#------------------------------------------------------------------------------
#$Date: 2018-01-17 08:23:55 +0200 (Wed, 17 Jan 2018) $
#$Revision: 205305 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/09/2020902.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_2020902
loop_
_publ_author_name
'Schroeder, Zachary W.'
'Hiscock, L. K.'
'Dawe, Louise Nicole'
_publ_section_title
;
 Copper(II)- and gold(III)-mediated cyclization of a thiourea to a
 substituted 2-aminobenzothiazole
;
_journal_coeditor_code           YF3126
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              905
_journal_page_last               910
_journal_paper_doi               10.1107/S205322961701381X
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          '(C13 H12 N3 O S)2 [Au Cl2] Cl, H2 O'
_chemical_formula_moiety         '2(C13 H12 N3 O S +), Au Cl2 -, Cl -, H2 O'
_chemical_formula_sum            'C26 H26 Au Cl3 N6 O3 S2'
_chemical_formula_weight         837.96
_chemical_name_systematic
;
Bis{2-[(5-methoxy-1,3-benzothiazol-2-yl)amino]pyridin-1-ium}
dichloridogold(I) chloride monohydrate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method
;
OLEX2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                111.8670(10)
_cell_angle_beta                 97.2710(10)
_cell_angle_gamma                99.7550(10)
_cell_formula_units_Z            2
_cell_length_a                   10.00520(10)
_cell_length_b                   12.5940(2)
_cell_length_c                   12.94120(10)
_cell_measurement_reflns_used    104589
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      50.4310
_cell_measurement_theta_min      1.9540
_cell_volume                     1459.04(3)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      110.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            85384
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.111
_exptl_absorpt_coefficient_mu    5.501
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47340
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.907
_exptl_crystal_description       prism
_exptl_crystal_F_000             820
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.114
_exptl_crystal_size_min          0.102
_refine_diff_density_max         0.759
_refine_diff_density_min         -0.852
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.209
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         5973
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.208
_refine_ls_R_factor_all          0.0185
_refine_ls_R_factor_gt           0.0182
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0122P)²+2.4258P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0408
_refine_ls_wR_factor_ref         0.0408
_reflns_number_gt                5961
_reflns_number_total             5973
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yf3126sup1.cif
_cod_data_source_block           b18056
_cod_original_cell_volume        1459.03(3)
_cod_database_code               2020902
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_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_occupancy
S S2 0.41939(6) 0.75769(5) 0.72552(5) 0.01731(12) Uani d 1
O O2 0.69431(19) 0.54362(16) 0.99756(15) 0.0200(4) Uani d 1
N N4 0.6790(2) 0.59876(18) 0.46614(18) 0.0151(4) Uani d 1
H H4 0.685(3) 0.588(3) 0.524(2) 0.026(9) Uiso d 1
N N5 0.5244(2) 0.71619(19) 0.53596(18) 0.0166(4) Uani d 1
H H5 0.475(3) 0.762(2) 0.527(3) 0.030(9) Uiso d 1
N N6 0.6055(2) 0.63748(18) 0.66463(17) 0.0162(4) Uani d 1
