Due to their versatile coordination modes and metal-binding conformations, triazolyl ligands can provide a wide range of possibilities for the construction of supramolecular structures. Seven mononuclear transition metal complexes with different structural forms, namely aquabis[3-(4-methylphenyl)-5-(pyridin-2-yl)-1H-1,2,4-triazolato-κ2N1,N5]zinc(II), [Zn(C14H11N4)2(H2O)], (I), bis[5-(4-methylphenyl)-3-(pyridin-2-yl)-1H-1,2,4-triazole-κ2N3,N4]bis(nitrato-κO)zinc(II), [Zn(NO3)2(C14H12N4)2], (II), bis(methanol-κO)bis[3-(4-methylphenyl)-5-(pyridin-2-yl)-1H-1,2,4-triazolato-κ2N1,N5]zinc(II), [Zn(C14H11N4)2(CH4O)2], (III), diiodidobis[5-(4-methylphenyl)-3-(pyridin-2-yl)-1H-1,2,4-triazole-κ2N3,N4]cadmium(II), [CdI2(C14H12N4)2], (IV), bis[5-(4-methylphenyl)-3-(pyridin-2-yl)-1H-1,2,4-triazole-κ2N3,N4]bis(nitrato-κO)cadmium(II), [Cd(NO3)2(C14H12N4)2], (V), aquabis[3-(4-methylphenyl)-5-(pyridin-2-yl)-1H-1,2,4-triazolato-κ2N1,N5]cobalt(II), [Co(C14H11N4)2(H2O)], (VI), and diaquabis[3-(4-methylphenyl)-5-(pyridin-2-yl)-1H-1,2,4-triazolato-κ2N1,N5]nickel(II), [Ni(C14H11N4)2(H2O)2], (VII), have been prepared by the reaction of transition metal salts (ZnII, CdII, CoII and NiII) with 3-(4-methylphenyl)-5-(pyridin-2-yl)-1H-1,2,4-triazole (pymphtzH) under either ambient or hydrothermal conditions. These compounds have been characterized by elemental analysis, IR spectroscopy and single-crystal X-ray diffraction. All the complexes form three-dimensional supramolecular structures through hydrogen bonds or through π–π stacking interactions between the centroids of the pyridyl or arene rings. The pymphtzH and pymphtz− entities act as bidentate coordinating ligands in each structure. Moreover, all the pyridyl N atoms are coordinated to metal atoms (Zn, Cd, Co or Ni). The N atom in the 4-position of the triazole group is coordinated to the Zn and Cd atoms in the crystal structures of (II), (IV) and (V), while the N atom in the 1-position of the triazolate group is coordinated to the Zn, Co and Ni atoms in (I), (III), (VI) and (VII).
Supporting information
CCDC references: 1488086; 1488087; 1488088; 1488089; 1488090; 1488092; 1488093
For all compounds, data collection: CrystalStructure (Rigaku/MSC, 2006); cell refinement: CrystalStructure (Rigaku/MSC, 2006); data reduction: CrystalStructure (Rigaku/MSC, 2006); program(s) used to solve structure: SHELXL2014/7 (Sheldrick, 2015); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: SHELXL2014/7 (Sheldrick, 2015); software used to prepare material for publication: SHELXL2014/7 (Sheldrick, 2015).
(I) Aquabis[5-(4-methylphenyl)-3-(pyridin-2-yl)-1
H-1,2,4-triazolato-
κ2N1,
N5]zinc(II)
top
Crystal data top
[Zn(C14H11N4)2(H2O)] | F(000) = 1144 |
Mr = 553.94 | Dx = 1.473 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 28.730 (6) Å | Cell parameters from 11889 reflections |
b = 7.5129 (15) Å | θ = 3.1–25.0° |
c = 12.476 (3) Å | µ = 1.02 mm−1 |
β = 111.97 (3)° | T = 293 K |
V = 2497.3 (11) Å3 | Block, colourless |
Z = 4 | 0.30 × 0.27 × 0.25 mm |
Data collection top
Rigaku MM007-HF CCD (Saturn 724+) diffractometer | 1422 reflections with I > 2σ(I) |
Radiation source: rotating anode | Rint = 0.098 |
ω scans at fixed χ = 45° | θmax = 25.0°, θmin = 3.1° |
Absorption correction: multi-scan ABSCOR | h = −34→34 |
Tmin = 0.743, Tmax = 0.774 | k = −8→8 |
9211 measured reflections | l = −14→14 |
2194 independent 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)] = 0.062 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.145 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0716P)2] where P = (Fo2 + 2Fc2)/3 |
2194 reflections | (Δ/σ)max < 0.001 |
177 parameters | Δρmax = 0.42 e Å−3 |
1 restraint | Δρmin = −0.63 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. SHELXL-2014/7 (Sheldrick, 2015) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Zn1 | 0.0000 | 0.38474 (10) | 0.7500 | 0.0521 (3) | |
N1 | 0.03174 (14) | 0.2829 (5) | 0.9088 (3) | 0.0512 (10) | |
N2 | 0.08020 (14) | 0.2435 (5) | 0.9822 (3) | 0.0540 (10) | |
N3 | 0.06436 (14) | 0.3620 (5) | 0.6965 (3) | 0.0485 (9) | |
N4 | 0.02756 (14) | 0.2102 (5) | 1.0789 (3) | 0.0487 (10) | |
O1W | 0.0000 | 0.6501 (6) | 0.7500 | 0.0698 (14) | |
H1WA | −0.0090 (15) | 0.721 (4) | 0.788 (3) | 0.105* | |
C1 | 0.00230 (17) | 0.2630 (6) | 0.9692 (4) | 0.0464 (11) | |
C2 | 0.07519 (17) | 0.2014 (6) | 1.0818 (4) | 0.0468 (11) | |
C3 | 0.05145 (17) | 0.2975 (6) | 0.5873 (4) | 0.0456 (11) | |
C4 | 0.08626 (18) | 0.2672 (6) | 0.5381 (4) | 0.0564 (13) | |
H4 | 0.0766 | 0.2229 | 0.4633 | 0.068* | |
C5 | 0.13637 (19) | 0.3045 (7) | 0.6031 (4) | 0.0660 (14) | |
H5 | 0.1608 | 0.2845 | 0.5724 | 0.079* | |
C6 | 0.14941 (19) | 0.3710 (7) | 0.7130 (4) | 0.0624 (13) | |
H6 | 0.1826 | 0.3995 | 0.7571 | 0.075* | |
C7 | 0.11251 (19) | 0.3946 (6) | 0.7561 (4) | 0.0572 (13) | |
H7 | 0.1217 | 0.4358 | 0.8315 | 0.069* | |
C8 | 0.11915 (17) | 0.1484 (6) | 1.1852 (4) | 0.0478 (11) | |
C9 | 0.11328 (18) | 0.0706 (6) | 1.2800 (4) | 0.0524 (12) | |
H9 | 0.0812 | 0.0509 | 1.2793 | 0.063* | |
C10 | 0.15490 (19) | 0.0218 (6) | 1.3759 (4) | 0.0573 (13) | |
H10 | 0.1501 | −0.0325 | 1.4381 | 0.069* | |
C11 | 0.2029 (2) | 0.0514 (6) | 1.3816 (4) | 0.0569 (13) | |
C12 | 0.20898 (19) | 0.1295 (7) | 1.2867 (4) | 0.0629 (13) | |
H12 | 0.2411 | 0.1503 | 1.2881 | 0.076* | |
C13 | 0.16755 (19) | 0.1769 (6) | 1.1899 (4) | 0.0568 (13) | |
H13 | 0.1723 | 0.2286 | 1.1271 | 0.068* | |
C14 | 0.2483 (2) | 0.0004 (7) | 1.4868 (4) | 0.0767 (17) | |
H14A | 0.2375 | −0.0516 | 1.5439 | 0.115* | |
H14B | 0.2680 | 0.1046 | 1.5183 | 0.115* | |
H14C | 0.2682 | −0.0842 | 1.4650 | 0.115* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.0514 (6) | 0.0692 (5) | 0.0403 (5) | 0.000 | 0.0225 (4) | 0.000 |
N1 | 0.046 (3) | 0.070 (2) | 0.043 (2) | 0.000 (2) | 0.022 (2) | −0.0003 (18) |
N2 | 0.046 (3) | 0.075 (3) | 0.046 (2) | 0.004 (2) | 0.022 (2) | 0.0030 (19) |
N3 | 0.049 (3) | 0.057 (2) | 0.038 (2) | −0.0004 (19) | 0.0139 (18) | −0.0031 (17) |
N4 | 0.049 (3) | 0.060 (2) | 0.042 (2) | −0.0015 (18) | 0.0230 (19) | −0.0022 (17) |
O1W | 0.106 (4) | 0.062 (3) | 0.065 (3) | 0.000 | 0.060 (3) | 0.000 |
C1 | 0.045 (3) | 0.057 (3) | 0.043 (3) | −0.003 (2) | 0.022 (2) | −0.006 (2) |
C2 | 0.047 (3) | 0.057 (3) | 0.041 (3) | 0.000 (2) | 0.021 (2) | −0.004 (2) |
C3 | 0.046 (3) | 0.050 (3) | 0.043 (3) | 0.002 (2) | 0.020 (2) | 0.003 (2) |
C4 | 0.047 (3) | 0.079 (3) | 0.048 (3) | 0.001 (3) | 0.023 (2) | −0.007 (2) |
C5 | 0.049 (3) | 0.089 (4) | 0.070 (4) | 0.005 (3) | 0.034 (3) | 0.001 (3) |
C6 | 0.047 (3) | 0.085 (4) | 0.053 (3) | −0.003 (3) | 0.015 (3) | −0.003 (3) |
C7 | 0.058 (4) | 0.074 (3) | 0.039 (3) | −0.001 (3) | 0.019 (3) | −0.003 (2) |
C8 | 0.050 (3) | 0.057 (3) | 0.041 (3) | 0.002 (2) | 0.022 (2) | −0.003 (2) |
C9 | 0.047 (3) | 0.064 (3) | 0.050 (3) | 0.001 (2) | 0.022 (2) | −0.001 (2) |
C10 | 0.060 (4) | 0.064 (3) | 0.047 (3) | 0.004 (3) | 0.018 (3) | 0.003 (2) |
C11 | 0.056 (3) | 0.058 (3) | 0.051 (3) | 0.006 (2) | 0.013 (3) | −0.002 (2) |
C12 | 0.044 (3) | 0.088 (4) | 0.059 (3) | −0.003 (3) | 0.021 (3) | 0.002 (3) |
C13 | 0.059 (3) | 0.070 (3) | 0.046 (3) | −0.002 (3) | 0.025 (3) | −0.001 (2) |
C14 | 0.070 (4) | 0.078 (4) | 0.069 (4) | 0.006 (3) | 0.010 (3) | 0.009 (3) |
Geometric parameters (Å, º) top
Zn1—O1W | 1.994 (5) | C5—C6 | 1.373 (6) |
Zn1—N1 | 1.997 (4) | C5—H5 | 0.9300 |
Zn1—N1i | 1.997 (4) | C6—C7 | 1.368 (7) |
Zn1—N3i | 2.195 (4) | C6—H6 | 0.9300 |
Zn1—N3 | 2.195 (4) | C7—H7 | 0.9300 |
N1—C1 | 1.335 (5) | C8—C9 | 1.385 (6) |
N1—N2 | 1.382 (5) | C8—C13 | 1.386 (6) |
N2—C2 | 1.341 (5) | C9—C10 | 1.388 (6) |
N3—C7 | 1.325 (6) | C9—H9 | 0.9300 |
N3—C3 | 1.360 (5) | C10—C11 | 1.372 (7) |
N4—C1 | 1.347 (5) | C10—H10 | 0.9300 |
N4—C2 | 1.357 (6) | C11—C12 | 1.390 (7) |
O1W—H1WA | 0.8200 (11) | C11—C14 | 1.514 (6) |
C1—C3i | 1.461 (6) | C12—C13 | 1.388 (6) |
C2—C8 | 1.483 (6) | C12—H12 | 0.9300 |
C3—C4 | 1.374 (6) | C13—H13 | 0.9300 |
C3—C1i | 1.461 (6) | C14—H14A | 0.9600 |
C4—C5 | 1.391 (6) | C14—H14B | 0.9600 |
C4—H4 | 0.9300 | C14—H14C | 0.9600 |
| | | |
O1W—Zn1—N1 | 112.52 (11) | C6—C5—H5 | 120.3 |
O1W—Zn1—N1i | 112.52 (11) | C4—C5—H5 | 120.3 |
N1—Zn1—N1i | 135.0 (2) | C7—C6—C5 | 118.5 (5) |
O1W—Zn1—N3i | 94.47 (9) | C7—C6—H6 | 120.7 |
