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
CCDC references: 1903962; 1903961; 1903960
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{µ
2-4-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)2·4H2O | F(000) = 926 |
Mr = 894.48 | Dx = 1.557 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 9.1819 (4) Å | Cell parameters from 2984 reflections |
b = 18.0782 (7) Å | θ = 4.6–71.1° |
c = 11.7932 (5) Å | µ = 3.46 mm−1 |
β = 102.977 (4)° | T = 293 K |
V = 1907.58 (14) Å3 | Block, clear pale blue |
Z = 2 | 0.15 × 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 Source | 2735 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.030 |
Detector resolution: 16.0793 pixels mm-1 | θmax = 67.1°, θmin = 4.6° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | k = −21→20 |
Tmin = 0.913, Tmax = 1.000 | l = −10→14 |
6493 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: iterative |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.143 | H 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 parameters | Δρmax = 0.41 e Å−3 |
0 restraints | Δρmin = −0.44 e Å−3 |
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 1–3 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
4.56≤θ≤67.04°, 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 | x | y | z | Uiso*/Ueq | |
C1 | 0.2992 (4) | −0.11847 (17) | 0.5508 (3) | 0.0372 (8) | |
H1 | 0.2327 | −0.1560 | 0.5200 | 0.045* | |
C2 | 0.4493 (4) | −0.13536 (19) | 0.5855 (3) | 0.0426 (8) | |
H2 | 0.4830 | −0.1833 | 0.5787 | 0.051* | |
C3 | 0.5478 (4) | −0.08003 (19) | 0.6304 (3) | 0.0408 (8) | |
H3 | 0.6496 | −0.0901 | 0.6530 | 0.049* | |
C4 | 0.4956 (4) | −0.00942 (17) | 0.6420 (3) | 0.0337 (7) | |
H4 | 0.5603 | 0.0286 | 0.6736 | 0.040* | |
C5 | 0.3428 (3) | 0.00278 (15) | 0.6046 (3) | 0.0250 (6) | |
C6 | 0.2726 (3) | 0.07532 (15) | 0.6083 (2) | 0.0234 (6) | |
C7 | 0.2185 (3) | 0.18983 (16) | 0.6331 (3) | 0.0287 (6) | |
C8 | 0.0584 (4) | 0.31482 (17) | 0.6426 (3) | 0.0355 (7) | |
H8A | 0.0205 | 0.3135 | 0.5589 | 0.043* | |
H8B | −0.0063 | 0.2851 | 0.6789 | 0.043* | |
C9 | 0.0652 (3) | 0.39288 (17) | 0.6865 (3) | 0.0296 (7) | |
C10 | 0.1112 (4) | 0.45039 (18) | 0.6244 (3) | 0.0365 (7) | |
H10 | 0.1347 | 0.4413 | 0.5529 | 0.044* | |
C11 | 0.1215 (4) | 0.52103 (19) | 0.6699 (3) | 0.0388 (8) | |
H11 | 0.1527 | 0.5601 | 0.6297 | 0.047* | |
C12 | 0.0852 (4) | 0.53288 (17) | 0.7756 (3) | 0.0309 (7) | |
H12 | 0.0917 | 0.5806 | 0.8057 | 0.037* | |
C13 | 0.0313 (3) | 0.40940 (16) | 0.7918 (3) | 0.0285 (6) | |
H13 | 0.0006 | 0.3712 | 0.8337 | 0.034* | |
C14 | 0.3889 (8) | 0.5824 (3) | 0.3991 (5) | 0.103 (2) | |
H14A | 0.3050 | 0.5766 | 0.3344 | 0.154* | |
H14B | 0.3871 | 0.5441 | 0.4551 | 0.154* | |
H14C | 0.4799 | 0.5792 | 0.3722 | 0.154* | |
Cu1 | 0.0000 | 0.0000 | 0.5000 | 0.0222 (2) | |
N1 | 0.2455 (3) | −0.05047 (13) | 0.5594 (2) | 0.0292 (6) | |
N2 | 0.1291 (3) | 0.08548 (13) | 0.5658 (2) | 0.0235 (5) | |
N3 | 0.0918 (3) | 0.15853 (13) | 0.5798 (2) | 0.0287 (6) | |
N4 | 0.3334 (3) | 0.14049 (13) | 0.6507 (2) | 0.0268 (5) | |
N5 | 0.4854 (3) | 0.15295 (16) | 0.7073 (3) | 0.0427 (7) | |
H5A | 0.5196 | 0.1927 | 0.6662 | 0.064* | |
H5B | 0.4747 | 0.1671 | 0.7790 | 0.064* | |
N6 | 0.0405 (3) | 0.47795 (13) | 0.8369 (2) | 0.0266 (5) | |
O1 | 0.2588 (3) | 0.6622 (2) | 0.5223 (3) | 0.0717 (9) | |
O2 | 0.3502 (4) | 0.7212 (2) | 0.3702 (3) | 0.0876 (12) | |
O3 | 0.5205 (3) | 0.6812 (2) | 0.5425 (3) | 0.0728 (9) | |
O4 | 0.1204 (4) | 0.7194 (2) | 0.6872 (3) | 0.0953 (13) | |
H4A | 0.1744 | 0.7104 | 0.6390 | 0.143* | |
H4B | 0.1849 | 0.7446 | 0.7345 | 0.143* | |
O5 | 0.8265 (4) | 0.6332 (2) | 0.6211 (3) | 0.0949 (13) | |
H5C | 0.8606 | 0.6761 | 0.6132 | 0.142* | |
H5D | 0.7336 | 0.6274 | 0.5926 | 0.142* | |
S1 | 0.24915 (9) | 0.28024 (4) | 0.68101 (8) | 0.0426 (3) | |
S2 | 0.37890 (10) | 0.66810 (5) | 0.46314 (8) | 0.0420 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.045 (2) | 0.0223 (16) | 0.0421 (19) | 0.0016 (13) | 0.0057 (15) | −0.0019 (13) |
C2 | 0.047 (2) | 0.0313 (18) | 0.049 (2) | 0.0143 (15) | 0.0092 (17) | 0.0028 (15) |
C3 | 0.0323 (18) | 0.043 (2) | 0.045 (2) | 0.0125 (15) | 0.0042 (14) | 0.0078 (16) |
C4 | 0.0270 (17) | 0.0329 (17) | 0.0385 (19) | 0.0013 (12) | 0.0017 (14) | 0.0025 (14) |
C5 | 0.0287 (16) | 0.0219 (15) | 0.0236 (15) | 0.0005 (11) | 0.0041 (12) | 0.0026 (11) |
C6 | 0.0264 (15) | 0.0205 (14) | 0.0233 (14) | −0.0031 (11) | 0.0059 (11) | 0.0003 (11) |
C7 | 0.0307 (16) | 0.0224 (14) | 0.0332 (17) | −0.0019 (12) | 0.0078 (13) | −0.0035 (12) |
C8 | 0.0295 (16) | 0.0312 (17) | 0.0449 (19) | −0.0013 (13) | 0.0062 (14) | −0.0116 (14) |
C9 | 0.0246 (15) | 0.0277 (16) | 0.0345 (17) | 0.0031 (12) | 0.0026 (12) | −0.0056 (12) |
C10 | 0.0435 (19) | 0.0359 (18) | 0.0311 (17) | 0.0059 (14) | 0.0106 (14) | −0.0018 (13) |
C11 | 0.047 (2) | 0.0290 (16) | 0.043 (2) | 0.0030 (15) | 0.0169 (16) | 0.0061 (14) |
C12 | 0.0355 (17) | 0.0227 (15) | 0.0347 (17) | 0.0018 (12) | 0.0081 (13) | 0.0004 (12) |
C13 | 0.0263 (15) | 0.0241 (15) | 0.0345 (17) | 0.0004 (12) | 0.0054 (12) | 0.0013 (12) |
C14 | 0.136 (6) | 0.076 (4) | 0.094 (4) | 0.026 (4) | 0.022 (4) | −0.036 (3) |
Cu1 | 0.0246 (3) | 0.0171 (3) | 0.0246 (3) | −0.0043 (2) | 0.0051 (2) | −0.0014 (2) |
N1 | 0.0323 (14) | 0.0233 (13) | 0.0309 (14) | −0.0006 (10) | 0.0049 (11) | −0.0022 (10) |
N2 | 0.0265 (13) | 0.0189 (12) | 0.0247 (13) | −0.0014 (9) | 0.0048 (10) | −0.0029 (9) |
N3 | 0.0287 (13) | 0.0189 (12) | 0.0377 (15) | −0.0009 (10) | 0.0057 (11) | −0.0052 (10) |
N4 | 0.0228 (12) | 0.0247 (12) | 0.0318 (14) | −0.0043 (9) | 0.0036 (10) | −0.0044 (10) |
N5 | 0.0329 (15) | 0.0384 (16) | 0.0522 (18) | −0.0079 (12) | 0.0001 (13) | −0.0090 (13) |
N6 | 0.0280 (13) | 0.0213 (12) | 0.0304 (14) | 0.0032 (10) | 0.0064 (10) | −0.0011 (10) |
O1 | 0.063 (2) | 0.095 (2) | 0.067 (2) | −0.0004 (17) | 0.0349 (16) | −0.0002 (18) |
O2 | 0.094 (3) | 0.093 (3) | 0.071 (2) | −0.012 (2) | 0.0091 (19) | 0.036 (2) |
O3 | 0.0505 (18) | 0.099 (3) | 0.064 (2) | 0.0038 (17) | 0.0024 (15) | −0.0130 (18) |
O4 | 0.075 (2) | 0.123 (3) | 0.096 (3) | −0.004 (2) | 0.036 (2) | −0.043 (2) |
O5 | 0.085 (3) | 0.127 (4) | 0.070 (2) | 0.040 (2) | 0.012 (2) | −0.015 (2) |
S1 | 0.0335 (5) | 0.0234 (4) | 0.0663 (6) | −0.0024 (3) | 0.0018 (4) | −0.0164 (4) |
S2 | 0.0428 (5) | 0.0478 (5) | 0.0364 (5) | 0.0037 (4) | 0.0112 (4) | 0.0007 (4) |
Geometric parameters (Å, º) top
C1—H1 | 0.9300 | C12—H12 | 0.9300 |
