#------------------------------------------------------------------------------
#$Date: 2016-03-04 13:39:15 +0200 (Fri, 04 Mar 2016) $
#$Revision: 177475 $
#$URL: svn://www.crystallography.net/cod/cif/2/02/03/2020396.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_2020396
loop_
_publ_author_name
'Jiao, Chen'
'Zhang, Si-Si'
'Li, Zuo-Yin'
'Liu, Jian-Jun'
'Lin, Mei-Jin'
'Huang, Chang-Cang'
_publ_section_title
;
 Syntheses and structures of discrete copper(II) and cadmium(II)
 supramolecular complexes based on 1,4-diacylthiosemicarbazone ligands
;
_journal_coeditor_code           QS3052
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              119
_journal_page_last               123
_journal_paper_doi               10.1107/S2053229616000310
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac
'[Cu4 (C11 H10 N3 O3 S)2 (C2 H3 O2)2], 2C3 H7 N O'
_chemical_formula_moiety         'C26 H26 Cu4 N6 O10 S2, 2(C3 H7 N O)'
_chemical_formula_sum            'C32 H40 Cu4 N8 O12 S2'
_chemical_formula_weight         1047.00
_chemical_name_systematic
;Di-μ-acetato-bis{μ₄-1-[(2-oxidophenyl)carbonyl]-2-(propanamidomethanethioyl)hydrazine-1,2-diido}tetracopper(II) dimethylformamide
disolvate
;
_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   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                111.67(3)
_cell_angle_beta                 107.76(3)
_cell_angle_gamma                95.87(3)
_cell_formula_units_Z            1
_cell_length_a                   8.4421(17)
_cell_length_b                   11.435(2)
_cell_length_c                   11.909(2)
_cell_measurement_reflns_used    2965
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4894
_cell_measurement_theta_min      3.1642
_cell_volume                     987.0(5)
_computing_cell_refinement
;
CrystalClear (Rigaku, 2002)
;
_computing_data_collection
;
CrystalClear (Rigaku, 2002)
;
_computing_data_reduction
;
CrystalClear (Rigaku, 2002)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 2004)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Rigaku Saturn 724 CCD area-detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8309
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.488
_diffrn_reflns_theta_min         3.164
_exptl_absorpt_coefficient_mu    2.302
_exptl_absorpt_correction_T_max  0.9189
_exptl_absorpt_correction_T_min  0.7153
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(RAPID-AUTO; Rigaku, 1998)
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.761
_exptl_crystal_description       block
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.499
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4355
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0483
_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)+(0.0342P)²+1.2320P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1060
_reflns_number_gt                3779
