#------------------------------------------------------------------------------
#$Date: 2025-08-22 13:33:34 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301861 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/13/7151325.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_7151325
loop_
_publ_author_name
'Moloney, Mark G.'
'Panchal, Terry'
'Pike, Richard'
_publ_section_title
;
 trans-2,5-Disubstituted pyrrolidines: Rapid stereocontrolled access
 from sulfones.
;
_journal_issue                   21
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3894
_journal_page_last               3897
_journal_paper_doi               10.1039/b611583g
_journal_volume                  4
_journal_year                    2006
_chemical_absolute_configuration ad
_chemical_compound_source
;
synthesis as described
;
_chemical_formula_moiety         ' C18 H25 N O6 S '
_chemical_formula_sum            'C18 H25 N O6 S'
_chemical_formula_weight         383.47
_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
_cell_angle_alpha                90
_cell_angle_beta                 98.9319(17)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.6783(3)
_cell_length_b                   8.1891(2)
_cell_length_c                   11.1365(3)
_cell_measurement_reflns_used    9083
_cell_measurement_temperature    150
_cell_measurement_theta_max      28
_cell_measurement_theta_min      5
_cell_volume                     962.03(4)
_computing_cell_refinement
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
_computing_data_collection
;
KappaCCD software 'Collect' (Nonius, 2000)
;
_computing_data_reduction
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
_computing_publication_material
;
CRYSTALS (Watkin et al, 2001)
;
_computing_structure_refinement
;
CRYSTALS (Watkin et al, 2001)
;
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1992)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
;
Nonius KappaCCD
;
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.039
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9083
_diffrn_reflns_theta_full        27.476
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_min         5.177
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Denzo/Scalepack (Otwinowski & Minor, 1996)
;
_exptl_crystal_colour            ' colourless '
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_description       ' fragment '
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.18
_exptl_crystal_thermal_history
;
The material was crystallised at ambient temperature. A suitable crystal
was cooled rapidly to 150K for single-crystal X-ray diffraction analysis.
;
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.42
_refine_ls_abs_structure_details 'Flack, 1848 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.04(7)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1154
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3226
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0334
_refine_ls_shift/su_max          0.002349
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)]
where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)²]²
Ai are:
0.310 0.0240 0.0616
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0553
_refine_ls_wR_factor_gt          0.0340
_refine_ls_wR_factor_ref         0.0340
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              10
_reflns_limit_k_min              -10
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                3226
_reflns_number_total             4175
_reflns_threshold_expression     I>3.00u(I)
_cod_data_source_file            b611583g.txt
_cod_data_source_block           arc1288
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 
;