C1—C2 | 1.381 (5) | C12—N6 | 1.346 (4) |
C1—N1 | 1.337 (4) | C13—H13 | 0.9300 |
C2—H2 | 0.9300 | C13—N6 | 1.344 (4) |
C2—C3 | 1.373 (5) | C14—H14A | 0.9600 |
C3—H3 | 0.9300 | C14—H14B | 0.9600 |
C3—C4 | 1.381 (5) | C14—H14C | 0.9600 |
C4—H4 | 0.9300 | C14—S2 | 1.735 (5) |
C4—C5 | 1.390 (4) | Cu1—N1i | 2.386 (3) |
C5—C6 | 1.466 (4) | Cu1—N1 | 2.386 (3) |
C5—N1 | 1.340 (4) | Cu1—N2 | 1.996 (2) |
C6—N2 | 1.313 (4) | Cu1—N2i | 1.996 (2) |
C6—N4 | 1.351 (4) | Cu1—N6ii | 2.078 (2) |
C7—N3 | 1.318 (4) | Cu1—N6iii | 2.078 (2) |
C7—N4 | 1.362 (4) | N2—N3 | 1.383 (3) |
C7—S1 | 1.732 (3) | N4—N5 | 1.424 (4) |
C8—H8A | 0.9700 | N5—H5A | 0.9582 |
C8—H8B | 0.9700 | N5—H5B | 0.9099 |
C8—C9 | 1.500 (4) | N6—Cu1iv | 2.078 (2) |
C8—S1 | 1.818 (3) | O1—S2 | 1.435 (3) |
C9—C10 | 1.391 (5) | O2—S2 | 1.436 (3) |
C9—C13 | 1.379 (4) | O3—S2 | 1.441 (3) |
C10—H10 | 0.9300 | O4—H4A | 0.8499 |
C10—C11 | 1.380 (5) | O4—H4B | 0.8498 |
C11—H11 | 0.9300 | O5—H5C | 0.8500 |
C11—C12 | 1.378 (4) | O5—H5D | 0.8501 |
| | | |
C2—C1—H1 | 118.6 | H14B—C14—H14C | 109.5 |
N1—C1—H1 | 118.6 | S2—C14—H14A | 109.5 |
N1—C1—C2 | 122.8 (3) | S2—C14—H14B | 109.5 |
C1—C2—H2 | 120.6 | S2—C14—H14C | 109.5 |
C3—C2—C1 | 118.7 (3) | N1—Cu1—N1i | 180.00 (6) |
C3—C2—H2 | 120.6 | N2i—Cu1—N1i | 75.08 (9) |
C2—C3—H3 | 120.1 | N2—Cu1—N1i | 104.92 (9) |
C2—C3—C4 | 119.9 (3) | N2i—Cu1—N1 | 104.92 (9) |
C4—C3—H3 | 120.1 | N2—Cu1—N1 | 75.08 (9) |
C3—C4—H4 | 121.2 | N2i—Cu1—N2 | 180.00 (8) |
C3—C4—C5 | 117.6 (3) | N2i—Cu1—N6iii | 90.15 (9) |
C5—C4—H4 | 121.2 | N2—Cu1—N6iii | 89.85 (9) |
C4—C5—C6 | 123.5 (3) | N2i—Cu1—N6ii | 89.85 (9) |
N1—C5—C4 | 123.2 (3) | N2—Cu1—N6ii | 90.15 (9) |
N1—C5—C6 | 113.3 (3) | N6iii—Cu1—N1 | 89.50 (9) |
N2—C6—C5 | 121.6 (3) | N6ii—Cu1—N1 | 90.50 (9) |
N2—C6—N4 | 108.4 (2) | N6ii—Cu1—N1i | 89.50 (9) |
N4—C6—C5 | 130.0 (3) | N6iii—Cu1—N1i | 90.50 (9) |
N3—C7—N4 | 111.2 (2) | N6ii—Cu1—N6iii | 180.0 |
N3—C7—S1 | 128.5 (2) | C1—N1—C5 | 117.8 (3) |
N4—C7—S1 | 120.3 (2) | C1—N1—Cu1 | 132.0 (2) |
H8A—C8—H8B | 108.7 | C5—N1—Cu1 | 110.11 (18) |
C9—C8—H8A | 110.5 | C6—N2—Cu1 | 119.83 (19) |
C9—C8—H8B | 110.5 | C6—N2—N3 | 110.0 (2) |
C9—C8—S1 | 106.0 (2) | N3—N2—Cu1 | 130.12 (18) |
S1—C8—H8A | 110.5 | C7—N3—N2 | 104.5 (2) |
S1—C8—H8B | 110.5 | C6—N4—C7 | 105.9 (2) |
C10—C9—C8 | 121.0 (3) | C6—N4—N5 | 126.3 (2) |
C13—C9—C8 | 121.0 (3) | C7—N4—N5 | 127.8 (2) |
C13—C9—C10 | 118.0 (3) | N4—N5—H5A | 106.2 |
C9—C10—H10 | 120.4 | N4—N5—H5B | 100.4 |
C11—C10—C9 | 119.3 (3) | H5A—N5—H5B | 112.0 |
C11—C10—H10 | 120.4 | C12—N6—Cu1iv | 119.7 (2) |
C10—C11—H11 | 120.5 | C13—N6—C12 | 117.8 (3) |
C12—C11—C10 | 119.1 (3) | C13—N6—Cu1iv | 122.4 (2) |
C12—C11—H11 | 120.5 | H4A—O4—H4B | 96.7 |
C11—C12—H12 | 118.8 | H5C—O5—H5D | 115.6 |
N6—C12—C11 | 122.5 (3) | C7—S1—C8 | 99.56 (15) |
N6—C12—H12 | 118.8 | O1—S2—C14 | 105.5 (3) |
C9—C13—H13 | 118.3 | O1—S2—O2 | 113.0 (2) |
N6—C13—C9 | 123.3 (3) | O1—S2—O3 | 112.1 (2) |
N6—C13—H13 | 118.3 | O2—S2—C14 | 106.5 (3) |
H14A—C14—H14B | 109.5 | O2—S2—O3 | 111.7 (2) |
H14A—C14—H14C | 109.5 | O3—S2—C14 | 107.5 (3) |
| | | |
C1—C2—C3—C4 | 1.2 (5) | N1i—Cu1—N1—C5 | −173.4 (6) |
C2—C1—N1—C5 | −0.4 (5) | N1—Cu1—N2—C6 | −1.0 (2) |
C2—C1—N1—Cu1 | 176.2 (2) | N1i—Cu1—N2—C6 | 179.0 (2) |
C2—C3—C4—C5 | −1.3 (5) | N1i—Cu1—N2—N3 | 1.7 (2) |
C3—C4—C5—C6 | −178.1 (3) | N1—Cu1—N2—N3 | −178.3 (2) |
C3—C4—C5—N1 | 0.6 (5) | N2—C6—N4—C7 | 0.9 (3) |
C4—C5—C6—N2 | 175.9 (3) | N2—C6—N4—N5 | 178.1 (3) |
C4—C5—C6—N4 | −3.6 (5) | N2i—Cu1—N1—C1 | 2.6 (3) |
C4—C5—N1—C1 | 0.3 (4) | N2—Cu1—N1—C1 | −177.4 (3) |
C4—C5—N1—Cu1 | −177.0 (2) | N2—Cu1—N1—C5 | −0.50 (18) |
C5—C6—N2—Cu1 | 2.5 (4) | N2i—Cu1—N1—C5 | 179.50 (18) |
C5—C6—N2—N3 | −179.8 (2) | N2i—Cu1—N2—C6 | −78 (15) |
C5—C6—N4—C7 | −179.5 (3) | N2i—Cu1—N2—N3 | 105 (15) |
C5—C6—N4—N5 | −2.3 (5) | N3—C7—N4—C6 | −1.5 (3) |
C6—C5—N1—C1 | 179.1 (3) | N3—C7—N4—N5 | −178.5 (3) |
C6—C5—N1—Cu1 | 1.7 (3) | N3—C7—S1—C8 | 2.6 (3) |
C6—N2—N3—C7 | −0.7 (3) | N4—C6—N2—Cu1 | −177.88 (17) |
C8—C9—C10—C11 | −177.5 (3) | N4—C6—N2—N3 | −0.1 (3) |
C8—C9—C13—N6 | 177.6 (3) | N4—C7—N3—N2 | 1.3 (3) |
C9—C8—S1—C7 | 176.4 (2) | N4—C7—S1—C8 | −176.2 (3) |
C9—C10—C11—C12 | −0.4 (5) | N6iii—Cu1—N1—C1 | −87.4 (3) |
C9—C13—N6—C12 | 0.0 (4) | N6ii—Cu1—N1—C1 | 92.6 (3) |
C9—C13—N6—Cu1iv | −176.5 (2) | N6ii—Cu1—N1—C5 | −90.5 (2) |
C10—C9—C13—N6 | 0.0 (5) | N6iii—Cu1—N1—C5 | 89.5 (2) |
C10—C11—C12—N6 | 0.4 (5) | N6ii—Cu1—N2—C6 | 89.5 (2) |
C11—C12—N6—C13 | −0.2 (5) | N6iii—Cu1—N2—C6 | −90.5 (2) |
C11—C12—N6—Cu1iv | 176.4 (2) | N6iii—Cu1—N2—N3 | 92.2 (2) |
C13—C9—C10—C11 | 0.2 (5) | N6ii—Cu1—N2—N3 | −87.8 (2) |
Cu1—N2—N3—C7 | 176.7 (2) | S1—C7—N3—N2 | −177.5 (2) |
N1—C1—C2—C3 | −0.3 (5) | S1—C7—N4—C6 | 177.5 (2) |
N1—C5—C6—N2 | −2.8 (4) | S1—C7—N4—N5 | 0.5 (4) |
N1—C5—C6—N4 | 177.6 (3) | S1—C8—C9—C10 | 80.0 (3) |
N1i—Cu1—N1—C1 | 9.8 (7) | S1—C8—C9—C13 | −97.5 (3) |
Symmetry codes: (i) −x, −y, −z+1; (ii) −x, y−1/2, −z+3/2; (iii) x, −y+1/2, z−1/2; (iv) −x, y+1/2, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5A···O2v | 0.96 | 2.07 | 2.985 (5) | 160 |
N5—H5B···O3vi | 0.91 | 2.11 | 3.007 (5) | 168 |
O4—H4A···O1 | 0.85 | 1.93 | 2.752 (4) | 162 |
O4—H4B···O2vii | 0.85 | 2.04 | 2.867 (5) | 165 |
O5—H5C···O4viii | 0.85 | 2.48 | 3.062 (6) | 127 |
O5—H5D···O3 | 0.85 | 2.15 | 2.887 (5) | 146 |
Symmetry codes: (v) −x+1, −y+1, −z+1; (vi) −x+1, y−1/2, −z+3/2; (vii) x, −y+3/2, z+1/2; (viii) x+1, y, z. |
catena-Poly[[copper(II)-bis{µ
2-4-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)2·2CH4O | Z = 2 |
Mr = 820.34 | F(000) = 846 |
Triclinic, P1 | Dx = 1.535 Mg m−3 |
a = 9.5651 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.6688 (6) Å | Cell parameters from 5210 reflections |
c = 15.2716 (6) Å | θ = 3.6–27.3° |
α = 85.727 (4)° | µ = 0.80 mm−1 |
β = 80.360 (4)° | T = 293 K |
γ = 76.734 (4)° | Block, clear light green |
V = 1774.52 (14) Å3 | 0.41 × 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 Source | 4944 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.028 |
Detector resolution: 16.0793 pixels mm-1 | θmax = 25.1°, θmin = 3.0° |
ω scans | h = −9→11 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | k = −15→15 |
Tmin = 0.660, Tmax = 1.000 | l = −18→18 |
12794 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.126 | H 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 parameters | Δρmax = 0.51 e Å−3 |
0 restraints | Δρmin = −0.44 e Å−3 |
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 1–3 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
