#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/78/2017826.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2017826
loop_
_publ_author_name
'Bon, Vladimir V.'
_publ_section_title
;
 The first square-planar copper(II) 1:2 complex with differently
 coordinated 2-hydroxybenzaldehyde 4-allylthiosemicarbazone ligands
;
_journal_coeditor_code           GD3359
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m300
_journal_page_last               m302
_journal_paper_doi               10.1107/S0108270110035754
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac
'[Cu (C11 H11 N3 O S) (C11 H13 N3 O S)] , H2 O'
_chemical_formula_moiety         'C22 H24 Cu N6 O2 S2 , H2 O'
_chemical_formula_sum            'C22 H26 Cu N6 O3 S2'
_chemical_formula_weight         550.15
_chemical_melting_point          231
_chemical_name_systematic
;[(E)-4-Allyl-1-(2-oxidobenzylidene)thiosemicarbazidato-
κ³O,N¹,S][(Z)-4-allyl-2-(2-
hydroxybenzylidene)thiosemicarbazide-κS]copper(II) monohydrate
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_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                 116.458(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.763(3)
_cell_length_b                   8.5526(9)
_cell_length_c                   24.496(3)
_cell_measurement_reflns_used    5321
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.17
_cell_measurement_theta_min      2.54
_cell_volume                     4832.1(10)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0477
_diffrn_reflns_av_sigmaI/netI    0.0545
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            25072
_diffrn_reflns_theta_full        26.55
_diffrn_reflns_theta_max         26.55
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    1.114
_exptl_absorpt_correction_T_max  0.9464
_exptl_absorpt_correction_T_min  0.6058
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             2280
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.359
_refine_ls_abs_structure_details 'Flack (1983), 3047 Friedel pairs'
_refine_ls_abs_structure_Flack   0.464(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     656
_refine_ls_number_reflns         8043
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0294P)²+1.6385P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0683
_refine_ls_wR_factor_ref         0.0742
_reflns_number_gt                6716
_reflns_number_total             8043
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gd3359.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2017826
_cod_database_fobs_code          2017826
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
Cu Cu1 0.40946(2) 0.23917(5) 0.11016(2) 0.01915(11) Uani d . 1 . .
S S1 0.47493(6) 0.36162(13) 0.19397(5) 0.0226(3) Uani d . 1 . .
S S2 0.34069(5) 0.35102(12) 0.13596(5) 0.0242(2) Uani d . 1 . .
O O1 0.35948(12) 0.1031(3) 0.04694(14) 0.0253(7) Uani d . 1 . .
O O2 0.09263(13) 0.0620(4) -0.02904(15) 0.0274(8) Uani d . 1 . .
H H2O 0.121(2) 0.099(6) -0.009(2) 0.041 Uiso d . 1 . .
N N1 0.52671(19) 0.2851(5) 0.1227(2) 0.0223(10) Uani d . 1 . .
N N2 0.47390(15) 0.2075(4) 0.09008(15) 0.0203(8) Uani d . 1 . .
N N3 0.5797(2) 0.4281(6) 0.2074(2) 0.0355(12) Uani d D 1 B .
H H3N 0.581(2) 0.475(6) 0.2354(19) 0.043 Uiso d D 1 . .
N N4 0.25815(19) 0.2184(5) 0.0390(2) 0.0197(10) Uani d D 1 . .
H H4N 0.2821(17) 0.170(5) 0.032(2) 0.024 Uiso d D 1 . .
N N5 0.20338(15) 0.1575(4) 0.00493(15) 0.0196(8) Uani d . 1 . .
N N6 0.22710(17) 0.3505(4) 0.10128(17) 0.0225(9) Uani d D 1 . .
H H6N 0.1949(16) 0.325(6) 0.079(2) 0.027 Uiso d D 1 . .
C C1 0.52978(19) 0.3554(5) 0.17135(18) 0.0224(10) Uani d . 1 . .
C C2 0.47400(19) 0.1148(4) 0.04825(19) 0.0199(9) Uani d . 1 . .
H H2A 0.5089 0.1077 0.0442 0.024 Uiso calc R 1 . .
C C3 0.42584(19) 0.0218(4) 0.00742(18) 0.0207(9) Uani d . 1 . .
C C4 0.3718(3) 0.0167(5) 0.0087(3) 0.0196(12) Uani d . 1 . .
C C5 0.3299(2) -0.0849(5) -0.0319(2) 0.0248(10) Uani d . 1 . .
H H5A 0.2935 -0.0931 -0.0310 0.030 Uiso calc R 1 . .
C C6 0.3399(2) -0.1725(5) -0.07291(19) 0.0258(10) Uani d . 1 . .
H H6A 0.3103 -0.2400 -0.0999 0.031 Uiso calc R 1 . .
C C7 0.3919(2) -0.1649(5) -0.0758(2) 0.0283(12) Uani d . 1 . .
H H7A 0.3981 -0.2244 -0.1051 0.034 Uiso calc R 1 . .
C C8 0.4347(2) -0.0693(5) -0.0353(2) 0.0258(10) Uani d . 1 . .
H H8A 0.4711 -0.0649 -0.0363 0.031 Uiso calc R 1 . .
C C9 0.6313(2) 0.4200(8) 0.1973(2) 0.0569(17) Uani d D 1 . .