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_original_formula_sum        ' C18 H25 N O6 S '
_cod_database_code               7151325
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_occupancy
_atom_site_adp_type
N1 N 0.39679(14) 0.3820(2) 0.26585(14) 0.0161 1.0000 Uani
C1 C 0.50485(18) 0.3652(3) 0.36097(17) 0.0179 1.0000 Uani
C2 C 0.4913(2) 0.1948(3) 0.4158(2) 0.0231 1.0000 Uani
C3 C 0.4053(2) 0.1023(3) 0.3153(2) 0.0230 1.0000 Uani
C4 C 0.3161(2) 0.2362(3) 0.2541(2) 0.0192 1.0000 Uani
C5 C 0.2046(2) 0.2617(3) 0.3225(2) 0.0203 1.0000 Uani
O1 O 0.20913(15) 0.3446(2) 0.41247(14) 0.0285 1.0000 Uani
O2 O 0.10289(14) 0.1778(2) 0.27051(14) 0.0252 1.0000 Uani
C6 C -0.0123(2) 0.1965(3) 0.3264(2) 0.0297 1.0000 Uani
C7 C -0.0139(2) 0.0828(3) 0.4314(2) 0.0337 1.0000 Uani
C8 C 0.3439(2) 0.5373(3) 0.24604(19) 0.0176 1.0000 Uani
O3 O 0.39237(16) 0.65974(18) 0.29006(15) 0.0226 1.0000 Uani
O4 O 0.23534(14) 0.52368(18) 0.16735(13) 0.0207 1.0000 Uani
C9 C 0.1545(2) 0.6701(3) 0.1353(2) 0.0245 1.0000 Uani
C10 C 0.0448(3) 0.5982(3) 0.0480(3) 0.0406 1.0000 Uani
C11 C 0.1101(2) 0.7354(3) 0.2484(2) 0.0346 1.0000 Uani
C12 C 0.2270(2) 0.7943(3) 0.0722(2) 0.0329 1.0000 Uani
S1 S 0.65473(5) 0.37412(8) 0.30277(5) 0.0193 1.0000 Uani
O5 O 0.65482(16) 0.24686(19) 0.21271(16) 0.0268 1.0000 Uani
O6 O 0.75137(13) 0.3740(3) 0.40889(14) 0.0301 1.0000 Uani
C13 C 0.6573(2) 0.5645(3) 0.2299(2) 0.0188 1.0000 Uani
C14 C 0.6065(2) 0.5768(3) 0.1069(2) 0.0218 1.0000 Uani
C15 C 0.6026(2) 0.7287(3) 0.0514(2) 0.0287 1.0000 Uani
C16 C 0.6501(2) 0.8651(3) 0.1180(2) 0.0306 1.0000 Uani
C17 C 0.7007(2) 0.8514(3) 0.2396(2) 0.0293 1.0000 Uani
C18 C 0.7050(2) 0.6993(3) 0.2965(2) 0.0235 1.0000 Uani
H11 H 0.5059 0.4563 0.4210 0.0214 1.0000 Uiso
H21 H 0.5757 0.1401 0.4353 0.0280 1.0000 Uiso
H22 H 0.4512 0.2022 0.4910 0.0280 1.0000 Uiso
H31 H 0.4558 0.0526 0.2562 0.0279 1.0000 Uiso
H32 H 0.3564 0.0149 0.3504 0.0279 1.0000 Uiso
H41 H 0.2793 0.2091 0.1683 0.0231 1.0000 Uiso
H61 H -0.0168 0.3114 0.3558 0.0362 1.0000 Uiso
H62 H -0.0879 0.1733 0.2636 0.0362 1.0000 Uiso
H71 H -0.0936 0.0997 0.4665 0.0413 1.0000 Uiso
H72 H 0.0610 0.1055 0.4950 0.0413 1.0000 Uiso
H73 H -0.0101 -0.0326 0.4029 0.0413 1.0000 Uiso
H101 H -0.0175 0.6864 0.0193 0.0461 1.0000 Uiso
H102 H 0.0775 0.5492 -0.0233 0.0461 1.0000 Uiso
H103 H 0.0021 0.5118 0.0906 0.0461 1.0000 Uiso
H111 H 0.0557 0.8339 0.2271 0.0421 1.0000 Uiso
H112 H 0.1853 0.7662 0.3095 0.0421 1.0000 Uiso
H113 H 0.0599 0.6495 0.2835 0.0421 1.0000 Uiso
H121 H 0.1727 0.8927 0.0506 0.0390 1.0000 Uiso
H122 H 0.3057 0.8270 0.1278 0.0390 1.0000 Uiso
H123 H 0.2504 0.7452 -0.0035 0.0390 1.0000 Uiso
H141 H 0.5735 0.4778 0.0597 0.0266 1.0000 Uiso
H151 H 0.5657 0.7402 -0.0363 0.0351 1.0000 Uiso
H161 H 0.6476 0.9743 0.0774 0.0375 1.0000 Uiso
H171 H 0.7341 0.9503 0.2866 0.0349 1.0000 Uiso
H181 H 0.7419 0.6880 0.3843 0.0281 1.0000 Uiso
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 International_Tables_Vol_IV_Table_2.2B
'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 International_Tables_Vol_IV_Table_2.2B
'N ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 International_Tables_Vol_IV_Table_2.2B
'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 International_Tables_Vol_IV_Table_2.2B
'S ' 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 International_Tables_Vol_IV_Table_2.2B
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 . N1 . C4 . 112.28(18) yes
C1 . N1 . C8 . 117.34(18) yes
C4 . N1 . C8 . 120.69(16) yes
N1 . C1 . C2 . 105.24(18) yes
N1 . C1 . S1 . 112.41(13) yes
C2 . C1 . S1 . 108.63(15) yes
N1 . C1 . H11 . 110.100 no
C2 . C1 . H11 . 113.776 no
S1 . C1 . H11 . 106.797 no
C1 . C2 . C3 . 103.95(17) yes
C1 . C2 . H21 . 110.835 no
C3 . C2 . H21 . 110.835 no
