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Three new one- (1D) and two-dimensional (2D) CuII coordination polymers, namely poly[[bis­{μ2-4-amino-3-(pyridin-2-yl)-5-[(pyri­din-3-ylmeth­yl)sulfan­yl]-1,2,4-triazole}copper(II)] bis­(methane­sulfonate) tetra­hydrate], {[Cu(C13H12N5S)2](CH3SO3)2·4H2O}n (1), catena-poly[[copper(II)-bis­{μ2-4-amino-3-(pyri­din-2-yl)-5-[(pyridin-4-ylmeth­yl)sulfan­yl]-1,2,4-triazole}] dinitrate methanol disolvate], {[Cu(C13H12N5S)2](NO3)2·2CH3OH}n (2), and catena-poly[[copper(II)-bis­{μ2-4-amino-3-(pyridin-2-yl)-5-[(pyridin-4-ylmeth­yl)sulfan­yl]-1,2,4-triazole}] bis­(perchlorate) monohydrate], {[Cu(C13H12N5S)2](ClO4)2·H2O}n (3), were obtained from 4-amino-3-(pyridin-2-yl)-5-[(pyridin-3-ylmeth­yl)sulfan­yl]-1,2,4-triazole with pyridin-3-yl terminal groups and from 4-amino-3-(pyridin-2-yl)-5-[(pyridin-4-ylmeth­yl)sulfan­yl]-1,2,4-triazole with pyridin-4-yl terminal groups. Compound 1 displays a 2D net-like structure. The 2D layers are further linked through hydrogen bonds between methanesulfonate anions and amino groups on the framework and guest H2O mol­ecules in the lattice to form a three-dimensional (3D) structure. Compound 2 and 3 exhibit 1D chain structures, in which the complicated hydrogen-bonding inter­actions play an important role in the formation of the 3D network. These experimental results indicate that the coordination orientation of the heteroatoms on the ligands has a great influence on the polymeric structures. Moreover, the selection of different counter-anions, together with the inclusion of different guest solvent mol­ecules, would also have a great effect on the hydrogen-bonding systems in the crystal structures.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619003747/yp3177sup1.cif
Contains datablocks global, exp_2488, exp_2623, exp_2484

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003747/yp3177exp_2488sup2.hkl
Contains datablock exp_2488

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003747/yp3177exp_2484sup3.hkl
Contains datablock exp_2484

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003747/yp3177exp_2623sup4.hkl
Contains datablock exp_2623

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229619003747/yp3177sup5.pdf
Packing diagrams, IR spectra and TGA curves

CCDC references: 1903962; 1903961; 1903960

Computing details top

For all structures, data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015). Program(s) used to solve structure: olex2.solve (Bourhis et al., 2011) for exp_2488; SHELXS97 (Sheldrick, 2008) for exp_2484; SUPERFLIP (Palatinus & Chapuis, 2007) for exp_2623. For all structures, program(s) used to refine structure: SHEXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Poly[[bis{µ2-4-amino-3-(pyridin-2-yl)-5-[(pyridin-3-ylmethyl)sulfanyl]-1,2,4-triazole}copper(II)] bis(methanesulfonate) tetrahydrate] (exp_2488) top
Crystal data top
[Cu(C13H12N5S)2](CH3SO3)2·4H2OF(000) = 926
Mr = 894.48Dx = 1.557 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
a = 9.1819 (4) ÅCell parameters from 2984 reflections
b = 18.0782 (7) Åθ = 4.6–71.1°
c = 11.7932 (5) ŵ = 3.46 mm1
β = 102.977 (4)°T = 293 K
V = 1907.58 (14) Å3Block, clear pale blue
Z = 20.15 × 0.09 × 0.08 mm
Data collection top
Rigaku OD SuperNova Dual source
diffractometer with an Eos detector
3379 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source2735 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.030
Detector resolution: 16.0793 pixels mm-1θmax = 67.1°, θmin = 4.6°
ω scansh = 1010
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2015)
k = 2120
Tmin = 0.913, Tmax = 1.000l = 1014
6493 measured reflections
Refinement top
Refinement on F2Primary atom site location: iterative
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143H atoms treated by a mixture of independent and constrained refinement
S = 1.12 w = 1/[σ2(Fo2) + (0.0876P)2 + 0.1736P]
where P = (Fo2 + 2Fc2)/3
3379 reflections(Δ/σ)max < 0.001
251 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = 0.44 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

X-ray intensity data of 13 were measured separately at 293 (2), 293 (2) and 150 (10) K on a Bruker SMART APEX CCD-based diffractometer equipped with a Cu-Kα radiation (λ = 1.54184 Å) for 1 and 3, and Mo-Kα radiation (λ = 0.71073 Å) for 2 by using phi and omega scan mode. For compound 1, a total of 6493 reflections were collected in the range of 4.56θ67.04°, of which 3379 were unique with Rint = 0.0302 and 2735 observed reflections with I > 2σ(I) were used in structure solution. All calculations were carried out with OLEX2. The structures were solved by direct methods and refined on F2 by full-matrix least-squares techniques. All non-hydrogen atoms were refined with anisotropic displacement parameters.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.2992 (4)0.11847 (17)0.5508 (3)0.0372 (8)
H10.23270.15600.52000.045*
C20.4493 (4)0.13536 (19)0.5855 (3)0.0426 (8)
H20.48300.18330.57870.051*
C30.5478 (4)0.08003 (19)0.6304 (3)0.0408 (8)
H30.64960.09010.65300.049*
C40.4956 (4)0.00942 (17)0.6420 (3)0.0337 (7)
H40.56030.02860.67360.040*
C50.3428 (3)0.00278 (15)0.6046 (3)0.0250 (6)
C60.2726 (3)0.07532 (15)0.6083 (2)0.0234 (6)
C70.2185 (3)0.18983 (16)0.6331 (3)0.0287 (6)
C80.0584 (4)0.31482 (17)0.6426 (3)0.0355 (7)
H8A0.02050.31350.55890.043*
H8B0.00630.28510.67890.043*
C90.0652 (3)0.39288 (17)0.6865 (3)0.0296 (7)
C100.1112 (4)0.45039 (18)0.6244 (3)0.0365 (7)
H100.13470.44130.55290.044*
C110.1215 (4)0.52103 (19)0.6699 (3)0.0388 (8)
H110.15270.56010.62970.047*
C120.0852 (4)0.53288 (17)0.7756 (3)0.0309 (7)
H120.09170.58060.80570.037*
C130.0313 (3)0.40940 (16)0.7918 (3)0.0285 (6)
H130.00060.37120.83370.034*
C140.3889 (8)0.5824 (3)0.3991 (5)0.103 (2)
H14A0.30500.57660.33440.154*
H14B0.38710.54410.45510.154*
H14C0.47990.57920.37220.154*
Cu10.00000.00000.50000.0222 (2)
N10.2455 (3)0.05047 (13)0.5594 (2)0.0292 (6)
N20.1291 (3)0.08548 (13)0.5658 (2)0.0235 (5)
N30.0918 (3)0.15853 (13)0.5798 (2)0.0287 (6)
N40.3334 (3)0.14049 (13)0.6507 (2)0.0268 (5)
N50.4854 (3)0.15295 (16)0.7073 (3)0.0427 (7)
H5A0.51960.19270.66620.064*
H5B0.47470.16710.77900.064*
N60.0405 (3)0.47795 (13)0.8369 (2)0.0266 (5)
O10.2588 (3)0.6622 (2)0.5223 (3)0.0717 (9)
O20.3502 (4)0.7212 (2)0.3702 (3)0.0876 (12)
O30.5205 (3)0.6812 (2)0.5425 (3)0.0728 (9)
