metal-organic compounds
Diaquabis[3-(4-methylphenyl)-5-(pyridin-2-yl-κN)-1H-1,2,4-triazolato-κN1]cadmium trihydrate
aCollege of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650500, People's Republic of China
*Correspondence e-mail: lfy20110407@163.com
In the title compound, [Cd(C14H11N4)2(H2O)2]·3H2O, the CdII cation is chelated by two 3-(4-methylphenyl)-5-(pyridin-2-yl)-1H-1,2,4-triazolate anions and coordinated by two water molecules in a distorted N4O2 octahedral geometry. Within the organic ligands, the methylphenyl rings are twisted with respect to the mean planes of chelating rings by 18.31 (16) and 14.89 (15)°. In the crystal, extensive O—H⋯O and O—H⋯N hydrogen bonds and weak C—H⋯O interactions link the molecules into a three-dimensional supramolecular architecture.
Keywords: crystal structure; triazolyl ligand; CdII complex; hydrogen bonds.
Structure description
Metal–azolate coordination polymers have attracted intense attention in recent years due to their interesting structures and potential applications (Yan et al., 2012). Many efforts have focused on symmetrical molecules based on the flexible bridging mode of 1,2,4-triazoles and their derivatives (Chen et al., 2011). It was found that the size and shape of the 3- and 5-substituents may be a crucial factor in determining the final structures of coordination polymers. However, there are few reports using asymmetrical triazolate ligands in the synthesis of metal–azolate coordination polymers (Liu et al., 2017). Here, we report the synthesis and of the title complex.
The title mononuclear complex consists of one CdII cation, two bidentate organic anions, two coordinating water molecules and three crystal water molecules. As shown in Fig. 1, the CdII cation is chelated by two organic ligands and is coordinated by two water molecules in a distorted octahedral geometry. In the organic ligands, the methylphenyl rings are twisted with respect to the mean planes of chelating rings by 18.31 (16) and 14.89 (15)°.
In the crystal, extensive O—H⋯O and O—H⋯N hydrogen bonds and weak C—H⋯O interactions link the molecules into a three-dimensional supramolecular architecture (Table 1, Fig. 2).
Synthesis and crystallization
A mixture of cadmium acetate dihydrate (26.7 mg, 0.1 mmol), aqueous ammonia (25%, 0.2 ml), water (4 ml) and 3-(4-methylphenyl)-5-(pyridin-2-yl)-1H-1,2,4-triazole (47.2 mg, 0.2 mmol) was sealed in a 20 ml Teflon-lined reactor and placed in an oven at 393 K for 72 h. The resulting mixture was filtered and the resulting colorless blocks were washed with ethanol (yield 75%, based on Cd). Analysis calculated (wt%) for C28H32CdN8O5: C 49.92, H 4.75, N 16.64; found: C 49.02, H 5.15, N 17.13..