2.99≤θ≤25.12°, 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 | x | y | z | Uiso*/Ueq | |
C1 | 0.2169 (4) | 1.1323 (3) | 0.5988 (2) | 0.0397 (8) | |
H1 | 0.1793 | 1.0708 | 0.5989 | 0.048* | |
C2 | 0.1300 (4) | 1.2235 (3) | 0.6394 (2) | 0.0482 (9) | |
H2 | 0.0351 | 1.2232 | 0.6658 | 0.058* | |
C3 | 0.1835 (4) | 1.3141 (3) | 0.6406 (3) | 0.0515 (10) | |
H3 | 0.1258 | 1.3760 | 0.6677 | 0.062* | |
C4 | 0.3246 (4) | 1.3127 (3) | 0.6009 (2) | 0.0445 (9) | |
H4 | 0.3638 | 1.3734 | 0.6011 | 0.053* | |
C5 | 0.4059 (3) | 1.2192 (2) | 0.56102 (19) | 0.0316 (7) | |
C6 | 0.5585 (3) | 1.2002 (2) | 0.52254 (19) | 0.0299 (7) | |
C7 | 0.7830 (4) | 1.2041 (3) | 0.4761 (2) | 0.0336 (7) | |
C8 | 1.0646 (4) | 1.1398 (3) | 0.4058 (2) | 0.0422 (8) | |
H8A | 1.1617 | 1.1530 | 0.3997 | 0.051* | |
H8B | 1.0600 | 1.0787 | 0.4476 | 0.051* | |
C9 | 1.0414 (3) | 1.1085 (3) | 0.3172 (2) | 0.0359 (7) | |
C10 | 1.0728 (4) | 1.0021 (3) | 0.2950 (2) | 0.0440 (9) | |
H10 | 1.1038 | 0.9473 | 0.3361 | 0.053* | |
C11 | 1.0582 (4) | 0.9768 (3) | 0.2118 (2) | 0.0468 (9) | |
H11 | 1.0798 | 0.9039 | 0.1983 | 0.056* | |
C12 | 0.9847 (6) | 1.1515 (3) | 0.1721 (3) | 0.0709 (14) | |
H12 | 0.9536 | 1.2047 | 0.1299 | 0.085* | |
C13 | 0.9956 (5) | 1.1846 (3) | 0.2540 (3) | 0.0635 (12) | |
H13 | 0.9721 | 1.2580 | 0.2661 | 0.076* | |
C14 | 0.7610 (4) | 0.8898 (3) | 0.0929 (2) | 0.0398 (8) | |
H14 | 0.6989 | 0.9578 | 0.0905 | 0.048* | |
C15 | 0.7043 (4) | 0.8035 (3) | 0.1306 (2) | 0.0439 (8) | |
H15 | 0.6063 | 0.8132 | 0.1541 | 0.053* | |
C16 | 0.7953 (4) | 0.7032 (3) | 0.1327 (3) | 0.0513 (10) | |
H16 | 0.7587 | 0.6430 | 0.1553 | 0.062* | |
C17 | 0.9414 (4) | 0.6917 (3) | 0.1012 (3) | 0.0481 (9) | |
H17 | 1.0052 | 0.6245 | 0.1045 | 0.058* | |
C18 | 0.9909 (3) | 0.7809 (2) | 0.0649 (2) | 0.0314 (7) | |
C19 | 1.1410 (3) | 0.7846 (2) | 0.02981 (19) | 0.0307 (7) | |
C20 | 1.3719 (4) | 0.7567 (2) | −0.0176 (2) | 0.0343 (7) | |
C21 | 1.6296 (4) | 0.7973 (3) | −0.0890 (2) | 0.0439 (8) | |
H21A | 1.5995 | 0.8557 | −0.0476 | 0.053* | |
H21B | 1.7345 | 0.7738 | −0.0946 | 0.053* | |
C22 | 1.5920 (4) | 0.8421 (3) | −0.1781 (2) | 0.0376 (8) | |
C23 | 1.5883 (4) | 0.9485 (3) | −0.2031 (2) | 0.0431 (8) | |
H23 | 1.6044 | 0.9951 | −0.1635 | 0.052* | |
C24 | 1.5607 (4) | 0.9871 (3) | −0.2868 (2) | 0.0447 (9) | |
H24 | 1.5601 | 1.0597 | −0.3019 | 0.054* | |
C25 | 1.5397 (6) | 0.8241 (3) | −0.3212 (3) | 0.0787 (15) | |
H25 | 1.5227 | 0.7789 | −0.3616 | 0.094* | |
C26 | 1.5676 (6) | 0.7789 (3) | −0.2401 (3) | 0.0757 (15) | |
H26 | 1.5699 | 0.7057 | −0.2272 | 0.091* | |
C27 | 0.5734 (8) | 0.4751 (7) | 0.2636 (5) | 0.138 (3) | |
H27A | 0.4843 | 0.4580 | 0.2935 | 0.208* | |
H27B | 0.6034 | 0.4380 | 0.2088 | 0.208* | |
H27C | 0.5587 | 0.5520 | 0.2515 | 0.208* | |
C28 | 0.1614 (9) | 0.4482 (5) | 0.3857 (5) | 0.139 (3) | |
H28A | 0.2356 | 0.3892 | 0.4030 | 0.208* | |
H28B | 0.1452 | 0.4375 | 0.3270 | 0.208* | |
H28C | 0.0729 | 0.4507 | 0.4267 | 0.208* | |
Cu1 | 1.0000 | 1.0000 | 0.0000 | 0.03498 (16) | |
Cu2 | 0.5000 | 1.0000 | 0.5000 | 0.03680 (17) | |
N1 | 0.6304 (3) | 1.10175 (19) | 0.50229 (17) | 0.0326 (6) | |
N2 | 0.7747 (3) | 1.1025 (2) | 0.47220 (17) | 0.0346 (6) | |
N3 | 0.6511 (3) | 1.26794 (19) | 0.50428 (17) | 0.0329 (6) | |
N4 | 0.6124 (4) | 1.3816 (2) | 0.5119 (2) | 0.0538 (8) | |
H4A | 0.6636 | 1.3929 | 0.5570 | 0.081* | |
H4B | 0.6356 | 1.4219 | 0.4535 | 0.081* | |
N5 | 1.0152 (3) | 1.0496 (2) | 0.14934 (18) | 0.0462 (7) | |
N6 | 0.9011 (3) | 0.87987 (19) | 0.05994 (17) | 0.0329 (6) | |
N7 | 1.1734 (3) | 0.8773 (2) | 0.00075 (17) | 0.0337 (6) | |
N8 | 1.3204 (3) | 0.8614 (2) | −0.02991 (18) | 0.0375 (6) | |
N9 | 1.2641 (3) | 0.70585 (19) | 0.01780 (17) | 0.0325 (6) | |
N10 | 1.2913 (3) | 0.5940 (2) | 0.0406 (2) | 0.0508 (8) | |
H10A | 1.2260 | 0.5660 | 0.0155 | 0.076* | |
H10B | 1.2647 | 0.5843 | 0.1031 | 0.076* | |
N11 | 1.5350 (3) | 0.9266 (2) | −0.34685 (18) | 0.0466 (7) | |
N12 | 0.3526 (3) | 1.12957 (19) | 0.55952 (17) | 0.0321 (6) | |
N13 | 0.3002 (4) | 0.7362 (3) | 0.2448 (2) | 0.0565 (8) | |
N14 | 0.9798 (5) | 0.4257 (3) | 0.1421 (3) | 0.0702 (11) | |
O1 | 0.3604 (4) | 0.7788 (3) | 0.1802 (2) | 0.0945 (11) | |
O2 | 0.3105 (6) | 0.7547 (3) | 0.3184 (2) | 0.1245 (17) | |
O3 | 0.2152 (4) | 0.6788 (3) | 0.2323 (2) | 0.0884 (10) | |
O4 | 0.2031 (7) | 0.5403 (5) | 0.3866 (3) | 0.147 (2) | |
H4C | 0.2121 | 0.5673 | 0.3360 | 0.221* | |
O5 | 0.6786 (5) | 0.4430 (4) | 0.3164 (3) | 0.1130 (14) | |
H5 | 0.7589 | 0.4334 | 0.2855 | 0.170* | |
O6 | 0.8772 (5) | 0.4065 (3) | 0.1113 (3) | 0.1043 (13) | |
O7 | 1.0987 (5) | 0.4143 (3) | 0.1000 (4) | 0.1325 (19) | |
O8 | 0.9533 (5) | 0.4598 (3) | 0.2198 (3) | 0.0910 (11) | |
S1 | 1.55076 (10) | 0.68567 (7) | −0.04139 (6) | 0.0439 (2) | |
S2 | 0.93662 (10) | 1.25768 (7) | 0.45205 (6) | 0.0446 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.035 (2) | 0.0410 (19) | 0.043 (2) | −0.0107 (15) | −0.0007 (15) | −0.0064 (15) |
C2 | 0.035 (2) | 0.051 (2) | 0.054 (2) | −0.0040 (16) | 0.0027 (16) | −0.0135 (18) |
C3 | 0.047 (2) | 0.045 (2) | 0.057 (2) | 0.0004 (17) | 0.0019 (18) | −0.0188 (18) |
C4 | 0.047 (2) | 0.0329 (18) | 0.052 (2) | −0.0057 (15) | −0.0033 (17) | −0.0101 (15) |
C5 | 0.0359 (19) | 0.0310 (16) | 0.0286 (16) | −0.0076 (13) | −0.0062 (13) | −0.0015 (12) |
C6 | 0.0377 (19) | 0.0257 (15) | 0.0289 (16) | −0.0111 (13) | −0.0062 (13) | −0.0026 (12) |
C7 | 0.0382 (19) | 0.0365 (18) | 0.0292 (17) | −0.0143 (14) | −0.0042 (14) | −0.0034 (13) |
C8 | 0.038 (2) | 0.048 (2) | 0.043 (2) | −0.0145 (16) | −0.0047 (15) | −0.0060 (16) |
C9 | 0.0330 (19) | 0.0384 (18) | 0.0354 (18) | −0.0116 (14) | 0.0021 (14) | −0.0014 (14) |
C10 | 0.051 (2) | 0.0357 (19) | 0.042 (2) | −0.0026 (16) | −0.0107 (16) | 0.0030 (15) |
C11 | 0.061 (3) | 0.0319 (18) | 0.046 (2) | −0.0040 (16) | −0.0126 (18) | −0.0027 (15) |
C12 | 0.129 (4) | 0.036 (2) | 0.045 (2) | −0.003 (2) | −0.030 (2) | 0.0030 (17) |
C13 | 0.114 (4) | 0.034 (2) | 0.043 (2) | −0.010 (2) | −0.021 (2) | −0.0044 (17) |
C14 | 0.039 (2) | 0.0314 (17) | 0.046 (2) | −0.0024 (14) | −0.0044 (15) | 0.0014 (14) |
C15 | 0.039 (2) | 0.046 (2) | 0.046 (2) | −0.0151 (16) | −0.0005 (16) | 0.0049 (16) |
C16 | 0.052 (2) | 0.0340 (19) | 0.067 (3) | −0.0166 (17) | −0.0019 (19) | 0.0090 (17) |
C17 | 0.052 (2) | 0.0265 (17) | 0.062 (2) | −0.0068 (16) | −0.0037 (18) | 0.0094 (16) |
C18 | 0.0367 (19) | 0.0273 (16) | 0.0297 (16) | −0.0056 (13) | −0.0066 (13) | 0.0004 (12) |