O40.1204 (4)0.7194 (2)0.6872 (3)0.0953 (13)
H4A0.17440.71040.63900.143*
H4B0.18490.74460.73450.143*
O50.8265 (4)0.6332 (2)0.6211 (3)0.0949 (13)
H5C0.86060.67610.61320.142*
H5D0.73360.62740.59260.142*
S10.24915 (9)0.28024 (4)0.68101 (8)0.0426 (3)
S20.37890 (10)0.66810 (5)0.46314 (8)0.0420 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.045 (2)0.0223 (16)0.0421 (19)0.0016 (13)0.0057 (15)0.0019 (13)
C20.047 (2)0.0313 (18)0.049 (2)0.0143 (15)0.0092 (17)0.0028 (15)
C30.0323 (18)0.043 (2)0.045 (2)0.0125 (15)0.0042 (14)0.0078 (16)
C40.0270 (17)0.0329 (17)0.0385 (19)0.0013 (12)0.0017 (14)0.0025 (14)
C50.0287 (16)0.0219 (15)0.0236 (15)0.0005 (11)0.0041 (12)0.0026 (11)
C60.0264 (15)0.0205 (14)0.0233 (14)0.0031 (11)0.0059 (11)0.0003 (11)
C70.0307 (16)0.0224 (14)0.0332 (17)0.0019 (12)0.0078 (13)0.0035 (12)
C80.0295 (16)0.0312 (17)0.0449 (19)0.0013 (13)0.0062 (14)0.0116 (14)
C90.0246 (15)0.0277 (16)0.0345 (17)0.0031 (12)0.0026 (12)0.0056 (12)
C100.0435 (19)0.0359 (18)0.0311 (17)0.0059 (14)0.0106 (14)0.0018 (13)
C110.047 (2)0.0290 (16)0.043 (2)0.0030 (15)0.0169 (16)0.0061 (14)
C120.0355 (17)0.0227 (15)0.0347 (17)0.0018 (12)0.0081 (13)0.0004 (12)
C130.0263 (15)0.0241 (15)0.0345 (17)0.0004 (12)0.0054 (12)0.0013 (12)
C140.136 (6)0.076 (4)0.094 (4)0.026 (4)0.022 (4)0.036 (3)
Cu10.0246 (3)0.0171 (3)0.0246 (3)0.0043 (2)0.0051 (2)0.0014 (2)
N10.0323 (14)0.0233 (13)0.0309 (14)0.0006 (10)0.0049 (11)0.0022 (10)
N20.0265 (13)0.0189 (12)0.0247 (13)0.0014 (9)0.0048 (10)0.0029 (9)
N30.0287 (13)0.0189 (12)0.0377 (15)0.0009 (10)0.0057 (11)0.0052 (10)
N40.0228 (12)0.0247 (12)0.0318 (14)0.0043 (9)0.0036 (10)0.0044 (10)
N50.0329 (15)0.0384 (16)0.0522 (18)0.0079 (12)0.0001 (13)0.0090 (13)
N60.0280 (13)0.0213 (12)0.0304 (14)0.0032 (10)0.0064 (10)0.0011 (10)
O10.063 (2)0.095 (2)0.067 (2)0.0004 (17)0.0349 (16)0.0002 (18)
O20.094 (3)0.093 (3)0.071 (2)0.012 (2)0.0091 (19)0.036 (2)
O30.0505 (18)0.099 (3)0.064 (2)0.0038 (17)0.0024 (15)0.0130 (18)
O40.075 (2)0.123 (3)0.096 (3)0.004 (2)0.036 (2)0.043 (2)
O50.085 (3)0.127 (4)0.070 (2)0.040 (2)0.012 (2)0.015 (2)
S10.0335 (5)0.0234 (4)0.0663 (6)0.0024 (3)0.0018 (4)0.0164 (4)
S20.0428 (5)0.0478 (5)0.0364 (5)0.0037 (4)0.0112 (4)0.0007 (4)
Geometric parameters (Å, º) top
C1—H10.9300C12—H120.9300
C1—C21.381 (5)C12—N61.346 (4)
C1—N11.337 (4)C13—H130.9300
C2—H20.9300C13—N61.344 (4)
C2—C31.373 (5)C14—H14A0.9600
C3—H30.9300C14—H14B0.9600
C3—C41.381 (5)C14—H14C0.9600
C4—H40.9300C14—S21.735 (5)
C4—C51.390 (4)Cu1—N1i2.386 (3)
C5—C61.466 (4)Cu1—N12.386 (3)
C5—N11.340 (4)Cu1—N21.996 (2)
C6—N21.313 (4)Cu1—N2i1.996 (2)
C6—N41.351 (4)Cu1—N6ii2.078 (2)
C7—N31.318 (4)Cu1—N6iii2.078 (2)
C7—N41.362 (4)N2—N31.383 (3)
C7—S11.732 (3)N4—N51.424 (4)
C8—H8A0.9700N5—H5A0.9582
C8—H8B0.9700N5—H5B0.9099
C8—C91.500 (4)N6—Cu1iv2.078 (2)
C8—S11.818 (3)O1—S21.435 (3)
C9—C101.391 (5)O2—S21.436 (3)
C9—C131.379 (4)O3—S21.441 (3)
C10—H100.9300O4—H4A0.8499
C10—C111.380 (5)O4—H4B0.8498
C11—H110.9300O5—H5C0.8500
C11—C121.378 (4)O5—H5D0.8501
C2—C1—H1118.6H14B—C14—H14C109.5
N1—C1—H1118.6S2—C14—H14A109.5
N1—C1—C2122.8 (3)S2—C14—H14B109.5
C1—C2—H2120.6S2—C14—H14C109.5
C3—C2—C1118.7 (3)N1—Cu1—N1i180.00 (6)
C3—C2—H2120.6N2i—Cu1—N1i75.08 (9)
C2—C3—H3120.1N2—Cu1—N1i104.92 (9)
C2—C3—C4119.9 (3)N2i—Cu1—N1104.92 (9)
C4—C3—H3120.1N2—Cu1—N175.08 (9)
C3—C4—H4121.2N2i—Cu1—N2180.00 (8)
C3—C4—C5117.6 (3)N2i—Cu1—N6iii90.15 (9)
C5—C4—H4121.2N2—Cu1—N6iii89.85 (9)
C4—C5—C6123.5 (3)N2i—Cu1—N6ii89.85 (9)
N1—C5—C4123.2 (3)N2—Cu1—N6ii90.15 (9)
N1—C5—C6113.3 (3)N6iii—Cu1—N189.50 (9)
N2—C6—C5121.6 (3)N6ii—Cu1—N190.50 (9)
N2—C6—N4108.4 (2)N6ii—Cu1—N1i89.50 (9)
N4—C6—C5130.0 (3)N6iii—Cu1—N1i90.50 (9)
N3—C7—N4111.2 (2)N6ii—Cu1—N6iii180.0
N3—C7—S1128.5 (2)C1—N1—C5117.8 (3)
N4—C7—S1120.3 (2)C1—N1—Cu1132.0 (2)
H8A—C8—H8B108.7C5—N1—Cu1110.11 (18)
C9—C8—H8A110.5C6—N2—Cu1119.83 (19)
C9—C8—H8B110.5C6—N2—N3110.0 (2)
C9—C8—S1106.0 (2)N3—N2—Cu1130.12 (18)
S1—C8—H8A110.5C7—N3—N2104.5 (2)
S1—C8—H8B110.5C6—N4—C7105.9 (2)
C10—C9—C8121.0 (3)C6—N4—N5126.3 (2)
C13—C9—C8121.0 (3)C7—N4—N5127.8 (2)
C13—C9—C10118.0 (3)N4—N5—H5A106.2
C9—C10—H10120.4N4—N5—H5B100.4
C11—C10—C9119.3 (3)H5A—N5—H5B112.0
C11—C10—H10120.4C12—N6—Cu1iv119.7 (2)
C10—C11—H11120.5C13—N6—C12117.8 (3)
C12—C11—C10119.1 (3)C13—N6—Cu1iv122.4 (2)
C12—C11—H11120.5H4A—O4—H4B96.7
C11—C12—H12118.8H5C—O5—H5D115.6
N6—C12—C11122.5 (3)C7—S1—C899.56 (15)
N6—C12—H12118.8O1—S2—C14105.5 (3)
C9—C13—H13118.3O1—S2—O2113.0 (2)
N6—C13—C9123.3 (3)O1—S2—O3112.1 (2)
N6—C13—H13118.3O2—S2—C14106.5 (3)
H14A—C14—H14B109.5O2—S2—O3111.7 (2)
H14A—C14—H14C109.5O3—S2—C14107.5 (3)
C1—C2—C3—C41.2 (5)N1i—Cu1—N1—C5173.4 (6)
C2—C1—N1—C50.4 (5)N1—Cu1—N2—C61.0 (2)
C2—C1—N1—Cu1176.2 (2)N1i—Cu1—N2—C6179.0 (2)
C2—C3—C4—C51.3 (5)N1i—Cu1—N2—N31.7 (2)
C3—C4—C5—C6178.1 (3)N1—Cu1—N2—N3178.3 (2)
C3—C4—C5—N10.6 (5)N2—C6—N4—C70.9 (3)
C4—C5—C6—N2175.9 (3)N2—C6—N4—N5178.1 (3)
C4—C5—C6—N43.6 (5)N2i—Cu1—N1—C12.6 (3)
C4—C5—N1—C10.3 (4)N2—Cu1—N1—C1177.4 (3)
C4—C5—N1—Cu1177.0 (2)N2—Cu1—N1—C50.50 (18)
C5—C6—N2—Cu12.5 (4)N2i—Cu1—N1—C5179.50 (18)
C5—C6—N2—N3179.8 (2)N2i—Cu1—N2—C678 (15)
C5—C6—N4—C7179.5 (3)N2i—Cu1—N2—N3105 (15)
C5—C6—N4—N52.3 (5)N3—C7—N4—C61.5 (3)
C6—C5—N1—C1179.1 (3)N3—C7—N4—N5178.5 (3)
C6—C5—N1—Cu11.7 (3)N3—C7—S1—C82.6 (3)
C6—N2—N3—C70.7 (3)N4—C6—N2—Cu1177.88 (17)
C8—C9—C10—C11177.5 (3)N4—C6—N2—N30.1 (3)
C8—C9—C13—N6177.6 (3)N4—C7—N3—N21.3 (3)
C9—C8—S1—C7176.4 (2)N4—C7—S1—C8176.2 (3)
C9—C10—C11—C120.4 (5)N6iii—Cu1—N1—C187.4 (3)
C9—C13—N6—C120.0 (4)N6ii—Cu1—N1—C192.6 (3)
C9—C13—N6—Cu1iv176.5 (2)N6ii—Cu1—N1—C590.5 (2)
C10—C9—C13—N60.0 (5)N6iii—Cu1—N1—C589.5 (2)
C10—C11—C12—N60.4 (5)N6ii—Cu1—N2—C689.5 (2)
C11—C12—N6—C130.2 (5)N6iii—Cu1—N2—C690.5 (2)
C11—C12—N6—Cu1iv176.4 (2)N6iii—Cu1—N2—N392.2 (2)
C13—C9—C10—C110.2 (5)N6ii—Cu1—N2—N387.8 (2)
Cu1—N2—N3—C7176.7 (2)S1—C7—N3—N2177.5 (2)
N1—C1—C2—C30.3 (5)S1—C7—N4—C6177.5 (2)
N1—C5—C6—N22.8 (4)S1—C7—N4—N50.5 (4)
N1—C5—C6—N4177.6 (3)S1—C8—C9—C1080.0 (3)
N1i—Cu1—N1—C19.8 (7)S1—C8—C9—C1397.5 (3)
Symmetry codes: (i) x, y, z+1; (ii) x, y1/2, z+3/2; (iii) x, y+1/2, z1/2; (iv) x, y+1/2, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5A···O2v0.962.072.985 (5)160
N5—H5B···O3vi0.912.113.007 (5)168
O4—H4A···O10.851.932.752 (4)162
O4—H4B···O2vii0.852.042.867 (5)165
O5—H5C···O4viii0.852.483.062 (6)127
O5—H5D···O30.852.152.887 (5)146
Symmetry codes: (v) x+1, y+1, z+1; (vi) x+1, y1/2, z+3/2; (vii) x, y+3/2, z+1/2; (viii) x+1, y, z.
