#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/88/2228854.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_2228854
loop_
_publ_author_name
'Bon, Vladimir V.'
'Orysyk, Svitlana I.'
'Pekhnyo, Vasily I.'
_publ_section_title
;
 Poly[[μ₂-(1Z,N'E)-2-(1,3-benzothiazol-2-ylsulfanyl)-N'-(2-oxidobenzylidene-κ²O:O)acetohydrazidato-κ²O,N'](pyridine-κN)copper(II)]
;
_journal_coeditor_code           RK2250
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m11
_journal_paper_doi               10.1107/S160053681004986X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '[Cu (C16 H11 N3 O2 S2) (C5 H5 N)]'
_chemical_formula_moiety         'C21 H16 Cu N4 O2 S2'
_chemical_formula_sum            'C21 H16 Cu N4 O2 S2'
_chemical_formula_weight         484.04
_chemical_melting_point          553
_chemical_name_systematic
;
Poly[[μ₂-(1Z,N'E)-2-(1,3-benzothiazol-2-ylsulfanyl)-
N'-(2-oxidobenzylidene-κ²O:O)acetohydrazidato-
κ²O,N'](pyridine-κN)copper(II)]
;
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.6256(5)
_cell_length_b                   25.3751(7)
_cell_length_c                   7.1230(2)
_cell_measurement_reflns_used    2558
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.04
_cell_measurement_theta_min      2.47
_cell_volume                     3908.76(18)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2010)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_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  0.0549
_diffrn_reflns_av_sigmaI/netI    0.0467
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            18118
_diffrn_reflns_theta_full        26.41
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    1.359
_exptl_absorpt_correction_T_max  0.9229
_exptl_absorpt_correction_T_min  0.5498
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1976
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.332
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4003
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0368
_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)+(0.0326P)²+3.0387P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0886
_reflns_number_gt                2903
_reflns_number_total             4003
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rk2250.cif
_cod_data_source_block           I
_cod_database_code               2228854
_cod_database_fobs_code          2228854
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'x+1/2, -y, -z+1/2'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'-x-1/2, y, z-1/2'
'x, -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
Cu Cu1 0.753102(15) -0.037321(13) 0.25835(5) 0.02055(11) Uani d . 1 . .
S S1 0.60090(3) 0.11100(3) -0.02890(11) 0.02363(19) Uani d . 1 . .
S S2 0.53776(3) 0.21393(3) -0.09219(12) 0.02583(19) Uani d . 1 . .
N N1 0.66488(10) -0.03048(9) 0.2427(3) 0.0187(5) Uani d . 1 . .
N N2 0.64317(10) 0.01688(9) 0.1648(4) 0.0200(5) Uani d . 1 . .
N N3 0.65432(11) 0.20772(9) -0.0010(4) 0.0237(6) Uani d . 1 . .
N N4 0.84545(10) -0.04057(9) 0.2569(3) 0.0205(5) Uani d . 1 . .
O O1 0.74669(8) -0.09381(8) 0.4338(3) 0.0256(5) Uani d . 1 . .
O O2 0.74812(8) 0.02913(7) 0.1199(3) 0.0251(5) Uani d . 1 . .
C C1 0.69993(13) -0.12735(11) 0.4391(4) 0.0215(7) Uani d . 1 . .
C C2 0.64019(12) -0.11621(11) 0.3652(4) 0.0204(6) Uani d . 1 . .
C C3 0.62496(13) -0.06622(11) 0.2816(4) 0.0207(7) Uani d . 1 . .
H H3 0.5828 -0.0593 0.2535 0.025 Uiso calc R 1 . .
C C4 0.69083(12) 0.04394(11) 0.1080(4) 0.0194(6) Uani d . 1 . .
C C5 0.68084(12) 0.09696(11) 0.0213(5) 0.0246(7) Uani d . 1 . .
H H5A 0.7048 0.0990 -0.0969 0.030 Uiso calc R 1 . .
H H5B 0.6970 0.1243 0.1074 0.030 Uiso calc R 1 . .
C C6 0.60595(13) 0.17951(11) -0.0371(4) 0.0213(7) Uani d . 1 . .
C C7 0.57858(13) 0.27236(11) -0.0661(4) 0.0222(7) Uani d . 1 . .
C C8 0.63975(13) 0.26134(11) -0.0164(4) 0.0225(7) Uani d . 1 . .
C C9 0.68083(14) 0.30265(12) 0.0145(5) 0.0282(7) Uani d . 1 . .
H H9 0.7226 0.2958 0.0483 0.034 Uiso calc R 1 . .
