#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/69/2016922.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_2016922
loop_
_publ_author_name
'Trzesowska-Kruszynska, Agata'
'Kruszynski, Rafal'
_publ_section_title
;
 2,3-Dihydro-1,3-benzothiazol-2-iminium hydrogen oxydiacetate: a
 combined structural and theoretical study
;
_journal_coeditor_code           GA3105
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o19
_journal_page_last               o23
_journal_paper_doi               10.1107/S0108270108038365
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C4 H5 O5 + , C7 H7 N2 S -'
_chemical_formula_moiety         'C4 H5 O5 + , C7 H7 N2 S -'
_chemical_formula_sum            'C11 H12 N2 O5 S'
_chemical_formula_weight         284.29
_chemical_name_systematic
;
2,3-Dihydro-1,3-benzothiazol-2-iminium hydrogen oxydiacetate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                87.216(3)
_cell_angle_beta                 89.845(3)
_cell_angle_gamma                85.364(3)
_cell_formula_units_Z            2
_cell_length_a                   7.0414(3)
_cell_length_b                   7.6933(3)
_cell_length_c                   11.4621(6)
_cell_measurement_reflns_used    2981
_cell_measurement_temperature    291.0(3)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      2
_cell_volume                     618.16(5)
_computing_cell_refinement       'CrysAlis RED (UNIL IC & Kuma 2000)'
_computing_data_collection       'CrysAlis CCD (UNIL IC & Kuma 2000)'
_computing_data_reduction        'CrysAlis RED (UNIL IC & Kuma 2000)'
_computing_molecular_graphics
;
XP in SHELXTL/PC (Sheldrick, 2008) and ORTEP-3 (version 1.062; Farrugia
1997)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      291.0(3)
_diffrn_detector_area_resol_mean 1048576
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Kuma KM4 CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6112
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.66
_diffrn_standards_decay_%        0.09
_diffrn_standards_interval_time  12.66
_diffrn_standards_number         14
_exptl_absorpt_coefficient_mu    0.281
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.967
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(X-RED; Stoe & Cie, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.381
_exptl_crystal_size_mid          0.083
_exptl_crystal_size_min          0.079
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.277
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2182
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0331
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0551P)²+] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0905
_reflns_number_gt                1662
_reflns_number_total             2182
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ga3105.cif
_cod_data_source_block           I
_cod_database_code               2016922
_cod_database_fobs_code          2016922
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.02638(18) 0.31143(17) 0.16983(11) 0.0361(3) Uani d . 1 . .
H H1N -0.0453 0.3655 0.2213 0.043 Uiso d R 1 . .
C C1 0.2067(2) 0.2544(2) 0.19006(15) 0.0374(4) Uani d . 1 . .
S S1 0.31425(6) 0.16495(6) 0.06783(4) 0.04831(18) Uani d . 1 . .
C C2 -0.0381(2) 0.2899(2) 0.05704(14) 0.0340(4) Uani d . 1 . .
C C3 0.1018(2) 0.2096(2) -0.01154(15) 0.0391(4) Uani d . 1 . .
C C4 0.0646(3) 0.1755(2) -0.12662(17) 0.0537(5) Uani d . 1 . .
H H4 0.1574 0.1195 -0.1726 0.064 Uiso calc R 1 . .
C C5 -0.1130(3) 0.2268(3) -0.17064(17) 0.0610(6) Uani d . 1 . .
H H5 -0.1401 0.2070 -0.2480 0.073 Uiso calc R 1 . .
C C6 -0.2530(3) 0.3076(3) -0.10198(17) 0.0568(6) Uani d . 1 . .
H H6 -0.3724 0.3406 -0.1340 0.068 Uiso calc R 1 . .
C C7 -0.2179(2) 0.3400(2) 0.01340(16) 0.0437(4) Uani d . 1 . .
H H7 -0.3119 0.3934 0.0598 0.052 Uiso calc R 1 . .
N N2 0.2957(2) 0.2653(2) 0.28827(14) 0.0520(4) Uani d . 1 . .
H H2NA 0.2272 0.3016 0.3540 0.062 Uiso d R 1 . .
H H2NB 0.4216 0.2176 0.2988 0.062 Uiso d R 1 . .
O O1 0.65382(17) 0.09502(16) 0.31142(10) 0.0493(3) Uani d . 1 . .
C C8 0.7523(2) 0.0840(2) 0.39999(15) 0.0369(4) Uani d . 1 . .
O O2 0.92056(17) 0.00620(18) 0.40394(11) 0.0595(4) Uani d . 1 . .
H H2O 0.9646 -0.0105 0.4681 0.071 Uiso d PR 0.50 . .
C C9 0.6850(2) 0.1588(2) 0.51319(14) 0.0342(4) Uani d . 1 . .
H H9A 0.6788 0.0650 0.5724 0.041 Uiso calc R 1 . .
H H9B 0.7757 0.2373 0.5391 0.041 Uiso calc R 1 . .
O O3 0.50322(15) 0.25077(14) 0.50037(10) 0.0399(3) Uani d . 1 . .
