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By the solvothermal reactions of 2,5-bis(1H-1,2,4-triazol-1-yl)terephthalic acid (H2L) with transition-metal ions, two novel polymeric complexes, namely, poly[diaqua[μ4-2,5-bis(1H-1,2,4-triazol-1-yl)terephthalato]cobalt(II)], [Co(C12H6N6O4)(H2O)2]n, (1), and poly[[diaqua[μ4-2,5-bis(1H-1,2,4-triazol-1-yl)terephthalato]nickel(II)] dihydrate], {[Ni(C12H6N6O4)(H2O)2]·2H2O}n, (2), were isolated. Both polymers have been characterized by FT–IR spectroscopy, elemental analysis and single-crystal X-ray diffraction analysis. The complexes have similar two-dimensional layered structures and coordination modes. Furthermore, the two-dimensional layered structures bear distinct intermolecular hydrogen-bonding interactions and π–π stacking interactions to form two different three-dimensional supramolecular networks based on 44-subnets. The structural variation depends on the nature of the metal cations. The results of variable-temperature magnetization measurements (χMT−T and χM−1−T) show that complexes (1) and (2) display antiferromagnetic behaviour.
Supporting information
CCDC references: 1967884; 1566991
For both structures, data collection: SMART (Bruker, 2010); cell refinement: SMART (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Bruker, 2010); software used to prepare material for publication: SHELXTL (Bruker, 2010).
Poly[diaqua[µ
4-2,5-bis(1
H-1,2,4-triazol-1-yl)terephthalato]cobalt(II)] (160717a)
top
Crystal data top
[Co(C12H6N6O4)(H2O)2] | F(000) = 398 |
Mr = 393.19 | Dx = 1.829 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 7.134 (3) Å | Cell parameters from 959 reflections |
b = 9.882 (3) Å | θ = 2.9–26.8° |
c = 10.300 (4) Å | µ = 1.25 mm−1 |
β = 100.484 (4)° | T = 296 K |
V = 714.0 (4) Å3 | Block, pale-red |
Z = 2 | 0.22 × 0.16 × 0.10 mm |
Data collection top
Bruker SMART CCD area detector diffractometer | 1408 independent reflections |
Radiation source: fine-focus sealed tube | 1007 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
phi and ω scans | θmax = 26.0°, θmin = 2.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2010) | h = −8→8 |
Tmin = 0.770, Tmax = 0.885 | k = −6→12 |
3624 measured reflections | l = −12→11 |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.122 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0598P)2 + 0.5618P] where P = (Fo2 + 2Fc2)/3 |