C19 | 0.0370 (19) | 0.0229 (15) | 0.0296 (16) | −0.0025 (13) | −0.0044 (13) | 0.0010 (12) |
C20 | 0.0373 (19) | 0.0313 (17) | 0.0298 (17) | −0.0006 (14) | −0.0037 (14) | 0.0018 (13) |
C21 | 0.034 (2) | 0.055 (2) | 0.040 (2) | −0.0050 (16) | −0.0073 (15) | 0.0051 (16) |
C22 | 0.0349 (19) | 0.0421 (19) | 0.0319 (18) | −0.0053 (15) | 0.0004 (14) | 0.0005 (14) |
C23 | 0.046 (2) | 0.044 (2) | 0.041 (2) | −0.0138 (16) | −0.0065 (16) | −0.0009 (15) |
C24 | 0.053 (2) | 0.0371 (19) | 0.043 (2) | −0.0101 (16) | −0.0059 (17) | 0.0040 (15) |
C25 | 0.153 (5) | 0.051 (3) | 0.048 (3) | −0.041 (3) | −0.035 (3) | 0.005 (2) |
C26 | 0.148 (5) | 0.043 (2) | 0.046 (2) | −0.035 (3) | −0.028 (3) | 0.0111 (18) |
C27 | 0.102 (6) | 0.183 (8) | 0.150 (7) | −0.065 (6) | −0.012 (5) | −0.040 (6) |
C28 | 0.176 (8) | 0.108 (5) | 0.172 (7) | −0.083 (5) | −0.089 (6) | 0.041 (5) |
Cu1 | 0.0306 (3) | 0.0226 (3) | 0.0462 (4) | −0.0027 (2) | 0.0021 (2) | 0.0059 (2) |
Cu2 | 0.0316 (3) | 0.0261 (3) | 0.0513 (4) | −0.0092 (2) | 0.0051 (2) | −0.0105 (2) |
N1 | 0.0314 (15) | 0.0280 (14) | 0.0373 (15) | −0.0078 (11) | −0.0002 (11) | −0.0031 (11) |
N2 | 0.0341 (16) | 0.0315 (14) | 0.0385 (15) | −0.0108 (11) | −0.0004 (12) | −0.0032 (11) |
N3 | 0.0393 (16) | 0.0241 (13) | 0.0357 (15) | −0.0086 (11) | −0.0032 (12) | −0.0058 (11) |
N4 | 0.066 (2) | 0.0269 (15) | 0.069 (2) | −0.0159 (14) | −0.0008 (17) | −0.0086 (14) |
N5 | 0.065 (2) | 0.0360 (16) | 0.0365 (16) | −0.0096 (14) | −0.0066 (14) | −0.0032 (12) |
N6 | 0.0368 (16) | 0.0257 (13) | 0.0339 (15) | −0.0048 (11) | −0.0029 (12) | 0.0007 (11) |
N7 | 0.0309 (15) | 0.0287 (14) | 0.0375 (15) | −0.0029 (11) | −0.0010 (11) | 0.0027 (11) |
N8 | 0.0337 (16) | 0.0332 (15) | 0.0412 (16) | −0.0030 (12) | −0.0013 (12) | 0.0039 (12) |
N9 | 0.0373 (16) | 0.0246 (13) | 0.0331 (14) | −0.0033 (11) | −0.0048 (11) | 0.0033 (10) |
N10 | 0.057 (2) | 0.0246 (14) | 0.064 (2) | −0.0001 (13) | −0.0052 (16) | 0.0093 (13) |
N11 | 0.057 (2) | 0.0464 (18) | 0.0363 (17) | −0.0149 (15) | −0.0053 (14) | 0.0041 (13) |
N12 | 0.0343 (16) | 0.0280 (13) | 0.0346 (15) | −0.0083 (11) | −0.0033 (11) | −0.0038 (11) |
N13 | 0.063 (2) | 0.055 (2) | 0.049 (2) | −0.0091 (17) | −0.0072 (17) | −0.0020 (16) |
N14 | 0.083 (3) | 0.0302 (18) | 0.090 (3) | −0.0060 (19) | −0.005 (3) | 0.0079 (18) |
O1 | 0.084 (3) | 0.137 (3) | 0.069 (2) | −0.048 (2) | 0.0000 (19) | 0.000 (2) |
O2 | 0.227 (5) | 0.094 (3) | 0.062 (2) | −0.027 (3) | −0.062 (3) | −0.006 (2) |
O3 | 0.094 (3) | 0.108 (3) | 0.077 (2) | −0.052 (2) | −0.0106 (19) | 0.000 (2) |
O4 | 0.218 (6) | 0.162 (5) | 0.105 (3) | −0.118 (4) | −0.054 (4) | 0.031 (3) |
O5 | 0.118 (4) | 0.099 (3) | 0.096 (3) | 0.005 (3) | 0.015 (3) | −0.002 (2) |
O6 | 0.129 (4) | 0.090 (3) | 0.107 (3) | −0.035 (3) | −0.041 (3) | 0.001 (2) |
O7 | 0.092 (3) | 0.080 (3) | 0.188 (5) | 0.006 (2) | 0.043 (3) | 0.011 (3) |
O8 | 0.133 (3) | 0.063 (2) | 0.081 (3) | −0.025 (2) | −0.022 (2) | −0.0084 (19) |
S1 | 0.0375 (5) | 0.0393 (5) | 0.0447 (5) | 0.0057 (4) | −0.0013 (4) | 0.0089 (4) |
S2 | 0.0450 (5) | 0.0458 (5) | 0.0488 (5) | −0.0243 (4) | 0.0009 (4) | −0.0124 (4) |
Geometric parameters (Å, º) top
C1—H1 | 0.9300 | C21—H21B | 0.9700 |
C1—C2 | 1.380 (5) | C21—C22 | 1.503 (4) |
C1—N12 | 1.329 (4) | C21—S1 | 1.802 (4) |
C2—H2 | 0.9300 | C22—C23 | 1.368 (5) |
C2—C3 | 1.362 (5) | C22—C26 | 1.364 (5) |
C3—H3 | 0.9300 | C23—H23 | 0.9300 |
C3—C4 | 1.380 (5) | C23—C24 | 1.379 (5) |
C4—H4 | 0.9300 | C24—H24 | 0.9300 |
C4—C5 | 1.381 (4) | C24—N11 | 1.325 (4) |
C5—C6 | 1.451 (4) | C25—H25 | 0.9300 |
C5—N12 | 1.351 (4) | C25—C26 | 1.366 (6) |
C6—N1 | 1.311 (4) | C25—N11 | 1.321 (5) |
C6—N3 | 1.352 (4) | C26—H26 | 0.9300 |
C7—N2 | 1.313 (4) | C27—H27A | 0.9600 |
C7—N3 | 1.354 (4) | C27—H27B | 0.9600 |
C7—S2 | 1.731 (3) | C27—H27C | 0.9600 |
C8—H8A | 0.9700 | C27—O5 | 1.365 (7) |
C8—H8B | 0.9700 | C28—H28A | 0.9600 |
C8—C9 | 1.502 (4) | C28—H28B | 0.9600 |
C8—S2 | 1.805 (3) | C28—H28C | 0.9600 |
C9—C10 | 1.368 (4) | C28—O4 | 1.318 (7) |
C9—C13 | 1.364 (5) | Cu1—N5i | 2.446 (3) |
C10—H10 | 0.9300 | Cu1—N5 | 2.446 (3) |
C10—C11 | 1.371 (5) | Cu1—N6i | 2.052 (3) |
C11—H11 | 0.9300 | Cu1—N6 | 2.052 (3) |
C11—N5 | 1.325 (4) | Cu1—N7 | 1.997 (2) |
C12—H12 | 0.9300 | Cu1—N7i | 1.997 (2) |
C12—C13 | 1.377 (5) | Cu2—N1 | 1.994 (3) |
C12—N5 | 1.316 (5) | Cu2—N1ii | 1.994 (3) |
C13—H13 | 0.9300 | Cu2—N12ii | 2.059 (2) |
C14—H14 | 0.9300 | Cu2—N12 | 2.059 (2) |
C14—C15 | 1.376 (5) | N1—N2 | 1.382 (4) |
C14—N6 | 1.331 (4) | N3—N4 | 1.411 (3) |
C15—H15 | 0.9300 | N4—H4A | 0.9461 |
C15—C16 | 1.367 (5) | N4—H4B | 1.0110 |
C16—H16 | 0.9300 | N7—N8 | 1.378 (4) |
C16—C17 | 1.377 (5) | N9—N10 | 1.409 (3) |
C17—H17 | 0.9300 | N10—H10A | 0.9296 |
C17—C18 | 1.369 (5) | N10—H10B | 0.9529 |
C18—C19 | 1.456 (4) | N13—O1 | 1.211 (4) |
C18—N6 | 1.353 (4) | N13—O2 | 1.191 (4) |
C19—N7 | 1.309 (4) | N13—O3 | 1.254 (4) |
C19—N9 | 1.353 (4) | N14—O6 | 1.234 (5) |
C20—N8 | 1.315 (4) | N14—O7 | 1.193 (5) |
C20—N9 | 1.355 (4) | N14—O8 | 1.258 (5) |
C20—S1 | 1.733 (3) | O4—H4C | 0.8200 |
C21—H21A | 0.9700 | O5—H5 | 0.8200 |
| | | |
C2—C1—H1 | 119.0 | N11—C25—H25 | 117.3 |
N12—C1—H1 | 119.0 | N11—C25—C26 | 125.4 (4) |
N12—C1—C2 | 122.1 (3) | C22—C26—C25 | 119.5 (4) |
C1—C2—H2 | 120.1 | C22—C26—H26 | 120.3 |
C3—C2—C1 | 119.8 (3) | C25—C26—H26 | 120.3 |
C3—C2—H2 | 120.1 | H27A—C27—H27B | 109.5 |
C2—C3—H3 | 120.4 | H27A—C27—H27C | 109.5 |
C2—C3—C4 | 119.1 (3) | H27B—C27—H27C | 109.5 |
C4—C3—H3 | 120.4 | O5—C27—H27A | 109.5 |
C3—C4—H4 | 120.8 | O5—C27—H27B | 109.5 |
C3—C4—C5 | 118.4 (3) | O5—C27—H27C | 109.5 |
C5—C4—H4 | 120.8 | H28A—C28—H28B | 109.5 |
C4—C5—C6 | 126.0 (3) | H28A—C28—H28C | 109.5 |
N12—C5—C4 | 122.4 (3) | H28B—C28—H28C | 109.5 |
N12—C5—C6 | 111.4 (3) | O4—C28—H28A | 109.5 |
N1—C6—C5 | 119.9 (3) | O4—C28—H28B | 109.5 |
N1—C6—N3 | 108.6 (3) | O4—C28—H28C | 109.5 |
N3—C6—C5 | 131.5 (3) | N5i—Cu1—N5 | 180.0 |
N2—C7—N3 | 111.3 (3) | N6i—Cu1—N5i | 87.12 (10) |
N2—C7—S2 | 127.8 (3) | N6—Cu1—N5i | 92.88 (10) |
N3—C7—S2 | 120.9 (2) | N6—Cu1—N5 | 87.12 (10) |
H8A—C8—H8B | 107.5 | N6i—Cu1—N5 | 92.88 (10) |
C9—C8—H8A | 108.4 | N6—Cu1—N6i | 180.00 (8) |
C9—C8—H8B | 108.4 | N7i—Cu1—N5 | 88.22 (10) |
C9—C8—S2 | 115.4 (2) | N7i—Cu1—N5i | 91.78 (10) |
S2—C8—H8A | 108.4 | N7—Cu1—N5i | 88.22 (10) |
S2—C8—H8B | 108.4 | N7—Cu1—N5 | 91.78 (10) |
C10—C9—C8 | 120.9 (3) | N7i—Cu1—N6 | 99.99 (10) |
C13—C9—C8 | 121.7 (3) | N7—Cu1—N6 | 80.01 (10) |
