#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/58/2235862.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_2235862
loop_
_publ_author_name
'Cai, Hua'
'Guo, Ying'
'Li, Jian-Gang'
_publ_section_title
;
 Bis[1-phenyl-3-(1H-1,2,4-triazol-1-yl-κN⁴)propan-1-one]bis(thiocyanato-κN)copper(II)
;
_journal_coeditor_code           HY2568
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1115
_journal_paper_doi               10.1107/S160053681203108X
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '[Cu (N C S)2 (C11 H11 N3 O)2]'
_chemical_formula_moiety         'C24 H22 Cu N8 O2 S2'
_chemical_formula_sum            'C24 H22 Cu N8 O2 S2'
_chemical_formula_weight         582.16
_chemical_name_systematic
;
Bis[1-phenyl-3-(1H-1,2,4-triazol-1-yl-κN⁴)propan-1-
one]bis(thiocyanato-κN)copper(II)
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                91.1490(10)
_cell_angle_beta                 101.2700(10)
_cell_angle_gamma                110.8570(10)
_cell_formula_units_Z            2
_cell_length_a                   9.8643(8)
_cell_length_b                   10.1267(9)
_cell_length_c                   14.3538(12)
_cell_measurement_reflns_used    3208
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.73
_cell_measurement_theta_min      2.49
_cell_volume                     1307.75(19)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0127
_diffrn_reflns_av_sigmaI/netI    0.0217
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7171
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    1.033
_exptl_absorpt_correction_T_max  0.848
_exptl_absorpt_correction_T_min  0.749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             598
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.408
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         4559
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0313
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0456P)²+0.6431P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0909
_reflns_number_gt                3860
_reflns_number_total             4559
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hy2568.cif
_cod_data_source_block           I
_cod_database_code               2235862
_cod_database_fobs_code          2235862
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_symmetry_multiplicity
Cu Cu1 0.0000 0.5000 0.0000 0.03694(13) Uani d S 1 2
Cu Cu2 0.5000 0.0000 0.0000 0.04017(13) Uani d S 1 2
S S1 -0.48000(8) 0.29758(9) 0.06142(7) 0.0654(2) Uani d . 1 1
S S2 0.06035(8) -0.21058(9) 0.10990(6) 0.0600(2) Uani d . 1 1
O O1 0.4874(2) 0.1466(2) 0.35980(13) 0.0532(5) Uani d . 1 1
O O2 0.87681(19) 0.03667(17) 0.56084(12) 0.0431(4) Uani d . 1 1
N N1 0.0706(2) 0.4157(2) 0.11707(14) 0.0378(5) Uani d . 1 1
N N2 0.0832(3) 0.3365(3) 0.26177(17) 0.0553(6) Uani d . 1 1
