#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/08/2200891.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_2200891
loop_
_publ_author_name
'Sridhar, B.'
'Srinivasan, N.'
'Rajaram, R. K.'
_publ_section_title
;
 Bis(<small>L</small>-tyrosinium) sulfate monohydrate
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o211
_journal_page_last               o214
_journal_paper_doi               10.1107/S1600536802001174
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          '2C9 H12 N O3 1+, O4 S 2-, H2 O'
_chemical_formula_moiety         '2C9 H12 N O3 1+, O4 S 2-, H2 O'
_chemical_formula_sum            'C18 H26 N2 O11 S'
_chemical_formula_weight         478.47
_chemical_name_common            'Bis(L-tyrosinium)sulfate monohydrate'
_chemical_name_systematic
;
Bis(L-tyrosinium)sulfate monhydrate
;
_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                 109.51(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.473(2)
_cell_length_b                   6.1340(10)
_cell_length_c                   13.785(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14.208
_cell_measurement_theta_min      11.254
_cell_volume                     1073.8(4)
_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 .999
_diffrn_measured_fraction_theta_max .999
_diffrn_measurement_device_type  'Enraf-Nonis CAD-4'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0152
_diffrn_reflns_av_sigmaI/netI    .0144
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3011
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         1.57
_diffrn_standards_decay_%        none
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .215
_exptl_absorpt_correction_T_max  .939
_exptl_absorpt_correction_T_min  .862
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_meas      1.478
_exptl_crystal_density_method
'flotation using a mixture of carbon tetrachloride and xylene'
_exptl_crystal_description       needle
_exptl_crystal_F_000             504
_exptl_crystal_size_max          .5
_exptl_crystal_size_mid          .4
_exptl_crystal_size_min          .3
_refine_diff_density_max         .352
_refine_diff_density_min         -.244
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   .04(8)
_refine_ls_extinction_coef       .011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         2459
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          .0325
_refine_ls_R_factor_gt           .0300
_refine_ls_shift/su_max          .007
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0589P)²+0.1816P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          .0826
_refine_ls_wR_factor_ref         .0844
_reflns_number_gt                2322
_reflns_number_total             2455
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv6082.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_cell_volume        1073.8(3)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2200891
_cod_database_fobs_code          2200891
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
S1 .25941(4) .81125(11) .89163(4) .02933(16) Uani d . 1 . . S
O1 .36827(14) .8817(4) .93233(19) .0640(6) Uani d . 1 . . O
O2 .21975(19) .8441(4) .78079(14) .0628(6) Uani d . 1 . . O
O3 .25070(14) .5815(4) .91718(14) .0468(5) Uani d . 1 . . O
O4 .19654(17) .9470(4) .93750(16) .0536(6) Uani d . 1 . . O
O1A -.03433(13) .8380(4) .00376(12) .0477(5) Uani d . 1 . . O
O1B .13875(13) .8430(4) .09357(12) .0508(6) Uani d . 1 . . O
H1B .1451 .8601 .0370 .076 Uiso calc R 1 . . H