H H9A 0.6398 0.3087 0.1935 0.068 Uiso calc PR 0.67 A 1
H H9B 0.6228 0.4718 0.1581 0.068 Uiso calc PR 0.67 A 1
H H9C 0.6228 0.3516 0.1617 0.068 Uiso calc PR 0.33 A 2
H H9D 0.6395 0.5259 0.1869 0.068 Uiso calc PR 0.33 A 2
C C10A 0.6819(3) 0.4904(10) 0.2442(3) 0.0441(17) Uani d PD 0.67 B 1
H H10A 0.6791 0.5986 0.2512 0.053 Uiso calc PR 0.67 B 1
C C11A 0.7319(8) 0.423(3) 0.2788(19) 0.064(2) Uani d PD 0.67 B 1
H H11A 0.7374 0.3153 0.2739 0.077 Uiso calc PR 0.67 B 1
H H11B 0.7626 0.4829 0.3086 0.077 Uiso calc PR 0.67 B 1
C C10B 0.6810(6) 0.364(2) 0.2467(6) 0.0441(17) Uani d PD 0.33 B 2
H H10B 0.6789 0.2607 0.2598 0.053 Uiso calc PR 0.33 B 2
C C11B 0.7307(15) 0.439(6) 0.277(4) 0.064(2) Uani d PD 0.33 B 2
H H11C 0.7351 0.5428 0.2661 0.077 Uiso calc PR 0.33 B 2
H H11D 0.7618 0.3891 0.3103 0.077 Uiso calc PR 0.33 B 2
Cu Cu2 0.71165(2) 0.00134(5) 0.43649(2) 0.01832(11) Uani d . 1 . .
S S3 0.64769(5) 0.12090(13) 0.35181(5) 0.0222(3) Uani d . 1 . .
S S4 0.78095(5) 0.11502(13) 0.41212(5) 0.0239(2) Uani d . 1 . .
O O3 0.76156(12) -0.1299(3) 0.50184(13) 0.0226(7) Uani d . 1 . .
O O4 1.02785(14) -0.1829(4) 0.57227(14) 0.0286(7) Uani d D 1 . .
H H4O 0.9978(17) -0.142(6) 0.553(2) 0.043 Uiso d D 1 . .
N N7 0.59260(18) 0.0427(5) 0.4206(2) 0.0215(10) Uani d . 1 . .
N N8 0.64498(15) -0.0347(4) 0.45353(16) 0.0180(8) Uani d . 1 . .
N N9 0.54375(18) 0.1984(5) 0.3380(2) 0.0230(9) Uani d D 1 . .
H H9N 0.5393(19) 0.240(5) 0.3066(16) 0.028 Uiso d D 1 . .
N N10 0.8642(2) -0.0147(4) 0.5090(2) 0.0191(10) Uani d D 1 . .
H H10N 0.8382(16) -0.053(5) 0.516(2) 0.023 Uiso d D 1 . .
N N11 0.91835(15) -0.0831(4) 0.54169(15) 0.0196(8) Uani d . 1 . .
N N12 0.89361(18) 0.1033(4) 0.44378(18) 0.0209(9) Uani d . 1 . .
H H12N 0.929(2) 0.085(5) 0.467(2) 0.025 Uiso d . 1 . .
C C12 0.26968(19) 0.3038(5) 0.08882(19) 0.0197(10) Uani d . 1 . .
C C13 0.19869(18) 0.0857(4) -0.04314(18) 0.0199(9) Uani d . 1 . .
H H13A 0.2303 0.0918 -0.0531 0.024 Uiso calc R 1 . .
C C14 0.14868(18) -0.0034(4) -0.08293(19) 0.0185(9) Uani d . 1 . .
C C15 0.0981(3) -0.0129(5) -0.0749(3) 0.0230(13) Uani d . 1 . .
C C16 0.0518(2) -0.1037(5) -0.1141(2) 0.0295(11) Uani d . 1 . .
H H16A 0.0178 -0.1114 -0.1082 0.035 Uiso calc R 1 . .
C C17 0.0552(2) -0.1827(6) -0.1614(3) 0.0327(13) Uani d . 1 . .
H H17A 0.0229 -0.2420 -0.1888 0.039 Uiso calc R 1 . .
C C18 0.1052(2) -0.1768(5) -0.1697(2) 0.0323(11) Uani d . 1 . .
H H18A 0.1076 -0.2338 -0.2018 0.039 Uiso calc R 1 . .
C C19 0.1508(2) -0.0881(5) -0.1310(2) 0.0263(12) Uani d . 1 . .
H H19A 0.1849 -0.0834 -0.1368 0.032 Uiso calc R 1 . .
C C20 0.23493(19) 0.4489(5) 0.15240(19) 0.0244(10) Uani d . 1 . .
H H20A 0.1996 0.5128 0.1411 0.029 Uiso calc R 1 . .
H H20B 0.2676 0.5213 0.1609 0.029 Uiso calc R 1 . .
C C21 0.2467(2) 0.3597(6) 0.2091(2) 0.0343(11) Uani d . 1 . .
H H21A 0.2707 0.2697 0.2179 0.041 Uiso calc R 1 . .
C C22 0.2264(2) 0.3972(7) 0.2471(2) 0.0495(15) Uani d . 1 . .