catena-Poly[[copper(II)-bis{µ2-4-amino-3-(pyridin-2-yl)-5-[(pyridin-4-ylmethyl)sulfanyl]-1,2,4-triazole}] dinitrate methanol disolvate] (exp_2484) top
Crystal data top
[Cu(C13H12N5S)2](NO3)2·2CH4OZ = 2
Mr = 820.34F(000) = 846
Triclinic, P1Dx = 1.535 Mg m3
a = 9.5651 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.6688 (6) ÅCell parameters from 5210 reflections
c = 15.2716 (6) Åθ = 3.6–27.3°
α = 85.727 (4)°µ = 0.80 mm1
β = 80.360 (4)°T = 293 K
γ = 76.734 (4)°Block, clear light green
V = 1774.52 (14) Å30.41 × 0.2 × 0.14 mm
Data collection top
Rigaku OD SuperNova Dual source
diffractometer with an Eos detector
6331 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source4944 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.028
Detector resolution: 16.0793 pixels mm-1θmax = 25.1°, θmin = 3.0°
ω scansh = 911
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2015)
k = 1515
Tmin = 0.660, Tmax = 1.000l = 1818
12794 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0533P)2 + 1.5039P]
where P = (Fo2 + 2Fc2)/3
6331 reflections(Δ/σ)max = 0.001
485 parametersΔρmax = 0.51 e Å3
0 restraintsΔρmin = 0.44 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

X-ray intensity data of 13 were measured separately at 293 (2), 293 (2) and 150 (10) K on a Bruker SMART APEX CCD-based diffractometer equipped with a Cu-Kα radiation (λ = 1.54184 Å) for 1 and 3, and Mo-Kα radiation (λ = 0.71073 Å) for 2 by using phi and omega scan mode. For 2, a total of 12794 reflections were collected in the range of 2.99θ25.12°, of which 6331 were unique with Rint = 0.0279 and 4944 observed reflections with I > 2σ(I) were used in structure solution. All calculations were carried out with OLEX2. The structures were solved by direct methods and refined on F2 by full-matrix least-squares techniques. All non-hydrogen atoms were refined with anisotropic displacement parameters.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.2169 (4)1.1323 (3)0.5988 (2)0.0397 (8)
H10.17931.07080.59890.048*
C20.1300 (4)1.2235 (3)0.6394 (2)0.0482 (9)
H20.03511.22320.66580.058*
C30.1835 (4)1.3141 (3)0.6406 (3)0.0515 (10)
H30.12581.37600.66770.062*
C40.3246 (4)1.3127 (3)0.6009 (2)0.0445 (9)
H40.36381.37340.60110.053*
C50.4059 (3)1.2192 (2)0.56102 (19)0.0316 (7)
C60.5585 (3)1.2002 (2)0.52254 (19)0.0299 (7)
C70.7830 (4)1.2041 (3)0.4761 (2)0.0336 (7)
C81.0646 (4)1.1398 (3)0.4058 (2)0.0422 (8)
H8A1.16171.15300.39970.051*
H8B1.06001.07870.44760.051*
C91.0414 (3)1.1085 (3)0.3172 (2)0.0359 (7)
C101.0728 (4)1.0021 (3)0.2950 (2)0.0440 (9)
H101.10380.94730.33610.053*
C111.0582 (4)0.9768 (3)0.2118 (2)0.0468 (9)
H111.07980.90390.19830.056*
C120.9847 (6)1.1515 (3)0.1721 (3)0.0709 (14)
H120.95361.20470.12990.085*
C130.9956 (5)1.1846 (3)0.2540 (3)0.0635 (12)
H130.97211.25800.26610.076*
C140.7610 (4)0.8898 (3)0.0929 (2)0.0398 (8)
H140.69890.95780.09050.048*
C150.7043 (4)0.8035 (3)0.1306 (2)0.0439 (8)
H150.60630.81320.15410.053*
C160.7953 (4)0.7032 (3)0.1327 (3)0.0513 (10)
H160.75870.64300.15530.062*
C170.9414 (4)0.6917 (3)0.1012 (3)0.0481 (9)
H171.00520.62450.10450.058*
C180.9909 (3)0.7809 (2)0.0649 (2)0.0314 (7)
C191.1410 (3)0.7846 (2)0.02981 (19)0.0307 (7)
C201.3719 (4)0.7567 (2)0.0176 (2)0.0343 (7)
C211.6296 (4)0.7973 (3)0.0890 (2)0.0439 (8)
H21A1.59950.85570.04760.053*
H21B1.73450.77380.09460.053*
C221.5920 (4)0.8421 (3)0.1781 (2)0.0376 (8)
C231.5883 (4)0.9485 (3)0.2031 (2)0.0431 (8)
H231.60440.99510.16350.052*
C241.5607 (4)0.9871 (3)0.2868 (2)0.0447 (9)
H241.56011.05970.30190.054*
C251.5397 (6)0.8241 (3)0.3212 (3)0.0787 (15)
H251.52270.77890.36160.094*
C261.5676 (6)0.7789 (3)0.2401 (3)0.0757 (15)
H261.56990.70570.22720.091*
C270.5734 (8)0.4751 (7)0.2636 (5)0.138 (3)
H27A0.48430.45800.29350.208*
H27B0.60340.43800.20880.208*
H27C0.55870.55200.25150.208*
C280.1614 (9)0.4482 (5)0.3857 (5)0.139 (3)
H28A0.23560.38920.40300.208*
H28B0.14520.43750.32700.208*
H28C0.07290.45070.42670.208*
Cu11.00001.00000.00000.03498 (16)
Cu20.50001.00000.50000.03680 (17)
N10.6304 (3)1.10175 (19)0.50229 (17)0.0326 (6)
N20.7747 (3)1.1025 (2)0.47220 (17)0.0346 (6)
N30.6511 (3)1.26794 (19)0.50428 (17)0.0329 (6)
N40.6124 (4)1.3816 (2)0.5119 (2)0.0538 (8)
H4A0.66361.39290.55700.081*
H4B0.63561.42190.45350.081*
N51.0152 (3)1.0496 (2)0.14934 (18)0.0462 (7)
N60.9011 (3)0.87987 (19)0.05994 (17)0.0329 (6)
N71.1734 (3)0.8773 (2)0.00075 (17)0.0337 (6)
N81.3204 (3)0.8614 (2)0.02991 (18)0.0375 (6)
N91.2641 (3)0.70585 (19)0.01780 (17)0.0325 (6)
N101.2913 (3)0.5940 (2)0.0406 (2)0.0508 (8)
H10A1.22600.56600.01550.076*
H10B1.26470.58430.10310.076*
N111.5350 (3)0.9266 (2)0.34685 (18)0.0466 (7)
N120.3526 (3)1.12957 (19)0.55952 (17)0.0321 (6)
N130.3002 (4)0.7362 (3)0.2448 (2)0.0565 (8)
N140.9798 (5)0.4257 (3)0.1421 (3)0.0702 (11)
O10.3604 (4)0.7788 (3)0.1802 (2)0.0945 (11)
O20.3105 (6)0.7547 (3)0.3184 (2)0.1245 (17)
O30.2152 (4)0.6788 (3)0.2323 (2)0.0884 (10)
O40.2031 (7)0.5403 (5)0.3866 (3)0.147 (2)
H4C0.21210.56730.33600.221*
O50.6786 (5)0.4430 (4)0.3164 (3)0.1130 (14)
H50.75890.43340.28550.170*
O60.8772 (5)0.4065 (3)0.1113 (3)0.1043 (13)
O71.0987 (5)0.4143 (3)0.1000 (4)0.1325 (19)
O80.9533 (5)0.4598 (3)0.2198 (3)0.0910 (11)
S11.55076 (10)0.68567 (7)0.04139 (6)0.0439 (2)
S20.93662 (10)1.25768 (7)0.45205 (6)0.0446 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.035 (2)0.0410 (19)0.043 (2)0.0107 (15)0.0007 (15)0.0064 (15)
C20.035 (2)0.051 (2)0.054 (2)0.0040 (16)0.0027 (16)0.0135 (18)
C30.047 (2)0.045 (2)0.057 (2)0.0004 (17)0.0019 (18)0.0188 (18)
