#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/17/2201704.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_2201704
loop_
_publ_author_name
'B. Sridhar'
'N. Srinivasan'
'Bjoern Dalhus'
'R. K. Rajaram'
_publ_section_title
;
 <small>L</small>-Methionine <small>L</small>-methioninium perchlorate
 monohydrate
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o779
_journal_page_last               o781
_journal_paper_doi               10.1107/S1600536802010656
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac
'C5 H12 N O2 S 1+,Cl O4 1-, C5 H11 N O2 S, H2 O'
_chemical_formula_moiety
'C5 H12 N O2 S 1+,Cl O4 1-, C5 H11 N O2 S, H2 O'
_chemical_formula_sum            'C10 H25 Cl N2 O9 S2'
_chemical_formula_weight         416.89
_chemical_name_common
'L-methionine L-methioninium perchlorate monohydrate'
_chemical_name_systematic
;
L-methionine L-methioninium perchlorate monohydrate
;
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.782(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.3720(15)
_cell_length_b                   5.5876(8)
_cell_length_c                   15.323(2)
_cell_measurement_reflns_used    7529
_cell_measurement_temperature    105(2)
_cell_measurement_theta_max      37.6
_cell_measurement_theta_min      2.7
_cell_volume                     927.1(2)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_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      105(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.022
_diffrn_reflns_av_sigmaI/netI    0.033
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            17119
_diffrn_reflns_theta_full        37.6
_diffrn_reflns_theta_max         37.6
_diffrn_reflns_theta_min         1.4
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.48
_exptl_absorpt_correction_T_max  0.913
_exptl_absorpt_correction_T_min  0.677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_meas      1.472
_exptl_crystal_density_method
'flotation in carbon tetrachloride and xylene'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.62
_refine_diff_density_min         -0.60
_refine_ls_abs_structure_details 'Flack (1983), 3692 Friedel pairs'
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         9018
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.07
_refine_ls_R_factor_all          0.032
_refine_ls_R_factor_gt           0.029
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0501P)²+0.1368P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.082
_refine_ls_wR_factor_ref         0.086
_reflns_number_gt                8635
_reflns_number_total             9018
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ya6110.cif
_cod_data_source_block           I
_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 

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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2201704
_cod_database_fobs_code          2201704
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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
Cl 0.521360(19) 0.65794(4) 0.605643(14) 0.01177(4) Uani d . 1 . . Cl
O1 0.56965(9) 0.6632(2) 0.52947(6) 0.02188(15) Uani d . 1 . . O
O2 0.57325(8) 0.45792(17) 0.66442(6) 0.01972(15) Uani d . 1 . . O
O3 0.55157(8) 0.87874(17) 0.65699(6) 0.02051(15) Uani d . 1 . . O
O4 0.38773(7) 0.63508(16) 0.57392(6) 0.01849(14) Uani d . 1 . . O
O1A 0.11741(7) 1.42468(17) 0.59291(6) 0.01835(14) Uani d . 1 . . O