H H22A 0.2022 0.4865 0.2396 0.059 Uiso calc R 1 . .
H H22B 0.2355 0.3353 0.2824 0.059 Uiso calc R 1 . .
C C23 0.59128(19) 0.1173(5) 0.37296(19) 0.0207(9) Uani d . 1 . .
C C24 0.64412(18) -0.1295(5) 0.49362(19) 0.0207(9) Uani d . 1 . .
H H24A 0.6083 -0.1413 0.4955 0.025 Uiso calc R 1 . .
C C25 0.69211(18) -0.2196(4) 0.53584(19) 0.0187(9) Uani d . 1 . .
C C26 0.7479(2) -0.2177(6) 0.5380(2) 0.0194(12) Uani d . 1 . .
C C27 0.7900(2) -0.3162(5) 0.5804(2) 0.0233(10) Uani d . 1 . .
H H27A 0.8273 -0.3206 0.5815 0.028 Uiso calc R 1 . .
C C28 0.7791(2) -0.4067(5) 0.6205(2) 0.0268(10) Uani d . 1 . .
H H28A 0.8090 -0.4704 0.6492 0.032 Uiso calc R 1 . .
C C29 0.7249(2) -0.4060(5) 0.6194(2) 0.0258(11) Uani d . 1 . .
H H29A 0.7173 -0.4679 0.6473 0.031 Uiso calc R 1 . .
C C30 0.6825(2) -0.3140(5) 0.5773(2) 0.0245(10) Uani d . 1 . .
H H30A 0.6451 -0.3142 0.5760 0.029 Uiso calc R 1 . .
C C31 0.49110(18) 0.2020(5) 0.34599(19) 0.0272(10) Uani d . 1 . .
H H31A 0.4669 0.2912 0.3226 0.033 Uiso calc R 1 . .
H H31B 0.5017 0.2198 0.3896 0.033 Uiso calc R 1 . .
C C32 0.45642(18) 0.0564(5) 0.32585(19) 0.0284(10) Uani d . 1 . .
H H32A 0.4732 -0.0380 0.3467 0.034 Uiso calc R 1 . .
C C33 0.4036(2) 0.0507(7) 0.2808(2) 0.0497(14) Uani d . 1 . .
H H33A 0.3858 0.1433 0.2592 0.060 Uiso calc R 1 . .
H H33B 0.3834 -0.0460 0.2698 0.060 Uiso calc R 1 . .
C C34 0.85155(18) 0.0637(5) 0.45776(19) 0.0168(9) Uani d . 1 . .
C C35 0.92363(18) -0.1547(4) 0.59007(18) 0.0197(9) Uani d . 1 . .
H H35A 0.8934 -0.1441 0.6020 0.024 Uiso calc R 1 . .
C C36 0.97292(19) -0.2500(5) 0.6271(2) 0.0193(9) Uani d . 1 . .
C C37 1.0220(3) -0.2640(5) 0.6178(3) 0.0199(12) Uani d . 1 . .
C C38 1.0670(2) -0.3603(5) 0.65349(19) 0.0275(10) Uani d . 1 . .
H H38A 1.1004 -0.3682 0.6465 0.033 Uiso calc R 1 . .
C C39 1.0635(2) -0.4452(6) 0.6995(2) 0.0280(12) Uani d . 1 . .
H H39A 1.0945 -0.5125 0.7241 0.034 Uiso calc R 1 . .
C C40 1.0158(2) -0.4336(5) 0.71008(19) 0.0273(10) Uani d . 1 . .
H H40A 1.0137 -0.4929 0.7418 0.033 Uiso calc R 1 . .
C C41 0.9711(2) -0.3366(5) 0.6750(2) 0.0235(11) Uani d . 1 . .
H H41A 0.9384 -0.3277 0.6831 0.028 Uiso calc R 1 . .
C C42 0.88606(19) 0.1936(5) 0.39004(19) 0.0237(10) Uani d . 1 . .
H H42A 0.9231 0.2453 0.3981 0.028 Uiso calc R 1 . .
H H42B 0.8568 0.2763 0.3826 0.028 Uiso calc R 1 . .
C C43 0.8672(2) 0.0940(6) 0.3343(2) 0.0339(11) Uani d . 1 . .
H H43A 0.8360 0.0238 0.3259 0.041 Uiso calc R 1 . .
C C44 0.8898(2) 0.0953(6) 0.2964(2) 0.0431(13) Uani d . 1 . .
H H44A 0.9211 0.1637 0.3031 0.052 Uiso calc R 1 . .
H H44B 0.8751 0.0278 0.2620 0.052 Uiso calc R 1 . .
O O5 1.01768(14) 0.1061(4) 0.50618(15) 0.0272(7) Uani d D 1 . .
H H51O 1.0408(19) 0.052(5) 0.506(2) 0.041 Uiso d D 1 . .
H H52O 1.031(2) 0.132(5) 0.540(2) 0.041 Uiso d . 1 . .
O O6 0.10257(14) 0.3495(4) 0.03666(14) 0.0284(7) Uani d D 1 . .
H H61O 0.089(2) 0.362(5) -0.0033(14) 0.043 Uiso d D 1 . .