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2
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Structural data
https://doi.org/10.1107/S2414314617009683/xu4028sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617009683/xu4028Isup2.hkl
Data collection: CrystalStructure (Rigaku/MSC, 2006); cell
CrystalStructure (Rigaku/MSC, 2006); data reduction: CrystalStructure (Rigaku/MSC, 2006); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: SHELXL2014 (Sheldrick, 2015b); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b).[Cd(C14H11N4)2(H2O)2]·3H2O | F(000) = 1376 |
Mr = 673.01 | Dx = 1.529 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.919 (2) Å | Cell parameters from 24845 reflections |
b = 23.045 (5) Å | θ = 3.1–25.0° |
c = 12.154 (2) Å | µ = 0.80 mm−1 |
β = 107.11 (3)° | T = 293 K |
V = 2922.8 (11) Å3 | Block, colorless |
Z = 4 | 0.30 × 0.27 × 0.25 mm |
Rigaku MM007-HF CCD (Saturn 724+) diffractometer | 4037 reflections with I > 2σ(I) |
Radiation source: rotating anode | Rint = 0.053 |
ω scans at fixed χ = 45° | θmax = 25.2°, θmin = 3.1° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −12→12 |
Tmin = 0.787, Tmax = 0.819 | k = −27→26 |
20295 measured reflections | l = −14→14 |
5124 independent reflections |
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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.080 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0319P)2 + 1.8376P] where P = (Fo2 + 2Fc2)/3 |
5124 reflections | (Δ/σ)max = 0.001 |
381 parameters | Δρmax = 0.37 e Å−3 |
0 restraints | Δρmin = −0.49 e Å−3 |
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. H atoms attached to carbons were constrained with C—H = 0.96 Å, and Uiso(H) = 1.5Ueq(C) of the attached C atom for methyl H atoms and C—H = 0.93 Å and 1.2Ueq(C) for other H atoms. The water H atoms were located from a Fourier map and restrained with O—H distance of 0.82–0.94 Å with Uiso(H) = 1.5Ueq(O). |
x | y | z | Uiso*/Ueq | ||
Cd1 | 0.80813 (2) | 0.08471 (2) | 0.89399 (2) | 0.03269 (9) | |
C1 | 0.7173 (3) | 0.19928 (13) | 0.5853 (3) | 0.0300 (7) | |
C2 | 0.7754 (3) | 0.20571 (13) | 0.7663 (3) | 0.0309 (7) | |
C3 | 0.8164 (3) | 0.22497 (13) | 0.8865 (3) | 0.0304 (7) | |
C4 | 0.8298 (3) | 0.28247 (15) | 0.9193 (3) | 0.0428 (9) | |
H4 | 0.8093 | 0.3116 | 0.8639 | 0.051* | |
C5 | 0.8737 (4) | 0.29671 (17) | 1.0343 (3) | 0.0518 (10) | |