C40.047 (2)0.0329 (18)0.052 (2)0.0057 (15)0.0033 (17)0.0101 (15)
C50.0359 (19)0.0310 (16)0.0286 (16)0.0076 (13)0.0062 (13)0.0015 (12)
C60.0377 (19)0.0257 (15)0.0289 (16)0.0111 (13)0.0062 (13)0.0026 (12)
C70.0382 (19)0.0365 (18)0.0292 (17)0.0143 (14)0.0042 (14)0.0034 (13)
C80.038 (2)0.048 (2)0.043 (2)0.0145 (16)0.0047 (15)0.0060 (16)
C90.0330 (19)0.0384 (18)0.0354 (18)0.0116 (14)0.0021 (14)0.0014 (14)
C100.051 (2)0.0357 (19)0.042 (2)0.0026 (16)0.0107 (16)0.0030 (15)
C110.061 (3)0.0319 (18)0.046 (2)0.0040 (16)0.0126 (18)0.0027 (15)
C120.129 (4)0.036 (2)0.045 (2)0.003 (2)0.030 (2)0.0030 (17)
C130.114 (4)0.034 (2)0.043 (2)0.010 (2)0.021 (2)0.0044 (17)
C140.039 (2)0.0314 (17)0.046 (2)0.0024 (14)0.0044 (15)0.0014 (14)
C150.039 (2)0.046 (2)0.046 (2)0.0151 (16)0.0005 (16)0.0049 (16)
C160.052 (2)0.0340 (19)0.067 (3)0.0166 (17)0.0019 (19)0.0090 (17)
C170.052 (2)0.0265 (17)0.062 (2)0.0068 (16)0.0037 (18)0.0094 (16)
C180.0367 (19)0.0273 (16)0.0297 (16)0.0056 (13)0.0066 (13)0.0004 (12)
C190.0370 (19)0.0229 (15)0.0296 (16)0.0025 (13)0.0044 (13)0.0010 (12)
C200.0373 (19)0.0313 (17)0.0298 (17)0.0006 (14)0.0037 (14)0.0018 (13)
C210.034 (2)0.055 (2)0.040 (2)0.0050 (16)0.0073 (15)0.0051 (16)
C220.0349 (19)0.0421 (19)0.0319 (18)0.0053 (15)0.0004 (14)0.0005 (14)
C230.046 (2)0.044 (2)0.041 (2)0.0138 (16)0.0065 (16)0.0009 (15)
C240.053 (2)0.0371 (19)0.043 (2)0.0101 (16)0.0059 (17)0.0040 (15)
C250.153 (5)0.051 (3)0.048 (3)0.041 (3)0.035 (3)0.005 (2)
C260.148 (5)0.043 (2)0.046 (2)0.035 (3)0.028 (3)0.0111 (18)
C270.102 (6)0.183 (8)0.150 (7)0.065 (6)0.012 (5)0.040 (6)
C280.176 (8)0.108 (5)0.172 (7)0.083 (5)0.089 (6)0.041 (5)
Cu10.0306 (3)0.0226 (3)0.0462 (4)0.0027 (2)0.0021 (2)0.0059 (2)
Cu20.0316 (3)0.0261 (3)0.0513 (4)0.0092 (2)0.0051 (2)0.0105 (2)
N10.0314 (15)0.0280 (14)0.0373 (15)0.0078 (11)0.0002 (11)0.0031 (11)
N20.0341 (16)0.0315 (14)0.0385 (15)0.0108 (11)0.0004 (12)0.0032 (11)
N30.0393 (16)0.0241 (13)0.0357 (15)0.0086 (11)0.0032 (12)0.0058 (11)
N40.066 (2)0.0269 (15)0.069 (2)0.0159 (14)0.0008 (17)0.0086 (14)
N50.065 (2)0.0360 (16)0.0365 (16)0.0096 (14)0.0066 (14)0.0032 (12)
N60.0368 (16)0.0257 (13)0.0339 (15)0.0048 (11)0.0029 (12)0.0007 (11)
N70.0309 (15)0.0287 (14)0.0375 (15)0.0029 (11)0.0010 (11)0.0027 (11)
N80.0337 (16)0.0332 (15)0.0412 (16)0.0030 (12)0.0013 (12)0.0039 (12)
N90.0373 (16)0.0246 (13)0.0331 (14)0.0033 (11)0.0048 (11)0.0033 (10)
N100.057 (2)0.0246 (14)0.064 (2)0.0001 (13)0.0052 (16)0.0093 (13)
N110.057 (2)0.0464 (18)0.0363 (17)0.0149 (15)0.0053 (14)0.0041 (13)
N120.0343 (16)0.0280 (13)0.0346 (15)0.0083 (11)0.0033 (11)0.0038 (11)
N130.063 (2)0.055 (2)0.049 (2)0.0091 (17)0.0072 (17)0.0020 (16)
N140.083 (3)0.0302 (18)0.090 (3)0.0060 (19)0.005 (3)0.0079 (18)
O10.084 (3)0.137 (3)0.069 (2)0.048 (2)0.0000 (19)0.000 (2)
O20.227 (5)0.094 (3)0.062 (2)0.027 (3)0.062 (3)0.006 (2)
O30.094 (3)0.108 (3)0.077 (2)0.052 (2)0.0106 (19)0.000 (2)
O40.218 (6)0.162 (5)0.105 (3)0.118 (4)0.054 (4)0.031 (3)
O50.118 (4)0.099 (3)0.096 (3)0.005 (3)0.015 (3)0.002 (2)
O60.129 (4)0.090 (3)0.107 (3)0.035 (3)0.041 (3)0.001 (2)
O70.092 (3)0.080 (3)0.188 (5)0.006 (2)0.043 (3)0.011 (3)
O80.133 (3)0.063 (2)0.081 (3)0.025 (2)0.022 (2)0.0084 (19)
S10.0375 (5)0.0393 (5)0.0447 (5)0.0057 (4)0.0013 (4)0.0089 (4)
S20.0450 (5)0.0458 (5)0.0488 (5)0.0243 (4)0.0009 (4)0.0124 (4)
Geometric parameters (Å, º) top
C1—H10.9300C21—H21B0.9700
C1—C21.380 (5)C21—C221.503 (4)
C1—N121.329 (4)C21—S11.802 (4)
C2—H20.9300C22—C231.368 (5)
C2—C31.362 (5)C22—C261.364 (5)
C3—H30.9300C23—H230.9300
C3—C41.380 (5)C23—C241.379 (5)
C4—H40.9300C24—H240.9300
C4—C51.381 (4)C24—N111.325 (4)
C5—C61.451 (4)C25—H250.9300
C5—N121.351 (4)C25—C261.366 (6)
C6—N11.311 (4)C25—N111.321 (5)
C6—N31.352 (4)C26—H260.9300
C7—N21.313 (4)C27—H27A0.9600
C7—N31.354 (4)C27—H27B0.9600
C7—S21.731 (3)C27—H27C0.9600
C8—H8A0.9700C27—O51.365 (7)
C8—H8B0.9700C28—H28A0.9600
C8—C91.502 (4)C28—H28B0.9600
C8—S21.805 (3)C28—H28C0.9600
C9—C101.368 (4)C28—O41.318 (7)
C9—C131.364 (5)Cu1—N5i2.446 (3)
C10—H100.9300Cu1—N52.446 (3)
C10—C111.371 (5)Cu1—N6i2.052 (3)
C11—H110.9300Cu1—N62.052 (3)
C11—N51.325 (4)Cu1—N71.997 (2)
C12—H120.9300Cu1—N7i1.997 (2)
C12—C131.377 (5)Cu2—N11.994 (3)
C12—N51.316 (5)Cu2—N1ii1.994 (3)
C13—H130.9300Cu2—N12ii2.059 (2)
C14—H140.9300Cu2—N122.059 (2)
C14—C151.376 (5)N1—N21.382 (4)
C14—N61.331 (4)N3—N41.411 (3)
C15—H150.9300N4—H4A0.9461
C15—C161.367 (5)N4—H4B1.0110
C16—H160.9300N7—N81.378 (4)
C16—C171.377 (5)N9—N101.409 (3)
C17—H170.9300N10—H10A0.9296
C17—C181.369 (5)N10—H10B0.9529
C18—C191.456 (4)N13—O11.211 (4)
C18—N61.353 (4)N13—O21.191 (4)
C19—N71.309 (4)N13—O31.254 (4)
C19—N91.353 (4)N14—O61.234 (5)
C20—N81.315 (4)N14—O71.193 (5)
C20—N91.355 (4)N14—O81.258 (5)
C20—S11.733 (3)O4—H4C0.8200
C21—H21A0.9700O5—H50.8200
C2—C1—H1119.0N11—C25—H25117.3
N12—C1—H1119.0N11—C25—C26125.4 (4)
N12—C1—C2122.1 (3)C22—C26—C25119.5 (4)
C1—C2—H2120.1C22—C26—H26120.3
C3—C2—C1119.8 (3)C25—C26—H26120.3
C3—C2—H2120.1H27A—C27—H27B109.5
C2—C3—H3120.4H27A—C27—H27C109.5
C2—C3—C4119.1 (3)H27B—C27—H27C109.5
C4—C3—H3120.4O5—C27—H27A109.5
C3—C4—H4120.8O5—C27—H27B109.5
C3—C4—C5118.4 (3)O5—C27—H27C109.5
C5—C4—H4120.8H28A—C28—H28B109.5
C4—C5—C6126.0 (3)H28A—C28—H28C109.5
N12—C5—C4122.4 (3)H28B—C28—H28C109.5
N12—C5—C6111.4 (3)O4—C28—H28A109.5
N1—C6—C5119.9 (3)O4—C28—H28B109.5
N1—C6—N3108.6 (3)O4—C28—H28C109.5
N3—C6—C5131.5 (3)N5i—Cu1—N5180.0
N2—C7—N3111.3 (3)N6i—Cu1—N5i87.12 (10)
N2—C7—S2127.8 (3)N6—Cu1—N5i92.88 (10)
N3—C7—S2120.9 (2)N6—Cu1—N587.12 (10)