_reflns_number_total             4355
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            qs3052sup1.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 2020396--2020397.cif.'
_cod_original_cell_volume        987.0(4)
_cod_database_code               2020396
_cod_database_fobs_code          2020396
_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.
;
_shelxl_version_number           2014/6
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 S1 0.30091(14) -0.21492(9) 0.48375(10) 0.0428(2) Uani d 1
Cu Cu1 0.17118(6) -0.11507(4) 0.62211(4) 0.03556(13) Uani d 1
Cu Cu2 0.19996(6) 0.12971(4) 0.39528(4) 0.03636(13) Uani d 1
O O1 0.0974(3) -0.0171(2) 0.7556(2) 0.0394(6) Uani d 1
O O2 0.1568(3) 0.2107(2) 0.5535(2) 0.0400(6) Uani d 1
O O3 0.2854(3) 0.0413(2) 0.2591(2) 0.0404(6) Uani d 1
O O4 0.1590(4) 0.2701(2) 0.3473(3) 0.0449(6) Uani d 1
O O5 -0.1058(4) 0.2701(2) 0.3527(3) 0.0437(6) Uani d 1
O O6 0.4395(5) 0.6377(3) 0.2128(3) 0.0651(9) Uani d 1
N N1 0.2097(4) 0.0277(3) 0.5768(3) 0.0337(6) Uani d 1
N N2 0.2482(4) 0.0051(3) 0.4654(3) 0.0329(6) Uani d 1
N N3 0.3370(4) -0.1308(3) 0.3097(3) 0.0377(7) Uani d 1
H H3 0.3718 -0.2007 0.2846 0.045 Uiso calc 1
N N4 0.5064(5) 0.4571(4) 0.2321(4) 0.0568(10) Uani d 1
C C1 0.1089(5) 0.1099(3) 0.8028(3) 0.0354(7) Uani d 1
C C2 0.0844(5) 0.1688(4) 0.9206(4) 0.0441(9) Uani d 1
H H4 0.0707 0.1197 0.9657 0.053 Uiso calc 1
C C3 0.0802(6) 0.2974(4) 0.9712(4) 0.0527(10) Uani d 1
H H3A 0.0632 0.3337 1.0492 0.063 Uiso calc 1
C C4 0.1013(6) 0.3736(4) 0.9061(4) 0.0544(11) Uani d 1
H H2 0.0978 0.4603 0.9397 0.065 Uiso calc 1
C C5 0.1274(5) 0.3189(4) 0.7918(4) 0.0449(9) Uani d 1
H H1 0.1402 0.3694 0.7478 0.054 Uiso calc 1
C C6 0.1355(4) 0.1888(3) 0.7392(3) 0.0355(8) Uani d 1
C C7 0.1674(4) 0.1409(3) 0.6178(3) 0.0334(7) Uani d 1
C C8 0.2930(4) -0.1032(3) 0.4187(3) 0.0331(7) Uani d 1
C C9 0.3320(5) -0.0617(4) 0.2381(3) 0.0374(8) Uani d 1
C C10 0.3912(6) -0.1179(5) 0.1266(4) 0.0550(11) Uani d 1
H H10A 0.5148 -0.0873 0.1587 0.066 Uiso calc 1
H H10B 0.3647 -0.2116 0.0952 0.066 Uiso calc 1
C C11 0.3140(8) -0.0853(6) 0.0159(5) 0.0836(18) Uani d 1
H H11A 0.1918 -0.1176 -0.0188 0.125 Uiso calc 1
H H11B 0.3585 -0.1243 -0.0506 0.125 Uiso calc 1
H H11C 0.3417 0.0071 0.0452 0.125 Uiso calc 1
C C12 0.0276(6) 0.3158(4) 0.3427(4) 0.0416(9) Uani d 1
C C13 0.0351(6) 0.4398(4) 0.3253(5) 0.0596(12) Uani d 1
H H13A -0.0673 0.4308 0.2560 0.089 Uiso calc 1
H H13B 0.1332 0.4580 0.3042 0.089 Uiso calc 1
H H13C 0.0441 0.5098 0.4044 0.089 Uiso calc 1
C C14 0.5265(10) 0.3825(8) 0.3076(9) 0.128(3) Uani d 1
H H14A 0.5328 0.4355 0.3937 0.192 Uiso calc 1
H H14B 0.6300 0.3531 0.3128 0.192 Uiso calc 1
H H14C 0.4302 0.3090 0.2668 0.192 Uiso calc 1
C C15 0.5271(7) 0.4010(5) 0.1085(5) 0.0760(15) Uani d 1
H H15A 0.5081 0.4582 0.0662 0.114 Uiso calc 1
H H15B 0.4456 0.3188 0.0546 0.114 Uiso calc 1