H5 | 0.8838 | 0.3354 | 1.0571 | 0.062* | |
C6 | 0.9023 (4) | 0.25300 (16) | 1.1149 (3) | 0.0522 (10) | |
H6 | 0.9327 | 0.2614 | 1.1930 | 0.063* | |
C7 | 0.8848 (4) | 0.19643 (15) | 1.0768 (3) | 0.0434 (9) | |
H7 | 0.9032 | 0.1668 | 1.1312 | 0.052* | |
C8 | 0.6779 (3) | 0.21194 (14) | 0.4612 (3) | 0.0333 (8) | |
C9 | 0.6327 (3) | 0.26643 (14) | 0.4183 (3) | 0.0354 (8) | |
H9 | 0.6294 | 0.2961 | 0.4692 | 0.043* | |
C10 | 0.5927 (3) | 0.27715 (15) | 0.3011 (3) | 0.0397 (8) | |
H10 | 0.5625 | 0.3139 | 0.2750 | 0.048* | |
C11 | 0.5966 (3) | 0.23440 (15) | 0.2213 (3) | 0.0375 (8) | |
C12 | 0.6422 (4) | 0.18072 (15) | 0.2648 (3) | 0.0470 (10) | |
H12 | 0.6466 | 0.1513 | 0.2138 | 0.056* | |
C13 | 0.6815 (4) | 0.16917 (15) | 0.3814 (3) | 0.0427 (9) | |
H13 | 0.7108 | 0.1322 | 0.4070 | 0.051* | |
C14 | 0.7809 (3) | 0.00303 (13) | 1.2148 (3) | 0.0321 (7) | |
C15 | 0.6657 (3) | 0.04953 (13) | 1.0738 (3) | 0.0293 (7) | |
C16 | 0.5604 (3) | 0.07886 (12) | 0.9891 (3) | 0.0307 (7) | |
C17 | 0.4412 (3) | 0.08834 (14) | 1.0045 (3) | 0.0386 (8) | |
H17 | 0.4246 | 0.0761 | 1.0716 | 0.046* | |
C18 | 0.3472 (3) | 0.11615 (15) | 0.9192 (3) | 0.0419 (9) | |
H18 | 0.2666 | 0.1228 | 0.9281 | 0.050* | |
C19 | 0.3745 (4) | 0.13391 (15) | 0.8208 (3) | 0.0445 (9) | |
H19 | 0.3132 | 0.1529 | 0.7623 | 0.053* | |
C20 | 0.4946 (3) | 0.12285 (15) | 0.8111 (3) | 0.0428 (9) | |
H20 | 0.5124 | 0.1344 | 0.7441 | 0.051* | |
C21 | 0.8285 (3) | −0.02893 (13) | 1.3246 (3) | 0.0334 (8) | |
C22 | 0.7610 (4) | −0.03023 (15) | 1.4050 (3) | 0.0441 (9) | |
H22 | 0.6841 | −0.0101 | 1.3907 | 0.053* | |
C23 | 0.8074 (4) | −0.06140 (16) | 1.5070 (3) | 0.0461 (9) | |
H23 | 0.7605 | −0.0618 | 1.5597 | 0.055* | |
C24 | 0.9211 (4) | −0.09165 (14) | 1.5315 (3) | 0.0409 (9) | |
C25 | 0.9867 (4) | −0.09115 (16) | 1.4503 (3) | 0.0498 (10) | |
H25 | 1.0633 | −0.1116 | 1.4646 | 0.060* | |
C26 | 0.9411 (3) | −0.06092 (16) | 1.3479 (3) | 0.0450 (9) | |
H26 | 0.9864 | −0.0620 | 1.2941 | 0.054* | |
C27 | 0.5511 (4) | 0.24619 (18) | 0.0937 (3) | 0.0556 (11) | |
H27A | 0.5987 | 0.2226 | 0.0555 | 0.083* | |
H27B | 0.5640 | 0.2864 | 0.0798 | 0.083* | |
H27C | 0.4616 | 0.2370 | 0.0644 | 0.083* | |
C28 | 0.9733 (4) | −0.12478 (18) | 1.6430 (3) | 0.0590 (11) | |
H28A | 0.9876 | −0.1645 | 1.6263 | 0.089* | |
H28B | 0.9127 | −0.1232 | 1.6863 | 0.089* | |
H28C | 1.0527 | −0.1077 | 1.6872 | 0.089* | |
N1 | 0.7680 (3) | 0.14903 (11) | 0.7420 (2) | 0.0348 (7) | |
N2 | 0.7305 (3) | 0.14447 (11) | 0.6243 (2) | 0.0357 (7) | |