H8A—C8—H8B107.5N6i—Cu1—N592.88 (10)
C9—C8—H8A108.4N6—Cu1—N6i180.00 (8)
C9—C8—H8B108.4N7i—Cu1—N588.22 (10)
C9—C8—S2115.4 (2)N7i—Cu1—N5i91.78 (10)
S2—C8—H8A108.4N7—Cu1—N5i88.22 (10)
S2—C8—H8B108.4N7—Cu1—N591.78 (10)
C10—C9—C8120.9 (3)N7i—Cu1—N699.99 (10)
C13—C9—C8121.7 (3)N7—Cu1—N680.01 (10)
C13—C9—C10117.2 (3)N7—Cu1—N6i99.99 (10)
C9—C10—H10120.3N7i—Cu1—N6i80.01 (10)
C9—C10—C11119.4 (3)N7—Cu1—N7i179.999 (1)
C11—C10—H10120.3N1ii—Cu2—N1179.999 (2)
C10—C11—H11117.9N1—Cu2—N12ii100.02 (10)
N5—C11—C10124.2 (3)N1ii—Cu2—N12ii79.98 (10)
N5—C11—H11117.9N1ii—Cu2—N12100.02 (10)
C13—C12—H12117.8N1—Cu2—N1279.98 (10)
N5—C12—H12117.8N12—Cu2—N12ii180.00 (10)
N5—C12—C13124.4 (3)C6—N1—Cu2112.7 (2)
C9—C13—C12119.2 (3)C6—N1—N2109.5 (2)
C9—C13—H13120.4N2—N1—Cu2136.43 (19)
C12—C13—H13120.4C7—N2—N1104.9 (2)
C15—C14—H14118.7C6—N3—C7105.6 (2)
N6—C14—H14118.7C6—N3—N4125.4 (3)
N6—C14—C15122.7 (3)C7—N3—N4128.9 (3)
C14—C15—H15120.7N3—N4—H4A102.8
C16—C15—C14118.6 (3)N3—N4—H4B112.6
C16—C15—H15120.7H4A—N4—H4B114.7
C15—C16—H16120.2C11—N5—Cu1122.7 (2)
C15—C16—C17119.6 (3)C12—N5—C11115.5 (3)
C17—C16—H16120.2C12—N5—Cu1121.7 (2)
C16—C17—H17120.6C14—N6—C18118.2 (3)
C18—C17—C16118.8 (3)C14—N6—Cu1127.0 (2)
C18—C17—H17120.6C18—N6—Cu1114.8 (2)
C17—C18—C19126.5 (3)C19—N7—Cu1113.7 (2)
N6—C18—C17122.0 (3)C19—N7—N8109.7 (2)
N6—C18—C19111.5 (3)N8—N7—Cu1136.2 (2)
N7—C19—C18119.7 (3)C20—N8—N7105.0 (3)
N7—C19—N9108.4 (3)C19—N9—C20105.9 (2)
N9—C19—C18131.9 (3)C19—N9—N10131.7 (3)
N8—C20—N9111.0 (3)C20—N9—N10122.3 (3)
N8—C20—S1127.6 (3)N9—N10—H10A106.3
N9—C20—S1121.4 (2)N9—N10—H10B109.1
H21A—C21—H21B107.4H10A—N10—H10B105.0
C22—C21—H21A108.2C25—N11—C24114.8 (3)
C22—C21—H21B108.2C1—N12—C5118.1 (3)
C22—C21—S1116.3 (3)C1—N12—Cu2127.5 (2)
S1—C21—H21A108.2C5—N12—Cu2114.2 (2)
S1—C21—H21B108.2O1—N13—O3117.8 (4)
C23—C22—C21121.0 (3)O2—N13—O1121.9 (4)
C26—C22—C21122.6 (3)O2—N13—O3120.0 (4)
C26—C22—C23116.3 (3)O6—N14—O8117.2 (5)
C22—C23—H23119.8O7—N14—O6121.8 (5)
C22—C23—C24120.3 (3)O7—N14—O8121.0 (5)
C24—C23—H23119.8C28—O4—H4C109.5
C23—C24—H24118.2C27—O5—H5109.5
N11—C24—C23123.7 (3)C20—S1—C2198.06 (16)
N11—C24—H24118.2C7—S2—C898.96 (16)
C26—C25—H25117.3
C1—C2—C3—C40.0 (6)N3—C6—N1—N21.7 (3)
C2—C1—N12—C50.8 (5)N3—C7—N2—N12.0 (3)
C2—C1—N12—Cu2177.6 (3)N3—C7—S2—C8172.7 (2)
C2—C3—C4—C50.3 (6)N5—C12—C13—C90.3 (8)
C3—C4—C5—C6174.8 (3)N5i—Cu1—N5—C1164 (34)
C3—C4—C5—N120.1 (5)N5i—Cu1—N5—C12118 (34)
C4—C5—C6—N1166.8 (3)N5—Cu1—N6—C1483.5 (3)
C4—C5—C6—N310.6 (5)N5i—Cu1—N6—C1496.5 (3)
C4—C5—N12—C10.5 (5)N5i—Cu1—N6—C1883.2 (2)
C4—C5—N12—Cu2177.7 (2)N5—Cu1—N6—C1896.8 (2)
C5—C6—N1—Cu215.0 (3)N5—Cu1—N7—C1992.0 (2)
C5—C6—N1—N2176.2 (3)N5i—Cu1—N7—C1988.0 (2)
C5—C6—N3—C7174.8 (3)N5i—Cu1—N7—N883.9 (3)
C5—C6—N3—N46.7 (5)N5—Cu1—N7—N896.1 (3)
C6—C5—N12—C1174.9 (3)N6—C14—C15—C161.2 (5)
C6—C5—N12—Cu22.2 (3)N6—C18—C19—N71.6 (4)
C6—N1—N2—C70.2 (3)N6—C18—C19—N9176.5 (3)
C8—C9—C10—C11176.3 (3)N6i—Cu1—N5—C11134.8 (3)
C8—C9—C13—C12176.1 (4)N6—Cu1—N5—C1145.2 (3)
C9—C8—S2—C769.4 (3)N6—Cu1—N5—C12136.8 (4)
C9—C10—C11—N50.2 (6)N6i—Cu1—N5—C1243.2 (4)
C10—C9—C13—C120.6 (6)N6i—Cu1—N6—C14112 (52)
C10—C11—N5—C120.6 (6)N6i—Cu1—N6—C1868 (52)
C10—C11—N5—Cu1177.6 (3)N6—Cu1—N7—C195.2 (2)
C13—C9—C10—C110.4 (5)N6i—Cu1—N7—C19174.8 (2)
C13—C12—N5—C110.4 (7)N6—Cu1—N7—N8177.1 (3)
C13—C12—N5—Cu1177.8 (4)N6i—Cu1—N7—N82.9 (3)
C14—C15—C16—C173.0 (6)N7—C19—N9—C201.6 (3)
C15—C14—N6—C180.9 (5)N7—C19—N9—N10176.9 (3)
C15—C14—N6—Cu1178.8 (3)N7—Cu1—N5—C1134.7 (3)
C15—C16—C17—C182.7 (6)N7i—Cu1—N5—C11145.3 (3)
C16—C17—C18—C19178.9 (3)N7i—Cu1—N5—C1236.7 (4)
C16—C17—C18—N60.6 (5)N7—Cu1—N5—C12143.3 (4)
C17—C18—C19—N7176.9 (3)N7i—Cu1—N6—C144.1 (3)
C17—C18—C19—N95.1 (6)N7—Cu1—N6—C14175.9 (3)
C17—C18—N6—C141.2 (5)N7i—Cu1—N6—C18175.5 (2)
C17—C18—N6—Cu1178.5 (3)N7—Cu1—N6—C184.5 (2)
C18—C19—N7—Cu15.4 (4)N7i—Cu1—N7—C1921.0 (3)
C18—C19—N7—N8179.5 (3)N7i—Cu1—N7—N8150.9 (4)
C18—C19—N9—C20179.8 (3)N8—C20—N9—C191.6 (3)
C18—C19—N9—N104.9 (6)N8—C20—N9—N10177.5 (3)
C19—C18—N6—C14177.4 (3)N8—C20—S1—C212.2 (3)
C19—C18—N6—Cu12.9 (3)N9—C19—N7—Cu1173.07 (19)
C19—N7—N8—C200.0 (3)N9—C19—N7—N81.0 (3)
C21—C22—C23—C24176.8 (3)N9—C20—N8—N71.0 (3)
C21—C22—C26—C25177.3 (4)N9—C20—S1—C21177.7 (3)
C22—C21—S1—C2070.0 (3)N11—C25—C26—C220.6 (9)
C22—C23—C24—N110.8 (6)N12—C1—C2—C30.6 (6)
C23—C22—C26—C250.8 (7)N12—C5—C6—N18.5 (4)
C23—C24—N11—C250.9 (6)N12—C5—C6—N3174.2 (3)
C26—C22—C23—C240.1 (6)N12ii—Cu2—N1—C6168.2 (2)
C26—C25—N11—C240.3 (8)N12—Cu2—N1—C611.8 (2)
Cu1—N7—N8—C20172.2 (2)N12ii—Cu2—N1—N23.6 (3)
Cu2—N1—N2—C7165.1 (2)N12—Cu2—N1—N2176.4 (3)
N1—C6—N3—C72.8 (3)N12ii—Cu2—N12—C163 (54)
N1—C6—N3—N4175.7 (3)N12ii—Cu2—N12—C5114 (54)
N1ii—Cu2—N1—C663 (17)S1—C20—N8—N7179.0 (2)
N1ii—Cu2—N1—N2101 (17)S1—C20—N9—C19178.4 (2)
N1—Cu2—N12—C1169.2 (3)S1—C20—N9—N102.6 (4)
N1ii—Cu2—N12—C110.8 (3)S1—C21—C22—C23151.1 (3)
N1ii—Cu2—N12—C5172.4 (2)S1—C21—C22—C2632.5 (5)
N1—Cu2—N12—C57.6 (2)S2—C7—N2—N1176.9 (2)
N2—C7—N3—C63.0 (3)S2—C7—N3—C6176.0 (2)
N2—C7—N3—N4175.4 (3)S2—C7—N3—N45.6 (4)
N2—C7—S2—C88.5 (3)S2—C8—C9—C10146.7 (3)
N3—C6—N1—Cu2167.13 (19)S2—C8—C9—C1336.7 (5)
Symmetry codes: (i) x+2, y+2, z; (ii) x+1, y+2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4A···O2ii0.952.573.103 (5)116
N4—H4A···O4ii0.952.022.907 (6)156
N4—H4B···O5iii1.012.073.026 (5)156
N10—H10A···O6iv0.932.293.039 (5)138
N10—H10A···O70.932.653.233 (6)122
N10—H10B···O3v0.952.313.107 (5)141
O4—H4C···O30.822.042.834 (6)162
O5—H5···O80.822.052.835 (6)162
Symmetry codes: (ii) x+1, y+2, z+1; (iii) x, y+1, z; (iv) x+2, y+1, z; (v) x+1, y, z.