N1—Zn1—N3i | 78.01 (15) | C5—C6—H6 | 120.7 |
N1i—Zn1—N3i | 98.51 (14) | N3—C7—C6 | 123.7 (4) |
O1W—Zn1—N3 | 94.47 (9) | N3—C7—H7 | 118.1 |
N1—Zn1—N3 | 98.51 (14) | C6—C7—H7 | 118.1 |
N1i—Zn1—N3 | 78.02 (14) | C9—C8—C13 | 118.0 (4) |
N3i—Zn1—N3 | 171.06 (19) | C9—C8—C2 | 121.3 (4) |
C1—N1—N2 | 107.2 (3) | C13—C8—C2 | 120.6 (4) |
C1—N1—Zn1 | 116.9 (3) | C8—C9—C10 | 120.5 (5) |
N2—N1—Zn1 | 135.4 (3) | C8—C9—H9 | 119.8 |
C2—N2—N1 | 103.5 (4) | C10—C9—H9 | 119.8 |
C7—N3—C3 | 117.7 (4) | C11—C10—C9 | 121.8 (5) |
C7—N3—Zn1 | 129.5 (3) | C11—C10—H10 | 119.1 |
C3—N3—Zn1 | 112.8 (3) | C9—C10—H10 | 119.1 |
C1—N4—C2 | 101.3 (4) | C10—C11—C12 | 118.0 (4) |
Zn1—O1W—H1WA | 131 (3) | C10—C11—C14 | 121.8 (5) |
N1—C1—N4 | 113.1 (4) | C12—C11—C14 | 120.2 (5) |
N1—C1—C3i | 119.1 (4) | C13—C12—C11 | 120.6 (5) |
N4—C1—C3i | 127.8 (4) | C13—C12—H12 | 119.7 |
N2—C2—N4 | 114.9 (4) | C11—C12—H12 | 119.7 |
N2—C2—C8 | 121.2 (4) | C8—C13—C12 | 121.2 (4) |
N4—C2—C8 | 123.9 (4) | C8—C13—H13 | 119.4 |
N3—C3—C4 | 122.3 (4) | C12—C13—H13 | 119.4 |
N3—C3—C1i | 112.9 (4) | C11—C14—H14A | 109.5 |
C4—C3—C1i | 124.7 (4) | C11—C14—H14B | 109.5 |
C3—C4—C5 | 118.3 (4) | H14A—C14—H14B | 109.5 |
C3—C4—H4 | 120.9 | C11—C14—H14C | 109.5 |
C5—C4—H4 | 120.9 | H14A—C14—H14C | 109.5 |
C6—C5—C4 | 119.4 (5) | H14B—C14—H14C | 109.5 |
| | | |
C1—N1—N2—C2 | 0.4 (5) | C4—C5—C6—C7 | 1.5 (8) |
Zn1—N1—N2—C2 | 171.6 (3) | C3—N3—C7—C6 | 1.6 (7) |
N2—N1—C1—N4 | −0.8 (5) | Zn1—N3—C7—C6 | 178.5 (4) |
Zn1—N1—C1—N4 | −173.9 (3) | C5—C6—C7—N3 | −2.2 (8) |
N2—N1—C1—C3i | 179.6 (4) | N2—C2—C8—C9 | −166.7 (4) |
Zn1—N1—C1—C3i | 6.5 (5) | N4—C2—C8—C9 | 12.8 (7) |
C2—N4—C1—N1 | 0.8 (5) | N2—C2—C8—C13 | 13.8 (6) |
C2—N4—C1—C3i | −179.7 (4) | N4—C2—C8—C13 | −166.7 (4) |
N1—N2—C2—N4 | 0.0 (5) | C13—C8—C9—C10 | −0.5 (7) |
N1—N2—C2—C8 | 179.5 (4) | C2—C8—C9—C10 | 179.9 (4) |
C1—N4—C2—N2 | −0.5 (5) | C8—C9—C10—C11 | 1.3 (7) |
C1—N4—C2—C8 | −180.0 (4) | C9—C10—C11—C12 | −1.2 (7) |
C7—N3—C3—C4 | −0.5 (6) | C9—C10—C11—C14 | 179.2 (4) |
Zn1—N3—C3—C4 | −177.8 (3) | C10—C11—C12—C13 | 0.4 (7) |
C7—N3—C3—C1i | 178.8 (4) | C14—C11—C12—C13 | −179.9 (4) |
Zn1—N3—C3—C1i | 1.4 (4) | C9—C8—C13—C12 | −0.2 (7) |
N3—C3—C4—C5 | −0.1 (7) | C2—C8—C13—C12 | 179.3 (4) |
C1i—C3—C4—C5 | −179.2 (4) | C11—C12—C13—C8 | 0.3 (7) |
C3—C4—C5—C6 | −0.5 (7) | | |
Symmetry code: (i) −x, y, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1WA···N4ii | 0.82 (1) | 1.99 (2) | 2.748 (4) | 153 (4) |
Symmetry code: (ii) −x, −y+1, −z+2. |
(II) Bis[5-(4-methylphenyl)-3-(pyridin-2-yl)-1
H-1,2,4-triazole-
κ2N3,
N4]bis(nitrato-
κO)zinc(II)
top
Crystal data top
[Zn(NO3)2(C14H12N4)2] | F(000) = 1360 |
Mr = 661.94 | Dx = 1.574 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 16.869 (3) Å | Cell parameters from 12787 reflections |
b = 12.488 (3) Å | θ = 3.1–25.0° |
c = 14.626 (3) Å | µ = 0.94 mm−1 |
β = 114.98 (3)° | T = 293 K |
V = 2792.9 (11) Å3 | Block, colourless |
Z = 4 | 0.29 × 0.25 × 0.23 mm |
Data collection top
Rigaku MM007-HF CCD (Saturn 724+) diffractometer | 2247 reflections with I > 2σ(I) |
Radiation source: rotating anode | Rint = 0.031 |
ω scans at fixed χ = 45° | θmax = 25.0°, θmin = 3.1° |
Absorption correction: multi-scan ABSCOR | h = −20→19 |
Tmin = 0.761, Tmax = 0.805 | k = −14→14 |
10060 measured reflections | l = −15→17 |
2451 independent 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)] = 0.028 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.074 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.041P)2 + 1.7059P] where P = (Fo2 + 2Fc2)/3 |
2451 reflections | (Δ/σ)max = 0.001 |
208 parameters | Δρmax = 0.26 e Å−3 |
1 restraint | Δρmin = −0.34 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. SHELXL-2014/7 (Sheldrick, 2015) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Zn1 | 0.5000 | 0.88204 (2) | 0.7500 | 0.03176 (12) | |
N1 | 0.61243 (10) | 1.15005 (13) | 0.66917 (12) | 0.0386 (4) | |
N2 | 0.53227 (10) | 1.17340 (13) | 0.59492 (12) | 0.0378 (4) | |
H2 | 0.5261 (14) | 1.2282 (12) | 0.5558 (14) | 0.045* | |
N3 | 0.63825 (10) | 0.89979 (12) | 0.80187 (11) | 0.0314 (3) | |
N4 | 0.51444 (9) | 1.02035 (12) | 0.65421 (11) | 0.0298 (3) | |
N5 | 0.52104 (10) | 0.69679 (12) | 0.62964 (12) | 0.0362 (4) | |
O1 | 0.47666 (9) | 0.78093 (10) | 0.62533 (10) | 0.0403 (3) | |
O2 | 0.57618 (11) | 0.66514 (14) | 0.71065 (12) | 0.0625 (5) | |
O3 | 0.50665 (10) | 0.65091 (12) | 0.54813 (11) | 0.0464 (3) | |
C1 | 0.59807 (11) | 1.05699 (14) | 0.70195 (13) | 0.0306 (4) | |
C2 | 0.66656 (11) | 0.99222 (14) | 0.77859 (13) | 0.0319 (4) | |
C3 | 0.75421 (12) | 1.02048 (17) | 0.81933 (15) | 0.0404 (5) | |
H3A | 0.7718 | 1.0851 | 0.8021 | 0.049* | |
C4 | 0.81500 (12) | 0.95106 (18) | 0.88586 (15) | 0.0442 (5) | |
H4 | 0.8740 | 0.9693 | 0.9161 | 0.053* | |
C5 | 0.78687 (13) | 0.85418 (18) | 0.90685 (16) | 0.0445 (5) | |
H5 | 0.8268 | 0.8047 | 0.9491 | 0.053* | |
C6 | 0.69831 (12) | 0.83199 (16) | 0.86391 (15) | 0.0379 (4) | |
H6 | 0.6796 | 0.7670 | 0.8788 | 0.046* | |
C7 | 0.47423 (12) | 1.09556 (14) | 0.58526 (13) | 0.0312 (4) | |
C8 | 0.38316 (12) | 1.09571 (15) | 0.51027 (14) | 0.0337 (4) | |
C9 | 0.34081 (13) | 1.19056 (17) | 0.46581 (17) | 0.0469 (5) | |
H9 | 0.3712 | 1.2551 | 0.4814 | 0.056* | |
C10 | 0.25363 (13) | 1.18846 (19) | 0.39845 (18) | 0.0529 (6) | |
H10 | 0.2261 | 1.2521 | 0.3689 | 0.063* | |
C11 | 0.20634 (13) | 1.09440 (18) | 0.37388 (16) | 0.0454 (5) | |
C12 | 0.25005 (13) | 1.00015 (18) | 0.41521 (15) | 0.0442 (5) | |
H12 | 0.2201 | 0.9355 | 0.3976 | 0.053* | |
C13 | 0.33736 (12) | 1.00033 (16) | 0.48215 (14) | 0.0378 (4) | |
H13 | 0.3655 | 0.9360 | 0.5085 | 0.045* | |
C14 | 0.10968 (15) | 1.0948 (2) | 0.3065 (2) | 0.0658 (7) | |
H14A | 0.0776 | 1.0852 | 0.3467 | 0.099* | |
H14B | 0.0961 | 1.0375 | 0.2585 | 0.099* | |
H14C | 0.0938 | 1.1619 | 0.2714 | 0.099* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.02389 (17) | 0.03534 (19) | 0.03164 (18) | 0.000 | 0.00743 (13) | 0.000 |
N1 | 0.0295 (8) | 0.0411 (9) | 0.0378 (9) | −0.0020 (7) | 0.0070 (7) | 0.0059 (7) |
N2 | 0.0311 (8) | 0.0387 (9) | 0.0373 (9) | 0.0002 (7) | 0.0084 (7) | 0.0096 (7) |
N3 | 0.0251 (7) | 0.0358 (8) | 0.0311 (8) | 0.0037 (6) | 0.0098 (7) | 0.0026 (6) |
N4 | 0.0251 (7) | 0.0341 (8) | 0.0287 (8) | 0.0013 (6) | 0.0099 (6) | 0.0024 (6) |
N5 | 0.0324 (8) | 0.0338 (8) | 0.0380 (9) | 0.0018 (7) | 0.0107 (7) | 0.0016 (7) |
O1 | 0.0390 (7) | 0.0374 (7) | 0.0385 (7) | 0.0096 (6) | 0.0104 (6) | −0.0019 (6) |
O2 | 0.0639 (10) | 0.0598 (10) | 0.0432 (9) | 0.0252 (8) | 0.0025 (8) | 0.0055 (8) |
O3 | 0.0497 (8) | 0.0418 (8) | 0.0433 (8) | 0.0016 (6) | 0.0154 (7) | −0.0107 (7) |
C1 | 0.0276 (9) | 0.0348 (10) | 0.0287 (9) | −0.0007 (7) | 0.0113 (8) | 0.0002 (7) |
C2 | 0.0277 (9) | 0.0370 (10) | 0.0290 (9) | 0.0018 (7) | 0.0100 (8) | 0.0015 (8) |
C3 | 0.0291 (9) | 0.0485 (12) | 0.0402 (11) | −0.0037 (8) | 0.0113 (9) | 0.0022 (9) |
C4 | 0.0241 (9) | 0.0617 (14) | 0.0410 (11) | 0.0019 (9) | 0.0081 (9) | 0.0001 (10) |
C5 | 0.0326 (10) | 0.0567 (13) | 0.0392 (11) | 0.0141 (9) | 0.0104 (9) | 0.0060 (10) |
C6 | 0.0322 (10) | 0.0391 (10) | 0.0385 (10) | 0.0082 (8) | 0.0110 (9) | 0.0067 (8) |
C7 | 0.0281 (9) | 0.0350 (10) | 0.0298 (9) | 0.0026 (7) | 0.0115 (8) | 0.0010 (7) |
C8 | 0.0285 (9) | 0.0408 (10) | 0.0303 (9) | 0.0040 (8) | 0.0109 (8) | 0.0036 (8) |
C9 | 0.0309 (10) | 0.0425 (12) | 0.0587 (14) | 0.0020 (9) | 0.0105 (10) | 0.0088 (10) |
C10 | 0.0338 (11) | 0.0496 (13) | 0.0627 (15) | 0.0096 (9) | 0.0083 (11) | 0.0143 (11) |
C11 | 0.0302 (10) | 0.0603 (14) | 0.0396 (11) | 0.0019 (9) | 0.0088 (9) | 0.0015 (10) |
C12 | 0.0382 (11) | 0.0483 (12) | 0.0375 (11) | −0.0083 (9) | 0.0077 (9) | −0.0026 (9) |
C13 | 0.0373 (10) | 0.0400 (11) | 0.0308 (10) | 0.0018 (8) | 0.0091 (9) | 0.0028 (8) |
C14 | 0.0329 (12) | 0.0810 (18) | 0.0656 (17) | 0.0003 (11) | 0.0033 (12) | 0.0021 (13) |
Geometric parameters (Å, º) top
Zn1—O1 | 2.1138 (13) | C4—C5 | 1.381 (3) |
Zn1—O1i | 2.1138 (13) | C4—H4 | 0.9300 |
Zn1—N3i | 2.1376 (16) | C5—C6 | 1.382 (3) |
Zn1—N3 | 2.1376 (16) | C5—H5 | 0.9300 |
Zn1—N4i | 2.3007 (15) | C6—H6 | 0.9300 |
Zn1—N4 | 2.3007 (15) | C7—C8 | 1.463 (3) |
N1—C1 | 1.318 (2) | C8—C13 | 1.384 (3) |
N1—N2 | 1.361 (2) | C8—C9 | 1.394 (3) |
N2—C7 | 1.344 (2) | C9—C10 | 1.382 (3) |