1408 reflections | (Δ/σ)max < 0.001 |
115 parameters | Δρmax = 0.69 e Å−3 |
0 restraints | Δρmin = −0.81 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Co1 | 0.5000 | 0.5000 | 0.5000 | 0.0219 (3) | |
O1 | 0.6815 (4) | 0.5172 (3) | 0.6808 (2) | 0.0282 (7) | |
O2 | 0.6061 (5) | 0.3321 (4) | 0.7816 (3) | 0.0513 (10) | |
O3 | 0.4703 (5) | 0.7116 (3) | 0.5001 (3) | 0.0456 (9) | |
H3A | 0.3750 | 0.7287 | 0.4398 | 0.068* | |
H3B | 0.4753 | 0.7530 | 0.5730 | 0.068* | |
N1 | 1.2599 (5) | 0.4664 (4) | 0.5935 (3) | 0.0291 (9) | |
N2 | 1.0440 (5) | 0.3469 (4) | 0.6781 (3) | 0.0380 (10) | |
N3 | 1.1054 (5) | 0.4546 (4) | 0.7554 (3) | 0.0260 (8) | |
C1 | 1.2321 (6) | 0.5256 (5) | 0.7032 (4) | 0.0296 (11) | |
H1 | 1.2916 | 0.6045 | 0.7385 | 0.035* | |
C2 | 1.1425 (6) | 0.3592 (5) | 0.5829 (4) | 0.0369 (12) | |
H2 | 1.1317 | 0.2982 | 0.5131 | 0.044* | |
C3 | 1.0474 (5) | 0.4786 (4) | 0.8789 (3) | 0.0236 (10) | |
C4 | 0.8584 (5) | 0.4673 (4) | 0.8902 (3) | 0.0216 (9) | |
C5 | 1.1870 (5) | 0.5100 (4) | 0.9858 (3) | 0.0253 (9) | |
H5 | 1.3133 | 0.5161 | 0.9749 | 0.030* | |
C6 | 0.7012 (5) | 0.4366 (5) | 0.7745 (4) | 0.0253 (9) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Co1 | 0.0228 (4) | 0.0382 (5) | 0.0058 (3) | −0.0002 (4) | 0.0057 (2) | −0.0003 (3) |
O1 | 0.0292 (15) | 0.045 (2) | 0.0094 (13) | −0.0060 (13) | 0.0008 (10) | 0.0060 (12) |
O2 | 0.049 (2) | 0.069 (3) | 0.0283 (18) | −0.0297 (19) | −0.0123 (15) | 0.0211 (17) |
O3 | 0.071 (3) | 0.043 (2) | 0.0216 (15) | 0.0079 (18) | 0.0061 (16) | −0.0032 (15) |
N1 | 0.0268 (18) | 0.050 (3) | 0.0116 (16) | 0.0008 (16) | 0.0066 (13) | −0.0005 (15) |
N2 | 0.043 (2) | 0.053 (3) | 0.0219 (19) | −0.010 (2) | 0.0163 (17) | −0.0117 (17) |
N3 | 0.0257 (18) | 0.045 (2) | 0.0096 (15) | −0.0043 (15) | 0.0078 (13) | −0.0036 (14) |
C1 | 0.029 (2) | 0.047 (3) | 0.0145 (19) | −0.0033 (19) | 0.0091 (16) | −0.0024 (18) |
C2 | 0.034 (3) | 0.061 (3) | 0.019 (2) | −0.010 (2) | 0.0135 (19) | −0.016 (2) |
C3 | 0.0244 (19) | 0.039 (3) | 0.0094 (16) | −0.0034 (17) | 0.0080 (14) | 0.0011 (16) |
C4 | 0.0190 (19) | 0.036 (3) | 0.0101 (17) | −0.0015 (16) | 0.0030 (14) | 0.0036 (15) |
C5 | 0.0197 (17) | 0.045 (3) | 0.0123 (17) | −0.0057 (19) | 0.0055 (14) | 0.0037 (18) |
C6 | 0.020 (2) | 0.043 (3) | 0.0124 (19) | −0.0039 (19) | 0.0009 (15) | 0.0000 (18) |