C11 .03881(18) .8262(5) .08282(16) .0354(5) Uani d . 1 . . C
C12 .02644(16) .7944(5) .18729(15) .0322(5) Uani d . 1 . . C
H12 .0589 .9184 .2312 .039 Uiso calc R 1 . . H
N11 -.08765(14) .7891(4) .17486(13) .0342(5) Uani d . 1 . . N
H11A -.0951 .7707 .2361 .051 Uiso calc R 1 . . H
H11B -.1185 .6793 .1336 .051 Uiso calc R 1 . . H
H11C -.1175 .9143 .1475 .051 Uiso calc R 1 . . H
C13 .0803(2) .5842(5) .23941(18) .0372(6) Uani d . 1 . . C
H13A .0396 .4605 .2034 .045 Uiso calc R 1 . . H
H13B .1494 .5753 .2322 .045 Uiso calc R 1 . . H
C14 .09296(18) .5661(5) .35209(17) .0333(5) Uani d . 1 . . C
C15 .0662(2) .3757(5) .39208(19) .0395(6) Uani d . 1 . . C
H15 .0332 .2637 .3475 .047 Uiso calc R 1 . . H
C16 .0875(2) .3486(5) .49709(18) .0405(6) Uani d . 1 . . C
H16 .0697 .2192 .5224 .049 Uiso calc R 1 . . H
C17 .13504(19) .5141(5) .56336(18) .0372(6) Uani d . 1 . . C
C18 .1615(2) .7074(6) .52584(19) .0425(6) Uani d . 1 . . C
H18 .1925 .8207 .5705 .051 Uiso calc R 1 . . H
C19 .14098(19) .7292(5) .42106(18) .0393(6) Uani d . 1 . . C
H19 .1601 .8578 .3962 .047 Uiso calc R 1 . . H
O1C .15267(16) .4830(4) .66619(12) .0516(5) Uani d . 1 . . O
H1C .1801 .5924 .6982 .077 Uiso calc R 1 . . H
O2A .4923(2) .4812(5) .84442(17) .0744(8) Uani d . 1 . . O
O2B .44252(15) .7111(5) .71149(14) .0569(6) Uani d . 1 . . O
H2B .4049 .6086 .6832 .085 Uiso calc R 1 . . H
C21 .4946(2) .6597(5) .8041(2) .0469(7) Uani d . 1 . . C
C22 .56712(18) .8353(5) .86455(17) .0381(6) Uani d . 1 . . C
H22 .5340 .9775 .8430 .046 Uiso calc R 1 . . H
N22 .58447(15) .8046(5) .97646(14) .0381(4) Uani d . 1 . . N
H22A .6269 .9090 1.0123 .057 Uiso calc R 1 . . H
H22B .6139 .6750 .9965 .057 Uiso calc R 1 . . H
H22C .5230 .8115 .9873 .057 Uiso calc R 1 . . H
C23 .67344(18) .8307(7) .84647(19) .0496(7) Uani d . 1 . . C
H23A .7164 .9511 .8832 .060 Uiso calc R 1 . . H
H23B .7098 .6963 .8743 .060 Uiso calc R 1 . . H
C24 .66165(18) .8467(6) .7338(2) .0430(7) Uani d . 1 . . C
C25 .6832(2) .6712(6) .6820(2) .0477(7) Uani d . 1 . . C
H25 .7091 .5433 .7176 .057 Uiso calc R 1 . . H
C26 .6666(2) .6823(6) .5766(2) .0486(7) Uani d . 1 . . C
H26 .6807 .5621 .5422 .058 Uiso calc R 1 . . H
C27 .6294(2) .8711(5) .5241(2) .0422(7) Uani d . 1 . . C
C28 .6082(2) 1.0494(5) .5748(2) .0464(7) Uani d . 1 . . C
H28 .5832 1.1776 .5389 .056 Uiso calc R 1 . . H
C29 .6241(2) 1.0372(6) .6786(2) .0481(7) Uani d . 1 . . C
H29 .6097 1.1579 .7125 .058 Uiso calc R 1 . . H
O2C .61082(17) .8829(4) .42014(15) .0611(6) Uani d . 1 . . O
H2C .6252 .7656 .3996 .092 Uiso calc R 1 . . H
O1W .6820(5) .6122(12) .3231(6) .093(3) Uani d P .609(12) . . O
O2W .6395(7) .6870(13) .2538(7) .066(3) Uani d P .391(12) . . O
H1W .696(5) .586(12) .264(5) .12(2) Uiso d . 1 . . H
H2W1 .6411 .4836 .3110 .050 Uiso d P .609(12) . . H
H2W2 .5963 .7836 .2239 .050 Uiso d P .391(12) . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 '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 .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S .1246 .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 S1 O2 109.53(14) ?
O1 S1 O3 110.20(13) ?
O2 S1 O3 110.77(14) ?
O1 S1 O4 108.53(15) ?
O2 S1 O4 108.09(13) ?
O3 S1 O4 109.66(13) ?
C11 O1B H1B 109.5 ?
O1A C11 O1B 126.8(2) yes
O1A C11 C12 123.5(2) yes
O1B C11 C12 109.74(18) yes
N11 C12 C11 109.27(17) ?
N11 C12 C13 110.1(2) ?
C11 C12 C13 111.6(2) ?
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 114.6(2) ?
C14 C13 H13A 108.6 ?
C12 C13 H13A 108.6 ?
C14 C13 H13B 108.6 ?
C12 C13 H13B 108.6 ?