N3 | 0.8429 (3) | 0.18203 (11) | 0.9658 (2) | 0.0337 (6) | |
N4 | 0.7449 (3) | 0.23935 (11) | 0.6715 (2) | 0.0317 (6) | |
N5 | 0.7766 (3) | 0.03969 (11) | 1.0512 (2) | 0.0338 (6) | |
N6 | 0.8526 (3) | 0.00898 (11) | 1.1428 (2) | 0.0355 (7) | |
N7 | 0.5872 (3) | 0.09635 (11) | 0.8928 (2) | 0.0359 (7) | |
N8 | 0.6631 (3) | 0.02817 (11) | 1.1765 (2) | 0.0323 (6) | |
O1W | 1.0361 (2) | 0.07738 (10) | 0.9683 (2) | 0.0555 (7) | |
H1A | 1.0613 | 0.0520 | 0.9283 | 0.083* | |
H1B | 1.0889 | 0.0931 | 1.0232 | 0.083* | |
O2W | 0.8212 (3) | 0.00599 (12) | 0.7820 (3) | 0.0758 (9) | |
H2A | 0.8997 | −0.0008 | 0.7901 | 0.114* | |
H2B | 0.7597 | −0.0156 | 0.7521 | 0.114* | |
O3W | 0.7291 (3) | 0.36566 (11) | 0.6538 (2) | 0.0561 (7) | |
H3A | 0.7389 | 0.3299 | 0.6600 | 0.084* | |
H3B | 0.7924 | 0.3841 | 0.6928 | 0.084* | |
O4W | 0.5469 (3) | 0.06085 (14) | 0.5259 (3) | 0.0922 (12) | |
H4A | 0.6092 | 0.0820 | 0.5514 | 0.138* | |
H4B | 0.5420 | 0.0305 | 0.5755 | 0.138* | |
O5W | 0.5504 (3) | −0.04741 (14) | 0.7179 (3) | 0.0719 (9) | |
H5A | 0.4896 | −0.0362 | 0.7410 | 0.108* | |
H5B | 0.5206 | −0.0556 | 0.6567 | 0.108* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cd1 | 0.03730 (16) | 0.03264 (14) | 0.03062 (15) | 0.00326 (11) | 0.01385 (11) | 0.00511 (10) |
C1 | 0.0311 (18) | 0.0261 (17) | 0.0333 (19) | −0.0016 (13) | 0.0101 (14) | 0.0009 (13) |
C2 | 0.0297 (18) | 0.0332 (18) | 0.0298 (19) | 0.0011 (13) | 0.0086 (14) | 0.0027 (14) |
C3 | 0.0304 (18) | 0.0329 (18) | 0.0285 (18) | 0.0031 (13) | 0.0098 (14) | −0.0004 (13) |
C4 | 0.054 (2) | 0.035 (2) | 0.036 (2) | 0.0035 (16) | 0.0088 (18) | 0.0013 (15) |
C5 | 0.069 (3) | 0.044 (2) | 0.037 (2) | 0.0007 (19) | 0.007 (2) | −0.0083 (17) |
C6 | 0.067 (3) | 0.055 (2) | 0.028 (2) | 0.007 (2) | 0.0047 (19) | −0.0080 (17) |
C7 | 0.052 (2) | 0.044 (2) | 0.032 (2) | 0.0063 (17) | 0.0074 (18) | 0.0044 (16) |
C8 | 0.0329 (19) | 0.0380 (19) | 0.0287 (19) | −0.0053 (14) | 0.0085 (15) | −0.0008 (14) |
C9 | 0.042 (2) | 0.0351 (19) | 0.0295 (19) | −0.0031 (15) | 0.0106 (16) | −0.0020 (14) |
C10 | 0.041 (2) | 0.041 (2) | 0.035 (2) | −0.0007 (15) | 0.0076 (17) | 0.0062 (15) |
C11 | 0.035 (2) | 0.048 (2) | 0.0277 (19) | −0.0042 (15) | 0.0063 (15) | 0.0020 (15) |
C12 | 0.062 (3) | 0.043 (2) | 0.036 (2) | 0.0020 (18) | 0.0131 (19) | −0.0062 (16) |
C13 | 0.056 (2) | 0.035 (2) | 0.033 (2) | 0.0041 (16) | 0.0078 (18) | 0.0018 (15) |
C14 | 0.038 (2) | 0.0324 (18) | 0.0266 (18) | 0.0014 (14) | 0.0107 (15) | 0.0004 (13) |
C15 | 0.0337 (19) | 0.0271 (17) | 0.0294 (19) | 0.0001 (13) | 0.0129 (15) | 0.0019 (13) |
