.3(2) . . ?
C4 C3 C2 102.7(2) . . ?
N1 C4 C3 103.8(2) . . ?
C6 C5 C10 120.5(2) . . ?
C6 C5 S1 120.43(19) . . ?
C10 C5 S1 119.02(19) . . ?
C7 C6 C5 119.0(2) . . ?
C8 C7 C6 121.7(2) . . ?
C7 C8 C9 118.5(2) . . ?
C7 C8 C8' 120.9(2) . . ?
C9 C8 C8' 120.5(2) . . ?
C10 C9 C8 121.2(2) . . ?
C9 C10 C5 119.0(2) . . ?
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
Br1 C2 1.962(2) . ?
S1 O4 1.4289(18) . ?
S1 O3 1.4331(17) . ?
S1 N1 1.629(2) . ?
S1 C5 1.758(2) . ?
N1 C4 1.474(3) . ?
N1 C1 1.486(3) . ?
O1 C1' 1.417(3) . ?
O2 C3 1.410(3) . ?
C1 C1' 1.523(3) . ?
C1 C2 1.534(3) . ?
C2 C3 1.526(4) . ?
C3 C4 1.518(4) . ?
C5 C6 1.386(3) . ?
C5 C10 1.402(3) . ?
C6 C7 1.384(4) . ?
C7 C8 1.383(4) . ?
C8 C9 1.393(4) . ?
C8 C8' 1.511(4) . ?
C9 C10 1.381(4) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21196873
2 PubChem 23655225