O1B 0.12625(8) 1.41499(17) 0.74137(6) 0.01938(14) Uani d . 1 . . O
C11 0.16270(9) 1.35608(17) 0.67458(7) 0.01322(14) Uani d . 1 . . C
C12 0.27300(8) 1.18507(17) 0.69587(6) 0.01156(14) Uani d . 1 . . C
H12 0.2478 1.0303 0.7144 0.014 Uiso calc R 1 . . H
N11 0.30826(7) 1.15005(18) 0.61010(5) 0.01364(12) Uani d . 1 . . N
H11A 0.2435 1.0955 0.5657 0.020 Uiso calc R 1 . . H
H11B 0.3697 1.0448 0.6206 0.020 Uiso calc R 1 . . H
H11C 0.3325 1.2891 0.5930 0.020 Uiso calc R 1 . . H
C13 0.38321(9) 1.27857(19) 0.77340(7) 0.01450(15) Uani d . 1 . . C
H13A 0.4587 1.2132 0.7662 0.017 Uiso calc R 1 . . H
H13B 0.3870 1.4514 0.7687 0.017 Uiso calc R 1 . . H
C14 0.37581(11) 1.2128(2) 0.86843(7) 0.01780(18) Uani d . 1 . . C
H14A 0.2983 1.2714 0.8743 0.021 Uiso calc R 1 . . H
H14B 0.4421 1.2932 0.9143 0.021 Uiso calc R 1 . . H
S11 0.38650(3) 0.89384(6) 0.891692(18) 0.01910(5) Uani d . 1 . . S
C15 0.54450(12) 0.8390(3) 0.89445(9) 0.0247(2) Uani d . 1 . . C
H15A 0.5636 0.6725 0.9063 0.037 Uiso calc R 1 . . H
H15B 0.5992 0.9336 0.9421 0.037 Uiso calc R 1 . . H
H15C 0.5545 0.8819 0.8365 0.037 Uiso calc R 1 . . H
O2A 0.84774(9) -0.28937(18) 0.63593(8) 0.0265(2) Uani d . 1 . . O
O2B 1.02666(8) -0.18599(18) 0.74094(7) 0.02335(17) Uani d . 1 . . O
H2B 1.0484 -0.3205 0.7310 0.035 Uiso calc R 1 . . H
C21 0.91375(9) -0.14753(19) 0.68887(7) 0.01533(16) Uani d . 1 . . C
C22 0.86929(9) 0.10138(18) 0.70495(7) 0.01375(15) Uani d . 1 . . C
H22 0.9359 0.2167 0.7099 0.016 Uiso calc R 1 . . H
N21 0.76185(8) 0.1652(2) 0.62420(6) 0.01641(14) Uani d . 1 . . N
H21A 0.7345 0.3101 0.6324 0.025 Uiso calc R 1 . . H
H21B 0.7018 0.0584 0.6182 0.025 Uiso calc R 1 . . H
H21C 0.7852 0.1650 0.5738 0.025 Uiso calc R 1 . . H
C23 0.83376(10) 0.1067(2) 0.79420(7) 0.01655(17) Uani d . 1 . . C
H23A 0.7499 0.0487 0.7820 0.020 Uiso calc R 1 . . H
H23B 0.8880 0.0009 0.8389 0.020 Uiso calc R 1 . . H
C24 0.84328(11) 0.3598(2) 0.83367(8) 0.01893(18) Uani d . 1 . . C
H24A 0.7990 0.4685 0.7855 0.023 Uiso calc R 1 . . H
H24B 0.9294 0.4078 0.8532 0.023 Uiso calc R 1 . . H
S21 0.78281(3) 0.39046(6) 0.92960(2) 0.02403(6) Uani d . 1 . . S
C25 0.87637(14) 0.1791(3) 1.00959(9) 0.0299(3) Uani d . 1 . . C
H25A 0.8527 0.1787 1.0646 0.045 Uiso calc R 1 . . H
H25B 0.9617 0.2236 1.0240 0.045 Uiso calc R 1 . . H
H25C 0.8647 0.0221 0.9829 0.045 Uiso calc R 1 . . H
OW 0.12675(8) 1.83730(16) 0.50284(6) 0.01686(13) Uani d . 1 . . O
H1W 0.115(2) 1.718(4) 0.5277(16) 0.027(5) Uiso d . 1 . . H
H2W 0.058(2) 1.875(5) 0.4691(15) 0.032(5) Uiso d . 1 . . H
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'
Cl Cl 0.1484 0.1585 '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_publ_flag
O1 Cl O2 109.79(6) ?
O1 Cl O3 109.80(6) ?
O2 Cl O3 109.69(6) ?
O1 Cl O4 110.55(5) ?
O2 Cl O4 109.10(5) ?
O3 Cl O4 107.89(5) ?
O1B C11 O1A 126.29(9) y
O1B C11 C12 116.20(9) y
O1A C11 C12 117.51(9) y
N11 C12 C11 108.41(7) ?
N11 C12 C13 110.47(8) ?
C11 C12 C13 112.06(8) ?
N11 C12 H12 108.6 ?
C11 C12 H12 108.6 ?
C13 C12 H12 108.6 ?
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 ?
C14 C13 C12 112.74(9) ?
C14 C13 H13A 109.0 ?
C12 C13 H13A 109.0 ?
C14 C13 H13B 109.0 ?
C12 C13 H13B 109.0 ?
H13A C13 H13B 107.8 ?
C13 C14 S11 113.80(8) ?
C13 C14 H14A 108.8 ?
S11 C14 H14A 108.8 ?
C13 C14 H14B 108.8 ?
S11 C14 H14B 108.8 ?
H14A C14 H14B 107.7 ?
C15 S11 C14 100.21(6) ?
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 O2B H2B 109.5 ?
