#------------------------------------------------------------------------------
#$Date: 2025-07-05 13:10:14 +0300 (Sat, 05 Jul 2025) $
#$Revision: 300370 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/17/1571767.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1571767
loop_
_publ_author_name
'Waters, James K.'
'Kelley, Steven P.'
'Mossine, Valeri V.'
'Mawhinney, Thomas P.'
_publ_section_title
;
 (S)-2-Carboxyethyl L-cysteinyl sulfone
;
_journal_coeditor_code           PK4044
_journal_issue                   5
_journal_name_full               IUCrData
_journal_page_first              x240480
_journal_paper_doi               10.1107/S2414314624004802
_journal_volume                  9
_journal_year                    2024
_chemical_absolute_configuration rmad
_chemical_formula_iupac          'C6 H11 N O6 S'
_chemical_formula_moiety         'C6 H11 N O6 S'
_chemical_formula_sum            'C6 H11 N O6 S'
_chemical_formula_weight         225.22
_chemical_name_common
;
(S)-2-Carboxyethyl L-cysteinyl sulfone
;
_chemical_name_systematic
;
(2S)-2-Azaniumyl-3-[(2-carboxyethane)sulfonyl]propanoate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 110.3246(16)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.8838(2)
_cell_length_b                   18.3867(7)
_cell_length_c                   5.1522(2)
_cell_measurement_reflns_used    9939
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.56
_cell_measurement_theta_min      3.32
_cell_volume                     433.85(3)
_computing_cell_refinement
;
APEX3 V.2018.1-0 and SAINT V8.38A (Bruker, 2014)
;
_computing_data_collection
;
APEX3 V.2018.1-0 (Bruker, 2014)
;
_computing_data_reduction
;
APEX3 V.2018.1-0 and SAINT V8.38A (Bruker, 2014)
;
_computing_molecular_graphics
;
CrystalExplorer 17.5 (Mackenzie et al.,  2017), Mercury (Macrae
et al.,  2020)
;
_computing_publication_material
;
Olex2 (Dolomanov et al.,  2009), and publCIF
(Westrip, 2010)
;
_computing_structure_refinement
;
ShelXL (Sheldrick, 2015)
;
_computing_structure_solution
;
ShelXS (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII area detector'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_av_unetI/netI     0.0108
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            15133
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.571
_diffrn_reflns_theta_min         2.215
_diffrn_source                   'Sealed Source Mo with TRIUMPH optics'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.379
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7047
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(AXScale; Bruker, 2014)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_description       plate
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.179
_refine_ls_abs_structure_details
;
Flack x determined using 1277 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   -0.001(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2656
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0190
_refine_ls_R_factor_gt           0.0189
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0333P)²+0.0609P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0508
_refine_ls_wR_factor_ref         0.0508
_reflns_number_gt                2644
_reflns_number_total             2656
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            pk4044.cif
_cod_data_source_block           I
_cod_database_code               1571767
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.848
_shelx_estimated_absorpt_t_max   0.992
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.85411(6) 0.89496(2) 0.84809(6) 0.01103(8) Uani d 1 . .
O O6 0.1220(2) 0.69175(6) 0.5230(2) 0.01356(19) Uani d 1 . .
H H6 0.006(6) 0.6645(14) 0.561(5) 0.020 Uiso d 1 . .
O O4 1.0462(3) 0.92863(7) 1.0965(3) 0.0239(3) Uani d 1 . .
O O5 0.2537(2) 0.72208(6) 0.9711(2) 0.0144(2) Uani d 1 . .
C C1 0.4393(3) 1.06770(7) 0.3928(3) 0.0085(2) Uani d 1 . .
C C6 0.2813(3) 0.72813(7) 0.7474(3) 0.0100(2) Uani d 1 . .
O O2 0.2657(2) 1.09831(6) 0.4873(2) 0.0141(2) Uani d 1 . .
N N1 0.8143(3) 1.07575(6) 0.8579(2) 0.0091(2) Uani d 1 . .
H H1A 0.998(5) 1.0653(13) 0.951(5) 0.014 Uiso d 1 . .
H H1B 0.801(5) 1.1210(14) 0.816(4) 0.014 Uiso d 1 . .
H H1C 0.707(5) 1.0726(13) 0.957(5) 0.014 Uiso d 1 . .
O O1 0.4180(2) 1.06328(6) 0.14494(19) 0.01234(18) Uani d 1 . .
C C4 0.6697(3) 0.82185(7) 0.9387(3) 0.0115(2) Uani d 1 . .