N2—H2 | 0.870 (10) | C9—H9 | 0.9300 |
N3—C6 | 1.338 (2) | C10—C11 | 1.380 (3) |
N3—C2 | 1.347 (2) | C10—H10 | 0.9300 |
N4—C7 | 1.335 (2) | C11—C12 | 1.385 (3) |
N4—C1 | 1.362 (2) | C11—C14 | 1.508 (3) |
N5—O2 | 1.223 (2) | C12—C13 | 1.382 (3) |
N5—O3 | 1.251 (2) | C12—H12 | 0.9300 |
N5—O1 | 1.276 (2) | C13—H13 | 0.9300 |
C1—C2 | 1.467 (3) | C14—H14A | 0.9600 |
C2—C3 | 1.386 (3) | C14—H14B | 0.9600 |
C3—C4 | 1.381 (3) | C14—H14C | 0.9600 |
C3—H3A | 0.9300 | | |
| | | |
O1—Zn1—O1i | 106.64 (8) | C2—C3—H3A | 120.6 |
O1—Zn1—N3i | 88.73 (6) | C5—C4—C3 | 118.95 (18) |
O1i—Zn1—N3i | 98.39 (6) | C5—C4—H4 | 120.5 |
O1—Zn1—N3 | 98.39 (6) | C3—C4—H4 | 120.5 |
O1i—Zn1—N3 | 88.73 (6) | C4—C5—C6 | 118.79 (19) |
N3i—Zn1—N3 | 168.10 (8) | C4—C5—H5 | 120.6 |
O1—Zn1—N4i | 160.86 (5) | C6—C5—H5 | 120.6 |
O1i—Zn1—N4i | 87.26 (5) | N3—C6—C5 | 123.02 (19) |
N3i—Zn1—N4i | 76.00 (6) | N3—C6—H6 | 118.5 |
N3—Zn1—N4i | 94.95 (6) | C5—C6—H6 | 118.5 |
O1—Zn1—N4 | 87.26 (5) | N4—C7—N2 | 108.32 (16) |
O1i—Zn1—N4 | 160.86 (5) | N4—C7—C8 | 127.23 (17) |
N3i—Zn1—N4 | 94.95 (6) | N2—C7—C8 | 124.45 (16) |
N3—Zn1—N4 | 76.00 (6) | C13—C8—C9 | 118.73 (18) |
N4i—Zn1—N4 | 82.70 (7) | C13—C8—C7 | 119.95 (17) |
C1—N1—N2 | 101.88 (15) | C9—C8—C7 | 121.32 (18) |
C7—N2—N1 | 111.29 (15) | C10—C9—C8 | 119.8 (2) |
C7—N2—H2 | 128.3 (15) | C10—C9—H9 | 120.1 |
N1—N2—H2 | 119.8 (15) | C8—C9—H9 | 120.1 |
C6—N3—C2 | 117.78 (16) | C11—C10—C9 | 121.7 (2) |
C6—N3—Zn1 | 125.12 (13) | C11—C10—H10 | 119.1 |
C2—N3—Zn1 | 116.70 (11) | C9—C10—H10 | 119.1 |
C7—N4—C1 | 103.70 (15) | C10—C11—C12 | 117.85 (19) |
C7—N4—Zn1 | 146.90 (12) | C10—C11—C14 | 121.0 (2) |
C1—N4—Zn1 | 107.04 (11) | C12—C11—C14 | 121.2 (2) |
O2—N5—O3 | 122.53 (16) | C13—C12—C11 | 121.3 (2) |
O2—N5—O1 | 120.29 (16) | C13—C12—H12 | 119.4 |
O3—N5—O1 | 117.16 (15) | C11—C12—H12 | 119.4 |
N5—O1—Zn1 | 123.89 (11) | C12—C13—C8 | 120.40 (19) |
N1—C1—N4 | 114.79 (16) | C12—C13—H13 | 119.8 |
N1—C1—C2 | 123.90 (16) | C8—C13—H13 | 119.8 |
N4—C1—C2 | 121.17 (16) | C11—C14—H14A | 109.5 |
N3—C2—C3 | 122.50 (17) | C11—C14—H14B | 109.5 |
N3—C2—C1 | 114.64 (15) | H14A—C14—H14B | 109.5 |
C3—C2—C1 | 122.75 (17) | C11—C14—H14C | 109.5 |
C4—C3—C2 | 118.88 (19) | H14A—C14—H14C | 109.5 |
C4—C3—H3A | 120.6 | H14B—C14—H14C | 109.5 |
| | | |
C1—N1—N2—C7 | −0.5 (2) | Zn1—N3—C6—C5 | −170.49 (15) |
O2—N5—O1—Zn1 | 6.3 (2) | C4—C5—C6—N3 | 0.7 (3) |
O3—N5—O1—Zn1 | −172.31 (12) | C1—N4—C7—N2 | −1.39 (19) |
N2—N1—C1—N4 | −0.5 (2) | Zn1—N4—C7—N2 | 156.45 (17) |
N2—N1—C1—C2 | 175.30 (17) | C1—N4—C7—C8 | 178.10 (17) |
C7—N4—C1—N1 | 1.2 (2) | Zn1—N4—C7—C8 | −24.1 (3) |
Zn1—N4—C1—N1 | −166.37 (13) | N1—N2—C7—N4 | 1.2 (2) |
C7—N4—C1—C2 | −174.71 (16) | N1—N2—C7—C8 | −178.28 (17) |
Zn1—N4—C1—C2 | 17.74 (19) | N4—C7—C8—C13 | −21.6 (3) |
C6—N3—C2—C3 | −2.5 (3) | N2—C7—C8—C13 | 157.78 (18) |
Zn1—N3—C2—C3 | 170.59 (14) | N4—C7—C8—C9 | 158.42 (19) |
C6—N3—C2—C1 | 173.69 (16) | N2—C7—C8—C9 | −22.2 (3) |
Zn1—N3—C2—C1 | −13.21 (19) | C13—C8—C9—C10 | 2.8 (3) |
N1—C1—C2—N3 | 179.79 (17) | C7—C8—C9—C10 | −177.2 (2) |
N4—C1—C2—N3 | −4.7 (2) | C8—C9—C10—C11 | 0.4 (4) |
N1—C1—C2—C3 | −4.0 (3) | C9—C10—C11—C12 | −3.1 (4) |
N4—C1—C2—C3 | 171.49 (17) | C9—C10—C11—C14 | 175.3 (2) |
N3—C2—C3—C4 | 0.4 (3) | C10—C11—C12—C13 | 2.6 (3) |
C1—C2—C3—C4 | −175.49 (18) | C14—C11—C12—C13 | −175.8 (2) |
C2—C3—C4—C5 | 2.3 (3) | C11—C12—C13—C8 | 0.6 (3) |
C3—C4—C5—C6 | −2.8 (3) | C9—C8—C13—C12 | −3.3 (3) |
C2—N3—C6—C5 | 2.0 (3) | C7—C8—C13—C12 | 176.73 (18) |
Symmetry code: (i) −x+1, y, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···N5ii | 0.87 (1) | 2.65 (1) | 3.425 (2) | 148 (2) |
N2—H2···O1ii | 0.87 (1) | 2.63 (2) | 3.212 (2) | 125 (2) |
N2—H2···O3ii | 0.87 (1) | 2.05 (1) | 2.909 (2) | 172 (2) |
C6—H6···O1i | 0.93 | 2.62 | 3.088 (2) | 112 |
Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x+1, −y+2, −z+1. |
(III) Bis(methanol-
κO)bis[5-(4-methylphenyl)-3-(pyridin-2-yl)-1
H-1,2,4-triazolato-
κ2N1,
N5]zinc(II)
top
Crystal data top
[Zn(C14H11N4)2(CH4O)2] | F(000) = 624 |
Mr = 599.99 | Dx = 1.377 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 12.297 (3) Å | Cell parameters from 14234 reflections |
b = 12.663 (3) Å | θ = 3.2–25.0° |
c = 9.990 (2) Å | µ = 0.89 mm−1 |
β = 111.58 (3)° | T = 293 K |
V = 1446.6 (6) Å3 | Block, colourless |
Z = 2 | 0.31 × 0.28 × 0.26 mm |
Data collection top
Rigaku MM007-HF CCD (Saturn 724+) diffractometer | 1625 reflections with I > 2σ(I) |
Radiation source: rotating anode | Rint = 0.083 |
ω scans at fixed χ = 45° | θmax = 25.0°, θmin = 3.2° |
Absorption correction: multi-scan ABSCOR | h = −14→14 |
Tmin = 0.759, Tmax = 0.793 | k = −15→14 |
11056 measured reflections | l = −11→11 |
2526 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: structure-invariant direct methods |
R[F2 > 2σ(F2)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.113 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0582P)2] where P = (Fo2 + 2Fc2)/3 |
2526 reflections | (Δ/σ)max = 0.003 |
197 parameters | Δρmax = 0.35 e Å−3 |
2 restraints | Δρmin = −0.69 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. SHELXL-2014/7 (Sheldrick, 2015) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Zn1 | 1.0000 | 0.0000 | 0.5000 | 0.0377 (2) | |
N1 | 0.9038 (2) | 0.0748 (2) | 0.3088 (3) | 0.0371 (7) | |
N2 | 0.8097 (2) | 0.0535 (2) | 0.1852 (3) | 0.0380 (7) | |
N3 | 1.0890 (2) | 0.1492 (2) | 0.5249 (3) | 0.0350 (7) | |
N4 | 0.8768 (2) | 0.2179 (2) | 0.1694 (3) | 0.0336 (7) | |
O1 | 0.8864 (2) | 0.07444 (18) | 0.6045 (3) | 0.0446 (6) | |
H1 | 0.885 (3) | 0.1387 (4) | 0.613 (4) | 0.067* | |
C1 | 0.9404 (3) | 0.1715 (2) | 0.2957 (3) | 0.0327 (8) | |
C2 | 1.0392 (3) | 0.2174 (2) | 0.4146 (3) | 0.0328 (8) | |
C3 | 1.0791 (3) | 0.3191 (3) | 0.4186 (4) | 0.0450 (9) | |
H3 | 1.0440 | 0.3650 | 0.3421 | 0.054* | |
C4 | 1.1724 (3) | 0.3520 (3) | 0.5380 (4) | 0.0544 (11) | |
H4 | 1.2003 | 0.4208 | 0.5430 | 0.065* | |
C5 | 1.2239 (3) | 0.2828 (3) | 0.6498 (4) | 0.0499 (10) | |
H5 | 1.2874 | 0.3036 | 0.7304 | 0.060* | |
C6 | 1.1793 (3) | 0.1819 (3) | 0.6394 (4) | 0.0425 (9) | |
H6 | 1.2134 | 0.1350 | 0.7149 | 0.051* | |
C7 | 0.7965 (3) | 0.1408 (2) | 0.1050 (3) | 0.0337 (8) | |
C8 | 0.7024 (3) | 0.1505 (3) | −0.0373 (3) | 0.0380 (8) | |
C9 | 0.6950 (3) | 0.2383 (3) | −0.1237 (4) | 0.0458 (9) | |
H9 | 0.7482 | 0.2933 | −0.0895 | 0.055* | |
C10 | 0.6090 (3) | 0.2449 (3) | −0.2610 (4) | 0.0548 (11) | |
H10 | 0.6051 | 0.3047 | −0.3166 | 0.066* | |
C11 | 0.5295 (3) | 0.1644 (4) | −0.3161 (4) | 0.0560 (11) | |
C12 | 0.5339 (3) | 0.0787 (4) | −0.2280 (4) | 0.0600 (11) | |
H2 | 0.4796 | 0.0245 | −0.2619 | 0.072* | |
C13 | 0.6182 (3) | 0.0723 (3) | −0.0896 (4) | 0.0501 (10) | |
H13 | 0.6181 | 0.0149 | −0.0316 | 0.060* | |
C14 | 0.4431 (4) | 0.1677 (4) | −0.4705 (4) | 0.0841 (16) | |
H14A | 0.4305 | 0.2396 | −0.5028 | 0.126* | |
H14B | 0.3703 | 0.1370 | −0.4756 | 0.126* | |
H14C | 0.4739 | 0.1284 | −0.5308 | 0.126* | |
C15 | 0.8322 (10) | 0.0210 (7) | 0.6900 (13) | 0.064 (2) | 0.637 (15) |
H15A | 0.8049 | −0.0469 | 0.6487 | 0.096* | 0.637 (15) |
H15B | 0.7673 | 0.0621 | 0.6924 | 0.096* | 0.637 (15) |
H15C | 0.8880 | 0.0122 | 0.7861 | 0.096* | 0.637 (15) |
C15B | 0.7833 (12) | 0.0312 (15) | 0.616 (2) | 0.064 (2) | 0.363 (15) |
H15D | 0.7174 | 0.0463 | 0.5298 | 0.096* | 0.363 (15) |
H15E | 0.7710 | 0.0620 | 0.6971 | 0.096* | 0.363 (15) |
H15F | 0.7919 | −0.0439 | 0.6289 | 0.096* | 0.363 (15) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.0479 (4) | 0.0262 (3) | 0.0298 (3) | −0.0032 (3) | 0.0033 (2) | 0.0033 (2) |
N1 | 0.0448 (16) | 0.0292 (16) | 0.0309 (16) | −0.0026 (13) | 0.0065 (13) | −0.0028 (12) |
N2 | 0.0452 (17) | 0.0313 (16) | 0.0285 (15) | −0.0032 (13) | 0.0031 (13) | 0.0012 (13) |
N3 | 0.0407 (16) | 0.0340 (16) | 0.0262 (15) | −0.0002 (13) | 0.0074 (12) | 0.0025 (12) |
N4 | 0.0400 (16) | 0.0282 (15) | 0.0266 (15) | 0.0024 (13) | 0.0052 (12) | 0.0042 (12) |
O1 | 0.0561 (15) | 0.0317 (14) | 0.0464 (15) | −0.0001 (13) | 0.0193 (12) | −0.0029 (12) |
C1 | 0.0406 (19) | 0.0262 (18) | 0.0290 (18) | −0.0006 (15) | 0.0102 (15) | −0.0006 (15) |
C2 | 0.0371 (18) | 0.0294 (18) | 0.0286 (18) | 0.0020 (15) | 0.0084 (15) | 0.0000 (15) |
C3 | 0.058 (2) | 0.033 (2) | 0.036 (2) | −0.0034 (18) | 0.0081 (18) | 0.0067 (16) |