O2A C21 O2B 126.30(11) y
O2A C21 C22 122.32(10) y
O2B C21 C22 111.34(9) y
N21 C22 C21 108.16(9) ?
N21 C22 C23 111.17(8) ?
C21 C22 C23 110.54(8) ?
N21 C22 H22 109.0 ?
C21 C22 H22 109.0 ?
C23 C22 H22 109.0 ?
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 111.28(9) ?
C24 C23 H23A 109.4 ?
C22 C23 H23A 109.4 ?
C24 C23 H23B 109.4 ?
C22 C23 H23B 109.4 ?
H23A C23 H23B 108.0 ?
C23 C24 S21 114.20(8) ?
C23 C24 H24A 108.7 ?
S21 C24 H24A 108.7 ?
C23 C24 H24B 108.7 ?
S21 C24 H24B 108.7 ?
H24A C24 H24B 107.6 ?
C25 S21 C24 101.47(6) ?
S21 C25 H25A 109.5 ?
S21 C25 H25B 109.5 ?
H25A C25 H25B 109.5 ?
S21 C25 H25C 109.5 ?
H25A C25 H25C 109.5 ?
H25B C25 H25C 109.5 ?
H1W OW H2W 104(2) ?
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
Cl O1 . 1.4339(8) ?
Cl O2 . 1.4435(9) ?
Cl O3 . 1.4471(9) ?
Cl O4 . 1.4529(8) ?
O1A C11 . 1.2587(13) y
O1B C11 . 1.2596(13) y
C11 C12 . 1.5306(13) ?
C12 N11 . 1.4994(12) ?
C12 C13 . 1.5316(14) ?
C12 H12 . 0.9800 ?
N11 H11A . 0.8900 ?
N11 H11B . 0.8900 ?
N11 H11C . 0.8900 ?
C13 C14 . 1.5289(15) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 S11 . 1.8140(12) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
S11 C15 . 1.8105(14) ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
O2A C21 . 1.2156(14) y
O2B C21 . 1.3060(14) y
O2B H2B . 0.8200 ?
C21 C22 . 1.5254(15) ?
C22 N21 . 1.4925(13) ?
C22 C23 . 1.5400(14) ?
C22 H22 . 0.9800 ?
N21 H21A . 0.8900 ?
N21 H21B . 0.8900 ?
N21 H21C . 0.8900 ?
C23 C24 . 1.5290(16) ?
C23 H23A . 0.9700 ?
C23 H23B . 0.9700 ?
C24 S21 . 1.8112(11) ?
C24 H24A . 0.9700 ?
C24 H24B . 0.9700 ?
S21 C25 . 1.7979(15) ?
C25 H25A . 0.9600 ?
C25 H25B . 0.9600 ?
C25 H25C . 0.9600 ?
OW H1W . 0.80(2) ?
OW H2W . 0.82(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
N11 H11A OW 1_545 0.89 2.00 2.8180(10) 153
N11 H11B O3 . 0.89 2.18 3.0420(10) 164
N11 H11C O4 1_565 0.89 2.08 2.9620(10) 171
O2B H2B O1B 1_635 0.82 1.71 2.5000(10) 163
N21 H21A O2 . 0.89 2.20 2.9090(10) 137
N21 H21A O2A 1_565 0.89 2.57 3.189(2) 127
N21 H21B O3 1_545 0.89 2.21 3.0440(10) 155
N21 H21C OW 2_636 0.89 2.01 2.7980(10) 147
OW H1W O1A . 0.80(2) 1.92(3) 2.7060(10) 169(2)
OW H2W O1A 2_556 0.82(2) 1.95(2) 2.7590(10) 168(2)
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
O1A C11 C12 N11 3.82(12) y
O1B C11 C12 N11 -176.01(9) ?
O1B C11 C12 C13 -53.83(12) ?
O1A C11 C12 C13 126.01(10) ?
N11 C12 C13 C14 -153.83(9) y
C11 C12 C13 C14 85.17(11) ?
C12 C13 C14 S11 65.58(11) y
C13 C14 S11 C15 67.02(9) y
O2A C21 C22 N21 -21.62(15) y
O2B C21 C22 N21 160.75(10) ?
O2A C21 C22 C23 100.30(13) ?
O2B C21 C22 C23 -77.33(12) ?
N21 C22 C23 C24 -84.52(11) y
C21 C22 C23 C24 155.34(9) ?
C22 C23 C24 S21 171.84(7) y
C23 C24 S21 C25 58.75(10) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654681