N N3 0.1774(2) 0.3051(2) 0.21618(14) 0.0397(5) Uani d . 1 1
N N4 0.6443(2) 0.0025(2) 0.11758(14) 0.0389(5) Uani d . 1 1
N N5 0.7402(2) -0.0004(2) 0.26570(13) 0.0349(4) Uani d . 1 1
N N6 0.8416(2) -0.0119(3) 0.21731(15) 0.0511(6) Uani d . 1 1
N N7 -0.1992(2) 0.4382(2) 0.02640(15) 0.0429(5) Uani d . 1 1
N N8 0.3355(2) -0.0705(2) 0.06659(15) 0.0470(5) Uani d . 1 1
C C1 0.1693(3) 0.3532(3) 0.13169(17) 0.0419(6) Uani d . 1 1
H H1 0.2249 0.3445 0.0882 0.050 Uiso calc R 1 1
C C2 0.0219(3) 0.4019(3) 0.19914(19) 0.0530(7) Uani d . 1 1
H H2 -0.0498 0.4363 0.2103 0.064 Uiso calc R 1 1
C C3 0.2643(3) 0.2222(3) 0.25970(19) 0.0491(6) Uani d . 1 1
H H3A 0.3470 0.2360 0.2291 0.059 Uiso calc R 1 1
H H3B 0.2023 0.1221 0.2499 0.059 Uiso calc R 1 1
C C4 0.3223(3) 0.2669(3) 0.36542(17) 0.0398(6) Uani d . 1 1
H H4A 0.3629 0.3698 0.3756 0.048 Uiso calc R 1 1
H H4B 0.2403 0.2330 0.3976 0.048 Uiso calc R 1 1
C C5 0.4406(3) 0.2112(2) 0.40930(18) 0.0366(5) Uani d . 1 1
C C6 0.5010(2) 0.2403(2) 0.51463(17) 0.0346(5) Uani d . 1 1
C C7 0.4606(3) 0.3234(3) 0.57345(19) 0.0425(6) Uani d . 1 1
H H7 0.3920 0.3636 0.5475 0.051 Uiso calc R 1 1
C C8 0.5217(3) 0.3471(3) 0.6704(2) 0.0482(6) Uani d . 1 1
H H8 0.4929 0.4020 0.7094 0.058 Uiso calc R 1 1
C C9 0.6246(3) 0.2897(3) 0.7096(2) 0.0499(7) Uani d . 1 1
H H9 0.6665 0.3070 0.7747 0.060 Uiso calc R 1 1
C C10 0.6655(3) 0.2065(3) 0.6520(2) 0.0495(7) Uani d . 1 1
H H10 0.7351 0.1677 0.6782 0.059 Uiso calc R 1 1
C C11 0.6040(3) 0.1811(3) 0.55633(18) 0.0421(6) Uani d . 1 1
H H11 0.6310 0.1234 0.5183 0.050 Uiso calc R 1 1
C C12 0.7786(3) -0.0106(3) 0.12931(18) 0.0486(7) Uani d . 1 1
H H12 0.8219 -0.0181 0.0784 0.058 Uiso calc R 1 1
C C13 0.6252(3) 0.0090(3) 0.20563(16) 0.0372(5) Uani d . 1 1
H H13 0.5429 0.0188 0.2228 0.045 Uiso calc R 1 1
C C14 0.7671(3) 0.0026(3) 0.36889(16) 0.0360(5) Uani d . 1 1
H H14A 0.7983 -0.0751 0.3887 0.043 Uiso calc R 1 1
H H14B 0.6758 -0.0100 0.3897 0.043 Uiso calc R 1 1
C C15 0.8855(3) 0.1414(2) 0.41492(16) 0.0364(5) Uani d . 1 1
H H15A 0.9720 0.1595 0.3874 0.044 Uiso calc R 1 1
H H15B 0.8488 0.2175 0.4011 0.044 Uiso calc R 1 1
C C16 0.9308(2) 0.1423(2) 0.52113(16) 0.0314(5) Uani d . 1 1
C C17 1.0427(2) 0.2750(2) 0.57691(16) 0.0316(5) Uani d . 1 1
C C18 1.0867(3) 0.2771(3) 0.67518(17) 0.0398(6) Uani d . 1 1
H H18 1.0451 0.1966 0.7053 0.048 Uiso calc R 1 1
C C19 1.1913(3) 0.3976(3) 0.72822(19) 0.0496(7) Uani d . 1 1
H H19 1.2211 0.3979 0.7938 0.060 Uiso calc R 1 1
C C20 1.2523(3) 0.5184(3) 0.6840(2) 0.0528(7) Uani d . 1 1
H H20 1.3223 0.6000 0.7201 0.063 Uiso calc R 1 1
C C21 1.2093(3) 0.5178(3) 0.5862(2) 0.0490(7) Uani d . 1 1
H H21 1.2502 0.5992 0.5568 0.059 Uiso calc R 1 1
C C22 1.1058(3) 0.3970(3) 0.53216(19) 0.0399(6) Uani d . 1 1
H H22 1.0781 0.3964 0.4664 0.048 Uiso calc R 1 1
C C23 -0.3161(3) 0.3805(3) 0.03986(17) 0.0383(5) Uani d . 1 1