C4 | 0.070 (3) | 0.038 (2) | 0.046 (2) | −0.019 (2) | 0.010 (2) | −0.0013 (18) |
C5 | 0.055 (2) | 0.045 (2) | 0.034 (2) | −0.0153 (19) | −0.0022 (17) | 0.0003 (18) |
C6 | 0.051 (2) | 0.041 (2) | 0.0290 (19) | −0.0002 (18) | 0.0067 (17) | 0.0025 (16) |
C7 | 0.0393 (19) | 0.0289 (19) | 0.0295 (18) | 0.0036 (16) | 0.0087 (15) | 0.0017 (15) |
C8 | 0.0382 (19) | 0.041 (2) | 0.0307 (19) | 0.0015 (17) | 0.0079 (15) | −0.0037 (16) |
C9 | 0.047 (2) | 0.050 (2) | 0.037 (2) | −0.0026 (18) | 0.0107 (17) | 0.0053 (18) |
C10 | 0.048 (2) | 0.075 (3) | 0.035 (2) | 0.004 (2) | 0.0082 (18) | 0.016 (2) |
C11 | 0.045 (2) | 0.085 (3) | 0.031 (2) | 0.008 (2) | 0.0052 (17) | 0.002 (2) |
C12 | 0.047 (2) | 0.071 (3) | 0.049 (3) | −0.012 (2) | 0.0015 (19) | −0.015 (2) |
C13 | 0.047 (2) | 0.049 (2) | 0.045 (2) | −0.0021 (19) | 0.0059 (18) | −0.0008 (19) |
C14 | 0.062 (3) | 0.136 (5) | 0.035 (2) | 0.004 (3) | −0.005 (2) | 0.000 (3) |
C15 | 0.063 (6) | 0.056 (4) | 0.081 (7) | −0.012 (5) | 0.037 (5) | −0.008 (5) |
C15B | 0.063 (6) | 0.056 (4) | 0.081 (7) | −0.012 (5) | 0.037 (5) | −0.008 (5) |
Geometric parameters (Å, º) top
Zn1—N1i | 2.070 (3) | C5—H5 | 0.9300 |
Zn1—N1 | 2.070 (3) | C6—H6 | 0.9300 |
Zn1—N3i | 2.151 (3) | C7—C8 | 1.472 (4) |
Zn1—N3 | 2.151 (3) | C8—C13 | 1.389 (5) |
Zn1—O1 | 2.236 (2) | C8—C9 | 1.390 (5) |
Zn1—O1i | 2.236 (2) | C9—C10 | 1.393 (5) |
N1—C1 | 1.328 (4) | C9—H9 | 0.9300 |
N1—N2 | 1.373 (3) | C10—C11 | 1.379 (5) |
N2—C7 | 1.340 (4) | C10—H10 | 0.9300 |
N3—C6 | 1.333 (4) | C11—C12 | 1.386 (6) |
N3—C2 | 1.356 (4) | C11—C14 | 1.518 (5) |
N4—C1 | 1.350 (4) | C12—C13 | 1.392 (5) |
N4—C7 | 1.368 (4) | C12—H2 | 0.9300 |
O1—C15B | 1.425 (8) | C13—H13 | 0.9300 |
O1—C15 | 1.432 (6) | C14—H14A | 0.9600 |
O1—H1 | 0.8200 (11) | C14—H14B | 0.9600 |
C1—C2 | 1.471 (4) | C14—H14C | 0.9600 |
C2—C3 | 1.374 (4) | C15—H15A | 0.9600 |
C3—C4 | 1.381 (5) | C15—H15B | 0.9600 |
C3—H3 | 0.9300 | C15—H15C | 0.9600 |
C4—C5 | 1.377 (5) | C15B—H15D | 0.9600 |
C4—H4 | 0.9300 | C15B—H15E | 0.9600 |
C5—C6 | 1.379 (5) | C15B—H15F | 0.9600 |
| | | |
N1i—Zn1—N1 | 180.00 (15) | N3—C6—C5 | 122.3 (3) |
N1i—Zn1—N3i | 78.40 (10) | N3—C6—H6 | 118.8 |
N1—Zn1—N3i | 101.60 (10) | C5—C6—H6 | 118.8 |
N1i—Zn1—N3 | 101.60 (10) | N2—C7—N4 | 113.6 (3) |
N1—Zn1—N3 | 78.40 (10) | N2—C7—C8 | 121.7 (3) |
N3i—Zn1—N3 | 180.0 | N4—C7—C8 | 124.7 (3) |
N1i—Zn1—O1 | 90.31 (10) | C13—C8—C9 | 117.9 (3) |
N1—Zn1—O1 | 89.69 (10) | C13—C8—C7 | 121.1 (3) |
N3i—Zn1—O1 | 92.61 (10) | C9—C8—C7 | 121.0 (3) |
N3—Zn1—O1 | 87.39 (10) | C8—C9—C10 | 120.8 (4) |
N1i—Zn1—O1i | 89.69 (10) | C8—C9—H9 | 119.6 |
N1—Zn1—O1i | 90.31 (10) | C10—C9—H9 | 119.6 |
N3i—Zn1—O1i | 87.39 (10) | C11—C10—C9 | 121.3 (4) |
N3—Zn1—O1i | 92.61 (10) | C11—C10—H10 | 119.3 |
O1—Zn1—O1i | 180.0 | C9—C10—H10 | 119.3 |
C1—N1—N2 | 107.3 (3) | C10—C11—C12 | 117.9 (3) |
C1—N1—Zn1 | 114.4 (2) | C10—C11—C14 | 120.9 (4) |
N2—N1—Zn1 | 138.3 (2) | C12—C11—C14 | 121.1 (4) |
C7—N2—N1 | 104.6 (2) | C11—C12—C13 | 121.2 (4) |
C6—N3—C2 | 118.9 (3) | C11—C12—H2 | 119.4 |
C6—N3—Zn1 | 126.8 (2) | C13—C12—H2 | 119.4 |
C2—N3—Zn1 | 114.0 (2) | C8—C13—C12 | 120.8 (4) |
C1—N4—C7 | 101.5 (3) | C8—C13—H13 | 119.6 |
C15B—O1—Zn1 | 127.1 (8) | C12—C13—H13 | 119.6 |
C15—O1—Zn1 | 126.0 (4) | C11—C14—H14A | 109.5 |
C15B—O1—H1 | 108 (3) | C11—C14—H14B | 109.5 |
C15—O1—H1 | 112 (3) | H14A—C14—H14B | 109.5 |
Zn1—O1—H1 | 121 (3) | C11—C14—H14C | 109.5 |
N1—C1—N4 | 113.1 (3) | H14A—C14—H14C | 109.5 |
N1—C1—C2 | 119.6 (3) | H14B—C14—H14C | 109.5 |
N4—C1—C2 | 127.2 (3) | O1—C15—H15A | 109.5 |
N3—C2—C3 | 121.6 (3) | O1—C15—H15B | 109.5 |
N3—C2—C1 | 113.3 (3) | H15A—C15—H15B | 109.5 |
C3—C2—C1 | 125.1 (3) | O1—C15—H15C | 109.5 |
C2—C3—C4 | 118.9 (3) | H15A—C15—H15C | 109.5 |
C2—C3—H3 | 120.6 | H15B—C15—H15C | 109.5 |
C4—C3—H3 | 120.6 | O1—C15B—H15D | 109.5 |
C5—C4—C3 | 119.8 (3) | O1—C15B—H15E | 109.5 |
C5—C4—H4 | 120.1 | H15D—C15B—H15E | 109.5 |
C3—C4—H4 | 120.1 | O1—C15B—H15F | 109.5 |
C4—C5—C6 | 118.5 (3) | H15D—C15B—H15F | 109.5 |
C4—C5—H5 | 120.7 | H15E—C15B—H15F | 109.5 |
C6—C5—H5 | 120.7 | | |
| | | |
C1—N1—N2—C7 | 0.1 (4) | Zn1—N3—C6—C5 | −174.2 (3) |
Zn1—N1—N2—C7 | −179.3 (3) | C4—C5—C6—N3 | 0.5 (6) |
N2—N1—C1—N4 | −0.2 (4) | N1—N2—C7—N4 | 0.0 (4) |
Zn1—N1—C1—N4 | 179.4 (2) | N1—N2—C7—C8 | −179.1 (3) |
N2—N1—C1—C2 | 178.3 (3) | C1—N4—C7—N2 | −0.1 (4) |
Zn1—N1—C1—C2 | −2.1 (4) | C1—N4—C7—C8 | 178.9 (3) |
C7—N4—C1—N1 | 0.2 (4) | N2—C7—C8—C13 | 4.8 (5) |
C7—N4—C1—C2 | −178.2 (3) | N4—C7—C8—C13 | −174.2 (3) |
C6—N3—C2—C3 | −0.3 (5) | N2—C7—C8—C9 | −175.2 (3) |
Zn1—N3—C2—C3 | 174.7 (3) | N4—C7—C8—C9 | 5.8 (5) |
C6—N3—C2—C1 | −179.8 (3) | C13—C8—C9—C10 | −2.9 (5) |
Zn1—N3—C2—C1 | −4.8 (4) | C7—C8—C9—C10 | 177.0 (3) |
N1—C1—C2—N3 | 4.8 (5) | C8—C9—C10—C11 | −0.7 (6) |
N4—C1—C2—N3 | −177.0 (3) | C9—C10—C11—C12 | 3.1 (6) |
N1—C1—C2—C3 | −174.7 (3) | C9—C10—C11—C14 | −174.4 (4) |
N4—C1—C2—C3 | 3.5 (6) | C10—C11—C12—C13 | −1.9 (6) |
N3—C2—C3—C4 | 0.0 (6) | C14—C11—C12—C13 | 175.6 (4) |
C1—C2—C3—C4 | 179.5 (3) | C9—C8—C13—C12 | 4.1 (5) |
C2—C3—C4—C5 | 0.5 (6) | C7—C8—C13—C12 | −175.8 (3) |
C3—C4—C5—C6 | −0.8 (6) | C11—C12—C13—C8 | −1.8 (6) |
C2—N3—C6—C5 | 0.0 (5) | | |
Symmetry code: (i) −x+2, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N4ii | 0.82 (1) | 1.91 (1) | 2.722 (3) | 169 (4) |
C3—H3···O1iii | 0.93 | 2.57 | 3.437 (4) | 156 |
C6—H6···N2i | 0.93 | 2.64 | 3.435 (5) | 144 |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) x, −y+1/2, z+1/2; (iii) x, −y+1/2, z−1/2. |
(IV) Diiodidobis[5-(4-methylphenyl)-3-(pyridin-2-yl)-1H-1,2,4-triazole-
κ2N3,
N4]cadmium(II)
top
Crystal data top
[CdI2(C14H12N4)2] | F(000) = 1608 |
Mr = 838.75 | Dx = 1.920 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 18.848 (4) Å | Cell parameters from 14086 reflections |
b = 11.254 (2) Å | θ = 3.2–25.0° |
c = 15.707 (3) Å | µ = 2.91 mm−1 |
β = 119.44 (3)° | T = 293 K |
V = 2901.4 (13) Å3 | Block, colourless |
Z = 4 | 0.27 × 0.26 × 0.24 mm |
Data collection top
Rigaku MM007-HF CCD (Saturn 724+) diffractometer | 2414 reflections with I > 2σ(I) |
Radiation source: rotating anode | Rint = 0.061 |
ω scans at fixed χ = 45° | θmax = 25.0°, θmin = 3.2° |
Absorption correction: multi-scan ABSCOR | h = −22→22 |
Tmin = 0.474, Tmax = 0.497 | k = −13→13 |
10864 measured reflections | l = −18→18 |
2528 independent 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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.102 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0693P)2 + 1.7102P] where P = (Fo2 + 2Fc2)/3 |
2528 reflections | (Δ/σ)max = 0.001 |
181 parameters | Δρmax = 1.10 e Å−3 |
1 restraint | Δρmin = −1.67 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. SHELXL-2014/7 (Sheldrick, 2015) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cd1 | 0.5000 | 0.67530 (4) | 0.2500 | 0.03911 (16) | |
I1 | 0.48448 (2) | 0.85102 (2) | 0.10686 (2) | 0.04451 (16) | |
N1 | 0.5146 (2) | 0.3485 (3) | 0.0663 (3) | 0.0452 (8) | |
H1 | 0.501 (3) | 0.301 (3) | 0.0169 (17) | 0.054* | |
N2 | 0.59155 (19) | 0.3833 (4) | 0.1292 (3) | 0.0483 (8) | |
N3 | 0.36863 (17) | 0.6357 (3) | 0.2137 (2) | 0.0376 (7) | |
N4 | 0.49983 (16) | 0.4984 (3) | 0.14289 (19) | 0.0360 (7) | |
C1 | 0.5804 (2) | 0.4726 (3) | 0.1743 (2) | 0.0360 (7) | |
C2 | 0.4599 (2) | 0.4178 (3) | 0.0730 (2) | 0.0343 (7) | |
C3 | 0.3720 (2) | 0.4008 (3) | 0.0105 (2) | 0.0371 (8) | |
C4 | 0.3408 (2) | 0.2979 (4) | −0.0444 (3) | 0.0448 (9) | |
H4 | 0.3763 | 0.2379 | −0.0403 | 0.054* | |
C5 | 0.2574 (2) | 0.2831 (4) | −0.1052 (3) | 0.0497 (10) | |
H5 | 0.2380 | 0.2135 | −0.1414 | 0.060* | |
C6 | 0.2029 (2) | 0.3708 (4) | −0.1126 (3) | 0.0436 (9) | |
C7 | 0.2339 (2) | 0.4724 (4) | −0.0566 (3) | 0.0467 (9) | |
H7 | 0.1983 | 0.5310 | −0.0587 | 0.056* | |
C8 | 0.3169 (2) | 0.4883 (4) | 0.0024 (3) | 0.0439 (9) | |
H8 | 0.3362 | 0.5587 | 0.0373 | 0.053* | |
C9 | 0.35142 (19) | 0.5430 (3) | 0.2527 (2) | 0.0360 (8) | |
C10 | 0.2705 (2) | 0.5147 (4) | 0.2278 (3) | 0.0485 (10) | |
H10 | 0.2591 | 0.4494 | 0.2554 | 0.058* | |
C11 | 0.2095 (2) | 0.5857 (5) | 0.1623 (3) | 0.0557 (12) | |
H11 | 0.1555 | 0.5667 | 0.1423 | 0.067* | |
C12 | 0.2273 (2) | 0.6860 (5) | 0.1251 (3) | 0.0548 (11) | |
H12 | 0.1862 | 0.7371 | 0.0830 | 0.066* | |