H13A C13 H13B 107.6 ?
C19 C14 C15 117.3(2) ?
C19 C14 C13 121.4(2) ?
C15 C14 C13 121.0(2) ?
C16 C15 C14 121.6(2) ?
C16 C15 H15 119.2 ?
C14 C15 H15 119.2 ?
C17 C16 C15 119.6(3) ?
C17 C16 H16 120.2 ?
C15 C16 H16 120.2 ?
O1C C17 C16 117.8(2) ?
O1C C17 C18 121.8(2) ?
C16 C17 C18 120.3(2) ?
C19 C18 C17 119.1(3) ?
C19 C18 H18 120.5 ?
C17 C18 H18 120.5 ?
C14 C19 C18 122.1(3) ?
C14 C19 H19 118.9 ?
C18 C19 H19 118.9 ?
C17 O1C H1C 109.5 ?
C21 O2B H2B 109.5 ?
O2A C21 O2B 125.7(3) yes
O2A C21 C22 119.7(3) yes
O2B C21 C22 114.6(3) yes
N22 C22 C21 109.3(2) ?
N22 C22 C23 109.46(18) ?
C21 C22 C23 111.4(3) ?
N22 C22 H22 108.9 ?
C21 C22 H22 108.9 ?
C23 C22 H22 108.9 ?
C22 N22 H22A 109.5 ?
C22 N22 H22B 109.5 ?
H22A N22 H22B 109.5 ?
C22 N22 H22C 109.5 ?
H22A N22 H22C 109.5 ?
H22B N22 H22C 109.5 ?
C24 C23 C22 112.49(19) ?
C24 C23 H23A 109.1 ?
C22 C23 H23A 109.1 ?
C24 C23 H23B 109.1 ?
C22 C23 H23B 109.1 ?
H23A C23 H23B 107.8 ?
C25 C24 C29 118.3(2) ?
C25 C24 C23 121.0(3) ?
C29 C24 C23 120.7(3) ?
C24 C25 C26 121.0(3) ?
C24 C25 H25 119.5 ?
C26 C25 H25 119.5 ?
C27 C26 C25 119.7(3) ?
C27 C26 H26 120.2 ?
C25 C26 H26 120.2 ?
C26 C27 O2C 120.3(3) ?
C26 C27 C28 120.3(3) ?
O2C C27 C28 119.4(3) ?
C29 C28 C27 119.8(3) ?
C29 C28 H28 120.1 ?
C27 C28 H28 120.1 ?
C28 C29 C24 121.0(3) ?
C28 C29 H29 119.5 ?
C24 C29 H29 119.5 ?
C27 O2C H2C 109.5 ?
O2W O1W H1W 58(4) ?
O2W O1W H2W1 95.5(7) ?
H1W O1W H2W1 89(4) ?
O1W O2W H1W 54(4) ?
O1W O2W H2W1 39.7(5) ?
H1W O2W H2W1 60(4) ?
O1W O2W H2W2 147.4(9) ?
H1W O2W H2W2 157(4) ?
H2W1 O2W H2W2 138.3(8) ?
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 . 1.4501(19) ?
S1 O2 . 1.4545(18) ?
S1 O3 . 1.467(2) ?
S1 O4 . 1.472(2) ?
O1A C11 . 1.203(3) yes
O1B C11 . 1.309(3) yes
O1B H1B . .8200 ?
C11 C12 . 1.517(3) ?
C12 N11 . 1.489(3) ?
C12 C13 . 1.535(4) ?
C12 H12 . .9800 ?
N11 H11A . .8900 ?
N11 H11B . .8900 ?
N11 H11C . .8900 ?
C13 C14 . 1.509(3) ?
C13 H13A . .9700 ?
C13 H13B . .9700 ?
C14 C19 . 1.383(4) ?
C14 C15 . 1.390(4) ?
C15 C16 . 1.389(3) ?
C15 H15 . .9300 ?
C16 C17 . 1.373(4) ?
C16 H16 . .9300 ?
C17 O1C . 1.370(3) ?
C17 C18 . 1.387(4) ?
C18 C19 . 1.384(4) ?
C18 H18 . .9300 ?
C19 H19 . .9300 ?
O1C H1C . .8200 ?
O2A C21 . 1.233(4) yes
O2B C21 . 1.274(3) yes
O2B H2B . .8200 ?