C16 | 0.0352 (19) | 0.0281 (17) | 0.0307 (18) | 0.0008 (14) | 0.0125 (15) | −0.0010 (13) |
C17 | 0.041 (2) | 0.043 (2) | 0.036 (2) | 0.0051 (16) | 0.0176 (16) | 0.0035 (15) |
C18 | 0.033 (2) | 0.049 (2) | 0.045 (2) | 0.0059 (16) | 0.0139 (17) | 0.0048 (17) |
C19 | 0.038 (2) | 0.049 (2) | 0.044 (2) | 0.0088 (16) | 0.0074 (18) | 0.0103 (17) |
C20 | 0.040 (2) | 0.054 (2) | 0.036 (2) | 0.0049 (17) | 0.0137 (17) | 0.0145 (16) |
C21 | 0.038 (2) | 0.0334 (18) | 0.0285 (19) | −0.0032 (14) | 0.0092 (15) | 0.0004 (14) |
C22 | 0.048 (2) | 0.051 (2) | 0.034 (2) | 0.0160 (17) | 0.0143 (18) | 0.0040 (16) |
C23 | 0.059 (3) | 0.054 (2) | 0.028 (2) | 0.0041 (19) | 0.0177 (18) | 0.0037 (16) |
C24 | 0.047 (2) | 0.042 (2) | 0.030 (2) | −0.0058 (16) | 0.0059 (17) | 0.0047 (15) |
C25 | 0.036 (2) | 0.062 (3) | 0.049 (2) | 0.0102 (18) | 0.0100 (18) | 0.0175 (19) |
C26 | 0.043 (2) | 0.057 (2) | 0.040 (2) | 0.0059 (18) | 0.0192 (18) | 0.0142 (17) |
C27 | 0.060 (3) | 0.069 (3) | 0.034 (2) | 0.003 (2) | 0.008 (2) | 0.0082 (18) |
C28 | 0.070 (3) | 0.069 (3) | 0.033 (2) | 0.003 (2) | 0.007 (2) | 0.0153 (19) |
N1 | 0.0478 (18) | 0.0317 (15) | 0.0266 (16) | −0.0010 (12) | 0.0133 (13) | 0.0027 (11) |
N2 | 0.0466 (18) | 0.0341 (16) | 0.0269 (16) | −0.0057 (12) | 0.0117 (14) | 0.0008 (11) |
N3 | 0.0385 (17) | 0.0357 (16) | 0.0260 (16) | 0.0015 (12) | 0.0082 (13) | 0.0018 (11) |
N4 | 0.0363 (16) | 0.0323 (15) | 0.0255 (15) | −0.0003 (12) | 0.0073 (12) | 0.0017 (11) |
N5 | 0.0360 (17) | 0.0376 (16) | 0.0287 (16) | 0.0058 (12) | 0.0111 (13) | 0.0071 (11) |
N6 | 0.0377 (17) | 0.0403 (16) | 0.0298 (16) | 0.0068 (12) | 0.0120 (13) | 0.0090 (12) |
N7 | 0.0345 (17) | 0.0430 (16) | 0.0302 (16) | 0.0055 (12) | 0.0096 (13) | 0.0069 (12) |
N8 | 0.0376 (17) | 0.0338 (15) | 0.0280 (15) | 0.0057 (12) | 0.0139 (13) | 0.0028 (11) |
O1W | 0.0401 (15) | 0.0577 (17) | 0.0672 (19) | 0.0064 (12) | 0.0135 (14) | −0.0171 (13) |
O2W | 0.084 (2) | 0.069 (2) | 0.081 (2) | −0.0120 (16) | 0.0345 (19) | −0.0199 (16) |
O3W | 0.0701 (19) | 0.0436 (15) | 0.0519 (17) | 0.0050 (13) | 0.0137 (15) | 0.0053 (12) |
O4W | 0.112 (3) | 0.087 (2) | 0.084 (3) | −0.056 (2) | 0.038 (2) | −0.0258 (19) |
O5W | 0.0491 (18) | 0.109 (3) | 0.058 (2) | −0.0082 (16) | 0.0167 (15) | −0.0098 (17) |
Cd1—N5 | 2.288 (3) | C16—N7 | 1.349 (4) |
Cd1—O2W | 2.298 (3) | C16—C17 | 1.386 (5) |
Cd1—N1 | 2.308 (3) | C17—C18 | 1.383 (5) |
Cd1—O1W | 2.391 (3) | C17—H17 | 0.9300 |
Cd1—N3 | 2.396 (3) | C18—C19 | 1.377 (5) |
Cd1—N7 | 2.423 (3) | C18—H18 | 0.9300 |