C13—C9—C10 | 117.2 (3) | N7—Cu1—N6i | 99.99 (10) |
C9—C10—H10 | 120.3 | N7i—Cu1—N6i | 80.01 (10) |
C9—C10—C11 | 119.4 (3) | N7—Cu1—N7i | 179.999 (1) |
C11—C10—H10 | 120.3 | N1ii—Cu2—N1 | 179.999 (2) |
C10—C11—H11 | 117.9 | N1—Cu2—N12ii | 100.02 (10) |
N5—C11—C10 | 124.2 (3) | N1ii—Cu2—N12ii | 79.98 (10) |
N5—C11—H11 | 117.9 | N1ii—Cu2—N12 | 100.02 (10) |
C13—C12—H12 | 117.8 | N1—Cu2—N12 | 79.98 (10) |
N5—C12—H12 | 117.8 | N12—Cu2—N12ii | 180.00 (10) |
N5—C12—C13 | 124.4 (3) | C6—N1—Cu2 | 112.7 (2) |
C9—C13—C12 | 119.2 (3) | C6—N1—N2 | 109.5 (2) |
C9—C13—H13 | 120.4 | N2—N1—Cu2 | 136.43 (19) |
C12—C13—H13 | 120.4 | C7—N2—N1 | 104.9 (2) |
C15—C14—H14 | 118.7 | C6—N3—C7 | 105.6 (2) |
N6—C14—H14 | 118.7 | C6—N3—N4 | 125.4 (3) |
N6—C14—C15 | 122.7 (3) | C7—N3—N4 | 128.9 (3) |
C14—C15—H15 | 120.7 | N3—N4—H4A | 102.8 |
C16—C15—C14 | 118.6 (3) | N3—N4—H4B | 112.6 |
C16—C15—H15 | 120.7 | H4A—N4—H4B | 114.7 |
C15—C16—H16 | 120.2 | C11—N5—Cu1 | 122.7 (2) |
C15—C16—C17 | 119.6 (3) | C12—N5—C11 | 115.5 (3) |
C17—C16—H16 | 120.2 | C12—N5—Cu1 | 121.7 (2) |
C16—C17—H17 | 120.6 | C14—N6—C18 | 118.2 (3) |
C18—C17—C16 | 118.8 (3) | C14—N6—Cu1 | 127.0 (2) |
C18—C17—H17 | 120.6 | C18—N6—Cu1 | 114.8 (2) |
C17—C18—C19 | 126.5 (3) | C19—N7—Cu1 | 113.7 (2) |
N6—C18—C17 | 122.0 (3) | C19—N7—N8 | 109.7 (2) |
N6—C18—C19 | 111.5 (3) | N8—N7—Cu1 | 136.2 (2) |
N7—C19—C18 | 119.7 (3) | C20—N8—N7 | 105.0 (3) |
N7—C19—N9 | 108.4 (3) | C19—N9—C20 | 105.9 (2) |
N9—C19—C18 | 131.9 (3) | C19—N9—N10 | 131.7 (3) |
N8—C20—N9 | 111.0 (3) | C20—N9—N10 | 122.3 (3) |
N8—C20—S1 | 127.6 (3) | N9—N10—H10A | 106.3 |
N9—C20—S1 | 121.4 (2) | N9—N10—H10B | 109.1 |
H21A—C21—H21B | 107.4 | H10A—N10—H10B | 105.0 |
C22—C21—H21A | 108.2 | C25—N11—C24 | 114.8 (3) |
C22—C21—H21B | 108.2 | C1—N12—C5 | 118.1 (3) |
C22—C21—S1 | 116.3 (3) | C1—N12—Cu2 | 127.5 (2) |
S1—C21—H21A | 108.2 | C5—N12—Cu2 | 114.2 (2) |
S1—C21—H21B | 108.2 | O1—N13—O3 | 117.8 (4) |
C23—C22—C21 | 121.0 (3) | O2—N13—O1 | 121.9 (4) |
C26—C22—C21 | 122.6 (3) | O2—N13—O3 | 120.0 (4) |
C26—C22—C23 | 116.3 (3) | O6—N14—O8 | 117.2 (5) |
C22—C23—H23 | 119.8 | O7—N14—O6 | 121.8 (5) |
C22—C23—C24 | 120.3 (3) | O7—N14—O8 | 121.0 (5) |
C24—C23—H23 | 119.8 | C28—O4—H4C | 109.5 |
C23—C24—H24 | 118.2 | C27—O5—H5 | 109.5 |
N11—C24—C23 | 123.7 (3) | C20—S1—C21 | 98.06 (16) |
N11—C24—H24 | 118.2 | C7—S2—C8 | 98.96 (16) |
C26—C25—H25 | 117.3 | | |
| | | |
C1—C2—C3—C4 | 0.0 (6) | N3—C6—N1—N2 | 1.7 (3) |
C2—C1—N12—C5 | 0.8 (5) | N3—C7—N2—N1 | −2.0 (3) |
C2—C1—N12—Cu2 | 177.6 (3) | N3—C7—S2—C8 | −172.7 (2) |
C2—C3—C4—C5 | 0.3 (6) | N5—C12—C13—C9 | 0.3 (8) |
C3—C4—C5—C6 | −174.8 (3) | N5i—Cu1—N5—C11 | 64 (34) |
C3—C4—C5—N12 | −0.1 (5) | N5i—Cu1—N5—C12 | −118 (34) |
C4—C5—C6—N1 | 166.8 (3) | N5—Cu1—N6—C14 | 83.5 (3) |
C4—C5—C6—N3 | −10.6 (5) | N5i—Cu1—N6—C14 | −96.5 (3) |
C4—C5—N12—C1 | −0.5 (5) | N5i—Cu1—N6—C18 | 83.2 (2) |
C4—C5—N12—Cu2 | −177.7 (2) | N5—Cu1—N6—C18 | −96.8 (2) |
C5—C6—N1—Cu2 | 15.0 (3) | N5—Cu1—N7—C19 | 92.0 (2) |
C5—C6—N1—N2 | −176.2 (3) | N5i—Cu1—N7—C19 | −88.0 (2) |
C5—C6—N3—C7 | 174.8 (3) | N5i—Cu1—N7—N8 | 83.9 (3) |
C5—C6—N3—N4 | −6.7 (5) | N5—Cu1—N7—N8 | −96.1 (3) |
C6—C5—N12—C1 | 174.9 (3) | N6—C14—C15—C16 | −1.2 (5) |
C6—C5—N12—Cu2 | −2.2 (3) | N6—C18—C19—N7 | 1.6 (4) |
C6—N1—N2—C7 | 0.2 (3) | N6—C18—C19—N9 | −176.5 (3) |
C8—C9—C10—C11 | −176.3 (3) | N6i—Cu1—N5—C11 | −134.8 (3) |
C8—C9—C13—C12 | 176.1 (4) | N6—Cu1—N5—C11 | 45.2 (3) |
C9—C8—S2—C7 | 69.4 (3) | N6—Cu1—N5—C12 | −136.8 (4) |
C9—C10—C11—N5 | 0.2 (6) | N6i—Cu1—N5—C12 | 43.2 (4) |
C10—C9—C13—C12 | −0.6 (6) | N6i—Cu1—N6—C14 | 112 (52) |
C10—C11—N5—C12 | −0.6 (6) | N6i—Cu1—N6—C18 | −68 (52) |
C10—C11—N5—Cu1 | 177.6 (3) | N6—Cu1—N7—C19 | 5.2 (2) |
C13—C9—C10—C11 | 0.4 (5) | N6i—Cu1—N7—C19 | −174.8 (2) |
C13—C12—N5—C11 | 0.4 (7) | N6—Cu1—N7—N8 | 177.1 (3) |
C13—C12—N5—Cu1 | −177.8 (4) | N6i—Cu1—N7—N8 | −2.9 (3) |
C14—C15—C16—C17 | 3.0 (6) | N7—C19—N9—C20 | 1.6 (3) |
C15—C14—N6—C18 | −0.9 (5) | N7—C19—N9—N10 | 176.9 (3) |
C15—C14—N6—Cu1 | 178.8 (3) | N7—Cu1—N5—C11 | −34.7 (3) |
C15—C16—C17—C18 | −2.7 (6) | N7i—Cu1—N5—C11 | 145.3 (3) |
C16—C17—C18—C19 | 178.9 (3) | N7i—Cu1—N5—C12 | −36.7 (4) |
C16—C17—C18—N6 | 0.6 (5) | N7—Cu1—N5—C12 | 143.3 (4) |
C17—C18—C19—N7 | −176.9 (3) | N7i—Cu1—N6—C14 | −4.1 (3) |
C17—C18—C19—N9 | 5.1 (6) | N7—Cu1—N6—C14 | 175.9 (3) |
C17—C18—N6—C14 | 1.2 (5) | N7i—Cu1—N6—C18 | 175.5 (2) |
C17—C18—N6—Cu1 | −178.5 (3) | N7—Cu1—N6—C18 | −4.5 (2) |
C18—C19—N7—Cu1 | −5.4 (4) | N7i—Cu1—N7—C19 | −21.0 (3) |
C18—C19—N7—N8 | −179.5 (3) | N7i—Cu1—N7—N8 | 150.9 (4) |
C18—C19—N9—C20 | 179.8 (3) | N8—C20—N9—C19 | −1.6 (3) |
C18—C19—N9—N10 | −4.9 (6) | N8—C20—N9—N10 | −177.5 (3) |
C19—C18—N6—C14 | −177.4 (3) | N8—C20—S1—C21 | −2.2 (3) |
C19—C18—N6—Cu1 | 2.9 (3) | N9—C19—N7—Cu1 | 173.07 (19) |
C19—N7—N8—C20 | 0.0 (3) | N9—C19—N7—N8 | −1.0 (3) |
C21—C22—C23—C24 | 176.8 (3) | N9—C20—N8—N7 | 1.0 (3) |
C21—C22—C26—C25 | −177.3 (4) | N9—C20—S1—C21 | 177.7 (3) |
C22—C21—S1—C20 | −70.0 (3) | N11—C25—C26—C22 | 0.6 (9) |
C22—C23—C24—N11 | 0.8 (6) | N12—C1—C2—C3 | −0.6 (6) |
C23—C22—C26—C25 | −0.8 (7) | N12—C5—C6—N1 | −8.5 (4) |
C23—C24—N11—C25 | −0.9 (6) | N12—C5—C6—N3 | 174.2 (3) |
C26—C22—C23—C24 | 0.1 (6) | N12ii—Cu2—N1—C6 | 168.2 (2) |
C26—C25—N11—C24 | 0.3 (8) | N12—Cu2—N1—C6 | −11.8 (2) |
Cu1—N7—N8—C20 | −172.2 (2) | N12ii—Cu2—N1—N2 | 3.6 (3) |
Cu2—N1—N2—C7 | 165.1 (2) | N12—Cu2—N1—N2 | −176.4 (3) |
N1—C6—N3—C7 | −2.8 (3) | N12ii—Cu2—N12—C1 | −63 (54) |
N1—C6—N3—N4 | 175.7 (3) | N12ii—Cu2—N12—C5 | 114 (54) |
N1ii—Cu2—N1—C6 | 63 (17) | S1—C20—N8—N7 | −179.0 (2) |
N1ii—Cu2—N1—N2 | −101 (17) | S1—C20—N9—C19 | 178.4 (2) |
N1—Cu2—N12—C1 | −169.2 (3) | S1—C20—N9—N10 | 2.6 (4) |
N1ii—Cu2—N12—C1 | 10.8 (3) | S1—C21—C22—C23 | 151.1 (3) |
N1ii—Cu2—N12—C5 | −172.4 (2) | S1—C21—C22—C26 | −32.5 (5) |
N1—Cu2—N12—C5 | 7.6 (2) | S2—C7—N2—N1 | 176.9 (2) |
N2—C7—N3—C6 | 3.0 (3) | S2—C7—N3—C6 | −176.0 (2) |
N2—C7—N3—N4 | −175.4 (3) | S2—C7—N3—N4 | 5.6 (4) |
N2—C7—S2—C8 | 8.5 (3) | S2—C8—C9—C10 | −146.7 (3) |
N3—C6—N1—Cu2 | −167.13 (19) | S2—C8—C9—C13 | 36.7 (5) |
Symmetry codes: (i) −x+2, −y+2, −z; (ii) −x+1, −y+2, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4A···O2ii | 0.95 | 2.57 | 3.103 (5) | 116 |
N4—H4A···O4ii | 0.95 | 2.02 | 2.907 (6) | 156 |
N4—H4B···O5iii | 1.01 | 2.07 | 3.026 (5) | 156 |
N10—H10A···O6iv | 0.93 | 2.29 | 3.039 (5) | 138 |
N10—H10A···O7 | 0.93 | 2.65 | 3.233 (6) | 122 |