H H62O 0.0763(18) 0.293(5) 0.041(2) 0.043 Uiso d 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'
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
_geom_angle_publ_flag
O1 Cu1 N2 . . 93.03(13) y
O1 Cu1 S1 . . 170.07(10) ?
N2 Cu1 S1 . . 85.32(11) y
O1 Cu1 S2 . . 98.68(9) y
N2 Cu1 S2 . . 163.67(10) ?
S1 Cu1 S2 . . 85.02(5) y
C1 S1 Cu1 . . 94.62(15) ?
C12 S2 Cu1 . . 115.49(15) ?
C4 O1 Cu1 . . 128.4(3) ?
C15 O2 H2O . . 109(4) ?
C1 N1 N2 . . 112.8(4) ?
C2 N2 N1 . . 113.4(4) ?
C2 N2 Cu1 . . 125.9(3) ?
N1 N2 Cu1 . . 120.7(3) ?
C1 N3 C9 . . 122.9(4) ?
C1 N3 H3N . . 118(4) ?
C9 N3 H3N . . 119(4) ?
C12 N4 N5 . . 120.6(4) ?
C12 N4 H4N . . 126(3) ?
N5 N4 H4N . . 110(3) ?
C13 N5 N4 . . 112.8(4) ?
C12 N6 C20 . . 124.4(4) ?
C12 N6 H6N . . 118(4) ?
C20 N6 H6N . . 117(4) ?
N1 C1 N3 . . 117.7(4) ?
N1 C1 S1 . . 125.4(4) ?
N3 C1 S1 . . 116.9(3) ?
N2 C2 C3 . . 125.7(4) ?
N2 C2 H2A . . 117.2 ?
C3 C2 H2A . . 117.2 ?
C8 C3 C4 . . 119.4(4) ?
C8 C3 C2 . . 116.7(4) ?
C4 C3 C2 . . 123.8(4) ?
O1 C4 C5 . . 119.5(5) ?
O1 C4 C3 . . 123.1(5) ?
C5 C4 C3 . . 117.5(4) ?
C6 C5 C4 . . 121.7(5) ?
C6 C5 H5A . . 119.1 ?
C4 C5 H5A . . 119.1 ?
C5 C6 C7 . . 121.2(4) ?
C5 C6 H6A . . 119.4 ?
C7 C6 H6A . . 119.4 ?
C8 C7 C6 . . 118.5(5) ?
C8 C7 H7A . . 120.7 ?
C6 C7 H7A . . 120.7 ?
C7 C8 C3 . . 121.6(5) ?
C7 C8 H8A . . 119.2 ?
C3 C8 H8A . . 119.2 ?
C10B C9 C10A . . 45.0(7) ?
C10B C9 N3 . . 115.1(7) ?
C10A C9 N3 . . 114.7(5) ?
C10B C9 H9A . . 66.2 ?
C10A C9 H9A . . 108.6 ?
N3 C9 H9A . . 108.6 ?
C10B C9 H9B . . 135.6 ?
C10A C9 H9B . . 108.6 ?
N3 C9 H9B . . 108.6 ?
H9A C9 H9B . . 107.6 ?
C10B C9 H9C . . 108.5 ?
C10A C9 H9C . . 136.0 ?
N3 C9 H9C . . 108.5 ?
H9A C9 H9C . . 47.2 ?
H9B C9 H9C . . 62.8 ?
C10B C9 H9D . . 108.5 ?
C10A C9 H9D . . 66.3 ?
N3 C9 H9D . . 108.5 ?
H9A C9 H9D . . 140.6 ?
H9B C9 H9D . . 47.1 ?
H9C C9 H9D . . 107.5 ?
C11A C10A C9 . . 127.9(14) ?
C11A C10A H10A . . 116.1 ?
C9 C10A H10A . . 116.1 ?
C10A C11A H11A . . 120.0 ?
C10A C11A H11B . . 120.0 ?
H11A C11A H11B . . 120.0 ?
C11B C10B C9 . . 127(3) ?
C11B C10B H10B . . 116.4 ?
C9 C10B H10B . . 116.4 ?
C10B C11B H11C . . 120.0 ?
C10B C11B H11D . . 120.0 ?
H11C C11B H11D . . 120.0 ?
O3 Cu2 N8 . . 93.19(13) y
O3 Cu2 S3 . . 171.12(9) ?
N8 Cu2 S3 . . 85.19(11) y
O3 Cu2 S4 . . 98.83(9) y
N8 Cu2 S4 . . 164.03(10) ?
S3 Cu2 S4 . . 84.48(4) y
C23 S3 Cu2 . . 94.78(15) ?
C34 S4 Cu2 . . 115.93(15) ?
C26 O3 Cu2 . . 127.9(3) ?
C37 O4 H4O . . 105(4) ?
C23 N7 N8 . . 112.3(4) ?
C24 N8 N7 . . 113.7(4) ?
C24 N8 Cu2 . . 125.3(3) ?
N7 N8 Cu2 . . 121.0(3) ?
C23 N9 C31 . . 124.7(4) ?
C23 N9 H9N . . 123(3) ?
C31 N9 H9N . . 112(3) ?
C34 N10 N11 . . 121.1(4) ?
C34 N10 H10N . . 121(3) ?
N11 N10 H10N . . 115(3) ?