C13 | 0.3078 (2) | 0.7078 (4) | 0.1525 (3) | 0.0486 (9) | |
H13 | 0.3204 | 0.7747 | 0.1278 | 0.058* | |
C14 | 0.1119 (3) | 0.3549 (4) | −0.1785 (4) | 0.0619 (13) | |
H14A | 0.0847 | 0.3645 | −0.1408 | 0.093* | |
H14B | 0.1012 | 0.2769 | −0.2068 | 0.093* | |
H14C | 0.0922 | 0.4134 | −0.2296 | 0.093* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cd1 | 0.0264 (2) | 0.0459 (3) | 0.0431 (3) | 0.000 | 0.01552 (18) | 0.000 |
I1 | 0.0496 (2) | 0.0469 (2) | 0.0385 (2) | 0.00765 (10) | 0.02279 (16) | 0.00098 (9) |
N1 | 0.0426 (18) | 0.048 (2) | 0.0496 (19) | 0.0016 (13) | 0.0258 (16) | −0.0142 (14) |
N2 | 0.0402 (17) | 0.053 (2) | 0.0542 (18) | 0.0058 (15) | 0.0255 (15) | −0.0035 (17) |
N3 | 0.0271 (14) | 0.0418 (18) | 0.0423 (16) | 0.0025 (11) | 0.0158 (13) | −0.0034 (13) |
N4 | 0.0338 (14) | 0.0409 (19) | 0.0355 (15) | 0.0043 (12) | 0.0187 (12) | 0.0025 (13) |
C1 | 0.0368 (17) | 0.038 (2) | 0.0374 (16) | 0.0057 (14) | 0.0215 (15) | 0.0069 (15) |
C2 | 0.0388 (17) | 0.0335 (19) | 0.0337 (16) | 0.0045 (14) | 0.0202 (15) | 0.0018 (14) |
C3 | 0.0420 (18) | 0.038 (2) | 0.0356 (16) | 0.0010 (15) | 0.0223 (15) | 0.0005 (15) |
C4 | 0.045 (2) | 0.038 (2) | 0.050 (2) | 0.0017 (16) | 0.0229 (18) | −0.0044 (17) |
C5 | 0.049 (2) | 0.046 (2) | 0.050 (2) | −0.0048 (18) | 0.0206 (18) | −0.0107 (18) |
C6 | 0.041 (2) | 0.050 (2) | 0.0386 (18) | −0.0026 (16) | 0.0191 (17) | 0.0024 (16) |
C7 | 0.043 (2) | 0.045 (2) | 0.048 (2) | 0.0066 (16) | 0.0187 (18) | 0.0000 (18) |
C8 | 0.046 (2) | 0.039 (2) | 0.0418 (18) | 0.0053 (16) | 0.0177 (16) | −0.0061 (16) |
C9 | 0.0336 (17) | 0.040 (2) | 0.0374 (17) | −0.0046 (14) | 0.0199 (15) | −0.0099 (15) |
C10 | 0.0390 (19) | 0.061 (3) | 0.053 (2) | −0.0077 (18) | 0.0280 (18) | −0.0104 (19) |
C11 | 0.0307 (19) | 0.082 (3) | 0.056 (2) | −0.003 (2) | 0.0225 (18) | −0.017 (2) |
C12 | 0.035 (2) | 0.067 (3) | 0.059 (2) | 0.0131 (19) | 0.0197 (19) | −0.003 (2) |
C13 | 0.0365 (19) | 0.049 (2) | 0.055 (2) | 0.0077 (17) | 0.0181 (17) | 0.0006 (18) |
C14 | 0.049 (3) | 0.065 (3) | 0.056 (3) | 0.000 (2) | 0.014 (2) | −0.005 (2) |
Geometric parameters (Å, º) top
Cd1—N3i | 2.295 (3) | C5—C6 | 1.388 (6) |
Cd1—N3 | 2.295 (3) | C5—H5 | 0.9300 |
Cd1—N4i | 2.605 (3) | C6—C7 | 1.385 (6) |
Cd1—N4 | 2.605 (3) | C6—C14 | 1.517 (6) |
Cd1—I1i | 2.8990 (6) | C7—C8 | 1.382 (5) |
Cd1—I1 | 2.8990 (6) | C7—H7 | 0.9300 |
N1—C2 | 1.337 (5) | C8—H8 | 0.9300 |
N1—N2 | 1.351 (5) | C9—C10 | 1.413 (5) |
N1—H1 | 0.8700 (11) | C9—C1i | 1.465 (5) |
N2—C1 | 1.305 (5) | C10—C11 | 1.362 (7) |
N3—C9 | 1.329 (5) | C10—H10 | 0.9300 |
N3—C13 | 1.347 (5) | C11—C12 | 1.385 (7) |
N4—C2 | 1.334 (5) | C11—H11 | 0.9300 |
N4—C1 | 1.377 (4) | C12—C13 | 1.381 (6) |
C1—C9i | 1.465 (5) | C12—H12 | 0.9300 |
C2—C3 | 1.465 (5) | C13—H13 | 0.9300 |
C3—C4 | 1.390 (6) | C14—H14A | 0.9600 |
C3—C8 | 1.391 (5) | C14—H14B | 0.9600 |
C4—C5 | 1.391 (6) | C14—H14C | 0.9600 |
C4—H4 | 0.9300 | | |
| | | |
N3i—Cd1—N3 | 157.63 (16) | C3—C4—H4 | 119.5 |
N3i—Cd1—N4i | 91.87 (10) | C5—C4—H4 | 119.5 |
N3—Cd1—N4i | 70.79 (10) | C6—C5—C4 | 120.8 (4) |
N3i—Cd1—N4 | 70.79 (10) | C6—C5—H5 | 119.6 |
N3—Cd1—N4 | 91.87 (10) | C4—C5—H5 | 119.6 |
N4i—Cd1—N4 | 80.36 (13) | C7—C6—C5 | 118.0 (4) |
N3i—Cd1—I1i | 104.74 (9) | C7—C6—C14 | 120.9 (4) |
N3—Cd1—I1i | 90.59 (8) | C5—C6—C14 | 121.0 (4) |
N4i—Cd1—I1i | 93.02 (6) | C8—C7—C6 | 121.2 (4) |
N4—Cd1—I1i | 171.74 (6) | C8—C7—H7 | 119.4 |
N3i—Cd1—I1 | 90.59 (8) | C6—C7—H7 | 119.4 |
N3—Cd1—I1 | 104.74 (9) | C7—C8—C3 | 121.2 (4) |
N4i—Cd1—I1 | 171.74 (6) | C7—C8—H8 | 119.4 |
N4—Cd1—I1 | 93.02 (6) | C3—C8—H8 | 119.4 |
I1i—Cd1—I1 | 93.98 (2) | N3—C9—C10 | 121.6 (3) |
C2—N1—N2 | 111.4 (3) | N3—C9—C1i | 117.8 (3) |
C2—N1—H1 | 121 (3) | C10—C9—C1i | 120.5 (4) |
N2—N1—H1 | 125 (3) | C11—C10—C9 | 118.2 (4) |
C1—N2—N1 | 102.6 (3) | C11—C10—H10 | 120.9 |
C9—N3—C13 | 119.1 (3) | C9—C10—H10 | 120.9 |
C9—N3—Cd1 | 121.1 (2) | C10—C11—C12 | 120.4 (4) |
C13—N3—Cd1 | 119.8 (3) | C10—C11—H11 | 119.8 |
C2—N4—C1 | 103.2 (3) | C12—C11—H11 | 119.8 |
C2—N4—Cd1 | 150.6 (2) | C13—C12—C11 | 118.1 (4) |
C1—N4—Cd1 | 106.2 (2) | C13—C12—H12 | 121.0 |
N2—C1—N4 | 114.3 (3) | C11—C12—H12 | 121.0 |
N2—C1—C9i | 121.8 (3) | N3—C13—C12 | 122.3 (4) |
N4—C1—C9i | 123.7 (3) | N3—C13—H13 | 118.8 |
N4—C2—N1 | 108.5 (3) | C12—C13—H13 | 118.8 |
N4—C2—C3 | 129.4 (3) | C6—C14—H14A | 109.5 |
N1—C2—C3 | 122.1 (3) | C6—C14—H14B | 109.5 |
C4—C3—C8 | 117.6 (3) | H14A—C14—H14B | 109.5 |
C4—C3—C2 | 121.2 (3) | C6—C14—H14C | 109.5 |
C8—C3—C2 | 121.1 (3) | H14A—C14—H14C | 109.5 |
C3—C4—C5 | 121.1 (4) | H14B—C14—H14C | 109.5 |
| | | |
C2—N1—N2—C1 | 1.5 (5) | C3—C4—C5—C6 | −0.2 (6) |
N1—N2—C1—N4 | −0.7 (4) | C4—C5—C6—C7 | −0.9 (6) |
N1—N2—C1—C9i | −176.9 (3) | C4—C5—C6—C14 | −179.7 (4) |
C2—N4—C1—N2 | −0.3 (4) | C5—C6—C7—C8 | 2.3 (6) |
Cd1—N4—C1—N2 | 178.6 (3) | C14—C6—C7—C8 | −178.9 (4) |
C2—N4—C1—C9i | 175.8 (3) | C6—C7—C8—C3 | −2.5 (7) |
Cd1—N4—C1—C9i | −5.3 (4) | C4—C3—C8—C7 | 1.2 (6) |
C1—N4—C2—N1 | 1.2 (4) | C2—C3—C8—C7 | 180.0 (4) |
Cd1—N4—C2—N1 | −176.5 (4) | C13—N3—C9—C10 | 3.3 (5) |
C1—N4—C2—C3 | −178.7 (4) | Cd1—N3—C9—C10 | −177.2 (3) |
Cd1—N4—C2—C3 | 3.5 (7) | C13—N3—C9—C1i | −174.6 (3) |
N2—N1—C2—N4 | −1.8 (5) | Cd1—N3—C9—C1i | 4.9 (4) |
N2—N1—C2—C3 | 178.2 (3) | N3—C9—C10—C11 | −0.3 (6) |
N4—C2—C3—C4 | −166.5 (4) | C1i—C9—C10—C11 | 177.5 (3) |
N1—C2—C3—C4 | 13.5 (6) | C9—C10—C11—C12 | −3.1 (6) |
N4—C2—C3—C8 | 14.8 (6) | C10—C11—C12—C13 | 3.3 (7) |
N1—C2—C3—C8 | −165.2 (4) | C9—N3—C13—C12 | −3.0 (6) |
C8—C3—C4—C5 | 0.1 (6) | Cd1—N3—C13—C12 | 177.5 (3) |
C2—C3—C4—C5 | −178.7 (4) | C11—C12—C13—N3 | −0.3 (7) |
Symmetry code: (i) −x+1, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···I1ii | 0.87 (1) | 2.71 (2) | 3.534 (3) | 159 (4) |
C12—H12···I1iii | 0.93 | 3.29 | 3.884 (5) | 124 |
Symmetry codes: (ii) −x+1, −y+1, −z; (iii) −x+1/2, −y+3/2, −z. |
(V) Bis[5-(4-methylphenyl)-3-(pyridin-2-yl)-1
H-1,2,4-triazole-
κ2N3,
N4]bis(nitrato-
κO)cadmium(II)
top
Crystal data top
[Cd(NO3)2(C14H12N4)2] | F(000) = 1432 |
Mr = 708.98 | Dx = 1.649 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 17.113 (3) Å | Cell parameters from 12693 reflections |
b = 12.603 (3) Å | θ = 3.1–25.0° |
c = 14.708 (3) Å | µ = 0.83 mm−1 |
β = 115.80 (3)° | T = 293 K |
V = 2855.9 (12) Å3 | Block, colourless |
Z = 4 | 0.31 × 0.28 × 0.26 mm |
Data collection top
Rigaku MM007-HF CCD (Saturn 724+) diffractometer | 2336 reflections with I > 2σ(I) |
Radiation source: rotating anode | Rint = 0.048 |
ω scans at fixed χ = 45° | θmax = 25.0°, θmin = 3.1° |
Absorption correction: multi-scan ABSCOR | h = −20→20 |
Tmin = 0.774, Tmax = 0.807 | k = −14→14 |
9965 measured reflections | l = −17→17 |
2495 independent reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.030 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.068 | w = 1/[σ2(Fo2) + (0.0348P)2 + 0.6811P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.001 |
2495 reflections | Δρmax = 0.40 e Å−3 |
209 parameters | Δρmin = −0.48 e Å−3 |
1 restraint | Extinction correction: SHELXL-2014/7 (Sheldrick 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0019 (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. SHELXL-2014/7 (Sheldrick, 2015) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cd1 | 0.5000 | 0.37028 (2) | 0.2500 | 0.02761 (12) | |
N1 | 0.53288 (14) | 0.67516 (17) | 0.10020 (15) | 0.0379 (5) | |
H1 | 0.5261 (19) | 0.7278 (13) | 0.0592 (15) | 0.057* | |
N2 | 0.61303 (14) | 0.65221 (17) | 0.17397 (16) | 0.0392 (5) | |
N3 | 0.64694 (12) | 0.40041 (15) | 0.30256 (14) | 0.0303 (4) | |
N4 | 0.51837 (12) | 0.51949 (15) | 0.15311 (13) | 0.0282 (4) | |
N5 | 0.51830 (12) | 0.19354 (16) | 0.12028 (15) | 0.0354 (5) | |
O1 | 0.46517 (11) | 0.26928 (13) | 0.10618 (12) | 0.0412 (4) | |
O2 | 0.51257 (13) | 0.14472 (14) | 0.04362 (15) | 0.0476 (5) | |
O3 | 0.57316 (14) | 0.17370 (18) | 0.20563 (15) | 0.0623 (6) | |
C1 | 0.47705 (15) | 0.59533 (19) | 0.08706 (16) | 0.0298 (5) | |
C2 | 0.60083 (14) | 0.55744 (18) | 0.20319 (16) | 0.0297 (5) | |
C3 | 0.67073 (14) | 0.49398 (18) | 0.27933 (16) | 0.0291 (5) | |
C4 | 0.75733 (15) | 0.5262 (2) | 0.32137 (18) | 0.0379 (6) | |
H4A | 0.7726 | 0.5918 | 0.3049 | 0.045* | |
C5 | 0.81950 (15) | 0.4598 (2) | 0.38722 (19) | 0.0420 (6) | |
H5 | 0.8775 | 0.4804 | 0.4170 | 0.050* | |
