#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/19/2221945.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_2221945
loop_
_publ_author_name
'Zhang, Na'
'Liu, Kai-Sheng'
'Zhao, Xiao-Jun'
_publ_section_title
;
 2-Aminobenzothiazolium 2,4-dicarboxybenzoate monohydrate
;
_journal_coeditor_code           BT2963
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1398
_journal_paper_doi               10.1107/S160053680901890X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C7 H7 N2 S +, C9 H5 O6 -, H2 O'
_chemical_formula_moiety         'C7 H7 N2 S +, C9 H5 O6 -, H2 O'
_chemical_formula_sum            'C16 H14 N2 O7 S'
_chemical_formula_weight         378.35
_chemical_name_systematic
;
2-Aminobenzothiazolium 2,4-dicarboxybenzoate monohydrate
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.8510(4)
_cell_length_b                   24.3789(15)
_cell_length_c                   9.7043(6)
_cell_measurement_reflns_used    4384
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.91
_cell_measurement_theta_min      3.09
_cell_volume                     1620.81(17)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg & Berndt,
1999)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0247
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7728
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_T_max  0.9596
_exptl_absorpt_correction_T_min  0.9527
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.183
_refine_ls_abs_structure_details 'Flack (1983), 1116 Friedel pairs'
_refine_ls_abs_structure_Flack   0.10(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         2632
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0298
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0386P)²+0.1846P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0686
_refine_ls_wR_factor_ref         0.0703
_reflns_number_gt                2446
_reflns_number_total             2632
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2963.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 'Orthorhombic' changed to
'orthorhombic' 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_database_code               2221945
_cod_database_fobs_code          2221945
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'
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
S S1 0.41587(9) 0.29601(2) 0.74515(7) 0.04137(16) Uani d . 1 . .
O O1 0.6936(2) 0.09280(7) 1.31365(15) 0.0397(4) Uani d . 1 . .
O O2 0.3712(2) 0.10037(7) 1.34480(16) 0.0415(4) Uani d . 1 . .
O O3 0.5680(3) 0.20862(7) 1.2595(2) 0.0566(5) Uani d . 1 . .
O O4 0.4844(3) 0.25690(7) 1.07597(17) 0.0464(4) Uani d . 1 . .
H H4 0.5055 0.2826 1.1284 0.070 Uiso calc R 1 . .
O O5 0.3884(3) 0.17106(7) 0.63412(16) 0.0484(5) Uani d . 1 . .
O O6 0.3848(3) 0.08050(6) 0.61157(14) 0.0382(4) Uani d . 1 . .
H H6 0.3681 0.0882 0.5302 0.057 Uiso calc R 1 . .
N N1 0.3226(3) 0.35998(8) 0.54800(19) 0.0397(5) Uani d . 1 . .
H H1 0.2880 0.3717 0.4681 0.048 Uiso calc R 1 . .
N N2 0.3039(3) 0.26695(9) 0.4919(2) 0.0515(6) Uani d . 1 . .
H H2A 0.2647 0.2740 0.4096 0.062 Uiso calc R 1 . .
H H2B 0.3190 0.2335 0.5180 0.062 Uiso calc R 1 . .
C C1 0.3639(3) 0.39498(10) 0.6569(3) 0.0369(5) Uani d . 1 . .
C C2 0.4157(3) 0.36673(10) 0.7762(3) 0.0376(6) Uani d . 1 . .
C C3 0.4535(4) 0.39391(12) 0.8975(3) 0.0497(7) Uani d . 1 . .
H H3 0.4875 0.3751 0.9773 0.060 Uiso calc R 1 . .
C C4 0.4387(4) 0.45033(13) 0.8957(4) 0.0601(8) Uani d . 1 . .
H H4A 0.4624 0.4699 0.9763 0.072 Uiso calc R 1 . .
C C5 0.3892(4) 0.47875(11) 0.7767(4) 0.0625(9) Uani d . 1 . .
H H5 0.3814 0.5168 0.7790 0.075 Uiso calc R 1 . .
C C6 0.3515(4) 0.45135(10) 0.6548(3) 0.0508(7) Uani d . 1 . .
H H6A 0.3191 0.4702 0.5747 0.061 Uiso calc R 1 . .
C C7 0.3406(3) 0.30693(10) 0.5769(2) 0.0393(6) Uani d . 1 . .
C C8 0.4935(3) 0.10831(9) 1.1180(2) 0.0288(5) Uani d . 1 . .
C C9 0.4830(3) 0.16013(9) 1.0568(2) 0.0287(5) Uani d . 1 . .