C35 N11 N10 . . 113.4(4) ?
C34 N12 C42 . . 125.0(4) ?
C34 N12 H12N . . 122(4) ?
C42 N12 H12N . . 113(4) ?
N6 C12 N4 . . 120.3(4) ?
N6 C12 S2 . . 121.1(3) ?
N4 C12 S2 . . 118.5(3) ?
N5 C13 C14 . . 124.3(4) ?
N5 C13 H13A . . 117.8 ?
C14 C13 H13A . . 117.8 ?
C19 C14 C15 . . 118.1(4) ?
C19 C14 C13 . . 118.9(4) ?
C15 C14 C13 . . 122.9(4) ?
O2 C15 C16 . . 117.6(5) ?
O2 C15 C14 . . 122.3(5) ?
C16 C15 C14 . . 120.1(5) ?
C17 C16 C15 . . 119.9(5) ?
C17 C16 H16A . . 120.0 ?
C15 C16 H16A . . 120.0 ?
C16 C17 C18 . . 121.0(5) ?
C16 C17 H17A . . 119.5 ?
C18 C17 H17A . . 119.5 ?
C19 C18 C17 . . 118.9(5) ?
C19 C18 H18A . . 120.5 ?
C17 C18 H18A . . 120.5 ?
C18 C19 C14 . . 121.9(5) ?
C18 C19 H19A . . 119.1 ?
C14 C19 H19A . . 119.1 ?
N6 C20 C21 . . 113.6(4) ?
N6 C20 H20A . . 108.8 ?
C21 C20 H20A . . 108.8 ?
N6 C20 H20B . . 108.8 ?
C21 C20 H20B . . 108.8 ?
H20A C20 H20B . . 107.7 ?
C22 C21 C20 . . 124.2(5) ?
C22 C21 H21A . . 117.9 ?
C20 C21 H21A . . 117.9 ?
C21 C22 H22A . . 120.0 ?
C21 C22 H22B . . 120.0 ?
H22A C22 H22B . . 120.0 ?
N7 C23 N9 . . 118.3(4) ?
N7 C23 S3 . . 125.1(3) ?
N9 C23 S3 . . 116.6(3) ?
N8 C24 C25 . . 126.1(4) ?
N8 C24 H24A . . 116.9 ?
C25 C24 H24A . . 116.9 ?
C30 C25 C26 . . 118.9(4) ?
C30 C25 C24 . . 117.2(4) ?
C26 C25 C24 . . 123.8(4) ?
O3 C26 C27 . . 119.2(5) ?
O3 C26 C25 . . 123.4(4) ?
C27 C26 C25 . . 117.4(4) ?
C28 C27 C26 . . 122.1(5) ?
C28 C27 H27A . . 119.0 ?
C26 C27 H27A . . 119.0 ?
C27 C28 C29 . . 120.6(4) ?
C27 C28 H28A . . 119.7 ?
C29 C28 H28A . . 119.7 ?
C30 C29 C28 . . 118.4(5) ?
C30 C29 H29A . . 120.8 ?
C28 C29 H29A . . 120.8 ?
C29 C30 C25 . . 122.5(4) ?
C29 C30 H30A . . 118.7 ?
C25 C30 H30A . . 118.7 ?
N9 C31 C32 . . 113.4(4) ?
N9 C31 H31A . . 108.9 ?
C32 C31 H31A . . 108.9 ?
N9 C31 H31B . . 108.9 ?
C32 C31 H31B . . 108.9 ?
H31A C31 H31B . . 107.7 ?
C33 C32 C31 . . 123.7(5) ?
C33 C32 H32A . . 118.2 ?
C31 C32 H32A . . 118.2 ?
C32 C33 H33A . . 120.0 ?
C32 C33 H33B . . 120.0 ?
H33A C33 H33B . . 120.0 ?
N12 C34 N10 . . 119.4(4) ?
N12 C34 S4 . . 121.4(3) ?
N10 C34 S4 . . 119.2(3) ?
N11 C35 C36 . . 123.5(4) ?
N11 C35 H35A . . 118.3 ?
C36 C35 H35A . . 118.3 ?
C37 C36 C41 . . 117.6(4) ?
C37 C36 C35 . . 123.9(4) ?
C41 C36 C35 . . 118.5(4) ?
C38 C37 O4 . . 116.8(5) ?
C38 C37 C36 . . 121.3(5) ?
O4 C37 C36 . . 121.8(4) ?
C37 C38 C39 . . 119.5(5) ?
C37 C38 H38A . . 120.2 ?
C39 C38 H38A . . 120.2 ?
C40 C39 C38 . . 120.6(5) ?
C40 C39 H39A . . 119.7 ?
C38 C39 H39A . . 119.7 ?
C39 C40 C41 . . 120.1(4) ?
C39 C40 H40A . . 120.0 ?
C41 C40 H40A . . 120.0 ?
C40 C41 C36 . . 120.9(5) ?
C40 C41 H41A . . 119.6 ?
C36 C41 H41A . . 119.6 ?
N12 C42 C43 . . 112.3(4) ?
N12 C42 H42A . . 109.1 ?
C43 C42 H42A . . 109.1 ?
N12 C42 H42B . . 109.1 ?
C43 C42 H42B . . 109.1 ?