C6 | 0.79557 (17) | 0.3622 (2) | 0.4091 (2) | 0.0412 (6) | |
H6 | 0.8371 | 0.3152 | 0.4520 | 0.049* | |
C7 | 0.70863 (16) | 0.3359 (2) | 0.36583 (19) | 0.0380 (6) | |
H7 | 0.6923 | 0.2705 | 0.3814 | 0.046* | |
C8 | 0.38581 (15) | 0.5943 (2) | 0.01227 (16) | 0.0319 (5) | |
C9 | 0.34220 (16) | 0.6877 (2) | −0.0315 (2) | 0.0461 (7) | |
H9 | 0.3715 | 0.7522 | −0.0158 | 0.055* | |
C10 | 0.25472 (17) | 0.6842 (2) | −0.0988 (2) | 0.0527 (7) | |
H10 | 0.2262 | 0.7469 | −0.1280 | 0.063* | |
C11 | 0.20923 (17) | 0.5900 (2) | −0.1233 (2) | 0.0435 (6) | |
C12 | 0.25412 (16) | 0.4973 (2) | −0.08254 (19) | 0.0431 (6) | |
H12 | 0.2251 | 0.4327 | −0.1002 | 0.052* | |
C13 | 0.34168 (16) | 0.49901 (19) | −0.01579 (17) | 0.0362 (5) | |
H13 | 0.3708 | 0.4357 | 0.0102 | 0.043* | |
C14 | 0.11312 (19) | 0.5877 (3) | −0.1908 (2) | 0.0637 (9) | |
H14A | 0.0833 | 0.5584 | −0.1545 | 0.095* | |
H14B | 0.1021 | 0.5447 | −0.2490 | 0.095* | |
H14C | 0.0928 | 0.6586 | −0.2120 | 0.095* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cd1 | 0.02055 (15) | 0.02801 (17) | 0.02983 (17) | 0.000 | 0.00685 (11) | 0.000 |
N1 | 0.0343 (11) | 0.0332 (12) | 0.0385 (12) | −0.0011 (9) | 0.0087 (10) | 0.0090 (9) |
N2 | 0.0316 (11) | 0.0372 (12) | 0.0405 (13) | −0.0031 (9) | 0.0079 (10) | 0.0069 (9) |
N3 | 0.0224 (9) | 0.0304 (11) | 0.0342 (11) | 0.0016 (8) | 0.0088 (8) | 0.0018 (8) |
N4 | 0.0239 (9) | 0.0301 (11) | 0.0284 (10) | 0.0006 (8) | 0.0093 (8) | 0.0025 (7) |
N5 | 0.0298 (10) | 0.0294 (11) | 0.0407 (12) | −0.0010 (8) | 0.0096 (10) | −0.0034 (9) |
O1 | 0.0407 (9) | 0.0346 (10) | 0.0411 (10) | 0.0096 (8) | 0.0110 (8) | −0.0058 (7) |
O2 | 0.0464 (11) | 0.0398 (11) | 0.0542 (13) | 0.0022 (8) | 0.0196 (10) | −0.0151 (8) |
O3 | 0.0526 (12) | 0.0643 (14) | 0.0485 (13) | 0.0177 (11) | 0.0019 (10) | 0.0046 (10) |
C1 | 0.0289 (12) | 0.0306 (12) | 0.0306 (12) | 0.0016 (10) | 0.0136 (10) | 0.0010 (9) |
C2 | 0.0287 (12) | 0.0285 (12) | 0.0319 (12) | −0.0004 (9) | 0.0134 (10) | 0.0002 (9) |
C3 | 0.0252 (11) | 0.0310 (13) | 0.0289 (12) | 0.0008 (9) | 0.0096 (10) | −0.0014 (9) |
C4 | 0.0271 (12) | 0.0390 (14) | 0.0435 (14) | −0.0057 (10) | 0.0115 (11) | 0.0022 (10) |
C5 | 0.0213 (11) | 0.0554 (17) | 0.0429 (15) | −0.0014 (11) | 0.0081 (11) | 0.0005 (11) |
C6 | 0.0246 (12) | 0.0467 (17) | 0.0431 (16) | 0.0090 (10) | 0.0061 (12) | 0.0038 (10) |
C7 | 0.0288 (12) | 0.0351 (14) | 0.0446 (15) | 0.0047 (10) | 0.0109 (11) | 0.0074 (11) |
C8 | 0.0289 (12) | 0.0370 (13) | 0.0280 (13) | 0.0038 (10) | 0.0106 (10) | 0.0042 (9) |
C9 | 0.0322 (13) | 0.0365 (15) | 0.0610 (18) | 0.0039 (11) | 0.0122 (13) | 0.0102 (12) |
C10 | 0.0340 (14) | 0.0458 (18) | 0.0644 (19) | 0.0121 (12) | 0.0085 (13) | 0.0163 (13) |
C11 | 0.0303 (13) | 0.0557 (17) | 0.0378 (14) | 0.0024 (12) | 0.0085 (11) | 0.0024 (12) |
C12 | 0.0382 (14) | 0.0454 (16) | 0.0362 (14) | −0.0055 (11) | 0.0072 (12) | −0.0017 (11) |
C13 | 0.0368 (13) | 0.0350 (14) | 0.0291 (13) | 0.0055 (10) | 0.0073 (11) | 0.0031 (9) |
C14 | 0.0323 (15) | 0.077 (2) | 0.064 (2) | 0.0014 (15) | 0.0048 (14) | 0.0021 (17) |
Geometric parameters (Å, º) top
Cd1—O1i | 2.3135 (17) | C4—H4A | 0.9300 |
Cd1—O1 | 2.3136 (17) | C5—C6 | 1.377 (4) |
Cd1—N3 | 2.3179 (19) | C5—H5 | 0.9300 |
Cd1—N3i | 2.3180 (19) | C6—C7 | 1.380 (4) |
Cd1—N4i | 2.4609 (18) | C6—H6 | 0.9300 |
Cd1—N4 | 2.4609 (18) | C7—H7 | 0.9300 |
N1—C1 | 1.342 (3) | C8—C13 | 1.383 (3) |
N1—N2 | 1.359 (3) | C8—C9 | 1.392 (3) |
N1—H1 | 0.8700 (11) | C9—C10 | 1.390 (4) |
N2—C2 | 1.316 (3) | C9—H9 | 0.9300 |
N3—C7 | 1.336 (3) | C10—C11 | 1.379 (4) |
N3—C3 | 1.339 (3) | C10—H10 | 0.9300 |
N4—C1 | 1.326 (3) | C11—C12 | 1.383 (4) |
N4—C2 | 1.363 (3) | C11—C14 | 1.507 (4) |
N5—O3 | 1.222 (3) | C12—C13 | 1.389 (3) |
N5—O2 | 1.250 (3) | C12—H12 | 0.9300 |
N5—O1 | 1.271 (3) | C13—H13 | 0.9300 |
C1—C8 | 1.467 (3) | C14—H14A | 0.9600 |
C2—C3 | 1.469 (3) | C14—H14B | 0.9600 |
C3—C4 | 1.395 (3) | C14—H14C | 0.9600 |
C4—C5 | 1.369 (4) | | |
| | | |
O1i—Cd1—O1 | 113.24 (9) | C4—C3—C2 | 122.3 (2) |
O1i—Cd1—N3 | 88.56 (7) | C5—C4—C3 | 119.0 (2) |
O1—Cd1—N3 | 101.86 (7) | C5—C4—H4A | 120.5 |
O1i—Cd1—N3i | 101.86 (7) | C3—C4—H4A | 120.5 |
O1—Cd1—N3i | 88.56 (7) | C4—C5—C6 | 119.5 (2) |
N3—Cd1—N3i | 161.14 (10) | C4—C5—H5 | 120.3 |
O1i—Cd1—N4i | 86.44 (6) | C6—C5—H5 | 120.3 |
O1—Cd1—N4i | 154.54 (6) | C5—C6—C7 | 118.5 (2) |
N3—Cd1—N4i | 94.31 (7) | C5—C6—H6 | 120.7 |
N3i—Cd1—N4i | 71.00 (7) | C7—C6—H6 | 120.7 |
O1i—Cd1—N4 | 154.54 (6) | N3—C7—C6 | 122.7 (2) |
O1—Cd1—N4 | 86.44 (6) | N3—C7—H7 | 118.6 |
N3—Cd1—N4 | 71.00 (7) | C6—C7—H7 | 118.6 |
N3i—Cd1—N4 | 94.31 (7) | C13—C8—C9 | 118.9 (2) |
N4i—Cd1—N4 | 80.34 (9) | C13—C8—C1 | 119.7 (2) |
C1—N1—N2 | 111.30 (19) | C9—C8—C1 | 121.4 (2) |
C1—N1—H1 | 126.9 (19) | C10—C9—C8 | 119.8 (3) |
N2—N1—H1 | 120 (2) | C10—C9—H9 | 120.1 |
C2—N2—N1 | 101.85 (19) | C8—C9—H9 | 120.1 |
C7—N3—C3 | 118.5 (2) | C11—C10—C9 | 121.6 (3) |
C7—N3—Cd1 | 123.10 (16) | C11—C10—H10 | 119.2 |
C3—N3—Cd1 | 117.72 (14) | C9—C10—H10 | 119.2 |
C1—N4—C2 | 103.85 (19) | C10—C11—C12 | 118.0 (2) |
C1—N4—Cd1 | 144.39 (15) | C10—C11—C14 | 121.2 (3) |
C2—N4—Cd1 | 108.56 (14) | C12—C11—C14 | 120.7 (3) |
O3—N5—O2 | 123.3 (2) | C11—C12—C13 | 121.2 (2) |
O3—N5—O1 | 119.7 (2) | C11—C12—H12 | 119.4 |
O2—N5—O1 | 116.91 (19) | C13—C12—H12 | 119.4 |
N5—O1—Cd1 | 112.49 (13) | C8—C13—C12 | 120.3 (2) |
N4—C1—N1 | 108.4 (2) | C8—C13—H13 | 119.8 |
N4—C1—C8 | 126.7 (2) | C12—C13—H13 | 119.8 |
N1—C1—C8 | 124.9 (2) | C11—C14—H14A | 109.5 |
N2—C2—N4 | 114.6 (2) | C11—C14—H14B | 109.5 |
N2—C2—C3 | 123.4 (2) | H14A—C14—H14B | 109.5 |
N4—C2—C3 | 121.9 (2) | C11—C14—H14C | 109.5 |
N3—C3—C4 | 121.7 (2) | H14A—C14—H14C | 109.5 |
N3—C3—C2 | 115.89 (19) | H14B—C14—H14C | 109.5 |
| | | |
C1—N1—N2—C2 | −0.7 (3) | N4—C2—C3—C4 | 171.4 (2) |
O3—N5—O1—Cd1 | 8.5 (3) | N3—C3—C4—C5 | 0.7 (4) |
O2—N5—O1—Cd1 | −169.48 (15) | C2—C3—C4—C5 | −176.0 (2) |
C2—N4—C1—N1 | −1.5 (2) | C3—C4—C5—C6 | 1.2 (4) |
Cd1—N4—C1—N1 | 153.7 (2) | C4—C5—C6—C7 | −2.0 (4) |
C2—N4—C1—C8 | 179.0 (2) | C3—N3—C7—C6 | 0.8 (4) |
Cd1—N4—C1—C8 | −25.9 (4) | Cd1—N3—C7—C6 | −169.7 (2) |
N2—N1—C1—N4 | 1.4 (3) | C5—C6—C7—N3 | 1.0 (4) |
N2—N1—C1—C8 | −179.0 (2) | N4—C1—C8—C13 | −19.8 (4) |
N1—N2—C2—N4 | −0.3 (3) | N1—C1—C8—C13 | 160.8 (2) |
N1—N2—C2—C3 | 176.3 (2) | N4—C1—C8—C9 | 160.2 (2) |
C1—N4—C2—N2 | 1.1 (3) | N1—C1—C8—C9 | −19.2 (4) |
Cd1—N4—C2—N2 | −163.91 (16) | C13—C8—C9—C10 | 2.8 (4) |
C1—N4—C2—C3 | −175.6 (2) | C1—C8—C9—C10 | −177.2 (2) |
Cd1—N4—C2—C3 | 19.4 (2) | C8—C9—C10—C11 | 0.4 (4) |
C7—N3—C3—C4 | −1.7 (3) | C9—C10—C11—C12 | −3.0 (4) |
Cd1—N3—C3—C4 | 169.32 (17) | C9—C10—C11—C14 | 175.9 (3) |
C7—N3—C3—C2 | 175.2 (2) | C10—C11—C12—C13 | 2.4 (4) |
Cd1—N3—C3—C2 | −13.8 (3) | C14—C11—C12—C13 | −176.4 (3) |
N2—C2—C3—N3 | 178.2 (2) | C9—C8—C13—C12 | −3.3 (4) |
N4—C2—C3—N3 | −5.4 (3) | C1—C8—C13—C12 | 176.7 (2) |
N2—C2—C3—C4 | −5.0 (4) | C11—C12—C13—C8 | 0.7 (4) |
Symmetry code: (i) −x+1, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N5ii | 0.87 (1) | 2.60 (1) | 3.398 (3) | 152 (2) |
N1—H1···O1ii | 0.87 (1) | 2.50 (2) | 3.129 (3) | 130 (2) |
N1—H1···O2ii | 0.87 (1) | 2.11 (1) | 2.967 (3) | 170 (3) |
C6—H6···O1iii | 0.93 | 2.60 | 3.500 (3) | 164 |
Symmetry codes: (ii) −x+1, −y+1, −z; (iii) x+1/2, −y+1/2, z+1/2. |
(VI) Aquabis[5-(4-methylphenyl)-3-(pyridin-2-yl)-1
H-1,2,4-triazolato-
κ2N1,
N5]cobalt(II)
top
Crystal data top
[Co(C14H11N4)2(H2O)] | F(000) = 1132 |
Mr = 547.48 | Dx = 1.471 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 28.735 (6) Å | Cell parameters from 12169 reflections |
b = 7.4617 (15) Å | θ = 3.1–25.0° |
c = 12.421 (3) Å | µ = 0.73 mm−1 |
β = 111.79 (3)° | T = 293 K |
V = 2472.9 (10) Å3 | Block, red |
Z = 4 | 0.31 × 0.27 × 0.25 mm |
Data collection top
Rigaku MM007-HF CCD (Saturn 724+) diffractometer | 1866 reflections with I > 2σ(I) |
Radiation source: rotating anode | Rint = 0.032 |
ω scans at fixed χ = 45° | θmax = 25.0°, θmin = 3.1° |
Absorption correction: multi-scan ABSCOR | h = −34→34 |
Tmin = 0.796, Tmax = 0.832 | k = −8→8 |
9301 measured reflections | l = −14→14 |
2177 independent 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)] = 0.029 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.071 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0315P)2 + 1.7253P] where P = (Fo2 + 2Fc2)/3 |