H H15C 0.6412 0.3888 0.1227 0.114 Uiso calc 1
C C16 0.4658(6) 0.5703(5) 0.2711(5) 0.0641(13) Uani d 1
H H16 0.4565 0.6013 0.3523 0.077 Uiso calc 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'
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'
H H 0.0000 0.0000 '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
C8 S1 Cu1 . . 93.93(12)
O1 Cu1 N1 . . 92.53(11)
O1 Cu1 O5 . 2_556 89.60(11)
N1 Cu1 O5 . 2_556 172.58(12)
O1 Cu1 S1 . . 171.24(9)
N1 Cu1 S1 . . 85.48(9)
O5 Cu1 S1 2_556 . 93.46(8)
O1 Cu1 Cu2 . 2_556 53.58(9)
N1 Cu1 Cu2 . 2_556 100.31(9)
O5 Cu1 Cu2 2_556 2_556 75.30(8)
S1 Cu1 Cu2 . 2_556 135.18(4)
N2 Cu2 O4 . . 172.78(12)
N2 Cu2 O2 . . 81.04(11)
O4 Cu2 O2 . . 92.43(11)
N2 Cu2 O3 . . 89.95(11)
O4 Cu2 O3 . . 96.06(11)
O2 Cu2 O3 . . 167.88(11)
N2 Cu2 Cu1 . 2_556 98.75(9)
O4 Cu2 Cu1 . 2_556 80.60(9)
O2 Cu2 Cu1 . 2_556 61.18(9)
O3 Cu2 Cu1 . 2_556 128.80(9)
C1 O1 Cu1 . . 126.9(2)
C7 O2 Cu2 . . 112.7(2)
C9 O3 Cu2 . . 126.9(2)
C12 O4 Cu2 . . 124.9(2)
C12 O5 Cu1 . 2_556 131.1(2)
C7 N1 N2 . . 110.9(3)
C7 N1 Cu1 . . 128.7(2)
N2 N1 Cu1 . . 118.5(2)
C8 N2 N1 . . 115.3(3)
C8 N2 Cu2 . . 130.4(2)
N1 N2 Cu2 . . 113.8(2)
C9 N3 C8 . . 128.3(3)
C9 N3 H3 . . 115.9
C8 N3 H3 . . 115.9
C16 N4 C14 . . 122.1(5)
C16 N4 C15 . . 121.0(4)
C14 N4 C15 . . 116.9(5)
O1 C1 C2 . . 117.8(3)
O1 C1 C6 . . 124.5(3)
C2 C1 C6 . . 117.6(3)
C3 C2 C1 . . 121.7(4)
C3 C2 H4 . . 119.1
C1 C2 H4 . . 119.1
C2 C3 C4 . . 120.4(4)
C2 C3 H3A . . 119.8
C4 C3 H3A . . 119.8
C5 C4 C3 . . 119.0(4)
C5 C4 H2 . . 120.5
C3 C4 H2 . . 120.5
C4 C5 C6 . . 121.9(4)
C4 C5 H1 . . 119.1
C6 C5 H1 . . 119.1
C5 C6 C1 . . 119.3(3)
C5 C6 C7 . . 117.4(3)
C1 C6 C7 . . 123.3(3)
O2 C7 N1 . . 121.0(3)
O2 C7 C6 . . 118.9(3)
N1 C7 C6 . . 120.0(3)
N2 C8 N3 . . 118.5(3)
N2 C8 S1 . . 123.9(3)
N3 C8 S1 . . 117.6(2)
O3 C9 N3 . . 125.2(3)
O3 C9 C10 . . 119.9(3)
N3 C9 C10 . . 114.9(3)
C11 C10 C9 . . 114.7(4)
C11 C10 H10A . . 108.6
C9 C10 H10A . . 108.6
C11 C10 H10B . . 108.6
C9 C10 H10B . . 108.6
H10A C10 H10B . . 107.6
C10 C11 H11A . . 109.5
C10 C11 H11B . . 109.5
H11A C11 H11B . . 109.5
C10 C11 H11C . . 109.5
H11A C11 H11C . . 109.5
H11B C11 H11C . . 109.5
O5 C12 O4 . . 127.2(3)
O5 C12 C13 . . 116.7(4)
O4 C12 C13 . . 116.0(4)
C12 C13 H13A . . 109.5
C12 C13 H13B . . 109.5
H13A C13 H13B . . 109.5
C12 C13 H13C . . 109.5
H13A C13 H13C . . 109.5
H13B C13 H13C . . 109.5
N4 C14 H14A . . 109.5
N4 C14 H14B . . 109.5
H14A C14 H14B . . 109.5
N4 C14 H14C . . 109.5
H14A C14 H14C . . 109.5
H14B C14 H14C . . 109.5
N4 C15 H15A . . 109.5
N4 C15 H15B . . 109.5
H15A C15 H15B . . 109.5
N4 C15 H15C . . 109.5
H15A C15 H15C . . 109.5
H15B C15 H15C . . 109.5
O6 C16 N4 . . 127.2(5)
O6 C16 H16 . . 116.4
N4 C16 H16 . . 116.4
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
S1 C8 . 1.719(3) ?
Cu1 S1 . 2.2771(12) y
Cu1 N1 . 1.927(3) y
Cu1 O1 . 1.898(3) y
Cu1 O2 2_556 2.719(3) y
Cu1 O5 2_556 1.957(2) y
Cu1 Cu2 2_556 3.0592(9) ?