H42A C42 H42B . . 107.9 ?
C44 C43 C42 . . 125.6(5) ?
C44 C43 H43A . . 117.2 ?
C42 C43 H43A . . 117.2 ?
C43 C44 H44A . . 120.0 ?
C43 C44 H44B . . 120.0 ?
H44A C44 H44B . . 120.0 ?
H51O O5 H52O . . 102(5) ?
H61O O6 H62O . . 105(4) ?
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(3) y
Cu1 N2 . 1.949(4) y
Cu1 S1 . 2.2519(13) y
Cu1 S2 . 2.3347(12) y
S1 C1 . 1.733(5) y
S2 C12 . 1.721(4) y
O1 C4 . 1.337(6) ?
O2 C15 . 1.354(6) ?
O2 H2O . 0.75(5) ?
N1 C1 . 1.305(6) ?
N1 N2 . 1.401(5) ?
N2 C2 . 1.296(5) ?
N3 C1 . 1.345(6) ?
N3 C9 . 1.457(6) ?
N3 H3N . 0.78(3) ?
N4 C12 . 1.338(6) ?
N4 N5 . 1.382(5) ?
N4 H4N . 0.83(3) ?
N5 C13 . 1.285(5) ?
N6 C12 . 1.324(6) ?
N6 C20 . 1.447(5) ?
N6 H6N . 0.79(3) ?
C2 C3 . 1.437(6) ?
C2 H2A . 0.9500 ?
C3 C8 . 1.403(6) ?
C3 C4 . 1.407(7) ?
C4 C5 . 1.398(7) ?
C5 C6 . 1.366(6) ?
C5 H5A . 0.9500 ?
C6 C7 . 1.375(7) ?
C6 H6A . 0.9500 ?
C7 C8 . 1.376(6) ?
C7 H7A . 0.9500 ?
C8 H8A . 0.9500 ?
C9 C10B . 1.396(14) ?
C9 C10A . 1.431(8) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C9 H9C . 0.9900 ?
C9 H9D . 0.9900 ?
C10A C11A . 1.317(18) ?
C10A H10A . 0.9500 ?
C11A H11A . 0.9500 ?
C11A H11B . 0.9500 ?
C10B C11B . 1.33(2) ?
C10B H10B . 0.9500 ?
C11B H11C . 0.9500 ?
C11B H11D . 0.9500 ?
Cu2 O3 . 1.908(3) y
Cu2 N8 . 1.964(4) y
Cu2 S3 . 2.2401(13) y
Cu2 S4 . 2.3320(12) y
S3 C23 . 1.747(4) y
S4 C34 . 1.714(4) y
O3 C26 . 1.323(6) ?
O4 C37 . 1.377(6) ?
O4 H4O . 0.79(3) ?
N7 C23 . 1.317(6) ?
N7 N8 . 1.393(5) ?
N8 C24 . 1.282(5) ?
N9 C23 . 1.334(6) ?
N9 C31 . 1.454(6) ?
N9 H9N . 0.81(3) ?
N10 C34 . 1.330(6) ?
N10 N11 . 1.391(5) ?
N10 H10N . 0.82(3) ?
N11 C35 . 1.286(5) ?
N12 C34 . 1.318(6) ?
N12 C42 . 1.463(5) ?
N12 H12N . 0.84(5) ?
C13 C14 . 1.439(5) ?
C13 H13A . 0.9500 ?
C14 C19 . 1.404(6) ?
C14 C15 . 1.405(7) ?
C15 C16 . 1.387(7) ?
C16 C17 . 1.378(7) ?
C16 H16A . 0.9500 ?
C17 C18 . 1.394(7) ?
C17 H17A . 0.9500 ?
C18 C19 . 1.364(6) ?
C18 H18A . 0.9500 ?
C19 H19A . 0.9500 ?
C20 C21 . 1.493(6) ?
C20 H20A . 0.9900 ?
C20 H20B . 0.9900 ?
C21 C22 . 1.296(7) ?
C21 H21A . 0.9500 ?
C22 H22A . 0.9500 ?
C22 H22B . 0.9500 ?
C24 C25 . 1.432(6) ?
C24 H24A . 0.9500 ?
C25 C30 . 1.404(6) ?
C25 C26 . 1.414(6) ?
C26 C27 . 1.401(7) ?
C27 C28 . 1.374(6) ?
C27 H27A . 0.9500 ?
C28 C29 . 1.386(7) ?
C28 H28A . 0.9500 ?
C29 C30 . 1.368(7) ?
C29 H29A . 0.9500 ?
C30 H30A . 0.9500 ?
C31 C32 . 1.483(6) ?
C31 H31A . 0.9900 ?
C31 H31B . 0.9900 ?
C32 C33 . 1.316(6) ?
C32 H32A . 0.9500 ?
C33 H33A . 0.9500 ?
C33 H33B . 0.9500 ?
C35 C36 . 1.440(6) ?
C35 H35A . 0.9500 ?
C36 C37 . 1.386(7) ?
C36 C41 . 1.405(6) ?
C37 C38 . 1.373(6) ?
C38 C39 . 1.378(7) ?
C38 H38A . 0.9500 ?
C39 C40 . 1.368(7) ?
C39 H39A . 0.9500 ?
C40 C41 . 1.367(6) ?