C C10 0.65983(14) 0.35356(12) -0.0049(5) 0.0295(7) Uani d . 1 . .
H H10 0.6874 0.3821 0.0165 0.035 Uiso calc R 1 . .
C C11 0.59887(14) 0.36401(12) -0.0552(4) 0.0270(7) Uani d . 1 . .
H H11 0.5857 0.3995 -0.0680 0.032 Uiso calc R 1 . .
C C12 0.55732(13) 0.32394(12) -0.0868(4) 0.0247(7) Uani d . 1 . .
H H12 0.5157 0.3311 -0.1214 0.030 Uiso calc R 1 . .
C C13 0.59384(13) -0.15471(12) 0.3780(5) 0.0291(8) Uani d . 1 . .
H H13 0.5541 -0.1475 0.3272 0.035 Uiso calc R 1 . .
C C14 0.60447(15) -0.20236(13) 0.4619(5) 0.0371(9) Uani d . 1 . .
H H14 0.5727 -0.2282 0.4666 0.045 Uiso calc R 1 . .
C C15 0.66156(15) -0.21258(13) 0.5395(5) 0.0382(9) Uani d . 1 . .
H H15 0.6688 -0.2453 0.6002 0.046 Uiso calc R 1 . .
C C16 0.70815(14) -0.17588(12) 0.5300(5) 0.0313(8) Uani d . 1 . .
H H16 0.7469 -0.1836 0.5865 0.038 Uiso calc R 1 . .
C C17 0.87917(12) -0.00032(11) 0.1905(4) 0.0221(7) Uani d . 1 . .
H H17 0.8584 0.0293 0.1384 0.027 Uiso calc R 1 . .
C C18 0.94300(13) -0.00042(12) 0.1953(5) 0.0273(7) Uani d . 1 . .
H H18 0.9654 0.0287 0.1463 0.033 Uiso calc R 1 . .
C C19 0.97394(14) -0.04243(12) 0.2708(4) 0.0294(8) Uani d . 1 . .
H H19 1.0178 -0.0426 0.2788 0.035 Uiso calc R 1 . .
C C20 0.93942(13) -0.08465(12) 0.3352(5) 0.0271(7) Uani d . 1 . .
H H20 0.9594 -0.1149 0.3850 0.033 Uiso calc R 1 . .
C C21 0.87554(13) -0.08248(12) 0.3266(4) 0.0239(7) Uani d . 1 . .
H H21 0.8522 -0.1116 0.3715 0.029 Uiso calc 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'
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
O1 Cu1 N1 . . 91.94(9) ?
O1 Cu1 O2 . . 167.00(9) ?
N1 Cu1 O2 . . 80.68(9) ?
O1 Cu1 N4 . . 92.59(9) ?
N1 Cu1 N4 . . 175.39(10) ?
O2 Cu1 N4 . . 95.04(9) ?
O1 Cu1 O1 . 7_755 99.26(8) ?
N1 Cu1 O1 . 7_755 89.99(8) ?
O2 Cu1 O1 . 7_755 91.47(8) ?
N4 Cu1 O1 . 7_755 88.40(8) ?
C6 S1 C5 . . 98.27(13) ?
C7 S2 C6 . . 88.50(14) ?
C3 N1 N2 . . 117.7(2) ?
C3 N1 Cu1 . . 126.36(19) ?
N2 N1 Cu1 . . 115.64(16) ?
C4 N2 N1 . . 108.0(2) ?
C6 N3 C8 . . 109.9(2) ?
C17 N4 C21 . . 118.1(2) ?
C17 N4 Cu1 . . 120.92(19) ?
C21 N4 Cu1 . . 121.00(19) ?
C1 O1 Cu1 . . 123.95(19) ?
C4 O2 Cu1 . . 109.57(17) ?
O1 C1 C16 . . 118.8(3) ?
O1 C1 C2 . . 123.8(3) ?
C16 C1 C2 . . 117.4(3) ?
C13 C2 C1 . . 119.1(3) ?
C13 C2 C3 . . 118.5(3) ?
C1 C2 C3 . . 122.4(2) ?
N1 C3 C2 . . 123.9(3) ?
N1 C3 H3 . . 118.0 ?
C2 C3 H3 . . 118.0 ?
O2 C4 N2 . . 125.6(3) ?
O2 C4 C5 . . 115.2(2) ?
N2 C4 C5 . . 119.2(2) ?
C4 C5 S1 . . 113.48(19) ?
C4 C5 H5A . . 108.9 ?
S1 C5 H5A . . 108.9 ?