C C24 0.2211(3) -0.1283(3) 0.08425(16) 0.0389(6) Uani d . 1 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'
Cu Cu 0.3201 1.2651 '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
N7 Cu1 N7 2_565 . 180.00(18)
N7 Cu1 N1 2_565 2_565 90.26(8)
N7 Cu1 N1 . 2_565 89.74(8)
N7 Cu1 N1 2_565 . 89.74(8)
N7 Cu1 N1 . . 90.26(8)
N1 Cu1 N1 2_565 . 180.00(11)
N8 Cu2 N8 2_655 . 180.00(19)
N8 Cu2 N4 2_655 . 89.33(8)
N8 Cu2 N4 . . 90.67(8)
N8 Cu2 N4 2_655 2_655 90.67(8)
N8 Cu2 N4 . 2_655 89.33(8)
N4 Cu2 N4 . 2_655 180.00(16)
C1 N1 C2 . . 102.3(2)
C1 N1 Cu1 . . 129.55(16)
C2 N1 Cu1 . . 128.06(16)
C2 N2 N3 . . 102.5(2)
C1 N3 N2 . . 109.74(19)
C1 N3 C3 . . 129.3(2)
N2 N3 C3 . . 120.9(2)
C13 N4 C12 . . 103.1(2)
C13 N4 Cu2 . . 126.30(16)
C12 N4 Cu2 . . 130.52(16)
C13 N5 N6 . . 110.04(19)
C13 N5 C14 . . 128.9(2)
N6 N5 C14 . . 121.02(19)
C12 N6 N5 . . 102.6(2)
C23 N7 Cu1 . . 169.1(2)
C24 N8 Cu2 . . 163.5(2)
N3 C1 N1 . . 110.6(2)
N3 C1 H1 . . 124.7
N1 C1 H1 . . 124.7
N2 C2 N1 . . 114.9(2)
N2 C2 H2 . . 122.6
N1 C2 H2 . . 122.6
N3 C3 C4 . . 110.8(2)
N3 C3 H3A . . 109.5
C4 C3 H3A . . 109.5
N3 C3 H3B . . 109.5
C4 C3 H3B . . 109.5
H3A C3 H3B . . 108.1
C5 C4 C3 . . 113.0(2)
C5 C4 H4A . . 109.0
C3 C4 H4A . . 109.0
C5 C4 H4B . . 109.0
C3 C4 H4B . . 109.0
H4A C4 H4B . . 107.8
O1 C5 C6 . . 120.9(2)
O1 C5 C4 . . 120.6(2)
C6 C5 C4 . . 118.5(2)
C7 C6 C11 . . 118.1(2)
C7 C6 C5 . . 123.3(2)
C11 C6 C5 . . 118.6(2)
C8 C7 C6 . . 120.4(2)
C8 C7 H7 . . 119.8
C6 C7 H7 . . 119.8
C9 C8 C7 . . 120.4(3)
C9 C8 H8 . . 119.8
C7 C8 H8 . . 119.8
C8 C9 C10 . . 119.7(3)
C8 C9 H9 . . 120.1
C10 C9 H9 . . 120.1
C11 C10 C9 . . 120.1(2)
C11 C10 H10 . . 119.9
C9 C10 H10 . . 119.9
C10 C11 C6 . . 121.2(2)
C10 C11 H11 . . 119.4
C6 C11 H11 . . 119.4
N6 C12 N4 . . 114.5(2)
N6 C12 H12 . . 122.8
N4 C12 H12 . . 122.8
N4 C13 N5 . . 109.8(2)
N4 C13 H13 . . 125.1
N5 C13 H13 . . 125.1
N5 C14 C15 . . 110.65(18)
N5 C14 H14A . . 109.5
C15 C14 H14A . . 109.5
N5 C14 H14B . . 109.5
C15 C14 H14B . . 109.5
H14A C14 H14B . . 108.1
C16 C15 C14 . . 112.52(18)
C16 C15 H15A . . 109.1
C14 C15 H15A . . 109.1
C16 C15 H15B . . 109.1
C14 C15 H15B . . 109.1
H15A C15 H15B . . 107.8
O2 C16 C17 . . 120.8(2)
O2 C16 C15 . . 120.6(2)
C17 C16 C15 . . 118.55(19)
C18 C17 C22 . . 119.4(2)
C18 C17 C16 . . 119.2(2)
C22 C17 C16 . . 121.4(2)
C19 C18 C17 . . 120.4(2)
C19 C18 H18 . . 119.8
C17 C18 H18 . . 119.8
C18 C19 C20 . . 120.1(3)
C18 C19 H19 . . 120.0
C20 C19 H19 . . 120.0
C21 C20 C19 . . 120.1(2)
C21 C20 H20 . . 120.0
C19 C20 H20 . . 120.0
C22 C21 C20 . . 120.3(3)
C22 C21 H21 . . 119.8
C20 C21 H21 . . 119.8
C21 C22 C17 . . 119.7(2)
C21 C22 H22 . . 120.2
C17 C22 H22 . . 120.2
N7 C23 S1 . . 178.5(2)
N8 C24 S2 . . 179.5(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cu1 N7 2_565 1.955(2)
Cu1 N7 . 1.955(2)
Cu1 N1 2_565 2.0150(18)
Cu1 N1 . 2.0150(18)