catena-Poly[[copper(II)-bis{µ2-4-amino-3-(pyridin-2-yl)-5-[(pyridin-4-ylmethyl)sulfanyl]-1,2,4-triazole}] bis(perchlorate) monohydrate] (exp_2623) top
Crystal data top
[Cu(C13H12N5S)2](ClO4)2·H2OF(000) = 1732
Mr = 849.15Dx = 1.673 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54184 Å
a = 9.6589 (3) ÅCell parameters from 4224 reflections
b = 23.1463 (5) Åθ = 4.8–71.0°
c = 15.5643 (4) ŵ = 4.16 mm1
β = 104.305 (3)°T = 150 K
V = 3371.79 (15) Å3Needle, clear light green
Z = 40.34 × 0.08 × 0.06 mm
Data collection top
Rigaku OD SuperNova Dual source
diffractometer with an Eos detector
6016 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source4595 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.029
Detector resolution: 16.0793 pixels mm-1θmax = 67.1°, θmin = 3.8°
ω scansh = 1111
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2015)
k = 2427
Tmin = 0.506, Tmax = 1.000l = 1718
12396 measured reflections
Refinement top
Refinement on F2Primary atom site location: iterative
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.182H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.1015P)2 + 6.635P]
where P = (Fo2 + 2Fc2)/3
6016 reflections(Δ/σ)max < 0.001
469 parametersΔρmax = 1.32 e Å3
0 restraintsΔρmin = 0.94 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

X-ray intensity data of 13 were measured separately at 293 (2), 293 (2) and 150 (10) K on a Bruker SMART APEX CCD-based diffractometer equipped with a Cu-Kα radiation (λ = 1.54184 Å) for 1 and 3, and Mo-Kα radiation (λ = 0.71073 Å) for 2 by using phi and omega scan mode. For compound 3, a total of 12396 reflections were collected in the range of 3.82θ67,07°, of which 6016 were unique with Rint = 0.0286 and 4595 observed reflections with I > 2σ(I) were used in structure solution. All calculations were carried out with OLEX2. The structures were solved by direct methods and refined on F2 by full-matrix least-squares techniques. All non-hydrogen atoms were refined with anisotropic displacement parameters.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.2006 (4)0.18264 (18)0.6594 (3)0.0270 (9)
H10.15090.21660.66270.032*
C20.1264 (5)0.13495 (18)0.6174 (3)0.0301 (9)
H20.02820.13690.59380.036*
C30.1990 (5)0.08511 (18)0.6111 (3)0.0311 (10)
H30.15060.05300.58260.037*
C40.3463 (5)0.08262 (17)0.6475 (3)0.0283 (9)
H40.39790.04920.64380.034*
C50.4129 (4)0.13156 (16)0.6891 (2)0.0210 (8)
C60.5656 (4)0.13822 (16)0.7274 (2)0.0214 (8)
C70.7956 (4)0.13123 (17)0.7741 (3)0.0240 (8)
C81.0630 (4)0.15969 (19)0.8592 (3)0.0283 (9)
H8A1.16350.14940.87450.034*
H8B1.05110.19180.81800.034*
C91.0239 (4)0.18009 (18)0.9424 (3)0.0248 (8)
C101.0510 (4)0.23635 (18)0.9699 (3)0.0262 (9)
H101.08630.26240.93510.031*
C111.0257 (5)0.25409 (18)1.0495 (3)0.0292 (9)
H111.04500.29231.06660.035*
C120.9434 (5)0.16537 (19)1.0733 (3)0.0328 (10)
H120.90200.14081.10720.039*
C130.9680 (5)0.14391 (18)0.9961 (3)0.0313 (10)
H130.94740.10560.98010.038*
C140.7382 (4)0.31454 (19)0.8481 (3)0.0280 (9)
H140.78700.28030.84510.034*
C150.8131 (5)0.36148 (18)0.8885 (3)0.0303 (9)
H150.91120.35900.91230.036*
C160.7412 (5)0.41257 (18)0.8935 (3)0.0315 (10)
H160.79060.44480.92100.038*
C170.5952 (5)0.41543 (18)0.8574 (3)0.0283 (9)
H170.54490.44940.85960.034*
C180.5262 (4)0.36606 (16)0.8176 (2)0.0205 (8)
C190.3734 (4)0.35932 (16)0.7810 (2)0.0211 (8)
C200.1423 (4)0.36608 (17)0.7342 (3)0.0234 (8)
C210.1266 (4)0.33849 (19)0.6498 (3)0.0284 (9)
H21A0.11380.30520.68890.034*
H21B0.22720.34870.63570.034*
C220.0881 (4)0.32119 (18)0.5653 (3)0.0248 (8)
C230.0446 (5)0.36051 (18)0.5100 (3)0.0296 (9)
H230.03240.39930.52580.036*
C240.0197 (5)0.34127 (19)0.4314 (3)0.0333 (10)
H240.01020.36820.39540.040*
C250.0749 (5)0.24880 (18)0.4581 (3)0.0282 (9)
H250.08500.21010.44150.034*
C260.1012 (4)0.26433 (18)0.5387 (3)0.0261 (9)
H260.12750.23640.57460.031*
Cl10.71671 (12)0.08210 (4)0.50514 (6)0.0313 (3)
Cl20.25606 (14)0.49586 (6)0.56479 (10)0.0543 (4)
Cu10.46947 (6)0.24888 (2)0.75251 (4)0.0241 (2)
N10.3422 (3)0.18109 (14)0.6953 (2)0.0223 (7)
N20.6173 (3)0.18974 (14)0.7517 (2)0.0220 (7)
N30.7643 (4)0.18600 (14)0.7816 (2)0.0251 (7)
N40.6745 (4)0.09964 (14)0.7415 (2)0.0223 (7)
N50.6600 (4)0.04031 (15)0.7219 (3)0.0346 (9)
N60.5963 (3)0.31634 (14)0.8124 (2)0.0223 (7)
N70.3208 (3)0.30798 (14)0.7537 (2)0.0216 (7)
N80.1740 (3)0.31159 (14)0.7244 (2)0.0246 (7)
N90.2635 (4)0.39750 (14)0.7691 (2)0.0230 (7)
N100.2750 (4)0.45586 (15)0.7928 (2)0.0319 (8)
N110.0360 (4)0.28598 (15)0.4032 (2)0.0272 (8)
N120.9751 (4)0.21940 (15)1.1029 (2)0.0262 (7)
O10.3161 (5)0.54430 (18)0.5296 (3)0.0634 (12)
H9A0.31510.52530.39670.095*
H9B0.41510.53550.36140.095*
H10A0.24080.47580.74330.095*
H5A0.72060.02410.77370.095*
H5B0.71650.03550.68820.095*
H10B0.22380.46230.83730.095*
O20.1681 (7)0.5196 (3)0.6197 (4)0.139 (3)
O30.1844 (8)0.4624 (3)0.4904 (5)0.146 (3)
O40.3661 (5)0.46299 (18)0.6224 (3)0.0666 (12)
O50.6300 (4)0.04374 (18)0.4415 (3)0.0561 (10)
O60.6231 (6)0.11149 (19)0.5492 (3)0.0765 (16)
O70.7859 (6)0.12172 (19)0.4611 (3)0.0813 (17)
O80.8177 (4)0.04955 (18)0.5695 (3)0.0594 (11)
O90.3254 (4)0.54163 (16)0.3493 (2)0.0463 (9)
S10.02472 (11)0.39841 (5)0.70932 (7)0.0297 (3)