C21 C22 . 1.505(4) ?
C22 N22 . 1.493(3) ?
C22 C23 . 1.534(3) ?
C22 H22 . .9800 ?
N22 H22A . .8900 ?
N22 H22B . .8900 ?
N22 H22C . .8900 ?
C23 C24 . 1.511(3) ?
C23 H23A . .9700 ?
C23 H23B . .9700 ?
C24 C25 . 1.375(4) ?
C24 C29 . 1.394(4) ?
C25 C26 . 1.396(4) ?
C25 H25 . .9300 ?
C26 C27 . 1.369(4) ?
C26 H26 . .9300 ?
C27 O2C . 1.371(3) ?
C27 C28 . 1.378(4) ?
C28 C29 . 1.377(4) ?
C28 H28 . .9300 ?
C29 H29 . .9300 ?
O2C H2C . .8200 ?
O1W O2W . 1.042(8) ?
O1W H1W . .91(6) ?
O1W H2W1 . .945(7) ?
O2W H1W . .96(7) ?
O2W H2W1 . 1.472(9) ?
O2W H2W2 . .837(9) ?
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
O1B H1B O4 1_554 .82 1.81 2.600(2) 161.2
N11 H11A O1C 2_556 .89 2.19 2.875(3) 133.0
N11 H11B O4 2_546 .89 1.85 2.727(3) 170.1
N11 H11C O3 2_556 .89 2.00 2.791(3) 147.4
O1C H1C O2 . .82 1.89 2.695(3) 168.5
O2B H2B O2C 2_646 .82 1.95 2.644(3) 142.4
N22 H22A O3 2_657 .89 1.93 2.792(3) 163.3
N22 H22B O1 2_647 .89 2.02 2.860(4) 155.9
N22 H22C O1 . .89 2.01 2.810(3) 148.4
N22 H22C O2A 2_657 .89 2.61 3.170(3) 121.4
O2C H2C O1W . .82 1.77 2.514(6) 150.8
O2C H2C O2W . .82 2.14 2.728(7) 129.0
O1W H2W1 O2B 2_646 .945 1.981 2.926(7) 178.7
O2W H2W2 O2A 2_656 .837 1.740 2.577(10) 176.9
O1W H1W O2 2_646 .91 2.08 2.788(6) 134
O2W H1W O2 2_646 .96 2.08 2.975(8) 154
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 -2.0(4) yes
O1B C11 C12 N11 176.6(3) ?
O1A C11 C12 C13 120.0(3) ?
O1B C11 C12 C13 -61.4(3) ?
N11 C12 C13 C14 -71.6(3) yes
C11 C12 C13 C14 166.9(2) ?
C12 C13 C14 C15 133.1(3) yes
C12 C13 C14 C19 -53.4(3) yes
C19 C14 C15 C16 -.6(4) ?
C13 C14 C15 C16 173.2(2) ?
C14 C15 C16 C17 .8(4) ?
C15 C16 C17 O1C 178.6(2) ?
C15 C16 C17 C18 .1(4) ?
O1C C17 C18 C19 -179.6(2) ?
C16 C17 C18 C19 -1.2(4) ?
C15 C14 C19 C18 -.5(4) ?
C13 C14 C19 C18 -174.3(2) ?
C17 C18 C19 C14 1.4(4) ?
O2A C21 C22 N22 -28.2(4) yes
O2B C21 C22 N22 154.2(2) ?
O2A C21 C22 C23 92.9(3) ?
O2B C21 C22 C23 -84.7(3) ?
N22 C22 C23 C24 176.4(3) yes
C21 C22 C23 C24 55.4(4) ?
C22 C23 C24 C25 -110.1(3) yes
C22 C23 C24 C29 67.1(4) yes
C29 C24 C25 C26 -.9(4) ?
C23 C24 C25 C26 176.3(2) ?
C24 C25 C26 C27 .7(4) ?
C25 C26 C27 O2C -178.7(2) ?
C25 C26 C27 C28 -.1(4) ?
C26 C27 C28 C29 -.2(4) ?
O2C C27 C28 C29 178.4(2) ?
C27 C28 C29 C24 .1(4) ?
C25 C24 C29 C28 .5(4) ?
C23 C24 C29 C28 -176.7(2) ?
