#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/03/2200391.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_2200391
loop_
_publ_author_name
'N. Srinivasan'
'B. Sridhar'
'R. K. Rajaram'
_publ_section_title
;
 Bis(<small>DL</small>-methioninium) sulfate
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o746
_journal_page_last               o748
_journal_paper_doi               10.1107/S1600536801012016
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         '2C5 H12 N O2 S1 + , S O4 2-'
_chemical_formula_sum            'C10 H24 N2 O8 S3'
_chemical_formula_weight         396.49
_chemical_name_common            Bis(DL-Methioninium)sulfate
_chemical_name_systematic
;
Bis(DL-Methioninium)sulfate
;
_space_group_IT_number           143
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'P 3'
_symmetry_space_group_name_H-M   'P 3'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            3
_cell_length_a                   10.281(3)
_cell_length_b                   10.281(3)
_cell_length_c                   14.788(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.41
_cell_measurement_theta_min      14.54
_cell_volume                     1353.7(8)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'CAD-4 Software'
_computing_molecular_graphics    'PLATON (Spek, 1999)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .996
_diffrn_measured_fraction_theta_max .996
_diffrn_measurement_device_type  'Enraf-Nonius sealed tube'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  .0658
_diffrn_reflns_av_sigmaI/netI    .0473
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2818
_diffrn_reflns_theta_full        69.99
_diffrn_reflns_theta_max         69.99
_diffrn_reflns_theta_min         4.97
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 3
_diffrn_standards_interval_time  60
_diffrn_standards_number         25
_exptl_absorpt_coefficient_mu    4.123
_exptl_absorpt_correction_T_max  .438
_exptl_absorpt_correction_T_min  .221
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_meas      1.454
_exptl_crystal_density_method    flotation
_exptl_crystal_description       Needle
_exptl_crystal_F_000             630
_exptl_crystal_size_max          .5
_exptl_crystal_size_mid          .35
_exptl_crystal_size_min          .2
_refine_diff_density_max         .603
_refine_diff_density_min         -.507
_refine_ls_abs_structure_Flack   -.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         1786
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          .0540
_refine_ls_R_factor_gt           .0507
_refine_ls_shift/su_max          .000
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1004P)²+0.3922P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1473
_reflns_number_gt                1690
_reflns_number_total             1786
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6061.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Trigonal' changed to 'trigonal' 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:

'_symmetry_cell_setting' value 'Trigonal' changed to 'trigonal'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1353.5(8)
_cod_database_code               2200391
_cod_database_fobs_code          2200391
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
loop_
_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