S20.96262 (11)0.09890 (5)0.80271 (7)0.0300 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.024 (2)0.024 (2)0.030 (2)0.0003 (16)0.0018 (17)0.0044 (16)
C20.027 (2)0.027 (2)0.033 (2)0.0066 (17)0.0004 (18)0.0013 (17)
C30.034 (2)0.023 (2)0.032 (2)0.0095 (18)0.0009 (19)0.0007 (17)
C40.033 (2)0.018 (2)0.032 (2)0.0010 (17)0.0045 (19)0.0014 (16)
C50.0244 (19)0.0208 (19)0.0169 (18)0.0010 (15)0.0037 (15)0.0031 (14)
C60.027 (2)0.0170 (18)0.0206 (18)0.0029 (16)0.0060 (16)0.0017 (14)
C70.026 (2)0.025 (2)0.0200 (19)0.0053 (16)0.0035 (16)0.0023 (15)
C80.0211 (19)0.036 (2)0.025 (2)0.0031 (17)0.0016 (17)0.0005 (17)
C90.0203 (19)0.028 (2)0.024 (2)0.0064 (16)0.0007 (16)0.0017 (16)
C100.026 (2)0.027 (2)0.023 (2)0.0039 (17)0.0019 (17)0.0026 (16)
C110.035 (2)0.023 (2)0.026 (2)0.0074 (17)0.0010 (18)0.0004 (16)
C120.045 (3)0.024 (2)0.032 (2)0.0064 (19)0.014 (2)0.0004 (17)
C130.043 (3)0.020 (2)0.031 (2)0.0011 (18)0.009 (2)0.0019 (17)
C140.022 (2)0.027 (2)0.032 (2)0.0015 (17)0.0019 (17)0.0011 (17)
C150.025 (2)0.029 (2)0.032 (2)0.0057 (17)0.0021 (18)0.0020 (18)
C160.039 (2)0.022 (2)0.031 (2)0.0083 (18)0.006 (2)0.0040 (17)
C170.035 (2)0.019 (2)0.028 (2)0.0014 (17)0.0039 (18)0.0009 (16)
C180.0245 (19)0.0198 (19)0.0168 (18)0.0006 (15)0.0045 (15)0.0007 (14)
C190.025 (2)0.0179 (19)0.0196 (18)0.0013 (15)0.0043 (16)0.0002 (14)
C200.027 (2)0.024 (2)0.0188 (18)0.0048 (16)0.0050 (16)0.0020 (15)
C210.0217 (19)0.032 (2)0.031 (2)0.0034 (17)0.0057 (17)0.0039 (18)
C220.0194 (19)0.028 (2)0.025 (2)0.0017 (16)0.0010 (16)0.0017 (16)
C230.035 (2)0.023 (2)0.029 (2)0.0036 (18)0.0042 (18)0.0034 (16)
C240.045 (3)0.029 (2)0.027 (2)0.008 (2)0.011 (2)0.0006 (18)
C250.037 (2)0.022 (2)0.025 (2)0.0038 (17)0.0053 (18)0.0011 (16)
C260.025 (2)0.028 (2)0.024 (2)0.0025 (17)0.0033 (17)0.0040 (16)
Cl10.0446 (6)0.0187 (5)0.0267 (5)0.0006 (4)0.0012 (5)0.0005 (4)
Cl20.0432 (7)0.0530 (8)0.0695 (9)0.0036 (6)0.0190 (6)0.0142 (7)
Cu10.0189 (3)0.0170 (3)0.0328 (4)0.0010 (2)0.0006 (3)0.0079 (2)
N10.0254 (17)0.0175 (16)0.0235 (16)0.0001 (13)0.0049 (14)0.0001 (13)
N20.0199 (16)0.0218 (17)0.0222 (16)0.0014 (13)0.0010 (13)0.0043 (13)
N30.0216 (17)0.0251 (18)0.0272 (17)0.0026 (14)0.0034 (14)0.0044 (14)
N40.0275 (17)0.0173 (16)0.0207 (16)0.0046 (13)0.0033 (14)0.0008 (12)
N50.042 (2)0.0193 (18)0.039 (2)0.0056 (16)0.0027 (17)0.0014 (15)
N60.0237 (17)0.0205 (16)0.0222 (16)0.0005 (13)0.0048 (14)0.0029 (13)
N70.0193 (16)0.0218 (17)0.0219 (16)0.0001 (13)0.0017 (13)0.0032 (13)
N80.0211 (16)0.0236 (17)0.0267 (17)0.0034 (14)0.0013 (14)0.0028 (13)
N90.0298 (18)0.0168 (16)0.0221 (16)0.0052 (13)0.0059 (14)0.0018 (12)
N100.041 (2)0.0185 (17)0.034 (2)0.0040 (15)0.0056 (17)0.0038 (14)
N110.0305 (18)0.0261 (18)0.0242 (17)0.0041 (15)0.0054 (15)0.0021 (14)
N120.0294 (18)0.0239 (18)0.0226 (17)0.0011 (14)0.0014 (14)0.0007 (13)
O10.082 (3)0.051 (2)0.060 (2)0.026 (2)0.023 (2)0.002 (2)
O20.139 (5)0.185 (7)0.125 (5)0.118 (5)0.092 (5)0.103 (5)
O30.115 (5)0.138 (6)0.155 (6)0.092 (5)0.026 (5)0.014 (5)
O40.068 (3)0.052 (2)0.088 (3)0.018 (2)0.033 (2)0.012 (2)
O50.053 (2)0.064 (3)0.053 (2)0.026 (2)0.0165 (19)0.0267 (19)
O60.123 (4)0.065 (3)0.041 (2)0.057 (3)0.019 (2)0.0014 (19)
O70.140 (5)0.053 (3)0.045 (2)0.055 (3)0.013 (3)0.006 (2)
O80.046 (2)0.060 (2)0.070 (3)0.0121 (19)0.009 (2)0.028 (2)
O90.046 (2)0.050 (2)0.0391 (19)0.0028 (17)0.0023 (16)0.0076 (16)
S10.0267 (5)0.0306 (6)0.0299 (5)0.0103 (4)0.0036 (4)0.0072 (4)
S20.0261 (5)0.0304 (6)0.0306 (5)0.0104 (4)0.0015 (4)0.0070 (4)
Geometric parameters (Å, º) top
C1—H10.9300C20—N81.316 (5)
C1—C21.388 (6)C20—N91.371 (5)
C1—N11.344 (5)C20—S11.733 (4)
C2—H20.9300C21—H21A0.9700
C2—C31.366 (6)C21—H21B0.9700
C3—H30.9300C21—C221.507 (6)
C3—C41.397 (6)C21—S11.817 (4)
C4—H40.9300C22—C231.386 (6)
C4—C51.382 (6)C22—C261.376 (6)
C5—C61.456 (5)C23—H230.9300
C5—N11.350 (5)C23—C241.379 (6)
C6—N21.312 (5)C24—H240.9300
C6—N41.355 (5)C24—N111.349 (6)
C7—N31.315 (5)C25—H250.9300
C7—N41.367 (5)C25—C261.387 (6)
C7—S21.734 (4)C25—N111.331 (5)
C8—H8A0.9700C26—H260.9300
C8—H8B0.9700Cl1—O51.436 (4)
C8—C91.511 (6)Cl1—O61.434 (4)
C8—S21.809 (4)Cl1—O71.409 (4)
C9—C101.376 (6)Cl1—O81.428 (4)
C9—C131.383 (6)Cl2—O11.432 (4)
C10—H100.9300Cl2—O21.454 (6)
C10—C111.382 (6)Cl2—O31.422 (6)
C11—H110.9300Cl2—O41.429 (4)
C11—N121.333 (6)Cu1—N12.056 (3)
C12—H120.9300Cu1—N21.980 (3)
C12—C131.374 (6)Cu1—N62.060 (3)
C12—N121.342 (6)Cu1—N71.986 (3)
C13—H130.9300Cu1—N12i2.454 (3)
C14—H140.9300N2—N31.382 (5)
C14—C151.369 (6)N4—N51.406 (5)
C14—N61.346 (5)N5—H5A0.9482
C15—H150.9300N5—H5B0.8517
C15—C161.383 (6)N7—N81.381 (4)
C16—H160.9300N9—N101.398 (5)
C16—C171.385 (6)N10—H10A0.8889
C17—H170.9300N10—H10B0.9574
C17—C181.389 (6)N12—Cu1ii2.454 (3)
C18—C191.453 (5)O9—H9A0.8562
C18—N61.348 (5)O9—H9A0.8562
C19—N71.321 (5)O9—H9B0.8516
C19—N91.358 (5)
C2—C1—H1119.1C26—C22—C23117.4 (4)
N1—C1—H1119.1C22—C23—H23120.5
N1—C1—C2121.9 (4)C24—C23—C22119.0 (4)
C1—C2—H2120.3C24—C23—H23120.5
C3—C2—C1119.4 (4)C23—C24—H24117.9
C3—C2—H2120.3N11—C24—C23124.3 (4)
C2—C3—H3120.2N11—C24—H24117.9
C2—C3—C4119.7 (4)C26—C25—H25118.1
C4—C3—H3120.2N11—C25—H25118.1
C3—C4—H4121.1N11—C25—C26123.8 (4)
C5—C4—C3117.8 (4)C22—C26—C25119.7 (4)
C5—C4—H4121.1C22—C26—H26120.1
C4—C5—C6125.8 (4)C25—C26—H26120.1
N1—C5—C4123.0 (4)O6—Cl1—O5107.1 (3)