C4 C5 H5B . . 108.9 ?
S1 C5 H5B . . 108.9 ?
H5A C5 H5B . . 107.7 ?
N3 C6 S1 . . 126.6(2) ?
N3 C6 S2 . . 116.6(2) ?
S1 C6 S2 . . 116.77(16) ?
C12 C7 C8 . . 121.8(3) ?
C12 C7 S2 . . 128.5(2) ?
C8 C7 S2 . . 109.7(2) ?
C9 C8 C7 . . 119.6(3) ?
C9 C8 N3 . . 125.1(3) ?
C7 C8 N3 . . 115.3(3) ?
C10 C9 C8 . . 118.7(3) ?
C10 C9 H9 . . 120.6 ?
C8 C9 H9 . . 120.6 ?
C9 C10 C11 . . 121.1(3) ?
C9 C10 H10 . . 119.4 ?
C11 C10 H10 . . 119.4 ?
C12 C11 C10 . . 121.3(3) ?
C12 C11 H11 . . 119.3 ?
C10 C11 H11 . . 119.3 ?
C11 C12 C7 . . 117.4(3) ?
C11 C12 H12 . . 121.3 ?
C7 C12 H12 . . 121.3 ?
C14 C13 C2 . . 121.6(3) ?
C14 C13 H13 . . 119.2 ?
C2 C13 H13 . . 119.2 ?
C13 C14 C15 . . 119.5(3) ?
C13 C14 H14 . . 120.3 ?
C15 C14 H14 . . 120.3 ?
C16 C15 C14 . . 120.7(3) ?
C16 C15 H15 . . 119.7 ?
C14 C15 H15 . . 119.7 ?
C15 C16 C1 . . 121.7(3) ?
C15 C16 H16 . . 119.2 ?
C1 C16 H16 . . 119.2 ?
N4 C17 C18 . . 122.2(3) ?
N4 C17 H17 . . 118.9 ?
C18 C17 H17 . . 118.9 ?
C19 C18 C17 . . 120.0(3) ?
C19 C18 H18 . . 120.0 ?
C17 C18 H18 . . 120.0 ?
C18 C19 C20 . . 118.0(3) ?
C18 C19 H19 . . 121.0 ?
C20 C19 H19 . . 121.0 ?
C21 C20 C19 . . 119.5(3) ?
C21 C20 H20 . . 120.2 ?
C19 C20 H20 . . 120.2 ?
N4 C21 C20 . . 122.1(3) ?
N4 C21 H21 . . 118.9 ?
C20 C21 H21 . . 118.9 ?
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 O1 . 1.906(2) ?
Cu1 N1 . 1.919(2) ?
Cu1 O2 . 1.9566(19) ?
Cu1 N4 . 1.999(2) ?
Cu1 O1 7_755 2.720(2) ?
S1 C6 . 1.743(3) ?
S1 C5 . 1.801(3) ?
S2 C7 . 1.736(3) ?
S2 C6 . 1.758(3) ?
N1 C3 . 1.282(3) ?
N1 N2 . 1.405(3) ?
N2 C4 . 1.303(3) ?
N3 C6 . 1.293(4) ?
N3 C8 . 1.401(4) ?
N4 C17 . 1.341(4) ?
N4 C21 . 1.342(4) ?
O1 C1 . 1.322(3) ?
O2 C4 . 1.298(3) ?
C1 C16 . 1.403(4) ?
C1 C2 . 1.423(4) ?
C2 C13 . 1.403(4) ?
C2 C3 . 1.440(4) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.496(4) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C7 C12 . 1.395(4) ?
C7 C8 . 1.398(4) ?
C8 C9 . 1.391(4) ?
C9 C10 . 1.376(4) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.392(4) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.375(4) ?
C11 H11 . 0.9500 ?
C12 H12 . 0.9500 ?
C13 C14 . 1.368(4) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.377(5) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.374(4) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C17 C18 . 1.381(4) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.369(4) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.384(4) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.384(4) ?
C20 H20 . 0.9500 ?
C21 H21 . 0.9500 ?
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
O1 Cu1 N1 C3 . . . . -22.8(3) ?
O2 Cu1 N1 C3 . . . . 168.0(3) ?
O1 Cu1 N1 C3 7_755 . . . 76.5(2) ?
O1 Cu1 N1 N2 . . . . 163.35(19) ?
O2 Cu1 N1 N2 . . . . -5.89(19) ?
O1 Cu1 N1 N2 7_755 . . . -97.38(19) ?
C3 N1 N2 C4 . . . . -169.8(3) ?