S1 .3333 .6667 .77391(13) .0310(4) Uani d S 1 . . S
O1 .3333 .6667 .8717(5) .0434(14) Uani d S 1 . . O
O2 .4427(4) .8170(4) .7397(3) .0438(9) Uani d . 1 . . O
S2 1.0000 1.0000 .98814(13) .0305(4) Uani d S 1 . . S
O3 1.0000 1.0000 .8912(5) .062(2) Uani d S 1 . . O
O4 .8825(4) .8538(4) 1.0219(3) .0452(9) Uani d . 1 . . O
S3 .6667 .3333 .86420(13) .0314(4) Uani d S 1 . . S
O5 .6667 .3333 .9608(5) .0534(17) Uani d S 1 . . O
O6 .5636(6) .1826(5) .8286(4) .0715(14) Uani d . 1 . . O
O11 1.0169(5) .3728(5) .6607(3) .0501(9) Uani d . 1 . . O
H11 1.0871 .4506 .6810 .075 Uiso calc R 1 . . H
O12 1.0378(5) .2760(5) .7908(3) .0515(10) Uani d . 1 . . O
N11 .7559(5) .0500(5) .7821(3) .0437(10) Uani d . 1 . . N
H11A .8198 .0413 .8188 .066 Uiso calc R 1 . . H
H11B .6772 -.0406 .7715 .066 Uiso calc R 1 . . H
H11C .7249 .1078 .8080 .066 Uiso calc R 1 . . H
C11 .9748(6) .2651(6) .7207(4) .0399(11) Uani d . 1 . . C
C12 .8326(6) .1193(5) .6949(4) .0400(10) Uani d . 1 . . C
H12 .8634 .0524 .6669 .048 Uiso calc R 1 . . H
C13 .7291(7) .1375(7) .6291(4) .0532(14) Uani d . 1 . . C
H13A .7296 .2301 .6428 .064 Uiso calc R 1 . . H
H13B .6273 .0550 .6375 .064 Uiso calc R 1 . . H
C14 .7749(9) .1408(9) .5302(5) .0708(19) Uani d . 1 . . C
H14A .8768 .2231 .5224 .085 Uiso calc R 1 . . H
H14B .7100 .1609 .4923 .085 Uiso calc R 1 . . H
S11 .7659(3) -.0287(3) .49214(15) .0864(7) Uani d . 1 . . S
C15 .5623(13) -.1487(12) .4901(8) .109(4) Uani d . 1 . . C
H15A .5370 -.2475 .4702 .164 Uiso calc R 1 . . H
H15B .5198 -.1074 .4493 .164 Uiso calc R 1 . . H
H15C .5228 -.1545 .5497 .164 Uiso calc R 1 . . H
O21 .7156(4) .0723(5) .0797(3) .0503(10) Uani d . 1 . . O
H21 .7936 .0769 .0624 .075 Uiso calc R 1 . . H
O22 .6232(5) -.0585(5) -.0462(3) .0535(10) Uani d . 1 . . O
C21 .6119(6) .0030(6) .0200(4) .0366(10) Uani d . 1 . . C
C22 .4706(5) .0103(5) .0384(3) .0375(10) Uani d . 1 A . C
H22 .4987 .1148 .0509 .045 Uiso calc R 1 . . H
N21 .3763(5) -.0402(5) -.0446(3) .0411(10) Uani d . 1 . . N
H21A .2925 -.0367 -.0353 .062 Uiso calc R 1 . . H
H21B .3528 -.1339 -.0576 .062 Uiso calc R 1 . . H
H21C .4270 .0199 -.0905 .062 Uiso calc R 1 . . H
C23 .3778(7) -.0877(9) .1178(4) .0641(18) Uani d D 1 . . C
H23A .3766 -.1826 .1179 .077 Uiso calc PR .576(10) A 1 H
H23B .2753 -.1074 .1146 .077 Uiso calc PR .576(10) A 1 H
H23C .2941 -.0698 .1240 .077 Uiso calc PR .424(10) A 2 H
H23D .3353 -.1905 .0970 .077 Uiso calc PR .424(10) A 2 H
C24 .4590(16) .007(3) .2046(6) .093(7) Uani d PD .576(10) A 1 C
H24A .4908 .1114 .1938 .112 Uiso calc PR .576(10) A 1 H
H24B .5479 -.0006 .2165 .112 Uiso calc PR .576(10) A 1 H
C24' .432(3) -.086(2) .2133(11) .079(7) Uani d PD .424(10) A 2 C
H24C .5274 -.0844 .2126 .095 Uiso calc PR .424(10) A 2 H
H24D .3595 -.1749 .2462 .095 Uiso calc PR .424(10) A 2 H
S21 .3392(7) -.0573(9) .3016(3) .121(3) Uani d PD .576(10) A 1 S
S21' .4523(12) .0817(10) .2647(5) .126(4) Uani d PD .424(10) A 2 S
C25 .2501(18) .038(2) .2777(9) .166(8) Uani d D 1 . . C
H25A .1459 -.0318 .2665 .250 Uiso calc PR .576(10) A 1 H
H25B .2943 .0988 .2250 .250 Uiso calc PR .576(10) A 1 H
H25C .2593 .1009 .3280 .250 Uiso calc PR .576(10) A 1 H
H25D .1994 -.0416 .3210 .250 Uiso calc PR .424(10) A 2 H
H25E .1998 .0070 .2204 .250 Uiso calc PR .424(10) A 2 H
H25F .2492 .1259 .2983 .250 Uiso calc PR .424(10) A 2 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0492 .0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S .3331 .5567 '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