Geometric parameters (Å, º) top
Co1—O1 | 2.073 (2) | N2—C2 | 1.312 (5) |
Co1—O1i | 2.073 (2) | N2—N3 | 1.353 (5) |
Co1—O3 | 2.102 (3) | N3—C1 | 1.332 (5) |
Co1—O3i | 2.102 (3) | N3—C3 | 1.427 (4) |
Co1—N1ii | 2.138 (3) | C1—H1 | 0.9300 |
Co1—N1iii | 2.138 (3) | C2—H2 | 0.9300 |
O1—C6 | 1.239 (5) | C3—C5 | 1.379 (5) |
O2—C6 | 1.245 (5) | C3—C4 | 1.380 (5) |
O3—H3A | 0.8501 | C4—C5v | 1.391 (5) |
O3—H3B | 0.8501 | C4—C6 | 1.511 (5) |
N1—C1 | 1.319 (5) | C5—C4v | 1.391 (5) |
N1—C2 | 1.342 (5) | C5—H5 | 0.9300 |
N1—Co1iv | 2.138 (3) | | |
| | | |
O1—Co1—O1i | 179.999 (1) | C2—N2—N3 | 102.0 (4) |
O1—Co1—O3 | 87.97 (12) | C1—N3—N2 | 110.3 (3) |
O1i—Co1—O3 | 92.03 (12) | C1—N3—C3 | 126.9 (4) |
O1—Co1—O3i | 92.03 (12) | N2—N3—C3 | 122.7 (3) |
O1i—Co1—O3i | 87.97 (12) | N1—C1—N3 | 109.3 (4) |
O3—Co1—O3i | 180.0 | N1—C1—H1 | 125.3 |
O1—Co1—N1ii | 88.34 (11) | N3—C1—H1 | 125.3 |
O1i—Co1—N1ii | 91.66 (11) | N2—C2—N1 | 115.0 (4) |
O3—Co1—N1ii | 86.24 (13) | N2—C2—H2 | 122.5 |
O3i—Co1—N1ii | 93.76 (13) | N1—C2—H2 | 122.5 |
O1—Co1—N1iii | 91.66 (11) | C5—C3—C4 | 121.7 (3) |
O1i—Co1—N1iii | 88.34 (11) | C5—C3—N3 | 117.7 (3) |
O3—Co1—N1iii | 93.76 (13) | C4—C3—N3 | 120.6 (3) |
O3i—Co1—N1iii | 86.24 (13) | C3—C4—C5v | 117.3 (3) |
N1ii—Co1—N1iii | 180.0 | C3—C4—C6 | 123.1 (3) |
C6—O1—Co1 | 127.6 (3) | C5v—C4—C6 | 119.6 (3) |
Co1—O3—H3A | 105.4 | C3—C5—C4v | 121.0 (3) |
Co1—O3—H3B | 119.4 | C3—C5—H5 | 119.5 |
H3A—O3—H3B | 116.6 | C4v—C5—H5 | 119.5 |
C1—N1—C2 | 103.4 (3) | O1—C6—O2 | 126.4 (4) |
C1—N1—Co1iv | 125.0 (3) | O1—C6—C4 | 116.6 (4) |
C2—N1—Co1iv | 128.7 (3) | O2—C6—C4 | 117.0 (4) |
| | | |
O1i—Co1—O1—C6 | −160 (12) | N2—N3—C3—C5 | 132.7 (4) |
O3—Co1—O1—C6 | 146.2 (3) | C1—N3—C3—C4 | 138.7 (4) |
O3i—Co1—O1—C6 | −33.8 (3) | N2—N3—C3—C4 | −45.8 (6) |
N1ii—Co1—O1—C6 | −127.5 (3) | C5—C3—C4—C5v | 0.6 (7) |
N1iii—Co1—O1—C6 | 52.5 (3) | N3—C3—C4—C5v | 178.9 (4) |
C2—N2—N3—C1 | 0.9 (5) | C5—C3—C4—C6 | 178.4 (4) |
C2—N2—N3—C3 | −175.2 (4) | N3—C3—C4—C6 | −3.2 (6) |
C2—N1—C1—N3 | 0.9 (5) | C4—C3—C5—C4v | −0.6 (7) |
Co1iv—N1—C1—N3 | −161.2 (3) | N3—C3—C5—C4v | −179.0 (4) |
N2—N3—C1—N1 | −1.2 (5) | Co1—O1—C6—O2 | −4.8 (6) |
C3—N3—C1—N1 | 174.8 (4) | Co1—O1—C6—C4 | 174.1 (2) |
N3—N2—C2—N1 | −0.4 (5) | C3—C4—C6—O1 | −58.7 (6) |
C1—N1—C2—N2 | −0.3 (5) | C5v—C4—C6—O1 | 119.0 (4) |
Co1iv—N1—C2—N2 | 160.9 (3) | C3—C4—C6—O2 | 120.3 (5) |