Cu2 N8 2_655 1.966(2)
Cu2 N8 . 1.966(2)
Cu2 N4 . 1.9771(19)
Cu2 N4 2_655 1.9771(19)
S1 C23 . 1.629(3)
S2 C24 . 1.626(3)
O1 C5 . 1.213(3)
O2 C16 . 1.221(3)
N1 C1 . 1.325(3)
N1 C2 . 1.348(3)
N2 C2 . 1.307(3)
N2 N3 . 1.355(3)
N3 C1 . 1.315(3)
N3 C3 . 1.466(3)
N4 C13 . 1.318(3)
N4 C12 . 1.356(3)
N5 C13 . 1.318(3)
N5 N6 . 1.359(3)
N5 C14 . 1.451(3)
N6 C12 . 1.297(3)
N7 C23 . 1.149(3)
N8 C24 . 1.152(3)
C1 H1 . 0.9300
C2 H2 . 0.9300
C3 C4 . 1.511(4)
C3 H3A . 0.9700
C3 H3B . 0.9700
C4 C5 . 1.507(3)
C4 H4A . 0.9700
C4 H4B . 0.9700
C5 C6 . 1.494(3)
C6 C7 . 1.387(3)
C6 C11 . 1.400(3)
C7 C8 . 1.383(4)
C7 H7 . 0.9300
C8 C9 . 1.377(4)
C8 H8 . 0.9300
C9 C10 . 1.379(4)
C9 H9 . 0.9300
C10 C11 . 1.367(4)
C10 H10 . 0.9300
C11 H11 . 0.9300
C12 H12 . 0.9300
C13 H13 . 0.9300
C14 C15 . 1.506(3)
C14 H14A . 0.9700
C14 H14B . 0.9700
C15 C16 . 1.501(3)
C15 H15A . 0.9700
C15 H15B . 0.9700
C16 C17 . 1.490(3)
C17 C18 . 1.390(3)
C17 C22 . 1.402(3)
C18 C19 . 1.375(4)
C18 H18 . 0.9300
C19 C20 . 1.385(4)
C19 H19 . 0.9300
C20 C21 . 1.384(4)
C20 H20 . 0.9300
C21 C22 . 1.380(4)
C21 H21 . 0.9300
C22 H22 . 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C13 H13 O1 0.93 2.58 3.330(3) 138
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
N7 Cu1 N1 C1 2_565 -34.9(2)
N7 Cu1 N1 C1 . 145.1(2)
N7 Cu1 N1 C2 2_565 149.3(2)
N7 Cu1 N1 C2 . -30.7(2)
C2 N2 N3 C1 . 0.7(3)
C2 N2 N3 C3 . -176.3(3)
N8 Cu2 N4 C13 2_655 157.5(2)
N8 Cu2 N4 C13 . -22.5(2)
N8 Cu2 N4 C12 2_655 -27.2(2)
N8 Cu2 N4 C12 . 152.8(2)
C13 N5 N6 C12 . -0.9(3)
C14 N5 N6 C12 . -179.9(2)
N1 Cu1 N7 C23 2_565 117.2(11)
N1 Cu1 N7 C23 . -62.8(11)
N4 Cu2 N8 C24 . -146.7(8)
N4 Cu2 N8 C24 2_655 33.3(8)
N2 N3 C1 N1 . -0.7(3)
C3 N3 C1 N1 . 176.0(2)
C2 N1 C1 N3 . 0.4(3)
Cu1 N1 C1 N3 . -176.23(17)
N3 N2 C2 N1 . -0.5(4)
C1 N1 C2 N2 . 0.1(3)
Cu1 N1 C2 N2 . 176.8(2)
C1 N3 C3 C4 . 143.1(3)
N2 N3 C3 C4 . -40.5(3)
N3 C3 C4 C5 . -166.5(2)
C3 C4 C5 O1 . 5.0(3)
C3 C4 C5 C6 . -176.4(2)
O1 C5 C6 C7 . 174.5(2)
C4 C5 C6 C7 . -4.1(3)
O1 C5 C6 C11 . -5.3(3)
C4 C5 C6 C11 . 176.0(2)
C11 C6 C7 C8 . 0.3(4)
C5 C6 C7 C8 . -179.5(2)
C6 C7 C8 C9 . 0.8(4)
C7 C8 C9 C10 . -0.9(4)
C8 C9 C10 C11 . -0.1(4)
C9 C10 C11 C6 . 1.2(4)
C7 C6 C11 C10 . -1.3(4)
C5 C6 C11 C10 . 178.5(2)
N5 N6 C12 N4 . 0.7(3)
C13 N4 C12 N6 . -0.3(3)
Cu2 N4 C12 N6 . -176.39(19)
C12 N4 C13 N5 . -0.3(3)
Cu2 N4 C13 N5 . 176.02(16)
N6 N5 C13 N4 . 0.8(3)
C14 N5 C13 N4 . 179.7(2)
C13 N5 C14 C15 . -107.1(3)
N6 N5 C14 C15 . 71.7(3)
N5 C14 C15 C16 . -172.76(19)
C14 C15 C16 O2 . 2.3(3)
C14 C15 C16 C17 . -177.49(19)
O2 C16 C17 C18 . 0.7(3)
C15 C16 C17 C18 . -179.5(2)
O2 C16 C17 C22 . 179.9(2)
C15 C16 C17 C22 . -0.3(3)
C22 C17 C18 C19 . -0.1(3)
C16 C17 C18 C19 . 179.1(2)
C17 C18 C19 C20 . 0.8(4)
C18 C19 C20 C21 . -0.6(4)
C19 C20 C21 C22 . -0.2(4)
C20 C21 C22 C17 . 0.9(4)
C18 C17 C22 C21 . -0.8(3)
C16 C17 C22 C21 . -179.9(2)