N10—H10B···O3v | 0.95 | 2.31 | 3.107 (5) | 141 |
O4—H4C···O3 | 0.82 | 2.04 | 2.834 (6) | 162 |
O5—H5···O8 | 0.82 | 2.05 | 2.835 (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{µ
2-4-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·H2O | F(000) = 1732 |
Mr = 849.15 | Dx = 1.673 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54184 Å |
a = 9.6589 (3) Å | Cell parameters from 4224 reflections |
b = 23.1463 (5) Å | θ = 4.8–71.0° |
c = 15.5643 (4) Å | µ = 4.16 mm−1 |
β = 104.305 (3)° | T = 150 K |
V = 3371.79 (15) Å3 | Needle, clear light green |
Z = 4 | 0.34 × 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 Source | 4595 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.029 |
Detector resolution: 16.0793 pixels mm-1 | θmax = 67.1°, θmin = 3.8° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | k = −24→27 |
Tmin = 0.506, Tmax = 1.000 | l = −17→18 |
12396 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: iterative |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.182 | H 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 parameters | Δρmax = 1.32 e Å−3 |
0 restraints | Δρmin = −0.94 e Å−3 |
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 1–3 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
3.82≤θ≤67,07°, 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 | x | y | z | Uiso*/Ueq | |
C1 | 0.2006 (4) | 0.18264 (18) | 0.6594 (3) | 0.0270 (9) | |
H1 | 0.1509 | 0.2166 | 0.6627 | 0.032* | |
C2 | 0.1264 (5) | 0.13495 (18) | 0.6174 (3) | 0.0301 (9) | |
H2 | 0.0282 | 0.1369 | 0.5938 | 0.036* | |
C3 | 0.1990 (5) | 0.08511 (18) | 0.6111 (3) | 0.0311 (10) | |
H3 | 0.1506 | 0.0530 | 0.5826 | 0.037* | |
C4 | 0.3463 (5) | 0.08262 (17) | 0.6475 (3) | 0.0283 (9) | |
H4 | 0.3979 | 0.0492 | 0.6438 | 0.034* | |
C5 | 0.4129 (4) | 0.13156 (16) | 0.6891 (2) | 0.0210 (8) | |
C6 | 0.5656 (4) | 0.13822 (16) | 0.7274 (2) | 0.0214 (8) | |
C7 | 0.7956 (4) | 0.13123 (17) | 0.7741 (3) | 0.0240 (8) | |
C8 | 1.0630 (4) | 0.15969 (19) | 0.8592 (3) | 0.0283 (9) | |
H8A | 1.1635 | 0.1494 | 0.8745 | 0.034* | |
H8B | 1.0511 | 0.1918 | 0.8180 | 0.034* | |
C9 | 1.0239 (4) | 0.18009 (18) | 0.9424 (3) | 0.0248 (8) | |
C10 | 1.0510 (4) | 0.23635 (18) | 0.9699 (3) | 0.0262 (9) | |
H10 | 1.0863 | 0.2624 | 0.9351 | 0.031* | |
C11 | 1.0257 (5) | 0.25409 (18) | 1.0495 (3) | 0.0292 (9) | |
H11 | 1.0450 | 0.2923 | 1.0666 | 0.035* | |
C12 | 0.9434 (5) | 0.16537 (19) | 1.0733 (3) | 0.0328 (10) | |
H12 | 0.9020 | 0.1408 | 1.1072 | 0.039* | |
C13 | 0.9680 (5) | 0.14391 (18) | 0.9961 (3) | 0.0313 (10) | |
H13 | 0.9474 | 0.1056 | 0.9801 | 0.038* | |
C14 | 0.7382 (4) | 0.31454 (19) | 0.8481 (3) | 0.0280 (9) | |
H14 | 0.7870 | 0.2803 | 0.8451 | 0.034* | |
C15 | 0.8131 (5) | 0.36148 (18) | 0.8885 (3) | 0.0303 (9) | |
H15 | 0.9112 | 0.3590 | 0.9123 | 0.036* | |
C16 | 0.7412 (5) | 0.41257 (18) | 0.8935 (3) | 0.0315 (10) | |
H16 | 0.7906 | 0.4448 | 0.9210 | 0.038* | |
C17 | 0.5952 (5) | 0.41543 (18) | 0.8574 (3) | 0.0283 (9) | |
H17 | 0.5449 | 0.4494 | 0.8596 | 0.034* | |
C18 | 0.5262 (4) | 0.36606 (16) | 0.8176 (2) | 0.0205 (8) | |
C19 | 0.3734 (4) | 0.35932 (16) | 0.7810 (2) | 0.0211 (8) | |
C20 | 0.1423 (4) | 0.36608 (17) | 0.7342 (3) | 0.0234 (8) | |
C21 | −0.1266 (4) | 0.33849 (19) | 0.6498 (3) | 0.0284 (9) | |
H21A | −0.1138 | 0.3052 | 0.6889 | 0.034* | |
H21B | −0.2272 | 0.3487 | 0.6357 | 0.034* | |
C22 | −0.0881 (4) | 0.32119 (18) | 0.5653 (3) | 0.0248 (8) | |
C23 | −0.0446 (5) | 0.36051 (18) | 0.5100 (3) | 0.0296 (9) | |
H23 | −0.0324 | 0.3993 | 0.5258 | 0.036* | |
C24 | −0.0197 (5) | 0.34127 (19) | 0.4314 (3) | 0.0333 (10) | |
H24 | 0.0102 | 0.3682 | 0.3954 | 0.040* | |
C25 | −0.0749 (5) | 0.24880 (18) | 0.4581 (3) | 0.0282 (9) | |
H25 | −0.0850 | 0.2101 | 0.4415 | 0.034* | |
C26 | −0.1012 (4) | 0.26433 (18) | 0.5387 (3) | 0.0261 (9) | |
H26 | −0.1275 | 0.2364 | 0.5746 | 0.031* | |
Cl1 | 0.71671 (12) | 0.08210 (4) | 0.50514 (6) | 0.0313 (3) | |
Cl2 | 0.25606 (14) | 0.49586 (6) | 0.56479 (10) | 0.0543 (4) | |
Cu1 | 0.46947 (6) | 0.24888 (2) | 0.75251 (4) | 0.0241 (2) | |
N1 | 0.3422 (3) | 0.18109 (14) | 0.6953 (2) | 0.0223 (7) | |
N2 | 0.6173 (3) | 0.18974 (14) | 0.7517 (2) | 0.0220 (7) | |
N3 | 0.7643 (4) | 0.18600 (14) | 0.7816 (2) | 0.0251 (7) | |
N4 | 0.6745 (4) | 0.09964 (14) | 0.7415 (2) | 0.0223 (7) | |
N5 | 0.6600 (4) | 0.04031 (15) | 0.7219 (3) | 0.0346 (9) | |
N6 | 0.5963 (3) | 0.31634 (14) | 0.8124 (2) | 0.0223 (7) | |
N7 | 0.3208 (3) | 0.30798 (14) | 0.7537 (2) | 0.0216 (7) | |
N8 | 0.1740 (3) | 0.31159 (14) | 0.7244 (2) | 0.0246 (7) | |
N9 | 0.2635 (4) | 0.39750 (14) | 0.7691 (2) | 0.0230 (7) | |
N10 | 0.2750 (4) | 0.45586 (15) | 0.7928 (2) | 0.0319 (8) | |
N11 | −0.0360 (4) | 0.28598 (15) | 0.4032 (2) | 0.0272 (8) | |
N12 | 0.9751 (4) | 0.21940 (15) | 1.1029 (2) | 0.0262 (7) | |
O1 | 0.3161 (5) | 0.54430 (18) | 0.5296 (3) | 0.0634 (12) | |
H9A | 0.3151 | 0.5253 | 0.3967 | 0.095* | |
H9B | 0.4151 | 0.5355 | 0.3614 | 0.095* | |
H10A | 0.2408 | 0.4758 | 0.7433 | 0.095* | |
H5A | 0.7206 | 0.0241 | 0.7737 | 0.095* | |
H5B | 0.7165 | 0.0355 | 0.6882 | 0.095* | |
H10B | 0.2238 | 0.4623 | 0.8373 | 0.095* | |
O2 | 0.1681 (7) | 0.5196 (3) | 0.6197 (4) | 0.139 (3) | |
O3 | 0.1844 (8) | 0.4624 (3) | 0.4904 (5) | 0.146 (3) | |
O4 | 0.3661 (5) | 0.46299 (18) | 0.6224 (3) | 0.0666 (12) | |
O5 | 0.6300 (4) | 0.04374 (18) | 0.4415 (3) | 0.0561 (10) | |
O6 | 0.6231 (6) | 0.11149 (19) | 0.5492 (3) | 0.0765 (16) | |
O7 | 0.7859 (6) | 0.12172 (19) | 0.4611 (3) | 0.0813 (17) | |
O8 | 0.8177 (4) | 0.04955 (18) | 0.5695 (3) | 0.0594 (11) | |
O9 | 0.3254 (4) | 0.54163 (16) | 0.3493 (2) | 0.0463 (9) | |
S1 | −0.02472 (11) | 0.39841 (5) | 0.70932 (7) | 0.0297 (3) | |
S2 | 0.96262 (11) | 0.09890 (5) | 0.80271 (7) | 0.0300 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.024 (2) | 0.024 (2) | 0.030 (2) | −0.0003 (16) | 0.0018 (17) | −0.0044 (16) |
C2 | 0.027 (2) | 0.027 (2) | 0.033 (2) | −0.0066 (17) | 0.0004 (18) | 0.0013 (17) |
C3 | 0.034 (2) | 0.023 (2) | 0.032 (2) | −0.0095 (18) | −0.0009 (19) | −0.0007 (17) |
C4 | 0.033 (2) | 0.018 (2) | 0.032 (2) | −0.0010 (17) | 0.0045 (19) | 0.0014 (16) |
C5 | 0.0244 (19) | 0.0208 (19) | 0.0169 (18) | −0.0010 (15) | 0.0037 (15) | 0.0031 (14) |
C6 | 0.027 (2) | 0.0170 (18) | 0.0206 (18) | 0.0029 (16) | 0.0060 (16) | 0.0017 (14) |
C7 | 0.026 (2) | 0.025 (2) | 0.0200 (19) | 0.0053 (16) | 0.0035 (16) | −0.0023 (15) |
C8 | 0.0211 (19) | 0.036 (2) | 0.025 (2) | 0.0031 (17) | 0.0016 (17) | −0.0005 (17) |