N1—C5—C6111.1 (3)O7—Cl1—O5109.4 (2)
N2—C6—C5119.3 (3)O7—Cl1—O6110.8 (3)
N2—C6—N4109.1 (3)O7—Cl1—O8111.2 (3)
N4—C6—C5131.5 (4)O8—Cl1—O5109.8 (3)
N3—C7—N4110.7 (3)O8—Cl1—O6108.5 (3)
N3—C7—S2127.8 (3)O1—Cl2—O2106.2 (4)
N4—C7—S2121.4 (3)O3—Cl2—O1106.1 (4)
H8A—C8—H8B107.4O3—Cl2—O2116.5 (5)
C9—C8—H8A108.2O3—Cl2—O4111.0 (4)
C9—C8—H8B108.2O4—Cl2—O1110.3 (3)
C9—C8—S2116.2 (3)O4—Cl2—O2106.5 (3)
S2—C8—H8A108.2N1—Cu1—N6178.80 (13)
S2—C8—H8B108.2N1—Cu1—N12i88.18 (12)
C10—C9—C8119.6 (4)N2—Cu1—N179.90 (13)
C10—C9—C13117.3 (4)N2—Cu1—N6100.23 (13)
C13—C9—C8123.1 (4)N2—Cu1—N7179.74 (15)
C9—C10—H10120.1N2—Cu1—N12i90.91 (13)
C9—C10—C11119.9 (4)N6—Cu1—N12i93.01 (12)
C11—C10—H10120.1N7—Cu1—N199.99 (13)
C10—C11—H11118.2N7—Cu1—N679.87 (13)
N12—C11—C10123.6 (4)N7—Cu1—N12i89.32 (13)
N12—C11—H11118.2C1—N1—C5118.3 (3)
C13—C12—H12117.8C1—N1—Cu1126.7 (3)
N12—C12—H12117.8C5—N1—Cu1114.9 (3)
N12—C12—C13124.3 (4)C6—N2—Cu1114.0 (3)
C9—C13—H13120.4C6—N2—N3109.0 (3)
C12—C13—C9119.1 (4)N3—N2—Cu1136.3 (2)
C12—C13—H13120.4C7—N3—N2105.7 (3)
C15—C14—H14118.9C6—N4—C7105.4 (3)
N6—C14—H14118.9C6—N4—N5125.2 (3)
N6—C14—C15122.2 (4)C7—N4—N5129.3 (3)
C14—C15—H15120.4N4—N5—H5A101.2
C14—C15—C16119.3 (4)N4—N5—H5B102.5
C16—C15—H15120.4H5A—N5—H5B96.8
C15—C16—H16120.2C14—N6—C18118.5 (3)
C15—C16—C17119.5 (4)C14—N6—Cu1126.5 (3)
C17—C16—H16120.2C18—N6—Cu1115.0 (3)
C16—C17—H17121.0C19—N7—Cu1113.7 (3)
C16—C17—C18118.1 (4)C19—N7—N8109.5 (3)
C18—C17—H17121.0N8—N7—Cu1136.4 (2)
C17—C18—C19126.3 (4)C20—N8—N7105.6 (3)
N6—C18—C17122.4 (4)C19—N9—C20105.7 (3)
N6—C18—C19111.2 (3)C19—N9—N10125.7 (3)
N7—C19—C18119.7 (3)C20—N9—N10128.4 (3)
N7—C19—N9108.4 (3)N9—N10—H10A106.5
N9—C19—C18131.9 (3)N9—N10—H10B108.7
N8—C20—N9110.7 (3)H10A—N10—H10B113.4
N8—C20—S1128.2 (3)C25—N11—C24115.7 (4)
N9—C20—S1121.1 (3)C11—N12—C12115.7 (4)
H21A—C21—H21B107.5C11—N12—Cu1ii120.6 (3)
C22—C21—H21A108.4C12—N12—Cu1ii123.3 (3)
C22—C21—H21B108.4H9A—O9—H9A0.0
C22—C21—S1115.4 (3)H9A—O9—H9B93.7
S1—C21—H21A108.4H9A—O9—H9B93.7
S1—C21—H21B108.4C20—S1—C2198.15 (19)
C23—C22—C21123.0 (4)C7—S2—C898.17 (19)
C26—C22—C21119.5 (4)
C1—C2—C3—C40.6 (7)N1—Cu1—N7—C19174.6 (3)
C2—C1—N1—C50.6 (6)N1—Cu1—N7—N83.1 (4)
C2—C1—N1—Cu1175.9 (3)N2—C6—N4—C71.2 (4)
C2—C3—C4—C50.1 (6)N2—C6—N4—N5178.9 (4)
C3—C4—C5—C6177.1 (4)N2—Cu1—N1—C1172.3 (4)
C3—C4—C5—N10.5 (6)N2—Cu1—N1—C53.1 (3)
C4—C5—C6—N2168.8 (4)N2—Cu1—N6—C146.4 (4)
C4—C5—C6—N48.4 (7)N2—Cu1—N6—C18175.7 (3)
C4—C5—N1—C10.1 (6)N2—Cu1—N7—C19119 (36)
C4—C5—N1—Cu1175.7 (3)N2—Cu1—N7—N870 (37)
C5—C6—N2—Cu111.1 (5)N3—C7—N4—C61.1 (4)
C5—C6—N2—N3176.9 (3)N3—C7—N4—N5178.7 (4)
C5—C6—N4—C7176.2 (4)N3—C7—S2—C88.9 (4)
C5—C6—N4—N51.6 (7)N4—C6—N2—Cu1171.2 (2)
C6—C5—N1—C1177.2 (3)N4—C6—N2—N30.9 (4)
C6—C5—N1—Cu11.4 (4)N4—C7—N3—N20.6 (4)
C6—N2—N3—C70.2 (4)N4—C7—S2—C8169.2 (3)
C8—C9—C10—C11175.0 (4)N6—C14—C15—C160.3 (7)
C8—C9—C13—C12176.2 (4)N6—C18—C19—N74.2 (5)
C9—C8—S2—C763.8 (3)N6—C18—C19—N9177.0 (4)
C9—C10—C11—N120.1 (7)N6—Cu1—N1—C191 (6)
C10—C9—C13—C120.4 (6)N6—Cu1—N1—C593 (6)
C10—C11—N12—C122.7 (6)N6—Cu1—N2—C6171.3 (3)
C10—C11—N12—Cu1ii170.4 (3)N6—Cu1—N2—N32.1 (4)
C13—C9—C10—C111.6 (6)N6—Cu1—N7—C196.6 (3)
C13—C12—N12—C114.1 (7)N6—Cu1—N7—N8178.1 (4)
C13—C12—N12—Cu1ii168.8 (4)N7—C19—N9—C200.8 (4)
C14—C15—C16—C170.2 (7)N7—C19—N9—N10177.6 (3)
C15—C14—N6—C180.5 (6)N7—Cu1—N1—C17.9 (4)
C15—C14—N6—Cu1178.4 (3)N7—Cu1—N1—C5176.6 (3)
C15—C16—C17—C180.4 (6)N7—Cu1—N2—C659 (37)
C16—C17—C18—C19176.0 (4)N7—Cu1—N2—N3110 (36)
C16—C17—C18—N60.7 (6)N7—Cu1—N6—C14173.3 (4)
C17—C18—C19—N7172.8 (4)N7—Cu1—N6—C184.6 (3)
C17—C18—C19—N96.1 (7)N8—C20—N9—C190.4 (4)
C17—C18—N6—C140.8 (6)N8—C20—N9—N10177.0 (4)
C17—C18—N6—Cu1178.9 (3)N8—C20—S1—C219.8 (4)
C18—C19—N7—Cu18.1 (5)N9—C19—N7—Cu1172.8 (2)
C18—C19—N7—N8178.1 (3)N9—C19—N7—N81.0 (4)
C18—C19—N9—C20178.1 (4)N9—C20—N8—N70.2 (4)
C18—C19—N9—N101.4 (7)N9—C20—S1—C21170.3 (3)
C19—C18—N6—C14176.3 (3)N11—C25—C26—C220.4 (7)
C19—C18—N6—Cu11.7 (4)N12—C12—C13—C92.7 (7)
C19—N7—N8—C200.7 (4)N12i—Cu1—N1—C181.1 (3)
C21—C22—C23—C24176.1 (4)N12i—Cu1—N1—C594.4 (3)
C21—C22—C26—C25175.8 (4)N12i—Cu1—N2—C695.5 (3)
C22—C21—S1—C2063.7 (3)N12i—Cu1—N2—N395.4 (4)
C22—C23—C24—N110.5 (7)N12i—Cu1—N6—C1497.9 (3)
C23—C22—C26—C251.8 (6)N12i—Cu1—N6—C1884.2 (3)
C23—C24—N11—C251.9 (7)N12i—Cu1—N7—C1986.5 (3)
C26—C22—C23—C241.3 (6)N12i—Cu1—N7—N884.9 (4)
C26—C25—N11—C241.4 (6)S1—C20—N8—N7179.9 (3)
Cu1—N2—N3—C7169.3 (3)S1—C20—N9—C19179.5 (3)
Cu1—N7—N8—C20171.0 (3)S1—C20—N9—N102.9 (6)
N1—C1—C2—C30.9 (7)S1—C21—C22—C2334.1 (5)
N1—C5—C6—N28.2 (5)S1—C21—C22—C26148.5 (3)
N1—C5—C6—N4174.6 (4)S2—C7—N3—N2178.8 (3)
N1—Cu1—N2—C67.5 (3)S2—C7—N4—C6179.5 (3)
N1—Cu1—N2—N3176.6 (4)S2—C7—N4—N52.9 (6)
N1—Cu1—N6—C1490 (6)S2—C8—C9—C10155.1 (3)
N1—Cu1—N6—C1888 (6)S2—C8—C9—C1328.5 (5)
Symmetry codes: (i) x1/2, y+1/2, z1/2; (ii) x+1/2, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O9—H9A···O10.862.112.831 (6)141
O9—H9A···O30.862.603.393 (9)155
O9—H9B···O4iii0.852.072.904 (6)168
N10—H10A···O20.892.133.021 (6)176
N10—H10A···O40.892.492.999 (6)117
N5—H5A···O9ii0.952.032.918 (5)154
N5—H5B···O80.852.323.127 (6)159
N10—H10B···O5iv0.962.052.986 (5)166
Symmetry codes: (ii) x+1/2, y+1/2, z+1/2; (iii) x+1, y+1, z+1; (iv) x1/2, y+1/2, z+1/2.
 

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