C1—N3—C3—C5 | −42.8 (6) | C5v—C4—C6—O2 | −62.0 (6) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+1, −z+1; (iii) x−1, y, z; (iv) x+1, y, z; (v) −x+2, −y+1, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3A···O2i | 0.85 | 2.39 | 2.886 (4) | 118 |
O3—H3B···O2vi | 0.85 | 1.87 | 2.686 (5) | 160 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (vi) −x+1, y+1/2, −z+3/2. |
Poly[[diaqua[µ
4-2,5-bis(1
H-1,2,4-triazol-1-yl)terephthalato]nickel(II)] dihydrate] (160716b)
top
Crystal data top
[Ni(C12H6N6O4)(H2O)2]·2H2O | Z = 1 |
Mr = 429.00 | F(000) = 220 |
Triclinic, P1 | Dx = 1.772 Mg m−3 |
a = 7.3533 (11) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.9541 (12) Å | Cell parameters from 1018 reflections |
c = 8.1396 (12) Å | θ = 2.8–28.9° |
α = 65.416 (2)° | µ = 1.27 mm−1 |
β = 88.890 (2)° | T = 296 K |
γ = 69.788 (2)° | Block, pale-blue |
V = 401.92 (10) Å3 | 0.24 × 0.16 × 0.10 mm |
Data collection top
Bruker SMART CCD area detector diffractometer | 1554 independent reflections |
Radiation source: fine-focus sealed tube | 1404 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.015 |
phi and ω scans | θmax = 26.0°, θmin = 2.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2010) | h = −9→9 |
Tmin = 0.751, Tmax = 0.884 | k = −9→8 |
2275 measured reflections | l = −9→10 |
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)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.074 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.029P)2 + 0.3943P] where P = (Fo2 + 2Fc2)/3 |
1554 reflections | (Δ/σ)max < 0.001 |
124 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.35 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Ni1 | 0.0000 | 0.0000 | 0.0000 | 0.01590 (14) | |
O1 | 0.1783 (3) | 0.0696 (3) | 0.1277 (2) | 0.0238 (4) | |
O2 | −0.0129 (3) | 0.2317 (3) | 0.2726 (3) | 0.0421 (6) | |
O3 | −0.2351 (3) | 0.0953 (3) | 0.1293 (2) | 0.0275 (4) | |
H3A | −0.3420 | 0.1628 | 0.0559 | 0.041* | |
H3B | −0.1994 | 0.1532 | 0.1825 | 0.041* | |
O4 | 0.6086 (3) | 0.6950 (4) | 0.0815 (3) | 0.0509 (6) | |
H4A | 0.6568 | 0.6149 | 0.1923 | 0.076* | |
H4B | 0.6589 | 0.7818 | 0.0281 | 0.076* | |
N1 | 0.0940 (3) | 0.7165 (3) | 0.2172 (3) | 0.0201 (5) | |
N2 | 0.2247 (3) | 0.4829 (3) | 0.5033 (3) | 0.0223 (5) | |
N3 | 0.2541 (3) | 0.4001 (3) | 0.3823 (3) | 0.0187 (4) | |
C1 | 0.1760 (4) | 0.5418 (4) | 0.2138 (3) | 0.0214 (5) | |