C C14 0.7519(3) 0.5493(2) 0.3865(2) 0.0188(5) Uani d 1
H H14 0.809858 0.500715 0.398392 0.023 Uiso calc 1
C C15 0.7421(3) 0.5692(2) 0.2899(2) 0.0203(5) Uani d 1
H H15 0.792297 0.534357 0.233677 0.024 Uiso calc 1
C C16 0.6570(3) 0.6418(2) 0.2745(2) 0.0192(5) Uani d 1
H H16 0.650252 0.657322 0.207853 0.023 Uiso calc 1
C C17 0.5831(3) 0.6909(2) 0.3550(2) 0.0176(5) Uani d 1
H H17 0.524868 0.739685 0.344054 0.021 Uiso calc 1
C C18 0.5944(2) 0.6682(2) 0.4532(2) 0.0147(5) Uani d 1
C C19 0.5267(2) 0.6976(2) 0.6343(2) 0.0151(5) Uani d 1
C C20 0.5867(2) 0.6376(2) 0.7700(2) 0.0154(5) Uani d 1
C C21 0.6560(2) 0.5815(2) 0.8265(2) 0.0158(5) Uani d 1
H H21 0.719188 0.537189 0.793601 0.019 Uiso calc 1
C C22 0.6301(2) 0.5923(2) 0.9322(2) 0.0162(5) Uani d 1
C C23 0.5347(3) 0.6558(2) 0.9798(2) 0.0169(5) Uani d 1
H H23 0.518375 0.661493 1.052217 0.020 Uiso calc 1
C C24 0.4644(3) 0.7100(2) 0.9233(2) 0.0180(5) Uani d 1
H H24 0.399545 0.752526 0.955570 0.022 Uiso calc 1
C C25 0.4912(2) 0.7005(2) 0.8175(2) 0.0149(5) Uani d 1
C C26 0.7772(3) 0.4653(3) 0.9462(2) 0.0249(6) Uani d 1
H H26A 0.721112 0.401457 0.875988 0.037 Uiso calc 1
H H26B 0.811827 0.432201 0.998916 0.037 Uiso calc 1
H H26C 0.855757 0.508348 0.928260 0.037 Uiso calc 1
S S1 0.67232(6) 1.00715(5) 0.96345(5) 0.01600(12) Uani d 1
O O1 0.93392(19) 0.79817(16) 1.24720(14) 0.0197(4) Uani d 1
N N1 0.9505(2) 0.85301(18) 0.71852(18) 0.0162(4) Uani d 1
H H1 0.960(3) 0.849(3) 0.779(2) 0.025(8) Uiso d 1
N N2 0.7788(2) 0.95630(18) 0.77372(17) 0.0158(4) Uani d 1
H H2 0.723(3) 0.993(3) 0.755(3) 0.041(10) Uiso d 1
N N3 0.8627(2) 0.88981(18) 0.91125(17) 0.0149(4) Uani d 1
C C1 1.0317(3) 0.8078(2) 0.6446(2) 0.0195(5) Uani d 1
H H1A 1.097152 0.768019 0.663529 0.023 Uiso calc 1
C C2 1.0195(3) 0.8194(2) 0.5435(2) 0.0219(5) Uani d 1
H H2A 1.075907 0.787838 0.491432 0.026 Uiso calc 1
C C3 0.9224(3) 0.8786(2) 0.5176(2) 0.0204(5) Uani d 1
H H3 0.911822 0.886335 0.446918 0.024 Uiso calc 1
C C4 0.8424(3) 0.9256(2) 0.5936(2) 0.0182(5) Uani d 1
H H4A 0.777686 0.966903 0.576547 0.022 Uiso calc 1
C C5 0.8574(2) 0.9118(2) 0.6971(2) 0.0155(5) Uani d 1
C C6 0.7823(2) 0.9451(2) 0.8760(2) 0.0140(5) Uani d 1
C C7 0.8413(2) 0.8923(2) 1.0163(2) 0.0143(5) Uani d 1
C C8 0.9101(2) 0.8387(2) 1.0766(2) 0.0148(5) Uani d 1
H H8 0.978627 0.798434 1.048471 0.018 Uiso calc 1
C C9 0.8748(3) 0.8464(2) 1.1788(2) 0.0161(5) Uani d 1
C C10 0.7728(3) 0.9049(2) 1.2202(2) 0.0177(5) Uani d 1
H H10 0.750185 0.907910 1.290212 0.021 Uiso calc 1
C C11 0.7047(3) 0.9584(2) 1.1609(2) 0.0179(5) Uani d 1
H H11 0.635812 0.998071 1.189050 0.021 Uiso calc 1
C C12 0.7408(2) 0.9520(2) 1.0584(2) 0.0146(5) Uani d 1
C C13 1.0300(3) 0.7290(2) 1.2054(2) 0.0228(5) Uani d 1
H H13A 0.984946 0.664647 1.131747 0.034 Uiso calc 1
H H13B 1.060746 0.696365 1.259637 0.034 Uiso calc 1
H H13C 1.110250 0.778632 1.196026 0.034 Uiso calc 1
Au Au1 0.95986(2) 0.55935(2) 0.71308(2) 0.01682(3) Uani d 1
Cl Cl1 1.11166(7) 0.70866(6) 0.86031(6) 0.02465(13) Uani d 1
Cl Cl2 0.80710(7) 0.41058(6) 0.56663(6) 0.02767(14) Uani d 1
O O3 0.3768(2) 0.87843(19) 0.5227(2) 0.0272(4) Uani d 1
H H3A 0.425(4) 0.938(3) 0.566(3) 0.037(11) Uiso d 1
H H3B 0.380(4) 0.885(4) 0.465(3) 0.053(13) Uiso d 1
Cl Cl3 0.58921(7) 1.10213(6) 0.71166(6) 0.02530(14) 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'
Au Au -2.0133 8.8022 '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'
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
_geom_angle_publ_flag
C25 S2 C19 88.15(11) ?