C9 | 0.0203 (19) | 0.028 (2) | 0.024 (2) | 0.0064 (16) | 0.0007 (16) | 0.0017 (16) |
C10 | 0.026 (2) | 0.027 (2) | 0.023 (2) | −0.0039 (17) | 0.0019 (17) | 0.0026 (16) |
C11 | 0.035 (2) | 0.023 (2) | 0.026 (2) | −0.0074 (17) | 0.0010 (18) | −0.0004 (16) |
C12 | 0.045 (3) | 0.024 (2) | 0.032 (2) | −0.0064 (19) | 0.014 (2) | 0.0004 (17) |
C13 | 0.043 (3) | 0.020 (2) | 0.031 (2) | −0.0011 (18) | 0.009 (2) | −0.0019 (17) |
C14 | 0.022 (2) | 0.027 (2) | 0.032 (2) | 0.0015 (17) | 0.0019 (17) | −0.0011 (17) |
C15 | 0.025 (2) | 0.029 (2) | 0.032 (2) | −0.0057 (17) | −0.0021 (18) | −0.0020 (18) |
C16 | 0.039 (2) | 0.022 (2) | 0.031 (2) | −0.0083 (18) | 0.006 (2) | −0.0040 (17) |
C17 | 0.035 (2) | 0.019 (2) | 0.028 (2) | −0.0014 (17) | 0.0039 (18) | −0.0009 (16) |
C18 | 0.0245 (19) | 0.0198 (19) | 0.0168 (18) | −0.0006 (15) | 0.0045 (15) | 0.0007 (14) |
C19 | 0.025 (2) | 0.0179 (19) | 0.0196 (18) | 0.0013 (15) | 0.0043 (16) | −0.0002 (14) |
C20 | 0.027 (2) | 0.024 (2) | 0.0188 (18) | 0.0048 (16) | 0.0050 (16) | −0.0020 (15) |
C21 | 0.0217 (19) | 0.032 (2) | 0.031 (2) | 0.0034 (17) | 0.0057 (17) | −0.0039 (18) |
C22 | 0.0194 (19) | 0.028 (2) | 0.025 (2) | 0.0017 (16) | 0.0010 (16) | 0.0017 (16) |
C23 | 0.035 (2) | 0.023 (2) | 0.029 (2) | −0.0036 (18) | 0.0042 (18) | −0.0034 (16) |
C24 | 0.045 (3) | 0.029 (2) | 0.027 (2) | −0.008 (2) | 0.011 (2) | 0.0006 (18) |
C25 | 0.037 (2) | 0.022 (2) | 0.025 (2) | −0.0038 (17) | 0.0053 (18) | −0.0011 (16) |
C26 | 0.025 (2) | 0.028 (2) | 0.024 (2) | −0.0025 (17) | 0.0033 (17) | 0.0040 (16) |
Cl1 | 0.0446 (6) | 0.0187 (5) | 0.0267 (5) | −0.0006 (4) | 0.0012 (5) | −0.0005 (4) |
Cl2 | 0.0432 (7) | 0.0530 (8) | 0.0695 (9) | −0.0036 (6) | 0.0190 (6) | 0.0142 (7) |
Cu1 | 0.0189 (3) | 0.0170 (3) | 0.0328 (4) | 0.0010 (2) | −0.0006 (3) | −0.0079 (2) |
N1 | 0.0254 (17) | 0.0175 (16) | 0.0235 (16) | 0.0001 (13) | 0.0049 (14) | 0.0001 (13) |
N2 | 0.0199 (16) | 0.0218 (17) | 0.0222 (16) | 0.0014 (13) | 0.0010 (13) | −0.0043 (13) |
N3 | 0.0216 (17) | 0.0251 (18) | 0.0272 (17) | 0.0026 (14) | 0.0034 (14) | −0.0044 (14) |
N4 | 0.0275 (17) | 0.0173 (16) | 0.0207 (16) | 0.0046 (13) | 0.0033 (14) | −0.0008 (12) |
N5 | 0.042 (2) | 0.0193 (18) | 0.039 (2) | 0.0056 (16) | 0.0027 (17) | −0.0014 (15) |
N6 | 0.0237 (17) | 0.0205 (16) | 0.0222 (16) | −0.0005 (13) | 0.0048 (14) | −0.0029 (13) |
N7 | 0.0193 (16) | 0.0218 (17) | 0.0219 (16) | −0.0001 (13) | 0.0017 (13) | −0.0032 (13) |
N8 | 0.0211 (16) | 0.0236 (17) | 0.0267 (17) | 0.0034 (14) | 0.0013 (14) | −0.0028 (13) |
N9 | 0.0298 (18) | 0.0168 (16) | 0.0221 (16) | 0.0052 (13) | 0.0059 (14) | −0.0018 (12) |
N10 | 0.041 (2) | 0.0185 (17) | 0.034 (2) | 0.0040 (15) | 0.0056 (17) | −0.0038 (14) |
N11 | 0.0305 (18) | 0.0261 (18) | 0.0242 (17) | −0.0041 (15) | 0.0054 (15) | −0.0021 (14) |
N12 | 0.0294 (18) | 0.0239 (18) | 0.0226 (17) | −0.0011 (14) | 0.0014 (14) | −0.0007 (13) |
O1 | 0.082 (3) | 0.051 (2) | 0.060 (2) | −0.026 (2) | 0.023 (2) | −0.002 (2) |
O2 | 0.139 (5) | 0.185 (7) | 0.125 (5) | 0.118 (5) | 0.092 (5) | 0.103 (5) |
O3 | 0.115 (5) | 0.138 (6) | 0.155 (6) | −0.092 (5) | −0.026 (5) | −0.014 (5) |
O4 | 0.068 (3) | 0.052 (2) | 0.088 (3) | 0.018 (2) | 0.033 (2) | 0.012 (2) |
O5 | 0.053 (2) | 0.064 (3) | 0.053 (2) | −0.026 (2) | 0.0165 (19) | −0.0267 (19) |
O6 | 0.123 (4) | 0.065 (3) | 0.041 (2) | 0.057 (3) | 0.019 (2) | −0.0014 (19) |
O7 | 0.140 (5) | 0.053 (3) | 0.045 (2) | −0.055 (3) | 0.013 (3) | 0.006 (2) |
O8 | 0.046 (2) | 0.060 (2) | 0.070 (3) | 0.0121 (19) | 0.009 (2) | 0.028 (2) |
O9 | 0.046 (2) | 0.050 (2) | 0.0391 (19) | 0.0028 (17) | 0.0023 (16) | −0.0076 (16) |
S1 | 0.0267 (5) | 0.0306 (6) | 0.0299 (5) | 0.0103 (4) | 0.0036 (4) | −0.0072 (4) |
S2 | 0.0261 (5) | 0.0304 (6) | 0.0306 (5) | 0.0104 (4) | 0.0015 (4) | −0.0070 (4) |
Geometric parameters (Å, º) top
C1—H1 | 0.9300 | C20—N8 | 1.316 (5) |
C1—C2 | 1.388 (6) | C20—N9 | 1.371 (5) |
C1—N1 | 1.344 (5) | C20—S1 | 1.733 (4) |
C2—H2 | 0.9300 | C21—H21A | 0.9700 |
C2—C3 | 1.366 (6) | C21—H21B | 0.9700 |
C3—H3 | 0.9300 | C21—C22 | 1.507 (6) |
C3—C4 | 1.397 (6) | C21—S1 | 1.817 (4) |
C4—H4 | 0.9300 | C22—C23 | 1.386 (6) |
C4—C5 | 1.382 (6) | C22—C26 | 1.376 (6) |
C5—C6 | 1.456 (5) | C23—H23 | 0.9300 |
C5—N1 | 1.350 (5) | C23—C24 | 1.379 (6) |
C6—N2 | 1.312 (5) | C24—H24 | 0.9300 |
C6—N4 | 1.355 (5) | C24—N11 | 1.349 (6) |
C7—N3 | 1.315 (5) | C25—H25 | 0.9300 |
C7—N4 | 1.367 (5) | C25—C26 | 1.387 (6) |
C7—S2 | 1.734 (4) | C25—N11 | 1.331 (5) |
C8—H8A | 0.9700 | C26—H26 | 0.9300 |
C8—H8B | 0.9700 | Cl1—O5 | 1.436 (4) |
C8—C9 | 1.511 (6) | Cl1—O6 | 1.434 (4) |
C8—S2 | 1.809 (4) | Cl1—O7 | 1.409 (4) |
C9—C10 | 1.376 (6) | Cl1—O8 | 1.428 (4) |
C9—C13 | 1.383 (6) | Cl2—O1 | 1.432 (4) |
C10—H10 | 0.9300 | Cl2—O2 | 1.454 (6) |
C10—C11 | 1.382 (6) | Cl2—O3 | 1.422 (6) |
C11—H11 | 0.9300 | Cl2—O4 | 1.429 (4) |
C11—N12 | 1.333 (6) | Cu1—N1 | 2.056 (3) |
C12—H12 | 0.9300 | Cu1—N2 | 1.980 (3) |
C12—C13 | 1.374 (6) | Cu1—N6 | 2.060 (3) |
C12—N12 | 1.342 (6) | Cu1—N7 | 1.986 (3) |
C13—H13 | 0.9300 | Cu1—N12i | 2.454 (3) |
C14—H14 | 0.9300 | N2—N3 | 1.382 (5) |
C14—C15 | 1.369 (6) | N4—N5 | 1.406 (5) |
C14—N6 | 1.346 (5) | N5—H5A | 0.9482 |
C15—H15 | 0.9300 | N5—H5B | 0.8517 |
C15—C16 | 1.383 (6) | N7—N8 | 1.381 (4) |
C16—H16 | 0.9300 | N9—N10 | 1.398 (5) |
C16—C17 | 1.385 (6) | N10—H10A | 0.8889 |
C17—H17 | 0.9300 | N10—H10B | 0.9574 |
C17—C18 | 1.389 (6) | N12—Cu1ii | 2.454 (3) |
C18—C19 | 1.453 (5) | O9—H9A | 0.8562 |
C18—N6 | 1.348 (5) | O9—H9A | 0.8562 |
C19—N7 | 1.321 (5) | O9—H9B | 0.8516 |
C19—N9 | 1.358 (5) | | |
| | | |
C2—C1—H1 | 119.1 | C26—C22—C23 | 117.4 (4) |
N1—C1—H1 | 119.1 | C22—C23—H23 | 120.5 |
N1—C1—C2 | 121.9 (4) | C24—C23—C22 | 119.0 (4) |
C1—C2—H2 | 120.3 | C24—C23—H23 | 120.5 |
C3—C2—C1 | 119.4 (4) | C23—C24—H24 | 117.9 |
C3—C2—H2 | 120.3 | N11—C24—C23 | 124.3 (4) |
C2—C3—H3 | 120.2 | N11—C24—H24 | 117.9 |
C2—C3—C4 | 119.7 (4) | C26—C25—H25 | 118.1 |
C4—C3—H3 | 120.2 | N11—C25—H25 | 118.1 |
C3—C4—H4 | 121.1 | N11—C25—C26 | 123.8 (4) |
C5—C4—C3 | 117.8 (4) | C22—C26—C25 | 119.7 (4) |
C5—C4—H4 | 121.1 | C22—C26—H26 | 120.1 |
C4—C5—C6 | 125.8 (4) | C25—C26—H26 | 120.1 |
N1—C5—C4 | 123.0 (4) | O6—Cl1—O5 | 107.1 (3) |
N1—C5—C6 | 111.1 (3) | O7—Cl1—O5 | 109.4 (2) |
N2—C6—C5 | 119.3 (3) | O7—Cl1—O6 | 110.8 (3) |
N2—C6—N4 | 109.1 (3) | O7—Cl1—O8 | 111.2 (3) |
N4—C6—C5 | 131.5 (4) | O8—Cl1—O5 | 109.8 (3) |