C1—N2 | 1.342 (4) | C19—C20 | 1.374 (5) |
C1—N4 | 1.362 (4) | C19—H19 | 0.9300 |
C1—C8 | 1.471 (4) | C20—N7 | 1.338 (4) |
C2—N1 | 1.336 (4) | C20—H20 | 0.9300 |
C2—N4 | 1.347 (4) | C21—C22 | 1.387 (5) |
C2—C3 | 1.465 (4) | C21—C26 | 1.390 (5) |
C3—N3 | 1.352 (4) | C22—C23 | 1.393 (5) |
C3—C4 | 1.379 (4) | C22—H22 | 0.9300 |
C4—C5 | 1.376 (5) | C23—C24 | 1.378 (5) |
C4—H4 | 0.9300 | C23—H23 | 0.9300 |
C5—C6 | 1.375 (5) | C24—C25 | 1.380 (5) |
C5—H5 | 0.9300 | C24—C28 | 1.513 (5) |
C6—C7 | 1.378 (5) | C25—C26 | 1.384 (5) |
C6—H6 | 0.9300 | C25—H25 | 0.9300 |
C7—N3 | 1.333 (4) | C26—H26 | 0.9300 |
C7—H7 | 0.9300 | C27—H27A | 0.9600 |
C8—C13 | 1.391 (5) | C27—H27B | 0.9600 |
C8—C9 | 1.393 (4) | C27—H27C | 0.9600 |
C9—C10 | 1.383 (5) | C28—H28A | 0.9600 |
C9—H9 | 0.9300 | C28—H28B | 0.9600 |
C10—C11 | 1.392 (5) | C28—H28C | 0.9600 |
C10—H10 | 0.9300 | N1—N2 | 1.370 (4) |
C11—C12 | 1.379 (5) | N5—N6 | 1.373 (4) |
C11—C27 | 1.508 (5) | O1W—H1A | 0.8557 |
C12—C13 | 1.380 (5) | O1W—H1B | 0.8263 |
C12—H12 | 0.9300 | O2W—H2A | 0.8470 |
C13—H13 | 0.9300 | O2W—H2B | 0.8287 |
C14—N6 | 1.341 (4) | O3W—H3A | 0.8318 |
C14—N8 | 1.362 (4) | O3W—H3B | 0.8307 |
C14—C21 | 1.478 (4) | O4W—H4A | 0.8201 |
C15—N5 | 1.338 (4) | O4W—H4B | 0.9352 |
C15—N8 | 1.350 (4) | O5W—H5A | 0.8342 |
C15—C16 | 1.464 (4) | O5W—H5B | 0.7430 |
N5—Cd1—O2W | 100.82 (10) | C16—C17—H17 | 120.3 |
N5—Cd1—N1 | 156.95 (10) | C19—C18—C17 | 119.1 (3) |
O2W—Cd1—N1 | 93.61 (10) | C19—C18—H18 | 120.5 |
N5—Cd1—O1W | 92.76 (10) | C17—C18—H18 | 120.5 |
O2W—Cd1—O1W | 85.91 (10) | C20—C19—C18 | 118.4 (3) |
N1—Cd1—O1W | 106.22 (10) | C20—C19—H19 | 120.8 |
N5—Cd1—N3 | 99.62 (9) | C18—C19—H19 | 120.8 |
O2W—Cd1—N3 | 157.52 (10) | N7—C20—C19 | 123.6 (3) |
N1—Cd1—N3 | 70.29 (9) | N7—C20—H20 | 118.2 |
O1W—Cd1—N3 | 83.85 (9) | C19—C20—H20 | 118.2 |
N5—Cd1—N7 | 70.18 (9) | C22—C21—C26 | 117.8 (3) |
O2W—Cd1—N7 | 108.61 (10) | C22—C21—C14 | 121.9 (3) |
N1—Cd1—N7 | 88.27 (10) | C26—C21—C14 | 120.2 (3) |
O1W—Cd1—N7 | 159.08 (9) | C21—C22—C23 | 120.6 (3) |
N3—Cd1—N7 | 87.11 (9) | C21—C22—H22 | 119.7 |
N2—C1—N4 | 112.9 (3) | C23—C22—H22 | 119.7 |
N2—C1—C8 | 121.2 (3) | C24—C23—C22 | 121.4 (3) |
N4—C1—C8 | 125.9 (3) | C24—C23—H23 | 119.3 |
N1—C2—N4 | 112.9 (3) | C22—C23—H23 | 119.3 |
N1—C2—C3 | 119.9 (3) | C23—C24—C25 | 117.8 (3) |
N4—C2—C3 | 127.2 (3) | C23—C24—C28 | 121.8 (3) |
N3—C3—C4 | 121.0 (3) | C25—C24—C28 | 120.5 (3) |
N3—C3—C2 | 115.3 (3) | C24—C25—C26 | 121.5 (3) |
C4—C3—C2 | 123.7 (3) | C24—C25—H25 | 119.3 |
C5—C4—C3 | 119.9 (3) | C26—C25—H25 | 119.3 |