C1 . C2 . H22 . 110.835 no
C3 . C2 . H22 . 110.834 no
H21 . C2 . H22 . 109.467 no
C2 . C3 . C4 . 103.34(18) yes
C2 . C3 . H31 . 110.982 no
C4 . C3 . H31 . 110.982 no
C2 . C3 . H32 . 110.982 no
C4 . C3 . H32 . 110.982 no
H31 . C3 . H32 . 109.467 no
N1 . C4 . C3 . 103.05(18) yes
N1 . C4 . C5 . 109.71(17) yes
C3 . C4 . C5 . 110.70(19) yes
N1 . C4 . H41 . 113.861 no
C3 . C4 . H41 . 112.921 no
C5 . C4 . H41 . 106.634 no
C4 . C5 . O1 . 124.0(2) yes
C4 . C5 . O2 . 110.94(19) yes
O1 . C5 . O2 . 125.0(2) yes
C5 . O2 . C6 . 116.09(18) yes
O2 . C6 . C7 . 112.2(2) yes
O2 . C6 . H61 . 108.791 no
C7 . C6 . H61 . 108.791 no
O2 . C6 . H62 . 108.791 no
C7 . C6 . H62 . 108.791 no
H61 . C6 . H62 . 109.467 no
C6 . C7 . H71 . 109.467 no
C6 . C7 . H72 . 109.467 no
H71 . C7 . H72 . 109.475 no
C6 . C7 . H73 . 109.467 no
H71 . C7 . H73 . 109.476 no
H72 . C7 . H73 . 109.476 no
N1 . C8 . O3 . 124.1(2) yes
N1 . C8 . O4 . 108.31(17) yes
O3 . C8 . O4 . 127.6(2) yes
C8 . O4 . C9 . 119.92(16) yes
O4 . C9 . C10 . 101.68(18) yes
O4 . C9 . C11 . 109.29(18) yes
C10 . C9 . C11 . 111.1(2) yes
O4 . C9 . C12 . 109.47(18) yes
C10 . C9 . C12 . 111.2(2) yes
C11 . C9 . C12 . 113.4(2) yes
C9 . C10 . H101 . 109.467 no
C9 . C10 . H102 . 109.467 no
H101 . C10 . H102 . 109.476 no
C9 . C10 . H103 . 109.467 no
H101 . C10 . H103 . 109.475 no
H102 . C10 . H103 . 109.476 no
C9 . C11 . H111 . 109.467 no
C9 . C11 . H112 . 109.467 no
H111 . C11 . H112 . 109.476 no
C9 . C11 . H113 . 109.466 no
H111 . C11 . H113 . 109.476 no
H112 . C11 . H113 . 109.476 no
C9 . C12 . H121 . 109.467 no
C9 . C12 . H122 . 109.466 no
H121 . C12 . H122 . 109.476 no
C9 . C12 . H123 . 109.466 no
H121 . C12 . H123 . 109.476 no
H122 . C12 . H123 . 109.476 no
C1 . S1 . O5 . 108.27(10) yes
C1 . S1 . O6 . 105.37(9) yes
O5 . S1 . O6 . 119.35(11) yes
C1 . S1 . C13 . 106.11(11) yes
O5 . S1 . C13 . 108.46(10) yes
O6 . S1 . C13 . 108.53(11) yes
S1 . C13 . C14 . 118.98(16) yes
S1 . C13 . C18 . 119.37(17) yes
C14 . C13 . C18 . 121.6(2) yes
C13 . C14 . C15 . 118.8(2) yes
C13 . C14 . H141 . 120.600 no
C15 . C14 . H141 . 120.600 no
C14 . C15 . C16 . 119.9(2) yes
C14 . C15 . H151 . 120.025 no
C16 . C15 . H151 . 120.025 no
C15 . C16 . C17 . 120.7(2) yes
C15 . C16 . H161 . 119.644 no
C17 . C16 . H161 . 119.644 no
C16 . C17 . C18 . 119.9(2) yes
C16 . C17 . H171 . 120.050 no
C18 . C17 . H171 . 120.050 no
C13 . C18 . C17 . 119.0(2) yes
C13 . C18 . H181 . 120.486 no
C17 . C18 . H181 . 120.487 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C1 . 1.447(2) yes
N1 . C4 . 1.466(3) yes
N1 . C8 . 1.395(3) yes
C1 . C2 . 1.539(3) yes
C1 . S1 . 1.8191(19) yes
C1 . H11 . 1.000 no
C2 . C3 . 1.533(3) yes
C2 . H21 . 1.000 no
C2 . H22 . 1.000 no
C3 . C4 . 1.540(3) yes
C3 . H31 . 1.000 no
C3 . H32 . 1.000 no
C4 . C5 . 1.524(3) yes
C4 . H41 . 1.000 no
C5 . O1 . 1.205(3) yes
C5 . O2 . 1.339(3) yes
O2 . C6 . 1.470(3) yes
C6 . C7 . 1.497(4) yes
C6 . H61 . 1.000 no
C6 . H62 . 1.000 no
C7 . H71 . 1.000 no
C7 . H72 . 1.000 no
C7 . H73 . 1.000 no
C8 . O3 . 1.198(3) yes
C8 . O4 . 1.345(3) yes
O4 . C9 . 1.488(3) yes
C9 . C10 . 1.520(3) yes
C9 . C11 . 1.512(3) yes
C9 . C12 . 1.515(3) yes
C10 . H101 . 1.000 no
C10 . H102 . 1.000 no
C10 . H103 . 1.000 no
C11 . H111 . 1.000 no
C11 . H112 . 1.000 no
C11 . H113 . 1.000 no
C12 . H121 . 1.000 no
C12 . H122 . 1.000 no
C12 . H123 . 1.000 no
S1 . O5 . 1.4465(17) yes
S1 . O6 . 1.4431(15) yes
S1 . C13 . 1.760(2) yes
C13 . C14 . 1.396(3) yes
C13 . C18 . 1.382(3) yes
C14 . C15 . 1.387(3) yes
C14 . H141 . 1.000 no
C15 . C16 . 1.393(4) yes
C15 . H151 . 1.000 no
C16 . C17 . 1.382(3) yes
C16 . H161 . 1.000 no
C17 . C18 . 1.395(3) yes
C17 . H171 . 1.000 no
C18 . H181 . 1.000 no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 17249726
2 PubChem 16091132