N3—C7—N4 | 110.7 (3) | O8—Cl1—O6 | 108.5 (3) |
N3—C7—S2 | 127.8 (3) | O1—Cl2—O2 | 106.2 (4) |
N4—C7—S2 | 121.4 (3) | O3—Cl2—O1 | 106.1 (4) |
H8A—C8—H8B | 107.4 | O3—Cl2—O2 | 116.5 (5) |
C9—C8—H8A | 108.2 | O3—Cl2—O4 | 111.0 (4) |
C9—C8—H8B | 108.2 | O4—Cl2—O1 | 110.3 (3) |
C9—C8—S2 | 116.2 (3) | O4—Cl2—O2 | 106.5 (3) |
S2—C8—H8A | 108.2 | N1—Cu1—N6 | 178.80 (13) |
S2—C8—H8B | 108.2 | N1—Cu1—N12i | 88.18 (12) |
C10—C9—C8 | 119.6 (4) | N2—Cu1—N1 | 79.90 (13) |
C10—C9—C13 | 117.3 (4) | N2—Cu1—N6 | 100.23 (13) |
C13—C9—C8 | 123.1 (4) | N2—Cu1—N7 | 179.74 (15) |
C9—C10—H10 | 120.1 | N2—Cu1—N12i | 90.91 (13) |
C9—C10—C11 | 119.9 (4) | N6—Cu1—N12i | 93.01 (12) |
C11—C10—H10 | 120.1 | N7—Cu1—N1 | 99.99 (13) |
C10—C11—H11 | 118.2 | N7—Cu1—N6 | 79.87 (13) |
N12—C11—C10 | 123.6 (4) | N7—Cu1—N12i | 89.32 (13) |
N12—C11—H11 | 118.2 | C1—N1—C5 | 118.3 (3) |
C13—C12—H12 | 117.8 | C1—N1—Cu1 | 126.7 (3) |
N12—C12—H12 | 117.8 | C5—N1—Cu1 | 114.9 (3) |
N12—C12—C13 | 124.3 (4) | C6—N2—Cu1 | 114.0 (3) |
C9—C13—H13 | 120.4 | C6—N2—N3 | 109.0 (3) |
C12—C13—C9 | 119.1 (4) | N3—N2—Cu1 | 136.3 (2) |
C12—C13—H13 | 120.4 | C7—N3—N2 | 105.7 (3) |
C15—C14—H14 | 118.9 | C6—N4—C7 | 105.4 (3) |
N6—C14—H14 | 118.9 | C6—N4—N5 | 125.2 (3) |
N6—C14—C15 | 122.2 (4) | C7—N4—N5 | 129.3 (3) |
C14—C15—H15 | 120.4 | N4—N5—H5A | 101.2 |
C14—C15—C16 | 119.3 (4) | N4—N5—H5B | 102.5 |
C16—C15—H15 | 120.4 | H5A—N5—H5B | 96.8 |
C15—C16—H16 | 120.2 | C14—N6—C18 | 118.5 (3) |
C15—C16—C17 | 119.5 (4) | C14—N6—Cu1 | 126.5 (3) |
C17—C16—H16 | 120.2 | C18—N6—Cu1 | 115.0 (3) |
C16—C17—H17 | 121.0 | C19—N7—Cu1 | 113.7 (3) |
C16—C17—C18 | 118.1 (4) | C19—N7—N8 | 109.5 (3) |
C18—C17—H17 | 121.0 | N8—N7—Cu1 | 136.4 (2) |
C17—C18—C19 | 126.3 (4) | C20—N8—N7 | 105.6 (3) |
N6—C18—C17 | 122.4 (4) | C19—N9—C20 | 105.7 (3) |
N6—C18—C19 | 111.2 (3) | C19—N9—N10 | 125.7 (3) |
N7—C19—C18 | 119.7 (3) | C20—N9—N10 | 128.4 (3) |
N7—C19—N9 | 108.4 (3) | N9—N10—H10A | 106.5 |
N9—C19—C18 | 131.9 (3) | N9—N10—H10B | 108.7 |
N8—C20—N9 | 110.7 (3) | H10A—N10—H10B | 113.4 |
N8—C20—S1 | 128.2 (3) | C25—N11—C24 | 115.7 (4) |
N9—C20—S1 | 121.1 (3) | C11—N12—C12 | 115.7 (4) |
H21A—C21—H21B | 107.5 | C11—N12—Cu1ii | 120.6 (3) |
C22—C21—H21A | 108.4 | C12—N12—Cu1ii | 123.3 (3) |
C22—C21—H21B | 108.4 | H9A—O9—H9A | 0.0 |
C22—C21—S1 | 115.4 (3) | H9A—O9—H9B | 93.7 |
S1—C21—H21A | 108.4 | H9A—O9—H9B | 93.7 |
S1—C21—H21B | 108.4 | C20—S1—C21 | 98.15 (19) |
C23—C22—C21 | 123.0 (4) | C7—S2—C8 | 98.17 (19) |
C26—C22—C21 | 119.5 (4) | | |
| | | |
C1—C2—C3—C4 | 0.6 (7) | N1—Cu1—N7—C19 | −174.6 (3) |
C2—C1—N1—C5 | 0.6 (6) | N1—Cu1—N7—N8 | −3.1 (4) |
C2—C1—N1—Cu1 | 175.9 (3) | N2—C6—N4—C7 | −1.2 (4) |
C2—C3—C4—C5 | 0.1 (6) | N2—C6—N4—N5 | −178.9 (4) |
C3—C4—C5—C6 | −177.1 (4) | N2—Cu1—N1—C1 | −172.3 (4) |
C3—C4—C5—N1 | −0.5 (6) | N2—Cu1—N1—C5 | 3.1 (3) |
C4—C5—C6—N2 | 168.8 (4) | N2—Cu1—N6—C14 | −6.4 (4) |
C4—C5—C6—N4 | −8.4 (7) | N2—Cu1—N6—C18 | 175.7 (3) |
C4—C5—N1—C1 | 0.1 (6) | N2—Cu1—N7—C19 | 119 (36) |
C4—C5—N1—Cu1 | −175.7 (3) | N2—Cu1—N7—N8 | −70 (37) |
C5—C6—N2—Cu1 | 11.1 (5) | N3—C7—N4—C6 | 1.1 (4) |
C5—C6—N2—N3 | −176.9 (3) | N3—C7—N4—N5 | 178.7 (4) |
C5—C6—N4—C7 | 176.2 (4) | N3—C7—S2—C8 | 8.9 (4) |
C5—C6—N4—N5 | −1.6 (7) | N4—C6—N2—Cu1 | −171.2 (2) |
C6—C5—N1—C1 | 177.2 (3) | N4—C6—N2—N3 | 0.9 (4) |
C6—C5—N1—Cu1 | 1.4 (4) | N4—C7—N3—N2 | −0.6 (4) |
C6—N2—N3—C7 | −0.2 (4) | N4—C7—S2—C8 | −169.2 (3) |
C8—C9—C10—C11 | −175.0 (4) | N6—C14—C15—C16 | 0.3 (7) |
C8—C9—C13—C12 | 176.2 (4) | N6—C18—C19—N7 | 4.2 (5) |
C9—C8—S2—C7 | 63.8 (3) | N6—C18—C19—N9 | −177.0 (4) |
C9—C10—C11—N12 | −0.1 (7) | N6—Cu1—N1—C1 | 91 (6) |
C10—C9—C13—C12 | −0.4 (6) | N6—Cu1—N1—C5 | −93 (6) |
C10—C11—N12—C12 | −2.7 (6) | N6—Cu1—N2—C6 | 171.3 (3) |
C10—C11—N12—Cu1ii | 170.4 (3) | N6—Cu1—N2—N3 | 2.1 (4) |
C13—C9—C10—C11 | 1.6 (6) | N6—Cu1—N7—C19 | 6.6 (3) |
C13—C12—N12—C11 | 4.1 (7) | N6—Cu1—N7—N8 | 178.1 (4) |
C13—C12—N12—Cu1ii | −168.8 (4) | N7—C19—N9—C20 | 0.8 (4) |
C14—C15—C16—C17 | −0.2 (7) | N7—C19—N9—N10 | 177.6 (3) |
C15—C14—N6—C18 | −0.5 (6) | N7—Cu1—N1—C1 | 7.9 (4) |
C15—C14—N6—Cu1 | −178.4 (3) | N7—Cu1—N1—C5 | −176.6 (3) |
C15—C16—C17—C18 | 0.4 (6) | N7—Cu1—N2—C6 | 59 (37) |
C16—C17—C18—C19 | 176.0 (4) | N7—Cu1—N2—N3 | −110 (36) |
C16—C17—C18—N6 | −0.7 (6) | N7—Cu1—N6—C14 | 173.3 (4) |
C17—C18—C19—N7 | −172.8 (4) | N7—Cu1—N6—C18 | −4.6 (3) |
C17—C18—C19—N9 | 6.1 (7) | N8—C20—N9—C19 | −0.4 (4) |
C17—C18—N6—C14 | 0.8 (6) | N8—C20—N9—N10 | −177.0 (4) |
C17—C18—N6—Cu1 | 178.9 (3) | N8—C20—S1—C21 | −9.8 (4) |
C18—C19—N7—Cu1 | −8.1 (5) | N9—C19—N7—Cu1 | 172.8 (2) |
C18—C19—N7—N8 | 178.1 (3) | N9—C19—N7—N8 | −1.0 (4) |
C18—C19—N9—C20 | −178.1 (4) | N9—C20—N8—N7 | −0.2 (4) |
C18—C19—N9—N10 | −1.4 (7) | N9—C20—S1—C21 | 170.3 (3) |
C19—C18—N6—C14 | −176.3 (3) | N11—C25—C26—C22 | 0.4 (7) |
C19—C18—N6—Cu1 | 1.7 (4) | N12—C12—C13—C9 | −2.7 (7) |
C19—N7—N8—C20 | 0.7 (4) | N12i—Cu1—N1—C1 | −81.1 (3) |
C21—C22—C23—C24 | −176.1 (4) | N12i—Cu1—N1—C5 | 94.4 (3) |
C21—C22—C26—C25 | 175.8 (4) | N12i—Cu1—N2—C6 | −95.5 (3) |
C22—C21—S1—C20 | −63.7 (3) | N12i—Cu1—N2—N3 | 95.4 (4) |
C22—C23—C24—N11 | 0.5 (7) | N12i—Cu1—N6—C14 | −97.9 (3) |
C23—C22—C26—C25 | −1.8 (6) | N12i—Cu1—N6—C18 | 84.2 (3) |
C23—C24—N11—C25 | −1.9 (7) | N12i—Cu1—N7—C19 | −86.5 (3) |
C26—C22—C23—C24 | 1.3 (6) | N12i—Cu1—N7—N8 | 84.9 (4) |
C26—C25—N11—C24 | 1.4 (6) | S1—C20—N8—N7 | 179.9 (3) |
Cu1—N2—N3—C7 | 169.3 (3) | S1—C20—N9—C19 | 179.5 (3) |
Cu1—N7—N8—C20 | −171.0 (3) | S1—C20—N9—N10 | 2.9 (6) |
N1—C1—C2—C3 | −0.9 (7) | S1—C21—C22—C23 | −34.1 (5) |
N1—C5—C6—N2 | −8.2 (5) | S1—C21—C22—C26 | 148.5 (3) |
N1—C5—C6—N4 | 174.6 (4) | S2—C7—N3—N2 | −178.8 (3) |
N1—Cu1—N2—C6 | −7.5 (3) | S2—C7—N4—C6 | 179.5 (3) |
N1—Cu1—N2—N3 | −176.6 (4) | S2—C7—N4—N5 | −2.9 (6) |
N1—Cu1—N6—C14 | 90 (6) | S2—C8—C9—C10 | −155.1 (3) |
N1—Cu1—N6—C18 | −88 (6) | S2—C8—C9—C13 | 28.5 (5) |
Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) x+1/2, −y+1/2, z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O9—H9A···O1 | 0.86 | 2.11 | 2.831 (6) | 141 |
O9—H9A···O3 | 0.86 | 2.60 | 3.393 (9) | 155 |
O9—H9B···O4iii | 0.85 | 2.07 | 2.904 (6) | 168 |
N10—H10A···O2 | 0.89 | 2.13 | 3.021 (6) | 176 |
N10—H10A···O4 | 0.89 | 2.49 | 2.999 (6) | 117 |
N5—H5A···O9ii | 0.95 | 2.03 | 2.918 (5) | 154 |
N5—H5B···O8 | 0.85 | 2.32 | 3.127 (6) | 159 |
N10—H10B···O5iv | 0.96 | 2.05 | 2.986 (5) | 166 |
Symmetry codes: (ii) x+1/2, −y+1/2, z+1/2; (iii) −x+1, −y+1, −z+1; (iv) x−1/2, −y+1/2, z+1/2. |