O1 S1 O2 . 2_665 110.08(18)
O1 S1 O2 . . 110.08(19)
O2 S1 O2 2_665 . 108.85(19)
O1 S1 O2 . 3_565 110.08(18)
O2 S1 O2 2_665 3_565 108.85(19)
O2 S1 O2 . 3_565 108.85(19)
O3 S2 O4 . 3_675 109.9(2)
O3 S2 O4 . 2_765 109.9(2)
O4 S2 O4 3_675 2_765 109.1(2)
O3 S2 O4 . . 109.9(2)
O4 S2 O4 3_675 . 109.1(2)
O4 S2 O4 2_765 . 109.1(2)
O5 S3 O6 . 2_655 111.0(2)
O5 S3 O6 . . 111.0(2)
O6 S3 O6 2_655 . 107.9(2)
O5 S3 O6 . 3_665 111.0(2)
O6 S3 O6 2_655 3_665 107.9(2)
O6 S3 O6 . 3_665 107.9(2)
C11 O11 H11 . . 109.5
C12 N11 H11A . . 109.5
C12 N11 H11B . . 109.5
H11A N11 H11B . . 109.5
C12 N11 H11C . . 109.5
H11A N11 H11C . . 109.5
H11B N11 H11C . . 109.5
O12 C11 O11 . . 124.9(5)
O12 C11 C12 . . 121.0(5)
O11 C11 C12 . . 114.1(5)
N11 C12 C13 . . 112.0(5)
N11 C12 C11 . . 105.7(4)
C13 C12 C11 . . 115.1(4)
N11 C12 H12 . . 107.9
C13 C12 H12 . . 107.9
C11 C12 H12 . . 107.9
C12 C13 C14 . . 112.7(5)
C12 C13 H13A . . 109.0
C14 C13 H13A . . 109.0
C12 C13 H13B . . 109.0
C14 C13 H13B . . 109.0
H13A C13 H13B . . 107.8
C13 C14 S11 . . 114.5(5)
C13 C14 H14A . . 108.6
S11 C14 H14A . . 108.6
C13 C14 H14B . . 108.6
S11 C14 H14B . . 108.6
H14A C14 H14B . . 107.6
C14 S11 C15 . . 98.5(5)
S11 C15 H15A . . 109.5
S11 C15 H15B . . 109.5
H15A C15 H15B . . 109.5
S11 C15 H15C . . 109.5
H15A C15 H15C . . 109.5
H15B C15 H15C . . 109.5
C21 O21 H21 . . 109.5
O22 C21 O21 . . 125.3(5)
O22 C21 C22 . . 121.2(5)
O21 C21 C22 . . 113.4(4)
N21 C22 C21 . . 108.0(4)
N21 C22 C23 . . 108.7(4)
C21 C22 C23 . . 113.7(5)
N21 C22 H22 . . 108.8
C21 C22 H22 . . 108.8
C23 C22 H22 . . 108.8
C22 N21 H21A . . 109.5
C22 N21 H21B . . 109.5
H21A N21 H21B . . 109.5
C22 N21 H21C . . 109.5
H21A N21 H21C . . 109.5
H21B N21 H21C . . 109.5
C24' C23 C22 . . 127.2(12)
C24' C23 C24 . . 32.4(9)
C22 C23 C24 . . 104.9(8)
C24' C23 H23A . . 80.0
C22 C23 H23A . . 110.8
C24 C23 H23A . . 110.8
C24' C23 H23B . . 113.8
C22 C23 H23B . . 110.8
C24 C23 H23B . . 110.8
H23A C23 H23B . . 108.8
C24' C23 H23C . . 105.5
C22 C23 H23C . . 105.5
C24 C23 H23C . . 93.0
H23A C23 H23C . . 128.6
H23B C23 H23C . . 21.6
C24' C23 H23D . . 105.5
C22 C23 H23D . . 105.5
C24 C23 H23D . . 137.8
H23A C23 H23D . . 29.8
H23B C23 H23D . . 84.6
H23C C23 H23D . . 106.1
C23 C24 S21 . . 111.9(10)
C23 C24 H24A . . 109.2
S21 C24 H24A . . 109.2
C23 C24 H24B . . 109.2
S21 C24 H24B . . 109.2
H24A C24 H24B . . 107.9
C23 C24' S21' . . 105.4(10)
C23 C24' H24C . . 110.7
S21' C24' H24C . . 110.7
C23 C24' H24D . . 110.7
S21' C24' H24D . . 110.7
H24C C24' H24D . . 108.8
C25 S21 C24 . . 95.3(9)
C24' S21' C25 . . 103.1(11)
S21 C25 S21' . . 46.4(5)
S21 C25 H25A . . 109.5
S21' C25 H25A . . 147.1
S21 C25 H25B . . 109.5
S21' C25 H25B . . 70.1
H25A C25 H25B . . 109.5
S21 C25 H25C . . 109.5
S21' C25 H25C . . 101.0
H25A C25 H25C . . 109.5
H25B C25 H25C . . 109.5
S21 C25 H25D . . 65.6
S21' C25 H25D . . 109.5
H25A C25 H25D . . 63.4
H25B C25 H25D . . 167.0
H25C C25 H25D . . 83.5
S21 C25 H25E . . 110.7
S21' C25 H25E . . 109.5
H25A C25 H25E . . 52.0
H25B C25 H25E . . 60.0
H25C C25 H25E . . 139.6
H25D C25 H25E . . 109.5
S21 C25 H25F . . 138.5
S21' C25 H25F . . 109.5
H25A C25 H25F . . 102.9
H25B C25 H25F . . 82.3
H25C C25 H25F . . 32.9
H25D C25 H25F . . 109.5
H25E C25 H25F . . 109.5
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 O1 . 1.446(7) ?