C22 O2 C26 117.14(19) ?
C14 N4 H4 121(2) ?
C18 N4 H4 117(2) ?
C18 N4 C14 122.3(2) ?
C18 N5 H5 118(2) ?
C18 N5 C19 125.7(2) ?
C19 N5 H5 117(2) ?
C19 N6 C20 109.9(2) ?
N4 C14 H14 119.9 ?
C15 C14 N4 120.2(2) ?
C15 C14 H14 119.9 ?
C14 C15 H15 120.6 ?
C14 C15 C16 118.9(2) ?
C16 C15 H15 120.6 ?
C15 C16 H16 119.7 ?
C17 C16 C15 120.6(2) ?
C17 C16 H16 119.7 ?
C16 C17 H17 120.4 ?
C16 C17 C18 119.3(2) ?
C18 C17 H17 120.4 ?
N4 C18 N5 119.9(2) ?
N4 C18 C17 118.7(2) ?
N5 C18 C17 121.3(2) ?
N5 C19 S2 119.11(18) ?
N6 C19 S2 117.11(18) ?
N6 C19 N5 123.8(2) ?
N6 C20 C25 114.7(2) ?
C21 C20 N6 124.3(2) ?
C21 C20 C25 120.9(2) ?
C20 C21 H21 121.0 ?
C22 C21 C20 117.9(2) ?
C22 C21 H21 121.0 ?
O2 C22 C21 123.5(2) ?
O2 C22 C23 115.5(2) ?
C21 C22 C23 121.0(2) ?
C22 C23 H23 119.4 ?
C24 C23 C22 121.2(2) ?
C24 C23 H23 119.4 ?
C23 C24 H24 121.0 ?
C23 C24 C25 118.1(2) ?
C25 C24 H24 121.0 ?
C20 C25 S2 110.04(18) ?
C24 C25 S2 129.11(19) ?
C24 C25 C20 120.9(2) ?
O2 C26 H26A 109.5 ?
O2 C26 H26B 109.5 ?
O2 C26 H26C 109.5 ?
H26A C26 H26B 109.5 ?
H26A C26 H26C 109.5 ?
H26B C26 H26C 109.5 ?
C12 S1 C6 87.80(11) ?
C9 O1 C13 117.33(19) ?
C1 N1 H1 120(2) ?
C5 N1 H1 117(2) ?
C5 N1 C1 122.5(2) ?
C5 N2 H2 115(2) ?
C5 N2 C6 125.4(2) ?
C6 N2 H2 119(2) ?
C6 N3 C7 110.1(2) ?
N1 C1 H1A 119.9 ?
N1 C1 C2 120.3(2) ?
C2 C1 H1A 119.9 ?
C1 C2 H2A 120.6 ?
C1 C2 C3 118.8(2) ?
C3 C2 H2A 120.6 ?
C2 C3 H3 119.8 ?
C4 C3 C2 120.5(2) ?
C4 C3 H3 119.8 ?
C3 C4 H4A 120.4 ?
C3 C4 C5 119.2(2) ?
C5 C4 H4A 120.4 ?
N1 C5 N2 120.6(2) ?
N1 C5 C4 118.7(2) ?
N2 C5 C4 120.6(2) ?
N2 C6 S1 119.11(18) ?
N3 C6 S1 117.41(18) ?
N3 C6 N2 123.5(2) ?