2177 reflections | (Δ/σ)max < 0.001 |
174 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.23 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. SHELXL-2014/7 (Sheldrick, 2015) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Co1 | 0.0000 | 0.88006 (5) | 0.2500 | 0.03214 (13) | |
O1W | 0.0000 | 1.1468 (3) | 0.2500 | 0.0430 (5) | |
H1 | 0.0088 | 1.2041 | 0.2045 | 0.065* | |
N1 | −0.03312 (6) | 0.7797 (2) | 0.08970 (12) | 0.0342 (4) | |
N2 | −0.08111 (6) | 0.7396 (2) | 0.01684 (13) | 0.0365 (4) | |
N3 | 0.06247 (6) | 0.8606 (2) | 0.19489 (13) | 0.0322 (4) | |
N4 | −0.02919 (6) | 0.7113 (2) | −0.08164 (12) | 0.0306 (4) | |
C1 | −0.07690 (7) | 0.6996 (3) | −0.08404 (15) | 0.0302 (4) | |
C2 | −0.00365 (7) | 0.7615 (2) | 0.02813 (14) | 0.0291 (4) | |
C3 | 0.04983 (7) | 0.7986 (3) | 0.08521 (15) | 0.0297 (4) | |
C4 | 0.08522 (7) | 0.7711 (3) | 0.03616 (17) | 0.0393 (5) | |
H4 | 0.0758 | 0.7282 | −0.0393 | 0.047* | |
C5 | 0.13471 (8) | 0.8083 (3) | 0.10114 (19) | 0.0465 (5) | |
H5 | 0.1592 | 0.7910 | 0.0698 | 0.056* | |
C6 | 0.14772 (8) | 0.8712 (3) | 0.21247 (18) | 0.0439 (5) | |
H6 | 0.1809 | 0.8972 | 0.2574 | 0.053* | |
C7 | 0.11054 (7) | 0.8950 (3) | 0.25617 (17) | 0.0390 (5) | |
H7 | 0.1194 | 0.9369 | 0.3317 | 0.047* | |
C8 | −0.12048 (7) | 0.6482 (3) | −0.18666 (15) | 0.0319 (4) | |
C9 | −0.11495 (8) | 0.5704 (3) | −0.28298 (16) | 0.0367 (5) | |
H9 | −0.0830 | 0.5504 | −0.2830 | 0.044* | |
C10 | −0.15641 (8) | 0.5224 (3) | −0.37867 (17) | 0.0403 (5) | |
H10 | −0.1518 | 0.4703 | −0.4420 | 0.048* | |
C11 | −0.20464 (8) | 0.5500 (3) | −0.38274 (17) | 0.0401 (5) | |
C12 | −0.21000 (8) | 0.6271 (3) | −0.28589 (18) | 0.0451 (5) | |
H12 | −0.2420 | 0.6465 | −0.2859 | 0.054* | |
C13 | −0.16890 (8) | 0.6752 (3) | −0.19002 (17) | 0.0412 (5) | |
H13 | −0.1736 | 0.7266 | −0.1266 | 0.049* | |
C14 | −0.24995 (9) | 0.4998 (3) | −0.4882 (2) | 0.0572 (6) | |
H14A | −0.2392 | 0.4464 | −0.5453 | 0.086* | |
H14B | −0.2693 | 0.6054 | −0.5199 | 0.086* | |
H14C | −0.2702 | 0.4159 | −0.4663 | 0.086* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Co1 | 0.0335 (2) | 0.0426 (2) | 0.02309 (19) | 0.000 | 0.01376 (16) | 0.000 |
O1W | 0.0610 (14) | 0.0456 (12) | 0.0366 (10) | 0.000 | 0.0344 (10) | 0.000 |
N1 | 0.0304 (9) | 0.0483 (10) | 0.0271 (8) | −0.0022 (8) | 0.0145 (7) | −0.0019 (7) |
N2 | 0.0317 (9) | 0.0521 (11) | 0.0282 (8) | −0.0058 (8) | 0.0141 (7) | −0.0039 (8) |
N3 | 0.0314 (9) | 0.0391 (9) | 0.0271 (7) | 0.0019 (7) | 0.0121 (7) | 0.0006 (7) |
N4 | 0.0326 (9) | 0.0373 (9) | 0.0253 (7) | −0.0001 (7) | 0.0147 (7) | 0.0016 (7) |
C1 | 0.0320 (10) | 0.0341 (10) | 0.0269 (9) | −0.0006 (8) | 0.0137 (8) | 0.0035 (8) |
C2 | 0.0312 (10) | 0.0336 (10) | 0.0256 (9) | 0.0023 (8) | 0.0143 (8) | 0.0032 (8) |
C3 | 0.0333 (10) | 0.0323 (10) | 0.0261 (9) | 0.0027 (8) | 0.0138 (8) | 0.0040 (8) |
C4 | 0.0359 (11) | 0.0535 (13) | 0.0325 (10) | 0.0005 (10) | 0.0174 (9) | −0.0034 (9) |
C5 | 0.0341 (12) | 0.0631 (15) | 0.0494 (12) | 0.0008 (11) | 0.0237 (11) | −0.0002 (11) |
C6 | 0.0298 (11) | 0.0554 (14) | 0.0453 (12) | −0.0026 (10) | 0.0125 (10) | −0.0011 (11) |
C7 | 0.0349 (12) | 0.0481 (13) | 0.0317 (10) | −0.0013 (10) | 0.0095 (9) | −0.0032 (9) |
C8 | 0.0344 (11) | 0.0344 (11) | 0.0286 (9) | −0.0017 (9) | 0.0137 (9) | 0.0044 (8) |
C9 | 0.0354 (11) | 0.0433 (12) | 0.0340 (10) | 0.0002 (9) | 0.0161 (9) | −0.0005 (9) |
C10 | 0.0458 (13) | 0.0428 (12) | 0.0321 (10) | −0.0008 (10) | 0.0141 (10) | −0.0049 (9) |
C11 | 0.0396 (12) | 0.0388 (11) | 0.0354 (10) | −0.0019 (10) | 0.0063 (9) | 0.0030 (9) |
C12 | 0.0302 (11) | 0.0587 (14) | 0.0460 (12) | 0.0020 (10) | 0.0139 (10) | 0.0006 (11) |
C13 | 0.0399 (12) | 0.0538 (13) | 0.0338 (10) | 0.0009 (10) | 0.0181 (10) | −0.0020 (10) |
C14 | 0.0498 (14) | 0.0558 (16) | 0.0522 (13) | −0.0024 (12) | 0.0031 (12) | −0.0059 (12) |
Geometric parameters (Å, º) top
Co1—O1W | 1.990 (2) | C5—H5 | 0.9300 |
Co1—N1 | 2.0061 (16) | C6—C7 | 1.378 (3) |
Co1—N1i | 2.0062 (16) | C6—H6 | 0.9300 |
Co1—N3i | 2.1504 (15) | C7—H7 | 0.9300 |
Co1—N3 | 2.1505 (15) | C8—C9 | 1.391 (3) |
O1W—H1 | 0.8199 | C8—C13 | 1.391 (3) |
N1—C2 | 1.342 (2) | C9—C10 | 1.382 (3) |
N1—N2 | 1.372 (2) | C9—H9 | 0.9300 |
N2—C1 | 1.337 (2) | C10—C11 | 1.383 (3) |
N3—C7 | 1.331 (3) | C10—H10 | 0.9300 |
N3—C3 | 1.355 (2) | C11—C12 | 1.393 (3) |
N4—C2 | 1.340 (2) | C11—C14 | 1.511 (3) |
N4—C1 | 1.363 (2) | C12—C13 | 1.378 (3) |
C1—C8 | 1.468 (3) | C12—H12 | 0.9300 |
C2—C3 | 1.460 (3) | C13—H13 | 0.9300 |
C3—C4 | 1.381 (3) | C14—H14A | 0.9600 |
C4—C5 | 1.378 (3) | C14—H14B | 0.9600 |
C4—H4 | 0.9300 | C14—H14C | 0.9600 |
C5—C6 | 1.374 (3) | | |
| | | |
O1W—Co1—N1 | 111.93 (5) | C6—C5—H5 | 120.2 |
O1W—Co1—N1i | 111.93 (5) | C4—C5—H5 | 120.2 |
N1—Co1—N1i | 136.14 (10) | C5—C6—C7 | 118.65 (19) |
O1W—Co1—N3i | 93.86 (4) | C5—C6—H6 | 120.7 |
N1—Co1—N3i | 98.41 (6) | C7—C6—H6 | 120.7 |
N1i—Co1—N3i | 78.66 (6) | N3—C7—C6 | 122.79 (18) |
O1W—Co1—N3 | 93.86 (4) | N3—C7—H7 | 118.6 |
N1—Co1—N3 | 78.66 (6) | C6—C7—H7 | 118.6 |
N1i—Co1—N3 | 98.41 (6) | C9—C8—C13 | 117.85 (18) |
N3i—Co1—N3 | 172.28 (9) | C9—C8—C1 | 121.54 (17) |
Co1—O1W—H1 | 121.4 | C13—C8—C1 | 120.62 (16) |
C2—N1—N2 | 107.11 (14) | C10—C9—C8 | 120.71 (18) |
C2—N1—Co1 | 115.86 (12) | C10—C9—H9 | 119.6 |
N2—N1—Co1 | 136.57 (12) | C8—C9—H9 | 119.6 |
C1—N2—N1 | 104.38 (15) | C9—C10—C11 | 121.69 (18) |
C7—N3—C3 | 118.35 (16) | C9—C10—H10 | 119.2 |
C7—N3—Co1 | 128.06 (13) | C11—C10—H10 | 119.2 |
C3—N3—Co1 | 113.53 (12) | C10—C11—C12 | 117.41 (19) |
C2—N4—C1 | 101.93 (14) | C10—C11—C14 | 121.61 (19) |
N2—C1—N4 | 113.92 (16) | C12—C11—C14 | 121.0 (2) |
N2—C1—C8 | 121.84 (16) | C13—C12—C11 | 121.3 (2) |
N4—C1—C8 | 124.24 (15) | C13—C12—H12 | 119.3 |
N4—C2—N1 | 112.66 (16) | C11—C12—H12 | 119.3 |
N4—C2—C3 | 128.84 (15) | C12—C13—C8 | 120.99 (18) |
N1—C2—C3 | 118.50 (15) | C12—C13—H13 | 119.5 |
N3—C3—C4 | 121.87 (17) | C8—C13—H13 | 119.5 |
N3—C3—C2 | 113.22 (15) | C11—C14—H14A | 109.5 |
C4—C3—C2 | 124.90 (17) | C11—C14—H14B | 109.5 |
C5—C4—C3 | 118.71 (18) | H14A—C14—H14B | 109.5 |
C5—C4—H4 | 120.6 | C11—C14—H14C | 109.5 |
C3—C4—H4 | 120.6 | H14A—C14—H14C | 109.5 |
C6—C5—C4 | 119.63 (19) | H14B—C14—H14C | 109.5 |
| | | |
C2—N1—N2—C1 | 0.1 (2) | C2—C3—C4—C5 | −178.56 (19) |
Co1—N1—N2—C1 | 171.60 (15) | C3—C4—C5—C6 | 0.1 (3) |
N1—N2—C1—N4 | −0.1 (2) | C4—C5—C6—C7 | 0.1 (3) |
N1—N2—C1—C8 | 179.93 (17) | C3—N3—C7—C6 | 0.4 (3) |
C2—N4—C1—N2 | 0.1 (2) | Co1—N3—C7—C6 | 177.52 (15) |
C2—N4—C1—C8 | −179.97 (18) | C5—C6—C7—N3 | −0.4 (3) |
C1—N4—C2—N1 | 0.0 (2) | N2—C1—C8—C9 | −166.02 (19) |
C1—N4—C2—C3 | −179.29 (19) | N4—C1—C8—C9 | 14.0 (3) |
N2—N1—C2—N4 | −0.1 (2) | N2—C1—C8—C13 | 13.6 (3) |
Co1—N1—C2—N4 | −173.59 (12) | N4—C1—C8—C13 | −166.38 (18) |
N2—N1—C2—C3 | 179.31 (16) | C13—C8—C9—C10 | 0.2 (3) |
Co1—N1—C2—C3 | 5.8 (2) | C1—C8—C9—C10 | 179.83 (18) |
C7—N3—C3—C4 | −0.2 (3) | C8—C9—C10—C11 | 0.2 (3) |
Co1—N3—C3—C4 | −177.68 (15) | C9—C10—C11—C12 | −0.5 (3) |
C7—N3—C3—C2 | 178.45 (17) | C9—C10—C11—C14 | 179.1 (2) |
Co1—N3—C3—C2 | 1.0 (2) | C10—C11—C12—C13 | 0.4 (3) |
N4—C2—C3—N3 | 174.89 (18) | C14—C11—C12—C13 | −179.2 (2) |
N1—C2—C3—N3 | −4.4 (3) | C11—C12—C13—C8 | −0.1 (3) |
N4—C2—C3—C4 | −6.5 (3) | C9—C8—C13—C12 | −0.3 (3) |
N1—C2—C3—C4 | 174.20 (18) | C1—C8—C13—C12 | −179.89 (19) |
N3—C3—C4—C5 | −0.1 (3) | | |
Symmetry code: (i) −x, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1···N4ii | 0.82 | 1.93 | 2.7386 (17) | 167 |
Symmetry code: (ii) −x, −y+2, −z. |
(VII) Diaquabis[5-(4-methylphenyl)-3-(pyridin-2-yl)-1
H-1,2,4-triazolato-
κ2N1,
N5]nickel(II)
top
Crystal data top
[Ni(C14H11N4)2(H2O)2] | F(000) = 1176 |
Mr = 565.28 | Dx = 1.504 Mg m−3 |
Monoclinic, I2/a | Mo Kα radiation, λ = 0.71073 Å |
a = 26.778 (5) Å | Cell parameters from 12342 reflections |
b = 7.4858 (15) Å | θ = 3.1–25.0° |
c = 12.472 (3) Å | µ = 0.82 mm−1 |
β = 92.91 (3)° | T = 293 K |
V = 2496.8 (9) Å3 | Block, purple |
Z = 4 | 0.32 × 0.28 × 0.26 mm |
Data collection top
Rigaku MM007-HF CCD (Saturn 724+) diffractometer | 2016 reflections with I > 2σ(I) |
Radiation source: rotating anode | Rint = 0.023 |
ω scans at fixed χ = 45° | θmax = 25.0°, θmin = 3.1° |
Absorption correction: multi-scan ABSCOR | h = −31→31 |