H1 | 0.1789 | 0.5208 | 0.1094 | 0.026* | |
C2 | 0.1266 (4) | 0.6718 (4) | 0.3973 (3) | 0.0220 (5) | |
H2 | 0.0829 | 0.7674 | 0.4414 | 0.026* | |
C3 | 0.3723 (4) | 0.1949 (3) | 0.4425 (3) | 0.0175 (5) | |
C4 | 0.3308 (4) | 0.0778 (4) | 0.3714 (3) | 0.0187 (5) | |
C5 | 0.4630 (4) | −0.1177 (4) | 0.4310 (3) | 0.0197 (5) | |
H5 | 0.4397 | −0.1983 | 0.3844 | 0.024* | |
C6 | 0.1472 (4) | 0.1363 (4) | 0.2464 (3) | 0.0203 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ni1 | 0.0176 (2) | 0.0123 (2) | 0.0159 (2) | −0.00286 (18) | −0.00463 (17) | −0.00636 (19) |
O1 | 0.0235 (9) | 0.0297 (10) | 0.0231 (9) | −0.0099 (8) | −0.0032 (7) | −0.0158 (8) |
O2 | 0.0230 (11) | 0.0562 (14) | 0.0578 (15) | −0.0008 (10) | −0.0065 (10) | −0.0453 (13) |
O3 | 0.0226 (10) | 0.0313 (10) | 0.0300 (10) | −0.0069 (8) | 0.0001 (8) | −0.0170 (9) |
O4 | 0.0391 (13) | 0.0659 (16) | 0.0376 (13) | −0.0241 (12) | −0.0034 (10) | −0.0093 (12) |
N1 | 0.0226 (11) | 0.0144 (10) | 0.0194 (11) | −0.0041 (9) | −0.0049 (9) | −0.0056 (9) |
N2 | 0.0281 (12) | 0.0174 (11) | 0.0206 (11) | −0.0062 (9) | −0.0021 (9) | −0.0092 (9) |
N3 | 0.0226 (11) | 0.0146 (10) | 0.0171 (10) | −0.0045 (9) | −0.0047 (8) | −0.0068 (9) |
C1 | 0.0272 (14) | 0.0147 (12) | 0.0177 (13) | −0.0036 (10) | −0.0063 (10) | −0.0058 (10) |
C2 | 0.0253 (13) | 0.0177 (12) | 0.0239 (13) | −0.0062 (11) | 0.0003 (11) | −0.0112 (11) |
C3 | 0.0210 (12) | 0.0123 (11) | 0.0164 (12) | −0.0047 (10) | −0.0033 (10) | −0.0045 (10) |
C4 | 0.0209 (13) | 0.0164 (12) | 0.0167 (12) | −0.0051 (10) | −0.0047 (10) | −0.0065 (10) |
C5 | 0.0238 (13) | 0.0184 (12) | 0.0200 (13) | −0.0080 (10) | −0.0041 (10) | −0.0107 (10) |
C6 | 0.0239 (13) | 0.0160 (12) | 0.0197 (13) | −0.0067 (10) | −0.0057 (10) | −0.0066 (10) |
Geometric parameters (Å, º) top
Ni1—O1 | 2.0347 (16) | N1—Ni1iv | 2.084 (2) |
Ni1—O1i | 2.0347 (16) | N2—C2 | 1.311 (3) |
Ni1—N1ii | 2.084 (2) | N2—N3 | 1.372 (3) |
Ni1—N1iii | 2.084 (2) | N3—C1 | 1.333 (3) |
Ni1—O3i | 2.0878 (18) | N3—C3 | 1.425 (3) |
Ni1—O3 | 2.0879 (18) | C1—H1 | 0.9300 |
O1—C6 | 1.265 (3) | C2—H2 | 0.9300 |
O2—C6 | 1.231 (3) | C3—C5v | 1.384 (3) |
O3—H3A | 0.8500 | C3—C4 | 1.395 (3) |
O3—H3B | 0.8500 | C4—C5 | 1.394 (3) |
O4—H4A | 0.8500 | C4—C6 | 1.517 (3) |
O4—H4B | 0.8501 | C5—C3v | 1.384 (3) |
N1—C1 | 1.322 (3) | C5—H5 | 0.9300 |
N1—C2 | 1.361 (3) | | |
| | | |