C5—C4—H4 | 120.0 | C25—C26—C21 | 120.9 (3) |
C3—C4—H4 | 120.0 | C25—C26—H26 | 119.6 |
C6—C5—C4 | 119.1 (3) | C21—C26—H26 | 119.6 |
C6—C5—H5 | 120.4 | C11—C27—H27A | 109.5 |
C4—C5—H5 | 120.4 | C11—C27—H27B | 109.5 |
C5—C6—C7 | 118.3 (3) | H27A—C27—H27B | 109.5 |
C5—C6—H6 | 120.9 | C11—C27—H27C | 109.5 |
C7—C6—H6 | 120.9 | H27A—C27—H27C | 109.5 |
N3—C7—C6 | 123.2 (3) | H27B—C27—H27C | 109.5 |
N3—C7—H7 | 118.4 | C24—C28—H28A | 109.5 |
C6—C7—H7 | 118.4 | C24—C28—H28B | 109.5 |
C13—C8—C9 | 117.2 (3) | H28A—C28—H28B | 109.5 |
C13—C8—C1 | 121.0 (3) | C24—C28—H28C | 109.5 |
C9—C8—C1 | 121.8 (3) | H28A—C28—H28C | 109.5 |
C10—C9—C8 | 121.1 (3) | H28B—C28—H28C | 109.5 |
C10—C9—H9 | 119.5 | C2—N1—N2 | 106.6 (2) |
C8—C9—H9 | 119.5 | C2—N1—Cd1 | 117.7 (2) |
C9—C10—C11 | 121.7 (3) | N2—N1—Cd1 | 135.56 (19) |
C9—C10—H10 | 119.1 | C1—N2—N1 | 105.4 (2) |
C11—C10—H10 | 119.1 | C7—N3—C3 | 118.5 (3) |
C12—C11—C10 | 116.7 (3) | C7—N3—Cd1 | 124.9 (2) |
C12—C11—C27 | 121.9 (3) | C3—N3—Cd1 | 116.6 (2) |
C10—C11—C27 | 121.4 (3) | C2—N4—C1 | 102.2 (3) |
C11—C12—C13 | 122.3 (3) | C15—N5—N6 | 106.8 (2) |
C11—C12—H12 | 118.8 | C15—N5—Cd1 | 117.5 (2) |
C13—C12—H12 | 118.8 | N6—N5—Cd1 | 135.0 (2) |
C12—C13—C8 | 121.0 (3) | C14—N6—N5 | 104.6 (3) |
C12—C13—H13 | 119.5 | C20—N7—C16 | 118.1 (3) |
C8—C13—H13 | 119.5 | C20—N7—Cd1 | 126.1 (2) |
N6—C14—N8 | 114.1 (3) | C16—N7—Cd1 | 115.5 (2) |
N6—C14—C21 | 121.5 (3) | C15—N8—C14 | 101.3 (3) |
N8—C14—C21 | 124.5 (3) | Cd1—O1W—H1A | 107.8 |
N5—C15—N8 | 113.3 (3) | Cd1—O1W—H1B | 132.5 |
N5—C15—C16 | 120.3 (3) | H1A—O1W—H1B | 119.7 |
N8—C15—C16 | 126.4 (3) | Cd1—O2W—H2A | 108.2 |
N7—C16—C17 | 121.5 (3) | Cd1—O2W—H2B | 123.3 |
N7—C16—C15 | 115.0 (3) | H2A—O2W—H2B | 127.1 |
C17—C16—C15 | 123.5 (3) | H3A—O3W—H3B | 113.1 |
C18—C17—C16 | 119.4 (3) | H4A—O4W—H4B | 113.5 |
C18—C17—H17 | 120.3 | H5A—O5W—H5B | 105.0 |
N1—C2—C3—N3 | −0.7 (4) | C23—C24—C25—C26 | 0.6 (6) |
N4—C2—C3—N3 | −179.2 (3) | C28—C24—C25—C26 | −179.7 (4) |
N1—C2—C3—C4 | 178.3 (3) | C24—C25—C26—C21 | 1.3 (6) |
N4—C2—C3—C4 | −0.2 (5) | C22—C21—C26—C25 | −2.5 (5) |
N3—C3—C4—C5 | 1.5 (5) | C14—C21—C26—C25 | −179.9 (3) |
C2—C3—C4—C5 | −177.4 (3) | N4—C2—N1—N2 | 0.0 (4) |
C3—C4—C5—C6 | −0.6 (6) | C3—C2—N1—N2 | −178.7 (3) |
C4—C5—C6—C7 | −0.5 (6) | N4—C2—N1—Cd1 | −177.3 (2) |
C5—C6—C7—N3 | 0.8 (6) | C3—C2—N1—Cd1 | 4.0 (4) |
N2—C1—C8—C13 | −14.9 (5) | N4—C1—N2—N1 | 0.3 (4) |
N4—C1—C8—C13 | 164.5 (3) | C8—C1—N2—N1 | 179.8 (3) |
N2—C1—C8—C9 | 163.5 (3) | C2—N1—N2—C1 | −0.2 (3) |
N4—C1—C8—C9 | −17.1 (5) | Cd1—N1—N2—C1 | 176.4 (2) |