Cu2 N2 . 1.919(3) y
Cu2 O1 2_556 2.645(3) y
Cu2 O2 . 1.934(3) y
Cu2 O3 . 1.955(3) y
Cu2 O4 . 1.922(2) y
Cu2 Cu1 2_556 3.0592(9) ?
O1 C1 . 1.330(4) ?
O2 C7 . 1.287(4) ?
O3 C9 . 1.241(4) ?
O4 C12 . 1.269(5) ?
O5 C12 . 1.251(5) ?
O5 Cu1 2_556 1.957(2) ?
O6 C16 . 1.209(5) ?
N1 C7 . 1.332(4) ?
N1 N2 . 1.399(4) ?
N2 C8 . 1.304(4) ?
N3 C9 . 1.354(4) ?
N3 C8 . 1.393(4) ?
N3 H3 . 0.8600 ?
N4 C16 . 1.323(6) ?
N4 C14 . 1.439(6) ?
N4 C15 . 1.446(6) ?
C1 C2 . 1.405(5) ?
C1 C6 . 1.416(5) ?
C2 C3 . 1.377(5) ?
C2 H4 . 0.9300 ?
C3 C4 . 1.394(6) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.369(6) ?
C4 H2 . 0.9300 ?
C5 C6 . 1.403(5) ?
C5 H1 . 0.9300 ?
C6 C7 . 1.464(5) ?
C9 C10 . 1.506(5) ?
C10 C11 . 1.480(6) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 C13 . 1.505(5) ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 H16 . 0.9300 ?
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
N3 H3 O6 1_545 0.86 1.95 2.812(4) 175.3
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
N1 Cu1 O1 C1 . -10.5(3)
O5 Cu1 O1 C1 2_556 176.6(3)
Cu2 Cu1 O1 C1 2_556 -111.4(3)
C7 N1 N2 C8 . 179.3(3)
Cu1 N1 N2 C8 . -15.1(4)
C7 N1 N2 Cu2 . -7.6(3)
Cu1 N1 N2 Cu2 . 157.98(15)
Cu1 O1 C1 C2 . -165.4(3)
Cu1 O1 C1 C6 . 17.9(5)
O1 C1 C2 C3 . -174.7(4)
C6 C1 C2 C3 . 2.2(6)
C1 C2 C3 C4 . -0.3(7)
C2 C3 C4 C5 . -0.4(7)
C3 C4 C5 C6 . -0.7(7)
C4 C5 C6 C1 . 2.7(6)
C4 C5 C6 C7 . -178.8(4)
O1 C1 C6 C5 . 173.3(4)
C2 C1 C6 C5 . -3.3(5)
O1 C1 C6 C7 . -5.1(6)
C2 C1 C6 C7 . 178.2(3)
Cu2 O2 C7 N1 . 2.0(4)
Cu2 O2 C7 C6 . -179.2(2)
N2 N1 C7 O2 . 3.7(5)
Cu1 N1 C7 O2 . -160.1(3)
N2 N1 C7 C6 . -175.1(3)
Cu1 N1 C7 C6 . 21.1(5)
C5 C6 C7 O2 . -12.0(5)
C1 C6 C7 O2 . 166.5(3)
C5 C6 C7 N1 . 166.8(3)
C1 C6 C7 N1 . -14.7(5)
N1 N2 C8 N3 . -178.5(3)
Cu2 N2 C8 N3 . 9.8(5)
N1 N2 C8 S1 . 1.5(4)
Cu2 N2 C8 S1 . -170.12(18)
C9 N3 C8 N2 . -3.7(6)
C9 N3 C8 S1 . 176.3(3)
Cu1 S1 C8 N2 . 9.3(3)
Cu1 S1 C8 N3 . -170.7(3)
Cu2 O3 C9 N3 . -2.2(6)
Cu2 O3 C9 C10 . 178.7(3)
C8 N3 C9 O3 . 0.0(6)
C8 N3 C9 C10 . 179.1(4)
O3 C9 C10 C11 . -28.5(6)
N3 C9 C10 C11 . 152.3(5)
Cu1 O5 C12 O4 2_556 -0.3(6)
Cu1 O5 C12 C13 2_556 -179.3(3)
Cu2 O4 C12 O5 . -9.2(6)
Cu2 O4 C12 C13 . 169.9(3)
C14 N4 C16 O6 . -176.9(6)
C15 N4 C16 O6 . 1.1(9)