O1—Ni1—O1i | 180.0 | C2—N2—N3 | 102.5 (2) |
O1—Ni1—N1ii | 91.32 (8) | C1—N3—N2 | 109.73 (19) |
O1i—Ni1—N1ii | 88.68 (8) | C1—N3—C3 | 129.8 (2) |
O1—Ni1—N1iii | 88.68 (8) | N2—N3—C3 | 120.12 (19) |
O1i—Ni1—N1iii | 91.32 (8) | N1—C1—N3 | 109.9 (2) |
N1ii—Ni1—N1iii | 180.0 | N1—C1—H1 | 125.0 |
O1—Ni1—O3i | 87.59 (7) | N3—C1—H1 | 125.0 |
O1i—Ni1—O3i | 92.41 (7) | N2—C2—N1 | 114.5 (2) |
N1ii—Ni1—O3i | 89.88 (8) | N2—C2—H2 | 122.8 |
N1iii—Ni1—O3i | 90.12 (8) | N1—C2—H2 | 122.8 |
O1—Ni1—O3 | 92.41 (7) | C5v—C3—C4 | 120.8 (2) |
O1i—Ni1—O3 | 87.59 (7) | C5v—C3—N3 | 117.1 (2) |
N1ii—Ni1—O3 | 90.12 (8) | C4—C3—N3 | 122.0 (2) |
N1iii—Ni1—O3 | 89.88 (8) | C5—C4—C3 | 117.4 (2) |
O3i—Ni1—O3 | 180.0 | C5—C4—C6 | 116.0 (2) |
C6—O1—Ni1 | 130.31 (17) | C3—C4—C6 | 126.4 (2) |
Ni1—O3—H3A | 111.9 | C3v—C5—C4 | 121.8 (2) |
Ni1—O3—H3B | 105.5 | C3v—C5—H5 | 119.1 |
H3A—O3—H3B | 116.5 | C4—C5—H5 | 119.1 |
H4A—O4—H4B | 116.3 | O2—C6—O1 | 126.8 (2) |
C1—N1—C2 | 103.4 (2) | O2—C6—C4 | 119.5 (2) |
C1—N1—Ni1iv | 128.76 (17) | O1—C6—C4 | 113.6 (2) |
C2—N1—Ni1iv | 126.28 (16) | | |
| | | |
O1i—Ni1—O1—C6 | −53 (100) | N2—N3—C3—C5v | −38.0 (3) |
N1ii—Ni1—O1—C6 | 93.1 (2) | C1—N3—C3—C4 | −42.7 (4) |
N1iii—Ni1—O1—C6 | −86.9 (2) | N2—N3—C3—C4 | 145.1 (2) |
O3i—Ni1—O1—C6 | −177.1 (2) | C5v—C3—C4—C5 | −0.9 (4) |
O3—Ni1—O1—C6 | 2.9 (2) | N3—C3—C4—C5 | 175.9 (2) |
C2—N2—N3—C1 | 0.9 (3) | C5v—C3—C4—C6 | 173.8 (2) |
C2—N2—N3—C3 | 174.6 (2) | N3—C3—C4—C6 | −9.4 (4) |
C2—N1—C1—N3 | −0.2 (3) | C3—C4—C5—C3v | 0.9 (4) |
Ni1iv—N1—C1—N3 | 166.03 (16) | C6—C4—C5—C3v | −174.4 (2) |
N2—N3—C1—N1 | −0.5 (3) | Ni1—O1—C6—O2 | −24.4 (4) |
C3—N3—C1—N1 | −173.3 (2) | Ni1—O1—C6—C4 | 152.05 (17) |
N3—N2—C2—N1 | −1.1 (3) | C5—C4—C6—O2 | 135.4 (3) |
C1—N1—C2—N2 | 0.8 (3) | C3—C4—C6—O2 | −39.5 (4) |
Ni1iv—N1—C2—N2 | −165.83 (17) | C5—C4—C6—O1 | −41.4 (3) |
C1—N3—C3—C5v | 134.2 (3) | C3—C4—C6—O1 | 143.8 (3) |
Symmetry codes: (i) −x, −y, −z; (ii) −x, −y+1, −z; (iii) x, y−1, z; (iv) x, y+1, z; (v) −x+1, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3A···O4vi | 0.85 | 1.97 | 2.812 (3) | 171 |
O3—H3B···O2 | 0.85 | 1.95 | 2.749 (3) | 155 |
O4—H4A···N2vii | 0.85 | 2.35 | 3.148 (3) | 157 |
O4—H4B···O1viii | 0.85 | 2.03 | 2.852 (3) | 163 |
Symmetry codes: (vi) −x, −y+1, −z+1; (vii) −x+1, −y+1, −z+1; (viii) −x+1, −y+1, −z. |
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