#------------------------------------------------------------------------------
#$Date: 2018-01-17 08:23:55 +0200 (Wed, 17 Jan 2018) $
#$Revision: 205305 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/09/2020901.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_2020901
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          '[Cu (C13 H11 N3 O1 S1)2 (H2 O)] (N O3)2'
_chemical_formula_moiety         'C26 H24 Cu N6 O3 S2 2+, 2(N O3 -)'
_chemical_formula_sum            'C26 H24 Cu N8 O9 S2'
_chemical_formula_weight         720.19
_chemical_name_systematic
'Aquabis[5-methoxy-N-(pyridin-2-yl-κN)benzothiazol-2-amine-κN³]copper(II) dinitrate'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.1534(4)
_cell_length_b                   7.18140(10)
_cell_length_c                   21.8523(4)
_cell_measurement_reflns_used    62086
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      39.5420
_cell_measurement_theta_min      2.2300
_cell_volume                     2848.82(9)
_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  0.0439
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            72311
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.679
_diffrn_reflns_theta_min         2.918
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.984
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83496
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_description       prism
_exptl_crystal_F_000             1476
_exptl_crystal_size_max          0.332
_exptl_crystal_size_mid          0.225
_exptl_crystal_size_min          0.173
_refine_diff_density_max         0.785
_refine_diff_density_min         -0.657
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.335
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         2703
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.334
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0497
_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)+(0.0189P)²+9.2626P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1052
_reflns_number_gt                2703
_reflns_number_total             2703
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yf3126sup1.cif
_cod_data_source_block           b17199
_cod_original_cell_volume        2848.81(9)
_cod_database_code               2020901
_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+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, 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
Cu Cu1 0.500000 0.47025(8) 0.750000 0.01397(16) Uani d 1
S S1 0.35592(5) 0.40264(13) 0.58540(4) 0.0215(2) Uani d 1
O O1 0.66894(15) 0.2340(4) 0.56003(12) 0.0299(6) Uani d 1
O O2 0.500000 0.1889(5) 0.750000 0.0364(10) Uani d 1
H H2A 0.5393(11) 0.1272(12) 0.759(3) 0.055 Uiso d 0.5
H H2B 0.468(2) 0.1274(12) 0.729(2) 0.055 Uiso d 0.5
N N1 0.41384(14) 0.6490(4) 0.77375(12) 0.0149(6) Uani d 1
N N2 0.33369(15) 0.5337(4) 0.69802(13) 0.0179(6) Uani d 1
H H2 0.2892(12) 0.525(6) 0.6845(16) 0.021 Uiso d 1
N N3 0.45591(15) 0.4536(4) 0.66819(12) 0.0145(6) Uani d 1
C C1 0.42390(19) 0.7627(5) 0.82261(15) 0.0190(7) Uani d 1
H H1 0.472590 0.782092 0.837217 0.023 Uiso calc 1
C C2 0.3669(2) 0.8512(5) 0.85188(16) 0.0238(8) Uani d 1
H H2C 0.375935 0.931356 0.885621 0.029 Uiso calc 1
C C3 0.2957(2) 0.8207(5) 0.83105(16) 0.0245(8) Uani d 1
H H3 0.255062 0.873649 0.852165 0.029 Uiso calc 1
C C4 0.28424(18) 0.7144(5) 0.78011(16) 0.0204(7) Uani d 1
H H4 0.236004 0.695842 0.764397 0.024 Uiso calc 1
C C5 0.34564(18) 0.6334(4) 0.75162(15) 0.0166(7) Uani d 1
C C6 0.38493(18) 0.4711(5) 0.65788(14) 0.0159(7) Uani d 1
C C7 0.49227(19) 0.3806(4) 0.61717(15) 0.0179(7) Uani d 1
C C8 0.5671(2) 0.3422(5) 0.61330(15) 0.0209(7) Uani d 1
H H8 0.598738 0.364950 0.647094 0.025 Uiso calc 1
C C9 0.5946(2) 0.2700(5) 0.55917(16) 0.0229(8) Uani d 1
C C10 0.5492(2) 0.2336(5) 0.50918(16) 0.0248(8) Uani d 1
H H10 0.569235 0.183235 0.472601 0.030 Uiso calc 1
C C11 0.4744(2) 0.2715(5) 0.51330(16) 0.0246(8) Uani d 1
H H11 0.442796 0.248001 0.479545 0.030 Uiso calc 1
C C12 0.44650(19) 0.3441(5) 0.56721(15) 0.0199(7) Uani d 1
C C13 0.7001(2) 0.1407(6) 0.50876(18) 0.0347(10) Uani d 1
H H13A 0.696266 0.220385 0.472504 0.052 Uiso calc 1
H H13B 0.673452 0.024068 0.501516 0.052 Uiso calc 1
H H13C 0.752063 0.113305 0.516961 0.052 Uiso calc 1
O O3 0.36773(14) 0.0698(4) 0.70721(12) 0.0281(6) Uani d 1
O O4 0.29737(14) -0.0570(4) 0.63928(12) 0.0302(6) Uani d 1
O O5 0.41492(14) -0.0873(4) 0.63256(13) 0.0340(7) Uani d 1
N N4 0.36037(15) -0.0238(4) 0.65980(13) 0.0197(6) 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'
Cu Cu 0.3201 1.2651 '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
O2 Cu1 N1 . . 127.91(8) y
O2 Cu1 N1 . 3_656 127.91(7) ?
N1 Cu1 N1 3_656 . 104.18(15) y
N3 Cu1 O2 . . 86.51(8) y
N3 Cu1 O2 3_656 . 86.51(8) ?