C13—C8—C9—C10 | 0.3 (5) | C6—C7—N3—C3 | 0.1 (5) |
C1—C8—C9—C10 | −178.2 (3) | C6—C7—N3—Cd1 | −179.3 (3) |
C8—C9—C10—C11 | −0.4 (5) | C4—C3—N3—C7 | −1.3 (5) |
C9—C10—C11—C12 | 0.1 (5) | C2—C3—N3—C7 | 177.8 (3) |
C9—C10—C11—C27 | 179.1 (3) | C4—C3—N3—Cd1 | 178.2 (2) |
C10—C11—C12—C13 | 0.4 (6) | C2—C3—N3—Cd1 | −2.8 (3) |
C27—C11—C12—C13 | −178.6 (4) | N1—C2—N4—C1 | 0.2 (4) |
C11—C12—C13—C8 | −0.6 (6) | C3—C2—N4—C1 | 178.7 (3) |
C9—C8—C13—C12 | 0.2 (5) | N2—C1—N4—C2 | −0.3 (4) |
C1—C8—C13—C12 | 178.7 (3) | C8—C1—N4—C2 | −179.8 (3) |
N5—C15—C16—N7 | −2.6 (4) | N8—C15—N5—N6 | 1.2 (4) |
N8—C15—C16—N7 | 179.9 (3) | C16—C15—N5—N6 | −176.6 (3) |
N5—C15—C16—C17 | 177.2 (3) | N8—C15—N5—Cd1 | −171.0 (2) |
N8—C15—C16—C17 | −0.2 (5) | C16—C15—N5—Cd1 | 11.3 (4) |
N7—C16—C17—C18 | 0.3 (5) | N8—C14—N6—N5 | −0.4 (4) |
C15—C16—C17—C18 | −179.6 (3) | C21—C14—N6—N5 | 179.0 (3) |
C16—C17—C18—C19 | −0.2 (5) | C15—N5—N6—C14 | −0.5 (3) |
C17—C18—C19—C20 | 0.4 (5) | Cd1—N5—N6—C14 | 169.7 (2) |
C18—C19—C20—N7 | −0.8 (6) | C19—C20—N7—C16 | 0.9 (5) |
N6—C14—C21—C22 | 173.1 (3) | C19—C20—N7—Cd1 | −172.5 (3) |
N8—C14—C21—C22 | −7.6 (5) | C17—C16—N7—C20 | −0.6 (5) |
N6—C14—C21—C26 | −9.6 (5) | C15—C16—N7—C20 | 179.2 (3) |
N8—C14—C21—C26 | 169.7 (3) | C17—C16—N7—Cd1 | 173.5 (2) |
C26—C21—C22—C23 | 1.8 (5) | C15—C16—N7—Cd1 | −6.7 (3) |
C14—C21—C22—C23 | 179.1 (3) | N5—C15—N8—C14 | −1.3 (3) |
C21—C22—C23—C24 | 0.2 (6) | C16—C15—N8—C14 | 176.3 (3) |
C22—C23—C24—C25 | −1.4 (6) | N6—C14—N8—C15 | 1.0 (4) |
C22—C23—C24—C28 | 179.0 (4) | C21—C14—N8—C15 | −178.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1A···N6i | 0.86 | 2.02 | 2.869 (4) | 170 |
O1W—H1B···O3Wii | 0.83 | 2.08 | 2.907 (4) | 176 |
O2W—H2A···N6i | 0.85 | 2.59 | 3.424 (4) | 167 |
O2W—H2B···O5W | 0.83 | 2.32 | 3.084 (4) | 154 |
O3W—H3A···N4 | 0.83 | 2.09 | 2.920 (3) | 175 |
O3W—H3B···O5Wiii | 0.83 | 2.35 | 3.168 (4) | 168 |
O4W—H4A···N2 | 0.82 | 1.98 | 2.785 (4) | 167 |
O4W—H4B···O5W | 0.94 | 2.48 | 3.408 (5) | 175 |
O5W—H5A···N8iv | 0.83 | 2.19 | 3.006 (4) | 165 |
O5W—H5B···O4Wv | 0.74 | 2.13 | 2.854 (5) | 167 |
C17—H17···O5Wiv | 0.93 | 2.58 | 3.479 (5) | 163 |
Symmetry codes: (i) −x+2, −y, −z+2; (ii) x+1/2, −y+1/2, z+1/2; (iii) −x+3/2, y+1/2, −z+3/2; (iv) −x+1, −y, −z+2; (v) −x+1, −y, −z+1. |
Funding information
Funding for this research was provided by: National Natural Science Foundation of China (grant No. 21161023); Natural Science Foundation of Yunnan Province (grant No. 2009CD048).
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