H H4A 0.818(5) 0.7954(13) 1.063(4) 0.014 Uiso d 1 . .
H H4B 0.548(5) 0.8430(13) 1.023(4) 0.014 Uiso d 1 . .
C C3 0.5730(3) 0.95792(7) 0.6791(3) 0.0095(2) Uani d 1 . .
C C2 0.6965(3) 1.02859(7) 0.6080(2) 0.0076(2) Uani d 1 . .
H H2 0.854(5) 1.0212(12) 0.541(4) 0.009 Uiso d 1 . .
O O3 0.9803(3) 0.87027(6) 0.6484(3) 0.0207(2) Uani d 1 . .
C C5 0.4975(3) 0.77739(7) 0.6867(3) 0.0117(2) Uani d 1 . .
H H5A 0.395(5) 0.8068(13) 0.533(4) 0.014 Uiso d 1 . .
H H5B 0.618(5) 0.7471(14) 0.621(4) 0.014 Uiso d 1 . .
H H3A 0.445(5) 0.9346(13) 0.517(5) 0.014 Uiso d 1 . .
H H3B 0.459(5) 0.9664(12) 0.797(5) 0.014 Uiso d 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O4 S1 C4 . . 109.09(7) ?
O4 S1 C3 . . 108.07(7) ?
O4 S1 O3 . . 117.48(9) ?
C4 S1 C3 . . 104.31(6) ?
O3 S1 C4 . . 109.37(7) ?
O3 S1 C3 . . 107.71(7) ?
O2 C1 C2 . . 115.16(11) ?
O1 C1 O2 . . 127.01(13) ?
O1 C1 C2 . . 117.75(12) ?
O6 C6 C5 . . 111.32(11) ?
O5 C6 O6 . . 123.82(13) ?
O5 C6 C5 . . 124.85(12) ?
C5 C4 S1 . . 111.44(9) ?
C2 C3 S1 . . 111.67(9) ?
N1 C2 C1 . . 108.94(10) ?
N1 C2 C3 . . 110.69(10) ?
C3 C2 C1 . . 106.21(10) ?
C6 C5 C4 . . 111.54(11) ?
C6 O6 H6 . . 109.9(17) ?
C2 N1 H1A . . 111.0(16) ?
C2 N1 H1B . . 112.0(13) ?
C2 N1 H1C . . 110.2(16) ?
H1A N1 H1B . . 109(2) ?
H1A N1 H1C . . 113(2) ?
H1B N1 H1C . . 102(2) ?
N1 C2 H2 . . 106.1(13) ?
C1 C2 H2 . . 111.4(12) ?
C3 C2 H2 . . 113.5(13) ?
S1 C3 H3A . . 107.2(15) ?
S1 C3 H3B . . 108.2(14) ?
C2 C3 H3A . . 111.4(15) ?
C2 C3 H3B . . 112.0(13) ?
H3A C3 H3B . . 106(2) ?
S1 C4 H4A . . 103.6(15) ?
S1 C4 H4B . . 105.7(15) ?
C5 C4 H4A . . 112.3(14) ?
C5 C4 H4B . . 111.7(14) ?
H4A C4 H4B . . 111.7(19) ?
C4 C5 H5A . . 112.5(14) ?
C4 C5 H5B . . 113.0(14) ?
C6 C5 H5A . . 108.2(15) ?
C6 C5 H5B . . 106.7(15) ?
H5A C5 H5B . . 104.4(19) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O4 . 1.4380(12) ?
S1 C4 . 1.7686(13) ?
S1 C3 . 1.7756(13) ?
S1 O3 . 1.4440(12) ?
O6 C6 . 1.3285(16) ?
O5 C6 . 1.2107(16) ?
C1 O2 . 1.2489(16) ?
C1 O1 . 1.2471(15) ?
C1 C2 . 1.5353(18) ?
C6 C5 . 1.5038(19) ?
N1 C2 . 1.4919(16) ?
C4 C5 . 1.5174(19) ?
C3 C2 . 1.5293(18) ?
O6 H6 . 0.83(3) ?
N1 H1A . 0.88(3) ?
N1 H1B . 0.86(3) ?
N1 H1C . 0.85(3) ?
C2 H2 . 0.96(2) ?
C3 H3A . 0.95(2) ?
C3 H3B . 0.97(3) ?
C4 H4A . 0.92(2) ?
C4 H4B . 0.93(2) ?
C5 H5A . 0.95(2) ?