S1 O2 2_665 1.474(3) ?
S1 O2 . 1.474(3) ?
S1 O2 3_565 1.474(3) ?
S2 O3 . 1.433(8) ?
S2 O4 3_675 1.466(3) ?
S2 O4 2_765 1.466(3) ?
S2 O4 . 1.466(3) ?
S3 O5 . 1.429(8) ?
S3 O6 2_655 1.469(4) ?
S3 O6 . 1.469(4) ?
S3 O6 3_665 1.469(4) ?
O11 C11 . 1.312(7) yes
O11 H11 . .8200 ?
O12 C11 . 1.198(7) yes
N11 C12 . 1.494(7) ?
N11 H11A . .8900 ?
N11 H11B . .8900 ?
N11 H11C . .8900 ?
C11 C12 . 1.529(7) ?
C12 C13 . 1.521(8) ?
C12 H12 . .9800 ?
C13 C14 . 1.532(10) ?
C13 H13A . .9700 ?
C13 H13B . .9700 ?
C14 S11 . 1.789(9) ?
C14 H14A . .9700 ?
C14 H14B . .9700 ?
S11 C15 . 1.823(12) ?
C15 H15A . .9600 ?
C15 H15B . .9600 ?
C15 H15C . .9600 ?
O21 C21 . 1.289(7) yes
O21 H21 . .8200 ?
O22 C21 . 1.202(7) yes
C21 C22 . 1.517(7) ?
C22 N21 . 1.486(7) ?
C22 C23 . 1.530(8) ?
C22 H22 . .9800 ?
N21 H21A . .8900 ?
N21 H21B . .8900 ?
N21 H21C . .8900 ?
C23 C24' . 1.517(16) ?
C23 C24 . 1.574(14) ?
C23 H23A . .9700 ?
C23 H23B . .9700 ?
C23 H23C . .9700 ?
C23 H23D . .9700 ?
C24 S21 . 1.787(12) ?
C24 H24A . .9700 ?
C24 H24B . .9700 ?
C24' S21' . 1.803(17) ?
C24' H24C . .9700 ?
C24' H24D . .9700 ?
S21 C25 . 1.678(13) ?
S21' C25 . 1.903(15) ?
C25 H25A . .9600 ?
C25 H25B . .9600 ?
C25 H25C . .9600 ?
C25 H25D . .9600 ?
C25 H25E . .9600 ?
C25 H25F . .9600 ?
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
O11 H11 O2 2_765 .82 1.79 2.569(6) 158.9
N11 H11A O3 1_545 .89 2.36 3.233(7) 169.0
N11 H11B O2 1_545 .89 2.16 2.964(6) 150.6
N11 H11B O12 2_645 .89 2.33 2.816(6) 114.5
N11 H11C O6 . .89 2.17 2.989(8) 152.8
N11 H11C O6 2_655 .89 2.49 3.209(8) 138.0
O21 H21 O4 3_664 .82 1.76 2.576(5) 170.8
N21 H21A O4 2_654 .89 2.11 2.956(6) 159.1
N21 H21B O1 1_544 .89 2.22 3.079(6) 162.4
N21 H21B O22 2_545 .89 2.65 3.083(7) 110.8
N21 H21C O6 1_554 .89 1.96 2.839(7) 167.8
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_publ_flag
O12 C11 C12 N11 30.7(6) ?
O11 C11 C12 N11 -148.4(5) yes
O12 C11 C12 C13 154.8(5) ?
O11 C11 C12 C13 -24.3(6) ?
N11 C12 C13 C14 -154.7(5) yes
C11 C12 C13 C14 84.5(6) yes
C12 C13 C14 S11 63.1(7) yes
C13 C14 S11 C15 70.8(7) yes
O22 C21 C22 N21 -11.1(7) ?
O21 C21 C22 N21 166.7(4) yes
O22 C21 C22 C23 109.5(6) ?
O21 C21 C22 C23 -72.6(6) ?
N21 C22 C23 C24' 173.9(10) yes
C21 C22 C23 C24' 53.6(12) yes
N21 C22 C23 C24 -159.6(9) yes
C21 C22 C23 C24 80.1(10) yes
C24' C23 C24 S21 -60(2) ?
C22 C23 C24 S21 161.4(10) yes
C22 C23 C24' S21' 74.6(17) yes
C24 C23 C24' S21' 21.0(12) ?
C23 C24 S21 C25 -82.4(15) yes
C23 C24' S21' C25 70.0(15) yes
C24 S21 C25 S21' -37.2(7) ?
C24' S21' C25 S21 47.2(8) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139064869