N3 Cu1 N1 . . 87.61(11) y
N3 Cu1 N1 . 3_656 96.69(11) y
N3 Cu1 N1 3_656 3_656 87.61(11) ?
N3 Cu1 N1 3_656 . 96.69(11) ?
N3 Cu1 N3 . 3_656 173.03(16) y
C6 S1 C12 . . 89.44(16) ?
C9 O1 C13 . . 117.9(3) ?
Cu1 O2 H2A . . 121.0 ?
Cu1 O2 H2A . 3_656 121.0(8) ?
Cu1 O2 H2B . . 120.9 ?
Cu1 O2 H2B . 3_656 120.9(8) ?
H2A O2 H2A . 3_656 118.0 ?
H2A O2 H2B . . 114.6 ?
H2A O2 H2B 3_656 3_656 114.6 ?
H2B O2 H2B . 3_656 118.2 ?
C1 N1 Cu1 . . 117.7(2) ?
C5 N1 Cu1 . . 123.6(2) ?
C5 N1 C1 . . 117.4(3) ?
C5 N2 H2 . . 118(3) ?
C6 N2 H2 . . 113(3) ?
C6 N2 C5 . . 127.5(3) ?
C6 N3 Cu1 . . 123.4(2) ?
C6 N3 C7 . . 111.2(3) ?
C7 N3 Cu1 . . 123.8(2) ?
N1 C1 H1 . . 118.5 ?
N1 C1 C2 . . 122.9(3) ?
C2 C1 H1 . . 118.5 ?
C1 C2 H2C . . 120.8 ?
C1 C2 C3 . . 118.5(3) ?
C3 C2 H2C . . 120.8 ?
C2 C3 H3 . . 120.1 ?
C4 C3 C2 . . 119.9(3) ?
C4 C3 H3 . . 120.1 ?
C3 C4 H4 . . 120.9 ?
C3 C4 C5 . . 118.2(3) ?
C5 C4 H4 . . 120.9 ?
N1 C5 N2 . . 119.6(3) ?
N1 C5 C4 . . 122.8(3) ?
N2 C5 C4 . . 117.6(3) ?
N2 C6 S1 . . 118.4(2) ?
N3 C6 S1 . . 115.2(2) ?
N3 C6 N2 . . 126.4(3) ?
C8 C7 N3 . . 125.8(3) ?
C8 C7 C12 . . 119.8(3) ?
C12 C7 N3 . . 114.4(3) ?
C7 C8 H8 . . 120.7 ?
C9 C8 C7 . . 118.6(3) ?
C9 C8 H8 . . 120.7 ?
O1 C9 C8 . . 114.4(3) ?
O1 C9 C10 . . 123.8(3) ?
C8 C9 C10 . . 121.8(3) ?
C9 C10 H10 . . 120.3 ?
C11 C10 C9 . . 119.4(3) ?
C11 C10 H10 . . 120.3 ?
C10 C11 H11 . . 120.4 ?
C12 C11 C10 . . 119.2(3) ?
C12 C11 H11 . . 120.4 ?
C7 C12 S1 . . 109.7(3) ?
C11 C12 S1 . . 129.1(3) ?
C11 C12 C7 . . 121.2(3) ?
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 ?
O3 N4 O4 . . 120.0(3) ?
O3 N4 O5 . . 120.8(3) ?
O5 N4 O4 . . 119.1(3) ?
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
Cu1 O2 . 2.020(4) y
Cu1 N1 3_656 2.089(3) ?
Cu1 N1 . 2.089(3) y
Cu1 N3 3_656 1.962(3) ?
Cu1 N3 . 1.962(3) y
S1 C6 . 1.740(3) ?
S1 C12 . 1.743(4) ?
O1 C9 . 1.374(4) ?
O1 C13 . 1.423(4) ?
O2 H2A 3_656 0.861(7) ?
O2 H2A . 0.861(14) ?
O2 H2B 3_656 0.861(7) ?
O2 H2B . 0.861(14) ?
N1 C1 . 1.357(4) ?
N1 C5 . 1.334(4) ?
N2 H2 . 0.861(18) ?
N2 C5 . 1.390(4) ?
N2 C6 . 1.355(4) ?
N3 C6 . 1.314(4) ?
N3 C7 . 1.398(4) ?
C1 H1 . 0.9500 ?
C1 C2 . 1.372(5) ?
C2 H2C . 0.9500 ?
C2 C3 . 1.387(5) ?
C3 H3 . 0.9500 ?
C3 C4 . 1.366(5) ?
C4 H4 . 0.9500 ?
C4 C5 . 1.403(5) ?
C7 C8 . 1.388(5) ?
C7 C12 . 1.397(5) ?
C8 H8 . 0.9500 ?
C8 C9 . 1.385(5) ?
C9 C10 . 1.393(5) ?
C10 H10 . 0.9500 ?
C10 C11 . 1.387(5) ?
C11 H11 . 0.9500 ?
C11 C12 . 1.384(5) ?
C13 H13A . 0.9800 ?
C13 H13B . 0.9800 ?
C13 H13C . 0.9800 ?
O3 N4 . 1.242(4) ?
O4 N4 . 1.251(4) ?
O5 N4 . 1.242(4) ?
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
O2 H2B O3 . 0.86 1.92 2.715(3) 151(3)
O2 H2A O3 3_656 0.86 1.89 2.715(3) 159.9
N2 H2 O4 8_665 0.861(18) 1.95(2) 2.781(4) 162(4)
C1 H1 O5 3_666 0.95 2.34 3.268(4) 164.7

_cod_database_fobs_code 2020901