C5 H5B . 0.95(2) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1A O1 1_656 0.88(3) 1.95(3) 2.8113(17) 168(2) yes
N1 H1A O4 . 0.88(3) 2.61(2) 3.0239(17) 109.9(19) yes
N1 H1B O5 2_657 0.86(3) 2.22(2) 2.8860(16) 134.4(18) yes
N1 H1B O6 2_656 0.86(3) 2.31(2) 2.9869(15) 136.0(19) yes
N1 H1C O1 1_556 0.85(3) 1.98(3) 2.8238(17) 173(2) yes
O6 H6 O2 2_546 0.83(3) 1.75(3) 2.5436(15) 159(2) yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O3 S1 C3 C2 . . . . -69.00(11) ?
O4 S1 C3 C2 . . . . 58.88(12) ?
C4 S1 C3 C2 . . . . 174.85(9) ?
O3 S1 C4 C5 . . . . -41.94(13) ?
O4 S1 C4 C5 . . . . -171.68(11) ?
C3 S1 C4 C5 . . . . 73.05(11) ?
O1 C1 C2 N1 . . . . 139.90(13) ?
O1 C1 C2 C3 . . . . -100.88(14) ?
O2 C1 C2 N1 . . . . -43.00(16) ?
O2 C1 C2 C3 . . . . 76.23(14) ?
N1 C2 C3 S1 . . . . -78.37(13) ?
C1 C2 C3 S1 . . . . 163.54(9) ?
S1 C4 C5 C6 . . . . -165.17(10) ?
C4 C5 C6 O5 . . . . -2.7(2) ?
C4 C5 C6 O6 . . . . 177.18(12) ?
O3 S1 C3 H3A . . . . 53.3(16) ?
O3 S1 C3 H3B . . . . 167.4(15) ?
O4 S1 C3 H3A . . . . -178.8(16) ?
O4 S1 C3 H3B . . . . -64.8(15) ?
C4 S1 C3 H3A . . . . -62.8(16) ?
C4 S1 C3 H3B . . . . 51.2(15) ?
O3 S1 C4 H4A . . . . 79.0(14) ?
O3 S1 C4 H4B . . . . -163.4(13) ?
O4 S1 C4 H4A . . . . -50.8(14) ?
O4 S1 C4 H4B . . . . 66.8(13) ?
C3 S1 C4 H4A . . . . -166.1(14) ?
C3 S1 C4 H4B . . . . -48.4(13) ?
H6 O6 C6 O5 . . . . -1(2) ?
H6 O6 C6 C5 . . . . 179(2) ?
O1 C1 C2 H2 . . . . 23.2(14) ?
O2 C1 C2 H2 . . . . -159.7(14) ?
C1 C2 N1 H1A . . . . -155.6(17) ?
C1 C2 N1 H1B . . . . -33.7(18) ?
C1 C2 N1 H1C . . . . 79.2(18) ?
C3 C2 N1 H1A . . . . 88.0(17) ?
C3 C2 N1 H1B . . . . -150.1(18) ?
C3 C2 N1 H1C . . . . -37.2(18) ?
H2 C2 N1 H1A . . . . -36(2) ?
H2 C2 N1 H1B . . . . 86(2) ?
H2 C2 N1 H1C . . . . -161(2) ?
N1 C2 C3 H3A . . . . 161.7(17) ?
N1 C2 C3 H3B . . . . 43.1(16) ?
C1 C2 C3 H3A . . . . 43.7(17) ?
C1 C2 C3 H3B . . . . -75.0(16) ?
H2 C2 C3 S1 . . . . 40.8(13) ?
H2 C2 C3 H3A . . . . -79(2) ?
H2 C2 C3 H3B . . . . 162(2) ?
S1 C4 C5 H5A . . . . -43.3(17) ?
S1 C4 C5 H5B . . . . 74.7(16) ?
H4A C4 C5 C6 . . . . 79.1(16) ?
H4A C4 C5 H5A . . . . -159(2) ?
H4A C4 C5 H5B . . . . -41(2) ?
H4B C4 C5 C6 . . . . -47.2(15) ?
H4B C4 C5 H5A . . . . 75(2) ?
H4B C4 C5 H5B . . . . -167(2) ?
H5A C5 C6 O5 . . . . -127.0(14) ?
H5A C5 C6 O6 . . . . 52.9(14) ?
H5B C5 C6 O5 . . . . 121.2(13) ?
H5B C5 C6 O6 . . . . -59.0(13) ?