C C10 0.4490(3) 0.16392(9) 0.9160(2) 0.0303(5) Uani d . 1 . .
H H10 0.4394 0.1983 0.8753 0.036 Uiso calc R 1 . .
C C11 0.4293(3) 0.11747(10) 0.8351(2) 0.0281(5) Uani d . 1 . .
C C12 0.4424(3) 0.06607(10) 0.8962(2) 0.0308(5) Uani d . 1 . .
H H12 0.4298 0.0345 0.8431 0.037 Uiso calc R 1 . .
C C13 0.4741(3) 0.06218(9) 1.0367(2) 0.0325(5) Uani d . 1 . .
H H13 0.4826 0.0277 1.0773 0.039 Uiso calc R 1 . .
C C14 0.5236(3) 0.10060(9) 1.2723(2) 0.0307(5) Uani d . 1 . .
C C15 0.5155(3) 0.21044(9) 1.1409(2) 0.0324(5) Uani d . 1 . .
C C16 0.3977(3) 0.12557(10) 0.6837(2) 0.0314(5) Uani d . 1 . .
O O7 0.0300(2) 0.15288(7) 0.2293(2) 0.0530(5) Uani d . 1 . .
H H7A -0.0728 0.1356 0.2522 0.080 Uiso d R 1 . .
H H7B 0.1377 0.1409 0.2607 0.080 Uiso d R 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
C7 S1 C2 . . 90.61(12) ?
C15 O4 H4 . . 109.5 ?
C16 O6 H6 . . 109.5 ?
C7 N1 C1 . . 114.8(2) ?
C7 N1 H1 . . 122.6 ?
C1 N1 H1 . . 122.6 ?
C7 N2 H2A . . 120.0 ?
C7 N2 H2B . . 120.0 ?
H2A N2 H2B . . 120.0 ?
C6 C1 N1 . . 126.2(2) ?
C6 C1 C2 . . 121.4(2) ?
N1 C1 C2 . . 112.4(2) ?
C3 C2 C1 . . 121.4(2) ?
C3 C2 S1 . . 128.4(2) ?
C1 C2 S1 . . 110.14(19) ?
C2 C3 C4 . . 117.1(3) ?
C2 C3 H3 . . 121.5 ?
C4 C3 H3 . . 121.5 ?
C3 C4 C5 . . 121.7(3) ?
C3 C4 H4A . . 119.1 ?
C5 C4 H4A . . 119.1 ?
C6 C5 C4 . . 121.1(3) ?
C6 C5 H5 . . 119.5 ?
C4 C5 H5 . . 119.5 ?
C1 C6 C5 . . 117.3(3) ?
C1 C6 H6A . . 121.4 ?
C5 C6 H6A . . 121.4 ?
N2 C7 N1 . . 125.3(2) ?
N2 C7 S1 . . 122.65(19) ?
N1 C7 S1 . . 112.06(18) ?
C13 C8 C9 . . 119.23(19) ?
C13 C8 C14 . . 118.3(2) ?
C9 C8 C14 . . 122.44(19) ?
C10 C9 C8 . . 119.1(2) ?
C10 C9 C15 . . 120.6(2) ?
C8 C9 C15 . . 120.23(19) ?
C11 C10 C9 . . 121.3(2) ?
C11 C10 H10 . . 119.3 ?
C9 C10 H10 . . 119.3 ?
C10 C11 C12 . . 119.3(2) ?
C10 C11 C16 . . 117.6(2) ?
C12 C11 C16 . . 123.2(2) ?
C13 C12 C11 . . 119.5(2) ?
C13 C12 H12 . . 120.2 ?
C11 C12 H12 . . 120.2 ?
C8 C13 C12 . . 121.5(2) ?
C8 C13 H13 . . 119.3 ?
C12 C13 H13 . . 119.3 ?
O1 C14 O2 . . 126.5(2) ?
O1 C14 C8 . . 117.49(18) ?
O2 C14 C8 . . 115.9(2) ?
O3 C15 O4 . . 122.5(2) ?
O3 C15 C9 . . 122.5(2) ?
O4 C15 C9 . . 115.03(19) ?
O5 C16 O6 . . 123.6(2) ?
O5 C16 C11 . . 121.2(2) ?
O6 C16 C11 . . 115.1(2) ?
H7A O7 H7B . . 117.1 ?
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 C7 . 1.733(2) ?
S1 C2 . 1.750(2) ?
O1 C14 . 1.246(3) ?
O2 C14 . 1.259(3) ?
O3 C15 . 1.207(3) ?
O4 C15 . 1.313(3) ?