C C10 0.4434(2) 0.3251(2) 0.60564(15) 0.0410(4) Uani d . 1 . .
H H10A 0.5357 0.4040 0.6287 0.049 Uiso calc R 1 . .
H H10B 0.4396 0.2332 0.6664 0.049 Uiso calc R 1 . .
O O4 0.15973(16) 0.42035(16) 0.49886(14) 0.0590(4) Uani d . 1 . .
H H4O 0.0530 0.4737 0.5110 0.071 Uiso d PR 0.50 . .
C C11 0.2501(3) 0.4238(2) 0.59567(19) 0.0476(5) Uani d . 1 . .
O O5 0.1932(2) 0.5020(2) 0.68088(14) 0.0752(5) Uani 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
C1 N1 C2 . . 115.08(15) n
C1 N1 H1N . . 123.0 n
C2 N1 H1N . . 121.7 n
N2 C1 N1 . . 124.95(17) n
N2 C1 S1 . . 123.14(14) n
N1 C1 S1 . . 111.90(13) n
C1 S1 C3 . . 90.38(8) n
C7 C2 C3 . . 121.42(16) n
C7 C2 N1 . . 126.53(16) n
C3 C2 N1 . . 112.05(15) n
C2 C3 C4 . . 120.71(17) n
C2 C3 S1 . . 110.59(13) n
C4 C3 S1 . . 128.70(15) n
C5 C4 C3 . . 118.04(19) n
C5 C4 H4 . . 121.0 n
C3 C4 H4 . . 121.0 n
C4 C5 C6 . . 121.22(18) n
C4 C5 H5 . . 119.4 n
C6 C5 H5 . . 119.4 n
C7 C6 C5 . . 121.14(19) n
C7 C6 H6 . . 119.4 n
C5 C6 H6 . . 119.4 n
C2 C7 C6 . . 117.46(18) n
C2 C7 H7 . . 121.3 n
C6 C7 H7 . . 121.3 n
C1 N2 H2NA . . 119.5 n
C1 N2 H2NB . . 121.2 n
H2NA N2 H2NB . . 118.2 n
O1 C8 O2 . . 122.70(16) n
O1 C8 C9 . . 122.78(14) n
O2 C8 C9 . . 114.52(14) n
C8 O2 H2O . . 114.8 n
O3 C9 C8 . . 111.26(13) n
O3 C9 H9A . . 109.4 n
C8 C9 H9A . . 109.4 n
O3 C9 H9B . . 109.4 n
C8 C9 H9B . . 109.4 n
H9A C9 H9B . . 108.0 n
C10 O3 C9 . . 111.06(12) n
O3 C10 C11 . . 112.68(15) n
O3 C10 H10A . . 109.1 n
C11 C10 H10A . . 109.1 n
O3 C10 H10B . . 109.1 n
C11 C10 H10B . . 109.1 n
H10A C10 H10B . . 107.8 n
C11 O4 H4O . . 104.7 n
O5 C11 O4 . . 125.47(18) n
O5 C11 C10 . . 116.76(19) n
O4 C11 C10 . . 117.77(17) n
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
N1 C1 . 1.327(2) y
N1 C2 . 1.393(2) y
N1 H1N . 0.87 n
C1 N2 . 1.299(2) y
C1 S1 . 1.7360(18) y
S1 C3 . 1.7544(18) y
C2 C7 . 1.381(2) n
C2 C3 . 1.384(2) n
C3 C4 . 1.387(2) n
C4 C5 . 1.371(3) n
C4 H4 . 0.93 n
C5 C6 . 1.386(3) n
C5 H5 . 0.93 n
C6 C7 . 1.384(3) n
C6 H6 . 0.93 n
C7 H7 . 0.93 n
N2 H2NA . 0.94 n
N2 H2NB . 0.94 n
O1 C8 . 1.2267(19) y
C8 O2 . 1.283(2) y
C8 C9 . 1.505(2) n
O2 H2O . 0.80 n
C9 O3 . 1.4160(17) n
C9 H9A . 0.97 n
C9 H9B . 0.97 n
O3 C10 . 1.409(2) n
C10 C11 . 1.506(2) n
C10 H10A . 0.97 n
C10 H10B . 0.97 n
O4 C11 . 1.283(2) y
O4 H4O . 0.84 n
C11 O5 . 1.222(3) y
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 H1N O5 2_566 0.87 1.82 2.6915(19) 174.2 n
N2 H2NA O4 . 0.94 1.97 2.872(2) 160.7 n
N2 H2NB O1 . 0.94 1.82 2.7535(19) 171.5 n
N2 H2NA O3 . 0.94 2.56 2.8328(18) 97 n
N2 H2NB O3 . 0.94 2.41 2.8328(18) 107.0 n
O2 H2O O2 2_756 0.80 1.68 2.467(2) 167.8 n
O4 H4O O4 2_566 0.84 1.65 2.474(2) 166.6 n
C10 H10B O1 2_656 0.97 2.66 3.446(2) 138.4 n
C4 H4 O1 2_655 0.93 2.63 3.534(2) 164.4 n