N3 C7 C8 124.4(2) ?
N3 C7 C12 114.6(2) ?
C8 C7 C12 121.0(2) ?
C7 C8 H8 121.2 ?
C9 C8 C7 117.5(2) ?
C9 C8 H8 121.2 ?
O1 C9 C8 124.0(2) ?
O1 C9 C10 114.6(2) ?
C8 C9 C10 121.5(2) ?
C9 C10 H10 119.4 ?
C11 C10 C9 121.2(2) ?
C11 C10 H10 119.4 ?
C10 C11 H11 121.1 ?
C10 C11 C12 117.7(2) ?
C12 C11 H11 121.1 ?
C7 C12 S1 110.12(17) ?
C11 C12 S1 128.73(19) ?
C11 C12 C7 121.1(2) ?
O1 C13 H13A 109.5 ?
O1 C13 H13B 109.5 ?
O1 C13 H13C 109.5 ?
H13A C13 H13B 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
Cl2 Au1 Cl1 179.62(3) y
H3A O3 H3B 102(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S2 C19 1.747(2) ?
S2 C25 1.746(2) ?
O2 C22 1.373(3) ?
O2 C26 1.426(3) ?
N4 H4 0.81(3) ?
N4 C14 1.360(3) ?
N4 C18 1.354(3) ?
N5 H5 0.851(15) ?
N5 C18 1.361(3) ?
N5 C19 1.375(3) ?
N6 C19 1.301(3) ?
N6 C20 1.400(3) ?
C14 H14 0.9500 ?
C14 C15 1.358(4) ?
C15 H15 0.9500 ?
C15 C16 1.400(4) ?
C16 H16 0.9500 ?
C16 C17 1.372(4) ?
C17 H17 0.9500 ?
C17 C18 1.398(3) ?
C20 C21 1.392(3) ?
C20 C25 1.400(3) ?
C21 H21 0.9500 ?
C21 C22 1.386(3) ?
C22 C23 1.403(3) ?
C23 H23 0.9500 ?
C23 C24 1.378(4) ?
C24 H24 0.9500 ?
C24 C25 1.394(3) ?
C26 H26A 0.9800 ?
C26 H26B 0.9800 ?
C26 H26C 0.9800 ?
S1 C6 1.747(2) ?
S1 C12 1.745(2) ?
O1 C9 1.376(3) ?
O1 C13 1.428(3) ?
N1 H1 0.80(3) ?
N1 C1 1.359(3) ?
N1 C5 1.347(3) ?
N2 H2 0.852(15) ?
N2 C5 1.360(3) ?
N2 C6 1.379(3) ?
N3 C6 1.294(3) ?
N3 C7 1.393(3) ?
C1 H1A 0.9500 ?
C1 C2 1.363(4) ?
C2 H2A 0.9500 ?
C2 C3 1.401(4) ?
C3 H3 0.9500 ?
C3 C4 1.373(4) ?
C4 H4A 0.9500 ?
C4 C5 1.406(3) ?
C7 C8 1.397(3) ?
C7 C12 1.401(3) ?
C8 H8 0.9500 ?
C8 C9 1.385(3) ?
C9 C10 1.404(3) ?
C10 H10 0.9500 ?
C10 C11 1.383(4) ?
C11 H11 0.9500 ?
C11 C12 1.396(3) ?
C13 H13A 0.9800 ?
C13 H13B 0.9800 ?
C13 H13C 0.9800 ?
Au1 Cl1 2.2592(7) y
Au1 Cl2 2.2560(7) y
O3 H3A 0.78(3) ?
O3 H3B 0.78(3) ?
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
N5 H5 O3 . 0.851(15) 1.911(16) 2.758(3) 173(3)
N2 H2 Cl3 . 0.852(15) 2.233(16) 3.084(2) 176(4)
C3 H3 O1 1_554 0.95 2.46 3.284(3) 145.0
O3 H3A Cl3 . 0.78(3) 2.39(3) 3.155(2) 171(4)
O3 H3B Cl3 2_676 0.78(3) 2.41(3) 3.188(2) 174(4)

_cod_database_fobs_code 2020902