O4 H4 . 0.8200 ?
O5 C16 . 1.211(3) ?
O6 C16 . 1.306(3) ?
O6 H6 . 0.8200 ?
N1 C7 . 1.329(3) ?
N1 C1 . 1.388(3) ?
N1 H1 . 0.8600 ?
N2 C7 . 1.301(3) ?
N2 H2A . 0.8600 ?
N2 H2B . 0.8600 ?
C1 C6 . 1.377(3) ?
C1 C2 . 1.393(3) ?
C2 C3 . 1.376(4) ?
C3 C4 . 1.379(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.389(5) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.382(4) ?
C5 H5 . 0.9300 ?
C6 H6A . 0.9300 ?
C8 C13 . 1.380(3) ?
C8 C9 . 1.398(3) ?
C8 C14 . 1.523(3) ?
C9 C10 . 1.389(3) ?
C9 C15 . 1.490(3) ?
C10 C11 . 1.385(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.389(3) ?
C11 C16 . 1.498(3) ?
C12 C13 . 1.384(3) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
O7 H7A . 0.8502 ?
O7 H7B . 0.8498 ?
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
O4 H4 O7 3_556 0.82 1.86 2.674(2) 171.4
O6 H6 O2 1_554 0.82 1.82 2.635(2) 170.5
N1 H1 O1 3_454 0.86 1.85 2.698(2) 169.7
N2 H2A O3 3_454 0.86 2.03 2.838(3) 156.3
N2 H2B O5 . 0.86 1.95 2.776(3) 159.8
O7 H7A O1 1_454 0.85 2.00 2.851(2) 176.9
O7 H7B O2 1_554 0.85 2.05 2.891(2) 170.4
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
C7 N1 C1 C6 . . . . -178.2(2) ?
C7 N1 C1 C2 . . . . -0.3(3) ?
C6 C1 C2 C3 . . . . 1.1(4) ?
N1 C1 C2 C3 . . . . -177.0(2) ?
C6 C1 C2 S1 . . . . 179.4(2) ?
N1 C1 C2 S1 . . . . 1.4(2) ?
C7 S1 C2 C3 . . . . 176.6(2) ?
C7 S1 C2 C1 . . . . -1.59(18) ?
C1 C2 C3 C4 . . . . -0.3(4) ?
S1 C2 C3 C4 . . . . -178.29(19) ?
C2 C3 C4 C5 . . . . -0.4(4) ?
C3 C4 C5 C6 . . . . 0.4(4) ?
N1 C1 C6 C5 . . . . 176.7(2) ?
C2 C1 C6 C5 . . . . -1.1(4) ?
C4 C5 C6 C1 . . . . 0.4(4) ?
C1 N1 C7 N2 . . . . 178.0(2) ?
C1 N1 C7 S1 . . . . -1.0(3) ?
C2 S1 C7 N2 . . . . -177.5(2) ?
C2 S1 C7 N1 . . . . 1.47(18) ?
C13 C8 C9 C10 . . . . 1.4(3) ?
C14 C8 C9 C10 . . . . -178.0(2) ?
C13 C8 C9 C15 . . . . -176.3(2) ?
C14 C8 C9 C15 . . . . 4.4(3) ?
C8 C9 C10 C11 . . . . -1.3(3) ?
C15 C9 C10 C11 . . . . 176.37(19) ?
C9 C10 C11 C12 . . . . 0.5(3) ?
C9 C10 C11 C16 . . . . -178.6(2) ?
C10 C11 C12 C13 . . . . 0.2(3) ?
C16 C11 C12 C13 . . . . 179.2(2) ?
C9 C8 C13 C12 . . . . -0.7(3) ?
C14 C8 C13 C12 . . . . 178.6(2) ?
C11 C12 C13 C8 . . . . -0.1(3) ?
C13 C8 C14 O1 . . . . 84.9(3) ?
C9 C8 C14 O1 . . . . -95.7(3) ?
C13 C8 C14 O2 . . . . -92.1(2) ?
C9 C8 C14 O2 . . . . 87.3(3) ?
C10 C9 C15 O3 . . . . -171.0(2) ?
C8 C9 C15 O3 . . . . 6.6(3) ?
C10 C9 C15 O4 . . . . 8.4(3) ?
C8 C9 C15 O4 . . . . -173.95(19) ?
C10 C11 C16 O5 . . . . -0.5(3) ?
C12 C11 C16 O5 . . . . -179.5(2) ?
C10 C11 C16 O6 . . . . 178.40(19) ?
C12 C11 C16 O6 . . . . -0.6(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655778