Cu1 N1 N2 C4 . . . . 4.6(3) ?
O1 Cu1 N4 C17 . . . . -163.1(2) ?
O2 Cu1 N4 C17 . . . . 6.4(2) ?
O1 Cu1 N4 C17 7_755 . . . 97.7(2) ?
O1 Cu1 N4 C21 . . . . 15.2(2) ?
O2 Cu1 N4 C21 . . . . -175.4(2) ?
O1 Cu1 N4 C21 7_755 . . . -84.0(2) ?
N1 Cu1 O1 C1 . . . . 29.8(2) ?
O2 Cu1 O1 C1 . . . . 84.8(4) ?
N4 Cu1 O1 C1 . . . . -149.3(2) ?
O1 Cu1 O1 C1 7_755 . . . -60.5(2) ?
O1 Cu1 O2 C4 . . . . -50.3(5) ?
N1 Cu1 O2 C4 . . . . 5.74(19) ?
N4 Cu1 O2 C4 . . . . -175.98(19) ?
O1 Cu1 O2 C4 7_755 . . . 95.49(19) ?
Cu1 O1 C1 C16 . . . . 160.3(2) ?
Cu1 O1 C1 C2 . . . . -22.8(4) ?
O1 C1 C2 C13 . . . . 179.9(3) ?
C16 C1 C2 C13 . . . . -3.2(4) ?
O1 C1 C2 C3 . . . . -1.7(5) ?
C16 C1 C2 C3 . . . . 175.3(3) ?
N2 N1 C3 C2 . . . . -178.7(3) ?
Cu1 N1 C3 C2 . . . . 7.5(4) ?
C13 C2 C3 N1 . . . . -171.6(3) ?
C1 C2 C3 N1 . . . . 10.0(5) ?
Cu1 O2 C4 N2 . . . . -5.4(4) ?
Cu1 O2 C4 C5 . . . . 174.4(2) ?
N1 N2 C4 O2 . . . . 0.7(4) ?
N1 N2 C4 C5 . . . . -179.1(3) ?
O2 C4 C5 S1 . . . . 170.0(2) ?
N2 C4 C5 S1 . . . . -10.2(4) ?
C6 S1 C5 C4 . . . . 158.5(2) ?
C8 N3 C6 S1 . . . . -178.0(2) ?
C8 N3 C6 S2 . . . . -0.3(3) ?
C5 S1 C6 N3 . . . . -4.6(3) ?
C5 S1 C6 S2 . . . . 177.81(18) ?
C7 S2 C6 N3 . . . . 0.6(3) ?
C7 S2 C6 S1 . . . . 178.43(19) ?
C6 S2 C7 C12 . . . . 180.0(3) ?
C6 S2 C7 C8 . . . . -0.6(2) ?
C12 C7 C8 C9 . . . . 0.3(5) ?
S2 C7 C8 C9 . . . . -179.1(2) ?
C12 C7 C8 N3 . . . . -180.0(3) ?
S2 C7 C8 N3 . . . . 0.6(3) ?
C6 N3 C8 C9 . . . . 179.5(3) ?
C6 N3 C8 C7 . . . . -0.2(4) ?
C7 C8 C9 C10 . . . . 0.0(5) ?
N3 C8 C9 C10 . . . . -179.6(3) ?
C8 C9 C10 C11 . . . . -0.3(5) ?
C9 C10 C11 C12 . . . . 0.2(5) ?
C10 C11 C12 C7 . . . . 0.1(5) ?
C8 C7 C12 C11 . . . . -0.4(5) ?
S2 C7 C12 C11 . . . . 178.9(2) ?
C1 C2 C13 C14 . . . . 0.9(5) ?
C3 C2 C13 C14 . . . . -177.6(3) ?
C2 C13 C14 C15 . . . . 1.4(5) ?
C13 C14 C15 C16 . . . . -1.3(6) ?
C14 C15 C16 C1 . . . . -1.1(5) ?
O1 C1 C16 C15 . . . . -179.6(3) ?
C2 C1 C16 C15 . . . . 3.3(5) ?
C21 N4 C17 C18 . . . . -1.3(4) ?
Cu1 N4 C17 C18 . . . . 177.0(2) ?
N4 C17 C18 C19 . . . . -0.4(5) ?
C17 C18 C19 C20 . . . . 2.0(5) ?
C18 C19 C20 C21 . . . . -1.9(5) ?
C17 N4 C21 C20 . . . . 1.4(4) ?
Cu1 N4 C21 C20 . . . . -176.9(2) ?
C19 C20 C21 N4 . . . . 0.2(5) ?