C40 H40A . 0.9500 ?
C41 H41A . 0.9500 ?
C42 C43 . 1.495(6) ?
C42 H42A . 0.9900 ?
C42 H42B . 0.9900 ?
C43 C44 . 1.297(7) ?
C43 H43A . 0.9500 ?
C44 H44A . 0.9500 ?
C44 H44B . 0.9500 ?
O5 H51O . 0.75(3) ?
O5 H52O . 0.78(4) ?
O6 H61O . 0.89(3) ?
O6 H62O . 0.87(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
O2 H2O N5 . 0.75(5) 2.05(5) 2.718(5) 148(6)
N4 H4N O1 . 0.83(3) 1.94(3) 2.715(5) 155(4)
N6 H6N O6 . 0.79(3) 2.14(4) 2.876(5) 154(5)
O4 H4O N11 . 0.79(3) 2.00(4) 2.714(5) 151(6)
N9 H9N S1 . 0.81(3) 2.71(3) 3.460(4) 154(4)
N10 H10N O3 . 0.82(3) 1.96(3) 2.753(5) 160(4)
N12 H12N O5 . 0.84(5) 2.06(5) 2.864(5) 159(5)
O5 H51O O2 2_655 0.75(3) 2.13(4) 2.833(4) 157(5)
O5 H52O N1 4 0.78(4) 2.19(5) 2.912(6) 155(5)
O6 H61O N7 4_454 0.89(3) 2.07(3) 2.890(5) 153(4)
O6 H62O O4 2_454 0.87(3) 1.97(3) 2.827(4) 165(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
O1 Cu1 S1 C1 . . . . 88.0(6) ?
N2 Cu1 S1 C1 . . . . 7.14(17) ?
S2 Cu1 S1 C1 . . . . -159.67(14) ?
O1 Cu1 S2 C12 . . . . -7.56(19) ?
N2 Cu1 S2 C12 . . . . 127.8(4) ?
S1 Cu1 S2 C12 . . . . -178.27(17) ?
N2 Cu1 O1 C4 . . . . 3.7(4) ?
S1 Cu1 O1 C4 . . . . -76.5(7) ?
S2 Cu1 O1 C4 . . . . 172.3(3) ?
C1 N1 N2 C2 . . . . -168.4(4) ?
C1 N1 N2 Cu1 . . . . 10.2(5) ?
O1 Cu1 N2 C2 . . . . -2.7(3) ?
S1 Cu1 N2 C2 . . . . 167.5(3) ?
S2 Cu1 N2 C2 . . . . -138.6(3) ?
O1 Cu1 N2 N1 . . . . 178.9(3) ?
S1 Cu1 N2 N1 . . . . -10.9(3) ?
S2 Cu1 N2 N1 . . . . 43.1(6) ?
C12 N4 N5 C13 . . . . 176.5(4) ?
N2 N1 C1 N3 . . . . 177.3(4) y
N2 N1 C1 S1 . . . . -2.1(6) ?
C9 N3 C1 N1 . . . . -5.4(8) ?
C9 N3 C1 S1 . . . . 174.0(4) ?
Cu1 S1 C1 N1 . . . . -5.0(4) ?
Cu1 S1 C1 N3 . . . . 175.7(4) ?
N1 N2 C2 C3 . . . . -179.3(4) ?
Cu1 N2 C2 C3 . . . . 2.2(6) ?
N2 C2 C3 C8 . . . . 179.1(4) ?
N2 C2 C3 C4 . . . . -1.7(7) ?
Cu1 O1 C4 C5 . . . . 175.4(3) ?
Cu1 O1 C4 C3 . . . . -4.2(6) ?
C8 C3 C4 O1 . . . . -178.2(4) ?
C2 C3 C4 O1 . . . . 2.6(7) ?
C8 C3 C4 C5 . . . . 2.3(6) ?
C2 C3 C4 C5 . . . . -177.0(4) ?
O1 C4 C5 C6 . . . . 178.3(4) ?
C3 C4 C5 C6 . . . . -2.1(7) ?
C4 C5 C6 C7 . . . . 0.2(7) ?
C5 C6 C7 C8 . . . . 1.5(7) ?
C6 C7 C8 C3 . . . . -1.4(7) ?
C4 C3 C8 C7 . . . . -0.6(7) ?
C2 C3 C8 C7 . . . . 178.8(4) ?
C1 N3 C9 C10B . . . . -123.5(9) ?
C1 N3 C9 C10A . . . . -173.4(6) ?
C10B C9 C10A C11A . . . . 19(3) ?
N3 C9 C10A C11A . . . . 120(3) ?
C10A C9 C10B C11B . . . . -18(5) ?
N3 C9 C10B C11B . . . . -119(5) ?
O3 Cu2 S3 C23 . . . . 89.0(6) ?
N8 Cu2 S3 C23 . . . . 9.12(16) ?
S4 Cu2 S3 C23 . . . . -158.68(14) ?
O3 Cu2 S4 C34 . . . . -3.31(18) ?
N8 Cu2 S4 C34 . . . . 135.1(4) ?
S3 Cu2 S4 C34 . . . . -175.00(17) ?
N8 Cu2 O3 C26 . . . . 5.2(4) ?
S3 Cu2 O3 C26 . . . . -74.0(8) ?