Tmin = 0.769, Tmax = 0.808 | k = −8→8 |
9388 measured reflections | l = −13→14 |
2186 independent 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)] = 0.024 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.067 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0409P)2 + 1.0824P] where P = (Fo2 + 2Fc2)/3 |
2186 reflections | (Δ/σ)max < 0.001 |
185 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.21 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. SHELXL-2014/7 (Sheldrick, 2015) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Ni1 | 0.2500 | −0.03344 (4) | 0.0000 | 0.02241 (11) | |
N1 | 0.21155 (5) | −0.01668 (17) | 0.13760 (10) | 0.0262 (3) | |
N2 | 0.16365 (5) | 0.01555 (18) | 0.16472 (11) | 0.0287 (3) | |
N3 | 0.19172 (5) | −0.04746 (16) | −0.11687 (10) | 0.0250 (3) | |
N4 | 0.21437 (5) | 0.02969 (17) | 0.31469 (10) | 0.0269 (3) | |
O1 | 0.2500 | −0.3149 (2) | 0.0000 | 0.0385 (4) | |
H1WA | 0.2384 (9) | −0.372 (3) | −0.0472 (17) | 0.058* | |
O2 | 0.2500 | 0.2501 (2) | 0.0000 | 0.0351 (4) | |
H2WA | 0.2441 (9) | 0.306 (3) | −0.0535 (16) | 0.053* | |
C1 | 0.16687 (6) | 0.0426 (2) | 0.27055 (12) | 0.0255 (3) | |
C2 | 0.24037 (6) | −0.0064 (2) | 0.22750 (12) | 0.0244 (3) | |
C3 | 0.20562 (6) | −0.0326 (2) | −0.21889 (12) | 0.0251 (3) | |
C4 | 0.17112 (7) | −0.0449 (3) | −0.30512 (13) | 0.0390 (4) | |
H4 | 0.1811 | −0.0328 | −0.3751 | 0.047* | |
C5 | 0.12170 (7) | −0.0755 (3) | −0.28513 (15) | 0.0454 (5) | |
H5 | 0.0979 | −0.0839 | −0.3419 | 0.055* | |
C6 | 0.10769 (6) | −0.0936 (3) | −0.18138 (14) | 0.0393 (4) | |
H6 | 0.0745 | −0.1157 | −0.1669 | 0.047* | |
C7 | 0.14384 (6) | −0.0783 (2) | −0.09896 (13) | 0.0316 (4) | |
H7 | 0.1345 | −0.0899 | −0.0285 | 0.038* | |
C8 | 0.12222 (6) | 0.0883 (2) | 0.32949 (12) | 0.0271 (3) | |
C9 | 0.12556 (6) | 0.1509 (2) | 0.43446 (12) | 0.0337 (4) | |
H9 | 0.1566 | 0.1575 | 0.4711 | 0.040* | |
C10 | 0.08310 (6) | 0.2036 (2) | 0.48518 (13) | 0.0370 (4) | |
H10 | 0.0863 | 0.2441 | 0.5557 | 0.044* | |
C11 | 0.03630 (6) | 0.1978 (2) | 0.43428 (14) | 0.0355 (4) | |
C12 | 0.03294 (7) | 0.1337 (3) | 0.32928 (15) | 0.0446 (5) | |
H12 | 0.0018 | 0.1273 | 0.2929 | 0.054* | |
C13 | 0.07497 (7) | 0.0794 (3) | 0.27817 (13) | 0.0395 (4) | |
H13 | 0.0716 | 0.0363 | 0.2083 | 0.047* | |
C14 | −0.00982 (7) | 0.2557 (3) | 0.49021 (17) | 0.0494 (5) | |
H14A | −0.0001 | 0.3085 | 0.5582 | 0.074* | |
H14B | −0.0307 | 0.1537 | 0.5014 | 0.074* | |
H14C | −0.0280 | 0.3416 | 0.4465 | 0.074* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ni1 | 0.02456 (17) | 0.02787 (17) | 0.01480 (15) | 0.000 | 0.00105 (11) | 0.000 |
N1 | 0.0261 (7) | 0.0337 (7) | 0.0187 (7) | 0.0002 (5) | 0.0015 (5) | −0.0007 (5) |
N2 | 0.0253 (7) | 0.0401 (8) | 0.0209 (7) | 0.0005 (6) | 0.0025 (5) | −0.0017 (5) |
N3 | 0.0273 (7) | 0.0278 (7) | 0.0198 (6) | −0.0006 (5) | 0.0017 (5) | −0.0002 (5) |
N4 | 0.0270 (7) | 0.0358 (7) | 0.0179 (6) | 0.0015 (5) | 0.0012 (5) | 0.0001 (5) |
O1 | 0.0656 (13) | 0.0273 (9) | 0.0215 (8) | 0.000 | −0.0073 (8) | 0.000 |
O2 | 0.0497 (10) | 0.0274 (9) | 0.0269 (8) | 0.000 | −0.0100 (8) | 0.000 |
C1 | 0.0281 (8) | 0.0278 (8) | 0.0207 (7) | −0.0003 (6) | 0.0016 (6) | 0.0018 (6) |
C2 | 0.0271 (8) | 0.0271 (8) | 0.0189 (8) | −0.0005 (6) | 0.0014 (6) | 0.0008 (6) |
C3 | 0.0282 (8) | 0.0272 (8) | 0.0199 (7) | −0.0002 (6) | 0.0022 (6) | 0.0000 (6) |
C4 | 0.0332 (10) | 0.0640 (12) | 0.0197 (8) | −0.0039 (8) | 0.0002 (7) | 0.0002 (8) |
C5 | 0.0302 (9) | 0.0745 (13) | 0.0307 (9) | −0.0064 (9) | −0.0069 (7) | −0.0029 (9) |
C6 | 0.0259 (9) | 0.0563 (11) | 0.0357 (9) | −0.0070 (8) | 0.0025 (7) | −0.0009 (8) |
C7 | 0.0299 (9) | 0.0412 (9) | 0.0242 (8) | −0.0038 (7) | 0.0051 (6) | 0.0000 (7) |
C8 | 0.0285 (8) | 0.0304 (8) | 0.0225 (7) | −0.0003 (7) | 0.0039 (6) | 0.0025 (6) |
C9 | 0.0285 (9) | 0.0463 (10) | 0.0263 (8) | −0.0006 (7) | 0.0009 (7) | −0.0031 (7) |
C10 | 0.0373 (10) | 0.0451 (10) | 0.0291 (8) | −0.0014 (8) | 0.0077 (7) | −0.0065 (7) |
C11 | 0.0319 (9) | 0.0363 (9) | 0.0391 (9) | −0.0009 (7) | 0.0110 (7) | 0.0014 (7) |
C12 | 0.0254 (9) | 0.0689 (13) | 0.0393 (10) | 0.0000 (9) | −0.0016 (7) | −0.0010 (9) |
C13 | 0.0340 (9) | 0.0595 (11) | 0.0246 (8) | −0.0018 (9) | −0.0004 (7) | −0.0040 (8) |
C14 | 0.0371 (10) | 0.0518 (11) | 0.0608 (12) | 0.0021 (9) | 0.0172 (9) | −0.0043 (10) |
Geometric parameters (Å, º) top
Ni1—N1i | 2.0495 (14) | C4—H4 | 0.9300 |
Ni1—N1 | 2.0495 (14) | C5—C6 | 1.372 (3) |
Ni1—N3 | 2.0834 (14) | C5—H5 | 0.9300 |
Ni1—N3i | 2.0834 (14) | C6—C7 | 1.380 (2) |
Ni1—O1 | 2.1066 (17) | C6—H6 | 0.9300 |
Ni1—O2 | 2.1223 (17) | C7—H7 | 0.9300 |
N1—C2 | 1.331 (2) | C8—C9 | 1.389 (2) |
N1—N2 | 1.365 (2) | C8—C13 | 1.390 (2) |
N2—C1 | 1.334 (2) | C9—C10 | 1.386 (2) |
N3—C7 | 1.333 (2) | C9—H9 | 0.9300 |
N3—C3 | 1.348 (2) | C10—C11 | 1.376 (2) |
N4—C2 | 1.348 (2) | C10—H10 | 0.9300 |
N4—C1 | 1.363 (2) | C11—C12 | 1.393 (3) |
O1—H1WA | 0.78 (2) | C11—C14 | 1.512 (2) |
O2—H2WA | 0.80 (2) | C12—C13 | 1.382 (3) |
C1—C8 | 1.475 (2) | C12—H12 | 0.9300 |
C2—C3i | 1.469 (2) | C13—H13 | 0.9300 |
C3—C4 | 1.385 (2) | C14—H14A | 0.9600 |
C3—C2i | 1.469 (2) | C14—H14B | 0.9600 |
C4—C5 | 1.378 (3) | C14—H14C | 0.9600 |
| | | |
N1i—Ni1—N1 | 172.98 (7) | C5—C4—H4 | 120.7 |
N1i—Ni1—N3 | 78.90 (5) | C3—C4—H4 | 120.7 |
N1—Ni1—N3 | 101.45 (5) | C6—C5—C4 | 119.87 (16) |
N1i—Ni1—N3i | 101.46 (5) | C6—C5—H5 | 120.1 |
N1—Ni1—N3i | 78.91 (5) | C4—C5—H5 | 120.1 |
N3—Ni1—N3i | 174.22 (7) | C5—C6—C7 | 118.62 (16) |
N1i—Ni1—O1 | 93.51 (4) | C5—C6—H6 | 120.7 |
N1—Ni1—O1 | 93.51 (4) | C7—C6—H6 | 120.7 |
N3—Ni1—O1 | 87.11 (3) | N3—C7—C6 | 122.26 (15) |
N3i—Ni1—O1 | 87.11 (3) | N3—C7—H7 | 118.9 |
N1i—Ni1—O2 | 86.49 (4) | C6—C7—H7 | 118.9 |
N1—Ni1—O2 | 86.49 (4) | C9—C8—C13 | 117.60 (15) |
N3—Ni1—O2 | 92.89 (3) | C9—C8—C1 | 122.20 (15) |
N3i—Ni1—O2 | 92.89 (3) | C13—C8—C1 | 120.09 (14) |
O1—Ni1—O2 | 180.0 | C10—C9—C8 | 120.74 (16) |
C2—N1—N2 | 107.05 (13) | C10—C9—H9 | 119.6 |
C2—N1—Ni1 | 114.50 (11) | C8—C9—H9 | 119.6 |
N2—N1—Ni1 | 137.47 (10) | C11—C10—C9 | 121.96 (15) |
C1—N2—N1 | 104.93 (13) | C11—C10—H10 | 119.0 |
C7—N3—C3 | 119.12 (13) | C9—C10—H10 | 119.0 |
C7—N3—Ni1 | 125.76 (11) | C10—C11—C12 | 117.27 (15) |
C3—N3—Ni1 | 115.03 (11) | C10—C11—C14 | 121.60 (16) |
C2—N4—C1 | 101.42 (13) | C12—C11—C14 | 121.13 (17) |
Ni1—O1—H1WA | 123.2 (17) | C13—C12—C11 | 121.29 (16) |
Ni1—O2—H2WA | 121.7 (16) | C13—C12—H12 | 119.4 |
N2—C1—N4 | 113.65 (14) | C11—C12—H12 | 119.4 |
N2—C1—C8 | 120.99 (14) | C12—C13—C8 | 121.14 (16) |
N4—C1—C8 | 125.33 (14) | C12—C13—H13 | 119.4 |
N1—C2—N4 | 112.96 (14) | C8—C13—H13 | 119.4 |
N1—C2—C3i | 117.50 (14) | C11—C14—H14A | 109.5 |
N4—C2—C3i | 129.54 (14) | C11—C14—H14B | 109.5 |
N3—C3—C4 | 121.46 (15) | H14A—C14—H14B | 109.5 |
N3—C3—C2i | 113.59 (13) | C11—C14—H14C | 109.5 |
C4—C3—C2i | 124.94 (15) | H14A—C14—H14C | 109.5 |
C5—C4—C3 | 118.65 (16) | H14B—C14—H14C | 109.5 |
| | | |
C2—N1—N2—C1 | −0.27 (16) | C4—C5—C6—C7 | 0.8 (3) |
Ni1—N1—N2—C1 | −167.63 (12) | C3—N3—C7—C6 | −0.8 (2) |
N1—N2—C1—N4 | −0.07 (17) | Ni1—N3—C7—C6 | −177.00 (13) |
N1—N2—C1—C8 | 177.85 (13) | C5—C6—C7—N3 | −0.3 (3) |
C2—N4—C1—N2 | 0.37 (17) | N2—C1—C8—C9 | −167.16 (16) |
C2—N4—C1—C8 | −177.44 (15) | N4—C1—C8—C9 | 10.5 (2) |
N2—N1—C2—N4 | 0.54 (17) | N2—C1—C8—C13 | 9.0 (2) |
Ni1—N1—C2—N4 | 171.18 (10) | N4—C1—C8—C13 | −173.35 (16) |
N2—N1—C2—C3i | −178.69 (13) | C13—C8—C9—C10 | −0.5 (3) |
Ni1—N1—C2—C3i | −8.05 (17) | C1—C8—C9—C10 | 175.77 (15) |
C1—N4—C2—N1 | −0.55 (16) | C8—C9—C10—C11 | −0.5 (3) |
C1—N4—C2—C3i | 178.56 (15) | C9—C10—C11—C12 | 1.0 (3) |
C7—N3—C3—C4 | 1.4 (2) | C9—C10—C11—C14 | −179.97 (18) |
Ni1—N3—C3—C4 | 178.00 (13) | C10—C11—C12—C13 | −0.5 (3) |
C7—N3—C3—C2i | −177.52 (14) | C14—C11—C12—C13 | −179.52 (19) |
Ni1—N3—C3—C2i | −0.88 (16) | C11—C12—C13—C8 | −0.5 (3) |
N3—C3—C4—C5 | −0.9 (3) | C9—C8—C13—C12 | 1.0 (3) |
C2i—C3—C4—C5 | 177.87 (17) | C1—C8—C13—C12 | −175.34 (17) |
C3—C4—C5—C6 | −0.2 (3) | | |
Symmetry code: (i) −x+1/2, y, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1WA···N4ii | 0.78 (2) | 2.16 (2) | 2.9351 (17) | 174 (3) |
O2—H2WA···N4iii | 0.80 (2) | 2.17 (2) | 2.9575 (17) | 169 (2) |
C7—H7···N2 | 0.93 | 2.62 | 3.378 (2) | 139 |
Symmetry codes: (ii) x, −y−1/2, z−1/2; (iii) x, −y+1/2, z−1/2. |