S4 Cu2 O3 C26 . . . . 174.7(3) ?
C23 N7 N8 C24 . . . . -168.7(4) ?
C23 N7 N8 Cu2 . . . . 10.2(5) ?
O3 Cu2 N8 C24 . . . . -5.0(3) ?
S3 Cu2 N8 C24 . . . . 166.2(3) ?
S4 Cu2 N8 C24 . . . . -143.9(3) ?
O3 Cu2 N8 N7 . . . . 176.2(3) ?
S3 Cu2 N8 N7 . . . . -12.6(3) ?
S4 Cu2 N8 N7 . . . . 37.3(6) ?
C34 N10 N11 C35 . . . . -179.9(4) ?
C20 N6 C12 N4 . . . . -177.0(4) ?
C20 N6 C12 S2 . . . . 3.0(6) ?
N5 N4 C12 N6 . . . . -10.0(7) y
N5 N4 C12 S2 . . . . 170.0(3) ?
Cu1 S2 C12 N6 . . . . 174.9(3) ?
Cu1 S2 C12 N4 . . . . -5.0(4) ?
N4 N5 C13 C14 . . . . 172.7(4) ?
N5 C13 C14 C19 . . . . -174.4(4) ?
N5 C13 C14 C15 . . . . 3.9(6) ?
C19 C14 C15 O2 . . . . 178.6(4) ?
C13 C14 C15 O2 . . . . 0.3(7) ?
C19 C14 C15 C16 . . . . -0.2(7) ?
C13 C14 C15 C16 . . . . -178.5(4) ?
O2 C15 C16 C17 . . . . -179.8(4) ?
C14 C15 C16 C17 . . . . -1.0(7) ?
C15 C16 C17 C18 . . . . 1.9(8) ?
C16 C17 C18 C19 . . . . -1.6(8) ?
C17 C18 C19 C14 . . . . 0.4(7) ?
C15 C14 C19 C18 . . . . 0.5(7) ?
C13 C14 C19 C18 . . . . 178.9(4) ?
C12 N6 C20 C21 . . . . -89.1(5) ?
N6 C20 C21 C22 . . . . -141.8(5) ?
N8 N7 C23 N9 . . . . -178.9(4) y
N8 N7 C23 S3 . . . . 0.3(6) ?
C31 N9 C23 N7 . . . . -4.6(7) ?
C31 N9 C23 S3 . . . . 176.1(3) ?
Cu2 S3 C23 N7 . . . . -8.1(4) ?
Cu2 S3 C23 N9 . . . . 171.2(3) ?
N7 N8 C24 C25 . . . . -177.1(4) ?
Cu2 N8 C24 C25 . . . . 4.1(6) ?
N8 C24 C25 C30 . . . . 178.4(4) ?
N8 C24 C25 C26 . . . . -1.3(7) ?
Cu2 O3 C26 C27 . . . . 174.8(3) ?
Cu2 O3 C26 C25 . . . . -4.3(6) ?
C30 C25 C26 O3 . . . . -178.4(4) ?
C24 C25 C26 O3 . . . . 1.3(7) ?
C30 C25 C26 C27 . . . . 2.5(6) ?
C24 C25 C26 C27 . . . . -177.8(4) ?
O3 C26 C27 C28 . . . . 178.0(4) ?
C25 C26 C27 C28 . . . . -2.8(7) ?
C26 C27 C28 C29 . . . . 1.4(7) ?
C27 C28 C29 C30 . . . . 0.5(7) ?
C28 C29 C30 C25 . . . . -0.8(7) ?
C26 C25 C30 C29 . . . . -0.7(7) ?
C24 C25 C30 C29 . . . . 179.5(4) ?
C23 N9 C31 C32 . . . . -74.2(6) ?
N9 C31 C32 C33 . . . . -116.7(5) ?
C42 N12 C34 N10 . . . . -177.9(4) ?
C42 N12 C34 S4 . . . . 0.6(6) ?
N11 N10 C34 N12 . . . . -13.1(6) y
N11 N10 C34 S4 . . . . 168.3(3) ?
Cu2 S4 C34 N12 . . . . 170.7(3) ?
Cu2 S4 C34 N10 . . . . -10.7(4) ?
N10 N11 C35 C36 . . . . 172.2(4) ?
N11 C35 C36 C37 . . . . 5.8(7) ?
N11 C35 C36 C41 . . . . -173.0(4) ?
C41 C36 C37 C38 . . . . 0.7(7) ?
C35 C36 C37 C38 . . . . -178.1(4) ?
C41 C36 C37 O4 . . . . -179.6(4) ?
C35 C36 C37 O4 . . . . 1.7(7) ?
O4 C37 C38 C39 . . . . -179.6(4) ?
C36 C37 C38 C39 . . . . 0.2(7) ?
C37 C38 C39 C40 . . . . -0.5(7) ?
C38 C39 C40 C41 . . . . -0.2(7) ?
C39 C40 C41 C36 . . . . 1.1(7) ?
C37 C36 C41 C40 . . . . -1.4(6) ?
C35 C36 C41 C40 . . . . 177.5(4) ?
C34 N12 C42 C43 . . . . -82.6(5) ?
N12 C42 C43 C44 . . . . -132.2(5) ?
